Active energy ray-curable composition and cured product

Abstract

To provide an active energy ray-curable resin composition which has high curability and excellent storage stability and whose cured product is excellent in water vapor barrier properties, adhesion, and hardness of a cured coating film.SOLUTION: An active energy ray-curable composition comprises: a nitrogen atom-containing monomer(s) (A); a mono- to bi-functional (meth)acrylate (B) having an aromatic ring; a mono- to bi-functional (meth)acrylate (C) having an alicyclic skeleton; a bifunctional (meth)acrylate (D) represented by general formula (1); and a photopolymerization initiator (E). (A) is an N-substituted (meth)acrylamide (A-1) and / or an N-vinyl compound (A-2). Based on the total weight of the (A), (B), (C), (D), and (E), the total content of (A) is 8-35 wt.%, the content of (B) is 15-50 wt.%, the content of (C) is 5-35 wt.%, the content of (D) is 5-35 wt.%, and the content of (E) is 2-20 wt.%.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an active energy ray-curable composition and a cured product thereof. [Background technology]

[0002] Conventionally, development of curable compositions that are cured by active energy rays such as ultraviolet rays or electron beams or by heat has been progressing. In recent years, active energy ray-curable compositions, among others, have been increasingly used in fields such as coating agents, paints, and printing inks due to their fast curing rate. In recent years, the development of various active energy ray-curable compositions that are particularly compatible with plastic substrates has become important, and it is desired that these compositions wet and spread well on plastic substrates, adhere well after curing, form coating films with high hardness, and further have high water vapor barrier properties. As a method for improving adhesion to plastic substrates, Patent Document 1 proposes a coating resin composition comprising a component compatible with the plastic substrate (triacetyl cellulose; TAC) and a compound having a polar group. However, the water vapor barrier properties of this composition were insufficient (Patent Document 1).

[0003] Meanwhile, there is growing demand for curable compositions with high curability that can be cured using ultraviolet irradiation equipment with LED light sources. LED light sources have the advantages of low power consumption and low ozone generation, resulting in low running costs and minimal impact on the natural environment. However, because LED light sources emit light at a single wavelength, they emit less total ultraviolet energy and generate less radicals from photopolymerization initiators than ultraviolet lamp light sources, such as high-pressure mercury lamps, ultra-high-pressure mercury lamps, and metal halide lamps, which emit ultraviolet light over a wide wavelength range. This has resulted in the problem of reduced curability of conventional curable compositions, making it difficult to obtain coatings with high hardness.

[0004] Patent Document 2 proposes a hard coat coating liquid containing a monomer or oligomer having acrylate as the main component and a polythiol compound having two or more thiol groups as a curable composition that has high curability and can produce a coating film with high hardness. However, this composition has insufficient storage stability and thickens when stored at room temperature. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2011-132322 [Patent Document 2] Japanese Patent Application Laid-Open No. 2012-197383 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide an active energy ray-curable resin composition that has high curability and excellent storage stability, and that produces a cured product that is excellent in water vapor barrier property, adhesion to a TAC film substrate, and hardness of a cured coating film. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to achieve the above-mentioned object, and have arrived at the present invention. That is, the present invention relates to an active energy ray-curable composition containing a nitrogen atom-containing monomer (A), a mono- or bifunctional (meth)acrylate (B) having an aromatic ring, a mono- or bifunctional (meth)acrylate (C) having an alicyclic skeleton, a bifunctional (meth)acrylate (D) represented by the following general formula (1), and a photopolymerization initiator (E), wherein the nitrogen atom-containing monomer (A) is an N-substituted (meth)acrylamide (A-1) and / or an N-vinyl compound (A-2), the mono- or difunctional (meth)acrylate (C) having an alicyclic skeleton is at least one selected from the group consisting of cyclohexyl methacrylate, t-butylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, 1-ethylcyclopentyl acrylate, and tricyclodecane dimethanol diacrylate; Based on the total weight of (A), (B), (C), (D) and (E), the total content of (A) is 8% by weight to 35% by weight, the content of (B) is 15% by weight to 50% by weight, and the content of (C) is10 The content of (D) is 5% by weight to 35% by weight, and the content of (E) is 2% by weight to 20% by weight. CH2=CR 2 -COO-R 1 -OCOCR 2 =CH2(1) [In general formula (1), R 1 represents an alkylene group having 4 to 12 carbon atoms, and two R 2 are each independently a hydrogen atom or a methyl group. [Effects of the Invention]

[0008] The active energy ray-curable composition of the present invention has high curability and excellent storage stability, and exhibits the effects of providing a cured product with excellent water vapor barrier properties, adhesion to a TAC film substrate, and hardness of the cured coating film. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention provides an active energy ray-curable composition containing a nitrogen atom-containing monomer (A), a mono- or difunctional (meth)acrylate having an aromatic ring (B), a mono- or difunctional (meth)acrylate having an alicyclic skeleton (C), a bifunctional (meth)acrylate (D) represented by the following general formula (1), and a photopolymerization initiator (E), wherein the nitrogen atom-containing monomer (A) is an N-substituted (meth)acrylamide (A-1) and / or an N-vinyl compound (A-2), and the total content of (A) is 8% by weight to 35% by weight, the content of (B) is 15% by weight to 50% by weight, the content of (C) is 5% by weight to 35% by weight, the content of (D) is 5% by weight to 35% by weight, and the content of (E) is 2% by weight to 20% by weight, based on the total weight of (A), (B), (C), (D), and (E), respectively. CH2=CR 2 -COO-R 1 -OCOCR 2 =CH2(1) [In general formula (1), R 1 represents an alkylene group having 4 to 12 carbon atoms, and two R2 are each independently a hydrogen atom or a methyl group.

[0010] In the present invention, "(meth)acrylate" means methacrylate or acrylate. In the present invention, "(meth)acrylic" means methacrylic or acrylic.

