KR20190057237A - A method of preparing thioepoxy based optical material - Google Patents

Abstract

The present invention relates to a method for manufacturing a thioepoxy-based optical material. Specifically, the present invention relates to the method for manufacturing a high-quality optical material having a high yield without occurrence of striae or white turbidity due to imbalanced polymerization and is colorless, transparent, and changeless. In the present invention, provided is the method for manufacturing the thioepoxy-based optical material in which a polymerization composition, comprising a compound having at least one thioepoxy group, is in-mold polymerized, and is characterized in that mixing, defoaming, and injection into a mold are performed within the -5 to 20°C temperature range. The thioepoxy-based optical material manufactured according to the present invention can replace existing optical materials, thereby being able to be widely used in a variety of industries.

Description

[0001] The present invention relates to a method for preparing a thioepoxy-based optical material,

TECHNICAL FIELD The present invention relates to a method for producing a thioepoxy-based optical material, and more particularly, to a method for producing a high-quality optical material that is colorless and transparent and has no deformation at a high yield without causing marsuplication or opacity due to polymerization imbalance.

The plastic optical lens was introduced as a substitute for the high specific gravity and low impact properties of the glass lens. Representative examples thereof include polyethylene glycol bisallyl carbonate, polymethylmethacrylate, diallyl phthalate, and the like. However, the optical lens made of these polymers is excellent in physical properties such as main formation, dyeability, hard coat film adhesion and impact resistance, but has a refractive index as low as 1.50 (nD) and 1.55 (nD) . Therefore, various attempts have been made to develop an optical material having a high refractive index in order to reduce the thickness of the lens.

Korean Patent No. 10-0681218 proposes a thioepoxy-based plastic lens. Thioepoxy-based lenses have excellent properties with a high refractive index and a high Abbe number, while the lens is fragile and does not dye well. In order to solve these problems, a method of copolymerizing these two kinds of resins having different properties, that is, a method of copolymerizing a thioepoxy compound with a polythiol compound and a polyisocyanate compound is disclosed in Korean Patent Publication No. 10-0417985, Japanese Patent Application Laid- -352302.

In the case of a thioepoxy-based lens or a thioepoxy-based lens copolymerizing a thioepoxy and a thiourethane, when the polymerizable composition is subjected to the template polymerization, manganese or opacity due to polymerization imbalance is often caused to deteriorate the quality of the lens. Since the occurrence of such marsh or cloudiness deteriorates the quality of the lens, improvement has been required in the meantime. In addition, the reduction of production cost is a major concern in the recent lens field. The occurrence of malignant and opacity causes a decrease in lens yield and raises the production cost, and therefore, improvement in production cost is also urgently required.

Korean Patent Publication No. 10-0681218 Korean Patent Publication No. 10-0417985 Japanese Patent Application Laid-Open No. 11-352302

A thioepoxy-based optical material or a thioepoxy-based optical material that coats a thioepoxy and a thiourethane may generate fog or whitish due to polymerization imbalance. "McGee" refers to a phenomenon that differs locally from normal refractive index due to differences in composition. &Quot; Whitening " refers to a case where the optical lens exhibits turbidity due to polymerization non-uniformity when the resin composition for an optical lens is cured. McLean or whitak has a bad influence on the quality and performance of optical materials.

The inventors of the present invention have unexpectedly found that the temperature in the process of compounding the polymerizable composition and defoaming and injecting has an important correlation with occurrence of fog and clouding of the finally obtained lens. That is, when the polymerizable composition is compounded at a specific temperature, defoamed, and injected into a mold to polymerize, there is almost no occurrence of fog and clouding in the finally obtained lens. The present invention confirms and completes the advantages. The present invention provides a method of producing a high-quality thioepoxy-based optical material at a high yield without generation of white turbidity by using a polymerizable composition comprising a compound having at least one thioepoxy group And to provide the above objects.

In the present invention,

A method of producing an optical material for polymerizing a polymerizable composition comprising a compound having at least one thioepoxy group, wherein the compounding of the polymerizable composition, defoaming, and injection into a mold are carried out in a temperature range of -5 to 20 캜 And a method for producing the thioepoxy-based optical material.

Further, in the present invention, an optical material obtained by the above production method and an optical lens made of this optical material are provided. The optical lens particularly includes a spectacle lens or a polarizing lens.

