KR20030075401A - Ultra-high refractive optical material and lens manufacturing method from novel polythiol compound - Google Patents

Ultra-high refractive optical material and lens manufacturing method from novel polythiol compound Download PDF

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KR20030075401A
KR20030075401A KR1020020014596A KR20020014596A KR20030075401A KR 20030075401 A KR20030075401 A KR 20030075401A KR 1020020014596 A KR1020020014596 A KR 1020020014596A KR 20020014596 A KR20020014596 A KR 20020014596A KR 20030075401 A KR20030075401 A KR 20030075401A
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South Korea
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diisocyanate
bis
benzene
optical material
tris
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KR1020020014596A
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Korean (ko)
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장동규
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장동규
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/52—Polythioethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses

Abstract

PURPOSE: A sulfur-containing urethane optical material obtained from a novel polythiol compound, its preparation method and a plastic glasses lens prepared from the optical material are provided, to improve the refractive index, the Abbe's number, the impact resistance, the lightweightness, the dyeing property, the moldability and the light transmissivity. CONSTITUTION: The sulfur-containing urethane optical material is prepared by mixing the polythiol compound of the formula I and poly(diisocyanate) in the NCO/SH ratio of 0.5-2.5 by mol; and heating the mixture to cure them, wherein X is CH2CH2, CH2CH2SCH2CH2, CH2CH2OCH2CH2 or a phenyl group. Preferably the poly(diisocyanate) is at least one selected from the group consisting of m-xylene diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate.

Description

신규 폴리티올 화합물로 부터 얻은 초 고굴절 광학 재료 및 렌즈의 제조방법{omitted}Ultra High Refractive Optical Materials and Lenses from Novel Polythiol Compounds

본 발명은 폴리티올 화합물 및 이를 함유하는 광학재료 및 광학제품에 관한 것이다. 본 발명의 신규 폴리티올 화합물로 부터 수득한 광학재료는 굴절율 및 아베수가 높으며, 내 충격성, 경량성, 가공성, 투과율, 염색성, 내열성등의 광학특성이 우수하면서도 광투과율이 우수한 것이 특징이다.The present invention relates to a polythiol compound and an optical material and an optical article containing the same. The optical material obtained from the novel polythiol compound of the present invention has a high refractive index and Abbe number, and is characterized by excellent optical transmittance while excellent optical properties such as impact resistance, light weight, processability, transmittance, dyeing resistance and heat resistance.

플라스틱 렌즈는 경량이면서도 내 충격성이 우수 할 뿐 아니라, 유리렌즈에 비하여 염색이 용이하기 때문에 최근까지 각종 광학렌즈를 생산하기 위하여 사용하고 있다. 이러한 이유 때문에 폴리에틸렌 글리콜비스알릴카르보네이트(CR-39), 폴리메틸메타아크릴레이트(PMMA) 및 변성디아릴프탈레이트와 에틸렌글리콜비스알릴카르보네이트의 혼합물이 통상적으로 플라스틱 광학렌즈의 재료로 사용된다. 그러나, 이들 플라스틱 렌즈 재료들은 굴절율이 1.50-1.55 정도이기 때문에, 도수가 높은 렌즈에서는 이들 플라스틱 재료로 만든 렌즈는 두께가 두꺼워진다. 결과 적으로 플라스틱 렌즈의 경량성에 대한 우수성이 렌즈의 두께로 인하여 상쇄될 뿐만 아니라, 이들 재료로 만든 플라스틱렌즈의 미관이 나빠지는 불리함이 있다. 특히, 이 재료로 만든 근시렌즈는 플라스틱렌즈의 가장자리 두께가 두꺼워지고 복굴절 및 색수차가 발생하는 문제점이 있다. 따라서, 비중이 낮은 플라스틱 렌즈의 장점을 최대한 살리면서 렌즈의 두께를 감소시킬 수 있고, 색수차가 낮고, 굴절율이 높으면서도, 저분산을 나타내도록 플라스틱 렌즈의 재료를 개량함이 요망된다. 상기 목적을 달성하기 위한 재료로서, 한국특허 공개 1991-011993에서는 2,5-비스(2-머캅토에틸티오메틸)-1,4-디티안과 메타크실렌디이소시아네이트를 경화시켜서 얻은 플라스틱렌즈를 소개하고 있으며, 한국특허 공개 1987-0008928에서는 펜타에리스톨테트라키스메르캅토프로피오네이트, 1,2-디메르캅토벤젠과 메타크실렌디이소시아네이트를 경화하여 플라스틱 렌즈를 얻는 방법을 소개하였으며, 한국특허 공개 1994-004010에서는 1,2-비스(메르캅토에틸)-3-메르캅토프로판과 메타크실렌디이소시아네이트를 경화하여 플라스틱 안경렌즈를 얻는 방법을 소개하고 있으나, 이로 얻은 플라스틱렌즈들도내열성, 염색성, 굴절율등의 광학특성은 좋으나, 광투과율을 향상 시키지는 못하였다.Plastic lenses have been used to produce various optical lenses until recently because they are lightweight and have excellent impact resistance and are easier to dye than glass lenses. For this reason, polyethylene glycol bisallylcarbonate (CR-39), polymethyl methacrylate (PMMA), and a mixture of modified diaryl phthalates and ethylene glycol bisallylcarbonate are commonly used as materials for plastic optical lenses. . However, since these plastic lens materials have a refractive index of about 1.50-1.55, lenses made of these plastic materials become thicker in lenses with high degrees of power. As a result, not only the superiority of the lightness of the plastic lens is canceled due to the thickness of the lens, but also the disadvantage that the aesthetics of the plastic lens made of these materials is worsened. In particular, the myopia lens made of this material has a problem that the edge thickness of the plastic lens becomes thick and birefringence and chromatic aberration occur. Therefore, it is desirable to improve the material of the plastic lens so that the thickness of the lens can be reduced while maximizing the advantages of the low specific gravity plastic lens, the chromatic aberration is low, and the refractive index is high, while showing low dispersion. As a material for achieving the above object, Korean Patent Laid-Open Publication No. 1991-011993 introduces a plastic lens obtained by curing 2,5-bis (2-mercaptoethylthiomethyl) -1,4-dithiane and metha xylene diisocyanate. In addition, Korean Patent Publication No. 1987-0008928 introduced a method for obtaining a plastic lens by curing pentaerythritol tetrakismercaptopropionate, 1,2-dimercaptobenzene and methaxylene diisocyanate. 004010 introduces a method of obtaining plastic spectacle lenses by curing 1,2-bis (mercaptoethyl) -3-mercaptopropane and metha xylene diisocyanate, but the plastic lenses obtained also have heat resistance, dyeability, refractive index, and the like. The optical properties are good, but the light transmittance is not improved.

본 발명의 우수한 광학특성 즉, 내용제성, 경량성, 염색성, 고굴절율, 내열성이 높고, 높은 아베수등을 가지면서도, 광투과율을 향상 할 수 있는 신규폴리티올 및 이를 출발 물질로하여 제조한 광학제품을 제공하는 것이다.Excellent optical properties of the present invention, namely, solvent resistance, light weight, dyeing property, high refractive index, high heat resistance, and have a high Abbe number and the like, a novel polythiol which can improve the light transmittance and the optical material prepared by using this as a starting material To provide a product.

본 발명은 상기 목적을 달성하기 위하여 플라스틱의 황 함유율을 높이고, 한분자 내에 티올기를 여러개 가지게 함으로써 경화물의 가교밀도를 높여 플라스틱광학렌즈의 우수한 광학 특성을 가진 광학렌즈를 제공한다. 하기 화학식(Ⅰ)의 신규 폴리 티올 화합물을 제시하고In order to achieve the above object, the present invention provides an optical lens having high optical properties of a plastic optical lens by increasing the sulfur content of the plastic and increasing the crosslinking density of the cured product by having several thiol groups in one molecule. To present a novel poly thiol compound of formula (I)

화학식(Ⅰ)과 폴리디이소시아네이트 화합물을 반응시켜서 플라스틱렌즈를 제조하는 방법을 제시하는데 있다.The present invention provides a method for producing a plastic lens by reacting a compound of formula (I) with a polydiisocyanate compound.

