JP2003212937A - Resin composition and cured article thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a resin composition curable with a practical amount of light irradiation without using a photopolymerization initiator or with using it in a smaller amount than that used conventionally and to provide a cured article thereof. <P>SOLUTION: The resin composition contains a specific maleimide derivative (A<SB>1</SB>) and/or a urethane-modified maleimide derivative (A<SB>2</SB>) and a polymerizable compound (B) other than the component (A<SB>1</SB>) or (A<SB>2</SB>). <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to various coating materials, surface treatment agents, optical waveguide materials, molding materials, laminated plates,
Regarding a novel active energy ray-curable resin composition useful for adhesives, pressure-sensitive adhesives, printing inks, resist inks, binders, etc., more specifically, a photopolymerization initiator is not used, or less than the conventional amount used. The present invention relates to a novel resin composition and a cured product thereof which are cured by a practical dose of ultraviolet rays even when used.

[0002]

2. Description of the Related Art A resin composition which is polymerized and cured by active energy rays such as ultraviolet rays and visible rays has an advantage of rapid curing and is widely used for paints, printing inks, adhesives, coating agents and the like. . However, since the conventional active energy ray-curable composition itself does not initiate polymerization, it is necessary to use a photopolymerization initiator in combination. When the addition amount of the photopolymerization initiator is increased, a large amount of active radical species are generated by irradiation with active energy rays, and the curing speed tends to increase. Therefore, the addition amount tends to increase when the curing is desired to be accelerated. .

Further, in a cured product obtained from an active energy ray-curable resin composition containing a photopolymerization initiator, an unreacted photopolymerization initiator or a decomposed product of the photopolymerization initiator remains. , When light or heat acts on this cured product,
The cured product may turn yellow or generate a bad odor. Further, the cured product obtained from the active energy ray-curable resin composition containing a photopolymerization initiator, when left in water or the like,
Since the unreacted photopolymerization initiator and the like bleed, it was unsuitable for use as a food packaging material.

In order to improve the drawbacks of the active energy curable resin composition containing these photopolymerization initiators, as an active energy ray curable composition containing no photopolymerization initiator,
JP-A-6-298817 discloses a photopolymerization method using a maleimide compound as an electron acceptor and a charge transfer complex formed in combination with an electron donor.

In addition, "Polymer Materials Science and Engineering (Polymer Ma
terials Science and Engine
72) pp. 470-472 (199)
5) and "Papers at the 4th Fusion UV Technology Seminar", pp. 43-77 (1996), a method of using a maleimide derivative as an electron acceptor and vinyl ether as an electron donor is reported. In these documents, a photopolymerizable resin composition composed of a combination of 1,4-bis (vinyloxymethyl) cyclohexane and cyclohexylmaleimide, or 4-, which exhibits polymerizability in the absence of a photopolymerization initiator, or 4- A photopolymerizable resin composition comprising a combination of hydroxybutyl vinyl ether and hydroxyalkyl maleimide is described.
However, these resin compositions have a problem that a cured coating film is not formed although the reaction proceeds.

On the other hand, "Polymer preprints (Poly
Mer Preprints), Vol. 37, No. 2, 34
8 to 349 (1996), 1,6-hexanediol diacrylate and polyethylene glycol # 40.
N, N'-4,9 as a polymerization initiator of 0 diacrylate
Maleimides such as -dioxa-1,12-bismaleimidodecane are disclosed. However, these maleimides are often solid and have a problem of poor solubility in acrylate.

[0007]

The object of the present invention is to use a specific maleimide derivative so that a photopolymerization initiator is not used, or a practical irradiation dose is obtained even when the photopolymerization initiator is used in a smaller amount than the conventional amount. Provided are a novel resin composition curable by ultraviolet rays and a cured product thereof.

[0008]

The present inventor has made the above
In order to solve various problems, the specific maleimide derivative
(A₁) And / or certain urethane-modified maleimide derivatives
Body (A₂Use of a novel resin composition containing
The present invention has been completed by finding that the above-mentioned problems can be achieved by
It has come to do. That is, the present invention is (1),
Monocarboxylic acid (a) having a reimide group and in one molecule
Reaction product with compound (b) having one epoxy group
(X) a maleimide derivative (A₁) And / or reaction
Optional (X) and organic polyisocyanate compound (c)
It is a reaction product with the polyol compound (d) as a component.
Urethane-modified maleimide derivative (A ₂) And (A₁)as well as
(A₂) Containing a polymerizable compound (B) other than the component
A resin composition characterized by: (2) a polymerizable compound (B)
(Meth) acryloyl group, vinyl ether group or N-bi
One or more selected from the group consisting of compounds having a nyl group
The resin composition according to (1), which is a compound of
(A) A compound having an acryloyl group is a (poly) ester
(Meth) acrylate (B-1-1), urethane (me
A) acrylate (B-1-2), epoxy (meth) a
Crylate (B-1-3), (poly) ether (meth)
Acrylate (B-1-4), alkyl (meth) acry
Rate or alkylene (meth) acrylate (B-1-
5), (meth) acrylate having an aromatic ring (B-1-
6) and a (meth) acrylate having an alicyclic structure (B-
1-7) one or more compounds selected from the group consisting of
Resin composition according to (5), (4), vinyl ether group
If the compound having
Optionally substituted alkyl vinyl ether (B-2-
1), the other end is substituted with a halogen atom or a hydroxyl group
Cycloalkyl vinyl ether (B-2-
2), vinyl ether group is bonded to alkylene group,
An optionally substituted alkyl group, cycloalkyl
At least one selected from the group consisting of an aromatic group and an aromatic group.
And ether bond, urethane bond and ester bond
Connected via at least one bond selected from the group consisting of
Monovinyl ether, vinyl ether having a structure
It consists of ether and polyvinyl ether (B-2-3)
The tree according to (3), which is one or more compounds selected from the group
Contains a fat composition, (5), and a photopolymerization initiator (C)
The resin composition according to any one of (1) to (4)
Item, (6), described in any one of (1) to (5)
And a cured product of the resin composition.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The resin composition of the present invention is a maleimide which is a reaction product (X) of a monocarboxylic acid (a) having a maleimide group and a compound (b) having one epoxy group in the molecule. A urethane-modified maleimide derivative (A ₂ ), which is a reaction product of the derivative (A ₁ ) and / or the reaction product (X), the organic polyisocyanate compound (c) and, as an optional component, the polyol compound (d), (A ₁ ) and It is a mixture with the polymerizable compound (B) other than the component (A ₂ ).

