JP7848880B2 - Active energy ray curable resin composition, cured product, and laminate - Google Patents

Description

This disclosure relates to active energy ray curable resin compositions, cured products, and laminates.

When using active energy ray-curable resin compositions in flat panel display applications, good antistatic properties are required to prevent problems caused by static electricity during display assembly and operation, and to achieve high-definition images.

Japanese Patent Publication No. 2019-112630

The problem that this invention aims to solve is to provide an active energy ray curable composition for producing cured products with good antistatic properties.

The inventors have found that the above problem can be solved by using a specific component.

This disclosure provides the following items:
(Item 1)
A resin composition that is curable by active energy rays,
The active energy ray curable resin composition comprises a quaternary ammonium salt-containing polymer and a phosphate ester and/or salt,
The anion of the salt contains a polyoxyalkylene structure.
When the active energy ray-curable resin composition contains a phosphate ester, the acid value of the active energy ray-curable resin composition is 400 mg KOH/g to 600 mg KOH/g.
Active energy ray curable resin composition.
(Item 2)
An active energy ray curable resin composition as described above, comprising urethane poly(meth)acrylate.
(Item 3)
A cured product of an active energy ray curable resin composition as described in any one of the above items.
(Item 4)
A laminate containing the cured material described in the above items.
(Item A1)
A resin composition that is curable by active energy rays,
The aforementioned active energy ray curable resin composition comprises a quaternary ammonium salt-containing polymer and a phosphate ester,
The active energy ray-curable resin composition has an acid value of 400 mg KOH/g to 600 mg KOH/g.
(Item A2)
The quaternary ammonium salt-containing polymer comprises constituent unit (1), constituent unit (2), and constituent unit (3).
The aforementioned constituent unit (1) is derived from a quaternary ammonium salt-containing monomer,
The aforementioned constituent unit (2) is derived from the following compound α,
A-B-(C) _n -D
(A represents a (meth)acryloyloxy group. B represents a single bond or an alkylene group. _C represents -O-C(=O) _{CH₂CH₂CH₂CH₂CH₂CH₂-} or an _{oxyalkylene group} . D represents a hydroxyl group, an alkoxy group, or an alkyl group. _n represents an integer of 1 or more.)
The aforementioned constituent unit (3) is derived from alkyl (meth)acrylate.
The active energy ray curable resin composition described in the above items.
(Item A3)
An active energy ray curable resin composition according to any one of the above items, wherein the non-volatile content mass ratio (phosphate ester/quaternary ammonium salt-containing polymer) is 0.1 to 0.7.
(Item A4)
An active energy ray curable resin composition according to any one of the above items, comprising (poly)pentaerythritol poly(meth)acrylate and/or urethane poly(meth)acrylate having (poly)pentaerythritol poly(meth)acrylate as a constituent unit.
(Item A5)
A cured product of an active energy ray curable resin composition as described in any one of the above items.
(Item A6)
A laminate containing the cured material described in the above items.
(Item B1)
A resin composition that is curable by active energy rays,
The active energy ray curable resin composition comprises a quaternary ammonium salt-containing polymer and a salt,
The anion of the salt contains a polyoxyalkylene structure.
Active energy ray curable resin composition.
(Item B2)
An active energy ray curable resin composition as described above, comprising urethane poly(meth)acrylate.
(Item B3)
A cured product of an active energy ray curable resin composition as described in any one of the above items.
(Item B4)
A laminate containing the cured material described in the above items.

In this disclosure, one or more of the features described above may be provided in combinations other than those explicitly stated.

By using the active energy ray curable composition of this disclosure, a cured product with good antistatic properties can be produced.

Throughout this disclosure, the ranges of numerical values such as physical properties and content may be set as appropriate (for example, by selecting from the values listed in each of the items below). Specifically, if the examples of numerical value α are A3, A2, and A1 (A3 > A2 > A1), the range of numerical value α may include, for example, A3 or less, A2 or less, less than A3, less than A2, A1 or more, A2 or more, greater than A1, greater than A2, A1 to A2 (A1 or more and A2 or less), A1 to A3, A2 to A3, A1 or more and less than A3, A1 or more and less than A2, A2 or more and less than A3, greater than A1 and less than A3, greater than A1 and A3 or less, greater than A1 and A2 or less, greater than A2 and A3 or less, etc.

The components, conditions, numerical values, etc., are not limited to those described in the specification, as long as the problems that this invention aims to solve are resolved.

"αβ amount (A/B)" means the amount of β (α) of A relative to B100α. α can be expressed as mass%, mole%, or parts by mass, for example. β amount can be expressed as content, amount used, etc. αβ amount can be expressed as mass%, content, etc.

The "γ ratio (A/B)" refers to the γ ratio calculated using the formula "A ÷ B". Examples of γ ratios include mass ratios and molar ratios.

"Non-volatile content" refers to the total mass of components other than organic solvents and water. In one embodiment, the non-volatile content of object A is defined as the total mass of components remaining when 1 g of object A is heated at 105°C and a constant weight is reached.

"(Meth)acrylic" means "at least one selected from the group consisting of acrylic and methacrylic." "(Meth)acrylate" means "at least one selected from the group consisting of acrylate and methacrylate." "(Meth)acryloyl" means "at least one selected from the group consisting of acryloyl and methacryloyl."

"C..." means "having... carbon atoms." For example, "C1-6 alkyl group" means an alkyl group with 1 to 6 carbon atoms. "C6 alkyl group" means an alkyl group with 6 carbon atoms.

[Activated energy ray curable resin composition: Composition]
This disclosure relates to an active energy ray curable resin composition,
The active energy ray curable resin composition comprises a quaternary ammonium salt-containing polymer and a phosphate ester and/or salt,
The anion of the salt contains a polyoxyalkylene structure.
When the active energy ray-curable resin composition contains a phosphate ester, the acid value of the active energy ray-curable resin composition is 400 mg KOH/g to 600 mg KOH/g.
This invention relates to active energy ray curable resin compositions.

<Quaternary ammonium salt-containing polymer: polymer>
Quaternary ammonium salt-containing polymers can be used alone or in combination of two or more types.

In one embodiment, the quaternary ammonium salt-containing polymer comprises constituent unit (1), constituent unit (2), and constituent unit (3),
The aforementioned constituent unit (1) is derived from a quaternary ammonium salt-containing monomer,
The aforementioned constituent unit (2) is derived from the following compound α,
A-B-(C) _n -D
(A represents a (meth)acryloyloxy group. B represents a single bond or an alkylene group. _C represents -O-C(=O) _{CH₂CH₂CH₂CH₂CH₂CH₂-} or an _{oxyalkylene group} . D represents a hydroxyl group, an alkoxy group, or an alkyl group. _n represents an integer of 1 or more.)
The aforementioned constituent unit (3) is derived from alkyl (meth)acrylate.

