Active energy ray curable composition and its cured product

Abstract

To provide an active energy ray-curable composition excellent in high curability and storage stability, and capable of forming a high hardness-having cured film good in adhesion to a substrate ( particularly adhesion to a hardly adhesive olefin substrate).SOLUTION: An active energy ray-curable composition is an active ray-curable composition including a N-substituted (meth)acryl amide (A), a polymer (B), and a photopolymerization initiation agent (D), where the polymer (B) includes an alicyclic skeleton-having mono functional methacrylate (b1) having a SP value of lower than 10 (cal / cm3)1 / 2, and a monomer (b2) as constitutional monomers, the monomer (b2) is a mono functional (meth)acrylate (b21) having a SP value of 10 (cal / cm3)1 / 2 or higher, and / or a methacrylamide (b22) having a SP value of 10 (cal / cm3)1 / 2 or higher, and the weight average molecular weight of the polymer B is 5,000-70,000.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to an active energy ray curable composition. [Background technology]

[0002] Conventionally, curable compositions that harden with active energy rays such as ultraviolet light and electron beams have been increasingly used in fields such as coatings, paints, and printing inks due to their fast curing speed. In recent years, the development of various active energy ray curable compositions, particularly those for plastic substrates, has become increasingly important. There is a demand for compositions that wet well and spread smoothly on plastic substrates, adhere well after curing, and form highly hard coatings.

[0003] As a method to improve adhesion to plastic substrates, Patent Document 1 proposes a coating resin composition containing a polymer having vinyl ether groups. However, this composition exhibited insufficient adhesion to olefin substrates such as cycloolefin polymers (COP).

[0004] On the other hand, there is a growing demand for highly curable compositions that can be cured even with ultraviolet irradiation devices using LED light sources. LED light sources have the advantage of low running costs and minimal impact on the natural environment due to their low power consumption and low ozone generation. However, because LED light sources emit a single wavelength, the total amount of ultraviolet energy is smaller compared to ultraviolet lamp light sources such as high-pressure mercury lamps, ultra-high-pressure mercury lamps, and metal halide lamps that emit ultraviolet light across a wide range of wavelengths, resulting in less generation of radicals from photopolymerization initiators. As a result, conventional curable compositions suffer from reduced curability, making it difficult to obtain highly hard coating films.

[0005] Patent Document 2 proposes a hard coat solution containing a monomer or oligomer mainly composed of acrylate and a polythiol compound having two or more thiol groups as a curable composition that has high curability and yields a highly hard coating film. However, this composition has insufficient storage stability and thickens when stored at room temperature. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2011-74134 [Patent Document 2] Japanese Patent Publication No. 2012-197383 [Overview of the project] [Problems that the invention aims to solve]

[0007] The present invention has been made in view of the above-mentioned problems, and the object of the present invention is to provide an active energy ray curable composition that has high curability and excellent storage stability, and can form a highly hard cured coating film with good adhesion to the substrate (especially to olefin substrates which are difficult to adhere to). [Means for solving the problem]

[0008] The present inventors have conducted diligent studies to achieve the above objectives and have arrived at the present invention. Specifically, the present invention is an active energy ray curable composition containing an N-substituted (meth)acrylamide (A), a polymer (B), and a photopolymerization initiator (D), wherein the polymer (B) has an SP value of 10 (cal / cm²). 3 ) 1 / 2 It contains a monofunctional (meth)acrylate (b1) and a monomer (b2) having an alicyclic skeleton of less than 100% as constituent monomers, The content of (meth)acrylate (b1) is 50 to 98% by weight based on the total weight of (meth)acrylate (b1) and monomer (b2), and the content of monomer (b2) is 2 to 50% by weight based on the total weight of (meth)acrylate (b1) and monomer (b2). The monomer (b2) has an SP value of 10 (cal / cm³). 3 ) 1 / 2 The above monofunctional (meth)acrylate (b21) and / or SP value is 10 (cal / cm³). 3 ) 1 / 2The above (meth)acrylamide (b22), and an active energy ray-curable composition which is a polymer having a weight average molecular weight of 5000 to 70000 of the polymer (B); relates to a cured product of the active energy ray-curable composition.

Effects of the Invention

[0009] The active energy ray-curable composition of the present invention has high curability and excellent storage stability, and can form a high-hardness cured coating film with good adhesion to a substrate (particularly, adhesion to an olefin substrate with poor adhesion).

Modes for Carrying Out the Invention

[0010] The active energy ray-curable composition of the present invention is an active energy ray-curable composition containing an N-substituted (meth)acrylamide (A), a polymer (B), and a photopolymerization initiator (D), wherein the polymer (B) has a SP value of 10 (cal / cm 3 ) 1 / 2 and contains a monofunctional (meth)acrylate (b1) having an alicyclic skeleton of less than and a monomer (b2) as constituent monomers, and the monomer (b2) has a SP value of 10 (cal / cm 3 ) 1 / 2 or more of the monofunctional (meth)acrylate (b21) and / or a SP value of 10 (cal / cm 3 ) 1 / 2 or more of the (meth)acrylamide (b22), and is characterized in that the polymer (B) is a polymer having a weight average molecular weight of 5000 to 70000.

[0011] In the present invention, “(meth)acrylate” means “methacrylate or acrylate”. “(meth)acryl” means “methacryl or acryl”. “(meth)acryloyl” means “methacryloyl or acryloyl”.

[0012] Hereinafter, the N-substituted (meth)acrylamide (A), the polymer (B), and the photopolymerization initiator (D), which are essential components of the active energy ray-curable composition of the present invention, will be described in order.