The resin composition of the present invention contains a maleimide derivative (A ₁ ). The maleimide derivative (A ₁ ) is a monocarboxylic acid (a) having a maleimide group and 1 in one molecule.
It is a reaction product (X) obtained by reacting a compound (b) having one epoxy group. Specific examples of the maleimide group-containing monocarboxylic acid (a) include, for example,

[0011]

[Chemical 1]

From a maleic anhydride and a primary aminocarboxylic acid as shown in
DH Rich et al. "Journal
Of Medical Chemistry (Journal o
f Medical Chemistry) "18th
Vol. 1004-1010 (1975)] can be used to synthesize compound (a-1) or a half of a maleimide compound having a hydroxyl group and a compound having one acid anhydride group in the molecule. Ester compound (a-2)
Etc. can be mentioned.

Examples of the maleimide compound having a hydroxyl group include those represented by the reaction formula

[0014]

[Chemical 2]

As shown by the formula, from maleimide and formaldehyde, or the reaction formula

[0016]

[Chemical 3]

As shown in (1), it can be synthesized from maleic anhydride and a primary amino alcohol using a known technique (see, for example, US Pat. No. 2,526,517, JP-A-2-268155). it can.

Examples of the primary aminocarboxylic acid used in the above reaction include asparagine, alanine, β-alanine, arginine, isoleucine, glycine, glutamine, tryptophan, threonine, valine, phenylalanine, homophenylalanine, α-methyl-phenylalanine. , Lysine, leucine, cycloleucine, 3-
Aminopropionic acid, α-aminobutyric acid, 4-aminobutyric acid, aminovaleric acid, 6-aminocaproic acid, 7-aminoheptanoic acid, 2-aminocaprylic acid, 3-aminocaprylic acid, 6-aminocaprylic acid, 8-amino Caprylic acid,
Examples thereof include 9-aminononanoic acid, 2-aminocapric acid, 9-aminocapric acid, 15-aminopentadecanoic acid, 2-aminopalmitic acid, 16-aminopalmitic acid, but are not limited thereto.

The primary amino alcohol used in the above reaction is, for example, 2-aminoethanol, 1-amino-2-propanol, 3-amino-1-propanol, 2-amino-2-methyl-1-1 propanol. Two
-Amino-3-phenyl-1-propanol, 4-amino-1-butanol, 2-amino-1-butanol, 2
-Amino-3-methyl-1-butanol, 2-amino-
4-methylthio-1-butanol, 2-amino-1-pentanol (1-aminocyclopentane) methanol,
Examples thereof include 6-amino-1-hexanol, 7-amino-1-heptanol, 2- (2-aminoethoxy) ethanol, and the like, but are not limited thereto.

Specific examples of the compound having one acid anhydride group in the molecule include maleic anhydride, succinic anhydride, phthalic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride and methyl hexahydroanhydride. Examples thereof include phthalic acid and methyl-tetrahydrophthalic anhydride.

The half-esterified product (a-2) is
It can be obtained by reacting one chemical equivalent of a hydroxyl group in the maleimide compound having a hydroxyl group with about one chemical equivalent of an anhydride group in a compound having one acid anhydride group in the molecule. The reaction temperature is preferably 60 to 100 ° C., and the reaction time is preferably 1 to 10 hours. If necessary, an organic solvent may be used during the reaction.

Specific examples of the compound (b) having one epoxy group in one molecule include tert-butyl glycidyl ether, 2-ethylhexyl glycidyl ether,
Methoxy poly (n = 1-10) ethoxy glycidyl ether, ethoxy poly (n = 1-10) ethoxy glycidyl ether, butoxy poly (n = 1-10) ethoxy glycidyl ether, methoxy poly (n = 1-10) propoxy diglycidyl ether, phenyl Glycidyl ether, cresol glycidyl ether, o-phenylphenyl glycidyl ether, o-phenylphenyloxypoly (n = 1-10) ethoxyglycidyl ether,
Examples thereof include o-phenylphenyloxy poly (n = 1 to 10) propoxyglycidyl ether and n-nonylphenol poly (n = 1 to 10) ethoxyglycidyl ether.

The above-mentioned reaction of the monocarboxylic acid (a) having a maleimide group with the compound (b) having one epoxy group in one molecule can be carried out without solvent or with solvents such as acetone, ethylmethylketone, Ketones such as cyclohexanone, aromatic hydrocarbons such as benzene, toluene, xylene and tetramethylbenzene, glycols such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether and triethylene glycol dimethyl ether. Ethers, ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, propylene glycol monomethyl ether Ether acetate, dialkyl glutarate, dialkyl succinate, esters such as dialkyl adipates, cyclic esters such as γ- butyrolactone, petroleum ether, petroleum naphtha, can be preferably used petroleum solvents such Sorubensonafusa. Further, a compound having a (meth) acryloyl group described later can be preferably used.

During the reaction, it is preferable to use a catalyst for promoting the reaction, and the amount of the catalyst used is 0.1 to 10% by weight based on the reactant. Specific examples of the catalyst that can be used include triethylamine, benzyldimethylamine, 2-methylimidazole, triethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, triphenylphosphine, triphenylstibine, chromium octanoate, octane. Examples thereof include zirconium acid.

A polymerization inhibitor may be used for the purpose of preventing polymerization during the reaction. Specific examples of the polymerization inhibitor that can be used include P-methoxyphenol, hydroquinone, methylhydroquinone, phenothiazine and the like. The amount of the polymerization inhibitor used is 0.05 to 3% by weight based on the reaction product.

Regarding the reaction ratio of the above-mentioned components (a) and (b), it is preferable to react about 1 equivalent of the carboxylic acid in the component (b) per equivalent of the epoxy group in the component (a). The reaction temperature is preferably 70 to 150 ° C., and the reaction time is preferable.

