Active energy ray-curable composition, cured coating and laminated film

Abstract

To provide an active energy ray-curable composition capable of forming a cured coating that offers low viscosity and high hardness, and excels in adhesion and curling resistance; a cured coating; and a laminated film.SOLUTION: An active energy ray-curable composition comprises the following components (A) and (B). The component (A) is 40 mass%-89 mass% and the component (B) is 10 mass%-60 mass%. The organic solvent content is 5 mass% or less. The component (A): a polyfunctional (meth)acrylate with a viscosity at 25°C of 100 mPa s or less (excluding the component (B)). The component (B): a bifunctional monomer with a viscosity at 25°C of 10 mPa s or less, incorporating a reactive site represented by the formula below.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an active energy ray-curable composition, a cured coating film, and a laminate film. [Background technology]

[0002] A hard coat layer is provided on the surface of an optical display such as a liquid crystal display to protect the display from scratches. The coating material used for the hard coat layer of such an optical display needs to ensure adhesion to the substrate without any defective appearance of the coating film when applied. In addition, the coating material is generally diluted with an organic solvent to reduce the viscosity of the coating material and increase the wettability to the substrate. When forming a coating film from a solvent-based coating material, a process of drying the solvent after application is essential, but from the viewpoint of carbon neutrality, it is preferable to reduce the drying process, which is a large energy load during the manufacturing process. In addition, from the viewpoint of reducing VOCs to reduce the burden on the environment, the development of a solvent-free hard coat coating material is required.

[0003] When designing a solvent-free hard-coat coating material, the issues are how to reduce the viscosity of the coating material for application, how to ensure adhesion to the substrate, and how to achieve hard-coat properties. To achieve hard-coat properties, it is necessary to increase the crosslink density in the coating film, but polyfunctional monomers tend to have high viscosity depending on their molecular weight and polarity.

[0004] For example, in order to solve the above problems, the following Patent Document 1 uses a monofunctional (meth)acrylate having a vinyl ether group and / or an allyl ether group and no hydroxyl group, and a trifunctional or higher (meth)acrylate having no hydroxyl group. Also, the following Patent Document 2 uses an acrylate mixture mainly composed of a specific glycerin triacrylate, a compound having one or two ethylenically unsaturated groups, and a compound having three or more ethylenically unsaturated groups. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2013-136737 A [Patent Document 2] JP 2019-196461 A Summary of the Invention [Problem to be solved by the invention]

[0006] In Patent Document 1, a trifunctional or higher (meth)acrylate is used to provide hard coat properties, so the viscosity of the composition is still high. In Patent Document 2, the compound having an ethylenically unsaturated group used as a viscosity diluent has a viscosity of about 20 mPa·s, and there is a limit to how much the viscosity of the composition can be reduced. This makes coating difficult depending on the coating method. In addition, using a monofunctional monomer with a lower viscosity as a diluent as in these conventional technologies has the effect of reducing the viscosity, but there is a problem that the hardness of the coating film decreases and the hard coat properties are lost.

[0007] As mentioned above, in order to have excellent coating suitability regardless of the coating method, it is necessary to reduce the viscosity of the coating composition, but when a monofunctional monomer is used as a diluent, the viscosity can be reduced, but the crosslink density in the cured coating film decreases, resulting in a decrease in hard coat properties. When a bifunctional monomer is used as a diluent, the viscosity can be reduced to a certain extent while maintaining hardness, but there is a limit to the effect of reducing the viscosity.

[0008] Therefore, there has been a demand for materials that have sufficiently low viscosity even in solvent-free systems that use almost no solvent (solvent content of 5% by mass or less) and that can form cured coating films that have high hardness, adhesion, and curl resistance.

[0009] The problem to be solved by the present invention is to provide an active energy ray-curable composition, a cured coating film, and a laminate film that are capable of forming a cured coating film that has low viscosity with almost no use of a solvent and has high hardness, adhesion, and curl resistance, and that is excellent in terms of both hardness and adhesion and curl resistance. [Means for solving the problem]

[0010] Means for Solving the Problems The present inventors conducted intensive research to solve the above problems and discovered that by using a low-viscosity multifunctional (meth)acrylate and a bifunctional monomer having a specific reactive group, it is possible to form a cured coating film that has a sufficiently low viscosity (<20 mPa s) and is excellent in hardness, adhesion and curl resistance, even when the organic solvent content is 5 mass% or less, and thus completed the present invention.

[0011] That is, the present invention provides the following inventions. [1] An active energy ray-curable composition comprising the following components (A) and (B), in which the content of component (A) is 40% by mass to 89% by mass, the content of component (B) is 10% by mass to 60% by mass, and the content of organic solvent is 5% by mass or less: Component (A): A polyfunctional (meth)acrylate with a viscosity of 100 mPa s or less at 25°C (excluding component (B)) Component (B): a bifunctional monomer having a reactive site represented by the following formula (1) and a viscosity at 25°C of 10 mPa s or less [ka] Formula (1) [In formula (1), R1, R2, and R3 each independently represent a hydrogen atom or a methyl group, and R4 represents an alkyl chain having 0 to 3 carbon atoms.] [2] The active energy ray-curable composition according to [1], wherein the component (B) has a vinyl ether group, an allyl ether group, or an isoprenyl group as the reactive site represented by formula (1). [3] The active energy ray-curable composition according to [1] or [2], further comprising 1% by mass to 25% by mass of the following component (C): Component (C): Monofunctional or bifunctional monomer with a viscosity of 10 mPa s or less at 25°C (excluding component (B)) [4] The active energy ray-curable composition according to any one of [1] to [3], wherein the viscosity of the component (A) at 25°C is 70 mPa s or less. [5] The active energy ray-curable composition according to any one of [1] to [4], which contains a photopolymerization initiator. [6] The active energy ray-curable composition according to any one of [1] to [5], further comprising a leveling agent. [7] A cured coating film which is a cured reaction product of the active energy ray-curable composition according to any one of [1] to [6]. [8] A laminate film comprising the cured coating film described in [7] and a substrate. Effect of the Invention

