JP5916724B2 - 高分子量ポリエチレンの製造方法 - Google Patents
高分子量ポリエチレンの製造方法 Download PDFInfo
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- JP5916724B2 JP5916724B2 JP2013517592A JP2013517592A JP5916724B2 JP 5916724 B2 JP5916724 B2 JP 5916724B2 JP 2013517592 A JP2013517592 A JP 2013517592A JP 2013517592 A JP2013517592 A JP 2013517592A JP 5916724 B2 JP5916724 B2 JP 5916724B2
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Classifications
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- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- 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
- C08F4/74—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from refractory metals
- C08F4/76—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from refractory metals selected from titanium, zirconium, hafnium, vanadium, niobium or tantalum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
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- 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
- C08F4/44—Metals; 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
- C08F4/60—Metals; 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
-
- 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
- C08F4/44—Metals; 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
- C08F4/60—Metals; 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
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- 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
- C08F4/44—Metals; 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
- C08F4/60—Metals; 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
- C08F4/60003—Metals; 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 the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
- C08F4/60168—Tetra- or multi-dentate ligand
- C08F4/60186—Dianionic ligand
- C08F4/60193—OOOO
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| PCT/IB2011/002283 WO2012004680A2 (en) | 2010-07-06 | 2011-07-01 | Process for producing high molecular weight polyethylene |
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| JP2013533349A JP2013533349A (ja) | 2013-08-22 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102959144A (zh) | 2010-07-06 | 2013-03-06 | 提克纳有限公司 | 高分子量聚乙烯纤维和膜、它们的生产和用途 |
| EP2591017B1 (en) | 2010-07-06 | 2015-09-09 | Ticona GmbH | Process for producing high molecular weight polyethylene |
| WO2012004680A2 (en) | 2010-07-06 | 2012-01-12 | Ticona Gmbh | Process for producing high molecular weight polyethylene |
| BR112012032745A2 (pt) | 2010-07-06 | 2016-11-08 | Ticona Gmbh | processo para produção de polietileno de alto peso molecular |
| WO2013093540A1 (en) * | 2011-12-19 | 2013-06-27 | Ticona Gmbh | Process for producing high molecular weight polyethylene |
| EP2880006B1 (en) * | 2012-08-03 | 2017-12-20 | ExxonMobil Chemical Patents Inc. | Non-symmetric catalysts comprising salan ligands |
| EP2880098B1 (en) * | 2012-08-03 | 2018-01-10 | ExxonMobil Chemical Patents Inc. | Halogenated catalysts comprising salan ligands |
| BR112014031937A8 (pt) | 2012-08-03 | 2021-04-06 | Exxonmobil Chemical Patents Inc | catalisadores compreendendo ligantes salen, sistema de catalisador, poliolefina e processo para polimerizar olefinas |
| US9382349B2 (en) | 2012-08-03 | 2016-07-05 | Exxonmobil Chemical Patents Inc. | Polyalphaolefins prepared using modified Salan catalyst compounds |
| WO2014022013A1 (en) | 2012-08-03 | 2014-02-06 | Exxonmobil Chemical Patents Inc. | Polyalphaolefins prepared using modified salan catalyst compounds |
| CN104379680B (zh) | 2012-08-03 | 2017-11-28 | 埃克森美孚化学专利公司 | 具有长链支化的乙烯基封端的聚烯烃 |
| US9120879B2 (en) | 2012-11-02 | 2015-09-01 | Exxonmobil Chemical Patents Inc. | Supported Salan catalysts |
