JP3220614B2 - Composition for urethane-based plastic lens, plastic lens comprising the same, and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for a urethane-based plastic lens used for various optical lenses such as spectacle lenses, a lens obtained therefrom, and a method for producing a lens.

[0002]

2. Description of the Related Art A plastic lens is a molded product requiring a high degree of optical homogeneity, as is apparent from its use. The mechanism of optical non-uniformity in plastic lens molding is not well understood, but thermal non-uniformity probably occurs due to partial polymerization.
It is believed that this results in convection of the monomer, which is fixed and becomes optically non-uniform.

[0003] For molding plastic lenses, a casting polymerization method is generally employed in which the raw material monomer is injected into a mold and heated and cured. While the temperature is gradually increased, the polymer is polymerized over a period of about ten hours for a thick material which tends to cause optical non-uniformity over several days without causing thermal non-uniformity inside the lens.

On the other hand, various attempts have been made to obtain optically homogeneous molded products in a short time. A representative example is polymerization using light or radiation which is being attempted on radical polymerization type monomers. That is, by employing a light or radiation polymerization method having a high polymerization rate, the lens is cured at a stroke before thermal unevenness occurs inside the lens (Isao Kaetsu, Optical Technology Contact, Vol. 7, 7,
31, (1979)).

The present inventors have proposed a urethane-based plastic lens as a method for increasing the refractive index of a plastic lens. For example, JP-A-60-199016 discloses a urethane plastic lens comprising a polyisocyanate compound and a polythiol compound.
7229 proposed a urethane-based plastic lens comprising a polyisocyanate compound and a polyol compound.

Although there is a demand for shortening the polymerization time in molding these urethane-based plastic lenses, since the urethanization reaction is a reaction governed by heat, light or radiation is used as in the radical polymerization type. It is not possible to adopt a technique of polymerizing all at once.
In addition, in molding a plastic lens, generally, at least 2 to 5 hours are required from the adjustment of the monomer to the injection, and in order to increase the polymerization rate, a method of using a strongly active catalyst or increasing the amount of the catalyst is used. In such a case, the polymerization reaction proceeds during the preparation of the monomer, and there is a problem that it is not possible to inject into the mold, that is, a pot life cannot be obtained.

As a method for producing these urethane-based plastic lenses, the present inventors disclosed in Japanese Patent Laid-Open No. 3-840.
21 proposed a method using a tertiary amine or dibutyltin dilaurate and a tertiary amine. The tertiary amine used in this method needs to have an electron-withdrawing group in the molecule, and when using a tertiary amine having no electron-withdrawing group, for example, triethylamine, the activity is too large. As a result, the polymerization reaction exploded, and it was impossible to inject the monomer into the mold. In addition, even if this method is used, there is a problem that when heat polymerization is performed in a short time, optical inhomogeneity tends to occur in the obtained lens.

[0008]

SUMMARY OF THE INVENTION An object of the present invention is to provide one or more ester compounds selected from isocyanate compounds, isothiocyanate compounds and isothiocyanate compounds having an isocyanate group, and hydroxy compounds and mercapto compounds. In molding a urethane-based plastic lens from one or two or more active hydrogen compounds selected from hydroxy compounds having a mercapto group, a lens that is optically homogeneous and has no or very little optical distortion in a short time An object of the present invention is to provide a composition which can be manufactured, a lens obtained therefrom, and a manufacturing method for obtaining the lens.

[0009]

Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, have found that one or more compounds selected from isocyanate compounds, isothiocyanate compounds, and isothiocyanate compounds having an isocyanate group. In molding a urethane-based plastic lens from two or more ester compounds and one or more active hydrogen compounds selected from hydroxy compounds, mercapto compounds, and hydroxy compounds having a mercapto group, a Lewis acid and a catalyst are used as catalysts. By using a tertiary amine in combination, even a tertiary amine having no electron withdrawing group, which was conventionally considered impossible to take a pot life,
There must be no sudden runaway reaction and sufficient pot life can be obtained. Furthermore, depending on the combination of monomers,
At around room temperature, the pot life is extended as compared with the case where the catalyst is not used because the polymerizability is reduced as compared with the case where the catalyst is not used. Furthermore, they have found that even if the polymerization time is greatly shortened, it is difficult to cause optical nonuniformity in the obtained lens, and have reached the present invention.

That is, the present invention relates to an isocyanate compound,
Isothiocyanate compounds, one or two or more ester compounds selected from isothiocyanate compounds having an isocyanate group, and hydroxy compounds, mercapto compounds, one or two or more active hydrogen compounds selected from a hydroxy compound having a mercapto group The present invention relates to a composition for a urethane-based plastic lens containing a Lewis acid and a tertiary amine, a lens obtained therefrom, and a production method for obtaining the lens.

Hereinafter, the present invention will be described in detail. The ester compound used as a raw material of the sulfur-containing urethane-based plastic lens in the present invention is a compound having one or more isocyanate groups in one molecule (isocyanate compound), a compound having an isothiocyanate group (isothiocyanate compound) or isocyanate. It is selected from compounds having a group and an isothiocyanato group (isothiocyanate compounds having an isocyanato group).

