KR930006071A - 시클로 올레핀류의 개환 복분해 중합반응용 텅스텐-이미도 촉매 - Google Patents
시클로 올레핀류의 개환 복분해 중합반응용 텅스텐-이미도 촉매 Download PDFInfo
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- KR930006071A KR930006071A KR1019920017493A KR920017493A KR930006071A KR 930006071 A KR930006071 A KR 930006071A KR 1019920017493 A KR1019920017493 A KR 1019920017493A KR 920017493 A KR920017493 A KR 920017493A KR 930006071 A KR930006071 A KR 930006071A
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- catalyst composition
- tungsten
- phenyl
- substituted phenyl
- derivatives
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- 239000003054 catalyst Substances 0.000 title claims abstract 14
- 150000001925 cycloalkenes Chemical class 0.000 title claims 2
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 title 1
- -1 polycyclic cycloolefin Chemical class 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract 5
- 239000003446 ligand Substances 0.000 claims abstract 4
- 238000005649 metathesis reaction Methods 0.000 claims abstract 4
- 238000006116 polymerization reaction Methods 0.000 claims abstract 3
- 239000012190 activator Substances 0.000 claims abstract 2
- 239000000178 monomer Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims 4
- 239000013543 active substance Substances 0.000 claims 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
- 239000003607 modifier Substances 0.000 claims 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims 2
- 150000003658 tungsten compounds Chemical class 0.000 claims 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- UTBCLIMIBBSDLG-UHFFFAOYSA-N C12=CC=CCC2C2CC2C2C1C2 Chemical compound C12=CC=CCC2C2CC2C2C1C2 UTBCLIMIBBSDLG-UHFFFAOYSA-N 0.000 claims 1
- 239000002879 Lewis base Substances 0.000 claims 1
- QRJASDLTCXIYRK-UHFFFAOYSA-N [ethoxy(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(OCC)C1=CC=CC=C1 QRJASDLTCXIYRK-UHFFFAOYSA-N 0.000 claims 1
- 230000006208 butylation Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- RVDJLKVICMLVJQ-UHFFFAOYSA-N diethoxy(phenyl)phosphane Chemical compound CCOP(OCC)C1=CC=CC=C1 RVDJLKVICMLVJQ-UHFFFAOYSA-N 0.000 claims 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 claims 1
- 150000007527 lewis bases Chemical class 0.000 claims 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 claims 1
- XBFJAVXCNXDMBH-GEDKWGBFSA-N molport-035-785-283 Chemical compound C1[C@@H](C23)C=C[C@H]1C3[C@@H]1C[C@H]2CC1 XBFJAVXCNXDMBH-GEDKWGBFSA-N 0.000 claims 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 150000008442 polyphenolic compounds Chemical class 0.000 claims 1
- 235000013824 polyphenols Nutrition 0.000 claims 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 claims 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims 1
- IELLVVGAXDLVSW-UHFFFAOYSA-N tricyclohexyl phosphate Chemical compound C1CCCCC1OP(OC1CCCCC1)(=O)OC1CCCCC1 IELLVVGAXDLVSW-UHFFFAOYSA-N 0.000 claims 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims 1
- 239000013638 trimer Substances 0.000 claims 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims 1
- IUCXVGIUCHUPIW-UHFFFAOYSA-N trioctylstannane Chemical group CCCCCCCC[SnH](CCCCCCCC)CCCCCCCC IUCXVGIUCHUPIW-UHFFFAOYSA-N 0.000 claims 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 claims 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
Classifications
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
본 발명은 복분해 중합성 폴리시클릭 시클로올레핀의 중합반응을 위한 2성분 촉매 시스템에 관한 것으로, 상기 촉매는 (a) 텅스텐-이미도 화합물 및 (b) 활성제 화합물로 구성되어 있으며, 이때 상기 (a) 화합물은 식 W(NR1)X4-X(OR2)x·Ly을 갖고, 여기서 x는 0,1,2,3 또는 4이고; y는 0 또는 1이고; \1및 \2는 알킬, 페닐, 페닐-치환된 페닐, 페닐알킬, 또는 할로겐-치환된 알킬유도체, 할로겐-치환된 페닐 유도체, 할로겐-치환된 페닐-치환된 페닐 유도체, 또는 할로겐-치환된 페닐알킬 유도체이고; X는 Br 또는 Cl이고; 상기 알킬기는 C1내지 C8이고; 상기 페닐-치환된 페닐은 C12내지 C18이고 상기 페닐알킬은 C7내지 C20이고; 그리고 L은 공여체 리간드이다.