In the present invention, it is possible to manufacture a colorless transparent high-quality lens having no macroscopic or opacity due to polymerization imbalance, by blending, defoaming and injecting a polymerizable composition within a specific temperature range, have.

The method for producing a thioepoxy-based optical material of the present invention is a method for polymerizing a polymerizable composition containing at least one compound having a thioepoxy group by performing a casting polymerization while keeping the temperature within a specific range in the process of compounding, defoaming, and injecting a mold.

In the present invention, a polymerizable composition containing a compound having at least one thioepoxy group is compounded, and the entire process of defoaming and injection into a mold is carried out at a temperature range of from -5 to 20 ° C. If the temperature is lower than -5 ° C, the polymerization reaction does not occur smoothly, and the reaction time is prolonged and partial polymerization imbalance may occur. On the other hand, if it exceeds 20 ° C, the curing rate of the resin is high, so that the reaction proceeds explosively due to an overheating reaction during polymerization, resulting in a gas accompanied by a strong odor, and the resin becomes black and can not be used. More preferably, the polymerizable composition is compounded, degassed, and cast in a temperature range of -5 to 15 캜. Conventionally, it has been recognized that the reaction should be carried out at a low temperature, and the polymerization reaction has been carried out at a temperature as low as possible. However, in the present invention, it has been discovered for the first time that not only the temperature during the polymerization but also the temperature during the compounding and defoaming of the composition have an important correlation with the fouling and opacity of the finally obtained lens. , More preferably -5 to 15 ° C, it is confirmed that a high-quality lens free from fog and cloudiness can be obtained by a smooth polymerization reaction. In the conventional manufacturing method which does not recognize such a correlation, the temperature in the mixing and defoaming process is not controlled, whereas the temperature in the polymerization process is controlled to be excessively low. In the present invention, by controlling the temperature in the mixing, defoaming, and injection molding process of the thioepoxy polymerizable composition to an appropriate range, it is possible to suppress the whitening of the molybdenum compound without any change in other process conditions or raw material components, An acrylic optical material can be easily produced.

Examples of the compound having one or more thioepoxy groups include bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide, 1,3- (Β-epithiopropylthio) cyclohexane, 1,3-bis (β-epithiopropylthiomethyl) cyclohexane, 1,4-bis Bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] methane, 2,2- Thio) cyclohexyl] sulfide; an episulfide compound having an alicyclic skeleton; (Β-epithiopropylthio) phenyl] methane, 2, 3-bis (β-epithiopropylthiomethyl) benzene, Bis [4- (β-epithiopropylthio) phenyl] propane, bis [4- (β-epithiopropylthio) phenyl] sulfide, bis [4- Episulfide compounds having an aromatic skeleton such as bis [4- (β-epithiopropylthio) phenyl] sulfine and 4,4-bis (β-epithiopropylthio) biphenyl; 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthiomethyl) Epithiocene skeleton such as bis (β-epithiopropylthioethyl) -1,4-dithiane, 2,3,5-tri (β-epithiopropylthioethyl) -1,4- Sulfide compounds; Bis [(2 -? - epithiopropylthioethyl) thio] -1,3-bis (? - epithiopropylthio) propane, (Β-epithiopropylthiomethyl) propane, bis- (β-epithiopropylthio) propane, tetrakis (β-epithiopropylthiomethyl) methane, 1,1,1- Propyl) sulfide, and bis- (β-epithiopropyl) disulfide, and the like. In addition, a chlorine substituent of a compound having an episulfide group, a halogen substituent such as a bromine substituent, an alkyl substituent, an alkoxy substituent, a nitro substituent, and a prepolymer type modified form with a polythiol can also be used. As the compound having one or more thioepoxy groups, bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide, 1,3-bis Cyclohexane, 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3-bis (β-epithiopropylthiomethyl) cyclohexane, 1,4- ), 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, 2,5-bis And at least one of 2- (2-β-epithiopropylthioethylthio) -1,3-bis (β-epithiopropylthio) propane.

The polymerizable composition may further comprise a polyisocyanate compound and a polythiol compound, and may be made of a thioepoxy-based optical material in which thioepoxy and thiourethane are copolymerized.

