JP2003329801A - Composition for molding lens, and lens using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a composition for molding a lens having a high refractive index and scratch resistance, and to provide a lens using the above composition. <P>SOLUTION: The composition for molding a lens which is cured by irradiation of energy rays contains as essential components (a) a radical polymerizable organic compound expressed by general formula (1), (b) a radical polymerizable organic compound comprising (meth)acrylate having three or more (meth)acryl groups in average in one molecule, and (c) an energy ray-sensitive radical polymerization initiator. In formula (1), R represents a hydrogen atom or a methyl group and two of R may be same or different. <P>COPYRIGHT: (C)2004,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a lens-forming composition which can be cured by irradiating energy rays and a lens using the same, and particularly to a lens having a high refractive index and a high resistance. The present invention relates to a lens composition having scratches and a lens using the same.

[0002]

2. Description of the Related Art Conventionally, a plastic lens made of an energy ray-curable resin has been preferably used from the viewpoints of ease of molding and environmental safety. Among them, those having a high refractive index are disclosed in, for example, JP-A-7-268045.
Those disclosed in the issue are known.

[0003]

However, the conventional lens having a high refractive index is easily scratched and it is necessary to use a hard hard coating together. Therefore, a lens molding composition that can obtain a lens having a high refractive index and scratch resistance has been desired.

Therefore, an object of the present invention is to provide a lens molding composition which does not have the above-mentioned drawbacks and which can obtain a lens having a high refractive index and scratch resistance, and a lens using the same. is there.

[0005]

As a result of intensive studies to solve the above problems, the present inventors have found that the above problems can be achieved by using a specific resin, and have completed the present invention. It was

That is, the present invention provides a lens molding composition which is cured by irradiation with energy rays, in the following general formula (1): (In the formula, each R is a hydrogen atom or a methyl group and may be the same or different) and an average of 3 or more (meta) in one molecule.
A lens molding composition comprising a radically polymerizable organic compound (b) composed of (meth) acrylate having an acrylic group and an energy ray sensitive radical polymerization initiator (c) as essential components. is there.

Preferably, the radically polymerizable organic compound (b) is a urethane (meth) acrylate further having a urethane bond, and preferably the cationically polymerizable organic compound (d) and the energy ray sensitive cationic polymerization initiation. The agent (e) is further contained, and more preferably,
The energy ray sensitive radical polymerization initiator (c) is an acylphosphine oxide compound.

The present invention is also a lens characterized by being obtained by injecting the composition for molding a lens into a mold, curing the composition by irradiating with active energy rays, and then releasing the composition.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The embodiments of the present invention will be described below.
This will be specifically described. The radically polymerizable organic compound (a) that can be used in the present invention has the general formula (1): (In the formula, each R is a hydrogen atom or a methyl group and may be the same or different).

The radical-polymerizable organic compound (b) which can be used in the present invention is a radical-polymerizable organic compound which is polymerized or cross-linked by irradiation with energy rays in the presence of an energy ray-sensitive radical polymerization initiator. It is a radical-polymerizable organic compound composed of (meth) acrylate having an average of 3 or more (meth) acrylic groups in one molecule.

The compound having a (meth) acrylic group is preferable because it is easy to synthesize and obtain, and is easy to handle. Examples thereof include epoxy (meth) acrylate, urethane (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, and (meth) acrylic acid ester of alcohol.

Here, the epoxy (meth) acrylate is obtained, for example, by reacting a conventionally known aromatic epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin or the like with (meth) acrylic acid ( (Meth) acrylate.

Among these epoxy (meth) acrylates, the (meth) acrylate of an aromatic epoxy resin is particularly preferable, and polyglycidyl of a polyhydric phenol having at least one aromatic nucleus or its alkylene oxide adduct. It is a (meth) acrylate obtained by reacting ether with (meth) acrylic acid.

For example, glycidyl ether obtained by reacting bisphenol A or its alkylene oxide adduct with epichlorohydrin is reacted with (meth) acrylic acid to obtain (meth) acrylate,
Examples thereof include (meth) acrylate obtained by reacting an epoxy novolac resin with (meth) acrylic acid.

