JPH0411609A - Radiation-curable composition and its cured product - Google Patents

Abstract

PURPOSE:To obtain the title composition which is excellent in curability and can give a cured product excellent in adhesiveness and solvent resistance by mixing a (meth)acrylate compound and/or an epoxy resin with a specified vinyl ether compound and a specified sulfonium salt. CONSTITUTION:A (meth)acrylate compound and/or an epoxy resin (e.g. Epikote 828, an epoxy resin of Yuka-Shell Epoxy Ltd.), a vinyl ether compound having at least two vinyl ether groups per molecule (e.g. triethylene glycol divinyl ether), a sulfonium salt of the formula [wherein R1 is H, alkyl, Y-C(O)- (wherein Y is alkyl, alkoxy, phenyl or phenoxy which may be substituted); R2 and R3 are each H, halogen or alkyl; Q and R4 are each (substituted) alkyl; and X is SbF6, PF6, AsF6 or BF4] and a photopolymerization initiator as an optional component.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to radiation-curable compositions, in particular (meth)acrylate compounds and/or epoxy resins, compounds containing at least two vinyl ether groups, specific The present invention relates to a radiation-curable composition containing a sulfonium salt and a photopolymerization initiator as an optional component.

(Prior art) In recent years, ultraviolet curable compositions have been actively studied for reasons such as resource saving, energy saving, improved workability, and increased productivity, and have been put to practical use as coating agents for various substrates, paint compositions, printing inks, etc. has been made into

(Problem to be solved by the invention) UV-curable coating agents and various paints have been put into practical use for reasons such as energy saving, improved workability, and improved productivity. There is a need for coatings and paints with higher productivity, and it is important to provide novel, useful, and rapidly curable radiation-curable compositions.

(Means for Solving the Problems) In order to solve the above problems, the present inventors conducted extensive research and succeeded in providing a radiation-curable composition with excellent curing properties by ultraviolet rays.

That is, the present invention provides: 1) A (meth)acrylate compound (A) and/or an epoxy resin (B), a vinyl ether compound (C) having at least two vinyl ether groups per molecule, represented by the general formula [I] This shows a radiation-curable composition Y-C- characterized by containing a sulfonium salt (D) and a photopolymerization initiator (E) as an optional component, where Y is an optionally substituted alkyl group. , represents an alkoxyl group, a phenyl group or a phenoxy group. R and R each independently represent hydrogen, halogen or an alkyl group.

Q 1R4 each independently represents an optionally substituted alkyl group. X is SbF, PF6゜AsF
or BF 4), and 2) a cured product of the composition described in 1) above.

In formula [I], R1 represents hydrogen, an alkyl group, or Y-〇-, and the alkyl group is a methyl group.

An alkyl group having 1 to 4 carbon atoms such as an ethyl group is preferred. Y
Y in -C- represents an optionally substituted alkyl group, alkoxyl group, phenyl group or phenoxy group, and the alkyl group or alkoxyl group has 1 to 4 carbon atoms.
An alkyl group or an alkoxyl group is preferred. Also, these alkyl groups.

When the alkoxyl group, phenyl group or phenoxy group has a substituent, the substituent is an alkyl group or alkoxyl group which may be substituted with an alkoxyl group, etc., or a substituent with an alkyl group, an alkoxyl group, a halogen, a nitro group, etc. Various groups such as a phenyl group, a phenoxy group, or a fluorinyl group, which may be substituted, may be mentioned. Specific examples of Y-〇- include acetyl group, methoxycarbonyl group, ethoxycarbonyl group, benzyloxycarbonyl group, benzoyl group, phenoxycarbonyl group, 1erl-butoxycarbonyl group, p-methoxybenzyloxycarbonyl group, 9-fluor Examples include olenylmethoxycarbonyl group.

R and R each independently represent hydrogen, halogen, or an alkyl group, and examples of halogen include fluorine, chlorine, bromine,
Examples include iodine (chlorine is particularly preferred), and the alkyl group is preferably an alkyl group having 1 to 4 carbon atoms.

