JPH11269211A - Curable composition and cured product thereof - Google Patents

Abstract

(57) [PROBLEMS] To provide a radical or acid generator which has excellent properties in both solubility and photosensitivity and which loses an acid by-produced by heating, and a compound which can be cured by a radical or an acid. A curable composition and a cured product thereof are provided. A radical or acid generator having a structure of the general formula (1) or (2) is represented by the general formula (1): General formula (2) (Where R is a chlorine, bromine or alkyl group, R 'is an alkyl group, and n is an integer of 0 to 2), and a curable composition comprising a compound curable by a radical or an acid, and a cured product thereof. [0000]

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a curable composition and a cured product thereof. More specifically, an active radical or acid is generated by irradiation of light, and a compound curable by the radical or acid is radically polymerized, cationically polymerized or acid-cured in a short time, for example, a molding resin, a casting resin,
Resin for stereolithography, sealant, polymerization resin for dental use, printing ink, paint, photosensitive resin for printing plate, color proof for printing, resist for color filter, resist for printed circuit board, photoresist for semiconductor, resist for microelectronics , Hologram material, overcoat material,
The present invention relates to a curable composition for obtaining a polymer or a cured product having good physical properties in the fields of an adhesive, a pressure-sensitive adhesive, a release agent, an optical recording medium, various devices, and the like, and a cured product thereof.

[0002]

2. Description of the Related Art Onium salts represented by aromatic diazonium salts, iodonium salts, sulfonium salts and the like, and metal arene complexes are already known as compounds which initiate cationic polymerization of epoxy or the like upon irradiation with light. U.S. Patent Nos. 4069054 and 445.
No. 0360, No. 4576999, No. 464096
7, No. 1,274,646 and EP 203829. These are also Advances in PolymerS
science 62, Initiators-P
oly Reactions-Optical A
activity, pp.1-48, Springer-
Verlag (1984), "Latest UV curing technology",
It is compiled in Technical Information Association, page 29 (1991).

On the other hand, it has been reported that these onium salts are used as initiators for radical polymerization of acrylates and the like. For example, Japanese Patent Publication No. 63-2081 discloses triphenylsulfonium hexafluorophosphate, JP-140203 discloses triaryl and diarylsulfonium compounds.
No. 2 discloses various sulfonium and oxosulfonium compounds.

In recent years, it has been reported that iodonium compounds having a certain kind of organoboron anion exhibit good properties as initiators for cationic photopolymerization.
C. Priou et al. [(RadTech '94 North America Proceedings (RadTech '94
North America Proc. ,) Volume 1,
187 (1994) and Polymeric Materials Science and Engineering (Pol
ym. Mater. Sci. Eng. ,), Vol. 72,
417, (1995)] that diphenyliodonium tetrakis (pentafluorophenyl) borate is more effective at polymerizing epoxysilicon than conventional diphenyliodonium hexafluoroantimonate.
It has been reported to have higher polymerization properties and less toxicity. Further, JP-A-6-184170 and WO 95/03338 propose novel onium organoborates and metal arene organoborates (eg, iodonium, sulfonium, selenonium, phosphonium, ammonium, iron arenes). Have been.

[0005] Also recently, Taniguchi has described Rad
Tech Asia'97 Conference P
rosedings, p. 46 (1997), UV
This shows that sulfonium salts having high sensitivity to light are effective for cationic polymerization.

[0006]

Among the onium salts described in the prior art, iodonium salts and sulfonium salts are considered to be particularly useful industrially. Among these, as anions which provide high sensitivity characteristics, there can be mentioned. Is considered to be preferably hexafluoroantimonate. However, an onium salt containing hexafluoroantimonate has a danger of toxicity, and other anions, for example, hexafluorophosphate, have a drawback of poor sensitivity characteristics. In addition, among the above-mentioned onium salts, tetrafluoroborate, hexafluorophosphate, and hexafluoroantimonate salts generally have a solubility in various organic materials and resins that is not always at a satisfactory level. The development of anionic species that can improve the concentration was also one of the issues. Further, all of these onium salts have a fundamental problem that a Lewis acid by-produced by decomposition thereof remains in the reaction system forever and causes corrosion of metals and the like.

On the other hand, C.I. Although diphenyliodonium tetrakis (pentafluorophenyl) borate reported by Priou et al. Is reported to have higher polymerization properties for the polymerization of epoxysilicon than conventional diphenyliodonium hexafluoroantimonate. The other proposed onium borate structures are limited to diaryliodonium borate and triarylsulfonium borate, and radical polymerization represented by acrylate has not been studied at all.

Therefore, as described above, various onium salts have been studied. However, they exhibit higher sensitivity to light, have higher solubility in various organic materials and resins, and have a by-product Lewis acid. There has been a demand for a polymerization initiator which does not remain in the reaction system forever.

[0009]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above problems in consideration of the above problems, and as a result, have reached the present invention. That is, the present invention relates to a radical or acid generator (A) represented by the general formula (1) or (2).
And a curable composition comprising a compound (B) curable by a radical or an acid. General formula (1)

[0010]

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General formula (2)

[0012]

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(Where R represents chlorine, bromine or an alkyl group, R ′ represents an alkyl group, and n represents an integer of 0 to 2.) In the present invention, the compound (B) which can be cured by radicals or by an acid is used. Acrylates or methacrylates. The present invention also relates to a cured product of the curable composition.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. First, the radical or acid generator (A) of the present invention will be described. The radical or acid generator (A) of the present invention is characterized by having a thioxanthone or benzophenone structure that is highly sensitive to light, particularly ultraviolet light. Further, as the substituent R in the general formula (1) or (2), besides chlorine and bromine, an alkyl group can be mentioned, and R ′ can be an alkyl group. The alkyl group referred to herein means a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a cyclohexyl group, an octyl group, and an octadecyl group. Etc. can be given.