| CN105121558B (zh) | 2013-03-13 | 2017-09-26 | 埃克森美孚化学专利公司 | 二苯基胺salan催化剂 |
| US9150676B2 (en) | 2013-06-20 | 2015-10-06 | Exxonmobil Chemical Patents Inc. | Thio-salalen catalyst |
| CN105142777B (zh) | 2013-06-20 | 2017-12-26 | 埃克森美孚化学专利公司 | 长桥Salen催化剂 |
| WO2014204625A1 (en) | 2013-06-20 | 2014-12-24 | Exxonmobil Chemical Patents Inc. | Salenol catalyst |
| US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
| US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
| US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
| US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
| CN105814015B (zh) | 2013-12-13 | 2019-04-02 | 埃克森美孚化学专利公司 | 环戊二烯基取代的Salan催化剂 |
| CN106132924B (zh) | 2014-03-31 | 2019-03-19 | 埃克森美孚化学专利公司 | 亚苯基桥连的salalen催化剂 |
| JP6797694B6 (ja) | 2014-06-30 | 2021-01-20 | ダウ グローバル テクノロジーズ エルエルシー | オレフィン重合のためのプロセス |
| ES2796870T3 (es) * | 2014-06-30 | 2020-11-30 | Dow Global Technologies Llc | Sistemas catalíticos para la polimerización de olefina |
| BR112017000855B1 (pt) * | 2014-07-24 | 2022-02-08 | Dow Global Technologies Llc | Processo para formar um polímero à base de etileno |
| CN114616255B (zh) * | 2019-11-04 | 2024-09-13 | 陶氏环球技术有限责任公司 | 联苯酚聚合催化剂 |
| CN116724062B (zh) * | 2021-02-15 | 2026-07-31 | 陶氏环球技术有限责任公司 | 联苯酚聚合催化剂 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH062776B2 (ja) | 1984-12-21 | 1994-01-12 | 日本石油株式会社 | 超高分子量ポリエチレンの製造方法 |
| EP0205960B1 (en) | 1985-06-17 | 1990-10-24 | AlliedSignal Inc. | Very low creep, ultra high moduls, low shrink, high tenacity polyolefin fiber having good strength retention at high temperatures and method to produce such fiber |
| JPH0692509B2 (ja) | 1985-12-17 | 1994-11-16 | 日本石油株式会社 | 高強度・高弾性率繊維又はフイルム製造用ポリエチレン溶液の製造法 |
| US5153157A (en) | 1987-01-30 | 1992-10-06 | Exxon Chemical Patents Inc. | Catalyst system of enhanced productivity |
| IL85097A (en) | 1987-01-30 | 1992-02-16 | Exxon Chemical Patents Inc | Catalysts based on derivatives of a bis(cyclopentadienyl)group ivb metal compound,their preparation and their use in polymerization processes |
| US5384299A (en) | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| DE3833445A1 (de) | 1988-10-01 | 1990-04-05 | Basf Ag | Vermeidung von farbigen verunreinigungen bei der herstellung von ultrahochmolekularen ethylenpolymerisaten mittels eines titan enthaltenden katalysatorsystems |
| PL286365A1 (en) | 1989-08-03 | 1991-04-22 | Exxon Chemical Patents Inc | Method of polymerizing especially ethylene any polymerization catalyst and method of obtaining same |
| US5064802A (en) | 1989-09-14 | 1991-11-12 | The Dow Chemical Company | Metal complex compounds |
| US5453410A (en) | 1992-01-06 | 1995-09-26 | The Dow Chemical Company | Catalyst composition |
| JP2888639B2 (ja) | 1992-04-20 | 1999-05-10 | エクソン・ケミカル・パテンツ・インク | エチレン／分枝鎖オレフィンのコポリマー |
| DE59304393D1 (de) | 1992-06-24 | 1996-12-12 | Hoechst Ag | Verfahren zur Herstellung eines Katalysatorsystems für die Polymerisation und Copolymerisation von Ethylen zu ultrahochmolekularen Ethylpolymeren |
| ES2120534T3 (es) | 1993-04-29 | 1998-11-01 | Ticona Gmbh | Procedimiento para la fabricacion de un sistema de catalizador para la polimerizacion y copolimerizacion de etileno en homopolimeros y copolimeros de etileno de molecula ultraelevada. |
| IT1271406B (it) | 1993-09-13 | 1997-05-28 | Spherilene Srl | Procedimento per la preparazione di polimeri dell'etilene e prodotti ottenuti |
| ES2150529T3 (es) | 1994-04-07 | 2000-12-01 | Bp Chem Int Ltd | Procedimiento de polimerizacion. |
| US5616664A (en) | 1994-08-02 | 1997-04-01 | The Dow Chemical Company | Polymerization process with biscyclopentadienyl diene complex containing catalysts |