[0012] The active energy ray-curable composition of the present invention has a low viscosity (<20 mPa s) and therefore has excellent coatability regardless of the coating method, and can form a cured coating film that is excellent in hardness, adhesion, and curl resistance. Therefore, the composition can be suitably used as a protective coating agent for the surfaces of various substrates, and as an optical film for use in flat panel displays (FPDs) such as liquid crystal displays (LCDs), organic light-emitting diode displays (OLEDs), and plasma displays (PDPs). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] In this specification, "acrylate" and "methacrylate" are collectively referred to as "(meth)acrylate", and "(meth)acryloyl" and "acryloyl" are collectively referred to as "(meth)acryloyl". In addition, the active energy ray-curable composition may be simply referred to as "composition".

[0014] [Active energy ray-curable composition] The composition of the present invention comprises the following components (A) and (B), with the component (A) being 40% by mass to 89% by mass, the component (B) being 10% by mass to 60% by mass, and the content of the organic solvent being 5% by mass or less. Component (A): A polyfunctional (meth)acrylate with a viscosity of 100 mPa s or less at 25°C (excluding component (B)) Component (B): a bifunctional monomer having a reactive site represented by the following formula (1) and a viscosity at 25°C of 10 mPa s or less [ka] Formula (1) [In formula (1), R1, R2, and R3 each independently represent a hydrogen atom or a methyl group, and R4 represents an alkyl chain having 0 to 3 carbon atoms.] In addition to the components (A) and (B), an optional component such as a component (C) may be contained.

[0015] (Component (A)) In the composition of the present invention, by including component (A) which is a polyfunctional (meth)acrylate, it is possible to suppress the viscosity of the composition and achieve high hardness when cured. Polyfunctional (meth)acrylate refers to any compound having two or more (meth)acryloyl groups in one molecule (excluding component (B)). The viscosity of component (A) at 25°C is preferably 90 mPa·s or less, more preferably 80 mPa·s or less, and even more preferably 70 mPa·s or less.

[0016] Examples of such component (A) include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, di(meth)acrylate, Examples of di(meth)acrylates include 1,3-butylene glycol acrylate, 1,4-butanediol di(meth)acrylate, polybutylene glycol di(meth)acrylate, poly(1-methylbutylene glycol) di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, neopentyl glycol hydroxypivalate di(meth)acrylate, and dicyclopentanediol di(meth)acrylate.

[0017] Examples of component (A) include di(meth)acrylic acid ester of a caprolactone adduct of neopentyl glycol hydroxypivalate, di(meth)acrylic acid ester of a γ-butyrolactone adduct of neopentyl glycol hydroxypivalate, di(meth)acrylic acid ester of a caprolactone adduct of neopentyl glycol, di(meth)acrylic acid ester of a caprolactone adduct of butylene glycol, di(meth)acrylic acid ester of a caprolactone adduct of cyclohexanedimethanol, di(meth)acrylic acid ester of a caprolactone adduct of dicyclopentanediol, di(meth)acrylic acid ester of a caprolactone adduct of bisphenol A, di(meth)acrylic acid ester of a caprolactone adduct of bisphenol F, dimethyloltricyclodecane di(meth)acrylic acid ester, neopentyl glycol modified trimethylolpropane di(meth)acrylic acid ester, di(meth)acrylic acid ester of an ethylene oxide adduct of bisphenol A, and di(meth)acrylic acid ester of a propylene oxide adduct of bisphenol A. di(meth)acrylates such as di(meth)acrylic acid ester of bisphenol F ethylene oxide adduct and di(meth)acrylic acid ester of bisphenol F propylene oxide adduct; and poly(meth)acrylates such as trimethylolpropane tri(meth)acrylic acid ester, tri(meth)acrylic acid ester of trimethylolpropane ethylene oxide adduct, tri(meth)acrylic acid ester of trimethylolpropane propylene oxide adduct, glycerin tri(meth)acrylic acid ester, tri(meth)acrylic acid ester of glycerin ethylene oxide adduct, tetra(meth)acrylic acid ester of ditrimethylolpropane ethylene oxide adduct, tri(meth)acrylic acid ester of pentaerythritol ethylene oxide adduct, tetra(meth)acrylic acid ester of pentaerythritol ethylene oxide adduct, tri(meth)acrylic acid ester of pentaerythritol propylene oxide adduct, and tetra(meth)acrylic acid ester of pentaerythritol propylene oxide adduct.

[0018] Examples of the component (A) include tri(meth)acrylic acid esters of pentaerythritol caprolactone adducts, tetra(meth)acrylic acid esters of pentaerythritol caprolactone adducts, penta(meth)acrylic acid esters of dipentaerythritol caprolactone adducts, hexa(meth)acrylic acid esters of dipentaerythritol caprolactone adducts, poly(meth)acrylates such as N,N',N"-tris(acryloxyethyl)isocyanurate and N,N'-bis(acryloxyethyl)-N"-hydroxyethyl isocyanurate, hexamethylene diisocyanate, isophorone diisocyanate, and tolylene diisocyanate. Examples of the polyisocyanate include trimers of isocyanate compounds such as xylylene diisocyanate, diphenylmethane diisocyanate, and hydrogenated diphenylmethane diisocyanate; polyisocyanates as adducts of these diisocyanates with alkyl polyalcohols (e.g., trimethylolpropane, pentaerythritol, and glycerin); and urethane poly(meth)acrylates in which hydroxy group-containing (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and caprolactone adducts of these are added to tris(4-isocyanatophenyl)methane.

