KR102669070B1 - Novel episulfide compound, a composition for an episulfide-based optical material comprising the same, and a method for producing an optical material - Google Patents

Abstract

The present invention relates to a novel episulfide compound that can improve the light resistance, heat resistance, and transparency of optical materials by including a small amount in a composition for episulfide-based optical materials, a composition for episulfide-based optical materials containing the same, and a method for producing optical materials. It's about. The present invention provides a composition for an episulfide-based optical material comprising an episulfide compound represented by Formula 2 below, an episulfide compound represented by Formula 1 below, a polythiol compound, and a polymerization catalyst.
[Formula 1]

(X, Y are hydrogen, hydroxyl group, alkyl group, aryl group, alicyclic group, amino group, oxime or ester group, and X and Y are the same or different from each other.)

Description

Novel episulfide compound, composition for an episulfide-based optical material containing the same, and method for producing an optical material {Novel episulfide compound, a composition for an episulfide-based optical material comprising the same, and a method for producing an optical material}

The present invention relates to a novel episulfide compound and an episulfide-based optical material containing the same. In particular, a novel episulfide compound that can improve the light resistance, heat resistance, and transparency of an optical material by including a small amount in a composition for an episulfide-based optical material. It relates to compounds, compositions for episulfide-based optical materials containing the same, and methods for producing optical materials.

Plastic lenses are light, have good impact resistance, and are easy to tint, so plastic lenses are used in most spectacle lenses these days. Plastic eyeglass lenses have been developed to improve lightness, transparency, low yellowness, heat resistance, light resistance, and strength.

Korean Patent No. 10-0681218 discloses an episulfide-based plastic lens. Episulfide-based lenses have excellent properties of having a high refractive index and a high Abbe number, but they have many problems in terms of tensile strength, compressive strength, coloring, hard adhesion, and productivity. In order to solve this problem, a method of copolymerizing two types of resins with different properties, that is, a method of copolymerizing an episulfide compound and a polythiol compound or a polyisocyanate compound, is disclosed in Korean Patent No. 10-0417985 and Japanese Published Patent. It was proposed in No. 11-352302, etc.

Recently, in order to further increase the refractive index in episulfide-based lenses containing episulfide compounds and achieve an ultra-high refractive index and high Abbe number of 1.71 or more, a composition for optical materials that mixes inorganic compounds such as sulfur atoms or selenium atoms with the episulfide compound. This was proposed (Japanese Patent Publication 2001-2783).

However, episulfide-based lenses have problems with poor light fastness and heat resistance, and often reduced transparency.

Republic of Korea Registered Patent Publication 10-0417985 Japanese Patent Publication No. 11-352302 Japanese Patent Publication No. 2001-2783 Republic of Korea Patent Publication No. 10-2014-0122721

Episulfide-based high refractive index optical lenses have problems with poor light resistance and heat resistance, and often reduced transparency. This problem can cause deformation of the lens when the user is exposed to high temperature environments such as outdoor activities or saunas for long periods of time, and deteriorates the quality of the lens. In addition, in the case of reduced transparency, the resulting defects can reduce productivity and hinder commercialization.

The present invention seeks to solve this problem by including a new episulfide compound in a composition for episulfide-based optical materials. The purpose of the present invention is to provide a new episulfide compound that can solve the problems of low light resistance, heat resistance, and reduced transparency that occur in episulfide-based high refractive index optical lenses. In addition, the present invention provides a composition for episulfide-based optical materials with excellent light resistance, heat resistance, and transparency using this compound, and a method for producing optical materials.

In order to achieve the above object, in the present invention,

An episulfide compound represented by Formula 1 below is provided.

Additionally, in the present invention,

An episulfide compound represented by Formula 2 below,

An episulfide compound represented by Formula 1 below,

polythiol compounds and

A composition for an episulfide-based optical material containing a polymerization catalyst is provided.

[Formula 1]

(X, Y are hydrogen, hydroxyl group, alkyl group, aryl group, alicyclic group, amino group, oxime or ester group, and X and Y are the same or different from each other.)

[Formula 2]

(In the formula, X and Y are O or S, m is an integer from 0 to 4, and n represents an integer from 0 to 2.)

The composition for episulfide-based optical materials may further include sulfur.

The composition for episulfide-based optical materials may further include a polyisocyanate compound.

The composition for episulfide-based optical materials may further include a tin halogen compound as a polymerization regulator.

Additionally, the present invention provides a method for producing an episulfide-based high refractive index optical material, which includes polymerizing the composition for the episulfide-based optical material.

The episulfide compound of Formula 1 provided by the present invention is a novel compound, and can solve the problems of low light resistance, heat resistance, and reduced transparency that occur in episulfide-based optical materials. In the present invention, an episulfide-based optical material with excellent light resistance, heat resistance, and transparency can be obtained by a relatively simple method of polymerizing this compound by including a small amount of 10% by weight or less in a composition for an episulfide-based optical material.

In the present invention, unless specifically limited, 'high refraction' includes everything from 1.67 or higher to 1.71 or higher, commonly referred to as ultra-high refraction. Although not limited, the refractive index usually falls within the range of 1.67 to 1.77.

The present invention provides a novel episulfide compound represented by Formula 1 below.

(X, Y are hydrogen, hydroxyl group, alkyl group, aryl group, alicyclic group, amino group, oxime or ester group, and X and Y are the same or different from each other.)

By polymerizing a small amount of the episulfide compound represented by Formula 1 in a composition for an episulfide-based optical material, an optical material with much better light resistance, heat resistance, and transparency can be obtained. The compound represented by Formula 1 is preferably included in an amount of 0.01 to 10% by weight based on the total weight of the composition for episulfide-based optical materials. More preferably, it can be used in an amount of 0.01 to 7% by weight, and even more preferably in an amount of 0.05 to 5% by weight.

