Active energy line hardening components, hardeners and build-up

TWI934180BActive Publication Date: 2026-08-01ARAKAWA CHEM IND LTD
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Patent Information

Authority / Receiving Office
TW · TW
Patent Type
Patents
Current Assignee / Owner
ARAKAWA CHEM IND LTD
Filing Date
2024-02-21
Publication Date
2026-08-01
Patent Text Reader

Abstract

This invention provides an active energy line curable composition, a cured product, and a laminate. The active energy line curable composition comprises a low-molecular-weight anionic emulsifier, a high-molecular-weight anionic emulsifier, poly(meth)acrylate, and water. The low-molecular-weight anionic emulsifier has a weight-average molecular weight of less than 10,000, and the high-molecular-weight anionic emulsifier has a weight-average molecular weight of 10,000 to 500,000.
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Description

Actinic energy ray-curable composition, cured product, and laminate The present invention relates to an actinic energy ray-curable composition, a cured product, and a laminate. Compositions curable by actinic energy rays have been developed to impart surface functionality to various substrates. In recent years, from the perspective of global environmental protection, aqueous actinic energy ray-curable compositions have been demanded. [Prior Art Documents] [Patent Documents] [Patent Document 1] Japanese Patent Application Laid-Open No. 2008-303258 [Problems to be Solved by the Invention] The problem to be solved by the present invention is to provide an actinic energy ray-curable composition having good emulsifying properties, mechanical stability, and high-temperature stability. [Means for Solving the Problems] According to the present disclosure, the following items are provided. (Item 1) An actinic energy ray-curable composition, the actinic energy ray-curable composition containing a low-molecular-weight anionic emulsifier, a high-molecular-weight anionic emulsifier, a poly(meth)acrylate, and water, the weight-average molecular weight of the low-molecular-weight anionic emulsifier being less than 10,000, and the weight-average molecular weight of the high-molecular-weight anionic emulsifier being 10,000 to 500,000. (Item 2) The actinic energy ray-curable composition according to Item 1, wherein the low-molecular-weight anionic emulsifier is ammonium polyoxyalkylene sulfonate (meth)acrylate. (Item 3) A cured product of the actinic energy ray-curable composition of Item 1. (Item 4) A laminate containing the cured product of Item 1. In the present disclosure, in addition to the specific combinations, the one or more features may be further combined and provided. [Effects of the Invention] The actinic energy ray-curable composition of the present disclosure has good emulsifying properties, mechanical stability, and high-temperature stability. Throughout the present disclosure, the ranges of physical property values, contents, and other numerical values can be appropriately set (for example, selected from the values described in the following items). Specifically, regarding the numerical value α, when A3, A2, A1 (where A3 > A2 > A1) are cited as the numerical value α, the range of the numerical value α can be exemplified as 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 less than A2, greater than A2 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. As long as the problems to be solved by the present invention are solved, the respective components, conditions, numerical values, etc. are not particularly limited. "αβ quantity (A / B)" refers to the β quantity (α) of A relative to 100α of B. α includes, for example, mass %, mole %, parts by mass, etc. β quantity includes, for example, content, usage amount, etc. "Mass % content (A / B)" refers to the content (mass %) of A relative to 100 mass % of B. "γ ratio (A / B)" refers to the γ ratio calculated by the formula "A÷B". γ ratio includes, for example, mass ratio, mole ratio, etc. "Non-volatile component" represents the total mass of components other than organic solvents and water. In one embodiment, "the non-volatile component of A" refers to the total mass of the residual components when 1 g of A is heated to a constant weight at 105°C. "(Meth)acrylic acid" refers to "acrylic acid and / or methacrylic acid". "(Meth)acrylate" refers to "acrylate and / or methacrylate". "(Meth)acryloyl" refers to "acryloyl and / or methacryloyl". "(Meth)allyl" refers to "allyl and / or methallyl". "C…" refers to "having … carbon atoms". For example, "C1-C6 alkyl" refers to an alkyl having 1 to 6 carbon atoms. "C6 alkyl" refers to an alkyl having 6 carbon atoms. Examples of alkyl include linear alkyl, branched alkyl, cycloalkyl, etc. Examples of linear alkyl include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc. "Branched alkyl" refers to a group in which at least one hydrogen atom of a linear alkyl is substituted by an alkyl and which does not have a cyclic structure. Examples of branched alkyl include isopropyl, diethylpentyl, trimethylbutyl, trimethylpentyl, trimethylhexyl, etc. Examples of cycloalkyl include monocyclic cycloalkyl, crosslinked cycloalkyl, fused cycloalkyl, etc. In addition, a group in which at least one hydrogen atom of cycloalkyl is substituted by an alkyl is also regarded as cycloalkyl. "Monocyclic" refers to a cyclic structure formed by covalent bonds of carbon and having no bridging structure in the inner part. "Fused ring" refers to a cyclic structure in which two or more monocyclic rings share two atoms (i.e., each ring shares only one edge (fused)). "Crosslinked ring" refers to a cyclic structure in which two or more monocyclic rings share three or more atoms. Examples of monocyclic cycloalkyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclodecyl, 3,5,5-trimethylcyclohexyl, etc. Examples of crosslinked cycloalkyl include tricyclodecyl, adamantyl, norbornyl, etc. Furthermore, alkyl also includes groups combining linear alkyl, branched alkyl, and cycloalkyl. Examples of the combined groups include cycloalkylalkyl, etc. Cycloalkylalkyl is represented by the following formula. R CAlkyl -R Alkyl - (wherein, R CAlkyl represents a cycloalkyl group. R Alkyl represents an alkyl group.) Examples of the alkylene group include linear alkylene groups, branched alkylene groups, cycloalkylene groups, etc. Examples of the linear alkylene group include methylene, ethylene, propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene, n-octylene, n-nonylene, n-decamethylene, etc. Examples of the branched alkylene group include diethylpentylene, trimethylbutylene, trimethylpentylene, trimethylhexylene, etc. Examples of the cycloalkylene group include monocyclic cycloalkylene groups, crosslinked cycloalkylene groups, fused cycloalkylene groups, etc. In addition, one or more hydrogen atoms of the cycloalkylene group may be substituted with a linear alkyl group or a branched alkyl group. Examples of the monocyclic cycloalkylene group include cyclopentylene, cyclohexylene, cycloheptylene, cyclodecylene, 3,5,5-trimethylcyclohexylene, etc. Examples of the crosslinked cycloalkylene group include tricyclodecylene, adamantylene, norbornylene, etc. Examples