[0019] Examples of the component (A) include epoxy poly(meth)acrylates obtained by an addition reaction between a polyepoxy compound having a plurality of epoxy groups in the molecule, such as bisphenol A glycidyl ether, bisphenol F glycidyl ether, phenol novolac epoxy resin, cresol novolac epoxy resin, pentaerythritol polyglycidyl ether, trimethylolpropane triglycidyl ether, or triglycidyl tris(2-hydroxyethyl)isocyanurate, and (meth)acrylic acid; and polyester poly(meth)acrylates obtained by a condensation reaction between a polycarboxylic acid, such as phthalic acid, fumaric acid, or maleic acid, and two or more polyols, such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, butylene glycol, polybutylene glycol (number of repeating units: 2 to 14), bisphenol A ethylene oxide adduct, trimethylolpropane, or pentaerythritol, and (meth)acrylic acid.

[0020] Examples of the component (A) include epoxy poly(meth)acrylates obtained by an addition reaction between a polyepoxy compound having multiple epoxy groups in the molecule, such as bisphenol A glycidyl ether, bisphenol F glycidyl ether, phenol novolac epoxy resin, cresol novolac epoxy resin, pentaerythritol polyglycidyl ether, trimethylolpropane triglycidyl ether, or triglycidyl tris(2-hydroxyethyl)isocyanurate, and (meth)acrylic acid; and polyester poly(meth)acrylates obtained by a condensation reaction between a polycarboxylic acid, such as phthalic acid, fumaric acid, or maleic acid, and two or more polyols, such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, butylene glycol, polybutylene glycol, bisphenol A ethylene oxide adduct, trimethylolpropane, or pentaerythritol, and (meth)acrylic acid.

[0021] Among them, glycidyl triacrylate (GLYTA), EO-trimethylpropyl triacrylate (EO-TMPTA), and trimethylpropane triacrylate (TMPTA) are preferred as component (A) because they can provide high hardness even with low viscosity. These components (A) can be used alone or in combination of two or more.

[0022] The molecular weight of component (A) is, for example, from 190 g / mol to 320 g / mol, preferably from 200 g / mol to 300 g / mol. By setting it within these ranges, the increase in viscosity of the composition is further suppressed, and the hardness and curl resistance of the cured coating film are well balanced.

[0023] As the component (A), a commercially available product may be used. Examples of such a component (A) include ARONIX (registered trademark) M-930 (a mixture of glycerin diacrylate and glycerin triacrylate, manufactured by Toagosei Co., Ltd.), ARONIX (registered trademark) M-933 (pentaerythritol acrylate, manufactured by Toagosei Co., Ltd.), Miramer M300 (trimethylolpropane triacrylate, manufactured by MIWON Co., Ltd.), Miramer M3130, M3160, M3190 (trimethylolpropane EO-modified triacrylate, manufactured by MIWON Co., Ltd.), Miramer M360 (trimethylolpropane PO-modified triacrylate, manufactured by MIWON Co., Ltd.), Miramer M320 (glycerin propoxy triacrylate, manufactured by MIWON Co., Ltd.), Miramer Examples of the copolymer include M4004 (pentaerythritol EO modified tetraacrylate, manufactured by MIWON Corporation), TMPTA (trimethylolpropane triacrylate, manufactured by Daicel-Allnex Corporation), EBECRYL 160S (trimethylolpropane ethoxy triacrylate, manufactured by Daicel-Allnex Corporation), and OTA 480 (glycerin propoxy triacrylate, manufactured by Daicel-Allnex Corporation).

[0024] The amount of component (A) is 40% by mass to 89% by mass, preferably 45% by mass to 85% by mass, and more preferably 50% by mass to 80% by mass, based on the total amount of the composition as described above. The above proportion of component (A) further suppresses an increase in the viscosity of the composition, while providing a well-balanced improvement in the hardness and curl resistance of the cured coating film.

[0025] ((B) component) Component (B) is a bifunctional monomer having a reactive site represented by the following formula (1) and a viscosity at 25°C of 10 mPa·s or less. [ka] Formula (1) [In formula (1), R1, R2, and R3 each independently represent a hydrogen atom or a methyl group, and R4 represents an alkyl chain having 0 to 3 carbon atoms.] The reactive site shown in formula (1) is one of the functional groups in a bifunctional monomer.

[0026] The (B) component preferably has a vinyl ether group, an allyl ether group, or an isoprenyl group as the reactive site represented by formula (1). In the composition of the present invention, the (B) component can further reduce the viscosity of the composition while suppressing the decrease in hardness, and can provide a cured coating film with excellent adhesion and curl resistance. The (B) component may contain either a vinyl ether group or an allyl ether group, or may contain both. The bifunctional monomer refers to all compounds having two reactive groups (e.g., reactive vinyl groups such as vinyl ether and allyl ether groups, or (meth)acryloyl groups) in one molecule. The (B) component has a viscosity at 25°C of preferably 8 mPa·s or less, more preferably 6 mPa·s or less, and even more preferably 4 mPa·s or less.

[0027] Examples of the compound having a vinyl ether group of the component (B) include 2-(2-vinyloxyethoxy)ethyl acrylate (VEEA), 2-(2-vinyloxyethoxy)ethyl methacrylate (VEEM), diethylene glycol divinyl ether (DEGDVE), 1,4-butanediol divinyl ether (BDVE), cyclohexane dimethanol divinyl ether (CHDVE), triethylene glycol divinyl ether (TEGDVE), etc. Among them, 2-(2-vinyloxyethoxy)ethyl acrylate (VEEA), diethylene glycol divinyl ether (DEGDVE), isoprenyl methacrylate (IPEMA), and diprenyl glycerin ether (DPNG) are preferred.

