JPH1081726A - Urethane-based plastic lens composition, plastic lens comprising the same, and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition capable of producing a lens which is optically homogeneous and has no or very little optical distortion in a short time, a lens obtained therefrom, and a production method for obtaining the lens. I do. SOLUTION: One or more ester compounds selected from isocyanate compounds, isothiocyanate compounds, isothiocyanate compounds having an isocyanate group, and one selected from hydroxy compounds, mercapto compounds, and hydroxy compounds having a mercapto group Alternatively, a urethane-based plastic lens composition containing two or more active hydrogen compounds, a tertiary phosphine, and a Lewis acid, a lens obtained therefrom, and a method for producing a lens.

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] Therefore, in molding a plastic lens, a casting polymerization method in which a raw material monomer is usually injected into a mold and heat-cured is employed, but in order to obtain an optically homogeneous molded product, a low-temperature to high-temperature molding is required. 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 has been attempted for radical polymerization type monomers. That is, by adopting a light or radiation polymerization method having a high polymerization rate, the lens is cured at a stretch before thermal unevenness occurs inside the lens (Isao Kaetsu, Optical Technology Contact, Vol. 7, 7, 7).
31, (1979)).

The present inventors have proposed a urethane plastic lens as a method for increasing the refractive index of a plastic lens. For example, JP-A-60-199016 discloses a urethane-based plastic lens comprising a polyisocyanate compound and a polythiol compound.
JP-217229A proposed a urethane 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 controlled 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 preparation of a monomer to the injection thereof. In order to increase the polymerization rate, a method of using a strongly active catalyst or increasing the amount of the catalyst is used. Then, during the monomer preparation, the polymerization reaction proceeds and the viscosity increases,
There was a problem that the mold could not be injected, that is, the pot life could not be obtained.

[0007]

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 that can be manufactured, a lens obtained therefrom, and a manufacturing method for obtaining the lens.

[0008]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that one or more 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 two 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 in combination with graded phosphine, a sharp runaway reaction does not occur even if the amount of Lewis acid is large, and a sufficient pot life can be obtained. Furthermore, depending on the combination of monomers, at around room temperature, the polymerizability is lower than when no catalyst is used,
The pot life is longer than when no catalyst is used.
Furthermore, they have found that even if the polymerization time is greatly reduced, 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 more ester compounds selected from isothiocyanate compounds having an isocyanate group, and hydroxy compounds, mercapto compounds, one 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 phosphine, a lens obtained therefrom, and a production method for obtaining the lens.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION 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′-tetramethylxylylenediisocyanate, 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 isocyanates 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, 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 dibenzylsulfone, 4,4'-dimethyldiphenylsulfone-3,3'-diisocyanate, 4,4'-di-tert-butyldiphenylsulfone-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.

Further, halogen-substituted products such as chlorine-substituted products and bromine-substituted products, alkyl-substituted products, alkoxy-substituted products,
Nitro-substituted products, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, buret-modified products, 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,
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-benzenedicarbonyldiisothiocyanate 1,4 benzene dicarbonyl diisothiocyanate, and (2,2'-bipyridine) -4,4'-carbonyl isothiocyanate, such as dicarbonyl diisothiocyanate.

In addition to the isothiocyanate group used as a raw material in the present invention, examples of the difunctional or higher functional isothiocyanate having one or more sulfur atoms include thiobis (3-isothiocyanatopropane) and thiobis ( Sulfur-containing aliphatic isothiocyanates such as 2-isothiocyanatoethane) and dithiobis (2-isothiocyanatoethane);
-Isothiocyanato-4 -− (2-isothiocyanato)
Sulfonyl dibenzene, 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-substituted, alkoxy-substituted and nitro-substituted isothiocyanates such as chlorine- and bromine-substituted isothiocyanates, modified prepolymers with polyhydric alcohols, and modified carbodiimides , Urea modified, buret modified, dimerized or trimerized reaction products and the like 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′-isothiocyanatodiphenyl sulfide and 2-isocyanato-2′-isothiocyanatodiethyl disulfide 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,
Bullet modified products, dimerization or trimerization reaction products, and 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 for the sulfur-containing urethane-based 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 product of the above polyol with an organic acid such as salicylic acid, 3-bromopropionic acid, 2-bromoglycol, dicarboxycyclohexane, pyromellitic acid, butanetetracarboxylic acid, or bromophthalic acid, and the above 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 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 A halogen-substituted aromatic thiol such as a chlorine-substituted product such as 6-tetrachloro-1,5-bis (mercaptomethyl) benzene or a bromine-substituted product; 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.

Furthermore, 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 as a mixture of two or more.