Q and R4 each independently represent an alkyl group that may be substituted, such as an alkyl group having 1 to 4 carbon atoms or an alkyl group such as a methyl group.

Examples thereof include alkoxyl groups such as methoxy groups, and alkyl groups having 1 to 4 carbon atoms substituted with phenyl groups or naphthyl groups which may have substituents such as halogen and nitro groups.

In the present invention, (meth)acrylate compound (A) and/
Or use epoxy resin (B). As the (meth)acrylate compound (A), any known (meth)acrylate compound (A) may be used.
Acrylate compounds can also be used. For example 2
-Hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, ε-caprolactone modified product of 2-hydroxyethyl (meth)acrylate (e.g., manufactured by Daicel Chemical Industries, Ltd., Plaxel FA-1.FM-1) etc.), carpitol (meth)acrylate, 2-ethylhexyl (meth)acrylate,
Phenoxyethyl (meth)acrylate, phenoxypolyethoxy (meth)acrylate, phenyl glycidyl ether (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, nonylphenoxypolyethoxy (meth)acrylate, 1.6-hexanone (meth)acrylate, polyethoxy di(meth)acrylate of neopentyl glycol, hydroxypivalic acid neopentyl glycol di(meth)acrylate, polyprolene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, Di(meth)acrylate of ε-caprolactone adduct of neopentyl glycol hydroxypivalate (manufactured by Nippon Kayaku Co., Ltd., KAY
ARAD HK-220, HX-620), ■, di(meth)acrylate of 6-hexane dicrycidyl ether.

trimethylolpropane tri(meth)acrylate,
Trimethylolpropane polyproboxytri(meth)acrylate, glycerin polypropoxytri(meth)acrylate
Acrylate, polyethoxy di(meth)acrylate of bisphenol A, polyethoxy di(meth)acrylate of bisphenol F, pentaesritol tri(meth)acrylate, tris(hydroxyethyl)isocyanurate tri(meth)acrylate, tris(hydroxyethyl)isocyanurate ε- of tri(meth)acrylate, tris(hydroxyethyl)isocyanurate
caprolactone modified tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate,
Dipentaerythritol penta or hexa (meth)
Reactive monomers such as acrylates, epoxy resins (e.g. bisphenol A epoxy resin, bisphenol F
Type epoxy resin, phenol/novolac type epoxy resin, cresol/novolac type epoxy resin.

Trisphenol methane triglycidyl ether.

tris(2,3-epoxypropyl)isocyanurate,
Epoxy (meth)acrylate, which is a reaction product of rosin-modified epoxy resin) and (meth)acrylic acid, polyol compounds [e.g., ethylene glycol, neopentyl glycol, ■, 4-butanediol, propylene glycol, 1,4-cyclohexane diol, diol compounds such as 1,4-cyclohexane dimetatool, 1,6-hexanediol, polyether diol compounds such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyester diol compounds (e.g. phthalic acid, isophthalic acid) Tetrahydrophthalic acid, hexahydrophthalic acid.

(reaction products of tetrachlorophthalic acid, adipic acid, azelaic acid, sebacic acid, succinic acid, and acid anhydrides of the above acids with the above diol compounds, the above polyether diol compounds, etc.), polycarbonate diol compounds, lactone-modified diol compounds, etc. and organic polyisocyanates (e.g. toluene-24-diisocyanate, toluene-24-diisocyanate, toluene-24-diisocyanate,
2,6-diisocyanate and mixtures thereof, diphenylmethane-4,4'-diisocyanate, diphenylmethane-2,4'-diisocyanate and mixtures thereof, paraphenyl diisocyanate.

Biphenyl diisocyanate, 3,3'-dimethyl 4,4'-diphenylene diisocyanate, tetramethylene-14-diisocyanate, hexamethylene-1
, 6-diisocyanate, 2,2.4-1-limethylhexane-1,6-diisocyanate, lysine methyl ester diisocyanate, bis(isocyanate ethyl) fumarate, isophorone diisocyanate, ethylene diisocyanate, dodecane-1,2-diisocyanate, cyclobutane 13 -diisocyanate, cyclohexane-13-diisocyanate, hexahydrophenylene 1,4-diisocyanate, hexahydrophenylene-1,3-diisocyanate, and mixtures thereof)
and hydroxyl group-containing (meth)acrylates (e.g.
Hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate.

