Curable composition, cured product, and laminate

Abstract

To provide a curable composition enabling production of a cured product that is resistant to curling and hardness variation upon coating under a high-humidity condition; a cured product; and a laminate.SOLUTION: A curable composition comprises an alicyclic epoxy group-containing non-cyclic siloxane, a radical polymerizable group-containing compound, and a borate salt.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to curable compositions, cured products, and laminates. [Background technology]

[0002] Active energy ray-curable compositions are used in various fields such as coating agents (for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 62-021815 Summary of the Invention [Problem to be solved by the invention]

[0004] The problem to be solved by the present invention is to provide a curable composition that can produce a cured product that is suppressed in curling and in hardness change when coated in a humid environment. [Means for solving the problem]

[0005] The present disclosure provides the following: (Item 1) A curable composition comprising an alicyclic epoxy group-containing acyclic siloxane, a radically polymerizable group-containing compound, and a borate salt. (Item 2) The curable composition according to the preceding item, comprising a hindered phenol group-containing compound. (Item 3) A cured product of the curable composition according to any one of the preceding 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 cured product of the present invention is inhibited from curling and from changing in hardness when coated in a humid environment. 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] "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.

[0015] Examples of the alkyl group include a linear alkyl group, a branched alkyl group, and a cycloalkyl group.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] "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.

[0020] 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.

[0021] Examples of the bridged ring cycloalkyl group include a tricyclodecyl group, an adamantyl group, and a norbornyl group.

[0022] 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.

[0023] The aromatic group (aryl group, arylene group) may be substituted or unsubstituted. Examples of the substituent of the aromatic group include an alkyl group, a thioalkyl group, a thioaryl group, and a carbonylaryl group.

[0024] Examples of the aryl group include a monocyclic aryl group and a fused ring aryl group.

[0025] Examples of the monocyclic aryl group include a phenyl group, a tolyl group, and a mesityl group.

[0026] The fused ring aryl group may, for example, be a naphthyl group.

[0027] Examples of the arylene group include a monocyclic arylene group and a fused ring arylene group.

[0028] Examples of the monocyclic arylene group include a phenylene group and a tolylene group.

[0029] The fused ring arylene group may, for example, be a naphthylene group.

[0030] [Curable composition] The present disclosure relates to a curable composition, the curable composition comprising an alicyclic epoxy group-containing acyclic siloxane, a radically polymerizable group-containing compound, and a borate salt.

[0031] <Acyclic siloxane containing alicyclic epoxy groups> The alicyclic epoxy group-containing acyclic siloxanes may be used alone or in combination of two or more.

[0032] "Cyclic siloxane" is a compound whose composition formula of silicon atoms and oxygen atoms is SiO 2 / 2 and means a siloxane in which a ring structure is formed only by silicon atoms and oxygen atoms.

[0033] The term "non-cyclic siloxane" refers to a siloxane that does not fall under the category of the above-mentioned cyclic siloxanes.

[0034] Examples of the alicyclic epoxy group include an epoxycyclohexyl group.

[0035] Examples of the alicyclic epoxy group-containing acyclic siloxane include alicyclic epoxy group-containing acyclic alkoxysiloxane and alicyclic epoxy group-containing acyclic alkylsiloxane.

[0036] (alicyclic epoxy group-containing acyclic alkoxysiloxane) "Alkoxysiloxane" means a condensation product of an alkoxysilane.

[0037] Examples of the alkoxysilane include alkoxysilanes containing an alicyclic epoxy group and alkoxysilanes not containing an alicyclic epoxy group.

[0038] <Alkoxysilane containing alicyclic epoxy groups> In one embodiment, the alicyclic epoxy group-containing alkoxysilane is represented by the following formula: R sre1 -SiR sre2 s1 (OR sre3 ) 3-s1 (Rsre1 represents an alicyclic epoxy group-substituted alkyl group. R sre2 each independently represents a hydrogen atom, an alkyl group, an aryl group, or an aryl group-substituted alkyl group. R sre3 each independently represents a hydrogen atom or an alkyl group. s1 represents an integer from 0 to 2.