The preferred urethane (meth) acrylate is obtained by reacting one or more kinds of hydroxyl group-containing polyester, hydroxyl group-containing polyether, hydroxyl group-containing (meth) acrylic acid ester and the like with isocyanates. Examples thereof include (meth) acrylate and (meth) acrylate obtained by reacting hydroxyl group-containing (meth) acrylic acid with isocyanates.

Preferred as the hydroxyl group-containing polyester used here is a hydroxyl group-containing polyester obtained by reacting one or more polyhydric alcohols with one or more polybasic acids, Examples of the polyhydric alcohol include 1,3-butanediol, 1,
4-butanediol, 1,6-hexanediol, diethylene glycol, triethylene glycol, neopentyl glycol, polyethylene glycol, polypropylene glycol, polybutylene glycol, trimethylolpropane, glycerin, pentaerythritol, dipentaerythritol and the like can be mentioned. . Examples of the polybasic acid include adipic acid, terephthalic acid, phthalic anhydride, trimellitic acid and the like.

Further, the hydroxyl group-containing polyether is preferably a hydroxyl group-containing polyether obtained by adding one or more kinds of alkylene oxides to the polyhydric alcohol, and the polyhydric alcohol has been described above. The same thing as a compound can be illustrated. Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide and the like.

Further, a preferable hydroxyl group-containing (meth) acrylic acid ester is a hydroxyl group-containing (meth) acrylic acid ester obtained by an esterification reaction of a polyhydric alcohol and (meth) acrylic acid, Can be exemplified by the same compounds as those mentioned above. Among such hydroxyl group-containing (meth) acrylic acid, a hydroxyl group-containing (meth) acrylic acid ester obtained by an esterification reaction of a trihydric or higher alcohol and (meth) acrylic acid is particularly preferable, and for example, dipentaerythritol pentaacrylate is used. Can be mentioned.

As the isocyanates, compounds having at least one isocyanate group in the molecule are preferable, and divalent isocyanate compounds such as tolylene diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate, and 2-isocyanate ethyl-2. And trivalent isocyanate compounds such as 6-diisocyanatecaproate.

The polyester (meth) acrylate is preferably a polyester (meth) acrylate obtained by reacting a hydroxyl group-containing polyester with (meth) acrylic acid. Preferred as the hydroxyl group-containing polyester used here is a hydroxyl group-containing polyester obtained by an esterification reaction of one or more polyhydric alcohols with one or more monobasic acids and polybasic acids. Therefore, as the polyhydric alcohol, the same compounds as the above-mentioned compounds can be exemplified. As a monobasic acid,
For example, formic acid, acetic acid, butyric acid, benzoic acid, etc. can be mentioned. Examples of the polybasic acid include adipic acid, terephthalic acid, phthalic anhydride, trimellitic acid and the like.

Preferred polyether (meth) acrylates are hydroxyl group-containing polyethers and (meth) acrylates.
It is a polyether (meth) acrylate obtained by reacting with acrylic acid. The preferred hydroxyl group-containing polyether used here is a polyhydric alcohol containing 1
A hydroxyl group-containing polyether obtained by adding one or more alkylene oxides,
As the polyhydric alcohol, the same compounds as those mentioned above can be exemplified. Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide and the like.

Preferred (meth) acrylic acid esters of alcohols are aromatic or aliphatic alcohols having at least one hydroxyl group in the molecule, and their alkylene oxide adducts reacted with (meth) acrylic acid. (Meth) acrylate obtained by, for example, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, isoamyl (meth) acrylate, lauryl (meth) acrylate, Stearyl (meth) acrylate, isooctyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 1,3-butanediol di (meth)
Acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate,
Neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified tri Methylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ε-caprolactone modified dipentaerythritol hexa (meth) acrylate and the like can be mentioned.

Further, radically polymerizable organic compounds having a sulfur atom in the molecule can be exemplified.

