CA2902451C - Metal carbene olefin metathesis two catalyst composition - Google Patents

Metal carbene olefin metathesis two catalyst composition Download PDF

Info

Publication number
CA2902451C
CA2902451C CA2902451A CA2902451A CA2902451C CA 2902451 C CA2902451 C CA 2902451C CA 2902451 A CA2902451 A CA 2902451A CA 2902451 A CA2902451 A CA 2902451A CA 2902451 C CA2902451 C CA 2902451C
Authority
CA
Canada
Prior art keywords
olefin metathesis
composition
catalyst
metal carbene
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2902451A
Other languages
English (en)
French (fr)
Other versions
CA2902451A1 (en
Inventor
Anthony R. Stephen
Christopher J. Cruce
Michael A. Giardello
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Materia Inc
Original Assignee
Materia Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Materia Inc filed Critical Materia Inc
Publication of CA2902451A1 publication Critical patent/CA2902451A1/en
Application granted granted Critical
Publication of CA2902451C publication Critical patent/CA2902451C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F132/08—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
    • C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Catalysts (AREA)
  • Reinforced Plastic Materials (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerization Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2902451A 2013-02-27 2014-02-27 Metal carbene olefin metathesis two catalyst composition Active CA2902451C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361770284P 2013-02-27 2013-02-27
US61/770,284 2013-02-27
US201361799827P 2013-03-15 2013-03-15
US61/799,827 2013-03-15
PCT/US2014/019082 WO2014134333A1 (en) 2013-02-27 2014-02-27 Metal carbene olefin metathesis two catalyst composition

Publications (2)

Publication Number Publication Date
CA2902451A1 CA2902451A1 (en) 2014-09-04
CA2902451C true CA2902451C (en) 2021-05-25

Family

ID=51428812

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2902451A Active CA2902451C (en) 2013-02-27 2014-02-27 Metal carbene olefin metathesis two catalyst composition

Country Status (11)