[0013] In the present invention, N-substituted (meth)acrylamide (A) means a (meth)acrylamide in which one or two hydrogen atoms of the amino group are replaced with substituents such as hydrocarbon groups. Examples of N-substituted (meth)acrylamides include N-alkoxy(meth)acrylamide, N,N-dialkyl(meth)acrylamide, N-alkoxy-N-alkyl(meth)acrylamide, chain amides having an N-(meth)acryloyl group, and cyclic amides having an N-(meth)acryloyl group. 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,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-butoxymethyl(meth)acrylamide, N-methyl-N-methoxy(meth)acrylamide, N-methyl-N-ethoxy(meth)acrylamide, N-methyl-N-propoxy(meth)acrylamide, N-methyl-N-butoxy(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 chain-like amides having an N-(meth)acryloyl group include N-phenyl(meth)acrylamide, N-isopropyl(meth)acrylamide, and N-hydroxyethyl(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) may be used individually or in combination of two or more.

[0014] Of these N-substituted (meth)acrylamides (A), those preferred from the viewpoint of curability are N,N-dialkylacrylamide, N-alkoxy-N-alkylacrylamide, chain amides having an N-(meth)acryloyl group, and cyclic amides having an N-(meth)acryloyl group. More preferably, these are N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-acryloylmorpholine, Nn-butoxymethyl(meth)acrylamide, N-hydroxyethyl(meth)acrylamide, and N-phenyl(meth)acrylamide. Particularly preferred are N,N-dimethylacrylamide, N,N-diethylacrylamide, N-acryloylmorpholine, Nn-butoxymethylacrylamide, and N-hydroxyethylacrylamide.

[0015] In the present invention, polymer (B) has an SP value of 10 (cal / cm³). 3 ) 1 / 2 The material contains a monofunctional (meth)acrylate (b1) and a monomer (b2) having an alicyclic skeleton of less than 10 (cal / cm³) as constituent monomers, wherein the monomer (b2) has an SP value of 10 (cal / cm³). 3 ) 1 / 2 The above monofunctional (meth)acrylate (b21) and / or SP value is 10 (cal / cm³). 3 ) 1 / 2 The above is (meth)acrylamide (b22), a polymer with a weight-average molecular weight of 5,000 to 70,000.

[0016] In this invention, the SP value (solubility parameter) is a value calculated by the method described in the Fedors method (Polymer Engineering and Science, February, 1974, Vol. 14, No. 2, pp. 147-154).

[0017] The monofunctional (meth)acrylate (b1) having an alicyclic skeleton has one (meth)acryloyl group and an SP value of 10 (cal / cm³). 3 ) 1 / 2It is a (meth)acrylate having an alicyclic skeleton and is less than . The lower limit of the SP value is not particularly limited, but from the viewpoint of compatibility with other components it is preferably 8.5 or higher, and more preferably 8.7 or higher. Examples of monofunctional (meth)acrylates (b1) having an alicyclic skeleton include isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, and 1-ethylcyclopentyl (meth)acrylate. In the present invention, these monofunctional (meth)acrylates (b1) having an alicyclic skeleton may be used individually or in combination of two or more.

[0018] Of these, isobornyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, cyclohexyl (meth)acrylate, and 1-ethylcyclopentyl (meth)acrylate are preferred from the viewpoint of adhesion to the substrate.

[0019] The monomer (b2) has an SP value of 10 (cal / cm³). 3 ) 1 / 2 The above monofunctional (meth)acrylate (b21) and / or SP value is 10 (cal / cm³). 3 ) 1 / 2 The above is (meth)acrylamide (b22).

[0020] The aforementioned monofunctional (meth)acrylate (b21) has one (meth)acryloyl group and an SP value of 10 (cal / cm³). 3 ) 1 / 2 The above is a (meth)acrylate. The upper limit of the SP value is not particularly limited, but from the viewpoint of compatibility with other components, it is preferably 14 or less, and more preferably 13 or less. Examples of monofunctional (meth)acrylates (b21) include hydroxyalkyl (meth)acrylates {2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate, etc.}, polycaprolactone-modified hydroxyalkyl (meth)acrylates {ε-caprolactone n-mol adducts of the above hydroxyalkyl (meth)acrylates (n=1 to 5 is preferred)}, and 1,4-cyclohexyl Examples include xanedimethanol mono(meth)acrylate, methylphenoxyethyl acrylate, phenoxymethyl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, polyethylene glycol (PEG) mono(meth)acrylate, polypropylene glycol (PPG) mono(meth)acrylate, mono(meth)acrylate of o-, m- or p-phenylphenol, and mono(meth)acrylate of 3,3'-diphenyl-4,4'-dihydroxybiphenyl. In the present invention, these monofunctional (meth)acrylates (b21) may be used individually or in combination of two or more.

[0021] Of these, hydroxyalkyl (meth)acrylate and polycaprolactone-modified hydroxyalkyl (meth)acrylate are preferred from the viewpoint of adhesion to the substrate, and more preferably 2-hydroxyethyl (meth)acrylate and ε-caprolactone n-mol adducts (n=2-4) of 2-hydroxyethyl (meth)acrylate.

