JP6797420B2 - Light moisture curable resin composition - Google Patents

Description

The present invention relates to a light-moisture-curable resin composition and the like.

The surface of an electronic circuit board is treated with a coating agent to protect it in order to prevent malfunction due to water, humidity, gas, dust, and the like. Among the coating agents, resin compositions that are cured by light such as ultraviolet rays and electron beams have high productivity and have been reported in various ways (Patent Documents 1 and 2).

However, the photocurable coating agent of Patent Document 1 has a problem that the resin in the shadow portion not exposed to light is not cured on the substrate on which various parts are mounted. The photo-moisture-curable resin of Patent Document 2 has insufficient electrical insulation in both photo-curing and moisture-curing, and its viscosity is lowered by diluting with a solvent. Therefore, the environment is affected by the volatilization of the solvent during use. There is a problem that there is a risk of adversely affecting the operator.

JP-A-2017-179180 Japanese Unexamined Patent Publication No. 2014-201593

While the present inventor is proceeding with research, increasing the amount of isocyanate groups in urethane (meth) acrylate improves the moisture curability, and the resin that has entered the shadowed part that is not exposed to light can be sufficiently cured. Since the resin viscosity increases as the molecular weight increases, it has been found that it is difficult to apply a thin coating.

In view of these problems, the present invention provides light having excellent photocurability and moisture curability, low viscosity, and excellent electrical insulation (particularly, electrical insulation of shadows where light is difficult to hit). An object of the present invention is to provide a moisture-curable resin composition.

As a result of diligent research in view of the above problems, the present inventor has (1) a reaction of a hydroxyl group-containing monofunctional (meth) acrylate (A1), an isocyanurate-modified product of a polyisocyanate compound (A2), and a polyol (A3). Urethane (meth) acrylate (A), which is a product and has a weight average molecular weight of 1000 to 50,000, (2) hydroxyl group-free (meth) acrylate (B), and (3) photopolymerization initiator (C). It has been found that the above-mentioned problems can be solved by the light-moisture-curable resin composition contained therein. The present inventors have completed the present invention by conducting further research based on this finding.

That is, the present invention includes the following aspects:
Item 1. (1) Urethane (1) which is a reaction product of a hydroxyl group-containing monofunctional (meth) acrylate (A1), an isocyanurate-modified compound (A2) of a polyisocyanate compound, and a polyol (A3) and has a weight average molecular weight of 1000 to 50,000. Meta) Acrylate (A),
(2) Hydroxyl-free (meth) acrylate (B), and (3) Photopolymerization initiator (C),
A light-moisture-curable resin composition containing.

Item 2. Item 2. The photomoisture-curable resin composition according to Item 1, wherein the isocyanurate-modified product (A2) of the polyisocyanate compound is an isocyanurate-modified product of an aliphatic polyisocyanate compound.

Item 3. Item 2. The photomoisture-curable resin composition according to Item 1 or 2, wherein the urethane (meth) acrylate (A) has an NCO content of 1 to 10%.

Item 4. The content of the urethane (meth) acrylate (A) is 10 to 40% by mass with respect to a total of 100% by mass of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). , Item 3. The photomoisture-curable resin composition according to any one of Items 1 to 3.

Item 5. The content of the urethane (meth) acrylate (A) is 25 to 35% by mass with respect to a total of 100% by mass of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). , Item 4. The photomoisture-curable resin composition according to any one of Items 1 to 4.

Item 6. Item 2. The photomoisture-curable resin composition according to any one of Items 1 to 5, further containing polyisocyanate (D).

Item 7. Item 2. The light-moisture-curable resin composition according to any one of Items 1 to 6, which is used for coating.

Item 8. Item 2. The light-moisture-curable resin composition according to Item 7, wherein the object to be coated is an electronic substrate.

Item 9. Item 8. A cured product of the light-moisture-curable resin composition according to any one of Items 1 to 8.

Item 10. A resin-coated electronic substrate comprising an electronic substrate and a cured product according to Item 9, which is arranged on the electronic substrate.