[0028] Examples of the compound having an allyl ether group of component (B) include allyl ether of α-hydroxymethyl acrylate (RHMA) (AOMA), 1,3-diallyloxy-2-propanol, trimethylolpropane diallyl ether, etc. Among these, allyl ether of α-hydroxymethyl acrylate (RHMA) (AOMA) is preferred.

[0029] The compound having an isoprenyl group of the component (B) may be isoprenyl methacrylate (IPEMA), etc. Among them, isoprenyl methacrylate (IPEMA) is preferable. These components (B) may be used alone or in combination of two or more.

[0030] The molecular weight of component (B) is, for example, from 130 g / mol to 220 g / mol, preferably from 150 g / mol to 200 g / mol. By setting it within these ranges, the increase in viscosity of the composition is further suppressed, and the hardness and curl resistance of the cured coating film are well balanced.

[0031] As the component (B), a commercially available product may be used. Examples of such a component (B) include 2-(2-vinyloxyethoxy)ethyl acrylate (VEEA (registered trademark), manufactured by Nippon Shokubai Co., Ltd.), cyclopolymerizable monomer (AOMA (registered trademark), manufactured by Nippon Shokubai Co., Ltd.), diethylene glycol divinyl ether (DEGDVE, manufactured by Nippon Carbide Industries Co., Ltd.), 1,4-butanediol divinyl ether (BDVE, manufactured by Nippon Carbide Industries Co., Ltd.), cyclohexane dimethanol divinyl ether (CHDVE, manufactured by Nippon Carbide Industries Co., Ltd.), triethylene glycol divinyl ether (TEGDVE, manufactured by Nippon Carbide Industries Co., Ltd.), isoprenyl methacrylate (IPEMA, manufactured by Kuraray Co., Ltd.), Neoallyl (registered trademark) T-20 (trimethylolpropane diallyl ether, manufactured by Osaka Soda Co., Ltd.), IPEMA (registered trademark) (manufactured by Kuraray Co., Ltd.), and DPNG (registered trademark) (manufactured by Kuraray Co., Ltd.).

[0032] The amount of component (B) is 10% by mass to 60% by mass, preferably 15% by mass to 50% by mass, and more preferably 20% by mass to 40% by mass, based on the total amount of the composition as described above. The above proportion of component (B) further suppresses an increase in the viscosity of the composition, while providing a well-balanced improvement in the hardness and curl resistance of the cured coating film.

[0033] ((C) component) Component (C) is an optional component and is a monofunctional or bifunctional monomer other than component (B) that has a viscosity of 10 mPa·s or less at 25°C. Component (C) is a typical low-viscosity monofunctional or bifunctional monomer other than component (B), and may be contained within a range that does not impair the effects of the present invention. The viscosity of component (C) at 25°C is preferably 8 mPa·s or less, more preferably 6 mPa·s or less, and even more preferably 4 mPa·s or less.

[0034] Examples of the monofunctional monomer that is component (C) include acryloylmorpholine (ACMO), 4-hydroxybutyl acrylate (4-HBA), phenol EO modified acrylate (Ph(EO)2A), ethoxydiethylene glycol acrylate (EOEOEA), isoamyl acrylate (IAA), lauryl acrylate (LA), stearyl acrylate (SA), ethoxy-diethylene glycol acrylate (ECA), methoxy-triethylene glycol acrylate (MTGA), 2-ethylhexyl-diglycol acrylate (EHDGAT), methoxy-polyethylene glycol acrylate, methoxydipropylene glycol acrylate (DPMA), phenoxyethyl acrylate, phenoxyethyl acrylate, tetrahydrofurfuryl acrylate (THFA), isobornyl acrylate (IBXA), 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 2-hydroxybutyl acrylate. Among these, acryloylmorpholine (ACMO) and 4-hydroxybutyl acrylate (4-HBA) are preferable.

[0035] Examples of the bifunctional monomer that is the component (C) include hexanediol diacrylate (HDDA), hexanediol EO modified diacrylate (HD(EO)DA), hydroxypivalic acid neopentyl glycol diacrylate (HPNDA), neopentyl glycol PO modified diacrylate (NPG(PO)2DA), triethylene glycol diacrylate (TEGDA), tripropylene glycol diacrylate (TPGDA), dipropylene glycol diacrylate (DPGDA), PEG200# diacrylate, polytetramethylene glycol diacrylate (PTMGDA), neopentyl glycol diacrylate (NPGDA), 3-methyl-1,5-pentanediol diacrylate, 1,9-nonanediol diacrylate (1,9-NDDA), etc. Among them, hexanediol diacrylate (HDDA), triethylene glycol diacrylate (TEGDA), and 1,9-nonanediol diacrylate (1,9-NDDA) are preferred. These components (C) can be used alone or in combination of two or more.

[0036] The molecular weight of component (C) is, for example, from 120 g / mol to 240 g / mol, preferably from 120 g / mol to 235 g / mol, in which case the composition is prevented from increasing in viscosity, and the hardness and curl resistance of the cured coating film are well balanced.

[0037] As the component (C), a commercially available product may be used, such as Miramer M200 (hexanediol diacrylate, manufactured by MIWON Co., Ltd.), Viscoat #260 (1,9-nonanediol diacrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd.), Light Acrylate 3EG-A (triethylene glycol diacrylate, manufactured by Kyoeisha Chemical Co., Ltd.), and Acryloyl Morpholine (manufactured by KJ Chemicals Co., Ltd.).

[0038] When the composition of the present invention contains the component (C), the content thereof is, for example, 1% by mass to 25% by mass, and preferably 2% by mass to 20% by mass.