[0011] In the present invention, the nitrogen atom-containing monomer (A) is an N-substituted (meth)acrylamide (A-1) and / or an N-vinyl compound (A-2).

[0012] In the present invention, the N-substituted (meth)acrylamide (A-1) means a (meth)acrylamide in which one or two hydrogen atoms of the amino group have been substituted with a substituent such as a hydrocarbon group. Examples of N-substituted (meth)acrylamides include N-alkoxy(meth)acrylamides, N-alkyl(meth)acrylamides, N-alkoxyalkyl(meth)acrylamides, N-hydroxyalkyl(meth)acrylamides, N,N-dialkyl(meth)acrylamides, N-alkoxy-N-alkyl(meth)acrylamides, and cyclic amides having an N-(meth)acryloyl group (such as N-acryloylmorpholine). Examples of N-alkoxy(meth)acrylamides include N-methoxy(meth)acrylamide, N-ethoxy(meth)acrylamide, N-propoxy(meth)acrylamide, and N-butoxy(meth)acrylamide. Examples of N-alkyl(meth)acrylamides include N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, and N-butyl(meth)acrylamide. Examples of N-alkoxyalkyl(meth)acrylamides include Nn-butoxymethylacrylamide. Examples of N-hydroxyalkyl(meth)acrylamides include N-hydroxyethyl(meth)acrylamide. Examples of N,N-dialkyl(meth)acrylamides include N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-dipropyl(meth)acrylamide, N,N-diisopropyl(meth)acrylamide, N,N-dibutyl(meth)acrylamide, N,N-diisobutyl(meth)acrylamide, N,N-di-tert-butyl(meth)acrylamide, N,N-diheptyl(meth)acrylamide, N,N-dioctyl(meth)acrylamide, N,N-di-tert-octyl(meth)acrylamide, N,N-didodecyl(meth)acrylamide, and N,N-dioctadecyl(meth)acrylamide. Examples of N-alkoxy-N-alkyl(meth)acrylamides include Nn-butoxy-N-methyl(meth)acrylamide, N-methyl-N-methoxy(meth)acrylamide, N-methyl-N-ethoxy(meth)acrylamide, N-methyl-N-propoxy(meth)acrylamide, N-ethyl-N-methoxy(meth)acrylamide, N-ethyl-N-ethoxy(meth)acrylamide, N-ethyl-N-butoxy(meth)acrylamide, N-propyl-N-methoxy(meth)acrylamide, N-propyl-N-ethoxy(meth)acrylamide, N-butyl-N-methoxy(meth)acrylamide, and N-butyl-N-ethoxy(meth)acrylamide. Examples of cyclic amides having an N-(meth)acryloyl group include N-(meth)acryloylmorpholine, N-(meth)acryloylthiomorpholine, N-(meth)acryloylpiperidine, N-(meth)acryloylpyrrolidine, and N-(meth)acryloylpiperidine. In the present invention, these N-substituted (meth)acrylamides (A-1) may be used alone or in combination of two or more. Of these N-substituted (meth)acrylamides (A-1), from the viewpoint of curability, N-alkoxyalkyl(meth)acrylamides, N-hydroxyalkyl(meth)acrylamides, N,N-dialkyl(meth)acrylamides, N-alkoxy-N-alkyl(meth)acrylamides, and cyclic amides having an N-(meth)acryloyl group are preferred, and N,N-dimethylacrylamide, N,N-diethylacrylamide, N-acryloylmorpholine, Nn-butoxymethylacrylamide, and N-hydroxyethylacrylamide are more preferred.

[0013] In the present invention, examples of the N-vinyl compound (A-2) include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylacetamide, N-vinylformamide, 5-methyl-3-vinyl-2-oxazolidinone, N-vinylcarbazole, and N-vinylphthalimide. Of these, from the viewpoint of curability, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylacetamide, N-vinylformamide, and 5-methyl-3-vinyl-2-oxazolidinone are preferred, and N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, and 5-methyl-3-vinyl-2-oxazolidinone are more preferred. The N-vinyl compound (A-2) may be used alone or in combination of two or more.

[0014] The active energy ray-curable composition of the present invention contains a mono- or difunctional (meth)acrylate (B) having an aromatic ring. Examples of the mono- or difunctional (meth)acrylate (B) having an aromatic ring include (meth)acrylates having a benzene ring, a naphthalene ring, an anthracene ring, a biphenyl structure, a bisphenol structure, a fluorene structure, or the like. Examples of (meth)acrylates having a benzene ring include benzyl (meth)acrylate, phenoxybenzyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxyethylene glycol (meth)acrylate, 2-(meth)acryloyloxyethyl-phthalate, nonylphenoxypolyethylene glycol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, and 4-(meth)acryloyloxybenzophenone. Examples of (meth)acrylates having a naphthalene ring include 2-naphthyl (meth)acrylate. Examples of (meth)acrylates having an anthracene ring include 9-anthrylmethyl (meth)acrylate. Examples of (meth)acrylates containing a biphenyl structure include biphenylmethyl (meth)acrylate, o-phenylphenolethyl (meth)acrylate, and o-phenylphenoldiethylene glycol (meth)acrylate. Examples of (meth)acrylates having a bisphenol structure include EO adduct di(meth)acrylate of bisphenol A, PO adduct di(meth)acrylate of bisphenol A, cumylphenoxyethyl (meth)acrylate, etc. Examples of (meth)acrylates having a fluorene structure include bisphenoxyethanol fluorene di(meth)acrylate, 9,9-bis(4-hydroxyphenyl)fluorene EO adduct di(meth)acrylate, etc. In the present invention, these mono- or difunctional (meth)acrylates (B) may be used singly or in combination of two or more. Among these mono- or difunctional (meth)acrylates (B), from the viewpoint of curability and water vapor barrier properties, preferred are benzyl (meth)acrylate, phenoxybenzyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 2-naphthyl (meth)acrylate, 9-anthrylmethyl (meth)acrylate, biphenylmethyl (meth)acrylate, o-phenylphenolethyl (meth)acrylate, EO adduct di(meth)acrylate of bisphenol A, PO adduct di(meth)acrylate of bisphenol A, cumylphenoxyethyl (meth)acrylate, 9,9-bis(4-hydroxyphenyl)phenyl Preferred are fluorene EO adduct di(meth)acrylate, more preferred are benzyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, o-phenylphenolethyl (meth)acrylate, bisphenol A EO adduct di(meth)acrylate, and 9,9-bis(4-hydroxyphenyl)fluorene EO adduct di(meth)acrylate, and particularly preferred are benzyl acrylate, 2-phenoxyethyl acrylate, o-phenylphenolethyl acrylate, bisphenol A EO adduct diacrylate, and 9,9-bis(4-hydroxyphenyl)fluorene EO adduct diacrylate.

