KR950029287A - Styrene-based copolymer and preparation method thereof - Google Patents

Styrene-based copolymer and preparation method thereof Download PDF

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KR950029287A
KR950029287A KR1019940008723A KR19940008723A KR950029287A KR 950029287 A KR950029287 A KR 950029287A KR 1019940008723 A KR1019940008723 A KR 1019940008723A KR 19940008723 A KR19940008723 A KR 19940008723A KR 950029287 A KR950029287 A KR 950029287A
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copolymer
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KR0164878B1 (en
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박태호
조창기
김경희
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성재갑
주식회사 엘지화학
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Abstract

본 발명은 입체구조 스티렌계 중합체 또는 공중합체에 올레핀 또는 무정형 스티렌계 공중합체가 그라프트된 공중합체 및 그의 제조방법에 관한 것이다. 더욱 상세하게는, 주쇄의 입체규칙성이 주로 신디오탁틱(syndiotactic) 구조인 스티렌계 중합체 또는 공중합체에 입체규칙성이 주로 어탁틱(atactic)구조인 올레핀이나 축합 중합체 또는 공중합체가 그라프트된 공중합체 및 그의 제조 방법에 관한 것이다.The present invention relates to a copolymer in which an olefin or an amorphous styrene copolymer is grafted to a steric styrenic polymer or copolymer, and a method of preparing the copolymer. More specifically, styrene-based polymers or copolymers in which the stereoregularity of the main chain is mainly syndiotactic is grafted to olefins or condensation polymers or copolymers in which the stereoregularity is mainly atactic. It relates to a copolymer and a method for producing the same.

Description

스티렌계 공중합체 및 그의 제조방법Styrene-based copolymer and preparation method thereof

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

Claims (16)