첨부 제1도는 실시예1에서 얻은 폴리티올 화합물의 IR 스팩트럼 차트.FIG. 1 is an IR spectrum chart of the polythiol compound obtained in Example 1. FIG.

본 발명의 신규 폴리티올 화합물은 하기 도표에 표시한 방법에 의하여 합성할 수 있다.The novel polythiol compound of the present invention can be synthesized by the method shown in the following table.

즉, 에탄디티올과 보론트리프로라이드에 에피글로로히드린을 서서히 적하하여 반응시켜서 디올을 얻고, 이것을 수산화 나트륨 존재하에서 메르캅토에탄올과 반응시켜서 테트라올을 얻었다. 또, 여기에 티오우레아를 넣고 반응시켜서 이소우로늄염을 만든 후, 수산화나트륨용액으로 가수분해 시켜 4가 폴리티올 화합물을 얻었다. 폴리티올 합성에는 에탄디티올 대신 다가알코올인 에틸렌글리콜, 프로필렌글리콜, 디에틸렌글리콜을 사용 할 수 있으며, 또한 비스페놀 A, 다가알코올이 부가된 비스페놀 A, 티오에탄올등을 사용 할수 있으나, 폴리티올의 굴절율 혹은, 아베수가 낮아지는 문제점이 있다.That is, epiglohydrin was slowly added dropwise to ethanedithiol and boron triproide to react to obtain a diol, which was reacted with mercaptoethanol in the presence of sodium hydroxide to obtain tetraol. In addition, thiourea was added and reacted to form an isouronium salt, followed by hydrolysis with sodium hydroxide solution to obtain a tetravalent polythiol compound. For polythiol synthesis, polyhydric alcohols such as ethylene glycol, propylene glycol, and diethylene glycol may be used instead of ethanedithiol. In addition, bisphenol A, bisphenol A with polyhydric alcohol, and thioethanol may be used. Or, there is a problem that the Abbe number is lowered.