The episulfide compound represented by Formula 1 can be produced, for example, by reacting 2,3-epoxypropyl (2,3-epithiopropyl) sulfide with 2,2,6,6-tetramethylpiperidine, Alternatively, it can be obtained by reacting 2,3-epoxypropyl (2,3-epithiopropyl) sulfide with 2,2,6,6-tetramethylpiperidyl methacrylate. Bis(3-chloro-2-hydroxypropyl)sulfide can be obtained using picchlorohydrin as a starting material, and then treated with caustic soda solution to obtain bis(2,3-epoxypropyl)sulfide. Bis(2,3-epoxypropyl)sulfide can be selectively reacted with thiourea to obtain 2,3-epoxypropyl(2,3-epithiopropyl)sulfide. 2,3-Epoxypropyl (2,3-epithiopropyl) sulfide and hindered amine can be dissolved in an organic solvent and then reacted at 30-35°C to obtain the new episulfide compound (Formula 1) of the present invention. In some cases, without using an organic solvent, 2,3-epoxypropyl (2, A new episulfide compound (Formula 1) can be obtained through a 1:1 reaction of 3-epithiopropyl)sulfide and hindered amine.

The composition for an episulfide-based optical material of the present invention includes an episulfide compound represented by the following formula (2), an episulfide compound represented by the formula (1), a polythiol compound, and a polymerization catalyst.

(In the formula, X and Y are O or S, m is an integer from 0 to 4, and n represents an integer from 0 to 2.)

The episulfide compound represented by the above formula (2) is the main component of the composition for episulfide-based optical materials. The episulfide compound of Formula 2 is, for example, bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, 2,3-epoxypropyl(2,3-epithiopropyl) ) disulfide, 2,3-epoxypropyl (2,3-epithiopropyl) sulfide, 1,3 and 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3 and 1,4-bis ( β-Epitiopropylthiomethyl)cyclohexane, bis[4-(β-epithiopropylthio)cyclohexyl]methane, 2,2-bis[4-(β-epithiopropylthio)cyclohexyl]propane, bis Episulfide compounds having an alicyclic skeleton such as [4-(β-epithiopropylthio)cyclohexyl]sulfide; 1,3 and 1,4-bis(β-epithiopropylthiomethyl)benzene, bis[4-(β-epithiopropylthio)phenyl]methane, 2,2-bis[4-(β-epithiopropyl) thio)phenyl]propane, bis[4-(β-epithiopropylthio)phenyl]sulfide, bis[4-(β-epithiopropylthio)phenyl]sulfine, 4,4-bis(β-epithiopropylthio) ) Episulfide compounds having an aromatic skeleton such as biphenyl; 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithian, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithian, 2,5- Epi having a dithian chain skeleton such as bis(β-epithiopropylthioethyl)-1,4-dithiane, 2,3,5-tri(β-epithiopropylthioethyl)-1,4-dithiane, etc. sulfide compounds; 2-(2-β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane, 1,2-bis[(2-β-epithiopropylthioethyl)thio]- 3-(β-epithiopropylthio)propane, tetrakis(β-epithiopropylthiomethyl)methane, 1,1,1-tris(β-epithiopropylthiomethyl)propane, bis-(β-epithio) It can be an episulfide compound with an aliphatic skeleton such as propyl) sulfide. In addition, as episulfide compounds, halogen-substituted products such as chlorine-substituted products, bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, or prepolymer-type modified products with polythiol can also be used.

The episulfide compound is preferably bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, and 2,3-epoxypropyl(2,3-epithiopropyl)sulfide. , 2,3-epoxypropyl (2,3-epithiopropyl) disulfide, 1,3 and 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3 and 1,4-bis (β- Epithiopropylthiomethyl)cyclohexane, 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithian, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1, One or more of 4-dithiane, 2-(2-β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane can be used.

The polythiol compound is not particularly limited, and any compound having at least one thiol group can be used alone or in a mixture of two or more types. Preferably, bis(2-mercaptoethyl)sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithioctane, 2,3-bis(2-mercaptoethylthio)propane. -1-thiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, tetrakis(mercaptomethyl)methane; 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2-(2,3-bis(2-mercaptoethylthio)propylthio)ethanethiol, bis(2,3-dimercapto Propanyl) sulfide, bis (2,3-dimercaptopropanyl) disulfide, 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 1,2-bis (2- (2- Mercaptoethylthio)-3-mercaptopropylthio)ethane, bis(2-(2-mercaptoethylthio)-3-mercaptopropyl)sulfide, bis(2-(2-mercaptoethylthio)-3 -Mercaptopropyl)disulfide, 2-(2-mercaptoethylthio)-3-2-mercapto-3-[3-mercapto-2-(2-mercaptoethylthio)-propylthio]propylthio- Propane-1-thiol, 2,2-bis-(3-mercapto-propionyloxymethyl)-butyl ester, 2-(2-mercaptoethylthio)-3-(2-(2-[3-mer Capto-2-(2-mercaptoethylthio)-propylthio]ethylthio)ethylthio)propane-1-thiol, (4R,11S)-4,11-bis(mercaptomethyl)-3,6,9 ,12-tetrathiatetradecane-1,14-dithiol, (S)-3-((R-2,3-dimercaptopropyl)thio)propane-1,2-dithiol, (4R,14R) -4,14-bis(mercaptomethyl)-3,6,9,12,15-pentathiaheptane-1,17-dithiol, (S)-3-((R-3-mercapto-2- ((2-mercaptoethyl)thio)propyl)thio)propyl)thio)-2-((2-mercaptoethyl)thio)propane-1-thiol, 3,3'-dithiobis(propane-1,2 -dithiol), (7R,11S)-7,11-bis(mercaptomethyl)-3,6,9,12,15-pentathiaheptadecane-1,17-dithiol, (7R,12S)- 7,12-bis(mercaptomethyl)-3,6,9,10,13,16-hexathioctadecane-1,18-dithiol, 5,7-dimercaptomethyl-1,11-dimer Capto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaoundecane, 4,8-dimercaptomethyl- 1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), penta Ethritol tetrakis (2-mercaptoacetate), bispentaerythritol-ether-hexakis (3-mercaptopropionate), 1,1,3,3-tetrakis (mercaptomethylthio) propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithian and 2-(2,2-bis(mercaptodimethylthio) )Ethyl)-1,3-dithiane may be used. In addition, any compound having one or more thiol groups can be used one type or a mixture of two or more types. In addition, polymerized modified products obtained by prepolymerization of polythiol compounds with isocyanate compounds, episulfide compounds, thiethane compounds, or compounds with unsaturated bonds as a resin modifier can also be used.