The introduction of such a substituent improves the solubility in a radical polymerizable compound and an acid-curable compound described below. Among them, the preferred structure of the radical or acid generator (A) of the present invention is the following compound (1)
-Compound (28). Compound (1)

[0016]

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Compound (2)

[0018]

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Compound (3)

[0020]

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Compound (4)

[0022]

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Compound (5)

[0024]

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Compound (6)

[0026]

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Compound (7)

[0028]

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Compound (8)

[0030]

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Compound (9)

[0032]

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Compound (10)

[0034]

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Compound (11)

[0036]

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Compound (12)

[0038]

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Compound (13)

[0040]

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Compound (14)

[0042]

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Compound (15)

[0044]

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Compound (16)

[0046]

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Compound (17)

[0048]

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Compound (18)

[0050]

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Compound (19)

[0052]

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Compound (20)

[0054]

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Compound (21)

[0056]

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Compound (22)

[0058]

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Compound (23)

[0060]

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Compound (24)

[0062]

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Compound (25)

[0064]

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Compound (26)

[0066]

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Compound (27)

[0068]

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Compound (28)

[0070]

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The synthesis of the radical or acid generator (A)
It can be easily obtained by an ion exchange reaction between a sulfonium salt and metal tetrakis (pentafluorophenyl) borate. For example, 2,4-diethyl-7-diphenylsulfoniothioxanthen-9-onetetrakis (pentafluorophenyl) borate is a halide salt of 2,4-diethyl-7-diphenylsulfoniothioxanthen-9-one (or Hexafluorophosphate salt) and lithium tetrakis (pentafluorophenyl) borate. These sulfonium salts can be synthesized by a condensation reaction of the corresponding halogenated thioxanthone or halogenated benzophenone derivative with a diaryl sulfoxide. This synthesis method is based on the Journal of American Chemical Society,
73, p. 1965 (1951).

The radical or acid generator (A) of the present invention
Is characterized by being easily decomposed by light irradiation to generate a strong acid. The acid generated here is considered to be a stronger acid than the conventionally known onium salts having anions such as BF ₄ ⁻ , PF ₆ ⁻ , AsF ₆ ⁻ and SbF ₆ ⁻ . In addition, it is characterized in that no acid remains by heating after being decomposed to generate an acid.
Furthermore, the polymerization initiator (A) of the present invention can be used in various organic solvents, polymers and oligomers, rather than the conventionally known onium salts having anions such as BF ₄ ⁻ , PF ₆ ⁻ , AsF ₆ ⁻ and SbF ₆ ^−. Is extremely high in compatibility and solubility.

Next, the compound (B) curable by radicals or acids will be described. The compound (B) curable by a radical or an acid in the present invention means a compound having at least one radically polymerizable ethylenically unsaturated bond in a molecule. Further, each of them has a chemical form of a monomer, oligomer or polymer which is liquid or solid at normal temperature and normal pressure.

Examples of the compound (B) curable by radicals or acids include unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid and maleic acid, and salts thereof, Examples include esters, urethanes, acid amides and acid anhydrides, and further include acrylonitrile, styrene derivatives, various unsaturated polyesters, unsaturated polyethers, unsaturated polyamides, unsaturated polyurethanes, and the like. However, the present invention is not limited to this.

Hereinafter, specific examples of the compound (B) curable by a radical or an acid in the present invention will be described. Examples of acrylates: Examples of monofunctional alkyl acrylates: methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isoamyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, decyl acrylate, lauryl acrylate, stearyl acrylate , Isobornyl acrylate, cyclohexyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, benzyl acrylate.

Examples of monofunctional hydroxy-containing acrylates:
2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxy-3-chloropropyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-allyloxypropyl acrylate, 2-acryloyloxyethyl-2 -Hydroxypropyl phthalate.

Examples of monofunctional halogen-containing acrylates:
2,2,2-trifluoroethyl acrylate, 2,
2,3,3-tetrafluoropropyl acrylate, 1
H-hexafluoroisopropyl acrylate, 1H,
1H, 5H-octafluoropentyl acrylate, 1
H, 1H, 2H, 2H-heptadecafluorodecyl acrylate, 2,6-dibromo-4-butylphenyl acrylate, 2,4,6-tribromophenoxyethyl acrylate, 2,4,6-tribromophenol 3EO
Addition acrylate.

Examples of monofunctional ether-containing acrylates:
2-methoxyethyl acrylate, 1,3-butylene glycol methyl ether acrylate, butoxyethyl acrylate, methoxytriethylene glycol acrylate, methoxypolyethylene glycol # 400 acrylate, methoxydipropylene glycol acrylate, methoxytripropylene glycol acrylate,
Methoxy polypropylene glycol acrylate, ethoxydiethylene glycol acrylate, 2-ethylhexyl carbitol acrylate, tetrahydrofurfuryl acrylate, phenoxyethyl acrylate, phenoxydiethylene glycol acrylate, phenoxy polyethylene glycol acrylate, cresyl polyethylene glycol acrylate, p-nonylphenoxyethyl acrylate, p-nonyl Phenoxy polyethylene glycol acrylate, glycidyl acrylate.

Examples of monofunctional carboxyl-containing acrylates: β-carboxyethyl acrylate, monoacryloyloxyethyl succinate, ω-carboxypolycaprolactone monoacrylate, 2-acryloyloxyethyl hydrogen phthalate, 2-acryloyloxypropyl hydrogen phthalate, 2-acryloyloxypropyl hexahydrohydrogen phthalate, 2-acryloyloxypropyl tetrahydrohydrogen phthalate.

Examples of other monofunctional acrylates: N,
N-dimethylaminoethyl acrylate, N, N-dimethylaminopropyl acrylate, morpholinoethyl acrylate, trimethylsiloxyethyl acrylate,
Diphenyl-2-acryloyloxyethyl phosphate, 2-acryloyloxyethyl acid phosphate, caprolactone-modified 2-acryloyloxyethyl acid phosphate.