Country Link
US (2) US20140357820A1 (enExample)
EP (1) EP2961778B1 (enExample)
JP (3) JP6271595B2 (enExample)
KR (1) KR102211385B1 (enExample)
CN (1) CN105229040B (enExample)
BR (1) BR112015019868B1 (enExample)
CA (1) CA2902451C (enExample)
MX (1) MX2015010583A (enExample)
MY (2) MY188144A (enExample)
SG (1) SG11201506724VA (enExample)
WO (1) WO2014134333A1 (enExample)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9527982B2 (en) * 2012-12-19 2016-12-27 Materia, Inc. Storage stable adhesion promoter compositions for cyclic olefin resin compositions
EP3092204A4 (en) * 2014-01-10 2017-12-20 Materia, Inc. Method and composition for improving adhesion of metathesis compositions to substrates
EP3257885A4 (en) * 2015-02-09 2018-05-09 Asahi Glass Company, Limited Method for producing fluorine-containing polymer
CA2975259C (en) * 2015-02-14 2023-03-14 Materia, Inc. Romp polymers having improved resistance to hydrocarbon fluids
US9630151B2 (en) 2015-03-31 2017-04-25 Pall Corporation Hydrophilically modified fluorinated membrane (V)
US9724650B2 (en) 2015-03-31 2017-08-08 Pall Corporation Hydrophilically modified fluorinated membrane (II)
US9636641B2 (en) 2015-03-31 2017-05-02 Pall Corporation Hydrophilically modified fluorinated membrane (I)
US9643130B2 (en) 2015-03-31 2017-05-09 Pall Corporation Hydrophilically modified fluorinated membrane (IV)
US9649603B2 (en) 2015-03-31 2017-05-16 Pall Corporation Hydrophilically modified fluorinated membrane (III)
US9849428B2 (en) 2015-04-30 2017-12-26 Pall Corporation Hydrophilically modified fluorinated membrane (VI)
US9643131B2 (en) 2015-07-31 2017-05-09 Pall Corporation Hydrophilic porous polytetrafluoroethylene membrane (I)
US10315168B2 (en) 2015-07-31 2019-06-11 Pall Corporation Hydrophilic porous polytetrafluoroethylene membrane (II)
MX2018003639A (es) 2015-09-24 2019-04-25 Umicore Ag & Co Kg Catalizadores metálicos de metátesis olefínica de carbeno.
HUE053613T2 (hu) 2015-11-18 2021-07-28 Provivi Inc Mikroorganizmusok rovarferomonok és kapcsolódó vegyületek elõállítására
AU2016357756B2 (en) 2015-11-18 2021-09-30 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
JP2019517797A (ja) 2016-06-06 2019-06-27 プロヴィヴィ インコーポレイテッド 脂肪アルコールおよび脂肪アルデヒドの半生合成的生産
US10792651B2 (en) 2016-10-19 2020-10-06 Umicore Ag & Co. Kg Synthesis and characterization of Ru alkylidene complexes
JP7153937B2 (ja) 2017-02-17 2022-10-17 プロビビ インコーポレイテッド オレフィンメタセシスによるフェロモンおよび関連材料の合成方法
WO2018191373A1 (en) * 2017-04-12 2018-10-18 Materia, Inc. Synthesis and characterization of metathesis catalysts
US11104921B2 (en) 2017-05-17 2021-08-31 Provivi, Inc. Microorganisms for the production of insect pheromones and related compounds
WO2020061277A1 (en) * 2018-09-20 2020-03-26 Exxonmobil Chemical Patents Inc. Metathesis catalyst system for polymerizing cycloolefins
WO2020072776A1 (en) * 2018-10-03 2020-04-09 Materia, Inc. Polymers for specialty applications
CN109799528B (zh) * 2019-01-17 2022-08-19 中国辐射防护研究院 用于放射性污染金属浅层取样的氧化凝胶及其制备方法
CN111393554B (zh) * 2019-05-06 2022-05-20 派迈新材料(成都)有限责任公司 一种聚双环戊二烯坯料及其制备方法
CN112724298A (zh) * 2020-02-20 2021-04-30 派迈新材料(成都)有限责任公司 一种制备高透波天线罩的热固性材料及天线罩制备方法
WO2021202485A1 (en) * 2020-04-01 2021-10-07 3M Innovative Properties Company Compositions comprising romp catalyst and dispersant, cartridges, and methods
CN111662435A (zh) * 2020-06-16 2020-09-15 派迈新材料(成都)有限责任公司 一种绝缘基板及其制备方法和用途
CN111777701B (zh) * 2020-06-16 2022-07-22 派迈新材料(成都)有限责任公司 一种树脂组合物在制备绝缘基板或覆铜箔层压板中的用途
BR112023002624A2 (pt) * 2020-08-13 2023-04-04 Materia Inc Composições olefínicas compreendendo resinas de hidrocarboneto
CN112592635A (zh) * 2020-11-27 2021-04-02 济南大学 一种烯烃共聚物的制备及应用
CN112403525B (zh) * 2020-12-03 2021-12-31 大连理工大学 一种具有配体分子內异面结构的金属有机框架催化剂的制备方法及其应用
CN113004516B (zh) * 2021-03-09 2023-01-13 贵州大学 α,ω-多烯单体易位聚合制备聚氨酯的方法及聚氨酯
US20250026871A1 (en) * 2021-04-06 2025-01-23 University Of Washington Cyclic ruthenium benzylidene initiators for enhanced ring expansion metathesis polymerization
CN114907522B (zh) * 2021-07-16 2024-11-22 派迈新材料(成都)有限责任公司 一种防止地下动物破坏的树脂组合物及其在制备燃气管道中的用途
CN115160719B (zh) * 2021-08-06 2024-11-22 派迈新材料(成都)有限责任公司 一种保温油气管道
CN113941361B (zh) * 2021-10-27 2023-11-28 山东新和成维生素有限公司 一种芳构化催化剂及其制备方法和应用
CN114146729B (zh) * 2021-11-16 2023-01-17 大赛璐（中国）投资有限公司 一种双齿卡宾催化剂载体及非均相催化剂
CN115947761A (zh) * 2022-12-27 2023-04-11 上海中化科技有限公司 一种钌卡宾催化剂、含其的组合物、其制备方法及应用
CN115819724A (zh) * 2022-12-27 2023-03-21 上海中化科技有限公司 环氧-环烯烃树脂组合物、热固性树脂材料及其制备方法
WO2024197120A2 (en) * 2023-03-21 2024-09-26 Materia, Inc. Romp and thermal insulation compositions and materials and use thereof
CN116284735B (zh) * 2023-05-04 2023-12-29 辽宁奥克药业股份有限公司 一种制备嵌段聚醚的催化剂、嵌段聚醚的制备方法