[0039] Examples of alicyclic epoxy group-containing alkoxysilanes include 1-(3,4-epoxycyclohexyl)methyltrimethoxysilane, 1-(3,4-epoxycyclohexyl)methylmethyldimethoxysilane, 1-(3,4-epoxycyclohexyl)methyltriethoxysilane, 1-(3,4-epoxycyclohexyl)methylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl methyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane, 3-(3,4-epoxycyclohexyl)propyltrimethoxysilane, 3-(3,4-epoxycyclohexyl)propylmethyldimethoxysilane, 3-(3,4-epoxycyclohexyl)propyltriethoxysilane, 3-(3,4-epoxycyclohexyl)propylmethyldiethoxysilane silane, 4-(3,4-epoxycyclohexyl)butyltrimethoxysilane, 4-(3,4-epoxycyclohexyl)butylmethyldimethoxysilane, 4-(3,4-epoxycyclohexyl)butyltriethoxysilane, 4-(3,4-epoxycyclohexyl)butylmethyldiethoxysilane, 6-(3,4-epoxycyclohexyl)hexyltrimethoxysilane, 6-(3,4-epoxycyclohexyl)hexylmethyldimethoxysilane, 6- Examples include (3,4-epoxycyclohexyl)hexyltriethoxysilane, 6-(3,4-epoxycyclohexyl)hexylmethyldiethoxysilane, 8-(3,4-epoxycyclohexyl)octyltrimethoxysilane, 8-(3,4-epoxycyclohexyl)octylmethyldimethoxysilane, 8-(3,4-epoxycyclohexyl)octyltriethoxysilane, and 8-(3,4-epoxycyclohexyl)octylmethyldiethoxysilane.

[0040] Examples of the mass % content (alicyclic epoxy group-containing alkoxysilane unit / alicyclic epoxy group-containing acyclic alkoxysiloxane) include 100 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 %, etc. In one embodiment, the content is preferably 10 mass % to 100 mass %.

[0041] Examples of the molar content (alicyclic epoxy group-containing alkoxysilane units / alicyclic epoxy group-containing acyclic alkoxysiloxane) include 100 mol%, 95 mol%, 90 mol%, 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, etc. In one embodiment, the content is preferably 10 mol% to 100 mol%.

[0042] <Alkoxysilanes not containing alicyclic epoxy groups> In one embodiment, the alicyclic epoxy group-free alkoxysilane is represented by the following formula: R srn1 -SiR srn2 s2 (OR srn3 ) 3-s2 (R srn1 represents an alkyl group, a thiol group-substituted alkyl group, an isocyanate group-substituted alkyl group, a (meth)acryloyl group-substituted alkyl group, an aryl group-substituted alkyl group, a cyclohexyl group-substituted alkyl group, a chloro group-substituted alkyl group, an oxetanyloxy group-substituted alkyl group, an alkenyl group, or an alkenyl group-substituted aryl group. R srn2 each independently represents a hydrogen atom, an alkyl group, an aryl group, or an aryl group-substituted alkyl group. R srn3 each independently represents a hydrogen atom or an alkyl group. s2 represents an integer from 0 to 2.

[0043] Alicyclic epoxy-free alkoxysilane (R srn1 = alkyl group), for example, methyltrimethoxysilane, dimethyldimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, ethyltrimethoxysilane, ethylmethyldimethoxysilane, ethyltriethoxysilane, ethylmethyldiethoxysilane, propyltrimethoxysilane, propylmethyldimethoxysilane, propyltriethoxysilane, propylmethyldiethoxysilane, butyltrimethoxysilane, butylmethyldimethoxysilane, butyltriethoxysilane, butylmethyldiethoxysilane, hexyltrimethoxysilane, hexylmethyldimethoxysilane, hexyltriethoxysilane, hexylmethyldiethoxysilane, octyltrimethoxysilane, octylmethyldimethoxysilane, octyltriethoxysilane, octylmethyldiethoxysilane, and the like.

[0044] Alicyclic epoxy-free alkoxysilane (R srn1= thiol group-substituted alkyl group) includes, for example, 1-mercaptomethyltrimethoxysilane, 1-mercaptomethylmethyldimethoxysilane, 1-mercaptomethyltriethoxysilane, 1-mercaptomethylmethyldiethoxysilane, 2-mercaptoethyltrimethoxysilane, 2-mercaptoethylmethyldimethoxysilane, 2-mercaptoethyltriethoxysilane, 2-mercaptoethylmethyldiethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldiethoxysilane, Examples of such silane include silane, 4-mercaptobutyltrimethoxysilane, 4-mercaptobutylmethyldimethoxysilane, 4-mercaptobutyltriethoxysilane, 4-mercaptobutylmethyldiethoxysilane, 6-mercaptohexyltrimethoxysilane, 6-mercaptohexylmethyldimethoxysilane, 6-mercaptohexyltriethoxysilane, 6-mercaptohexylmethyldiethoxysilane, 8-mercaptooctyltrimethoxysilane, 8-mercaptooctylmethyldimethoxysilane, 8-mercaptooctyltriethoxysilane, and 8-mercaptooctylmethyldiethoxysilane.

