KR20090082719A - High Refractive Index Optical Resin Composition Comprising New Thioepoxy Compounds and Optical lens Using It - Google Patents

Abstract

The present invention relates to an optical resin composition comprising a novel thioepoxy compound and an optical lens using the same, and in particular, an optical resin composition excellent in impact resistance, transparency, light weight, etc., while maintaining high Abbe's number and exhibiting ultra high refractive index; It relates to an optical lens using the same. The optical resin composition of the present invention comprises a novel thioepoxy compound represented by the following Chemical Formula 1 in at least one molecule.

[Formula 1]

Description

High Refractive Index Optical Resin Composition Comprising New Thioepoxy Compounds and Optical Lens Using It

The present invention relates to an optical resin composition comprising a novel thioepoxy compound and an optical lens using the same, and more particularly, to an optical resin composition having excellent impact resistance, transparency, light weight, and high refractive index, and an optical lens using the same.

Plastic optical lenses are widely used because they are excellent in light weight and impact resistance compared to glass lenses. Resin of the plastic optical lens which is used a lot until now is polydiethylene glycolbis (allyl carbonate), modified diallyl phthalate. Although this resin has excellent impact resistance, light weight, and dyeing property, it has a low refractive index (nd) of about 1.50 to 1.55, so that the thickness of the lens becomes thick. Therefore, a resin having a higher refractive index while having properties comparable to this resin in impact resistance, light weight, workability, and the like is required.

Examples of the resin having a higher refractive index than polydiethylene glycol bis (allylcarbonate) and modified diallyl phthalate resin include polythiourethane resins into which sulfur atoms are introduced; Sulfur-containing O- (meth) acrylate resins; Thio (meth) acrylate resins; These resins are evaluated to have more appropriate characteristics in terms of high refractive index and impact resistance.

In addition, many optical resins have been developed so far, but the demand for lenses with higher refractive index and Abbe number continues. Especially in the case of high myopia, a new optical resin is required to make the thickness of the lens thinner.

However, since the refractive index and the Abbe number generally have opposite characteristics, the Abbe number decreases as the refractive index increases. Therefore, it is still difficult to develop an optical resin that obtains a high refractive index lens and keeps the Abbe number high and satisfies sufficient impact resistance.

An object of the present invention is to provide an optical resin composition comprising a novel thioepoxy compound having excellent impact resistance, transparency, light weight, and the like and maintaining a high Abbe number and exhibiting a high refractive index, and an optical lens using the same.

Other objects and advantages of the present invention will be described below and will be better understood by practice of the present invention.

In the present invention, there is provided an optical resin composition comprising a thioepoxy compound represented by the following formula (1).

[Formula 1]

In addition, the present invention provides an ultra-high refractive index plastic optical lens having excellent impact resistance, transparency, light weight, and the like, obtained by curing the optical resin composition, and maintaining a high Abbe number.

The optical lens manufactured using the optical resin composition containing the novel thioepoxy compound according to the present invention can be used as an ultra high refractive index lens that maintains a high Abbe number while being excellent in impact resistance, transparency, and lightness. In addition, the optical resin composition of the present invention can be used as an optical product such as a recording medium substrate and a color filter and an ultraviolet absorption filter for use in a prism, an optical fiber, an optical disk and a magnetic disk.

The optical resin composition of the present invention comprises a novel thioepoxy compound represented by the following formula (1).

[Formula 1]

