Active energy ray-curable composition, cured product, and laminate

Abstract

To provide an active energy ray-curable composition, a cured product, and a laminate.SOLUTION: An active energy ray-curable composition comprising an oxygen-hydrogen bond-containing poly(meth)acrylate, a fluorine-containing compound, and an amine.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] In recent years, liquid crystal display devices have been used as display devices for televisions, personal computers, etc. In such liquid crystal display devices, the use of an anti-reflection film including a low refractive index layer has been proposed to prevent reflection of external light and improve image quality (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-085383 Summary of the Invention [Problem to be solved by the invention]

[0004] The problem to be solved by the present invention is to provide an active energy ray-curable composition that can produce a cured product having good steel wool resistance. [Means for solving the problem]

[0005] The present disclosure provides the following: (Item 1) An active energy ray-curable composition, comprising an oxygen-hydrogen bond-containing poly(meth)acrylate, a fluorine-containing compound, and an amine. (Item 2) The active energy ray-curable composition according to the preceding item, which contains solid alumina particles. (Item 3) A cured product of the active energy ray-curable composition according to any one of the above items. (Item 4) A laminate comprising the cured product described in the above item.

[0006] In the present disclosure, one or more of the above-described features may be provided in further combinations in addition to the combinations explicitly stated. [Effects of the Invention]

[0007] The active energy ray-curable composition of the present invention exhibits good steel wool resistance. DETAILED DESCRIPTION OF THE INVENTION

[0008] Throughout this disclosure, the range of the values ​​of the physical properties, contents, etc. may be set as appropriate (for example, by selecting from the values ​​described in each item below). Specifically, when the value α includes A3, A2, A1 (where A3>A2>A1), the range of the value α may include A3 or less, A2 or less, less than A3, less than A2, A1 or more, A2 or more, greater than A1, greater than A2, A1 to A2 (A1 or more and less than A2), A1 to A3, A2 to A3, A1 or more and less than A3, A1 or more and less than A2, A2 or more and less than A3, greater than A1 and less than A3, greater than A1 and less than A2, greater than A2 and less than A3, greater than A1 ... and the like.

[0009] As long as the problem to be solved by the present invention is solved, there are no particular limitations on the components, conditions, values, etc.

[0010] "αβ amount (A / B)" means the β amount (α) of A relative to 100% by mass of B. α can be expressed, for example, in mass %, mol %, or parts by mass. β amount can be expressed, for example, in content or amount used. "% by mass content (A / B)" means the content (% by mass) of A relative to 100% by mass of B.

[0011] The term "γ ratio (A / B)" refers to the γ ratio calculated by the formula "A÷B." Examples of the γ ratio include a mass ratio and a molar ratio.

[0012] "Non-volatile content" refers to the total mass of components other than organic solvents and water. In one embodiment, "non-volatile content of A" refers to the total mass of components remaining when 1 g of A is heated at 105°C and reaches a constant weight.

[0013] "(Meth)acrylic" means "acrylic and / or methacrylic". "(Meth)acrylate" means "acrylate and / or methacrylate". "(Meth)acryloyl" means "acryloyl and / or methacryloyl".

[0014] "Poly(meth)acrylate" means a compound having two or more (meth)acryloyl groups.

[0015] "C···" means "having carbon number···." For example, a "C1-6 alkyl group" means an alkyl group having 1 to 6 carbon atoms. A "C6 alkyl group" means an alkyl group having 6 carbon atoms.

[0016] Examples of the alkyl group include a linear alkyl group, a branched alkyl group, and a cycloalkyl group.

[0017] Examples of the straight-chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0018] Examples of branched alkyl groups include an iso-propyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a 2-ethylhexyl group, a diethylpentyl group, a trimethylbutyl group, a trimethylpentyl group, and a trimethylhexyl group.

[0019] Examples of the cycloalkyl group include a monocyclic cycloalkyl group, a bridged ring cycloalkyl group, a fused ring cycloalkyl group, etc. A cycloalkyl group in which at least one hydrogen atom of the cycloalkyl group is substituted with an alkyl group is also considered to be a cycloalkyl group.

[0020] "Monocyclic ring" means a ring structure formed by covalent carbon bonds and having no internal bridges. "Fused ring" means a ring structure in which two or more monocyclic rings share two atoms (i.e., each ring shares only one edge (fused) with another). "Bridged ring" means a ring structure in which two or more monocyclic rings share three or more atoms.

[0021] Examples of the monocyclic cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclodecyl group, and a 3,5,5-trimethylcyclohexyl group.

[0022] Examples of the bridged ring cycloalkyl group include a tricyclodecyl group, an adamantyl group, and a norbornyl group.

[0023] The alkyl group also includes a group formed by combining a linear alkyl group, a branched alkyl group, and a cycloalkyl group. Examples of the combined group include a cycloalkylalkyl group.

[0024] The cycloalkylalkyl group is represented by the following formula: R calkyl -R alkyl - (In the formula, R calkyl represents a cycloalkyl group. alkyl represents an alkyl group.

[0025] Examples of the alkylene group include a linear alkylene group, a branched alkylene group, and a cycloalkylene group.

[0026] Examples of the straight-chain alkylene group include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, an n-pentylene group, an n-hexylene group, an n-heptylene group, an n-octylene group, an n-nonylene group, and an n-decamethylene group.

[0027] Examples of the branched alkylene group include a diethylpentylene group, a trimethylbutylene group, a trimethylpentylene group, and a trimethylhexylene group.

[0028] Examples of the cycloalkylene group include a monocyclic cycloalkylene group, a bridged ring cycloalkylene group, a fused ring cycloalkylene group, etc. In addition, one or more hydrogen atoms of the cycloalkylene group may be substituted with a linear or branched alkyl group.

[0029] Examples of the monocyclic cycloalkylene group include a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclodecylene group, and a 3,5,5-trimethylcyclohexylene group.

[0030] Examples of the bridged ring cycloalkylene group include a tricyclodecylene group, an adamantylene group, and a norbornylene group.

[0031] Examples of the fused ring cycloalkylene group include a bicyclodecylene group.

[0032] The alkylene group also includes a group formed by combining a linear alkylene group, a branched alkylene group, and a cycloalkylene group, such as a cycloalkylene alkylene group and an alkylene cycloalkylene alkylene group.

[0033] The cycloalkylene alkylene group is represented by the following formula: -R calkylene -R alkylene - (In the formula, R calkylene represents a cycloalkylene group. alkylene represents an alkylene group.

[0034] The alkylenecycloalkylenealkylene group is represented by the following formula: -R alkylene -R calkylene -R alkylene - (In the formula, R calkylene represents a cycloalkylene group. alkylene represents an alkylene group.