The polythiol compound is particularly preferably bis(2-mercaptoethyl)sulfide or 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane or other polythiol compounds. More than one species can be mixed and used.

Polythiol may preferably be contained in the composition for optical materials in an amount of 1 to 15% by weight, more preferably in an amount of 4 to 13% by weight, and even more preferably in an amount of 5 to 11% by weight.

The polymerization catalyst preferably uses at least one selected from amines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, and phosphine compounds. More preferably, one or more types selected from quaternary ammonium salts, quaternary phosphonium salts, and phosphine compounds can be used. As quaternary ammonium salts, for example, tetra-n-butylammonium bromide, tetraphenylammonium bromide, triethylbenzylammonium chloride, cetyldimethylbenzylammonium chloride, 1-n-dodecylpyridinium chloride, etc. can be used. . As quaternary phosphonium salts, for example, tetra-n-butylphosphonium bromide, tetraphenylphosphonium bromide, etc. can be used. Triphenylphosphine, etc. can be used as the phosphine compound. Particularly preferably, the polymerization catalyst is a quaternary phosphonium salt and includes either tetra-n-butylphosphonium bromide or tetraphenylphosphonium bromide. These polymerization catalysts can be used individually or in combination of two or more types.

The composition for episulfide-based optical materials may further include sulfur. If more sulfur is added, the refractive index can be increased to an ultra-high refraction of 1.71 or more. The sulfur contained in the composition preferably has a purity of 98% or more. If it is less than 98%, the transparency of the optical material may decrease due to the influence of impurities. The purity of sulfur is more preferably 99.0% or more, and particularly preferably 99.5% or more. Generally, commercially available sulfur is classified by differences in shape and purification method, and includes finely divided sulfur, colloidal sulfur, precipitated sulfur, crystalline sulfur, and sublimated sulfur. In the present invention, any sulfur can be used as long as it has a purity of 98% or higher. Preferably, finely powdered sulfur of fine particles that are easily soluble can be used when producing a composition for optical materials. The sulfur content in the composition is preferably 1 to 40% by weight, more preferably 2 to 30% by weight, and most preferably 3 to 22% by weight of the total weight of the composition for optical materials.

The composition for episulfide-based optical materials may further include a polyisocyanate compound. The polyisocyanate compound is not particularly limited, and a compound having at least one isocyanate group and/or isothiocyanate group may be used. For example, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, hexamethylene diisocyanate, 2,4, 4-trimethylhexamethylene diisocyanate, 1,6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate-4-isocyanatomethyloctane, bis(isocyanate) Aliphatic isocyanate compounds such as anatoethyl)carbonate and bis(isocyanatoethyl)ether; Isophorone diisocyanate, 1,2-bis(isocyanatomethyl)cyclohexane, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, Alicyclic isocyanate compounds such as dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, and 2,2-dimethyldicyclohexylmethane isocyanate; Xylylene diisocyanate (XDI), bis(isocyanatoethyl)benzene, bis(isocyanatopropyl)benzene, bis(isocyanatobutyl)benzene, bis(isocyanatomethyl)naphthalene, bis( Isocyanatomethyl) diphenyl ether, phenylene diisocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene tri. Isocyanate, diphenyl diisocyanate, toluidine diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, bibenzyl-4,4'-diisocyanate , bis(isocyanatephenyl)ethylene, 3,3'-dimethoxybiphenyl-4,4'-diisocyanate, hexahydrobenzened diisocyanate, hexahydrodiphenylmethane-4,4'-diisocyanate, etc. Aromatic isocyanate compounds; Bis(isocyanatoethyl)sulfide, bis(isocyanatopropyl)sulfide, bis(isocyanatohexyl)sulfide, bis(isocyanatomethyl)sulfone, bis(isocyanatomethyl)disulfide, Bis(isocyanatopropyl)disulfide, bis(isocyanatomethylthio)methane, bis(isocyanatoethylthio)methane, bis(isocyanatoethylthio)ethane, bis(isocyanatomethyl) Sulfur-containing aliphatic isocyanate compounds such as thio)ethane and 1,5-diisocyanato-2-isocyanatomethyl-3-thiapentane; Diphenyl sulfide-2,4-diisocyanate, diphenyl sulfide-4,4'-diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanatodibenzylthioether, bis(4-isocy) Anatomethylbenzene) sulfide, 4,4-methoxybenzenethioethylene glycol-3,3-diisocyanate, diphenyldisulfide-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'-dimethoxydiphenyldisulfide-4,4'-diisocyanate, 4,4'-dimethoxydiphenyldisulfide-3,3'-diisocyanate, etc. Sulfur-containing aromatics isocyanate compounds; 2,5-diisocyanatothiophene, 2,5-bis(isocyanatomethyl)thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis(isocyanatomethyl) Tetrahydrothiophene, 3,4-bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanato-1,4-dithian, 2,5-bis(isocyanatomethyl) -1,4-dithiane, 4,5-diisocyanato-1,3-dithiorane, 4,5-bis(isocyanatomethyl)-1,3-dithiolane, 4,5-bis( One or two or more compounds selected from sulfur-containing heterocyclic isocyanate compounds such as isocyanatomethyl)-2-methyl-1,3-dithiorane may be used. In addition, any compound having at least one isocyanate group and/or isothiocyanate group can be used one type or a mixture of two or more types. In addition, halogen-substituted products such as chlorine-substituted products, bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-type modified products with polyhydric alcohols or thiols, carbodiimide-modified products, urea-modified products, and biuret-modified products of these isocyanate compounds. Alternatively, dimerization or trimerization reaction products can also be used. The polyisocyanate compound is preferably isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), dicyclohexylmethane diisocyanate (H12MDI), xylylene diisocyanate (XDI), 3,8-bis(iso Cyanatomethyl)tricyclo[5,2,1,02,6]decane, 3,9-bis(isocyanatomethyl)tricyclo[5,2,1,02,6]decane, 4,8-bis (isocyanatomethyl)tricyclo[5,2,1,02,6]decane, 2,5-bis(isocyanatomethyl)bicyclo[2,2,1]heptane, 2,6-bis(iso One or more types selected from cyanatomethyl)bicyclo[2,2,1]heptane can be used.