화학식(Ⅱ)에서 얻어진 폴리티올화합물은 폴리이소시아네이트, 폴리티오이소시아네이트 화합물, 즉, 1-이소시아나토-4-이소티오시아나토벤젠, 4-메틸-3-이소시아나토-1-이소티오시아타노벤젠, 2-이소시아나토-4,6-디이소티오시아나토-1,3,5-트리아딘, 4-이소시아나토- 4'-이소티오시아나토디페닐술피드, 2-이소시아나토-2'-이소티오시아나토디에틸디슬피드, 에틸렌디이소시아네이트, 트리메틸렌디이소시아네이트, 데트라메틸렌디이소시아네이트, 헥사메틸렌디아소시아네이트, 옥타메틸렌디이소시아네이트, 노나디이소시아네이트, 1,2'-디메틸펜탄의이소시아네이트, 2,2,4-트리메틸헥사메틸렌디이소시아네이트, 데카메틸렌디이소시아네이트, 부탄디이소시아네이트, 1,3-비스부타디엔-1,4-디이소시아네이트, 2,4,4-트리메틸헥사메틸렌디이소시아네이트, 1,6,11-운데칸트리이소시아네이트, 1,3,6-헥사메틸텐트리이소시아네이트, 1,8디이소시아나토-4-이소시아나토메틸옥탄, 2,5,7-트리메틸-1,8-디이소시아나토-5이소시아나토메틸옥탄, 2,6-디(이소시아나토메틸)푸란, 이소포론디이소시아네이트, 비스(이소시아나토메틸)시클로헥산, 디시클로헥실메탄디이소시아네이트, 시글로헥산디이소시아네이트, 메틸시글로헥산디이소시아네이트, 시글로헥실디메틸메탄디이소시아네이트, 2,2'-디메틸 디시클로헥실메탄디이소시아네이트, 비스(4-이소시아나토-n-부틸리덴)펜타에리트리톨, 다이머산이이소시아네이트, 2-이소시아나토메틸-3-(3-이소시아나토프로필)-5-이소시아나토메틸-비시클로 [2,2,1] -헵탄, 2-이소시아나토메틸-3-(3-이소시아나토프로필)-6-이소시아나토메틸-비시클로 [2,2] -헵탄, 2-이소시아나토메틸-2-(3-이소시아나토프로필)-5-이소시아나토메틸-비시클로 [2,2] 헵탄, 2-이소시아나토메틸-2-(3-이소시아나토프로필)-6-이소시아나토메틸-비시클로 [2,2] -헵탄,2-이소시아나토메틸-3-(3-이소시아나토프로필)-5-(2-이소시아나토에틸)-비시클로- [2,2,1] 헵탄,2-이소시아나토메틸-3-(3-이소시아나토프로필)-6-(2-이소시아나토에틸)-비시클로- [2,2,] -헵탄, 2-이소시아나토메틸-2-)3-이소시아나토프로필)-5-(2-이소시아나토에틸)-비시클로- [2,2,] 헵탄, 2-이소시아나토메틸-2-(3-이소시아나토프로필-6-(2-이소시아나토에틸)-비스클로- [2,2,] -헵탄, 2.5(또는 6)-비스(이소시아나토메틸)-비시클로 [2,2,1] -헵탄, 페닐렌디아소시아네이트, 톨리렌디이소시아네이트, 에틸페닐렌디이소시아네이트, 이소프로필페닐렌디이소시아네이트, 디메틸페닐렌디이소시아네이트, 디에틸페닐렌디이소시아네이트, 디이소프로필페닐렌디이소시아네이트, 트리메틸벤젠트리이소시아네이트, 벤젠트리이소시아네이트, 나프탈린디이소시아네이트, 메틸나프탈렌디이소시아네이트,비스(이소시아나토에틸)카아보네이트, 비스(이소시아나토에틸)에테르, 1,4-부틸렌글리콜 디프로필에테르-α.α'-디이소시아네이트, 리신디이소시아네이트에틸에스테르, 리신트리이소시아네이트, 2-이소시아나토에틸-2,6-디이소시아나토헥사노에이트, 2-이소시아나토프로필-2,6-디이소시아나토헥사노에이트, 크실렌디이소시아네이트, 비스(이소시아트에틸)벤젠, 비스(이소시아트프로필)벤젠, 비스(이소시아나토메틸)벤젠, α,α,α',α'-테트라메틸크실렌디이소시아네이트, 비스(이소시아나토부틸)벤젠, 비스(이소시아나토메틸)나프탈린, 비스(이소시아나토메틸)디페닐에테르, 비스(이소시아나토에틸)프탈레이트, 메시틸렌트리아이소시아네이트, 비페닐디이소시아네이트, 롤리딘디이소시아네이트, 4,4'-디페닐메탄디이소시아네이트, 3,3'-디메틸디페닐메탄-4,4'-디이소시아네이트, 비벤질-4,4'-디이소시아네이트, 비스(이소시아나토페닐)에틸렌 3.3'-디메톡시비페닐메탄-디메틸디페닐-4,4'-디이소시아네이트, 트리페닐메탄트리이소시아네이트, 폴리메틸MD1(디페닐 메탄디이소시아네이트), 나프탈렌트리이소시아네이트, 디페닐메탄, 2,2,4'-트리이소시아네이트, 3-메틸디페닐메탄-4,6,4'-트리이소시아네이트, 4-메틸-디페닐메탄-3,5,2', 4', 6'-펜타이소시아네이트, 페닐이소시아나토메틸이소시아네이트, 페닐이소시아나토에틸이소시아네이트, 테트라히드로나트탈렌디이소시아네이트, 헥사히드로벤젠디이소시아네이트, 헥사히드로디페닐메탄-4,4'-디이소시아네이트, 디페닐에테르디이소시아네이트, 에틸렌글리콜디페닐에테르디이소시아네이트, 1,3-프로필렌글리콜디페닐에테르디이소시아네이트, 벤조페논디이소시아네이트, 디에틸렌글리콜디페닐에테르디이소시아네이트, 디벤조푸란디이소시아네이트, 카르바졸디이소시아네이트, 에틸카르바졸디이소시아네이트, 디클로로카르바디이소시아네이트, 티오디에틸렌디이소시아네이트, 티오디프로필디이소시아네이트, 비오디헥실디이소시아네이트, 디메틸술폰디이소시아네이트, 디티오디메틸디이소시아네이트, 디티오디메틸디이소시아네이트, 디티오디프로필디이소시아네이트, 디페닐술피드-2,4'-디이소시아네이트, 디페닐술피드-4,4'-디이소시아네이트, 3,3'-디메톡시-4,4'-디이소시아네이트디벤질티오에테르, 비스(4-이소시아나토메틸페닐)술피드, 4,4'-메톡시페닐티오에틸렌글리콜-3,3'-디이소시아네이트, 디페닐디술피드-4,4'-디이소시아네이트, 2,2'-디메틸디페닐디술피드-5,5'-디이소시아네이트, 3,3'-디메틸디페닐디술피드-5,5'-디이소시아네이트, 3.3'-디메틸디페닐디술피드-6,6'-디이소시아네이트, 4,4'-디메틸디페닐디슬피드-5,5'-디이소시아네이트, 3,3'-디메톡시디페닐술피드-4,4'-디이소시아네이트, 4,4'-디메톡시디페닐디술피드-3,3'-디이소시아네이트, 디페닐술폰-3,3'-디이소시아네이트, 벤지딘술폰-4,4'-이소시아네이트디페닐메탄술폰-4,4'-디이소시아네이트, 4-메틸디페닐술폰-2,4'-디이소시아네이트, 4,4'-디메톡시디페닐슬폰-3,3'-디이소시아네이트, 3,3'-디메톡시-4,4'-디이소시아나토벤질디술폰, 4,4'-디메틸디페닐술푼-3,3'-디이소시아네이트, 4,4'-디-tert-부틸디페닐술폰-3,3'-디이소시아네이트, 4,4'-메톡시페닐에틸렌술폰-3,3'-디이소시아네이트, 4,4'-디시클로디페닐술폰-3,3'-디이소시아네이트, 4-메틸-3-이소시아네이트술포닐-4'-이소시아나토페놀에스테르, 4-메톡시-3-디이소시아네이트페닐슬포닐-4-이소시아나토페놀에스테르, 4-메틸-3-이소시아나토페닐술포닐아닐리드-3'-메틸-4'-이소시아네이트, 디페닐술포닐-에틸렌디아민-4,4'-디이소시아네이트, 4,4'-메톡시페닐술포닐-에틸렌디아민-3,3'-디이소시아네이트, 4-메틸-3-이소시아나토페닐술포닐아닐리드-4-메틸-3'-이소시아네이트, 티오펜-2.5-디이소시아네이트, 1-이소시아나토-3-이소티오시아네이트프로판,1-이소시아나토-5-이소티오시아나토펜탄, 1-이소시아나토-6-이소티오시아나토헥산, 이소티오시아나토카르보닐이소시아네이트, 1-이소시아나토-4-이소디오시아나토시클로헥산등의 폴리이소시아네이트 화합물과 가열 경화시켜서 플라스틱렌즈를 제공할수 있다.The polythiol compound obtained in the formula (II) is a polyisocyanate, a polythioisocyanate compound, i.e., 1-isocyanato-4-isothiocyanatobenzene, 4-methyl-3-isocyanato-1-isothiociata Nobenzene, 2-isocyanato-4,6-diisothiocyanato-1,3,5-triadine, 4-isocyanato-4'-isothiocyanatodiphenylsulfide, 2-isosia Nato-2'-isothiocyanatodiethyldisulfide, ethylene diisocyanate, trimethylene diisocyanate, detramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonadiisocyanate, 1,2'-dimethyl Isocyanates of pentane, 2,2,4-trimethylhexamethylene diisocyanate, decamethylene diisocyanate, butane diisocyanate, 1,3-bisbutadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate , 1,6,11- Decane triisocyanate, 1,3,6-hexamethyltentriisocyanate, 1,8 diisocyanato-4-isocyanatomethyloctane, 2,5,7-trimethyl-1,8-diisocyanato-5 isocyanate Natomethyloctane, 2,6-di (isocyanatomethyl) furan, isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexyl methane diisocyanate, siglohexane diisocyanate, methyl siglohexane Diisocyanate, ciglohexyldimethylmethane diisocyanate, 2,2'-dimethyl dicyclohexyl methane diisocyanate, bis (4-isocyanato-n-butylidene) pentaerythritol, dimer isocyanate, 2-isosia Natomethyl-3- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo [2,2,1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo [2,2] -heptane, 2-isocyanatomethyl-2- (3-isocyanato Lofil) -5-isocyanatomethyl-bicyclo [2,2] heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo [2,2 ] -Heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -5- (2-isocyanatoethyl) -bicyclo- [2,2,1] heptane, 2-isocyanato Methyl-3- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -bicyclo- [2,2,]-heptane, 2-isocyanatomethyl-2-) 3-isosia Natopropyl) -5- (2-isocyanatoethyl) -bicyclo- [2,2,] heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl-6- (2-isosia Natoethyl) -bischloro- [2,2,]-heptane, 2.5 (or 6) -bis (isocyanatomethyl) -bicyclo [2,2,1] -heptane, phenylenedia isocyanate, tolyenedi Isocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diiso Lofilphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalin diisocyanate, methylnaphthalene diisocyanate, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether, 1, 4- butylene Glycol dipropyl ether-α.α'-diisocyanate, lysine diisocyanate ethyl ester, lysine triisocyanate, 2-isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2, 6-diisocyanatohexanoate, xylene diisocyanate, bis (isocyatethyl) benzene, bis (isocyatpropyl) benzene, bis (isocyanatomethyl) benzene, α, α, α ', α'- Tetramethylxylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalin, bis (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) Rate, mesitylenetriisocyanate, biphenyl diisocyanate, lollidine diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'- diisocyanate, bibenzyl-4 , 4'- diisocyanate, bis (isocyanatophenyl) ethylene 3.3'-dimethoxybiphenylmethane-dimethyldiphenyl-4,4'- diisocyanate, triphenylmethanetriisocyanate, polymethylMD1 (diphenyl methanedi Isocyanate), naphthalenetriisocyanate, diphenylmethane, 2,2,4'-triisocyanate, 3-methyldiphenylmethane-4,6,4'-triisocyanate, 4-methyl-diphenylmethane-3,5, 2 ', 4', 6'-penta isocyanate, phenyl isocyanatomethyl isocyanate, phenyl isocyanatoethyl isocyanate, tetrahydronaphthalene diisocyanate, hexahydrobenzenediisocyanate, hexahydrodiphenylmethane-4,4'- Diisocyanate, Diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate, benzophenone diisocyanate, diethylene glycol diphenyl ether diisocyanate, dibenzofurane diisocyanate, carbazole diisocyanate , Ethylcarbazole diisocyanate, dichlorocarbodiisocyanate, thiodiethylene diisocyanate, thiodipropyl diisocyanate, biodihexyl diisocyanate, dimethyl sulfon diisocyanate, dithiodimethyl diisocyanate, dithiodimethyl diisocyanate, dithiodipropyldi Isocyanate, diphenylsulfide-2,4'-diisocyanate, diphenylsulfide-4,4'-diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanate dibenzylthioether, bis ( 4-isocyanatomethylphenyl) sulfide, 4,4'-methoxyphenylthi Oethylene glycol-3,3'- diisocyanate, diphenyl disulfide-4,4'- diisocyanate, 2,2'- dimethyl diphenyl disulfide-5,5'- diisocyanate, 3,3'- dimethyl Diphenyldisulfide-5,5'-diisocyanate, 3.3'-dimethyldiphenyldisulfide-6,6'-diisocyanate, 4,4'-dimethyldiphenyldisulfide-5,5'-diisocyanate, 3 , 3'-dimethoxydiphenylsulphide-4,4'-diisocyanate, 4,4'-dimethoxydiphenyldisulfide-3,3'-diisocyanate, diphenylsulfon-3,3'-diisocyanate , Benzidine sulfone-4,4'-isocyanate diphenylmethanesulfone-4,4'-diisocyanate, 4-methyldiphenylsulfone-2,4'-diisocyanate, 4,4'-dimethoxydiphenylsulfone-3 , 3'- diisocyanate, 3,3'-dimethoxy-4,4'-diisocyanatobenzyldisulfone, 4,4'-dimethyldiphenylsulfon-3,3'- diisocyanate, 4,4'- Di-tert-butyldiphenylsulfon-3,3'-diisocyanate, 4,4'-methoxyphenylethylenesulfone-3,3 '-Diisocyanate, 4,4'-dicyclodiphenylsulfon-3,3'-diisocyanate, 4-methyl-3-isocyanatesulfonyl-4'-isocyanatophenol ester, 4-methoxy-3-di Isocyanatephenylsulfonyl-4-isocyanatophenol ester, 4-methyl-3-isocyanatophenylsulfonylanilide-3'-methyl-4'-isocyanate, diphenylsulfonyl-ethylenediamine-4,4'- Diisocyanate, 4,4'-methoxyphenylsulfonyl-ethylenediamine-3,3'-diisocyanate, 4-methyl-3-isocyanatophenylsulfonylanilide-4-methyl-3'-isocyanate, thiophene -2.5-diisocyanate, 1-isocyanato-3-isothiocyanate propane, 1-isocyanato-5-isothiocyanatopentane, 1-isocyanato-6-isothiocyanatohexane, isothio At the time of heat-hardening with polyisocyanate compounds, such as cyanatocarbonyl isocyanate and 1-isocyanato-4-isodiocyanatocyclohexane Books can provide a plastic lens.