[0035] Examples of the aryl group include a monocyclic aryl group and a fused ring aryl group.

[0036] Examples of the monocyclic aryl group include a phenyl group, a tolyl group, and a mesityl group.

[0037] The fused ring aryl group may, for example, be a naphthyl group.

[0038] Examples of the arylene group include a monocyclic arylene group and a fused-ring arylene group.

[0039] Examples of the monocyclic arylene group include a phenylene group and a tolylene group.

[0040] The fused ring arylene group may, for example, be a naphthylene group.

[0041] [Active energy ray-curable composition] The present disclosure relates to an active energy ray-curable composition, the active energy ray-curable composition comprising an oxygen-hydrogen bond-containing poly(meth)acrylate, a fluorine-containing compound, and an amine.

[0042] <Poly(meth)acrylate containing oxygen-hydrogen bonds> The oxygen-hydrogen bond-containing poly(meth)acrylates may be used alone or in combination of two or more.

[0043] The term "oxygen-hydrogen bond-containing poly(meth)acrylate" refers to a poly(meth)acrylate having oxygen-hydrogen bonds at a pH of 7 or less. The oxygen-hydrogen bond-containing poly(meth)acrylate may be in the form of a salt at a pH of more than 7.

[0044] Examples of oxygen-hydrogen bond-containing poly(meth)acrylates include hydroxyl group-containing poly(meth)acrylates, carboxyl group-containing poly(meth)acrylates, sulfonic acid group-containing poly(meth)acrylates, and phosphoric acid group-containing poly(meth)acrylates.

[0045] (Hydroxyl group-containing poly(meth)acrylate) Examples of hydroxyl group-containing poly(meth)acrylates include hydroxyl group-containing pentaerythritol poly(meth)acrylate, hydroxyl group-containing polypentaerythritol poly(meth)acrylate, hydroxyl group-containing trimethylolpropane poly(meth)acrylate, hydroxyl group-containing polytrimethylolpropane poly(meth)acrylate, hydroxyl group-containing glycerin poly(meth)acrylate, and hydroxyl group-containing polyglycerin poly(meth)acrylate.

[0046] Examples of the hydroxyl group-containing pentaerythritol poly(meth)acrylate include pentaerythritol di(meth)acrylate and pentaerythritol tri(meth)acrylate.

[0047] Examples of hydroxyl group-containing polypentaerythritol poly(meth)acrylates include dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, tripentaerythritol di(meth)acrylate, tripentaerythritol tri(meth)acrylate, tripentaerythritol tetra(meth)acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, and tripentaerythritol hepta(meth)acrylate.

[0048] Examples of the hydroxyl group-containing trimethylolpropane poly(meth)acrylate include trimethylolpropane di(meth)acrylate.

[0049] Examples of the hydroxyl group-containing polytrimethylolpropane poly(meth)acrylate include ditrimethylolpropane di(meth)acrylate and ditrimethylolpropane tri(meth)acrylate.

[0050] Examples of hydroxyl group-containing glycerin poly(meth)acrylates include glycerin di(meth)acrylate.

[0051] Examples of the hydroxyl group-containing polyglycerin poly(meth)acrylate include diglycerin di(meth)acrylate and diglycerin tri(meth)acrylate.

[0052] (Carboxyl group-containing poly(meth)acrylate) Examples of the carboxyl group-containing poly(meth)acrylate include a reaction product of a hydroxyl group-containing poly(meth)acrylate with a carboxylic acid anhydride.

[0053] Examples of carboxylic acid anhydrides include phthalic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, nadic anhydride, methylnadic anhydride, maleic anhydride, itaconic anhydride, and succinic anhydride.

[0054] Examples of the product (carboxyl group-containing poly(meth)acrylate) include Aronix M510 (acid value: 80 mg KOH / g to 120 mg KOH / g, manufactured by Toagosei Co., Ltd.) and Aronix M520 (acid value: 20 mg KOH / g to 40 mg KOH / g, manufactured by Toagosei Co., Ltd.).

[0055] In one embodiment, the oxygen-hydrogen bond-containing poly(meth)acrylate is preferably a carboxyl group-containing poly(meth)acrylate, more preferably a reaction product of pentaerythritol tri(meth)acrylate or dipentaerythritol penta(meth)acrylate with a carboxylic acid anhydride, even more preferably a reaction product of pentaerythritol tri(meth)acrylate with a carboxylic acid anhydride, and particularly preferably a reaction product of pentaerythritol tri(meth)acrylate with succinic anhydride.

[0056] Examples of the molecular weight (oxygen-hydrogen bond-containing poly(meth)acrylate) include 50,000, 40,000, 30,000, 20,000, 10,000, 5,000, 4,000, 2,000, 1,000, 900, 800, 700, 600, 500, 450, 400, 300, 250, and 200. In one embodiment, the molecular weight is preferably 200 to 50,000.

[0057] "Molecular weight" refers to either formula weight or number average molecular weight. When the structure of a compound can be unequivocally expressed by a specific chemical formula (i.e., the molecular weight distribution is 1), "molecular weight" refers to formula weight. On the other hand, when the structure of a compound cannot be unequivocally expressed by a specific chemical formula (i.e., the molecular weight distribution is greater than 1), "molecular weight" refers to number average molecular weight.

[0058] The acid value (oxygen-hydrogen bond-containing poly(meth)acrylate) is, for example, 300 mg KOH / g, 290 mg KOH / g, 280 mg KOH / g, 270 mg KOH / g, 260 mg KOH / g, 250 mg KOH / g, 240 mg KOH / g, 230 mg KOH / g, 220 mg KOH / g, 210 mg KOH / g, 200 mg KOH / g, 190 mg KOH / g, 180 mg KOH / g, 170 mg Examples of the acid value include 160 mgKOH / g, 150 mgKOH / g, 140 mgKOH / g, 130 mgKOH / g, 120 mgKOH / g, 110 mgKOH / g, 100 mgKOH / g, 90 mgKOH / g, 80 mgKOH / g, 70 mgKOH / g, 60 mgKOH / g, 50 mgKOH / g, 40 mgKOH / g, 30 mgKOH / g, 20 mgKOH / g, and 10 mgKOH / g. In one embodiment, the acid value is preferably 10 mgKOH / g to 300 mgKOH / g.