The polyisocyanate compound is not particularly limited and a compound having at least one isocyanate and / or isothiocyanate group may be used. For example, there may be mentioned 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, butene diisocyanate, 1,3-butadiene- , 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecatriisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate-4-isocyanatomethyloctane, Aliphatic isocyanate compounds such as bis (isocyanatoethyl) carbonate and bis (isocyanatoethyl) ether; (Isocyanatomethyl) cyclohexane, 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate, Dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,2-dimethyldicyclohexylmethane isocyanate, 3.8-bis (isocyanatomethyl) tricyclo [ 2,1,02,06] decane, 3.9-bis (isocyanatomethyl) tricyclo [5,2,1,02,0] decane, 4.8-bis (isocyanatomethyl) tricyclo [ (Isocyanatomethyl) tricyclo [5,2,1,02,0] decane, 2,5-bis (isocyanatomethyl) bicyclo [2,2, 1], 2,6-bis (isocyanatomethyl) bicyclo [2,2,1], and other alicyclic isocyanate compounds; Bis (isocyanatomethyl) benzene, bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, bis (isocyanatobutyl) There may be mentioned ether, phenylenediisocyanate, ethylphenylenediisocyanate, isopropylphenylenediisocyanate, dimethylphenylenediisocyanate, diethylphenylenediisocyanate, diisopropylphenylenediisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, biphenyl diisocyanate, toluidine Diisocyanate, 4,4-diphenylmethane diisocyanate, 3,3-dimethyldiphenylmethane-4,4-diisocyanate, bibenzyl-4,4-diisocyanate, bis (isocyanatophenyl) , 3-dimethoxybiphenyl-4,4-diisocyanate, hexahydrobenzene diisocyanate, hexahydrodiphenylmethane-4,4-diisocyanate Aromatic diisocyanate compounds such as carbonate; Bis (isocyanatoethyl) sulfide, bis (isocyanatoethyl) sulfide, bis (isocyanatopropyl) sulfide, bis (isocyanatohexyl) sulfide, bis (isocyanatomethyl) sulfide, Bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) ethane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) 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-diisocyanatodibenzyl thioether, bis (4- Isomethylbenzene) sulfide, 4,4-methoxybenzenethioethylene glycol-3,3-diisocyanate, diphenyl disulfide-4,4-diisocyanate, 2,2-dimethyl diphenyl disulfide-5,5 Diisocyanate, 3,3-dimethyldiphenyldisulfide-5,5-diisocyanate, 3,3-dimethyldiphenyldisulfide-6,6-diisocyanate, 4,4- Sulfided aromatic isocyanate compounds such as 5-diisocyanate, 3,3-dimethoxy diphenyl disulfide-4,4-diisocyanate, and 4,4-dimethoxydiphenyl disulfide-3,3-diisocyanate; 2,5-bis (isocyanatomethyl) thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis (isocyanatomethyl) (Isocyanatomethyl) tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis (isocyanatomethyl) Dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis (isocyanatomethyl) -1,3-dithiolane, 4,5-bis Isocyanatomethyl) -2-methyl-1,3-dithiolane, and the like can be used alone or in admixture of two or more. In addition, at least one compound having at least one isocyanate and / or isothiocyanate group may be used alone or in combination of two or more of them. Further, halogen substituents such as chlorine substituents and bromine substituents of these isocyanate compounds, alkyl substituents, , A nitro substituent, a prepolymer-type modified product with a polyhydric alcohol or thiol, a carbodiimide-modified product, a urea-modified product, a biuret-modified product, or a dimerized or trimarized reaction product. Preferred examples of the polyisocyanate compound include isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, bis (isocyanatomethyl) tricyclo [5,2,1,02,0] decane, bis Isocyanatomethyl) bicyclo [2,2,1] is used.