Examples of bifunctional acrylates: 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol # 200 diacrylate , Polyethylene glycol # 300 diacrylate, polyethylene glycol # 4
00 diacrylate, polyethylene glycol # 600
Diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, tetrapropylene glycol diacrylate, polypropylene glycol # 400 diacrylate, polypropylene glycol # 700 diacrylate, neopentyl glycol diacrylate, neopentyl glycol PO modified diacrylate, hydroxy Neopentyl glycol pivalate diacrylate, caprolactone adduct of hydroxypivalate neopentyl glycol ester, 1,6-hexanediol bis (2-hydroxy-3-acryloyloxypropyl)
Ether, 1,9-nonanediol diacrylate, pentaerythritol diacrylate, pentaerythritol diacrylate monostearate, pentaerythritol diacrylate monobenzoate, bisphenol A diacrylate, EO-modified bisphenol A diacrylate, PO-modified bisphenol A diacrylate,
Hydrogenated bisphenol A diacrylate, EO modified hydrogenated bisphenol A diacrylate, PO modified hydrogenated bisphenol A diacrylate, bisphenol F diacrylate, EO modified bisphenol F diacrylate, PO modified bisphenol F diacrylate, EO modified tetrabromobisphenol A Diacrylate, tricyclodecane dimethylol diacrylate, isocyanuric acid EO-modified diacrylate.

Examples of trifunctional acrylates: glycerin P
O-modified triacrylate, trimethylolpropane triacrylate, trimethylolpropane EO-modified triacrylate, trimethylolpropane PO-modified triacrylate, isocyanuric acid EO-modified triacrylate,
Isocyanuric acid EO-modified ε-caprolactone-modified triacrylate, 1,3,5-triacryloylhexahydro-s-triazine, pentaerythritol triacrylate, dipentaerythritol triacrylate tripropionate.

Examples of acrylates having four or more functional groups: pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate monopropionate, dipentaerythritol hexaacrylate, tetramethylol methane tetraacrylate, oligoester tetraacrylate, tris (acryloyloxy) phosphate .

Examples of methacrylates: Examples of monofunctional alkyl methacrylates: methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, isoamyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, decyl methacrylate, lauryl methacrylate , Stearyl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, dicyclopentenyl methacrylate, dicyclopentenyloxyethyl methacrylate, benzyl methacrylate.

Examples of monofunctional hydroxy methacrylates: 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxy-3-chloropropyl methacrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 2-hydroxy-3
-Allyloxypropyl methacrylate, 2-methacryloyloxyethyl-2-hydroxypropyl phthalate.

Examples of monofunctional halogen-containing methacrylates:
2,2,2-trifluoroethyl methacrylate, 2,
2,3,3-tetrafluoropropyl methacrylate,
1H-hexafluoroisopropyl methacrylate, 1
H, 1H, 5H-octafluoropentyl methacrylate, 1H, 1H, 2H, 2H-heptadecafluorodecyl methacrylate, 2,6-dibromo-4-butylphenyl methacrylate, 2,4,6-tribromophenoxyethyl methacrylate, 2 , 4,6-tribromophenol 3EO addition methacrylate.

Examples of monofunctional ether-containing methacrylates: 2-methoxyethyl methacrylate, 1,3-butylene glycol methyl ether methacrylate, butoxyethyl methacrylate, methoxytriethylene glycol methacrylate, methoxypolyethylene glycol # 400 methacrylate, methoxydipropylene glycol Methacrylate, methoxytripropylene glycol methacrylate, methoxy polypropylene glycol methacrylate, ethoxydiethylene glycol methacrylate, 2-ethylhexyl carbitol methacrylate, tetrahydrofurfuryl methacrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol methacrylate, phenoxy polyethylene glycol methacrylate Cresyl polyethylene glycol methacrylate, p- nonyl phenoxyethyl methacrylate, p- nonylphenoxy polyethylene glycol methacrylate, glycidyl methacrylate.

Examples of monofunctional carboxyl-containing methacrylates: β-carboxyethyl methacrylate, monomethacryloyloxyethyl succinate, ω-carboxypolycaprolactone monomethacrylate, 2-methacryloyloxyethyl hydrogen phthalate, 2-methacryloyloxypropyl hydrogen phthalate,
2-methacryloyloxypropyl hexahydrohydrogen phthalate, 2-methacryloyloxypropyl tetrahydrohydrogen phthalate.

Examples of other monofunctional methacrylates:
N, N-dimethylaminoethyl methacrylate, N, N
-Dimethylaminopropyl methacrylate, morpholinoethyl methacrylate, trimethylsiloxyethyl methacrylate, diphenyl-2-methacryloyloxyethyl phosphate, 2-methacryloyloxyethyl acid phosphate, caprolactone-modified 2-methacryloyloxyethyl acid phosphate.

Examples of bifunctional methacrylates: 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate,
Tetraethylene glycol dimethacrylate, polyethylene glycol # 200 dimethacrylate, polyethylene glycol # 300 dimethacrylate, polyethylene glycol # 400 dimethacrylate, polyethylene glycol # 600 dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate Methacrylate, polypropylene glycol # 400 dimethacrylate, polypropylene glycol # 700 dimethacrylate, neopentyl glycol dimethacrylate,
Neopentyl glycol PO-modified dimethacrylate, hydroxypivalate neopentyl glycol ester dimethacrylate, hydroxypivalate neopentyl glycol ester caprolactone adduct dimethacrylate, 1,6-hexanediol bis (2-hydroxy-3-methacryloyloxypropyl) Ether, 1,
9-nonanediol dimethacrylate, pentaerythritol dimethacrylate, pentaerythritol dimethacrylate monostearate, pentaerythritol dimethacrylate monobenzoate, bisphenol A dimethacrylate, EO-modified bisphenol A dimethacrylate, PO-modified bisphenol A dimethacrylate,
Hydrogenated bisphenol A dimethacrylate, EO modified hydrogenated bisphenol A dimethacrylate, PO modified hydrogenated bisphenol A dimethacrylate, bisphenol F dimethacrylate, EO modified bisphenol F dimethacrylate, PO modified bisphenol F dimethacrylate, EO modified tetrabromobisphenol A Dimethacrylate, tricyclodecane dimethylol dimethacrylate, isocyanuric acid EO-modified dimethacrylate.

