KR870011159A - Copolymer having high refractive index and manufacturing method thereof - Google Patents

Copolymer having high refractive index and manufacturing method thereof Download PDF

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KR870011159A
KR870011159A KR1019860004197A KR860004197A KR870011159A KR 870011159 A KR870011159 A KR 870011159A KR 1019860004197 A KR1019860004197 A KR 1019860004197A KR 860004197 A KR860004197 A KR 860004197A KR 870011159 A KR870011159 A KR 870011159A
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나오야 이마무라
요시오 스기야마
모도아끼 요시다
히사고끼 가야노끼
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사스까 노부오
니혼이따가라스 가부시끼가이샤
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/22Esters containing halogen
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10Esters
    • C08F222/1006Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10Esters
    • C08F222/1006Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses

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Abstract

내용 없음No content

Description

고굴절률을 갖는 공중합체 및 그의 제조방법Copolymer having high refractive index and manufacturing method thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (13)

고굴절률을 갖으며, 및Has a high refractive index, and (A) 최소한 1가지의하기 일반식(Ⅰ)을 갖는 단량체로부터 유도된 제1반복 유니트 1-90중량%(A) 1-90% by weight of a first repeating unit derived from at least one monomer having the general formula (I) (식중,(Meal, R1은 수소, 염소 또는 브롬원자 또는 메틸기이고,R 1 is hydrogen, chlorine or bromine atom or methyl group, R2는 다중고리지방족 탄화수소기이며, 및R 2 is a polycyclic aliphatic hydrocarbon group, and n은 0,1,2 또는 3이다).n is 0,1,2 or 3). (B) 지방족 다가알코올과 일반식의 불포화 카르복실산과의 에스테르인 일반식(식중, R3는 수소, 염소 또는 브롬원자 또는 메틸기이다)의 잔기를 최소한 2개 갖는 최소한 1가지 단량체로부터 유도된 제2반복 유니트 1-80중량 %, 및(B) aliphatic polyhydric alcohol and general formula General formula is an ester with an unsaturated carboxylic acid 1-80% by weight of a second repeating unit derived from at least one monomer having at least two residues of which R 3 is hydrogen, chlorine or bromine or a methyl group, and (C) 최소한 1.55의 굴절률을 갖는 단일중합체를 생성할 수 있으며 라디칼성-중합이 가능한 최소한 1가지 단량체로부터 유도된 제3반복 유니트 5-90중량 %를 함유하는 공중합체.(C) a copolymer containing 5-90% by weight of a third repeat unit derived from at least one monomer capable of producing a homopolymer having a refractive index of at least 1.55 and being radical-polymerizable. 제1항에 있어서, 일반식(Ⅰ)내에서 R2로 나타낸 다중고리 지방족 탄화수소기가 7-30개의 탄소원자를 갖으며, 특히 하기 일반식을 갖는 공중합체The copolymer according to claim 1, wherein the polycyclic aliphatic hydrocarbon group represented by R 2 in general formula (I) has 7-30 carbon atoms, in particular a copolymer having the general formula (식중, Y1및 Y2는 각각 수소, 염소 또는 브롬원자 또는 저급 알킬기이거나 또는 함께 또 다른 결합을 형성한다.)(Wherein Y 1 and Y 2 are each hydrogen, chlorine or bromine atom or lower alkyl group or together form another bond) 제1항에 있어서, 제2단량체가 하기 일반식(Ⅲ)-(Ⅳ)의 화합물들로 구성된 군으로부터 선택된 화합물 공중합체The compound copolymer according to claim 1, wherein the second monomer is selected from the group consisting of compounds of the following general formulas (III)-(IV) And (식중,(Meal, R3는 수소, 염소 또는 브롬원자 또는 메틸기이고,R 3 is hydrogen, chlorine or bromine atom or methyl group, R4는 2-18개의 탄소원자를 갖는 알킬렌기이며,R 4 is an alkylene group having 2-18 carbon atoms, R5는 2-10개의 탄소원자를 갖는 알킬렌기이고,R 5 is an alkylene group having 2-10 carbon atoms, A1, A2및 A3중 최소한 2개는 일반식의 잔기이고, 나머지는 알카노일기이며, A4-A9최소한 2개는 일반식의 잔기이고, 나머지는 알카노일기이며, 및At least two of A 1 , A 2, and A 3 are of the general formula , The remainder are alkanoyl groups, and at least two of A 4 -A 9 are of the general formula Is a residue of and the remainder is an alkanoyl group, and m은 2-25의 정수이다).m is an integer from 2-25). 