[0045] Alicyclic epoxy-free alkoxysilane (R srn1= isocyanate group-substituted alkyl group) includes, for example, 1-isocyanatemethyltrimethoxysilane, 1-isocyanatemethylmethyldimethoxysilane, 1-isocyanatemethyltriethoxysilane, 1-isocyanatemethylmethyldiethoxysilane, 2-isocyanateethyltrimethoxysilane, 2-isocyanateethylmethyldimethoxysilane, 2-isocyanateethyltriethoxysilane, 2-isocyanateethylmethyldiethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropylmethyldimethoxysilane, 3-isocyanatepropyltriethoxysilane, 3-isocyanatepropylmethyldiethoxysilane silane, 4-isocyanatebutyltrimethoxysilane, 4-isocyanatebutylmethyldimethoxysilane, 4-isocyanatebutyltriethoxysilane, 4-isocyanatebutylmethyldiethoxysilane, 6-isocyanatehexyltrimethoxysilane, 6-isocyanatehexylmethyldimethoxysilane, 6-isocyanatehexyltriethoxysilane, 6-isocyanatehexylmethyldiethoxysilane, 8-isocyanateoctyltrimethoxysilane, 8-isocyanateoctylmethyldimethoxysilane, 8-isocyanateoctyltriethoxysilane, 8-isocyanateoctylmethyldiethoxysilane, and the like.

[0046] Alicyclic epoxy-free alkoxysilane (R srn1= (meth)acryloyl group-substituted alkyl group) includes, for example, 1-(meth)acryloyloxymethyltrimethoxysilane, 1-(meth)acryloyloxymethylmethyldimethoxysilane, 1-(meth)acryloyloxymethyltriethoxysilane, 1-(meth)acryloyloxymethylmethyldiethoxysilane, 2-(meth)acryloyloxyethyltrimethoxysilane, 2-(meth)acryloyloxyethylmethyldimethoxysilane, 2-(meth)acryloyloxyethyltriethoxysilane, 2-(meth)acryloyloxyethylmethyldiethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 3-(meth)acryloyloxypropylmethyldi Examples of suitable silanes include ethoxysilane, 4-(meth)acryloyloxybutyltrimethoxysilane, 4-(meth)acryloyloxybutylmethyldimethoxysilane, 4-(meth)acryloyloxybutyltriethoxysilane, 4-(meth)acryloyloxybutylmethyldiethoxysilane, 6-(meth)acryloyloxyhexyltrimethoxysilane, 6-(meth)acryloyloxyhexylmethyldimethoxysilane, 6-(meth)acryloyloxyhexyltriethoxysilane, 6-(meth)acryloyloxyhexylmethyldiethoxysilane, 8-(meth)acryloyloxyoctyltrimethoxysilane, 8-(meth)acryloyloxyoctylmethyldimethoxysilane, 8-(meth)acryloyloxyoctyltriethoxysilane, and 8-(meth)acryloyloxyoctylmethyldiethoxysilane.

[0047] Alicyclic epoxy-free alkoxysilane (R srn1= aryl group-substituted alkyl group), examples of which include benzyltrimethoxysilane, benzyltriethoxysilane, 2-phenylethyltrimethoxysilane, 2-phenylethyltriethoxysilane, 3-phenylpropyltrimethoxysilane, 3-phenylpropyltriethoxysilane, 4-phenylbutyltrimethoxysilane, 4-phenylbutyltriethoxysilane, 5-phenylpentyltrimethoxysilane, 5-phenylpentyltriethoxysilane, 6-phenylhexyltrimethoxysilane, and 6-phenylhexyltriethoxysilane.

[0048] Alicyclic epoxy-free alkoxysilane (R srn1 = cyclohexyl group-substituted alkyl group), examples of which include cyclohexylmethyltrimethoxysilane, cyclohexylmethyltriethoxysilane, 2-cyclohexylethyltrimethoxysilane, 2-cyclohexylethyltriethoxysilane, 3-cyclohexylpropyltrimethoxysilane, 3-cyclohexylpropyltriethoxysilane, 4-cyclohexylbutyltrimethoxysilane, 4-cyclohexylbutyltriethoxysilane, 5-cyclohexylpentyltrimethoxysilane, 5-cyclohexylpentyltriethoxysilane, 6-cyclohexylhexyltrimethoxysilane, and 6-cyclohexylhexyltriethoxysilane.

[0049] Alicyclic epoxy-free alkoxysilane (R srn1 = chloro group-substituted alkyl group), examples of which include chloromethyltrimethoxysilane, chloromethyltriethoxysilane, 2-chloroethyltrimethoxysilane, 2-chloroethyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 4-chlorobutyltrimethoxysilane, 4-chlorobutyltriethoxysilane, 5-chloropentyltrimethoxysilane, 5-chloropentyltriethoxysilane, 6-chlorohexyltrimethoxysilane, and 6-chlorohexyltriethoxysilane.

