KR20190060420A - Cycloaliphatic polythiol compound for optical material and the composition using the same - Google Patents

Abstract

The present invention relates to an aliphatic polythiol compound for optical material and an optical material composition using the same, and more specifically, to a polythiol compound which uses a hybrid material of aliphatic and alicyclic polythiol compounds as the polythiol compound, and in which an alicyclic polythiol material is mainly a central material; and an optical material composition and an optical lens using the same. A hybrid polythiol compound for an optical material of the present invention comprises an aliphatic polythiol and an alicyclic polythiol wherein the aliphatic and alicyclic polythiols are formed such that a composition ratio of the aliphatic polythiol is lower than that of the alicyclic polythiol. Therefore, the optical material formed from the polythiol compound for an optical material has excellent hardness, excellent mechanical properties at high temperatures, and improved refractive index. Furthermore, the optical lens manufactured from a composition formed of such a hybrid polythiol compound and polyisocyanate has excellent refractive index.

Description

TECHNICAL FIELD The present invention relates to an alicyclic polythiol compound for optical materials and an optical material composition using the same.

TECHNICAL FIELD The present invention relates to an alicyclic polythiol compound for optical materials and an optical material composition using the same. More particularly, the present invention relates to an optical material composition using an aliphatic and alicyclic polythiol compound as a polythiol compound, And more particularly to an optical material composition and an optical lens using the same.

Plastic lenses are not only excellent in impact resistance but lightweight, and are easy to dye compared to glass lenses, so they have been used to produce various optical lenses until recently. In general, a mixture of polyethylene glycol bisallyl carbonate (CR-39), polymethyl methacrylate (PMMA), and modified diaryl phthalate and ethylene glycol bisallyl carbonate is used as a material of the plastic lens. However, since these plastic lens materials have a refractive index of about 1.50 to 1.55, a compound having a large number of halogen atoms or aromatic rings in the molecule is used in order to improve the refractive index, so that the plastic lens materials have a disadvantage of large dispersion and poor weatherability or specific gravity have. In addition, when the dioptric power is high, the lenses made of these plastic materials become thicker and less aesthetic. Further, the near-sight lenses made of these materials have problems such that the thickness of the edge of the plastic lens becomes thick and birefringence and chromatic aberration are generated. Therefore, it is desirable to improve the material of the plastic lens so as to reduce the thickness of the lens while making the most of the advantages of the plastic lens having a low specific gravity, and to exhibit a low dispersion with a low chromatic aberration and a high refractive index.

The optical lens is required to be further improved in performance such as high refraction rate, high Abbe number, and high heat resistance. In accordance with these demands, various compounds and compositions for optical materials have been developed so far. Among them, proposals concerning a composition and a lens made by polymerizing and curing a polythiol compound and a polyisocyanate compound are actively made. However, in the production of optical materials, it is difficult to satisfy a specific refractive index among the optical lenses, and many cases of cloudiness occur. In the past, 2,5-bis (3-mercaptopropyl) -1,4-dithiane (DMMD) has been mainly used as an alicyclic polythiol.

An object of the present invention is to provide a polythiol compound for optical materials having improved optical properties such as refractive index and Abbe number, colorless transparency and weakness of resin, and a polymerization composition containing the same.

The technical problem to be solved by the present invention is that the hardness of an optical material produced by using aliphatic and alicyclic polythiols together, rather than a polythiol compound which has been used only as an aliphatic or alicyclic compound A polythiol compound excellent in mechanical properties at a high temperature and having an improved refractive index, an optical material composition using the same, and an optical lens.

A preferred embodiment of the present invention relates to an aliphatic polythiol compound; And an alicyclic polythiol compound, wherein the composition ratio of the aliphatic polythiol compound to the alicyclic polythiol compound ranges from 5:95 to 35:65. do. Preferably, the aliphatic polythiol compound is 2,3-bis (2-mercaptoethylthio) propane-1-thiol (GST) and the alicyclic polythiol compound is 2,5- Propyl) -1,4-dithiane (DMMD).