제 1 항에 있어서, 제 3 단량체가 하기 일반식(Ⅶ)화합물 및 하기 일반식(Ⅷ)의 비스페놀 A유도체들로 구성된 군으로부터 선택되는 공중합체.The copolymer according to claim 1, wherein the third monomer is selected from the group consisting of the following general formula compounds and bisphenol A derivatives of the following general formula: (식중,(Meal, R6는 수소, 염소 또는 브롬원자 또는 메틸기이고,R 6 is hydrogen, chlorine or bromine atom or methyl group, R7 수소원자 또는 메틸기이며,R7silver A hydrogen atom or a methyl group, R8및 R9는, 서로 독립적으로 수소, 염소 또는 브롬원자 또는 메틸기이고,R 8 and R 9 are each independently hydrogen, chlorine or bromine atom or methyl group, X는 염소, 브롬 또는 요오드원자이며,X is a chlorine, bromine or iodine atom, Z1,Z,2Z3및 Z4는, 서로 독립적으로 수소, 염소, 브롬 또는 요오드원자이고,Z 1 , Z, 2 Z 3 and Z 4 are independently of each other hydrogen, chlorine, bromine or iodine atom, P는 0,1,2 또는3이며,P is 0,1,2 or 3, q는 0 또는1-5의 정수이고, 및q is an integer of 0 or 1-5, and r 및 s는, 서로 독립적으로, 0, 1,2 또는 3이다).r and s are, independently of each other, 0, 1,2 or 3). 제 1 항에 있어서, 제 2 단량체가 1,9-노난디올디(메트)아크릴레이트, 1,12-도데칸디올디(메트)아크릴레이트, 테트라에틸렌글리콜디(메트)아크릴레이트, 노나에틸렌글리콜디(메트)아크릴레이트, 트리메틸을 프로판트리(메트)아크릴레이트, 디펜타에리트리롤헥사(매트)아크릴레이트 및 디펜다에리트리롤펜타(메트)아크릴레이트 모노아세테이트로 구성된 군으로부터 선택되는 공중합체.The method of claim 1, wherein the second monomer is 1,9-nonanediol di (meth) acrylate, 1,12-dodecanediol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, nonaethylene glycol di A copolymer selected from the group consisting of (meth) acrylate, trimethyl, propanetri (meth) acrylate, dipentaerythritol hexa (mat) acrylate, and dipentaerythrolpenta (meth) acrylate monoacetate. 제 1 항에 있어서, 제 3 단량체가 트리브로모페닐 메타크릴레이트, 트리브로모페녹시에틸 아크릴레이트2,2-비스(4-메타크릴옥시에톡시-3,5-디브로모페닐)프로판, 벤질메타크릴레이트, p-클로로벤질 메타크릴레이트 및 p-브로모벤질 메타크릴레이트로 구성된 군으로부터 선택되는 공중합체.The method of claim 1, wherein the third monomer is tribromophenyl methacrylate, tribromophenoxyethyl acrylate 2,2-bis (4-methacryloxyethoxy-3,5-dibromophenyl) propane , Benzyl methacrylate, p-chlorobenzyl methacrylate and p-bromobenzyl methacrylate. 제 1 항에 있어서, 1-70중량 %의 제1반복 유니트(A), 5-70 중량 %의 제2반복 유니트(B) 및 10-80중량 %의 제3반복 유니트(C)를 함유하는 공중합체.The method according to claim 1, comprising 1-70% by weight of the first repeating unit (A), 5-70% by weight of the second repeating unit (B) and 10-80% by weight of the third repeating unit (C). Copolymer. 제 1 항에 있어서, 제1-3단량체들과는 다르며 라디칼성 중합이 가능한 최소한 1 가지의 제 4 단량체로부터 유도된 반복유니트 40 중량% 이하를 또한 함유하는 공중합체.A copolymer according to claim 1 which also contains up to 40% by weight of a repeating unit derived from at least one fourth monomer different from the 1-3 monomers and capable of radical polymerization. 제 8 항에 있어서, 제 4 단량체가 C6-C23알킬(메트)아크릴레이트 및 하기 일반식(Ⅸ)의 폴리알킬렌글리콜모노(메트)아크릴레이트로 구성된 군으로부터 선택되는 공중합체.9. The copolymer of claim 8, wherein the fourth monomer is selected from the group consisting of C 6 -C 23 alkyl (meth) acrylates and polyalkylene glycol mono (meth) acrylates of the general formula: (식중,(Meal, R10은 수소원자 또는 메틸기이고,R 10 is a hydrogen atom or a methyl group, R11은 수소원자 또는 메틸기이며,R 11 is a hydrogen atom or a methyl group, R12는 수소원자 또는 저급알킬기이고, 및R 12 is a hydrogen atom or a lower alkyl group, and t는 1-15이다).t is 1-15). 