Examples of trifunctional methacrylates: glycerin PO modified trimethacrylate, trimethylolpropane trimethacrylate, trimethylolpropane EO modified trimethacrylate, trimethylolpropane PO modified trimethacrylate, isocyanuric acid EO modified trimethacrylate, isocyanuric acid EO modified ε -Caprolactone-modified trimethacrylate, 1,3,5-trimethacryloylhexahydro-s-triazine, pentaerythritol trimethacrylate, dipentaerythritol trimethacrylate tripropionate.

Examples of tetrafunctional or higher methacrylates: pentaerythritol tetramethacrylate, dipentaerythritol pentamethacrylate monopropionate,
Dipentaerythritol hexamethacrylate, tetramethylolmethanetetramethacrylate, oligoestertetramethacrylate, tris (methacryloyloxy) phosphate.

Examples of arylates: allyl glycidyl ether, diallyl phthalate, triallyl trimellitate, isocyanuric acid triarylate.

Examples of acid amides: acrylamide, N-methylol acrylamide, diacetone acrylamide,
N, N-dimethylacrylamide, N, N-diethylacrylamide, N-isopropylacrylamide, acryloylmorpholine, methacrylamide, N-methylol methacrylamide, diacetone methacrylamide,
N, N-dimethylmethacrylamide, N, N-diethylmethacrylamide, N-isopropylmethacrylamide, methacryloylmorpholine.

Examples of styrenes: styrene, p-hydroxystyrene, p-chlorostyrene, p-bromostyrene, p-methylstyrene, p-methoxystyrene, p-
t-butoxystyrene, pt-butoxycarbonylstyrene, pt-butoxycarbonyloxystyrene,
2,4-diphenyl-4-methyl-1-pentene.

Examples of other vinyl compounds: vinyl acetate, vinyl monochloroacetate, vinyl benzoate, vinyl pivalate,
Vinyl butyrate, vinyl laurate, divinyl adipate,
Vinyl methacrylate, vinyl crotonate, vinyl 2-ethylhexanoate, N-vinylcarbazole, N-vinylpyrrolidone and the like.

The compound (B) curable by a radical or an acid can be easily obtained as a commercial product of the following manufacturer. Commercial products of such manufacturers include, for example, Kyoeisha Yushi Kagaku Kogyo Co., Ltd.'s "Light Acrylate", "Light Ester", "Epoxy Ester", "Urethane Acrylate" and "Highly Functional Oligomers" series, “NK Ester” and “NK Oligo” series manufactured by Shin-Nakamura Chemical Co., Ltd., “Fancryl” series manufactured by Hitachi Chemical Co., Ltd., “Aronix M” series manufactured by Toagosei Chemical Co., Ltd., "Functional monomer" series manufactured by Daihachi Chemical Industry Co., Ltd.
“Special acrylic monomer” series manufactured by Osaka Organic Chemical Industry Co., Ltd., “Acryester” and “Diabeam Oligomer” series manufactured by Mitsubishi Rayon Co., Ltd., “Kayarad” manufactured by Nippon Kayaku Co., Ltd. "Kayamar"
Series, "Acrylic acid / methacrylic acid ester monomer" series manufactured by Nippon Shokubai Co., Ltd., "NICHIGO-UV purple light urethane acrylate oligomer" series manufactured by Nippon Synthetic Chemical Industry Co., Ltd., Shin-Etsu Vinyl Acetate Co., Ltd.
And the "functional monomer" series manufactured by Kojin Co., Ltd.

The following cyclic compounds are also exemplified as the compound (B) curable by radicals or acids. Examples of three-membered ring compounds: Journal of Polymer Science Polymer Chemistry Edition (J.
Polym. Sci. Polym. Chem. E
d. ), Vol. 17, p. 3169 (1979).
Rapid Communication (Makromol. C)
hem. Rapid Commun. ), Vol. 5, 63
1-phenyl-2-vinylcyclopropane, Journal of Polymer Science Polymer Chemistry Edition (J. Po.)
lym. Sci. Polym. Chem. Ed. 23, 1931 (1985) and Journal
Of Polymer Science Polymer Letter Edition (J. Polym. Sci. Polym. Le
tt. Ed. ), Volume 21, p. 4331 (1983)
Described 2-phenyl-3-vinyloxiranes, Proceedings of the 50th Annual Meeting of the Chemical Society of Japan, 1564 (1985)
2,3-divinyloxiranes described in (Year).

Examples of cyclic ketene acetals: Journal of Polymer Science Polymer Chemistry Edition (J. Polym. Sci. Poly)
m. Chem. Ed. ), Volume 20, p. 3021 (19
1982) and the Journal of Polymer Science Polymer Letter Edition (J. Poly)
m. Sci. Polym. Lett. Ed. ), 21st
Vol., P. 373 (1983).
3-dioxepane, polymer pre-preprint (Po
lym. Preprints), Vol. 34, p. 152 (1985), dioxolanes, Journal of Polymer Science, Polymer Letter Edition (J. Polym. Sci. Polym. Let).
t. Ed. 20, 361 (1982), Macromolecular Chemie (Makromol. Che).
m. 183, 1913 (1982) and Macromolecular Chemie (Makromol. Ch.).
em. 186, p. 1543 (1985), 2-methylene-4-phenyl-1,3-dioxepane, Macromolecules.
s), Vol. 15, p. 1711 (1982), 4,
7-dimethyl-2-methylene-1,3-dioxepane,
Polymer Prepreprint (Polym. Prepr)
5,6-benzo-2-methylene-1,3-diosepan described in Vol. 34, pp. 154 (1985).