(Constituent unit (1))
Quaternary ammonium salt-containing monomers can be used alone or in combination of two or more.

Examples of quaternary ammonium salt-containing monomers include (meth)acrylates represented by the following formula.
[CH ₂ =C(R ¹ )-C(=O)-AB-N ⁺ (R ² )(R ³ )(R ⁴ )] _n・X ^n-
(In the formula, ^R1 represents H or _CH3 . ^R2 to ^R4 each independently represent a C1-4 alkyl group. A represents O or NH. B represents a C1-3 alkylene group. ^X- represents an anion. n represents an integer of 1 or more.)

Examples of C1-4 alkyl groups include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, and t-butyl group.

Examples of C1-3 alkylene groups include methylene, ethylene, propylene, and isopropylene groups.

Examples of X ^n- include halogen ions, sulfur-containing ions, and the like.

Examples of halogen ions include fluoride ions, chloride ions, bromide ions, and iodide ions.

Examples of sulfur-containing ions include sulfate ions, _sulfite ions, _{C₂H₅SO₄-} , _R₂S₁- ( ^OR₂S₂ ) _s - _OSO₃- ^{, etc. R₂S₁} represents an alkyl group or aryl group. ^R₂S₂ represents an alkylene group. s represents an integer greater than ^or equal to 1.

R ^S1 is preferably an alkyl group, more preferably a C1- to C4 alkyl group. R ^S2 is preferably a C2- to C3 alkylene group.

In one embodiment, X ^n- is preferably a chloride ion, R ^S1- (OR ^S2 ) _s ^- _OSO3- .

n can be, for example, 1, 2, etc. In one embodiment, n is preferably 1.

Examples of quaternary ammonium salt-containing monomers (excluding anions) include trimethyl-2-(meth)acryloyloxyethylammonium and (3-(meth)acryloylaminopropyl)trimethylammonium.

Examples of commercially available products (quaternary ammonium salt-containing monomers) include "Light Ester DQ-100" manufactured by Kyoeisha Chemical Co., Ltd., "DMAEA-Q" manufactured by Kojin Co., Ltd., and "Amino Ion RE3000MF" manufactured by Nippon Emulsifier Co., Ltd.

The mass percentage content (constituent unit (1) / total polymer constituent units) can be, for example, 70% by mass, 65% by mass, 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 35% by mass, etc. In one embodiment, the above content is preferably 25% by mass to 70% by mass, and more preferably 35% by mass to 60% by mass.

Examples of mol% content (constituent unit (1) / total polymer constituent units) include 84 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 21 mol%, 20 mol%, 15 mol%, 14 mol%, etc. In one embodiment, the above content is preferably 14 mol% to 84 mol%, and more preferably 21 mol% to 80 mol%.

(Constituent unit (2))
Compound α can be used alone or in combination of two or more compounds.

Compound α is represented by the following formula.
A-B-(C) _n -D
(A represents a (meth)acryloyloxy group. B represents a single bond or an alkylene group. _C represents -O-C(=O) _{CH₂CH₂CH₂CH₂CH₂CH₂-} or an _{oxyalkylene group} . D represents a hydroxyl group, an alkoxy group, or an alkyl group. _n represents an integer of 1 or more.)

Examples of compound α include lactone ring-opening polyadducts (C: -O-C _{( = O} ) _{CH2CH2CH2CH2CH2CH2-} ) and polyalkylene-containing products ₍ C: oxyalkylene group).

In compound α, the alkyl group can be, for example, a C1-C4 alkyl group.

In compound α, the alkoxy group can be, for example, a C1-C18 alkoxy group.

Examples of C1-18 alkoxy groups include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-octoxy group, 2-ethylhexylthoxy group, n-decatoxy group, 2-ethyloctoxy group, n-lauroxy group, n-stearoxy group, and the like.

<Lactone ring-opening polyadditive>
Lactone ring-opening polyadditions can be produced by ring-opening polyaddition using a hydroxyl group-containing vinyl monomer and a lactone.

Hydroxyl group-containing vinyl monomers can be used alone or in combination of two or more. Examples of hydroxyl group-containing vinyl monomers include hydroxyl group-containing (meth)acrylates and hydroxyl group-containing vinyl monomers.

Examples of hydroxyl group-containing (meth)acrylates include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, and hydroxyethyl (meth)acrylamide.

Examples of hydroxyl group-containing vinyl ethers include hydroxyethyl vinyl ether, hydroxybutyl vinyl ether, and hydroxydiethylene glycol vinyl ether.

Lactones can be used alone or in combination of two or more. Examples of lactones include β-propiolactone, γ-butyrolactone, δ-valerolactone, β-methyl-δ-valerolactone, and ε-caprolactone.

Examples of weight-average molecular weights (lactone ring-opening polyadducts) include 10,000, 9,000, 8,000, 7,000, 6,000, 5,000, 4,000, 3,999, 3,000, 2,000, and 1,000. In one embodiment, the above weight-average molecular weight is preferably 1,000 to 10,000, and more preferably 1,000 or more and less than 4,000.

The weight-average molecular weight (lactone ring-opening polyadditive) can be measured under the following conditions: Measuring instrument: Product name "HLC-8220GPC", manufactured by Tosoh Corporation Column: Product name "TSKgel SuperHZ-M", manufactured by Tosoh Corporation Developing solvent: Tetrahydrofuran Flow rate: 0.35 mL/min Sample concentration: 0.5%
Standard material: Polystyrene (Standard polystyrene kit PStQuick A, B, C, manufactured by Tosoh Corporation)

During ring-opening polyaddition, a catalyst may be optionally used. Examples of catalysts include mineral acids, alkali metals, alkyl metal compounds, metal alkoxides, and tin compounds.

Examples of mineral acids include sulfuric acid and phosphoric acid.

Examples of alkali metals include lithium, sodium, and potassium.

Examples of alkyl metal compounds include n-butyllithium, s-butyllithium, and t-butyllithium.

Examples of metal alkoxides include titanium tetrabutoxide.

Examples of tin compounds include dibutyltin dilaurate, dibutyltin dioctate, dibutyltin mercaptide, and tin octylate.

In one embodiment, the amount used (catalyst/hydroxyl group-containing vinyl monomer and lactone) is preferably 0.01 to 10 parts by mass.

<Polyalkylene-containing substances>
Examples of polyalkylene-containing materials include hydroxypolyalkylene glycol mono(meth)acrylate and alkoxypolyalkylene glycol mono(meth)acrylate.

Examples of hydroxypolyalkylene glycol mono(meth)acrylates include hydroxypolyethylene glycol mono(meth)acrylate and hydroxypolypropylene glycol mono(meth)acrylate.