[0059] The hydroxyl value (oxygen-hydrogen bond-containing poly(meth)acrylate) is, for example, 280 mg KOH / g, 270 mg KOH / g, 260 mg KOH / g, 250 mg KOH / g, 240 mg KOH / g, 230 mg KOH / g, 220 mg KOH / g, 210 mg KOH / g, 200 mg KOH / g, 190 mg KOH / g, 180 mg KOH / g, 170 mg KOH / g, 160 mg KOH / g, 15 Examples of the hydroxyl value include 0 mgKOH / g, 140 mgKOH / g, 130 mgKOH / g, 120 mgKOH / g, 110 mgKOH / g, 100 mgKOH / g, 90 mgKOH / g, 80 mgKOH / g, 70 mgKOH / g, 60 mgKOH / g, 50 mgKOH / g, 40 mgKOH / g, 30 mgKOH / g, 20 mgKOH / g, 10 mgKOH / g, 5 mgKOH / g, and 0 mgKOH / g. In one embodiment, the hydroxyl value is preferably 0 mgKOH / g to 280 mgKOH / g, and more preferably 10 mgKOH / g to 280 mgKOH / g.

[0060] The number of (meth)acryloyl groups (oxygen-hydrogen bond-containing poly(meth)acrylate) may be, for example, 30, 28, 26, 24, 22, 20, 18, 16, 14, 12, 10, 9, 8, 7, 6, 5, 4, 3, or 2. In one embodiment, the number is preferably 2 to 30.

[0061] The number of oxygen-hydrogen bonds (oxygen-hydrogen bond-containing poly(meth)acrylate) may be, for example, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1. In one embodiment, the number is preferably 1 to 10.

[0062] Examples of the mass % content (oxygen-hydrogen bond-containing poly(meth)acrylate / active energy ray-curable composition nonvolatile content) include 70 mass %, 65 mass %, 60 mass %, 57 mass %, 55 mass %, 54 mass %, 53 mass %, 52 mass %, 51 mass %, 50 mass %, 49 mass %, 48 mass %, 47 mass %, 46 mass %, 45 mass %, 44 mass %, 43 mass %, 42 mass %, 41 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, etc. In one embodiment, the content is preferably 5 mass % to 70 mass %.

[0063] <Fluorine-containing compounds> The fluorine-containing compounds may be used alone or in combination of two or more.

[0064] Examples of the fluorine-containing compound include fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, fluoroalkyl ammonium salts, fluoroalkyl ethylene oxide derivatives, fluoroadamantane derivatives, (meth)acryloyl group-containing perfluoropolyethers, etc. In one embodiment, the fluorine-containing compound is preferably (meth)acryloyl group-containing perfluoropolyethers.

[0065] ((Meth)acryloyl group-containing perfluoropolyether) In one embodiment, the active energy ray-curable composition may contain a (meth)acryloyl group-containing perfluoropolyether. The (meth)acryloyl group-containing perfluoropolyether may be used alone or in combination of two or more kinds.

[0066] "(Meth)acryloyl group-containing perfluoropolyether" means a compound in which one or more (meth)acryloyl groups are bonded to a perfluoropolyether. "Perfluoropolyether" means a compound in which perfluoroalkylene ether is a repeating unit.

[0067] Examples of the (meth)acryloyl group-containing perfluoropolyether include perfluoropolyethers containing (meth)acryloyl groups at both ends and perfluoropolyethers containing a (meth)acryloyl group at one end.

[0068] Examples of the product ((meth)acryloyl group-containing perfluoropolyether) include KY-1203 and KY-1207 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0069] In one embodiment, the (meth)acryloyl group-containing perfluoropolyether is preferably a silicon atom- and (meth)acryloyl group-containing perfluoropolyether. Examples of the product (silicon atom- and (meth)acryloyl group-containing perfluoropolyether) include KY-1203 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0070] Examples of the mass % content (fluorine-containing compound / non-volatile content of active energy ray-curable composition) include 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, etc. In one embodiment, the mass % content (fluorine-containing compound / non-volatile content of active energy ray-curable composition) is preferably 1 mass % to 40 mass %, and more preferably more than 3 mass % and 10 mass % or less.

[0071] <amine> The amines may be used alone or in combination of two or more.

[0072] Examples of the amine include hydrocarbon amines and non-hydrocarbon amines.

[0073] (hydrocarbon amines) "Hydrocarbon amine" means an amine composed solely of carbon, hydrogen, and nitrogen atoms.

[0074] Examples of the hydrocarbon amine include aliphatic hydrocarbon amines and aromatic hydrocarbon amines.

[0075] <Aliphatic hydrocarbon amine> "Aliphatic hydrocarbylamine" means a hydrocarbylamine in which all of the hydrocarbon moieties are aliphatic groups.

[0076] Examples of the aliphatic hydrocarbon amine include aliphatic hydrocarbon acyclic amines and aliphatic hydrocarbon cyclic amines.

[0077] "Acyclic amine" means an amine in which the ring-forming atoms do not include a nitrogen atom.

[0078] Examples of the acyclic aliphatic hydrocarbon amine include acyclic aliphatic hydrocarbon monoamines.

[0079] Examples of the acyclic aliphatic hydrocarbon monoamine include a primary acyclic aliphatic hydrocarbon monoamine, a secondary acyclic aliphatic hydrocarbon monoamine, and a tertiary acyclic aliphatic hydrocarbon monoamine.

[0080] Examples of aliphatic hydrocarbon primary acyclic monoamines include methylamine, ethylamine, n-propylamine, iso-propylamine, n-butylamine, sec-butylamine, iso-butylamine, tert-butylamine, and amantadine.

[0081] Examples of aliphatic hydrocarbon secondary acyclic monoamines include dimethylamine, diethylamine, di(n-propyl)amine, di(iso-propyl)amine, di(n-butyl)amine, di(sec-butyl)amine, di(iso-butyl)amine, and di(tert-butyl)amine.

[0082] Examples of aliphatic hydrocarbon tertiary acyclic monoamines include trimethylamine, triethylamine, tri(n-propyl)amine, tri(iso-propyl)amine, tri(n-butyl)amine, tri(sec-butyl)amine, tri(iso-butyl)amine, and tri(tert-butyl)amine.

[0083] In one embodiment, the aliphatic hydrocarbon acyclic amine is represented by the formula: NR as1 as H (3-as) (R as1 each independently represents an alkyl group (for example, a C1-4 alkyl group). as represents 1, 2, or 3.

[0084] "Cyclic amine" means an amine in which the atoms forming the ring include a nitrogen atom.

[0085] Examples of the aliphatic hydrocarbon cyclic amine include aliphatic hydrocarbon cyclic monoamines and aliphatic hydrocarbon cyclic diamines.

[0086] Examples of the aliphatic hydrocarbon cyclic monoamine include pyrrolidine, piperidine, and quinuclidine.

[0087] Examples of the aliphatic hydrocarbon cyclic diamine include piperazine and 1,4-diazabicyclo[2.2.2]octane.