According to the present invention, it is excellent in both photocurability and moisture curability, has low viscosity, and has excellent photoinsulation property at the time of curing (particularly, electroinsulation property in a shadow portion where light is hard to hit). A resin composition can be provided. Therefore, the photomoisture-curable resin composition of the present invention is suitable for coating, for example, particularly for coating an electronic substrate. Further, according to the present invention, it is also possible to provide an electronic substrate and a resin-coated electronic substrate containing a cured product of the light-moisture-curable resin composition of the present invention arranged on the electronic substrate.

In the present specification, the expressions "contains" and "contains" include the concepts of "contains", "contains", "substantially consists" and "consists of only".

1. 1. Light Moisture Curing Resin Composition In one embodiment of the present invention, a reaction product of (1) a hydroxyl group-containing monofunctional (meth) acrylate (A1), an isocyanurate-modified compound (A2) of a polyisocyanate compound, and a polyol (A3). Contains urethane (meth) acrylate (A) having a weight average molecular weight of 1000 to 50,000, (2) hydroxyl group-free (meth) acrylate (B), and (3) photopolymerization initiator (C). The present invention relates to a photomoisture-curable resin composition (in this specification, it may be referred to as "the photomoisture-curable resin composition of the present invention"). Hereinafter, the light-moisture-curable resin composition of the present invention will be described.

The hydroxyl group-containing monofunctional (meth) acrylate (A1) is not particularly limited as long as it contains hydroxyl groups (preferably has one hydroxyl group) and has one (meth) acryloyl group. , It is possible to use various components or components that can be used in the photo-moisture-curable resin composition (particularly, the photo-moisture-curable resin composition for coating electronic substrates).

Specific examples of the hydroxyl group-containing monofunctional (meth) acrylate (A1) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl. Hydroxyalkyl (meth) acrylates such as (meth) acrylate, hydroxypentyl (meth) acrylate, hydroxyhexyl (meth) acrylate hydroxyoctyl (meth) acrylate; 2-hydroxy-3-phenoxypropyl (meth) acrylate; 2-hydroxyethyl Acrylamide; examples thereof include modified lactones.

As the hydroxyl group-containing monofunctional (meth) acrylate (A1), preferably a hydroxyalkyl (meth) acrylate, more preferably a hydroxyalkyl (meth) acrylate having a hydroxyalkyl group having 1 to 8 carbon atoms, and further preferably a hydroxyalkyl group. A hydroxyalkyl (meth) acrylate having 1 to 5 carbon atoms, more preferably a hydroxyalkyl (meth) acrylate having a hydroxyalkyl group having 1 to 3 carbon atoms, and particularly preferably a hydroxyalkyl group having 2 carbon atoms. Examples include (meth) acrylate. In the hydroxyalkyl (meth) acrylate, the alkyl group in the hydroxyalkyl group is preferably a linear alkyl group. Further, in the hydroxyalkyl (meth) acrylate, the hydroxy group in the hydroxyalkyl group is preferably located at the end on the main chain of the alkyl group.

The hydroxyl group-containing monofunctional (meth) acrylate (A1) can be used alone or in combination of any two or more.

The isocyanurate-modified product (A2) of the polyisocyanate compound as the polyisocyanate is particularly limited as long as it is an isocyanurate-modified product of the polyisocyanate compound (in other words, a trimmer of the polyisocyanate compound or a polyisocyanate having an isocyanurate skeleton). However, it is possible to use various components or components that can be used in the photo-moisture-curable resin composition (particularly, the photo-moisture-curable resin composition for coating an electronic substrate).

Specific examples of the polyisocyanate compound include an aliphatic polyisocyanate compound, an alicyclic polyisocyanate compound, an aromatic polyisocyanate compound, and an aromatic aliphatic polyisocyanate compound.

Examples of the aliphatic polyisocyanate compound include tetramethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate (HDI), 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and 2-methyl. Alkylene diisocyanates such as pentane-1,5-diisocyanate and 3-methylpentane-1,5-diisocyanate; lysine diisocyanates and the like can be mentioned.

Examples of the alicyclic polyisocyanate compound include isophorone diisocyanate, hydrogenated xylylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,4-cyclohexanediisocyanate, methylcyclohexylene diisocyanate, and 1,3-bis (isocyanate methyl). Cyclohexane and the like can be mentioned.

