JP7558643B2 - Composition, member, and method for manufacturing member - Google Patents

Description

The present invention relates to a composition, a member, and a method for manufacturing the member, and more specifically to a composition that produces a cured product with an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion, a member in which the cured product of this composition exists as an adhesive layer, and a method for manufacturing the member.

Cationic curable compositions are used in fields such as inks, paints, various coatings, adhesives, and optical components. Various reports have been published on improvements to such curable compositions.

For example, Patent Document 1 proposes an active energy ray curable adhesive composition for plastic films, etc., which has low viscosity, excellent curing properties, and excellent adhesion to various plastic films or sheets and colorless transparency. Patent Document 2 proposes an active energy ray curable adhesive composition for plastic films, etc., which has low viscosity, excellent curing properties, excellent adhesion to various plastic films, etc., even when the atmospheric humidity during coating and curing is high, and excellent colorless transparency. Patent Document 3 proposes a photocurable adhesive that has excellent curing properties, good adhesion after a certain period of time, durability, and adhesion after completion of a moist heat test, even when the humidity of the coating environment is high, and has low viscosity. Patent Document 4 proposes an adhesive for polarizing plates that has good adhesion to polarizers and protective films, excellent heat resistance, and can suppress the occurrence of cracks in the polarizer.

JP 2015-034188 A JP 2015-057467 A JP 2015-143352 A JP 2016-018163 A

However, the adhesives described in Patent Documents 1 to 4 require a long time to achieve the desired adhesion, and if stress or the like is applied before the desired adhesion is achieved, peeling problems may occur.

The object of the present invention is to provide a composition that produces a cured product with an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion, a member in which the cured product of this composition exists as an adhesive layer, and a method for producing the member.

As a result of intensive research into solving the above problems, the inventors discovered that the initial curing speed can be improved and the above problems can be solved by further adding an aromatic alcohol to a composition containing a cationic polymerizable compound and an acid generator, and thus completed the present invention.

（一般式（ＩＩ－１）中、Ｒ^１は水素原子、メチル基またはハロゲン原子を表し、
Ｒ^３は、水素原子または炭素原子数１～６のアルキル基を表し、
ｔは、１～６の整数であり、＊は、結合手を表す。）
前記脂肪族エポキシ化合物および前記脂環式エポキシ化合物の合計量が、前記カチオン重合性化合物１００質量部に対して５０質量部以上９９質量部以下であり、
前記芳香族アルコールが、下記一般式（７）、

（芳香族環Ａｒは炭素原子数６～２０の置換基を有してもよいｐ価の芳香族炭化水素環または炭素原子数２～２０の置換基を有してもよいｐ価の芳香族複素環であり、Ｂは一般式（８）で表される基（ｐが２以上の場合は、それぞれのＢは同一であっても異なるものであってもよい。）であり、Ｙ^２は、炭素原子数１～２０の直鎖、分岐またはシクロアルキル環を有するアルキル基からｑ個の水素原子を除いた基である。
また、ｐは１～６を表し、ｑは１～１０を表し、＊は、結合手を表し、
前記置換基が、炭素原子数１～１０のアルキル基または炭素原子数１～１０のアルコキシ基から選択されるものである。）で表される芳香族アルコールであり、
前記芳香族アルコールの含有量が、前記カチオン重合性化合物、前記芳香族アルコール、および前記酸発生剤の合計量１００質量部中、０．９７質量部以上２０質量部以下であり、
接着剤用の組成物であることを特徴とするものである。 That is, the composition of the present invention contains a cationically polymerizable compound, an aromatic alcohol, and an acid generator,
the cationically polymerizable compound includes both an aliphatic epoxy compound and an alicyclic epoxy compound,
the aliphatic epoxy compound is a combination of a low molecular weight aliphatic epoxy compound having a molecular weight of 1,000 or less and a high molecular weight aliphatic epoxy compound having a molecular weight of more than 1,000 and 100,000 or less;
The high molecular weight aliphatic epoxy compound has the following structural unit (II-1):

In general formula (II-1), R ¹ represents a hydrogen atom, a methyl group, or a halogen atom;
^R3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
t is an integer of 1 to 6, and * represents a bond.
the total amount of the aliphatic epoxy compound and the alicyclic epoxy compound is 50 parts by mass or more and 99 parts by mass or less relative to 100 parts by mass of the cationically polymerizable compound,
The aromatic alcohol is represented by the following general formula (7):

(The aromatic ring Ar is a p-valent aromatic hydrocarbon ring which may have a substituent having 6 to 20 carbon atoms or a p-valent aromatic heterocycle which may have a substituent having 2 to 20 carbon atoms, B is a group represented by general formula (8) (when p is 2 or more, each B may be the same or different), and ^Y2 is a group in which q hydrogen atoms have been removed from an alkyl group having a straight chain, branched chain or cycloalkyl ring and having 1 to 20 carbon atoms.
In addition, p represents 1 to 6, q represents 1 to 10, * represents a bond,
the substituent is selected from an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms;
a content of the aromatic alcohol is 0.97 parts by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the cationically polymerizable compound, the aromatic alcohol, and the acid generator;
The composition is characterized as being an adhesive composition.

In the composition of the present invention, it is preferable that the cationic polymerizable compound contains a vinyl ether compound. In addition, in the composition of the present invention, it is preferable that the aromatic alcohol is a primary alcohol or a secondary alcohol. Furthermore, in the composition of the present invention, it is preferable that the composition further contains a radical polymerizable compound having a (meth)acryloyl group. Furthermore, in the composition of the present invention, it is preferable that the radical polymerizable compound having a (meth)acryloyl group is an acrylate or methacrylate having a hydroxyl group.

The member of the present invention is characterized in that the cured product of the composition of the present invention is present as an adhesive layer.

The method for producing a member of the present invention is characterized by having a curing step in which the composition of the present invention is applied to an object to be adhered and cured.

The present invention provides a composition that produces a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion, a cured product thereof, and a method for producing the cured product.

The composition of the present invention, its cured product, and the method for producing the cured product are described in detail below.

1. Composition
The composition of the present invention has a cationic polymerizable compound, an aromatic alcohol, and an acid generator. By using the cationic polymerizable compound, the aromatic alcohol, and the acid generator in combination, the composition of the present invention can obtain a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion. The reason why the cationic polymerizable compound, the aromatic alcohol, and the acid generator in combination produce the above-mentioned effects is not clear, but is presumed to be as follows.

That is, when a cationic polymerizable compound and an aromatic alcohol are used in combination, the initial curing speed of the cationic polymerizable compound itself, the cationic polymerizable compound, and the aromatic alcohol can be effectively improved due to the structure of the hydroxyl group of the aromatic alcohol and the effect of promoting the reaction of the epoxy group. As a result, the initial adhesion can also be effectively improved. In addition, the reaction of the cationic polymerizable compound and the aromatic alcohol proceeds easily in the presence of an acid, and a polymer having a hydroxyl group can be obtained. Such a polymer having a hydroxyl group can form, for example, a hydrogen bond with a polar group on the surface of the adherend. As a result, the cured product of the composition of the present invention has excellent adhesion to the adherend. From the above, the composition of the present invention can be obtained as a cured product by using a cationic polymerizable compound, an aromatic alcohol, and an acid generator in combination.

In addition, due to the effect of providing excellent initial curing speed, initial adhesion and adhesion, for example, it becomes easier to reduce the amount of acid generator added. In addition, the amount of unreacted cationically polymerizable groups remaining in the cured product formed using the composition of the present invention can be reduced, making it possible to suppress, for example, the reaction between the remaining cationically polymerizable groups and other atoms present on the adherend.

The initial adhesion refers to the degree of adhesion immediately after the composition is used to form a cured product, and can be evaluated, for example, by the adhesion 10 minutes after the start of the curing process. The subsequent adhesion refers to the degree of adhesion after the adhesion of the cured product has stabilized, and can be evaluated, for example, by the adhesion after the product is left to stand under specified conditions for 24 hours after the curing process. The initial curing speed indicates the rate at which the curing reaction progresses from the start of the curing process, and can be evaluated, for example, by the amount of heat generated per unit time associated with the curing reaction (the amount of heat generated observed from the start of the curing process to the peak top/the time required from the start of the curing process to the peak top). The amount of heat generated can be measured using a photochemical reaction calorimeter (photo-DSC).

The components of the composition of the present invention are described in detail below.

<1-1. Cationic polymerizable compound>
The cationic polymerizable compound is a compound having a cationic polymerizable group, and is a compound that undergoes polymerization or crosslinking reaction by an acid generator activated by irradiation with active energy rays or heating. For example, epoxy compounds, oxetane compounds, vinyl ether compounds, cyclic ether compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds, etc. can be used, and one or more of these can be used. Among these, from the viewpoint of obtaining a composition with excellent adhesion, it is preferable that the cationic polymerizable compound contains at least one of epoxy compounds, oxetane compounds, and vinyl ether compounds, and particularly preferably contains an epoxy compound. By using these compounds as the cationic polymerizable compound, the composition of the present invention has an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

Epoxy compounds include all those containing an epoxy structure. For example, a compound containing both an epoxy structure and an oxetane structure is an epoxy compound. Examples of such epoxy compounds include aliphatic epoxy compounds, alicyclic epoxy compounds, and aromatic epoxy compounds. Here, an alicyclic epoxy compound means a compound having an epoxy cycloalkyl group, and a compound simply having an aliphatic ring is classified as an aliphatic epoxy group. In the composition of the present invention, it is preferable that the cationic polymerizable compound contains at least one of an aliphatic epoxy compound and an alicyclic epoxy compound, and it is more preferable that the composition contains both. This makes it possible to obtain the effects of the present invention well.

<Aliphatic epoxy compound>
An aliphatic epoxy compound is a compound having an aliphatic epoxy group. In the composition of the present invention, an aliphatic epoxy compound refers to an epoxy compound that is not classified as an alicyclic epoxy compound or an aromatic epoxy compound, which will be described later. In the composition of the present invention, an aromatic epoxy compound means an epoxy compound containing an aromatic ring, and an alicyclic epoxy compound means a compound having an epoxycycloalkyl group, as described above, and a compound simply having an aliphatic ring is classified as an aliphatic epoxy group. In addition, an alicyclic epoxy compound is a compound that does not contain an aromatic ring.

The molecular weight of the aliphatic epoxy compound is preferably in the range of 50 to 100,000, more preferably in the range of 100 to 50,000, and particularly preferably in the range of 150 to 20,000. By having the molecular weight within this range, the composition of the present invention can provide a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

Specific examples of aliphatic epoxy compounds include monofunctional epoxy compounds such as glycidyl ethers of aliphatic alcohols and glycidyl esters of alkyl carboxylic acids, and polyfunctional epoxy compounds such as polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts, and polyglycidyl esters of aliphatic long-chain polybasic acids.

Representative aliphatic epoxy compounds include glycidyl ethers of polyhydric alcohols such as allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, bisphenol A diglycidyl ether, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, and diglycidyl ether of polypropylene glycol; polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane, and glycerin; and diglycidyl esters of aliphatic long-chain dibasic acids. Further examples include monoglycidyl ethers of higher aliphatic alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, epoxy octyl stearate, epoxy butyl stearate, epoxidized soybean oil, and epoxidized polybutadiene.

As the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct, which is used in the polyfunctional epoxy compound as the aliphatic epoxy compound, a diglycidyl ether of an aliphatic diol or its alkylene oxide adduct can be preferably used, and among them, a compound represented by the following general formula (1) can be preferably used. By using such a compound, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In general formula (1), Y represents a divalent hydrocarbon group. Examples of the divalent hydrocarbon group used for Y include an alkylene group having 1 to 20 carbon atoms, which is linear, branched, or has a cycloalkyl ring. In addition, one or more methylene groups of the alkylene group having 1 to 20 carbon atoms may be substituted with -O-.

As an alkylene group having 1 to 20 carbon atoms, a group in which one hydrogen atom has been removed from a linear or branched alkyl group having 1 to 20 carbon atoms can be used.

Examples of linear or branched alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and icosyl.

Examples of alkyl groups having a cycloalkyl group include monocyclic hydrocarbon groups and bridged hydrocarbon ring groups.

Examples of monocyclic hydrocarbon ring groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, methylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tetramethylcyclohexyl, pentamethylcyclohexyl, ethylcyclohexyl, and methylcycloheptyl groups, among which cyclopentyl, cyclohexyl, and cycloheptyl groups are particularly preferred.

Examples of bridged hydrocarbon ring groups include bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[4.3.1]decyl, bicyclo[3.3.1]nonyl, bornyl, bornenyl, norbornyl, norbornenyl, 6,6-dimethylbicyclo[3.1.1]heptyl, tricyclobutyl, and adamantyl.

Examples of alkyl groups having a cycloalkyl ring include groups that combine a cycloalkyl group with a linear or branched alkyl group. For example, there are groups in which one or more hydrogen atoms in a linear or branched alkyl group are replaced with a cycloalkyl group, groups in which one or more methylene groups in a linear or branched alkyl group are replaced with a group in which one hydrogen atom has been removed from the cycloalkyl group, and groups in which one or more hydrogen atoms of a cycloalkyl group are replaced with a linear or branched alkyl group.

In the composition of the present invention, the number of carbon atoms in a group means the number of carbon atoms in the group after the substitution when a hydrogen atom in the group is replaced with a substituent. For example, when a hydrogen atom in an alkyl group having 1 to 20 carbon atoms is replaced, the number of carbon atoms from 1 to 20 refers to the number of carbon atoms after the hydrogen atom is replaced, not the number of carbon atoms before the hydrogen atom is replaced. In addition, in the composition of the present invention, the number of carbon atoms in a group in which a methylene group in a group having a specified number of carbon atoms is replaced with a divalent group means the number of carbon atoms in the group before the substitution. For example, in this specification, the number of carbon atoms in a group in which a methylene group in an alkyl group having 1 to 20 carbon atoms is replaced with a divalent group is 1 to 20.

In the composition of the present invention, Y is preferably a group having a straight chain or a branched chain. By having such a structure, the composition of the present invention can form a cured product having a better balance of initial curing speed, initial adhesion, and subsequent adhesion. In the composition of the present invention, Y is preferably a straight chain or branched alkylene group having 1 to 10 carbon atoms, more preferably a straight chain or branched alkylene group having 2 to 8 carbon atoms, even more preferably a straight chain or branched alkylene group having 3 to 7 carbon atoms, and particularly preferably a straight chain or branched alkylene group having 4 to 6 carbon atoms, and among these, it is preferable that Y is a branched unsubstituted alkylene group in which the methylene group is not substituted with -O-. By having such a structure, the composition of the present invention can form a cured product having a better balance of initial curing speed, initial adhesion, and subsequent adhesion.

