JP2020101615A - Composition for optical material, and optical lens using the same - Google Patents

Abstract

To provide a composition for an optical material which gives high strength, refractive index and Abbe number, can make a lens thinner, and can improve color tone of a lens.SOLUTION: A composition for optical material in which a ratio [(c)/{(a)+(b)}] of the gross weight of (c) 1,2,3,5,6-pentathiepane to the gross weight of (a) a compound having two or more of isocyanate group and/or isothiocyanate group per molecule and (b) a compound having two or more of mercapto group per molecule is 0.03 to 0.30.SELECTED DRAWING: None

Description

The present invention relates to an optical material such as a plastic lens, a prism, an optical fiber, an information recording substrate, a filter, and the like, and more particularly to a composition for an optical material which is preferably used as a raw material for a plastic lens for eyeglasses and an optical lens using the same.

Plastic materials have been widely used in recent years for various optical materials, particularly spectacle lenses, because they are lightweight, rich in toughness, and easy to dye. The optical materials, especially the performance required for eyeglass lenses, are low specific gravity, high transparency, low yellowness, high strength, high refractive index and high Abbe number as optical performance, and high strength and high refractive index Enables thinning.
In recent years, in order to maintain a high refractive index and a high Abbe number, as a novel episulfide compound, a linear polyepisulfide compound is disclosed in Patent Document 1, a branched polyepisulfide compound is disclosed in Patent Document 2, and a cyclic skeleton is disclosed in Patent Document 3. Patent Document 4 proposes a polyepisulfide compound having a selenium atom, and the like.
Since these compounds were capable of homopolymerization, a sufficiently high balance between the refractive index of 1.70 or more and the Abbe number of 30 or more and the Abbe number was achieved, but the strength was not sufficiently high. Therefore, it became necessary to secure a certain thickness, and although the high refractive index made it possible to design a thin thickness, the strength was a major obstacle to thinning.
In order to improve these, Patent Document 5 proposed a composition for optical materials containing an isocyanate group, an isothiocyanate group and sulfur, but the lens produced by this method had a problem that the color tone was poor.

JP-A-9-110979 JP-A-9-71580 JP, 9-255781, A JP, 11-140046, A JP, 2002-082023, A

It is an object of the present invention to provide a composition for an optical material, which provides high strength, a refractive index and an Abbe's number, enables the lens to be thin, and improves the lens color tone, and an optical lens using the same. And

As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that (a) a compound having two or more isocyanate groups and/or isothiocyanate groups per molecule, and (b) two mercapto groups per molecule. It has been found that the above problems can be solved by a compound having the above and (c) a composition for an optical material containing 1,2,3,5,6-pentathiepan represented by the following structural formula in a specific weight ratio.

That is, the present invention is as follows.
<1> (c) 1,2 relative to the total weight of (a) a compound having two or more isocyanate groups and/or isothiocyanate groups per molecule and (b) a compound having two or more mercapto groups per molecule The composition for optical materials is characterized in that the ratio [(c)/{(a)+(b)}] of the total weight of 3,3,5,6-pentathiepan is 0.03 to 0.30. ..
<2> (a) A compound having two or more isocyanate groups and/or isothiocyanate groups per molecule is metaxylylene diisocyanate, 2,5-bis(isocyanatomethyl)-1,4-dithiane, dicyclohexylmethane- The composition for optical materials according to <1>, which contains at least one selected from the group consisting of 4,4′-diisocyanate, hexamethylene diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane. ..
<3> (b) A compound having two or more mercapto groups per molecule is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,5-bis(mercaptomethyl)-1,4- <1> or <2>, containing at least one selected from the group consisting of dithiane, 2-mercaptomethyl-1,5-dimercapto-3-thiapentane, and pentaerythritol tetrakis (3-mercaptopropionate). The composition for optical materials described in 1.
<4> (b) The composition for optical materials according to <1> or <2>, wherein the compound having two or more mercapto groups per molecule has a sulfide bond.
<5> An optical material obtained by polymerizing and curing the composition for optical material according to any one of <1> to <4>.
<6> An optical lens made of the optical material according to <5>.

ADVANTAGE OF THE INVENTION According to this invention, the composition for optical materials which can give sufficient high intensity|strength, a refractive index, and an Abbe's number which has not existed in the prior art, and an optical lens using the same can be provided. As a result, the lens can be made thinner and a lens having an excellent color tone can be provided.

Hereinafter, the composition for an optical material of the present invention, an optical material obtained by polymerizing and curing the same, and an optical lens made of the optical material will be specifically described. The materials, configurations, and the like described below do not limit the present invention and can be variously modified within the scope of the gist of the present invention.

One embodiment of the present invention includes (a) a compound having two or more isocyanate groups and/or isothiocyanate groups per molecule (hereinafter, may be referred to as “(a) compound”), and (b) a mercapto group. (C) 1,2,3,5,6-pentatiepan (hereinafter, referred to as “(c)”) based on the total weight of the compound having 2 or more per molecule (hereinafter, may be referred to as “(b) compound”). The composition for optical materials is characterized in that the ratio [(c)/{(a)+(b)}] of the total weight of the compound) is 0.03 to 0.30. .. The weight ratio represented by the above [(c)/{(a)+(b)}] is preferably 0.04 to 0.20, and more preferably 0.05 to 0.15.
The ratio of the compound (a), the compound (b) and the compound (c) in the composition for optical materials of the present invention is a weight ratio represented by the above [(c)/{(a)+(b)}]. Can be in any ratio as long as it satisfies the range of 0.03 to 0.30, preferably (a) compound 10 to 90 parts by weight, (b) compound 10 to 90 parts by weight, (c) compound 0. It is in the range of 1 to 50 parts by weight. When the respective ranges of the compound (a), the compound (b), and the compound (c) are exceeded, high impact resistance, which is the object of the present invention, may not be obtained. Further, there are cases in which sufficient heat resistance cannot be obtained, the color tone of the cured product deteriorates, and the high refractive index and high Abbe number, which are one of the objects of the present invention, cannot be obtained. The range is more preferably (a) compound 20 to 80 parts by weight, (b) compound 20 to 80 parts by weight, (c) compound 1 to 40 parts by weight, still more preferably (a) compound 20 to 70 parts by weight, It is in the range of 20 to 70 parts by weight of the compound (b) and 5 to 30 parts by weight of the compound (c). Further, in order to develop a high refractive index which is one of the objects of the present invention, the compound (b) preferably has a sulfur and/or selenium atom in addition to the mercapto group, more preferably a mercapto group. In addition, it has a sulfur atom, and more preferably has a sulfide bond in addition to the mercapto group.