The optical resin composition of the present invention may further include a mercapto compound for controlling the heat resistance and curing rate of the solid resin. That is, the mercapto compound can be used together with the compound of formula (1). As used herein, “comprising a mercapto compound” or “used with a compound of formula 1” means including reacting a mercapto compound with a compound of formula 1. As a mercapto compound, Monothiol, such as methyl mercaptan, benzene thiol, benzyl thiol; Methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithi Ol, 1,2,3-propane trithiol, 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] hepta-exo-cis-2,3- Dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl) thiomaleate, 2-mercaptoethyl-2,3-dimercaptosuccinate, 2,3-dimer Capto-1-propanol-2-mercaptoacetate, 2,3-dimercapto-1-propanol-3-mercaptoacetate, diethylene glycol bis (20 mercaptoacetate). Diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropylmethylether, 2,3-dimercaptopropylmethylether, 2,2-bis (mercaptomethyl) -1,3 Propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate). Ethylene glycol bis (3-mercaptopropionate) and trimethylolpropane tris (2-mercaptoacetate). Trimethylolpropane tris (3-mercaptopropionate). Aliphatic compounds such as pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate) and 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane Polythiol: 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercapto Methyl) benzene, 1,4-bis (mercaptomethyl) benzene, 1,2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis- (mercaptoethyl Tyl) benzene, 1,2-bis (mercaptomethyleneoxy) benzene, 1,3-bis (mercaptomethyleneoxy) benzene, 1,4-bis (mercaptomethyleneoxy) benzene, 1,2-bis (mer Captoethyleneoxy) benzene, 1,3-bis (mercaptoethyleneoxy) benzene, 1,4-bis (mercaptoethyleneoxy) benzene, 1,2,3-trimercaptobenzene, 1,2,4-tri Mercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercap Tomethyl) 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 (mercaptomethyleneoxy) benzene, 1,2,4-tris (mercaptomethyleneoxy) benzene, 1,3,5-tris (mer Captomethyleneoxy) benzene, 1,2,3-tris (mercaptomethyleneoxy) benzene, 1,2,4-tris (mercaptoethyleneoxy) benzene, 1,3,5-tris (mercaptoethyleneoxy) benzene , 1,2,3,4-tetra mercaptobenzene, 1,2,3,5-tetra mercaptobenzene, 1,2,4,5-tetra mercaptobenzene, 1,2,3,4-tetrakis (Mercaptomethyl) benzene, 1,2,3,5-tetrakis (mercaptomethyl) benzene, 1,2,4,5-tetrakis (mercaptomethyl) benzene, 1,2,3,4-tetra Kis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene. 1,2,4,5-tetrakis (mercaptoethyl) benzene, 1,2,3,4-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptomethyleneoxy ) Benzene, 1,2,4,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,4-tetrakis (mercaptoethyleneoxy) benzene, 1,2,3,5-tetrakis ( Mercaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptoethyleneoxy) benzene, 2,2-dimercaptobiphenyl, 4,4-dimercaptobiphenyl, 4,4-di Mercaptobibenzyl, 2,5-blueendiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphthalene Dithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracenedimethanediol, 1,3-di (p-methoxy Phenyl) propane-2, 2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol and 2,4-di (p-mercaptophenyl) pentane and the like Aromatic polyols; 2,5-dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimer Halogen-substituted aromatic polythiols such as chlorine-substituted aromatic polythiols such as captobenzene and 2,3,4,6-tetrachloro-1,5-bis (mercaptomethyl) benzene or substituted aromatic polythiols of bromine; 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-sym-triazine, 2-cyclonucleosilamino-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 and 2-thiobutyloxy-4,6-dithiol polytoys containing one or more heterocycles, such as -sym-triazine; 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 (mercaptomethylthio) 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 (mercaptomethyl Thio) benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, 1,2,3,4-tetrakis (mercaptoethylthio) benzene, 1,2,3,5-tetrakis Aromatic polythiols containing one or more sulfur atoms in mercapto groups such as (mercaptoethylthio) benzene and 1,2,4,5-tetrakis (mercaptoethylthio) benzene; Nuclear alkylated derivatives of aromatic polythiols: bis (mercaptomethyl) sulfide, bis (mercaptoethyl) sulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercapto Ethylthio) methane, bis (3-mercaptopropylthio) methane, 1,2-bis (mercaptomethylthio) ethane, 1,2- (2-mercaptoethylthio) ethane, 1,2- (3- Mercaptopropylthio) 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 (30 mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (20 mercapto Ethylthiomethyl) methane, tetrakis (3-mercaptopropyl thi Omethyl) methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide Aliphatic polyols containing one or more sulfur atoms in addition to mercapto groups such as feed and bis (mercaptopropyl) disulfide are water, for example, hydroxymethylsulphibis (2-mercaptoacetate), hydroxymethylsul Feedbis (3-mercaptopropionate). Hydroxyethyl 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-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate). Hydroxyethyl disulfide bis (3-mercaptopropionate). Hydroxypropyldisulfidebis (2-mercaptoacetate). Hydroxypropyldisulfide bis (3-mercaptopropionate). 2-mercaptoethyl etherbis (2-mercaptoacetate). 2-mercaptoethyl etherbis (3-mercaptopropionate). 1,4-dithiane-2,4-diolbis (2-mercaptoacetate), 1,4-dithiane-2,5-diolbis (3-mercaptopropionate). Bis (2-mercaptoethyl) thioglycolate, bis (2-mercaptoethyl) thiodipropionate, bis (2-mercaptoethyl) 4,4-thiodibutyrate, bis (2,3-dimer Captopropyl) thiodiglycolate, bis (2,3-dimercaptopropyl) thiodipropionate, bis (2,3-mercaptopropyl) dithioglycolate and (2,3-dimercaptopropyl) Thioglycolic acid and mercaptopropionic acid ester of the said polythiol, such as dithio dipropionate; And 3,4-thiophendithiol, tetrahydrothiophene-2,5-dimercaptomethyl, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1 And heterocyclic compounds containing one or more sulfur atoms in addition to mercapto groups such as, 4-dithiane and 2,5-dimercaptomethyl-1,4dithiane.

Mercapto group-containing hydroxy compounds may also be used together, for example 2-mercaptoethanol, 3-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-di Mercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris (3-mercaptopropionate), pentaerythritol mono (3-mercaptopropionate), penta Erythritol bis (3-mercaptopylopionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4- Mercaptodiphenylsulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethylsulfide mono (3-mercaptopropionate). Dimercaptoethanemono (salicylate) and hydroxyethylthiomethyl-tris (mercaptoethylthio) methane, 2 (2-mercaptoethylsulfonyl) propane-1,3-thiol, 2,3-bis ( 2-mercaptoethylsulfonyl) propane-1-thiol, 2- (2-mercaptoethylsulfonyl) -3- [2- (3-mercaptoethylsulfonyl) -propylsulfonyl] ethylsulfonyl-propane -1-thiol, 3- (3-mercapto-2- (2-mercaptoethylsulfonyl) propylsulfonyl propane-1,2-dithiol, 2- (2mercaptoethylsulfonyl) -3- [ One or two or more of 2-mercapto-2- (2-mercaptoethylsulfonyl) -propylsulfonyl] -propane-1-thiol may be added and used.