As the isocyanate compound, for example,
Butyl isocyanate, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2′-dimethylpentane diisocyanate,
2,2,4-trimethylhexamethylene diisocyanate, decamethylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate , 1,6,11-undecatriisocyanate,
1,3,6-hexamethylene triisocyanate, 1,
8-diisocyanato-4-isocyanatomethyloctane, 2,5,7-trimethyl-1,8-diisocyanato-5-isocyanatomethyloctane, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl)
Ether, 1,4-butylene glycol dipropyl ether-ω, ω'-diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate, 2-
Isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylene diisocyanate,
Bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α ′, α′-tetramethylxylylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis Aliphatic isocyanates such as (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) phthalate, mesitylylene triisocyanate, 2,6-di (isocyanatomethyl) furan, cyclohexyl isocyanate, isophorone diisocyanate, bis (Isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,
2′-dimethyldicyclohexylmethane diisocyanate, bis (4-isocyanato-n-butylidene) pentaerythritol, diisocyanate dimerate, 2-isocyanatomethyl-3- (3-isocyanatopropyl)-
5-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-
2- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl)-
6-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -bicyclo [2,2,1 ] -Heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6- (2-
Isocyanatoethyl) -bicyclo [2,1,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5- (2-isocyanatoethyl) -bicyclo [2,2,1] -Heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -bicyclo [2,2,1] -heptane, 1,3,5-tris (isocyanate Alicyclic isocyanate such as methyl) cyclohexane, phenyl isocyanate, phenylene diisocyanate, tolylene diisocyanate, ethyl phenylene diisocyanate, isopropyl phenylene diisocyanate, dimethyl phenylene diisocyanate, diethyl phenylene diisocyanate, diisopropyl Phenylene diisocyanate, trimethylben Triisocyanate, benzene triisocyanate, naphthalene diisocyanate, methyl naphthalene diisocyanate, biphenyl diisocyanate, tolidine diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyldiphenylmethane-4, 4'-diisocyanate, bibenzyl-4,4'-diisocyanate, bis (isocyanatophenyl) ethylene, 3,3'-dimethoxybiphenyl-4,4'-diisocyanate, triphenylmethane triisocyanate, Polymeric MDI, naphthalene triisocyanate, diphenylmethane-2,4,4 '
-Triisocyanate, 3-methyldiphenylmethane-
4,6,4'-triisocyanate, 4-methyl-diphenylmethane-3,5,2 ', 4', 6'-pentaisocyanate, phenylisocyanatomethylisocyanate, phenylisocyanatoethylisocyanate, tetrahydronaphthy Range isocyanate, hexahydrobenzene diisocyanate, hexahydrodiphenylmethane-4,4'-diisocyanate, diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate, benzophenone diisocyanate Nate, diethylene glycol diphenyl ether diisocyanate, dibenzofurandi isocyanate, carbazole diisocyanate, ethyl carbazole diisocyanate, Aromatic isocyanates such as chlorocarbazole diisocyanate, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, dimethyl sulfone diisocyanate, dithiodimethyl diisocyanate, dithiodiethyl diisocyanate, dithio Dipropyl diisocyanate, dicyclohexyl sulfide-4,4'-
Diisocyanate, 1-isocyanatomethylthia-
Sulfur-containing aliphatic isocyanates such as 2,3-bis (2-isoanatoethylthia) propane, diphenylsulfide-2,4'-diisocyanate, diphenylsulfide-4,4'-diisocyanate, 3,3 '-Dimethoxy-4,4'-diisocyanatodibenzylthioether,
Bis (4-isocyanatomethylbenzene) sulfide,
4,4'-methoxybenzenethioethylene glycol-
Aromatic sulfide isocyanates such as 3,3'-diisocyanate, diphenyl disulfide-4,4'-
Diisocyanate, 2,2'-dimethyldiphenyldisulfide-5,5'-diisocyanate, 3,3'-dimethyldiphenyldisulfide-5,5'-diisocyanate, 3,3'-dimethyldiphenyldisulfide-
6,6′-diisocyanate, 4,4′-dimethyldiphenyldisulfide-5,5′-diisocyanate,
3,3′-dimethoxydiphenyl disulfide-4,
Aromatic disulfide isocyanates such as 4'-diisocyanate and 4,4'-dimethoxydiphenyldisulfide-3,3'-diisocyanate, diphenylsulfone-4,4'-diisocyanate, diphenylsulfone-3, 3'-diisocyanate, benzylidenesulfone-4,4'-diisocyanate, diphenylmethanesulfone-4,4'-diisocyanate, 4-methyldiphenylmethanesulfone-2,4'-diisocyanate,
4,4'-dimethoxydiphenylsulfone-3,3'-
Diisocyanate, 3,3'-dimethoxy-4,4'-
Diisocyanate dibenzyl sulfone, 4,4′-dimethyldiphenyl sulfone-3,3′-diisocyanate, 4,4′-di-tert-butyldiphenyl sulfone-3,3′-diisocyanate, 4,4 '-Dimethoxybenzeneethylenedisulfone-3,3'-diisocyanate, 4,4'-dichlorodiphenylsulfone-3,
Aromatic sulfone isocyanates such as 3′-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester,
Methoxy-3-isocyanatobenzenesulfonyl-4 '
Sulfonic acid ester-based isocyanates such as isocyanatophenol esters, 4-methyl-3-isocyanatobenzenesulfonylanilide-3′-methyl-4′-
Isocyanate, dibenzenesulfonyl-ethylenediamine-4,4'-diisocyanate, 4,4'-dimethoxybenzenesulfonyl-ethylenediamine-3,3 '
Aromatic sulfonic acid amides such as diisocyanate, 4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3′-isocyanate, thiophene
2,5-diisocyanate, thiophene-2,5-diisocyanatomethyl, 1,4-dithian-2,5-diisocyanate, 1,4-dithian-2,5-diisocyanatomethyl, 1, 3-dithiolan-4,5-diisocyanate, 1,3-dithiolan-4,5-diisocyanatomethyl, 1,3-dithiolan-2-methyl-4,5-diisocyanatomethyl, 1,3- Dithiolane-2,2-diisocyanatoethyl, tetrahydrothiophene-2,5-
Diisocyanate, tetrahydrothiophene-2,5-
Diisocyanatomethyl, tetrahydrothiophene-2,
5-diisocyanatoethyl, tetrahydrothiophene-
And sulfur-containing heterocyclic compounds such as 3,4-diisocyanatomethyl. In addition, halogen-substituted, alkyl-substituted, alkoxy-substituted and nitro-substituted products such as chlorine-substituted product and bromine-substituted product, prepolymer-modified products with polyhydric alcohol, carbodiimide-modified products, urea-modified products, and burette-modified products Isomers, dimerization or trimerization reaction products and the like can also be used.

The isothiocyanate compound used as a raw material in the present invention includes a compound containing a sulfur atom in addition to the isothiocyanate group. Specifically, for example, butyl isothiocyanate, 1,2-diisothiocyanatoethane, 1,3-isothiocyanatopropane,
Aliphatic isothiocyanates such as 1,4-diisothiocyanatobutane, 1,6-diisothiocyanatohexane, p-phenylenediisopropylidene diisothiocyanate, cyclohexyl isothiocyanate, cyclohexane diisothiocyanate and the like; Alicyclic isothiocyanate, phenyl isothiocyanate, 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanate Toluene, 2,5-diisothiocyanato-m-xylene, 4,4'-diisothiocyanato-
1,1′-biphenyl, 1,1′-methylenebis (4-
Isothiocyanatobenzene), 1,1′-methylenebis (4-isothiocyanato-2-methylbenzene),
1′-methylenebis (4-isothiocyanato-3-methylbenzene), 1,1 ′-(1,2-ethanediyl) bis (4-isothiocyanatobenzene), 4,4′-diisothiocyanatobenzophenone, 4, 4'-diisothiocyanato-3,3'-dimethylbenzophenone, benzanilide-3,4'-diisothiocyanate, diphenylether-4,4'-diisothiocyanate, diphenylamine-4,4'-diisothiocyanate Aromatic isothiocyanates such as phenate, heterocyclic-containing isothiocyanates such as 2,4,6-triisothiocyanato-1,3,5-triazine, hexanedioil diisothiocyanate, and nonanedioil diisothiate Osocyanate, carbonic diisothiocyanate, 1,3-benzenedicarbonyl diisothiocyanate 1,4 benzene dicarbonyl diisothiocyanate, and (2,2'-bipyridine) -4,4'-carbonyl isothiocyanate, such as dicarbonyl diisothiocyanate.

Examples of the bifunctional or higher-functional isothiocyanate having one or more sulfur atoms in addition to the isothiocyanate group used as a raw material in the present invention include thiobis (3-isothiocyanatopropane) and thiobis ( Sulfur-containing aliphatic isothiocyanates such as 2-isothiocyanatoethane) and dithiobis (2-isothiocyanatoethane);
-Isothiocyanato-4 -− (2-isothiocyanato)
Sulfonyl @ benzene, thiobis (4-isothiocyanatobenzene), sulfonylbis (4-isothiocyanatobenzene), sulfinylbis (4-isothiocyanatobenzene), dithiobis (4-isothiocyanatobenzene), 4-isothiocyanato- 1-{(4-isothiocyanatophenyl) sulfonyl} -2-methoxy-benzene, 4-methyl-3-isothiocyanatobenzenesulfonyl-4′-isothiocyanatophenyl ester, 4-
Sulfur-containing aromatic isothiocyanates such as methyl-3-isothiocyanatobenzenesulfonylanilide-3′-methyl-4′-isothiocyanate; thiophene-2,5-
Examples thereof include sulfur-containing heterocyclic compounds such as diisothiocyanate and 1,4-dithiane-2,5-diisothiocyanate.

Further, halogen-substituted, alkyl-, alkoxy-, and nitro-substituted isothiocyanates such as chlorine- and bromine-substituted isothiocyanates, modified prepolymers with polyhydric alcohols, and modified carbodiimides Can also be used.

The isothiocyanate compound having an isocyanate group used as a raw material in the present invention includes, for example, 1-isocyanato-3-isothiocyanatopropane, 1-isocyanato-5-isothiocyanatopentane, and 1-isocyanato-pentane. 6-isothiocyanatohexane, isocyanatocarbonylisothiocyanate, 1-
Aliphatic or alicyclic compounds such as isocyanato-4-isothiocyanatocyclohexane, 1-isocyanato-
Aromatic compounds such as 4-isothiocyanatobenzene, 4-methyl-3-isocyanato-1-isothiocyanatobenzene, and complex compounds such as 2-isocyanato-4,5-diisothiocyanato-1,3,5-triazine Cyclic compounds, and compounds containing a sulfur atom in addition to isothiocyanato groups such as 4-isocyanato-4'-isothiocyanatodiphenylsulfide and 2-isocyanato-2'-isothiocyanatodiethyldisulfide are also included.

Further, halogen-substituted, alkyl-substituted, alkoxy-substituted or nitro-substituted compounds such as chlorine-substituted or bromine-substituted compounds, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products body,
A modified buret, a dimerization or trimerization reaction product, or the like can also be used. These ester compounds may be used alone or in combination of two or more.

The active hydrogen compound used in the sulfur-containing urethane plastic lens of the present invention is selected from a hydroxy compound, a mercapto compound and a mercapto compound having a hydroxy group.