of the fused cycloalkylene group include bicyclodecylene, etc. Furthermore, the alkylene group also includes a group combining a linear alkylene group, a branched alkylene group, and a cycloalkylene group. Examples of the combined group include cycloalkylalkylene, alkylenecycloalkylalkylene, etc. The cycloalkylalkylene is represented by the following formula. -R CAlkylene -R Alkylene - (wherein, R CAlkylene represents a cycloalkylene group. R Alkylene represents an alkylene group.) The alkylenecycloalkylalkylene is represented by the following formula. -R Alkylene -R CAlkylene -R Alkylene - (wherein, R CAlkylene represents a cycloalkylene group. R Alkylene represents an alkylene group.) The aromatic group (aryl, arylene) may be substituted or unsubstituted. Examples of the substituent of the aryl group include an alkyl group, a thioalkyl group, a thioaryl group, an arylcarbonyl group, etc. Examples of the aryl group include a monocyclic aryl group, a polycyclic aryl group, etc. Examples of the monocyclic aryl group include a phenyl group, a tolyl group, a mesityl group (2,4,6-trimethylphenyl), etc. Examples of the polycyclic aryl group include a naphthyl group, etc. Examples of the arylene group include a monocyclic arylene group, a polycyclic arylene group, etc. Examples of the monocyclic arylene group include a phenylene group, a tolylene group, etc. Examples of the polycyclic arylene group include a naphthylene group, etc. [Active energy ray curable composition] The present disclosure relates to an active energy ray curable composition comprising a low molecular weight anionic emulsifier, a high molecular weight anionic emulsifier, a poly(meth)acrylate, and water, wherein the weight average molecular weight of the low molecular weight anionic emulsifier is less than 10,000, and the weight average molecular weight of the high molecular weight anionic emulsifier is from 10,000 to 500,000. <Low molecular weight anionic emulsifier> The low molecular weight anionic emulsifier may be used alone or in combination of two or more. Examples of the anionic group include a sulfate group (-OSO 3 X), a sulfonate group (-SO 3 X), a phosphate group (-OPO(OX) 2 ), a phosphonate group (-PO(OX) 2 ), a carboxylate group (-COOX), a borate group (-B(OX) 2 ), (X = cationic group), etc. Examples of the low molecular weight anionic emulsifier include a reactive low molecular weight anionic emulsifier, a non-reactive low molecular weight anionic emulsifier, etc. (Reactive low molecular weight anionic emulsifier) The reactive low molecular weight anionic emulsifier may be used alone or in combination of two or more. Examples of the reactive group include a (meth)acryloyl group, a (meth)allyl group, etc. Examples of the reactive low molecular weight anionic emulsifier include ammonium polyoxyalkylene sulfonate (meth)acrylate, etc. Examples of ammonium polyoxyalkylene sulfonate (meth)acrylate include ammonium polyoxyalkylene polyaryl ether sulfonate (meth)acrylate, etc. In one embodiment, the ammonium polyoxyalkylene sulfonate (meth)acrylate is represented by the following formula. [Chemical formula 1] [In the formula, R 1 ~R 5 independently represent a hydrogen atom, an alkyl group, or an aralkyl group respectively. R 1 ~R 5 may be different. R 6 represents a C2-4 alkylene group. n represents an integer of 5 to 150. In each structural unit, R 6 may be different. R 7 independently represent a hydrogen atom or a C1-10 hydrocarbon group respectively. R 8 represents an alkylene group. R 9 represents a hydrogen atom or a methyl group.] Examples of the aralkyl group include 1-phenylethyl and the like. In one embodiment, in the above formula, R 1 and R 5 represent a hydrogen atom, R 2 and R 4 represent 1-phenylethyl, and R 3 represents a methyl group. (Non-reactive low-molecular-weight anionic emulsifier) The non-reactive low-molecular-weight anionic emulsifier can be used alone or in combination of two or more. Examples of the non-reactive low-molecular-weight anionic emulsifier include non-reactive low-molecular-weight carboxylic acid emulsifiers, non-reactive low-molecular-weight sulfate emulsifiers, non-reactive low-molecular-weight sulfonate emulsifiers, non-reactive low-molecular-weight phosphate ester salts emulsifiers, and the like. Examples of the non-reactive low-molecular-weight carboxylic acid emulsifier include rosin acid salts, fatty acid salts, acyl sarcosine salts, and the like. Examples of the non-reactive low-molecular-weight sulfate emulsifier include alkyl sulfate salts, alkyl ether sulfate salts, amide ether sulfates, polyoxyalkylene alkyl ether sulfate salts, polyoxyalkylene dialkyl ether sulfate salts, polyoxyalkylene trialkyl ether sulfate salts, polyoxyalkylene alkyl aryl ether sulfate salts, and the like. Examples of non-reactive low-molecular-weight sulfonate emulsifiers include polyoxyalkylene alkyl sulfosuccinates, diester salts of sulfosuccinic acid, sulfosuccinate esters, dialkyl sulfosuccinate salts, etc. Examples of non-reactive low-molecular-weight phosphate ester salts emulsifiers include alkyl phosphates, alkyl ether phosphates, etc. In one embodiment, preferred low-molecular-weight anionic emulsifiers include ammonium polyoxyalkylene sulfonate (meth)acrylates. The reasons for preference include, for example, improved scratch resistance of the cured product, improved resistance to humidity and heat, etc. In one embodiment, preferred low-molecular-weight anionic emulsifiers include ammonium polyoxyalkylene sulfonate (meth)acrylates. The reasons for preference include, for example, improved scratch resistance of the cured product, improved resistance to humidity and heat, etc. The weight average molecular weight (low-molecular-weight anionic emulsifier) is, for example, less than 10,000, 9999, 9500, 9000, 8500, 8000, 7500, 7000, 6500, 6000, 5500, 5000, 4500, 4000, 3500, 3000, 2500, 2000, 1900, 1800, 1700, 1600, 1500, 1400, 1300, 1200, 1100, 1000, 500, 300, 250, 100, etc. In one embodiment, the weight average molecular weight is preferably less than 10,000, more preferably 100 or more and less than 10,000, still more preferably 300 or more and less than 10,000, and particularly preferably 300 to 2000. The weight average molecular weight and number average molecular weight can be determined according to the following conditions. Measuring machine: manufactured by Tosoh Corporation, GPC (model: HLC-8220) Column: One guard column TSKgel guardcolumn α and two TSK-GEL α-M columns (temperature 40 °C) manufactured by Tosoh Corporation Detector: TDA model (MODEL) 301 manufactured by VISCOTECH (concentration detector, 90° light scattering detector, and viscosity detector (temperature 40 °C)) RALLS method Eluent: 0.02M NaNO 3 / CH 3CN = 80 / 20 wt% Sample concentration: 0.5 wt% Development temperature: 40°C Standard substance: Polyethylene oxide Flow rate: 1.0 mL / minute Test sample: First, prepare a test sample by adding the eluent so that the concentration of the test sample becomes 0.5% in terms of the non-volatile component concentration. Next, add an aqueous sodium hydroxide solution until the pH becomes 10 - 12. Further, immerse it in a hot water bath at 80°C or higher for 1 hour. Thereafter, adjust the pH to 6 - 8 with sulfuric acid