The composition for episulfide-based optical materials may further include a tin halogen compound as a polymerization regulator. The tin halogen compound is preferably one of dibutyltin dichloride, dimethyltin dichloride, or one containing a small amount of monomethyltin trichloride. More preferably, monomethyltin trichloride may be included in an amount of 0.1 to 3.5% by weight. When a composition for an episulfide-based optical material is polymerized and cured, the reaction proceeds quickly and the viscosity of the composition may rapidly increase. Since the polymerization regulator can suppress a rapid increase in viscosity by controlling the reaction rate, this problem can be solved by using the polymerization regulator. The polymerization regulator is preferably used in an amount of 0.01 to 5% by weight based on the total weight of the composition for optical materials. By using this polymerization regulator, not only can the polymerization rate be controlled to suppress a rapid increase in viscosity, but as a result, the polymerization yield is increased and the generation of bubbles is also eliminated.

When sulfur is included in the composition for the episulfide-based optical material, it is preferable to polymerize it after forming the prepolymer. In this case, in order to facilitate the formation of the prepolymer, it is preferable to further include an alkylimidazole as a polymerization regulator. there is. The alkylimidazole particularly preferably includes 2-mercapto-1-methylimidazole. 2-Mercapto-1-methylimidazole is preferably used with a purity of 98% or higher. The composition for optical materials may preferably contain 0.01 to 5% by weight, more preferably 0.1 to 3% by weight, and even more preferably 0.15 to 1% by weight.

The composition for optical materials of the present invention may further include an internal mold release agent. Preferably, the internal mold release agent may include a phosphoric acid ester compound. Phosphate ester compounds are produced by adding 2 to 3 moles of alcohol compounds to phosphorus pentoxide (P ₂ O ₅ ), and various types of phosphoric acid ester compounds can be obtained depending on the type of alcohol used. Representative examples include those in which ethylene oxide or propylene oxide is added to an aliphatic alcohol, or ethylene oxide or propylene oxide is added to a nonylphenol group, etc. When a phosphoric acid ester compound to which ethylene oxide or propylene oxide is added is included in the polymerizable composition of the present invention as an internal release agent, it is preferable to obtain an optical material with good release properties and excellent quality. The composition of the present invention contains an internal mold release agent, preferably 4-PENPP [polyoxyethylene nonylphenol ether phosphate (5% by weight with 5 moles of ethylene oxide added, 80% by weight with 4 moles added, 3 moles added) 10% by weight of those added, 5% by weight of those added by 1 mole)], 8-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of those added by 9 moles of ethylene oxide, 80% by weight of those added by 8 moles, 9 5% by weight of those added by mole, 6% by weight of those added by 7 moles, 6% by weight of those added by 6 moles)], 12-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of those added by 13 moles of ethylene oxide) , 80% by weight of those added by 12 moles, 8% by weight of those added by 11 moles, 3% by weight of those added by 9 moles, 6% by weight of those added by 4 moles)], 16-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight with 17 moles of ethylene oxide added, 79% by weight with 16 moles added, 10% by weight with 15 moles added, 4% by weight with 14 moles added, 4% by weight with 13 moles added)] , 20-PENPP [polyoxyethylene nonyl phenol ether phosphate (6% by weight with 21 moles of ethylene oxide added, 76% by weight with 20 moles added, 7% by weight with 19 moles added, 6% by weight with 18 moles added) %, 5% by weight of 17 moles added)], 4-PPNPP [polyoxypropylene nonyl phenol ether phosphate (5% by weight of 5 moles of propylene oxide added, 80% by weight of 4 moles added, 3 moles added) 10% by weight of that added, 5% by weight of 1 mole added)], 8-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of that added by 9 moles of propylene oxide, 80% by weight of 8 mole added, 9 moles) 5% by weight of those added, 6% by weight of those added by 7 moles, 6% by weight of those added by 6 moles)], 12-PPNPP [polyoxypropylenenonylphenol ether phosphate (3% by weight of those with 13 moles of propylene oxide added, 80% by weight of those added by 12 moles, 8% by weight of those added by 11 moles, 3% by weight of those added by 9 moles, 6% by weight of those added by 4 moles)], 16-PPNPP [polyoxypropylene nonylphenol ether phosphate ( 3% by weight of those with 17 moles of propylene oxide added, 79% by weight of those with 16 moles added, 10% by weight of those with 15 moles added, 4% by weight of those with 14 moles added, 4% by weight of those with 13 moles added)], 20 -PPNPP [polyoxypropylene nonylphenol ether phosphate (6% by weight with 21 moles of propylene oxide added, 76% by weight with 20 moles added, 7% by weight with 19 moles added, 6% by weight with 18 moles added, 17 mol added (5% by weight)] and Zelec UN ^TM Use one or more types selected from among. Various substituents, including halogen compound substituents of these phosphoric acid ester compounds, can also be used for the same purpose.