In one embodiment of the resin composition of the present invention, a urethane-modified maleimide derivative (A ₂ ) is used. The urethane-modified maleimide derivative (A ₂ ) is obtained by reacting the reaction product (X) of the components (a) and (b), the organic polyisocyanate (c), and the polyol compound (d) as an optional component. You can

Organic polyisocyanates (c) that can be used
As specific examples of, P-phenylene diisocyanate,
m-Phenylene diisocyanate, P-xylene diisocyanate, m-xylene diisocyanate, 2,4-
Aromatic diisocyanates such as tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, naphthalene diisocyanate; isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexyl methane diisocyanate, hydrogenated xylene diisocyanate, Examples include aliphatic or alicyclic diisocyanates such as norbornene diisocyanate and lysine isocyanate; burettes of one or more kinds of isocyanate monomers, and polyisocyanates such as isocyanates obtained by trimerizing the above diisocyanate compounds.

Specific examples of the polyol compound (d) which can be used if necessary include ethylene glycol, propylene glycol, 1,2-butylene glycol and 1,4.
-Butanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,9-nonanediol, 2-butyl-2-ethyl-1,3-propanediol, cyclohexane- 1,
A polyol (d-1) such as 4-dimethanol, bisphenol A polyethoxydiol, bisphenol F polyethoxydiol, hydrogenated bisphenol A, trimethylolpropane and glycerin, and these polyols (d-
1) and alkyroxide (eg ethylene oxide,
Polypropylene polyol (d-2), which is a reaction product of propylene oxide, butylene oxide, tetrahydrofuran), and polycarbonate polyol (d, which is a reaction product of a polyol (d-1) and a dialkyl carbonate (eg, dimethyl carbonate, diethyl carbonate). -3), a lactone-modified polyol (d-4) which is a reaction product of a polyolyl (d-1) and a lactone (eg, ε-caprolactone), a polyol (d-1) and maleic acid, fumaric acid, and amber Acid, adipic acid, phthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, dimer acid, sebacic acid, azelaic acid,
5-sodium sulfoisophthalic acid, trimellitic acid,
Polyester polyols (d-5) and polyols (d-1) which are reaction products of polybasic acids such as pyromellitic acid and their anhydrides, and the above-mentioned polybasic acids and their anhydrides and lactones (eg, Lactone-modified polyester polyol (d-6) that is a reaction product with ε-caprolactone, δ-valerolactone), silicon-modified polyol, polybutadiene diene, polymer polyol (eg, methyl methacrylate ester, 2-hydroxyethyl methacrylate, Acrylic acid, styrene, etc., a copolymer of one ethylenically unsaturated group-containing compound in one molecule), dimethylolpropionic acid, etc., a polyol having one carboxyl group and two hydroxyl groups in one molecule Other polyols (d-7) and the like can be mentioned.

The above-mentioned urethane-modified maleimide derivative (A
Examples of the reaction method for obtaining ₂ ) include the following methods.

The first method is a method obtained by reacting the reaction product (X) with the organic polyisocyanate compound (c),
The second method is a method in which the organic polyisocyanate compound (c) is reacted with the polyol compound (d) and then the reaction product (X) is reacted, and the third method is the reaction product (X) and the organic polyisocyanate compound. (C) is reacted, and then the polyol compound (d) is reacted, and the like. The first method and the second method are preferable.

The reaction ratio of the reaction product (X) and the component (c) in the first method is such that 1 equivalent of the hydroxyl group in the reaction product (X) reacts with 0.9 to 1.05 equivalent of the isocyanate group in the component (c). It is preferable that the amount is 0.95 to 1.00 equivalent. The reaction ratio of the component (c), the component (d) and the reaction product (X) in the second method is such that the isocyanate group in the component (c) is 1.05-2 with respect to 1 equivalent of the hydroxyl group in the component (d). ．
It is preferred to react 0 equivalents, particularly preferably 1.
It is 2 to 2.0 equivalents. 0.95 to 1.1 equivalents of hydroxyl acid in the reaction product (X) is preferable, and particularly preferably 0.99, relative to 1 equivalent of the isocyanate group in the reaction product of the components (d) and (c). ~ 1.05 equivalents.

The reaction temperature is 40 in both the first method and the second method.
The temperature is preferably -100 ° C, and a reaction catalyst such as di-n-butyltin dilaurylate is preferably added to accelerate the reaction, if necessary. The reaction time varies depending on the reaction temperature, the amount of the catalyst added, and the ratio of each component, but is 1 to 3.
0 hours is preferred.

A polymerization inhibitor may be used during the reaction for the purpose of preventing polymerization. Specific examples of the polymerization inhibitor that can be used include P-methoxyphenol, hydroquinone, methylhydroquinone, phenothiazine and the like. The resin composition of the present invention comprises (A ₁ ),
It contains a polymerizable compound (B) other than the component (A ₂ ). Specific examples of the polymerizable compound (B) include a compound having a (meth) acryloyloxy group, a compound having a vinyl ether group, a compound having an N-vinyl group, (A ₁ ),
Examples include maleimide compounds other than the component (A ₂ ), (meth) acrylamide compounds, unsaturated polyesters, and the like.

(Meth) which may be contained in the resin composition of the present invention
When a compound having an acryloyloxy group is roughly classified,
(Poly) ester (meth) acrylate (B-1-
1); Urethane (meth) acrylate (B-1-2);
Epoxy (meth) acrylate (B-1-3); (Poly) ether (meth) acrylate (B-1-4); Alkyl (meth) acrylate or alkylene (meth) acrylate (B-1-5); Aromatic ring Having (meth) acrylate (B-1-6); having an alicyclic structure (meth)
Examples thereof include acrylate (B-1-7), but are not limited thereto.