The optical resin composition of the present invention may further include an isocyanate compound. That is, an isocyanate compound can be used together with the compound of formula (1). As used herein, “comprises an isocyanate compound” or “used with a compound of formula 1” is meant to include reacting an isocyanate compound with a compound of formula 1. As an isocyanate compound, For example, phenyl isocyanate, butyl isocyanate, cyclohexyl isocyanate, phenyl isothiocyanate, butyl isothiocyanate, cyclohexyl isothiocyanate, ethylene diisocyanate, trimethylene diisocyanate, tetra Methylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexanediisocyanate, decamethylene diisocyanate, butene diisocyanate, 1, 3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecanetriisocyanate, 1,3,6-hexamethylenetriisocyanate, 1,8-di Socianate-4-isocyanatomethyloctane, 2,5,7-trimethyl-1,8-diisocyanato-5-isocy Neatomethyloctane, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether, 1, 4- butylene glycol dipropyl ether-ω, ω- diisocyanate, methyl lysine diisocyanate , Lysine triisoanate, 2-isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylenediisocyanate , Bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α, α-tetramethylxylylenediisocyanate, bis (isocyanatobutyl) benzene, bis (iso Cyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenylether, bis (isocyanatoethyl) phthalate, mesityrylylenetriisocyanate and 2,6-di (Isocyanatomethyl) furan and the like; Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexyl methane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2-dimethyldicyclohexyl Methane diisocyanate, bis (4-isocyanato-n-butylidene) pentaerythritol, dimer acid diisocyanate, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -5-iso Cyanatomethylbicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatoflofil) -6-isocyanatomethylbicyclo [2,2 , 1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocy Anatomethyl-2- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-iso city Neitopropyl) -6- (2-isocyanatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6 -(2-isocyanatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl- 2- (3-isocyanatopropyl) -5- (2-isocy Anatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -ratio Aliphatic cyclic polyisocyanates such as cyclo [2,2,1] -heptane and 1,3,5-tris (isocyanatomethyl) -cyclohexane; Phenylene diisocyanate, tolylene diisocyanate, ethyl phenylene diisocyanate, isopropylene phenylene diisocyanate, dimethyl phenylene diisocyanate, diethyl phenylene diisocyanate, diisopropyl phenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, Methylnaphthalene 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, bis (isocyanatophenyl) ethylene, triphenylmethanetriisocyanate, polymer MDI, naphthalene triisocyanate, di Phenylmethane-2,4,4-triisocyanate, 3-methyldipe Nyl methane-4, 6, 4-triisocyanate, 4-methyldiphenylmethane-3,5,2,4,6-penta isocyanate, phenyl isocyanatomethyl isocyanate, phenyl isocyanatoethyl isocyanate, tetra Hydronaphthylene diisocyanate, hexahydrobenzene diisocyanate, hexahydrodiphenylmethane-4,4-diisocyanate, diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate Aromatic polyisocyanates such as benzophenone diisocyanate, diethylene glycol diphenyl ether diisocyanate, dibenzofurane diisocyanate, carbazole diisocyanate, ethyl carbazole diisocyanate and dichlorocarbazole diisocyanate; Thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, dimethyl sulfon diisocyanate, dithiodimethyl diisocyanate, dithio diethyl diisocyanate, dithio dipropyl diisocyanate, dicyclohexyl sulfi-4,4- Aliphatic polyisocyanates containing sulfur such as diisocyanate and 1-isocyanatomethylthia-2,3-bis (2-isocyanatoethylthia) propane; Diphenylsulfide-2,4-diisocyanate, diphenylsulfide-4,4-diisocyanate, 3,3-dimethoxy-4,4-diisocyanatodibenzylthioether, bis (4-isocyane Aromatic sulfide polyisocyanates such as itomethylbenzene) sulfide and 4,4-methoxybenzenethioethylene glycol-3,3-diisocyanate; Diphenylsulfide-4,4-diisocyanate, 2,2-dimethyldiphenyldisulfide-5,5-diisocyanate, 3,3-dimethyldiphenyldisulfide-5,5-diisocyanate, 3,3- Dimethyldiphenylsulfide-6,6-diisocyanate, 4,4-dimethyldiphenylsulfide-5,5-diisocyanate, 3,3-dimethoxydiphenylsulfide-4,4-diisocyanate and 4 Aromatic disulfide polyisocyanates such as, 4-dimethoxydiphenyl sulfide-3,3-diisocyanate; Diphenylsulfone-4,4-diisocyanate, diphenylsulfone-3,3-diisocyanate, benzidinesulfone-4,4-diisocyanate, diphenylmethanesulphone 4,4`- diisocyanate, 4-methyldiphenylmethane Sulfone-2,4′-diisocyanate, 4,4-dimethoxydiphenylsulphone-3,3-diisocyanate, 3,3-dimethoxy-4,4-diisocyanatodibenzylsulfone, 4,4-dimethyl Diphenylsulfone-3,3-diisocyanate, 4,4-di-tert-butyldiphenylsulfone-3,3-diisocyanate, 4,4-methoxybenzeneethylenedisulfone-3,3-diisocyanate and 4 Aromatic sulfone polyisocyanates such as, 4-dichlorodiphenyl sulfone-3,3-diisocinate; 4-methyl-3-isocyanatobenzenesulfonyl- sulfonic acid ester, such as 4-isocyanatophenol ester and 4-methoxy-3-isocyanatobenzenesulfonyl-4-isocyanatophenol ester Polyisocyanate; 4-Methyl-3-isocyanatobenzenesulfonylanilideo-3-methyl-4-isocyanate, dibenzenesulfonyl-ethylenediamine-4,4-diisocyanate, 4,4-methoxybenzenesulfonyl-ethylene Aromatic sulfonamides such as diamine-3,3-diisocyanate and 4-methyl-3-isocyanatobenzenesulfonylanilideo-4-methyl-3-isocyanate, thiophene-2,5-diisocyanate, methyl thi Offen-2,5-diisocyanate, 1,4-dithiane-2,5-diisocyanate, methyl 1,4-dithiane-2,5-diisocyanate, 1,3-dithiolane-4,5-di Isocyanates, methyl 1,3-dithiolane-4,5-diisocyanate, methyl 1,3-dithiolane-2-methyl-4,5-diisocyanate, ethyl 1,3-dithiolane-2,2-diisocyanate , Tetrahydrothiophene-2,5-diisocyanate, methyltetrahydrothiophene-2,5-diisocyanate, ethyltetrahydrothiophene-2,5-diisocyanate, methyltetrahydrothiophene-3,4-dii Cyanate, 1,2-diisothiocyanatoethane, 1,3-diisothiocyanatopropane, 1,4-diisothiocyanatobutane, 1,6-diisothiocyanatohexane And aliphatic polyisothiocyanates such as p-phenylenediisopropylidene diisothiocyanate; Aliphatic ring polyisothiocyanates such as cyclohexanediisothiocyanate; 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanatotoluene, 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-isothiocyanatobenzene). 4,4-diisothiocyanatobenzophenyl, 4,4-diisothiosinganeto-3,3-dimethylbenzophenone, benzanilideo-3,4-diisothiocyanate, diphenyl ether Aromatic polyisothiocyanates such as 4,4-diisothiocyanate and diphenylamine-4,4-diisothiocyanate, 2,4,6-triisothiocyanato-1,3,5 Heterocyclic-containing isothiocyanate, hexanediyl diisothiocyanate, nonanediyl diisothiocyanate, carbonic diisothiocyanate, 1,3-benzenedicarbonyl diisothiocia, such as triazine Nate, 1,4-benzenedicarbonyl diisothiocyanate and (2,2-bipyridine) -4,4dicarbonyldiisocyanate, thiobis (3-isothiocyanatopropane), thiobis (2 Sulfur-containing aliphatic isothiocyanates such as isocyanatoethane) and dithiobis (2-isothiocyanatoethane); 1-isothiocyanato-4-[(2-isothiocyanato) sulfonyl] benzene. Thiobis (4-isothiocyanatobenzene). Sulfonylbis (4-isothiocyanatobenzene). Sulfonylbis (4-isothiocyanatobenzene), dithiobis (40isothiocyanatobenzene). 