Specific examples of diglycidyl ethers of aliphatic diols represented by general formula (1) or their alkylene oxide adducts include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, cyclohexanedimethylol diglycidyl ether, tripropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, 1,9-nonanediol diglycidyl ether, etc., of which propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, and neopentyl glycol diglycidyl ether are preferred, with neopentyl glycol diglycidyl ether being particularly preferred. By using such an aliphatic epoxy compound, the effects of the present invention can be obtained particularly well.

Among the diglycidyl ethers of aliphatic diols represented by general formula (1) or their alkylene oxide adducts, those in which Y contains a cycloalkyl ring include, for example, diglycidyl ethers of hydrogenated bisphenol diols such as hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol AF diglycidyl ether, hydrogenated bisphenol B diglycidyl ether, hydrogenated bisphenol C diglycidyl ether, hydrogenated bisphenol E diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol G diglycidyl ether, hydrogenated bisphenol M diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, hydrogenated bisphenol P diglycidyl ether, hydrogenated bisphenol TMC diglycidyl ether, hydrogenated bisphenol Z diglycidyl ether, bis[4-(glycidyloxy)cyclohexyl]ether, and 4,4'-bicyclohexanol diglycidyl ether, with hydrogenated bisphenol A diglycidyl ether being particularly preferred. By using such an aliphatic epoxy compound, the effects of the present invention can be obtained more effectively.

The content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct may be any content that provides the desired initial curing speed, etc. For example, it is preferably 20 parts by mass or more and 80 parts by mass or less, more preferably 30 parts by mass or more and 70 parts by mass or less, and particularly preferably 40 parts by mass or more and 65 parts by mass or less, per 100 parts by mass of the composition. By setting the content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct may be any content that provides the desired adhesion, etc., and is preferably 40 parts by mass or more, more preferably 60 parts by mass or more and 95 parts by mass or less, and particularly preferably 70 parts by mass or more and 90 parts by mass or less, per 100 parts by mass of the total aliphatic epoxy compounds. By setting the content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

As the monofunctional or polyfunctional aliphatic epoxy compound, in addition to epoxy compounds such as glycidyl ethers of aliphatic alcohols, glycidyl esters of alkyl carboxylic acids, polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts, and polyglycidyl esters of aliphatic long-chain polybasic acids, aliphatic epoxy polymers having a repeating unit containing an epoxy group can also be preferably used. By using such compounds, the composition of the present invention can form a cured product with an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion.

As such an aliphatic epoxy polymer, for example, a compound (aliphatic epoxy polymer) having a structure in which a compound having an ethylenically unsaturated bond is homopolymerized or copolymerized as a main chain structure can be preferably used. When such a polymer has the structure described above, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

As such an aliphatic epoxy polymer, for example, one having at least one of a structural unit represented by the following general formula (I) (hereinafter, sometimes referred to as "structural unit I") and a structural unit represented by the following general formula (II) (hereinafter, sometimes referred to as "structural unit II") (hereinafter, aliphatic epoxy polymer a) can be preferably used. This is because the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In the general formula (I), ^X1 is an alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, in which one or more hydrogen atoms have been substituted with an epoxy group. Note that * represents a bond.

In general formula (II), ^R1 represents a hydrogen atom, a methyl group, or a halogen atom, and ^X2 represents an alkyl group having 1 to 9 carbon atoms or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, in which one or more hydrogen atoms have been substituted with an epoxy group. Note that * represents a bond.

Examples of the alkyl group having 1 to 9 carbon atoms, in which a hydrogen atom is substituted by an epoxy group, used for ^X1 in general formula (I) include alkyl groups having 1 to 20 carbon atoms that can constitute the alkylene group used for Y in general formula (1), which have a carbon atom number of 1 to 9.

Examples of the alkoxy group having 1 to 9 carbon atoms in which a hydrogen atom is substituted by an epoxy group, which is used for X ¹ in general formula (I), include methoxy, ethoxy, propyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, amyloxy, iso-amyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, and tert-heptyloxy.

Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms in which a hydrogen atom is substituted by an epoxy group and which is used for ^X1 in general formula (I) include cyclohexyl, methylcyclohexyl, norbornyl, bicyclopentyl, bicyclooctyl, trimethylbicycloheptyl, tricyclooctyl, tricyclodecanyl, spirooctyl, spirobicyclopentyl, adamantyl, and isobornyl.

^X1 in general formula (I) is preferably an alkoxy group having 1 to 9 carbon atoms in which one or more hydrogen atoms have been substituted with an epoxy group, and more preferably an alkoxy group having 1 to 4 carbon atoms in which one hydrogen atom has been substituted with an epoxy group. This is because, by having such a structure, the composition of the present invention can form a cured product having an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion.

As the structural unit represented by general formula (I), for example, a structural unit represented by the following general formula (I-1) (hereinafter, sometimes referred to as "structural unit I-1", in which ^X1 is an alkoxy group and one of the hydrogen atoms of the alkoxy group is substituted with an epoxy group) can be preferably used. By having such a structure, the composition of the present invention can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In the general formula (I-1), R ² represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and s represents an integer of 1 to 6.

As the alkyl group having 1 to 6 carbon atoms used for R ² in the general formula (I-1), an alkyl group having 1 to 6 carbon atoms among those used for X ¹ in the general formula (I) can be used.

^R2 in general formula (I-1) is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom, because this enables the composition of the present invention to form a cured product having an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion.

In general formula (II), as the alkyl group having 1 to 9 carbon atoms and the alicyclic hydrocarbon group having 6 to 10 carbon atoms substituted with the epoxy group used for ^X2 , the same groups as those used for ^X1 in general formula (I) can be used.

R ¹ in general formula (II) is preferably a methyl group, because the composition of the present invention having such a structure can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

^X2 in general formula (II) is preferably an alkyl group having 1 to 9 carbon atoms in which one or more hydrogen atoms have been substituted with an epoxy group, and more preferably an alkyl group having 1 to 4 carbon atoms in which one hydrogen atom has been substituted with an epoxy group. This is because, by having such a structure, the composition of the present invention can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

As the structural unit (II), a structural unit represented by the following general formula (II-1) (hereinafter, sometimes referred to as "structural unit II-1", in which ^X2 is an alkyl group and one of the hydrogen atoms of the alkyl group is substituted with an epoxy group) can be preferably used. This is because the composition of the present invention can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In the general formula (II-1), R ¹ is the same as in the general formula (II), R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and t is an integer of 1 to 6.

As the alkyl group having 1 to 6 carbon atoms used for R ³ in the general formula (II-1), an alkyl group having 1 to 6 carbon atoms among those used for X ¹ in the general formula (I) can be used.

In the general formula (II), examples of the halogen atom represented by R ¹ include fluorine, chlorine, bromine, and iodine.

R ³ in general formula (II-1) is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom. By having such a structure, the composition of the present invention can form a cured product having an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion.

In general formula (II-1), t is an integer from 1 to 6, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and most preferably 1. This is because the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The aliphatic epoxy polymer a has at least one of structural unit I and structural unit II, and preferably has structural unit II.

The content of structural unit II may be any content that can exhibit the desired adhesion, etc., but for example, it is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, particularly preferably 90 parts by mass or more, and particularly preferably 100 parts by mass, out of a total of 100 parts by mass of structural unit I and structural unit II. By setting the content of structural unit II in this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The total content of structural unit I and structural unit II may be any amount that can exhibit the desired adhesion, etc., but is preferably 5 parts by mass or more in 100 parts by mass of aliphatic epoxy polymer a, and more preferably 10 parts by mass or more and 70 parts by mass or less, and more preferably 20 parts by mass or more and 40 parts by mass or less. By setting the total content of structural unit I and structural unit II within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The aliphatic epoxy polymer a has at least one of the structural units I and II, but may contain other structural units as necessary. As a monomer capable of forming such other structural units, any monomer that does not have an aromatic ring and an epoxycycloalkyl group may be used, and for example, alkyl acrylate, alkyl methacrylate, etc. can be preferably used. By having such a structure, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

Examples of alkyl acrylates and alkyl methacrylates include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, 2-ethylhexyl acrylate, and 2-ethylhexyl methacrylate.

In the present invention, the alkyl acrylate and alkyl methacrylate are preferably methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, and isopropyl methacrylate, and among these, methyl methacrylate, ethyl methacrylate, and n-propyl methacrylate are preferred, and methyl methacrylate is particularly preferred. By having such a structure, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The total content of the alkyl acrylate and alkyl methacrylate may be any amount that can exhibit the desired adhesion, etc., but is preferably 20 parts by mass or more, more preferably 30 parts by mass or more and 90 parts by mass or less, and more preferably 60 parts by mass or more and 80 parts by mass or less, per 100 parts by mass of the aliphatic epoxy polymer a. By setting the total content of the alkyl acrylate and alkyl methacrylate within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The weight average molecular weight of the aliphatic epoxy polymer may be any one that provides the desired adhesion, and is preferably, for example, more than 1,000 and not more than 100,000, more preferably 3,000 or more and not more than 50,000, particularly preferably 4,000 or more and not more than 30,000, and particularly preferably 5,000 or more and not more than 20,000. By setting the weight average molecular weight of the aliphatic epoxy polymer within this range, the composition of the present invention can form a cured product that has an excellent balance between initial curing speed, initial adhesion, and subsequent adhesion.

In the composition of the present invention, the weight average molecular weight can be determined by gel permeation chromatography (GPC) in terms of standard polystyrene. The weight average molecular weight Mw can be obtained, for example, by measuring using a GPC (LC-2000plus series) manufactured by JASCO Corporation, using tetrahydrofuran as the elution solvent, polystyrene standards for the calibration curve of Mw 1110000, 707000, 397000, 189000, 98900, 37200, 13700, 9490, 5430, 3120, 1010, and 589 (TSKgel standard polystyrene manufactured by Tosoh Corporation), and measuring columns of KF-804, KF-803, and KF-802 (manufactured by Showa Denko K.K.). The measurement temperature can be 40° C., and the flow rate can be 1.0 mL/min.

The content of the aliphatic epoxy polymer may be any amount that provides the desired adhesion, etc., and is preferably from 1 to 40 parts by mass, more preferably from 3 to 30 parts by mass, and particularly preferably from 5 to 20 parts by mass, per 100 parts by mass of the composition. By setting the content of the aliphatic epoxy polymer within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of the aliphatic epoxy polymer may be any amount that provides the desired adhesion, etc. For example, it is preferably 5 parts by mass or more and 50 parts by mass or less, more preferably 10 parts by mass or more and 40 parts by mass or less, and particularly preferably 15 parts by mass or more and 30 parts by mass or less, per 100 parts by mass of the total aliphatic epoxy compounds. By setting the content of the aliphatic epoxy polymer within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The aliphatic epoxy compound preferably contains a glycidyl ether of a polyhydric alcohol or its alkylene oxide adduct, an aliphatic epoxy polymer, etc., and more preferably contains a polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct, and more preferably contains both a polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct and an aliphatic epoxy polymer, and more preferably contains both a diglycidyl ether of an aliphatic diol or its alkylene oxide adduct and an aliphatic epoxy polymer. By using these compounds, the composition of the present invention can form a cured product with a better balance of initial curing speed, initial adhesion, and subsequent adhesion. In addition, the viscosity, coatability, and reactivity are improved.

When the aliphatic epoxy compound contains both a polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct and an aliphatic epoxy polymer, the content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct is preferably 40 parts by mass or more, more preferably 60 parts by mass or more and 95 parts by mass or less, and particularly preferably 70 parts by mass or more and 90 parts by mass or less, per 100 parts by mass of the total of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct and the aliphatic epoxy polymer. By setting the content of the polyglycidyl ether of an aliphatic polyhydric alcohol or its alkylene oxide adduct within this range, the composition of the present invention can form a cured product with a better balance between initial curing speed, initial adhesion, and subsequent adhesion.

In the composition of the present invention, the aliphatic epoxy compound may be used alone or in combination of two or more. For example, by using a relatively low molecular weight aliphatic epoxy compound in combination with a relatively high molecular weight aliphatic epoxy compound, the sensitivity can be increased and the physical properties such as the viscosity and glass transition temperature Tg of the composition can be appropriately adjusted, resulting in a composition with excellent handleability, which is preferable.

In this case, the low molecular weight aliphatic epoxy compound is preferably, for example, one having a molecular weight in the range of 50 to 1,000, more preferably in the range of 100 to 500. In addition, the high molecular weight aliphatic epoxy compound is preferably, for example, one having a molecular weight in the range of more than 1,000 to 100,000, more preferably in the range of 1,500 to 50,000, more preferably in the range of 2,000 to 30,000, and more preferably in the range of 2,000 to 20,000. Furthermore, in the case of using a low molecular weight aliphatic epoxy compound in combination with a high molecular weight aliphatic epoxy compound, the content of the low molecular weight compound is preferably 40 parts by mass or more in 100 parts by mass of the aliphatic epoxy compound, from the viewpoint of obtaining the effect of using them in combination, and more preferably 60 parts by mass or more and 95 parts by mass or less, and particularly preferably 70 parts by mass or more and 90 parts by mass or less. By setting the content of the low molecular weight compound within this range, the composition of the present invention can form a cured product with an excellent balance between the initial curing speed, initial adhesion, and subsequent adhesion. Note that the molecular weight of a high molecular weight aliphatic epoxy compound refers to the weight average molecular weight (Mw) when the compound is a polymer. The method for measuring the weight average molecular weight can be the same as the method for measuring the weight average molecular weight of an aliphatic epoxy polymer.