(Poly) which may be contained in the resin composition of the present invention
The ester (meth) acrylate (B-1-1) is a generic term for (meth) acrylate having one or more ester bonds in the main chain and is a urethane (meth) acrylate (B-.
1-2) is a general term for (meth) acrylates having one or more urethane bonds in the main chain, and is epoxy (meth)
Acrylate (B-1-3) is a general term for (meth) acrylate obtained by reacting a monofunctional or higher functional epoxy compound with (meth) acrylic acid, and is a (poly) ether (meth) acrylate (B-1- 4) is a general term for (meth) acrylate having at least one ether bond in the main chain, and alkyl (meth) acrylate or alkylene (meth) acrylate (B-1-5) is a straight-chain alkyl having a main chain. , Branched alkyl, and (meth) acrylate (B-1-6) having an aromatic ring as a general term for (meth) acrylate which may have a halogen atom and / or a hydroxyl group at a straight chain or at a terminal are the main chains. Or, as a general term for (meth) acrylates having an aromatic ring in the side chain, (meth) acrylate (B-1-7) having an alicyclic structure means that the main chain or side chain has an acid as a structural unit. As a general term that also contain an atom or a nitrogen atom having a good alicyclic structure-containing (meth) acrylate is used, respectively.

The resin composition of the present invention may contain (poly)
Examples of the ester (meth) acrylate (B-1-1) include caprolactone-modified 2-hydroxyethyl (meth) acrylate, ethylene oxide and / or propylene oxide-modified phthalic acid (meth) acrylate, ethylene oxide-modified succinic acid (meth ) Acrylate, monofunctional (poly) ester (meth) acrylates such as caprolactone modified tetrahydrofurfuryl (meth) acrylate; hydroxypivalic acid ester neopentyl glycol di (meth) acrylate, caprolactone modified hydroxypivalic acid ester neopentyl glycol di ( (Meth) acrylate, epichlorohydrin-modified phthalic acid di (meth) acrylate; 1 mol or more of ε- per 1 mol of trimethylolpropane or glycerin
Mono-, di- or tri (meth) acrylate of triol obtained by adding a cyclic lactone compound such as caprolactone, γ-butyrolactone, δ-valerolactone;

1 mol or more of ε-caprolactone per 1 mol of pentaerythritol or ditrimethylolpropane,
Mono-, di-, tri- or tetra (meth) acrylate of triol obtained by adding a cyclic lactone compound such as γ-butyrolactone or δ-valerolactone, 1 mol or more of ε-caprolactone and γ-butyrolactone per 1 mol of dipentaerythritol , A monool of triol obtained by adding a cyclic lactone compound such as δ-valerolactone, or a mono (meth) acrylate of polyhydric alcohol such as triol, tetraol, pentaol or hexaol of poly (meth) acrylate, or poly (Meth) acrylate;

(Poly) ethylene glycol, (poly) propylene glycol, (poly) tetramethylene glycol, (poly) butylene glycolyl, 3-methyl-1,
Diol components such as 5-pentanediol, hexanediol and maleic acid, fumaric acid, succinic acid, adipic acid,
Polybasic acids such as phthalic acid, isophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, dimer acid, sebacic acid, azelaic acid, 5-sodium sulfoisophthalic acid, etc., and polyester polyols that are the reaction products with their anhydrides. (Meth) acrylate; the diol component, polybasic acid and their anhydrides, ε-caprolactone, γ
Examples thereof include, but are not limited to, polyfunctional (poly) ester (meth) acrylates such as (meth) acrylate of a cyclic lactone-modified polyester diol composed of butyrolactone, δ-valerolactone and the like.

The urethane (meth) acrylate (B-1-2) that can be contained in the resin composition of the present invention is a hydroxy compound (B-1-2) having at least one (meth) acryloyloxy group and an isocyanate. Compound (B
It is a general term for (meth) acrylates obtained by the reaction with (1-2).

Examples of the hydroxy compound (B-1-2) having at least one (meth) acryloyloxy group are, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate and 2-hydroxy. Butyl (meth) acrylate, 4-
Hydroxyethyl (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, 2-hydroxy-
Examples thereof include (meth) acrylate compounds having various hydroxyl groups such as 3-phenoxypropyl (meth) acrylate, and ring-opening reaction products of the above-mentioned (meth) acrylate compounds having hydroxyl groups with ε-caprolactone.

Isocyanate compound (B-1-2)
As, for example, P-phenylene diisocyanate,
m-Phenylene diisocyanate, P-xylene diisocyanate, m-xylene diisocyanate, 2,4-
Aromatic diisocyanates such as tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, naphthalene diisocyanate; isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexyl methane diisocyanate, hydrogenated xylene diisocyanate, Aliphatic or alicyclic diisocyanates such as norbornene diisocyanate and lysine diisocyanate;
Examples include polyisocyanates such as burettes of one or more types of isocyanate monomers or isocyanates obtained by trimerizing the above diisocyanate compounds; and polyisocyanates obtained by urethanization reaction between the above isocyanate compounds and the above polyol compounds.

The epoxy (meth) acrylate (B-1-3) that can be contained in the resin composition of the present invention is obtained by reacting an epoxy resin containing a monofunctional or higher epoxy group with (meth) acrylic acid. It is a general term for the (meth) acrylates obtained. Examples of the epoxy resin used as a raw material for the epoxy (meth) acrylate include the compound (b-4) having an epoxy group described above.

(Poly) which may be contained in the resin composition of the present invention
Examples of the ether (meth) acrylate (B-1-4) include butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate,
Epichlorohydrin-modified butyl (meth) acrylate,
Dicyclopentenyloxyethyl (meth) acrylate,
Monofunctional (poly) ether (meth) acrylates such as 2-ethoxyethyl (meth) acrylate, ethylcarbitol (meth) acrylate, phenoxyethyl (meth) acrylate, nonylphenoxy polyethylene glycol (meth) acrylate;

Alkylene glycol di (meth) acrylates such as polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate; ethylene oxide and Polyhydric hydroxyl compounds such as copolymers of propylene oxide, copolymers of propylene glycol and tetrahydrofuran, polyisoprene glycol, hydrogenated polyisoprene glycol, polybutadiene glycol, hydrogenated polybutadiene glycol and other hydrocarbon-based polyols And (meth) acrylic acid-derived polyfunctional (meth) acrylates; neopentyl glycol 1
Di (meth) acrylate of diol in which 1 mole or more of a cyclic ether such as ethylene oxide, propylene oxide, butylene oxide is added to a mole;