Examples of the hydroxy compound include methanol, benzyl alcohol, phenol, ethoxyethanol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol,
Butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside,
Pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, allitol, mannitol, dorsitol, iditol, glycol, inositol, hexanetriol, triglycerol, digliperol, triethylene glycol, polyethylene glycol, Tris (2
-Hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,1,0,
2,6] decane-dimethanol, bicyclo [4,3
0] -nonanediol, dicyclohexanediol, tricyclo [5,3,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1] dodecane-diethanol, hydroxy Aliphatic alcohols such as propyltricyclo [5,3,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1'-bicyclohexylidenediol, cyclohexanetriol, maltitol and lactitol・ Polyol, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthrene, bisph Aromatic alcohols and polyols such as phenol A, bisphenol F, xylylene glycol, and tetrabromobisphenol A; addition reaction products thereof with alkylene oxides such as ethylene oxide and propylene oxide; halogenated alcohols such as dibromoneopentyl glycol; In addition to high molecular polyols such as polyols and epoxy resins, oxalic acid, glutamic acid, adipic acid, acetic acid, propionic acid,
Cyclohexanecarboxylic acid, β-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid,
Condensation reaction products of organic acids such as salicylic acid, 3-bromopropionic acid, 2-bromoglycol, dicarboxycyclohexane, pyromellitic acid, butanetetracarboxylic acid, and bromophthalic acid with the polyol, the polyol and ethylene oxide or propylene oxide An addition reaction product with an alkylene oxide, an addition reaction product with an alkylene polyamine and an alkylene oxide such as ethylene oxide or propylene oxide, further, bis- [4- (hydroxyethoxy) phenyl] sulfide, bis- [4- (2-hydroxypropoxy) phenyl] sulfide, bis- [4- (2,3-
Dihydroxypropoxy) phenyl] sulfide, bis- [4- (4-hydroxycyclohexyloxy) phenyl] sulfide, bis- [2-methyl-4- (hydroxyethoxy) -6-butylphenyl] sulfide and these compounds per hydroxyl group Compounds to which ethylene oxide and / or propylene oxide having an average of 3 molecules or less are added, di- (2-hydroxyethyl) sulfide, 1,2-bis- (2-hydroxyethylmercapto) ethane, bis (2-hydroxyethyl) disulfide , 1,4-dithiane-2,5-diol, bis (2,
3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4
-Hydroxyphenyl) sulfone (trade name: bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4'-thiobis (6-tert
-Butyl-3-methylphenol), 1,3-bis (2
-Hydroxyethylthioethyl) -cyclohexane and other polyols containing a sulfur atom.

Examples of the mercapto compound include, for example, methyl mercaptan, benzenethiol, benzylthiol, methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3 -Propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,
2,3-propanetrithiol, tetrakis (mercaptomethyl) methane, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1 , 2-Dithiol, 2-methylcyclohexane-2,3-dithiol, bicyclo [2,2,1] pepta-exo-cis-2,3-dithiol, 1,1-
Bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-
Mercapto acetate), 2,3-dimercapto-1-
Propanol (3-mercaptoacetate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether,
2,3-dimercaptopropyl methyl ether, 2,2
-Bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris ( 2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate),
Aliphatic thiols such as 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4
-Dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene,
1,2-bis (mercaptoethyl) benzene, 1,3-
Bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethoxy) benzene, 1,3-bis (mercaptomethoxy) benzene, 1,4-bis (mercaptomethoxy) benzene 1,2-bis (mercaptoethoxy) benzene, 1,3-bis (mercaptoethoxy) benzene,
1,4-bis (mercaptoethoxy) benzene, 1,
2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercapto Methyl) benzene, 1,3,5-tris (mercaptomethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris (mercaptoethyl) benzene, 1,3,5-tris (Mercaptoethyl) benzene, 1,2,3-tris (mercaptomethoxy) benzene, 1,2,4-tris (mercaptomethoxy) benzene, 1,3,5-tris (mercaptomethoxy) benzene, 1,2,3 Tris (mercaptoethoxy) benzene, 1,2,4-tris (mercaptoethoxy) benzene, 1,3,5-tris (mer Putoetokishi) benzene, 1,2,3,4-mercapto benzene, 1,
2,3,5-tetramercaptobenzene, 1,2,4
5-tetramercaptobenzene, 1,2,3,4-tetrakis (mercaptomethyl) benzene, 1,2,3,5
-Tetrakis (mercaptomethyl) benzene, 1,2,2
4,5-tetrakis (mercaptomethyl) benzene,
1,2,3,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 1,2,4,5-tetrakis (mercaptoethyl) benzene, 1,2,3 1,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptomethoxy) benzene, 1,2,4,5-
Tetrakis (mercaptomethoxy) benzene, 1,2,2
3,4-tetrakis (mercaptoethoxy) benzene,
1,2,3,5-tetrakis (mercaptoethoxy) benzene, 1,2,4,5-tetrakis (mercaptoethoxy) benzene, 2,2′-dimercaptobiphenyl,
4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-toluenedithiol,
4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphthalenedithiol, 2,4
-Dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracenedimethanethiol, 1,3-di (p-methoxyphenyl) propane-2,2-dithiol Aromatic thiols such as 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di (p-mercaptophenyl) pentane;
-Dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2,3,4 Chlorine-substituted products such as 6-tetrachloro-1,5-bis (mercaptomethyl) benzene, halogen-substituted aromatic thiols such as bromine-substituted products, 2-methylamino-4,6-dithiol-sym-triazine;
2-ethylamino-4,6-dithiol-sym-triazine, 2-amino-4,6-dithiol-sym-triazine, 2-morpholino-4,6-dithiol-sy
m-triazine, 2-cyclohexylamino-4,6-
Dithiol-sym-triazine, 2-methoxy-4,
6-dithiol-sym-triazine, 2-phenoxy-4,6-dithiol-sym-triazine, 2-thiobenzeneoxy-4,6-dithiol-sym-triazine, 2-thiobutyloxy-4,6-dithiol- s
thiol containing a heterocycle such as ym-triazine, furthermore 1,2-bis (mercaptomethylthio) benzene,
1,3-bis (mercaptomethylthio) benzene, 1,
4-bis (mercaptomethylthio) benzene, 1,2-
Bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,2,4 -Tris (mercaptomethylthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-
Tris (mercaptoethylthio) benzene, 1,2,4
-Tris (mercaptoethylthio) benzene, 1,3
5-tris (mercaptoethylthio) benzene, 1,
2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, 1,2,3,4 -Tetrakis (mercaptoethylthio) benzene, 1,2,3,5
-Tetrakis (mercaptoethylthio) benzene, 1,
2,4,5-tetrakis (mercaptoethylthio) benzene and the like, and aromatic thiols containing a sulfur atom in addition to mercapto groups such as alkylated nuclei thereof, bis (mercaptomethyl) sulfide, bis (mercaptoethyl)
Sulfide, bis (mercaptopropyl) sulfide,
Bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropyl) methane, 1,2-bis (mercaptomethylthio)
Ethane, 1,2- (2-mercaptoethylthio) ethane, 1,2- (3-mercaptopropyl) ethane, 1,
3-bis (mercaptomethylthio) propane, 1,3-
Bis (2-mercaptoethylthio) propane, 1,3-
Bis (3-mercaptopropylthio) propane, 1,2
-Bis (2-mercaptoethylthio) -3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2 -Mercaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) ) Methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, and the like, and These thioglycols And esters of mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3
-Mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercapto Propionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-
Mercaptoacetate), hydroxyethyldisulfidebis (3-mercaptopropionate), hydroxypropyldisulfidebis (2-mercaptoacetate), hydroxypropyldisulfidebis (3-mercaptopropionate), 2-mercaptoethyletherbis (2- Mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4-dithiane-2,5-diolbis (2-
Mercaptoacetate), 1,4-dithiane-2,5-
Diol bis (3-mercaptopropionate), thioglycolic acid bis (2-mercaptoethyl ester),
Bis (2-mercaptoethyl ester) thiodipropionate, bis (2-mercaptoethyl ester) 4,4'-thiodibutylate, bis (2-mercaptoethyl ester) dithiodiglycolate, bis (2-mercaptoethyl ester) dithiodipropionate Mercaptoethyl ester), 4,4'-dithiodibutyric acid bis (2-mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercapto Propyl ester), bis (2,3-dimercaptopropyl ester) dithiodiglycolate, aliphatic thiol containing sulfur atom in addition to mercapto group such as dithiodipropionic acid (2,3-dimercaptopropyl ester), 3 , 4-thiophenedithiol, tetrahydrothiophene-2,5 Dimercapto-methyl, 2,5
Dimercapto-1,3,4-thiadiazole, 2,5-
Heterocyclic compounds containing a sulfur atom in addition to a mercapto group, such as dimercapto-1,4-dithiane and 2,5-dimercaptomethyl-1,4-dithiane.