상기 촉매시스템은 잔존모노머의 농도가 낮은 열경화성 성형 제품을 제조하기 위하여 사용된다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 텅스텐 화합물 및 활성제를 함유하며, 하나이상의 변형된 고리형 비공역 폴리시클릭 시클로올레핀 모노머를 중합반응시키기 위한 촉매 조성물에 있어서, 상기 텅스텐 화합물이 하기 일반식으로 표시되는 텅스텐-이미도 화합물인 것을 특징으로 하는 촉매 조성물:W(NR1)X4-X(OR2)x·Ly상기 일반식에서 x는 0,1,2,3 또는 4이고; y는 0 또는 1이고; R1및 R2는 알킬, 페닐, 페닐-치환된 페닐, 페닐알킬 그리고 할로겐-치환된 알킬유도체, 할로겐-치환된 페닐 유도체, 할로겐-치환된 페닐-치환된 페닐 유도체, 및 할로겐-치환된 페닐알킬 유도체들로 부터 선택된 것이고; X는 Br 또는 Cl이고; L은 공여체 리간드이고; 상기 알킬기는 C1내지 C8을 함유하고; 상기 페닐-치환된 페닐은 C12내지 C18을 함유하고 상기 페닐알킬은 C7내지 C20을 함유한다.
- 제1항에 있어서, 공여체 리간드는 디에틸에테르, 에틸렌 글리콜 디메틸 에테르, 트리에틸렌 글리콜 디메틸에테르, 2-메톡시에틸 에테르, 테트라에틸렌 글리콜 디메틸 에테르, 테트라히드로푸란, 아세토니트릴, 벤조니트릴, 피리딘, 피라진 및 퀴누클리딘으로부터 선택된 것을 특징으로 하는 촉매 조성물.
- 제1 또는 2항에 있어서, 하나이상의 루이스 염기 안정화제 화합물을 추가로 함유하는 것을 특징으로 하는 촉매 조성물.
- 제3항에 있어서, 상기 안정화제는 디에틸 에테르, 에틸렌 글리콜 디메틸 에테르, 2-메톡시에틸 에테르, 트리에틸렌 글리콜 디메틸 에테르, 테트라에틸렌 글리콜 디메틸 에테르, 벤조니트릴, 아세토니트릴, 테트라히드로푸란, 모노페놀류, 비스페놀류, 폴리페놀류 및 p-크레졸의 부틸화 반응 생성물 및 디시클로펜타디엔 및 그들의 혼합물로부터 선택된 것을 특징으로 하는 촉매 조성물.
- 상기 제1 내지 4항중 어느 한 항에 있어서, 적어도 하나의 속도 조절제가 추가로 포함되고, 이 속도조절제는 피리딘, 피라진, 트리부틸 포스피트, 트리에틸포스핀, 트리부틸포스핀, 트리시클로 헥실포스핀, 트리페닐포스핀, 메틸디페닐포스핀, 디메틸페닐포스핀, 트리에틸포스피트, 트리이소프로필 포스피트, 에틸디페닐 포스포니트, 트리페닐 포스피트, 트리이소프로필포스핀, 트리메틸 포스피트, 트리-3차-부틸포스핀, 디에틸페닐 포스포니트 및 트리벤질포스핀으로부터 선택된 것을 특징으로 하는 촉매 조성물.
