JPH09263635A - Curable resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an one-pack curable resin composition excellent in adhesion to various base materials, long in pot life, and excellent in long-term preservability. SOLUTION: This curable resin composition comprises (A) a compound bearing at least two substituents selected from the group consisting of acyloxyimino, N-formylated aromatic amino, N-acylated aromatic amino, nitrobenzyl carbamate and alkoxybenzyl carbamate groups, (B) a compound selected from the group consisting of benzoquinone, naphthoquinone, anthraquinone and phenanthraquinone, and a compound bearing the above compound as a substituent, and (C) a compound bearing at least one substituent selected from the group consisting of epoxy, isocyanato and carbonate groups, [and (D) a photo- free-radical generator, (and (E) a vinyl group-bearing polymerizable compound)].

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel curable resin composition (hereinafter abbreviated as a curable resin composition or a curable composition) which is cured by light, and includes a coating agent, an ink and an adhesive. It is widely used as an agent, a resist, an insulating material, a casting agent, and the like.

[0002]

2. Description of the Related Art A conventional curable resin composition comprises an acrylic monomer or oligomer and a polymerization initiator.

[0003]

The above-mentioned conventional curable composition exhibits excellent photocurability, but has a large volume shrinkage upon curing, and is particularly suitable for non-absorbent substrates such as glass, plastic and metal. On the other hand, it has the problem of poor adhesion. In order to solve this problem, a two-pack type composition in which an epoxy compound is present in a curable resin composition and an epoxy curing agent is blended at the time of use has been proposed, but these are hardeners before use. Must be blended, and there is a problem in workability. In order to improve this workability, by using a type with a slow reaction rate as an epoxy curing agent, 1
Liquefaction has been proposed, but this type has a problem that the composition lacks long-term storage stability.

[0004]

Means for Solving the Problems The present inventors have developed a curable composition having excellent curability, excellent adhesion to various substrates, long pot life, excellent storage stability and good workability. As a result of intensive studies to find out, the present invention has been accomplished.

That is, the present invention is at least selected from the group consisting of (A) an acyloxyimino group, an N-formylated aromatic amino group, an N-acylated aromatic amino group, a nitrobenzylcarbamate group and an alcooxybenzylcarbamate group. A compound containing two substituents and (B) p
-Benzoquinone, o-benzoquinone, 1,4-naphthoquinone, 1,2-naphthoquinone, 2,6-naphthoquinone,
1,2-anthraquinone, 1,4-anthraquinone,
A compound selected from the group consisting of 1,2-phenanthraquinone, 1,4-phenanthraquinone, and 3,4-phenanthraquinone, a compound containing the compound as a substituent, a (C) epoxy group, and an isocyanate. -Based curable resin composition (claim 1), (A), (B), (C) and (D) containing as a main component a compound having at least one substituent selected from the group consisting of a group and a carbonate group. A curable resin composition containing a photoradical generator as a main component (claim 2),
And (A), (B), (C), (D) and (E)
A curable resin composition (Claim 3) containing a polymerizable compound having a vinyl group as a main component.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION It was found that the compound (A) produces an amine upon irradiation with light, and the produced amine rapidly reacts with the compound (B) to form a crosslinked body. At this time, when a hydroxyl group is generated in the crosslinked product and the compound (C) is allowed to coexist, the compound (C) reacts with the amine generated by light or the hydroxyl group generated by the reaction between the amine and the compound (B), It was also found that a strong crosslinked body was formed.
Further, they have found that the combined use of the compound (E) in this system has the effect of further increasing the crosslinking efficiency. Also (D)
The photoradical generator facilitates generation of an amine from the compound (A) and facilitates polymerization / crosslinking of the compound (E).

Specific examples of the compound (A) having at least two acyloxyimino groups include:
O, O′-diactophenone oxime succinate, O,
O′-dinaphthophenone oxime succinate, benzophenone oxime acrylate-styrene copolymer and the like can be mentioned.

Examples of the method for synthesizing the compound having at least two acyloxyimino groups include a method of synthesizing a carboxylic acid halide and an oxime, and a method of synthesizing a carboxylic acid and an oxime directly in the presence of dicyclohexylcarbodiimide. In order to obtain a polymer having an acyloxyimino group, oxime acrylate can be synthesized by the above method and homopolymerized or copolymerized with another monomer. Alternatively, a polymer containing a carboxyl group may be synthesized, and then the target product may be synthesized by the above method.