Examples of the aromatic polyisocyanide compound include tolylene diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate (MDI), and 4,4'-dibenzyldiisocyanate. Examples thereof include 1,5-naphthylene diisocyanis, xylylene diisocyanate, 1,3-phenylenediisocyanis, 1,4-phenylenediisocyanate, and preferably 2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'. − Diphenylmethane diisocyanate (MDI) and the like.

Examples of the aromatic aliphatic polyisocyanate compound include dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, α, α, α, α-tetramethylxylylene diisocyanate and the like.

The polyisocyanate compound is preferably an aliphatic polyisocyanate compound, more preferably an alkylene diisocyanate, further preferably an alkylene diisocyanate having 1 to 10 carbon atoms, and further preferably an alkylene group having 4 to 8 carbon atoms. Examples thereof include certain alkylene diisocyanates, particularly preferably alkylene diisocyanates having an alkylene group having 5 to 7 carbon atoms. In the alkylene diisocyanate, the alkylene group is preferably a linear alkylene group. Further, in the alkylene diisocyanate, it is preferable that the two isocyanate groups (-N = C = O) are located at the ends on the main chain of the alkylene group.

The isocyanurate-modified product (A2) of the polyisocyanate compound may be used alone or in combination of any two or more.

The polyol (A3) is not particularly limited, and various components used in the light-moisture-curable resin composition (particularly, the light-moisture-curable resin composition for coating electronic substrates) or components that can be used may be used. It is possible.

Specific examples of the polyol (A3) include polyether polyol, polyester polyol, polybutadiene polyol, castor oil-based polyol, dimer acid polyol, polycarbonate polyol, polyacrylic polyol, polycaprolactone polyol, and hydrides thereof (for example, polybutadiene). Examples thereof include hydrides of polyols, hydrides of polydiene polyols such as hydrides of polyisoprene polyols; hydrides of castor oil, etc.), and modified products.

As the polyol (A3), a polyether polyol is preferably used. Among these, polyalkylene oxide is more preferable, and polypropylene oxide is more preferable.

The polyol (A3) may be used alone or in combination of any two or more.

Urethane (meth) acrylate (A) is particularly a reaction product of a reaction component containing a hydroxyl group-containing monofunctional (meth) acrylate (A1), an isocyanurate-modified compound (A2) of a polyisocyanate compound, and a polyol (A3). Not limited. As long as the reaction component contains the A1 component, the A2 component, and the A3 component as the main components, other components (for example, (meth) acrylate, polyisocyanate, polyol) may be contained in addition to these components. The amounts of the A1 component, the A2 component and the A3 component are, for example, 90% by mass or more, preferably 95% by mass or more, more preferably 99% by mass or more, and particularly preferably 100% by mass, based on 100% by mass of the total amount of the reaction components. Is.

The weight average molecular weight of urethane (meth) acrylate (A) is 1000 to 50,000. The weight average molecular weight is a value measured by a gel permeation chromatography (GPC) method (in terms of polystyrene). The weight average molecular weight is preferably 1500 to 30000, more preferably 2000 to 20000, and even more preferably 2300 to 15000. The weight average molecular weight is preferably 5,000 to 30,000, more preferably 8,000 to 20,000, and even more preferably 1,000 to 15,000 in the case of obtaining a relatively highly viscous substance. On the other hand, the weight average molecular weight is preferably 1500 to 5000, more preferably 2000 to 4000, and even more preferably 2300 to 4000 in the case of obtaining a relatively low viscosity.

The NCO content of the urethane (meth) acrylate (A) is not particularly limited, but is, for example, 1 to 10%. The NCO content is preferably 2-8%, more preferably 3-7%.

The urethane (meth) acrylate (A) can be used alone or in combination of any two or more.

The urethane (meth) acrylate (A) can be produced according to a known production method of urethane (meth) acrylate. For example, a method of reacting all the components at once, a method of reacting some components first, and then reacting other components, and the like can be mentioned.

The content of the urethane (meth) acrylate (A) is not particularly limited, but is based on 100% by mass of the total of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). For example, it is 7 to 45% by mass, preferably 10 to 40% by mass, more preferably 20 to 40% by mass, still more preferably 25 to 35% by mass, and even more preferably 28 to 32% by mass.

The hydroxyl group-free (meth) acrylate (B) is not particularly limited as long as it does not contain a hydroxyl group and contains a (meth) acryloyl group, and is a light-moisture-curable resin composition (particularly, light-moisture for coating an electronic substrate). It is possible to use various components or components that can be used in the curable resin composition).