As the aliphatic epoxy compound, commercially available products may be used, for example, Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-211, Denacol EX-212, Denacol EX-313, Denacol EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX-51. 2. Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-622, Denacol EX-810, Denacol EX-811, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, Denacol EX-911, Denacol EX-941, Denacol EX-920, Denacol EX-931 (manufactured by Nagase ChemteX Corporation); Epolight M-1230, Epolight 40E, Epolight 100E, Epolight 200E, Epolight 400E, Epolight 70P, Epolight 200P, Epolight 400P, Epolight 1500NP, Epolight Examples include Adeka Glycirol 1600, Epolight 80MF, Epolight 100MF (manufactured by Kyoeisha Chemical Co., Ltd.), Adeka Glycirol ED-503, Adeka Glycirol ED-503G, Adeka Glycirol ED-506, Adeka Glycirol ED-523T, Adeka Resin EP-4088S, KRM-532P, KRM-140 (manufactured by ADEKA Corporation), and 2EH (manufactured by Yokkaichi Chemical Co., Ltd.).

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the aliphatic epoxy compound is, for example, preferably 20 parts by mass or more and 90 parts by mass or less, more preferably 40 parts by mass or more and 85 parts by mass or less, and particularly preferably 55 parts by mass or more and 75 parts by mass or less, relative to 100 parts by mass of the total of the cationic polymerizable compound, the aromatic alcohol, and the acid generator.

In addition, the content of the aliphatic epoxy compound is preferably 20 parts by mass or more, more preferably 40 parts by mass or more and 90 parts by mass or less, and particularly preferably 60 parts by mass or more and less than 85 parts by mass, per 100 parts by mass of the cationic polymerizable compound, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the aliphatic epoxy compound is preferably 20 parts by mass or more and 90 parts by mass or less, more preferably 40 parts by mass or more and 85 parts by mass or less, and even more preferably 55 parts by mass or more and 75 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention. Note that, in the composition of the present invention, the solid content refers to all components other than the solvent.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the aliphatic epoxy compound is preferably 20 parts by mass or more and 90 parts by mass or less, more preferably 40 parts by mass or more and 85 parts by mass or less, and even more preferably 55 parts by mass or more and 75 parts by mass or less, per 100 parts by mass of the composition of the present invention.

<Alicyclic epoxy compounds>
An alicyclic epoxy compound is a compound having at least one epoxy cycloalkyl group, and a compound having merely an aliphatic ring is not classified as an alicyclic epoxy compound, but is classified as an aliphatic epoxy group. An epoxy cycloalkyl group is a group having a structure in which an epoxy group and a cycloalkyl group share a part of the ring structure. In the composition of the present invention, a compound containing both an epoxy cycloalkyl group and an aromatic ring is considered to be an alicyclic epoxy compound.

Examples of alicyclic epoxy compounds include compounds having two or more epoxycycloalkyl groups (alicyclic epoxy compound 1) and compounds having an epoxycycloalkyl group and an oxiranyl group (alicyclic epoxy compound 2). In the composition of the present invention, it is particularly preferable that the alicyclic epoxy compound contains alicyclic epoxy compound 1. This is because the composition of the present invention can form a cured product with a better balance of initial curing speed, initial adhesion, and subsequent adhesion.

The alicyclic epoxy compound 1 may be any compound having two or more epoxycycloalkyl groups, and for example, a compound represented by the following general formula (2) can be preferably used.

In formula (2), ^X3 represents a single bond or a linking group (a divalent group having one or more atoms).

Examples of the linking group used for ^X3 include a divalent hydrocarbon group, an alkenylene group in which a part or all of the carbon-carbon double bonds have been epoxidized, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, and a group in which a plurality of these groups are linked together.

Divalent hydrocarbon groups include alkylene groups having 1 to 20 carbon atoms, linear, branched, or cycloalkyl rings.

As the linear or branched alkylene group having 1 to 20 carbon atoms and having a cycloalkyl ring used for ^X3 , the same groups as the linear or branched alkylene group having 1 to 20 carbon atoms and represented by Y used in general formula (1) can be used.

Examples of the alkenylene group in an alkenylene group in which some or all of the carbon-carbon double bonds have been epoxidized (hereinafter sometimes referred to as an "epoxidized alkenylene group") include linear or branched alkenylene groups having 2 to 8 carbon atoms, such as vinylene, propenylene, 1-butenylene, 2-butenylene, butadienylene, pentenylene, hexenylene, heptenylene, and octenylene.

In the general formula (2), ^X3 is preferably a linking group, and among them, ^X3 is preferably a divalent hydrocarbon group, an ester bond, or a group in which these are linked, and particularly, ^X3 is preferably a group in which a divalent hydrocarbon group and an ester bond are linked. This is because the effects of the present invention can be more effectively obtained by using such a compound.

In general formula (2), the divalent hydrocarbon group used for ^X3 is preferably a linear or branched alkylene group having 1 to 18 carbon atoms, more preferably a linear or branched alkylene group having 1 to 8 carbon atoms, particularly preferably a linear alkylene group having 1 to 5 carbon atoms, and most preferably a linear alkylene group having 1 to 3 carbon atoms. This is because the effects of the present invention can be better exhibited by having the number of carbon atoms within this range.

Specific examples of the compound represented by general formula (2) include 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, (3,4,3',4'-diepoxy)bicyclohexyl, bis(3,4-epoxycyclohexylmethyl)ether, 1,2-epoxy-1,2-bis(3,4-epoxycyclohexane-1-yl)ethane, 2,2-bis(3,4-epoxycyclohexane-1-yl)propane, 1,2-bis(3,4-epoxycyclohexane-1-yl)ethane, and among these, 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is preferred. This is because the effects of the present invention can be obtained particularly effectively by using such a compound.

The alicyclic epoxy compound 2 may be any compound having an epoxycycloalkyl group and an oxiranyl group. For example, compounds having an epoxycycloalkyl group and an oxiranyl group represented by the following general formulas (3) to (5) can be preferably used.

In the general formula (3), R ¹¹ and R ¹² each independently represent a hydrogen atom or an alkyl group having a straight chain, branched or cycloalkyl ring and having 1 to 20 carbon atoms. Here, when R ¹¹ is the above-mentioned alkyl group, the position of bonding to the cycloalkyl ring is any position from 1 to 6. Furthermore, L ¹ represents a direct bond, -O-, or an alkylene group having 1 to 6 carbon atoms, and one or more hydrogen atoms of the alkylene group having 1 to 6 carbon atoms used for L ¹ may be substituted with a hydroxyl group. Furthermore, one or more methylene groups of the alkylene group having 1 to 6 carbon atoms used for L ¹ may be substituted with -O-.

In the general formula (4), R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group having a straight chain, branched or cycloalkyl ring and having 1 to 20 carbon atoms. Here, when R ²¹ is the above-mentioned alkyl group, the position of bonding to the cycloalkyl ring is any position from 1 to 6. Furthermore, L ² represents a direct bond, -O-, or an alkylene group having 1 to 6 carbon atoms, and one or more hydrogen atoms of the alkylene group having 1 to 6 carbon atoms used in L ² may be substituted with a hydroxyl group. Furthermore, one or more methylene groups of the alkylene group having 1 to 6 carbon atoms used in L ² may be substituted with -O-.

In the general formula (5), R ³¹ and R ³² each independently represent a hydrogen atom or an alkyl group having a straight chain, branched or cycloalkyl ring and having 1 to 20 carbon atoms. Here, when R ³¹ is the above-mentioned alkyl group, the position of bonding to the cycloalkyl ring is any position from 1 to 5. Furthermore, L ³ represents a direct bond, -O-, or an alkylene group having 1 to 6 carbon atoms, and one or more hydrogen atoms of the alkylene group having 1 to 6 carbon atoms used in L ³ may be substituted with a hydroxyl group. Furthermore, one or more methylene groups of the alkylene group having 1 to 6 carbon atoms used in L ³ may be substituted with -O-.

As the alkyl group having a straight chain, branched chain, or cycloalkyl ring and having 1 to 20 carbon atoms used for R ¹¹ , R ¹² , R ²¹ , R ²² , R ³¹ , and R ³² (hereinafter sometimes referred to as R ¹¹ , etc.), the same groups as the alkyl group having 1 to 20 carbon atoms capable of constituting an alkylene group used for Y in general formula (1) can be used.

Examples of the alkylene group having 1 to 6 carbon atoms used for L ¹ to L ³ include groups in which one hydrogen atom has been removed from an alkyl group having 1 to 6 carbon atoms among alkyl groups having 1 to 20 carbon atoms that can constitute the alkylene group used for Y in general formula (1).

In general formula (3), it is preferable that R ¹¹ is a hydrogen atom and R ¹² is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and among these, it is preferable that R ¹¹ is a hydrogen atom and R ¹² is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and it is particularly preferable that R ¹¹ is a hydrogen atom and R ¹² is a hydrogen atom or a methyl group. This is because the effects of the present invention can be more effectively obtained by using such a compound.

In general formula (3), L ¹ is preferably a direct bond or an alkylene group having 1 to 6 carbon atoms, more preferably a direct bond or an alkylene group having 1 to 3 carbon atoms, and particularly preferably a direct bond, because the effects of the present invention can be more effectively achieved by using such a compound.

Specific examples of compounds represented by general formula (3) include vinylcyclohexene dioxide, limonene dioxide, and 3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane, and among these, it is preferable to use vinylcyclohexene dioxide and limonene dioxide. This is because the effects of the present invention can be obtained particularly effectively by using such compounds.

Examples of alicyclic epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4 -epoxycyclohexane), propane-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 7-oxabicyclo[4.1.0]heptane, poly[oxy-(1-oxo-1,6-hexanediyl)] derivatives, bis[(7-oxabicyclo[4.1.0]heptan-3-yl)methyl]hexanedioate, α-pinene oxide, limonene dioxide, etc.

As the alicyclic epoxy compound, commercially available products can be used, such as CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2000, CELLOXIDE 3000, and CYCLOMER M100 (manufactured by Daicel Corporation); CYRACURE UVR-6128 (manufactured by The Dow Chemical Company); and the like.

The content of alicyclic epoxy compound 1 may be any content that provides the desired initial curing properties, and is preferably 5 parts by mass or more and 60 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and particularly preferably 15 parts by mass or more and 35 parts by mass or less, per 100 parts by mass of the composition. By setting the content of alicyclic epoxy compound 1 within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of the alicyclic epoxy compound 1 may be any content that provides desired initial curing properties, etc., and is preferably 5 parts by mass or more and 60 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and particularly preferably 15 parts by mass or more and 35 parts by mass or less, in 100 parts by mass of the cationic polymerizable compound. By setting the content of the alicyclic epoxy compound 1 within this range, the composition of the present invention can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of alicyclic epoxy compound 2 may be any content that provides the desired initial curing properties, etc., and is preferably 5 parts by mass or more and 60 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and particularly preferably 15 parts by mass or more and 35 parts by mass or less, per 100 parts by mass of the composition. By setting the content of alicyclic epoxy compound 2 within this range, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of the alicyclic epoxy compound 2 may be any content that provides desired initial curing properties, etc., and is, for example, preferably 5 parts by mass or more and 60 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and particularly preferably 15 parts by mass or more and 35 parts by mass or less, in 100 parts by mass of the cationic polymerizable compound. By setting the content of the alicyclic epoxy compound 2 within this range, the composition of the present invention can form a cured product having an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the alicyclic epoxy compound is preferably 5 parts by mass or more and 70 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, even more preferably 12 parts by mass or more and 30 parts by mass or less, and particularly preferably 15 parts by mass or more and 25 parts by mass or less, relative to 100 parts by mass of the total of the cationic polymerizable compound, the aromatic alcohol, and the acid generator.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the alicyclic epoxy compound is preferably 5 parts by mass or more and 60 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and even more preferably 15 parts by mass or more and 35 parts by mass or less, per 100 parts by mass of the cationic polymerizable compound.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the alicyclic epoxy compound is preferably from 5 to 60 parts by mass, more preferably from 10 to 50 parts by mass, and even more preferably from 15 to 35 parts by mass, per 100 parts by mass of the solid content of the composition of the present invention.

As described above, in the composition of the present invention, it is more preferable that both an aliphatic epoxy compound and an alicyclic epoxy compound are included as the cationic polymerizable compound. In this case, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the total content of the aliphatic epoxy compound and the alicyclic epoxy compound is preferably 35 parts by mass or more relative to 100 parts by mass of the total of the cationic polymerizable compound, the aromatic alcohol, and the acid generator, more preferably 40 parts by mass or more, particularly preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 60 parts by mass or more and 98 parts by mass or less, even more preferably 70 parts by mass or more and 97 parts by mass or less, and particularly preferably 80 parts by mass or more and 96 parts by mass or less.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the total content of the aliphatic epoxy compound and the alicyclic epoxy compound is preferably 35 parts by mass or more, more preferably 40 parts by mass or more, particularly preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 60 parts by mass or more and 98 parts by mass or less, even more preferably 70 parts by mass or more and 97 parts by mass or less, and particularly preferably 85 parts by mass or more and 96 parts by mass or less, per 100 parts by mass of the cationic polymerizable compound.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the total content of the aliphatic epoxy compound and the alicyclic epoxy compound is preferably 35 parts by mass or more, more preferably 40 parts by mass or more, particularly preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 60 parts by mass or more and 98 parts by mass or less, and even more preferably 80 parts by mass or more and 96 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the total content of the aliphatic epoxy compound and the alicyclic epoxy compound is preferably 35 parts by mass or more, more preferably 40 parts by mass or more, particularly preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 60 parts by mass or more and 98 parts by mass or less, and even more preferably 80 parts by mass or more and 96 parts by mass or less, per 100 parts by mass of the composition of the present invention.

<Aromatic epoxy compounds>
An aromatic epoxy compound refers to a compound having an epoxy group and an aromatic ring.

Specific examples of aromatic epoxy compounds include mono- or polyglycidyl ethers of monohydric phenols having at least one aromatic ring, such as phenol, cresol, and butylphenol, or their alkylene oxide adducts, such as glycidyl ethers of bisphenol A, bisphenol F, bisphenol E, or compounds obtained by further adding alkylene oxides to these, and phenol novolac type epoxy compounds; glycidyl ethers of aromatic compounds having two or more phenolic hydroxyl groups, such as resorcinol, hydroquinone, and catechol; polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, such as benzene dimethanol, benzene diethanol, and benzene dibutanol; polyglycidyl esters of polybasic aromatic compounds having two or more carboxylic acids, such as phthalic acid, terephthalic acid, and trimellitic acid; polyglycidyl esters of benzoic acids, such as benzoic acid, toluic acid, and naphthoic acid; glycidyl esters of benzoic acid, styrene oxide, and divinylbenzene epoxidized products. Among them, from the viewpoint of reducing the viscosity of the composition, it is preferable to contain at least one selected from the group consisting of polyglycidyl ethers of phenols, polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, polyglycidyl ethers of polyhydric phenols, polyglycidyl esters of benzoic acids, and polyglycidyl esters of polybasic acids. As the aromatic epoxy compound, bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, bisphenol E type epoxy compounds, and phenol novolac type epoxy compounds are preferable because they have excellent adhesion.