[0039] (Photopolymerization initiator) The composition of the present invention may contain a photopolymerization initiator. Examples of photopolymerization initiators include various benzophenones such as benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 4,4'-bisdimethylaminobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, Michler's ketone, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; xanthones and thioxanthones such as xanthone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, and 2,4-diethylthioxanthone; various acyloin ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether; α-diketones such as benzyl and diacetyl; sulfides such as tetramethylthiuram disulfide and p-tolyl disulfide; various benzoic acids such as 4-dimethylaminobenzoic acid and ethyl 4-dimethylaminobenzoate;3,3′-Carbonyl-bis(7-diethylamino)coumarin, 1-hydroxycyclohexyl phenyl ketone, 2,2′-dimethoxy-1,2-diphenylethan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,4 ,6-Trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-benzoyl-4'-methyldimethylsulfide, 2,2'-diethoxyacetophenone, benzyl dimethylketal, benzyl-β-methoxyethyl acetal, o-benzoyl methyl benzoate, bis(4-dimethylaminophenyl)ketone, p-dimethylaminoacetophenone, α,α-dichloro-4-phenoxyacetophenone, pentyl-4-dimethylaminobenzoate, 2-(o-chlorophenyl)-4,5-diphenylimidazolyl Examples of the photopolymerization initiator include dimer, 2,4-bis-trichloromethyl-6-[di-(ethoxycarbonylmethyl)amino]phenyl-S-triazine, 2,4-bis-trichloromethyl-6-(4-ethoxy)phenyl-S-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-ethoxy)phenyl-S-triazineanthraquinone, 2-t-butylanthraquinone, 2-amyl anthraquinone, and β-chloroanthraquinone. These photopolymerization initiators can be used alone or in combination of two or more kinds.

[0040] Among photopolymerization initiators, it is preferable to use one or a mixture of two or more selected from the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, because they are active against light of a wider range of wavelengths and can improve the curing properties of the cured coating film of the composition.

[0041] The molecular weight of the photopolymerization initiator is not particularly limited, but is, for example, 50 to 500, preferably 50 to 300, and more preferably 50 to 210. From the viewpoint of reducing the viscosity of the composition, it is preferable to use a photopolymerization initiator with a lower molecular weight.

[0042] Commercially available photopolymerization initiators include, for example, "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-2959", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-754", "Omnirad-784", "Omnirad-500", and "Omnirad-4265". Examples of such antibacterial agents include "IGM" (manufactured by IGM), "Kayacure-DETX", "Kayacure-MBP", "Kayacure-DMBI", "Kayacure-EPA", "Kayacure-OA" (manufactured by Nippon Kayaku Co., Ltd.), "Baicure-10", "Baicure-55" (manufactured by Stouffer Chemical Co., Ltd.), "Trigonal P1" (manufactured by Akzo), "Sandray 1000" (manufactured by Sandoz), "Deep" (manufactured by Upjohn), "Quantacure-PDO", "Quantacure-ITX", "Quantacure-EPD" (manufactured by Ward Blenkinsop), and "Runtecure-1104" (manufactured by Runtec).

[0043] The amount of the photopolymerization initiator added is preferably within a range in which the photopolymerization initiator can fully function and does not cause crystal precipitation or deterioration of the coating film properties. Specifically, the amount is preferably within a range of 0.05 to 20 parts by mass, and more preferably 0.1 to 10 parts by mass, per 100 parts by mass of the resin solid content in the composition.

[0044] (Leveling agent) The composition of the present invention may contain a leveling agent. As the leveling agent, various known leveling agents can be used. The leveling agent is an additive that adjusts the fluidity of the composition and has the function of making the coating film obtained by applying the composition flatter, and examples thereof include silicone-based, polyacrylate-based and perfluoroalkyl-based leveling agents.

[0045] As the leveling agent, a commercially available product may be used. Specific examples of the leveling agent include DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341, X22-161A, KF6001 (all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (all manufactured by Momentive Performance Materials Co., Ltd.). Japan LLC), Fluorinert (registered trademark) FC-72, FC-40, FC-43, FC-3283 (all manufactured by Sumitomo 3M Limited), Megafac (registered trademark) R-08, R-30, R-90, F-410, F-411, F-443, F-445, F-470, F-477, F-479, F-480, F-481, F-482, F-483, F-484, F-485, F-486, F-487, F-488, F-489, F-490, F-500, F-501, F-502, F-503, F-504, F-505, F-506, F-507, F-508, F-509, F-510, F-511, F-512, F-513, F-514, F-515, F-516, F-517, F-518, F-520, F-521, F-522, F-523, F-524, F-525, F-526, F-527, F-528, F-529, F-530, F-531, F-532, F-533, F-534, F-535, F-536, F-537, F-538, F-539, F-540, F-541, F-542, F-543, F-544, F-545, F-546, F-547, F-548, F-549, F-548, F-549, F-549, F-549, F-549, F-549, F F-482, F-483, F-556 (all manufactured by DIC Corporation), F-top (trade name) EF301, EF303, EF351, EF352 (all manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S-381, S-382, S-383, S-393, SC-101, SC-105, KH-40, SA-100 (all manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), All of the above are manufactured by AGC Seimi Chemical Co., Ltd.), trade names E1830 and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-331, BYK-333, BYK-345, BYK-348, BYK-349, BYK-352, BYK-353, BYK-356, BYK-361N, BYK-377, Examples of the leveling agent include BYK-378, BYK-399, BYK-3450, BYK-3451, BYK-3455, BYK-UV3500, BYK-UV3505, BYK-UV3510, BYK-UV3530, BYK-UV3535, BYK-UV3570, BYK-UV3575, and BYK-UV3576 (all trade names manufactured by BYK-Chemie Japan Co., Ltd.). The leveling agent can be used alone or in combination of two or more kinds.