Examples of alkoxypolyalkylene glycol mono(meth)acrylates include methoxypolyalkylene glycol mono(meth)acrylate, ethoxypolyalkylene glycol mono(meth)acrylate, propoxypolyalkylene glycol mono(meth)acrylate, butoxypolyalkylene glycol mono(meth)acrylate, alkoxypolyethylene glycol mono(meth)acrylate, alkoxypolypropylene glycol mono(meth)acrylate, methoxypolyethylene glycol mono(meth)acrylate, methoxypolypropylene glycol mono(meth)acrylate, ethoxypolyethylene glycol mono(meth)acrylate, ethoxypolypropylene glycol mono(meth)acrylate, propoxypolyethylene glycol mono(meth)acrylate, propoxypolypropylene glycol mono(meth)acrylate, butoxypolyethylene glycol mono(meth)acrylate, butoxypolypropylene glycol mono(meth)acrylate, and the like.

Examples of commercially available polyalkylene-containing products include Bremmer PME-100, PME-200, PME-400, PME-1000, PME-4000, 50POEP-800B, PLE-200, PLE-1300, PSE-1300 (all manufactured by NOF Corporation), Light Ester BC, 130MA, 041MA (manufactured by Kyoeisha Chemical Co., Ltd.), and others.

The mass percentage content (constituent unit (2) / total polymer constituent units) can be, for example, 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, etc. In one embodiment, the above content is preferably 25% by mass to 60% by mass, and more preferably 30% by mass to 55% by mass.

Examples of mol% content (constituent units (2) / total polymer constituent units) include 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 5 mol%, 2 mol%, 1 mol%, 0.5 mol%, etc. In one embodiment, the above content is preferably 0.5 mol% to 50 mol%, and more preferably 1 mol% to 40 mol%.

(Constituent unit (3))
Alkyl (meth)acrylates can be used alone or in combination of two or more types.

Examples of alkyl (meth)acrylates include linear alkyl (meth)acrylates, branched alkyl (meth)acrylates, and cycloalkyl (meth)acrylates.

Examples of linear alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-pentyl (meth)acrylate, and n-hexyl (meth)acrylate.

Examples of branched alkyl (meth)acrylates include isopropyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 1-methylbutyl (meth)acrylate, 2-methylbutyl (meth)acrylate, 3-methylbutyl (meth)acrylate, 1-ethylpropyl (meth)acrylate, 1,1-dimethylpropyl (meth)acrylate, 1,2-dimethylpropyl (meth)acrylate, and 2,2-dimethylpropyl (meth)acrylate.

Examples of cycloalkyl (meth)acrylates include cyclopropyl (meth)acrylate, cyclobutyl (meth)acrylate, cyclopentyl (meth)acrylate, and cyclohexyl (meth)acrylate.

In one embodiment, the alkyl (meth)acrylate is preferably a branched alkyl (meth)acrylate, and more preferably a C3-5 branched alkyl (meth)acrylate.

Examples of mass percent content (constituent unit (3) / total polymer constituent units) include 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 20% by mass, 15% by mass, 10% by mass, and 5% by mass. In one embodiment, the above content is preferably 5% by mass to 50% by mass.

Examples of mol% content (constituent unit (3) / total polymer constituent units) include 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, etc. In one embodiment, the above content is preferably 10 mol% to 80 mol%.

(Component unit (4): Other component units)
The above polymer may optionally contain constituent unit (4). "Constituent unit (4)" means "constituent unit derived from other monomers.""Othermonomers" means monomers other than quaternary ammonium salt-containing monomers, compound α, and alkyl (meth)acrylates. Other monomers may be used alone or in combination of two or more.

Other monomers include, for example, vinyl monomers containing aromatic ring structures.

Examples of vinyl monomers containing aromatic ring structures include styrene, α-methylstyrene, and 4-methylstyrene.

Examples of mass percent content (constituent units (4) / total polymer constituent units) include less than 1 mass percent, less than 0.1 mass percent, less than 0.01 mass percent, 0 mass percent, etc.

Examples of mol% content (constituent units (4) / total polymer constituent units) include less than 1 mol%, less than 0.1 mol%, less than 0.01 mol%, 0 mol%, etc.

Examples of mass percentage content (constituent unit (4) / any one of constituent units (1) to (3)) include less than 1 mass%, less than 0.1 mass%, less than 0.01 mass%, 0 mass%, etc.

The molar percentage content (constituent unit (4) / any one of constituent units (1) to (3)) can be, for example, less than 1 mol%, less than 0.1 mol%, less than 0.01 mol%, 0 mol%, etc.

<Physical Properties (Polymers)>
Examples of weight-average molecular weight (polymer) (Mw) include 500,000, 450,000, 400,000, 350,000, 300,000, 250,000, 200,000, and 180,000. In one embodiment, the weight-average molecular weight is preferably between 180,000 and 500,000.

Examples of number-average molecular weights (polymer) (Mn) include 200,000, 175,000, 150,000, 125,000, 100,000, and 50,000. In one embodiment, the above number-average molecular weight is preferably 50,000 to 200,000.

Examples of molecular weight distributions (polymer) (Mw/Mn) include 5.0, 4.9, 4.5, 4.0, 3.5, 3.0, 2.5, 2.0, 1.9, 1.8, etc. In one embodiment, the above molecular weight distribution is preferably 1.8 to 5.0.

The weight-average molecular weight and number-average molecular weight (polymer) can be measured under the following conditions.
Measuring instrument: Product name "HLC-8320GPC", manufactured by Tosoh Corporation. Column: Product names "TSKgel G6000PW _XL -CP", "TSKgel G3000PW _XL -CP", manufactured by Tosoh Corporation. Developing solvent: 0.1 M _NaNO3 and 0.1 M aqueous acetic acid solution. Flow rate: 0.5 mL/min.
Sample concentration: 0.5 g/L
Standard substance: Polyethylene oxide (TSKgel Standard Polyethylene Oxide SE-Kit, manufactured by Tosoh Corporation)

<Manufacturing Method (Polymer)>
Examples of manufacturing methods (polymers) include radical polymerization.

Radical polymerization initiators can be used alone or in combination of two or more. Examples of radical polymerization initiators include inorganic peroxides, organic peroxides, and azo compounds.

Examples of inorganic peroxides include hydrogen peroxide, ammonium persulfate, and potassium persulfate.

Examples of organic peroxides include benzoyl peroxide, dicumyl peroxide, and lauryl peroxide.

Examples of azo compounds include 2,2'-azobisisobutyronitrile and dimethyl-2,2'-azobisisobutyrate.

The amount used (radical polymerization initiator/total monomer component) is preferably about 0.01 to 10 parts by mass.