Polyurethane (meth)acrylate, which is a reaction product with dicarboxylic acid or its acid anhydride [e.g., maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, isophthalic acid, adipic acid, azelaic acid, sebacic acid, malonic acid and the corresponding acid anhydrides of these acids (if anhydrides are present)] Polyols (e.g. diethylene glycol, ethylene glycol, propylene glycol, butylene glycol, glycerin.

Trimethylolpropane, pentaerythritol.

Sorbitol, 1.6-hexanediol, 1.4cyclohexanediol, +4-cyclohexane dimetatool, 2.2-dimethyl-3-hydroxypropyl-
22-dimethyl-3-hydroxypropionate, etc.) and reactive oligomers such as polyester poly(meth)acrylate, polycarbonate di(meth)acrylate, etc. can be mentioned. these(
The meth)acrylate compound (A) can be used alone or in a mixture of two or more in any ratio.

Examples of the epoxy resin (B) include bisphenol A epoxy resin, bisphenol F epoxy resin, tetrabromobisphenol A epoxy resin, and phenol novolac epoxy resin.

Cresol/novolac type epoxy resin, brominated phenol/novolac type epoxy resin, trisphenolmethane triglycidyl ether.

Silicon-modified novolac type epoxy resin, urethane-modified bisphenol A type epoxy resin, polyhydric alcohol (e.g., 1,4-butanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, glycerin, trimethylolpropane, etc.) Examples include glycidyl ether and the like.

In the present invention, a vinyl ether compound (C) having at least two vinyl ether groups per molecule is used.

Examples of vinyl ether compounds are di-, tri- or tetra-functional organic polyols.

Included are vinyl ethers prepared by known methods from acetylene and a basic catalyst under high pressure. Specific examples include tripropylene glycol divinyl ether, triethylene glycol divinyl ether, 1,4-butanediol divinyl ether, cyclohexane], 4-dimethylol divinyl ether, divinyl ether of bisphenol A, the above-mentioned polyol compound and the above-mentioned Organic polyisocyanates and hydroxyl group-containing vinyl ether compounds (e.g. hydroxybutyl vinyl ether).

Tripropylene glycol monovinyl ether.

Tetraethylene glycol monovinyl ether.

Examples include polyurethane polyvinyl ether. The preferred range of the amount of the vinyl ether compound (C) used is 100% of the amount of the component (A) and/or component (B).
It is preferably 10 to 900 parts by weight, particularly preferably 25 to 300 parts by weight.

In the present invention, a sulfonium salt (D) represented by general formula [1] is used. Specific examples of the sulfonium salt (D) include benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate,
4-hydroxyphenylmethylsulfonium hexafluorophosphate, benzyl-4-hydroxyphenylmethylsulfonium tetrafluoroborate, benzylethyl-4-hydroxyphenylsulfonium hexafluoroantimonate, benzylethyl-4hydroxyphenylsulfonium hexafluorophosphate, Benzyl-4-methoxyphenylmethylsulfonium hexafluoroantimonate, benzyl-4-methoxyphenylmethylsulfonium hexafluorophosphate, benzyl-3-chloro-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or
hexafluoroantimonate), benzyl-3-methyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), 4-acetoxyphenylbenzylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), benzyl- 4-(methoxycarbonyloxy)phenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), 4-methoxybenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (
or hexafluorophosphate), benzyl-4-
(Ethoxycarbonyloxy)phenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), benzylmethyl-4-(phenoxycarbonyloxy)phenylsulfonium hexafluoroantimonate (or hexafluorophosphate), benzyl-4- (benzoyloxy)phenylmethylammonium hexafluoroantimonate (or hexafluorophosphate), benzyl-4-(benzyloxycarbonyloxy)phenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), dibenzyl-4-hydroxyphenyl Sulfonium hexafluoroantimonate (or hexafluorophosphate), p-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), o-nitrobenzyl-4-hydroxydiphenylmethylsulfonium hexafluoro antimonate (
or hexafluorophosphate), m-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), dinitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluoroantimonate) ), 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate (or hexafluorophosphate), α
-Naphthylmethyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), α-naphthylmethyl-4-(
methoxycarbonyloxy)phenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate), 4methoxyphenyldibenzylsulfonium hexafluorophosphate, p-chlorobenzyl 4-acetoxyphenylethylsulfonium hexafluoroarsenate, 4-methyl Benzyl 4-methoxycarbonyloxy-3-chlorophenylmethylsulfonium tetrafluoroborate.