The number of (meth) acryloyl groups in the hydroxyl group-free (meth) acrylate (B) is not particularly limited, but is, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 2, and even more preferably 1.

The hydroxyl group-free (meth) acrylate (B) preferably does not contain not only a hydroxyl group but also other active hydrogen-containing groups (for example, polar groups such as a carboxy group, a sulfo group, and a phosphoric acid group).

Specific examples of the hydroxyl group-free (meth) acrylate (B) include isopropyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and isopentyl (meth). ) Acrylate, 2-methylbutyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, ethylhexyl (meth) acrylate and other aliphatic (mono) methacrylate; cyclohexyl (meth) acrylate, Isobornyl (meth) acrylate, adamantyl (meth) acrylate, tricyclodecanedimethylol (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, etc. Alicyclic (mono) methacrylate; phenoxyethyl (meth) acrylate, phenoxypropyl (meth) acrylate, phenoxy (polyalkyleneoxy) (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate and 2-hydroxy- 3-Phenoxypropyl acrylate (addition of phenylglycidyl ether and (meth) acrylic acid), (meth) acrylate of nonylphenol ethylene oxide adduct, o-phenylphenoxyethyl (meth) acrylate, m-phenylphenoxyethyl (meth) acrylate , P-phenylphenoxyethyl (meth) acrylate, o-phenylphenoxypropyl (meth) acrylate, m-phenylphenoxypropyl (meth) acrylate, p-phenylphenoxypropyl (meth) acrylate, o-phenylphenoxy (polyalkyleneoxy) (Meta) acrylate, m-phenylphenoxy (polyalkyleneoxy) (meth) acrylate, p-phenylphenoxy (polyalkyleneoxy) (meth) acrylate, o-phenylphenyl (meth) acrylate, m-phenylphenyl (meth) acrylate And p-phenylphenyl (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, p-cumylphenoxypropyl (meth) acrylate, p-cumylphenoxy (polyalkyleneoxy (meth)) acrylate and p-cumylphenyl. Aromatic (mono) metaacrylate such as (meth) acrylate G; Examples thereof include tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, and heterocyclic-containing mono (meth) acrylate such as (meth) acryloryloxyethyl hexahydrophthalimide.

Examples of the hydroxyl group-free (meth) acrylate (B) include alicyclic (mono) methacrylate, more preferably an alicyclic (mono) methacrylate having a bicyclic aliphatic ring, and further. Preferred are alicyclic (mono) methacrylates in which the aliphatic ring is bicyclic and the two rings share three or more (for example, 3 to 5) carbon atoms.

The hydroxyl group-free (meth) acrylate (B) can be used alone or in combination of any two or more.

The content of the hydroxyl group-free (meth) acrylate (B) is not particularly limited, but is based on 100% by mass of the total of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). For example, it is 55 to 93% by mass, preferably 60 to 90% by mass, more preferably 60 to 80% by mass, still more preferably 63 to 75% by mass, and even more preferably 68 to 72% by mass.

The photomoisture-curable resin composition of the present invention can contain polyisocyanate (D). The photomoisture-curable resin composition of the present invention does not contain polyisocyanate (D) in one aspect thereof, and contains polyisocyanate (D) in another aspect.

The polyisocyanate (D) is not particularly limited, and various components used in the photo-moisture-curable resin composition (particularly, the photo-moisture-curable resin composition for coating electronic substrates) or components that can be used are used. Is possible.

Specific examples of the polyisocyanate (D) include polyisocyanate compounds such as aliphatic polyisocyanate compounds, alicyclic polyisocyanate compounds, aromatic polyisocyanate compounds, and aromatic aliphatic polyisocyanate compounds; modification of polyisocyanate compounds. Examples thereof include isocyanurates, adducts, biurets, carbodiimides, allophanates, etc., polyisocyanate compounds, and the like. Each polyisocyanate compound is the same as the above-mentioned description regarding "isocyanurate modified product of polyisocyanate compound (A2)".

The polyisocyanate (D) may be used alone or in combination of any two or more.