As the aromatic epoxy compound, commercially available products can be used, for example, Denacol EX-145, Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711, Denacol EX-721, Oncoat EX-1020, Oncoat EX-1030, Oncoat EX-1040, Oncoat EX-1050, Oncoat EX-1060, Oncoat EX-1070, Oncoat EX-1080, Oncoat EX-1090, Oncoat EX-2010, Oncoat EX-2011, Oncoat EX-2012, Oncoat EX-2013, Oncoat EX-2014, Oncoat EX-2015, Oncoat EX-2016, Oncoat EX-2017, Oncoat EX-2018, Oncoat EX-2019, Oncoat EX-2020, Oncoat EX-2021, Oncoat EX-2022, Oncoat EX-2023, Oncoat EX-2024, Oncoat EX-2025, Oncoat EX-2026, Oncoat EX-2027, Oncoat EX-2028, Oncoat EX-2029, Oncoat EX-2030, Oncoat EX-2031, Oncoat EX-2032, Oncoat EX-2033, Oncoat EX-2034, Oncoat EX-2035, Oncoat EX-2036, Oncoat EX-2037, Oncoat EX-2038, Oncoat EX-2039, Oncoat EX-2040, Oncoat EX-2041, Oncoat EX-2042, Oncoat EX-2043, Oncoat EX-2044, Onco EX-1050, Oncoat EX-1051, Oncoat EX-1010, Oncoat EX-1011, Oncoat 1012 (manufactured by Nagase ChemteX Corporation); Oxol PG-100, Oxol EG-200, Oxol EG-210, Oxol EG-250 (manufactured by Osaka Gas Chemicals Co., Ltd.); HP4032, HP4032D, HP4700 (manufactured by DIC Corporation); ESN- 475V (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.); Epicoat YX8800 (manufactured by Mitsubishi Chemical Co., Ltd.); Marproof G-0105SA, Marproof G-0130SP (manufactured by NOF Corp.); Epicron N-665, Epicron HP-7200 (manufactured by DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN -501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); ADEKA RESIN EP-4000, ADEKA RESIN EP-4005, ADEKA RESIN EP-4100, ADEKA RESIN EP-4901, ADEKA RESIN EP-3300E, ADEKA RESIN EP-3950S, KRM-430, KRM-501 (manufactured by ADEKA Corporation); TECHMORE VG-3101L (manufactured by Printec Co., Ltd.), etc.

The content of the aromatic epoxy compound is preferably 30 parts by mass or less, more preferably 10 parts by mass or less, and even more preferably 5 parts by mass or less, per 100 parts by mass of the cationic polymerizable compound, from the viewpoint of the balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

<Oxetane Compound>
In the composition of the present invention, the oxetane compound has an oxetane structure and does not contain an epoxy structure.

Examples of oxetane compounds include 3,7-bis(3-oxetanyl)-5-oxa-nonane, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis(3-ethyl-3-oxetanylmethyl)ether, Examples of such compounds include bifunctional oxetane compounds such as 1,6-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, 3-ethyl-3-(3-ethyl-3-oxetanylmethyloxymethyl)oxetane, and xylylenebisoxetane; and monofunctional oxetane compounds such as 3-ethyl-3-[(phenoxy)methyl]oxetane, 3-ethyl-3-(hexyloxymethyl)oxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(hydroxymethyl)oxetane, and 3-ethyl-3-(chloromethyl)oxetane. Of these, bifunctional oxetane compounds are preferred. This is because the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

As the oxetane compound, commercially available products containing a cationic polymerizable monomer as the main component can be used, such as 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, and 4-hydroxybutyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.); Aron Oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, and OXT-212 (manufactured by Toagosei Co., Ltd.), and Ethanacol OXBP and OXTP (manufactured by Ube Industries, Ltd.).

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the oxetane compound is preferably 30 parts by mass or less, more preferably 10 parts by mass or less, and even more preferably 5 parts by mass or less, per 100 parts by mass of the cationic polymerizable compound.

<Vinyl ether compound>
The vinyl ether compound has a vinyl ether group and does not have a cyclic ether group such as an epoxy group. Specific examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, and 1,6-cyclohexanedimethanol divinyl ether.

In the composition of the present invention, the vinyl ether compound is preferably a hydroxyvinyl ether having a hydroxyl group, and is preferably a compound represented by the following general formula (6). Both the hydroxyl group and the vinyl ether group are capable of reacting with the cationic polymerizable compound and the aromatic alcohol, and as a result, the composition of the present invention is capable of forming a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

CH ₂ =CH-O-A-OH (6)

In general formula (6), A represents an alkylene group having a straight chain, branched chain, or cycloalkyl ring and having 1 to 20 carbon atoms.

As the alkylene group having 1 to 20 carbon atoms, which is linear, branched, or has a cycloalkyl ring, used for A in general formula (6), the same group as the group used for Y in general formula (1) can be used.

In the composition of the present invention, A in general formula (6) is preferably a linear, branched or cycloalkyl ring-containing alkylene group having 1 to 10 carbon atoms, more preferably a linear or branched alkylene group having 2 to 5 carbon atoms, and particularly preferably a linear alkylene group having 3 to 4 carbon atoms. When A in general formula (6) has the above-mentioned structure, the composition of the present invention can form a cured product with an excellent balance of initial curing speed, initial adhesion and subsequent adhesion.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the vinyl ether compound is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 15 parts by mass or less, and even more preferably 3 parts by mass or more and 10 parts by mass or less, per 100 parts by mass of the total of the cationic polymerizable compound, the aromatic alcohol, and the acid generator.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the vinyl ether compound is preferably from 1 to 20 parts by mass, more preferably from 2 to 15 parts by mass, and even more preferably from 3 to 10 parts by mass, per 100 parts by mass of the cationic polymerizable compound.

In addition, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the vinyl ether compound is preferably from 1 to 20 parts by mass, more preferably from 2 to 15 parts by mass, and even more preferably from 3 to 10 parts by mass, per 100 parts by mass of the solid content of the composition of the present invention.

＜Other＞
In the composition of the present invention, other compounds such as thiirane compounds, thietane compounds, etc. can also be used as the cationic polymerizable compound. Regarding such other compounds that can be used as the cationic polymerizable compound, such as vinyl compounds such as cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, and ethylenically unsaturated compounds, the contents thereof can be the same as those described in Japanese Patent No. 6103653, etc.

From the viewpoint of the ease of application of the composition of the present invention, the initial curing speed, etc., it is preferable that the cationic polymerizable compound contains a low molecular weight compound. In addition, since the low molecular weight compound has excellent dispersibility or solubility in the composition, etc., it is possible to obtain a cured product with excellent transparency. In addition, from the viewpoint of the initial adhesion of the composition, etc., it is also preferable that the cationic polymerizable compound contains a high molecular weight compound. In particular, in the composition of the present invention, it is preferable that the cationic polymerizable compound contains both a low molecular weight compound and a high molecular weight compound from the viewpoint of the balance of the ease of application of the composition, the initial curing speed, and the initial adhesion. Furthermore, by using the high molecular weight compound together with the low molecular weight compound, the dispersion or solubility in the composition of the present invention is improved, and a cured product with excellent transparency can be obtained.

The molecular weight of the low molecular weight compound and the molecular weight of the high molecular weight compound can be the same as the low molecular weight aliphatic epoxy compound and the high molecular weight aliphatic epoxy compound described above, respectively.

The content of the low molecular weight compound is not particularly limited as long as the desired initial curing speed and initial adhesion are obtained, and is appropriately adjusted, for example, from the viewpoint of the balance between adhesion and transparency. Specifically, the content of the low molecular weight compound can be 50 parts by mass or more and 99 parts by mass or less, preferably 70 parts by mass or more and 98 parts by mass or less, and more preferably 80 parts by mass or more and 95 parts by mass or less, in 100 parts by mass of the cationic polymerizable compound. By setting the content of the low molecular weight compound in this range, the composition of the present invention has excellent initial curing speed and initial adhesion, and can form a cured product that is particularly excellent in adhesion and transparency.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the cationic polymerizable compound is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more and 99 parts by mass or less, and more preferably 85 parts by mass or more and 98 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the cationic polymerizable compound is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more and 99 parts by mass or less, and more preferably 85 parts by mass or more and 98 parts by mass or less, per 100 parts by mass of the composition of the present invention.

<1-2. Aromatic alcohols>
In the composition of the present invention, the aromatic alcohol is an alcohol having an aromatic ring, which enables the composition of the present invention to exhibit excellent initial curing speed and initial adhesion.

The aromatic alcohol may be any alcohol having an alcoholic hydroxyl group, and any of primary, secondary, and tertiary alcohols may be used. In the composition of the present invention, the aromatic alcohol is preferably a primary or secondary alcohol, and is particularly preferably a primary alcohol. By using a primary or secondary alcohol, the composition of the present invention has a better balance of initial curing speed, initial adhesion, and subsequent adhesion.

The aromatic ring is not particularly limited, and examples include aromatic hydrocarbon rings having 6 to 20 carbon atoms and aromatic heterocycles having 2 to 20 carbon atoms.

The aromatic hydrocarbon ring may be a single ring or a condensed ring, so long as all atoms forming the ring structure are carbon atoms. Examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, and the like, and condensed rings thereof.

Aromatic heterocycles may be any ring structure that contains atoms other than carbon atoms, and may be either single or condensed rings, such as a furan ring, a benzofuran ring, a dibenzofuran ring, or a thiophene ring.

When the total number of ring structures is two or more, the aromatic ring is not limited to those containing fused rings in which aromatic rings are fused together, but may also contain structures in which aromatic rings are bonded by divalent bonding groups, such as biphenyl, benzophenone, etc.

In the composition of the present invention, the aromatic ring is preferably an aromatic hydrocarbon ring, more preferably an aromatic hydrocarbon ring having 6 to 10 carbon atoms, and more preferably an aromatic hydrocarbon ring having 6 carbon atoms, i.e., a benzene ring. This is because the aromatic ring has the above-mentioned ring structure, and thus the composition of the present invention has an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In the composition of the present invention, the number of alcoholic hydroxyl groups possessed by the aromatic alcohol is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1. By having the number of alcoholic hydroxyl groups in this range, the composition of the present invention will have an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The molecular weight is preferably 90 to 300, more preferably 95 to 200, even more preferably 100 to 180, and particularly preferably 105 to 160. When the molecular weight of the aromatic alcohol is within the above range, the composition of the present invention has an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

As such aromatic alcohols, those represented by the following general formula (7) are preferred. By using such aromatic alcohols, the composition of the present invention has a better balance of initial curing speed, initial adhesion, and subsequent adhesion, and it is possible to form a cured product that has excellent adhesion and transparency in particular.

In the general formula (7), the aromatic ring Ar is a p-valent aromatic hydrocarbon ring which may have a substituent having 6 to 20 carbon atoms or a p-valent aromatic heterocycle which may have a substituent having 2 to 20 carbon atoms, B is a group represented by the general formula (8) (when p is 2 or more, each B may be the same or different), and ^Y2 is a group in which q hydrogen atoms have been removed from an alkyl group having a straight chain, branched chain or cycloalkyl ring having 1 to 20 carbon atoms. In addition, p represents 1 to 6, and q represents 1 to 10.

As the linear, branched or cycloalkyl ring-containing alkyl group having 1 to 20 carbon atoms used for ^Y2 , the same groups as the linear or branched or cycloalkyl ring-containing alkylene group having 1 to 20 carbon atoms represented by Y used for general formula (1) can be used.

The aromatic hydrocarbon ring having 6 to 20 carbon atoms and the aromatic heterocycle having 2 to 20 carbon atoms used in the aromatic ring Ar can be the same as those listed as the aromatic rings that can be used in the aromatic alcohols described above. In addition, the aromatic ring Ar may have a substituent other than the substituent B.

Such substituents include halogen atoms and alkyl groups having a straight chain, branched or cycloalkyl ring with 1 to 10 carbon atoms, and one or more of the methylene groups of the substituent substituting one or more hydrogen atoms of the aromatic ring Ar may be substituted with -O-, -CO-, -CO-O-, -S-, etc.

As the alkyl group having 1 to 10 carbon atoms and a straight chain, branched chain, or cycloalkyl ring, which is used as a substituent other than the substituent B of the aromatic ring Ar, it is possible to use an alkylene group having 1 to 20 carbon atoms and a straight chain, branched chain, or cycloalkyl ring represented by Y used in general formula (1), which has 1 to 10 carbon atoms.

^Y2 is preferably a group in which q hydrogen atoms have been removed from an alkyl group having a straight chain, branched chain or cycloalkyl ring and 1 to 20 carbon atoms, and the number of carbon atoms is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. By using an aromatic alcohol having such a structure, the composition of the present invention has a better balance between the initial curing rate, initial adhesion and subsequent adhesion, and it is possible to form a cured product that is particularly excellent in adhesion and transparency.

The aromatic ring Ar may have a substituent other than the substituent B, but is preferably unsubstituted with no substituent other than the substituent B, or one or more of the hydrogen atoms of the aromatic ring Ar are substituted with an alkyl group or an alkoxy group. This structure provides the composition of the present invention with a better balance of initial curing speed, initial adhesion, and subsequent adhesion, and makes it possible to form a cured product that is particularly excellent in adhesion and transparency.

The alkyl group used as a substituent of the aromatic ring Ar is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and particularly preferably a branched alkyl group having 3 to 5 carbon atoms. By using such a substituent, the composition of the present invention has a better balance of initial curing speed, initial adhesion, and subsequent adhesion, and can form a cured product that is particularly excellent in adhesion and transparency.

As the alkoxy group (wherein the alkyl group end is substituted with -O-) used as a substituent of the aromatic ring Ar, an alkoxy group having 1 to 10 carbon atoms is more preferable, an alkoxy group having 1 to 5 carbon atoms is even more preferable, and an alkoxy group having 1 to 3 carbon atoms is particularly preferable. The number of the substituents is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1. By using an aromatic alcohol having such a structure, the composition of the present invention has a better balance between the initial curing speed, initial adhesion, and subsequent adhesion, and it is possible to form a cured product that is particularly excellent in adhesion and transparency.