The tertiary phosphine used in the present invention includes the following compounds. For example, trimethylphosphine, triethylphosphine, tripropylphosphine, triisopropylphosphine, tri-n-butylphosphine, trit-butylphosphine, tricyclohexylphosphine, tribenzylphosphine, triphenylphosphine, diphenylmethylphosphine, dimethylphenylphosphine, diethylphenyl Phosphine, tri-tolylphosphine, trimesitylphosphine,
1,2-bis (dimethylphosphino) ethane, 1,4-
Bis (diphenylphosphino) butane, 2,3-bis (diphenylphosphino) butane, 1,2-bis (diphenylphosphino) ethane, bis (diphenylphosphino) methane, 1,3-bis (diphenylphosphino) Propane, 1,2-bis (diphenylphosphino) propane, 1,5-bis (diphenylphosphino) pentane,
And the like.

The Lewis acid used in the present invention is capable of forming a strong complex with the above-mentioned tertiary phosphine, 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, tetraiodotin, 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 nitrocadmium,
Cobalt compounds such as cobalt chloride and cobalt bromide, thorium compounds such as nitrothorium, mercury compounds such as diphenylmercury, nickel 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, metal halides or organometallic halides are preferably used, more preferably tin compounds, and more preferably used are organotin halide compounds. It is.

In the present invention, it is important to use a tertiary phosphine in combination with a Lewis acid and use it as a catalyst.
By using both of them in combination, a sufficient pot life can be provided at around room temperature even if the Lewis acid is used more than usual.

The tertiary phosphine and the metal compound are used in an amount of 0.0005 to 5% by weight, preferably 0.1 to 5% by weight, based on the total amount of the ester compound and the active hydrogen compound.
It is 001 to 2% by weight, but it depends on the combination of the monomer used, the combination of the tertiary phosphine and the metal compound used, the type and amount of additives such as an internal mold 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.

In addition, depending on the purpose, as in a known molding method, 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 two or more ester compounds, one or two or more active hydrogen compounds, a tertiary phosphine, and a metal compound are mixed. After defoaming the mixed solution by an appropriate method as needed, 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 the catalyst, but are usually −20 to 200 ° C. and 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 if necessary. Further, 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 property, or impart fashionability, if necessary. Physical or chemical treatment such as hard coat treatment, anti-reflection coat treatment, dyeing treatment, light control treatment, and the like.

[0035]

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 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 8 parts (0.114 mol), 0.5% by weight of tri-n-butylphosphine (hereinafter abbreviated as TBP) (the same applies to the ester compound and the active hydrogen compound), dibutyltin dichloride (hereinafter abbreviated as DBC) 0.4% by weight (the same applies to the isocyanate compound and the active hydrogen compound), JP-506 (mixture of butoxyethyl acid phosphate, monoester and diester, manufactured by Johoku Chemical Co., Ltd.) as an internal release agent After mixing 2% by weight (the same applies to the isocyanate compound and the active hydrogen compound, the same applies hereinafter) 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 100 cp
At 50 cps below s, the injection was extremely easy. In addition, a similar test was separately conducted at 20 ° C. As a result, the viscosities after 5 hours were 90 cps and 100 cps or less, which were extremely low. Subsequently, the mold is heated at 40 ° C.
It was gradually heated to 0 ° 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. In addition, the obtained lens is colorless and transparent, and the optical properties are
The refractive index was 1.548, the Abbe number was 47, and the specific gravity was 1.18.

Example 2 The same test as in Example 1 was carried out except that the metal compound was changed to 0.3% by weight of dimethyltin dichloride (hereinafter abbreviated as DMC) and 0.5% by weight of TBP. The results were as good as in Example 1. The obtained lens was colorless and transparent, had no optical distortion, and had optical properties of a refractive index of 1.548, an Abbe number of 47, and a specific gravity of 1.18. Was similar to

Example 3 68.8 parts (0.262 mol) of hydrogenated MDi, 10.4 parts (0.096 mol) of 1-thioglycerin, 3,6-dioxaoctane-1,8-dimercaptan 8 parts (0.114 mol), triphenylphosphine (hereinafter T
Abbreviated as PP. ) 0.7% by weight, 0.4% by weight of DBC, and 1.2% by weight of JP-506 as an internal release agent were mixed to form a uniform solution, followed by defoaming at 20 ° C. 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 60 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 extremely low at 100 cps. 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. The obtained lens was colorless and transparent, had no optical distortion, and had optical properties of a refractive index of 1.548 and an Abbe number of 4
7, specific gravity 1.18.

Example 4 0.3% by weight of DMC and 0.7% by weight of TPP
The same test as in Example 3 was performed except that the test was changed to. The results were as good as in Example 3. The obtained lens was colorless and transparent, had no optical distortion, and had optical properties of a refractive index of 1.54.
8, similar to Example 3 with an Abbe number of 47 and a specific gravity of 1.18.

Example 5 m-xylylene diisoanatate (hereinafter abbreviated as XDi)
43.5 parts (0.23 mol) and pentaerythritol tetrakis (3-mercaptopropionate) (hereinafter PE
Abbreviated as MP. ) 56.5 parts (0.115 mol), TBP
The same test as in Example 1 was performed using 0.013% by weight, 0.01% by weight of DBC, and 0.1% by weight of Zelek UN (acid phosphate alkyl ester manufactured by Du Pont) as an internal release agent. The viscosity before injection was as good as 100 cps or less, and no optical distortion was observed in the obtained lens.
The obtained lens was colorless and transparent, and the optical properties were a refractive index of 1.594, an Abbe number of 36, and a specific gravity of 1.34.