하기 일반식 (A)로 나타내는 1종류 이상의 반복단위 및 하기 일반식 (B)로 나타내는 1종류 이상의 마크로머로 이루어진 중합체로, 주쇄의 입체규칙성이 주로 신디오탁틱(Syndiotactic)이고, 일반식 (B)로 나타내는 1종류 이상의 마크로머가 전체의 5 내지 90중량%인 공중합체.A polymer composed of one or more types of repeating units represented by the following General Formula (A) and one or more types of macromers represented by the following General Formula (B), wherein the stereoregularity of the main chain is mainly syndiotactic, and The copolymer which is 5 to 90 weight% of the whole 1 or more types of macromers represented by B). 상기 식에서, R1은 -H 또는 -CH3이고, R2는 -H, 할로겐원자, 탄소수 1 내지 10의 알킬, 할로겐치환알킬, 알콕시, 카르복시에스테르, 알킬실릴, 알킬아미노 또는 시아노이거나, 황 또는 인을 포함하는 치환기이고, h는 1 내지 3이며, h가 2 또는 3일 때 R2는 서로 동일하거나 상이하다.Wherein R 1 is —H or —CH 3 , R 2 is —H, a halogen atom, alkyl having 1 to 10 carbon atoms, halogen substituted alkyl, alkoxy, carboxyester, alkylsilyl, alkylamino or cyano, or sulfur Or a substituent containing phosphorous, h is 1 to 3, and when h is 2 or 3, R 2 is the same as or different from each other. 상기 식에서, R3, R6및 q는 각각 상기 일반식(A)에서 정의된 R1, R2및 h와 동일하며, R4및 R5는 각각 -H 또는 -CH3이고, X는, -(CH2)a-(O-(CH2)b)c- 또는 C(O)-(CH2)∝-O-이고, 여기서, a, b, c는 1 내지 4의 수이고, d는 0 내지 3의 수이고, Y는 -COOR7, -CN 또는 -CORN8R9이고, 여기서, R7은 -H, 탄소수 1 내지 8개의 알킬, 아릴, 아릴알킬, 2-하이드록시에틸, 디메틸아미노에틸 또는 글리시딜이고, R8및 R9는 각각 탄소수 1 내지 8개의 알킬이고, i=j=0일 때, k ＞ 4, i=k=0일 때, j ＞ 4, j=k=0일 때, i ＞ 4, k=0일 때, i + j ＞ 4이다.Wherein R 3 , R 6 and q are each the same as R 1 , R 2 and h defined in Formula (A), R 4 and R 5 are each -H or -CH 3 and X is ,-(CH 2 ) a- (O- (CH 2 ) b) c- or C (O)-(CH 2 ) ∝-O-, wherein a, b, c are numbers from 1 to 4, d is a number from 0 to 3 and Y is -COOR 7 , -CN or -CORN 8 R 9 , wherein R 7 is -H, alkyl having 1 to 8 carbons, aryl, arylalkyl, 2-hydroxyethyl , Dimethylaminoethyl or glycidyl, R 8 and R 9 are each alkyl having 1 to 8 carbon atoms, and when i = j = 0, k> 4 and when i = k = 0, j> 4, j When i = k = 0, i> 4 and i = j> 4 when k = 0. 제1항에 있어서, 주사슬의 중합도가 5 이상임을 특징으로 하는 공중합체.The copolymer according to claim 1, wherein the degree of polymerization of the main chain is 5 or more. 제1항에 있어서, 신디오탁틱도가 50% 이상임을 특징으로 하는 공중합체.The copolymer of claim 1 wherein the syndiotactic degree is at least 50%. 1) 티타늄 화합물 또는 티타늄 킬레이트 화합물, 2) 트리알킬알루미늄 화합물, 3) 트리알킬알루미늄 화합물과 물의 축합물로부터 선택된 1종 이상의 촉매 존재하에서, 하기 일반식 (A')로 표시되는 1종 이상의 단량체와 일반식 (B')로 표시되는 마크로머를 공중합시킴을 특징으로 하여, 제1항의 공중합체를 제조하는 방법.At least one monomer represented by the following general formula (A ') in the presence of at least one catalyst selected from a condensate of 1) a titanium compound or a titanium chelate compound, 2) a trialkylaluminum compound, 3) a trialkylaluminum compound and water; A method for producing the copolymer of claim 1, characterized in that the macromer represented by the general formula (B ') is copolymerized. 상기 시에서, R1, R2및 h는 제1항의 일반식(A)에서 정의된 것과 동일하다.In this context, R 1 , R 2 and h are the same as defined in general formula (A) of claim 1. 상기 식에서, R3, R6및 q는 각각 제1항의 일반식(A)에서 정의된 R1, R2및 h와 동일하며, R4, R5, X 및 Y는 제1항의 일반식(B)에서 정의된 것과 동일하며, i, j, k 관계 및 범위는 제1항의 일반식(B)에서 정의된 것과 동일하다.Wherein R 3 , R 6 and q are each the same as R 1 , R 2 and h defined in formula (A) of claim 1 , and R 4 , R 5 , X and Y are the general formula of claim 1 ( Same as defined in B), i, j, k relations and ranges are the same as defined in general formula (B) of claim 1. 