[0046] The content of the leveling agent is preferably in the range of 0.01 to 0.5 parts by mass, more preferably in the range of 0.05 to 0.3 parts by mass, and particularly preferably in the range of 0.08 to 0.2 parts by mass, relative to 100 parts by mass of the resin solid content. When the content of the leveling agent is within the above range, the composition can be smoothly applied to a substrate, and a composition capable of forming a cured coating film having high hardness, excellent adhesion, and curl resistance can be obtained.

[0047] (Organic solvent) The composition of the present invention has an organic solvent content of 5% by mass or less, and the content of the organic solvent is preferably less from the viewpoint of VOC reduction as long as the viscosity suitable for coating is maintained, and is preferably 3% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less. The organic solvent is not particularly limited, and examples thereof include aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, isopropanol, and t-butanol; esters such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and glycol ethers such as propylene glycol monomethyl ether. These organic solvents can be used alone or in combination of two or more kinds.

[0048] The composition of the present invention may further contain other additives within the scope of not impeding the solution of the problems of the present invention. Examples of other additives include photosensitizers, ultraviolet absorbers, antioxidants, silicon-based additives, fluorine-based additives, silane coupling agents, phosphate ester compounds, organic beads, inorganic fine particles, inorganic fillers, rheology control agents, defoamers, antifogging agents, colorants, etc.

[0049] Examples of the photosensitizer include amine compounds such as aliphatic amines and aromatic amines, urea compounds such as o-tolylthiourea, and sulfur compounds such as sodium diethyldithiophosphate and s-benzylisothiuronium-p-toluenesulfonate.

[0050] Examples of ultraviolet absorbents include triazine derivatives such as 2-[4-{(2-hydroxy-3-dodecyloxypropyl)oxy}-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2-[4-{(2-hydroxy-3-tridecyloxypropyl)oxy}-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2'-xanthenecarboxy-5'-methylphenyl)benzotriazole, 2-(2'-o-nitrobenzyloxy-5'-methylphenyl)benzotriazole, 2-xanthenecarboxy-4-dodecyloxybenzophenone, and 2-o-nitrobenzyloxy-4-dodecyloxybenzophenone. These ultraviolet absorbents can be used alone or in combination of two or more.

[0051] Examples of the antioxidant include hindered phenol-based antioxidants, hindered amine-based antioxidants, organic sulfur-based antioxidants, and phosphate-based antioxidants.

[0052] Examples of the silicon-based additive include polyorganosiloxanes having an alkyl group or a phenyl group, such as methylphenylpolysiloxane, cyclic dimethylpolysiloxane, methylhydrogenpolysiloxane, fluorine-modified dimethylpolysiloxane copolymer, and amino-modified dimethylpolysiloxane copolymer.

[0053] Examples of fluorine-based additives include the "Megaface" series manufactured by DIC Corporation.

[0054] Examples of the silane coupling agent include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, Examples of vinyl-based silane coupling agents include N-propyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane hydrochloride, special aminosilane, 3-ureidopropyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, 3-isocyanatopropyltriethoxysilane, allyltrichlorosilane, allyltriethoxysilane, allyltrimethoxysilane, diethoxymethylvinylsilane, trichlorovinylsilane, vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, and vinyltris(2-methoxyethoxy)silane.

[0055] Examples of phosphate ester compounds include those having a (meth)acryloyl group in the molecular structure. Commercially available products include, for example, "Kayamar PM-2" and "Kayamar PM-21" manufactured by Nippon Kayaku Co., Ltd., "Light Ester P-1M", "Light Ester P-2M", and "Light Acrylate P-1A(N)" manufactured by Kyoeisha Chemical Co., Ltd., "SIPOMER PAM 100", "SIPOMER PAM 200", "SIPOMER PAM 300", and "SIPOMER PAM 4000" manufactured by Solvay, "Viscoat #3PA" and "Viscoat #3PMA" manufactured by Osaka Organic Chemical Industry Co., Ltd., and "New Frontier S-23A" manufactured by Daiichi Kogyo Seiyaku Co., Ltd.; and "SIPOMER PAM 5000" manufactured by Solvay, which is a phosphate ester compound having an allyl ether group in its molecular structure.

[0056] Examples of organic beads include polymethylmethacrylate beads, polycarbonate beads, polystyrene beads, polyacrylicstyrene beads, silicone beads, glass beads, acrylic beads, benzoguanamine resin beads, melamine resin beads, polyolefin resin beads, polyester resin beads, polyamide resin beads, polyimide resin beads, polyethylene fluoride resin beads, polyethylene resin beads, etc. These organic beads can be used alone or in combination of two or more kinds. The average particle size of these organic beads is preferably in the range of 1 to 10 μm.

[0057] Examples of inorganic fine particles include fine particles of silica, alumina, zirconia, titania, barium titanate, antimony trioxide, etc. These inorganic fine particles can be used alone or in combination of two or more kinds. The average particle size of these inorganic fine particles is preferably in the range of 10 to 300 nm, more preferably in the range of 50 to 150 nm.

[0058] When inorganic fine particles are contained, a dispersion aid can be used. Examples of the dispersion aid include phosphate ester compounds such as isopropyl acid phosphate, triisodecyl phosphite, and ethylene oxide modified dimethacrylate phosphate. In addition, examples of commercially available dispersion aids include "Kayamer PM-21" and "Kayamer PM-2" manufactured by Nippon Kayaku Co., Ltd., and "Light Ester P-2M" manufactured by Kyoeisha Chemical Co., Ltd.

[0059] [Cured coating film] The cured coating film of the present invention is obtained by curing an active energy ray-curable composition, and is usually obtained by applying the active energy ray-curable composition onto a substrate and curing it as described below. Examples of a method for curing the active energy ray-curable composition include a heating method and a method for irradiating the composition with active energy rays such as ultraviolet rays.