The bonding position of the substituent substituting one or more hydrogen atoms of the aromatic ring Ar is preferably the meta or para position relative to the number of bonds of the substituent B, i.e., when p is 1, the bonding position of the substituent B. For example, when the substituent has an alkyl group, the bonding position of the alkyl group is preferably the meta position, and when the substituent has an alkoxy group, the bonding position of the alkoxy group is preferably the para position. By using an aromatic alcohol with such a structure, the composition of the present invention has a better balance of initial curing speed, initial adhesion, and subsequent adhesion, and can form a cured product that is particularly excellent in adhesion and transparency.

p represents the number of the substituents B represented by the general formula (8) bonded to the aromatic ring Ar, and may be 1 to 6, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1. q represents the number of hydroxyl groups bonded to the linking group ^Y2 , and may be 1 to 10, but is preferably 1 to 5, more preferably 1 to 3, and particularly preferably 1. By using such a substituent, the composition of the present invention has a better balance between the initial curing rate, the initial adhesion, and the subsequent adhesion, and it is possible to form a cured product that is particularly excellent in adhesion and transparency.

When p and q are in this range, the composition of the present invention has an excellent balance between the initial curing speed, initial adhesion, and subsequent adhesion, and is capable of forming a cured product that is particularly excellent in adhesion and transparency.

Examples of aromatic alcohols that can be used in the composition of the present invention include halogenated benzyl alcohols such as benzyl alcohol, 2-chlorobenzyl alcohol, 3-chlorobenzyl alcohol, 4-chlorobenzyl alcohol, 2-bromobenzyl alcohol, 3-bromobenzyl alcohol, 4-bromobenzyl alcohol, 2-iodobenzyl alcohol, 3-iodobenzyl alcohol, 4-iodobenzyl alcohol, and dichlorobenzyl alcohol; 2-methylbenzyl alcohol, 3-methylbenzyl alcohol, 4-methylbenzyl alcohol, dimethylbenzyl alcohol, and 3,4,5-trimethylbenzyl alcohol. Examples of such alcohols include alkyl-substituted benzyl alcohols such as benzyl alcohol, 4-ethylbenzyl alcohol, 4-isopropylbenzyl alcohol, 4-butylbenzyl alcohol, and 4-tert-butylbenzyl alcohol; alkoxy-substituted benzyl alcohols such as dimethoxybenzyl alcohol, 2-ethoxybenzyl alcohol, 3-ethoxybenzyl alcohol, 4-ethoxybenzyl alcohol, 4-butoxybenzyl alcohol, 2-methoxybenzyl alcohol, 3-methoxybenzyl alcohol, and 4-methoxybenzyl alcohol; phenethyl alcohol, benzoin, and phenylpropanol. These may be used alone or in combination of two or more.

In the composition of the present invention, the content of the aromatic alcohol is preferably 2 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the total of the cationic polymerizable compound, aromatic alcohol, and acid generator from the viewpoint of the balance of the initial curing speed, initial adhesion, and subsequent adhesion. If it is less than 2 parts by mass, the above effect may not be sufficiently obtained, while if it exceeds 20 parts by mass, the curable component becomes less and sufficient adhesion may not be obtained. More preferably, it is 2 parts by mass or more and 15 parts by mass or less, even more preferably, it is 3 parts by mass or more and 10 parts by mass or less, and particularly preferably, it is 4 parts by mass or more and 8 parts by mass or less. This is because the composition of the present invention can form a cured product with a better balance of the initial curing speed, initial adhesion, and subsequent adhesion.

In addition, from the viewpoint of the balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the aromatic alcohol is preferably 2 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, and even more preferably 4 parts by mass or more and 8 parts by mass or less, relative to 100 parts by mass of the cationic polymerizable compound.

In addition, from the viewpoint of the balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the aromatic alcohol is preferably 2 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, and even more preferably 4 parts by mass or more and 8 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention.

In addition, the content of aromatic alcohol is preferably 2 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, and more preferably 4 parts by mass or more and 8 parts by mass or less, per 100 parts by mass of the composition of the present invention, from the viewpoint of the balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

<1-3. Acid generator>
The acid generator used in the composition of the present invention is a compound capable of generating an acid upon irradiation with active energy rays (hereinafter also simply referred to as "energy rays") such as visible light, ultraviolet light, X-rays, electron beams, and high frequency waves (hereinafter also simply referred to as "photoacid generator"), or a compound capable of generating an acid upon heating (hereinafter also simply referred to as "thermal acid generator").

Either a photoacid generator or a thermal acid generator can be used in the composition of the present invention, but from the viewpoint of sensitivity, a photoacid generator is preferred. Examples of such acid generators include onium salts, naphthalimide sulfonate compounds, oxime sulfonate compounds, sulfonylimide compounds, sulfonic acid esters, etc., and among these, onium salts and naphthalimide sulfonate compounds are preferred in order to obtain the effects of the present invention better.

An example of an onium salt double salt or a derivative thereof is a salt of a cation and an anion represented by the following general formula (9).

[A] ^m+ [B] ^m- (9)

Here, the cation [A] ^m+ is preferably an onium, and the structure thereof can be represented, for example, by the following general formula (10).

[(R ⁴ ) ^a Q] ^m+ (10)

Here, R ⁴ is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms. a is an integer from 1 to 5. a R ^4s are each independent and may be the same or different. At least one of the a R ^4s is the organic group having an aromatic ring. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, and N=N. In addition, when the valence of Q in the cation [A] ^m+ is q, it is necessary that the relationship m=a-q holds. However, N=N is treated as having a valence of 0.

The anion [B] ^m− is preferably a halide complex, and the structure thereof can be represented, for example, by the following general formula (11).

[LX _b ] ^m- (11)

Here, L is a metal or semimetal (Metalloid) that is the central atom of the halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co, etc. X is a halogen atom. b is an integer of 3 to 7. In addition, when the valence of L in the anion [B] ^m- is p, it is necessary that the relationship m = b - p is established.

Specific examples of the anion [LX _b ] ^m- of general formula (11) include tetrakis(pentafluorophenyl)borate [(C ₆ F ₅ ) ₄ B] ⁻ , tetrafluoroborate (BF ₄ ) ⁻ , hexafluorophosphate (PF ₆ ) ⁻ , hexafluoroantimonate (SbF ₆ ) ⁻ , hexafluoroarsenate (AsF ₆ ) − , hexachloroantimonate (SbCl ₆ ) ^{− ,} and tris(pentafluoromethyl)trifluorophosphate ion (FAP anion).

In addition, the anion [B] ^m− may preferably have a structure represented by the following general formula (12).

[LX _b-1 (OH)] ^m- (12)

Here, L, X, and b are the same as above. Other usable anions include perchlorate ion (ClO ₄ ) ⁻ , trifluoromethylsulfite ion (CF ₃ SO ₃ ) ⁻ , fluorosulfonate ion (FSO ₃ ) ⁻ , toluenesulfonate anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctane sulfonate, tetraarylborate, and tetrakis(pentafluorophenyl)borate.

Of these onium salts, the use of the aromatic onium salts (a) to (c) below is particularly effective in the composition of the present invention. One of these can be used alone, or two or more can be used in combination.

(a) Aryl diazonium salts such as phenyl diazonium hexafluorophosphate, 4-methoxyphenyl diazonium hexafluoroantimonate, and 4-methylphenyl diazonium hexafluorophosphate.

(b) Diaryl iodonium salts such as diphenyl iodonium hexafluoroantimonate, di(4-methylphenyl) iodonium hexafluorophosphate, di(4-tert-butylphenyl) iodonium hexafluorophosphate, and triaryl cumyl iodonium tetrakis(pentafluorophenyl)borate.

(c) Sulfonium cations represented by the following Group I or Group II and sulfonium salts such as hexafluoroantimony ion and tetrakis(pentafluorophenyl)borate ion

<Group I>

<Group II>

Other preferred examples include iron-arene complexes such as (η5-2,4-cyclopentadien-1-yl)[(1,2,3,4,5,6-η)-(1-methylethyl)benzene]-iron-hexafluorophosphate, and mixtures of aluminum complexes such as tris(acetylacetonato)aluminum, tris(ethylacetonatoacetato)aluminum, and tris(salicylaldehydato)aluminum with silanols such as triphenylsilanol.

Among these, from the viewpoints of practicality and photosensitivity, it is preferable to use aromatic iodonium salts, aromatic sulfonium salts, and iron-arene complexes, and aromatic sulfonium salts represented by the following general formula (13) are more preferable in terms of sensitivity. In addition, the composition of the present invention has excellent curing speed and adhesion.

In the general formula (5), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms; R ¹¹¹ , R ¹¹² , R ¹¹³ and R ¹¹⁴ each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms; R ¹¹⁵ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or any of the substituents selected from the following chemical formulas (A) to (C); An ^q- represents a q-valent anion; and p represents a coefficient for neutralizing the charge.

In the chemical formulas (A) to (C), R ¹²¹ , R ¹²² , R ¹²³ , R ¹⁴⁴ , R ¹²⁵ , R ¹²⁶ , R ¹²⁷ , R 128 , R ¹²⁹ , R ^{130 ,} R ¹³¹ , R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ , R ¹⁴² , R ¹⁴³ and R ¹⁴⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group having ¹ to 10 carbon atoms, an alkoxy group having 1 to 10 carbon ^atoms or an ester group ^having 2 to 10 carbon atoms ^; Each of ¹⁴⁹ independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms, and * represents the bonding position with S in general formula (13).

^R101 , ^R102 , ^R103 , ^R104 , ^R105 , ^R106 , ^R107 , ^R108 , ^R109 , ^R110 , ^R111 , ^R112 , ^R113 , ^R114 , ^R115 , ^R121 , ^R122 , R ¹²³ , R ¹²⁴ , R ¹²⁵ , R ¹²⁶ , R ¹²⁷ , R ¹²⁸ , R ^{129 ,} R ¹³⁰ , R ¹³¹ , R 132 , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ Examples of the halogen atom represented by R142, ^R143 , ^R144 , ^R145 , ^R146 , ^R147 , ^R148 and ^R149 include fluorine, chlorine, bromine and iodine ^.

^R101 , ^R102 , ^R103 , ^R104 , ^R105 , ^R106 , ^R107 , ^R108 , ^R109 , ^R110 , ^R111 , ^R112 , ^R113 , ^R114 , ^R115 , ^R121 , ^R122 , R ¹²³ , R ¹²⁴ , R ¹²⁵ , R ¹²⁶ , R ¹²⁷ , R ¹²⁸ , R ^{129 ,} R ¹³⁰ , R ¹³¹ , R 132 , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ , R ¹⁴² , R ¹⁴³ , R ¹⁴⁴ , R ¹⁴⁵ , R ¹⁴⁶ , R ¹⁴⁷ , R ¹⁴⁸ and R Examples of the alkyl group having 1 to 10 carbon atoms represented by ¹⁴⁹ include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, and heptyl. , octyl, nonyl, ethyl octyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, difluoroethyl, trichloroethyl, dichlorodifluoroethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, decafluoropentyl , tridecafluorohexyl, pentadecafluoroheptyl, heptadecafluorooctyl, methoxymethyl, 1,2-epoxyethyl, methoxyethyl , methoxyethoxymethyl, methylthiomethyl, ethoxyethyl, butoxymethyl, t-butylthiomethyl, 4-pentenyloxymethyl, trichloroethoxymethyl, bis(2-chloroethoxy)methyl, methoxycyclohexyl, 1-(2-chloroethoxy) Ethyl, 1-methyl-1-methoxyethyl, ethyldithioethyl, trimethylsilylethyl, t-butyldimethylsilyloxymethyl, 2-(trimethylsilyl)ethoxymethyl, t-butoxycarbonylmethyl, ethyloxycarbonylmethyl, ethylcarbonylmethyl, t -butoxycarbonylmethyl, acryloyloxyethyl, methacryloyloxyethyl, 2-methyl-2-adamantyloxycarbonylmethyl, acetylethyl, 2-methoxy-1-propenyl, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 2- Examples of the hydroxypropyl group include hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl, 4-hydroxybutyl, and 1,2-dihydroxyethyl.

^R101 , ^R102 , ^R103 , ^R104 , ^R105 , ^R106 , ^R107 , ^R108 , ^R109 , ^R110 , ^R121 , ^R122 , ^R123 , ^R124 , ^R125 , ^R126 , ^R127 , R ¹²⁸ , R ¹²⁹ , R ¹³⁰ , R ¹³¹ , R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ^{141 , R 142 ,} R ¹⁴³ and R Examples of the alkoxy group having 1 to 10 carbon atoms represented by ¹⁴⁴ include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, Hexyloxy, cyclohexyloxy, cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxyethoxy Examples of the oxyalkyl group include ethoxyethyloxy, 3-methoxybutyloxy, 2-methylthioethyloxy, and trifluoromethyloxy.

^R101 , ^R102 , ^R103 , ^R104 , ^R105 , ^R106 , ^R107 , ^R108 , ^R109 , ^R110 , ^R121 , ^R122 , ^R123 , ^R124 , ^R125 , ^R126 , ^R127 , R ¹²⁸ , R ¹²⁹ , R ¹³⁰ , R ¹³¹ , R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ^{141 , R 142 ,} R ¹⁴³ and R Examples of the ester group having 2 to 10 carbon atoms represented by ¹⁴⁴ include methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarbonyl, acetoxy, propionyloxy, butyryloxy, chloroacetyloxy, dichloroacetyloxy, tri ... Examples thereof include fluoroacetyloxy, t-butylcarbonyloxy, methoxyacetyloxy, and benzoyloxy.

As the q-valent anion represented by pAn ^q- in the general formula (1), an anion having a predetermined valence can be used among those exemplified above as the anion [B] ^m- .

In the composition of the present invention, R ¹¹⁵ is preferably selected from the chemical formulae (A) to (C), and more preferably selected from the chemical formula (A) or (C). This is because R ¹¹⁵ having the above-mentioned structure provides excellent curing speed and adhesion. In the composition of the present invention, from the viewpoint of dispersion stability of the acid generator, R ¹¹⁵ is preferably the chemical formula (C). On the other hand, from the viewpoint of achieving even better curing speed and adhesion, R ¹¹⁵ is preferably the chemical formula (A). In the composition of the present invention, from the viewpoint of achieving excellent curing speed and adhesion, the acid generator preferably includes both R ¹¹⁵ of the chemical formula (A) and R 115 of the chemical formula (C).