Examples of the mercapto compound having a hydroxy group include 2-mercaptoethanol and 3-mercaptoethanol.
-Mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 1,3-dimercapto-2 -Propanol, 2,3-dimercapto-1-propanol, 1,2
-Dimercapto-1,3-butanediol, pentaerythritol tris (3-mercaptopropionate),
Pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), pentaerythritol pentakis (3-
Mercaptopropionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene,
4-hydroxy-4'-mercaptodiphenylsulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethylsulfide mono (3-mercaptopropionate), dimercaptoethane mono (sulfylate), hydroxyethylthiomethyl tris ( Mercaptoethylthio) methane and the like.

Further, a chlorine-substituted form of these active hydrogen compounds and a halogen-substituted form of bromine-substituted form may be used.
These may be used alone or in combination of two or more.

The tertiary amine used in the present invention includes:
The following compounds are mentioned. For example, triethylamine, tripropylamine, dipropylethylamine, tributylamine, trihexylamine, dimethylcyclohexylamine, dicyclohexylmethylamine, tricyclohexylamine, diethylcyclohexylamine, dicyclohexylethylamine, dipropylcyclohexylamine, dicyclohexylpropylamine, dibutylcyclohexylamine , Dicyclohexylbutylamine, N, N-dimethylbenzylamine, N, N-diethylbenzylamine, N, N-dipropylbenzylamine, N, N-dibutylbenzylamine, N-methyldibenzylamine, 2-dimethylaminomethylphenol , 2,4,6-tris (N, N-dimethylaminomethyl) phenol, triethylenediamine, tetramethyl Ethylenediamine, tetraethyl ethylene diamine, tetra ethylenediamine, tetrabutyl ethylenediamine, pentamethyldiethylenetriamine, penta ethyl diethylene triamine, penta diethylenetriamine, penta butyl diethylenetriamine, N
-Methylpiperidine, N-ethylpiperidine, N-propylpiperidine, N-butylpiperidine, N, N-dimethylpiperazine, N, N-diethylpiperazine, N, N
-Dipropylpiperazine, N, N-dibutylpiperazine, hexamethylenetetramine, dimethylaminoethylacetate, diethylaminoethylacetate, dimethylaminopropionitrile, diethylaminopropionitrile, N, N-dimethylaminoethanol, N, N-
Diethylaminoethanol, N, N-di-n-propylaminoethanol, N, N-diisopropylaminoethanol, N, N-dibutylaminoethanol, N, N-
Dihexylaminoethanol, N, N-dioctylaminoethanol, N-methylmorpholine, N-ethylmorpholine, N-propylmorpholine, N-butylmorpholine, N-cyclohexylmorpholine, N-methylpiperidone, N-ethylpiperidone, N-propylpiperidone , N-butylpiperidone, N-methylpyrrolidine, N
-Ethylpyrrolidine, N-propylpyrrolidine, N-butylpyrrolidine, N-methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrolidone, N-butylpyrrolidone, N, N-dimethylaniline, N, N-diethylaniline, N-dipropylaniline, N, N-dibutylaniline, N, N-cyclohexylmethylaniline,
N, N-dicyclohexylaniline, diphenylmethylamine, diphenylethylamine, triphenylamine, N, N-dimethyltoluidine, N, N-diethyltoluidine, N-cyclohexyl-N-methyltoluidine, N, N-dicyclohexyltoluidine, N, N N-dimethylnaphthylamine, N, N-diethylnaphthylamine, N, N-dimethylanisidine, N, N-diethylanisidine, N, N, N ′, N′-tetramethylphenylenediamine, pyridine, picoline, dimethylpyridine,
2,2′-bipyridyl, 4,4′-bipyridyl, pyrazine, N-methylpyrazole, N-ethylpyrazole, N
-Cyclohexylpyrazole, pyridazine, pyrimidine, pyrinoline, oxazole, thiazole, N-methylpyrazole, N-ethylpyrazole, N-propylpyrazole, N-butylpyrazole, N-cyclohexylpyrazole, 1-methylimidazole, 1-benzylimidazole, 1 -Methyl-2-methylimidazole, 1
-Benzyl-2-methylimidazole, 1-ethyl-4
-Methylimidazole, 1-ethyl-2-ethyl-4-
Methylimidazole, N-methylpyrrole, N-ethylpyrrole, N-butylpyrrole, N-methylpyrroline,
Examples include N-ethylpyrroline, N-butylpyrroline, pyrimidine, purine, quinoline, isoquinoline, N-methylcarbazole, N-ethylcarbazole, N-butylcarbazole and the like.

The Lewis acid used in the present invention is capable of forming a strong complex or salt with the above-mentioned tertiary amine, and dibutyltin dilaurate, dibutyltin diacetate, stannasoctoate and the like are not preferred.

Examples of the Lewis acid used in the present invention include the following compounds. Zinc compounds such as zinc chloride, zinc acetylacetone and zinc dibutyldithiocarbamate; iron compounds such as iron chloride and iron acetylacetone; aluminum compounds such as alumina, aluminum fluoride, aluminum chloride and triphenylaluminum; tetrafluorotin and tetrachlorotin , Tin tetrabromide, tin tetraiodo, methyltin trichloride, butyltin trichloride, dimethyltin dichloride, dibutyltin dichloride, trimethyltin chloride, tributyltin chloride, triphenyltin chloride, dibutyltin sulfide, di (2-ethylhexyl) Tin compounds such as tin oxide, tetrachlorotitanium,
Titanium compounds such as, trichloroantimony, pentachloroantimony, antimony compounds such as dichlorotriphenylantimony, uranium compounds such as nitrouranium, cadmium compounds such as nitrocadonium,
Cobalt-based compounds such as cobalt chloride and cobalt bromide; thorium-based compounds such as nitrothorium; mercury-based compounds such as diphenylmercury; nickel-based compounds such as nickelocene;
Nitrocalcium, calcium compounds such as calcium acetate, vanadium compounds such as trichlorovanadium,
Copper compounds such as copper chloride and copper iodide; manganese compounds such as manganese chloride; zirconium compounds such as zirconium chloride; arsenic compounds such as triphenylarsenic and trichloroarsenic; and boron compounds such as boron trifluorolide. No.

Among these Lewis acids used in the present invention, preferably used are metal halides or organometallic halides, more preferably tin compounds, and more preferably used tin compounds are organic tin halide compounds. It is.

In the present invention, it is important to use a tertiary amine and a Lewis acid in combination and to use them as a catalyst. By using both of them, a sufficient pot life can be obtained even at around room temperature. be able to.

The amount of the tertiary amine and the metal compound used is based on the total amount of the ester compound and the active hydrogen compound.
0.0005-5% by weight, preferably 0.005%
It is 1 to 2% by weight, but it depends on the combination of the monomer used, the combination of the tertiary amine and the metal compound used, and the type and amount of additives such as an internal release agent, and the shape of the molded product, and is determined as appropriate. .

The proportion of the ester compound and the active hydrogen compound used as the raw materials in the present invention is (NCO +
The functional group molar ratio of (NCS) / (OH + SH) is usually
It is in the range of 0.5 to 3.0, preferably in the range of 0.5 to 1.5.

Further, depending on the purpose, an internal release agent, a chain extender, a crosslinking agent, a light stabilizer,
Various substances such as an ultraviolet absorber, an antioxidant, an oil-soluble dye, and a filler may be added.

The plastic lens of the present invention is usually obtained by cast polymerization. Specifically, one or more ester compounds, one or more active hydrogen compounds, a tertiary amine and a metal compound are mixed. After defoaming the mixed solution by an appropriate method as required, the mixture is poured into a mold, and is usually gradually heated from a low temperature to a high temperature to be polymerized. The polymerization temperature and time vary depending on the type of the monomer, the shape of the lens, and additives such as a catalyst.
20 to 200 ° C., 0.5 to 10 hours.