The compound (a) used in the present invention includes all compounds having two or more isocyanate groups and/or isothiocyanate groups per molecule, and specific examples thereof include diethylene diisocyanate, tetramethylene diisocyanate and hexamethylene. Diisocyanate, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 2,6-bis(isocyanatomethyl)decahydronaphthalene , Lysine triisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, o-tolidine diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenyl ether diisocyanate, 3-(2'-isocyanatocyclohexyl)propyl isocyanate, tris (Phenylisocyanate) thiophosphate, isopropylidene bis(cyclohexyl isocyanate), 2,2'-bis(4-isocyanatophenyl)propane, triphenylmethane triisocyanate, bis(diisocyanate tolyl)phenylmethane, 4,4',4''-Triisocyanate-2,5-dimethoxyphenylamine,3,3'-dimethoxybenzidine-4,4'-diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4'-diisocyanato Biphenyl, 4,4'-diisocyanato-3,3'-dimethylbiphenyl, dicyclohexylmethane-4,4'-diisocyanate, 1,1'-methylenebis(4-isocyanatobenzene), 1,1'-methylenebis(3- Methyl-4-isocyanatobenzene), m-xylylene diisocyanate, p-xylylene diisocyanate, 1,3-bis(1-isocyanate-1-methylethyl)benzene, 1,4-bis(1-isocyanate-1-) Methylethyl)benzene, 1,3-bis(2-isocyanato-2-propyl)benzene, 2,6-bis(isocyanatomethyl)naphthalene, 1,5-naphthalene diisocyanate, bis(isocyanatomethyl)tetrahydrodicyclopentadiene, Bis(isocyanatomethyl)dicyclopentadiene, bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanate Tyl norbornene, bis(isocyanatomethyl)adamantane, dimer acid diisocyanate, 1,3,5-tri(1-isocyanatohexyl)isocyanuric acid, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, bis[(4-isocyanate Natomethyl)phenyl] sulfide, 2,5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl-1,4-dithiane, 2,5-diisocyanatomethylthiophene, dithiodiethyldiisocyanate, dithiodiene Isocyanates such as propyl diisocyanate, 2,5-bis(isocyanatomethyl)-1,4-dithiane, and compounds in which all or part of the isocyanate groups of the above isocyanates are replaced with isothiocyanate groups be able to. Further, among the above, polyisocyanates include isocyanates such as dimers, cyclized trimers and adducts of alcohols or thiols by a Burette type reaction.
Among these, metaxylylene diisocyanate, 2,5-bis(isocyanatomethyl)-1,4-dithiane, dicyclohexylmethane-4,4'-diisocyanate, hexamethylene diisocyanate, and 1,3-bis(isocyanatomethyl) ) Cyclohexane is preferred.