[0015] The active energy ray-curable composition of the present invention contains a mono- or difunctional (meth)acrylate (C) having an alicyclic skeleton. Examples of the mono- or difunctional (meth)acrylate (C) having an alicyclic skeleton include isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, adamantyl (meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, and 2-(meth)acryloyloxyethyl Examples of the alkyl acrylate include hexahydrophthalic acid, 3-hydroxy-1-adamantyl (meth)acrylate, 1-adamantyl (meth)acrylate, 2-methyl-2-adamantyl (meth)acrylate, 2-isopropyladamantyl-2-yl (meth)acrylate, tetrahydrodicyclopentadienyl (meth)acrylate, 5-(meth)acroyloxy-2,6-norbornane carbolactone, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, 1,3-adamantanediol di(meth)acrylate, cyclopentyl (meth)acrylate, and cyclodecane dimethanol di(meth)acrylate. In the present invention, one type of these mono- or difunctional (meth)acrylates (C) having an alicyclic skeleton may be used alone, or two or more types may be used in combination. Among these mono- or difunctional (meth)acrylates (C) having an alicyclic skeleton, preferred from the viewpoint of curability are isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, tetrahydrodicyclopentadienyl (meth)acrylate, 5-(meth)acroyloxy-2,6-norbornane carbolactone, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, cyclopentyl ( Preferred are isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclodecane dimethanol di(meth)acrylate, and particularly preferred are isobornyl acrylate, cyclohexyl methacrylate, t-butylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, 1-ethylcyclopentyl acrylate, and tricyclodecane dimethanol diacrylate.

[0016] The active energy ray-curable composition of the present invention contains a bifunctional (meth)acrylate (D) represented by general formula (1). CH2=CR 2 -COO-R 1 -OCOCR 2 =CH2(1) [In general formula (1), R 1 represents an alkylene group having 4 to 12 carbon atoms, and two R 2 are each independently a hydrogen atom or a methyl group. In general formula (1), R 1 represents an alkylene group having 4 to 12 carbon atoms, and specific examples thereof include a 1,4-butylene group, a neopentylene group, a 3-methyl-1,5-pentylene group, a 1,6-hexylene group, a 1,9-nonylene group, a 1,10-decylene group, and a 1,12-dodecane group. Of these, from the viewpoint of hardness of the cured product, 1,4-butylene group, neopentylene group, 3-methyl-1,5-pentylene group and 1,10-decylene group are preferred. Two R's 2 are each independently a hydrogen atom or a methyl group, and from the viewpoint of hardness of the cured product, preferably both are hydrogen atoms. Examples of the bifunctional methacrylate (D) represented by general formula (1) include 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,9-nonanediol diacrylate, 1,6-hexanediol diacrylate, and 1,12-dodecanediol di(meth)acrylate. These bifunctional (meth)acrylates (D) can be used alone or in combination of two or more. Of these, from the viewpoint of coating film curability, 1,4-butanediol di(meth)acrylate, neopentyl glycol diacrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,9-nonanediol diacrylate, and 1,10-decanediol diacrylate are preferred, and 1,4-butanediol diacrylate, neopentyl glycol diacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,9-nonanediol diacrylate, and 1,10-decanediol diacrylate are more preferred.

[0017] The active energy ray-curable composition of the present invention contains a photopolymerization initiator (E). The photopolymerization initiator (E) is not limited as long as it generates radicals, ions, etc. when irradiated with active energy rays and initiates a polymerization reaction of the monomers, and a photopolymerization initiator that generates radicals when irradiated with active energy rays can be preferably used. Examples of the photopolymerization initiator (E) include acylphosphine oxide compounds (E1), α-hydroxyalkylphenone compounds (E2), α-aminoalkylphenone compounds (E3), ketal compounds (E4), benzoyl formate compounds (E5), thioxanthone compounds (E6), benzophenone compounds (E7), and oxime ester compounds (E8).

[0018] Examples of the acylphosphine oxide compound (E1) include (2,4,6-trimethylbenzoyl)-diphenylphosphine oxide (Irgacure TPO), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure 819), and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0019] Examples of the α-hydroxyalkylphenone compound (E2) include 1-hydroxycyclohexyl phenyl ketone and 2-hydroxy-2-methyl-1-phenylpropan-1-one.

[0020] Examples of the α-aminoalkylphenone compound (E3) include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-butan-1-one, and 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-butan-1-one.

[0021] Examples of the ketal compound (E4) include benzyl dimethyl ketal.

[0022] Examples of the benzoyl formate compounds (E5) include methyl benzoyl formate.

[0023] Examples of the thioxanthone compounds (E6) include 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone.

[0024] Examples of the benzophenone-based compound (E7) include benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 4,4'-bismethylaminobenzophenone.