Specific examples of the compound having an N-formylated aromatic amino group and an N-acylated aromatic amino group include:
For example, di-N- (p-formylamino) diphenylmethane, di-N (p-acetylamino) diphenylmethane, di-N- (p-benzamido) diphenylmethane,
4-formylaminotoluylene, 4-acetylaminotoluylene, 2,4-diformylaminotoluylene, 1-
Formylaminonaphthalene, 1-acetylaminonaphthalene, 1,5-diformylaminonaphthalene, 1-formylaminoanthracene, 1,4-diformylaminoanthracene, 1-acetylaminoanthracene, 1,4
-Diformylaminoanthraquinone, 1,5-diformylaminoanthraquinone, 3,3'-dimethyl-4,
4′-diformylaminobiphenyl, 4,4′-diformylaminobenzophenone and the like can be mentioned.

As a method for synthesizing such a compound having an N-formylated aromatic amino group or an N-acylated aromatic amino group, for example, aromatic diisocyanate and formic acid, acetic acid, propionic acid, benzoic acid or the like can be used. Reaction, a method of synthesizing an aromatic amine and the above carboxylic acid using dicyclohexylcarbodiimide as a condensing agent, a method of synthesizing from an aromatic amine and a carboxylic acid halide of the above carboxylic acid, and the like can be mentioned.

Specific examples of the compound having a nitrobenzylcarbamate group and an alcoholoxybenzylcarbamate group include, for example, bis [{(2-nitrobenzyl) oxy} carbonyl] diaminodiphenylmethane and 2,4-
Di [{(2-nitrobenzyl) oxy} amidotoluylene], bis [{(2-nitrobenzyl) oxy} carbonyl] hexane-1,6-diamine], m-xylidine [{(2-nitro-4-chlorobenzyl] ) Oxy} amide], α, α′-dimethyl-3,5-dimethoxybenzyl carbamate and the like.

As a method for synthesizing such a compound having a nitrobenzyl carbamate group or an alcoholoxybenzyl carbamate group, for example, a polyfunctional aromatic, finger ring or aliphatic polyisocyanate and a benzyl alcohol containing a nitro group or a methoxy group are used. It is synthesized by the reaction. At this time, a catalyst such as triethylamine or dibutyltin dilaurate can be used as the catalyst.

Specific examples of the compound (C) having at least one epoxy group (hereinafter referred to as epoxy compound) include, for example, DER331J, DER661J,
(These are manufactured by Dow Chemical Co., Ltd.), Epicron 800 [manufactured by Dainippon Ink and Chemicals, Inc.], Epicoat 1001, Epicoat 828 [these are manufactured by Yuka Shell Epoxy Co., Ltd.]
Bisphenol A type epoxy resin; DER431
(Above, Dow Chemical Co., Ltd.), Araldite EPN11
38 (manufactured by Ciba Geigy), Epicoat 154 [above,
Yuka Shell Epoxy Co., Ltd.] and other novolac type epoxy resins; Syracure 6100, ERL2256 (above, Union Carbide Co.), Araldite CY-1.
75 (above, manufactured by Ciba Geigy), Chisso Knox 09
0, alicyclic epoxy resin such as Chisso nox 301 (above, manufactured by Chisso Corporation); 1,6-hexanediol diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, Aliphatics such as glycerin diglycidyl ether, trimethylolpropane diglycidyl ether, neopentyl glycol diglycidyl ether, propylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether Polyhydric glycidyl ether of polyhydric alcohol; bisphenol A alkylene oxide adduct diglycidyl ether, bisphenol F
Aromatic polyhydric alcohol derivatives such as alkylene oxide adduct diglycidyl ether and bisphenol S alkylene oxide adduct diglycidyl ether; diglycidyl p-oxybenzoic acid, dimer acid glycidyl ester, tetrahydrophthalic acid diglycidyl ester, phthal Glycidyl esters such as acid diglycidyl ester and hexahydrophthalic acid diglycidyl ester; N, N-diglycidylaniline, tetraglycidyldiaminodiphenylmethane, triglycidyl p
-Glycidyl amines such as aminophenol; triglycidyl isocyanurate, and heterocyclic epoxy resins such as hydantoin type epoxy resins. Further, the epoxy group part (meth) acrylate of the novolac type polyfunctional epoxy resin is also included.