Di (meth) acrylates of alkylene oxide-modified bisphenols such as bisphenol A, bisphenol F and bisphenol S; hydrogenated bisphenol A, hydrogenated bisphenol F and hydrogenated bisphenol S alkylene oxides Modified di (meth) acrylate; mono-, di- or tri (meth) acrylate of triol obtained by adding 1 mol or more of a cyclic ether compound such as ethylene oxide, propylene oxide or butylene oxide to 1 mol of trimethylolpropane or glycerin. ;

1 mol or more of ethylene oxide per 1 mol of pentaerythritol or ditrimethylolpropane,
Mono-, di-, tri- or tetra (meth) acrylate of triol to which cyclic ether compound such as propylene oxide and butylene oxide is added; 1 mol or more of cyclic ether compound such as ethylene oxide, propylene oxide and butylene oxide per 1 mol of dipentaerythritol Examples thereof include polyfunctional (poly) ether (meth) acrylates such as 3- to 6-functional (meth) acrylates of hexaol added with.

Examples of the alkyl (meth) acrylate or alkylene (meth) acrylate (B-1-5) that can be contained in the resin composition of the present invention include, for example, octyl (meth) acrylate, isooctyl (meth) acrylate and decyl ( Monofunctional (meth) acrylates such as (meth) acrylate and dodecyl (meth) acrylate;

Ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate,
1,4-butanediol di (meth) acrylate, 1,
6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1,8-octanediol di (meth) acrylate,
1,9-nonanediol di (meth) acrylate, 1,
Hydrocarbon diol di (meth) acrylates of 10-decanediol di (meth) acrylate;

Trimethylolpropane mono (meth) acrylate, di (meth) acrylate or tri (meth) acrylate
Acrylate (hereinafter, “poly” is used as a general term for polyfunctional such as di, tri, tetra, etc.), mono (meth) acrylate or poly (meth) acrylate of glycerin, mono- or poly (meth) acrylate of pentaerythritol, ditri. Methylol propane mono or poly (meta)
Acrylate, triol such as dipentaerythritol mono- or poly (meth) acrylate, tetraol,
Mono- or poly (meth) acrylates of polyhydric alcohols such as hexaol;

2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4
-Hydroxyl group-containing (meth) acrylates such as hydroxybutyl (meth) acrylate; and the like.

The aromatic ring-containing (meth) acrylate (B-1-6) that can be contained in the resin composition of the present invention is:
For example, monofunctional (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate;
Examples thereof include, but are not limited to, di (meth) acrylates such as bisphenol A di (meth) acrylate and bisphenol F di (meth) acrylate.

Examples of the (meth) acrylate (B-1-7) having an alicyclic structure which can be contained in the resin composition of the present invention include cyclohexyl (meth) acrylate, cyclopentyl (meth) acrylate and isobornyl (meth). Monofunctional (meth) acrylates having an alicyclic structure such as acrylate and dicyclopentenyl (meth) acrylate; Di (meth) acrylate of hydrogenated bisphenols such as hydrogenated bisphenol A and hydrogenated bisphenol F; tricyclodecanedi Examples include polyfunctional (meth) acrylates having a cyclic structure such as methylol di (meth) acrylate; alicyclic (meth) acrylates having an oxygen atom in the structure such as tetrafurfuryl (meth) acrylate, and the like. However, it is not limited to this.

As the compound having a (meth) acryloyl group which may be contained in the resin composition of the present invention, in addition to the above-mentioned compounds, for example, a reaction of a (meth) acrylic acid polymer with glycidyl (meth) acrylate Or a poly (meth) acrylic polymer (meth) acrylate such as a reaction product of a glycidyl (meth) acrylate polymer and (meth) acrylic acid; dimethylaminoethyl (meth)
(Meth) acrylate having an amino group such as acrylate; isocyanuric (meth) acrylate such as tris (meth) acryloxyethyl) isocyanurate; (meth) acrylate having a polysiloxane skeleton; polybutane-gen (meth) acrylate; melamine ( It is also possible to use (meth) acrylate.

Next, the compounds having a vinyl ether group which can be contained in the resin composition of the present invention are roughly classified, and an alkyl vinyl ether (B-2-1) in which the other end may be substituted with a halogen atom or a hydroxyl group, Cycloalkyl vinyl ether (B-2-2) which may have another terminal substituted with a halogen atom or a hydroxyl group, an alkyl group in which a vinyl ether group is bonded to an alkylene group, and which may further have a substituent, a cycloalkyl group And a mono-, di-, or polyvinyl ether having a structure in which at least one group selected from the group consisting of, and an aromatic group is bonded to each other through at least one bond selected from the group consisting of an ether bond, a urethane bond, and an ester bond. (B-2-3) and the like, but the invention is not limited thereto.

The above-mentioned alkyl vinyl ether (B-2-
As 1), for example, hydroxymethyl vinyl ether, chloromethyl vinyl ether, hydroxyethyl vinyl ether, 2-chloroethyl vinyl ether, 1,
4-butanediol divinyl ether, 1,6-hexanediol divinyl ether, 4-hydroxybutyl vinyl ether, trimethylolpropane trivinyl ether, pentaerythritol tetravinyl ether and the like can be mentioned, but not limited thereto.

Cycloalkyl vinyl ether (B
Examples of -2-2) include, but are not limited to, 2-hydroxycyclopropyl vinyl ether, cyclohexyl vinyl ether, cyclohexane dimethanol mono- or divinyl ether, cyclohexane diol mono- or divinyl ether, and the like.

As the above-mentioned mono-, di- and polyvinyl ethers (B-2-3), for example, as the compound having an ether bond (B-2-3), ethylene glycol methyl vinyl ether, diethylene glycol divinyl ether, triethylene can be mentioned. Examples thereof include glycol divinyl ether, propylene glycol methyl vinyl ether, dipropylene glycol divinyl ether and ditetramethylene glycol divinyl ether.

Compound having urethane bond (B-2-3
-) Is a monovinyl ether (m) of (poly) alkylene glycol having one hydroxyl group in one molecule.
And a compound (n) having at least one isocyanate group in one molecule can be obtained by a urethanization reaction.