Example 6 43.5 parts (0.23 mol) of XDi and 56.5 of PEMP
Parts (0.115 mol), TPP 0.018% by weight, DB
C, 0.01% by weight, Zelek UN0.
The same test as in Example 1 was performed using 1% by weight. The viscosity before injection was as good as 100 cps or less. The obtained lens had no optical distortion, was colorless and transparent, and had optical properties of a refractive index of 1.594, an Abbe number of 36, and a specific gravity of 1.3.
It was 4.

Example 7 52.0 parts (0.276 mol) of XDi and 48.0 parts (0.184 mol) of 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane (hereinafter abbreviated as GST) ), 0.020% by weight of TBP, 0.015% by weight of DBC, and 0.1% by weight of Zelek UN, and the same test as in Example 1 was performed. As a result, the viscosity immediately before the injection was 100 cp.
s or less can be injected very easily. 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. In this test, the internal release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 in addition to Zelek UN. The results were the same, and were good without any problems.

Example 8 52.0 parts (0.276 mol) of XDi and 48.0 parts of GST
Parts (0.184 mol), TPP 0.027% by weight, DB
The same test as in Example 1 was performed using 0.015% by weight of C and 0.1% 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, the refractive index was 1.660, the Abbe number was 32, the specific gravity was 1.35, and almost no optical distortion was observed. Was. Also in this test, the internal mold release agent was changed to dibutyl phosphoric acid, dioctyl phosphoric acid, or JP-506 in addition to Zelek UN, and the test was performed. The results were the same and were satisfactory without any problem. .

Comparative 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 After mixing 8 parts (0.114 mol), 0.4% by weight of DBC, and 1.2% by weight of Zelec UN as an internal mold release agent, a uniform solution was prepared, followed by defoaming 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 100c
At 150 cps or higher, injection was somewhat difficult.
In addition, a similar test was conducted separately at 20 ° C., and as a result, the viscosity after 5 hours was extremely high at 600 cps. The obtained lens is colorless and transparent, and has optical properties of a refractive index of 1.5.
Although it was 48, Abbe number 47 and specific gravity 1.18, optical distortion was large.

Comparative Example 2 43.5 parts (0.23 mol) of XDi and 56.5 of PEMP
Example 1 using 0.1 parts by weight (0.115 mol), 0.01% by weight of DBC, and 0.1% by weight of Zelek UN as an internal release agent.
The same test was performed. The viscosity before injection was as good as 100 cps or less, but the lens had a large optical distortion.
The obtained lens was colorless and transparent, and the optical properties were a refractive index of 1.594, an Abbe number of 36, and a specific gravity of 1.34.

Comparative Example 3 52.0 parts (0.276 mol) of XDi and 48.0 parts of GST
Part (0.184 mol), 0.1 g of dibutyltin dilaurate.
The same test as in Example 1 was conducted using 14% by weight and 0.1% by weight of Zelek UN. As a result, the viscosity immediately before the injection was 10
Injection was extremely easy at 0 cps or less, and the obtained lens was colorless and transparent. The refractive index was 1.660, the Abbe number was 32, and the specific gravity was 1.35, but the optical distortion was large.

[0047]

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

──────────────────────────────────────────────────の Continuation of the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical display location C08K 5/5313 C08K 5/5313 C08L 75/04 NGD C08L 75/04 NGD G02B 1/04 G02B 1 / 04 G02C 7/04 G02C 7/04 // B29K 75:00 (72) Inventor Yoshinobu Kanamura 30 Asamuta-cho, Omuta-shi, Fukuoka Mitsui Toatsu Chemicals Co., Ltd. (72) Inventor Teruyuki Nagata Asam-shi, Fukuoka 30 Mutacho Mitsui Toatsu Chemicals Co., Ltd.

Claims (24)

[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 phosphine 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 heat-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 phosphine, a Lewis acid, and an acidic phosphoric acid ester or an acidic phosphonic acid ester as an internal mold release agent. 10. The urethane-based plastic lens composition 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 heat-curing the urethane-based plastic lens composition according to claim 9. 12. A plastic lens obtained by heat-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 heat-curing the urethane-based plastic lens composition according to claim 2. 15. A method for producing a plastic lens, comprising heat-curing the urethane-based plastic lens composition 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 a urethane-based plastic lens according to claim 9. 18. A method for producing a plastic lens, comprising heating and curing the urethane-based plastic lens composition according to claim 10. 19. The method for producing a plastic lens according to claim 13, wherein a part of the heating is performed in water. 20. The method for producing a plastic lens 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 according to claim 17, wherein a part of the heating is performed in water. 24. The method for producing a plastic lens according to claim 18, wherein a part of the heating is performed in water.