The compound (b) used in the present invention includes all compounds having two or more mercapto groups per molecule, and specific examples thereof include methanedithiol, methanetrithiol, 3-mercaptopropanol and 2-mercapto. Propanol, 2-phenyl-2-mercaptoethanol, 1,2-dimercaptoethane, 1,2-dimercaptopropane, 1,3-dimercaptopropane, 2,2-dimercaptopropane, 1,4-dimercaptobutane 1,6-dimercaptohexane, bis(2-mercaptoethyl)ether, bis(2-mercaptoethyl)sulfide, 1,2-bis(2-mercaptoethyloxy)ethane, 1,2-bis(2-mercapto) Ethylthio)ethane, 2,3-dimercapto-1-propanol, 1,3-dimercapto-2-propanol, 1,2,3-trimercaptopropane, 2-mercaptomethyl-1,3-dimercaptopropane, 2- Mercaptomethyl-1,4-dimercaptobutane, 2-(2-mercaptoethylthio)-1,3-dimercaptopropane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,4- Dimercaptomethyl-1,5-dimercapto-3-thiapentane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11- Dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,1-tris(mercaptomethyl)propane, tetrakis (Mercaptomethyl)methane, ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1, 4-butanediol bis(2-mercaptoacetate), 1,4-butanediol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate) ), pentaerythritol tetrakis (2-mercaptocetate), pentaerythritol tetrakis (3-mercaptopropionate), 1,2-dimercaptocyclohexane, 1,3-dimercaptosic Rohexane, 1,4-dimercaptocyclohexane, 1,3-bis(mercaptomethyl)cyclohexane, 1,4-bis(mercaptomethyl)cyclohexane, 2,5-bis(mercaptomethyl)-1,4-dithiane, 2, 5-bis(2-mercaptoethyl)-1,4-dithiane, 2,5-bis(2-mercaptoethylthiomethyl)-1,4-dithiane, 2,5-bis(mercaptomethyl)-1-thiane, 2,5-bis(2-mercaptoethyl)-1-thiane, 2,5-bis(mercaptomethyl)thiophene, thiophenol, 4-tert-butylthiophenol, 2-methylthiophenol, 3-methylthiophenol, 4- Methylthiophenol, 2-vinylthiophenol, 3-vinylthiophenol, 4-vinylthiophenol, 2-hydroxythiophenol, 3-hydroxythiophenol, 4-hydroxythiophenol, 1,2-dimercaptobenzene, 1,3 -Dimercaptobenzene, 1,4-dimercaptobenzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 2,2'-dimercaptobiphenyl, 4,4'-di Mercaptobiphenyl, bis(4-mercaptophenyl)methane, 2,2-bis(4-mercaptophenyl)propane, bis(4-mercaptophenyl)ether, bis(4-mercaptophenyl)sulfide, bis(4-mercaptophenyl) Sulfone, bis(4-mercaptomethylphenyl)methane, 2,2-bis(4-mercaptomethylphenyl)propane, bis(4-mercaptomethylphenyl)ether, bis(4-mercaptomethylphenyl)sulfide, mercaptobenzoic acid, 2-mercaptoimidazole, 2-mercapto-1-methylimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 3,4-thiophenedithiol, glyceryl dithioglycolate, 2-selenoethanol, bis(2-mercapto Ethyl) selenide, bis(1,3-dimercapto-2-propyl) selenide, 2,3-bis(mercaptoethylseleno)-1-propanethiol, 2-mercaptomethyl-1,5-dimercapto-3-selenapentane, 2-mercaptomethyl-1,5-dimercapto-3-thiapentane, 4,8-bis(mercaptomethyl)-1,11-dimercapto-3,9-dithia-6-selenaundecane, 4,8 -Bis(mercaptomethyl)-1,11-dimercapto-6-thia-3,9-diselenaundecane, 4,8-bis(mercaptomethyl)-1,11-dimercapto-3,6,9-triselenaundecane , Bis(hydroxymercaptoethylselenomethyl)benzene, 1,4-dimercapto-2,3-bis(mercaptoethylseleno)butane, 1,2,3,4-tetrakis(mercaptoethylseleno)butane, 1,9-dimercapto -5,5-bis(mercaptomethyl)-3,7-diselenanane, tris(mercaptomethyl)-1,8-dimercapto-6-thia-3-selenaoctane, bis(mercaptoethylselenomethyl)benzene, 2,5 -Diseleno-1,4-dithiane, 2,5-bis(selenomethyl)-1,4-dithiane, 2,5-bis(mercaptoethylselenomethyl)-1,4-dithiane, 2,6-dimercapto-1- Serena-4-thian, 3,5-dimercapto-1-selena-4-thian, 2,6-bis(mercaptomethyl)-1-selena-4-thian, 3,5-bis(mercaptomethyl)-1- Serena-4-thian, 2,5-dimercapto-1,4-diselenan, 2,6-dimercapto-1,4-diselenan, 2,5-bis(mercaptomethyl)-1,4-diselenan, 2,6- Bis(mercaptomethyl)-1,4-diselenan, 2,5-dimercaptoselenane, 3,4-dimercaptoselenane, 2,5-bis(mercaptomethyl)selenane, 3,4-bis(mercaptomethyl) Selenane, 2,5-bis(selenomethyl)selenane, 3,4-bis(selenomethyl)selenane, 4,5-dimercapto-1,3-diselenolane, 4,5-bis(mercaptomethyl)-1,3-diselenolane, 3,6-dimercaptotriselenocyclooctane, 3,6-bis(mercaptomethyl)triselenocyclooctane, 3,6-diselenotriselenocyclooctane, 3,6-bis(selenomethyl)triselenocyclooctane, etc. Regarding mercaptans and polymercaptans among them, oligomers of dimers to 20-mers thereof can be mentioned.
Among these, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,5-bis(mercaptomethyl)-1,4-dithiane, 2-mercaptomethyl-1,5-dimercapto-3- Thiapentane, and pentaerythritol tetrakis(3-mercaptopropionate) are preferred.
Further, the compound (b) used in the present invention preferably has a sulfide bond, and examples of such a compound include bis(2-mercaptoethyl)sulfide, 2,5-dimercaptomethyl-1, 4-dithiane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-bis(2-mercaptoethylthiomethyl)-1,4-dithiane and the like can be mentioned.

The compound (c) used in the present invention is 1,2,3,5,6-pentathiepan represented by the above formula. 1,2,3,5,6-Pentiepan has the effect of improving the refractive index and color tone of the optical material (resin) obtained from the composition for optical materials of the present invention.
The method for obtaining 1,2,3,5,6-pentathiepan is not particularly limited. A commercially available product may be used, or it may be collected and extracted from a natural product such as crude oil or animals and plants, or may be synthesized by a known method.
As an example of the synthesis method, N. Takeda et al., Bull. Chem. Soc. Jpn. , 68, 2757 (1995), F.I. Feher et al., Angew. Chem. Int. Ed. , 7, 301 (1968), G.I. W. Kutney et al., Can. J. Chem, 58, 1233 (1980) and the like.

Specific examples of the compound (a), the compound (b) and the compound (c) have been described above. The compound (a) has a compound having two or more isocyanate groups and/or isothiocyanate groups per molecule, and (b) The compound is not limited to the compounds listed above as long as the compound has two or more mercapto groups per molecule. Each of these compounds may be used alone or in combination of two or more.