and dilute it to 0.025% with the eluent for measurement. Mass % content (low molecular weight anionic emulsifier / non-volatile content of the active energy ray curable composition) Examples include 20 mass%, 19 mass%, 17 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 9 mass%, 7 mass%, 5 mass%, 3 mass%, 2 mass%, 1.5 mass%, 1 mass%, 0.9 mass%, 0.7 mass%, 0.5 mass%, 0.3 mass%, 0.1 mass%, 0.09 mass%, 0.07 mass%, 0.05 mass%, 0.03 mass%, 0.01 mass%, etc. In one embodiment, the content is preferably 0.01 mass% - 20 mass%, more preferably 0.05 mass% - 10 mass%. The reason for preference is, for example, improvement of water resistance, etc. <High molecular weight anionic emulsifier> The high molecular weight anionic emulsifier can be used alone or in combination of two or more. Examples of the high molecular weight anionic emulsifier include polymers containing anionic group-containing monomer units and hydrophobic monomer units, etc. (Anionic group-containing monomer) The anionic group-containing monomer can be used alone or in combination of two or more. Examples of the anionic group-containing monomer include carboxyl group-containing monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, and their salts, etc. Mass % content (anionic group-containing monomer unit / high molecular weight anionic emulsifier) Examples include 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, etc. In one embodiment, the content is preferably 5 mass% - 95 mass%. The molar percentage (anionic group-containing monomer unit / polymeric anionic emulsifier) includes, for example, 95 mol%, 90 mol%, 85 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%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, etc. In one embodiment, the content is preferably 5 mol% to 95 mol%. Examples of the salt include inorganic salts, organic salts, etc. Examples of the inorganic salt include lithium salts, sodium salts, potassium salts, calcium salts, etc. Examples of the organic salt include ammonium salts, amine salts, etc. - Carboxyl group-containing monomer The carboxyl group-containing monomer can be used alone or in combination of two or more. Examples of the carboxyl group-containing monomer include mono(carboxyl) group-containing monomers, poly(carboxyl) group-containing monomers, etc. The "mono(carboxyl) group-containing monomer" refers to a monomer containing one carboxyl group. The "poly(carboxyl) group-containing monomer" refers to a monomer containing multiple carboxyl groups. The mass percentage (carboxyl group-containing monomer unit / polymeric anionic emulsifier) includes, for example, 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 95 mass%. The molar percentage (carboxyl group-containing monomer unit / polymeric anionic emulsifier) includes, for example, 95 mol%, 90 mol%, 85 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%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 95 mol%. Examples of the mono(carboxyl) group-containing monomer include (meth)acrylic acid, crotonic acid, etc. The mass % content (including the mono(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 95 mass %, 90 mass %, 85 mass %, 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 4 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 95 mass %. The molar % content (including the mono(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 95 mol %, 90 mol %, 85 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 %, 20 mol %, 15 mol %, 10 mol %, 5 mol %, 4 mol %, 2 mol %, 1 mol %, 0.5 mol %, 0.1 mol %, 0.05 mol %, 0.01 mol %, 0 mol %, etc. In one embodiment, the content is preferably 0 mol % to 95 mol %. The mass % content ((meth)acrylic acid unit / polymeric anionic emulsifier) includes, for example, 95 mass %, 90 mass %, 85 mass %, 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 4 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 95 mass %. The molar % content ((meth)acrylic acid unit / polymeric anionic emulsifier) includes, for example, 95 mol %, 90 mol %, 85 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 %, 20 mol %, 15 mol %, 10 mol %, 5 mol %, 4 mol %, 2 mol %, 1 mol %, 0.5 mol %, 0.1 mol %, 0.05 mol %, 0.01 mol %, 0 mol %, etc. In one embodiment, the content is preferably 0 mol % to 95 mol %. Examples of the poly(carboxyl) monomer include maleic acid, maleic anhydride, fumaric acid, itaconic acid, citraconic acid, and citraconic anhydride. The mass% content (including poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%, more preferably 0 mass% to 20 mass%. The molar% content (including poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%, more preferably 0 mol% to 20 mol%. The molar% content (itaconic acid unit / polymeric anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%. The mass% content (maleic acid unit / polymeric anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. The molar% content (maleic acid unit / high molecular anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%. In one embodiment, the poly(carboxyl) monomer unit-containing may have one or more esterified carboxyl groups. The "unesterified poly(carboxyl) monomer unit-containing" refers to a polycarboxyl-containing monomer unit in which the carboxyl group is not esterified at all. The mass% content (unesterified poly(carboxyl) monomer unit / high molecular anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. The molar% content (unesterified poly(carboxyl) monomer unit / high molecular anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%. The "partially esterified poly(carboxyl) monomer unit-containing" refers to a polycarboxyl-containing monomer unit in which a part of the carboxyl group is esterified. Examples of the partially esterified poly(carboxyl) monomer unit include partially aliphatic alcohol-esterified poly(carboxyl) monomer units, etc. Examples of the partially aliphatic alcohol-esterified poly(carboxyl) monomer unit include partially linear aliphatic alcohol-esterified poly(carboxyl) monomer units, partially branched aliphatic alcohol-esterified poly(carboxyl) monomer units, partially cyclic aliphatic alcohol-esterified poly(carboxyl) monomer units, etc. Partial linear aliphatic alcohol esterified poly(carboxyl) monomer units include, for example, methanol half-ester maleic acid units, ethanol half-ester maleic acid units, n-propanol half-ester maleic acid units, n-butanol half-ester maleic acid units, n-pentanol half-ester maleic acid units, n-hexanol half-ester maleic acid units, etc. Partial branched aliphatic alcohol esterified poly(carboxyl) monomer units include, for example, isopropyl alcohol half-ester maleic acid units, 2-ethylhexanol half-ester maleic acid units, etc. Partial cyclic aliphatic alcohol esterified poly(carboxyl) monomer units include, for example, cyclohexanol half-ester maleic acid units, etc. The mass% content (partially esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. The molar% content (partially esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%. The mass% content (partially aliphatic esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. Mole% content (partially aliphatic esterified poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mole%, 55 mole%, 50 mole%, 45 