또, 화학식(Ⅱ)에서 얻어진 폴리티올과 위의 폴리이소시아네이트 화합물에 활성화 수소화합물, 즉, 에틸렌글리콜, 디에틸렌글리콜, 프로필렌글리콜 디프로필렌글리콜, 부틸렌글리콜, 네오펜틸글리콜, 글리세린, 트리메틸롤에탄, 드리메틸롤프로판, 부탄트리올, 1,2-메티클로사이드, 펜타에리쓰리톨, 디펜타에리쓰리톨, 트리펜타에리쓰리톨, 소르비톨, 에틸렌글리콜, 트레이톨리비톨, 아라비니톨, 크실리톨, 알리톨, 마니톨, 돌시톨, 히데이톨, 글리콜, 이노시톨, 헥산트리올, 트리글리세로오스, 디글리페롤, 트리에틸렌글리콜, 폴리에틸렌글리콜, 트리스(2-히도특시에틸)이소시아누레이트, 시클로부탄디올, 시클로펜탄디올 시클로헥산디올, 시콜로헵탄디올, 시클로옥탄디올, 시클로헥산디메탄올, 히드록시프로필시클로헥산올, 디히드록시나프탈렌, 트리히드록시나프탈렌, 테트라히드록시나프탈렌, 디히드록시벤젠, 벤젠트리올, 디페닐테트라올, 피로갈올,(히드록시나프틸)피로갈올, 트리히드록시페난트텐, 비스페놀A-테트라브롬비스페놀A-비스-(2-히드록시에틸에테프), 1,3-비스(2,히드록시에틸티오에틸)-시클로헥산등의 유황원자를 함유한 폴리올, 1,2-에탄디티올, 1,1-프로판디티올, 1,2-프로판디티올, 1,3-프로판디티올, 2,2-프로판디티올, 1,6-헥산디티올, 1,2,3-프로판트리티옴 1,1-시클로헥산디티올, 1,2-시클로헥산디티올, 2,2-디메틸프로판-1,3-디티올, 3,4-디메톡시부탄-1,2-디티올, 2-메틸시클로헥산-2,3-디티올, 비시클로 [2,2] 헵타-exo-cis-2,3-디티올, 1,1-비스(메르캅토에틸)시클로헥산, 티오말산비스(2-메르캅토에틸에스테르), 2,3-디메르캅토숙신산(2-메르캅토에틸에스테르), 2,3-디에르캅토-1-프로판을(2-메르캅토아세테이트), 2,3-디메르캅토-1-프로판올(3-메르캅토아세테이트), 디에틸렌글리콜비스92-메르캅토아세테이트), 디에틸렌그리콜비스(3-메르캅토포로피오네이트), 1,2-디메르캅토프로필메틸에테르트), 2,3-디메르캅토프로필메틸에테르, 2,2-비스(메르캅토메틸)-1,3-프로판디티올, 비스(2-메프캅토에틸)에테르, 에틸렌글리콜비스(2-메르캅토이세테이트), 에틸렌글리콜비스(3-메르캅토프로피오네이트), 트리메틸플프로판트리스(2-메르캅토아세테이트), 트라메틸콜포로판트리스(3-메르캅토프로피오네이트), 펜타에리트리톨테트라키스(2-메르캅토아세테이트), 펜타에티트리톨레트리키스(3-메르캅토푸로피오네이트), 1,2-비스(메르캅토에틸)벤젠, 1,3-비스(메르캅토에틸)벤젠, 1,4-비스(메르캅토에틸)벤젠, 1,2-비스(에르캅토메틸렌옥시)벤젠, 1,3-비스(메르캅토메틸렌옥시)벤젠, 1,4-비스(메르캅토메틸렌옥시)벤젠, 1,2-비스(메르캅토에틸렌옥시)벤젠, 1,3-비스(메르캅토에틸렌옥시)벤젠 1,4-비스(메르캅토에틸렌옥시)벤젠, 1,2,3-트리메르캅토벤젠, 1,2,4-트리메르캅토벤젠, 1,3,5-트리메르캅토벤젠, 1,2,3-트리스(메르캅토메틸)벤젠, 1,2,4-트리스(메르캅토메틸)벤젠, 1,3,5-트리스(에르캅토에틸)벤젠, 1,2,3-트리스(메르캅토에틸)벤젠, 1,2,4-트리스(메르캅토에틸)벤젠, 1,3,5-트리스(메르캅토에틸)벤젠, 1,2,3-트리스(메르캅에틸렌옥시)벤젠, 1,2,4-트리스(메트캅토에틸렌옥시)벤젠, 1,3,5-트리스(메르캅토에틸렌옥시)벤젠, 1,2,3-트리스(메르캅토에틸렌옥시)벤젠, 1,2,4-트리스(메르캅토에틸렌옥시)벤젠, 1,3,5-트리스(메르캅토에틸렌옥시)벤젠, 1,2,3,4-테트라메르캅토벤젠, 1,2,3,5-테트라메르캅토벤젠, 1,2,4,5-테트라메르캅토벤젠,1,2,3,4-테트라카스(메르캅토메틸)벤젠, 1,2,3,5-테트라카스(메르캅토메틸)벤젠, 1,2,4,5-테트라카스(메르캅토메틸)벤젠, 1,2,3,4-테트라카스(메르캅토메틸)벤젠, 1,2,3,5-테트라카스(메르캅토메틸)벤젠, 1,2,4,5-테트라카스(메르캅토메틸)벤젠, 1,2,3,4-테트라카스(메르캅토메틸)벤젠, 1,2,3,5-테트라카스(메프캅토에틸렌옥시)벤젠, 1,2,4,5-테트라키스(메르캅토메틸렌옥시)벤젠, 1,2,3,4-테트라키스(메르캅토에틸렌옥시)벤젠, 1,2,3,5-테트라키스(메르캅토에틸렌옥시)벤젠, 1,2,4,5-테트라키스(메르캅토에틸렌옥시)벤젠, 2,2'-디메르캅토비페닐, 4,4'-디메르캅토비페닐, 4,4'-디메르캅토비벤진, 2,5-블로엔디티올, 3,4 블루엔디티올, 1,4-나프탈렌디티올, 1,5-나트탈렌디티올, 2,6-나프탈렌디티올, 2.7-나트탈렌디티올, 2,4-딤네틸벤젠-1,3-디티올, 4,5-디메틸벤젠 1,3-디티올, 9,10-안트라센디메탄디올, 1,3-나(P-메록시페닐)프로판-2,2,-디티올, 1,3,디페닐프로판-2,2-디티올, 페닐메탄-1,1-디티올, 2,4-디(P-메르캅토페닐)펩탄등의 방향족 폴리티올, 또한 2,5-니클로로벤젠-1,3-디티올, 1,3디(P-클로로페닐)프로판-2,2-디티올, 3,4,5-트리브콤-1,2-디에르캅토벤젠, 2,3,4,6-테트라클로르-1,5-비스(메르캅토메틸)벤젠등의 염소치환체, 브롬치환체 등의 할로겐치환 방향족 폴리티올, 또한 2-메틸아니노-4,6-디티올-sym-트리이딘, 2-에틸아미노-4-6-디티올-sym-트리아딘, 2-아미노-4,6-디티올-sym-트리아딘, 2-물폴리노-4,6-디티올-sym-트리아딘, 2-티오벤젠옥시-4-6-디티올-sym-트리아딘, 2-티오부틸옥시-4-6-디티올-sym-트리아딘 등의 복소고리를 함유한 폴리티올, 또는 1,2-비스(메르캅토메틸티오)벤젠, 1,3-비스(메르캅토메틸티오)벤젠, 1,4-비스(메르캅토에틸티오)벤젠, 1,2,3-트리스(메르캅토메틸티오)벤젠, 1,2,4-트리스(메르캅토메틸티오)벤젠, 1,3,5-트리스(에르캅토에틸티오)벤젠, 1,2,3-트리스(메르캅토에틸티오)벤젠, 1,2,4-트리스(메프캅토에틸)벤젠, 1,3,5-트리스(에르캅토메틸티오)벤젠, 1,2,3,트리스(에르캅토메틸티오)벤젠, 1,2,4-트리스(메프캅토에틸)벤젠. 1.3.5-트리스(에르캅토메틸티오)벤젠, 1,2,3,4,-테트라키스스(메르캅토메틸티오)벤젠, 1,2,3,5-테트라키스스(메르캅토메틸티오)벤젠, 1,2,4,5-테트라키스스(메르캅토메틸티오)벤젠, 1,2,3,4-테트라키스스(메르캅토메틸티오)벤젠, 1,2,3,5-테트라키스스(메르캅토메틸티오)벤젠, 1,2,4,5-테트라키스스(메르캅토메틸티오)벤젠 등 및 이들의 헥일킬화물 등의 메르캅토기이외에 유황원자를 함유하는 방향족 폴리티올,비스(에르캅토메틸)슬피드비스(레르캅토에틸)술피드, 비스(메르캅토포로필)술피드, 비스(메르캅토메틸디오)메탄, 비스(2-메르캅토메틸디오)메탄, 비스(3-메르캅토메틸디오)메탄, 1,2-비스(메르캅토메틸디오)메탄, 1,2-(2-메르캅토에틸티오)에탄, 1,2,(3-메르캅토프로필)에탄, 1,3-비스(2-메르캅토메틸디오)프로판, 1,3-비스(2-메르캅토에틸티오)프로판, 1,3-비스(3-메르캅토프로필티오)프로판, 1,2,3-트리스(레크캅토에틸티오)프로판, 1,2,3-트리스(2-메르캅토에틸티오)프로판, 1,2,3-트리스(3-메르캅토프로필티오)프로판, 네트라키스(에프캅토메틸티오메틸)메틴, 테트라키스(2-메르캅토에틸티오)프로판, 1,2,3-트리스(3-메르캅토프로필티오)프로판, 네트라키스(에프캅토메틸티오메틸)메틴, 테트라키스(2-메르캅토에틸티오메틸)메탈, 테트라키스(3-메르캅토프로필티오메틸)메탄, 비스(2,3-디메르캅토프로필)술피스, 2,5-디메르캅토-1,4-디티안, 비스(메르캅토메틸)디술피드, 비스(레르캅토에틸)디술피드, 비스(레르캅토포로필)다술피드등 및 이들의 티오글리콜산 및 메르캅토포로피온산의 에스테르, 히드록시메케닙술피드 비스(2-메르캅토아세테이트), 히드록시메틸술피드비스(3-메르캅토포로피오네이트), 하드록시에틸술피드비스(2-메프캅토아세테이트), 히드록시에틸술피드비스(32-메르캅토포로피오네이트), 히드록시포뢸디술피드비스(2-메르캅토아세테이트), 히드록시에딜디술필드술피드비스(3-메르캅토포로피오네이트), 히드록시에틸디술피드비스(2-메르캅토아세테이트)히드록시메틸디술피드비스(3-메르캅토포로피오네이트), 히드록시에틸디술피드비스(2-메르캅토아세테이트), 히드록시에틸디술피드비스(3-메르캅토포로피로네이트), 히드록시포로필디술피드비스(2-에르캅토아세테이트), 히드록시프로필 디술피드비스(3-메르캅토포로피오네이트), 2-메르캅토에틸에테르비스(2-메르캅토아세테이트), 2-메르캅토아세테르비스(3-메르캅토프로피오네이트), 1,4-디티안-2,5 디올비스(2-메르캅토아세테이트), 1,4-디티안-2,5-디올비스(3-메르캅토포르피오네이트), 티오글리콜산비스(2-메르캅토에틸에스테르), 티오디포로산비스(2-메르캅토에틸에스테르), 4,4-티오디부탈산비스(2-메르캅토에틸에스테르), 디티오디클리콜산비스(2-메르캅토에틸에스테르), 디티오디프로피온산비스(2-메르캅토에틸에스테르) 4,4-디티오디부틸산비스(2-메르캅토에틸에스테르), 티오디글리틀콜비스(2,3-디에르캅토포르필에스테르), 티오디프로피온산비스(2,3-디메르캅토프로필에스테르), 디티오클리콜산비스(2,3-디메르캅토프로필에스테르), 디티오디프로피온산(2,3 메르캅토프로필에스테르), 3,4-티오펜디티올, 2,5-니메르캅토-1,3,4-티아디아졸,2-메르캅토에탄올, 3-메르캅토-1,2-프로판디올, 글리세리딘(메르캅토아세테이트), 1-히드록시-4-메르캅토시글로로헥산, 2,4-디메르캅토페놀, 2-에르캅토히드록퀴논, 4-메르캅토페놀, 3,4-디메프캅토-2-포로판올, 1,3-디메르캅토-2=프로판올, 2,3-디메르캅토-1-프로판올, 1,2-디메르캅토-1, 3-부탄티올, 펜타에리트리틀트리스(3-메르캅토프로피오네이트), 펜타에리트리틀모노(3-메르캅토프로피오네이트), 펜타에리트리틀비스(3-메르캅토프로피오네이트), 펜타에리트리톱트리스(티오글리코레이트), 펜타에리트리톨펜타키스(3-메르캅토프로피오네이트), 히드록시메틸리스(메르캅토에틸티오에틸)메탄, 1,히드록시에틸티오-3-메르캅토에틸티오벤젠, 4-히드록시-4'-메르캅토디페닐술푼, 2-(2-메르캅토에틸티오)에탄올, 디히드록시에틸술피드모노(3-메르캅토프로피오네이트), 디메르캅토에탄모노(살리실레이트), 히드록시에틸티오에틸-트리스(메르캅토에틸티오)메탄등과 혼합하여 사용 할 수 있다.In addition, the activated hydrogen compound, ie, ethylene glycol, diethylene glycol, propylene glycol dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylol ethane, Drimethylolpropane, Butanetriol, 1,2-Methicloside, Pentaerythritol, Dipentaerythritol, Tripentaerythritol, Sorbitol, Ethylene Glycol, Thritololibitol, Arabinitol, Xyl Tol, allitol, mannitol, dolitol, hydritol, glycol, inositol, hexanetriol, triglycerose, diglyferol, triethylene glycol, polyethylene glycol, tris (2-dodooxyethyl) isocyanurate , Cyclobutanediol, cyclopentanediol cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, dihydroxynaphthalene, tri Doxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, diphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthene, bisphenol A-tetrabrom bisphenol A-bis Polyols containing sulfur atoms such as-(2-hydroxyethylether), 1,3-bis (2, hydroxyethylthioethyl) -cyclohexane, 1,2-ethanedithiol, 1,1-propane Dithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanethiom 1,1-cyclohexane Dithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3 -Dithiol, bicyclo [2,2] hepta-exo-cis-2,3-dithiol, 1,1-bis (mercaptoethyl) cyclohexane, thiomalic acid bis (2-mercaptoethyl ester), 2 , 3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3-diercapto-1-propane (2-mercaptoa Tate), 2,3-dimercapto-1-propanol (3-mercaptoacetate), diethylene glycol bis 92-mercapto acetate), diethylene glycol bis (3-mercaptophoropionate), 1 , 2-dimercaptopropylmethylether), 2,3-dimercaptopropylmethylether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mecaptoethyl) Ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylplepropane tris (2-mercaptoacetate), tramethylcolophane tris (3-mer Captopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptofulopionate), 1,2-bis (mercaptoethyl) benzene, 1, 3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (ercaptomethyleneoxy) benzene, 1,3-bis (mercaptomethyleneoxy) benne Zen, 1,4-bis (mercaptomethyleneoxy) benzene, 1,2-bis (mercaptoethyleneoxy) benzene, 1,3-bis (mercaptoethyleneoxy) benzene 1,4-bis (mercaptoethyleneoxy ) Benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,5-tris (ercaptoethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris ( Mercaptoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 1,2,3-tris (mercapethyleneoxy) benzene, 1,2,4-tris (methcaptoethyleneoxy) benzene, 1,3,5-tris (mercaptoethyleneoxy) benzene, 1,2,3-tris (mercaptoethyleneoxy) benzene, 1,2,4-tris (mercaptoethyleneoxy) benzene, 1,3,5 -Tris (mercaptoethyleneoxy) benzene, 1,2,3,4-tetramercaptobenzene, 1,2,3,5-tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1 , 2,3,4-tetracas (mercap) Methyl) benzene, 1,2,3,5-tetracas (mercaptomethyl) benzene, 1,2,4,5-tetracas (mercaptomethyl) benzene, 1,2,3,4-tetracas (mer) Captomethyl) benzene, 1,2,3,5-tetracas (mercaptomethyl) benzene, 1,2,4,5-tetracas (mercaptomethyl) benzene, 1,2,3,4-tetracas ( Mercaptomethyl) benzene, 1,2,3,5-tetracas (mecaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,4- Tetrakis (mercaptoethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptoethyleneoxy) benzene, 2,2 ' Dimercaptobiphenyl, 4,4'-dimercaptobiphenyl, 4,4'-dimercaptobibenzine, 2,5-bloenedithiol, 3,4 blueenedithiol, 1,4-naphthalenediti Ol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2.7-naphthalenedithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene 1,3 -Dithiol, 9,10-anthracenedimethanediol, 1,3-na (P-methoxyphenyl Propane-2,2, -dithiol, 1,3, diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (P-mercaptophenyl) peptane Of aromatic polythiols, also 2,5-nichlorobenzene-1,3-dithiol, 1,3di (P-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribcomb-1 Halogen-substituted aromatic polythiols such as chlorine substituents such as, 2-diercaptobenzene, 2,3,4,6-tetrachlor-1,5-bis (mercaptomethyl) benzene, and bromine substituents; No-4,6-dithiol-sym-triidine, 2-ethylamino-4-6-dithiol-sym-triadine, 2-amino-4,6-dithiol-sym-triadine, 2-water Polyno-4,6-dithiol-sym-triadine, 2-thiobenzeneoxy-4-6-dithiol-sym-triadine, 2-thiobutyloxy-4-6-dithiol-sym-triadine Polythiols containing heterocycles, or 1,2-bis (mercaptomethylthio) benzene, 1,3-bis (mercaptomethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,2,4-tri S (mercaptomethylthio) benzene, 1,3,5-tris (ercaptoethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4-tris (mecaptoethyl ) Benzene, 1,3,5-tris (ercaptomethylthio) benzene, 1,2,3, tris (ercaptomethylthio) benzene, 1,2,4-tris (mecaptoethyl) benzene. 1.3.5-tris (ercaptomethylthio) benzene, 1,2,3,4, -tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) Benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis Aromatic polythiols and bis containing sulfur atoms in addition to mercapto groups such as s (mercaptomethylthio) benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, and their hexyl chelates (Ercaptomethyl) sulfide bis (ercaptoethyl) sulfide, bis (mercaptoporophyll) sulfide, bis (mercaptomethyldio) methane, bis (2-mercaptomethyldio) methane, bis (3 Mercaptomethyldio) methane, 1,2-bis (mercaptomethyldio) methane, 1,2- (2-mercaptoethylthio) ethane, 1,2, (3-mercaptopropyl) ethane, 1, 3-bis (2-mercaptomethyldio) propane, 1,3-bis (2-mercaptoethylthio) propane, 1,3-bis (3-mer Captopropylthio) propane, 1,2,3-tris (reccaptoethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, 1,2,3-tris (3-mercapto Propylthio) propane, netrakis (ecaptomethylthiomethyl) methine, tetrakis (2-mercaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane, netrakis (ecapto) Methylthiomethyl) methine, tetrakis (2-mercaptoethylthiomethyl) metal, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulphate, 2,5- Dimercapto-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (lercaptoethyl) disulfide, bis (lercaptoporophyll) sulfide and the like and thioglycolic acid and mercaptopo Esters of lopionic acid, hydroxy mekenib sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptophoropionate), hydroxyethyl sulfide bis ( 2-methcaptoacetate), hydroxyethyl sulfide bis (32-mercaptophoropionate), hydroxy fortune disulfide bis (2-mercaptoacetate), hydroxyedyl disulfide sulfide bis (3- Mercaptophoropionate), hydroxyethyl disulfide bis (2-mercaptoacetate) hydroxymethyl disulfide bis (3-mercaptophosphopionate), hydroxyethyl disulfide bis (2-mercaptoacetate) ), Hydroxyethyl disulfide bis (3-mercaptophoropynate), hydroxy porphyil disulfide bis (2-ercaptoacetate), hydroxypropyl disulfide bis (3- mercaptophoropionate) , 2-mercaptoethyl etherbis (2-mercaptoacetate), 2-mercaptoaceterbis (3-mercaptopropionate), 1,4-dithiane-2,5 diolbis (2-mercapto Acetate), 1,4-dithiane-2,5-diolbis (3-mercaptophorpionate), thioglycolic acidbis (2-mer Toethyl ester), thiodiporoic acid bis (2-mercaptoethyl ester), 4,4-thiodibutalic acid bis (2-mercaptoethyl ester), dithiodi glycolic acid bis (2-mercaptoethyl ester ), Dithiodipropionate bis (2-mercaptoethyl ester) 4,4-dithiodibutyl acid bis (2-mercaptoethyl ester), thiodiglitol cobis (2,3-diercaptoformyl ester) , Thiodipropionic acid bis (2,3-dimercaptopropyl ester), dithio glycolic acid bis (2,3-dimercaptopropyl ester), dithiodipropionic acid (2,3 mercaptopropyl ester), 3,4- Thiophendithiol, 2,5-nimercapto-1,3,4-thiadiazole, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glyceride (mercaptoacetate), 1- Hydroxy-4-mercaptosigolohexane, 2,4-dimercaptophenol, 2-ercaptohydroxyquinone, 4-mercaptophenol, 3,4-dimecapto-2-poropanol, 1 , 3-dimercapto-2 = f Panol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1, 3-butanethiol, pentaerythritol tris (3-mercaptopropionate), pentaerythritol mono (3- Mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythrolitoptris (thioglycorate), pentaerythritol pentakis (3-mercaptopropionate), hydroxymethyl Lis (mercaptoethylthioethyl) methane, 1, hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptodiphenylsulfon, 2- (2-mercaptoethylthio) ethanol , Dihydroxyethyl sulfide mono (3-mercaptopropionate), dimercaptoethanemono (salicylate), hydroxyethylthioethyl-tris (mercaptoethylthio) methane and the like can be used. have.