[0050] Alicyclic epoxy-free alkoxysilane (Rsrn1 = oxetanyloxy group-substituted alkyl group) includes, for example, 1-oxetanyloxymethyltrimethoxysilane, 1-oxetanyloxymethylmethyldimethoxysilane, 1-oxetanyloxymethyltriethoxysilane, 1-oxetanyloxymethylmethyldiethoxysilane, 2-oxetanyloxyethyltrimethoxysilane, 2-oxetanyloxyethylmethyldimethoxysilane, 2-oxetanyloxyethyltriethoxysilane, 2-oxetanyloxyethylmethyldiethoxysilane, 3-oxetanyloxypropyltrimethoxysilane, 3-oxetanyloxypropylmethyldimethoxysilane, 3-oxetanyloxypropyltriethoxysilane, 3-oxetanyloxypropylmethyldiethoxysilane, oxetanyloxybutyltrimethoxysilane, 4-oxetanyloxybutylmethyldimethoxysilane, 4-oxetanyloxybutyltriethoxysilane, 4-oxetanyloxybutylmethyldiethoxysilane, 6-oxetanyloxyhexyltrimethoxysilane, 6-oxetanyloxyhexylmethyldimethoxysilane, 6-oxetanyloxyhexyltriethoxysilane, 6-oxetanyloxyhexylmethyldiethoxysilane, 8-oxetanyloxyoctyltrimethoxysilane, 8-oxetanyloxyoctylmethyldimethoxysilane, 8-oxetanyloxyoctyltriethoxysilane, 8-oxetanyloxyoctylmethyldiethoxysilane, and the like.

[0051] Alicyclic epoxy-free alkoxysilane (R srn1 (=alkenyl group) includes, for example, vinyltrimethoxysilane, vinylmethyldimethoxysilane, vinyltriethoxysilane, vinylmethyldiethoxysilane, allyltrimethoxysilane, allylmethyldimethoxysilane, allyltriethoxysilane, allylmethyldiethoxysilane, and the like.

[0052] Alicyclic epoxy-free alkoxysilane (R srn1 (=alkenyl-substituted aryl group) includes, for example, p-styryltrimethoxysilane, p-styryltriethoxysilane, and the like.

[0053] Examples of the mass % content (alicyclic epoxy group-free alkoxysilane units / alicyclic epoxy group-containing acyclic alkoxysiloxane) include 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 90 mass %.

[0054] Examples of the molar content (alicyclic epoxy group-free alkoxysilane units / alicyclic epoxy group-containing acyclic alkoxysiloxane) include 90 mol%, 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, 20 mol%, 15 mol%, 10 mol%, 5 mol%, 0 mol%, etc. In one embodiment, the content is preferably 0 mol% to 90 mol%.

[0055] <Production Method (Acyclic Alkoxysiloxane Containing Alicyclic Epoxy Groups)> Alicyclic epoxy-containing acyclic alkoxysiloxanes are produced by the hydrolysis and condensation reaction of alkoxysilanes.

[0056] The molar ratio (water / alkoxy group) is preferably 0.2 to 20, more preferably 0.4 to 3, and even more preferably 0.45 to 2.

[0057] The reaction solvent may be used alone or in combination of two or more kinds thereof. Examples of the reaction solvent include methanol, ethanol, 1-propanol, 2-propanol, 2-butanol, 2-methyl-2-propanol, 1-methoxy-2-propanol, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, and propylene glycol dimethyl ether.

[0058] The reaction temperature is preferably 40°C to 200°C, more preferably 50°C to 250°C, and even more preferably 60°C to 230°C.

[0059] The reaction time is preferably 0.5 to 10 hours, and more preferably 1 to 5 hours.

[0060] (alicyclic epoxy group-containing acyclic alkylsiloxane) "Alkylsiloxane" means a siloxane containing dialkylsiloxane units.

[0061] The dialkylsiloxane unit is represented by the following formula: [ka] (R sk1 ~R sk2 each independently represents an alkyl group or an alicyclic epoxy group-substituted alkyl group.

[0062] In one embodiment, the alicyclic epoxy group-containing acyclic alkylsiloxane is represented by the following formula: [ka] (R sk1 ~R sk6 R each independently represents a C1-6 alkyl group or an alicyclic epoxy group-substituted alkyl group. sk7 ~R sk8 each independently represents a C1-4 alkylene group, and sk represents an integer of 0 to 12.

[0063] In one embodiment, R sk1 ~R sk6 R is preferably a methyl group or an ethylepoxycyclohexyl group. sk7 ~R sk8 is preferably an ethyl group. sk is preferably 0.