The optical material of the present invention is obtained by heat-polymerizing a composition for an optical material containing a compound (a), a compound (b) and a compound (c) in a specific weight ratio in the presence or absence of a curing catalyst. It can be manufactured. A preferred method is to use a curing catalyst, and examples of the curing catalyst include amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acids, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, sulfenamides, thiuram Examples thereof include dithiocarbamates, xanthates, acidic phosphates and the like. Typical examples of these are shown below.
(1) Ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mistilyl Ruamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine , 3-propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3-(2-ethylhexyloxy)propylamine, aminocyclopentane, aminocyclohexane, aminonorbornene, amino Primary amines such as methylcyclohexane, aminobenzene, benzylamine, phenethylamine, α-phenylethylamine, naphthylamine and furfurylamine; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1 ,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, Bis-(3-aminopropyl)ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, aminoethylethanolamine, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- Alternatively, 1,4-bisaminopropylcyclohexane, hydrogenated 4,4′-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethyl Piperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine, isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-, m-, or p-phenylenediamine, 2, 4- or 2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl- m-phenylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, benzidine, 4,4'-bis(o-toluidine), dianisidine, 4,4'-diamino Diphenylmethane, 2,2-(4,4'-diaminodiphenyl)propane, 4,4'-diaminodiphenyl ether, 4,4'-thiodianiline, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminoditolyl sulfone , Methylenebis(o-chloroaniline), 3,9-bis(3-aminopropyl)2,4,8,10-tetraoxaspiro[5,5]undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine , Bis(hexamethylene)triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperazine, N-aminopropylpiperazine, 1,4-bis(aminoethylpiperazine), 1,4-bis( Aminopropylpiperazine), 2,6-diaminopyridine, bis(3,4-diaminophenyl)sulfone, and other primary polyamines; diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, diamine -N-pentylamine, di-3-pentylamine, dihexylamine, octylamine, di(2-ethylhexyl)amine, methylhexylamine, diallylamine, pyrrolidine, piperidine, 2-, 3-, 4-picoline, 2,4 Secondary amines such as -, 2,6-, 3,5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole and morpholine; N , N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N , N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1,4-diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1, 6-diaminohexane, N , N'-Dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N , N'-diethyl-1,2-diaminobutane, N,N'-diethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1, 6-diaminohexane, piperazine, 2-methylpiperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)methane, 1,2-di-(4-piperidyl) ) Secondary polyamines such as ethane, 1,3-di-(4-piperidyl)propane, 1,4-di-(4-piperidyl)butane; trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propyl Amine, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-pentylamine, tri-3-pentylamine, Tri-n-hexylamine, tri-n-octylamine, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, dicyclohexylethylamine, cyclohexyldiethylamine, tri-cyclohexylamine, N,N-dimethylhexylamine, N-methyldihexylamine, N,N-dimethylcyclohexylamine, N-methyldicyclohexylamine, N,N-diethylethanolamine, N,N-dimethylethanolamine, N-ethyldiethanolamine, triethanolamine, tribenzylamine, N , N-dimethylbenzylamine, diethylbenzylamine, triphenylamine, N,N-dimethylamino-p-cresol, N,N-dimethylaminomethylphenol, 2-(N,N-dimethylaminomethyl)phenol, N, 3 such as N-dimethylaniline, N,N-diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, 2-(2-dimethylaminoethoxy)-4-methyl-1,3,2-dioxabornane Secondary amine; tetramethylethylenediamine, pyrazine, N,N'-dimethylpiperazine, N,N'-bis((2-hydroxy)propyl)piperazine, hexamethylenetetramine, N,N,N',N'-tetramethyl- 1,3 -Butanamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N,N,N-tris(3-dimethylaminopropyl)amine, 2,4,6-tris(N,N-dimethylaminomethyl)phenol, Tertiary polyamines such as heptamethylisobiguanide; imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole, N-butylimidazole, 2- Butyl imidazole, N-undecyl imidazole, 2-undecyl imidazole, N-phenyl imidazole, 2-phenyl imidazole, N-benzyl imidazole, 2-benzyl imidazole, 2-mercapto imidazole, 2-mercapto-N-methyl imidazole, 2 -Mercaptobenzimidazole, 3-mercapto-4-methyl-4H-1,2,4-triazole, 5-mercapto-1-methyl-tetrazole, 2,5-dimercapto-1,3,4-thiadiazole 1-benzyl- 2-methylimidazole, N-(2'-cyanoethyl)-2-methylimidazole, N-(2'-cyanoethyl)-2-undecylimidazole, N-(2'-cyanoethyl)-2-phenylimidazole, 3, Various imidazoles such as 3-bis-(2-ethyl-4-methylimidazolyl)methane, an adduct of alkylimidazole and isocyanuric acid; 1,8-diazabicyclo(5,4,0)undecene-7,1,5 -Amidines such as diazabicyclo(4,3,0)nonene-5,6-dibutylamino-1,8-diazabicyclo(5,4,0)undecene-7; amine compounds represented by the above.