Another preferred embodiment of the present invention provides an optical material polymerizable composition wherein the hybrid polythiol compound for optical materials and the polyisocyanate compound are mixed in an equivalent ratio of 0.9 to 1.3.

Here, the polyisocyanate compound is characterized by being one or two kinds selected from the group consisting of 1,3-bis (isocyanatomethyl) benzene and 1,3-bis (isocyanatomethyl) cyclohexane.

Yet another preferred embodiment of the present invention provides an optical lens produced by casting together the above-mentioned optical material polymerizable composition.

The polythiol compound for an optical material of the present invention is characterized in that an aliphatic and alicyclic polythiol are included together and the aliphatic polythiol is constituted to have a lower composition ratio than the alicyclic polythiol. The optical material has excellent hardness, excellent mechanical properties at high temperature, and improved refractive index. Also, an optical lens made of a composition composed of such a hybrid polythiol compound and a polyisocyanate has an advantage of excellent refractive index.

The polythiol compound to be used in the present invention is not particularly limited and may be a compound having two or more thiol groups in one molecule and preferably a hybrid polythiol compound in which an aliphatic polythiol compound and an alicyclic polythiol compound are both included Can be used to make.

In the present invention, as the alicyclic polythiol, a polythiol compound having a 1,4-dithiane ring is used. Typically, 2,5-bis (3-mercaptopropyl) -1,4-dithiane (DMMD) Is preferably used. In general, DMMD is obtained by reacting bromine or chlorine in a diallyl disulfide solution dissolved in dichloromethane, stirring the mixture, removing dichloromethane, adding ethanol and thiourea to the remaining residue, filtering the precipitate, washing with ethanol and / Or water several times, dried, refluxed in a nitrogen atmosphere, dropped into a basic aqueous solution, refluxed and cooled, acidified with an acidic solution, and extracted with benzene or the like. The residue from which the benzene was removed from the resulting extract was distilled to obtain 2,5-dimercaptomethyl-1,4-dithiane. The resulting 2,5-dimercaptomethyl-1,4-dithiane can be reacted with hydrogen sulfide to give 2,5-bis (3-mercaptopropyl) -1,4-dithiane (DMMD). The manufacturing process of the DMMD is not limited to this process.

Examples of the alicyclic polythiol substance may include at least two sulfur atoms in an alicyclic ring other than DMMD, and may include trithiane, tetrathiane, and the like.

The basic polythiol of dithian typically has formula (1).

Equation (1)

 X is - (CH2CH2S) n2-H, n1 is an integer of 1 to 5, and n2 is an integer of 0 to 2.

Specific examples of typical polythiol compounds include methane dithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanediol 1,2-propane dithiol, 1,1-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, Diol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane- (2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1 Diethylene glycol bis (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2 , 3-dimercaptopropyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane bis (2-mercaptoacetate), trimethylolpropane bis (3-mercaptoacetate) Propionate), pentaerythritol tetrakis (2-mercaptoacetate, pentaerythritol tetrakis (3-mercaptopropionate), tetrakis (mercaptomethyl) methane, 2,3-bis Alicyclic polythiol compounds such as thio) propane-1-thiol;

(Mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, (Mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptoethyl) , 2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, Tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,5-tris (mercaptomethyl) Benzene, 1,3,5-tris (mercaptoethyl) benzene, 2,5-toluene dithiol, 3,4-toluene dithiol, 1,3-di (p- methoxyphenyl) Aromatic poly (meth) acrylates such as 2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol and 2,4-di (p-mercaptophenyl) Thiol compounds;

(Mercaptoethylthio) benzene, 1,2-bis (mercaptoethylthio) benzene, 1,3-bis Tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,3,5-tris , 2,4,5-tris (mercaptoethylthio) benzene, 1,3,5-tris (mercaptoethylthio) benzene, etc., and a nuclear alkylation thereof, compound;