mole%, 40 mole%, 35 mole%, 30 mole%, 25 mole%, 20 mole%, 15 mole%, 10 mole%, 9 mole%, 8 mole%, 7 mole%, 6 mole%, 5 mole%, 4 mole%, 3 mole%, 2 mole%, 1 mole%, 0.5 mole%, 0.1 mole%, 0.05 mole%, 0.01 mole%, 0 mole%, etc. In one embodiment, the content is preferably 0 mole% to 60 mole%. Mass% content (partially linear aliphatic esterified poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. Mole% content (partially linear aliphatic esterified poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mole%, 55 mole%, 50 mole%, 45 mole%, 40 mole%, 35 mole%, 30 mole%, 25 mole%, 20 mole%, 15 mole%, 10 mole%, 9 mole%, 8 mole%, 7 mole%, 6 mole%, 5 mole%, 4 mole%, 3 mole%, 2 mole%, 1 mole%, 0.5 mole%, 0.1 mole%, 0.05 mole%, 0.01 mole%, 0 mole%, etc. In one embodiment, the content is preferably 0 mole% to 60 mole%. Mass% content (partially branched aliphatic esterified poly(carboxyl) monomer unit / polymeric anionic emulsifier) includes, for example, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 60 mass%. Mole % content (partially branched aliphatic esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) examples include 60 mole %, 55 mole %, 50 mole %, 45 mole %, 40 mole %, 35 mole %, 30 mole %, 25 mole %, 20 mole %, 15 mole %, 10 mole %, 9 mole %, 8 mole %, 7 mole %, 6 mole %, 5 mole %, 4 mole %, 3 mole %, 2 mole %, 1 mole %, 0.5 mole %, 0.1 mole %, 0.05 mole %, 0.01 mole %, 0 mole %, etc. In one embodiment, the content preferably includes 0 mole % to 60 mole %. Mass % content (partially cyclic aliphatic esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) examples include 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content preferably includes 0 mass % to 60 mass %. Mole % content (partially cyclic aliphatic esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) examples include 60 mole %, 55 mole %, 50 mole %, 45 mole %, 40 mole %, 35 mole %, 30 mole %, 25 mole %, 20 mole %, 15 mole %, 10 mole %, 9 mole %, 8 mole %, 7 mole %, 6 mole %, 5 mole %, 4 mole %, 3 mole %, 2 mole %, 1 mole %, 0.5 mole %, 0.1 mole %, 0.05 mole %, 0.01 mole %, 0 mole %, etc. In one embodiment, the content preferably includes 0 mole % to 60 mole %. "Fully esterified poly(carboxyl) monomer unit" means a polycarboxyl monomer unit in which all carboxyl groups are esterified. Mass % content (fully esterified poly(carboxyl) monomer unit / high molecular weight anionic emulsifier) examples include 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content preferably includes 0 mass % to 60 mass %. The molar percentage content (fully esterified poly(carboxyl) monomer unit / high molecular anionic emulsifier) includes, for example, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 60 mol%. For salts, the esterified poly(carboxyl) monomer units include, for example, partially esterified poly(carboxyl) monomer inorganic salt units, partially esterified poly(carboxyl) monomer organic salt units, etc. The degree of neutralization (esterified poly(carboxyl) monomer unit) includes, for example, 100%, 95%, 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10%, 5%, 0%, etc. In one embodiment, the degree of neutralization is preferably 0% to 100%. (Partially or fully) esterified poly(carboxyl) monomer units can be introduced into the high molecular anionic emulsifier by the following methods. (1) After esterifying the anhydride of the poly(carboxyl) monomer, polymerization is carried out. (2) After polymerizing the anhydride of the poly(carboxyl) monomer, esterification is carried out. ・ Sulfonic acid group-containing monomer The sulfonic acid group-containing monomer can be used alone or in combination of two or more. The sulfonic acid group-containing monomer includes, for example, sulfonic acid group-containing aliphatic hydrocarbon monomers, sulfonic acid group-containing aromatic hydrocarbon monomers, sulfonic acid group-containing non-hydrocarbon monomers, etc. The mass% content (sulfonic acid group-containing monomer unit / high molecular anionic emulsifier) includes, for example, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 15 mass%. The molar percentage content (sulfonic acid group-containing monomer unit / high molecular anionic emulsifier) includes, for example, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 15 mol%. The sulfonic acid group-containing aliphatic hydrocarbon monomer includes, for example, (meth)allyl sulfonic acid, etc. The mass% content (sulfonic acid group-containing aliphatic hydrocarbon monomer unit / polymeric anionic emulsifier) includes, for example, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 15 mass%. The molar% content (sulfonic acid group-containing aliphatic hydrocarbon monomer unit / polymeric anionic emulsifier) includes, for example, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 15 mol%. Sulfonic acid group-containing aromatic hydrocarbon monomers include, for example, styrene sulfonic acid, vinyl sulfonic acid, 2-sulfonic acid group ethyl (meth)acrylate, etc. The mass% content (sulfonic acid group-containing aromatic hydrocarbon monomer unit / polymeric anionic emulsifier) includes, for example, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 15 mass%. The molar% content (sulfonic acid group-containing aromatic hydrocarbon monomer unit / polymeric anionic emulsifier) includes, for example, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 15 mol%. The "sulfonic acid group-containing non-hydrocarbon monomer" refers to a monomer containing atoms other than carbon atoms and hydrogen atoms in the structure other than the sulfonic acid (salt) group. Sulfonic acid group-containing non-hydrocarbon monomers include, for example, 2-sulfoethyl (meth)acrylate, tert-butyl sulfonic acid (meth)acrylamide, etc. The mass% content (sulfonic acid group-containing non-hydrocarbon monomer unit / polymeric anionic emulsifier) includes, for example, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 15 mass%. The molar% content (sulfonic acid group-containing non-hydrocarbon monomer unit / high molecular weight anionic emulsifier) includes, for example, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 15 mol%. ・ Phosphoric acid group-containing monomer The phosphoric acid group-containing monomer can be used alone or in combination of two or more. Examples of the phosphoric acid group-containing monomer include mono[(2-hydroxyethyl (meth)acrylate)] phosphate, mono[(2-hydroxypropyl (meth)acrylate)] phosphate, mono[(3-hydroxypropyl (meth)acrylate)] phosphate, mono[2-hydroxypropyl 3-chloro-(meth)acrylate] phosphate, (meth)allyl alcohol phosphate, mono[(2-hydroxyethyl (meth)acrylate)] phosphite, etc. The mass% content (phosphoric acid group-containing non-hydrocarbon monomer unit / high molecular weight anionic emulsifier) includes, for example, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 15 mass%. The molar% content (phosphoric acid group-containing non-hydrocarbon monomer unit / high molecular weight anionic emulsifier) includes, for example, 15 mol%, 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 15 mol%. (Hydrophobic monomer) The hydrophobic monomer can be used alone or in combination of two or more. Examples of the hydrophobic monomer include (meth)acrylate without a hydroxyl