(2) A complex of the amine of (1) with borane and boron trifluoride.
(3) Trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine Fin, tribenzylphosphine, tris(2-methylphenyl)phosphine, tris(3-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, tris(diethylamino)phosphine, tris(4-methylphenyl)phosphine, dimethylphenyl Phosphines such as phosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine and chlorodiphenylphosphine.
(4) Tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium acetate, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium acetate, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n -Butylammonium bromide, tetra-n-butylammonium iodide, tetra-n-butylammonium acetate, tetra-n-butylammonium borohydride, tetra-n-butylammonium hexafluorophosphite, tetra-n-butylammonium hydrogensal Fight, tetra-n-butylammonium tetrafluoroborate, tetra-n-butylammonium tetraphenylborate, tetra-n-butylammonium paratoluene sulfonate, tetra-n-hexylammonium chloride, tetra-n-hexylammonium bromide, Tetra-n-hexyl ammonium acetate, tetra-n-octyl ammonium chloride, tetra-n-octyl ammonium bromide, tetra-n-octyl ammonium acetate, trimethyl-n-octyl ammonium chloride, trimethyldecyl ammonium chloride, trimethyldodecyl ammonium chloride, Trimethylcetylammonium chloride, trimethyllaurylammonium chloride, trimethylbenzylammonium chloride, trimethylbenzylammonium bromide, triethyl-n-octylammonium chloride, triethylbenzylammonium chloride, triethylbenzylammonium bromide, tri-n-butyl-n-octylammonium chloride, Tri-n-butylbenzylammonium fluoride, tri-n-butylbenzylammonium chloride, tri-n-butylbenzylammonium bromide, tri-n-butylbenzylammonium iodide, n-butyldimethylbenzylammonium chloride, n-octyldimethyl Benzylammonium chloride, decyldimethylbenzylammonium chloride, dodecyldimethylbenzylammonium chloride, cetyldimethylbenzylammonium chloride, lauryldimethylbenzylammonium chloride, methyl Rutriphenylammonium chloride, methyltribenzylammonium chloride, methyltriphenylammonium bromide, methyltribenzylammonium bromide, ethyltriphenylammonium chloride, ethyltribenzylammonium chloride, ethyltriphenylammonium bromide, ethyltribenzylammonium bromide, n-butyl Triphenylammonium chloride, n-butyltribenzylammonium chloride, n-butyltriphenylammonium bromide, n-butyltribenzylammonium bromide, 1-methylpyridinium chloride, 1-methylpyridinium bromide, 1-ethylpyridinium chloride, 1-ethyl Pyridinium bromide, 1-n-butylpyridinium chloride, 1-n-butylpyridinium bromide, 1-n-hexylpyridinium chloride, 1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide, 1-n-dodecylpyridinium chloride , 1-n-dodecylpyridinium bromide, 1-n-cetylpyridinium chloride, 1-n-cetylpyridinium bromide, 1-phenylpyridinium chloride, 1-phenylpyridinium bromide, 1-benzylpyridinium chloride, 1-benzylpyridinium bromide, 1 -Methylpicolinium chloride, 1-methylpicolinium bromide, 1-ethylpicolinium chloride, 1-ethylpicolinium bromide, 1-n-butylpicolinium chloride, 1-n-butylpicolinium bromide, 1-n-hexyl Picolinium chloride, 1-n-hexylpicolinium bromide, 1-n-octylpicolinium chloride, 1-n-octylpicolinium bromide, 1-n-dodecylpicolinium chloride, 1-n-dodecylpicolinium bromide, 1 Quaternary ammonium salts such as -n-cetylpicolinium chloride, 1-n-cetylpicolinium bromide, 1-phenylpicolinium chloride, 1-phenylpicolinium bromide 1-benzylpicolinium chloride and 1-benzylpicolinium bromide.
(5) Tetramethylphosphonium chloride, tetramethylphosphonium bromide, tetraethylphosphonium chloride, tetraethylphosphonium bromide, tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide, tetra-n-butylphosphonium iodide, tetra-n- Hexylphosphonium bromide, tetra-n-octylphosphonium bromide, methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide, ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, n-butyltriphenylphosphonium bromide, n-butyltrinium Phenylphosphonium iodide, n-hexyltriphenylphosphonium bromide, n-octyltriphenylphosphonium bromide, tetraphenylphosphonium bromide, tetrakishydroxymethylphosphonium chloride, tetrakishydroxymethylphosphonium bromide, tetrakishydroxyethylphosphonium chloride, tetrakishydroxybutylphosphonium chloride, etc. Phosphonium salt.
(6) Trimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate, tri-n- Sulfonium salts such as hexylsulfonium bromide, tri-n-octylsulfonium bromide, triphenylsulfonium chloride, triphenylsulfonium bromide, triphenylsulfonium iodide.
(7) Iodonium salts such as diphenyliodonium chloride, diphenyliodonium bromide and diphenyliodonium iodide.
(8) Hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid and other mineral acids and their half-esters.