[0022] The aforementioned (meth)acrylamide (b22) has an SP value of 10 (cal / cm³). 3 ) 1 / 2 The above is the (meth)acrylamide. The upper limit of the SP value is not particularly limited, but from the viewpoint of compatibility with other components, it is preferably 14 or less, and more preferably 13 or less. Examples of (meth)acrylamide (b22) include (meth)acrylamide, N-alkoxy(meth)acrylamide, N-alkoxyalkyl(meth)acrylamide, N,N-dialkyl(meth)acrylamide, N-alkoxy-N-alkyl(meth)acrylamide, chain amides having an N-(meth)acryloyl group, and cyclic amides having an N-(meth)acryloyl group. Examples of N-alkoxy(meth)acrylamides include N-methoxy(meth)acrylamide, N-ethoxy(meth)acrylamide, N-propoxy(meth)acrylamide, N-isobutoxy(meth)acrylamide, and Nn-butoxy(meth)acrylamide. Examples of N-alkoxyalkyl(meth)acrylamides include N-methoxymethyl(meth)acrylamide, N-ethoxymethyl(meth)acrylamide, N-propoxymethyl(meth)acrylamide, N-isobutoxymethyl(meth)acrylamide, and Nn-butoxymethyl(meth)acrylamide. Examples of N,N-dialkyl(meth)acrylamides include N,N-dimethyl(meth)acrylamide and N,N-diethyl(meth)acrylamide. Examples of N-alkoxy-N-alkyl(meth)acrylamides include N-methyl-N-methoxy(meth)acrylamide, N-methyl-N-ethoxy(meth)acrylamide, N-methyl-N-propoxy(meth)acrylamide, N-methyl-N-butoxy(meth)acrylamide, N-ethyl-N-methoxy(meth)acrylamide, N-ethyl-N-ethoxy(meth)acrylamide, N-ethyl-N-propoxy(meth)acrylamide, N-propyl-N-methoxy(meth)acrylamide, N-propyl-N-ethoxyacrylamide, and N-butyl-N-methoxy(meth)acrylamide. Examples of chain-like amides having an N-(meth)acryloyl group include N-isopropyl(meth)acrylamide and N-hydroxyethyl(meth)acrylamide. Examples of cyclic amides having an N-(meth)acryloyl group include N-(meth)acryloylmorpholine, N-(meth)acryloylthiomorpholine, N-(meth)acryloylpiperidine, and N-(meth)acryloylpyrrolidine. In the present invention, these (meth)acrylamide (b22) may be used individually or in combination of two or more.

[0023] Of these (meth)acrylamides (b22), N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-acryloylmorpholine, Nn-butoxymethyl(meth)acrylamide, and N-hydroxyethyl(meth)acrylamide are preferred from the viewpoint of adhesion to the substrate, compatibility with other components, and storage stability.

[0024] The polymer (B) may contain other constituent monomers (b3) other than the monofunctional (meth)acrylate (b1) having the alicyclic skeleton and the monomer (b2). Other constituent monomers (b3) of polymer (B) include, for example, those with an SP value of 10 (cal / cm³). 3 ) 1 / 2 Examples include monofunctional (meth)acrylates with fewer than 2 carbon atoms and no alicyclic skeleton {esterified alcohols with 2 to 30 carbon atoms and (meth)acrylic acid, and tetrahydrofurfuryl acrylate, etc.}, but are not particularly limited as long as they are monofunctional monomers copolymerized with (meth)acrylate (b1) and monomer (b2) having an alicyclic skeleton.

[0025] The content of the monofunctional (meth)acrylate (b1) having an alicyclic skeleton, which is a constituent monomer of polymer (B), is preferably 50 to 98% by weight, more preferably 70 to 98% by weight, and particularly preferably 80 to 98% by weight, based on the total weight of the monofunctional (meth)acrylate (b1) having an alicyclic skeleton and the monomer (b2), from the viewpoint of adhesion to the substrate and storage stability. The content of monomer (b2), which is a constituent monomer of polymer (B), is preferably 2 to 50% by weight, more preferably 2 to 30% by weight, and particularly preferably 2 to 20% by weight, based on the total weight of the alicyclic skeleton-containing (meth)acrylate (b1) and monomer (b2), from the viewpoint of adhesion to the substrate and storage stability.

[0026] The total weight of the monofunctional (meth)acrylate (b1) having an alicyclic skeleton, which is a constituent monomer of polymer (B), and the monomer (b2) is preferably 60 to 100% by weight, more preferably 75 to 100% by weight, and particularly preferably 80 to 100% by weight, based on the weight of polymer (B), from the viewpoint of adhesion to the substrate. The content of other constituent monomers (b3) in polymer (B) is preferably 0 to 30% by weight, more preferably 0 to 20% by weight, and particularly preferably 0 to 10% by weight, based on the weight of polymer (B), from the viewpoint of adhesion to the substrate.

[0027] The weight-average molecular weight of polymer (B) in the present invention is 5,000 to 70,000, preferably 7,000 to 50,000, and more preferably 10,000 to 30,000. If the weight-average molecular weight of polymer (B) is less than 5,000, adhesion to the substrate will be insufficient, and if it exceeds 70,000, compatibility with other components and storage stability will be insufficient.

[0028] The weight-average molecular weight (hereinafter abbreviated as Mw) and number-average molecular weight (hereinafter abbreviated as Mn) of polymer (B) can be measured by gel permeation chromatography (hereinafter abbreviated as GPC) under the following conditions. [Measurement conditions for Mw and Mn] Device: "HLC-8320GPC" [Manufactured by Tosoh Corporation] Column: "TSKgel G4000H" XL "[Manufactured by Tosoh Corporation] 1 piece" TSKgel G3000H XL "[Manufactured by Tosoh Corporation] 1 piece" TSKgel G2000H XL"[Manufactured by Tosoh Corporation] 1 piece" Measurement temperature: 40℃ Sample solution: 0.25% by weight tetrahydrofuran solution Solution injection volume: 10.0μl Detection device: Refractive index detector Reference material: Standard polystyrene (TSK standard POLYSTYRENE) 7 points (Molecular weight: 500, 2630, 5970, 10200, 18100, 37900, 96400) [Manufactured by Tosoh Corporation]

[0029] Polymer (B) can be obtained by known manufacturing methods, specifically by solution polymerization of the monomer in a solvent in the presence of a polymerization catalyst.

[0030] Examples of solvents include toluene, xylene, alkylbenzenes having 9 to 10 carbon atoms, methyl ethyl ketone, diethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, and mixtures thereof. Examples of polymerization catalysts include azo catalysts (such as 2,2'-azobis(2-methylbutyronitrile) and 2,2'-azobis(2,4-dimethylvaleronitrile)), peroxide catalysts (such as benzoyl peroxide, cumyl peroxide, and lauryl peroxide), and redox catalysts (such as a mixture of benzoyl peroxide and a tertiary amine). Furthermore, known chain transfer agents (such as alkyl mercaptans with 2 to 20 carbon atoms) can be used as needed to adjust the molecular weight.