4-isothiocyanato-1-[(4-isothiocyanatophenyl) sulfonyl] -2-methoxybenzene, phenyl 4-methyl-3-isothiocyanatobenzenesulfonyl-4-iso Sulfur-containing aromatic isothiocyanates such as thiocyanate and 4-methyl-3-isothiocyanatobenzenesulfonylanilideo-3-methyl-4-isothiocyanate; And thiophenone-2,5-diisothiocyanate, 1,4-dithiane-2,5-diisothiocyanate, 1-isocyanato-3-isothiocyanatopropane, 1- Isocyanato-5-isothiocyanatopentane, 1-isocyanato-6-isothiocyanatohexane, isocyanatocarbonylisothiocyanate and 1-isocyanato-4- Aromatic compounds such as isothiocyanatobenzene and 4-methyl-3-isocyanato-1-isothiocyanatobenzene; Heterocyclic compounds such as 2-isocyanato-4,5-diisothiocyanato-1,3,5-triazine, 4-isocyanato-4-isothiocyanatodiphenylsulfide And 2-isocyanato-2-isothiocyanatodiethyldisulfide, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2, 2-dimethylpentane diisocyanate, 2,2,4-trimethylhexanediisocyanate, decamethylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene di Isocyanate, 1,6,11-undecanetriisocyanate, 1,3,6-hexamethylenetriisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane, 2,5,7-trimethyl- 1,8-Diisocyanato-5-iso Anatomethyloctane, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether, 1,4-butylene glycol dipropyl ether-ω, ω--isocyanate, methyllysine diisocyanate, lysine Triisoanate, 2-isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylenediisocyanate, bis (Isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, (alpha), (alpha), (alpha), (alpha)-tetramethyl xylylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocy Anatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenylether, bis (isocyanatoethyl) phthalate, mesityrylylenetriisocyanate and 2,6-di ( Aliphatic polyisocyanates such as isocyanatomethyl) furan Update; Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexyl methane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethyl methane diisocyanate, 2,2-dimethyldicyclo Hexyl methane diisocyanate, bis (4-isocyanato-n-butylidene) pentaerythritol, dimer acid diisocyanate, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -5- Isocyanatomethylbicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatoflofil) -6-isocyanatomethylbicyclo [2, 2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-iso Cyanatomethyl-2- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3- Iso City Anatopropyl) -6- (2-isocyanatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6 -(2-isocyanatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5- (2-isocy Anatoethyl) -bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -ratio Aliphatic cyclic polyisocyanates such as cyclo [2,2,1] -heptane and 1,3,5-tris (isocyanatomethyl) -cyclohexane; Phenylene diisocyanate, tolylene diisocyanate, ethyl phenylene diisocyanate, isopropylene phenylene diisocyanate, dimethyl phenylene diisocyanate, diethyl phenylene diisocyanate, diisopropyl phenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, Methylnaphthalene 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, bis (isocyanatophenyl) ethylene, triphenylmethanetriisocyanate, polymer MDI, naphthalene triisocyanate, Diphenylmethane-2,4,4-triisocyanate, 3-methyldi Nyl methane-4,6,4-triisocyanate, 4-methyldiphenylmethane-3,5,2,4,6-penta isocyanate, phenyl isocyanatomethyl isocyanate, phenyl isocyanatoethyl isocyanate, tetra Hydronaphthylene diisocyanate, hexahydrobenzene diisocyanate, hexahydrodiphenylmethane-4,4-diisocyanate, diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate Aromatic polyisocyanates such as benzophenone diisocyanate, diethylene glycol diphenyl ether diisocyanate, dibenzofurane diisocyanate, carbazole diisocyanate, ethyl carbazole diisocyanate and dichlorocarbazole diisocyanate; Thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, dimethyl sulfon diisocyanate, dithiodimethyl diisocyanate, dithio diethyl diisocyanate, dithio dipropyl diisocyanate, dicyclohexyl sulfi-4,4- Aliphatic polyisocyanates containing sulfur such as diisocyanate and 1-isocyanatomethylthia-2,3-bis (2-isocyanatoethylthia) propane; Diphenylsulfide-2,4-diisocyanate, diphenylsulfide-4,4-diisocyanate, 3,3-dimethoxy-4,4-diisocyanatodibenzylthioether, bis (4-isocyane Aromatic sulfide polyisocyanates such as itomethylbenzene) sulfide and 4,4-methoxybenzenethioethylene glycol-3,3-diisocyanate; Diphenylsulfide-4,4-diisocyanate, 2,2-dimethyldiphenyldisulfide-5,5-diisocyanate, 3,3-dimethyldiphenyldisulfide-5,5-diisocyanate, 3,3- Dimethyldiphenylsulfide-6,6-diisocyanate, 4,4-dimethyldiphenylsulfide-5,5-diisocyanate, 3,3-dimethoxydiphenylsulfide-4,4-diisocyanate and 4, Aromatic disulfide polyisocyanates such as 4-dimethoxydiphenyl sulfide-3,3-diisocyanate; Diphenylsulfone-4,4-diisocyanate, diphenylsulfone-3,3-diisocyanate, benzidinesulfone-4,4-diisocyanate, diphenylmethanesulphone 4,4`- diisocyanate, 4-methyldiphenylmethane Sulfone-2,4′-diisocyanate, 4,4-dimethoxydiphenylsulphone-3,3-diisocyanate, 3,3-dimethoxy-4,4-diisocyanatodibenzylsulfone, 4,4-dimethyl Diphenylsulfone-3,3-diisocyanate, 4,4-di-tert-butyldiphenylsulfone-3,3-diisocyanate, 4,4-methoxybenzeneethylenedisulfone-3,3-diisocyanate and 4 Aromatic sulfone polyisocyanates such as, 4-dichlorodiphenyl sulfone-3,3-diisocinate; Sulfonic acid esters such as 4-methyl-3-isocyanatobenzenesulfonyl-4-isocyanatophenol ester and 4-methoxy-3-isocyanatobenzenesulfonyl-4-isocyanatophenol ester Polyisocyanate; 4-Methyl-3-isocyanatobenzenesulfonylanilideo-3-methyl-4-isocyanate, dibenzenesulfonyl-ethylenediamine-4,4-diisocyanate, 4,4-methoxybenzenesulfonyl-ethylene Aromatic sulfonamides such as diamine-3,3-diisocyanate and 4-methyl-3-isocyanatobenzenesulfonylanilideo-4-methyl-3-isocyanate, thiophene-2,5-diisocyanate, methyl thi Offen-2,5-diisocyanate, 1,4-dithiane-2,5-diisocyanate, methyl 1,4-dithiane-2,5-diisocyanate, 1,3-dithiolane-4,5-di Isocyanates, methyl 1,3-dithiolane-4,5-diisocyanate, methyl 1,3-dithiolane-2-methyl-4,5-diisocyanate, ethyl 1,3-dithiolane-2,2-diisocyanate , Tetrahydrothiophene-2,5-diisocyanate, methyltetrahydrothiophene-2,5-diisocyanate, ethyltetrahydrothiophene-2,5-diisocyanate and methyltetrahydrothiophene-3,4- D Socyanate, 1,2-diisothiocyanatoethane, 1,3-diisothiocyanatopropane, 1,4-diisothiocyanatobutane, 1,6-diisothiocyanatohexane And aliphatic polyisothiocyanates such as p-phenylenediisopropylidene diisothiocyanate; Aliphatic ring polyisothiocyanates such as cyclohexanediisothiocyanate; 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanatotoluene, 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-isothiocyanatobenzene). 4,4-diisothiocyanatobenzophenyl, 4,4-diisothiosinganeto-3,3-dimethylbenzophenone, benzanilideo-3,4-diisothiocyanate, diphenyl ether Aromatic polyisothiocyanates such as 4,4-diisothiocyanate and diphenylamine-4,4-diisothiocyanate, 2,4,6-triisothiocyanato-1,3,5 Heterocyclic-containing isothiocyanate, hexanediyl diisothiocyanate, nonanediyl diisothiocyanate, carbonic diisothiocyanate, 1,3-benzenedicarbonyl diisothiocia, such as triazine Nate, 1,4-benzenedicarbonyl diisothiocyanate and (2,2-bipyridine) -4,4dicarbonyldiisocyanate, thiobis (3-isothiocyanatopropane), thiobis (2 Sulfur-containing aliphatic isothiocyanates such as isocyanatoethane) and dithiobis (2-isothiocyanatoethane); 1-isothiocyanato-4-[(2-isothiocyanato) sulfonyl] benzene. Thiobis (4-isothiocyanatobenzene). Sulfonylbis (4-isothiocyanatobenzene). Sulfonylbis (4-isothiocyanatobenzene), dithiobis (40isothiocia neitobenzene). 4-isothiocyanato-1-[(4-isothiocyanatophenyl) sulfonyl] -2-methoxybenzene, phenyl 4-methyl-3-isothiocyanatobenzenesulfonyl-4-iso Sulfur-containing aromatic isothiocyanates such as thiocyanate and 4-methyl-3-isothiocyanatobenzenesulfonylanilideo-3-methyl-4-isothiocyanate; And thiophenone-2,5-diisothiocyanate, 1,4-dithiane-2,5-diisothiocyanate, 1-isocyanato-3-isothiocyanatopropane, 1- Isocyanato-5-isothiocyanatopentane, 1-isocyanato-6-isothiocyanatohexane, isocyanatocarbonylisothiocyanate and 1-isocyanato-4- Aromatic compounds such as isothiocyanatobenzene and 4-methyl-3-isocyanato-1-isothiocyanatobenzene; Heterocyclic compounds such as 2-isocyanato-4,5-diisothiocyanato-1,3,5-triazine; In addition, one or two or more kinds of 4-isocyanato-4-isothiocyanatodiphenyl sulfide and 2-isocyanato-2-isothiocyanatodiethyl disulfide can be used. .