이들 활성화수소화합물과 폴리이소시아네이트화합물과의 사용 비율은 (NCO+NCS)/(OH+SH)의 관능기몰비가 통상 0.4-1.6의 범위가 바람직하다.As for the usage ratio of these activated hydrogen compounds and a polyisocyanate compound, the functional group molar ratio of (NCO + NCS) / (OH + SH) is normally preferable in the range of 0.4-1.6.

또, 광학렌즈의 내후성 및 초기색상을 개선하기 위하여, UV 흡수제, 착색방지제, 산화방지제, 염료등의 첨가제를 사용 할 수 있으며, 중합반응성을 향상하기 위하여 촉매로는 디부틸틴라우릴레이트, 디부틸틴디클로라이드, 트리에틸아민을 사용 할 수 있으며, 유리몰드에서 성형된 광학렌즈를 쉽게 불리하기 위하여 실리콘계, 불소계 계면활성제와 산성인산에스테르(젤렉UN)등을 위 화합물에 미리혼합하여 사용할 수도 있으며, 혹은 메탄올, 메틸렌디클로라이드등의 용매에 용해하여 유리몰드에 도포하여 사용 할 수 도있다.In addition, in order to improve weather resistance and initial color of the optical lens, additives such as UV absorbers, anti-colorants, antioxidants, and dyes may be used, and in order to improve polymerization reactivity, dibutyltinlaurylate, di Butyl tin dichloride, triethylamine may be used, and in order to easily disadvantage the optical lens molded in the glass mold, silicone-based, fluorine-based surfactants and acidic phosphate esters (GELEXUN), etc. may be premixed with the above compounds, Alternatively, it may be dissolved in a solvent such as methanol or methylene dichloride and applied to a glass mold.