- 상기 제1 내지 5항중 어느 한 항에 있어서, 활성제가 트리-n-부틸틴 히드리드인 것을 특징으로 하는 촉매 조성물.
- 상기 제1 내지 6항중 어느 한 항에 있어서, 활성제가 트리옥틸틴 히드리드인 것을 특징으로 하는 촉매조성물.
- 상기 제1 내지 7항중 어느 한 항에 있어서, 텅스텐-이미도 화합물이 식 W(NPh)(OC6H3-2,6-Cl2)2Cl2로 표시되는 것을 특징으로 하는 촉매조성물.
- 상기 제1 내지 8항중 어느 한 항에 있어서, 텅스텐-이미도 화합물이 식 W(NPh)(OC(CH3)3)4로 표시되는 것을 특징으로 하는 촉매조성물.
- 하나이상의 변형된 고리형 비공역 폴리스클릭 시클로올레핀을 복분해 중합반응시키기 위해 상기 제1 내지 9항중 어느 한 항의 촉매조성물을 사용하는 방법.
- 하나이상의 변형된 고리형 비공역 폴리시클릭 시클로올레핀을 복분해 중합반응시키기 위해 제1 내지 9항에 의한 촉매조성물을 사용하는 방법으로서, 상기 시클로올레핀이 디시클로펜타디엔, 시클로펜타디엔 3량체, 고차시크로펜타디엔 올리고머류, 노르보르넨, 노르보르나디엔, 4-알킬리덴노르보르넨, 디메타노헥사히드로나프탈렌, 디메타노옥타히드로 나프탈렌, 및 상기 시클로올리펜류의 알킬-치환된 유도체 및 그들의 혼합물로부터 선택된 것을 특징으로 하는 방법.
- 변형된 고리형 비공역 폴리시클릭 시클로올레핀 대 텅스텐-이미도 화합물의 비가 500:1 내지 15,000:1의 몰 비율로 존재하고, 텅스텐-이미도 화합물 대 활성제의 비가 1:1 내지 1:8의 몰비율로 존재하는 것을 특징으로 하는 하나이상의 상기 변형된 고리형 비공역 폴리시클릭 시클로올레핀을 복분해 중합반응시키기 위해 제1 내지 9항의 촉매조성물을 사용하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/764,657 US5194534A (en) | 1991-09-24 | 1991-09-24 | Tungsten-imido catalysts for ring-opening metathesis polymerization of cycloolefins |
US764,657 | 1991-09-24 |
Publications (2)
Publication Number | Publication Date |
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KR930006071A true KR930006071A (ko) | 1993-04-20 |
KR100211392B1 KR100211392B1 (ko) | 1999-08-02 |
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Application Number | Title | Priority Date | Filing Date |
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KR1019920017493A KR100211392B1 (ko) | 1991-09-24 | 1992-09-24 | 시클로올레핀류의 개환 복분해 중합반응용 텅스텐 이미도 촉매 |
Country Status (6)
Country | Link |
---|---|
US (1) | US5194534A (ko) |
EP (1) | EP0534388A1 (ko) |
JP (1) | JP3113091B2 (ko) |
KR (1) | KR100211392B1 (ko) |
CA (1) | CA2078093A1 (ko) |
TW (1) | TW209229B (ko) |
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WO2015047009A1 (ko) * | 2013-09-30 | 2015-04-02 | 코오롱인더스트리 주식회사 | 환상올레핀계 고분자 화합물의 개환중합용 촉매 및 이를 이용한 환상올레핀계 고분자 화합물의 제조방법 |
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US5198511A (en) * | 1991-12-20 | 1993-03-30 | Minnesota Mining And Manufacturing Company | Polymerizable compositions containing olefin metathesis catalysts and cocatalysts, and methods of use therefor |
JP3398381B2 (ja) * | 1992-07-01 | 2003-04-21 | エクソンモービル・ケミカル・パテンツ・インク | 遷移金属オレフィン重合触媒 |
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US5405924A (en) * | 1993-07-22 | 1995-04-11 | Shell Oil Company | Imido transition metal complex metathesis catalysts |
EP0864595B1 (en) * | 1997-03-13 | 2001-08-16 | Borealis Technology Oy | Supported catalysts for the ringopening metathesis polymerization of cycloolefins |