| JP3355572B2 (ja) | 1994-08-23 | 2002-12-09 | 新日本石油株式会社 | オレフィン類重合触媒およびそれを用いたポリオレフィンの製造方法 |
| FI101716B1 (fi) | 1995-09-19 | 1998-08-14 | Valtion Teknillinen | Sopeutettu UHMWPE-PA-seos |
| US6486089B1 (en) | 1995-11-09 | 2002-11-26 | Exxonmobil Oil Corporation | Bimetallic catalyst for ethylene polymerization reactions with uniform component distribution |
| EP0863919B1 (en) | 1995-11-27 | 2000-11-15 | The Dow Chemical Company | Supported catalyst containing tethered cation forming activator |
| US5780659A (en) | 1996-03-29 | 1998-07-14 | Phillips Petroleum Company | Substituted indenyl unbridged metallocenes |
| US6017975A (en) | 1996-10-02 | 2000-01-25 | Saum; Kenneth Ashley | Process for medical implant of cross-linked ultrahigh molecular weight polyethylene having improved balance of wear properties and oxidation resistance |
| US6051525A (en) | 1997-07-14 | 2000-04-18 | Mobil Corporation | Catalyst for the manufacture of polyethylene with a broad or bimodal molecular weight distribution |
| WO1999006413A1 (en) | 1997-08-01 | 1999-02-11 | The Dow Chemical Company | Catalyst activator |
| WO1999042467A1 (en) | 1998-02-20 | 1999-08-26 | The Dow Chemical Company | Catalyst activators comprising expanded anions |
| US6723267B2 (en) | 1998-10-28 | 2004-04-20 | Dsm N.V. | Process of making highly oriented polyolefin fiber |
| US6852811B1 (en) | 1998-12-30 | 2005-02-08 | The Dow Chemical Company | Process for preparing a supported polymerization catalyst using reduced amounts of solvent and polymerization process |
| US6211311B1 (en) | 1999-05-25 | 2001-04-03 | Equistar Chemicals, L.P. | Supported olefin polymerization catalysts |
| US6265504B1 (en) | 1999-09-22 | 2001-07-24 | Equistar Chemicals, Lp | Preparation of ultra-high-molecular-weight polyethylene |
| CN100436492C (zh) | 2000-01-26 | 2008-11-26 | 三井化学株式会社 | 烯烃聚合物 |
| KR100351386B1 (ko) | 2000-04-24 | 2002-09-05 | 삼성종합화학주식회사 | 초고분자량 폴리에틸렌 제조용 촉매 및 이를 이용한초고분자량 폴리에틸렌 제조방법 |
| US6503439B1 (en) | 2000-06-15 | 2003-01-07 | Albert H. Burstein | Process for forming shaped articles of ultra high molecular weight polyethylene suitable for use as a prosthetic device or a component thereof |
| DE10122111B4 (de) | 2001-05-08 | 2007-03-01 | Ticona Gmbh | Verfahren zur Herstellung von Olefinpolymeren, sowie ausgewählte Katalysatoren |
| US6841502B2 (en) | 2002-04-24 | 2005-01-11 | Symyx Technologies, Inc. | Bridged bi-aromatic ligands, catalysts, processes for polymerizing and polymers therefrom |
| US7060848B2 (en) | 2002-04-24 | 2006-06-13 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
| US7091292B2 (en) * | 2002-04-24 | 2006-08-15 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
| US20040110853A1 (en) | 2002-08-20 | 2004-06-10 | Wang Louis Chun | Process for preparing molded porous articles and the porous articles prepared therefrom |
| WO2005003184A1 (en) | 2003-06-11 | 2005-01-13 | Exxonmobil Chemical Patents Inc. | Polymerization processes using antistatic agents |
| US6767975B1 (en) | 2003-07-14 | 2004-07-27 | Equistar Chemicals, Lp | Olefin polymerization with pyridine moiety-containing singe-site catalysts |
| EP1722154A2 (en) | 2004-03-05 | 2006-11-15 | Salvador Plaxats Oller | Plug valve for liquefied gas containers |
| WO2005108406A1 (en) * | 2004-04-29 | 2005-11-17 | Symyx Tecnologies, Inc | Bridged bi-aromatic catalysts, complexes, and method of using the same |
| RU2379317C2 (ru) | 2004-06-07 | 2010-01-20 | ТИКОНА ЭлЭлСи | Полиэтиленовый формовочный порошок и изготовленные из него пористые изделия |
| US20080051537A1 (en) | 2004-08-09 | 2008-02-28 | Carnahan Edmund M | Supported Bis(Hydroxylarylaryloxy) Catalysts For Manufacture Of Polymers |