Bis (mercaptomethyl) sulfide, bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) sulfide, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane, 1,2-bis (mercaptomethylthio) (3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethylthio) Propane, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) Propylthio) propane, 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, 4,8-dimercaptomethyl-1,11- Trithiandecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecane, 5, 7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecane, bis (mercaptomethyl) -3,6,9-trithia-1,11-undecandithiol , Tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) , Bis (1,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl- (Mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, and other mercapto groups such as mercaptomethyl-2,5-dimethyl-1,4-dithiane, bis Aliphatic polythiol compounds, and esters of thioglycolic acid and mercaptopropionic acid thereof;

Hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis Acetate), hydroxypropyl disulfide bis (3-mercaptopropionate, 2-mercaptoethyl ether bis (2-mercaptoacetate), 2- Dithiane-2,5-diol bis (2-mercaptoacetate), 1,4-dithiane-2,5-diol bis (3-mercaptopropionate) 3-mercaptopropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), 4,4-thiodibutyl acid bis Ethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropionic acid bis (2-mercaptoethyl ester), 4,4-dithiodibutyl acid bis (2-mercaptoethyl ester) (2,3-dimercaptopropyl ester), dithioglycolic acid bis (2,3-dimercaptopropyl ester), dithiopropionic acid bis (2,3-dimercaptopropyl ester) (2,3-dimercapto propyl ester) and other mercapto groups, and aliphatic polyols containing an ester bond with a sulfur atom Yiol compound;

A heterocyclic compound containing a sulfur atom in addition to a mercapto group such as 3,4-thiophenedithiol, 2,5-dimercapto-1,3,4-thiadiazole and the like;

Mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, Dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto- Pentaerythritol tri (3-mercaptopropionate), pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tri But are not limited to, erythritol tris (thioglycolate), dipentaerythritol pentaquis (3-mercaptopropionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthio A compound containing a hydroxy group in addition to a mercapto group such as benzene;