During polymer production, chain transfer agents may be used as optional. These chain transfer agents may be used alone or in combination of two or more. Examples of chain transfer agents include lauryl mercaptan, dodecyl mercaptan, 2-mercaptobenzothiazole, bromotrichloromethane, and α-methylstyrene dimer.

The amount used (chain transfer agent/total monomer components) is preferably about 0 to 10 parts by mass.

In solution polymerization, the reaction solvent can be, for example, the following organic solvents.

The reaction time is preferably 2 to 12 hours.

The polymerization temperature is preferably 70 to 130°C.

The mass % content (quaternary ammonium salt-containing polymer/non-volatile content of the active energy ray-curable resin composition) can be, for example, 20% by mass, 19% by mass, 17% by mass, 15% by mass, 13% by mass, 11% by mass, 10% by mass, 9% by mass, 7% by mass, 5% by mass, 3% by mass, etc. In one embodiment, the above content is preferably 3% by mass to 20% by mass.

<Phosphate esters>
In one embodiment, the above composition may optionally contain a phosphate ester. The phosphate ester may be used alone or in combination of two or more.

In one embodiment, the phosphate ester is represented by the following formula.
(R ^P ) _m -P(=O)(OX) _3-m
(In the formula, m represents 1, 2, or 3. X represents a hydrogen atom, a metal atom, or an ammonium ion. ^RP represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a polyalkylene alkyl group.)

Examples of substituents include (meth)acryloyloxy groups and alkoxy groups.

Examples of metal atoms include alkali metal atoms and alkaline earth metal atoms.

Examples of phosphate monoesters include (meth)acryloyloxyalkyl phosphate and (poly)alkyleneoxyalkyl phosphate.

Examples of (meth)acryloyloxyalkyl phosphates include (meth)acryloyloxyethyl phosphate, (meth)acryloyloxypropyl phosphate, and (meth)acryloyloxybutyl phosphate.

Examples of (poly)alkylene oxyalkyl phosphates include ethyleneoxybutyl phosphate and decyl (ethyleneoxydecyl) phosphate.

Examples of commercially available phosphate esters include Light Ester P-1M, P-2M (Kyoeisha Chemical Co., Ltd.), MP-4, MP-8 (manufactured by Daihachi Chemical Co., Ltd.), and others.

Examples of acid values (phosphate esters) include 600 mg KOH/g, 590 mg KOH/g, 580 mg KOH/g, 570 mg KOH/g, 560 mg KOH/g, 550 mg KOH/g, 540 mg KOH/g, 530 mg KOH/g, 520 mg KOH/g, 510 mg KOH/g, 500 mg KOH/g, 490 mg KOH/g, 480 mg KOH/g, 470 mg KOH/g, 460 mg KOH/g, 450 mg KOH/g, 440 mg KOH/g, 430 mg KOH/g, 420 mg KOH/g, 410 mg KOH/g, 400 mg KOH/g, and the like. In one embodiment, the above acid values are preferably between 400 mg KOH/g and 600 mg KOH/g.

Examples of mass percent content (phosphate ester/non-volatile content of active energy ray curable resin composition) include 12% by mass, 10% by mass, 9% by mass, 7% by mass, 5% by mass, 3% by mass, 1% by mass, 0.9% by mass, 0.5% by mass, 0.3% by mass, 0% by mass, etc. In one embodiment, the above content is preferably 0% by mass to 12% by mass, and more preferably 0.3% by mass to 12% by mass.

Examples of non-volatile content mass ratios (phosphate ester/quaternary ammonium salt-containing polymer) include 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, 0.1, and 0. In one embodiment, the non-volatile content mass ratio (phosphate ester/quaternary ammonium salt-containing polymer) is preferably 0 to 0.7, more preferably 0.1 to 0.7, and even more preferably 0.1 to 0.6. Reasons for further preference include, for example, improved haze.

<Salt: Salt containing polyalkylene structure>
In one embodiment, the above composition may optionally include salts. The salts may be used alone or in combination of two or more.

A "salt" refers to a compound consisting only of anions and cations.

(Anion)
The anion contains a polyoxyalkylene structure.

A "polyoxyalkylene structure" refers to a structure in which two or more oxyalkylene structures (-O-C _{nH 2n-} ) are consecutive.

Examples of polyoxyalkylene structures include polyoxyethylene structures and polyoxypropylene structures.

In one embodiment, the polyoxyalkylene modification number is preferably 2 to 25, and more preferably 5 to 20.

Examples of anions include sulfate ions containing a polyoxyalkylene structure and phosphate ions containing a polyoxyalkylene structure.

In one embodiment, the anion is represented by the following formula.
R ^a1 - (OR ^a2 ) _n -OXO ₃ ^-
(R ^a1 represents an alkyl group (e.g., C1-6 alkyl group) or an unsaturated group-containing group. R ^a2 represents an alkylene group (e.g., ethylene group, propylene group). n represents an integer of 2 or more. X represents S or P.)

Examples of unsaturated groups include the following:
(R ^b1 represents an alkyl group. Y represents a single bond or an oxygen atom. ^{R b2} to R ^b4 each independently represent a hydrogen atom or a methyl group.)
(R ^c1 to R ^c3 each independently represent a hydrogen atom or a methyl group. ^{R c4} to R ^c7 each independently represent a hydrogen atom or
(This represents...)

(cation)
Examples of cations include ammonium ions ( _NH₄ ⁺ ), quaternary ammonium salt-containing monomers, and metal ions.

Examples of quaternary ammonium salt-containing monomers include the monomers mentioned above.

Examples of metal ions include alkali metal ions.

Examples of alkali metal ions include lithium ions, sodium ions, and potassium ions.

Salts (anions-cations) include, for example, alkyl polyethylene sulfate ion-ammonium ion, alkyl polyethylene sulfate ion-trimethyl-2-(meth)acryloyloxyethylammonium, alkyl polyethylene sulfate ion-(3-(meth)acryloylaminopropyl)trimethylammonium, alkyl polyethylene sulfate ion-sodium ion, alkyl polyethylene phosphate ion-ammonium ion, alkyl polyethylene phosphate ion-trimethyl-2-(meth)acryloyloxyethylammonium, alkyl polyethylene phosphate ion-(3-(meth)acryloylaminopropyl)trimethylammonium, alkyl polyethylene phosphate ion-sodium ion,
(In the formula, n1 to n5 each independently represent an integer greater than or equal to 2 (for example, 2 to 25, 5 to 20, etc.).)
These are some examples.

Examples of commercially available products (polyoxyalkylene structure-containing sulfates) include Aminoion RE3000MF (manufactured by Nippon Emulsifier Co., Ltd.), Adeka Soap SR-10, SR-20 (manufactured by ADEKA Corporation), and Aqualon KH-05, KH-10, AR-10, AR-20 (manufactured by Daiichi Kogyo Co., Ltd.).