[0060] The method of heating can be curing by heating for 0.5 to 60 minutes in a temperature range of 60 to 200°C. As a method of irradiating active energy rays, for example, in the case of ultraviolet rays, curing can be performed by using an ultraviolet lamp such as a low pressure mercury lamp, a high pressure mercury lamp, an ultra-high pressure mercury lamp, a xenon lamp, a gallium lamp, a metal halide lamp, sunlight, or an LED as an ultraviolet ray generating source. As the active energy rays, in addition to ultraviolet rays, for example, ionizing radiation such as electron beams, α rays, β rays, and γ rays can also be used. The irradiation dose of the active energy rays is 0.05 to 5 J / cm. 2 The range is preferably 0.1 to 3 J / cm 2 More preferably, the range is 0.1 to 1 J / cm 2 It is particularly preferable that the range is:

[0061] [Laminated film] The laminated film of the present invention has the above-mentioned cured coating film on a substrate. Examples of a method for producing the laminated film of the present invention include a method in which an active energy ray-curable resin composition is applied to at least one surface of a substrate, and then the substrate is irradiated with active energy rays.

[0062] Examples of the substrate include metal substrates, plastic substrates, glass substrates, paper substrates, wood substrates, and fibrous substrates. Among these substrates, plastic substrates are preferred because of their excellent adhesion. Examples of the material of the plastic substrate include polyethylene terephthalate, polyester, acrylic resin (polymethyl methacrylate, etc.), polycarbonate, acrylonitrile-butadiene-styrene copolymer (ABS resin), composite resin of ABS resin and polycarbonate, polystyrene, polyurethane, epoxy resin, polyvinyl chloride, polyamide, polyolefin (polyethylene, polypropylene, polycycloolefin (COP), etc.), triacetyl cellulose (TAC), and polyimide. Examples of the plastic substrate include plastic molded products such as mobile phones, home appliances, automobile interior and exterior materials, and office automation equipment. Film substrates made of plastic materials can also be used.

[0063] Examples of methods for applying the active energy ray-curable composition include application methods using a gravure coater, roll coater, comma coater, knife coater, air knife coater, curtain coater, kiss coater, shower coater, flow coater, spin coater, dipping, screen printing, spraying, brush coating, applicator, bar coater, etc. The thickness of the coating film formed using the active energy ray-curable composition can be appropriately adjusted depending on the application, but is usually preferably in the range of 0.01 to 50 μm.

[0064] The laminate film of the present invention may have, in addition to the substrate and the above-mentioned cured coating film, a functional film layer such as an anti-reflection film, a diffusion film, or a polarizing film.

[0065] The laminated film of the present invention has a cured coating film with high hardness and excellent curl resistance, and can therefore be used as a coating layer for protecting the surface of a substrate. For example, it can be suitably used as an optical film for use in flat panel displays (FPDs) such as liquid crystal displays (LCDs), organic electroluminescent displays (OLEDs), and plasma displays (PDPs). Examples of articles having the laminated film of the present invention include plastic molded products such as mobile phones, housings for home appliances, automobile bumpers, and office automation equipment. EXAMPLES

[0066] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. In the compositions of the following examples, "%" means "% by mass" and "parts" means "parts by mass".

[0067] (Example 1: Preparation of active energy ray-curable composition (1)) An active energy ray curable composition (1) was prepared by uniformly mixing 80 parts of glycerin triacrylate ("Aronix M-930" manufactured by Toagosei Co., Ltd., hydroxyl value: 30 mg KOH, viscosity 30 mPa·s), 20 parts of 2-(2-vinyloxyethoxy)ethyl acrylate (VEEA (registered trademark) manufactured by Nippon Shokubai Co., Ltd.), 0.1 parts of a leveling agent ("BYK-356" manufactured by BYK Japan Co., Ltd.), and 5 parts of a photopolymerization initiator ("Runtecure1104" manufactured by RUNTEC Chemical Co., Ltd.).

[0068] (Examples 2 to 11 and Comparative Examples 1 to 9: Preparation of active energy ray-curable compositions (2) to (11) and (R1) to (R9)) Except for changing the composition of each component as shown in Table 1 or 2, the same method as in Example 1 was used to obtain active energy ray-curable compositions (2) to (11) and (R1) to (R9).

[0069] The active energy ray-curable compositions obtained in the above Examples and Comparative Examples were subjected to the following measurements and evaluations.

[0070] [Viscosity measurement] The viscosity (mPa·s) at 25° C. of the active energy ray-curable composition obtained in each of the Examples and Comparative Examples was measured using an E-type viscometer (TV-25, manufactured by Toki Sangyo Co., Ltd.).

[0071] [Preparation of evaluation samples] The active energy ray-curable composition of each example was applied to a 40 μm-thick TAC substrate ("FTTD40UC" manufactured by Fuji Film Corporation) with a thickness of 40 μm using a bar coater, and then exposed to a light dose of 150 mJ / cm using an ultraviolet irradiation device (high-pressure mercury lamp manufactured by iGraphics Co., Ltd.) under a nitrogen atmosphere. 2 A TAC substrate having a cured coating film with a thickness of 5-6 μm was obtained, and this was used as an evaluation sample.

[0072] [Adhesion evaluation] The surface of the cured coating of the evaluation sample obtained above was scored with a cutter knife to create 100 1 mm x 1 mm grids. Cellophane tape (Cellotape (registered trademark) CT-18, manufactured by Nichiban Co., Ltd.) was then applied on top of the grids and quickly peeled off. The number of grids that remained unpeeled was counted and evaluated according to the following criteria, with A being a pass and B to D being failing. A: There were 100 remaining squares. B: The number of remaining grids was 95 or more but less than 100. C: The number of remaining grids was 10 or more but less than 95. D: Fewer than 10 grids remained.