WO1999020676A1 (fr) * | 1997-10-23 | 1999-04-29 | Nippon Zeon Co., Ltd. | Polymeres a cycles ouverts et a base dicyclopentadiene thermoplastique, derives hydrogenes de ceux-ci et procedes de preparation correspondants |
US6559088B1 (en) * | 1999-02-22 | 2003-05-06 | Fina Technology, Inc. | Ziegler-Natta catalyst with amine for polymerization |
JP2002540213A (ja) * | 1999-03-31 | 2002-11-26 | カリフォルニア インスティチュート オブ テクノロジー | 高いオレフィンメタセシス活性を示す、トリアゾールイリデン配位子により配位された新規なルテニウム金属アルキルジエン錯体 |
DE60015600T2 (de) * | 1999-08-25 | 2005-11-10 | Zeon Corp. | Geöffnete norbornenringpolymere, deren hydrierungsprodukte sowie verfahren zur herstellung beider produkte |
EP1303543A1 (en) * | 2000-07-17 | 2003-04-23 | Univation Technologies LLC | A catalyst system and its use in a polymerization process |
JP4466273B2 (ja) * | 2003-08-13 | 2010-05-26 | 日本ゼオン株式会社 | 開環重合体、開環重合体水素化物およびそれらの製造方法、並びに重合触媒組成物 |
US7608671B2 (en) * | 2003-08-13 | 2009-10-27 | Zeon Corporation | Norbornene ring-opened polymer hydrogenated product and process for producing same |
JP4466272B2 (ja) * | 2004-08-12 | 2010-05-26 | 日本ゼオン株式会社 | ノルボルネン系開環重合体水素化物の製造方法およびノルボルネン系開環重合体水素化物 |
WO2008010973A1 (en) * | 2006-07-18 | 2008-01-24 | Dow Global Technologies, Inc. | Method for preparing poly(dicyclopentadiene) |
US8906999B2 (en) | 2011-02-17 | 2014-12-09 | Ccp Composites Us Llc | Styrene-free unsaturated polyester |
US9631083B2 (en) | 2013-02-12 | 2017-04-25 | Zeon Corporation | Resin composition and molded product thereof |
JP6636804B2 (ja) * | 2013-03-14 | 2020-01-29 | フェルビオ フェルアイニクテ ビオエネルギー アクチェンゲゼルシャフト | メタセシス触媒及び触媒を用いた反応 |
JP6428614B2 (ja) | 2013-07-01 | 2018-11-28 | 日本ゼオン株式会社 | 延伸フィルムの製造方法 |
EP3019510B1 (en) | 2013-07-12 | 2020-12-02 | Verbio Vereinigte BioEnergie AG | Use of immobilized molybden- und tungsten-containing catalysts in olefin cross metathesis |
WO2015049047A1 (en) | 2013-10-01 | 2015-04-09 | Ximo Ag | Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis |
EP3085722A4 (en) | 2013-12-20 | 2017-08-16 | Zeon Corporation | Resin material and resin film |
US10233301B2 (en) | 2014-01-30 | 2019-03-19 | Zeon Corporation | Polymer composition and molded body |
KR102427223B1 (ko) | 2014-09-29 | 2022-07-28 | 니폰 제온 가부시키가이샤 | 환상 올레핀 개환 중합체 수소화물, 수지 성형체, 및 광학 부재 |
US10529494B2 (en) | 2014-09-30 | 2020-01-07 | Zeon Corporation | Dielectric film |
US10287408B2 (en) | 2014-10-28 | 2019-05-14 | Zeon Corporation | Resin film, barrier film, electrically conductive film, and manufacturing method therefor |
KR102567854B1 (ko) | 2015-09-28 | 2023-08-16 | 니폰 제온 가부시키가이샤 | 적층체 및 그 제조 방법, 그리고 플렉시블 프린트 기판 |
WO2017065222A1 (ja) | 2015-10-15 | 2017-04-20 | 日本ゼオン株式会社 | 位相差フィルム及びその製造方法 |