[0031] The polymerization temperature is preferably 25 to 140°C, and more preferably 50 to 120°C. In addition to the solution polymerization described above, polymer (B) can also be obtained by bulk polymerization, emulsion polymerization, or suspension polymerization. The polymerization form of polymer (B) may be either a random addition polymer or an alternating copolymer, and may also be either a graft copolymer or a block copolymer.

[0032] The photopolymerization initiator (D) contained in the active energy ray curable composition of the present invention is not limited as long as it generates radicals and ions, etc., upon irradiation with active energy rays to cause a monomer polymerization reaction, and a photopolymerization initiator that generates radicals upon irradiation with active energy rays can be preferably used. Preferred photopolymerization initiators (D) include acylphosphine oxide compounds (D1), α-hydroxyalkylphenone compounds (D2), α-aminoalkylphenone compounds (D3), ketal compounds (D4), benzoylformate compounds (D5), thioxanthone compounds (D6), benzophenone compounds (D7), and oxime ester compounds (D8).

[0033] Examples of acylphosphine oxide compounds (D1) include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0034] Examples of α-hydroxyalkylphenone compounds (D2) include 1-hydroxycyclohexylphenyl ketone and 2-hydroxy-2-methyl-1-phenylpropan-1-one.

[0035] Examples of α-aminoalkylphenone compounds (D3) 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.

[0036] Examples of ketal compounds (D4) include benzyldimethyl ketal.

[0037] Examples of benzoylformate compounds (D5) include methylbenzoylformate.

[0038] Examples of thioxanthone compounds (D6) include 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone.

[0039] Examples of benzophenone compounds (D7) include benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 4,4'-bismethylaminobenzophenone.

[0040] Examples of oxime ester compounds (D8) include 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyl oxime) and 1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazole-3-yl]-ethanone-1-(O-acetyl oxime). In the present invention, these photopolymerization initiators (D) may be used individually or in combination of two or more.

[0041] Of these photopolymerization initiators (D), acylphosphine oxide compounds (D1) and α-hydroxyalkylphenone compounds (D2) are preferred from the viewpoint of curability and coloration of the cured product, and acylphosphine oxide compounds (D1) are more preferred, with bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide being particularly preferred.

[0042] In the present invention, the content of N-substituted (meth)acrylamide (A) is preferably 4 to 75% by weight, more preferably 10 to 70% by weight, and particularly preferably 20 to 65% by weight, based on the weight of the active energy ray curable composition, from the viewpoint of curability and adhesion to the substrate. Note that the weight of the active energy ray curable composition does not include the weight of the reaction solvent and diluent.

[0043] The content of polymer (B) in the present invention is preferably 0.2 to 5% by weight, more preferably 0.2 to 4% by weight, and particularly preferably 0.2 to 2.5% by weight, based on the weight of the active energy ray curable composition, from the viewpoint of adhesion to the substrate, compatibility, and storage stability. Note that the weight of the active energy ray curable composition does not include the weight of the reaction solvent and diluent.

[0044] In the present invention, the content of the photopolymerization initiator (D) is preferably 2 to 20% by weight, more preferably 2 to 15% by weight, and particularly preferably 5 to 12% by weight, based on the weight of the active energy ray curable composition, from the viewpoint of adhesion to the substrate, curability, and coloration of the cured product. Note that the weight of the active energy ray curable composition does not include the weight of the reaction solvent and diluent.

[0045] The active energy ray curable composition of the present invention may contain a bifunctional (meth)acrylate (C).

[0046] Examples of bifunctional (meth)acrylates (C) include diesters of (meth)acrylic acid with a polyhydric (preferably 2-8 valent) alcohol having 2-30 carbon atoms, diesters of (meth)acrylic acid with 1-30 molar adducts of alkylene oxide (alkylene group with 2-4 carbon atoms) of a polyhydric (preferably 2-8 valent) alcohol having 2-30 carbon atoms, diesters of (meth)acrylic acid with diglycidyl ether, di(meth)acrylates of ethylene oxide adducts of bisphenol A, and di(meth)acrylates of ethylene oxide adducts of fluorene. In the present invention, these bifunctional (meth)acrylates (C) may be used individually or in combination of two or more.

[0047] Of these bifunctional (meth)acrylates (C), preferred from the viewpoint of the strength of the cured product are diesters of a dihydric alcohol having 4 to 12 carbon atoms and (meth)acrylic acid, and diesters of an alkylene oxide adduct (alkylene group with 2 to 4 carbon atoms) of a dihydric alcohol having 2 to 12 carbon atoms and (meth)acrylic acid. More preferred are neopentyl glycol diacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, 1,10-decanediol diacrylate, dimethylol-tricyclodecanediacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, tetramethylene glycol diacrylate, and polytetramethylene glycol diacrylate.

[0048] The content of the bifunctional (meth)acrylate (C) is preferably 10 to 80% by weight, more preferably 10 to 60% by weight, and particularly preferably 15 to 55% by weight, based on the weight of the active energy ray curable composition, from the viewpoint of curability and moist heat adhesion. Note that the weight of the active energy ray curable composition does not include the weight of the reaction solvent and diluent.

[0049] The active energy ray curable composition of the present invention may contain a leveling agent (E) from the viewpoint of reducing surface tension and improving wettability with the substrate. Examples of leveling agents (E) include silicone surfactants, fluorine surfactants, and nonionic surfactants such as polyoxyethylene adducts. Of these leveling agents (E), from the viewpoint of wettability and foam prevention, silicone surfactants and fluorine surfactants are preferred, and silicone surfactants are more preferred.

[0050] The content of the leveling agent (E) is preferably 0.01 to 1.0% by weight, more preferably 0.01 to 0.5% by weight, and particularly preferably 0.01 to 0.2% by weight, based on the weight of the active energy ray curable composition, from the viewpoint of wettability and foaming properties. Note that the weight of the active energy ray curable composition does not include the weight of the reaction solvent and diluent.