[0064] Examples of the epoxy equivalent (alicyclic epoxy group-containing acyclic siloxane) include 500 g / eq, 450 g / eq, 400 g / eq, 350 g / eq, 300 g / eq, 250 g / eq, 200 g / eq, 150 g / eq, etc. In one embodiment, the epoxy equivalent is preferably 150 g / eq to 500 g / eq.

[0065] Examples of the mass % content (alicyclic epoxy group-containing acyclic siloxane / nonvolatile content of the curable composition) include 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, 25 mass %, 20 mass %, 15 mass %, 10 mass %, 5 mass %, etc. In one embodiment, the content is preferably 5 mass % to 70 mass %.

[0066] <Radical polymerizable group-containing compound> The radical polymerizable group-containing compound may be used alone or in combination of two or more kinds.

[0067] The radical polymerizable group-containing compound may, for example, be poly(meth)acrylate.

[0068] "Poly(meth)acrylate" means a compound having two or more (meth)acryloyl groups.

[0069] Examples of poly(meth)acrylates include (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, (poly)glycerin poly(meth)acrylate, and urethane poly(meth)acrylate.

[0070] Examples of (poly)polypentaerythritol poly(meth)acrylates include pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol di(meth)acrylate, tripentaerythritol tri(meth)acrylate, tripentaerythritol tetra(meth)acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, and tripentaerythritol octa(meth)acrylate.

[0071] Examples of the (poly)trimethylolpropane poly(meth)acrylate include trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane di(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, and ditrimethylolpropane tetra(meth)acrylate.

[0072] Examples of the (poly)glycerin poly(meth)acrylate include glycerin di(meth)acrylate, glycerin tri(meth)acrylate, diglycerin di(meth)acrylate, diglycerin tri(meth)acrylate, and diglycerin tetra(meth)acrylate.

[0073] (urethane poly(meth)acrylate) Examples of urethane poly(meth)acrylates include reaction products of a compound group containing hydroxyl group-containing poly(meth)acrylate and polyisocyanate.

[0074] <Hydroxyl group-containing poly(meth)acrylate> Examples of the hydroxyl group-containing poly(meth)acrylate include (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, and (poly)glycerin poly(meth)acrylate.

[0075] The polyisocyanates may be used alone or in combination of two or more.

[0076] <Polyisocyanate> "Polyisocyanate" means a compound having two or more isocyanate groups (-N=C=O).

[0077] Examples of polyisocyanates include linear aliphatic polyisocyanates, branched aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and biurets, isocyanurates, allophanates, adducts, and the like thereof.

[0078] 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.

[0079] Examples of branched aliphatic polyisocyanates include diethylpentylene diisocyanate, trimethylbutylene diisocyanate, trimethylpentylene diisocyanate, and trimethylhexamethylene diisocyanate.

[0080] Examples of the alicyclic polyisocyanate include monocyclic alicyclic polyisocyanates, crosslinked cyclic alicyclic polyisocyanates, and condensed cyclic alicyclic polyisocyanates.

[0081] 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.

[0082] Examples of the crosslinked alicyclic polyisocyanate include tricyclodecylene diisocyanate, adamantane diisocyanate, and norbornene diisocyanate.

[0083] An example of the condensed ring alicyclic polyisocyanate is bicyclodecylene diisocyanate.

[0084] Examples of aromatic polyisocyanates include monocyclic aromatic polyisocyanates and condensed ring aromatic polyisocyanates.

[0085] 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 isocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and m-tetramethylxylylene diisocyanate.

[0086] The condensed ring aromatic polyisocyanate may, for example, be 1,5-naphthylene diisocyanate.

[0087] Examples of the mass % content (radical polymerizable group-containing compound / nonvolatile content of the curable composition) include 95 mass %, 90 mass %, 85 mass %, 80 mass %, 75 mass %, 70 mass %, 65 mass %, 60 mass %, 55 mass %, 50 mass %, 45 mass %, 40 mass %, 35 mass %, 30 mass %, etc. In one embodiment, the content is preferably 30 mass % to 95 mass %.

[0088] <Borate salt> The borate salts may be used alone or in combination of two or more.

[0089] Examples of the borate salt include sulfonium borate salt, iodonium borate salt, diazonium borate salt, and pyridinium borate salt.

[0090] Examples of the borate include tetrakis(pentafluorophenyl)borate and tetrafluoroborate.

[0091] Examples of sulfonium ions include bis(4-(diphenylsulfonio)phenyl)sulfide, diphenyl-4-(phenylthio)phenylsulfonium, triphenylsulfonium, and bis(4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl)sulfide.

[0092] Examples of sulfonium borate salts include bis(4-(diphenylsulfonio)phenyl)sulfide bistetrafluoroborate, bis(4-(diphenylsulfonio)phenyl)sulfide tetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, diphenyl-4-(phenylthio)phenylsulfonium tetrakis(pentafluorophenyl)borate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium tetrakis(pentafluorophenyl)borate, bis(4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl)sulfide bistetrafluoroborate, and bis(4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl)sulfide tetrakis(pentafluorophenyl)borate.