In the resin composition of the present invention, the ultraviolet absorber is added in an amount of 0.005 to 6% by weight (50 to 60,000 ppm), preferably 0.01 to 3% by weight (100 to 30,000 ppm), based on the total weight of the composition. If the amount of the ultraviolet absorber is less than 0.005% by weight, no effective ultraviolet absorbing capacity can be obtained, and yellowing may be severe when the lens is exposed to ultraviolet rays. In addition, when it is 6% by weight or more, not only it is difficult to dissolve in the composition, but also a poor polymerization may occur during curing. As the ultraviolet absorbent, any known ultraviolet absorbent usable for spectacle lenses can be used without limitation. For example, 2- (2'-hydroxy-5- methylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-amylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole; 2,4-dihydroxybenzophenone; 2-hydroxy-4-methoxybenzophenone; 2-hydroxy-4-octyloxybenzophenone; 4-dodecyloxy-2-hydroxybenzophenone; 4-benzooxy-2-hydroxybenzophenone; 2,2 ', 4,4'-tetrahydroxybenzophenone; 2,2'- dihydroxy-4,4'- dimethoxy benzophenone etc. can be used individually or in mixture of 2 or more types. Preferably, 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole or 2 having good ultraviolet absorption in the wavelength range of 400 nm or less and having good solubility in the composition of the present invention; , 2'-dihydroxy-4,4'-dimethoxybenzophenone and the like can be used.