Specific examples of the compound having at least one isocyanate group in the compound (C) (hereinafter referred to as urethane prepolymer) include, for example, toluene diisocyanate, xylene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, 1,5. -Polyisocyanates such as naphthalene diisocyanate, isophorone diisocyanate and triphenylmethane triisocyanate and their excess amounts with (poly) ethylene glycol, (poly) propylene glycol, 1,6-hexanediol, neopentyl glycol, trimethylolpropane Ure having an isocyanate residue at the molecular end obtained by reaction with polyols such as glycerin, glycerin, pentaerythritol, and dipentaerythritol. Emissions prepolymers [e.g., manufactured by Sanyo Chemical Industries, Ltd. of SANPRENE P-665, Sunprene S
EL-3 etc.] and the like.

Among the compounds (C), compounds having at least one carbonate group (hereinafter referred to as carbonate compounds) include various epoxy compounds as described above at a temperature of about 50 to 110 ° C. using tetrabutylammonium salt as a catalyst.
By reacting with carbon dioxide under normal pressure, a carbonate obtained by converting the epoxy group into a corresponding cyclic carbonate group, and at this time obtained by controlling the reaction rate of carbon dioxide, the cyclic at the end Examples thereof include compounds having a carbonate group and an epoxy group. Specific examples include bisphenol A di (2-oxy-1,3-dioxolan-4-yl) ether.

Specific examples of the compound (C) having at least one oxazoline group (hereinafter referred to as oxazoline compound) include bisoxazoline and hexamethylenebisoxazoline.

The photoradical generator (D) is one which easily generates radicals upon irradiation with light, and specific examples thereof include 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-. On, 1-hydroxycyclohexyl phenyl ketone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-methyl-1 -(4-
(Methylthio) phenyl) -2-morpholinopropane-
1,4-phenoxydichloroacetophenone, 4- (2
-Hydroxyethoxy) -phenyl (2-hydroxy-
2-propyl) ketone, pt-butyldichloroacetophenone, pt-butyltrichloroacetophenone,
Acetophenones such as p-dimethylaminoacetophenone; Benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, benzyl dimethyl ketal; benzophenone, benzophenone methyl ether, benzoyl benzoate Acid, methyl benzoylbenzoate, hydroxybenzophenone, 4-phenylbenzophenone, 3,3′-dimethyl-4-methoxybenzophenone, 3,3′-bis (N, N-diethylamino) benzophenone, 4,4′-bis (N , N-diethylamino) benzophenone, 4 ′, 4 ″ -diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophen Benzophenones such as 4-benzoyl-4'-methyldiphenyl sulfide and acrylated benzophenone; thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropyl Xanthones such as thioxanthone, 2-chlorothioxanthone, and 2,4-dichlorothioxanthone; diketones such as diacetyl and benzyl; 2-ethylanthraquinone,
Examples thereof include quinones such as 2-t-butylanthraquinone, 2,3-diphenylanthraquinone, 1,2-benzanthraquinone, octamethylanthraquinone, camphorquinone, dibenzosuberone, and 9,10-phenanthrenequinone.

Specific examples of the polymerizable compound (E) containing a vinyl group include ethylene glycol di (meth) acrylate, butanediol di (meth) acrylate,
Hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polytetrahydrofuran glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate (Meth) acrylate of polyhydric alcohol; Trade name Aronix M-12
00, Aronix M-6100, Aronix M-6
300, Aronix M-7100, Aronix M-
8030 [or more, manufactured by Toagosei Chemical Industry Co., Ltd.], trade name Kayarad DPCA-120 [or more, Nippon Kayaku Co., Ltd.
(Meth) acrylates such as
6-hexanediol diglycidyl ether di (meth)
In one molecule such as acrylate, trimethylolpropane triglycidyl ether tri (meth) acrylate, isocyanuric acid triglycidyl ether (meth) acrylate, (meth) acrylate of novolac type epoxy resin, (meth) acrylate of bisphenol A type epoxy resin A (meth) acrylate of a compound having at least two epoxy groups in; isophorone diisocyanate, diphenylmethane diisocyanate, trimethylhexamethylene diisocyanate, tolylene diisocyanate, a reaction product of hexamethylene diisocyanate and a hydroxy group-containing (meth) acrylate, and these The reaction product of the terminal isocyanate prepolymer consisting of polyisocyanate and polyol and the hydroxy group-containing acrylic monomer It is. For example, polyisocyanate compounds known under the trade names Sumijour N (a buret derivative of hexamethylene diisocyanate) and Sumijour L (a modified trimethylolpropane of tolylene diisocyanate) [above, manufactured by Sumitomo Bayer Urethane Co., Ltd.] are hydroxy. A reaction product to which a group-containing (meth) acrylate is added can be used. As the hydroxy group-containing (meth) acrylate referred to here, those mentioned in the above specific examples of the (meth) acrylate can be used.