[0093] Examples of iodonium ions include diphenyliodonium, bis(dodecylphenyl)iodonium, and 4-isopropylphenyl-4-methylphenyliodonium.

[0094] Examples of iodonium borate salts include diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, 4-isopropylphenyl-4-methylphenyliodonium tetrafluoroborate, and 4-isopropylphenyl-4-methylphenyliodonium tetrakis(pentafluorophenyl)borate.

[0095] The diazonium ion may, for example, be phenyldiazonium.

[0096] Examples of the diazonium borate salt include phenyldiazonium tetrafluoroborate and phenyldiazonium tetrakis(pentafluorophenyl)borate.

[0097] Examples of pyridinium ions include 1-benzyl-2-cyanopyridinium and 1-(naphthylmethyl)-2-cyanopyridinium.

[0098] Examples of pyridinium borate salts include 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-(naphthylmethyl)-2-cyanopyridinium tetrafluoroborate, 1-benzyl-2-cyanopyridinium tetrakis(pentafluorophenyl)borate, and 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate.

[0099] Examples of the mass % content (borate salt / nonvolatile content of the curable composition) include 10 mass %, 9.5 mass %, 9 mass %, 8.5 mass %, 8 mass %, 7.5 mass %, 7 mass %, 6.5 mass %, 6 mass %, 5.9 mass %, 5.5 mass %, 5 mass %, 4.5 mass %, 4 mass %, 3.5 mass %, 3 mass %, 2.9 mass %, 2.5 mass %, 2 mass %, 1.5 mass %, 1 mass %, 0.5 mass %, etc. In one embodiment, the content is preferably 0.5 mass % to 10 mass %.

[0100] <Hindered phenol group-containing compounds> In one embodiment, the curable composition may optionally contain a hindered phenol group-containing compound. The hindered phenol group-containing compound may be used alone or in combination of two or more.

[0101] Examples of the hindered phenol group-containing compound include a hindered phenol structure-containing compound, a semi-hindered phenol structure-containing compound, and a less hindered phenol structure-containing compound.

[0102] The hindered phenol structure is represented by the following formula: [ka]

[0103] Examples of compounds containing a hindered phenol structure include 3,5-di-tert-butyl-4-hydroxytoluene, tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid]pentaerythritol, and 2,4,6-tris(3',5'-di-tert-butyl-4'-hydroxybenzyl)mesitylene.

[0104] The semi-hindered phenol structure is represented by the following formula: [ka]

[0105] Examples of the semi-hindered phenol structure-containing compound include 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5,5]undecane, ethylene bis(oxyethylene) bis[3-(5-tert-butyl-hydroxy-m-tolyl)propionate], triethylene glycol bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate], and the like.

[0106] The less hindered phenol structure is represented by the following formula: [ka]

[0107] Examples of the less hindered phenol structure-containing compound include 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane and 4,4'-butylidenebis(3-methyl-6-tert-butylphenol).

[0108] Examples of the mass % content (hindered phenol group-containing compound / nonvolatile content of the curable composition) include 3 mass %, 2.5 mass %, 2 mass %, 1.5 mass %, 1 mass %, 0.5 mass %, 0.2 mass %, 0.15 mass %, 0.1 mass %, 0.05 mass %, and 0 mass %. In one embodiment, the content is preferably 0 mass % to 3 mass %, and more preferably 0.05 mass % to 1 mass %. A more preferable content is, for example, to suppress changes in hardness when applied in a humid environment.

[0109] <Radical initiator> In one embodiment, the curable composition may optionally contain a radical initiator. The radical initiators may be used alone or in combination of two or more.

[0110] Examples of the radical initiator include an α-hydroxydimethylacetophenone group-containing radical initiator, α-hydroxycycloalkylphenone, α-aminoalkylphenone, benzil dimethyl ketal, unsubstituted or substituted alkylphenone, unsubstituted or substituted benzil, unsubstituted or substituted benzophenone, acylphosphine oxide, substituted thioxanthone, and oxime ester.

[0111] Examples of the α-hydroxydimethylacetophenone group-containing radical initiator include 2-hydroxy-2-methyl-1-phenylpropanone, 1-[4-(2-hydroxyethoxyl)-phenyl]-2-hydroxy-methylpropanone, and 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one.

[0112] Examples of α-hydroxycycloalkylphenones include 1-hydroxycyclohexyl phenyl ketone.

[0113] Examples of α-aminoalkylphenones include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one.

[0114] Examples of benzyl dimethyl ketals include 2,2-dimethoxy-1,2-diphenylethan-1-one.