[0088] <Aromatic hydrocarbon amines> "Aromatic hydrocarbylamine" means a hydrocarbylamine containing an aromatic group in the hydrocarbon portion.

[0089] Examples of aromatic hydrocarbon amines include aromatic hydrocarbon acyclic amines and aromatic hydrocarbon cyclic amines.

[0090] Examples of the aromatic hydrocarbon acyclic amine include aromatic hydrocarbon acyclic monoamines and aromatic hydrocarbon acyclic diamines.

[0091] Examples of aromatic hydrocarbon acyclic monoamines include aromatic hydrocarbon acyclic primary monoamines, aromatic hydrocarbon acyclic secondary monoamines, and aromatic hydrocarbon acyclic tertiary monoamines.

[0092] Examples of aromatic hydrocarbon acyclic primary monoamines include aniline, benzylamine, and phenethylamine.

[0093] Examples of aromatic hydrocarbon acyclic secondary monoamines include N-methylaniline, N-methylbenzylamine, and phenethylmethylamine.

[0094] Examples of aromatic hydrocarbon acyclic tertiary monoamines include N,N-dimethylaniline, N,N-dimethylbenzylamine, and phenethyldimethylamine.

[0095] Examples of aromatic hydrocarbon acyclic diamines include aromatic hydrocarbon acyclic primary diamines, aromatic hydrocarbon acyclic secondary diamines, and aromatic hydrocarbon acyclic tertiary diamines.

[0096] Examples of aromatic hydrocarbon acyclic primary diamines include 1,2-xylylenediamine, 1,3-xylylenediamine, and 1,4-xylylenediamine.

[0097] Examples of aromatic hydrocarbon acyclic secondary diamines include 1,2-xylylenebis(methylamine), 1,3-xylylenebis(methylamine), and 1,4-xylylenebis(methylamine).

[0098] Examples of aromatic hydrocarbon acyclic tertiary diamines include 1,2-xylylenebis(dimethylamine), 1,3-xylylenebis(dimethylamine), and 1,4-xylylenebis(dimethylamine).

[0099] In one embodiment, the aromatic hydrocarbon acyclic amine is represented by the formula: H(3-ah1) R ah1 ah1 NR ah3 -NR ah2 ah2 H (3-ah2) (R ah1 ~R ah2 R each independently represents an alkyl group (for example, a C1-4 alkyl group). ah3 represents an alkylene group (for example, a C1-4 alkylene group). ah1 and ah2 each independently represent 1, 2, or 3.

[0100] Examples of aromatic hydrocarbon cyclic amines include aromatic hydrocarbon cyclic monoamines and aromatic hydrocarbon cyclic diamines.

[0101] Examples of aromatic hydrocarbon cyclic monoamines include pyrrole and pyridine.

[0102] Examples of aromatic hydrocarbon cyclic diamines include pyrazole, imidazole, pyridazine, pyrimidine, pyrazine, and 4-dimethylaminopyridine.

[0103] (Non-hydrocarbon amines) "Non-hydrocarbon amine" means an amine containing atoms other than carbon, hydrogen, and nitrogen atoms (other atoms).

[0104] The other atoms include, for example, oxygen atoms.

[0105] Examples of non-hydrocarbon amines include non-hydrocarbon acyclic amines and non-hydrocarbon cyclic amines.

[0106] Examples of non-hydrocarbon acyclic amines include alkanolamines and polyoxyalkyleneamines.

[0107] <Alkanolamine> Examples of alkanolamines include monoalkanolamines, dialkanolamines, and trialkanolamines.

[0108] Examples of monoalkanolamines include methanolamine, 2-hydroxyethylamine (ethanolamine), 1-hydroxyethylamine, 3-hydroxypropylamine, 1-hydroxy-1-methylethylamine, 2-hydroxy-1-methylethylamine, and N-(2-aminoethyl)ethanolamine.

[0109] Examples of dialkanolamines include dimethanolamine, di(2-hydroxyethyl)amine (diethanolamine), di(1-hydroxyethyl)amine, di(3-hydroxypropyl)amine, di(1-hydroxy-1-methylethyl)amine, di(2-hydroxy-1-methylethyl)amine, and di(N-(2-aminoethyl)ethanol)amine.

[0110] Examples of trialkanolamines include trimethanolamine, tri(2-hydroxyethyl)amine (triethanolamine), tri(1-hydroxyethyl)amine, tri(3-hydroxypropyl)amine, tri(1-hydroxy-1-methylethyl)amine, tri(2-hydroxy-1-methylethyl)amine, and tri(N-(2-aminoethyl)ethanol)amine.

[0111] In one embodiment, the alkanolamine is represented by the formula: NR ao1 ao R ao2 (3-ao) (R ao1 R each independently represents a hydroxyalkyl group. ao2 each independently represents a hydrogen atom, a substituted alkyl group (e.g., a substituted C1-4 alkyl group), an unsubstituted alkyl group (e.g., an unsubstituted C1-4 alkyl group), a substituted aryl group (e.g., a substituted C6-10 aryl group), or an unsubstituted aryl group (e.g., an unsubstituted C6-10 aryl group). ao represents 1, 2, or 3.

[0112] Examples of the hydroxyalkyl group include a hydroxyethyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, and a 2-hydroxy-1-methylethyl group.

[0113] Examples of the substituent include an amino group, an alkyl group, and an aryl group.

[0114] <Polyoxyalkyleneamine> Examples of polyoxyalkyleneamines include N,N-poly(oxyethylene)-hexylamine, N,N-poly(oxypropylene)-hexylamine, N,N-poly(oxyethylene·oxypropylene)-hexylamine, N,N-poly(oxyethylene)-decylamine, N,N-poly(oxypropylene)-decylamine, N,N-poly(oxyethylene·oxypropylene)-decylamine, N,N-poly(oxyethylene)-pentadecylamine, N,N-poly(oxypropylene)-pentadecylamine, N,N-poly(oxyethylene·oxypropylene)-pentadecylamine, Examples of the polyoxyethylene methyl ester include N,N-poly(oxyethylene)-icosylamine, N,N-poly(oxypropylene)-icosylamine, N,N-poly(oxyethylene·oxypropylene)-icosylamine, N,N-poly(oxyethylene)-hexacosylamine, N,N-poly(oxypropylene)-hexacosylamine, N,N-poly(oxyethylene·oxypropylene)-hexacosylamine, N,N-poly(oxyethylene)-triacontylamine, N,N-poly(oxypropylene)-triacontylamine, and N,N-poly(oxyethylene·oxypropylene)-triacontylamine.