Examples of commercially available products (phosphates containing polyoxyalkylene structures) include Disparon PW-36 (manufactured by Kusumoto Kasei Co., Ltd.).

Examples of mass percent content (salt/non-volatile content of active energy ray curable resin composition) include 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 20% by mass, 15% by mass, 10% by mass, 5% by mass, 2% by mass, 1% by mass, and 0% by mass. In one embodiment, the above content is preferably 0% by mass to 50% by mass, and more preferably 1% by mass to 50% by mass.

The parts by mass content (salt/quaternary ammonium salt-containing polymer) can be, for example, 1667 parts by mass, 1500 parts by mass, 1000 parts by mass, 500 parts by mass, 200 parts by mass, 100 parts by mass, 75 parts by mass, 50 parts by mass, 25 parts by mass, 20 parts by mass, 15 parts by mass, 10 parts by mass, 5 parts by mass, 0 parts by mass, etc. In one embodiment, the above content is preferably 0 to 1667 parts by mass, more preferably 5 to 1667 parts by mass, even more preferably 5 to 75 parts by mass, and particularly preferably 5 to 50 parts by mass. Reasons for further preference and particular preference include, for example, improvement of haze.

<Poly(meth)acrylate>
In one embodiment, the composition may optionally include poly(meth)acrylate. Poly(meth)acrylate may be used alone or in combination of two or more types.

"Poly(meth)acrylate" refers to a compound having two or more (meth)acryloyl groups.

Examples of poly(meth)acrylates include (poly)pentaerythritol poly(meth)acrylate and urethane poly(meth)acrylate.

((Poly)pentaerythritol poly(meth)acrylate)
Examples of (poly)pentaerythritol poly(meth)acrylate include pentaerythritol poly(meth)acrylate and polypentaerythritol poly(meth)acrylate.

Examples of pentaerythritol poly(meth)acrylate include pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate.

Examples of polypentaerythritol poly(meth)acrylate include dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol di(meth)acrylate, tripentaerythritol tri(meth)acrylate, tripentaerythritol tetra(meth)acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, and tripentaerythritol octa(meth)acrylate.

(Urethane poly(meth)acrylate)
Examples of urethane poly(meth)acrylates include reaction products of compounds containing hydroxyl group-containing poly(meth)acrylates and polyisocyanates.

<Hydroxygroup-containing poly(meth)acrylate>
Examples of hydroxyl group-containing poly(meth)acrylates include (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, and (poly)glycerin poly(meth)acrylate.

Polyisocyanates can be used alone or in combination of two or more types.

<Polyisocyanate>
"Polyisocyanate" refers to a compound having two or more isocyanate groups (-N=C=O).

Examples of polyisocyanates include linear aliphatic polyisocyanates, branched aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and their biuret, isocyanurate, allophanate, and adduct derivatives.

Examples of linear aliphatic polyisocyanates include methylene diisocyanate, dimethyl diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, and decamethylene diisocyanate.

Examples of branched aliphatic polyisocyanates include diethylpentylene diisocyanate, trimethylbutylene diisocyanate, trimethylpentylene diisocyanate, and trimethylhexamethylene diisocyanate.

Examples of alicyclic polyisocyanates include monocyclic alicyclic polyisocyanates, crosslinked cyclic alicyclic polyisocyanates, and condensed cyclic alicyclic polyisocyanates.

Examples of monocyclic alicyclic polyisocyanates include hydrogenated xylene diisocyanate, isophorone diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, cycloheptylene diisocyanate, cyclodecylene diisocyanate, 3,5,5-trimethylcyclohexylene diisocyanate, and dicyclohexylmethane diisocyanate.

Examples of cross-linked alicyclic polyisocyanates include tricyclodecile diisocyanate, adamantane diisocyanate, and norbornene diisocyanate.

Examples of condensed alicyclic polyisocyanates include bicyclodecile diisocyanate.

Examples of aromatic polyisocyanates include monocyclic aromatic polyisocyanates and fused-ring aromatic polyisocyanates.

Examples of monocyclic aromatic polyisocyanates include dialkyldiphenylmethane diisocyanates such as 4,4'-diphenyldimethylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanates such as 4,4'-diphenyltetramethylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-dibenzyli isocyanate, 1,3-phenylenedi isocyanate, 1,4-phenylenedi isocyanate, tolylene diisocyanate, xylylene diisocyanate, and m-tetramethylxylylene diisocyanate.

Examples of condensed ring aromatic polyisocyanates include 1,5-naphthylene diisocyanate.

In one embodiment, the urethane poly(meth)acrylate preferably includes a urethane poly(meth)acrylate having (poly)pentaerythritol poly(meth)acrylate as a constituent unit.

Examples of the mass % content (non-volatile content of poly(meth)acrylate/active energy ray curable resin composition) include 97% by mass, 95% by mass, 90% by mass, 85% by mass, 80% by mass, 75% by mass, 70% by mass, 65% by mass, 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 20% by mass, 15% by mass, 10% by mass, 5% by mass, 1% by mass, 0% by mass, etc. In one embodiment, the above content is preferably 0% by mass to 97% by mass.

<Photopolymerization initiator>
In one embodiment, the active energy ray curable composition may optionally include a photopolymerization initiator. The photopolymerization initiator may be used alone or in combination of two or more.

Examples of photopolymerization initiators include α-hydroxydimethylacetophenone group-containing photopolymerization initiators, α-hydroxycycloalkylphenone, α-aminoalkylphenone, benzyldimethylketal, unsubstituted or substituted alkylphenone, unsubstituted or substituted benzyl, unsubstituted or substituted benzophenone, acylphosphine oxide, substituted thioxanthone, oxime ester, and the like.

Examples of α-hydroxydimethylacetophenone group-containing photopolymerization initiators include 2-hydroxy-2-methyl-1-phenylpropanone, 1-[4-(2-hydroxyethoxyl)-phenyl]-2-hydroxymethylpropanone, and 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one.

Examples of α-hydroxycycloalkylphenones include 1-hydroxycyclohexylphenyl ketone.

Examples of α-aminoalkylphenones include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one.

Examples of benzyldimethyl ketals include 2,2-dimethoxy-1,2-diphenylethane-1-one.

Examples of unsubstituted or substituted alkylphenones include benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-phenyl-2-(p-toluenesulfonyloxy)acetophenone, benzoin, 2-benzyl-2-(dimethylamino)-4'-morpholinobylophenone, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, 2-isonitrosopropiophenone, and 2,2-dimethoxy-1,2-diphenylethane-1-one.

Examples of unsubstituted or substituted benzyls include benzyl, p-anisyl, and the like.

Examples of unsubstituted or substituted benzophenones include benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 1,4-dibenzoylbenzene, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid, and methyl 2-benzoylbenzoate.