group, aromatic vinyl compounds, etc. The mass% content (hydrophobic monomer unit / high molecular weight anionic emulsifier) includes, for example, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, etc. In one embodiment, the content is preferably 5 mass% to 70 mass%. The molar percentage (hydrophobic monomer unit / polymeric anionic emulsifier) includes, for example, 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%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, etc. In one embodiment, the content is preferably 5 mol% to 70 mol%. ・ (Meth)acrylate without hydroxyl group The (meth)acrylate without hydroxyl group can be used alone or in combination of two or more. The (meth)acrylate without hydroxyl group includes, for example, linear (meth)acrylate without hydroxyl group, branched (meth)acrylate without hydroxyl group, alicyclic (meth)acrylate without hydroxyl group, substituted (meth)acrylate without hydroxyl group, etc. The mass percentage (unit of (meth)acrylate without hydroxyl group / polymeric anionic emulsifier) includes, for example, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 50 mass%. The molar percentage (unit of (meth)acrylate without hydroxyl group / polymeric anionic emulsifier) includes, for example, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 50 mol%. The linear (meth)acrylate without hydroxyl group includes, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-pentyl (meth)acrylate, hexyl (meth)acrylate, n-octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, etc. The mass % content (linear (meth)acrylate unit without hydroxyl group / high molecular weight anionic emulsifier) includes, for example, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 4 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 50 mass %. The molar % content (linear (meth)acrylate unit without hydroxyl group / high molecular weight anionic emulsifier) includes, for example, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 50 mol%. Branched (meth)acrylate without hydroxyl group includes, for example, isopropyl (meth)acrylate, isobutyl (meth)acrylate, isopentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, etc. The mass % content (branched (meth)acrylate unit without hydroxyl group / high molecular weight anionic emulsifier) includes, for example, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 4 mass %, 2 mass %, 1 mass %, 0.5 mass %, 0.1 mass %, 0.05 mass %, 0.01 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 50 mass %. The molar % content (branched (meth)acrylate unit without hydroxyl group / high molecular weight anionic emulsifier) includes, for example, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 50 mol%. Alicyclic (meth)acrylate without hydroxyl group includes, for example, cyclohexyl (meth)acrylate, etc. The mass % content (alicyclic (meth)acrylate unit / high molecular weight anionic emulsifier excluding hydroxyl groups) includes, for example, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 50 mass%. The molar % content (alicyclic (meth)acrylate unit / high molecular weight anionic emulsifier excluding hydroxyl groups) includes, for example, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 50 mol%. ・Aromatic vinyl compound Aromatic vinyl compounds can be used alone or in combination of two or more. Examples of aromatic vinyl compounds include styrene, α-methylstyrene, p-methylstyrene, vinyltoluene, chlorostyrene, divinylbenzene, etc. The mass % content (aromatic vinyl compound unit / high molecular weight anionic emulsifier) includes, for example, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 70 mass%. The molar % content (aromatic vinyl compound unit / high molecular weight anionic emulsifier) includes, for example, 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%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 70 mol%. (Hydrophilic monomers other than those described above) In one embodiment, the high molecular weight anionic emulsifier may optionally contain hydrophilic monomers other than those described above. The hydrophilic monomers other than those described above can be used alone or in combination of two or more. Examples of hydrophilic monomers other than those described above include (meth)acrylamide, hydroxyl group-containing (meth)acrylate, polyalkylene glycol di(meth)acrylate, and the like. The mass% content (hydrophilic monomer unit other than those described above / polymer anionic emulsifier) is, for example, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the preferred content is, for example, 0 mass% to 90 mass%. The molar% content (hydrophilic monomer unit other than those described above / polymer anionic emulsifier) is, for example, 90 mol%, 85 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%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the preferred content is, for example, 0 mol% to 90 mol%. ・(Meth)acrylamide (Meth)acrylamide can be used alone or in combination of two or more. The mass% content ((meth)acrylamide unit / polymer anionic emulsifier) is, for example, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the preferred content is, for example, 0 mass% to 90 mass%. The molar percentage ((meth)acrylamide unit / polymeric anionic emulsifier) includes, for example, 90 mol%, 85 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%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 90 mol%. ・ Hydroxyl group-containing (meth)acrylate The hydroxyl group-containing (meth)acrylate can be used alone or in combination of two or more. Examples of the hydroxyl group-containing (meth)acrylate include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, etc. The mass percentage (hydroxyl group-containing (meth)acrylate unit / polymeric anionic emulsifier) includes, for example, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 30 mass%. The molar percentage (hydroxyl group-containing (meth)acrylate unit / polymeric anionic emulsifier) includes, for example, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 30 mol%. ・ Polyalkylene glycol di(meth)acrylate The polyalkylene glycol di(meth)acrylate can be used alone or in combination of two or more. Examples of the polyalkylene glycol di(meth)acrylate include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, etc. The mass percentage (polyalkylene glycol di(meth)acrylate unit / polymeric anionic emulsifier) includes, for example, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.5 mass%, 0.1 mass%, 0.05 mass%, 0.01 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 5 mass%. The molar% content (polyalkylene glycol di(meth)acrylate unit / polymer anionic emulsifier) includes, for example, 5 mol%, 4 mol%, 2 mol%, 1 mol%, 0.5 mol%, 0.1 mol%, 0.05 mol%, 0.01 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 5 mol%. (Monomers other than the above: other monomers) In one embodiment, the polymer anionic emulsifier may optionally contain monomers other than the above (other monomers). The other monomers may be used alone or in combination of two or more. Examples of the other monomers include amino(meth)acrylate and the like. The mass% content (other monomer unit / polymer anionic emulsifier) includes, for example, less than 1 mass%, less