In the present invention, among these radically polymerizable organic compounds (b), a (meth) acrylate having an average of 3 or more (meth) acryl groups in one molecule is preferable, and more preferably, Among them, it has a (meth) acrylic group equivalent of 80 to 200 g / mol.

Such a radically polymerizable organic compound (b) is preferable because the obtained lens has good scratch resistance.

Further, such a radical-polymerizable organic compound (b) is further a urethane (meth) acrylate having a urethane bond, and more preferably, it has a urethane bond equivalent of 400 to 3000 g / mol. It is preferable.

When such a radically polymerizable organic compound (b) is used, not only the resulting lens has scratch resistance but also good deformation resistance, and the surface of the surface caused by the lens deformability is deteriorated. It becomes possible to prevent fine cracks.

The weight ratio of the radically polymerizable organic compound (a) and the radically polymerizable organic compound (b) is preferably 80:20 to 40:60.

The energy ray sensitive radical polymerization initiator (c) that can be used in the present invention is a compound capable of initiating radical polymerization by irradiation with energy rays, and includes acetophenone compounds, benzyl compounds and benzophenone compounds. Compounds and ketone compounds such as thioxanthone compounds are preferred.

Examples of acetophenone compounds include diethoxyacetophenone and 2-hydroxy-2-
Methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenyl Ethane
1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidobenzalacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl-1- [4- ( Methylthio) phenyl] -2-morpholinopropanone-1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, Examples thereof include benzoin-n-butyl ether and benzoin isobutyl ether.

Examples of benzyl compounds include benzyl and anisyl.

Examples of benzophenone compounds include benzophenone, methyl o-benzoylbenzoate,
Michler's ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide and the like can be mentioned.

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, 2-
Ethylthioxanthone, 2-chlorothioxanthone, 2
-Isopropylthioxanthone, 2,4-diethylthioxanthone and the like can be mentioned.

These energy ray sensitive radical polymerization initiators (c) can be used alone or in combination of two or more depending on the desired performance.

Of these, acylphosphine oxide compounds are preferable from the viewpoint of curability, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2,4,6-trimethylbenzoylphenyl are particularly preferable. Ethoxyphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, bis (2,6-dimethoxybenzoyl)
Examples include 2,4,4-trimethylpentylphosphine oxide.

The energy ray-sensitive radical polymerization initiator (c) is 0 based on the weight of all radical-polymerizable organic compounds (including the above-mentioned radical-polymerizable organic compound (b)) in the lens molding composition of the present invention. From the viewpoint of curability and physical properties, it is preferable to set the content to 0.05 to 10% by weight, preferably 0.1 to 10% by weight.

When the lens molding composition of the present invention further contains a cationically polymerizable organic compound (d) and an energy ray-sensitive cationic polymerization initiator (e), the curing rate and the curing by oxygen during curing It is preferable in terms of resistance to inhibition and the like.

The cationically polymerizable organic compound (d) is not particularly limited as long as it is a substance which causes a polymerization reaction or a crosslinking reaction by a cationic polymerization initiator activated by irradiation with energy rays.

Examples of such substances include epoxy compounds, oxetane compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds (styrene, vinyl ether, etc.). , These one
One kind or two or more kinds can be used.

Among these, an epoxy compound which is easy to obtain and convenient to handle is suitable. As such an epoxy compound, an aromatic epoxy compound,
Suitable examples include alicyclic epoxy compounds and aliphatic epoxy compounds.

Specific examples of the alicyclic epoxy compound include:
Examples thereof include a polyglycidyl ether of a polyhydric alcohol having at least one alicyclic ring or a cyclohexene oxide structure or a cyclopentene oxide structure-containing compound obtained by epoxidizing a cyclohexene or a cyclopentene ring-containing compound with an oxidizing agent. For example, hydrogenated bisphenol A diglycidyl ether,
3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1
-Methylhexanecarboxylate, 6-methyl-3,
4-epoxycyclohexylmethyl-6-methyl-3,
4-epoxycyclohexanecarboxylate, 3,4
-Epoxy-3-methylcyclohexylmethyl-3,4
-Epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, 2- (3,4-epoxycyclohexyl-5,5-spiro) -3,4-Epoxy) cyclohexane-metadioxane, bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexylcarboxylate, methylenebis (3,4-epoxycyclohexane), dicyclopentadiene Diepoxide, ethylenebis (3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate and the like can be mentioned.