Examples of acylphosphine oxides include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

Examples of substituted thioxanthones include 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

Oxime esters include, for example, 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyloxime)] (i.e., 2-((benzoyloxy)imino)-1-(4-(phenylthio)phenyl)octan-1-one);
Examples include ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(O-acetyloxime) (i.e., 1-(((1-(9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl)ethylidene)amino)oxy)ethan-1-one).

When using electron beam curing, a photopolymerization initiator is not necessary.

The mass % content (photopolymerization initiator/non-volatile content of the active energy ray curable resin composition) can be, for example, 15% by mass, 13% by mass, 11% by mass, 10% by mass, 9% by mass, 7% by mass, 5% by mass, 3% by mass, 1% by mass, etc. In one embodiment, the above content is preferably 0% by mass to 15% by mass, and more preferably 1% by mass to 15% by mass.

<Leveling agent>
In one embodiment, the active energy ray curable composition may optionally include a leveling agent. The leveling agent may be used alone or in combination of two or more.

Leveling agents include silicone leveling agents and fluorine leveling agents.

The mass percentage content (leveling agent/non-volatile content of the active energy ray curable resin composition) can be, for example, 10% by mass, 9% by mass, 7% by mass, 5% by mass, 4% by mass, 2% by mass, 1% by mass, 0% by mass, etc. In one embodiment, the above content is preferably 0% by mass to 10% by mass.

<Soluble Organic Solvents>
In one embodiment, the active energy ray curable composition may optionally contain an organic solvent. The organic solvent may be used alone or in combination of two or more.

Examples of organic solvents include ketone solvents, aromatic solvents, alcohol solvents, glycol solvents, glycol ether solvents, ester solvents, petroleum-based solvents, haloalkane solvents, and amide solvents.

Examples of ketone solvents include methyl ethyl ketone, acetylacetone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone.

Examples of aromatic solvents include toluene and xylene.

Examples of alcoholic solvents include methanol, ethanol, n-propanol, isopropanol, and butanol.

Examples of glycol solvents include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol.

Examples of glycol ether solvents include ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, and ethylene glycol mono-t-butyl ether.

Examples of ester solvents include ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate.

Examples of petroleum-based solvents include Solvesso #100 (manufactured by Exxon Technologies) and Solvesso #150 (manufactured by Exxon Technologies).

Examples of haloalkane solvents include chloroform.

Examples of amide solvents include dimethylformamide.

The mass content (organic solvent/non-volatile content of the active energy ray curable resin composition) can be, for example, 1900 parts by mass, 1750 parts by mass, 1500 parts by mass, 1250 parts by mass, 1000 parts by mass, 500 parts by mass, 100 parts by mass, 75 parts by mass, 50 parts by mass, 25 parts by mass, 10 parts by mass, 0 parts by mass, etc. In one embodiment, the above content is preferably 0 to 1900 parts by mass, and more preferably 10 to 1000 parts by mass.

<Additives>
The active energy ray curable resin composition may optionally contain agents (additives) other than "quaternary ammonium salt-containing polymers, phosphate esters, (poly)(meth)acrylates, photopolymerization initiators, leveling agents, and organic solvents."

Examples of additives include antioxidants, UV absorbers, light stabilizers, defoamers, surface modifiers, antifouling agents, pigments, metal oxide particle dispersions, organic particle dispersions, and the like.

In one embodiment, the mass % content (additive/active energy ray curable resin composition) may be, for example, less than 10% by mass, less than 5% by mass, less than 1% by mass, less than 0.1% by mass, less than 0.01% by mass, or 0% by mass.

In one embodiment, the parts by mass content (additive/one of quaternary ammonium salt-containing polymer, phosphate ester, (poly)(meth)acrylate, photopolymerization initiator, or organic solvent) may be, for example, less than 5% by mass, less than 1 part by mass, less than 0.1 parts by mass, less than 0.01 parts by mass, or 0 parts by mass.

Active energy ray curable resin compositions can be produced by dispersing and mixing a quaternary ammonium salt-containing polymer and a phosphate ester, along with (poly)(meth)acrylate, a photopolymerization initiator, a leveling agent, an organic solvent, and additives as needed.

Dispersion and mixing means include, for example, emulsifying dispersers and ultrasonic dispersers.

The acid values (of the active energy ray-curable resin composition) are, for example, 600 mg KOH/g, 590 mg KOH/g, 580 mg KOH/g, 570 mg KOH/g, 560 mg KOH/g, 550 mg KOH/g, 540 mg KOH/g, 530 mg KOH/g, 520 mg KOH/g, 510 mg KOH/g, 500 mg KOH/g, 490 mg KOH/g, 480 mg Examples include gKOH/g, 470mgKOH/g, 460mgKOH/g, 450mgKOH/g, 440mgKOH/g, 430mgKOH/g, 420mgKOH/g, 410mgKOH/g, 400mgKOH/g, 200mgKOH/g, 100mgKOH/g, 50mgKOH/g, 25mgKOH/g, 10mgKOH/g, 0mgKOH/g, etc. In one embodiment, the above acid value is preferably 0mgKOH/g to 600mgKOH/g, and more preferably 400mgKOH/g to 600mgKOH/g.

The acid value can be measured under the following conditions. These conditions are based on JIS K-0070.
Reagent A: 0.5 mol/ ^dm³ potassium hydroxide ethanol solution. Reagent B: Toluene ethanol solution (volume ratio: toluene/ethanol = 1/1). Immediately before use, neutralize with Reagent A using phenolphthalein indicator. (1) Weigh 1 g of the sample, free from inorganic acid contamination, into a 300 mL Erlenmeyer flask.
(2) Add 100 mL of reagent B and a few drops of phenolphthalein indicator to the Erlenmeyer flask and shake well until the sample is completely dissolved. If the sample is solid, dissolve it by heating it on a water bath.
(3) The sample solution at room temperature is titrated with reagent A, and the endpoint of neutralization is determined when the phenolphthalein indicator remains faintly pink for 30 seconds.
(4) The acid value is calculated based on the following formula.
Acid value = (28.05 × A × f) / S
A: Titration volume of reagent A (mL)
f: Factor of reagent A S: Sample volume (g)
(5) If the reagent is dark in color, add 20 mL of saturated saline solution in (2), and in (3), the endpoint is reached when the color of the saline solution layer does not disappear after 30 seconds.

When the above composition contains a phosphate ester, the cured product of the composition also exhibits good transmittance. Furthermore, in phosphate ester-containing compositions, highly polar resins (such as urethane (meth)acrylate) may be used.

When the above composition contains a salt, the cured product of the composition exhibits good surface properties and good liquid compatibility. Furthermore, a low-polarity solvent (such as methyl isobutyl ketone) may be used in the salt-containing composition.