| US20060281879A1 (en) * | 2005-06-13 | 2006-12-14 | Univation Technologies, Llc | Catalyst compositions comprising small silica support materials and methods of use in polymerization reactions |
| DE102005052654A1 (de) | 2005-11-04 | 2007-05-16 | Ticona Gmbh | Verfahren zur Herstellung von ultrahochmolekularen Polymeren unter Verwendung von speziellen verbrückten Metallocen-Katalysatoren |
| US7598329B2 (en) | 2005-11-04 | 2009-10-06 | Ticona Gmbh | Process for manufacturing ultra high molecular weight polymers using novel bridged metallocene catalysts |
| BRPI0705994A2 (pt) | 2007-10-19 | 2009-10-06 | Braskem Sa | processo de preparação de suporte catalìtico e catalisadores bimetálicos suportados para a produção de homopolìmeros e copolìmeros de etileno com alfa-olefinas de alto e ultra alto peso molecular e com ampla distribuição de peso molecular em processos em lama, massa e fase gás e os produtos assim obtidos |
| BRPI0703586B1 (pt) | 2007-10-19 | 2018-02-06 | Braskem S.A | Catalisador metaloceno suportado, e, copolímeros de etileno com alfa-olefinas de alto e ultra alto peso molecular |
| WO2011087520A1 (en) | 2009-12-22 | 2011-07-21 | Univation Technologies, Llc | Catalyst systems having a tailored hydrogen response |
| US20090163679A1 (en) | 2007-12-19 | 2009-06-25 | Braskem S.A. | Suspension polymerization process for manufacturing ultra high molecular weight polyethylene, a multimodal ultra high molecular weight polyethylene homopolymeric or copolymeric composition, a ultra high molecular weight polyethylene, and their uses |
| CN101654492B (zh) | 2008-08-21 | 2012-06-20 | 中国石化扬子石油化工有限公司 | 超高分子量聚乙烯、其制备方法及其应用 |
| CA2786286C (en) * | 2008-12-31 | 2017-03-14 | Dassault Systemes Americas Corp. | Method for producing very-high or ultra-high molecular weight polyethylene |
| KR20130059355A (ko) | 2010-05-03 | 2013-06-05 | 티코나 엘엘씨 | 폴리에틸렌 분말 및 그로부터 제조된 다공성 제품 |
| BR112012032745A2 (pt) | 2010-07-06 | 2016-11-08 | Ticona Gmbh | processo para produção de polietileno de alto peso molecular |
| CN102959144A (zh) | 2010-07-06 | 2013-03-06 | 提克纳有限公司 | 高分子量聚乙烯纤维和膜、它们的生产和用途 |
| WO2012004680A2 (en) | 2010-07-06 | 2012-01-12 | Ticona Gmbh | Process for producing high molecular weight polyethylene |
| EP2591017B1 (en) | 2010-07-06 | 2015-09-09 | Ticona GmbH | Process for producing high molecular weight polyethylene |
| JP2013529718A (ja) | 2010-07-06 | 2013-07-22 | ティコナ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 高分子量ポリエチレンの製造方法 |
| BR112012032879A2 (pt) | 2010-07-06 | 2016-11-08 | Ticona Gmbh | artigos moldados de polietileno de alto peso molecular, sua produção e uso |
| EP2591021A2 (en) | 2010-07-06 | 2013-05-15 | Ticona GmbH | Ultra-high molecular weight polyethylene, its production and use |
-
2011
- 2011-07-01 WO PCT/IB2011/002283 patent/WO2012004680A2/en not_active Ceased
- 2011-07-01 US US13/700,879 patent/US9212234B2/en not_active Expired - Fee Related
- 2011-07-01 BR BR112012032539A patent/BR112012032539A2/pt not_active IP Right Cessation
- 2011-07-01 CN CN201180031659.8A patent/CN102958959B/zh not_active Expired - Fee Related
- 2011-07-01 KR KR1020127033704A patent/KR20130124171A/ko not_active Withdrawn
- 2011-07-01 EP EP11778675.6A patent/EP2591020B1/en not_active Not-in-force
- 2011-07-01 JP JP2013517592A patent/JP5916724B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9212234B2 (en) | 2015-12-15 |
| WO2012004680A2 (en) | 2012-01-12 |
| US20130072649A1 (en) | 2013-03-21 |
| JP2013533349A (ja) | 2013-08-22 |
| BR112012032539A2 (pt) | 2016-11-22 |
| CN102958959B (zh) | 2015-11-25 |
| CN102958959A (zh) | 2013-03-06 |
| EP2591020A2 (en) | 2013-05-15 |
| WO2012004680A3 (en) | 2012-03-29 |
| EP2591020B1 (en) | 2015-09-09 |
| KR20130124171A (ko) | 2013-11-13 |
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