Commercially available products which can be suitably used as the alicyclic epoxy compound are UVR-6100 and UVR-610.
5, UVR-6110, UVR-6128, UVR-6
200 (above, Union Carbide), Celoxide 2021, Celoxide 2021P, Celoxide 2
081, Celoxide 2083, Celoxide 208
5, Celoxide 2000, Celoxide 3000, Cyclomer A200, Cyclomer M100, Cyclomer M101, Eporide GT-301, Eporide G
T-302, Eporide GT-401, Eporide GT
-403, ETHB, Epolide HD300 (all manufactured by Daicel Chemical Industries, Ltd.), KRM-2110, KRM
-2199 (above, Asahi Denka Kogyo KK) etc. can be mentioned.

Among the alicyclic epoxy compounds, epoxy compounds having a cyclohexene oxide structure are preferable in terms of curability (curing speed).

Specific examples of the aromatic epoxy compound include:
Polyhydric phenol having at least one aromatic ring or polyglycidyl ether of its alkylene oxide adduct, for example, bisphenol A, bisphenol F, or glycidyl ether of a compound obtained by further adding alkylene oxide thereto, epoxy novolac resin, etc. Can be mentioned.

Specific examples of the aliphatic epoxy compound include polyglycidyl ethers of aliphatic polyhydric alcohols or alkylene oxide adducts thereof, polyglycidyl esters of aliphatic long-chain polybasic acids, vinyls of glycidyl acrylate or glycidyl methacrylate. Examples thereof include a homopolymer synthesized by polymerization, a copolymer synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and another vinyl monomer, and the like. Typical compounds include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, sorbitol tetraglycidyl ether, and dipentaerythritol. Hexaglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, and other polyhydric alcohol glycidyl ethers; and propylene glycol, trimethylolpropane, glycerin, and other aliphatic polyhydric alcohols. Polyglycidyl ether of polyether polyol obtained by adding alkylene oxide, diglycidyl ester of aliphatic long-chain dibasic acid It is below. Furthermore, monoglycidyl ethers and phenols of aliphatic higher alcohols, cresol, butylphenol, monoglycidyl ethers of polyether alcohols obtained by adding alkylene oxide to these, glycidyl esters of higher fatty acids, epoxidized soybean oil, Examples thereof include octyl epoxy stearate and butyl epoxy stearate.

Commercially available products that can be suitably used as the aromatic epoxy compound and the aliphatic epoxy compound are Epicoat 801, Epicoat 828 (all manufactured by Yuka Shell Epoxy Co., Ltd.), PY-306, 0163 and DY-022.
(Above, manufactured by Ciba Geigy), KRM-2720, EP
-4100, EP-4000, EP-4080, EP-
4088, EP-4900, ED-505, ED-50
6 (all manufactured by Asahi Denka Co., Ltd.), Epolite M-12
30, Epolite EHDG-L, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 4
00E, Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP, Epolite 1600, Epolite 80MF, Epolite 100M
F, Epolite 4000, Epolite 3002, Epolite FR-1500 (above, Kyoeisha Chemical Co., Ltd.), Suntote ST0000, YD-716, YH-300,
PG-202, PG-207, YD-172, YDPN
638 (above, Toto Kasei Co., Ltd. product) etc. can be mentioned.