When the acid generator includes both those in which R ¹¹⁵ is chemical formula (A) and those in which R ^{115 is chemical formula (C), the content of those in which R 115} is chemical formula (A) can be 10 parts by mass or more and 200 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less, and more preferably 80 parts by mass or more and 120 parts by mass or less, relative to 100 parts by mass of those in which R 115 is chemical formula (C). By setting the content in this range, the curing speed and adhesion are excellent.

R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ , R ¹¹⁰ , R ¹¹¹ , R ¹¹² , R ¹¹³ and R ¹¹⁴ are hydrogen atoms, halogen atoms, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or ester groups having 2 to 10 carbon atoms, among which hydrogen atoms, halogen atoms, alkyl groups having 1 to 10 carbon atoms, and alkoxy groups having 1 to 10 carbon atoms are preferred, and hydrogen atoms are particularly preferred. This is because the composition of the present invention has excellent curing speed and adhesion by being the above-mentioned functional group. In addition, this is because such an acid generator is easily synthesized.

R ¹²¹ , R ¹²² , R ¹²³ , R ¹²⁴ , R ¹²⁵ , R ¹²⁶ , R ¹²⁷ , R ¹²⁸ , R ¹²⁹ , R ¹³⁰ , R ¹³¹ , R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁶ , R ¹³⁷ , R ¹³⁸ , R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ , R ¹⁴² , R ¹⁴³ , R ¹⁴⁴ , R ¹⁴⁵ , R ¹⁴⁶ , R ¹⁴⁷ , R ¹⁴⁸ and R ¹⁴⁹ are preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom. The above-mentioned functional groups provide the composition of the present invention with excellent curing speed and adhesion. In addition, such acid generators have the advantage of being easy to synthesize.

As the naphthalimide sulfonate compound, the one represented by the following general formula (14) is preferred from the viewpoints of practical use and photosensitivity.

In general formula (14), R ⁴¹ represents an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an aryl group having 7 to 20 carbon atoms substituted with an acyl group, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or a 10-camphoryl group.

The aliphatic hydrocarbon group, aryl group, arylalkyl group and alicyclic hydrocarbon group are either unsubstituted or substituted with a group selected from a halogen atom, a halogenated alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 18 carbon atoms and an alkylthio group having 1 to 18 carbon atoms.

R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ , R ⁴⁶ and R ⁴⁷ each represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms.

Examples of the aliphatic hydrocarbon group having 1 to 18 carbon atoms used for R ⁴¹ in general formula (14) include an alkenyl group, an alkyl group, a group in which a methylene group in an alkyl group is substituted with an alicyclic hydrocarbon group, a group in which a proton of a methylene group in an alkyl group is substituted with an alicyclic hydrocarbon group, and a group in which an alicyclic hydrocarbon group exists at the terminal of the alkyl group.

The alkenyl group used for R ⁴¹ includes allyl and 2-methyl-2-propenyl.

Examples of the alkyl group used for R ⁴¹ include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl.

Examples of the alicyclic hydrocarbon group used for R ⁴¹ include cyclopropyl, cyclopentyl, cyclohexyl, and cycloheptyl.

Examples of the aryl group having 6 to 20 carbon atoms used for R ⁴¹ , R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ , R ⁴⁶ and R ⁴⁷ in the general formula (14) include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl. , 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, cyclohexylphenyl, biphenyl, 2,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, and the like.

Examples of the arylalkyl group having 7 to 20 carbon atoms used for R ⁴¹ , R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ , R ⁴⁶ and R ⁴⁷ in the general formula (14) include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, etc.

Examples of the aryl group having 7 to 20 carbon atoms substituted with an acyl group used for R ⁴¹ in general formula (14) include an acetylphenyl group, an acetylnaphthyl group, a benzoylphenyl group, a 1-anthraquinolyl group, and a 2-anthraquinolyl group.

Examples of the alicyclic hydrocarbon group having 3 to 12 carbon atoms used for R ⁴¹ in general formula (14) include, in terms of the names of the cycloalkanes that constitute it, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclodecane, bicyclo[2.1.1]hexane, bicyclo[2.2.1]heptane, bicyclo[3.2.1]octane, bicyclo[2.2.2]octane, and adamantane.

Examples of the alkyl group having 1 to 40 carbon atoms, which may have a substituent and is used for R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ , R ⁴⁶ and R ⁴⁷ in general formula (14), include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl and the like.

Examples of the heterocycle-containing group having 2 to 20 carbon atoms used for R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ , R ⁴⁶ and R ⁴⁷ in general formula (14) include groups in which a heterocycle such as a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, a triazine ring, a pyrroline ring, a quinoline ring, an isoquinoline ring, an imidazoline ring, a benzimidazoline ring, a triazoline ring, a furan ring, a benzofuran ring, a thiadiazoline ring, a thiazoline ring, a benzothiazoline ring, a thiophene ring, an oxazoline ring, a benzoxazoline ring, an isothiazolin ring, an isoxazoline ring, an indole ring, a pyrrolidine ring, a piperidone ring or a dioxane ring is combined with a methylene chain.

Halogen atoms used as substituents include chlorine, bromine, iodine, and fluorine.

Examples of halogenated alkyl groups having 1 to 4 carbon atoms that can be used as substituents include trifluoromethyl groups.

Examples of alkoxy groups having 1 to 18 carbon atoms that may be used as a substituent include methoxy, ethoxy, propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, and octadecyloxy.

Examples of alkylthio groups having 1 to 18 carbon atoms that may be used as a substituent include methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tert-amylthio, hexylthio, heptylthio, isoheptylthio, tert-heptylthio, octylthio, isooctylthio, tert-octylthio, 2-ethylhexylthio, nonylthio, decylthio, undecylthio, dodecylthio, tridecylthio, tetradecylthio, pentadecylthio, hexadecylthio, heptadecylthio, and octadecylthio.

As the oxime sulfonate compound, one represented by general formula (15) is preferred from the viewpoints of practical use and photosensitivity.

In general formula (15), R ⁵¹ represents an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an aryl group having 7 to 20 carbon atoms substituted with an acyl group, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or a 10-camphoryl group.

The aliphatic hydrocarbon group, aryl group, arylalkyl group and alicyclic hydrocarbon group are either unsubstituted or substituted with a group selected from a halogen atom, a halogenated alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 18 carbon atoms and an alkylthio group having 1 to 18 carbon atoms.

R ⁵² and R ⁵³ each represent a cyano group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms.

R ⁵² and R ⁵³ may be linked to each other to form a five-membered heterocycle.

As the aliphatic hydrocarbon group having 1 to 18 carbon atoms used for R ⁵¹ in the general formula (15), the same one used for R ⁴¹ can be used.

The aryl group having 6 to 20 carbon atoms used for R ⁵¹ , R ⁵² and R ⁵³ in the general formula (15) may be the same as that used for R ⁴¹ etc.

As the arylalkyl group having 7 to 20 carbon atoms used for R ⁵¹ , R ⁵² and R ⁵³ in the general formula (15), the same ones used for R ⁴¹ etc. can be used.

The aryl group having 7 to 20 carbon atoms substituted with an acyl group used for R ⁵¹ in the general formula (15) may be the same as that used for R ⁴¹ .

As the alicyclic hydrocarbon group having 3 to 12 carbon atoms used for R ⁵¹ in the general formula (15), the same ones used for R ⁴¹ can be used.

The alkyl group having 1 to 40 carbon atoms which may have a substituent and is used for R ⁵² and R ⁵³ in the general formula (15) may be the same as that used for R ⁴² etc.

As the heterocyclic ring-containing group having 2 to 20 carbon atoms used for R ⁵² and R ⁵³ in the general formula (15), the same ones used for R ⁴² and the like can be used.

Examples of the five-membered heterocyclic ring which may be formed by R ⁵² and R ⁵³ in general formula (15) include a furan ring, a thiophene ring, a pyrrole ring, a pyrrolidine ring, a pyrazolidine ring, a pyrazole ring, an imidazole ring, an imidazolidine ring, an oxazole ring, an isoxazole ring, an isoxazolidine ring, a thiazole ring, an isothiazole ring, and an isothiazolidine ring.

The halogen atoms, halogenated alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 18 carbon atoms, and alkylthio groups having 1 to 18 carbon atoms used as substituents can be the same as those in general formula (14).

In the composition of the present invention, the content of the acid generator may be any content that provides a desired balance of initial curing speed, initial adhesion, and subsequent adhesion, and is, for example, preferably 0.1 parts by mass to 5 parts by mass, more preferably 0.5 parts by mass to 4 parts by mass, even more preferably 0.6 parts by mass to 2.5 parts by mass, and particularly preferably 0.7 parts by mass to 1.5 parts by mass, per 100 parts by mass of the solid content of the composition of the present invention. By setting the content within this range, the composition of the present invention will have an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

The content of the acid generator is preferably 0.1 parts by mass or more and 2.5 parts by mass or less, more preferably 0.5 parts by mass or more and 1.5 parts by mass or less, even more preferably 0.7 parts by mass or more and 1.2 parts by mass or less, and particularly preferably 2.0 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention, from the viewpoint of achieving excellent curing speed and adhesion and suppressing corrosion of the coating target.

Note that some commercially available acid generators are in the form of an acid generator dispersed or dissolved in a solvent. When calculating the content of the acid generator in the composition of the present invention, the content refers to the content excluding the solvent in which the acid generator is dispersed, i.e., the solid content of the acid generator. Hereinafter, the content of the acid generator relative to the cationic polymerizable compound, the content of the sensitizer relative to the acid generator, etc. are also calculated based on the solid content of the acid generator.

In the composition of the present invention, the content of the acid generator is preferably 0.1 parts by mass or more and 10 parts by mass or less, more preferably 0.3 parts by mass or more and 5 parts by mass or less, even more preferably 0.5 parts by mass or more and 3 parts by mass or less, and particularly preferably 0.7 parts by mass or more and 2 parts by mass or less, relative to 100 parts by mass of the cationic polymerizable compound. By setting the content of the acid generator within this range, the composition of the present invention has an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

<1-4. Radically polymerizable compound>
The composition of the present invention may contain a radical polymerizable compound. The composition of the present invention can improve the curability by using a radical polymerizable compound in combination. As the radical polymerizable compound, a compound having an ethylenically unsaturated group such as an acryloyl group, a methacryloyl group, or a vinyl group can be used. As these radical polymerizable compounds, a compound having one or more ethylenically unsaturated groups can be used, and either a monofunctional compound having one ethylenically unsaturated group or a polyfunctional compound having two or more ethylenically unsaturated groups can be used.

Examples of such radical polymerizable compounds include unsaturated aliphatic hydrocarbons, unsaturated polybasic acids, esters of unsaturated monobasic acids and polyhydric alcohols or polyhydric phenols, acid anhydrides of unsaturated polybasic acids, amides of unsaturated monobasic acids and polyamines, unsaturated aldehydes, unsaturated aromatic compounds, unsaturated ketones, vinyl ethers, unsaturated imides, indenes, aliphatic conjugated dienes, macromonomers having monoacryloyl or methacryloyl groups at the ends of the polymer molecular chains, vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, etc. acrylate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, vinyl urethane compounds of hydroxyl group-containing vinyl monomers and polyisocyanate compounds, vinyl epoxy compounds of hydroxyl group-containing vinyl monomers and epoxy compounds, reaction products of hydroxyl group-containing polyfunctional acrylates and other functional isocyanates, and polyfunctional acrylates having an acid value that are reaction products of hydroxyl group-containing polyfunctional acrylates and dibasic acid anhydrides.

In addition, polyfunctional acrylate compounds, polyfunctional methacrylate compounds, acrylate compounds or methacrylate compounds having a hydroxyl group, etc. can also be used as radically polymerizable compounds.

In the composition of the present invention, polyfunctional acrylate compounds, polyfunctional methacrylate compounds, and acrylate or methacrylate compounds having a hydroxyl group can be preferably used, particularly from the viewpoint of improving the curing property. This is because being polyfunctional allows a cured product with a high crosslinking density to be formed, and as a result, a cured product with excellent adhesion can be obtained. In addition, having a hydroxyl group provides excellent adhesion to the adherend for the same reason as the adhesion to the adherend obtained by obtaining a polymer having a hydroxyl group from a cationic polymerizable compound and an aromatic alcohol. Among them, in the present invention, an acrylate or methacrylate compound having a hydroxyl group can be preferably used as the radical polymerizable compound. This is because it provides a better balance between the initial curing speed, initial adhesion, and subsequent adhesion.

As the acrylate compound having a hydroxyl group and the methacrylate compound having a hydroxyl group, a low molecular weight material such as a monomer or oligomer can be used, specifically, one having a molecular weight in the range of 100 to 1000, preferably in the range of 110 to 700.

Specific examples of acrylate compounds having a hydroxyl group and methacrylate compounds having a hydroxyl group may be monofunctional or polyfunctional, and include 2-hydroxy-3-acryloyloxypropyl acrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, 2-hydroxy-3-phenoxyethyl acrylate, 2-hydroxy-3-phenoxyethyl methacrylate, 1,4-cyclohexanedimethanol monoacrylate, 1,4-cyclohexanedimethanol monomethacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol monohydroxypentaacrylate, dipentaerythritol monohydroxypentamethacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, etc. The acrylate compound having a hydroxyl group and the methacrylate compound having a hydroxyl group may be used alone or in combination of two or more types.

Commercially available products include Aronix M-5700 (manufactured by Toagosei Co., Ltd.), 4HBA, 2HEA, CHDMMA (all manufactured by Nippon Kasei Co., Ltd.), BHEA, HPA, HEMA, HPMA (all manufactured by Nippon Shokubai Co., Ltd.), Light Ester HO, Light Ester HOP, Light Ester HOA (all manufactured by Kyoeisha Chemical Co., Ltd.), etc.

Among these, 2-hydroxy-3-acryloyloxypropyl acrylate, 2-hydroxy-3-phenoxyethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, and 1,4-cyclohexanedimethanol monoacrylate are particularly preferred. Furthermore, monofunctional acrylate compounds and monofunctional methacrylate compounds are preferred because of the ease of viscosity adjustment.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the acrylate compound having a hydroxyl group and the methacrylate compound having a hydroxyl group is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the total of the cationic polymerizable compound, aromatic alcohol, acid generator, and radical polymerizable compound.