[0115] 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.

[0116] Examples of unsubstituted or substituted benzyl include benzyl and p-anisyl.

[0117] 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.

[0118] Examples of the acylphosphine oxide include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0119] Examples of substituted thioxanthone include 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

[0120] 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).

[0121] When electron beam curing is used, a radical initiator is not required.

[0122] In one embodiment, the radical initiator is preferably acylphosphine oxide, for example, because it produces less precipitate after emulsification.

[0123] Examples of the mass % content (radical initiator / active energy ray-curable composition nonvolatile content) include 10 mass %, 9.5 mass %, 9 mass %, 8.5 mass %, 8 mass %, 7.5 mass %, 7 mass %, 6.5 mass %, 6 mass %, 5.9 mass %, 5.5 mass %, 5 mass %, 4.5 mass %, 4 mass %, 3.5 mass %, 3 mass %, 2.9 mass %, 2.5 mass %, 2 mass %, 1.5 mass %, 1 mass %, 0.5 mass %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 10 mass %.

[0124] <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.

[0125] 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.

[0126] Examples of the ketone solvent include methyl ethyl ketone, acetylacetone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone.

[0127] Examples of aromatic solvents include toluene and xylene.

[0128] Examples of the alcohol solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, i-butanol, and t-butanol.

[0129] Examples of glycol solvents include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol.

[0130] 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.

[0131] Examples of the ester solvent include ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate.

[0132] Examples of petroleum-based solvents include Solvesso #100 (manufactured by Exxon Chemical), Solvesso #150 (manufactured by Exxon Chemical), and the like.

[0133] Examples of haloalkane solvents include chloroform.

[0134] The amide solvent may, for example, be dimethylformamide.

[0135] In one embodiment, the organic solvent is preferably an alcohol solvent or a glycol ether solvent, more preferably isopropyl alcohol, n-butanol, isobutanol, or propylene glycol monomethyl ether, even more preferably a combination of isopropyl alcohol and propylene glycol monomethyl ether, or a combination of isopropyl alcohol and propylene glycol monomethyl ether, and particularly preferably a combination of isopropyl alcohol and propylene glycol monomethyl ether. The reason for this preference is, for example, improvement in leveling properties.

[0136] Examples of the mass % content (organic solvent / active energy ray-curable composition) 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 %, 0 mass %, etc. In one embodiment, the content is preferably 0 mass % to 80 mass %.

[0137] <Additives> The curable composition may optionally contain an agent (additive) that does not fall into any of the above categories.

[0138] Examples of the additives include ultraviolet absorbers, antifoaming agents, surface conditioners, antifouling agents, and pigments.

[0139] In one embodiment, the content in parts by mass (additive / curable composition) 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.

[0140] In one embodiment, the parts by mass content (additive / alicyclic epoxy group-containing acyclic siloxane), the parts by mass content (additive / radical polymerizable group-containing compound), the parts by mass content (additive / borate salt), the parts by mass content (additive / hindered phenol group-containing compound), the parts by mass content (additive / radical initiator), and the parts 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, and the like.

[0141] A curable composition can be produced by dispersing and mixing the above agents.

[0142] Examples of the dispersing and mixing means include an emulsifying disperser and an ultrasonic dispersing device.

[0143] The application (curable composition) can be, for example, a coating agent. [Cured product] The present disclosure relates to a cured product of the above curable composition.

[0144] Examples of the curing conditions include the following conditions.

[0145] [Laminate] The present disclosure relates to a laminate comprising the above-mentioned cured product.

[0146] In one embodiment, the laminate can be produced by a method comprising the following steps. Coating step: a step of coating the composition on at least one surface of a substrate. Active energy ray curing process: A process of forming a cured layer by irradiating active energy rays

[0147] 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.

[0148] In one embodiment, the thickness (substrate) is preferably 10 μm to 2000 μm.

[0149] In one embodiment, the thickness (of the cured product layer) is preferably 0.1 μm to 20 μm.

[0150] (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 coat coating, offset printing, flexographic printing, and screen printing.

[0151] (Active energy ray curing process) Examples of the active energy ray include ultraviolet rays and electron beams.

[0152] Examples of ultraviolet light sources include xenon lamps, high-pressure mercury lamps, and metal halide lamps.

[0153] 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

[0154] 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]

[0155] 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.

[0156] Production Example 1: Alicyclic epoxy group-containing acyclic alkoxysiloxane A reaction vessel equipped with a stirrer, thermometer, dropping funnel, condenser, and air inlet was mixed with 66 parts by mass of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (product name "KBM-303", manufactured by Shin-Etsu Chemical Co., Ltd.), 7 parts by mass of methanol, and 7 parts by mass of water, and the reaction was carried out at 70°C for 2 hours. After cooling the reaction system to room temperature, 20 parts by mass of 1-methoxy-2-propanol was added and mixed to obtain an alicyclic epoxy group-containing acyclic alkoxysiloxane (non-volatile content 66%).