Examples include p-methoxybenzyl-4-benzoyloxy-2-methylphenylmethylsulfonium hexafluorophosphate, 1,4-phenoxylphenyloxyphenyldimethylsulfonium hexafluoroantimonate, and the like.

These sulfonium salts (D) can be synthesized by known methods, such as the method described in JP-A-2-1470. Preferred sulfonium salts (D) include benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, l-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate (or hexafluorophosphate), p- Nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate (or hexafluorophosphate).

α-Naphthylmethyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate.

Examples include 4-penzyloxyphenoloxyphenyldimethylsulfonium hexafluoroantimonate and 4-(benzoyloxy)phenyldimethylsulfonium hexafluoroantimonate. The usage ratio of the sulfonium salt (D) in the composition of the present invention is 1 of the component (A) and/or the component (B) and the component (C).
0.01 to 20 parts by weight is preferred,
Particularly preferably 0.1 to 5 parts by weight.

Methods for curing the composition of the present invention include curing methods using radiation such as electron beams and ultraviolet rays, but it is preferable to cure by irradiating ultraviolet rays using a low-pressure or high-pressure mercury lamp or xenon lamp.

If desired, heat can be applied and heat curing can be combined. In the composition of the present invention, when component (A) is used and the composition is cured by ultraviolet light, a photopolymerization initiator (E) is used. As the photopolymerization initiator (E), any known photopolymerization initiator can be used, but one with good storage stability after blending is desirable. Examples of such photopolymerization initiators include benzoin, benzyl, benzoin methyl ether, benzoin isopropyl ether, acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-jethoxy-2-phenylacetophenone, 111- Dichloroacetophenone, 1-hydroxycyclohexylphenyl ketone, 2methyl-1-[4
-(methylthio)phenyl]2-morpholino-propan-1-one, N,N dimethylaminoacetophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-1er[-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone ,
2-aminoanthraquinone, 2,4-dimethylthioxanthone.

24-diethylthioxanthone, 2,4-diisopropylthioxanthone, acetophenone dimethyl ketal,
Benzophenone, methylbenzophenone, 4.4'
-dichlorobenzophenone, 4,4'bisdiethylaminobenzophenone, Michler's ketone and the like. These can be used alone or in combination of two or more.

Furthermore, these photoinitiators include N,N-dimethylaminobenzoic acid ethyl ester, N,N-dimethylaminobenzoic acid isoamyl ester, triethanolamine,
Known and commonly used photosensitizers such as triethylamine can be used alone or in combination with two or more. Preferred photoinitiators (E) include 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, benzophenone, 2-methyl 1-[4-(methylthio)phenyl]-2-morpholine -Propane-! -one, 2,4-diethylthioxanthone, and the like. The photopolymerization initiator (E) in the composition of the present invention
) is used in an amount of 0.00 parts by weight per 100 parts by weight of component (A).
5 to 50 parts by weight is preferred, particularly preferably 1 to 3 parts by weight.
5 parts by weight.

The composition of the present invention comprises (A) component and/or (B) component,
It is prepared by mixing and dissolving component (C), component (D), and optionally component (E).