Of these, examples of the monovinyl ether (m) of (poly) alkylene glycol having one hydroxyl group in one molecule include 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether,
Examples thereof include polyethylene glycol monovinyl ether.

On the other hand, the compound (n) containing at least one isocyanate group in one molecule is, for example,
The above-mentioned isocyanate compound (B-1-2) and the like can be mentioned.

A compound having an ester bond (B-2-3
-) Is the dehalogenation of the compound (l) having the monovinyl ether (m) of (poly) alkylene glycol having one hydroxyl group in one molecule and at least one carboxylic acid halide in one molecule. It can be obtained by an esterification reaction with hydrogen.

Examples of the compound (l) having at least one carboxylic acid halide in one molecule include known carboxylic acid halides such as chloride and bromide of carboxylic acid. Specific examples of the carboxylic acid include acetic acid, propionic acid, isophthalic acid, terephthalic acid, maleic acid, adipic acid, dimer acid, sebacic acid, tetrahydrophthalic acid and azelaic acid.

Next, N which can be used in combination with the resin composition of the present invention
Examples of the compound having a vinyl group include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide, N-vinylacetamide and the like.

Examples of the maleimide compound other than the components (A ₁ ) and (A ₂ ) that can be contained in the resin composition of the present invention include, for example, Nn-butylmaleimide, N-hexylmaleimide, 2- Monofunctional aliphatic maleimides such as maleimidoethyl-ethyl carbonate, 2-maleimidoethyl-propyl carbonate, N-ethyl- (2-maleimidoethyl) carbamate; alicyclic monofunctional maleimides such as N-cyclohexylmaleimide; N, Aliphatic bismaleimides such as N-hexamethylene bismaleimide, polypropylene glycol-bis (3-maleimidopropyl) ether, bis (2-maleimidoethyl) carbonate; 1,4-dimaleimidocyclohexane,
Isophorone bisurethane bis (N-ethylmaleimide)
Alicyclic bismaleimides such as; maleimide compounds obtained by esterification of maleimide acetic acid and polytetramethylene glycol; carboxymaleimide derivatives such as maleimide compounds by esterification of maleimide caproic acid with tetraethylene oxide adduct of pentaerythritol; Examples thereof include (poly) ester (poly) maleimide compounds obtained by esterifying various (poly) ols, but are not limited thereto.

(Meth) which may be contained in the resin composition of the present invention
Examples of the acrylamide compound include monofunctional (meth) acrylamides such as acryloylmorpholine and N-isopropyl (meth) acrylamide; and polyfunctional (meth) acrylamides such as methylenebis (meth) acrylamide.

Examples of the unsaturated polyester that can be contained in the resin composition of the present invention include fumaric acid esters such as dimethyl maleate and diethyl malate; polyunsaturated carboxylic acids such as maleic acid and fumaric acid, and polyunsaturated carboxylic acids. An esterification reaction product with a polyhydric alcohol may be mentioned.

The polymerizable compound (B) contained in the resin composition of the present invention is not limited to the above-mentioned compounds, but is a compound having copolymerizability with the above-mentioned (A ₁ ) and (A ₂ ) components. If so, the one or more kinds of compounds can be contained without particular limitation.

In the resin composition of the present invention, the above (A ₁ )
The content ratio of the components (A ₂ ) and (B) is not particularly limited, but the total content of the components (A ₁ ) and / or (A ₂ ) is 1
The component (B) is preferably contained in an amount of 10 to 1000 parts by weight, particularly preferably 50 to 500 parts by weight, based on 00 parts by weight.

The resin composition of the present invention is cured by irradiation with ultraviolet rays or visible light in the absence of a photopolymerization initiator, but in order to carry out the curing reaction more efficiently, a known conventional photopolymerization initiator is used. (C) can be added and cured.
The photopolymerization initiator (C) can be roughly classified into a cleavage type and a hydrogen abstraction type.

Examples of the cleavage type photopolymerization initiator include, for example,
Jetoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 1- (4-isopropylphenyl) -2-
Hydroxy-2-methylpropan-1-one, 4- (2
-Hydroxyethoxy) phenyl- (2-hydroxy-
2-propyl) ketone, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino (4-
Acetophenone-based compounds such as thiomethylphenyl) propan-1-one and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoins such as benzoin, benzoin methyl ether and benzoin isopropyl ether; Acylphosphine oxides such as 4,6-trimethylbenzoindiphenylphosphine oxide; benzyl, methylphenylglyoxy ester and the like.

On the other hand, examples of the hydrogen abstraction type photopolymerization initiator include, for example, benzophenone and 4-benzoyl-4 '.
-Methyl-diphenyl sulfide, benzophenone such as acrylated benzophenone; 2-isopropylthioxanthone, 2,4-diethoxythioxanthone, 2-
Thioxanthone series such as chlorothioxanthone; 4,4 '
-Aminobenzophenone type such as diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, camphorquinone and the like.

When the photopolymerization initiator is used, the compounding amount is
0.01 to 10.0 with respect to the resin content (resin non-volatile content)
A range of 0% by weight is preferred.

The resin composition obtained in the present invention is cured by irradiation with ultraviolet rays or visible rays in the absence of a photopolymerization initiator, but a photopolymerization agent is used in combination in order to carry out the curing reaction more efficiently. You can also do it.

Examples of such a photopolymerization accelerator include triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylaminobenzoic acid methyl ester, 4-dimethylaminobenzoic acid ethyl ester and 4-dimethylaminobenzoic acid. Examples include amines such as isoamyl ester.

When the photopolymerization accelerator is used, the compounding amount is
0.01 to 10.00 with respect to resin content (resin non-volatile content)
A weight% range is preferred.

Further, the resin composition obtained by the present invention is a non-reactive compound, an inorganic filler, an organic filler, a coupling agent, a tackifier, a defoaming agent, a leveling agent, a plasticizer depending on the use. , Antioxidants, ultraviolet absorbers, flame retardants, pigments, dyes and the like can be appropriately used.