(9) Boron trifluoride, boron trifluoride etherate, aluminum fluoride, aluminum chloride, triphenylaluminum, potassium octanoate, calcium acetate, tetraisopropoxy titanium, tetrabutoxy titanium, tetrachloro titanium, titanate 2- Ethylhexyl, dimethyltin oxide, dimethyltin dichloride, dibutyltin diacetate, dibutyltin acetate, dibutyltin dilaurate, dibutyltin laurate, dibutyltin octanoate, dibutyltin bis(dodecyl mercaptide), dibutyltin bis(isooctyl thioglycolate), dibutyltin oxide, Butyltin trichloride, dibutyltin dichloride, tributyltin chloride, tetrabutyltin, dioctyltin diacetate, dioctyltin acetate, dioctyltin dilaurate, dioctyltin laurate, dioctyltin diricinolate, dioctyltin dioleate, dioctyltin di(6-hydroxy) ) Caproate, dioctyl tin bis (isooctyl thioglycolate), dioctyl tin oxide, dioctyl tin dichloride, dioctyl tin maleate, dioctyl tin bis (butyl maleate), didodecyl tin diricinolate, tin stearate, zinc chloride, Lewis acids such as zinc acetylacetone, copper oleate, copper acetylacetone, iron acetylacetone, iron naphthenate, iron lactate, iron citrate, and iron gluconate.
(10) Organic acids and their half-esters.
(11) Silicic acid, tetrafluoroboric acid.
(12) Cumyl peroxy neodecanoate, diisopropyl peroxy dicarbonate, diallyl peroxy dicarbonate, di-n-propyl peroxy dicarbonate, dimyristyl peroxy dicarbonate, cumyl peroxy neohexanoate, tert- Hexyl peroxy neodecanoate, tert-butyl peroxy neodecanoate, tert-hexyl peroxy neohexanoate, tert-butyl peroxy neohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide , Peroxides such as dicumyl peroxide and di-ter-butyl peroxide; peroxides such as cumene hydroperoxide and tert-butyl hydroperoxide.
(13) 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2,4- Dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 1-[ (1-Cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethyl-valeronitrile 2,2′-azobis(2-methylpropane),2,2′-azobis( Azo compounds such as 2,4,4-trimethylpentane).
(14) Reaction product of acetaldehyde and ammonia, condensation product of formaldehyde and para-ylidine, condensation product of acetaldehyde and para-ylidine, reaction product of formaldehyde and aniline, reaction product of acetaldehyde and aniline, reaction product of butyraldehyde and aniline, formaldehyde and acetaldehyde Reaction of aniline, reaction of acetaldehyde and butyraldehyde and aniline, condensation of butyraldehyde and monobutylamine, reaction of butyraldehyde and butylideneaniline, reaction of heptaldehyde and aniline, reaction of tricrotonylidene-tetramine , A condensation product of α-ethyl-β-propylacrolein and aniline, a condensation product of formaldehyde and alkylimidazole, and the like, a condensation product of an aldehyde and an amine compound.
(15) Diphenylguanidine, phenyltolylguanidine, phenylxylylguanidine, tolylxylylguanidine, diortotolylguanidine, orthotolylguanide, diphenylguanidine phthalate, tetramethylguanidine, diorthotolylguanidine salt of dicatecholboric acid, etc. Guanidines.
(16) Thiourea compounds such as thiocarboanilide, dioltotolylthiourea, ethylenethiourea, diethylthiourea, dibutylthiourea, dilaurylthiourea, trimethylthiourea, dimethylethylthiourea and tetramethylthiourea.
(17) 2-mercaptobenzothiazole, dibenzothiazyl disulfide, cyclohexylamine salt of 2-mercaptobenzothiazole, 2-(2,4-dinitrophenylthio)benzothiazole, 2-(morpholinodithio)benzothiazole, 2-( 2,6-Dimethyl-4-morpholinothio)benzothiazole, N,N-diethylthiocarbamoyl-2-benzothiazolyl sulfide, 1,3-bis(2-benzothiazolylmercaptomethyl)urea, benzothiadiadi Thiazoles such as ruthiobenzoate, 2-mercaptothiazoline, sodium salt of 2-mercaptobenzothiazole, zinc salt of 2-mercaptobenzothiazole, complex salt of dibenzothiazyl disulfide and zinc chloride.
(18) N-cyclohexyl-2-benzothiazylsulfenamide, N-tert-butyl-2-benzothiazylsulfenamide, N-tert-octyl-2-benzothiazylsulfenamide, N-oxydiethylene 2-benzothiazylsulfenamide, N,N-diethyl-2-benzothiazylsulfenamide, N,N-diisopropyl-2-benzothiazylsulfenamide, N,N-dicyclohexyl-2-benzothia Sulfenamides such as dilsulfenamide.
(19) Tetramethylthiuram monosulfide, tetraethylthiuram monosulfide, tetrabutylthiuram monosulfide, dipentamethylenethiuram monosulfide, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetrabutylthiuram disulfide, N,N′-dimethyl-N, Thiurams such as N'-diphenylthiuram disulfide, N,N'-diethyl-N,N'-diphenylthiuram disulfide, dipentamethylene thiuram disulfide, dipentamethylene thiuram tetrasulfide, cyclic thiuram.
(20) Sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate, sodium dibutyldithiocarbamate, sodium pentamethylenedithiocarbamate, sodium cyclohexylethyldithiocarbamate, potassium dimethyldithiocarbamate, lead dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate, Zinc dibutyldithiocarbamate, zinc dibenzyldithiocarbamate, zinc pentamethylenedithiocarbamate, zinc dimethylpentamethylenedithiocarbamate, zinc ethylphenyldithiocarbamate, bismuth dimethyldithiocarbamate, cadmium diethyldithiocarbamate, cadmium pentamethylenedithiocarbamate, selenium dimethyldithiocarbamate , Selenium diethyldithiocarbamate, tellurium dimethyldithiocarbamate, tellurium diethyldithiocarbamate, iron dimethyldithiocarbamate, copper dimethyldithiocarbamate, diethylammonium diethyldithiocarbamate, dibutyldithiocarbamate N,N-cyclohexylammonium, piperidine pentamethylenedithiocarbamate, cyclohexylethyl Dithiocarbamate salts such as cyclohexylethylammonium sodium dithiocarbamate, pipecoline methylpentamethylenedithiocarbamate, and a complex compound of zinc pentamethylenedithiocarbamate and piperidine.
(21) Xanthates such as sodium isopropylxanthate, zinc isopropylxanthate, zinc butylxanthate, and dibutylxanthate disulfide. (22) Mono- and/or dimethylphosphoric acid, mono- and/or diethylphosphoric acid, mono- and/or dipropylphosphoric acid, mono- and/or dibutylphosphoric acid, mono- and/or dihexylphosphoric acid, mono- and/or Or an acid such as dioctylphosphoric acid, mono- and/or didecylphosphoric acid, mono- and/or didodecylphosphoric acid, mono- and/or diphenylphosphoric acid, mono- and/or dibenzylphosphoric acid, mono- and/or didecanol phosphoric acid Phosphate esters.

Although the curing catalyst for polymerizing and curing the optical material composition of the present invention has been exemplified above, the compounds are not limited to these listed compounds as long as they exhibit the effect of polymerizing and curing. These may be used alone or in combination of two or more. The addition amount of the catalyst used in the present invention is 0.0001 to 10.0 parts by weight, preferably 0.0005 to 5.0 parts by weight, based on 100 parts by weight of the composition for optical materials. When the amount of the curing catalyst is more than 10.0 parts by weight, the refractive index and heat resistance of the cured product are lowered, and coloring occurs. On the other hand, if the amount is less than 0.0001 parts by weight, the composition will not be sufficiently cured and heat resistance will be insufficient.