Further, the polymerization can be carried out in the air, in an inert gas such as nitrogen, or in a liquid medium such as water. In particular, for objects that are thick and tend to cause optical non-uniformity,
Good results are often obtained by performing part or all of the polymerization in a medium having good heat conductivity such as water.

The polymerized lens may be subjected to an annealing treatment as required. In addition, the lens of the present invention may be subjected to surface polishing, antistatic treatment to improve antireflection, impart high hardness, improve abrasion resistance, improve chemical resistance, impart antifogging properties, or impart fashionability, if necessary. Physical or chemical treatments such as hard coat treatment, anti-reflection coat treatment, dyeing treatment, and light control treatment.

[0034]

The present invention will be described below in more detail with reference to examples and comparative examples. The performance test, refractive index, Abbe number, specific gravity, and optical strain of the obtained lens were evaluated by the following test methods. Refractive index, Abbe number: 20 ° C. using a Pulfrich refractometer
Was measured. Specific gravity: measured by Archimedes' method. Optical distortion: Observed with a polarizing plate and a high-pressure mercury lamp.
The evaluation criteria were those where there was almost no distortion (○), those that had slight distortion (△), and those that had obvious distortion (x). The viscosity of the monomer before injection was measured using a B-type viscometer.
It was measured at 0 ° C.

Example 1 68.8 parts (0.262 mol) of hydrogenated MDi, 10.4 parts (0.096 mol) of 1-thioglycerin, 3,6-dioxaoctane-1,8-dimercaptan 20 0.8 parts (0.114 mol), 0.8% by weight of tributylamine (hereinafter abbreviated as TBA) (the same applies to the ester compound and the active hydrogen compound), dibutyltin dichloride (hereinafter abbreviated as DBC) 0 0.4 wt% (the same applies to the ester compound and the active hydrogen compound), JP-506 (butoxyethyl acid phosphate, monoester & diester mixture manufactured by Johoku Chemical Co., Ltd.) as an internal release agent
2% by weight (based on ester compound + active hydrogen compound
After that, the mixture was mixed to form a uniform solution, and then defoamed at 20 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. Viscosity immediately before injection is 35 cps below 100 cps
The injection was very easy. In addition, the same test was conducted separately at 20 ° C. As a result, the viscosity after 5 hours was 72 cp.
The viscosity was very low at s of 100 cps or less. Subsequently, the mold was gradually heated from 40 ° C. to 140 ° C. and cured for 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. The results are also shown in Table 1. The obtained lens was colorless and transparent, and had optical properties of a refractive index of 1.548, an Abbe number of 47, and a specific gravity of 1.1.
It was 8.

Example 2 The test of Example 1 was conducted by changing the metal compound to 0.3% by weight of dimethyltin dichloride (hereinafter abbreviated as DMC) and 0.5% by weight of TBA. The results are also shown in Table 1, but as good as in Example-1, and the obtained lens was colorless and transparent, there was no optical distortion, and the optical properties were a refractive index of 1.548,
As in Example 1, the Abbe number was 47 and the specific gravity was 1.18.

Examples 3 to 11 and Comparative Examples 1 to 3 Plastic lenses were manufactured by the method of Example 1 in order to confirm the effect of the combined use catalyst of a tertiary amine and a metal compound. The results are shown in Table 1. In addition, for these tests, the internal release agent was used as Zelek UN, dibutyl phosphoric acid, or J
The test was carried out by changing to P-506 (butoxyethyl ester of phosphoric acid, a mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.).

[0038]

[Table 1]

Example-12 m-xylylene diisoanaate (hereinafter abbreviated as XDi)
43.5 parts (0.23 mol) and pentaerythritol tetrakis (3-mercaptopropionate) (hereinafter referred to as PE
Abbreviated as MP. 56.5 parts (0.115 mol), N, N
Example using 0.005% by weight of diethylcyclohexylamine (hereinafter abbreviated as DEC), 0.01% by weight of DBC, and 0.1% by weight of Zelek UN (alkyl acid phosphate alkyl ester manufactured by Du Pont) as an internal release agent. The test similar to -1 was performed. The results are shown in Table 2. still,
The obtained lens is colorless and transparent, and the optical properties are as follows.
594, Abbe number 36, specific gravity 1.34.

Examples 13 to 47 and Comparative Examples 4 to 5 Plastic lenses were manufactured in the same manner as in Example 12 in order to confirm the effect of the combined use catalyst of a tertiary amine and a metal compound. The results are shown in Table 2. Also, for these tests including Example-12, the internal release agent was
N, dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506
(Butoxyethyl phosphate acid mixture, monoester & diester mixture, manufactured by Johoku Chemical Co., Ltd.), and the test was performed. The results were the same and were good without any problems.

[0041]

[Table 2]

[0042]

[Table 3]

[0043]

[Table 4]

Example-48 52.0 parts (0.276 mol) of XDi and 48.0 parts (0.184) of 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane (hereinafter abbreviated as GST). Mol), DEC 0.015% by weight, DBC 0.015% by weight, and Zelek UN 0.1% by weight, the same test as in Example 1 was performed. As a result, the viscosity immediately before injection was 100 cp.
s or less can be injected very easily, and the obtained lens is colorless and transparent, has a refractive index of 1.660, an Abbe number of 32, and a specific gravity of 1.3.
5. Almost no optical distortion was observed. Also in this test, the internal release agent was used in addition to Zelek UN.
The test was performed by changing to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 (a mixture of butoxyethyl ester of acid phosphate, monoester & diester, manufactured by Johoku Chemical Co., Ltd.).

Comparative Example-6 52.0 parts (0.276 mol) of XDi and 48.0 parts (0.184) of 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane (hereinafter abbreviated as GST) Mol), 0.014% by weight of dimethylaminoethyl acetate, 0.14% by weight of dibutyltin dilaurate, and 0.1% by weight of Zelec UN, and the same test as in Example 1 was conducted. This composition is described in Example-2 of JP-A-3-84021.
Corresponding to the composition As a result, the viscosity immediately before injection was 100 cp.
s or less can be injected very easily, and the obtained lens is colorless and transparent, has a refractive index of 1.660, an Abbe number of 32, and a specific gravity of 1.3.
5, but there was much optical distortion.

Comparative Example-7 52.0 parts (0.276 mol) of XDi and 48.0 parts (0.184) of 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane (hereinafter abbreviated as GST) Mol), 0.069% by weight of diethylaminoacrylonitrile and 0.1% by weight of Zelek UN, and the same test as in Example 1 was conducted. This composition corresponds to the composition of Example 4 in JP-A-3-84021. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, the refractive index was 1.660, the Abbe number was 32,
Although specific gravity was 1.35, optical distortion was large.

Example-49 60.2 parts (0.229 mol) of dicyclohexylmethane-4,4'-diisoanaate (hereinafter abbreviated as HMDi)
And 39.8 parts (0.153 mol) of GST, 0.00.0 of DMC
4% by weight, DCA 0.04% by weight, Zelek UN 0.0
A test was performed in the same manner as in Example 1 using 15% by weight.
As a result, the viscosity immediately before the injection was 100 cps or less, and the injection was extremely easy. The obtained lens was colorless and transparent, and the refractive index was 1.
594, Abbe number 42, specific gravity 1.22, and almost no optical distortion were observed. Also, for this test,
The test was carried out by changing the internal release agent to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 (mixed acid butoxyethyl ester of monophosphate & monoester & diester manufactured by Johoku Chemical Co., Ltd.) in addition to Zelek UN. The same was good without any problem.

Example-50 30.0 parts (0.114 mol) of HMDi, 30.0 parts (0.135 mol) of isophorone diisoanaate (hereinafter abbreviated as IPDi), 43.3 parts (0.166 mol) of GST 0.03% by weight of DMC, 0.03% by weight of DCA,
A test was conducted in the same manner as in Example 1 using 0.015% by weight of Zelek UN. As a result, the viscosity immediately before injection was 100c.
It can be injected very easily at ps or less, the obtained lens is colorless and transparent, the refractive index is 1.594, the Abbe number is 40, and the specific gravity is 1.
23, almost no optical distortion was observed. Also,
Also in this test, dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 was used as the internal release agent in addition to Zelek UN.
(Butoxyethyl phosphate acid mixture, monoester & diester mixture, manufactured by Johoku Chemical Co., Ltd.), and the test was performed. The results were the same and were good without any problems.