The composition for an optical material of the present invention may further include an olefin compound as a reactive resin modifier for the purpose of controlling impact resistance, specific gravity, monomer viscosity, etc., in order to improve the optical properties of the optical material. Olefin compounds that can be added as a resin modifier include, for example, benzyl acrylate, benzyl methacrylate, butoxyethyl acrylate, butoxymethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2 -Hydroxyethyl acrylate, 2-hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxy ethyl acrylate, phenoxyethyl methacrylate, phenyl methacrylate, ethylene glycol dichloride. Acrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol Dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, ethylene glycol bisglycidyl acrylate, ethylene glycol bisglycidyl methacrylate rate, bisphenol A diacrylate, bisphenol A dimethacrylate, 2,2-bis(4-acroxyethoxyphenyl)propane, 2,2-bis(4-methacroxyethoxyphenyl)propane, 2, 2-bis(4-acroxydiethoxyphenyl)propane, 2,2-bis(4-methacroxydiethoxyphenyl)propane, bisphenol F diacrylate, bisphenol F dimethacrylate, 1,1-bis( 4-acroxyethoxyphenyl) methane, 1,1-bis (4-methacroxyethoxyphenyl) methane, 1,1-bis (4-acroxydiethoxyphenyl) methane, 1,1-bis (4 -Methacryloxydiethoxyphenyl) methane, dimethylol tricyclodecane diacrylate, trimethylol propane triacrylate, trimethylol propane trimethacrylate, glycerol diacrylate, glycerol dimethacrylate, pentaerythritol Triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, methylthioacrylate, methylthiomethacrylate, phenylthioacrylate, benzylthiomethacrylate, xylylene dithiol diacrylate, (meth)acrylate compounds such as silylenedithiol dimethacrylate, mercaptoethyl sulfide diacrylate, mercaptoethyl sulfide dimethacrylate, allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, di Allyl compounds such as allyl isophthalate, diallyl carbonate, diethylene glycol bisallyl carbonate, and styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene, 3,9-divinylspirobi (m -dioxane) and other vinyl compounds, and the compounds that can be used are not limited to these exemplary compounds. These olefin compounds may be used alone or in combination of two or more types.

The composition for optical materials of the present invention may further include an ultraviolet absorber, if necessary. Ultraviolet absorbers are used to improve the light resistance of optical materials and block ultraviolet rays. Known ultraviolet absorbers used in optical materials can be used without limitation. For example, ethyl-2-cyano-3,3-diphenylacrylate, 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-benzoloxy-2-hydroxybenzophenone; 2,2',4,4'-tetrahydroxybenzophenone; 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, etc. may be used alone or in combination of two or more types.

Preferably, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5, which has good ultraviolet absorption ability in the wavelength range of 400 nm or less and has good solubility in the composition of the present invention. -Chloro-2H-benzotriazole and 2-(2'-hydroxy-5'-t-octylphenyl)-2H-benzotriazole can be used. Such an ultraviolet absorber is capable of blocking 400 nm or more when used in an amount of 0.6 g or more per 100 g of the composition for optical materials.

In addition, the composition for optical materials of the present invention may further include various additives such as chain extenders, cross-linking agents, light stabilizers, antioxidants, discoloration inhibitors, organic dyes, fillers, and adhesion improvers, if necessary.

The composition for optical materials of the present invention formulated as described above preferably has a liquid viscosity of 500 cps (20°C) or less, and a solid phase refractive index (Ne) after polymerization of 1.67 to 1.70 when it does not contain sulfur, and when it contains sulfur. It is 1.71~1.77.

By performing mold polymerization of the composition as described above, an episulfide-based optical material can be obtained. To explain in more detail, it is as follows. First, the polymerizable composition of the present invention is injected between molds held by gaskets or tapes. At this time, in many cases, it is desirable to perform degassing treatment under reduced pressure or filtration treatment such as pressurization or reduced pressure, depending on the physical properties required for the obtained optical material and as necessary. Polymerization conditions are not limited as they vary greatly depending on the polymerizable composition, the type and amount of catalyst used, the shape of the mold, etc., but are carried out at a temperature of about -50 to 130°C for 1 to 50 hours. In some cases, it is preferable to maintain the temperature in the range of 10 to 130°C or gradually increase the temperature to cure for 1 to 48 hours.

The episulfide compound-based optical material obtained by curing may be subjected to treatment such as annealing, if necessary. The treatment temperature is usually between 50 and 130°C, and is preferably between 90 and 120°C.

Since the optical material of the present invention can be obtained as a molded body of various shapes by changing the mold during cast polymerization, it can be used in various optical materials such as spectacle lenses, camera lenses, and light-emitting diodes (LEDs). In particular, it is suitable as optical materials and optical elements such as spectacle lenses, camera lenses, and light-emitting diodes.

The episulfide-based optical material obtained according to the present invention has excellent hard adhesion, allows hard coating without a primer, is very easy to coat, and has excellent coating stability. In addition, the plastic optical lens obtained according to the present invention can be used by forming various coating layers on one or both sides as needed. As a coating layer, a primer layer, a hard coating layer, an anti-reflection layer, an anti-fog coating layer, an anti-fouling layer, a water-repellent layer, etc. can all be used. These coating layers may be used individually or may be used by forming a plurality of coating layers. Additionally, when forming a coating layer on both sides, it is possible to form the same coating layer on each side or to form different coating layers.

The present invention will be described in more detail below through specific examples. However, these examples are only for illustrating the present invention in more detail, and the scope of the present invention is not limited by these examples.

[ Synthesis example One]

Synthesis of bis(3-chloro-2-hydroxypropyl)sulfide

Epichlorohydrin (5563g, 60.12 mol) and methanol (3500g) were added to a 10 liter reactor and the reaction temperature was set to 6℃. When the reaction temperature reached 6℃, caustic soda (50% (aq), 5g) was added. was added. In another 10 liter reactor, add NaSH. By adding epichlorohydrin to the solution, bis(3-chloro-2-hydroxypropyl)sulfide and 3-chloro-2-hydroxy-propane-1-thiol were obtained, and epichlorohydrin was added to this reaction solution. Bis(3-chloro-2-hydroxypropyl)sulfide was obtained. The reaction was terminated when the final product was confirmed by GC and epichlorohydrin and 3-chloro-2-hydroxypropane-1-thiol compound completely disappeared.