Furthermore, in the curable resin composition of the present invention, if necessary, a condensation crosslinking catalyst, a thermal polymerization inhibitor, a filler, a coloring agent such as a dye or a pigment, a heat stabilizer, an adhesion promoter, and a plasticizer. A pigment such as silica or talc, a leveling agent that imparts coating suitability, or the like may be added.

Next, the composition ratio will be described. The acyloxyimino group, N-formylated aromatic amino group, N-acylated aromatic amino group, nitrobenzylcarbamate group, and alcooxybenzyl group in the compound (A) are respectively a, b, c, and d and e, the number of moles of the quinone group in the compound (B) is f, and the number of moles of the epoxy group isocyanate group, oxazoline group, and carbonate group in the compound (C) are g, h, i, and j, respectively. Compound (A), compound (B), compound (C), compound (D),
When the weight of the compound (E) is v, w, x, y, z, respectively, the compound (A), the compound (B), the compound (C),
Alternatively, in the compounding system of the compound (A), the compound (B), the compound (C) and the compound (D), (a + b + c + d + e + f
/ 2): (2g + h + i + 2j) = 1: 0.2 to 3,
(A + b + c + d + e): f = 1: 0.1 to 3, (v +
w + x + y): y = 100: 40 is preferable. In the compounding system of the compound (A), the compound (B), the compound (C), the compound (D) and the compound (E), (a + b + c + d + e + f)
/ 2): (2g + h + i + 2j) = 1: 0.2 to 3,
(A + b + c + d + e): f = 1: 0.1 to 1.5, (v
+ W + x + y + z): y = 100: 40 is preferable.

The cured product of the present invention can be applied to any thickness by a dip method, a spray method, a roll coating method, a flow coating method, a spin coating method, an applicator method, a bar coating method or the like. At this time, if necessary, a solvent capable of dissolving the curable composition can be used. For example, toluene, acetone, methyl ethyl ketone, tetrahydrofuran, acetonitrile, dimethylformamide, methylene chloride, dichloroethane, diethylene glycol dimethyl ether, dimethylformamide and the like can be mentioned. These solvents may be used alone or as a mixture.

Examples of the light source for light irradiation include a high pressure mercury lamp, a low pressure mercury lamp, a metal halide lamp, a xenon lamp, a fluorescent lamp, a tungsten lamp, an argon laser, and a helium cadmium laser.

After the light irradiation, the reaction can be promoted by heating if necessary. The temperature is usually 30 to 180 ° C, preferably 80 to 150 ° C.

Next, a method of using the curable resin composition of the present invention will be described. First, the curable resin composition is applied onto a substrate by the method described above, and the solvent is removed by heat drying or hot air drying as necessary to form a coating film on the substrate. After that, light irradiation is performed. If necessary, post-heating may be performed.

When forming a pattern, the dry coating film is irradiated with light through a negative mask or a positive mask. Then, the unexposed portion is developed using a developing solution. For the development, for example, an organic solvent such as 1,1,1-trichloroethane, toluene, methyl ethyl ketone, butyl carbitol, triethylene glycol dimethyl ether is used. After development, if necessary, post-exposure and post-heating may be performed.

[0026]

EXAMPLES Next, the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

Synthesis Example-1 (Synthesis of SDAPO) 18 g of pyridine and 30 g of benzophenone oxime were put in 100 ml of methylene chloride, and methylene chloride 2 was added at room temperature.
A liquid in which 00 ml and 12.4 g of succinic acid chloride were dissolved was added dropwise. This mixture was reacted at 40 ° C. for 2 hours, filtered, and after removing methylene chloride, recrystallized with a toluene-cyclohexane mixed solvent, and O, O′-diacetophenonone succinate (SDAPO) (mp = 15)
5-158 ° C) was obtained.