Example 51 510.0 parts (0.225 mol) of IPDi, 10.0 parts (0.059 mol) of hexamethylene diisoanaate (hereinafter abbreviated as HDi), 49.4 parts (0.190 mol) of GST ), DMC 0.08% by weight, DEC 0.15% by weight,
A test was conducted in the same manner as in Example 1 using 0.015% by weight of Zelek UN. As a result, the viscosity immediately before injection was 100c.
It can be injected very easily at ps or less, and the obtained lens is colorless and transparent, has a refractive index of 1.596, an Abbe number of 40, and a specific gravity of 1.
24, almost no optical distortion was observed. Also,
Also in this test, dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 was used as the internal release agent in addition to Zelek UN.
(Butoxyethyl phosphate acid mixture, monoester & diester mixture, manufactured by Johoku Chemical Co., Ltd.), and the test was performed. The results were the same and were good without any problems.

Example-52 63.0 parts (0.334 mol) of XDi, 15.0 parts (0.139 mol) of TG, 30.0 (0.061 mol) of PEMP, 0.01% by weight of DBC, N, N-dibutyl A test was performed in the same manner as in Example 1 using 0.005% by weight of aminoethanol and 0.5% by weight of dibutyl phosphoric acid. result,
The viscosity immediately before the injection is 100 cps or less and the injection is extremely easy. The obtained lens is colorless and transparent, and has a refractive index of 1.59.
8, Abbe number 35, specific gravity 1.33, and almost no optical distortion. Also in this test, in addition to dibutylphosphoric acid, Zelek UN, dioctylphosphoric acid, or JP-506 (butoxyethyl ester of acidic phosphoric acid, monoester & diester manufactured by Johoku Chemical Co., Ltd.) was used as the internal release agent.
The mixture was changed to (mixture), and the test was carried out. The result was the same and was good without any problem.

Example 53 530.0 parts (0.225 mol) of IPDi and trimethylolpropane tris (3-mercaptopropionate) 5
9.8 parts (0.150 mol), 0.10% by weight of DMC,
DEC 0.05% by weight, Zelek UN 0.015% by weight
, A test was conducted in the same manner as in Example 1. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and had a refractive index of 1.541.
The Abbe number was 47, the specific gravity was 1.21, and almost no optical distortion was observed. Also in this test, the internal mold release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 (butoxyethyl ester of acid phosphate, a mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.) in addition to Zelek UN. The result was the same, and was good without any problem.

Example 54 540.0 parts (0.225 mol) of IPDi and pentaerythritol tetrakis (3-mercaptopropionate)
A test was conducted in the same manner as in Example 1 using 55.0 parts (0.113 mol), 0.10% by weight of DMC, 0.05% by weight of DEC, and 0.015% by weight of Zelek UN. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and the refractive index was 1.5.
50, Abbe number 47, specific gravity 1.22, and almost no optical distortion. Also in this test, the internal mold release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 (butoxyethyl ester of acid phosphate, a mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.) in addition to Zelek UN. But the results are similar,
It was good without any problems.

Comparative Example-8 50.0 parts (0.225 mol) of IPDi and pentaerythritol tetrakis (3-mercaptopropionate)
A test was conducted in the same manner as in Example 1 using 55.0 parts (0.113 mol), dimethylaminoethyl acetate 0.02% by weight, dibutyltin dilaurate 0.1% by weight, and Zelek UN 0.1% by weight. Was. This composition is disclosed in
84021 corresponds to the composition of Example-1. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and had a refractive index of 1.550 and
Although the Abbe number was 47 and the specific gravity was 1.22, optical distortion was large.

Example 55 550.0 parts (0.191 mol) of HMDi and trimethylolpropane tris (3-mercaptopropionate) 5
0.6 parts (0.127 mol), DMC 0.10% by weight,
DEC 0.05% by weight, Zelek UN 0.015% by weight
, A test was conducted in the same manner as in Example 1. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and had a refractive index of 1.546.
The Abbe number was 48, the specific gravity was 1.21, and almost no optical distortion was observed. Also in this test, the internal mold release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 (butoxyethyl ester of acid phosphate, a mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.) in addition to Zelek UN. The result was the same, and was good without any problem.

Example-56 1,3-Bis (isoanatomethyl) chlorohexane (H
6XDi) 58.3 parts (0.300 mol), 2,5-bis (mercaptomethyl) -1,4-dithiane 38.2 parts (0.180 mol), pentaerythritol tetrakis (thioglycolate) 26.0 Parts (0.06 mol), T
BA 0.10% by weight, DMC 0.10% by weight, JP-5
The same test as in Example 1 was conducted using 0.15% by weight of 06 (butoxyethyl phosphate, monoester & diester mixture, manufactured by Johoku Chemical Co., Ltd.). result,
The viscosity immediately before the injection is 100 cps or less and the injection is extremely easy. The obtained lens is colorless and transparent, and has a refractive index of 1.59.
2, Abbe number 41, specific gravity 1.30, and almost no optical distortion. This test was also performed by changing the internal release agent to dibutyl phosphoric acid, dioctyl phosphoric acid, or Zelek UN, in addition to JP-506.
The results were similar and good without any problems.

Example-57 50.5 parts (0.260 mol) of H6XDi, 42.5 parts (0.200 mol) of 2,5-bis (mercaptomethyl) -1,4-dithiane, 4.3 parts of TG (0 0.040 mol)
And TBA 0.10% by weight, DBC 0.10% by weight, JP
-506 (Johoku Chemical Co., Ltd. acid phosphate butoxyethyl ester, monoester & diester mixture) 0.70
The same test as in Example 1 was performed using the weight%. As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and the refractive index was 1.5.
90, Abbe number 42, specific gravity 1.29, and almost no optical distortion. Also in this test, the internal mold release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or Zelek UN, in addition to JP-506, and the test was performed. .

Example-58 47.1 parts (0.250 mol) of XDi, 21.2 parts (0.100 mol) of 2,5-bis (mercaptomethyl) -1,4-dithiane, 26.1 parts of GST (0. .100 mol), 0.01% by weight of TBA, 0.01% by weight of DMC,
JP-506 (Johoku Chemical Co., Ltd. acid butoxyethyl phosphate, monoester & diester mixture)
The same test as in Example 1 was performed using 10% by weight.
As a result, the viscosity immediately before the injection was 100 cps or less, and the injection was extremely easy. The obtained lens was colorless and transparent, and the refractive index was 1.
660, Abbe number 32, specific gravity 1.35, and almost no optical distortion. Also, for this test,
The test was carried out by changing the internal release agent to dibutyl phosphoric acid, dioctyl phosphoric acid, or Zelek UN, in addition to JP-506, and the results were the same and were good without any problems.

Example 59 598.8 parts (0.262 mol) of HMDi, 8.8 parts (0.096 mol) of glycerin, and 20.8 parts (0,0) of 3,6-dioxaoctane-1,8-dimercaptan .114 mol), 0.8% by weight of TBA, 0.4% by weight of DBC, J
P-506 (Butoxyethyl acid phosphate, monoester & diester mixture manufactured by Johoku Chemical Co., Ltd.) 1.2
The same test as in Example 1 was performed using the weight%. As a result, the viscosity immediately before the injection can be extremely easily injected at 100 cps or less, and the obtained lens is colorless and transparent, and has a refractive index of 1.
535, Abbe number 50, specific gravity 1.17, and almost no optical distortion. Also, for this test,
The test was carried out by changing the internal release agent to dibutyl phosphoric acid, dioctyl phosphoric acid, or Zelek UN, in addition to JP-506, and the results were the same and were good without any problems.