As the organic dye, known organic dyes may be used. In one embodiment of the present invention, Kyungin Yang Co., Ltd. 1-hydroxy-4- (p-toludine) enthraquinone [1-HYDROXY-4- (P-TOLUIDIN) ANTHRAQUINONE], Perinone dye (PERINONE DYE) ) And the like. By adding 0.5 to 10,000 ppm, preferably 5 to 1000 ppm, of such organic dye per kg of the monomer, it is possible to prevent the optical lens from becoming yellow by the addition of an ultraviolet absorber.

In the present invention, the releasing agent, a component selected from fluorine-based nonionic surfactants, silicone-based nonionic surfactants, alkyl quaternary ammonium salts, phosphate esters, and phosphonic acid esters may be used alone or in combination of two or more thereof in the monomer composition. Preferably acidic phosphate esters or acidic phosphonic acid esters are used. The use of the composition by applying it to a metal or glass mold also makes excellent deforming. As phosphate ester, Isopropyl acid four state; Diisopropyl acid phosphate; Butyl phosphate; Octylic acid phosphate; Dioctyl acid phosphate; Isodecyl phosphate; Diisodecyl acid phosphate; Tridecanoic acid phosphate; Bis (tridecanoic acid) phosphate or the like may be used alone or in combination of two or more thereof. As a result of using in the embodiment of the present invention, when using the phosphate ester ZELEC UN (DUPONT) and KPSS-1000 (Zeta Chemtech) was found that the best demolding when the mold is demolded in the lens after curing. The addition amount of the release agent may be used in an amount of 0.001 to 5% by weight relative to the monomer, but preferably 0.005 to 2% by weight of the mold release property of the lens and high polymerization yield.