Synthesis Example-2 (Synthesis of AAPO-St Copolymer) Methylene chloride 300
18 g pyridine and 30 benzophenone oximes in ml
g, and acrylic acid chloride 13.6g at room temperature
Was dripped. The mixture was reacted at 40 ° C. for 2 hours, filtered, methylene chloride was removed, and recrystallized from cyclohexane to give benzophenone oxime acrylate (AAP).
O) was obtained. Obtained AAPO 11.6 g, styrene 1
8.45 g, lauryl mercaptan dodecanethiol 1.1 ml as a chain transfer agent, 2,2 'as a polymerization initiator
-Azobisisobutyronitrile (AIBN) 0.09 g
Was blocked from light in 30 ml of benzene, and solution polymerization was carried out at 60 ° C. for 14 hours. Re-precipitation was performed three times with a THF-n-hexane system to obtain a benzophenone oxime acrylate-styrene copolymer (AAPO-St copolymer). The number average molecular weight of this copolymer was 5,200.

Synthesis Example-3 (Synthesis of BDODE) 4.75 g of bisphenol A type epoxy resin (Epicoat 828 manufactured by Yuka Shell Epoxy Co., Ltd.) was added to 30 ml of toluene.
It was dissolved therein, and 0.81 g of tetrabutylammonium bromide as a catalyst was added thereto. While blowing carbon dioxide at a flow rate of 40 ml / min into it, at 7
The reaction was performed for 0 hours. The product precipitated in the reaction solution was filtered, washed with water and then washed with n-hexane to give bisphenol A.
Di (2-oxy-1,3-dioxolan-4-yl) ether (BDODE) was obtained.

Synthesis Example-4 (Synthesis of DFADM) 25 g of 4,4'-diphenylmethane diisocyanate was dissolved in 400 ml of toluene, 10.1 g of formic acid was added, and the mixture was reacted at 80 ° C. for 2 hours. A white product was precipitated as the reaction proceeded. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, then the product was filtered and washed with methanol to obtain di-N- (P-formylamino) diphenylmethane (DFADM).

Synthesis Example-5 (Synthesis of DBADM) 19.8 g of diaminodiphenylmethane was dissolved in 400 ml of tetrahydrofuran to prepare triethanolamine 2
2.3 g was added, and 30.9 g of benzoyl chloride was added dropwise at 2 to 5 ° C while stirring under ice cooling. After completion of the dropping, the reaction was carried out at 5 ° C. for 6 hours. The reaction mixture was added to 1000 ml petroleum ether, the precipitate was filtered, washed with methanol, and di-N- (P-benzamido) diphenylmethane (DBA
DM) was obtained.

Synthesis Example 6 (Synthesis of BNCA) 15.3 g of 2-nitrobenzyl alcohol was added to toluene 3
It was dissolved in 00 ml, 8.4 g of hexamethylene diisocyanate was added, and a catalytic amount of dibutyl tin dilaurate was further added, followed by reaction at 80 ° C. for 4 hours. The product precipitated in the reaction solution was filtered, washed with toluene, and bis-
[{(2-Nitrobenzyl) oxy} carbonyl] hexane-1,6-diamine (BNCA) was obtained.

Examples 1 to 5 and Comparative Examples 1 to 4 The compounds having the compositions shown in Table 1 were uniformly blended to prepare Examples 1 to 5
And the curable composition of Comparative Examples 1-4 was obtained. This curable resin composition was applied to a glass plate with an applicator to obtain 10
It was applied to a film thickness of −15 μm and dried at 40 ° C. for 30 minutes. Next, after irradiation with light of 500 mJ / cm ² by a high-pressure mercury lamp, it was heated at 150 ° C. for 30 minutes to obtain a cured film. The surface tack of the thus-obtained cured film was measured by the touching method and used as an index of curability. Further, the cured film on the glass plate was immersed in dichloroethane for 30 minutes. The weight before immersion is W ₁ , the weight after immersion is W ₂ , and the weight of the glass plate before application is W ₃ (W ₁ −W ₃ ) − (W ₂ −W ₃ ) × 1
00 / (W ₁ -W ₃₎ calculates from dissolution rate, and the results are shown in Table 2. Furthermore, this curable resin composition was placed in a constant temperature bath at 40 ° C. for 14 days, and the viscosity after 14 days was measured by a rotational viscometer. The viscosity at the time of blending was V ₁ , the viscosity after 14 days at 40 ° C. was V _2, and (V ₂ −V ₁ ) × 100 / V ₁ was summarized in Table 2 as the viscosity increase rate.