[0051] The active energy ray curable composition of the present invention may contain various additives other than the leveling agent (E) as needed, as long as they do not inhibit the effects of the present invention. Examples of additives include charge regulators, light stabilizers, UV absorbers, surface treatment agents, antioxidants, anti-aging agents, crosslinking accelerators, plasticizers, preservatives, pH adjusters, defoamers, and humectants.

[0052] The active energy ray curable composition of the present invention can be obtained by stirring and mixing the above components in a suitable container such as a glass beaker, can, or plastic cup using a stirring rod, spatula, etc., or by mixing them using a known mixing device (such as a mixing device equipped with a stirring spring such as a paddle, a dissolver, a ball mill, and a planetary mixer). The active energy ray curable composition of the present invention is preferably liquid at room temperature, and its viscosity can be measured using an E-type viscometer [such as the "VISCOMETER TV-25L" manufactured by Toki Sangyo Co., Ltd.] and a B-type viscometer.

[0053] To obtain a cured product of an active energy ray-curable composition, the active energy ray-curable ink composition is applied to a substrate by a known method, and then cured by irradiation with active energy rays. In this invention, active energy rays 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 a photopolymerization initiator. When the aforementioned photopolymerization initiator (D) is used, photocuring is possible by irradiation with active energy rays having a wavelength of 200 to 700 nm, and it is preferable that curing is possible by irradiation with light (ultraviolet light) having a wavelength of 200 to 400 nm.

[0054] As light sources that emit ultraviolet light, in addition to high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps and high-power metal halide lamps, etc. (Latest Trends in UV / EB Curing Technology, edited by Radtech Research Group, CMC Publishing, p. 138, 2006), and LEDs can be used. Among these, LEDs consume less power and generate less ozone compared to other light sources, resulting in lower running costs and a lower environmental impact. When curing with an LED light source, an LED light source ultraviolet irradiation device [for example, the LED light source ultraviolet irradiation device "FJ100 150×20 365, manufactured by Phoseon Technology Co., Ltd."] can be used. The amount of ultraviolet light irradiated when curing the active energy ray-curable composition of the present invention is preferably 10 to 10,000 mJ / cm² from the viewpoint of the curability of the composition and the flexibility of the cured product. 2 More preferably 20 to 2,000 mJ / cm² 2 That is the case.

[0055] Film, sheet, or plate-shaped substrates can be used as the substrates to which the active energy ray-curable composition of the present invention is applied. The material of the substrate can be appropriately selected depending on the application, and examples of resin substrates include polyester resins {polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), etc.}, acrylic resins (triacetylcellulose, polycarbonate resin and methyl methacrylate copolymer, etc.), styrene resins, polysulfone resins, polyethersulfone resins, polycarbonate resins, vinyl chloride resins, polymethacrylimide resins, and polyolefin resins (polyethylene, polypropylene and cycloolefin polymers, etc.). Inorganic substrates such as glass substrates can also be used in the same manner.

[0056] The active energy ray-curable composition of the present invention can be applied to a substrate using known coating methods such as spin coating, roll coating, and spray coating, as well as known printing methods such as lithographic printing, cardboard printing, metal printing, offset printing, screen printing, and gravure printing. It can also be applied to inkjet coating methods that continuously eject fine droplets.

[0057] Examples of cured products of the present invention include those obtained by curing an active energy ray-curable composition of the present invention, which has been applied to the aforementioned substrate, by irradiation with active energy. The cured product can be widely used for various coatings, inks (such as UV printing inks and UV inkjet printing inks), and paints, and is extremely useful. [Examples]

[0058] The present invention will be further described below with reference to examples and comparative examples, but the present invention is not limited thereto. In the following, Examples 5, 8, and 9 refer to Reference Examples 1 to 3.

[0059] <Manufacturing Example 1: Manufacturing of Polymer (B-1)> In a reaction vessel equipped with a stirring device, a heating and cooling device, a thermometer, a dropping funnel, a nitrogen blowing tube, and a vacuum device, 40.0 parts by weight of the reaction solvent, propylene glycol monomethyl ether acetate, was added. In another glass beaker, 75.0 parts by weight of isobornyl acrylate (b1-1), 25.0 parts by weight of 2-hydroxyethyl methacrylate (b21-1), 1.5 parts by weight of dodecyl mercaptan as a chain transfer agent, and 0.3 parts by weight of 2,2-azobis(2-methylbutyronitrile) as a polymerization initiator were added. The mixture was stirred and mixed at 20°C to prepare a monomer solution, which was then added to the dropping funnel. After purging the gas phase of the reaction vessel with nitrogen (gas phase oxygen concentration: 100 ppm or less), the monomer solution was added dropwise over 2 hours while maintaining the internal temperature at 85-90°C under a sealed system. After maturation at 85°C for 2 hours following the completion of dropwise addition, the temperature was raised to 100°C and held for 30 minutes to obtain a polymer composition containing 70% by weight of polymer (B-1). The Mw of the obtained polymer (B-1) was 20,000.

[0060] <Manufacturing Examples 2-11 and Comparative Manufacturing Examples 1-8: Manufacturing of polymers (B-2)-(B-11) and comparative polymers (B'-1)-(B'-8)> Production Examples 2-11 and Comparative Production Examples 1-8 were carried out in the same manner as Production Example 1, except that the raw materials used had the formulations shown in Table 1, to obtain polymer compositions containing 70% by weight of polymers (B-2) to (B-11) and comparative polymers (B'-1) to (B'-8), respectively.