The compound (B) which can reduce the solubility of the novolak resin in alkali by a crosslinking or polymerization reaction in the presence of an acid catalyst or in combination with heating is a compound (B) curable by radicals or acids. . Typical examples include compounds having a methylol group as a formaldehyde precursor, or substituted methylol groups, and various aminoblasts or phenoblasts, i.e., urea-formaldehyde, melamine-formaldehyde, benzoguanamine-formaldehyde, glycol. There are uryl-formaldehyde resins and their monomers or oligomers. Many of these are commercially available for applications such as vehicles for paints.
For example, Cym manufactured by American Cyanamid
el (registered trademark) 300, 301, 303, 350, 3
70, 380, 1116, 1130, 1123, 112
5, 1170, etc., or Nikarac (registered trademark) Mw30, Mw 30M, Mw30HM, manufactured by Sanwa Chemical Co., Ltd.
Series such as Mx45 and Bx4000 can be mentioned as typical examples. These may be used alone or in combination of two or more.

Specific examples of another compound (B) which is radically polymerizable or curable by an acid include a methylolated or alkoxydimethylated phenol derivative which can be a formaldehyde precursor. These may be used as a monomer or may be used as a resin such as a resole resin or a benzyl ether resin.

Further, as another system of the compound (B) curable by a radical or an acid, compounds having a silanol group, for example, JP-A-2-154266 and JP-A-2-1-1
Compounds as disclosed in JP 73647 can be mentioned.

Also, a mixture of a polyene and a polythiol,
For example, as polyene, diallyl phthalate, diallyl isophthalate, diallyl maleate, diallyl carbonate, triallyl isocyanurate, urethane-based polyene produced from polyisocyanate and allyl alcohol (for example, obtained by polycondensation reaction of hexamethylene diisocyanate and allyl alcohol) A mixture of a compound selected from, for example, a urethane compound) and a compound selected from, for example, trimethylolpropanetrithiol glycolate, pentaerythritol-tetra-3-mercaptopropionate as a polythiol can also be prepared by radical or acid. It can be exemplified as the curable compound (B).

The following alkoxysilanes can also be mentioned as the compound (B) curable by radicals or acids. Specific examples include tetraalkoxysilanes such as tetramethoxysilane and tetraethoxysilane, γ-chloropropyltrimethoxysilane, γ-aminopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-glycidoxypropyl Compounds having an alkoxysilyl group such as trimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, and more specifically, a product catalog of Toray Dow Corning Co., page 59, or Shin-Etsu Silicone Silane "Silane Coupling Agent" described in the Coupling Agent Product Catalog (issued in September 1987), or Toray Dow Corning Product Catalog, page 61 or Toshiba Silicone General Catalog, page 27 (issued in April 1986) Compounds having an alkoxysilyl group, known in the industry as "silane compound" described is, can be cited as alkoxysilanes.

Further, as the compound (B) curable by radicals or acid, there can be mentioned a compound capable of cationic polymerization or a mixture thereof. The term "cationically polymerizable compound" as used herein means, for example, epoxy compounds, styrenes, vinyl compounds, vinyl ethers, spiroorthoesters, bicycloorthoesters, spiroorthocarbonates, cyclic ethers, lactones, oxazolines. , Aziridine, cyclosiloxanes, ketals, cyclic acid anhydrides, lactams and aryl dialdehydes.

First, examples of the epoxy compound include conventionally known aromatic epoxy compounds, alicyclic epoxy compounds, aliphatic epoxy compounds, epoxide monomers and episulfite monomers. Examples of the aromatic epoxy compound include a monofunctional epoxy compound such as phenylglycidyl ether and a polyglycidyl ether of a polyhydric phenol having at least one aromatic nucleus or an alkylene oxide adduct thereof, such as bisphenol A. Glycidyl ethers produced by reacting bisphenol compounds such as tetrabromobisphenol A, bisphenol F, bisphenol S or alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, etc.) adducts of bisphenol compounds with epichlorohydrin;
Novolak type epoxy resins (for example, phenol novolak type epoxy resin, cresol novolak type epoxy resin, brominated phenol novolak type epoxy resin, etc.), trisphenol methane triglycidyl ether and the like.

Examples of the alicyclic epoxy compounds include 4-vinylcyclohexene monoepoxide, norbornene monoepoxide, limonene monoepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, and bis- (3,4 -Epoxycyclohexylmethyl) adipate, 2- (3,4-
Epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexanone-meta-dioxane, bis (2,3-epoxycyclopentyl) ether, 2-
(3,4-epoxycyclohexyl-5,5-spiro-
3,4-epoxy) cyclohexane-meta-dioxane, 2,2-bis [4- (2,3-epoxypropoxy) cyclohexyl] hexafluoropropane, BHP
E-3150 (manufactured by Daicel Chemical Industries, Ltd., alicyclic epoxy resin (softening point: 71 ° C.)) and the like.

As the aliphatic epoxy compound, for example, 1,4-butanediol dicricidyl ether, 1,6
-Hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, ethylene glycol monoglycidyl ether, propylene glycol diglycidyl ether, propylene glycol monoglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether , Neopentyl glycol monoglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane diglycidyl ether,
Examples include trimethylolpropane monoglycidyl ether, trimethylolpropane triglycidyl ether, diglycerol triglycidyl ether, sorbitol tetraglycidyl ether, allyl glycidyl ether, and 2-ethylhexyl glycidyl ether.

Examples of the styrenes include styrene, α-methylstyrene, p-methylstyrene, p-chloromethylstyrene and the like. Examples of the vinyl compound include N-vinylcarbazole, N-vinylpyrrolidone, and the like.