[0025] Examples of the oxime ester compound (E8) include 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) and 1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl]-ethanone-1-(O-acetyloxime).

[0026] In the present invention, these photopolymerization initiators (E) may be used alone or in combination of two or more. Of these photopolymerization initiators (E), from the viewpoints of curability and coloration of the cured product, the acylphosphine oxide-based compound (E1) and the α-hydroxyalkylphenone-based compound (E2) are preferred, the acylphosphine oxide-based compound (E1) is more preferred, and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide and (2,4,6-trimethylbenzoyl)-diphenylphosphine oxide are particularly preferred.

[0027] In the active energy ray-curable composition of the present invention, when the composition contains an N-substituted (meth)acrylamide (A-1) and an N-vinyl compound (A-2), the content of the nitrogen atom-containing monomer (A) is the sum of the contents of (A-1) and (A-2), and is 8 to 35% by weight, preferably 8 to 30% by weight, and more preferably 10 to 25% by weight, based on the total weight of (A), (B), (C), (D), and (E). If it is less than 8% by weight, the hardness and adhesion of the cured product will be insufficient, and if it exceeds 35% by weight, the storage stability and water vapor barrier properties of the cured product will be insufficient.

[0028] The content of the aromatic ring-containing mono- or di-functional (meth)acrylate (B) is 15% by weight to 50% by weight, preferably 20% by weight to 45% by weight, and more preferably 20% by weight to 40% by weight, based on the total weight of (A), (B), (C), (D) and (E). If it is less than 15% by weight, the hardness and water vapor barrier properties will be insufficient, and if it exceeds 50% by weight, the adhesiveness of the cured product will be insufficient.

[0029] The content of the mono- or difunctional (meth)acrylate (C) having an alicyclic skeleton is 5% by weight to 35% by weight, preferably 10% by weight to 35% by weight, and more preferably 10% by weight to 30% by weight, based on the total weight of (A), (B), (C), (D), and (E). If it is less than 5% by weight, the adhesion will be insufficient, and if it exceeds 35% by weight, the hardness of the cured product will be insufficient.

[0030] The content of the bifunctional (meth)acrylate (D) represented by general formula (1) is 5 to 35% by weight, preferably 10 to 35% by weight, and more preferably 10 to 30% by weight, based on the total weight of (A), (B), (C), (D), and (E). If it is less than 5% by weight, the curability will be insufficient, and if it exceeds 35% by weight, the adhesiveness of the cured product will be insufficient.

[0031] The content of the photopolymerization initiator (E) is 2% by weight to 20% by weight, more preferably 3% by weight to 15% by weight, and even more preferably 4% by weight to 13% by weight, based on the total weight of (A), (B), (C), (D) and (E). If it is less than 2% by weight, the curability will be insufficient, and if it exceeds 20% by weight, the hardness and storage stability of the cured product will be insufficient.

[0032] The active energy ray-curable composition of the present invention may contain at least one polymer (F) selected from the group consisting of styrene (anhydride) maleic acid copolymer, styrene (meth)acrylic copolymer, and polystyrene. Styrene (and maleic anhydride) copolymer is a polymer containing styrene and maleic acid and / or maleic anhydride as essential constituent monomers.

[0033] A styrene (meth)acrylic copolymer is a polymer containing styrene and (meth)acrylate as essential constituent monomers. Examples of the (meth)acrylate include (meth)acrylic acid, isobornyl acrylate, cyclohexyl acrylate, cyclohexyl methacrylate, t-butylcyclohexyl acrylate, t-butylcyclohexyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, dicyclopentanyl acrylate, dicyclopentenyl acrylate, methyl (meth)acrylate, t-butyl (meth)acrylate, n-butyl acrylate, isobutyl acrylate, tert-butyl acrylate, acrylate, hexyl acrylate, isoamyl acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, isostearyl (meth)acrylate, benzyl acrylate, phenoxyethyl acrylate, methylphenoxyethyl acrylate, phenoxydiethylene glycol acrylate, phenyl (meth)acrylate p) acrylate, phenoxymethyl (meth)acrylate, 2-ethylhexyl diglycol (meth)acrylate, butoxyethyl (meth)acrylate, butoxymethyl (meth)acrylate, methoxypropylene mono(meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-(2-methoxyethoxy)ethyl (meth)acrylate, 2-(2-butoxyethoxy)ethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl acrylate, glycidyl acrylate, tetrahydrofurfuryl acrylate, Examples include cyclic trimethylolpropane formal acrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, polyethylene oxide monomethyl ether (meth)acrylate, methoxydipropylene glycol acrylate, polyethylene glycol (PEG) mono(meth)acrylate, polypropylene glycol (PPG) mono(meth)acrylate, and polycaprolactone 2-hydroxyethyl acrylate ester.

[0034] Of these, from the viewpoint of compatibility with other components, monofunctional (meth)acrylates are preferred, and (meth)acrylic acid, methyl (meth)acrylate and n-butyl acrylate are more preferred.

[0035] From the viewpoint of water vapor barrier property, the content of styrene in the styrene (meth)acrylic copolymer is preferably 65% ​​by weight or more, more preferably 70% by weight or more, and particularly preferably 80% by weight or more, based on the weight of polymer (F) as a constituent monomer.

[0036] Polystyrene is a polymer whose constituent monomer is styrene. The weight average molecular weight of the polymer (F) is preferably more than 2,000 and not more than 20,000 from the viewpoint of water vapor barrier properties and solubility.

[0037] From the viewpoint of curability and water vapor barrier property, the content of polymer (F) is preferably 0.5 to 40% by weight, more preferably 1 to 35% by weight, and particularly preferably 5 to 30% by weight, based on the total weight of (A) to (E).