상기에서 수득한 광학재료는 하기와 같이 한정되지는 않을지라도, 플라스틱안경렌즈등과 같은 광학제품에 사용하는 것이 바람직하다.Although the optical material obtained above is not limited as follows, it is preferable to use it for optical products, such as a plastic eyeglass lens.

[실시예]EXAMPLE

이하에서, 본 발명의 실시예 및 비교예를 상세히 설명하지만, 본 발명이 이에 한정되는 것은 아니다.Hereinafter, examples and comparative examples of the present invention will be described in detail, but the present invention is not limited thereto.

실시예1Example 1

에탄디티올 0.5몰, 트리에틸아민 0.01 몰에 에피클롤로히드린 1몰을 5-10℃로 반응물을 유지하면서 2시간에 걸쳐서 서서히 적하 한 후, 2시간동안 교반한다. 여기에 50% NaOH 수용액 1 몰과 메르캅토에탄올 1몰의 혼합액을 3시간에 걸쳐서 적하한 후, 35℃에서 3시간 교반한다. 36% 염산 303.8g(3몰)과 티오우레아190.3g(2.5몰)을 상온에서 투입하고 110℃에서 6시간 유지한다. 반응물을 25℃로 냉각하여 톨루엔 400ml를 넣고, 45% NaOH 수용액 360 g를 서서히 적하한다. 반응물을 110℃에서 2시간 동안 반응시킨다.0.5 mol of ethanedithiol and 0.01 mol of triethylamine were slowly added dropwise over 2 hours while maintaining the reaction at 5-10 ° C., followed by stirring for 2 hours. The mixture liquid of 1 mol of 50% NaOH aqueous solution and 1 mol of mercaptoethanols is dripped here over 3 hours, and it stirred at 35 degreeC for 3 hours. 303.8 g (3 mol) of 36% hydrochloric acid and 190.3 g (2.5 mol) of thiourea are added at room temperature and maintained at 110 ° C for 6 hours. The reaction was cooled to 25 ° C, 400 ml of toluene was added, and 360 g of 45% NaOH aqueous solution was slowly added dropwise. The reaction is reacted at 110 ° C. for 2 hours.

톨루엔 250ml를 사용하여 추출하고, 염산 50ml로 세척한 후, 200ml의 탈이온 수를 사용하여 2회 더 세척한 후 망초로 수분을 제거 하였다. 감압농축하여 폴리티올 성분(Ⅰ)을 192g(수율 90%) 얻었다250 ml of toluene was extracted, washed with 50 ml of hydrochloric acid, and then washed twice more with 200 ml of deionized water, and then water was removed with a forget-me-not. Concentration under reduced pressure afforded 192 g (yield 90%) of polythiol component (I).

위 성분(Ⅰ)의 구조를 결정하는 분석 결과는 하기와 같다.Analysis results for determining the structure of the above component (I) are as follows.

실시예 2Example 2

실시예 1에서 에탄디티올 대신 2-메르캅토에틸술피드를 사용하여 실시예1과같은 방법으로 합성하여 성분(Ⅱ)의 티올화합물 197g(수율 86%)을 얻었다.In Example 1, using the 2-mercaptoethyl sulfide instead of ethanedithiol, it was synthesized in the same manner as in Example 1 to obtain 197 g (yield 86%) of a thiol compound of component (II).

실시예 3Example 3

실시예 1에서 에탄디티올 대신 2-메르캅토에틸에테르를 사용하여 실시예1과 같은 방법으로 합성하여 성분(Ⅲ)의 티올화합물 187g(수율 82%)을 얻었다.In Example 1, using the 2-mercaptoethyl ether instead of ethanedithiol was synthesized in the same manner as in Example 1 to obtain 187 g (yield 82%) of a thiol compound of component (III).

실시예 4Example 4

실시예 1에서 에탄디티올 대신 벤젠 디티올을 사용하여 실시예1과 같은 방법으로 합성하여 성분(IV)의 티올화합물 150.6g(수율 65%)을 얻었다.In Example 1, benzene dithiol instead of ethanedithiol was synthesized in the same manner as in Example 1 to obtain 150.6 g (yield 65%) of a thiol compound of component (IV).

실시예 5Example 5

본 발명의 광학재료 및 렌즈의 제조는 성분(Ⅰ)의 화합물 0.1몰(42.6g), m-크실렌디이소시아네이트(XDI) 0.2몰(37.6g), 디부틸틴 디클로라이드 1.6x10-5(0.005g)의 혼합물을 감압하에서 2시간 동안 교반하고, 플라스틱 가스켓으로 조립된 유리몰드에 주입한다. 혼합물이 주입된 유리몰드를 강제순환식오븐에 넣고 30℃에서 2시간 유지, 30℃에서 40℃까지 4시간 승온, 40℃에서 4 시간 유지, 40℃에서 120℃ 까지 8시간 승온, 120℃ 2시간유지, 120℃에서 60℃까지 4시간 냉각 후, 유리몰드를 탈착하여 렌즈를 얻었다.Preparation of the optical material and lens of the present invention comprises 0.1 mole (42.6 g) of compound (I), 0.2 mole (37.6 g) of m-xylene diisocyanate (XDI), 1.6 x 10 -5 (0.005 g) dibutyltin dichloride. ) Is stirred under reduced pressure for 2 hours and poured into a glass mold assembled with a plastic gasket. The glass mold into which the mixture was injected was placed in a forced circulation oven and maintained at 30 ° C. for 2 hours, heated at 30 ° C. to 40 ° C. for 4 hours, held at 40 ° C. for 4 hours, and heated at 40 ° C. to 120 ° C. for 8 hours, and 120 ° C. 2. After holding for 4 hours from 120 ° C to 60 ° C for a while, the glass mold was detached to obtain a lens.

제조된 렌즈는 아래와 같은 방법으로 물성평가를 하여 그 결과를 표1에 나타내었다.The manufactured lens was evaluated for physical properties in the following manner and the results are shown in Table 1.

굴절율 및 분산치: 아베굴절계 아타코사 1T 모델을 사용하여 측정하였다.Refractive Index and Dispersion: Measured using an Abe refractometer Atacosa 1T model.

내열성:더어모메카니컬아나라이저[파아킨엘마사제사]를 사용하여 시험편에 5g을 가하고 분당 2.5℃씩 가열하여 열변형 개시온도를 측정하였다.Heat resistance: 5 g was added to the test piece using the thermomechanical analyzer (manufactured by Parkin Elmar Co., Ltd.), and heated at 2.5 ° C. per minute to measure the heat deformation start temperature.