[0115] In one embodiment, the polyoxyalkylene amine is represented by the formula: NR ap1 ap (R ap2 H) (3-ap) (R ap1R each independently represents an alkyl group (for example, a C1-40 alkyl group), an alkenyl group (for example, a C2-40 alkenyl group), or an arylalkyl group (for example, a C7-40 arylalkyl group). ap2 each independently represents a polyoxyalkylene group (e.g., a polyoxyethylene group, a polyoxypropylene group). a p represents 1, 2, or 3.

[0116] Examples of non-hydrocarbon cyclic amines include morpholine, oxazole, and thiazole.

[0117] In one embodiment, the amine is preferably an amine that does not contain a (meth)acryloyl group.

[0118] In one embodiment, the amine is preferably an amine containing two or more heteroatoms, more preferably a diamine or an alkanolamine. "Heteroatom" refers to an atom other than carbon or hydrogen atoms.

[0119] The number of amino groups (amines) may be, for example, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1. In one embodiment, the number of amino groups (amines) is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 4.

[0120] mechanism Generally, the polarity of amines is greater than that of fluorine-containing compounds. "High polarity" means that there is a large imbalance between positive and negative polarities within a single molecule. Compounds with different polarities (amines and fluorine-containing compounds) do not mix easily. Therefore, the fluorine-containing compounds are pushed to the surface. As a result, they have good steel wool resistance. It should be noted that the above is merely one theory, and it is not intended that the present invention be restricted to the above theory.

[0121] Examples of the mass % content (amine / active energy ray-curable composition nonvolatile content) include 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0.7 mass %, 0.6 mass %, 0.5 mass %, 0.4 mass %, 0.2 mass %, 0.1 mass %, etc. In one embodiment, the content is preferably 0.1 mass % to 10 mass %, more preferably 0.1 mass % to 5 mass %, and even more preferably 0.2 mass % to 2 mass %.

[0122] In one embodiment, the content in parts by mass (amine / active energy ray-curable compound) is preferably less than 8 parts by mass.

[0123] <Solid alumina particles> In one embodiment, the active energy ray-curable composition may optionally contain solid alumina particles. The solid alumina particles may be used alone or in combination of two or more kinds.

[0124] "Alumina" means aluminum oxide (Al2O3).

[0125] Examples of the form (alumina) include α-type, γ-type, σ-type, and mixtures thereof.

[0126] Examples of the shape (solid alumina particles) include spherical, rod-like, plate-like, fibrous, and irregular shapes.

[0127] In one embodiment, the solid alumina particles are preferably modified solid alumina particles, such as (meth)acrylic-modified solid alumina particles and silicone-modified solid alumina particles.

[0128] Examples of products (solid alumina particles) include Aluminisol F-3000 (manufactured by Kawaken Fine Chemicals Co., Ltd.), Bylar AL-7 (manufactured by Taki Chemical Co., Ltd.), NANOBYK-3610, 3611 (manufactured by BYK Chemie), Optisol LAA530U (manufactured by RANCO), and ALMIBK-M47 (manufactured by CIK Nanotech).

[0129] Examples of primary particle diameters (solid alumina particles) include 160 nm, 150 nm, 140 nm, 130 nm, 120 nm, 110 nm, 100 nm, 90 nm, 80 nm, 70 nm, 60 nm, 50 nm, 40 nm, 30 nm, 20 nm, 15 nm, 10 nm, 7 nm, and 3 nm. In one embodiment, the primary particle diameter is 3 nm to 160 nm.

[0130] The primary particle size (solid alumina particles) can be measured by the following method. (1) Preparation of the measurement solution A solution is prepared by adding a measurement sample (particles) to methyl ethyl ketone (hereinafter, MEK) or methyl isobutyl ketone (hereinafter, MIBK) so that the measurement sample concentration becomes 1 mass %. (2) Measurement of particle size distribution by volume Measuring equipment: Dynamic light scattering particle size distribution analyzer "LB-550" (Horiba Ltd.) Number of measurements: 5 Measurement temperature: 25±0.5℃ Measurement time: 60 seconds Measurement upper limit: 6000nm Measurement lower limit: 1nm Measurement solvent: MEK or MIBK

[0131] Examples of secondary particle diameters (solid alumina particles) include 350 nm, 325 nm, 300 nm, 275 nm, 250 nm, 225 nm, 200 nm, 190 nm, 175 nm, 150 nm, 125 nm, 110 nm, 100 nm, 90 nm, 80 nm, 70 nm, 60 nm, 55 nm, 50 nm, 45 nm, 40 nm, 35 nm, 30 nm, and 25 nm. In one embodiment, the secondary particle diameter is 25 nm to 350 nm.

[0132] The secondary particle size (solid alumina particles) is measured in the same manner as the primary particle size measurement procedure described above.

[0133] Examples of the mass % content (solid alumina particles / nonvolatile content of the active energy ray-curable composition) include 15 mass %, 14 mass %, 13 mass %, 12 mass %, 11 mass %, 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 15 mass %, more preferably 2 mass % to 15 mass %, and even more preferably 6 mass % to 15 mass %.

[0134] <Hollow inorganic particles> In one embodiment, the active energy ray-curable composition may optionally contain hollow inorganic particles. The hollow inorganic particles may be used alone or in combination of two or more kinds.

[0135] Examples of hollow inorganic particles include hollow silica particles, hollow aluminosilicate particles, hollow alumina particles, hollow mullite particles, hollow titanium oxide particles, hollow magnesium fluoride particles, and fly ash balloons.

[0136] Examples of the shape (hollow inorganic particles) include spherical, rod-like, plate-like, fibrous, and irregular shapes.

[0137] In one embodiment, the hollow inorganic particles are preferably modified hollow inorganic particles.

[0138] Examples of the modified hollow inorganic particles include (meth)acrylic modified hollow inorganic particles and silicone modified hollow inorganic particles.

[0139] Examples of the mass % content (modified portion / modified hollow inorganic particles) include 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 1 mass %, 0.1 mass %, 0.01 mass %, etc. In one embodiment, the content is preferably 0.01 mass % to 40 mass %, more preferably 0.1 mass % to 30 mass %, and even more preferably 1 mass % to 20 mass %.

[0140] Examples of the product (hollow inorganic particles) include Sururia 5320, Sururia 4320, Sururia 4110, Sururia 2320, Sururia 1110, JX1008SIV, JX1009SIV (manufactured by JGC Catalysts and Chemicals Industries, Ltd.), and Silinax (manufactured by Nittetsu Mining Co., Ltd.).

