TW200535158A - Single component cationic palladium proinitiators for the latent polymerization of cycloolefins - Google Patents

Single component cationic palladium proinitiators for the latent polymerization of cycloolefins Download PDF

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Publication number
TW200535158A
TW200535158A TW093133204A TW93133204A TW200535158A TW 200535158 A TW200535158 A TW 200535158A TW 093133204 A TW093133204 A TW 093133204A TW 93133204 A TW93133204 A TW 93133204A TW 200535158 A TW200535158 A TW 200535158A
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Taiwan
Prior art keywords
bismuth
patent application
item
group
hydrazone
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TW093133204A
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English (en)
Chinese (zh)
Inventor
Andrew Bell
Dino Amoroso
John D Protasiewicz
Natesan Thirupathi
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Promerus Llc
Univ Case Western Reserve
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Publication of TW200535158A publication Critical patent/TW200535158A/zh

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006Palladium compounds
    • C07F15/0066Palladium compounds without a metal-carbon linkage
    • 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
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
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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
    • C08F10/00Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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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
    • C08F32/00Homopolymers 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
    • 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
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/607Catalysts containing a specific non-metal or metal-free compound
    • C08F4/608Catalysts containing a specific non-metal or metal-free compound inorganic
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213Complexes without C-metal linkages
    • B01J2531/0216Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/824Palladium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/143Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • BPERFORMING OPERATIONS; TRANSPORTING
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1895Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • BPERFORMING OPERATIONS; TRANSPORTING
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    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
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    • B01J31/22Organic complexes
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    • B01J31/226Sulfur, e.g. thiocarbamates
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    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • BPERFORMING OPERATIONS; TRANSPORTING
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    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2438Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member and further hetero atoms as ring members, excluding the positions adjacent to P
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • B01J31/248Bridged ring systems, e.g. 9-phosphabicyclononane

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  • Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerization Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
TW093133204A 2003-10-31 2004-10-29 Single component cationic palladium proinitiators for the latent polymerization of cycloolefins TW200535158A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51605403P 2003-10-31 2003-10-31
US10/976,350 US20050187398A1 (en) 2003-10-31 2004-10-28 Single component cationic palladium proinitiators for the latent polymerization of cycloolefins

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TW200535158A true TW200535158A (en) 2005-11-01

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TW093133204A TW200535158A (en) 2003-10-31 2004-10-29 Single component cationic palladium proinitiators for the latent polymerization of cycloolefins

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US (1) US20050187398A1 (enExample)
EP (1) EP1680218A2 (enExample)
JP (1) JP2007521326A (enExample)
KR (1) KR20060127396A (enExample)
TW (1) TW200535158A (enExample)
WO (1) WO2005042147A2 (enExample)

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JP2008536956A (ja) 2005-02-22 2008-09-11 プロメラス, エルエルシー ノルボルネン系ポリマー、その組成物、及び該組成物を使用するリソグラフィ法
JP5017793B2 (ja) * 2005-04-06 2012-09-05 Jsr株式会社 環状オレフィン系付加重合体の製造方法
JP4826242B2 (ja) * 2005-12-12 2011-11-30 Jsr株式会社 環状オレフィン系付加重合体の製造方法
AU2007254464B2 (en) * 2006-02-21 2013-02-21 Avrum Belzer Hyperpolarization methods, systems and compositions
US8120168B2 (en) 2006-03-21 2012-02-21 Promerus Llc Methods and materials useful for chip stacking, chip and wafer bonding
EP2083293A4 (en) 2006-11-16 2010-09-01 Sumitomo Bakelite Co GUIDE OF LIGHT AND STRUCTURE OF GUIDE OF LIGHT
JP2009102654A (ja) * 2009-02-05 2009-05-14 Sumitomo Bakelite Co Ltd 光導波路構造体
US8541523B2 (en) 2010-04-05 2013-09-24 Promerus, Llc Norbornene-type polymers, compositions thereof and lithographic process using such compositions
JP2012121956A (ja) * 2010-12-07 2012-06-28 Sumitomo Bakelite Co Ltd 付加型ノルボルネン系樹脂、その製造方法、該樹脂を含む樹脂組成物、ならびに該樹脂を含む成形体および該成形体を含む複合部材
US8716421B2 (en) 2012-06-25 2014-05-06 Promerus, Llc Norbornene-type formate monomers and polymers and optical waveguides formed therefrom
US9468890B2 (en) 2012-08-07 2016-10-18 Promerus, Llc Cycloalkylnorbornene monomers, polymers derived therefrom and their use in pervaporation
CN105283459B (zh) * 2013-05-15 2018-01-02 广荣化学工业株式会社 新型四芳基硼酸盐化合物及其制备方法
RU2626745C2 (ru) * 2015-07-20 2017-07-31 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный университет" Способ аддитивной полимеризации норборнена и его производных
TWI867226B (zh) * 2020-06-24 2024-12-21 日商住友電木股份有限公司 作為光學材料之受阻胺穩定型uv活性有機鈀催化聚環烯烴組成物
WO2022118175A1 (en) 2020-12-02 2022-06-09 3M Innovative Properties Company Curable compositions, composite foam, method of making the same, and article including the same
US20240279251A1 (en) 2021-05-14 2024-08-22 3M Innovative Properties Company Monomer, Polymerizable Composition, and Polymers Derived Therefrom
TW202348614A (zh) * 2022-04-05 2023-12-16 美商普羅梅勒斯有限公司 具有改進的成膜特性之乙烯基加成聚合物形成用鈀觸媒
EP4612126A1 (en) 2022-10-31 2025-09-10 3M Innovative Properties Company Compositions including a mixture of isomers of itaconimide norbornene and citraconimide norbornene
CN120152999A (zh) 2022-11-07 2025-06-13 3M创新有限公司 可固化和固化的热固性组合物

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US6262200B1 (en) * 1996-08-19 2001-07-17 Northwestern University (Polyfluoroaryl)fluoroanions of aluminum, gallium, and indium of enhanced utility, uses thereof, and products based thereon
AU6291999A (en) * 1998-10-05 2000-04-26 B.F. Goodrich Company, The Catalyst and methods for polymerizing cycloolefins
KR100739482B1 (ko) * 1998-12-09 2007-07-13 스미토모 베이클라이트 가부시키가이샤 제 10족 금속 착물을 사용하는 노르보르넨형 단량체의 몰드내 첨가 중합반응
GB2378182A (en) * 2001-07-31 2003-02-05 Johnson Matthey Plc Heterocycle-containing phosphines & their use as ligands in palladium catalysed coupling reactions
US7674847B2 (en) * 2003-02-21 2010-03-09 Promerus Llc Vinyl addition polycyclic olefin polymers prepared with non-olefinic chain transfer agents and uses thereof

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WO2005042147A3 (en) 2005-08-04
KR20060127396A (ko) 2006-12-12
EP1680218A2 (en) 2006-07-19
WO2005042147A2 (en) 2005-05-12
JP2007521326A (ja) 2007-08-02
US20050187398A1 (en) 2005-08-25

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