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4899005A (en) 1987-11-19 1990-02-06 The B. F. Goodrich Company Method for preparing cycloolefin copolymers with improved heat stability
US5268232A (en) * 1991-10-15 1993-12-07 Hercules Incorporated Dicyclopentadiene polymers with heat-resistant dimensional integrity and high Tg
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US5831108A (en) 1995-08-03 1998-11-03 California Institute Of Technology High metathesis activity ruthenium and osmium metal carbene complexes
US5939504A (en) * 1995-12-07 1999-08-17 Advanced Polymer Technologies Method for extending the pot life of an olefin metathesis polymerization reaction
US6162883A (en) 1996-04-04 2000-12-19 Ciba Specialty Chemcials Corporation Catalyst mixture and polymerizable composition
US6310121B1 (en) 1996-12-02 2001-10-30 Cymetech, Llc Polymeric composites including dicyclopentadiene and related monomers
US5998326A (en) * 1997-05-23 1999-12-07 Ciba Specialty Chemicals Corp. Two-component catalyst for ROMP
US6284852B1 (en) * 1997-10-30 2001-09-04 California Institute Of Technology Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
US5977393A (en) 1997-11-21 1999-11-02 California Institute Of Technology Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts
DE19815275B4 (de) 1998-04-06 2009-06-25 Evonik Degussa Gmbh Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese
US6107420A (en) 1998-07-31 2000-08-22 California Institute Of Technology Thermally initiated polymerization of olefins using Ruthenium or osmium vinylidene complexes
DE19902439A1 (de) 1999-01-22 2000-08-03 Aventis Res & Tech Gmbh & Co Homo- und heterobimetallische Alkylidenkomplexe des Rutheniums mit N-heterocyclischen Carbenliganden und deren Anwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese
BR0008022A (pt) 1999-02-05 2001-11-06 Materia Inc Composições de poliolefina com densidade variável e processos para sua produção e uso
US6225488B1 (en) * 1999-04-02 2001-05-01 Nippon Zeon Co., Ltd. Ruthenium or osmium catalysts for olefin metathesis reactions
US7329758B1 (en) 1999-05-24 2008-02-12 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
JP2001131264A (ja) * 1999-11-01 2001-05-15 Nippon Zeon Co Ltd シクロオレフィンポリマーの製造方法
US6436476B1 (en) 2000-02-14 2002-08-20 Owens Corning Fiberglas Technology, Inc. Polyolefin fiber-reinforced composites using a fiber coating composition compatible with romp catalysts
CA2419485C (en) 2000-08-10 2007-10-30 The Trustees Of Boston College Recyclable metathesis catalysts
US6838489B2 (en) 2001-03-23 2005-01-04 Cymetech, Llc High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor
DE60238829D1 (de) * 2001-03-23 2011-02-17 California Inst Of Techn Unter verwendung eines thermisch aktivierten n-heterocyclischen carbenvorläufers gebildete hochaktive metallcarbenmetathesekatalysatoren
US6759537B2 (en) 2001-03-23 2004-07-06 California Institute Of Technology Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
WO2002079208A2 (en) 2001-04-02 2002-10-10 California Institute Of Technology One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts
US7683180B2 (en) 2001-04-16 2010-03-23 California Institute Of Technology Group 8 transition metal carbene complexes as enantionselective olefin metathesis catalysts
JP2002363264A (ja) * 2001-06-11 2002-12-18 Nippon Zeon Co Ltd ノルボルネン系樹脂の製造方法
CN1265882C (zh) 2001-08-01 2006-07-26 加州理工学院 六配位钌或锇金属卡宾易位催化剂
EP1421121A4 (en) * 2001-08-29 2007-05-23 California Inst Of Techn RING-OPENING METETHESEPOLYMERIZATION OF BROKEN BICYCLIC AND POLYCLYCLINIC OLEFINS WITH TWO OR MORE HETEROATOMES
WO2003044060A2 (en) 2001-11-15 2003-05-30 Materia, Inc. Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
ES2279117T3 (es) 2002-01-22 2007-08-16 Universiteit Gent Complejos metalicos para utilizar en una metatesis.
KR20050030634A (ko) 2002-07-23 2005-03-30 피피지 인더스트리즈 오하이오 인코포레이티드 유리 섬유 사이징 조성물, 사이징된 유리 섬유, 및폴리올레핀 복합체
PL1577282T3 (pl) 2004-02-26 2011-11-30 Rimtec Corp Kompleksy metali do stosowania w metatezie olefin i reakcjach przeniesienia atomu lub grupy
CN101090915A (zh) * 2004-03-29 2007-12-19 加州理工学院 含有n－杂环卡宾配体的潜伏的高活性烯烃置换催化剂
WO2005094345A2 (en) 2004-03-29 2005-10-13 California Institute Of Technology Latent, high-activity olefin metathesis catalysts containing an n-heterocyclic carbene ligand
GB0514612D0 (en) 2005-07-15 2005-08-24 Sasol Technology Uk Ltd The use of a phosphorus containing ligand and a cyclic organic ligand in a metathesis catalyst
JP5032479B2 (ja) 2005-08-22 2012-09-26 テレーヌ ソシエテ パル アクシオン サンプリフィエー 転換反応に使用する多座配位金属錯体
GB0517137D0 (en) 2005-08-22 2005-09-28 Viacatt N V Multicoordinated metal complexes for use in metalthesis reactions
WO2008027283A2 (en) * 2006-08-25 2008-03-06 Dow Global Technologies Inc. Production of meta-block copolymers by polymer segment interchange
EP2183205A4 (en) * 2007-08-09 2013-10-02 Elevance Renewable Sciences CHEMICAL PROCESSES FOR TREATING METATHESIS RAW MATERIAL
WO2009107844A1 (ja) * 2008-02-29 2009-09-03 日本ゼオン株式会社 硬化性樹脂組成物、それを用いた成形体、プリプレグ及び積層体
CA2718147A1 (en) * 2008-03-28 2009-10-01 Isp Investments Inc. Process of making a stable aqueous dispersion of concentrated, finely divided particles of a biocide
CN102083798B (zh) * 2008-04-09 2016-10-26 马特里亚公司 带有具有取代骨架的n-杂环卡宾配体的钌烯烃易位催化剂
EP2143489A1 (de) * 2008-07-08 2010-01-13 Lanxess Deutschland GmbH Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen
WO2010037550A1 (en) 2008-10-04 2010-04-08 Umicore Ag & Co. Kg Method for preparation of ruthenium-indenylidene carbene catalysts
US8283410B2 (en) * 2009-03-30 2012-10-09 Isp Investments Inc. Ring-opening metathesis polymerization of norbornene and oxanorbornene moieties and uses thereof
EP2280017B1 (en) 2009-07-21 2013-01-02 Rimtec Corporation Catalytic complex for olefin metathesis reactions, process for the preparation thereof and use thereof
WO2011079439A1 (en) 2009-12-30 2011-07-07 Zannan Scitech Co., Ltd. Highly active metathesis catalysts selective for romp and rcm reactions
US10457597B2 (en) * 2011-06-17 2019-10-29 Materia, Inc. Adhesion promoters and gel-modifiers for olefin metathesis compositions
WO2013025284A1 (en) * 2011-08-12 2013-02-21 Exxonmobil Chemical Patents Inc. Polymers prepared by ring opening/cross metathesis