내충격성: 제조된 플라스틱렌즈의 중심 부분에 16.8g의 강철구를 127cm 높이에서 낙하하여 렌즈가 부서지지 않으면로 표시하고 부서지면로 표시하였다.Impact resistance: If the 16.8g steel ball is dropped from the height of 127cm to the center of the plastic lens, the lens will not be broken. Marked with broken Marked as.

광투과율: 분광 광도계를 사용하여 측정하였다.Light transmittance: Measured using a spectrophotometer.

내광성: 플라스틱 렌즈를 Q-Pannel lad products사의 QUV/Spray 모델(5w)에 200시간 폭로하여 렌즈의 색상변화가 없으면, 있으면로 표시 하였다.Light resistance: 200 hours of exposure to the Q-Pannel lad products' QUV / Spray model (5w). , if there is Marked as.

얻어진 렌즈는 굴절률(nD)이 1.66으로 높고, 아베수도 32로 높다. 또, 이 렌즈는 내후성, 내충격성, 내광성, 투명성과 같은 광학 특성이 아주 우수하다.The obtained lens has a high refractive index (nD) of 1.66 and an Abbe number of 32. This lens also has excellent optical properties such as weather resistance, impact resistance, light resistance and transparency.

실시예 6 -24Example 6-24

본 발명의 다른 광학 재료의 제조 및 렌즈의 제조는The manufacture of other optical materials and the manufacture of lenses of the present invention

표1에서 표기한 단량체 조성물을 사용하여 중합 조건이 적당히 변화는 것외에는 실시예 5의 공정을 반복하여 렌즈를 제조하였다. 표 1에서는 실시예 5-24에서 얻은 중합체 뿐만 아니라 이들 중합체들의 물성도 나타 내었다. 표 1에서 알 수 있듯이 신규 폴리치올 화합물을 사용하여 얻은 중합체는 굴절율이 1.592-1.685로 높고, 내열성, 광안정성등 광학 특성이 우수하다.The lens was manufactured by repeating the process of Example 5 except that the polymerization conditions were appropriately changed using the monomer composition shown in Table 1. Table 1 shows not only the polymers obtained in Example 5-24 but also the physical properties of these polymers. As can be seen from Table 1, the polymer obtained using the novel polythiol compound has a high refractive index of 1.592-1.685, and is excellent in optical properties such as heat resistance and light stability.

비교예 1Comparative Example 1

펜타에리트리톨테트라키스메르캅토프로피오네이트(PETMP) 0.1몰, m-크실렌디이소시아네이트 0.2몰 및 디부틸틴디클로라이드 1.610-5몰을 사용한 것외에는 실시예 5와 같이하여 중합체를 얻은 후, 그 물성을 표1에 나타내었다.Pentaerythritol tetrakismercaptopropionate (PETMP) 0.1 mol, m-xylene diisocyanate 0.2 mol and dibutyl tin dichloride 1.6 A polymer was obtained in the same manner as in Example 5 except that 10-5 mol was used, and the physical properties thereof are shown in Table 1.

비교예 2-3Comparative Example 2-3

표1에서 나타낸 단량체 조성물을 사용한 것 외에는 비교예1과 같이하여, 중합체를 얻은 후, 그 물성을 표1에 나타내었다.A polymer was obtained in the same manner as in Comparative Example 1 except that the monomer composition shown in Table 1 was obtained, and the physical properties thereof are shown in Table 1.

표1의 약자표Abbreviation Table of Table 1

S-1S-1

S-2S-2

S-3S-3

S-4S-4

XDI: m-크실렌디이소시아네이트XDI: m-xylene diisocyanate

IPDI:이소프론디이소시아네이트IPDI: isopron diisocyanate

HMDI: 헥사메틸렌디이소시아네이트HMDI: hexamethylene diisocyanate

1,3,5-TMB: 1,3,5-트리머캅토벤젠1,3,5-TMB: 1,3,5-trimercaptobenzene

PETMP: 펜타에리트리톨테트라키스메르캅토프로피오네이트PETMP: pentaerythritol tetrakismercaptopropionate

PETMA: 펜타에리트리톨테트라키스메르캅토아세테이트PETMA: pentaerythritol tetrakis mercaptoacetate

본 발명의 신규 폴리티올 화합물은 높은 황함유율 및 한분자 내에 4개의 티올반응기를 가지므로, 디이소시아네이트와의 경화물은 높은 굴절율을 가지면서도고아베수, 고 내열성, 광안정성, 고 투명성등의 우수한 광학 특성을 가진다. 따라서, 본발명의 광학재료는 안경 및 카메라 렌즈로 사용하는 것이 바람직하나, 프리즘, 광섬유, 광디스크와 자기디스크등에 사용하는 기록 매체 기판 및 착색 필더와 자외선 흡수 필터등의 광학제품에도 사용이 가능하다.Since the novel polythiol compound of the present invention has a high sulfur content and four thiol reaction groups in one molecule, the cured product with diisocyanate has excellent refractive index, high Gobe number, high heat resistance, light stability, and high transparency. Has optical properties. Therefore, the optical material of the present invention is preferably used for eyeglasses and camera lenses, but can be used for optical media such as recording media substrates, color filters, and ultraviolet absorbing filters used in prisms, optical fibers, optical disks and magnetic disks.

..

Claims (8)

식(Ⅰ)로 표기되는 폴리티올화합물과 폴리디이소시아네이트를 NCO/SH 몰비 0.5-2.5 이 되도록 가열경화 시켜서 얻게되는 황함우레탄 광학 수지.A sulfur-containing urethane optical resin obtained by heating and curing a polythiol compound represented by formula (I) and a polydiisocyanate so as to have an NCO / SH molar ratio of 0.5-2.5. 제1항의 기재의 수지로 이루어진 플라스틱 안경렌즈.A plastic spectacle lens made of the resin of claim 1. 제1항에 있어서 폴리이소시아네이트로서 m-크실렌디이소시아네이트, 이소프론디이소시아네이트, 헥사메틸렌디이소시아네이트 중 단독 혹은 2종이상을 혼합 사용하여 얻은 황함우레탄수지.The sulfur-containing urethane resin according to claim 1, obtained by using alone or two or more of m-xylene diisocyanate, isopron diisocyanate and hexamethylene diisocyanate as polyisocyanate. 제3항의 기재의 수지로 이루어진 플라스틱 안경렌즈.A plastic spectacle lens made of the resin of claim 3. 제1항에 있어서, 식(Ⅰ)로 표시되는 폴리티올의 30몰% 이하를 펜타에리트리톨테트라키스메르캅토프로피오네이트로 대체 사용하여 얻어진 황함 우레탄 광학 수지.The sulfur-containing urethane optical resin according to claim 1, wherein 30 mol% or less of the polythiol represented by formula (I) is replaced with pentaerythritol tetrakismercaptopropionate. 제5항의 기재의 수지로 이루어진 플라스틱 안경렌즈.A plastic spectacle lens made of the resin of claim 5. 제1항에 있어서, 식(Ⅰ)로 표시되는 폴리티올의 30몰% 이하를 펜타에리트리톨테트라키스메르캅토아세테이트로 대체 사용하여 얻어진 황함 우레탄 광학수지.The sulfur-containing urethane optical resin according to claim 1, wherein 30 mol% or less of the polythiol represented by formula (I) is replaced with pentaerythritol tetrakismercaptoacetate. 제7항의 기재의 수지로 이루어진 플라스틱 안경렌즈.A plastic spectacle lens made of the resin of claim 7.
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KR100515391B1 (en) * 2002-06-27 2005-09-15 주식회사 창우정밀화학 Polythiols and their use for Optical Plastic Lens
KR100771176B1 (en) * 2007-06-19 2007-10-29 주식회사 신대특수재료 Resin composition for optical lens having high light resistance and light transmissivity, and the optical lens using it
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KR20180024749A (en) * 2016-08-31 2018-03-08 에스케이씨 주식회사 Aromatic polythiol compound used in the manufacture of an optical material
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KR100515391B1 (en) * 2002-06-27 2005-09-15 주식회사 창우정밀화학 Polythiols and their use for Optical Plastic Lens
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