The polythiol compound is not particularly limited, and any compound having at least one thiol group may be used alone or in combination of two or more. For example, there may be mentioned bis (2-mercaptoethyl) sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,3- -1-thiol, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, tetrakis (mercaptomethyl) methane; (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol, bis (2,3-dimercapto Bis (2- (2-mercaptoethyl) thiophene) sulfide, bis (2,3-dimercaptopropanyl) disulfide, 1,2- Mercaptoethylthio) -3-mercaptopropylthio) ethane, bis (2- (2-mercaptoethylthio) -3-mercaptopropyl) sulfide, 2- (2-mercaptoethylthio) -3- 2-mercapto-3- [3-mercapto-2- (2-mercaptoethylthio) -propylthio] propylthio-propane- 1 -thiol, 2,2-bis- (3-mercapto-propionyl (2-mercaptoethylthio) -propylthio] ethylthio) ethyl ester was obtained in the same manner as in 2- (2-mercaptoethylthio) -3- (S) -3 (3R, 3S, 3S, 3S, 3S) - ((R-2,3-dimercaptopropyl) thio) propane-1,2-dithiol, (4R, R) -4,14-bis (mercaptomethyl) -3,6,9,12,15-pentatihaheptane-1,17-dithiol, (S) -3 - ((R- 2-mercaptoethyl) thio) propane-1-thiol, 3,3'-dithiobis (propane-1 Dithiol, (7R, 11S) -7,11-bis (mercaptomethyl) -3,6,9,12,15-pentathiaheptadecane-1,17- ) -7,12-bis (mercaptomethyl) -3,6,9,10,13,16-hexatiaoctadecane-1,18-dithiol, 5,7-dimercaptomethyl- Dimercapto-3,6,9-trithiandecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecane, 4,8-dimercapto Methyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate) , Pentaerythritol tetrakis (2-mercaptoacetate), bispentaerythritol-ether-hexakis (3-mercaptopropionate), 1, Tetrakis (mercaptomethylthio) propane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) Dithiane, and 2- (2,2-bis (mercaptodimethylthio) ethyl) -1,3-dithiane. In addition, compounds having one or more thiol groups may be used alone or in combination of two or more. It is also possible to use a modified polymer obtained by prepolymerization of a polythiol compound with an isocyanate, a thioepoxy compound, a thiotane compound or a compound having an unsaturated bond as a resin modifier. As the polythiol compound, one or more other polythiol compounds may be preferably used in combination with bis (2-mercaptoethyl) sulfide or bis (2-mercaptoethyl) sulfide.

The polymerizable composition may further comprise an olefin compound as a reactive resin modifier for the purpose of controlling impact resistance, specific gravity, monomer viscosity and the like in order to improve the optical properties of the copolymer optical resin (optical material). Examples of the olefin compound which can be added as the reactive resin modifier include benzyl acrylate, benzyl methacrylate, butoxy ethyl acrylate, butoxy methyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenyl methacrylate, ethylene glycol Diethylene glycol dimethacrylate, diethylene glycol dimethacrylate, diethylene 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 di But are not limited to, acrylate, acrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, ethylene glycol bisglycidyl acrylate, ethylene glycol bisglycidyl methacrylate, bisphenol A diacrylate, bisphenol A dimethacrylate (4-alkoxyethoxyphenyl) propane, 2,2-bis (4-methoxyethoxyphenyl) propane, Bis (4-methoxyethoxyphenyl) propane, bisphenol F diacrylate, bisphenol F dimethacrylate, 1,1-bis (4-acroxyethoxyphenyl) Bis (4-methacryloxyethoxyphenyl) methane, 1,1-bis (4-acryloxy diethoxyphenyl) methane, 1,1- Decane diacrylate, trimethylol propane triacrylate, trimethylol propane trimethacrylate, glycerol diacrylate Acrylates such as methyl methacrylate, ethyl methacrylate, ethyl methacrylate, ethyl methacrylate, ethyl methacrylate, ethyl methacrylate, ethyl methacrylate, ethyl methacrylate, butyl methacrylate, (Meth) acrylate compounds such as xylylene dithiol diacrylate, xylylene dithiol dimethacrylate, mercaptoethyl sulfide diacrylate, and mercaptoethyl sulfide dimethacrylate; Allyl compounds such as allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, and diethylene glycol bisallylcarbonate; And vinyl compounds such as styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene and 3,9-divinyl spirobi (meta-dioxane). However, the usable compounds are not limited to these exemplified compounds. These olefin compounds may be used alone or in combination of two or more.

The polymerizable composition of the present invention may further contain an internal mold release agent, a heat stabilizer, an ultraviolet absorber, an organic dye, an inorganic pigment, a coloring inhibitor, an antioxidant, a light stabilizer, a catalyst and the like according to a conventional method.