[0141] Examples of particle diameters (hollow inorganic particles) include 120 nm, 115 nm, 110 nm, 105 nm, 100 nm, 95 nm, 90 nm, 85 nm, 80 nm, 75 nm, 70 nm, 65 nm, 60 nm, 55 nm, 50 nm, 45 nm, and 40 nm. In one embodiment, the particle diameter is preferably 40 nm to 120 nm.

[0142] The particle diameter (hollow inorganic particles) is measured using a scanning electron microscope (for example, JSM-7800F Prime (manufactured by JEOL Ltd.)) and a STEM detector (manufactured by DEBEN UK Ltd.). Specifically, the measurement is performed according to the following procedure. (1) Dilute the particle sample with methyl isobutyl ketone to an active ingredient concentration of 0.2% and stir thoroughly. (2) A drop of the above dispersion was placed on a microgrid with a support film for STEM (Hi-Res Carbon HRC-C10 STEM Cu100P grid specification (manufactured by Stem Corporation)) and dried to prepare a measurement sample. (3) Using a scanning electron microscope, images are taken at a magnification (e.g., 300k times) that allows the length of particles in the field of view to be measured sufficiently under conditions of an accelerating voltage of 30kV, and the particle diameters of 50 randomly selected particles are measured to determine the particle diameter on a number basis. The particle diameter measurement can be done manually or using a measuring tool.

[0143] Examples of the refractive index (hollow inorganic particles) include 1.5, 1.4, 1.3, 1.2, 1.1, etc. In one embodiment, the refractive index of the hollow inorganic particles is preferably 1.1 to 1.5.

[0144] The refractive index (hollow inorganic particles) is calculated by forming a film of a composition containing the object to be measured at a non-volatile content ratio of 1 mass %, 10 mass %, or 20 mass % in an active energy ray-curable resin (for example, dipentaerythritol polyacrylate manufactured by Shin-Nakamura Chemical Co., Ltd.: product name NK Ester A-9550W), measuring the refractive index at the wavelength of the sodium D line using an Abbe refractometer (product name "NAR-1T SOLID" manufactured by Atago Co., Ltd.) in accordance with JIS K7142:2014, and extrapolating the result to a non-volatile content ratio of 100 mass %.

[0145] Examples of the mass % content (hollow inorganic particles / nonvolatile content of the active energy ray-curable composition) include 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 44 mass %, 43 mass %, 42 mass %, 41 mass %, 40 mass %, 39 mass %, 38 mass %, 37 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, and 0 mass %. In one embodiment, the content is preferably 0 mass % to 80 mass %, and more preferably 20 mass % to 65 mass %.

[0146] <Poly(meth)acrylates that are not oxygen-hydrogen bond-containing poly(meth)acrylates: Other poly(meth)acrylates> In one embodiment, the active energy ray-curable composition may optionally contain a poly(meth)acrylate other than the oxygen-hydrogen bond-containing poly(meth)acrylate (other poly(meth)acrylate). The other poly(meth)acrylates may be used alone or in combination of two or more.

[0147] Other poly(meth)acrylates include, for example, pentaerythritol tetra(alkylene oxide-modified) (meth)acrylate, dipentaerythritol hexa(alkylene oxide-modified) (meth)acrylate, trimethylolpropane tri(alkylene oxide-modified) (meth)acrylate, ditrimethylolpropane tetra(alkylene oxide-modified) (meth)acrylate, glycerin tri(alkylene oxide-modified) (meth)acrylate, diglycerin tetra(alkylene oxide-modified) (meth)acrylate, and urethane poly(meth)acrylate.

[0148] Examples of urethane poly(meth)acrylates include reaction products of compounds containing hydroxyl group-containing poly(meth)acrylate and polyisocyanate, and optionally polyol.

[0149] Examples of the hydroxyl group-containing poly(meth)acrylate include the compounds described above.

[0150] Examples of polyisocyanates include linear aliphatic polyisocyanates, branched aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and biurets, isocyanurates, allophanates, adducts, and the like thereof.

[0151] Examples of the linear aliphatic polyisocyanate include methylene diisocyanate, dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, and decamethylene diisocyanate.

[0152] Examples of branched aliphatic polyisocyanates include diethylpentylene diisocyanate, trimethylbutylene diisocyanate, trimethylpentylene diisocyanate, and trimethylhexamethylene diisocyanate.

[0153] Examples of the alicyclic polyisocyanate include monocyclic alicyclic polyisocyanates, crosslinked cyclic alicyclic polyisocyanates, and condensed cyclic alicyclic polyisocyanates.

[0154] Examples of monocyclic alicyclic polyisocyanates include hydrogenated xylene diisocyanate, isophorone diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, cycloheptylene diisocyanate, cyclodecylene diisocyanate, 3,5,5-trimethylcyclohexylene diisocyanate, and dicyclohexylmethane diisocyanate.

[0155] Examples of the crosslinked alicyclic polyisocyanate include tricyclodecylene diisocyanate, adamantane diisocyanate, and norbornene diisocyanate.

[0156] An example of the condensed ring alicyclic polyisocyanate is bicyclodecylene diisocyanate.

[0157] Examples of aromatic polyisocyanates include monocyclic aromatic polyisocyanates and condensed ring aromatic polyisocyanates.

[0158] Examples of the monocyclic aromatic polyisocyanate include dialkyldiphenylmethane diisocyanates such as 4,4'-diphenyldimethylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanates such as 4,4'-diphenyltetramethylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and m-tetramethylxylylene diisocyanate.

[0159] An example of the condensed ring aromatic polyisocyanate is 1,5-naphthylene diisocyanate.

[0160] Examples of polyols include alkylene polyols, polyether polyols, polyester polyols, polycarbonate polyols, acrylic polyols, and polyolefin polyols.

[0161] Examples of the mass % content (other poly(meth)acrylate / active energy ray-curable composition nonvolatile content) include 42 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 42 mass %. <Photopolymerization initiator> In one embodiment, the active energy ray-curable composition may optionally contain a photopolymerization initiator. The photopolymerization initiators may be used alone or in combination of two or more.

[0162] Examples of the photopolymerization initiator include an α-hydroxydimethylacetophenone group-containing photopolymerization initiator, α-hydroxycycloalkylphenone, α-aminoalkylphenone, benzyl dimethyl ketal, unsubstituted or substituted alkylphenone, unsubstituted or substituted benzyl, unsubstituted or substituted benzophenone, acylphosphine oxide, substituted thioxanthone, and oxime ester.

[0163] Examples of the α-hydroxydimethylacetophenone group-containing photopolymerization initiator include 2-hydroxy-2-methyl-1-phenylpropanone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-methylpropanone, and 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one.

[0164] Examples of α-hydroxycycloalkylphenones include 1-hydroxycyclohexyl phenyl ketone.