Specific examples of the oxetane compound include:
3-ethyl-3-hydroxymethyl oxetane, 3-
(Meth) allyloxymethyl-3-ethyloxetane,
(3-Ethyl-3-oxetanylmethoxy) methylbenzene, 4-fluoro- [1- (3-ethyl-3-oxetanylmethoxy) methyl] benzene, 4-methoxy-
[1- (3-Ethyl-3-oxetanylmethoxy) methyl] benzene, [1- (3-Ethyl-3-oxetanylmethoxy) ethyl] phenyl ether, isobutoxymethyl (3-ethyl-3-oxetanylmethyl) ether, Isobornyloxyethyl (3-ethyl-3-oxetanylmethyl) ether, isobornyl (3-ethyl-3-oxetanylmethyl) ether, 2-ethylhexyl (3-ethyl-3-oxetanylmethyl) ether, ethyldiethylene glycol (3- Ethyl-3-oxetanylmethyl) ether, dicyclopentadiene (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenyloxyethyl (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenyl (3-
Ethyl-3-oxetanylmethyl) ether, tetrahydrofurfuryl (3-ethyl-3-oxetanylmethyl) ether, tetrabromophenyl (3-ethyl-3)
-Oxetanylmethyl) ether, 2-tetrabromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether, tribromophenyl (3-ethyl-3-)
Oxetanylmethyl) ether, 2-tribromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether, 2-hydroxyethyl (3-ethyl-3-oxetanylmethyl) ether, 2-hydroxypropyl (3-ethyl-3-) Oxetanylmethyl) ether, butoxyethyl (3-ethyl-3-oxetanylmethyl)
Ether, pentachlorophenyl (3-ethyl-3-oxetanylmethyl) ether, pentabromophenyl (3-ethyl-3-oxetanylmethyl) ether, bornyl (3-ethyl-3-oxetanylmethyl) ether, 3,7-bis ( 3-oxetanyl) -5-oxa-
Nonane, 3,3 ′-(1,3- (2-methylenyl) propanediylbis (oxymethylene)) bis- (3-ethyloxetane), 1,4-bis [(3-ethyl-3-oxetanylmethoxy) Methyl] benzene, 1,2-bis [(3-ethyl-3-oxetanylmethoxy) methyl]
Ethane, 1,3-bis [(3-ethyl-3-oxetanylmethoxy) methyl] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether,
Dicyclopentenyl bis (3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis (3
-Ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tricyclodecanediyldimethylene (3-ethyl-3-oxetanylmethyl) ether,
Trimethylolpropane tris (3-ethyl-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, 1,6-bis (3-ethyl-3-oxetanylmethoxy) hexane,
Pentaerythritol tris (3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, polyethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexakis (3-Ethyl-3-oxetanylmethyl) ether, dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol Hexakis (3-ethyl-3-oxetanylmethyl) ether, caprolactone modified dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, dito Trimethylolpropane tetrakis (3-ethyl-3-oxetanylmethyl) ether, E
O-modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, PO-modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether,
EO modified hydrogenated bisphenol A bis (3-ethyl-3-
Oxetanylmethyl) ether, PO modified hydrogenated bisphenol A bis (3-ethyl-3-oxetanylmethyl)
Ether, EO modified bisphenol F (3-ethyl-3
-Oxetanylmethyl) ether and the like can be exemplified, and these can be used alone or in combination of two or more.

A suitable blending weight ratio of the cationically polymerizable organic compound (d) is preferably 1 to 100 parts by weight of the total amount of the radically polymerizable organic compounds (sum of (a) and (b)). 30 parts by weight, more preferably 5 to
20 parts by weight.

The energy ray-sensitive cationic polymerization initiator (e) may be any compound as long as it is a compound capable of releasing a substance which initiates cationic polymerization upon irradiation with energy rays, but preferably,
A double salt, which is an onium salt that releases a Lewis acid upon irradiation with energy rays, or a derivative thereof. Representative examples of such compounds include salts of cations and anions represented by the following general formula, [A] ^{m +} [B] ^m- .

The cation [A] ^{m +} is preferably onium, and its structure can be represented by, for example, the following general formula: [(R ³ ) _a Q] ^{m +} .