The polymerization initiator used in the present invention is amine-based, for example triethylamine, tripropylamine, dipropylethylamine, tributylamine, trihexylamine, dimethylcyclohexylamine, dicyclohexylethylamine, tricyclohexylamine , Diethylcyclohexylamine, dicyclohexylethylamine, dipropylcyclohexylamine, dicyclohexylpropylamine, dibutylcyclohexylamine, dicyclohexylbutynamine, N, N-dimethylbenzylamine, N, N- Diethylbenzylamine, N, N-dipropylbenzylamine, N, N-dibutylbenzylamine, N-methylbenzylamine, 2-dimethylaminomethylphenol, 2,4,6-tris (N, N-dimethylamino Methyl) phenol, triethylenediamine, tetramethylethylenediamine, tetraethylethylenediamine, N, N-dimethylcyclohexylamine, N, N-dicyclohexylmethylamine, tetrapropylethylenediamine, tetrabutylethylenediamine, pentamethyldi Ethylenetri amine, pentaethyldiethylenetri Min, pentapropyldiethylenetriamine, pentabutyldiethylenetriamine, N-methylpiperidine, N-ethylpiperidine, N-propylpiperidine, N-butylpiperidine, N, N-dimethylpipepe Razine, N, N-diethylpiperazine, N, N-dipropylpyrazine, N, N-dibutylperazine, hexamethylenetetramine, dimethylaminoethylacetate, diethylaminoethylacetate, dimethylaminopropionitrile , Diethylaminopropionitrile, 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 and N-butylpyrrolidone. Examples of aromatic tertiary amines include N, N-dimethylaniline, N, N-diethylaniline, N, 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-dicy Clohexyltoluidine, N, N-dimethylnaphthylamine, N, N_diethylnaphthylamine, N, N-dimethylanisidine, N, N-diethylanisidine and N, N, N`, N`- Tetramethylphenylenediamine and the like. Pyridine, picoline, dimethylpyridine, 2,2'-bipyridine, 4,4'-bipyridine, pyridine, N-methylpyrazole, N-ethylpyrazole, N-propylpyrazole, N-butylpyrazole , N-cyclosecsilpyrazole, pyridazine, pyrimidine, pyriline, oxazole, thiazole, 1-methylimidazole, 1-benzylimidazole, 1-methyl-2methylimidazole, 1-benzyl 2-methylimidazole, 1-ethyl-4-methylimidazole, 1-ethyl-2-ethyl-4-methylol, N-methylpyrrole, N-ethylpyrrole, N-butylpyrrole, N-methyl Pyrroline, N-ethylpyrroline, N-butylpyrroline, pyrimidine, purine, quinoline, isoquinoline, N-methylcarbazole, N-ethylcarbazole and N-butylcarbazole can be used, Moreover, as a tin type compound, Butyl tin dilaurate; Dibutyl tin dichloride; Dibutyl tin diacetate; Oxalic acid stannous; Dibutyl dilaurate; Tetrafluorotin; Tetrachlorotin; Tetrabromotin; Tetraiodine tin; Methyl tin trichloride; Butyltin trichloride; Dimethyltin dichloride; Dibutyltin dichloride; Trimethyltin chloride; Tributyltin chloride; triphenyltin chloride; Dibutyltin sulfide; Di (2-ethylsecyl) tin oxide and the like may be used alone or in combination of two or more thereof.

Examples of the Lewis acid include zinc-based compounds such as zinc chloride, acetylacetone zinc and zinc dibutyldithiocarbamate; Iron compounds, such as iron chloride and acetylacetone iron: Aluminum compounds, such as alumina, aluminum fluoride, aluminum chloride, and triphenyl aluminum, etc. can be used. It is preferable to use the usage-amount 0.001-5 weight% in the whole composition.

The optical resin composition of the present invention is thermally cured to obtain plastic optical lenses, in particular spectacle lenses. Preferred embodiments for preparing the spectacle lens by thermal curing the composition of the present invention are as follows. First, after finally adding the polymerization initiator to the composition of the present invention, by substituting with nitrogen to remove air in the mixing vessel (reactor), stirring under reduced pressure is carried out for 2 to 5 hours, stopping stirring, and then degassing under reduced pressure. Inject into the mold. The mold is preferably a glass mold or a metal mold fixed with a plastic gasket or polyester or polypropylene adhesive tape. The glass mold into which the mixture was injected is placed in a forced circulation oven, held at a temperature of 33 ° C. for 12 hours, heated at 33 ° C. to 80 ° C. for 10 hours, held at 80 ° C. for 2 hours, heated at 80 ° C. to 100 ° C. for 3 hours, and heated at 100 ° C. for 2 hours. After holding for a period of time and cooling for 2 hours at 80 ° C., the solids are released from the mold to obtain an optical lens. The optical lens thus obtained is subjected to annealing at a temperature of 100 to 120 ° C. for 1 to 4 hours to obtain a final desired plastic optical lens.

In addition, the optical lens obtained by the above method was subjected to hard coating and multi-coating treatment in order to increase optical characteristics. The hard coat layer may be formed of at least one silane compound having functional groups such as an epoxy group, an alkoxy group, a vinyl group, and at least one metal oxide colloid such as silicic acid oxide, titanium oxide, antimony oxide, tin oxide, tungsten oxide, and aluminum oxide. The coating composition was coated with a thickness of 0.5 to 10 μm on the surface of the optical lens by impregnation or spin coating, followed by heating or UV curing to complete the coating film.

The multi-coating layer, that is, the anti-reflective coating layer may be formed by vacuum deposition or sputtering of metal oxides such as silicon oxide, magnesium fluoride, aluminum oxide, zirconium oxide, titanium oxide, tantalum oxide and yttrium oxide. Most preferably, the silicon oxide film and the zirconium oxide film are repeatedly vacuum-deposited three times on both surfaces of the lens and the silicon oxide film is finally vacuum deposited. In addition, depending on demand, an ITO layer may be further provided between the silicon oxide and zirconium oxide film as a water film layer in the last layer.

The optical lens of the present invention may be used after coloring treatment using a disperse dye or a photochromic dye, as necessary.

The optical resin composition of the present invention is not limited to plastic spectacle lenses, and can be used in various optical products.

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, the scope of the present invention is not limited by the following examples, and those skilled in the art to which the present invention pertains should be within the equivalent scope of the technical concept of the present invention and the claims to be described below. Of course, various modifications and variations are possible.

Manufacturing example Formula 1 )

1) 1 mole of glycidol is slowly added to a mixed solution of 1 mole of 2-mercaptoethanol and 3 ml of ethylenetriamine while maintaining the temperature at 30 ^° C. or lower and stirred at 40 ^° C. for 1 hour.