Example-60 18.5 parts (0.110 mol) of HDi and 30.
0 parts (1.14 mol), glycerin 30.0 parts (0.3
26 mol), tributylamine (hereinafter abbreviated as TBA)
0.02% by weight (isocyanates + active hydrogen compound,
The same applies hereinafter), 0.01% by weight of dibutyltin dichloride (hereinafter abbreviated as DBC), JP-506 as an internal release agent.
(Butoxyethyl ester of phosphoric acid, mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.) 1.2% by weight was mixed to form a homogeneous solution, and then defoamed at 20 ° C. After 1 hour, the center thickness consisting of the glass mold and gasket
The injection was made into a 5 mm concave lens mold. The viscosity immediately before the injection was 35 cps of 100 cps or less, and the injection was extremely easy. In addition, the same test was separately conducted at 20 ° C. As a result, the viscosity after 5 hours was 96 cps and 100 cps.
Below, the viscosity was extremely low. Subsequently, the mold was gradually heated from 40 ° C. to 140 ° C. and cured for 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. The results are also shown in Table 1. The obtained lens was colorless and transparent, and had optical properties of a refractive index of 1.52.
3, Abbe number 51, specific gravity 1.20.

Example-61 The test of Example-60 was performed by changing the metal compound to 0.007% by weight of dimethyltin dichloride (hereinafter abbreviated as DMC) and 0.02% by weight of TBA. The results are also shown in Table 1, but as good as in Example-60, the obtained lens was also color-transparent, and the optical properties were a refractive index of 1.523, an Abbe number of 50, and a specific gravity of 1.24. Same as Example-60.

Examples 62 to 70 and Comparative Examples 10 to 12 Plastic lenses were manufactured by the method of Example 60 in order to confirm the effect of the combined use catalyst of a tertiary amine and a metal compound. The results are shown in Table 3. In addition, these tests were conducted by changing the internal release agent to Zelek UN, dibutyl phosphoric acid, or JP-506 (butoxyethyl ester of phosphoric acid, monoester & diester mixture manufactured by Johoku Chemical Co., Ltd.). Similarly, the examples were good.

[0062]

[Table 5]

Example 71 m-xylylene diisoanatate (hereinafter abbreviated as XDi)
108.0 parts (0.574 mol) and glycerin 30.0
Part (0.326 mol), 40.0 parts (0.154 mol) of 1,2-bis (3-mercaptoethylthio) -3-mercaptopropane, N, N-diethylcyclohexylamine (hereinafter abbreviated as DEC). 0.005% by weight, DB
C 0.01% by weight, dibutyl phosphoric acid 1.
A test similar to that of Example-59 was performed using 0% by weight.
The results are shown in Table 4. The obtained lens was colorless and transparent, and the optical properties were a refractive index of 1.593, an Abbe number of 36, and a specific gravity of 1.33.

Examples -72 to 106, Comparative Examples -13 to 1
4 A plastic lens was manufactured by the method of Example-71 in order to confirm the effect of the combined use catalyst of a tertiary amine and a metal compound. The results are shown in Table 4. In addition, for these tests including Example-71, the internal release agent was
N, dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506
(Butoxyethyl phosphate acid mixture, monoester & diester mixture, manufactured by Johoku Chemical Co., Ltd.), and the test was performed. The results were the same and were good without any problems.

[0065]

[Table 6]

[0066]

[Table 7]

[0067]

[Table 8]

Example-107 53.0 parts (0.282 mol) of XDi and 48.0 parts (0.184 mol) of 1,3-bis (2-hydroxyethylthio) -2-propanol (hereinafter abbreviated as GSA) ), D
EC 0.005% by weight, DBC 0.005% by weight, JP
The same test as that of Example-59 was performed using 1.0% by weight of -506 (butoxyethyl ester of phosphoric acid, mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.). As a result, the viscosity immediately before the injection was 100 cps or less and the injection was extremely easy. The obtained lens was colorless and transparent, and the refractive index was 1.5.
92, Abbe number 36, specific gravity 1.32, and almost no optical distortion. This test was also performed by changing the internal release agent to Zelek UN, dibutyl phosphoric acid, or dioctyl phosphoric acid. The results were the same, and were good without any problems.

Example-108 84.5 parts (0.322 mol) of HMDi and GSA30.
0 parts (0.141 mol), 3,6-dioxaoctane-
A test similar to that of Example-59 was performed using 20.0 parts (0.110 mol) of 1,8-dimercaptan, 0.005% by weight of DEC, and 0.005% by weight of DBC. result,
The viscosity immediately before the injection is 100 cps or less, and the injection is extremely easy. The obtained lens is colorless and transparent and has a refractive index of 1.56.
0, Abbe number 45, specific gravity 1.19, and almost no optical distortion.

Example-109 13.5 parts of 1,4-diisothiocyanatobenzene (0.
070 mol) and 7.7 parts (0.07 mol) of hydroquinone tributylamine (hereinafter abbreviated as TBA) 0.02.
% By weight (isocyanates + active hydrogen compound, the same applies hereinafter), dibutyltin dichloride (hereinafter abbreviated as DBC)
After mixing 0.01% by weight and 1.2% by weight of JP-506 (mixture of butoxyethyl ester of acid phosphate, monoester and diester, manufactured by Johoku Chemical Co., Ltd.) as an internal release agent to form a homogeneous solution, the mixture was removed at 20 ° C. Foam went. One hour later,
1.5mm center thickness consisting of glass mold and gasket
Was injected into the concave lens mold. The viscosity immediately before the injection was 35 cps of 100 cps or less, and the injection was extremely easy. In addition, a similar test was conducted separately at 20 ° C. As a result, the viscosity after 5 hours was 75 cps and was 100 cps or less, which was extremely low. Then, this mold,
It was gradually heated from 40 ° C. to 140 ° C. and cured in 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. The obtained lens was colorless and transparent, and had a refractive index of 1.78.

Example-110 10 parts of hexamethylene diisothiocyanate (0.05 part)
Mol) and 11 parts (0.025 mol) of tetrakis (mercaptoethylthiomethyl) methane 0.02% by weight of tributylamine (hereinafter abbreviated as TBA) (isocyanates +
Active hydrogen compound, the same applies hereinafter), dibutyltin dichloride (hereinafter abbreviated as DBC) 0.01% by weight, JP-506 (Johoku Chemical Co., Ltd. acid butoxyethyl phosphate, monoester & diester mixture) as an internal release agent
After mixing 1.2% by weight to form a homogeneous solution, defoaming was performed at 20 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. Viscosity immediately before injection is 35 cps below 100 cps
The injection was very easy. In addition, the same test was conducted separately at 20 ° C. As a result, the viscosity after 5 hours was 60 cp.
The viscosity was very low at s of 100 cps or less. Subsequently, the mold was gradually heated from 40 ° C. to 140 ° C. and cured for 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. Incidentally, the obtained lens was colorless and transparent, and had a refractive index of 1.70.

Example-111 16.3 parts of diisothiocyanatoethyl sulfide (0.
08 mol), 17.0 parts of hydroxyethylthiomethyl-tris (mercaptoethylthiomethyl) methane (0.0
4 mol) tributylamine (hereinafter abbreviated as TBA)
02% by weight (isocyanates + active hydrogen compound, the same applies hereinafter), 0.01% by weight of dibutyltin dichloride (hereinafter abbreviated as DBC), JP-506 as an internal mold release agent
(Butoxyethyl ester of phosphoric acid, mixture of monoester and diester, manufactured by Johoku Chemical Co., Ltd.) 1.2% by weight was mixed to form a homogeneous solution, and then defoamed at 20 ° C. After 1 hour, the center thickness consisting of the glass mold and gasket
The injection was made into a 5 mm concave lens mold. The viscosity immediately before the injection was 35 cps of 100 cps or less, and the injection was extremely easy. In addition, the same test was separately performed at 20 ° C. As a result, the viscosity after 5 hours was 100 cps at 75 cps.
Below, the viscosity was extremely low. Subsequently, the mold was gradually heated from 40 ° C. to 140 ° C. and cured for 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. The obtained lens was colorless and transparent, and had a refractive index of 1.71.