[ Synthesis example 2]

Synthesis of 2,3-epoxypropyl (2,3-epithiopropyl) sulfide

Add 1071.15 g (4.89 mol) of bis(3-chloro-2-hydroxypropyl)sulfide, 1300 g of toluene, and 800 g of methanol to a 10 liter reaction vessel, and adjust the internal reaction temperature to 30°C while stirring. When the internal reaction temperature reached around 25℃, 783.08g (9.78mol) of 50% NaOH(aq) was added dropwise, and the reaction temperature during dropwise addition was 35-37℃, and the reaction was carried out while maintaining this temperature. Dropping is done within 1 hour and maturation is performed at 37°C for about 30 minutes. After maturation, 2000 g of toluene is added, stirred for about 10 minutes, the layers are separated, the supernatant organic layer is washed three times with water, water is removed as much as possible, and the organic layer solution is mixed. An additional 400 g of methanol was added and stirred, and 372.23 g (4.89 mol) of thiourea and acetic anhydride (35 g) were added at a reaction temperature of 8°C, and the reaction was performed at a reaction temperature of 18°C for 24 hours. After completion of the reaction, stirring was stopped, the layers were separated, the lower layer was removed, the organic layer was washed three times with water, the toluene layer was removed, developed with dichloromethane and cyclohexane solvents, and purified using a silica gel column. By purification, 277.87 g (1.71 mol) of 2,3-epoxypropyl (2,3-epithiopropyl) sulfide compound was obtained.

[ Synthesis example 3]

1-(2,2,6,6- tetramethylpiperidine -1-Lil)-3-((Tyran-2- Lilmethylthio ) Propan-2-ol ( TMPP ) synthesis of

In a 1 liter reaction vessel, 2,3-epoxypropyl (2,3-epithiopropyl) sulfide compound (100.00 g, 0.61 mol), 2,2,6,6-tetramethylpiperidine (87.05 g, 0.61 mol) ) and dichloromethane (500g) were added and stirred at 35°C for 3 hours to react. After reaction, the solvent was removed and 1-(2,2,6,6-tetramethylpiperidin-1-yl)-3-((tyran-2-ylmethylthio)propan-2-ol (187 g) was obtained. .

¹³ C NMR (CDCl ₃ ): 17 ppm (5C), 26 ppm (1C), 28 ppm (2C), 32 ppm (1C), 42 ppm (1C), 44 ppm (1C), 51 ppm (1C), 52 ppm (2C), 75 ppm ( 1C).

MS (EI-MS method): 303.17 (m/z).

[ Synthesis example 4]

1-(2-hydroxy-3-(( diiran -2- lil methyl ) Tio )Profile)-2,2,6,6- tetramethylpiperidine -4-reel Methacrylate Synthesis of TMPMA

In a 1L reaction vessel, 2,3-epoxypropyl (2,3-epithiopropyl) sulfide compound (100.00 g, 0.61 mol), 2,2,6,6-tetramethylpiperidyl methacrylate (138.87 g, 0.61 mol) and dichloromethane (500 g) were added and stirred at 35°C for 3 hours to react. After reaction, the solvent was removed and 1-(2,2,6,6-tetramethylpiperidin-1-yl)-3-((tyran-2-ylmethylthio)propan-2-ol (238 g) was obtained. .

¹³ C NMR (CDCl ₃ ): 18ppm(1C), 26ppm(5C), 33ppm(1C), 43ppm(1C), 44ppm(1C), 46ppm(2C), 51ppm(1C), 56ppm(2C), 63ppm( 1C), 75ppm(1C), 125ppm(1C), 136ppm(1C), 167ppm(1C).

MS (EI-MS method): 387.19 (m/z).

[ Example One]

The reactor was reduced to 1.0 torr or less, and the external temperature was adjusted to 54°C. While stirring the reactor, 77.5 g of bis (2,3-epithiopropyl) sulfide compound and 1.5 g of 2,3-epoxypropyl (2,3-epithiopropyl), 1-(2-hydroxy-3-(( Add 0.15 g of diiran-2-ylmethyl)thio)propyl)-2,2,6,6-detramethylpiperidin-4-yl methacrylate, 16 g of sulfur, 0.8 g of sunscreen UV 31, and organic The dyes HTAQ (88 ppm) and PRD (30 ppm) were added and degassed under reduced pressure for 30 minutes, then 0.75 g of 2-mercapto-1-methylimidazole was added and stirred for 1 hour. After cooling to 30°C, 4g of 2,3-bis(2-mercaptoethylthio)propane-1-thiol, 1g of bis(mercaptomethyl)sulfide, 0.5g of dibutyltin dichloride, 0.3g of tetrabutylphosphonium bromide, and As an internal release agent, 8-PENPP [polyoxyethylene nonylphenol ester phosphate (3% by weight with 9 moles of ethylene oxide added, 80% by weight with 8 moles added, 5% by weight with 9 moles added, 7 moles)] 0.08 g of the mixed solution (6% by weight added, 6% by weight added by 6 moles) was placed in the reactor, a resin composition for optical lenses was prepared, and optical lenses were manufactured in the following manner, and the physical properties of the optical lenses were measured. .

(1) The resin composition for optical lenses prepared as above was stirred and degassed under reduced pressure at 43°C for 1 hour, cooled to 30°C, filtered, and then degassed under reduced pressure for an additional 5 minutes, and assembled with polyester adhesive tape. It was injected into a glass mold.