2) Add 3.3 moles of thiourea and 4.5 moles of concentrated hydrochloric acid to reflux for 3 hours, cool down, and add 5.8 moles of ammonia water to it at 30 ^o C or lower.

3) After the dropwise addition of ammonia water, add 500 ml of toluene and stir at 70 ^° C for one hour. After the reaction, the organic layer was separated, washed with 10% hydrochloric acid solution, washed three times with water, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed to obtain a colorless liquid.

4) To 0.008 mol of sodium hydroxide dissolved in 5 ml of secondary distilled water and 3.0 mol of epichlorohydrin, slowly added dropwise while keeping the colorless liquid substance below 20 ^° C. After completion of the dropping, the mixture was aged at 30 ^° C. for 1 hour, and then 500 ml of toluene and 500 ml of methanol were added thereto, and 3.0 mol of NaOH aqueous solution was slowly added dropwise at 40 ^° C.

5) After completion of the dropping, stir for 3 more hours and add water to separate the organic layer, wash the organic layer several times with water, dry and filter with anhydrous magnesium sulfate, and remove the solvent to give a colorless liquid. .

6) To the obtained species, 1440 ml of toluene and 1330 ml of methanol are added, followed by cooling to 15 ^° C., 6.0 mol of thiourea and 0.3 mol of acetic anhydride. The reaction was stirred for 8 hours with stirring at 30 ^° C. under a nitrogen stream, and the termination of the reaction was stopped when the reaction was no longer performed on TLC.

7) After completion of the reaction, add 300 ml of 25% aqueous sulfuric acid solution, stir at 15 ^o C for 30 minutes, separate the organic layer, wash the organic layer three times with 300 ml of distilled water, and separate the organic layer, anhydrous magnesium sulfate After drying and filtration, the solvent was removed to obtain component 1 of formula (1), the yield was 82%.

[Formula 1]

Example 1

(1) 100 g of component (I) represented by the formula (1), 2 g of 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole as a ultraviolet absorber, 0.01 g of isopropyl acid as a release agent , 20 ppm of 1-hydroxy-4- (p-toluidino) anthraquinone (blue) as organic dye, 10 ppm of perrinone di (Red), and 0.05 g of triethylamine as polymerization initiator were placed in a mixing vessel equipped with a stirrer. After substituting with nitrogen to remove air in the mixing vessel, stirring was carried out under reduced pressure for 2 hours, stirring was stopped, and degassed under reduced pressure and injected into a glass mold fixed with a polyester adhesive tape (diopta -5.00).

(2) The glass mold into which the mixture was injected is placed in a forced circulation oven, held at 33 ° C. for 12 hours, heated at 33 ° C. to 80 ° C. for 10 hours, held at 80 ° C. for 2 hours, and heated to 80 to 100 ° C. for 3 hours, 100. After holding for 2 hours at 80 ° C. and cooling for 2 hours at 80 ° C., the solid was released from the mold to obtain an optical lens having a center thickness of 1 mm.

(3) The optical lens obtained in (2) was processed to a diameter of 72 mm and then ultrasonically washed with an alkaline aqueous washing solution, followed by annealing at 100 ° C. for 2 hours.

(4) The lens obtained in (3) was impregnated with hard solution of Finecoder ST11 Water-8H, and then thermally cured. Silicon oxide, zirconium oxide, silicon oxide, ITO, oxide, zirconium film, silicon oxide, Zirconium oxide and a water film (fluorine resin) were vacuum-deposited to obtain hard-coated and multi-coated optical lenses.

Property test method

The physical properties of each optical lens were measured by the following experimental method, and the results are reported in Table 1.

1. Refractive index and Abbe number: It was measured using an Abbe refractometer, an Atacota Co 1T model.

2. Light transmittance: It measured using the spectrophotometer.

3. Light resistance: The optical lens (degree of -5.00) was exposed to QUV / Spray model (5w) of Q-Pannellad products for 200 hours, and if there was no color change of the lens, O and X were indicated.

4. Specific gravity: It was calculated by measuring the volume and weight of the optical lens by using the underwater substitution method.

Examples 2-6

In the manufacture of the other optical material of the present invention and the manufacture of the lens, the procedure of Example 1 was repeated except that polymerization conditions were appropriately changed using the resin composition shown in Table 1, thereby producing a lens. The physical properties are shown in Table 1.

Abbreviation notation

GMT: 2 (2-mercaptoethylsulfonyl) propane-1,3-thiol

GST: 2,3-bis (2-mercaptoethylsulfonyl) propane-1-thiol

ETS4: 2- (2-mercaptoethylsulfonyl) -3- [2- (3-mercaptoethylsulfonyl) -propylsulfonyl] ethylsulfonyl-propane-1-thiol

GMS4: 3- (3-mercapto-2- (2-mercaptoethylsulfonyl) propylsulfonyl propane-1,2-dithiol

GMS5: 2- (2 mercaptoethylsulfonyl) -3- [2-mercapto-2- (2-mercaptoethylsulfonyl) -propylsulfonyl] -propane-1-thiol

Claims (5)

An optical resin composition comprising a thioepoxy compound represented by Formula 1 below. [Formula 1]

The optical resin composition of claim 1, further comprising a mercapto compound. The optical resin composition of claim 1, further comprising an isocyanate compound. The optical resin composition according to any one of claims 1 to 3, further comprising a polymerization initiator, an ultraviolet absorber, an internal mold release agent, and an organic dye. The optical lens obtained by thermosetting the optical resin composition of any one of Claims 1-3.