As the internal release agent, a phosphoric acid ester compound, a silicone surfactant, and a fluorine surfactant may be used singly or in combination of two or more. The internal blowing agent is preferably contained in an amount of 0.001 to 10% by weight in the polymerizable composition. Preferably, a phosphoric acid ester compound is used as an inner mold release agent. The phosphoric acid ester compound is prepared by adding 2 to 3 moles of an alcohol compound to phosphorus pentoxide (P ₂ O ₅ ). Various types of phosphoric acid ester compounds can be obtained depending on the type of alcohol used. Representative examples include ethylene oxide or propylene oxide added to an aliphatic alcohol, or ethylene oxide or propylene oxide added to a nonylphenol group. When the polymerizable composition of the present invention contains a phosphoric acid ester compound to which ethylene oxide or propylene oxide has been added as an internal mold release agent, an optical material having good releasability and excellent quality can be obtained. The phosphoric acid ester compound used as the inner mold release agent is preferably a polyoxyethylene nonylphenol ether phosphate (5 mol% of ethylene oxide, 5 mol% of ethylene oxide, 80 mol% of 4 mol of the ethylene oxide, 10 mol% 5% by weight of ethylene oxide, 9% by weight of ethylene oxide, 8% by weight of ethylene oxide and 80% by weight of ethylene oxide, and 7% by weight of ethylene oxide), polyoxyethylene nonylphenyl phosphate 10 wt% of ethylene oxide and 6 wt% or less of ethylene oxide), polyoxyethylene nonylphenol ether phosphate (3 mol% of ethylene oxide, 3 mol% of ethylene oxide, 80 mol% of ethylene oxide, 9 mol% 5 parts by weight of ethylene oxide, 6 parts by weight of 7 parts by weight, 6 parts by weight of 6 parts by weight), polyoxyethylene nonylphenol ether phosphate (3 parts by weight of ethylene oxide 13 parts by weight and 12 parts by weight of 80 parts by weight of ethylene oxide) 8 wt% of 11 mol%, 3 wt% of 9 mol%, 4 mol 6 wt% of ethylene oxide), polyoxyethylene nonylphenol ether phosphate (3 mol% of 17 mol of ethylene oxide, 79 wt% of 16 mol of ethylene oxide, 10 mol% of ethylene oxide of 14 mol% 4% by weight, and 13% by mole), polyoxyethylene nonylphenol ether phosphate (containing 21% by mole of ethylene oxide, 5% by weight, 20% by mole and 78% by mole, By weight, 6% by weight of 18 mol% and 4% by weight of 17 mol%) and Zelec UN ™.

In the present invention, the polymerizable composition is defoamed while maintaining a constant temperature condition, and is injected into a mold to obtain a thioepoxy-based optical material through casting polymerization. First, the polymerizable composition defoamed under constant temperature conditions (-5 to 20 ° C) is injected between molding molds held by gasket or tape or the like under the same temperature condition to polymerize. The polymerization conditions are not limited because the conditions vary greatly depending on the kind of the polymerizable composition, the type and amount of the catalyst used, the shape of the mold, etc. However, the polymerization is carried out at a temperature of about -50 to 130 캜 for 1 to 50 hours. In some cases, it is preferable to maintain or slowly raise the temperature in the range of 10 to 130 占 폚 and cure in 1 to 48 hours.

The optical material obtained by the curing may be subjected to treatment such as annealing if necessary. The treatment temperature is usually from 50 to 130 占 폚, preferably from 90 to 100 占 폚.

Various additives such as a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, a coloring inhibitor, a useful dye, a filler, and an adhesion improver may be added as well as a known molding method according to the purpose of polymerization. The catalyst used plays an important role. Known epoxy curing agents are mainly used as catalysts, but strong amines cause intense isocyanate reaction, so use with caution is required. In the present invention, mainly amine salts, phosphonium salts, phosphines and tertiary amines having no electron attracting group, Lewis acids, radical initiators and the like are mainly used, and the kind and amount of the catalyst are suitably adjusted by a person skilled in the art You can choose.

The optical material of the present invention can be obtained as a molded article of various shapes by changing a mold at the time of casting polymerization, and can be used as various optical materials such as a spectacle lens, a camera lens, and a light emitting diode (LED). In particular, it is suitable as an optical material such as a spectacle lens, a camera lens, a light emitting diode, and an optical element.

The lens made of the optical material of the present invention may be used by applying a coating layer on one or both sides, if necessary. Examples of the coating layer include a primer layer, a hard coat layer, an antireflection film layer, an antifogging coat film layer, an antifouling layer, and a water-repellent layer. Each of these coating layers may be carried out alone or in multiple layers with a plurality of coating layers. When the coating layer is applied to both surfaces, the same coating layer may be applied to each surface or a different coating layer may be applied to each surface.

[ Example ]

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, these embodiments are only for describing the present invention more specifically, and the scope of the present invention is not limited by these embodiments.