[0157] Example The substances listed in the table below were mixed as non-volatile components and then diluted to obtain a coating agent (dilution solvent: methyl isobutyl ketone, non-volatile content: 30%).

[0158] Unless otherwise specified, other examples were carried out in the same manner as above, except for the changes shown in the table below.

[0159] [Table 1] X-40-2669: Shin-Etsu Chemical Co., Ltd. [ka] KR-470: Shin-Etsu Chemical Co., Ltd. [ka] X-40-2678: Alicyclic epoxy group-containing cyclic siloxane bifunctional oligomer, manufactured by Shin-Etsu Chemical Co., Ltd. Epolead GT-401: butanetetracarboxylic acid tetra(3,4-epoxycyclohexylmethyl) modified ε-caprolactone, manufactured by Daicel Corporation NK Ester A-9550: Dipentaerythritol polyacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd. Aronix M305: Pentaerythritol polyacrylate, manufactured by Toagosei Co., Ltd. Compound A: 4-isopropylphenyl-4-methylphenyliodonium tetrakis(pentafluorophenyl)borate, manufactured by Tokyo Chemical Industry Co., Ltd. CPI-110B: diphenyl-4-(phenylthio)phenylsulfonium tetrakis(pentafluorophenyl)borate, manufactured by San-Apro Co., Ltd. IK-1: 4-Isopropylphenyl(p-tolyl)iodonium tris(pentafluoroethyl)trifluorophosphate, manufactured by San-Apro Co., Ltd. CPI-100P: 4-(phenylthio)phenyl-diphenylsulfonium hexafluorophosphate, manufactured by San-Apro Co., Ltd. CPI-210S: 4-(phenylthio)phenyl-diphenylsulfonium tris(pentafluoroethyl)trifluorophosphate, manufactured by San-Apro Co., Ltd. OMNIRAD184: 1-hydroxycyclohexyl-phenyl ketone, manufactured by IGM Regins Co., Ltd. BHT: 3,5-di-tert-butyl-4-hydroxytoluene

[0160] The prepared coating agent was applied to the adhesive surface of polyester film Cosmoshine A4160 (manufactured by Toyobo Co., Ltd., thickness 100 μm) using a bar coater under a room temperature and humidity environment (air temperature 23.0°C, relative humidity 50%) adjusted in a humidity-control booth so that the film thickness after drying would be 10 μm, and the coating agent was then dried in a commercially available hot air dryer at 80°C for 60 seconds. After that, the coating agent was dried in a nitrogen atmosphere using a high-pressure mercury lamp at 900 mJ / cm. 2 The laminate was obtained by irradiating the film with ultraviolet light.

[0161] curl Each laminate was cut into a 10 cm x 10 cm square and placed on a horizontal table. The vertical height of each of the four corners of the cut-out laminate square from the table was measured, and the average value was taken as the curl value and evaluated as follows: Good: The curl value is less than 5 mm. △: Curl value is 5 mm or more and less than 10 mm. ×: The curl value is 10 mm or more, or the cut laminate is cylindrical.

[0162] Hardness change when applied in a humid environment A laminate was prepared in a high humidity environment (temperature 26.0°C, relative humidity 70%) adjusted using a humidity control booth, and the pencil hardness was measured in the same manner as in the normal temperature and humidity environment. The pencil hardness values ​​measured in the normal temperature and humidity environment and the high humidity environment were compared and evaluated as follows: ⊚: There is no difference in the evaluation value of pencil hardness, including the difference in defects due to plastic deformation, compared to under normal temperature and humidity conditions. ○: There is a slight difference due to differences in defects caused by plastic deformation compared to under normal temperature and humidity conditions, but there is no difference in the evaluation value of pencil hardness due to scratches. ×: The pencil hardness is clearly reduced compared to that under normal temperature and humidity conditions.

[0163] Evaluation example [Table 2]

[0164] Total light transmittance% Measurement was carried out using a haze meter manufactured by Suga Test Instruments Co., Ltd.

[0165] Hayes Measurement was carried out using a haze meter manufactured by Suga Test Instruments Co., Ltd.

[0166] pencil hardness The pencil hardness of the cured product was measured in accordance with JIS K5600-5-4.

Claims

1. A curable composition comprising an alicyclic epoxy group-containing acyclic siloxane, a radically polymerizable group-containing compound, and a borate salt.

2. The curable composition of claim 1 , comprising a hindered phenol group-containing compound.

3. A cured product of the curable composition according to claim 1 or 2.

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

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