than 0.5 mass%, less than 0.1 mass%, 0 mass%, etc. The molar% content (other monomer unit / polymer anionic emulsifier) includes, for example, less than 1 mol%, less than 0.5 mol%, less than 0.1 mol%, 0 mol%, etc. The weight average molecular weight (polymer anionic emulsifier) includes, for example, 500,000, 450,000, 400,000, 350,000, 300,000, 250,000, 200,000, 150,000, 145,000, 140,000, 135,000, 130,000, 125,000, 124,000, 120,000, 115,000, 110,000, 105,000, 100,000, 95,000, 90,000, 85,000, 80,000, 75,000, 70,000, 65,000, 64,000, 60,000, 55,000, 50,000, 45,000, 40,000, 35,000, 30,000, 29,000, 25,000, 20,000, 15,000, 10,000, etc. In one embodiment, the weight average molecular weight is preferably 10,000 to 500,000, more preferably 10,000 to 150,000. The number average molecular weight (polymer anionic emulsifier) includes, for example, 10,000, 9,500, 9,000, 8,500, 8,000, 7,500, 7,000, 6,500, 6,000, 5,500, 5,000, 4,500, 4,000, 3,500, 3,000, etc. In one embodiment, the number average molecular weight is preferably 3,000 to 10,000, more preferably 5,000 to 7,500. The mass percentage content (polymeric anionic emulsifier / non-volatile content of the active energy ray curable composition) includes, 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, 2% by mass, 1.5% by mass, 1% by mass, 0.9% by mass, 0.7% by mass, 0.5% by mass, 0.3% by mass, 0.1% by mass, 0.09% by mass, 0.07% by mass, 0.05% by mass, 0.03% by mass, 0.01% by mass, etc. In one embodiment, the content is preferably 0.01% by mass to 20% by mass, more preferably 0.5% by mass to 10% by mass. The mass ratio (polymeric anionic emulsifier / low molecular weight anionic emulsifier) includes, for example, 2000, 1750, 1500, 1250, 1000, 750, 500, 250, 100, 75, 50, 25, 10, 9, 7, 5, 3, 2, 1, 0.9, 0.7, 0.5, 0.3, 0.2, 0.1, 0.09, 0.05, 0.02, 0.01, 0.009, 0.007, 0.005, 0.002, 0.001, 0.0009, 0.0007, 0.0005, etc. In one embodiment, the mass ratio is preferably 0.0005 to 2000, more preferably 0.1 to 5. The mass ratio (polymeric anionic emulsifier / poly(meth)acrylate) includes, for example, 0.5, 0.45, 0.4, 0.35, 0.3, 0.25, 0.2, 0.15, 0.1, 0.06, 0.055, 0.05, 0.04, 0.03, 0.025, 0.02, 0.01, etc. In one embodiment, the mass ratio is preferably 0.01 to 0.5, more preferably 0.01 to 0.2. <Poly(meth)acrylate> Poly(meth)acrylate can be used alone or in combination of two or more. "Poly(meth)acrylate" refers to a compound having two or more (meth)acryloyl groups. Examples of poly(meth)acrylate include (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, (poly)glycerol poly(meth)acrylate, urethane poly(meth)acrylate, etc. (Poly)pentaerythritol poly(meth)acrylate includes, for example, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 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, tripentaerythritol octa(meth)acrylate, etc. (Poly)trimethylolpropane poly(meth)acrylate includes, for example, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, di-trimethylolpropane di(meth)acrylate, di-trimethylolpropane tri(meth)acrylate, di-trimethylolpropane tetra(meth)acrylate, etc. (Poly)glycerol poly(meth)acrylate includes, for example, glycerol di(meth)acrylate, glycerol tri(meth)acrylate, diglycerol di(meth)acrylate, diglycerol tri(meth)acrylate, diglycerol tetra(meth)acrylate, etc. (Urethane poly(meth)acrylate) Urethane poly(meth)acrylate includes, for example, the reaction products of a compound group containing a hydroxyl group-containing poly(meth)acrylate and a polyisocyanate. <Hydroxyl group-containing poly(meth)acrylate> Hydroxyl group-containing poly(meth)acrylate includes, for example, (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, (poly)glycerol poly(meth)acrylate, etc. The polyisocyanate can be used alone or in combination of two or more. <Polyisocyanate> "Polyisocyanate" refers to a compound having two or more isocyanate groups (-N=C=O). Polyisocyanate includes, for example, linear aliphatic polyisocyanate, branched aliphatic polyisocyanate, alicyclic polyisocyanate, aromatic polyisocyanate, and their biuret bodies, isocyanurate bodies, urethane bodies, adduct bodies, etc. Linear aliphatic polyisocyanate includes, for example, methylene diisocyanate, dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, decamethylene diisocyanate, etc. Examples of branched aliphatic polyisocyanates include diethyl pentamethylene diisocyanate, trimethyl butylene diisocyanate, trimethyl pentamethylene diisocyanate, trimethyl hexamethylene diisocyanate, etc. Examples of alicyclic polyisocyanates include monocyclic alicyclic polyisocyanates, crosslinked cyclic alicyclic polyisocyanates, fused-ring alicyclic polyisocyanates, etc. Examples of monocyclic alicyclic polyisocyanates include hydrogenated xylene diisocyanate, isophorone diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, cycloheptylene diisocyanate, cyclodecylene diisocyanate, 3,5,5-trimethyl cyclohexylene diisocyanate, dicyclohexylmethane diisocyanate, etc. Examples of crosslinked cyclic alicyclic polyisocyanates include tricyclodecene diisocyanate, adamantane diisocyanate, norbornene diisocyanate, etc. Examples of fused-ring alicyclic polyisocyanates include bicyclodecene diisocyanate, etc. Examples of aromatic polyisocyanates include monocyclic aromatic polyisocyanates, fused-ring aromatic polyisocyanates, etc. Examples of monocyclic aromatic polyisocyanates include dialkyl diphenylmethane diisocyanates such as 4,4'-diphenyl dimethylmethane diisocyanate, tetraalkyl diphenylmethane diisocyanates such as 4,4'-diphenyl tetramethylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-dibenzyl isocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, toluene diisocyanate, xylylene diisocyanate, m-tetramethyl xylylene diisocyanate, etc. Examples of fused-ring aromatic polyisocyanates include 1,5-naphthalene diisocyanate, etc. In one embodiment, preferred poly(meth)acrylates include (poly)pentaerythritol poly(meth)acrylate. The reasons for preference include, for example, improved curability. The mass% content (poly(meth)acrylate / non-volatile matter of the active energy ray curable composition) includes, for example, 99 mass%, 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, etc. In one embodiment, the content is preferably 50 mass% to 99 mass%, and more preferably 70 mass% to 99 mass%. <Water> Water can be used alone or in combination of two or more. Examples of water include ultrapure water, pure water, distilled water, ion-exchanged water, tap water, etc. Mass % content (water / energy ray curable composition) includes, for example, 99 mass%, 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 2 mass%, 1 mass%, 0.9 mass%, 0.7 mass%, 0.5 mass%, etc. In one embodiment, the content is preferably 0.5 mass% to 99 mass%, more preferably 10 mass% to 60 mass%. <Photoinitiator> In one embodiment, the energy ray curable composition may optionally contain a photoinitiator. The photoinitiator may be used alone or in combination of two or more kinds. Photoinitiators include, for example, α-hydroxy dimethyl acetophenone group-containing photoinitiators, α-hydroxy cycloalkyl ketones, α-amino phenyl alkyl ketones, benzil dimethyl ketal, unsubstituted or substituted phenyl alkyl ketones, unsubstituted or substituted benzyls, unsubstituted