[Example 1]

89 g of bis (2,3-epithiopropyl) sulfide (BEPS) as a thioepoxy compound, 5 g of isophorone diisocyanate as an isocyanate compound, 6 g of bis (2-mercaptoethyl) sulfide as a thiol compound, 8-PENPP {polyoxyethylene nonylphenylphosphate (containing 9 mol of ethylene oxide and 5 mol% of ethylene oxide, 8 mol of ethylene oxide and 80 mol% of ethylene oxide, 7 mol of ethylene oxide) 0.15 g of TBPB, 0.1 g of triphenylphosphine, 1.5 g of organic dye HTAQ (20 ppm) and PRD (10 ppm), and 1.5 g of ultraviolet absorber HOPBT And mixed at 5 DEG C to obtain a homogeneous solution. Thereafter, while keeping the temperature in the above range, filtration was performed with a 1 탆 PTFE filter, and the mixture was injected into the mold with the glass mold and the tape while maintaining the temperature at 5 캜. The mold was placed in a polymerization oven, and the temperature was gradually elevated to 25 ° C to 130 ° C over 21 hours to polymerize. After completion of the polymerization, the mold was removed from the oven, and the mold was released from the mold to obtain a lens. The obtained resin was further annealed at 130 캜 for 4 hours. In this manner, 100 lenses of the lens were produced, and the maly phenomenon and clouding phenomenon were confirmed by the following method, and the results are shown in Table 1 below.

Experiment and Evaluation Method

The physical properties of the optical lens manufactured by the following physical property test method were measured, and the results were recorded in Table 1 below.

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

2) McLean: The 100 lens was observed with the naked eye under a mercury arc lamp of USHIO USH-10D, and the mallearity of the lens was confirmed to be malleus, and the malleus incidence was calculated.

3) Whitening: 100 lenses were visually observed under a mercury arc lamp of USHIO USH-10D. The cloudy lens was judged to be opaque and the opacity was calculated.

[Example 2-5]

In the same manner as in Example 1, compositions and optical lenses were prepared according to the compositions shown in Table 1, respectively, and their properties were tested. The results are shown in Table 1.

[Comparative Example 1]

89 g of bis (2,3-epithiopropyl) sulfide (BEPS-1) as a thioepoxy compound, 5 g of isophorone diisocyanate as an isocyanate compound and 5 g of bis (2-mercaptoethyl) 6 g of sulfide, 8 g of polyphosphoric acid ester phosphate 8-PENPP [polyoxyethylene nylonylphenol ether phosphate (3 mol% of ethylene oxide 9 mol), 8 mol of 80 mol% of ethylene oxide, 9 mol of 5 mol% 0.15 g of TBPB, 0.1 g of triphenylphosphine, organic dye HTAQ (20 ppm) and PRD (10 ppm), ultraviolet absorber HOPBT Were mixed at -10 DEG C to obtain a homogeneous solution. Thereafter, while keeping the temperature in the above range, filtration was performed with a 1 μm PTFE filter, and the mold was injected while keeping the mold at a temperature of -10 ° C. The mold was placed in a polymerization oven, and the temperature was gradually elevated to 25 ° C to 130 ° C over 21 hours to polymerize. After completion of the polymerization, the mold was removed from the oven, and the mold was released from the mold to obtain a lens. The obtained resin was further annealed at 130 캜 for 4 hours. In this manner, 100 lenses of the lens were produced, and a maly phenomenon and a cloudiness phenomenon were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.

[Comparative Example 2]

In the same manner as in Comparative Example 1, a composition and an optical lens were prepared according to the composition shown in Table 1, and their physical properties were tested.

division Injection temperature
(° C) Thioepoxy compound Isocyanate compound Thiol compound Refractive index
(nE) Fertility rate (%) Rate of opacity (%) Example 1 5 BEPS 89g IPDI 5g BMES 6g 1.699 5 4 Example 2 -5 BEPS 89g IPDI 5g BMES 6g 1.699 3 6 Example 3 10 BEPS 89g IPDI 5g BMES 6g 1.700 6 2 Example 4 15 ETPDS 89g IPDI 5g BMES 6g 1.738 4 2 Example 5 18 BEPS 89g IPDI 5g BMES 6g 1.699 13 2 Comparative Example 1 -10 BEPS 89g IPDI 5g BMES 6g 1.698 35 30 Comparative Example 2 25 BEPS 89g IPDI 5g BMES 6g 1.699 60 3

[Abbreviation]

BEPS: bis (2,3-epithiopropyl) sulphide (bis (2,3-epithiopropyl) sulfide)

ETPDS: 2,3-epoxypropyl (2,3-epithiopropyl) disulfide (2,3-epoxypropyl)

IPDI: isophorone diisocyanate

BMES: Bis (2-mercaptoethyl) sulfide (bis (2-mercaptoethyl) sulfide)

HOPBT: 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole) 2- (2'-

TBPB: tetrabutylphosphonium bromide

HTQA: 1-hydroxy-4- (p-toluidine) anthraquinone.