(2) The glass mold into which the resin composition for spectacle lenses was injected was cured by heating in a forced circulation oven from 30°C to 110°C for 20 hours, then cooled to 70°C and the glass mold was detached to obtain a lens. The obtained lens was processed to a diameter of 72 mm, ultrasonic cleaned in an aqueous alkaline cleaning solution, and then annealed at 100°C for 2 hours. The physical properties were measured using the method below and the results are shown in Table 1 .

Physical property test method

The physical properties of the optical lenses manufactured in the examples were measured using the experimental method below, and the results are listed in Table 1 .

1) Refractive index and Abbe number: Measured using Atago's DR-M4 model Abbe refractometer.

2) Transparency: Observe 100 lenses with the naked eye under the USHIO USH-10D Mercury Arc Lamp, and if less than 1 cloudiness is found in the lens, mark it as "◎", and if 2 to 3 cloudiness is found, If found, it was marked with "○", and if more than 4 were found, it was marked with "×".

3) Strain (polymerization imbalance): Prepare 100 lenses with a lens diameter of 80 mm and a power of +11 D, and observe them using the Schlieren method under a USHIO USH-10D mercury arc lamp. did. Those in which no striae were observed among 100 lenses are marked with “◎,” those with striae observed in 1 to 5 lenses out of 100 lenses are marked with “○,” and those in which striae was observed in 1 to 5 lenses out of 100 lenses are marked with “○.” Those in which striae were observed were marked with "Δ", and those in which striae was observed in more than 10 lenses out of 100 were marked with "×".

4) Light resistance: QUV/SE model Accelerated Weathering Tester from Q-Lab. was used. The QUV test is performed by irradiating a flat lens with a thickness of 1.2mm for 24 hours under the conditions of UVA-340 (340nm), light intensity of 0.76W/m2, 4 hours BPT (Black Panel Temperature) (60℃), and 4 hours condensation (50℃). after, In the measurement of color change, if the APHA value changes from 0 to less than 2, it is indicated as "◎", if the APHA value changes from 2 to less than 5, it is indicated as "○", and if the APHA value changes from 5 or more, it is indicated as "×". .

5) Thermal stability: The cured optical lens is maintained at 100℃ for 3 hours, and in the measurement of color change, if the APHA value changes from less than 2, it is marked as "◎", and if the APHA value changes from more than 2 to less than 5, it is marked as "○". ", and when the APHA value changes from 5 or more to less than 9, it is indicated with "Δ", and when the APHA value changes from 9 or more, it is indicated with "×".

6) Release property: When the epoxy acrylic resin composition is heat-cured and demolded at 70℃, when separating the plastic lens and the mold, if it is easily separated and nothing breaks, it is "○"; it is not easily separated, so it is more than 1 out of 100 glass molds. If it was broken, it was marked as "X" (for uniform evaluation, a mold of -0.00 diopter was used).

[ Example 2~9]

Each composition and optical lens were prepared in the same manner as in Example 1 , except for the composition shown in Table 1 below, and their physical properties were tested. The results are shown in Tables 1 and 2 below.

[ Example 10]

In a reactor, 90 g of bis(2,3-epithiopropyl)sulfide compound, 10 g of 2,3-bis(2-mercaptoethylthio)propane-1-thiol, 1-(2-hydroxy-3-((diiran -2-ylmethyl)thio)propyl)-2,2,6,6-detramethylpiperidin-4-yl methacrylate 0.2 g and 8-PENNP [polyoxyethylenenonyl], a phosphoric acid ester as an internal release agent Ether phosphate (3% by weight of 9 moles of ethylene oxide added, 80% of those added by 8 moles, 5% by weight of those added by 9 moles, 6% by weight of those added by 7 moles, 6% by weight of those added by 6 moles) 0.2 Part by weight, 0.1 part by weight of N,N-dimethylcyclohexylamine, HTAQ (88ppm) and PRD (30ppm), and 0.6g of ultraviolet absorber HOPBT were mixed and dissolved at 20°C to prepare a resin composition of a homogeneous solution, Example 1 and An optical lens was manufactured using the same method and its physical properties were evaluated. The results are shown in Table 2 below.

[ Comparative example One]

Hindered amine of 1-(2-hydroxy-3-((diiran-2-ylmethyl)thio)propyl)-2,2,6,6-detramethylpiperidin-4-yl methacrylate It was carried out in the same manner as in Example 1 , except that no was added.

The reactor was reduced to 1.0 torr or less, and the external temperature was adjusted to 54°C. While stirring the reactor, 77.5 g of bis (2,3-epithiopropyl) sulfide compound, 1.5 g of 2,3-epoxypropyl (2,3-epithiopropyl), 16 g of sulfur, 0.8 g of ultraviolet blocker UV 31, and organic dye. HTAQ (88 ppm) and PRD (30 ppm) were added and degassed under reduced pressure for 30 minutes, then 0.75 g of 2-mercapto-1-methylimidazole was added and stirred for 1 hour. After cooling to 30°C, 4g of 2,3-bis(2-mercaptoethylthio)propane-1-thiol, 1g of bis(mercaptomethyl)sulfide, 0.5g of dibutyltin dichloride, 0.3g of tetrabutylphosphonium bromide, and As an internal release agent, 8-PENPP [polyoxyethylene nonylphenol ester phosphate (3% by weight with 9 moles of ethylene oxide added, 80% by weight with 8 moles added, 5% by weight with 9 moles added, 7 moles)] 0.08 g of the mixed solution (6% by weight added, 6% by weight added by 6 moles) was placed in a reactor, a resin composition for an optical lens was prepared, and an optical lens was manufactured and evaluated. The results are shown in Table 2 below.

[ Comparative example 2~3]

An optical lens was manufactured in the same manner as Comparative Example 1 , except that the composition shown in Table 2 was followed, and its physical properties were tested. The results are listed in Table 2 .

[ Comparative example 4]

Hindered amine of 1-(2-hydroxy-3-((diiran-2-ylmethyl)thio)propyl)-2,2,6,6-detramethylpiperidin-4-yl methacrylate The same procedure as Example 10 was carried out except that no addition was made.