[0073] [Hardness rating; pencil hardness] The hardness of the cured coating film surface of the curable resin composition obtained above was measured under a load of 500 g according to JIS K5600-5-4 [Scratch hardness (pencil method)]. Five measurements were made for each hardness, and the hardness at which no scratches were observed four or more times was regarded as the hardness of the cured coating film. The hardness of pencils, from highest to lowest, is 3H, 2H, H, F, HB, and B.

[0074] [Scratch resistance evaluation: Steel wool (SW) test] The contact area of ​​the evaluation sample obtained above is 4 cm 2 A #0000 steel wool was attached to a loading plate (2cm x 2cm square) and a weight of 1000g was placed on it, which was then moved back and forth over the test piece 10 times. The surface was then visually observed for scratches.

[0075] [Evaluation of bending resistance; mandrel test] The evaluation sample obtained above was wrapped around a 10 mm diameter mandrel test rod with the coated surface facing outward, and the occurrence of breaks or cracks in the cured coating was confirmed. The diameter of the mandrel was changed to smaller and smaller ones until breaks or cracks occurred in the cured coating, and the smallest mandrel value at which breaks or cracks did not occur was evaluated.

[0076] The above evaluation results are shown in Tables 1 and 2. The viscosity (mPa·s) of each component is listed for reference.

[0077] [Table 1]

[0078] [Table 2]

[0079] The abbreviations in Tables 1 and 2 other than those mentioned above represent the following compounds. Miramer M300: Trimethylolpropane triacrylate (MIWON, Miramer M300) ARONIX M-305: A reaction product of pentaerythritol and acrylic acid, the main component of which is pentaerythritol tri / tetraacrylate ("ARONIX M-305" manufactured by Toagosei Co., Ltd.) Luxidia 17-806: Luxidia 17-806 manufactured by DIC DEGDVE: "Diethylene glycol divinyl ether" manufactured by Nippon Carbide Industries Co., Ltd. AOMA: Cyclopolymerizable monomer, "AOMA (registered trademark)" manufactured by Nippon Shokubai Co., Ltd. IPEMA: Isoprenyl methacrylate, Kuraray's "IPEMA (registered trademark)" Aronix M-920: Glycerin di / triacrylate (Aronix M-920 manufactured by Toagosei Co., Ltd.) Miramer M200: Hexanediol diacrylate (MIWON, Miramer M200) Viscoat #260: 1,9-nonanediol diacrylate (1,9-NDDA), Osaka Organic Chemical Industry Co., Ltd. "Viscoat #260" Light Acrylate 3EG-A: Triethylene glycol diacrylate (Kyoei Chemical Co., Ltd. "Light Acrylate 3EG-A") ACMO: acryloylmorpholine (ACMO (registered trademark), manufactured by KJ Chemicals) Miramer M221: Dipropylene glycol diacrylate (MIWON "Miramer M221") 4-HBA: 4-hydroxybutyl acrylate (Osaka Organic Chemical Industry Co., Ltd.) Runtecure 1104: 1-Hydroxy-cyclohexylphenyl-ketone (IGM Resins, photoinitiator; Runtecure® 1104) BYK-356: Leveling agent (polyacrylate surface conditioner) (BYK-356 manufactured by BYK Japan)

[0080] From the evaluation results of the cured coating film using the compositions of Examples 1 to 11, it was confirmed that the composition of the present invention can form a cured coating film with low viscosity and excellent adhesion, hardness, and curl resistance without using a solvent. On the other hand, in Comparative Example 1, in which the content of component (B) is less than 10 mass%, the viscosity of the coating material (composition) was high and the curl resistance was reduced. In Comparative Examples 2 to 6 and 8, which do not contain component (B), the viscosity of the composition was increased or the hardness and scratch resistance of the cured coating film were reduced depending on the combination of compounds. Similarly, in Comparative Examples 7 and 9, which do not contain component (A), the viscosity of the composition was increased or the hardness and scratch resistance of the cured coating film were reduced.

Claims

1. 1. An active energy ray-curable composition comprising the following components (A) and (B), wherein the content of component (A) is 40% by mass to 89% by mass, the content of component (B) is 10% by mass to 60% by mass, and the content of an organic solvent is 5% by mass or less: Component (A): A polyfunctional (meth)acrylate having a viscosity of 100 mPa·s or less at 25° C. (excluding component (B)) Component (B): a bifunctional monomer having a reactive site represented by the following formula (1) and a viscosity at 25° C. of 10 mPa·s or less 【Chemistry 1】 Formula (1) [In formula (1), R １ , R ２ , and R ３ are each independently a hydrogen atom or a methyl group, R ４ represents an alkyl chain having 0 to 3 carbon atoms.

2. 2. The active energy ray-curable composition according to claim 1, wherein the component (B) has a vinyl ether group, an allyl ether group, or an isoprenyl group as the reactive site represented by formula (1).

3. The active energy ray-curable composition according to claim 1 or 2, further comprising 1% by mass to 25% by mass of the following component (C): Component (C): a monofunctional or bifunctional monomer having a viscosity of 10 mPa·s or less at 25° C. (excluding component (B))

4. 3. The active energy ray-curable composition according to claim 1, wherein the viscosity of the component (A) at 25° C. is 70 mPa·s or less.

5. 3. The active energy ray-curable composition according to claim 1, further comprising a photopolymerization initiator.

6. The active energy ray-curable composition according to claim 1 or 2, further comprising a leveling agent.

7. A cured coating film which is a cured reaction product of the active energy ray-curable composition according to claim 1 or 2.

8. A laminate film comprising the cured coating film according to claim 7 and a substrate.

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