1,1,3,2-tetrakis (mercaptomethylthio) propane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) Tetrakis (mercaptomethylthio) -3-thiapentane, 1,1,6,6-tetrakis (mercaptomethylthio) -3,4- Bis (mercaptomethylthio) ethanethiol, 2- (4,5-dimercapto-2-thiapentyl) -1,3-dithiacyclopentane, 2,2-bis (Mercaptomethylthio) -2-thiabutyl) -1,4-dithiane, 2,2-bis (mercaptomethylthio) Bis (mercaptomethylthio) -1,3-propanedithiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis ) -1,9-dimercapto-2,5,8-trithianonane, 4,6-bis (mercaptomethylthio) -1,9-dimercapto- 3-mercaptomethylthio-1,6-dimercapto-2,5-dithiahexane, 2- (2,2-bis (mercaptomethylthio) ethyl) (Mercaptomethylthio) -5- (3,3-bis (mercaptomethylthio) -1-thiadiopropyl) 3,7-dithianone, tris Bis (mercaptomethylthio) ethyl methane, tris (4,4-bis (mercaptomethylthio) -2-thiabutyl) methane, tetrakis (2,2- Ethyl) methane, tetrakis (4,4-bis (mercaptomethylthio) -2-thiabutyl) methane, 3,5,9,11-tetrakis (mercaptomethylthio) -1,13-dimercapto -2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexakis (mercaptomethylthio) -1,19-dimercapto-2,6,8,12 , 14,18-hexanedonadecane, 9- (2,2-bis (mercaptomethylthio) ethyl) -3,5,13,15-tetrakis (mercaptomethylthio) -1,17- (Mercaptomethylthio) -1,11-dimercapto-2, 5, 7, 8-tetraheptadecane, Tetrastihydrocane, 3,4,8,9,13,14-hexakis (mercaptomethylthio) -1,16-dimercapto-2,5,7,10,12,15- (Mercaptomethylthio) methyl-3,4,12,13-tetrakis (mercaptomethylthio) -1,15-dimercapto-2,5,7,9,11 (Mercaptomethylthio) -7-mercapto-2,6-dithiaheptylthio-1,3-dithiane, 4-, (Mercaptomethylthio) -7-mercapto-2,6-dithiaheptylthio-6-mercaptomethylthio-1,3-dithiane, 1,1-bis 4- (6-mercapto Methylthio) -1,3-dithianylthio-3,3 bis (mercaptomethylthio) propane, 1,3-bis 4- (6-mercaptomethylthio) 3-bis (mercaptomethylthio) propane, 1-4- (6-mercaptomethylthio) -1,3-dithianylthio-3-2,2-bis -1,4-dithianylthio-3-2- (1, < / RTI > 2-mercaptomethylthio) (3-dithiethanyl) methyl-7,9-bis (mercaptomethylthio) -2,4,6,10-tetrathianedecane, 1,5-bis 4- (6-mercaptomethylthio) -1 , 3-dithianylthio-3-2- (1,3-dithiethanyl) methyl-2,4-dithiapentane, 4,6-bis [ -5-mercapto-2,4-dithianylthio] -1,3-dithiane, 4,6-bis 4- (6-mercaptomethylthio) -1,3-dithianylthio- -Dithiane, 4-4- (6-mercaptomethylthio) -1,3-dithianylthio-6-4- (6-mercaptomethylthio) -1,3-dithianylthio- Dithiane, 3-2- (1,3-dithiethanyl) methyl-7,9-bis (mercaptomethylthio) -1,11-dimercapto-2,4,6,10-tetthaliaundecane , 9-2- (1,3-dithiethanyl) methyl-3,5,13,15-tetrakis (mercaptomethylthio) -1,17-dimercapto-2,6,8,10,12 , 16-hexatiaheptadecane, 3-2- (1,3-dithiethanyl) methyl-7,9,13,15-tetrakis (mercaptomethylthio) -1,17-dimercapto- 4,6,10,12,16-hexatiaheptadecane, 3,7-bis 2- (1,3-dithiethanyl) methyl-1,9-dimercapto-2,4,6,8-tetra Thianonane, 4-3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto-2,5,7,10-tetrathiandecyl-5-mer 4,5-bis 3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio-1,3-dithiolane, 4 -3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio-5-mercaptomethylthio-1,3-dithiolane, 4-3-bis Thio) methyl-5,6-bis (mercaptomethylthio) -8-mercapto-2,4,7-trithiooctyl-5-mercaptomethylthio-1,3-dithiolane, 2- [bis (Mercaptomethylthio) -6-mercapto-2,5-dithiahexylthiomethyl] -1,3-dithiethane, 2-3,4-bis (mercaptomethylthio) -6- Mercapto-2,5-dithiahexylthiomercaptomethylthiomethyl-1,3-dithiethane, 2-3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto- (Mercaptomethylthio) methyl-5,6-bis (mercaptomethylthio) -8 (mercaptomethylthio) -8,10-tetrathiuantylthiomercaptomethylthiomethyl-1,3- Mercapto-2,4,7-trithiooctylmercaptomethylthiomethyl-1,3-dithiane, 4,5- Bis [1-2- (1,3-dithiethanyl) -3-mercapto-2- thiapropthio] -1,3-dithiolane, 4- [1-2- (1,3- ) -3-mercapto-2- thiopropylthio] -5-1,2-bis (mercaptomethylthio) -4-mercapto-3-thiabutylthio-1,3-dithiolane, 2- [bis (5-mercaptomethylthio-1,3-dithiolanyl) thio] methyl-1,3-dithiane, 4-4- -5- [1-2- (1,3-dithiethanyl) -3-mercapto-2-thiapropthio] -1,3-dithiolane, dithioacetals such as these oligomers, ≪ / RTI >