In a reactor, 90 g of bis(2,3-epithiopropyl)sulfide compound, 10 g of 2,3-bis(2-mercaptoethylthio)propane-1-thiol, and 8-PENNP [polyoxyethylene, a phosphate ester as an internal release agent. Nonyl ether phosphate (3% by weight with 9 moles of ethylene oxide added, 80% with 8 moles added, 5% by weight with 9 moles added, 6% by weight with 7 moles added, 6% by weight with 6 moles added) 0.2 g, 0.1 part by weight of N,N-dimethylcyclohexylamine, HTAQ (88 ppm) and PRD (30 ppm), and 0.6 g of ultraviolet absorber HOPBT were mixed and dissolved at 20°C to prepare a resin composition of a homogeneous solution, and an optical lens was manufactured. After that, the physical properties were tested. The results are shown in Table 2 below.

division Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 EPS(g) 77.5 77.5 77.5 77.5 EEPS(g) 1.5 1.5 1.5 1.5 1.4 1.6 1.5 EPDS(g) 80 76.4 72.5 Sulfur (g) 16 16 16 16 9.4 7 16 BMMS(g) One One 7 14 9 BMS(g) One One GST(g) 4 4 4 4 2 One One TMPP 0.2 0.05 0.15 0.15 TMPMA 0.15 0.1 0.2 0.2 Refractive index (Ne, 20℃) 1.7376 1.7176 1.7373 1.7373 1.7570 1.7570 1.7750 Abesu 32 34 32 32 30 30 28 transparency ◎ ◎ ◎ ◎ ◎ ◎ ○ polymerization imbalance ◎ ◎ ◎ ◎ ○ ○ ○ lightfastness ◎ ◎ ◎ ◎ Δ Δ Δ thermal stability ◎ ◎ ○ ○ Δ Δ Δ Dysplasia ○ ○ ○ ○ ○ ○ ○

division Example 8 Example 9 Example 10 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 EPS(g) 68.1 76.5 77.5 68.1 EEPS(g) 1.9 1.5 1.5 1.4 1.9 EPDS(g) 10 5 90 80 10 90 Sulfur (g) 14 10 16 20 14 BMMS(g) 4 5 One 7 4 BMS(g) One One One GST(g) One One 10 4 2 One 10 TMPP 0.1 TMPMA 0.15 0.1 0.2 Refractive index (Ne, 20℃) 1.7183 1.7165 1.7375 1.7376 1.7570 1.7183 1.7375 Abesu 34 34 32 32 30 34 32 transparency ◎ ◎ ◎ ○ × ○ ○ polymerization imbalance ◎ ◎ Δ ○ ○ ○ × lightfastness ◎ ◎ ○ × × × × thermal stability ◎ ◎ ○ × × × × Dysplasia ○ ○ ○ ○ × ○ ○

[abbreviation]

EPS: Bis(2,3-epithiopropyl)sulfide

EEPS: 2,3-Epoxypropyl(2,3-epithiopropyl)sulfide)

EPDS: Bis(2,3-epithiopropyl)disulfide

BMMS: Bis(mercaptomethyl)sulfide

BMS: Bis(2-mercaptoethyl)sulfide

GST: 2,3-Bis(2-mercaptoethylthio)propane-1-thiol

TMPP: 1-(2,2,6,6-tetramethylpiperidin-1-yl)-3-((thiran-2-ylmethylthio)propan-2-ol (1-(1-(2, 2,6,6-tetramethylpiperidin-1-yl)-3-((thiiran-2-ylmethylthio)propan-2-ol)

TMPMA: 1-(2-hydroxy-3-(diiran-2-ylmethylthio)propyl)-2,2,6,6-detramethylpiperidin-4-yl methacrylate (1-( 2-hydroxy-3-(thiiran-2-ylmethylthio)propyl)-2,2,6,6-tetramethylpiperidin-4-yl methacrylate)

The novel episulfide compound of the present invention can be added to episulfide-based optical materials and used to improve light resistance, heat resistance, and transparency.

The episulfide-based optical material obtained according to the present invention is a high-quality lens with excellent light resistance, heat resistance, and transparency, and can be usefully used in lenses for corrective sunglasses, fashion lenses, photochromic lenses, camera lenses, and lenses for optical devices.

Claims (10)

Episulfide compound represented by Formula 1 below.
[Formula 1]

(X and Y are each independently a hydrogen or ester group.) An episulfide compound represented by Formula 2 below,
An episulfide compound represented by Formula 1 below,
polythiol compounds and
A composition for an episulfide-based optical material containing a polymerization catalyst.
[Formula 1]

(X and Y are each independently a hydrogen or ester group.)
[Formula 2]

(In the formula, X and Y are O or S, m is an integer from 0 to 4, and n represents an integer from 0 to 2.) According to paragraph 2,
A composition for an episulfide-based optical material further containing sulfur. According to paragraph 2,
A composition for an episulfide-based optical material further comprising a polyisocyanate compound. According to any one of claims 2 to 4,
A composition for an episulfide-based optical material further comprising a tin halogen compound as a polymerization regulator. According to clause 5,
A composition for an episulfide-based optical material, characterized in that the tin halogen compound contains either dibutyltin dichloride, dimethyltin dichloride, or a small amount of 0.1 to 3.5% by weight of monomethyltin trichloride. According to any one of claims 2 to 4,
A composition for an episulfide-based optical material containing 0.01 to 10% by weight of the episulfide compound represented by Formula 1. According to any one of claims 2 to 4,
The polymerization catalyst is a composition for an episulfide-based optical material, characterized in that one or more types selected from amines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, and phosphine compounds. . According to clause 5,
The polymerization catalyst is a quaternary phosphonium salt and contains either tetra-n-butylphosphonium bromide or tetraphenylphosphonium bromide. A method for producing an episulfide-based high refractive index optical material, comprising polymerizing the composition of any one of claims 2 to 4.