[0165] Examples of α-aminoalkylphenones include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one.

[0166] Examples of benzyl dimethyl ketals include 2,2-dimethoxy-1,2-diphenylethan-1-one.

[0167] Examples of unsubstituted or substituted alkylphenones include benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-phenyl-2-(p-toluenesulfonyloxy)acetophenone, benzoin, 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, 2-isonitrosopropiophenone, and 2,2-dimethoxy-1,2-diphenylethan-1-one.

[0168] Examples of unsubstituted or substituted benzyl include benzyl and p-anisyl.

[0169] Examples of unsubstituted or substituted benzophenones include benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 1,4-dibenzoylbenzene, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid, and methyl 2-benzoylbenzoate.

[0170] Examples of the acylphosphine oxide include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0171] Examples of substituted thioxanthone include 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

[0172] Oxime esters include, for example, 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (i.e., 2-((benzoyloxy)imino)-1-(4-(phenylthio)phenyl)octan-1-one); Examples include ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (i.e., 1-(((1-(9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl)ethylidene)amino)oxy)ethan-1-one).

[0173] When electron beam curing is used, a photoinitiator is not required.

[0174] Examples of the mass % content (photopolymerization initiator / active energy ray-curable composition nonvolatile content) include 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 10 mass %, and more preferably 1 mass % to 6 mass %.

[0175] <Organic solvents> In one embodiment, the active energy ray-curable composition may optionally contain an organic solvent. The organic solvent may be used alone or in combination of two or more kinds.

[0176] Examples of the organic solvent include ketone solvents, aromatic solvents, alcohol solvents, glycol solvents, glycol ether solvents, ester solvents, petroleum-based solvents, haloalkane solvents, and amide solvents.

[0177] Examples of the ketone solvent include methyl ethyl ketone, acetylacetone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone.

[0178] Examples of aromatic solvents include toluene and xylene.

[0179] Examples of the alcohol solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, i-butanol, and t-butanol.

[0180] Examples of glycol solvents include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol.

[0181] Examples of glycol ether solvents include ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, and ethylene glycol mono-t-butyl ether.

[0182] Examples of the ester solvent include ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate.

[0183] Examples of petroleum-based solvents include Solvesso #100 (manufactured by Exxon Chemical), Solvesso #150 (manufactured by Exxon Chemical), and the like.

[0184] Examples of haloalkane solvents include chloroform.

[0185] The amide solvent may, for example, be dimethylformamide.

[0186] Examples of the mass % content (organic solvent / active energy ray-curable composition) include 99 mass %, 98.5 mass %, 98 mass %, 97 mass %, 95 mass %, 90 mass %, 85 mass %, 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 99 mass %.

[0187] <Additives> The active energy ray-curable composition may optionally contain an agent (additive) that does not fall into any of the above categories.

[0188] Examples of the additives include ultraviolet absorbers, antifoaming agents, antifouling agents, pigments, and the like.

[0189] In one embodiment, the content in parts by mass (additive / active energy ray-curable composition) is preferably less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, or 0 part by mass.

[0190] In one embodiment, the part by mass content (additive / oxygen-hydrogen bond-containing poly(meth)acrylate), part by mass content (additive / fluorine-containing compound), part by mass content (additive / amine), part by mass content (additive / solid alumina particles), part by mass content (additive / hollow inorganic particles), part by mass content (additive / photopolymerization initiator), and part by mass content (additive / organic solvent) are preferably less than 1 part by mass, less than 0.1 parts by mass, less than 0.01 parts by mass, 0 parts by mass, etc.

[0191] An active energy ray-curable composition can be produced by dispersing and mixing the above-mentioned agents.

[0192] Examples of the dispersing and mixing means include an emulsifying disperser and an ultrasonic dispersing device.

[0193] Examples of uses (of the active energy ray-curable composition) include coating agents, hard coating agents, clear coating agents, clear hard coating agents, anti-glare coating agents, anti-glare hard coating agents, coating agents for optical films, hard coating agents for optical films, low refractive index coating agents, and low refractive index hard coating agents.

[0194] [Cured product] The present disclosure relates to a cured product of the above-mentioned active energy ray-curable composition.

[0195] Examples of the curing conditions include the following conditions.

[0196] [Laminate] The present disclosure relates to a laminate comprising the above-mentioned cured product.

[0197] In one embodiment, the laminate has a cured product layer made of a cured product of the active energy ray-curable composition on at least one surface of the substrate. In one embodiment, the laminate has an anchor agent cured product layer made of a cured product of the anchor agent on at least one surface of the substrate, and an active energy ray-curable composition cured product layer made of a cured product of the active energy ray-curable composition on the anchor agent cured product layer.

[0198] Examples of the substrate include polycarbonate film, acrylic film (such as polymethyl methacrylate film), polystyrene film, polyester film, polyolefin film, epoxy resin film, melamine resin film, triacetyl cellulose film, ABS film, AS film, norbornene-based resin film, cyclic olefin film, and polyvinyl alcohol film.

[0199] In one embodiment, the thickness (base material) is preferably 1 μm to 125 μm.

[0200] In one embodiment, the thickness (of the layer of the cured product of the active energy ray-curable composition) is preferably 55 nm to 200 nm.

[0201] In one embodiment, the thickness (of the anchor agent cured product layer) is preferably 1 μm to 6 μm.

[0202] <Anchor agent> Examples of the solid alumina particles, poly(meth)acrylate, photopolymerization initiator, and organic solvent used in the anchoring agent include the above-mentioned compounds, etc. The solid alumina particles, poly(meth)acrylate, photopolymerization initiator, and organic solvent may each be used alone or in combination of two or more.

[0203] Examples of the mass% content (solid alumina particles / anchoring agent nonvolatile content) include 18 mass%, 17 mass%, 16 mass%, 15 mass%, 14 mass%, 13 mass%, 12 mass%, 11 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 18 mass%, and more preferably 2 mass% to 18 mass%.

[0204] Examples of the mass % content (poly(meth)acrylate / anchoring agent nonvolatile content) include 94 mass%, 90 mass%, 88 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 66 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 1 mass%, 0 mass%, etc. In one embodiment, the content is preferably 0 mass% to 94 mass%.

[0205] Examples of the mass % content (photopolymerization initiator / anchoring agent nonvolatile content) include 10 mass %, 9 mass %, 8 mass %, 7 mass %, 6 mass %, 5 mass %, 4 mass %, 3 mass %, 2 mass %, 1 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 10 mass %.

[0206] Examples of the mass % content (organic solvent / anchor agent) include 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, 2 mass %, 1 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 80 mass %.