(Mercaptomethylthio) methane, tris (mercaptoethylthio) methane, 1,1,5,5-tetrakis (mercaptomethylthio) -2,4-dithiapentane, bis (Mercaptomethylthio) -1,3-dithiabutyl (mercaptomethylthio) methane, tris (4,4-bis (mercaptomethylthio) -1,3-dithiabutyl) Tris (mercaptomethylthio) -1,3,5-trithiacyclohexane, 2,4-bis (mercaptomethylthio) -1,3,5-trithiacyclohexane, 1,1,3,3- (Mercaptomethylthio) -2-thiopropane, bis (mercaptomethyl) methylthio-1,3,5-trithiacyclohexane, tris ((4-mercaptomethyl- Thiocyclohexyl-1-yl) methylthio) methane, 2,4-bis (mercaptomethylthio) -1,3-dithiacyclopentane, 2-mercaptoethylthio-4-mercaptomethyl- -Dithiacyclopentane, 2- (2,3-dimercaptopropylthio) -1,3-dithiacyclopentane, 4-mercaptomethyl-2- (2,3- , 3-dithia (2,2-bis (mercaptomethylthio) -1, 3-dimercapto-2-propylthio) -1,3-dithiacyclopentane, 2-thiopropyl) methane, tris (4,4-bis (mercaptomethylthio) -3-thiabutyl) methane, 2, (3,3-bis (mercaptomethylthio) -2-thiopropyl) -1,3,5-trithiacyclohexane, tetrakis 2-thiopropyl) methane, and the like, and also compounds having an orthotritoformic acid ester skeleton such as these oligomers;

Di (mercaptomethylthio) -1,5-dimercapto-2,4-dithiapentane, 2,2'-di (mercaptomethylthio) -1,3-dithiacyclopentane , 2,7-di (mercaptomethyl) -1,4,5,9-tetrathiaspiro [4.4] nonane, 3,9-dimercapto-1,5,7,11- tetrathiaspiro [5.5] Undecane, and compounds having an ortho-tetrathiocarbonate ester skeleton such as these oligomers.

However, the polythiol compound is not limited to each of the above-exemplified compounds. Each of the above-exemplified compounds may be used alone or in combination of two or more.

Among the above exemplified compounds, the present invention is characterized in that an aliphatic polythiol compound and an alicyclic polythiol compound are used together. More preferably, the aliphatic polythiol compound is GST, and the alicyclic polythiol compound is DMMD. The composition ratio of the aliphatic polythiol compound to the alicyclic polythiol compound is preferably 5:95 to 35:65.

The polythiol compound may form a composition for polymerization together with the polyisocyanate compound, and it is preferable to prepare an optical lens by polymerizing the composition for polymerization.

Specific examples of the polyisocyanate compound generally include hexamethylene diisocyanate, 2,5-bis (isocyanatomethyl) -bicyclo [2.2.1] heptane, 2,6-bis (isocyanatomethyl) (Isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, isophorone diisocyanate, 1,2-diisocyanatobenzene, 1,3-diisocyanatobenzene, 1, Diisocyanatotoluene, ethylphenylene diisocyanate, dimethylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, biphenyl diisocyanate, toluidine diisocyanate, 4,4'-methylene Bis (isocyanatomethyl) benzene, 1,4-bis (isocyanatomethyl) benzene, 1,2-bis (isocyanatomethyl) benzene, (Isocyanatoethyl) benzene, 1,3-bis Bis (isocyanatoethyl) benzene,?,? ',?' - tetramethyl xylylene diisocyanate, bis (isocyanatomethyl) naphthalene, bis Bis (isocyanatomethyl) sulfide, bis (isocyanatopropyl) sulfide, 2,5-diisocyanatotetrahydrothiophene, 2,5-diisocyanate Diisocyanatomethyltetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl-1,4-dithiane, , And the like.

Further, it is also possible to use a chlorine substituent, a halogen substituent such as a bromine substituent, an alkyl substituent, an alkoxy substituent, a prepolymer type modified product with a nitro substituent or a polyhydric alcohol, a carbodiimide modified product, a urea modified product, a biuret modified product, A reaction product or the like may also be used.