PRD: Perinone dye

According to the present invention, a thioepoxy-based optical material having excellent whiteness and high quality can be easily produced, and the thioepoxy-based optical material produced according to the present invention can be widely used in various fields in place of existing optical materials have. Specifically, it can be used as a plastic spectacle lens, a 3D polarized lens in which a polarizing film is attached to a spectacle lens, a camera lens, etc. In addition, a recording medium substrate used for a prism, an optical fiber, Products.

Claims (10)

A method of producing an optical material for polymerizing a polymerizable composition comprising a compound having at least one thioepoxy group, wherein the compounding of the polymerizable composition, defoaming, and injection into a mold are carried out in a temperature range of -5 to 20 캜 Based optical material. The composition according to claim 1, wherein the compound having a thioepoxy group is bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide, 1,3- Cyclohexane, 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3-bis (β-epithiopropylthiomethyl) cyclohexane, 1,4- ), 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, and 2,5-bis And at least one selected from the group consisting of 2- (2-β-epithiopropylthioethylthio) -1,3-bis (β-epithiopropylthio) propane. The method for producing a thioepoxy-based optical material according to claim 1, wherein the polymerizable composition further comprises a polyisocyanate compound and a polythiol compound. 4. The method for producing a thioepoxy-based optical material according to any one of claims 1 to 3, wherein the polymerizable composition is compounded, defoamed, and injected into a mold at a temperature ranging from -5 to 15 캜 . The method for producing a thioepoxy-based optical material according to any one of claims 1 to 3, wherein the polymerizable composition further comprises an olefin compound as a reactive resin modifier. The method for producing a thioepoxy-based optical material according to any one of claims 1 to 3, wherein the polymerizable composition further comprises a phosphoric acid ester compound as an internal mold release agent. 7. The phosphoric acid ester compound according to claim 6, wherein the phosphoric acid ester compound is at least one selected from the group consisting of polyoxyethylene nonylphenol ether phosphate (5 mol% of ethylene oxide, 5 mol% of ethylene oxide, 80 mol% of 4 mol% 5 mol% of ethylene oxide, 9 mol of ethylene oxide, 5 mol% of ethylene oxide, 8 mol of ethylene oxide, 80 mol% of ethylene oxide, 7 mol of ethylene oxide, 10 mol% of ethylene oxide), polyoxyethylene nonylphenyl phosphate 5% by weight of ethylene oxide and 6% by mole or less of ethylene oxide), polyoxyethylene nonylphenol ether phosphate (containing 3 mol% of ethylene oxide and 10 mol% of ethylene oxide and 9 mol% of ethylene oxide) 5 parts by weight, 6 parts by weight of 7 parts by weight and 6 parts by weight of 6 parts by weight), polyoxyethylene nonylphenol ether phosphate (3 parts by weight of ethylene oxide 13 parts by weight and 80 parts by weight of 12 parts by weight of ethylene oxide, , 8 parts by weight of 11 parts by mol, 3 parts by weight of 9 parts by weight and 6 parts by weight of 4 parts by weight) , Polyoxyethylene nonylphenol ether phosphate (3 mol% of ethylene oxide and 17 mol% of ethylene oxide, 79 wt% of 16 mol%, 10 wt% of 15 mol%, 4 wt% of 13 mol% of 13 mol (4 wt% added) and polyoxyethylene nonylphenol etherphosphate (21 wt% of ethylene oxide, 7 wt% of 20 mol%, 78 wt% of ethylene oxide, 18 wt% of ethylene oxide, 6% by weight, and 17% by weight of 17% by weight of the total weight of the thermosetting resin composition). An optical material produced by the manufacturing method according to any one of claims 1 to 3. An optical lens comprising the optical material of claim 8. The optical lens according to claim 9, wherein the optical lens is a spectacle lens or a polarizing lens.