[0207] Additives for anchoring agents The anchoring agent may optionally contain an agent that does not fall into any of the above categories (anchor agent additive).

[0208] Examples of the additive for the anchoring agent include the additives described above.

[0209] In one embodiment, the content in parts by mass (additive for anchoring agent / anchor agent) is preferably less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass, or the like.

[0210] In one embodiment, the part by mass content (anchor agent additive / solid alumina particles), the part by mass content (anchor agent additive / poly(meth)acrylate), the part by mass content (anchor agent additive / photopolymerization initiator), and the part by mass content (anchor agent additive / organic solvent) are preferably less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass, etc.

[0211] The anchoring agent can be produced by dispersing and mixing the above agents.

[0212] In one embodiment, the present disclosure relates to a kit comprising the active energy ray-curable composition and the anchoring agent.

[0213] <Manufacturing method (laminate)> The manufacturing method (laminate) may include, for example, a method including the following steps. Anchor agent application process: A process of applying an anchor agent to at least one side of the substrate Active energy ray curable composition coating step: A step of coating the active energy ray curable composition onto the anchor agent coating layer. Curing step: A step of forming a cured layer of the active energy ray-curable composition by irradiating with active energy rays. The anchor agent coating step and the active energy ray-curable composition coating step are collectively referred to as the coating step.

[0214] (Coating process) Examples of the coating method include bar coater coating, wire bar coating, Mayer bar coating, air knife coating, gravure coating, reverse gravure coating, flow coater coating, offset printing, flexographic printing, and screen printing.

[0215] (hardening process) Examples of the active energy ray include ultraviolet rays and electron beams.

[0216] Examples of ultraviolet light sources include xenon lamps, high-pressure mercury lamps, and metal halide lamps.

[0217] When a high-pressure mercury lamp is used, the curing conditions are preferably the following conditions. Lamp output: 25W / cm~160W / cm UV illuminance: 10mW / cm 2 ~800mW / cm 2 Accumulated light output: 25mJ / cm 2 ~2000mJ / cm 2 Conveying speed: 1m / min to 50m / min

[0218] When electron beams are used, the curing conditions are preferably the following conditions. Acceleration voltage: 10 kV to 300 kV Conveying speed: 5m / min to 50m / min [Example]

[0219] The present invention will be described in detail below through examples and comparative examples. However, the above description and the following examples are not intended to limit the present invention. The present invention is limited only by the claims. Unless otherwise specified below, numerical values ​​such as parts and % are based on mass.

[0220] Example 1 The substances shown in the table below were mixed and then diluted to obtain an active energy ray-curable composition (dilution solvent: propylene glycol monomethyl ether, non-volatile content: 2%).

[0221] [Table 1]

[0222] Aronix M510: Carboxyl group-containing poly(meth)acrylate, manufactured by Toagosei Co., Ltd. Aronix M306: Pentaerythritol triacrylate, manufactured by Toagosei Co., Ltd. Amino alcohol EA: N-(2-aminoethyl)ethanolamine, manufactured by Nippon Nyukazai Co., Ltd. KY-1203: (meth)acryloyl group-containing perfluoropolyether, manufactured by Shin-Etsu Chemical Co., Ltd. NANOBYK-3611: solid alumina particles, manufactured by BYK Chemie Sururia 5320: Hollow silica particles, particle diameter 75 nm, manufactured by JGC Catalysts and Chemicals Co., Ltd. Sururia 4320: Hollow silica particles, particle diameter 60 nm, manufactured by JGC Catalysts and Chemicals Co., Ltd. Sururia 2320: Hollow silica particles, particle diameter 50 nm, manufactured by JGC Catalysts and Chemicals Co., Ltd. Omnirad 127D: 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one, IGM Resins

[0223] (anchor agent) An anchoring agent (non-volatile content 40% by mass) was prepared by mixing 66 parts by mass of aliphatic urethane acrylate (product name "BEAMSET 577" manufactured by Arakawa Chemical Industries, Ltd.), 22 parts by mass of dipentaerythritol polyacrylate (product name "NK Ester A-9550" manufactured by Shin-Nakamura Chemical Co., Ltd.), 9 parts by mass of solid alumina particles (product name "NANOBYK-3611" manufactured by BYK Chemie, 30% by mass methoxypropyl acetate), and 3 parts by mass of 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxymethylpropanone (product name "Omnirad 2959" manufactured by IGM Resins) and diluting the mixture with methyl isobutyl ketone.

[0224] (laminate) (1) Anchor film was produced as follows: Substrate: PET film (product name: Lumirror 50U48, manufactured by Toray Industries, Inc.) Coating step: The anchor agent was applied to the substrate using a bar coater so that the film thickness after drying would be 4 μm. Curing process: After drying at 80°C for 1 minute, the product is immersed in a high-pressure mercury lamp (200 mJ / cm 2 ) and cured. (2) A laminate was produced in the following manner. Coating step: The active energy ray-curable composition was applied to the anchor film using a bar coater so that the film thickness after drying would be 100 nm. Curing process: After drying at 80°C for 1 minute, the product is cured under a nitrogen stream and exposed to a high-pressure mercury lamp (600 mJ / cm 2 ) and cured.

[0225] (Refractive index of cured product) The produced laminates were measured as follows. Standard: JIS K7142:2014 Equipment: Abbe refractometer (product name "NAR-1T SOLID", manufactured by Atago Co., Ltd.) Refractive index: Refractive index of sodium at the wavelength of the D line

[0226] (Steel wool test) The laminate was placed in a steel wool tester with the active energy ray-curable composition cured product layer facing upward, and a steel wool test was carried out using #0000 steel wool according to the following criteria. Test load: 1 kg Area: 4cm 2 Number of round trips: As shown in the table Steel wool: #0000 ○: 5 or fewer scratches △: 6 to less than 10 scratches ×: 10 or more scratches

[0227] Evaluation example: Coefficient of dynamic friction The laminate was placed in a friction coefficient measuring device manufactured by Imada Co., Ltd. with the active energy ray-curable composition cured product layer facing upward, and the dynamic friction coefficient was measured according to the following criteria using a sliding piece with a medicine wrapping paper attached. Slider: Contact area (63mm x 63mm), Load: 200g Medicine wrapping paper: Paraffin made by HAKUAI Pulling speed: 100 mm / min

[0228] [Table 2]

Claims

1. An active energy ray-curable composition, comprising an oxygen-hydrogen bond-containing poly(meth)acrylate, a fluorine-containing compound, and an amine.

2. The active energy ray-curable composition according to claim 1 , comprising solid alumina particles.

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

4. A laminate comprising the cured product according to claim 3.

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