As the vinyl ethers, for example, n-
(Or iso-, t-) butyl vinyl ether, cyclohexyl vinyl ether, hydroxybutyl vinyl ether, 1,4 butanediol divinyl ether, ethylene glycol divinyl ether, ethylene glycol monovinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, propylene Glycol divinyl ether, propylene glycol monovinyl ether, neopentyl glycol divinyl glycol, neopentyl glycol monovinyl glycol, glycerol divinyl ether, glycerol trivinyl ether, trimethylolpropane monovinyl ether, trimethylolpropane divinyl ether, trimethylolpropane trivinyl ether, diglycerol Li ether, sorbitol tetravinyl ether, cyclohexanedimethanol divinyl ether, hydroxybutyl vinyl ether, dodecyl vinyl ether 2,2-bis (4-cyclohexanol) propane divinyl ether, 2,2-bis (4
-Cyclohexanol) alkyl vinyl ethers such as trifluoropropane divinyl ether, alkenyl vinyl ethers such as allyl vinyl ether, alkynyl vinyl ethers such as ethynyl vinyl ether, 1-methyl-2-propenyl vinyl ether, 4-vinyl ether styrene, hydroquinone divinyl ether, phenyl Aryl vinyl ethers such as vinyl ether, p-methoxyphenyl vinyl ether, bisphenol A divinyl ether, tetrabromobisphenol A divinyl ether, bisphenol F divinyl ether, phenoxyethylene vinyl ether, p-bromophenoxyethylene vinyl ether, and 1,4-benzenedimethanol divinyl ether , Nm-chlorophenyldiethanol alcohol Nji ether, m- phenylene bis (ethylene glycol) aralkyl divinyl et one ether such as divinyl ether, urethane polyvinyl ether (e.g., ALLIED-SIGNAL Inc., V
ECtomer 2010).

Examples of spiroorthoesters include 1,1
4,6-trioxaspiro (4,4) nonane, 2-methyl-1,4,6-trioxaspiro (4,4) nonane,
1,4,6-trioxaspiro (4,5) decane and the like, as bicycloorthoesters, 1-phenyl-4-ethyl-2,6,7-trioxabicyclo (2,5
2,2) octane, 1-ethyl-4-hydroxymethyl-2,6,7-trioxabicyclo (2,2,2) octane and the like include spiroorthocarbonates,
Cyclic ethers such as 1,5,7,11-tetraoxaspiro (5,5) undecane, 3,9-dibenzyl-1,5,7,11-tetraoxaspiro (5,5) undecane Is raised.

Examples of the cyclic ethers include oxetanes such as oxetane and phenyloxetane; tetrahydrofurans such as tetrahydrofuran and 2-methyltetrahydrofuran; tetrahydropyrans such as tetrahydropyran and 3-propyltetrahydropyran; trimethylene oxide; and s-trioxane. And so on. Lactones include β-propiolactone, γ-
Butyl lactone, δ-caprolactone, δ-valerolactone and the like can be mentioned. Examples of the oxazolines include oxazoline, 2-phenyloxazoline, 2-decyloxazoline and the like.

As the aziridine, aziridine, N-
Ethyl aziridine and the like. Examples of cyclosiloxanes include hexamethyltrisiloxane, octamethylcyclotetrasiloxane, triphenyltrimethylcyclotrisiloxane, and the like. Ketals include 1,3-dioxolan, 1,3-dioxane,
2,2-dimethyl-1,3-dioxane, 2-phenyl-1,3-dioxane, 2,2-dioctyl-1,3-
Dioxolan and the like. The cyclic acid anhydrides include phthalic anhydride, maleic anhydride, succinic anhydride and the like, and the lactams include β-propiolactam, γ-butyrolactam, δ-caprolactam and the like.
In addition, examples of the aryl dialdehydes include 1,2-benzenedicarboxaldehyde, 1,2-naphthalenedialdehyde, and the like.

Further, the curable composition obtained by mixing the radical or acid generator (A) of the present invention with a compound (B) curable by a radical or an acid has a high sensitivity, a high curing speed, and a cured product. Has good hardness and physical properties. further,
The curable composition of the present invention can be used by being mixed with a binder such as an organic high molecular polymer and applied to a glass plate, an aluminum plate, another metal plate, or a polymer film such as polyethylene terephthalate.

The compound (B) of the present invention which can be cured with a radical or an acid may be used singly or as a mixture of two or more kinds at an arbitrary ratio in order to improve desired properties. I do not care. In addition, the radical or acid generator (A) of the present invention is preferably used in an amount of 0.01 to 20 parts by weight based on 100 parts by weight of the compound (B) curable by the radical or acid. 0.1 to 1
More preferably, it is used in the range of 0 parts by weight.

Examples of the binder which can be used by mixing with the curable composition of the present invention include polyacrylates and poly-α.
-Alkyl acrylates, polyamides, polyvinyl acetals, polyformaldehydes, polyurethanes, polycarbonates, polystyrenes, polymers such as polyvinyl esters, copolymers, and more specifically, polymethacrylate, polymethacrylate Methyl methacrylate, polyethyl methacrylate, polyvinyl carbazole, polyvinyl pyrrolidone, polyvinyl butyral,
Polyvinyl acetate, novolak resin, phenolic resin, epoxy resin, alkyd resin, etc., supervised by Kiyoshi Akamatsu, "Practical technology of new photosensitive resin", (CMC,
1987) and "10188 Chemical Products", 657-7
An organic polymer known in the art described on page 67 (Kagaku Kogyo Nippo, 1988) can be used.

Further, the curable composition of the present invention can be used in combination with other general-purpose polymerization initiators for the purpose of further improving the sensitivity. Other general-purpose polymerization initiators which can be used in combination by mixing with the curable composition of the present invention include JP-B-59-128.
No. 1, JP-B-61-9621 and JP-A-60-6
0104, triazine derivatives described in JP-A-59-15
No. 04 and JP-A-61-243807, JP-B-43-23684, JP-B-44-6.
No. 413, JP-B-47-1604 and USP No. 3
No. 567453, diazonium compound, USP No. 2
No. 848328, US Pat. No. 2,852,379 and U
Organic azide compounds described in SP No. 290853, JP-B-36-22062, JP-B-37-13109, JP-B-38-18015 and JP-B-45-9610.
Ortho-quinonediazides described in JP-B-55-39
No. 162, JP-A-59-140203 and "Macromolecules", Vol. 10, No. 13
Various onium compounds including an iodonium compound described on page 07 (1977), JP-A-59-14220.
No. 5, azo compounds described in JP-A-1-54440, European Patent No. 109851, European Patent No. 126
No. 712, "Journal of Imaging Science (J. Imag. Sci.)", Vol. 30, p. 174 (1986)
Year) metal allene complex described in JP-A-61-151197.
Titanocenes described in Coordination Chemistry Revie
w), Vol. 84, pp. 85-277 (1988) and a transition metal complex containing a transition metal such as ruthenium described in JP-A-2-182701, JP-A-3-2094.
No. 77, an aluminate complex described in JP-A-2-15776
No. 0, JP-A-55-127550
And 2,4 described in JP-A-60-202037.
Examples include 5-triarylimidazole dimer, carbon tetrabromide, and organic halogen compounds described in JP-A-59-107344. These general-purpose polymerization initiators are compounds (B) curable by radicals or acids. It is preferably contained in the range of 0.01 to 10 parts by weight based on 100 parts by weight.

