RU2232766C2 - Связанные мостиками металлоцены, способ полимеризации - Google Patents
Связанные мостиками металлоцены, способ полимеризации Download PDFInfo
- Publication number
- RU2232766C2 RU2232766C2 RU2001113445/04A RU2001113445A RU2232766C2 RU 2232766 C2 RU2232766 C2 RU 2232766C2 RU 2001113445/04 A RU2001113445/04 A RU 2001113445/04A RU 2001113445 A RU2001113445 A RU 2001113445A RU 2232766 C2 RU2232766 C2 RU 2232766C2
- Authority
- RU
- Russia
- Prior art keywords
- cyclopentadienyl
- polymerization
- methylene
- substituted
- fluorenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 55
- 239000003446 ligand Substances 0.000 claims abstract description 60
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000005977 Ethylene Substances 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 16
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- 229920001038 ethylene copolymer Polymers 0.000 claims abstract description 7
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 4
- -1 di (p-trimethylsilylphenyl) methylene (cyclopentadienyl) Chemical group 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 30
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 26
- 239000012190 activator Substances 0.000 claims description 21
- 150000001450 anions Chemical class 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 14
- 229910052735 hafnium Inorganic materials 0.000 claims description 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004711 α-olefin Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000010348 incorporation Methods 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
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- VCHQGHCBFOFZJK-UHFFFAOYSA-N 1-cyclopenta-1,3-dien-1-ylcyclopenta-1,3-diene Chemical group C1C=CC=C1C1=CC=CC1 VCHQGHCBFOFZJK-UHFFFAOYSA-N 0.000 claims 1
- OJOWICOBYCXEKR-UHFFFAOYSA-N 5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CC)CC1C=C2 OJOWICOBYCXEKR-UHFFFAOYSA-N 0.000 claims 1
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005517 carbenium group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 229910052782 aluminium Inorganic materials 0.000 description 6
- 239000012683 anionic precursor Substances 0.000 description 6
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- 238000007429 general method Methods 0.000 description 6
- 239000012041 precatalyst Substances 0.000 description 6
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- 150000001721 carbon Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000012968 metallocene catalyst Substances 0.000 description 5
- 229910052752 metalloid Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
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- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 3
- 0 C*c1c(C)c(*)c(*C)c(*)c1C Chemical compound C*c1c(C)c(*)c(*C)c(*)c1C 0.000 description 3
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- 150000001342 alkaline earth metals Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
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Images
Classifications
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- C07F17/00—Metallocenes
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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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
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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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
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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
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
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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
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- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
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- 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
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- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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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
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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
- C08F2420/00—Metallocene catalysts
- C08F2420/10—Heteroatom-substituted bridge, i.e. Cp or analog where the bridge linking the two Cps or analogs is substituted by at least one group that contains a heteroatom
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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
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| US60/131,067 | 1999-04-26 |
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Cited By (1)
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| RU2410388C2 (ru) * | 2005-03-18 | 2011-01-27 | Базелль Полиолефине Гмбх | Металлоценовые соединения |
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| US6476164B1 (en) | 1999-10-22 | 2002-11-05 | Exxonmobil Chemical Patents Inc. | Carbenium cationic complexes suitable for polymerization catalysts |
| US6475946B1 (en) | 1999-10-22 | 2002-11-05 | Exxonmobil Chemical Patents Inc. | Olefin polymerization catalysis with aryl substituted carbenium cationic complexes |
| MXPA02004002A (es) * | 1999-10-22 | 2003-03-27 | Exxon Chemical Patents Inc | Complejos cationicos de carbenio adecuados para catalizadores de polimerizacion. |