The content of the polyisocyanate (D) is not particularly limited as long as the components A and B are the main components, and urethane (meth) acrylate (A), hydroxyl group-free (meth) acrylate (B), and polyisocyanate ( For example, it is 0 to 15% by mass, preferably 0 to 10% by mass, and more preferably 0 to 7% by mass with respect to the total 100% by mass of D).

The photopolymerization initiator (C) is not particularly limited, and various components used in the photo-moisture-curable resin composition (particularly, the photo-moisture-curable resin composition for coating electronic substrates) or components that can be used are used. It is possible to do.

Specific examples of the photopolymerization initiator (C) include 2,2-dimethoxy-2-phenylacetophenone, phenoxydichloroacetophenone, butyldichloroacetophenone, diethoxyacetophenone, hydroxymethylphenylpropanone, and isopropylphenylhydroxy. Acetphenone-based initiators such as methylpropanone, hydroxycyclohexylphenylketone and hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one; benzophenone, benzoylbenzoic acid, methyl o-benzoylbenzoate Benzophenone-based polymerization initiators such as esters, p-dimethylaminobenzoic acid esters, methyl benzoyl benzoates, phenylbenzophenones, trimethylbenzophenones and hydroxybenzophenones; thioxanthone, chlorthioxanthone, methylthioxanthone, isopropylthioxanthone, dichlorothioxanthone, diethylthioxanthone and diisopropylthioxanthone. And other thioxanthone-based initiators; phosphine-based initiators such as bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide and the like can be mentioned.

The photopolymerization initiator (C) may be used alone or in combination of any two or more.

The content of the photopolymerization initiator (C) is not particularly limited, and is based on 100 parts by mass of the total of urethane (meth) acrylate (A), hydroxyl group-free (meth) acrylate (B), and polyisocyanate (D). For example, it is 0.1 to 15 parts by mass, preferably 0.3 to 10 parts by mass, and more preferably 1 to 5 parts by mass.

The light-moisture-curable resin composition of the present invention can contain components other than the components A to D. Examples of other components include urethane (meth) acrylates other than the A component, (meth) acrylates other than the B component, and various additives. As the additive, various components used in the light-moisture-curable resin composition (particularly, the light-moisture-curable resin composition for coating electronic substrates) or components that can be used can be used, for example, moisture. Examples thereof include curing catalysts, polymerization inhibitors, antioxidants, defoaming agents, leveling agents, silane coupling agents, fluorescent agents, ultraviolet absorbers, pigments and solvents.

The other components may be used alone or in combination of any two or more.

The content of the other components is not particularly limited, and is, for example, 15% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less, based on 100% by mass of the photomoisture-curable resin composition of the present invention. , More preferably 1% by mass or less. The lower limit of the content is, for example, 0% by mass, 0.1% by mass, and 0.5% by mass.

2. 2. Method for Producing Photo-Moisture Curable Resin Composition The method for producing the photo-moisture-curable resin composition of the present invention is not particularly limited, and the photo-moisture-curable resin composition (particularly, photo-moisture-curable resin composition for electronic substrate coating) is not particularly limited. It can be produced according to a conventionally known method used as a method for producing a product), or by a method similar thereto.

In the photomoisture-curable resin composition of the present invention, each component containing, for example, urethane (meth) acrylate (A), hydroxyl group-free (meth) acrylate (B), and photopolymerization initiator (C) is stirred and mixed. Can be obtained by

All of the components can be mixed at the same time or substantially at the same time, or only a part of the components can be mixed first, and then other components can be added and mixed in sequence.

The mixing temperature is not particularly limited, but is, for example, 15 to 40 ° C.

The mixing time is not particularly limited, but is, for example, 10 to 30 minutes.

3. 3. Applications of the photo-moisture-curable resin composition The photo-moisture-curable resin composition of the present invention has excellent photocurability and moisture-curable properties, has a low viscosity, and has electrical insulation properties during curing (particularly, it is difficult to be exposed to light). Excellent electrical insulation in the shadow area). Therefore, the photomoisture-curable resin composition of the present invention is suitable for coating, for example, particularly for coating an electronic substrate. Further, according to the present invention, it is also possible to provide an electronic substrate and a resin-coated electronic substrate containing a cured product of the light-moisture-curable resin composition of the present invention arranged on the electronic substrate.