The curable composition of the present invention can contain a thermal polymerization inhibitor for the purpose of preventing polymerization during storage. Specific examples of the thermal polymerization inhibitor that can be added to the curable composition of the present invention include p-methoxyphenol, hydroquinone, alkyl-substituted hydroquinone, catechol,
Examples thereof include tert-butylcatechol and phenothiazine. These thermal polymerization inhibitors are added in a range of 0.001 to 5 parts by weight based on 100 parts by weight of the compound (B) curable by radicals or acids. Preferably.

The polymerizable composition of the present invention may further contain a polymerization accelerator represented by an amine, thiol, disulfide or the like, or a chain transfer catalyst, for the purpose of accelerating the polymerization. Specific examples of polymerization accelerators and chain transfer catalysts that can be added to the polymerizable composition of the present invention include, for example, N-
Amines such as phenylglycine, triethanolamine and N, N-diethylaniline, US Pat. No. 4,414,312
And thiols described in JP-A-64-13144, disulfides described in JP-A-2-291561, thiones described in US Pat. No. 3,558,322 and JP-A-64-17048, and described in JP-A-2-291560. O-acylthiohydroxamate and N-alkoxypyridinethiones are mentioned.

The curable composition of the present invention may further contain, depending on the purpose, dyes, organic and inorganic pigments, oxygen removing agents such as phosphines, phosphonates, phosphites and the like, reducing agents, antifoggants, anti-fading agents, antihalation agents. , Optical brightener,
A surfactant, a colorant, a plasticizer, a flame retardant, an antioxidant, an ultraviolet absorber, a fungicide, an antistatic agent, a magnetic substance, a solvent for dilution, or the like may be used in combination.

The curable composition of the present invention comprises a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a xenon lamp, a carbon arc lamp, a metal halide lamp, a fluorescent lamp, a tungsten lamp, an argon ion laser, a helium cadmium laser, Helium neon laser, krypton ion laser, various semiconductor lasers, YAG laser,
By irradiation with light from various light sources such as a light emitting diode, a CRT light source, and a plasma light source, a target polymer or a cured product having excellent characteristics can be obtained.

Therefore, various inks, various printing plate materials, photoresist,
It can be applied to various recording media such as photosensitive materials such as electrophotography, direct printing plate materials, hologram materials and microcapsules, as well as adhesives, adhesives, adhesives, sealants and various paints. .

[0123]

The radical or acid generator (A) of the present invention acts very effectively as a curing agent for the compound (B) which can be cured with a radical or acid, and gives good sensitivity characteristics.

Although the detailed photoreaction mechanism is not clear, the radical or acid generator (A) causes an electron transfer reaction or an energy transfer reaction in the molecule by irradiation of light, and as a result, the radical and the acid are converted. Occur. It is considered that the radicals and acids generated in such a manner caused the polymerization or crosslinking reaction of the compound (B) curable by the radicals or acids to be cured.

Further, the acid by-produced during the decomposition of the radical or acid generator (A) of the present invention easily disappears by heating. Therefore, in applications where it is difficult for the acid to remain, for example, in the fields of paints and sealants for metals and resists,
It can be suitably used.

[0126]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. In the examples, “parts” means “parts by weight” unless otherwise specified. First, prior to Examples, synthesis examples of the radical or acid generator (A) of the present invention will be described.

(Synthesis Example 1) Synthesis of 2,4-diethyl-7-diphenylsulfoniothioxanthen-9-one tetrakis (pentafluorophenyl) borate (compound (1)) RadTech Asia'97 Conference
e Proceedings, p. 46 (1997), 2,4-diethyl-7-diphenylsulfoniothioxanthen-9-one 0.98 part of hexafluorophosphate is dissolved in 50 parts of acetonitrile, and lithium tetrakis is stirred. 50 parts of an aqueous solution containing 1.00 part of (pentafluorophenyl) borate
It was added dropwise at 25 ° C. over 0 minutes. The resulting white crystals were filtered, washed with distilled water, dried under reduced pressure, and 2,4-diethyl-7-diphenylsulfoniothioxanthen-9-onetetrakis (pentafluorophenyl) borate.
28 parts were obtained.

Elemental analysis C ₄₉ H ₂₅ OS ₂ BF ₂₀ theoretical value C: 54.26%, H: 2.32%, S; 5.91% Measurement value C: 54.52%, H: 2.61% , S; 6.08%

Example 1 Compound (1) was used as a radical or acid generator (A).
A curable composition comprising 100 parts of pentaerythritol triacrylate as a compound (B) curable by a radical or an acid is applied on an aluminum plate to a thickness of about 10 μm by using a bar coater, and is manufactured by Toshiba Corporation. UV irradiation device (Metal halide lamp 3KW2 lamp, 120W / c
m, at an irradiation distance of 180 mm) at a conveyor speed of 25 m / min, the curable composition was cured, and a tack-free cured film was obtained.

Examples 2 to 28 Except that the radical or acid generator (A) shown in Table 1 was used instead of 3 parts of the compound (1) in Example 1,
Experiments were carried out in exactly the same manner as in Example 1. In each case, a tack-free cured film was obtained.