Specific examples of the non-reactive compound include:
Liquid or solid oligomers or resins with low or no reactivity, alkyl (meth) acrylate copolymers, epoxy resins, liquid polybutadienes, dicyclopentadiene derivatives, saturated polyester oligomers, xylene resins, Examples thereof include, but are not limited to, a polyurethane polymer, a ketone resin, a diallyl phthalate polymer (dap resin), a petroleum resin, a rosin resin, a fluorine-based oligomer, and a silicon-based oligomer.

As the above-mentioned inorganic filler, for example, silicon dioxide, silicon oxide, calcium carbonate, calcium silicate,
Magnesium carbonate, magnesium oxide, talc, kaolin clay, calcined clay, zinc oxide, zinc sulfate, aluminum hydroxide, aluminum oxide, glass, mica, barium sulfate, alumina white, zeolite, silica balloon, glass balloon and the like can be mentioned. To these inorganic fillers, a silane coupling agent, a titanate coupling agent, an aluminum coupling agent, a zirconate coupling agent, etc. are added and reacted by a method such as a halogen group, an epoxy group, a hydroxyl group, a thiol group. It is also possible to have a functional group of the group.

Examples of the organic filler include benzoguanamine resin, silicone resin, low density polyethylene, high density polyethylene, polyolefin resin, ethylene / acrylic acid copolymer, polystyrene, acrylic copolymer, polymethylmethacrylate resin, Examples thereof include fluororesin, nylon 12, nylon 6/66, phenol resin, epoxy resin, urethane resin, and polyimide resin.

As the coupling agent, for example, silane coupling agent tetra (2,2-diallyloxymethyl-1-butyl) such as γ-glycidoxypropyltrimethoxysilane or γ-chloropropyltrimethoxysilane.
Titanate coupling agents such as bis (ditridecyl) phosphite titanate and bis (dioctylpyrophosphate) ethylene titanate; aluminum coupling agents such as acetoalkoxyaluminum diisopropylate; zirconium coupling agents such as acetylacetone / zirconium complex; And so on.

The tackifier, defoaming agent, leveling agent, plasticizer, antioxidant, ultraviolet absorber, flame retardant, pigment and dye which can be used in the resin composition of the present invention are known and commonly used. Any material can be used without particular limitation as long as its curability and resin properties are not impaired.

In order to obtain the resin composition of the present invention, the above components may be mixed, and the order and method of mixing are not particularly limited.

The resin composition of the present invention does not substantially require a solvent, but examples thereof include ketones such as methyl ethyl ketone and methyl isobutyl ketone, acetic acid esters such as ethyl acetate and butyl acetate, benzene, toluene and xylene. It is also possible to dilute and use the resin composition of the present invention with other commonly used organic solvents such as aromatic hydrocarbons.

The resin composition of the present invention is 180 to 500 n
It can be polymerized by irradiating ultraviolet rays or visible rays having a wavelength of m. It can also be cured by irradiation with energy rays other than ultraviolet rays or by heat.

Examples of light sources of ultraviolet rays or visible rays having a wavelength of 180 to 500 nm include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, chemical lamps, black light lamps, mercury-xenon lamps, excimers. Lamp, short arc lamp,
Helium / Cadmium laser, Argon laser,
Examples include excimer laser and sunlight.

The resin composition of the present invention is used in inks, metals such as aluminum, iron and copper, plastics such as vinyl chloride, acrylic, polycarbonate, polyethylene terephthalate, polyethylene and polypropylene, ceramics such as glass, wood, paper and printing paper. As various coating materials for fibers, etc., they are useful for applications such as surface treatment agents, binders, plastic materials, molding materials, laminated plates, adhesives and pressure-sensitive adhesives. More specific uses include planographic ink,
Ink fields such as flexo ink, gravure ink, screen ink, gloss field, paper coating field, wood coating field, beverage can coating or printing ink field, soft packaging film coating agent, printing ink or adhesive , Thermal paper, coating film for thermal film, printing ink, adhesive, pressure-sensitive adhesive or optical fiber coating agent.

The novel resin composition of the present invention is capable of forming a coating film having a high gel fraction and a high hardness, which cures at a practical light irradiation amount even in the absence of a photopolymerization initiator. The coating film is uniform and transparent.

[0089]

The present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the scope of these Examples.

(Synthesis Example of Maleimide Derivative (A ₁ )) Synthesis Example 1 150 g of phenylglycidyl ether, 211 g of maleimidocaproic acid, 0.04 g of P-methoxyphenol and 0.9 g of triphenylphosphine were charged, and the mixture was heated at 95 ° C. for about 32 hours. The reaction is carried out and the acid value of the reaction solution is 1.0 (mgKO
H / g), the reaction was terminated, and the product was subjected to MS measurement to obtain a reaction product (A ₁ −) having a molecular weight of 361 and having the following structural formula as a product.

[0091]

[Chemical 4]

(Synthesis Example of Maleimide Derivative (A ₂ )) Synthesis Example 2 Bisphenol A Poly (n≈10) ethoxydiol 6
68 g and 315 g of trimethylhexamethylene diisocyanate (mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate) were charged and reacted at 85 ° C. for about 10 hours to remove the isocyanate group in the reaction mixture. Concentration 4.
When 2% was reached, the mixture was cooled to 60 ° C., and then 373 g of the reaction product (A ₁ −) obtained in Synthesis Example 1 and 0.2 g of di-n-butyltin dilaurylate were charged, and the mixture was heated at 85 ° C. for about 10
The reaction was carried out for a period of time, and when the isocyanate group concentration in the reaction mixture became 0.1% or less, the reaction was terminated and a liquid product (A ₂ −) was obtained. The number average molecular weight of the product (A ₂ −) was about 3000.

Synthesis Example 3 Reaction product (A ₁ −) 723.8 obtained in Synthesis Example 1 above
g, 2,4-diisocyanate toluene 184 g and P
-Methoxyphenol was charged and the reaction was carried out at 85 ° C. for about 10 hours to give an isocyanate group concentration of 0.
The reaction is terminated when the amount becomes 1% or less, and the obtained product (A ₂ −) is mainly composed of the following structural formula having a molecular weight of 906 by MS measurement.