The polyisocyanate compound preferably used in the present invention is not limited to each of the above-exemplified compounds. Each of the above exemplified compounds may be used alone or in combination of two or more.

Among the above exemplified compounds, preferred polyisocyanate compounds are 1,3-bis (isocyanatomethyl) benzene (MXDI) and 3-bis (isocyanatomethyl) cyclohexane (HXDI).

In the present invention, it is preferable to use MXDI and HXDI alone or in combination as a polyisocyanate compound, and the composition ratio of MXDI and HXDI is preferably 100: 0 to 0: 100. More preferably, the composition ratio of MXDI is higher.

The ratio of the polythiol compound to the polyisocyanate compound is usually in the range of SH group / NCO group = 0.5 to 3.0, preferably 0.6 to 2.0, and more preferably 0.9 to 1.3. When the SH group / NCO group is less than 0.5 or more than 3.0, the heat resistance of the polythiourethane resin obtained by polymerization curing may be considerably lowered.

It is of course possible to further improve the practicality of the resulting material by adding optional components such as a catalyst, an internal mold release agent, an ultraviolet absorber and a bluing agent to the composition for optical material polymerization of the present invention, if necessary.

In the present invention, as a catalyst for polymerizing and curing a composition for optical material polymerization comprising a polythiol compound and a polyisocyanate compound to obtain a polythiourethane resin, a known urethane formation catalyst is used. The amount of the polymerization catalyst to be added varies depending on the composition of the composition, the mixing ratio, and the polymerization curing method, and is usually not more than 0.001% by mass and not more than 5% by mass relative to the total amount of the composition for optical material polymerization, 0.01% by mass or more and 1% by mass or less, and most preferably 0.01% by mass or more and 0.5% by mass or less. If the addition amount of the polymerization catalyst is more than 5% by mass, the refractive index and heat resistance of the cured product may be lowered and coloring may occur. If it is less than 0.001% by mass, it is not sufficiently cured and the heat resistance may be insufficient.

When the composition for optical material polymerization of the present invention is hardly peeled off from the mold after polymerization, it is possible to improve releasability from the mold of the obtained cured product by using or adding a known external and / or internal mold release agent. Examples of releasing agents include fluorine-based nonionic surfactants, silicone-based nonionic surfactants, phosphoric acid esters, acidic phosphate esters, oxyalkylene acidic phosphate esters, alkali metal salts of acidic phosphate esters, alkali metal salts of oxyalkylene acidic phosphate esters, , Higher fatty acid esters, paraffins, waxes, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, and aliphatic amine ethylene oxide adducts. These may be used singly or in combination of two or more. The addition amount is usually 0.0001 to 5 mass% with respect to the total amount of the composition for optical material polymerization.

Preferable examples of the ultraviolet absorber when added to the composition for optical material polymerization of the present invention include a benzotriazole-based compound. Specific examples of preferred compounds include 2- (2-hydroxy-5-methylphenyl) -2H-benzotriazole, 5-chloro-2- ) -2H-benzotriazole, 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) 2-hydroxyphenyl) -2H-benzotriazole, 2- (3,5-di-tert-butyl- Benzotriazole and 2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole. These may be used singly or in combination of two or more. Does not matter. The addition amount is usually 0.01 to 10 mass% with respect to the total amount of the composition for optical material polymerization.

As a preferable example of the bluing agent when it is added to the composition for optical material polymerization of the present invention, there may be mentioned anthraquinone-based compounds, and these may be used singly or in combination of two or more kinds. The addition amount is usually 0.0001 to 5 mass% with respect to the total amount of the composition for optical material polymerization.

The optical material made of a polythiourethane resin obtained by polymerizing and curing a composition for optical material polymerization containing a polythiol compound in the present invention is usually produced by casting polymerization. Specifically, a polythiol compound and a polyisocyanate compound are mixed. This mixture solution (composition for optical material polymerization) is defoamed by an appropriate method if necessary, and then injected into molds for optical materials, and is usually polymerized by heating slowly at a low temperature and a high temperature. Thereafter, an optical lens is obtained by demoulding.