Further, R ³ has 1 to 60 carbon atoms.
And is an organic group that may contain any number of atoms other than carbon atoms. a is an integer of 1 to 5. a R
Each ³ is independent and may be the same or different. Also,
At least one is preferably an organic group having an aromatic ring as described above. Q is S, N, Se, Te, P,
It is an atom or atomic group selected from the group consisting of As, Sb, Bi, O, I, Br, Cl, F, and N = N. When the valence of Q in the cation [A] ^{m +} is q,
It is necessary that the relation of m = a−q holds (however, N = N is treated as a valence of 0).

The anion [B] ^m- is preferably a halide complex, and the structure thereof can be represented by, for example, the following general formula, [LX _b ] ^m- .

Further, L is a metal or metalloid which is the central atom of the halide complex, and B, P, As, Sb, Fe, Sn, Bi, Al,
Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co
Etc. X is a halogen atom. b is an integer of 3 to 7. In addition, the valence of L in the anion [B] ^m- is p
Then, it is necessary that the relation of m = bp holds.

Specific examples of the anion [LX _b ] ^m-in the above general formula include tetrafluoroborate (BF ₄ ) ^- , hexafluorophosphate (PF ₆ ) ^- , hexafluoroantimonate (SbF ₆ ) ^- , Hexafluoroarsenate (AsF ₆ ) ^- , Hexachloroantimonate (Sb
Cl ₆₎ ^-, and the like.

As the anion [B] ^m ₋ , those having a structure represented by the following general formula, [LX _b-1 (OH)] ^m ₋ can also be preferably used.
L, X and b are the same as above. Other anions that can be used include perchlorate ion (ClO).
₄₎ ^-, trifluoromethyl sulfite ion (CF ₃ SO ₃₎
^- , Fluorosulfonate ion (FSO ₃ ) ^- , toluenesulfonate anion, trinitrobenzenesulfonate anion, tetrakis (pentafluorophenyl) borate and the like.

In the present invention, it is particularly effective to use the following aromatic onium salts (a) to (c) among these onium salts. Of these, one type may be used alone, or two or more types may be mixed and used.

(A) Aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate and 4-methylphenyldiazonium hexafluorophosphate

(B) Diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-ter)
Diaryl iodonium salts such as t-butylphenyl) iodonium hexafluorophosphate and tolylcumyl iodonium tetrakis (pentafluorophenyl) borate

(C) Triphenylsulfonium hexafluoroantimonate, tris (4-methoxyphenyl) sulfonium hexafluorophosphate, diphenyl-4-thiophenoxyphenylsulfonium hexafluoroantimonate, diphenyl-4-thiophenoxyphenylsulfonium hexafluorophosphate 4,4′-bis (diphenylsulfonio) phenyl sulfide-bis-hexafluoroantimonate,
4,4'-bis (diphenylsulfonio) phenyl sulfide-bis-hexafluorophosphate, 4,
4′-bis [di (β-hydroxyethoxy) phenylsulfonio] phenyl sulfide-bis-hexafluoroantimonate, 4,4′-bis [di (β-hydroxyethoxy) phenylsulfonio] phenyl sulfide-bis -Hexafluorophosphate, 4- [4'-
(Benzoyl) phenylthio] phenyl-di- (4-fluorophenyl) sulfonium hexafluoroantimonate, 4- [4 ′-(benzoyl) phenylthio] phenyl-di- (4-fluorophenyl) sulfonium hexafluorophosphate, 4- ( Triarylsulfonium salts such as 2-chloro-4-benzoylphenylthio) phenyl-di- (4-fluorophenyl) sulfonium hexafluoroantimonate

As another preferable example, (η
⁵ -2,4-cyclopentadiene-1-yl) [(1,
2,3,4,5,6-η)-(1-methylethyl) benzene] -iron-hexafluorophosphate and other iron-arene complexes, tris (acetylacetonato) aluminum, tris (ethylacetonatoacetato) ) A mixture of an aluminum complex such as aluminum or tris (salicylaldehdato) aluminum and a silanol such as triphenylsilanol can also be used.