[0094]

[Chemical 5]

Examples 1 to 3 The resin compositions of the present invention were obtained by mixing and dissolving according to the composition of Table 1. Regarding the resin composition thus prepared,
UV curability and gel fraction of the cured coating film and pencil hardness were evaluated according to the following evaluation methods, and the results are summarized in Table 1.

Comparative Examples 1 and 2 Resin compositions were obtained by blending and dissolving according to the blending composition of Table 2. With respect to the resin composition thus prepared, UV curability, gel fraction of cured coating and pencil hardness were evaluated according to the following evaluation methods, and the results are summarized in Table 2.

(1) Ultraviolet curability: Each resin composition was applied onto a glass plate so that the film thickness after curing was 50 μm, and then 80 W / cm high pressure mercury lamp (eye graphics ( Manufactured by K.K.), the lamp height is 8 cm,
Ultraviolet rays were irradiated under the condition of a conveyor speed of 10 m / min, and the number of times of irradiation required to make the coating film surface tack-free was evaluated. The UV irradiation dose per time is about 80 mJ / c.
It was m ² .

(2) Gel fraction: A coating film was prepared by passing under the lamp four times under the above curing conditions. The cured coating film (weight: W ₁ ) peeled from the glass plate was refluxed in methyl ethyl ketone at 80 ° C. for 3 hours, dried at 100 ° C. for 1 hour, and then weighed (weight: W ₂ ) to obtain a gel fraction (%). ) = W ₂ ÷ W ₁
× 100 was obtained.

(3) Surface hardness: A coating film was prepared in the same manner as in the above gel fraction evaluation, and the pencil hardness was measured according to JIS K-5400.

Example 1 2 3 Composition ratio (numerical values are parts by weight) Reactant (A ₁ −) 20 obtained in Synthesis Example 1 Reactant (A ₂ −) 50 obtained in Synthesis Example 2 Obtained in Synthesis Example 3 Reaction product (A ₂ −) 30 KAYARAD DPHA * 1 80 25 60 KAYARAD R-551 * 2 25 10 N-ethylmaleimide N, N-4,9-dioxa-1,12-bismaleimidododecane ○ Test UV-curable (Times) 2 3 2 Gel fraction (%) 98.0 98.5 98.7 Pencil hardness 5H 3H 4H

Table 2 Comparative Example 1 2 ○ Composition ratio (numerical values are parts by weight) Reactant (A ₁ −) obtained in Synthesis Example 1 Reactant (A ₂ −) obtained in Synthesis Example 2 Obtained in Synthesis Example 3 Reaction product (A ₂ −) KAYARAD DPHA * 1 70 KAYARAD R-551 * 2 50 N-ethylmaleimide 30 N, N-4,9-dioxa-1,12-bismaleimidododecane 50 ○ Test UV curability (times) 10 or more 6 Gel fraction (%) 0 47 Pencil hardness-less than 4B

Note) * 1. KAYARAD DPHA: a mixture of dipentaerythritol penta and hexaacrylate manufactured by Nippon Kayaku Co., Ltd. * 2. KAYARAD R-551: Nippon Kayaku Co., Ltd.
Manufactured by Bisphenol A poly (n≈4) ethoxydiacrylate.

From the results shown in Table 1, the resin composition of the present invention can be easily cured by irradiation with ultraviolet rays to form a uniform and transparent coating film, even though no photopolymerization initiator is used. Is clear.

[0104]

Industrial Applicability The novel resin composition of the present invention cures at a practical light irradiation amount even in the absence of a photopolymerization initiator,
Moreover, a coating film having a high gel fraction can be formed.

Continued front page    F-term (reference) 4F071 AA33X AA36X AA53 AH12                       AH19 BA02 BB01 BB12 BC02                 4J027 AB10 AC06 AG04 AG12 AG27                       CD01 CD08 CD09 CD10                 4J034 BA02 BA05 BA09 CA02 CA04                       CA22 CB01 CB03 CB07 CB08                       CC33 CC38 CC44 CC52 CC62                       CD01 CD05 FA02 FB01 FB04                       FD09 FE01 HA07 HC03 HC12                       HC17 HC46 HC52 HC54 RA05                       RA07 RA08

Claims (6)

[Claims] 1. A maleimide derivative (A ₁ ) and / or a reaction which is a reaction product (X) of a monocarboxylic acid (a) having a maleimide group and a compound (b) having one epoxy group in one molecule. A urethane-modified maleimide derivative (A ₂ ) which is a reaction product of the compound (X), the organic polyisocyanate compound (c), and the polyol compound (d) as an optional component, and other than the components (A ₁ ) and (A ₂ ) A resin composition comprising a polymerizable compound (B). 2. The resin composition according to claim 1, wherein the polymerizable compound (B) is at least one compound selected from the group consisting of compounds having a (meth) acryloyl group, a vinyl ether group or an N-vinyl group. 3. A compound having a (meth) acryloyl group is a (poly) ester (meth) acrylate (B-1-).
1), urethane (meth) acrylate (B-1-2),
Epoxy (meth) acrylate (B-1-3), (poly) ether (meth) acrylate (B-1-4), alkyl (meth) acrylate or alkylene (meth) acrylate (B-1-5), aromatic ring The resin according to claim 2, which is one or more compounds selected from the group consisting of a (meth) acrylate compound (B-1-6) having an alicyclic structure and a (meth) acrylate (B-1-7) having an alicyclic structure. Composition. 4. A compound having a vinyl ether group, an alkyl vinyl ether (B-2-1) in which the other end may be substituted with a halogen atom or a hydroxyl group, and a cycloalkyl group in which the other end may be substituted with a halogen atom or a hydroxyl group. Alkyl vinyl ether (B-2-2), at least one selected from the group consisting of an alkyl group, a cycloalkyl group and an aromatic group in which a vinyl ether group is bonded to an alkylene group and which may further have a substituent, and an ether 1 selected from the group consisting of monovinyl ether, divinyl ether and polyvinyl ether (B-2-3) having a structure in which they are bonded via at least one bond selected from the group consisting of a bond, a urethane bond and an ester bond. The resin composition according to claim 2, which is one or more compounds. 5. The resin composition according to claim 1, which contains a photopolymerization initiator (C). 6. A cured product of the resin composition according to claim 1.