 The optical material may be subjected to surface polishing, antistatic treatment, hard coat treatment, anti-reflection treatment or the like for the purpose of improving antireflection, hardening, abrasion resistance, chemical resistance, Physical and chemical treatments such as a coating treatment, a dyeing treatment, and a dimming treatment can be performed.

The composition for optical material polymerization, which has undergone the above-described reaction and treatment, is injected into a mold made of glass or metal, and after the polymerization curing reaction is carried out by irradiation with active energy rays such as heat or ultraviolet rays, the composition is separated from mold. Thus, an optical material is produced. The composition for optical material polymerization is preferably polymerized and cured by heating to produce an optical material. In this case, the curing time is preferably 2 to 30 hours, more preferably 5 to 22 hours, and the curing temperature is 20 to 150 ° C, preferably 80 to 120 ° C. The polymerization may be carried out at a predetermined polymerization temperature, for a predetermined time, at a temperature of 1 to 10 占 폚 / hour, at a temperature of 5 to 50 占 폚 / hour, or a combination thereof. Further, in the method for producing an optical material of the present invention, after completion of the polymerization, the cured product is subjected to the annealing treatment at a temperature of 50 to 150 ° C for 10 minutes to 5 hours to remove the deformation of the optical material to be.

The polythiol compound produced by the method of the present invention can be obtained by preparing a composition for optical material polymerization by using an aliphatic polythiol compound or an alicyclic polythiol compound singly to produce a lens having a hardness And has an excellent mechanical property at high temperature and an improved refractive index. The optical lens thus produced is particularly suitable for use in lenses such as spectacle lenses and camera lenses. In addition, the optical lens is subjected to physical and chemical treatments such as surface polishing, antistatic treatment, hard coat treatment and the like for the purpose of improving antireflection, hardening, abrasion resistance, chemical resistance, .

Example

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail with reference to the following examples. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention should not be construed as being limited to the following embodiments. Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art

The ratios of the thiol and isocyanate compounds used in the following examples and comparative examples are as follows, and they are subjected to cast polymerization and demolding to obtain optical lenses

Cial 1 Thiol 2 Isocyanate 1 Isocyanate 2 GST DMMD MXDI HXDI Example 1 5 95 0 100 Example 2 5 95 100 0 Example 3 5 95 50 50 Example 4 20 80 0 100 Example 5 20 80 100 0 Example 6 20 80 50 50 Example 7 35 65 0 100 Example 8 35 65 100 0 Example 9 35 65 50 50 Comparative Example 1 100 0 0 100 Comparative Example 2 100 0 100 0 Comparative Example 3 100 0 50 50 Comparative Example 4 0 100 0 100 Comparative Example 5 0 100 100 0 Comparative Example 6 0 100 50 50

Claims (5)

Aliphatic polythiol compounds; And
An alicyclic polythiol compound,
Wherein the composition ratio of the aliphatic polythiol compound to the alicyclic polythiol compound is from 5:95 to 35:65.
The method according to claim 1,
The aliphatic polythiol compound is 2,3-bis (2-mercaptoethylthio) propane-1-thiol (GST), and the alicyclic polythiol compound is 2,5- ) -1,4-dithiane (DMMD). ≪ / RTI >
The optical material polymerizable composition according to claim 1, wherein the hybrid polythiol compound for optical material and the polyisocyanate compound are mixed at an equivalent ratio of 0.9 to 1.3.
The method of claim 3,
Wherein the polyisocyanate compound is at least one selected from the group consisting of 1,3-bis (isocyanatomethyl) benzene and 1,3-bis (isocyanatomethyl) cyclohexane. Composition.
An optical lens produced by mixing the optical material polymerizable composition of claim 3 with a mold.