[0061] [Table 1]

[0062] The raw materials used in Table 1 are as follows: (b1-1): Isobornyl acrylate [Product name: Light Acrylate IB-XA, manufactured by Kyoeisha Chemical Co., Ltd.] (SP value: 9.6) (b1-2): Cyclohexyl methacrylate [Product name: Light Ester CH, manufactured by Kyoeisha Chemical Co., Ltd.] (SP value: 9.5) (b1-3): t-Butylcyclohexyl acrylate [Product name: Miramer M1150, manufactured by Miwon] (SP value: 9.0) (b1-4): Trimethylcyclohexyl acrylate [Product name: Miramer M1130, manufactured by Miwon] (SP value: 9.0) (b1-5): Trimethylcyclohexyl methacrylate [Trade name: Satomer CD421, manufactured by Arkema] (SP value: 8.9) (b1-6): Isobornyl methacrylate [Product name: Light Ester IB-X, manufactured by Kyoeisha Chemical Co., Ltd.] (SP value: 9.5) (b1-7): 1-Ethylcyclopentyl acrylate [Product name: 1-Ethylcyclopentyl acrylate, manufactured by Tokyo Chemical Industry Co., Ltd.] (SP value: 9.4) (b21-1): 2-Hydroxyethyl methacrylate [Product name: Light Ester HO-250(N), manufactured by Kyoeisha Chemical Co., Ltd.] (SP value: 12.1) (b21-2): 4-Hydroxybutyl acrylate [Product name: 4-HBA, manufactured by Osaka Organic Chemical Co., Ltd.] (SP value: 11.6) (b21-3): 2-hydroxyethyl acrylate ε-caprolactone 4-mol adduct [Product name: PLACCEL FA4DT, manufactured by Daicel Corporation] (SP value: 10.7) (b21-4): 1,4-Cyclohexanedimethanol monoacrylate [Trade name: CHDMMA, manufactured by Mitsubishi Chemical Corporation] (SP value: 11.6) (b22-1): N,N-dimethylacrylamide [Product name: DMAA, manufactured by KJ Chemicals Co., Ltd.] (SP value: 10.6) (b22-2): N,N-Diethylacrylamide [Product name: DEAA, manufactured by KJ Chemicals Co., Ltd.] (SP value: 10.1) (b22-3): N-Acryloylmorpholine [Trade name: ACMO, manufactured by KJ Chemicals Co., Ltd.] (SP value: 11.9) (b22-4): Nn-Butoxymethylacrylamide [Product name: NBMA, manufactured by MCC Unitech Co., Ltd.] (SP value: 10.4) (b22-5): N-phenylacrylamide [Product name: N-phenylacrylamide, manufactured by Tokyo Chemical Industry Co., Ltd.] (SP value: 12.0) (b22-6): N-Hydroxyethylacrylamide [Product name: N-(2-Hydroxyethyl)acrylamide, manufactured by Tokyo Chemical Industry Co., Ltd.] (SP value: 14.4) (b3-1): Lauryl acrylate [Product name: Light Acrylate LA, manufactured by Kyoeisha Chemical Co., Ltd.] (SP value: 8.7)

[0063] <Preparation of Active Energy Ray Curable Compositions> (Example 1) The active energy ray curable composition of Example 1 was prepared by uniformly mixing 50.0 parts by weight of N-acryloylmorpholine (A-1) and 4.3 parts by weight of a polymer composition containing polymer (B-1) (3.0 parts by weight in terms of the purity of polymer (B-1)) with 37.0 parts by weight of dipropylene glycol diacrylate (C-1). Then, 10.0 parts by weight of Irgacure TPO (D-1) and 0.1 parts by weight of BYK-333 (E-1) were added and uniformly mixed. The amount of polymer (B) shown in Table 2 (parts by weight) is converted to its purity.

[0064] (Examples 2-18 and Comparative Examples 1-10) The active energy ray curable compositions of Examples 2 to 18 and Comparative Examples 1 to 10 were prepared in the same manner as in Example 1, except that the raw materials used had the formulations shown in Tables 2 and 3.

[0065] [Table 2]

[0066] [Table 3]

[0067] The raw materials used in Tables 2 and 3 are as follows: (A-1): N-Acryloylmorpholine [Trade name: ACMO, manufactured by KJ Chemicals Co., Ltd.] (A-2): N,N-dimethylacrylamide [Product name: DMAA, manufactured by KJ Chemicals Co., Ltd.] (A-3): N,N-Diethylacrylamide [Product name: DEAA, manufactured by KJ Chemicals Co., Ltd.] (A-4): Nn-Butoxymethylacrylamide [Product name: NBMA, manufactured by MCC Unitech Co., Ltd.] (A-5): N-hydroxyethylacrylamide [Product name: HEAA, manufactured by KJ Chemicals Co., Ltd.] (A-6): N-phenylacrylamide [Product name: N-phenylacrylamide, manufactured by Tokyo Chemical Industry Co., Ltd.] (A'-1): Phenoxyethyl acrylate [Product name: Viscoat #192, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (C-1): Dipropylene glycol diacrylate [Product name: NK Ester APG-100, manufactured by Shin Nakamura Chemical Industry Co., Ltd.] (C-2): Tripropylene glycol diacrylate [Product name: Viscoat #30HP, manufactured by Osaka Organic Chemical Industry Co., Ltd.] (C-3): Diethylene glycol diacrylate [Product name: FA-222A, manufactured by Hitachi Chemical Co., Ltd.] (C-4): Polytetramethylene glycol diacrylate [Product name: PTMG, manufactured by Mitsubishi Chemical Corporation] (C-5): Neopentyl glycol diacrylate [Product name: Light Acrylate NP-A, manufactured by Kyoeisha Chemical Co., Ltd.] (C-6):3-Methyl-1,5-pentanediol diacrylate [Product name: Light Acrylate MPD-A, manufactured by Kyoeisha Chemical Co., Ltd.] (C-7): 1,10-Decanediol diacrylate [Product name: A-DOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.] (C-8):1,9-nonanediol diacrylate [Product name: NK ester A-NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.] (D-1): (2,4,6-trimethylbenzoyl)-phenylphosphine oxide [Trade name: Irgacure TPO, manufactured by BASF] (D-2): Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [Trade name: Irgacure 819, manufactured by BASF] (E-1): Silicone-based surfactant [Product name: BYK-333, manufactured by Big Chemie Japan Co., Ltd.] (E-2): Siloxane-based surfactant [Product name: TEGO Twin4299, manufactured by Tomoe Engineering Co., Ltd.]