The photomoisture-curable resin composition of the present invention has a viscosity at the time of preparation (viscosity at 23 ° C. measured by a B-type rotational viscometer), for example, 5 to 1000 mPa · s, preferably 5 to 500 mPa · s, more preferably. It is 5 to 400 mPa · s.

The coating method is not particularly limited, and examples thereof include spray coating and inkjet coating.

The curing treatment method after coating is not particularly limited, but for example, it is irradiated with light and then left for several hours to several days (for example, 8 hours to 2 days, preferably 12 hours to 24 hours) to be cured by moisture in the air. There is a way to make it.

The light irradiation conditions are not particularly limited as long as they are curable conditions. The illuminance is, for example, 10 mW / cm ² or more, preferably 20 mW / cm ² or more, and more preferably 30 mW / cm ² or more. The upper limit of the illuminance is not particularly limited, for example, ^{1000mW / cm 2, 500mW / cm} 2, 100mW / cm 2, 45mW / cm 2. The light irradiation time is appropriately set according to the illuminance and is not particularly limited. The light irradiation time is, for example, 1 to 180 seconds, 5 to 150 seconds, 15 to 120 seconds, 25 to 90 seconds, and 30 to 60 seconds.

The electronic board is not particularly limited, and examples thereof include electronic boards used for various purposes such as power supplies, control circuits, and communications. The material and shape of the electronic substrate are not particularly limited, but are inflexible rigid substrates obtained by composite molding of phenolic resin, epoxy resin, paper, glass cloth, etc., and flexible substrates made of sheet-shaped polyimide or polyester. Is common. Further, the electrodes and wiring materials formed on the electronic substrate are not particularly limited, and these may be formed at desired positions on the electronic substrate.

Hereinafter, the present invention will be described in detail based on examples, but the present invention is not limited to these examples.

(1) Preparation of Light-Moisture Curable Resin Composition A light-moisture-curable resin composition was prepared according to the formulation shown in Table 1 (the unit of the numerical value is a mass part). Specifically, urethane acrylate, acrylate monomer (hydroxyl-free acrylate (monofunctional acrylate or polyfunctional acrylate), or hydroxyl group-containing acrylate), photopolymerization initiator (further isocyanate in the case of Example 5), moisture curing catalyst. Dibutyltin dilaurate was put into a separable flask and kept warm at 25 ° C. for 30 minutes under stirring to obtain a light-moisture-curable resin composition.

Details of the materials used are as follows.

<Urethane acrylate>
<Urethane acrylate A>
"Hydroxyethyl acrylate (monofunctional acrylate containing hydroxyl group), polypropylene oxide (polyol), and isocyanurate modified product of hexamethylene diisocyanate"
NCO content = about 4.2%
Weight average molecular weight about 13000.

<Urethane acrylate B>
"Hydroxyethyl acrylate (monofunctional acrylate containing hydroxyl group), polypropylene oxide (polyol), and isocyanurate modified product of hexamethylene diisocyanate"
NCO content = about 5.9%
Weight average molecular weight about 2650.

<Urethane acrylate C>
"Hydroxyethyl acrylate (monofunctional acrylate containing hydroxyl group), polypropylene oxide (polyol), and isocyanurate modified product of hexamethylene diisocyanate"
NCO content = about 3.2%
Weight average molecular weight about 76000.

<Urethane acrylate D>
Reactant NCO content with a molar ratio of hydroxypropyl acrylate to hexamethylene diisocyanate of 1: 1 = about 14%
Weight average molecular weight 450.

<Acrylate monomer>
IBXA (isobornyl acrylate, manufactured by Osaka Organic Chemical Co., Ltd.) alicyclic monofunctional acrylate THFA (tetrahydrofurfuryl acrylate, manufactured by Osaka Organic Chemical Co., Ltd.) monofunctional acrylate 1,9-NDA (1,9-nonanediol diacrylate, Kyoeisha Chemical Co., Ltd.) Bifunctional acrylate HPA (hydrixipropyl diacrylate, manufactured by Osaka Organic Chemical Co., Ltd.) hydroxylated acrylate.

<Isocyanate>
TPA-100 (manufactured by Asahi Kasei Chemicals Co., Ltd.) A modified isocyanurate of hexamethylene diisocyanate.

<Photopolymerization initiator>
Irgacure651 (2,2-dimethoxy-2-phenylacetophen, manufactured by BASF).