or substituted benzophenones, acylphosphine oxides, substituted thioxanthones, oxime esters, etc. α-hydroxy dimethyl acetophenone group-containing photoinitiators include, for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methylpropan-1-one, 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropanoyl)benzyl)phenyl)-2-methylpropane-1-one, etc. α-hydroxy cycloalkyl ketones include, for example, 1-hydroxycyclohexyl phenyl ketone, etc. α-amino phenyl alkyl ketones include, for example, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, etc. Benzil dimethyl ketal includes, for example, 2,2-dimethoxy-1,2-diphenylethane-1-one, etc. Unsubstituted or substituted phenyl alkyl ketones include, for example, 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'-morpholinobutyrophenone, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, 2-isonitroacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, etc. Unsubstituted or substituted benzyls include, for example, benzyl, p-methoxybenzyl, etc. Unsubstituted or substituted benzophenones include, for example, benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 1,4-dibenzoylbenzene, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid, methyl 2-benzoylbenzoate, and the like. Acylphosphine oxides include, for example, 2,4,6-trimethylbenzoyl-diphenyl-oxide phosphine, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and the like. Substituted thioxanthones include, for example, 2-chlorothioxanthone, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, and the like. Oxime esters include, for example, 1,2-octanedione, 1-[4-(phenylthio)-, 2-(o-benzoyl oxime)] (i.e., 2-((benzoyloxy)imino)-1-(4-(phenylthio)phenyl)octan-1-one); acetone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyl oxime) (i.e., 1-(((1-(9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl)ethylidene)amino)oxy)ethan-1-one), and the like. When electron beam curing is carried out, a photoinitiator is not required. In one embodiment, preferred photoinitiators include acylphosphine oxides. The reasons for preference include, for example, less precipitate after emulsification, and the like. The mass% content (photoinitiator / non-volatile content of the active energy ray curable composition) includes, for example, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.9 mass%, 0.7 mass%, 0.5 mass%, 0.3 mass%, 0.1 mass%, 0 mass%, and the like. In one embodiment, the content is preferably 0 mass% to 30 mass%, more preferably 0.1 mass% to 10 mass%. <Additives> The active energy ray curable composition may optionally contain an agent (additive) that does not conform to any of the above. Additives include, for example, organic solvents, antioxidants, ultraviolet absorbers, light stabilizers, defoamers, surface modifiers, anti-pollution agents, pigments, metal oxide fine particle dispersions, organic fine particle dispersions, and the like. In one embodiment, the mass part content (additive / active energy ray curable composition) is preferably less than 1 mass part, less than 0.1 mass part, less than 0.01 mass part, 0 mass part, and the like. In one embodiment, the content in parts by mass (any one of the additive / low-molecular anionic emulsifier, high-molecular anionic emulsifier, poly(meth)acrylate, water, and photoinitiator) is preferably less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass, etc. Examples of the emulsification method include a mechanical emulsification method, a phase inversion emulsification method, a forced emulsification method, an inverse emulsification method, a high-pressure emulsification method, etc. Examples of the emulsification equipment include a propeller mixer, a turbine mixer, a homogenizing mixer, a dispersion mixer, a super mixer, a colloid mill, a high-pressure homogenizer, etc. Examples of the addition order include the following orders. (1) Poly(meth)acrylate and, if necessary, a photoinitiator and an additive (2) Low-molecular anionic emulsifier, high-molecular anionic emulsifier (3) Water In one embodiment, the emulsification temperature is preferably 10°C to 80°C. In one embodiment, the emulsification time is preferably 1 minute to 24 hours. Examples of the kneading concentration include 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass, 83% by mass, 82% by mass, 81% by mass, 80% by mass, etc. In one embodiment, the kneading concentration is preferably 80% by mass to 90% by mass. The volume average particle diameter (of the active energy ray-curable composition) is, for example, 10 μm, 7.5 μm, 5 μm, 2.5 μm, 1 μm, 0.9 μm, 0.8 μm, 0.7 μm, 0.6 μm, 0.5 μm, 0.4 μm, 0.3 μm, 0.2 μm, 0.1 μm, 0.05 μm, 0.01 μm, 0.005 μm, 0.001 μm, etc. In one embodiment, the volume average particle diameter is preferably 0.1 μm to 10 μm, more preferably 0.05 μm to 1 μm. Examples of the reason for preference include reducing sediment, etc. The volume average particle diameter can be measured according to the following conditions. Measuring instrument: MICROTRAC NT 3300 (manufactured by Nikkiso Co., Ltd.) Number of measurements: 3 Measurement temperature: 25 ± 5°C Measurement time: 30 seconds Particle size classification: Standard Calculation method: MT3000II Measurement upper limit: 2000 μm Measurement lower limit: 0.021 μm Residual ratio: 0.00% Pass rate: 0.00% Remaining ratio setting: Disabled Particle permeability: Transparent Particle shape: Non-spherical Viscosity (active energy ray curable composition) examples include 500000 mPa・s, 300000 mPa・s, 250000 mPa・s, 100000 mPa・s, 75000 mPa・s, 50000 mPa・s, 25000 mPa・s, 10000 mPa・s, 7500 mPa・s, 5000 mPa・s, 2000 mPa・s, 1000 mPa・s, etc. In one embodiment, the viscosity is preferably 1000 mPa・s to 500000 mPa・s, more preferably 5000 mPa・s to 300000 mPa・s. The reason for the preference is, for example, improved curability, etc. The viscosity can be measured according to the following conditions. Measuring machine: VISCOMETER TVK-10, manufactured by Toki Sangyo Co., Ltd. Non-volatile content concentration: 15 mass% Measuring temperature: 25 °C Use (active energy ray curable composition) examples include coating agents, adhesives, active energy ray curable coating agents, active energy ray curable adhesives, etc. [Cured product] The present disclosure relates to a cured product of the active energy ray curable composition. Curing conditions examples include the following conditions, etc. [Laminate] The present disclosure relates to a laminate comprising the cured product. In one embodiment, the laminate can be manufactured by a method including the following steps. Coating step: A step of coating the composition on at least one side of a substrate. Active energy ray curing step: A step of irradiating active energy rays to form a cured product layer. Substrates examples include polycarbonate films, acrylic films (such as polymethyl methacrylate films), polystyrene films, polyester films, polyolefin films, alkylene resin films, melamine resin films, triacetyl cellulose films, ABS films, AS films, norbornene-based resin films, cyclic olefin films, polyvinyl alcohol films, etc. In one embodiment, the thickness (substrate) is preferably 10 μm to 2000 μm. In one embodiment, the thickness (cured product layer) is preferably 0.1 μm to 20 