[0068] The initial viscosity, coating curability, and storage stability of each active energy ray curable composition obtained in Examples 1-18 and Comparative Examples 1-10, as well as the total light transmittance, pencil hardness, substrate adhesion, and moist heat adhesion of the cured film, were measured or evaluated using the following test methods, and the results are shown in Tables 2 and 3.

[0069] <Measurement of initial viscosity> Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was temperature-controlled at 25°C for 30 minutes, and the viscosity was measured using an E-type viscometer [VISCOMETER TV-25L manufactured by Toki Sangyo Co., Ltd.] under the following conditions. [Measurement conditions] Cone rotor: Standard cone rotor (1°34' × R24) Measurement temperature: 25℃ Measurement range: M Rotation speed: 20 rpm

[0070] (1) Evaluation of coating film hardening properties Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was applied to a surface-treated 100 μm thick PET (polyethylene terephthalate) film [Cosmoshine A4300, manufactured by Toyobo Co., Ltd.] using an applicator to a film thickness of 10 μm. The film was then heated at 80°C for 3 minutes and then cooled to 25°C. 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 irradiate the film at an intensity of 1500 mW / cm². 2 Exposure was performed using [a specific method / equipment]. The exposure dose was 500 mJ / cm². 2 That was the case. The curability of the cured coating film immediately after light irradiation and 10 seconds after light irradiation was evaluated by touch, specifically by the presence or absence of tackiness. ○: No pleats ×: With pleats

[0071] (2) Evaluation of storage stability (a) Storage stability (viscosity change after storage at 70°C for 1000 hours) Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was placed in a light-shielding plastic container with a lid, stored in a constant temperature bath at 70°C for 1000 hours, then temperature-controlled at 25°C for 1 hour, and the viscosity was measured under the same conditions as for the initial viscosity measurement. Next, the viscosity change rate (%) was calculated using the following formula (1), and the storage stability was evaluated according to the following criteria. Viscosity change rate (%) = (Y a -X) / X×100 ···(1) X: Initial viscosity (unit: mPa·s) Y a Viscosity after storage at 70°C for 1000 hours (unit: mPa·s) [Evaluation Criteria] 5: The absolute value of the viscosity change rate (%) is less than 10. 4: The absolute value of the viscosity change rate (%) is 10 or more and less than 30. 3: The absolute value of the viscosity change rate (%) is 30 or more and less than 50. 2: The absolute value of the viscosity change rate (%) is 50 or more and less than 100. 1: The absolute value of the viscosity change rate (%) is 100 or more.

[0072] (b) Storage stability (viscosity change after storage at 60°C for 5000 hours) Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was placed in a light-shielding plastic container with a lid, stored in a constant temperature bath at 60°C for 5000 hours, then temperature-controlled at 25°C for 1 hour, and the viscosity was measured under the same conditions as for the initial viscosity measurement. Next, the viscosity change rate (%) was calculated using the following formula (2), and the storage stability was evaluated according to the following criteria. Viscosity change rate (%) = (Y b -X) / X×100 ···(2) X: Initial viscosity (unit: mPa·s) Y b Viscosity after storage at 60°C for 5000 hours (unit: mPa·s) [Evaluation Criteria] 5: The absolute value of the viscosity change rate (%) is less than 10. 4: The absolute value of the viscosity change rate (%) is 10 or more and less than 30. 3: The absolute value of the viscosity change rate (%) is 30 or more and less than 50. 2: The absolute value of the viscosity change rate (%) is 50 or more and less than 100. 1: The absolute value of the viscosity change rate (%) is 100 or more.

[0073] (c) Storage stability (uniformity after storage at -5°C for 500 hours) Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was placed in a light-shielding plastic container with a lid, stored in a freezer at -5°C for 500 hours, then temperature-controlled at 25°C for 1 hour, and solubility was confirmed by visual inspection and filtration tests. [Method of Filtration Test] Approximately 3 mL of each active energy ray-curable composition was drawn into a 5 mL glass syringe. A syringe filter with a pore size of 0.45 μm was then attached to the end of the syringe, and the active energy ray-curable composition was filtered by pushing the syringe with a finger. If filtration was successful without clogging, the same filtration was performed using a syringe filter with a pore size of 0.20 μm. [Evaluation Criteria] 5. It is transparent to the naked eye and can be filtered without clogging using a syringe filter with a filter pore size of 0.20 μm. 4. It is transparent to the naked eye and can be filtered without clogging using a syringe filter with a filter pore size of 0.45 μm. 3: It appears transparent to the naked eye, but it clogs a syringe filter with a filter pore size of 0.45 μm. 2: The liquid appears cloudy to the naked eye. 1: Sediment can be visually confirmed.

[0074] (3) Evaluation of total light transmittance The total light transmittance (%) of each cured product obtained in "(1) Evaluation of coating film curability" above was measured using a total light transmittance measuring device [product name "haze-garddual", manufactured by BYK gardner Co., Ltd.] in accordance with JIS K 7375:2008. Furthermore, when prepared under these sample preparation conditions and used for general coating applications, the total light transmittance must be 88% or higher, and preferably 90% or higher.

[0075] (4) Evaluation of pencil hardness (hardness of the coating) After the cured materials obtained in "(1) Evaluation of coating film hardening properties" above were left to stand in a room at a temperature of 23±2℃ for 16 hours, they were placed on a flat glass plate and their pencil hardness was measured according to the description in JIS K 5600-5-4:1999.