[0034]

[Table 1]

Acrylate-1: Aronix M-6300 [manufactured by Toagosei Co., Ltd.] Acrylate-2: Acrylate of bisphenol A type epoxy resin Acrylate-3: Trimethylolpropane triacrylate acrylate-4: Neopentyl glycol diacrylate urethane Prepolymer: Sampren SEL-3 [manufactured by Sanyo Kasei Co., Ltd.] Hardener-1: Ethylenediamine Hardener-2: Methylene-bis-O-chloroaniline Initiator-1: Benzophenone Initiator-2: Irgacure 651 Solvent: Dichloroethane

[0036]

[Table 2]

[0037]

EFFECTS OF THE INVENTION The curable composition of the present invention has excellent adhesiveness to various substrates, is one-part and has good workability, has a long pot life, and has excellent long-term storage stability. Have
In addition, it exhibits excellent solvent resistance, chemical resistance, and heat resistance due to its low elution rate, making it suitable for paints, coating agents, inks,
It is effective for applications such as resists and insulating materials.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C08G 65/00 NQC C08G 65/00 NQC G03F 7/004 503 G03F 7/004 503 7/028 7 / 028 7/038 7/038 503 503

Claims (4)

[Claims] 1. (A) an acyloxyimino group, an N-formylated aromatic amino group, an N-acylated aromatic amino group,
A compound having at least two substituents selected from the group consisting of a nitrobenzylcarbamate group and an alkooxybenzylcarbamate group, (B) p-benzoquinone, o-benzoquinone, 1,4-
Naphthoquinone, 1,2-naphthoquinone, 2,6-naphthoquinone, 1,2-anthraquinone, 1,4-anthraquinone, 1,2-phenanthraquinone, 1,4-phenanthraquinone, 3,4-phenanthate A compound selected from the group consisting of laquinone and a compound having the same as a substituent, and (C) a compound having at least one substituent selected from the group consisting of an epoxy group, an isocyanate group, an oxazoline group and a carbonate group. Curable resin composition containing the main component. 2. (A) Acyloxyimino group, N-formylated aromatic amino group, N-acylated aromatic amino group,
A compound having at least two substituents selected from the group consisting of a nitrobenzylcarbamate group and an alkooxybenzylcarbamate group, (B) p-benzoquinone, o-benzoquinone, 1,4-
Naphthoquinone, 1,2-naphthoquinone, 2,6-naphthoquinone, 1,2-anthraquinone, 1,4-anthraquinone, 1,2-phenanthraquinone, 1,4-phenanthraquinone, 3,4-phenanthate A compound selected from the group consisting of laquinone and a compound having the same as a substituent, (C) a compound having at least one substituent selected from the group consisting of an epoxy group, an isocyanate group, an oxazoline group and a carbonate group, and (D) A curable composition containing a photoradical generator as a main component. 3. (A) an acyloxyimino group, an N-formylated aromatic amino group, an N-acylated aromatic amino group,
A compound having at least two substituents selected from the group consisting of a nitrobenzylcarbamate group and an alkooxybenzylcarbamate group, (B) p-benzoquinone, o-benzoquinone, 1,4-
Naphthoquinone, 1,2-naphthoquinone, 2,6-naphthoquinone, 1,2-anthraquinone, 1,4-anthraquinone, 1,2-phenanthraquinone, 1,4-phenanthraquinone, 3,4-phenanthate A compound selected from the group consisting of laquinone and a compound having the same as a substituent, (C) a compound having at least one substituent selected from the group consisting of an epoxy group, an isocyanate group, an oxazoline group and a carbonate group, A curable resin composition containing D) a photoradical generator and (E) a polymerizable compound having a vinyl group as main components. 4. The composition according to claim 2 or 3, wherein the photoradical generator is acetophenone, benzophenone and derivatives thereof.