In addition, the content of the acrylate compound having a hydroxyl group and the methacrylate compound having a hydroxyl group is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

As the polyfunctional acrylate compound and polyfunctional methacrylate compound, difunctional to hexafunctional acrylate compounds and difunctional to hexafunctional methacrylate compounds can be suitably used, with bifunctional acrylate compounds and bifunctional methacrylate compounds being particularly preferred. By using difunctional to hexafunctional compounds, the composition of the present invention will have a better balance of initial curing speed, initial adhesion, and subsequent adhesion.

Specific examples of bifunctional acrylate compounds and bifunctional methacrylate compounds include diol diacrylates such as 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, and 1,10-decanediol diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, polypropylene glycol diacrylate, neopentyl glycol diacrylate, diol diacrylates obtained by adding at least one of ethylene oxide and propylene oxide to neopentyl glycol, glycol diacrylates such as caprolactone-modified hydroxypivalic acid neopentyl glycol diacrylate, bisphenol A EO (ethylene oxide) adduct diacrylate, and bisphenol A Examples of the polyfunctional acrylates and polyfunctional methacrylates having no hydroxyl groups include diacrylate compounds having a cyclic structure such as PO (propylene oxide) adduct diacrylate, tricyclodecane dimethanol diacrylate, hydrogenated dicyclopentadienyl diacrylate, and cyclohexyl diacrylate. The polyfunctional (meth)acrylate compounds may be used alone or in combination of two or more.

Commercially available products include Light Acrylate 1,6HX-A, 1,9ND-A, 3EG-A, 4EG-A (manufactured by Kyoeisha Chemical Co., Ltd.), HDDA, 1,9-NDA, DPGDA, TPGDA (manufactured by Daicel-Cytec Co., Ltd.), Viscoat #195, #230, #230D, #260, #310HP, #335HP, #700HV (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Aronix M-208, M-211B, M-220, M-225, M-240, M-270 (manufactured by Toagosei Co., Ltd.), etc.

Among these, from the viewpoint of viscosity and compatibility, diacrylates of diols having alkyl chains with 4 to 12 carbon atoms, particularly 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, and 1,10-decanediol diacrylate, are preferred.

From the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion, the content of the polyfunctional acrylate compound and the polyfunctional methacrylate compound is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the total of the cationic polymerizable compound, the aromatic alcohol, the acid generator, and the radical polymerizable compound.

In addition, in the composition of the present invention, the content of the polyfunctional acrylate compound and the polyfunctional methacrylate compound is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

In the composition of the present invention, the content of the radical polymerizable compound is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the solid content of the composition of the present invention, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

In addition, in the composition of the present invention, the content of the radical polymerizable compound is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 5 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the composition of the present invention, from the viewpoint of achieving a better balance between the initial curing speed, the initial adhesion, and the subsequent adhesion.

<1-5. Radical polymerization initiator>
The composition of the present invention contains a cationic polymerizable compound, an aromatic alcohol, and an acid generator, but when the composition of the present invention contains a radical polymerizable compound, it may contain a radical polymerization initiator. This is because the polymerization of the radical polymerizable compound becomes easier. As the radical polymerization initiator, either a photoradical polymerization initiator or a thermal radical polymerization initiator can be used, but from the viewpoint of excellent curing speed, etc., a photoradical polymerization initiator is preferable.

Examples of photoradical polymerization initiators include benzoins such as benzoin, benzoin methyl ether, benzoin propyl ether, and benzoin butyl ether; benzil ketals such as benzil dimethyl ketal; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1-benzyl-1-dimethylamino-1-(4'-morpholinobenzoyl)propane, 2-morpholyl-2-(4'-methylmercapto)benzoylpropane, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 1-hydroxy-1-benzoylcyclohexane, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4'-isopropyl)benzoylpropane, N,N-dimethyl acetophenones such as ethylaminoacetophenone, 1,1-dichloroacetophenone, 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyldichloromethane; anthraquinones such as 2-methylanthraquinone, 1-chloroanthraquinone, and 2-amylanthraquinone; thioxanthones such as 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, and 2,4-diisopropylthioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, methylbenzophenone, 4,4'-dichlorobenzophenone, 4,4'-bisdiethylaminobenzophenone, Michler's ketone, and 4-benzoyl-4'-methyldiphenyl sulfide; 2,4,6-trimethylbenzoyldiphenylphosphine thioxanthone; oxides such as bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; carbazoles such as 3-(2-methyl-2-morpholinopropionyl)-9-methylcarbazole; α-dicarbonyls such as benzyl and methyl benzoylformate; JP-A Nos. 2000-80068, 2001-233842, 2005-97141, and JP-T No. 2006-516246, Oxime esters such as the compounds described in Japanese Patent No. 3860170, Japanese Patent No. 3798008, WO2006/018973, JP2011-132215A, and WO2015/152153A; p-methoxyphenyl-2,4-bis(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl) )-s-triazine, 2-naphthyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-butoxystyryl)-s-triazine and other triazines; benzoyl peroxide, 2,2'-azobisisobutyronitrile, ethyl anthraquinone, 1,7-bis(9'-acridinyl)heptane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, benzophenone, phenyl biphenyl ketone, 4-benzoyl-4'-methyldiphenyl sulfide, 2-(p-butoxystyryl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-dimethylbenzphenazine, benzophenone/Michler's ketone, hexaarylbiimidazole/mercaptobenzimidazole, thioxanthone/amine, etc.

Examples of thermal radical polymerization initiators include peroxides such as benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, 1,1-di(t-butylperoxy)-3,3,5-trimethylcyclohexane, 4,4-di(t-butylperoxy)butylvalerate, and dicumyl peroxide; azo compounds such as 2,2'-azobisisobutyronitrile; and tetramethylthiuranium disulfide.

The content of the radical polymerization initiator may be any content that can provide a composition with excellent adhesion. For example, the content is preferably 1 part by mass or more and 50 parts by mass or less, more preferably 5 parts by mass or more and 30 parts by mass or less, and even more preferably 15 parts by mass or more and 25 parts by mass or less, relative to 100 parts by mass of the radical polymerizable compound. By setting the content of the radical polymerization initiator within this range, the composition of the present invention will have excellent adhesion.

The content of the radical polymerization initiator may be any content that provides a composition with excellent adhesion. For example, the content is preferably 0.01 parts by mass or more and 20 parts by mass or less, more preferably 0.1 parts by mass or more and 10 parts by mass or less, even more preferably 0.5 parts by mass or more and 5 parts by mass or less, and particularly preferably 1 part by mass or more and 3 parts by mass or less, relative to 100 parts by mass of the total solid content. By setting the content of the radical polymerization initiator within this range, the composition of the present invention has excellent adhesion.

<1-6. Solvent>
The composition of the present invention may contain a solvent capable of dissolving or dispersing each of the above components, if necessary. The solvent is liquid at 25°C and atmospheric pressure, and capable of dissolving or dispersing each of the components of the composition. The solvent is also one that does not react with the cationic polymerizable compound, aromatic alcohol, acid generator, etc. Therefore, for example, even if a substance classified as a cationic polymerizable compound is liquid at 25°C and atmospheric pressure, it does not fall under the category of a solvent in the composition of the present invention.

Examples of such solvents include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate, and diethyl carbonate; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, and 2-heptanone; polyhydric alcohols and derivatives thereof such as ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol, and the monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, or monophenyl ether of dipropylene glycol monoacetate; cyclic ethers such as dioxane; ethyl formate, methyl lactate, ethyl lactate, and the like. Examples of the solvent include esters such as butyl acetate, methyl acetate, methyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl pyruvate, ethyl ethoxyacetate, methyl methoxypropionate, ethyl ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, and 3-methyl-3-methoxybutyl acetate; aromatic hydrocarbons such as toluene and xylene; and lactones such as γ-caprolactone, δ-caprolactone, ε-caprolactone, dimethyl-ε-caprolactone, δ-valerolactone, γ-valerolactone, and γ-butyrolactone. These solvents can be used alone or in the form of a mixed solvent of two or more kinds. Among the solvents, derivatives of polyhydric alcohols, lactones, and carbonates are preferred, and carbonates are particularly preferred, with propylene carbonate being particularly preferred. By using these as organic solvents, the composition of the present invention has an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

In the composition of the present invention, the content of the solvent is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 1 part by mass or less, and most preferably 0 part by mass, per 100 parts by mass of the composition of the present invention, from the viewpoint of facilitating use of the composition of the present invention as an adhesive.

<1-7. Other ingredients>
The composition of the present invention contains as essential components a cationic polymerizable compound, an aromatic alcohol, and an acid generator, and optionally contains the above-mentioned radically polymerizable compound, a radical polymerization initiator, a solvent, and the like, and may further contain other components as necessary.

Other components may include, for example, various resin additives such as thiol compounds, inorganic fillers, organic fillers, pigments, silane coupling agents, colorants such as dyes, photosensitizers, defoamers, thickeners, thixotropic agents, surfactants, leveling agents, flame retardants, plasticizers, stabilizers, polymerization inhibitors, UV absorbers, antioxidants, antistatic agents, flow regulators, and adhesion promoters, as necessary.

As a thiol compound, for example, the thiol compound described in JP 2016-102185 A can be used.

As the ultraviolet absorber and antioxidant, a latent additive can be used in which the phenolic hydroxyl group is protected with a protecting group, and the function of the ultraviolet absorber or antioxidant is expressed by removing the protecting group by heating or the like. Examples of such latent additives include the latent additives described in WO2017/170465.

The total content of these other components is preferably 30 parts by mass or less per 100 parts by mass of the total of the cationic polymerizable compound, aromatic alcohol, and acid generator.

<1-8. Method for producing composition>
The method for producing the composition of the present invention is not particularly limited as long as it is a method that can uniformly mix each component, and for example, a known mixing method can be used. As the mixing method, a method using a known mixing device can be adopted, and for example, a method using a three-roll mill, a sand mill, a ball mill, etc. can be used.

<1-9. Uses>
The uses of the composition of the present invention are not particularly limited as long as they are used to form a cured product that requires initial curing speed, initial adhesion and adhesion, and include optical films, adhesives, optical materials such as glasses and imaging lenses, paints, coating agents, lining agents, inks, high refractive index materials, water-soluble materials, resists for semiconductors, displays, MEMS and medical devices, liquid resists, printing plates, insulating varnishes, insulating sheets, laminates, printed circuit boards, sealants for semiconductor devices, LED packages, liquid crystal injection ports, organic EL, optical elements, electrical insulation, electronic components and separation membranes, etc., molding materials, putties, glass fiber impregnating agents, fillers, passivation films for semiconductors and solar cells, etc., interlayer insulating films, protective films, color Examples of the composition of the present invention include protective films for filters, spacers, DNA separation chips, microreactors, nanobiodevices, recording materials for hard disks, solid-state imaging elements, light-emitting diodes, organic light-emitting devices, luminescent films, fluorescent films, actuators, holograms, plasmon devices, polarizing plates, polarizing films, retardation films, prism lens sheets used in the backlights of liquid crystal display devices, Fresnel lens sheets used in screens such as projection televisions, lens parts of lens sheets such as lenticular lens sheets, or backlights using such sheets, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, and casting agents for optical molding. In particular, the composition of the present invention is preferably used as an adhesive. This is because the characteristics of the composition of the present invention can be effectively exhibited.

When the composition of the present invention is used as an adhesive, the material of the object to be adhered and the object on which a member containing the cured product of the composition of the present invention is to be formed may be either an organic material or an inorganic material.

Examples of organic materials include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamides, polyimides; polyurethanes; epoxy resins; polycarbonates; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene, polymethylpentene, polytetrafluoroethylene, and cycloolefin polymers; vinyl compounds such as polyvinyl alcohol, polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic resins such as polymethyl methacrylate and polyacrylic acid esters; polycarbonates; polysulfones; polyethersulfones; polyetherketones; polyetherimides; polyoxyethylene, norbornene resins; and polymeric materials such as liquid crystal materials.

Examples of inorganic materials include glasses such as soda glass and quartz glass, metals such as iron, copper, aluminum, and stainless steel, and their oxides (metal oxides).

The composition of the present invention can be formed into a sheet-like film by a film-forming method such as calendaring, rolling, T-die extrusion, or inflation. For adhesion, for example, one side of the sheet-like adhesive is attached to an object to be adhered, and then heated or irradiated with light, and the other side of the sheet-like adhesive attached to the object to be adhered is then attached to another object to be adhered, and the composition can be used. Alternatively, one side of the sheet-like adhesive may be attached to an object to be adhered, and then the other side of the sheet-like adhesive attached to the object to be adhered may be attached to another object to be adhered, and then heated or irradiated with light.

[2. Cured product]
The cured product of the present invention is made of the composition of the present invention and has a polymer containing a structural unit derived from a cationic polymerizable compound. The shape of the cured product of the present invention can be appropriately set depending on the application, etc. The application, etc. of the cured product of the present invention can be the same as the contents described in the section "1. Composition", so the description here is omitted. The composition of the present invention can be the same as the contents described in the section "A. Composition", so the description here is omitted. Furthermore, the method for producing the cured product of the present invention may be any method that can polymerize cationic polymerizable compounds together and cure the composition, and can be, for example, the same as the contents described in the section "3. Method for producing a cured product" described later.

[3. Manufacturing method of the cured product]
Next, the method for producing the cured product of the present invention will be described.
The method for producing a cured product of the present invention includes a curing step of curing the composition of the present invention. According to the method for producing a cured product of the present invention, since the composition of the present invention contains the above-mentioned components, a cured product having excellent adhesion can be easily obtained. Each step included in the method for producing a cured product of the present invention will be described below.

<3-1. Curing process＞
The curing step is a step of curing the composition of the present invention. The method of curing the composition of the present invention in this step is a method capable of forming a polymer containing a structural unit derived from a cationic polymerizable compound. That would be good.

As such a method, for example, a method can be used in which an acid is generated from an acid generator in the composition of the present invention, and the acid is used to polymerize cationic polymerizable compounds. The method for generating an acid from an acid generator varies depending on the type of acid generator, and can be, for example, a method of heating or irradiating with light, or a combination of both heating and irradiating with light.