To the composition for optical materials of the present invention, a compound capable of reacting with a part or all of the composition components is added as a performance improving agent for the purpose of improving various performances such as oxidation resistance, weather resistance, dyeability, and strength. It is also possible to polymerize and cure. In this case, a polymerization and curing catalyst can be added separately for this reaction if necessary. Examples of the performance improver include alcohols containing phenols, carboxylic acids, carboxylic anhydrides, vinyl compounds containing (meth)acrylates, and (thio)epoxy compounds. These compounds can be added within a range where there is no problem until the required physical properties are obtained.

In addition, when the optical material composition of the present invention is polymerized and cured to obtain an optical material, known additives such as an antioxidant, an ultraviolet absorber, an anti-yellowing agent, a bluing agent, and a pigment are added to obtain an optical material. It is of course possible to further improve the practicality of the material used. When the composition for optical materials of the present invention easily peels from the mold during polymerization, a known external and/or internal adhesion improver is used or added to control the adhesion between the obtained optical material and the mold. It can be improved. Examples of the internal adhesion improver here include 3-methacryloxypropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, and 3 Examples thereof include silane compounds such as mercaptopropyltrimethoxysilane, which can be used in an amount of 0.00001 to 5 parts by weight based on 100 parts by weight of the optical material composition of the present invention. On the contrary, when the composition for an optical material of the present invention is difficult to be peeled from the mold after polymerization, a known external and/or internal mold release agent is used or added to improve the mold releasability of the obtained optical material from the mold. It is possible to improve it. The internal release agent referred to here is a fluorine-based nonionic surfactant, a silicon-based nonionic surfactant, an alkyl quaternary ammonium salt, a phosphoric acid ester, an acidic phosphoric acid ester, an oxyalkylene-type acidic phosphoric acid ester, or an alkali of an acidic phosphoric acid ester. Metal salts, alkali metal salts of oxyalkylene type acidic phosphoric acid esters, metal salts of higher fatty acids, higher fatty acid esters, paraffins, waxes, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, aliphatic amine ethylene oxide adducts, etc. For example, 0.00001 to 5 parts by weight can be used with respect to 100 parts by weight of the composition for optical materials of the present invention.

As an example of the method for producing an optical material of the present invention, a composition for an optical material containing a compound (a), a compound (b), a compound (c) and a performance improver, a catalyst, an adhesion improver or a releasability improver. After mixing and homogenizing additives such as antioxidants, UV absorbers, yellowing agents, bluing agents, pigments, etc., and then injecting them into a glass or metal mold and heating to proceed the polymerization and curing reaction. , Can be removed from the mold.

In the method for producing an optical material of the present invention, a part or all of the compound (a), the compound (b), the compound (c) and the performance improving agent is cast in the presence or absence of a catalyst and stirring before casting. Alternatively, it is also possible to preliminarily polymerize at -100 to 160° C. for 0.1 to 480 hours without stirring and then prepare a composition for optical material and perform casting. In particular, when the compound in the composition for optical material contains a solid component and handling is not easy, this preliminary polymerization is effective. The preliminary polymerization conditions are preferably −10 to 120° C. for 0.1 to 240 hours, more preferably 0 to 100° C. for 0.1 to 120 hours, depending on the case, an adhesion improver or a mold release agent. Additives such as a sex improving agent, an antioxidant, an ultraviolet absorber, an anti-yellowing agent, a bluing agent and a pigment may be added at the same time.

The manufacturing method of the optical material of the present invention will be described below in more detail. As described above, it is produced by mixing the main raw material and the auxiliary raw material and then injecting and curing into a mold. One of the composition components used as the (a) compound, the (b) compound and the (c) compound, and the performance improving agent. Additives such as compounds, catalysts, adhesion improvers or releasability improvers, antioxidants, UV absorbers, anti-yellowing agents, bluing agents, pigments, etc. that can react with all or part of them are all in the same container. At the same time, the raw materials may be mixed with stirring at the same time, the respective raw materials may be added and mixed in stages, or several components may be separately mixed and then remixed in the same container. The respective raw materials and additives may be mixed in any order. Upon mixing, the set temperature, the time required for this, etc. may basically be the conditions under which the respective components are sufficiently mixed, but the excessive temperature and time are each raw material, an unfavorable reaction between the additives occurs, Further, it is not suitable because it causes an increase in viscosity and makes casting operation difficult. The mixing temperature should be in the range of -50°C to 100°C, and the preferred temperature range is -30°C to 70°C, more preferably -5°C to 50°C. The mixing time is 1 minute to 12 hours, preferably 5 minutes to 10 hours, and most preferably about 5 minutes to 6 hours. Degassing operation under reduced pressure before, during, or after mixing of the raw materials and additives is a preferable method from the viewpoint of preventing bubbles from being generated during the subsequent casting polymerization and curing. The degree of pressure reduction at this time is about 0.1 mmHg to 700 mmHg, but 0.5 mmHg to 300 mmHg is preferable. Furthermore, it is preferable that the mixture or the main and auxiliary raw materials before mixing are purified by filtering impurities with a filter having a pore size of about 0.05 to 3 μm from the viewpoint of further improving the quality of the optical material of the present invention. .. After pouring into a mold made of glass or metal, polymerization and hardening are carried out in an electric furnace, water or an oil bath, etc., but the hardening time is usually 0.1 to 100 hours, preferably 1 to 72 hours, and the hardening temperature is usually − The temperature is 10 to 160°C, preferably 0 to 140°C. The polymerization can be carried out by holding at a predetermined polymerization temperature for a predetermined time, increasing the temperature by 0.1° C. to 100° C./h, decreasing the temperature by 0.1° C. to 100° C./h, and a combination thereof. Further, it is preferable to anneal the optical material at a temperature of 50 to 150° C. for about 10 minutes to 5 hours after the curing, in order to remove the strain of the optical material of the present invention. Further, if necessary, surface treatment such as dyeing, hard coating, antireflection, antifogging and impact resistance can be performed.

Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited thereto. The evaluation of the obtained optical material was performed by the following methods.
Refractive index (nD), Abbe number (νD): Measured at 25° C. using an Abbe refractometer.
Impact resistance: 480 g of an iron ball was dropped from a height of 127 cm on a flat plate having a thickness of 3.0 mm.
Color tone: A 3.0 mm thick flat plate was prepared by the method described in the example, and the YI value was measured using a colorimeter JS-555 manufactured by Color Techno System. A YI value of less than 3.0 was evaluated as ◯, 3.0 or more and 5.0 or less as Δ, and more than 5.0 was evaluated as x. ○ and △ are acceptable, and ○ is particularly preferable.

(Example 1)
Under a nitrogen atmosphere, 45 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 6 parts by weight of 1,2,3,5,6-pentathiepan were mixed and stirred at 100° C. for 1 hour. After cooling, 49 parts by weight of metaxylylene diisocyanate, 0.01 part by weight of cetyldimethylbenzylammonium chloride as a catalyst and 0.005 part by weight of dibutyltin dilaurate, and 0.05 part by weight of dioctylphosphoric acid as an internal release agent are mixed. After that, a uniform solution was prepared. Then, this was filtered through a 0.5 μm PTFE filter, poured into a 3.0 mm thick flat lens mold, and heated in an oven from 10° C. to 120° C. over 22 hours to polymerize and cure to produce a lens. .. The obtained lens exhibited good heat resistance and physical properties, and had good transparency and surface condition. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and color tone of the lens.

(Examples 2 to 8)
The same operation as in Example 1 was repeated except that the composition and catalyst shown in Table 1 were used. In all cases, the lenses obtained exhibited good heat resistance and physical properties, and good transparency and surface conditions. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and color tone of the lens.

(Comparative Example 1)
Under a nitrogen atmosphere, 45 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5 parts by weight of elemental sulfur and 1 part by weight of selenium sulfide were mixed and stirred at 100° C. for 1 hour. After cooling, 49 parts by weight of metaxylylene diisocyanate, 0.01 part by weight of cetyldimethylbenzylammonium chloride as a catalyst and 0.005 part by weight of dibutyltin dilaurate, and 0.05 part by weight of dioctylphosphoric acid as an internal release agent are mixed. After that, a uniform solution was prepared. Then, this was filtered through a 0.5 μm PTFE filter, poured into a 3.0 mm thick flat lens mold, and heated in an oven from 10° C. to 120° C. over 22 hours to polymerize and cure to produce a lens. .. The obtained lens exhibited good heat resistance and physical properties, and had good transparency and surface condition. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and color tone of the lens.

(Comparative Examples 2-8)
The same operation as in Comparative Example 1 was repeated except that the composition and catalyst shown in Table 1 were used. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and color tone of the lens.

(Comparative Examples 9 to 10)
The same operation as in Example 1 was repeated except that the amounts shown in Table 1 were changed. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and color tone of the lens.

Compound abbreviation <(a) compound>
MXDI: Metaxylylene diisocyanate
BIMDT: 2,5-bis(isocyanatomethyl)-1,4-dithiane
DCHMDI: Dicyclohexylmethane-4,4'-diisocyanate
HMDI: Hexamethylene diisocyanate
BIMC: 1,3-bis(isocyanatomethyl)cyclohexane <(b) compound>
MDMDTO: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane
BMMDT: 2,5-bis(mercaptomethyl)-1,4-dithiane
MDMTP: 2-mercaptomethyl-1,5-dimercapto-3-thiapentane
PETMP: Pentaerythritol tetrakis (3-mercaptopropionate)
<Comparative compound of (c) compound>
S: Sulfur
SSE: Selenium sulfide
SE: Selenium <Catalyst>
CDMBAC: Cetyl dimethyl benzyl ammonium chloride
DBTDL: Di-n-butyltin dilaurylate
TBPB: Tetrabutylphosphonium bromide

Claims (6)

(C) 1, 2, 3, relative to the total weight of (a) a compound having two or more isocyanate groups and/or isothiocyanate groups per molecule and (b) a compound having two or more mercapto groups per molecule. A composition for optical materials, characterized in that the ratio [(c)/{(a)+(b)}] of the total weight of 5,6-pentathiepan is 0.03 to 0.30. (A) The compound having two or more isocyanate groups and/or isothiocyanate groups per molecule is metaxylylene diisocyanate, 2,5-bis(isocyanatomethyl)-1,4-dithiane, dicyclohexylmethane-4,4. The composition for optical materials according to claim 1, comprising at least one selected from the group consisting of'-diisocyanate, hexamethylene diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane. (B) The compound having two or more mercapto groups per molecule is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,5-bis(mercaptomethyl)-1,4-dithiane, 2 -Mercaptomethyl-1,5-dimercapto-3-thiapentane, and for at least one selected from the group consisting of pentaerythritol tetrakis(3-mercaptopropionate), for an optical material according to claim 1 or 2. Composition. The composition for optical materials according to claim 1 or 2, wherein (b) the compound having two or more mercapto groups per molecule has a sulfide bond. An optical material obtained by polymerizing and curing the composition for optical material according to claim 1. An optical lens comprising the optical material according to claim 5.