Examples of applications (active energy ray curable compositions) include antistatic agents, coating agents, and the like.

[Cured product]
This disclosure relates to a cured product of the above-mentioned active energy ray curable resin composition.

Examples of curing conditions include the following:

[Laminates]
This disclosure relates to a laminate including the cured product described above.

The above-mentioned laminates are manufactured by various known methods. In one embodiment, the method for manufacturing the laminate includes a step of coating the above-mentioned composition onto at least one side of a substrate (coating step), and a step of forming a cured layer by irradiating with active energy rays (active energy ray curing step).

Examples of substrates include polycarbonate film, acrylic film (such as polymethyl methacrylate film), polystyrene film, polyester film, polyolefin film, epoxy resin film, melamine resin film, triacetylcellulose film, ABS film, AS film, norbornene-based resin film, cyclic olefin film, and polyvinyl alcohol film.

In one embodiment, the thickness (substrate) is preferably 10 μm to 2000 μm.

In one embodiment, the thickness (cured layer) is preferably 0.1 μm to 20 μm.

(Coating process)
Coating methods include, for example, bar coating, wire bar coating, Meyer bar coating, air knife coating, gravure coating, reverse gravure coating, flow coating, offset printing, flexographic printing, and screen printing.

(Activated energy ray curing process)
Examples of active energy rays include ultraviolet rays and electron beams.

Examples of ultraviolet light sources include xenon lamps, high-pressure mercury lamps, and metal halide lamps.

When using a high-pressure mercury lamp, the curing conditions are preferably as follows:
Lamp output: 25W/cm to 160W/cm
UV illuminance: 10mW/cm ² ~800mW/cm ²
Cumulative light intensity: 25 mJ/ ^cm² to 2000 mJ/ ^cm²
Conveying speed: 1 m/min to 50 m/min

When using an electron beam, the curing conditions are preferably as follows:
Acceleration voltage: 10kV to 300kV
Conveying speed: 5 m/min to 50 m/min

The present invention will be specifically described below through examples and comparative examples. However, the above description and the following examples are not intended to limit the present invention. The present invention is limited only to the claims. Unless otherwise specified below, numerical values such as parts and percentages are based on mass.

Synthesis Example 1
In a reaction apparatus equipped with a stirrer and a condenser, 130 parts of hydroxyethyl methacrylate, 1140 parts of ε-caprolactone, and 1.3 parts of tin octylate were added, the temperature was raised to 150°C, and after being kept warm for 6 hours, the mixture was cooled to obtain a ring-opening polyaddition of a hydroxyl group-containing vinyl monomer and a lactone, with a weight-average molecular weight of approximately 2750.

The weight-average molecular weight of the above ring-opening polyadditive was determined using a commercially available molecular weight analyzer (main unit product name "HLC-8220GPC", manufactured by Tosoh Corporation; column product name "TSKgel SuperHZ-M", manufactured by Tosoh Corporation) with the following conditions: developing solvent: tetrahydrofuran, flow rate: 0.35 mL/min, sample concentration: 0.5%.
Standard material: Polystyrene (Standard polystyrene kit PStQuick A, B, C, manufactured by Tosoh Corporation)
These values were obtained by taking measurements under the following conditions.

Production Example 1: Quaternary Ammonium Salt-Containing Polymer In the same reaction apparatus as in Synthesis Example 1, 100 parts of methacryloyloxyethyltrimethylammonium chloride (DMC) (hereinafter referred to as component (a1-1)), 80 parts of component (a2-1), 20 parts of tert-butyl methacrylate (tBMA) (hereinafter referred to as component (a3-1)), and 800 parts of propylene glycol monomethyl ether (hereinafter referred to as PGM) were added, and the temperature was raised to 80°C. Then, 8 parts of 2,2'-azobis(methylbutyronitrile) (hereinafter referred to as AMBN) and 32 parts of PGM were added, and the polymerization reaction was started. After being kept warm at 85°C for 6 hours, the mixture was cooled to obtain a solution of quaternary ammonium salt-containing polymer (non-volatile content 20%).

Manufacturing Example 2
A solution of a quaternary ammonium salt-containing polymer (20% non-volatile content) was obtained by the same procedure as in Production Example 1, except that component (a2-1) was replaced with Bremmer 50POEP-800B (manufactured by NOF Corporation).

Example 1-1 Active Energy Ray Curable Resin Composition Five parts of the polymer from Production Example 1, 0.5 parts of 2-methacryloyloxyethyl phosphate (manufactured by Kyoeisha Chemical Co., Ltd., trade name "Light Ester P-1M"), 89.5 parts of a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (manufactured by Shin Nakamura Chemical Industry Co., Ltd., trade name "NK Ester A-9550W"), and five parts of a photopolymerization initiator (manufactured by IGM Resins, trade name "Omnirad 184") were mixed in proportion to their non-volatile content. Furthermore, 50.0 parts of methyl ethyl ketone and 50.0 parts of PGM were added as organic solvents to produce an active energy ray curable resin composition.

Unless otherwise specified, the following examples were carried out in the same manner as in Example 1-1, except for the modifications shown in the table.

<Explanation of Abbreviations>
P-1M: 2-methacryloyloxyethyl phosphate, manufactured by Kyoeisha Chemical Co., Ltd. Product name: "Light Ester P-1M"
P-2M: Di(2-methacryloyloxyethyl) phosphate, manufactured by Kyoeisha Chemical Co., Ltd., product name "Light Ester P-2M"

9550W: A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, manufactured by Shin Nakamura Chemical Industry Co., Ltd., product name "NK Ester A-9550W"
A-TMM-3: Pentaerythritol triacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd., product name "A-TMM-3"
V#802: Tripentaerythritol poly(meth)acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd., product name "Viscoat #802"
UA: Urethane acrylate (a reaction product of isophorone diisocyanate and pentaerythritol triacrylate)

Acid value The acid value was measured under the following conditions.
Reagent A: 0.5 mol/ ^dm³ potassium hydroxide ethanol solution. Reagent B: toluene ethanol solution (volume ratio: toluene/ethanol = 1/1). Immediately before use, the reagents were neutralized with Reagent A using phenolphthalein indicator.
(1) Weigh 1 g of the sample, free from inorganic acid contamination, into a 300 mL Erlenmeyer flask.
(2) Add 100 mL of reagent B and a few drops of phenolphthalein indicator to the Erlenmeyer flask and shake well until the sample is completely dissolved.
(3) The sample solution at room temperature was titrated with reagent A, and the endpoint of neutralization was defined as the point at which the phenolphthalein indicator remained faintly pink for 30 seconds.
(4) The acid value was calculated based on the following formula.
Acid value = (28.05 × A × f) / S
A: Titration volume of reagent A (mL)
f: Factor of reagent A S: Sample volume (g)

Laminate Manufacturing: Each active energy ray-curable resin composition was applied to a triacetylcellulose film (FT TD60UL, manufactured by Fujifilm Corporation, film thickness: 60 μm) using a #11 bar coater to a cured layer thickness of 5 μm, and dried at 80°C for 1 minute. Then, a UV curing device (product name: UBT-080-7A/BM, manufactured by Multiply Co., Ltd., high-pressure mercury lamp 600 mJ/ ^cm² ) was used to obtain a laminate containing the cured material.