Among these, aromatic iodonium salts, aromatic sulfonium salts, and iron-arene complexes are preferably used from the viewpoint of practical use and photosensitivity.

The ratio of the energy ray-sensitive cationic polymerization initiator (e) to the above-mentioned cationically polymerizable organic compound (d) is not particularly limited, and it may be used at a generally usual ratio within the range not impairing the object of the present invention. However, for example, with respect to 100 parts by weight of a cationically polymerizable organic compound having one or more epoxide structures in the molecule,
Energy ray sensitive cationic polymerization initiator 0.05-10
It may be part by weight, preferably 0.5 to 10 parts by weight. If the amount is too small, the curing tends to be insufficient, and if the amount is too large, the strength of the cured product may be adversely affected.

The lens of the present invention is obtained by injecting the energy ray-curable resin composition of the present invention into an arbitrary mold that transmits energy rays, irradiating it with active energy rays to cure the resin composition, and releasing it. be able to.

[0064]

EXAMPLES [Examples 1 to 8 and Comparative Example 1] The following materials were used and mixed in the proportions shown in Tables 1 and 2 below to obtain respective lens molding compositions. Each of these compositions was poured into a mirror-finished glass mold (diameter: 70 mm, thickness: 2 mm), irradiated with ultraviolet rays of 10 J / cm ² from both sides of the mold to cure, and released from the mold to obtain a lens. The refractive index and surface scratch resistance of these lenses were measured. The obtained results are shown in Tables 1 and 2 below.

The ingredients used in Tables 1 and 2 are as shown below. Radical polymerizable organic compound (a-1): compound having the following structural formula Radical polymerizable organic compound (a-2): compound having the following structural formula Radical polymerizable organic compound (a-3): compound having the following structural formula Radical polymerizable organic compound (b-1): dipentaerythritol hexaacrylate Radical polymerizable organic compound (b-2): 2-isocyanatoethyl-2,6-diisocyanatocaproate and dipentaerythritol pentaacrylate are reacted. The resulting 15-functional urethane acrylate energy ray-sensitive radical polymerization initiator (c-1):
2,4,6-Trimethylbenzoyldiphenylphosphine oxide cationically polymerizable organic compound (d-1): 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate energy ray sensitive cationic polymerization initiator (e-1) :
4,4′-Bis [di (β-hydroxyethoxy) phenylsulfonio] phenyl sulfide-bis-hexafluoroantimonate

The scratch resistance in Tables 1 and 2 was measured as follows. Scratch resistance: 30 cm under a load of 4.9 N / 6 cm ² (500 g / 6 cm ² ) on which # 0000 steel wool is placed.
The sample was rubbed 100 times at a speed of / minute and the haze difference before and after the test was measured with a turbidimeter.

[0067]

[Table 1]

[0068]

[Table 2]

[0069]

According to the present invention, it is possible to provide a lens molding composition which can obtain a lens having a high refractive index and a scratch resistance, and a lens using the same.

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Claims (5)

[Claims] 1. A lens molding composition which is cured by irradiation with energy rays, wherein the following general formula (1): (In the formula, each R is a hydrogen atom or a methyl group and may be the same or different) and an average of 3 or more (meta) in one molecule.
A lens molding composition comprising a radically polymerizable organic compound (b) composed of (meth) acrylate having an acrylic group and an energy ray sensitive radical polymerization initiator (c) as essential components. 2. The radically polymerizable organic compound (b)
The lens-forming composition according to claim 1, wherein is a urethane (meth) acrylate further having a urethane bond. 3. The lens-forming composition according to claim 1, further comprising a cationically polymerizable organic compound (d) and an energy ray-sensitive cationic polymerization initiator (e). 4. The lens molding composition according to claim 1, wherein the energy ray-sensitive radical polymerization initiator (c) is an acylphosphine oxide compound. 5. The lens molding composition according to claim 1, which is obtained by injecting the composition for lens molding according to any one of claims 1 to 4 into a mold, curing the composition by irradiation with active energy rays, and releasing the composition from the mold. Lens to be.