[0038] The active energy ray-curable composition of the present invention may contain a sensitizer (G). Examples of the sensitizer (G) include sensitizers having a thioxanthone skeleton and other sensitizers. Examples of sensitizers having a thioxanthone skeleton include thioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and Omnipol TX. Examples of sensitizers other than those having a thioxanthone skeleton include Anthracure UVS-581. These sensitizers can be used alone or in combination of two or more. From the viewpoint of photosensitivity, 2,4-diethylthioxanthone is preferred. The sensitizer (G) may be used alone or in combination of two or more kinds.

[0039] From the viewpoint of photosensitivity, the content of the sensitizer (G) is preferably 0.2 to 10% by weight, and more preferably 0.5 to 5% by weight, based on the total weight of the (A), (B), (C), (D), and (E).

[0040] The active energy ray-curable composition of the present invention may contain a leveling agent (H). Examples of the leveling agent (H) include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, fluorine surfactants, and silicone surfactants. Of these leveling agents (H), from the viewpoints of wettability and prevention of foaming, silicone surfactants and fluorosurfactants are preferred, and silicone surfactants are more preferred. The leveling agent (H) may be used alone or in combination of two or more kinds. The amount of the leveling agent (H) used is preferably 0.01 to 3% by weight, and more preferably 0.05 to 1% by weight, based on the total weight of (A), (B), (C), (D), and (E).

[0041] The active energy ray-curable composition of the present invention may contain a solvent (I). Examples of the solvent (I) include ketone solvents, ester solvents, alcohol solvents, ether solvents, glycol solvents, carbonate solvents, aromatic hydrocarbon solvents, aliphatic hydrocarbon solvents, and mixed solvents of two or more of these. Of these solvents (I), from the viewpoint of compatibility with other components and adhesion, ketone solvents and ester solvents are preferred, and ketone solvents are more preferred. The amount of solvent (I) used is preferably 20% by weight to 240% by weight, and more preferably 40% by weight to 100% by weight, based on the total weight of (A), (B), (C), (D), and (E).

[0042] The active energy ray-curable composition of the present invention may further contain a polymerization inhibitor, a tackifier, an antifoaming agent, a thixotropy-imparting agent, a slip agent, a flame retardant, an antistatic agent, a solvent, an antioxidant, and the like, depending on the intended use.

[0043] The active energy ray-curable composition of the present invention can be obtained by stirring and mixing the above-mentioned components in a suitable container such as a glass beaker, a can, or a plastic cup with a stirring rod, spatula, or the like, or by mixing with a known mixing device (a mixing device equipped with a stirring spring such as a paddle-type mixing device, a dissolver, a ball mill, or a planetary mixer). The active energy ray-curable composition is preferably liquid at room temperature, and its viscosity at 25°C is preferably 1 to 100 mPa·s, more preferably 2 to 50 mPa·s.

[0044] To obtain a cured product of the active energy ray-curable composition, the active energy ray-curable composition is applied to a substrate by a known method and then cured by irradiating with active energy rays. The active energy rays in the present invention include ultraviolet rays, electron beams, X-rays, infrared rays, and visible light. The active energy rays used for curing the active energy ray-curable composition of the present invention can be adjusted by selecting the photopolymerization initiator. The photopolymerization initiator (E) can be photocured by irradiation with active energy rays having a wavelength of preferably 200 to 700 nm, and more preferably by irradiation with light (ultraviolet light) having a wavelength of 200 to 400 nm. Examples of light sources that can be used to emit ultraviolet light include high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and high-power metal halide lamps (see "Latest Trends in UV / EB Curing Technology," edited by RadTech Research Group, CMC Publishing, p. 138, 2006) and LEDs. Compared to other light sources, LEDs consume less power and generate less ozone, have lower running costs, and are less environmentally hazardous. The irradiation dose of ultraviolet light when photocuring the active energy ray-curable composition of the present invention is preferably 10 to 10,000 mJ / cm from the viewpoints of the curability of the composition and the flexibility of the cured product. 2, and more preferably 20 to 2,000 mJ / cm 2 is. For the purpose of accelerating the curing rate of the active energy ray-curable composition of the present invention, heating may be carried out during and / or after irradiation with active energy rays. The heating temperature is preferably 30°C to 200°C, more preferably 35°C to 150°C, and particularly preferably 40°C to 120°C.

[0045] The substrate to which the active energy ray-curable composition of the present invention is applied may be a film-, sheet-, or plate-shaped substrate. The material of the substrate may be appropriately selected depending on the intended use, and examples thereof include polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylic resins such as triacetyl cellulose (TAC), polycarbonate resins, methyl methacrylate copolymers, styrene resins, polysulfone resins, polyethersulfone resins, polycarbonate resins, vinyl chloride resins, and polymethacrylimide resins. Inorganic substrates such as glass substrates can also be used.

[0046] The active energy ray-curable composition of the present invention can be applied to a substrate by known coating methods such as spin coating, roll coating, and spray coating, as well as known printing methods such as lithographic printing, carton printing, metal printing, offset printing, screen printing, and gravure printing. In addition, the composition can also be applied by an inkjet method in which fine droplets are continuously ejected.

[0047] The cured product of the present invention may be obtained by irradiating the active energy ray-curable composition of the present invention, which has been applied to the substrate, with active energy, and curing the composition. The cured product can be used for various coatings, inks (UV printing inks, UV inkjet printing inks, etc.), and paints. [Example]

[0048] The present invention will be further explained below with reference to examples, but the present invention is not limited to these examples. In addition In the following, Examples 4, 7, 9 and 11 refer to Reference Examples 1 to 4.