Surface Resistance: The surface resistance of the laminate immediately after manufacturing was measured using a commercially available resistivity meter (Mitsubishi Chemical Corporation, product name "Highresta MCP-HT-450") in accordance with JIS K 6911, at an applied voltage of 500V.
"OVER" means the measurement range has been exceeded.
In Comparative Examples 1-3, precipitates formed in the active energy ray curable compositions. Therefore, Comparative Examples 1-3 could not be evaluated.

Evaluation Example: Transmittance In accordance with the JIS K 7361-1 (1997) standard, the total light transmittance of the laminate was measured using a haze meter (product name "HZ-V3", manufactured by Suga Test Instruments Co., Ltd.).
If the transmittance is low, the coating is cloudy or discolored.

Evaluation example: HAZE
In accordance with JIS K 7361-1 (1997), the haze of the laminate was measured using a haze meter (product name "HZ-V3", manufactured by Suga Test Instruments Co., Ltd.).

Example 2-1 Active Energy Ray Curable Resin Composition 25 parts of the polymer from Production Example 1 and 1 part of salt (amino ion RE3000MF, manufactured by Nippon Emulsifier Co., Ltd.) were heated at 60°C for 1 hour, and then mixed in a shaker to obtain a polymer composition.
Next, 5 parts of a photopolymerization initiator (Omnirad 2959, manufactured by IGM Resins B.V.), the above polymer composition, 70.5 parts of propylene glycol monomethyl ether, and 215.5 parts of methyl isobutyl ketone were mixed in a shaker.
Then, 125 parts of poly(meth)acrylate A and 1.5 parts of a leveling agent (Futergent 602A) were added and mixed in a shaker to produce an active energy ray curable resin composition.

Unless otherwise specified, the following examples were carried out in the same manner as in Example 2-1, except for the modifications shown in the table.

Laminate Manufacturing: An active energy ray-curable resin composition was applied to a polyethylene terephthalate film (Lumirror 100, manufactured by Toray Industries, Inc., film thickness: 100 μm) using a #11 bar coater to a cured layer thickness of 5 μm, and dried at 80°C for 1 minute. Then, a UV curing device (product name: UBT-080-7A/BM, manufactured by Multiply Co., Ltd., high-pressure mercury lamp 200 mJ/ ^cm² ) was used to obtain a laminate containing the cured material.

Liquid compatibility was evaluated according to the following criteria. For cases where liquid compatibility was marked as "×", other evaluations were not possible.
○...It completely dissolved.
×...Partially dissolved or not dissolved at all

Surface Resistance: The surface resistance of the laminate immediately after manufacturing was measured using a commercially available resistivity meter (Mitsubishi Chemical Corporation, product name "Highresta MCP-HT-450") in accordance with JIS K 6911, at an applied voltage of 500V.

The ratio of salt to quaternary ammonium salt-containing polymer was calculated based on the following formula.
Salt/quaternary ammonium salt-containing polymer ratio = [(A × a) / (B × b)] × 100
A: Salt blending ratio a: Non-volatile content of salt B: Blending ratio of quaternary ammonium salt-containing polymer b: Non-volatile content of quaternary ammonium salt-containing polymer

<Explanation of Abbreviations>
Manufacturing example 1: Non-volatile content 20%
1SX-1055F: Quaternary ammonium salt-containing polymer, 40% non-volatile content, manufactured by Taisei Fine Chemical Co., Ltd.

RE3000MF: Aminoion RE3000MF (polyoxyalkylene structure-containing sulfate, 50% non-volatile content, manufactured by Nippon Emulsifier Co., Ltd.)
SR-20: ADEKA Soap SR-20 (Polyoxyalkylene structure-containing sulfate, 100% non-volatile content, manufactured by ADEKA Corporation)
KH-10: Aqualon KH-10 (polyoxyalkylene structure-containing sulfate, 100% non-volatile content, manufactured by Daiichi Kogyo Co., Ltd.)
PW-36: Disparon PW-36 (polyoxyalkylene structure-containing phosphate, 50% non-volatile content, manufactured by Kusumoto Kasei Co., Ltd.)

Fatty acid amide S: Stearic acid amide, 100% non-volatile content, manufactured by Kao Chemical Co., Ltd. P-1M: Light ester P-1M, 2-methacryloyloxyethyl phosphate, 100% non-volatile content, manufactured by Kyoeisha Chemical Co., Ltd.

Poly(meth)acrylate A: Reaction product of biuret form of hexamethylene diisocyanate and pentaerythritol triacrylate (urethane acrylate), non-volatile content 80%
Poly(meth)acrylate B: Reaction product of hexamethylene diisocyanate nurate and pentaerythritol triacrylate (urethane acrylate), non-volatile content 80%
Poly(meth)acrylate C: Product name "SC-2152", reaction product of hexamethylene diisocyanate nurate and dipentaerythritol pentaacrylate (urethane acrylate), manufactured by MIWON, 100% non-volatile content.

Omnirad 2959, manufactured by IGM Resins B.V., 100% non-volatile content.

FT602A: Futergent 602A, a fluorine-based leveling agent having a radical polymerizable group and a branched fluoroaliphatic hydrocarbon group, manufactured by Neos Co., Ltd.

MIBK: Methyl isobutyl keto PGME: Propylene glycol monomethyl ether

Evaluation Example: Surfaceness Evaluated according to the following criteria.
○...Transparent and smooth.
×...Transparent but uneven or opaque.

Evaluation example: HAZE
In accordance with JIS K 7361-1 (1997), the haze of the laminate was measured using a haze meter (product name "HZ-V3", manufactured by Suga Test Instruments Co., Ltd.).

Claims (4)

A resin composition that is curable by active energy rays,
The active energy ray curable resin composition comprises a quaternary ammonium salt-containing polymer and a phosphate ester and/or salt,
The anion of the salt contains a polyoxyalkylene structure.
When the active energy ray-curable resin composition contains a phosphate ester, the acid value of the active energy ray-curable resin composition is 400 mg KOH/g to 600 mg KOH/g.
Active energy ray curable resin composition. The active energy ray curable resin composition according to claim 1, comprising urethane poly(meth)acrylate. A cured product of the active energy ray curable resin composition according to claim 1 or 2. A laminate comprising the cured product described in claim 3.