Also Published As

Publication number Publication date
SG11201506724VA (en) 2015-09-29
US20160185885A1 (en) 2016-06-30
EP2961778A4 (en) 2016-10-05
WO2014134333A1 (en) 2014-09-04
BR112015019868A2 (pt) 2017-07-18
JP2018087338A (ja) 2018-06-07
MX2015010583A (es) 2016-04-07
KR102211385B1 (ko) 2021-02-03
CN105229040A (zh) 2016-01-06
EP2961778A1 (en) 2016-01-06
US20140357820A1 (en) 2014-12-04
JP6840191B2 (ja) 2021-03-10
MY191997A (en) 2022-07-22
CA2902451A1 (en) 2014-09-04
JP6607913B2 (ja) 2019-11-20
JP6271595B2 (ja) 2018-01-31
KR20150122208A (ko) 2015-10-30
JP2016511789A (ja) 2016-04-21
BR112015019868B1 (pt) 2020-06-09
EP2961778B1 (en) 2025-02-26
CN105229040B (zh) 2017-05-31
JP2019203130A (ja) 2019-11-28
MY188144A (en) 2021-11-23

Similar Documents

Publication Publication Date Title
CA2902451C (en) Metal carbene olefin metathesis two catalyst composition
CA2903574C (en) In-mold coating of romp polymers
CA2915871C (en) Liquid molding compositions
US10239965B2 (en) Cyclic olefin resin compositions comprising functional elastomers
US20210403654A1 (en) Adhesion promoter compositions for cyclic olefin resin compositions
US9527982B2 (en) Storage stable adhesion promoter compositions for cyclic olefin resin compositions
US9598531B2 (en) Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190115