[0049] <Production example 1> Polymer (F-1) An autoclave was charged with 250 parts by weight of xylene, purged with nitrogen, and then heated to 185°C in a sealed state with stirring. A mixed solution of 472 parts by weight of styrene, 15 parts by weight of n-butyl acrylate, 13 parts by weight of acrylic acid, 5 parts by weight of di-t-butyl peroxide, and 100 parts by weight of xylene was added dropwise over 3 hours while controlling the temperature inside the autoclave at 185°C to allow polymerization. The temperature was maintained at 185°C for another hour to complete the polymerization. The temperature was then increased to 170°C while distilling off the xylene, and the pressure was reduced. Desolvation was continued at a pressure of 1 kPa or less, and the xylene content in the resin was confirmed to be 400 ppm or less, yielding Polymer (F-1). The Mw of the resulting Polymer (F-1) was 10,000.

[0050] <Production example 2> Polymer (F-2) An autoclave was charged with 250 parts by weight of xylene, purged with nitrogen, and then heated to 170°C in a sealed state with stirring. A mixed solution of 411 parts by weight of styrene, 80 parts by weight of n-butyl acrylate, 9 parts by weight of methacrylic acid, 3 parts by weight of di-t-butyl peroxide, and 100 parts by weight of xylene was added dropwise over 3 hours while controlling the temperature inside the autoclave at 170°C to allow polymerization. The temperature was maintained at 170°C for another hour to complete the polymerization, and the temperature was then raised to 170°C while distilling off the xylene, after which the pressure was reduced. Desolvation was continued at a pressure of 1 kPa or less, and the xylene content in the resin was confirmed to be 400 ppm or less, yielding Polymer (F-2). The Mw of the resulting Polymer (F-2) was 15,000.

[0051] <Production Example 3> Polymer (F-3) An autoclave was charged with 250 parts by weight of xylene, purged with nitrogen, and then heated to 200°C in a sealed state with stirring. A mixed solution of 487 parts by weight of styrene, 13 parts by weight of maleic anhydride, 15 parts by weight of di-t-butyl peroxide, and 110 parts by weight of xylene was added dropwise over 3 hours while controlling the temperature inside the autoclave at 200°C, allowing polymerization to occur. The temperature was maintained for another 1 hour to complete the polymerization, and the temperature was then raised to 170°C while distilling off the xylene, after which the pressure was reduced. Desolvation was continued at a pressure of 1 kPa or less, and the xylene content in the resin was confirmed to be 400 ppm or less, yielding Polymer (F-3). The Mw of the resulting Polymer (F-3) was 5000.

[0052] <Production example 4> Polymer (F-4) An autoclave was charged with 250 parts by weight of xylene, purged with nitrogen, and then heated to 200°C in a sealed state with stirring. A mixed solution of 500 parts by weight of styrene, 25 parts by weight of di-t-butyl peroxide, and 110 parts by weight of xylene was added dropwise over 3 hours while controlling the temperature inside the autoclave at 200°C, allowing polymerization. The temperature was maintained for another 1 hour to complete the polymerization, and the temperature was then raised to 170°C while distilling off the xylene, after which the pressure was reduced. Desolvation was continued at a pressure of 1 kPa or less, and the xylene content in the resin was confirmed to be 400 ppm or less, yielding Polymer (F-4). The Mw of the resulting Polymer (F-4) was 3,000.

[0053] <Examples 1 to 13 and Comparative Examples 1 to 10> According to the blending parts (parts by weight) in Table 1 or Table 2, a nitrogen atom-containing monomer (A), a mono- or difunctional (meth)acrylate (B) having an aromatic ring, a mono- or difunctional (meth)acrylate (C) having an alicyclic skeleton, a bifunctional (meth)acrylate (D) represented by general formula (1), a photopolymerization initiator (E), and, if necessary, a polymer (F), a leveling agent (H), and a solvent (I) were charged into a glass container and stirred until uniform, thereby obtaining active energy ray-curable compositions of Examples 1 to 13 and Comparative Examples 1 to 10.

[0054] [Table 1]

[0055] [Table 2]