Example-112 1-Isocyanato-4-isothiocyanatobenzene 1
0.6 parts (0.06 mol) and 6.6 parts (0.06 mol) of hydroquinone 0.02% by weight of tributylamine (hereinafter abbreviated as TBA) (isocyanates + active hydrogen compound, the same applies hereinafter), dibutyl Tin dichloride (hereinafter DB)
Abbreviated as C. ) 0.01% by weight, JP-
506 (mixture of butoxyethyl ester of acid phosphate, monoester & diester, manufactured by Johoku Chemical Co., Ltd.) was mixed to form a homogeneous solution, and then defoamed at 20 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. The viscosity immediately before injection was 45 cps of 100 cps or less, and the injection was extremely easy. In addition, the same test was separately conducted at 20 ° C. As a result, the viscosity after 5 hours was 10 cps at 75 cps.
At 0 cps or less, the viscosity was extremely low. Subsequently, the mold was gradually heated to 40 ° C. to 140 ° C.
Cured in time. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. When the obtained lens was observed with a polarizing plate and a high-pressure mercury lamp,
Almost no optical distortion was seen. Incidentally, the obtained lens was colorless and transparent, and had a refractive index of 1.70.

Example-113 1-isocyanato-3-isothiocyanatopropane
5 parts (0.06 mol), 7.0 parts (0.04 mol) of benzenetrithiol, 0.02% by weight of tributylamine (hereinafter abbreviated as TBA) (isocyanates + active hydrogen compound, the same applies hereinafter), dibutyl Tin dichloride (hereinafter DB)
Abbreviated as C. ) 0.01% by weight, JP-
506 (mixture of butoxyethyl ester of acid phosphate, monoester & diester, manufactured by Johoku Chemical Co., Ltd.) was mixed to form a homogeneous solution, and then defoamed at 20 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. The viscosity immediately before injection was 45 cps of 100 cps or less, and the injection was extremely easy. In addition, the same test was separately conducted at 20 ° C. As a result, the viscosity after 5 hours was 10 cps at 75 cps.
At 0 cps or less, the viscosity was extremely low. Subsequently, the mold was gradually heated to 40 ° C. to 140 ° C.
Cured in time. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. When the obtained lens was observed with a polarizing plate and a high-pressure mercury lamp,
Almost no optical distortion was seen. The obtained lens was colorless and transparent, and had a refractive index of 1.75.

Example-114 4-isocyanato-4'-isothiocyanatodiphenyl sulfide 17.0 parts (0.06 mol), 4-mercaptophenol 7.6 parts (0.06 mol) tributylamine (hereinafter referred to as TBA) 0.02 wt. Butoxyethyl ester of acid phosphate, monoester & diester
Mixture) to obtain a homogeneous solution after mixing 1.2% by weight.
Degassing was performed at 0 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. The viscosity immediately before injection is less than 100 cps.
At 5 cps, the injection was very easy. Also, 2
As a result of performing the same test at 0 ° C., the viscosity after 5 hours was 100 cps or less of 75 cps, which was extremely low. Subsequently, the mold was gradually heated from 40 ° C. to 140 ° C. and cured for 5 hours. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion. Incidentally, the obtained lens was colorless and transparent, and had a refractive index of 1.74.

Example-115 43.5 parts of m-xylylene diisocyanate (0.23
Mol) and 56.5 parts (0.115 mol) of pentaerythritol tetrakis (3-mercaptopropionate),
After mixing 0.005% by weight of N, N-diethylcyclohexylamine, 0.01% by weight of DBC, and 0.1% by weight of Zelek UN as an internal release agent to make a uniform liquid, defoaming was performed at 20 ° C. One hour later, injection was performed into a concave lens mold having a center thickness of 1.5 mm and composed of a glass mold and a gasket. Subsequently, the mold was heated in water at 40 ° C. for 2 hours and then in water at 60 ° C. for 1 hour, then transferred to an oven, and heated and cured at 100 for 30 minutes and 140 ° C. for 1 hour. After cooling, remove the lens from the mold and
Reheating was performed at 20 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion.

Example-116 43.5 parts of m-xylylene diisocyanate (0.23
Mol) and 56.5 parts (0.115 mol) of pentaerythritol tetrakis (3-mercaptopropionate),
After mixing 0.005% by weight of N, N-diethylcyclohexylamine and 0.01% by weight of DBC to form a uniform liquid,
Degassing was performed at 20 ° C. One hour later, a baking mold release agent YSR-6209 manufactured by Toshiba Silicone Co., Ltd. was injected into a 1.5 mm center concave lens mold composed of a baked glass mold and a gasket. Subsequently, the mold was heated in water at 40 ° C. for 2 hours and then in water at 60 ° C. for 1 hour, then transferred to an oven, and heated and cured at 100 for 30 minutes and 140 ° C. for 1 hour. After cooling, the lens was taken out of the mold and reheated at 120 ° C. for 1 hour. Observation of the obtained lens with a polarizing plate and a high-pressure mercury lamp showed almost no optical distortion.

[0078]

According to the present invention, an optically uniform urethane-based plastic lens can be molded in a short time.

Continued on the front page (31) Priority claim number Japanese Patent Application No. 6-300612 (32) Priority date December 5, 1994 (12.5 December 1994) (33) Priority claim country Japan (JP) (72) Inventor Teruyuki Nagata 30 Asamuta-cho, Omuta-shi, Fukuoka Prefecture Inside Mitsui-Higashi Toka Chemical Co., Ltd. 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa-ken Mitsui Toatsu Chemicals Co., Ltd. (72) Inventor Keiya Kawauchi 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Mitsui Toatsu Chemicals Co., Ltd. 1190 Kasama-cho, Sakae-ku, Yokohama Mitsui Toatsu Chemicals, Inc. Examiner Takeshi Sato (56) References JP-A-3-287641 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 18/00-18/87 G02B 1/04 G02C 7/02

Claims (24)

(57) [Claims] 1. One or more ester compounds selected from isocyanate compounds, isothiocyanate compounds, and isothiocyanate compounds having an isocyanate group, and hydroxy compounds, mercapto compounds, and hydroxy compounds having a mercapto group. A composition for a urethane-based plastic lens comprising one or more active hydrogen compounds, a tertiary amine and a Lewis acid. 2. The composition for a urethane-based plastic lens according to claim 1, wherein the Lewis acid is a metal halide. 3. The composition for a urethane-based plastic lens according to claim 1, wherein the Lewis acid is an organometallic halide. 4. The composition for a urethane-based plastic lens according to claim 3, wherein the organometallic halide is an organotin halide. 5. A plastic lens obtained by heat-curing the urethane-based plastic lens composition according to claim 1. 6. A plastic lens obtained by heating and curing the urethane-based plastic lens composition according to claim 2. 7. A plastic lens obtained by heating and curing the urethane-based plastic lens composition according to claim 3. 8. A plastic lens obtained by heat-curing the urethane-based plastic lens composition according to claim 4. 9. An ester compound selected from one or more of an isocyanate compound, an isothiocyanate compound, and an isothiocyanate compound having an isocyanate group, and a hydroxy compound, a mercapto compound, and a hydroxy compound having a mercapto group. A composition for a urethane-based plastic lens, comprising one or more active hydrogen compounds, a tertiary amine, a Lewis acid, and an acidic phosphoric acid ester or an acidic phosphonic acid ester as an internal mold release agent. 10. The composition for a urethane-based plastic lens according to claim 9, wherein the acidic phosphate is a mixture of an alkoxyalkyl diester and a monoester of phosphoric acid. 11. A plastic lens obtained by heating and curing the urethane-based plastic lens composition according to claim 9. 12. A plastic lens obtained by heating and curing the urethane-based plastic lens composition according to claim 10. 13. A method for producing a plastic lens, comprising heating and curing the composition for a urethane-based plastic lens according to claim 1. 14. A method for producing a plastic lens, comprising heating and curing the composition for a urethane-based plastic lens according to claim 2. 15. A method for producing a plastic lens, comprising heating and curing the composition for a urethane-based plastic lens according to claim 3. 16. A method for producing a plastic lens, comprising heating and curing the composition for a urethane-based plastic lens according to claim 4. 17. A method for producing a plastic lens, comprising heating and curing the composition for urethane-based plastic lens according to claim 9. 18. A method for producing a plastic lens, comprising heating and curing the composition for a urethane-based plastic lens according to claim 10. 19. The method according to claim 13, wherein a part of the heating is performed in water. 20. The method according to claim 14, wherein a part of the heating is performed in water. 21. The method for producing a plastic lens according to claim 15, wherein a part of the heating is performed in water. 22. The method according to claim 16, wherein a part of the heating is performed in water. 23. The method for producing a plastic lens according to claim 17, wherein a part of the heating is performed in water. 24. The method according to claim 18, wherein a part of the heating is performed in water.