The composition of the present invention may further include, if necessary, leveling agents such as silicone-based, fluorine-based, and acrylic copolymers, silane coupling agents, antifoaming agents, antioxidants, light stabilizers, 9 polymerization inhibitors, etc. 1 Colorants and diluents such as toluene, ethyl acetate, butyl acetate, n-butanol, methyl ethyl ketone.

Organic solvents such as ethyl cellosolve and ethyl cellosolve acetate can also be used.

The composition of the present invention can be applied to various substrates [e.g., paper, plastics (e.g., polycarbonate, acrylic).

ABS, polyester, polypropylene, etc.), metals (e.g., iron, copper, aluminum, zinc, chromium, tin, etc.), glass, wood, rubber, stone, concrete, etc.)] using various coating methods (e.g., spin cord). After coating to a film thickness of 1 to 30/71111 by method, spray painting, electrostatic coating 2-coat method, curtain flow coating method, gravure printing method, screen printing method, offset printing method, etc., UV rays are irradiated. By curing, the cured product of the present invention can be obtained. The composition of the present invention is useful as a surface coating material for various substrates, a paint, an overcoat agent for optical disks, an adhesive, and the like.

(Example) Hereinafter, the present invention will be specifically explained with reference to Examples.

Note that parts in the examples are parts by weight.

[Synthesis of (meth)acrylate compound (A) (Synthesis Example 1
．． 2)] Synthesis Example 1 Polytetramethylene glycol (molecular weight 2000) 70
0 parts, 67.6 parts of neopentyl glycol, and 444.6 parts of isophorone diisocyanate were charged, and the reaction was carried out at 80°C for about 10 hours until the NCO group in the reaction solution became 6.9% by weight. . Next, 244 parts of 2-hydroxyethyl acrylate and 0.7 parts of methoquinone were charged, and the reaction was carried out at 80°C for about 15 hours until the NGO group in the reaction solution became 0.3% by weight or less. ) 1456 parts were obtained.

Synthesis Example 2 Bisphenol A epoxy resin (manufactured by Yuka Shell Epoxy Co., Ltd., epoxy equivalent 175. Epicote 828)
350 parts of acrylic acid, 135.4 parts of acrylic acid, 2.4 parts of triphenolstibine, and 0.2 parts of methoquinone were added, and at 95°C, the acid value (■
The reaction was carried out for about 24 hours until the amount of 488 parts of epoxy acrylate (A=2) was obtained.

[Synthesis of sulfonium salt (D) (Synthesis Examples 3 to 7) 1 Synthesis Example 3 40 g (0.15 mol) of benzyl-4-hydroxyphenylmethylsulfonium chloride was dissolved in methanol 36
K P F 627.6 g (0,
15 mol) is added. Stir for an additional hour. The reaction solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried, and concentrated. 48.5 g of white crystals of benzyl-4-hydroxylphenylmethylsulfonium hexafluorophosphate (Ill) were obtained from the residue.

Synthesis Example 4 3.12 g (0.01 mol) of p-nitrobenzyl-4-hydroxyphenylmethylsulfonium chloride was dissolved in 300 ml of methanol, and while stirring, 2.
At 5° C., 62.75 g (0.01 mol) of KSbF are added.

Thereafter, in the same manner as in Synthesis Example 3, 4.04 g of white crystal p-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimone-1-(D2) was obtained.

Synthesis Example 5 3.17 g (0.01 mol) of α-naphthylmethyl-4-hydroxyphenylmethylsulfonium chloride was dissolved in 300 ml of methanol, and while stirring, 2
At 5°C 1.84 g of K P F s (0.1 mol of O) are added. Thereafter, white crystal α-naphthylmethyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate (D-3) was obtained in the same manner as in Synthesis Example 3.
23g was obtained.

Synthesis Example 6 4-benzyloxycarbonyloxyphenyldimethylsulfonium methylsulfate 4g (0.01 mol) was dissolved in 250 ml of methanol, and while stirring, 62.75 g (0.0
1 mol). Thereafter, in the same manner as in Synthesis Example 3, white crystals of 4-penzyloxyphenoloxyphenyldimethylsulfonium hexafluoroantimonate (
D-4) 4.22g was obtained.