[0056] Details of the raw materials represented by the symbols in Tables 1 and 2 are as follows: (A-1-1): N-acryloylmorpholine [ACMO: manufactured by KJ Chemicals Co., Ltd.] (A-1-2): N,N-dimethylacrylamide [DMAA: manufactured by KJ Chemicals Co., Ltd.] (A-1-3): N,N-diethylacrylamide [DEAA: manufactured by KJ Chemicals Co., Ltd.] (A-1-4): Nn-butoxymethylacrylamide [NBMA: manufactured by Shinryo Corporation] (A-1-5): N-hydroxyethyl acrylamide [HEAA: manufactured by KJ Chemicals Co., Ltd.] (A-2-1): N-vinylpyrrolidone [Tokyo Chemical Industry Co., Ltd.] (A-2-2): 5-methyl-3-vinyl-2-oxazolidinone [trade name: vinylmethyloxazolidinone (VMOX), manufactured by BASF] (A-2-3): N-vinylcaprolactam [manufactured by BASF] (A-2-4): N-vinylimidazole [Tokyo Chemical Industry Co., Ltd.] (B-1): Benzyl acrylate [trade name: Viscoat 160, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (B-2): 2-phenoxyethyl methacrylate [Tokyo Chemical Industry Co., Ltd.] (B-3): Phenoxybenzyl methacrylate [trade name: Light Ester POB-A, manufactured by Kyoeisha Chemical Co., Ltd.] (B-4): o-Phenylphenol ethyl acrylate [product name: NK Ester A-LEN-10, Shin-Nakamura Chemical Co., Ltd.] (B-5): EO adduct of bisphenol A (4 moles) [trade name: NK Ester BPE-200, Shin-Nakamura Chemical Co., Ltd.] (B-6): Bisphenoxyethanol fluorene diacrylate [trade name: Miramer HR6042, manufactured by MIWON Co., Ltd.] (C-1): Isobornyl acrylate [product name: Light Acrylate IB-XA, manufactured by Kyoeisha Chemical Co., Ltd.] (C-2): Cyclohexyl methacrylate [product name: Light Ester CH, manufactured by Kyoeisha Chemical Co., Ltd.] (C-3): t-butylcyclohexyl acrylate [trade name: Miramer M1150, manufactured by Miwon] (C-4): Trimethylcyclohexyl methacrylate [trade name: Satomer CD421, manufactured by Arkema] (C-5): 1-Ethylcyclopentyl acrylate [trade name: 1-Ethylcyclopentyl acrylate, manufactured by Tokyo Chemical Industry Co., Ltd.] (C-6): Tricyclodecane dimethanol diacrylate [product name: Light Acrylate DCPA, manufactured by Kyoeisha Chemical Co., Ltd.] (D-1): Neopentyl glycol diacrylate [product name: Light Acrylate NP-A, manufactured by Kyoeisha Chemical Co., Ltd.] (D-2): 3-methyl-1,5-pentanediol diacrylate [product name: Light Acrylate MPD-A, manufactured by Kyoeisha Chemical Co., Ltd.] (D-3): 1,10-decanediol diacrylate [product name: A-DOD-N, manufactured by Shin-Nakamura Chemical Co., Ltd.] (D-4): 1,9-nonanediol diacrylate [trade name: NK Ester A-NOD-N, manufactured by Shin-Nakamura Chemical Co., Ltd.] (D-5): 1,4-butanediol diacrylate [trade name: Viscoat 195, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (E-1): (2,4,6-trimethylbenzoyl)-diphenylphosphine oxide [trade name: Irgacure TPO, manufactured by BASF] (E-2): Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [trade name: Irgacure 819, manufactured by BASF] (H-1): Silicone surfactant [product name: BYK-333, manufactured by Big Chemie Japan Co., Ltd.] (H-2): Siloxane surfactant [product name: TEGO Twin 4299, manufactured by Tomoe Engineering Co., Ltd.] (I-1): Methyl ethyl ketone [manufactured by Sankyo Chemical Co., Ltd.] (I-2): Diethyl ketone [Tokyo Chemical Industry Co., Ltd.] (I-3): Methyl propyl ketone [Tokyo Chemical Industry Co., Ltd.] (I-4): Cyclopentanone [Tokyo Chemical Industry Co., Ltd.] (I-5): Cyclohexanone [manufactured by Sankyo Chemical Co., Ltd.]

[0057] The viscosity, coating film curability and storage stability of the active energy ray-curable compositions of Examples 1 to 13 and Comparative Examples 1 to 10, as well as the water vapor barrier property, pencil hardness and substrate adhesion of the cured films, were measured or evaluated by the following test methods. The results are shown in Table 3.

[0058] [Table 3]

[0059] [Viscosity evaluation] The viscosity of the active energy ray-curable composition was measured at 25°C using a viscosity measuring device ("Visco Elite B" manufactured by FUNGILAB).

[0060] (1) Coating hardening evaluation Each of the active energy ray-curable compositions obtained in Examples 1 to 13 and Comparative Examples 1 to 10 was applied to a surface-treated 100-μm-thick PET (polyethylene terephthalate) film [Cosin A4 μm 300, manufactured by Toyobo Co., Ltd.] using an applicator to a film thickness of 20 μm. Subsequently, an LED light source ultraviolet irradiation device [model number FJ100 150×20 385, manufactured by Phoseon Technology Co., Ltd., irradiation wavelength 385 nm] was used to apply the coating at an irradiation intensity of 1500 mW / cm. 2 The exposure was performed at a dose of 500 mJ / cm 2 It was. The cured coating film was evaluated for curability immediately after light irradiation and 10 seconds after light irradiation by touching with a finger to determine whether or not there was tack. ○: No tuck ×: With tuck In addition, for the active energy ray-curable compositions rated as × (tacky) in the comparative examples, the water vapor barrier properties and substrate adhesion of the cured film described below could not be evaluated, and this is indicated by × in the table.

[0061] (2) Evaluation of storage stability Each of the active energy ray-curable compositions obtained in Examples 1 to 13 and Comparative Examples 1 to 10 was placed in a light-shielding plastic container with a lid, and was left to stand in a thermostatic chamber at 60°C for 1000 hours, and then the temperature was regulated at 25°C for 1 hour, and the Hazen color index was measured using OME2000 manufactured by Nippon Denshoku Industries Co., Ltd. [Evaluation criteria] 5: Hazen unit color count less than 200 4: Number of Hazen unit colors is 200 or more but less than 250 3: Number of Hazen unit colors is 250 or more but less than 300 2: Number of Hazen unit colors is 300 or more but less than 400 1: Number of Hazen unit colors is 400 or more

[0062] (3) Evaluation of water vapor barrier properties Each of the active energy ray-curable compositions obtained in Examples 1 to 13 and Comparative Examples 1 to 10 was applied to a 40 μm-thick TAC (triacetyl cellulose) film [Fujifilm Corporation, triacetyl cellulose film "TD80UL"] using an applicator to a film thickness of 20 μm. Subsequently, an LED light source ultraviolet irradiation device [model number "FJ100 150 × 20 385, Phoseon Technology Corporation, irradiation wavelength 385 nm] was used to apply the composition to a film thickness of 20 μm. 2 The exposure dose was 500 mJ / cm to prepare a sample for evaluation. 2 In accordance with JIS Z 0208, the moisture permeability after 24 hours at 40°C and 90% RH was measured by the cup method. 5: Moisture permeability [g / m 2 24h is less than 100 4: Moisture permeability [g / m 2 24h] is between 100 and 150 3: Moisture permeability [g / m 2 24h] is between 150 and 250 2: Moisture permeability [g / m 2 24h] is between 250 and 500 1: Moisture permeability [g / m 2 24h] is 500 or more

[0063] (4) Evaluation of pencil hardness (hardness of coating film) Each cured product obtained in "(1) Evaluation of coating film curability" above was left to stand for 16 hours in a room at a temperature of 23±2°C, then placed on a flat glass plate, and the pencil hardness was measured according to the description in JIS K 5600-5-4:1999.