US10522793B2 (en) | 2015-11-30 | 2019-12-31 | Zeon Corporation | Multilayer film, manufacturing method, circular-polarizing plate, antireflective film, and organic electroluminescence display device |
US10744494B2 (en) | 2015-12-23 | 2020-08-18 | Ximo Ag | Immobilized metal alkylidene catalysts and use thereof in olefin metathesis |
WO2017188160A1 (ja) | 2016-04-27 | 2017-11-02 | 日本ゼオン株式会社 | フィルムセンサ部材及びその製造方法、円偏光板及びその製造方法、並びに、画像表示装置 |
CN110325590B (zh) | 2016-08-08 | 2022-04-12 | 日本瑞翁株式会社 | 树脂组合物和树脂成型体 |
KR102491838B1 (ko) | 2017-03-21 | 2023-01-25 | 니폰 제온 가부시키가이샤 | 성형 재료, 수지 성형체, 화장료 용기, 반도체 용기, 및 반도체 용기의 제조 방법 |
EP3761330A4 (en) | 2018-02-28 | 2022-01-19 | Zeon Corporation | CAPACITOR FILM AND METHOD OF MANUFACTURING THEREOF |
WO2021072231A1 (en) * | 2019-10-11 | 2021-04-15 | Exxonmobil Chemical Patents Inc. | Catalysts for olefin metathesis, methods of preparation, and processes for the use thereof |
US20240109984A1 (en) * | 2019-10-11 | 2024-04-04 | Exxonmobil Chemical Patents Inc. | Catalysts for Olefin Metathesis, Methods of Preparation, and Processes for the use Thereof |
CN114651026A (zh) | 2019-11-29 | 2022-06-21 | 日本瑞翁株式会社 | 环状烯烃聚合物及其制造方法以及光学元件 |
WO2022181635A1 (ja) | 2021-02-26 | 2022-09-01 | 日本ゼオン株式会社 | 環状オレフィン共重合体およびその水素化物、並びに、光学素子 |
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IT979092B (it) * | 1973-02-14 | 1974-09-30 | Montedison Spa | Catalizzatori di metatesi a 3 componenti |
US4727215A (en) * | 1985-09-25 | 1988-02-23 | Massachusetts Institute Of Technology | Catalyst composition for effecting metathesis of olefins |
EP0303969A3 (en) * | 1987-08-14 | 1990-10-17 | The B.F. Goodrich Company | Bulk polymerized cycloolefin circuit boards |
-
1991
- 1991-09-24 US US07/764,657 patent/US5194534A/en not_active Expired - Fee Related
-
1992
- 1992-09-10 TW TW081107170A patent/TW209229B/zh active
- 1992-09-11 CA CA002078093A patent/CA2078093A1/en not_active Abandoned
- 1992-09-22 JP JP04252394A patent/JP3113091B2/ja not_active Expired - Lifetime
- 1992-09-23 EP EP92116252A patent/EP0534388A1/en not_active Withdrawn
- 1992-09-24 KR KR1019920017493A patent/KR100211392B1/ko not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015047009A1 (ko) * | 2013-09-30 | 2015-04-02 | 코오롱인더스트리 주식회사 | 환상올레핀계 고분자 화합물의 개환중합용 촉매 및 이를 이용한 환상올레핀계 고분자 화합물의 제조방법 |
Also Published As
Publication number | Publication date |
---|---|
JPH05345817A (ja) | 1993-12-27 |
CA2078093A1 (en) | 1993-03-25 |
KR100211392B1 (ko) | 1999-08-02 |
JP3113091B2 (ja) | 2000-11-27 |
US5194534A (en) | 1993-03-16 |
EP0534388A1 (en) | 1993-03-31 |
TW209229B (ko) | 1993-07-11 |
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