<Moisture curing catalyst>
TN-12 (dibutyltin dilaurate, manufactured by Sakai Chemical Industry Co., Ltd.)
(2) Viscosity The viscosity (23 ° C.) of the photomoisture-curable resin composition was measured by measuring with a B-type rotational viscometer. Based on the viscosity, it was evaluated according to the following evaluation criteria.
<Evaluation criteria>
◯: ~ 500 mPa · s.
Δ: 501 to 1000 mPa · s.
X: 1001 mPa · s or more.

(3) A photo- moisture-curable resin composition was applied onto a photocurable glass so as to have a film thickness of 100 μm, and was cured by irradiating with ultraviolet rays (34 mW / cm ² , 45 seconds) with a high-pressure mercury lamp. The surface of the cured coating film was evaluated by touch. The evaluation criteria are as follows.
<Evaluation criteria>
◯: No fingerprint remains.
△: There is tack.
×: There is deposit on the finger.

(4) A light-moisture-curable resin composition was placed in a moisture-curable plaster can so as to have a film thickness of 100 μm, and left at 23 ° C. and 25% humidity in a light-shielded state. The coating film was held in a vertical state on a regular basis, it was examined whether or not the coating film flowed, and the period until it stopped flowing (the period until it hardened to the extent that it did not flow) was measured. Based on the measured values, evaluation was performed according to the following evaluation criteria.
<Evaluation criteria>
◯: The period until it stops flowing is less than 3 days.
Δ: The period until the fluid stops flowing is 3 days or more and less than 3 weeks.
X: Flows even after 3 weeks have passed.

(5) An electrically insulating JIS2 type comb-shaped substrate was coated with a light-moisture-curable resin composition so as to have a film thickness of 100 μm. After curing by the following two methods, the electrical insulation was measured with a digital super insulation meter.
<Method 1> After irradiating ultraviolet rays with a high-pressure mercury lamp (34 mW / cm ² , 45 seconds), the mixture was left at 23 ° C. and 25% humidity for 16 hours to obtain a cured product.
<Method 2> A cured product was obtained by leaving it in a light-shielded state at 23 ° C. and 25% humidity for 3 days without irradiating it with ultraviolet rays.

The electrical insulation of the cured product according to Method 1 was defined as the electrical insulation of the photocured portion, and the electrical insulation of the cured product according to Method 2 was defined as the electrical insulation of the pubic portion.

(6) Results The results are shown in Tables 1 and 2.

Claims (9)

(1) Urethane (1) which is a reaction product of a hydroxyl group-containing monofunctional (meth) acrylate (A1), an isocyanurate-modified compound (A2) of a polyisocyanate compound, and a polyol (A3) and has a weight average molecular weight of 1000 to 50,000. Meta) Acrylate (A),
(2) Hydroxyl-free (meth) acrylate (B), and (3) Photopolymerization initiator (C),
Contain,
The NCO content of the urethane (meth) acrylate (A) is 1 to 10%, and
The content of the urethane (meth) acrylate (A) is 7 to 45% by mass with respect to a total of 100% by mass of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). ,
Light and moisture curable resin composition. The photomoisture-curable resin composition according to claim 1, wherein the isocyanurate-modified product (A2) of the polyisocyanate compound is an isocyanurate-modified product of an aliphatic polyisocyanate compound. The content of the urethane (meth) acrylate (A) is 10 to 40% by mass with respect to a total of 100% by mass of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). The photomoisture-curable resin composition according to claim 1 or 2 . The content of the urethane (meth) acrylate (A) is 25 to 35% by mass with respect to a total of 100% by mass of the urethane (meth) acrylate (A) and the hydroxyl group-free (meth) acrylate (B). , The photomoisture-curable resin composition according to any one of claims 1 to 3 . The light-moisture-curable resin composition according to any one of claims 1 to 4 , further containing a polyisocyanate (D). The light-moisture-curable resin composition according to any one of claims 1 to 5 , which is used for coating. The light-moisture-curable resin composition according to claim 6 , wherein the object to be coated is an electronic substrate. A cured product of the light-moisture-curable resin composition according to any one of claims 1 to 7 . A resin-coated electronic substrate comprising an electronic substrate and a cured product according to claim 8 arranged on the electronic substrate.