[0064] (5) Evaluation of substrate adhesion (to PET film) Each of the active energy ray-curable compositions obtained in Examples 1 to 13 and Comparative Examples 1 to 10 was applied to a surface-treated 100 μm-thick PET (polyethylene terephthalate) film [trade name: Cosmoshine A4300, manufactured by Toyobo Co., Ltd.] using an applicator to a film thickness of 20 μm. Subsequently, an LED light source ultraviolet irradiation device [model number "FJ100 150×20 385, manufactured by Phoseon Technology Co., Ltd., irradiation wavelength 385 nm] was used to apply the coating at an irradiation intensity of 1500 mW / cm. 2 The exposure dose was 500 mJ / cm to prepare a sample for evaluation. 2 The obtained evaluation sample was allowed to stand for 24 hours in an environment of 23°C and 50% relative humidity, and then the cured coating film on the substrate was cross-cut into 2 mm x 2 mm grids (100 pieces), cellophane adhesive tape was applied to the grids, and the tape was peeled off at a 90-degree angle, and the state of peeling of the cured product from the substrate was visually observed. Two grids were created per sample and evaluated, and the average number of grids where the cured product was not peeled off and adhered to the substrate is shown in Table 3. A grid of 97 or more is necessary, and 100 is preferable.

[0065] (6) Evaluation of substrate adhesion (to TAC film) Samples for evaluation were prepared in the same manner as in "(5) Evaluation of adhesion to substrate" above, except that the substrate was changed from PET film to TAC (triacetyl cellulose) film [triacetyl cellulose film "TD80UL" manufactured by Fujifilm Corporation]. 90-degree peeling was performed on two grids in the same manner as above, and the average number of squares in which the cured product adhered to the substrate without peeling was calculated and is shown in Table 3. The average number must be 97 or more, and 100 is preferable.

[0066] (7) Evaluation of humidity and heat adhesion after 24 hours (against PET film and TAC film) The same evaluation samples as those used in the evaluation of substrate adhesion in (5) and (6) above were prepared and placed in a thermo-hygrostat at a temperature of 85°C and a relative humidity of 85% for 24 hours, and then allowed to stand for 3 hours at 25°C. For each sample, a 90-degree peel test was performed on a grid in the same manner as above, and the average number of squares in which the cured product adhered to the substrate without peeling is shown in Table 3.

[0067] The results in Table 3 show that the active energy ray-curable compositions of Examples 1 to 13 of the present invention have high curability and excellent storage stability, and the coating films of the cured products have excellent water vapor barrier properties, adhesion to the TAC film substrate, and hardness of the cured coating films. On the other hand, the active energy ray-curable composition of Comparative Example 1 was insufficient in storage stability and in water vapor barrier property of the cured product, the active energy ray-curable composition of Comparative Example 2 was insufficient in hardness of the cured product and in adhesion to the TAC film substrate, the active energy ray-curable compositions of Comparative Examples 3, 6, and 7 were insufficient in adhesion to the TAC film substrate, the active energy ray-curable composition of Comparative Example 4 was insufficient in water vapor barrier property and hardness of the cured product, the active energy ray-curable composition of Comparative Example 5 was insufficient in hardness of the cured product, the active energy ray-curable compositions of Comparative Examples 8 and 10 were insufficient in curability of the coating film and were not evaluable, and the active energy ray-curable composition of Comparative Example 9 was insufficient in storage stability and in hardness of the cured product. [Industrial Applicability]

[0068] The active energy ray-curable composition of the present invention has high curability and excellent storage stability, and the cured product has excellent water vapor barrier properties, adhesion to TAC film substrates, and hardness of the cured coating film. Therefore, the composition can be suitably used as a material for various coating agents, inks (UV printing inks, UV inkjet printing inks, etc.), and paints.

Claims

1. An active energy ray-curable composition containing a nitrogen atom-containing monomer (A), a mono- or difunctional (meth)acrylate having an aromatic ring (B), a mono- or difunctional (meth)acrylate having an alicyclic skeleton (C), a bifunctional (meth)acrylate (D) represented by the following general formula (1), and a photopolymerization initiator (E), wherein the nitrogen atom-containing monomer (A) is an N-substituted (meth)acrylamide (A-1) and / or an N-vinyl compound (A-2), and the mono- or difunctional (meth)acrylate having an alicyclic skeleton (C) is cyclohexyl methacrylate, t-butylcyclohexyl ... and the total content of (A) is 8% by weight to 35% by weight, the content of (B) is 15% by weight to 50% by weight, the content of (C) is 10% by weight to 35% by weight, the content of (D) is 5% by weight to 35% by weight, and the content of (E) is 2% by weight to 20% by weight, based on the total weight of (A), (B), (C), (D), and (E). CH ２ =CR ２ -COO-R １ -OCOCR ２ =CH ２ (1) [In general formula (1), R １ represents an alkylene group having 4 to 12 carbon atoms, and two R ２ are each independently a hydrogen atom or a methyl group.

2. The active energy ray-curable composition according to claim 1, wherein the N-substituted (meth)acrylamide (A-1) is at least one selected from the group consisting of N,N-dimethylacrylamide, N,N-diethylacrylamide, N-acryloylmorpholine, N-n-butoxymethylacrylamide, and N-hydroxyethylacrylamide, and the N-vinyl compound (A-2) is at least one selected from the group consisting of N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylacetamide, N-vinylformamide, 5-methyl-3-vinyl-2-oxazolidinone, N-vinylcarbazole, and N-vinylphthalimide.

3. A cured product of the active energy ray-curable composition according to claim 1 or 2.

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