| EP2465879B1 (en) * | 2002-09-27 | 2019-04-24 | Mitsui Chemicals, Inc. | Bridged metallocene compound for olefin polymerization and method of polymerizing olefin using the same |
| JP4610859B2 (ja) * | 2002-09-27 | 2011-01-12 | 三井化学株式会社 | オレフィン重合用の架橋メタロセン化合物およびそれを用いたオレフィンの重合方法 |
| WO2005108442A1 (en) | 2002-10-15 | 2005-11-17 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| EP1518867B1 (en) | 2003-08-11 | 2007-01-10 | ExxonMobil Chemical Patents Inc. | Polymers of ethylene and optionally, copolymerizable esters, films using such polymers and stretch hood packaging processesusing such films |
| EP1727838B1 (en) * | 2004-03-24 | 2013-04-17 | ExxonMobil Chemical Patents Inc. | Process for making ethylene interpolymers and interpolymers made thereby; compositions and electrical devices containing such interpolymers |
| US7741419B2 (en) * | 2004-03-31 | 2010-06-22 | Mitsui Chemicals, Inc. | Process for producing olefin polymers |
| WO2006044149A1 (en) * | 2004-10-13 | 2006-04-27 | Exxonmobil Chemical Patents Inc. | Elastomeric reactor blend compositions |
| EP1734059A1 (en) * | 2005-06-13 | 2006-12-20 | Total Petrochemicals Research Feluy | Carbon-bridged cyclopentadienyl-fluorenyl ligands |
| US8222358B2 (en) * | 2006-03-02 | 2012-07-17 | Exxonmobil Chemical Patents Inc. | Process for producing propylene copolymers |
| BRPI0711029A2 (pt) * | 2006-05-17 | 2011-05-31 | Dow Global Technologies Inc | processo para polimerização de etileno e uma ou mais a-olefinas ou diolefinas de c3-30 |
| EP1903061A1 (en) * | 2006-09-25 | 2008-03-26 | Total Petrochemicals Research Feluy | Preparation of diphenyl-bridged substituted cyclopentadienyl-fluorenyl ligands |
| EP2083046A1 (en) | 2008-01-25 | 2009-07-29 | ExxonMobil Chemical Patents Inc. | Thermoplastic elastomer compositions |
| US9234093B2 (en) | 2008-03-31 | 2016-01-12 | Exxonmobil Chemical Patents Inc. | Thermoplastic vulcanizates |
| FR2934599B1 (fr) * | 2008-07-29 | 2012-12-21 | Arkema France | Fabrication de polyethylene a partir de matieres renouvelables, polyethylene obtenu et utilisations |
| US8378042B2 (en) * | 2009-04-28 | 2013-02-19 | Exxonmobil Chemical Patents Inc. | Finishing process for amorphous polymers |
| MX2012007401A (es) | 2009-12-23 | 2012-07-17 | Invista Tech Sarl | Articulos elasticos que incluyen fibra elastica de poliolefina. |
| MX2012007399A (es) | 2009-12-23 | 2012-07-17 | Invista Tech Sarl | Fibra elastica de poliolefina. |
| CN102762782A (zh) | 2009-12-23 | 2012-10-31 | 英威达技术有限公司 | 包含抗粘添加剂的弹性纤维 |
| BR112012015365A2 (pt) | 2009-12-23 | 2020-09-15 | Invista Technologies S.A.R.L. | artigo e método para preparar um pano |
| WO2011087729A2 (en) | 2010-01-14 | 2011-07-21 | Exxonmobil Chemical Patents Inc. | Processes and apparatus for polymer finishing and packaging |
| WO2011087731A1 (en) | 2010-01-14 | 2011-07-21 | Exxonmobil Chemical Patents Inc. | Processes and apparatus for continuous solution polymerization |
| CN102190749B (zh) * | 2010-03-05 | 2013-02-20 | 中国石油天然气股份有限公司 | 一种乙烯/α-烯烃共聚合的方法 |
| KR101791810B1 (ko) | 2014-03-21 | 2017-10-30 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 에틸렌 프로필렌 공중합체의 제조 방법 |
| CN107075209B (zh) | 2014-09-30 | 2020-05-19 | 埃克森美孚化学专利公司 | 低乙烯的无定形丙烯-乙烯-二烯三元共聚物组合物 |
| KR101973880B1 (ko) | 2015-01-14 | 2019-04-29 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 개선된 유동학적 특성을 가진 중합체 조성물 |
| US10618989B2 (en) | 2015-04-20 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Polyethylene composition |
| EP3274380B1 (en) | 2015-04-20 | 2020-08-19 | ExxonMobil Chemical Patents Inc. | Catalyst composition comprising fluorided support and processes for use thereof |
| JP2018522099A (ja) | 2015-06-15 | 2018-08-09 | エクソンモービル・ケミカル・パテンツ・インク | 連続溶液重合プロセス |
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- 1999-10-22 CA CA2345628A patent/CA2345628C/en not_active Expired - Fee Related
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- 1999-10-22 WO PCT/US1999/024944 patent/WO2000024793A1/en not_active Ceased
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- 1999-10-22 AT AT99974265T patent/ATE284422T1/de not_active IP Right Cessation
- 1999-10-22 JP JP2000578362A patent/JP4689829B2/ja not_active Expired - Lifetime
- 1999-10-22 US US09/426,099 patent/US6528670B1/en not_active Expired - Lifetime
- 1999-10-22 HK HK02103341.8A patent/HK1041705A1/zh unknown
- 1999-10-22 BR BR9914717-3A patent/BR9914717A/pt not_active IP Right Cessation
- 1999-10-22 KR KR1020017004930A patent/KR100568839B1/ko not_active Expired - Fee Related
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| JP2002528463A (ja) | 2002-09-03 |
| EP1196464B9 (en) | 2005-03-23 |
| JP4689829B2 (ja) | 2011-05-25 |
| AU757241B2 (en) | 2003-02-06 |
| US20020137959A1 (en) | 2002-09-26 |
| MXPA01003978A (es) | 2003-06-06 |
| EP1196464A1 (en) | 2002-04-17 |
| CN1138796C (zh) | 2004-02-18 |
| EP1196464B1 (en) | 2004-12-08 |
| DE69922548D1 (de) | 2005-01-13 |
| WO2000024793A8 (en) | 2001-10-11 |
| KR100568839B1 (ko) | 2006-04-10 |
| AU1321200A (en) | 2000-05-15 |
| WO2000024793A1 (en) | 2000-05-04 |
| CA2345628C (en) | 2010-02-16 |
| ATE284422T1 (de) | 2004-12-15 |
| DE69922548T2 (de) | 2006-01-05 |
| BR9914717A (pt) | 2001-07-10 |
| KR20010099705A (ko) | 2001-11-09 |
| CN1328580A (zh) | 2001-12-26 |
| CA2345628A1 (en) | 2000-05-04 |
| US6528670B1 (en) | 2003-03-04 |
| ES2233109T3 (es) | 2005-06-01 |
| HK1041705A1 (zh) | 2002-07-19 |
| US6506857B2 (en) | 2003-01-14 |
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