Synthesis Example 7 3.12 g (0.01 mol) of m-nitrobenzyl-4-hydroxyphenylmethylsulfonium chloride was dissolved in 300 ml of methanol and heated at 25°C with stirring.
, K P F 61.84 g (0.01 mol) are added. Thereafter, in the same manner as in Synthesis Example 3, a field of light yellow crystals was obtained.
Nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate (D-5) 3.18
I got g.

Examples 1 to 6, Comparative Example 1.2 The composition of the present invention was blended, dissolved and mixed according to the composition shown in Table 1, and then coated by roll coating to a film thickness of 51A.
Apply oil-based ink on the paper so that
/ffl, 1 lamp, parallel reflection type) to cure the film, and evaluate its curability.

Next, the adhesiveness and solvent resistance of the cured product were evaluated.

The evaluation methods for the above-mentioned curability, adhesion, and solvent resistance are as follows. These evaluation results are shown in Table 1.

Evaluation method [Curability] Curability was evaluated by rubbing the ultraviolet irradiated surface with a finger and using the amount of ultraviolet rays (mJ/aJ) that did not cause scratches on the irradiated surface as the curing dose.

[Adhesion] A peeling test was conducted using cellotape (registered trademark) on the surface of the cured film to evaluate adhesion.

○...Peeling occurs between paper and oil-based ink.

×...Peeling occurs between the cured film and the oil-based ink.

[Solvent Resistance] The surface of the cured film was rubbed 10 times with gauze impregnated with methanol, the condition of the surface was observed, and the solvent resistance was evaluated.

O: No change in surface gloss of cured film.

X......// is gone.

Made of genuine oil-based shell epoxy, bisphenol A type epoxy resin.

■Made of oil-based shell epoxy■, phenol novolac type epoxy resin.

Photopolymerization initiator manufactured by Ciba Geigy.

Car■ Acrylate compounds (A-1) and (A-2) have high viscosity and are difficult to apply alone, so in Comparative Examples 1 and 2, tripropylene glycol diacrylate or hydroxypivalic acid neo Pentyl glycol diacrylate was used as a diluent.

Examples 7 to 11 As the sulfonium salts, experiments were conducted using the following sulfonium salts synthesized in the same manner as described in the synthesis example above, and in the same manner as in Example 1. The same results as in Example 1 were also obtained when

■4-Methoxyphenyldibenzylsulfonium hexafluorophosphate (Example 7) ■p-chlorobenzyl 4-acetoxyphenylethylsulfonium hexafluoroacenate (Example 8) ■4-Methylbenzyl 4-methoxycarbonyl Oxy-3-chlorophenylmethylsulfonium tetrafluoroborate (Example 9) ■p-methoxybenzyl
4-Benzoyloxy 2-methylphenylmethylsulfonium hexafluorophosphate (Example 10)■
4-Phenoxycarbonyloxyphenyldimethylsulfonium hexafluoroantimonate (Example 11) (Effects of the invention) The radiation-curable composition of the present invention has excellent curability, and the resulting cured product has excellent adhesion. It has excellent solvent resistance and is useful as coating materials, paints, overcoating agents for optical disks, adhesives, etc.

Claims (2)

[Claims] (1) (meth)acrylate compound (A) and/or epoxy resin (B), vinyl ether compound (C) having at least two vinyl ether groups per molecule, formula [
A radiation-curable composition characterized by containing a sulfonium salt (D) represented by I ] and a photopolymerization initiator (E) as an optional component ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I ] ( In the formula [I], R_1 represents hydrogen, an alkyl group, or ▲a numerical formula, a chemical formula, a table, etc.▼, and Y represents an optionally substituted alkyl group, alkoxyl group, phenyl group, or phenoxy group. R_2 and R_3 each independently represent hydrogen, halogen or an alkyl group. Q and R_4 each independently represent an optionally substituted alkyl group. X is SbF_6, PF_6, AsF
_6 or BF_4). (2) A cured product of the radiation-curable composition according to claim 1.