Table 1 Example Radical or Example Radical or Acid Generator (A ) Acid generator (A)----------------------2 compound (2) 16 compound (16) 3 compound (3) 17 Compound (17) 4 Compound (4) 18 Compound (18) 5 Compound (5) 19 Compound (19) 6 Compound (6) 20 Compound (20) 7 Compound (7) 21 Compound (21) 8 Compound (8) 22 Compound (22) 9 Compound (9) 23 Compound (23) 10 Compound (10) 24 Compound (24) 11 Compound (11) 25 Compound (25) 12 Compound (12) 26 Compound (26) 13 Compound (13) 27 Compound (27) 14 Compound (14) 28 Compound (28) 15 Compound (15) ───────────── ──────────────

Comparative Example 1 The same procedures as in Example 1 were carried out except that dimethylphenacylsulfonium tetrakis (pentafluorophenyl) borate, which is a known radical or acid generator, was used in place of compound (1) in Example 1. When the operation was performed, a cured film was obtained at a conveyor speed of 10 m / min, but a tack-free cured product was not obtained at a conveyor speed of 25 m / min.

Examples 29 to 44 Example 1 was repeated except that 100 parts of pentaerythritol triacrylate in Example 1 was replaced with the compound (B) curable by a radical or acid shown in Table 2. Experiments were carried out in exactly the same manner as in the above, and in each case, a tack-free cured film was obtained.

Table 2 Examples Compounds (B) Curable by Radicals or Acids ───────────────────────────── 29 Trimethylol peroxy triacrylate 30 2-Ethylhexyl acrylate 31 2-Hydroxyethyl acrylate 32 1,6 -Hexanethiol acrylate 33 Ethylene glycol acrylate 34 Polypropylene glycol acrylate 35 Pentaerythritol acrylate 36 Pentaerythritol tetraacrylate 37 Polypentaerythritol hexaacrylate 38 2-Ethylhexyl methacrylate 39 Polymethacrylate methacrylate 40 1,6-Hexane methacrylate 41 Chirenku Bu Rikorushi Bu methacrylate 42 Torimechirorufu ° Ropa down trimethacrylate 43 Bu diallyl phthalate 44 triallyl trimellitate ───────────────────────────────

Example 45 Compound (1) was used as a radical or acid generator (A).
Part, ERL4221 (manufactured by Union Carbide Co.) as compound (B) curable by radical or acid
Parts of the curable composition, about 1 part using a bar coater.
It is applied on an aluminum plate to a thickness of 0 μm, and an ultraviolet irradiation device manufactured by Toshiba Corporation (metal halide lamp 3KW2, 120
W / cm, irradiation distance 180 mm) at 10 m / min
When the composition was irradiated at a conveyor speed of 3, the curable composition was cured, and a tack-free cured film was obtained.

Examples 46 to 63 In place of 100 parts of ERL4221 (manufactured by Union Carbide Co.) in Example 46, the compounds (B) curable by radicals or acids shown in Table 3 were used instead. Experiments were carried out in exactly the same manner as in Example 46. In each case, a tack-free cured film was obtained.

Table 3 Examples Compounds curable by radicals or acids (B) ────────────────────────────────── 46 Cymel300 (manufactured by American Cyanamit Co., Ltd.) 47 Niclac Mw30 (Manufactured by Sanwa Chemical Co., Ltd.) Cyclic acyl ether 54 1-Methylstyrene 56 N-Phenylcarboxyl 57 Ethylene glycol carbonyl ether 58 1,4,6-Trioxashydro (4,4) nonane 59 2-Methyl-1,4,6-trioxashiro ( 4,4) Nonane 60 1,4,6-Trioxadihydroxy (4,5) decan 61 1-Phenyl-4-ethyl-2,6,7-trioxadicyclo (2,2,2) octane 62 1, 5,7,11-tetraoxashydro (5,5) untecan 63 1-phenyloxetane ────

Example 64 The compound (1) was used as a radical or acid generator (A).
Part, pentaerythritol triacrylate 50 parts as compound (B) curable by radical or acid, ERL
A curable composition consisting of 50 parts of 4221 (manufactured by Union Carbide Co.) was applied on an aluminum plate to a thickness of about 10 μm using a bar coater, and an ultraviolet irradiation device manufactured by Toshiba Corporation (Metal halide lamp 3KW2 lamp, 120W) / Cm,
When irradiation was performed at a conveyor speed of 20 m / min at an irradiation distance of 180 mm), the curable composition was cured, and a tack-free cured film was obtained.

Reference Example As described above, the cured products obtained in Examples 1 to 64 were
After keeping the cured product in an oven at 10 ° C. for 10 minutes, the cured product was immersed in boiling distilled water for 10 minutes, and a test for measuring the pH of the water was performed. As a result, no change in pH was observed.

[0140]

The radical or acid generator (A) of the agent of the present invention is a compound (B) curable by a radical or acid.
Is effective as a curing agent, and a curable composition comprising these can obtain a cured product having good physical properties by light irradiation. Further, the radical or acid generator (A) of the present invention produces an acid as a by-product at the time of decomposition, but the acid generated here easily disappears by heating.

Accordingly, the curable composition of the present invention can be used as a molding resin, a casting resin, a sealant, a dental polymerized resin, an optical molding resin, a resist for a printed circuit board, a resist for a color filter, a resist for microelectronics, For photosensitive resin for plates, photosensitive ink jet, ink for printing (offset, gravure, silk screen), color proof for print proofing, paint, surface coating agent, adhesive, adhesive, release agent, hologram recording material, etc. It can be used for various materials, and in particular, can be suitably used in applications where it is difficult for acid to remain, for example, in the fields of metal paints, sealants, resists and the like.

Continued on the front page (51) Int.Cl. ⁶ Identification code FI C08G 4/00 C08G 4/00 63/08 63/08 65/00 65/00 73/00 73/00 77/08 77/08

Claims (3)

[Claims] 1. A curable composition comprising a radical or an acid generator (A) represented by the general formula (1) or (2) and a compound (B) curable by a radical or an acid. General formula (1) General formula (2) (However, R represents a chlorine, bromine or alkyl group, R ′ represents an alkyl group, and n represents an integer of 0 to 2.) 2. The curable composition according to claim 1, wherein the radical-curable or acid-curable compound (B) is an acrylate or a methacrylate. 3. A cured product of the curable composition according to claim 1 or 2.