제4항에 있어서, 티타늄 화합물 또는 티타늄킬레이트 화합물이 다음의 일반식(C)로 표시되는 1종 또는 2종 이상의 화합물임을 특징으로 하는 방법.The method according to claim 4, wherein the titanium compound or the titanium chelate compound is one or two or more compounds represented by the following general formula (C). TiR10 aX(4-a)(C)TiR 10 a X (4-a) (C) 상기 식에서, R10은 -H, 탄소수 1 내지 20의 알킬, 탄소수 1 내지 20의 아릴, 알킬아릴 또는 아릴알킬, π-결합된 사이클로펜타디에닐기, π-결합된 일치환 또는 다치환된 사이클로펜타디에닐기, 또는 사이클로펜타디엔의 π-결합된 1가 올리고머이고, X는 할로겐 원자, -OR11또는 -NR12 2이고, 여기서 R11및 R12는 각각 탄소수 1 내지 20의 지방족, 지환족, 방향족 탄화수소 또는 아실기이고, a가 2 내지 4일 때, R10은 모두 동일하거나 다를 수 있고, a가 2 이하일 때, X(4-a)는 모두 동일하거나 a는 4이하의 정수이고, 다를 수 있다.Wherein R 10 is —H, alkyl having 1 to 20 carbon atoms, aryl having 1 to 20 carbon atoms, alkylaryl or arylalkyl, π-bonded cyclopentadienyl group, π-bonded monocyclic or polysubstituted cyclopenta A dienyl group, or a π-bonded monovalent oligomer of cyclopentadiene, X is a halogen atom, -OR 11 or -NR 12 2 , wherein R 11 and R 12 are each aliphatic, cycloaliphatic, having 1 to 20 carbon atoms, Aromatic hydrocarbons or acyl groups, when a is 2 to 4, R 10 can all be the same or different, and when a is 2 or less, X (4-a) are all the same or a is an integer of 4 or less and different Can be. 제4항에 있어서, (B')로 표시되는 마크로머가 스티렌기 또는 메틸메타크릴레이트가 말단에 있는 폴리스티렌계 단일 또는 공중합체 또는 폴리메틸메타크릴레이트 단일 또는 공중합체이거나, 또는 메틸메타크릴레이트기가 말단에 있는 폴리카프로락톤 등이 가능하고 이들과 모노비닐리덴 방향족 단량체, 탄소수 1 내지 8의 알킬메타크릴레이트, 탄소수 1 내지 8의 알킬아크릴레이트, 2-하이드록시 에틸메타크릴레이트, 2-알킬이미노 에틸메타크릴레이트, 아크릴로니트릴, 메타크릴로니트릴, 아크릴아미드, 탄소수 1 내지 1o의 알킬비닐에테르, 이소부틸렌 중에서 선택된 1종 또는 2종 이상의 단량체와 공중합체를 이루고 있으면서 말단이나 사슬의 일부에 관능기를 가지고 있는 마크로머임을 특징으로 하는 방법.The method according to claim 4, wherein the macromer represented by (B ') is a polystyrene-based single or copolymer having a styrene group or methyl methacrylate at the terminal or a polymethyl methacrylate single or copolymer, or a methyl methacrylate group. Polycaprolactone and the like at the terminal, and monovinylidene aromatic monomer, alkyl methacrylate having 1 to 8 carbon atoms, alkyl acrylate having 1 to 8 carbon atoms, 2-hydroxy ethyl methacrylate and 2-alkyl. Part of the terminal or chain while being copolymerized with one or two or more monomers selected from mino ethyl methacrylate, acrylonitrile, methacrylonitrile, acrylamide, alkyl vinyl ether having 1 to 1 carbon atoms and isobutylene Characterized in that it is a macromer having a functional group. 제4항에 있어서, 트리알킬알루미늄 화합물 촉매가 하기 일반식(D)로 표시되는 1종 또는 2종 이상의 화합물임을 특징으로 하는 방법.The method according to claim 4, wherein the trialkylaluminum compound catalyst is one or two or more compounds represented by the following general formula (D). AIR13 3(D)AIR 13 3 (D) 상기 식에서, R13은 탄소수 1 내지 10의 알킬기이다.In the above formula, R 13 is an alkyl group having 1 to 10 carbon atoms. 제4항에 있어서, 트리알킬알루미늄과 물과의 축합물이 하기 일반식(E)로 표시되는 1종 또는 2종 이상의 화합물임을 특징으로 하는 방법.The method according to claim 4, wherein the condensate of trialkylaluminum and water is one or two or more compounds represented by the following general formula (E). 상기 식에서, R14는 탄소수 1 내지 8의 알킬기이고, e는 2 내지 70의 정수이다.In the above formula, R 14 is an alkyl group having 1 to 8 carbon atoms, and e is an integer of 2 to 70. 