[0076] (5) Evaluation of adhesion to substrate (compared to PET film) Each of the active energy ray-curable compositions obtained in Examples 1-18 and Comparative Examples 1-10 was applied to a surface-treated 100 μm thick PET (polyethylene terephthalate) film [product name: Cosmoshine A4300, manufactured by Toyobo Co., Ltd.] using an applicator to a film thickness of 10 μm, temperature-controlled at 80°C for 3 minutes, and then cooled to 25°C. 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 irradiate at an intensity of 1500 mW / cm². 2 The samples were exposed to light and prepared for evaluation. The exposure dose was 500 mJ / cm². 2 The obtained evaluation samples were left to stand for 24 hours in an environment of 23°C and 50% relative humidity. Then, the cured coating on the substrate was cross-cut into a 2mm x 2mm grid (100 squares), cellophane adhesive tape was applied to it, and peeled off at a 90-degree angle. The degree of peeling of the cured material from the substrate was visually observed. Two grids were created for each sample for evaluation, and the average number of squares in which the cured material remained firmly attached to the substrate is shown in Tables 2 and 3. A value of 97 or higher is required, and 100 is preferable.

[0077] (6) Evaluation of substrate adhesion (compared to COP film) A sample for evaluation was prepared in the same manner as described in "(5) Evaluation of substrate adhesion" above, except that the substrate was changed from PET film to COP (cycloolefin polymer) film [product name: Zeonor Film®, manufactured by Nippon Zeon Co., Ltd.]. In the same manner as above, 90-degree peeling was performed on two grid boards, and the average number of squares in which the cured material remained adhered to the substrate without peeling is shown in Tables 2 and 3. A value of 95 or higher is required, and 100 is preferable.

[0078] (7) Evaluation of moist heat adhesion after 24 hours (compared to PET film and COP film) The same evaluation samples used in the evaluation of substrate adhesion in (5) and (6) above were prepared and placed in a constant temperature and humidity chamber at 85°C and 85% relative humidity for 24 hours, and then left to stand at 25°C for 3 hours. For each sample, 90-degree peeling was performed on two grids in the same manner as above, and the average number of squares in which the cured material remained adhered to the substrate is shown in Tables 2 and 3. A value of 95 or higher is required, and 100 is preferable.

[0079] As shown in Table 2, the active energy ray curable compositions of Examples 1 to 18 of the present invention exhibited high curability and excellent storage stability, forming highly hard cured coatings with excellent adhesion to PET substrates and polyolefin substrates that are difficult to adhere to. Furthermore, the transparency of the cured coatings was also good. On the other hand, as shown in Table 3, the active energy ray curable compositions of Comparative Examples 1, 2, and 5 lacked sufficient hardness and substrate adhesion of the cured product; the active energy ray curable composition of Comparative Example 3 lacked sufficient storage stability; the active energy ray curable composition of Comparative Example 4 lacked sufficient storage stability, hardness of the cured product, and substrate adhesion; the active energy ray curable composition of Comparative Example 6 lacked sufficient substrate adhesion of the cured product; the active energy ray curable composition of Comparative Example 7 lacked sufficient storage stability and hardness of the cured product; the active energy ray curable compositions of Comparative Examples 8 and 9 lacked sufficient coating film curability, total light transmittance of the cured product, and hardness; and substrate adhesion could not be evaluated due to tack on the coating film surface. The active energy ray curable composition of Comparative Example 10 lacked sufficient substrate adhesion. [Industrial applicability]

[0080] The active energy ray curable composition of the present invention exhibits high curability and excellent storage stability, and its cured product has excellent adhesion to substrates, high hardness, and high transparency. Therefore, it can be suitably used, for example, as a material for various coatings, inks (such as UV printing inks and UV inkjet printing inks) or paints.

Claims

1. An active energy ray curable composition comprising an N-substituted (meth)acrylamide (A), a polymer (B), and a photopolymerization initiator (D), wherein the polymer (B) has an SP value of 10 (cal / cm²). ３ ) １／２ The material contains a monofunctional (meth)acrylate (b1) and a monomer (b2) having an alicyclic skeleton of less than 10 as constituent monomers, wherein the content of the (meth)acrylate (b1) is 50 to 98% by weight based on the total weight of the (meth)acrylate (b1) and the monomer (b2), and the content of the monomer (b2) is 2 to 50% by weight based on the total weight of the (meth)acrylate (b1) and the monomer (b2), and the monomer (b2) has an SP value of 10 (cal / cm³). ３ ) １／２ The above monofunctional (meth)acrylate (b21) and / or SP value of 10 (cal / cm³) ３ ) １／２ An active energy ray curable composition comprising the above (meth)acrylamide (b22), wherein the weight-average molecular weight of the polymer (B) is 5,000 to 70,000.

2. The active energy ray curable composition according to claim 1, wherein the N-substituted (meth)acrylamide (A) is at least one selected from the group consisting of N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-acryloylmorpholine, N-n-butoxymethyl(meth)acrylamide, N-hydroxyethyl(meth)acrylamide, and N-phenyl(meth)acrylamide.

3. The active energy ray curable composition according to claim 1 or 2, wherein the (meth)acrylate (b1) is at least one selected from the group consisting of isobornyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, cyclohexyl (meth)acrylate, and 1-ethylcyclopentyl (meth)acrylate.

4. The active energy ray curable composition according to any one of claims 1 to 3, wherein the monomer (b2) is at least one selected from the group consisting of hydroxyalkyl (meth)acrylate, polycaprolactone-modified hydroxyalkyl (meth)acrylate, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-acryloylmorpholine, N-n-butoxymethyl (meth)acrylamide, and N-hydroxyethyl (meth)acrylamide.

5. The active energy ray curable composition according to any one of claims 1 to 4, wherein the content of the N-substituted (meth)acrylamide (A) is 4 to 75% by weight based on the weight of the active energy ray curable composition, the content of the polymer (B) is 0.2 to 5% by weight based on the weight of the active energy ray curable composition, and the content of the photopolymerization initiator (D) is 2 to 20% by weight based on the weight of the active energy ray curable composition.

6. The active energy ray curable composition according to any one of claims 1 to 5, further containing a bifunctional (meth)acrylate (C).

7. A cured product of an active energy ray curable composition according to any one of claims 1 to 6.

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