μm. (Coating step) Coating methods examples include bar coater coating, wire bar coating, Mayer bar coating, air knife coating, gravure coating, reverse gravure coating, offset printing, flexographic printing, screen printing method, etc. (Active energy ray curing step) Active energy rays examples include ultraviolet rays, electron beams, etc. Ultraviolet light sources examples include xenon lamps, high-pressure mercury lamps, metal halide lamps, etc. In the case of using a high-pressure mercury lamp, preferable hardening conditions include the following conditions. Lamp output: 25 W / cm to 160 W / cm UV illuminance: 10 mW / cm 2 ~800 mW / cm 2 Accumulated light quantity: 25 mJ / cm 2 ~2000 mJ / cm 2 Transport speed: 1 m / min to 50 m / min In the case of using an electron beam, preferable hardening conditions include the following conditions. Acceleration voltage: 10 kV to 300 kV Transport speed: 5 m / min to 50 m / min [Examples] Hereinafter, the present invention will be specifically described by way of examples and comparative examples. However, the above description and the following examples are not described for the purpose of limiting the present invention. The present invention is limited to the scope of the patent application. Unless otherwise specified, values such as parts and % are based on mass. Production Example 1: Polymer anionic emulsifier 25.0 g of itaconic acid, 0.13 g of sodium methallylsulfonate, 13.2 g of sodium styrenesulfonate, 77.32 g of acrylamide, 5.9 g of 2-ethylhexyl acrylate, 37.7 g of cyclohexyl methacrylate, 220 g of water, 250 g of isopropanol, and 0.5 g of 2-mercaptoethanol were put into a reaction vessel equipped with a thermometer, a stirring device, a cooling tube, a dropping funnel, and a nitrogen inlet tube. With respect to the mixture, while stirring, nitrogen was bubbled, and at the same time, the temperature was raised to 50°C. Next, 2.2 g of ammonium persulfate (APS) was added and the temperature was raised to 80°C, and stirring was carried out for 180 minutes. Further, steam was blown in and isopropanol was distilled off. Then, water was added so that the solid content concentration became 25% and it was cooled to obtain a polymer anionic emulsifier. Unless otherwise specifically mentioned, other examples are changed as shown in the following table, and the rest is carried out in the same manner as described above. [Table 1] MAA: Methyl methacrylate IA: Itaconic acid SMAS: Sodium methallylsulfonate NASS: Sodium styrenesulfonate AM: Acrylamide HPA: 3-Hydroxypropyl acrylate 6EGA: Product name "New Frontier PE-300", manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., polyethylene glycol diacrylate MMA: Methyl methacrylate 2EHA: 2-Ethylhexyl acrylate CHMA: Cyclohexyl methacrylate ST: Styrene αST: α-Methylstyrene The weight average molecular weight was measured under the following conditions. Measuring instrument: manufactured by Tosoh Corporation, GPC (model: HLC-8220) Column: one guard column TSKgel guardcolumn α and two TSK-GEL α-M columns (temperature 40 °C) manufactured by Tosoh Corporation Detector: TDA model 301 (concentration detector, 90° light scattering detector, and viscosity detector (temperature 40 °C)) manufactured by VISCOTECH Co., Ltd., RALLS method Eluent: 0.02M NANO 3 / CH 3 CN = 80 / 20WT% Sample concentration: 0.5WT% Development temperature: 40 °C Standard substance: Polyethylene oxide Flow rate: 1.0 mL / minute Measurement sample: First, the eluent was added so that the concentration of the measurement sample became 0.5% in terms of the non-volatile component concentration. Next, an aqueous sodium hydroxide solution was added until the pH reached 10 to 12. Further, it was immersed in a hot water bath at 80 °C or higher for 1 hour. Thereafter, the pH was adjusted to 6 to 8 with sulfuric acid and diluted to 0.025% with the eluent for measurement. Example 1: Actinic energy ray curable composition 100 parts of dipentaerythritol hexaacrylate and 3 parts of 2,4,6-trimethylbenzoyl diphenylphosphine oxide were added to a flask equipped with a stirrer, thermometer, and reflux condenser, and uniformly stirred at 85 °C for 1 hour. After complete dissolution, 1 part of a low molecular weight anionic emulsifier (RE-1000L), 1 part of a high molecular weight anionic emulsifier (Production Example 1), and 4.7 parts of water were added while maintaining the temperature at 40 °C, and kneaded at 40 °C for 1 hour. Thereafter, 44.6 parts of water was slowly added to adjust the non-volatile component, and emulsification was carried out to obtain an actinic energy ray curable composition (non-volatile component concentration 50 mass%). Unless otherwise specified, other examples were changed as shown in the following table, and the rest was carried out in the same manner as described above. [Table 2] 2,4,6-Trimethylbenzoyl diphenylphosphine oxide: Product name "Omnirad TPO", manufactured by IGM Resins Co., Ltd. RE-1000L: Product name "Amino ion RE-1000L", manufactured by Nippon Emulsion Co., Ltd., ammonium methyl acrylate of epoxyethane sulfonic acid containing a polycyclic phenyl skeleton S-70: Product name "NEO-HITENOL S-70", manufactured by Daiichi Kogyo Seiyaku Co., Ltd., sodium polyoxyethylene alkyl sulfosuccinate F-13: Product name "NEO-HITENOL F-13", manufactured by Daiichi Kogyo Seiyaku Co., Ltd., sodium polyoxyethylene alkyl sulfosuccinate containing a styrene skeleton N-707: Product name "Newcol 707", manufactured by Nippon Emulsion Co., Ltd., anionic emulsifier DPHA: Dipentaerythritol hexaacrylate, product name "MIRAmER M600", manufactured by MIWON Co., Ltd. 40H: Polyfunctional urethane acrylate, product name "DPHA-40H", manufactured by Nippon Kayaku Co., Ltd. 9550W: A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, product name "NK ester A-9550W", manufactured by Shin-Nakamura Chemical Co., Ltd. Emulsifying property <Evaluation criteria> ○: The whole emulsion is dispersed. ×: A part of the emulsion is oily. Mechanical stability The active energy ray-curable composition was dispersed under the following conditions. Disperser: Disperser (T.K. HOMO DISPER, manufactured by PRIMIX Co., Ltd.) Evaluation temperature: 40 °C Rotational speed: 3000 rpm Centrifugal force: 300 g Rotation time: 30 minutes <Evaluation criteria> ○: No emulsion layering. ×: There is emulsion layering. High-temperature stability The active energy ray-curable composition was kept at 50 °C for three months. <Evaluation criteria> ○: No precipitation visually. ×: Complete precipitation

Claims

1. An active energy line curing composition, wherein the active energy line curing composition comprises a low molecular weight anionic emulsifier, a high molecular weight anionic emulsifier, poly(meth)acrylate, and water, wherein the low molecular weight anionic emulsifier has a weight average molecular weight of less than 10,000, wherein the low molecular weight anionic emulsifier is polyoxyalkylene sulfonate ammonium (meth)acrylate, and the high molecular weight anionic emulsifier has a weight average molecular weight of 10,000 to 500,000.

2. A hardener, which is a hardener of the active energy line hardener composition as described in claim 1.

3. A laminate comprising the hardened material as described in claim 2.