제4항에 있어서, 타티늄화합물 또는 티타늄킬레이트 화합물 촉매를 실리카, 알루미나 또는 마그네슘 화합물로부터 1종 이상의 담체와 함께 사용함을 특징으로 하는 방법.5. A process according to claim 4, wherein a titanium compound or titanium chelate compound catalyst is used with at least one carrier from silica, alumina or magnesium compounds. 제4항에 있어서, 사용되는 촉매를 1)성분, 2)성분 및 3)성분의 촉매를 동시에 사용하거나, 1)성분 및 3)성분을 동시에 사용하거나, 2)성분 및 3)성분을 동시에 사용하거나, 또는 3)성분을 단독으로 사용함을 특징으로 하는 방법.The catalyst used according to claim 4, wherein the catalyst used is a catalyst of 1) component, 2) component and 3) component simultaneously, 1) component and 3) component are used simultaneously, or 2) component and 3) component are used simultaneously. Or 3) using components alone. 제4항 또는 10항에 있어서, 사용되는 촉매를 탄소수 4 냐자 20의 알칸, 사이클로알칸 및 방향족 탄화수소용매로 희석시켜 사용함을 특징으로 하는 방법.The process according to claim 4 or 10, wherein the catalyst used is diluted with an alkanes, cycloalkanes and aromatic hydrocarbon solvents having 4 to 20 carbon atoms. 제4항 또는 10항에 있어서, 1)성분, 2)성분 및 3)성분을 동시에 사용하거나, 또는 1)성분 및 3)성분을 동시에 사용하는 경우에, 알루미늄과 티타늄의 비(A: Ti)가 5 : 1 내지 100,000 : 1임을 특징으로 하는 방법.The ratio of aluminum to titanium (A: Ti) according to claim 4 or 10, in the case where 1) component, 2) component and 3) component are used simultaneously or 1) component and 3) component are used simultaneously. Is 5: 1 to 100,000: 1. 제4항에 있어서, 공중합 온도가 0 내지 100℃임을 특징으로 하는 방법.The method of claim 4, wherein the copolymerization temperature is from 0 to 100 ° C. 6. 제4항에 있어서, 용액중합 또는 벌크중합으로 중합함을 특징으로 하는 방법.The process according to claim 4, characterized in that the polymerization is carried out by solution polymerization or bulk polymerization. 제4항에 있어서, β―수소제거반응이 용이한 단량체를 소량 첨가하거나 외부에서 수소기체를 공급함으로써 중합체의 분자량을 조절함을 특징으로 하는 방법.The method according to claim 4, wherein the molecular weight of the polymer is controlled by adding a small amount of a monomer which is easy to dehydrogenate or by supplying a hydrogen gas from the outside. 제15항에 있어서, 단량체가 알파메틸스티렌 또는 메틸메타크릴레이트임을 특징으로 하는 방법.The method of claim 15 wherein the monomer is alphamethylstyrene or methylmethacrylate. ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.※ Note: This is to be disclosed by the original application.
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WO2001092352A1 (en) * 2000-06-02 2001-12-06 Samsung General Chemicals Co., Ltd. Method of preparing monomer-grafted syndiotactic polystyrene with polarity
KR20170032713A (en) * 2015-09-15 2017-03-23 주식회사 엘지화학 Polymer, method for preparing the same, and solid electrolyte, electrode, seperator and lithium secondary battery comprising the same

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KR100332673B1 (en) * 1999-08-16 2002-04-17 윤종용 Styrene/Macromonomer Random Copolymer Having Excellent Melt Flowability and Method of Preparing The Same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001092352A1 (en) * 2000-06-02 2001-12-06 Samsung General Chemicals Co., Ltd. Method of preparing monomer-grafted syndiotactic polystyrene with polarity
US6767965B2 (en) 2000-06-02 2004-07-27 Samsung Atofina Co. Ltd. Method of preparing monomer-grafted syndiotactic polystyrene with polarity
KR20170032713A (en) * 2015-09-15 2017-03-23 주식회사 엘지화학 Polymer, method for preparing the same, and solid electrolyte, electrode, seperator and lithium secondary battery comprising the same

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