In this step, the light source for the light irradiation used to generate an acid from the acid generator can be, for example, an electromagnetic wave energy having a wavelength of 2000 angstroms to 7000 angstroms obtained from an ultra-high pressure mercury lamp, a high pressure mercury lamp, a medium pressure mercury lamp, a low pressure mercury lamp, a mercury vapor arc lamp, a xenon arc lamp, a carbon arc lamp, a metal halide lamp, a fluorescent lamp, a tungsten lamp, an excimer lamp, a germicidal lamp, a light emitting diode, a CRT light source, or the like, or a high energy ray such as an electron beam, an X-ray, or a radiation. Preferred examples include an ultra-high pressure mercury lamp, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, and the like that emit light with a wavelength of 300 to 450 nm. The composition of the present invention can also be cured by irradiation with an LED light source. Examples of energy rays from an LED light source include ultraviolet rays. Examples of wavelengths of energy rays from an LED light source include 350 nm to 405 nm.

The light to be irradiated may be laser light. By using laser light as an exposure light source, a direct laser drawing method in which an image is formed directly from digital information such as a computer without using a mask is useful because it improves not only productivity but also resolution and positional accuracy. As the laser light, light with a wavelength of 340 to 430 nm is preferably used, but lasers that emit light in the visible to infrared range, such as excimer lasers, nitrogen lasers, argon ion lasers, helium cadmium lasers, helium neon lasers, krypton ion lasers, various semiconductor lasers, and YAG lasers, are also used. When using these lasers, a sensitizing dye that absorbs the relevant visible to infrared range is added. It can also be used with a halftone mask. After the process of irradiating the energy beam, it is preferable to heat cure the material overnight at room temperature or at 40°C to 100°C for 1 minute to 10 minutes to ensure hardening.

The light irradiation intensity is appropriately determined depending on the composition of the composition, and is not particularly limited, but it is preferable that the irradiation intensity of the wavelength region effective for activating the acid generator is 0.1 mW/cm ² or more and 6000 mW/cm ² or less. When the irradiation intensity is 0.1 mW/cm ² or more, the reaction time is not too long, and when it is 6000 mW/cm ² or less, there is little risk of yellowing of the epoxy resin due to heat radiated from the light source and heat generated during curing of the composition. The light irradiation time is controlled for each composition of the composition to be cured and is not particularly limited, but it is preferable that the integrated light amount expressed as the product of the irradiation intensity and the irradiation time is set to 10 mJ/cm ² or more and 10,000 mJ/cm ² or less. When the integrated light amount for the composition is 10 mJ/cm ² or more, a sufficient amount of active species derived from the acid generator can be generated to more reliably proceed with the curing reaction, and when it is 10,000 mJ/cm ² or less, the irradiation time is not too long and good productivity can be maintained.

In this process, the conditions for the heat treatment used to generate acid from the acid generator may be any conditions that allow the composition of the present invention to be stably cured, and may be 60°C or higher, preferably 100°C or higher and 300°C or lower. The heating time may be about 10 seconds to 3 hours.

In the method for producing a cured product of the present invention, the type of polymerization method may include only one type, or may include two or more types.

<3-2. Other processes>
The method for producing the cured product of the present invention may include other steps as necessary, such as a post-bake step of heat-treating the cured product after the curing step, a pre-bake step of heat-treating the composition of the present invention before the curing step to remove the solvent in the composition of the present invention, a coating film formation step of forming a coating film of the composition of the present invention before the curing step, and a surface treatment step of the adherend to form the cured product of the composition of the present invention.

In the coating film forming process, the composition of the present invention can be applied by known methods such as using a spin coater, roll coater, bar coater, die coater, curtain coater, various printing methods, and immersion. The coating film can be formed on a substrate.

The substrate can be appropriately selected depending on the application of the cured product, and examples of the substrate on which the cured product is formed include those described in the above section "1. Composition." After the cured product of the present invention is formed on the substrate, it may be peeled off from the substrate and used, or transferred from the substrate to another adherend and used.

The heating conditions in the pre-baking step may be any conditions that can remove the solvent in the composition of the present invention, and may be, for example, 70°C or higher and 150°C or lower for 30 to 300 seconds.

The heating conditions in the post-bake process may be any conditions that can improve the strength of the cured product obtained in the curing process, and may be, for example, 200°C to 250°C for 20 to 90 minutes. This is because the cured product of the composition of the present invention has excellent adhesion.

In the surface treatment process, methods of surface treatment of the adherend that forms a cured product of the composition include corona discharge treatment, flame treatment, high frequency treatment, ultraviolet treatment, glow discharge treatment, active plasma treatment, laser treatment, etc.

The composition, its cured product, and the method for producing the cured product of the present invention are not limited to the above-mentioned embodiments. The above-mentioned embodiments are merely examples, and anything that has substantially the same configuration as the technical idea described in the claims of the present invention and exhibits similar effects is included in the technical scope of the present invention.

The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

The compositions shown in Tables 1 to 6 were prepared, and the initial curing speed, initial adhesion, and subsequent adhesion were evaluated according to the following conditions. The values in the tables indicate parts by weight.

[Adhesion]
Each composition obtained in the Examples, Reference Examples, and Comparative Examples was applied to a sheet of PMMA film (Technoloy 125S001, manufactured by Sumitomo Chemical Co., Ltd.) so that the thickness after curing was 3 μm, and then the film was laminated with another sheet of COP (cycloolefin polymer, manufactured by Zeon Corporation: product number Zeonorfilm 14-060) film that had been subjected to corona discharge treatment using a laminator, and light equivalent to 1000 mJ/ ^cm2 was irradiated through the COP film using a metal halide lamp to cure the composition. After that, the film was left to stand for 24 hours under conditions of 30°C, 50% RH, and atmospheric pressure, and then cut into a width of 2.5 cm to prepare evaluation sample A, which was subjected to a 90° peel test.

The 90° peel test was performed by pulling the COP film of the evaluation sample in a 90° direction using a tensile tester FTN1-13A (manufactured by Aiko Engineering Co., Ltd.) at 25°C and peeling it off, and measuring the maximum strength at which the COP film peeled off from the PMMA film as the adhesive strength. The evaluation was performed according to the following criteria. The results are shown in Tables 1 to 6 below. It can be determined that the greater the maximum strength, the better the adhesive strength.
++: 2N or more.
+: 1N or more but less than 2N.
-: Less than 1N.

[Initial adhesion]
An evaluation sample was prepared in the same manner as in the evaluation of adhesion, except that the treatment of leaving it for 24 hours under conditions of 30°C, 50% RH, and atmospheric pressure was not performed. Next, this evaluation sample was cut into a width of 2.5 cm to obtain evaluation sample B for evaluating adhesion. This evaluation sample B was left to stand for 10 minutes after completion of light irradiation with a metal halide lamp, and then a 90° peel test similar to that for evaluating adhesion was performed, and the maximum strength when the COP film was peeled off from the PMMA film was measured as the adhesive strength. Evaluation was performed according to the following criteria. The results are shown in Tables 1 to 6 below. It can be determined that the greater the maximum strength, the better the adhesive strength.
++: 1N or more.
+: 0.5N or more but less than 1N.
-: Less than 0.5N.

[Initial curing speed]
The compositions obtained in the Examples, Reference Examples, and Comparative Examples were used to measure the initial heat generation amount during light irradiation using a photochemical reaction calorimeter (photo DSC, Hitachi High-Tech Science Corporation DSC-7000X) to evaluate the curability. Each sample was 10 mg, and the light irradiation conditions were room temperature (25°C) and 200 mJ irradiation at 50 mW using a 365 nm light source, and the initial curing speed was calculated from the heat generation amount observed at that time. The initial curing speed was calculated by plotting the heat generation amount with time (min) on the horizontal axis and μW on the vertical axis, and measuring the slope (μW/min) from the start of UV irradiation to the peak top. It can be determined that the greater the slope, the faster the initial curing speed.
++: The initial curing rate (slope (μW/min)) is 5×10 ⁵ or more.
+: The initial curing rate (slope (μW/min)) is 4×10 ⁵ or more and less than 5×10 ⁵ .
-: The initial curing rate (slope (μW/min)) is less than 4×10 ⁵ .

Ａ２：脂肪族エポキシ化合物（一般式（１）で表される化合物（低分子量化合物））

Ａ３：脂肪族エポキシ化合物（脂肪族エポキシポリマーａ（メチルメタクリレート７０質量部とグリシジルメタクリレート３０質量部との共重合体、重量平均分子量Ｍｗ１５０００）、高分子量化合物））

Ａ４：脂環式エポキシ化合物（セロキサイド２０２１Ｐ（ダイセル社製、一般式（２）で表される化合物、低分子量化合物））

Ａ５：脂環式エポキシ化合物（セロキサイド３０００（ダイセル社製、一般式（３）で表される化合物、低分子量化合物））

Ａ６：オキセタン化合物（ＯＸＴ－２２１（東亞合成社製、二官能オキセタン化合物））

Ａ７：芳香族エポキシ化合物（１価フェノールのアルキレンオキサイド付加物のモノグリシジルエーテル化物（低分子量化合物））

Ａ８：芳香族エポキシ化合物（ビスフェノールＡ型エポキシ化合物（低分子量化合物））

Ａ９：４－ヒドロキシブチルビニルエーテル

Ｂ１：ベンジルアルコール

Ｂ２：４－イソプロピルベンジルアルコール

Ｂ３：２－メトキシベンジルアルコール

Ｂ４：フェネチルアルコール

Ｂ５：フェニルプロパノール

Ｃ１：トリプロピレングリコール

Ｃ２：ジプロピレングリコール

Ｃ３：２，２－ジメチル－１－プロパノール

Ｄ１：１，６－ヘキサンジオールジアクリレート

Ｄ２：４－ヒドロキシブチルアクリレート

Ｅ１：ＥＴ－２２０１（増感剤）

Ｆ１：東レダウコーニング社製ＳＨ－２９ Ｐａｉｎｔ ａｄｄｉｔｉｖｅ（レベリング剤）
Ｇ１：酸発生剤（芳香族スルホニウム塩、下記２種類の化合物の混合物の５０質量％プロピレンカーボネート溶液）

Ｇ２：ＬＵＮＡ２００（ＤＫＳＨジャパン社製）
A1: Aliphatic epoxy compound (compound represented by general formula (1) (low molecular weight compound))

A2: Aliphatic epoxy compound (compound represented by general formula (1) (low molecular weight compound))

A3: Aliphatic epoxy compound (aliphatic epoxy polymer a (copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate, weight average molecular weight Mw 15000), high molecular weight compound)

A4: Alicyclic epoxy compound (Celloxide 2021P (manufactured by Daicel Corporation, compound represented by general formula (2), low molecular weight compound))

A5: Alicyclic epoxy compound (Celloxide 3000 (manufactured by Daicel Corporation, compound represented by general formula (3), low molecular weight compound))

A6: Oxetane compound (OXT-221 (manufactured by Toagosei Co., Ltd., bifunctional oxetane compound))

A7: Aromatic epoxy compound (monoglycidyl ether of alkylene oxide adduct of monohydric phenol (low molecular weight compound))

A8: Aromatic epoxy compound (bisphenol A type epoxy compound (low molecular weight compound))

A9: 4-hydroxybutyl vinyl ether

B1: Benzyl alcohol

B2: 4-isopropylbenzyl alcohol

B3: 2-Methoxybenzyl alcohol

B4: Phenethyl alcohol

B5: Phenylpropanol

C1: Tripropylene glycol

C2: Dipropylene glycol

C3: 2,2-dimethyl-1-propanol

D1: 1,6-hexanediol diacrylate

D2: 4-hydroxybutyl acrylate

E1: ET-2201 (sensitizer)

F1: SH-29 Paint additive (leveling agent) manufactured by Dow Corning Toray Co., Ltd.
G1: Acid generator (aromatic sulfonium salt, a 50% by mass propylene carbonate solution of a mixture of the following two compounds)

G2: LUNA200 (manufactured by DKSH Japan)

From Tables 1 to 6, it can be seen that the composition of the present invention can give a cured product with an excellent balance of initial curing speed, initial adhesion, and subsequent adhesion.

Claims (7)

The composition contains a cationic polymerizable compound, an aromatic alcohol, and an acid generator,
the cationically polymerizable compound includes both an aliphatic epoxy compound and an alicyclic epoxy compound,
the aliphatic epoxy compound is a combination of a low molecular weight aliphatic epoxy compound having a molecular weight of 1,000 or less and a high molecular weight aliphatic epoxy compound having a molecular weight of more than 1,000 and 100,000 or less;
The high molecular weight aliphatic epoxy compound has the following structural unit (II-1):

In general formula (II-1), R ¹ represents a hydrogen atom, a methyl group, or a halogen atom;
^R3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
t is an integer of 1 to 6, and * represents a bond.
the total amount of the aliphatic epoxy compound and the alicyclic epoxy compound is 50 parts by mass or more and 99 parts by mass or less relative to 100 parts by mass of the cationic polymerizable compound,
The aromatic alcohol is represented by the following general formula (7):

(The aromatic ring Ar is a p-valent aromatic hydrocarbon ring which may have a substituent having 6 to 20 carbon atoms or a p-valent aromatic heterocycle which may have a substituent having 2 to 20 carbon atoms, B is a group represented by general formula (8) (when p is 2 or more, each B may be the same or different), and ^Y2 is a group in which q hydrogen atoms have been removed from an alkyl group having a straight chain, branched chain or cycloalkyl ring and having 1 to 20 carbon atoms.
In addition, p represents 1 to 6, q represents 1 to 10, * represents a bond,
the substituent is selected from an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms;
a content of the aromatic alcohol is 0.97 parts by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the cationically polymerizable compound, the aromatic alcohol, and the acid generator;
A composition characterized in that it is a composition for use as an adhesive. The composition according to claim 1, wherein the cationic polymerizable compound includes a vinyl ether compound. The composition according to claim 1 or 2, wherein the aromatic alcohol is a primary alcohol or a secondary alcohol. The composition according to any one of claims 1 to 3, further comprising a radically polymerizable compound having a (meth)acryloyl group. The composition according to claim 4, wherein the radical polymerizable compound having a (meth)acryloyl group is an acrylate or methacrylate having a hydroxyl group. A component comprising an adhesive layer formed from a cured product of the composition according to any one of claims 1 to 5. A method for manufacturing a member, comprising a curing step of applying the composition according to any one of claims 1 to 5 to an object to be adhered and curing it.