공중합체 제조에 있어서,In preparing the copolymer, (a) 최소한 1가지의 하기 일반식(Ⅰ)을 갖는 제 1 단량체 1-90중량 %(a) 1-90% by weight of the first monomer having at least one of the following general formulas (I) (식중,(Meal, R1은 수소, 염소 또는 브롬원자 또는 메틸기이고,R 1 is hydrogen, chlorine or bromine atom or methyl group, R2는 다중고리 지방족 탄화수소기이며, 및R 2 is a multicyclic aliphatic hydrocarbon group, and n은 0,1,2 또는 3이다).n is 0,1,2 or 3). (b) 지방족 다가알코올과 일반식의 불포화 카르복실산과의 에스테르인 일반식(b) aliphatic polyhydric alcohols and general formula General formula is an ester with an unsaturated carboxylic acid (식중, R3는 수소, 염소 또는 브롬원자 또는 메틸기이다)의 잔기를 최소한 2개 갖는 최소한 1가지의 제2단량체 1-80중량%, 및 1-80% by weight of at least one second monomer having at least two residues of which R 3 is hydrogen, chlorine or bromine or a methyl group, and (C) 최소한 1.55의 굴절률을 갖는 단일 중합체를 생성할 수 있으며 라디칼성-중합이 가능한 최소한 1가지의 제3단량체 5-90중량 %, 및(C) 5-90 wt% of at least one tertiary monomer capable of producing a single polymer having a refractive index of at least 1.55 and capable of radically-polymerizing, and (d) 임의로, 제1-3단량체들과는 다르며 라디칼성-중합이 가능한 최소한 1가지의 제4단량체 40%이하를 사용하여 라디칼성-공중합 반응을 수행함을 특징으로 하는, 고굴절률을 갖는 공중합체의 제조방법.(d) optionally a high refractive index copolymer, characterized in that the radical-copolymerization reaction is carried out using at least one fourth monomer which is different from the first monomers and capable of radical-polymerization. Manufacturing method. 제10항에 있어서, 공중합반을을 주조 중합을 이용하여 수행하는 방법.The method of claim 10, wherein the copolymerization group is carried out using cast polymerization. 고굴절률을 갖으며, 및Has a high refractive index, and (X) 하기 일반식(Ⅲ),(Ⅴ) 및 (Ⅵ)의 단량체들 중에서 최소한 1가지의 단량체로부터 유도된 반복유니트 1-80중량 %, 및(X) 1-80% by weight of the repeating unit derived from at least one monomer among the monomers of the following general formulas (III), (V) and (VI), and (식중,(Meal, R3는 수소, 염소 또는 브롬원자 또는 메틸기이고,R 3 is hydrogen, chlorine or bromine atom or methyl group, R4는 2-18개의 탄소원자를 갖는 알킬렌기이며,R 4 is an alkylene group having 2-18 carbon atoms, A1, A2및 A3중 최소한 2개는 일반식의 기이고, 나머지는 알카노일기이며,At least two of A 1 , A 2, and A 3 are of the general formula Group, the rest is an alkanoyl group, A4-A9중 최소한 2개는 일반식의 잔기이고, 나머지는 알카노일기이다).At least two of A 4 -A 9 are of the general formula Residues of which are alkanoyl groups). (Y)최소한 1.55의 굴절률을 갖는 단일 중합체를 생성할 수 있으며 라디칼성 중합이가능한 최소한 1가지의 단량체로부터 유도되 반복유니트 5-90중량 %를 함유하는 공중합체.(Y) A copolymer containing 5-90% by weight of repeating units derived from at least one monomer capable of producing a single polymer having a refractive index of at least 1.55 and capable of radical polymerization. 제12항에 있어서, (X) 및 (Y) 단량체들과는 다르며 라디칼성-중합이 가능한 최소한 1가지의 단량체로부터 유도된 반복유니트 40중량 %이하를 또한 함유하는 공중합체.13. The copolymer according to claim 12, which also contains up to 40% by weight of a repeat unit which is different from the (X) and (Y) monomers and derived from at least one monomer capable of radical-polymerization. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019860004197A 1985-05-28 1986-05-28 Copolymer having high refractive index and manufacturing method thereof KR870011159A (en)

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JP11457985 1985-05-28
JP114,579 1985-05-28
JP26180985 1985-11-21
JP261,809 1985-11-21

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GB2176794A (en) 1987-01-07
DE3617755A1 (en) 1986-12-04
FR2582658A1 (en) 1986-12-05
GB8612893D0 (en) 1986-07-02
FR2582658B1 (en) 1990-02-23
GB2176794B (en) 1989-10-25
AU596100B2 (en) 1990-04-26
AU5802386A (en) 1986-12-04

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