JP4173803B2 - オレフィンの重合用触媒系 - Google Patents
オレフィンの重合用触媒系 Download PDFInfo
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- JP4173803B2 JP4173803B2 JP2003506283A JP2003506283A JP4173803B2 JP 4173803 B2 JP4173803 B2 JP 4173803B2 JP 2003506283 A JP2003506283 A JP 2003506283A JP 2003506283 A JP2003506283 A JP 2003506283A JP 4173803 B2 JP4173803 B2 JP 4173803B2
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- Prior art keywords
- tris
- pentafluorophenyl
- sup
- group
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- Prior art date
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 32
- 239000003054 catalyst Substances 0.000 title claims description 29
- 150000001336 alkenes Chemical class 0.000 title claims description 19
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- -1 transition metal organometallic compound Chemical class 0.000 claims abstract description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000002841 Lewis acid Substances 0.000 claims abstract description 8
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052710 silicon Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
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- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
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- 239000004711 α-olefin Substances 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
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- 125000004437 phosphorous atom Chemical group 0.000 abstract description 2
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- 230000015572 biosynthetic process Effects 0.000 description 16
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- 238000003786 synthesis reaction Methods 0.000 description 15
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- 238000003756 stirring Methods 0.000 description 12
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- 239000007787 solid Substances 0.000 description 8
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- 239000012190 activator Substances 0.000 description 7
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- 238000001228 spectrum Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 7
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- 206010037660 Pyrexia Diseases 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 229910052732 germanium Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
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- 239000010936 titanium Substances 0.000 description 5
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 5
- IEKMPJDJWCSGKX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8,9,9-decafluorofluorene Chemical compound FC1(F)C2=C(F)C(F)=C(F)C(F)=C2C2=C1C(F)=C(F)C(F)=C2F IEKMPJDJWCSGKX-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- LLWIHPJMYMZACK-UHFFFAOYSA-N 1,2,3,5-tetrafluoro-4-(2,3,4,6-tetrafluorophenyl)benzene Chemical group FC1=C(F)C(F)=CC(F)=C1C1=C(F)C=C(F)C(F)=C1F LLWIHPJMYMZACK-UHFFFAOYSA-N 0.000 description 3
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- XRPDDDRNQJNHLQ-UHFFFAOYSA-N 2-ethyl-1h-pyrrole Chemical compound CCC1=CC=CN1 XRPDDDRNQJNHLQ-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
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- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000002346 iodo group Chemical group I* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- ZOICEQJZAWJHSI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boron Chemical compound [B]C1=C(F)C(F)=C(F)C(F)=C1F ZOICEQJZAWJHSI-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- QWCHHUZAAGRHDB-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3-(2,3,5,6-tetrafluorophenyl)benzene Chemical group FC1=CC(F)=C(F)C(C=2C(=C(F)C=C(F)C=2F)F)=C1F QWCHHUZAAGRHDB-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 2
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- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
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- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
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- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- HKABSXHXKCTVGW-UHFFFAOYSA-N n,2,4,6-tetramethylaniline Chemical compound CNC1=C(C)C=C(C)C=C1C HKABSXHXKCTVGW-UHFFFAOYSA-N 0.000 description 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
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- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
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- 239000002685 polymerization catalyst Substances 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 1
- JMNFGPITPHPZOF-UHFFFAOYSA-N tris[3-(2,3,4,5,6-pentafluorophenyl)-1H-indol-2-yl] borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(C1=CC=CC=C1N1)=C1OB(OC1=C(C2=CC=CC=C2N1)C=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(C=2C(=C(F)C(F)=C(F)C=2F)F)C2=CC=CC=C2N1 JMNFGPITPHPZOF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201904 | 2001-05-21 | ||
| PCT/EP2002/005087 WO2002102811A1 (en) | 2001-05-21 | 2002-05-07 | Catalyst system for the polymerization of olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004533467A JP2004533467A (ja) | 2004-11-04 |
| JP2004533467A5 JP2004533467A5 (enExample) | 2005-12-22 |
| JP4173803B2 true JP4173803B2 (ja) | 2008-10-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003506283A Expired - Fee Related JP4173803B2 (ja) | 2001-05-21 | 2002-05-07 | オレフィンの重合用触媒系 |
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| Country | Link |
|---|---|
| US (1) | US7417006B2 (enExample) |
| EP (1) | EP1392705B1 (enExample) |
| JP (1) | JP4173803B2 (enExample) |
| AT (1) | ATE286505T1 (enExample) |
| DE (1) | DE60202524T2 (enExample) |
| WO (1) | WO2002102811A1 (enExample) |
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| WO2002100909A1 (en) * | 2001-06-12 | 2002-12-19 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| WO2002100908A1 (en) * | 2001-06-12 | 2002-12-19 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| JP2004535505A (ja) | 2001-07-17 | 2004-11-25 | バセル ポリオレフィン ジーエムビーエイチ | オレフィン（共）重合のための多工程方法 |
| US6989341B2 (en) | 2002-01-28 | 2006-01-24 | Univation Technologies, Llc | Halogen substituted catalyst system for olefin polymerization |
| US6703338B2 (en) | 2002-06-28 | 2004-03-09 | Univation Technologies, Llc | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
| US7589160B2 (en) * | 2002-12-04 | 2009-09-15 | Basell Polyolefine Gmbh | Process for preparing 1-butene polymers |
| US7534848B2 (en) * | 2002-12-04 | 2009-05-19 | Basell Polyolefine Gmbh | 1-butene copolymers and process for preparing them |
| US7741417B2 (en) | 2004-01-07 | 2010-06-22 | Exxonmobil Chemical Patents Inc. | Preparation of polymerization catalyst activators utilizing indole-modified silica supports |
| US7220695B2 (en) | 2004-01-07 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Supported activator |
| US8178636B2 (en) * | 2004-05-04 | 2012-05-15 | Basell Polyolefine Gmbh | Process for the preparation of atactic 1-butene polymers |
| CN101039967B (zh) | 2004-10-18 | 2010-06-09 | 巴塞尔聚烯烃意大利有限责任公司 | 低全同立构规整度丁烯-1均聚物或共聚物 |
| DE602005026837D1 (de) * | 2004-10-21 | 2011-04-21 | Basell Polyolefine Gmbh | 1-buten-polymer und herstellungsverfahren dafür |
| EP1655314A1 (en) | 2004-11-09 | 2006-05-10 | Basell Polyolefine GmbH | Process for the preparation of 1-butene/propylene copolymers |
| CN101061142B (zh) * | 2004-11-22 | 2012-04-18 | 巴塞尔聚烯烃股份有限公司 | 基于丙烯的三元共聚物 |
| US20080160862A1 (en) * | 2004-12-13 | 2008-07-03 | Basell Poliolefine Italia S.R.L. | Polyolefin Composition, Fibres and Nonwoven Fabrics |
| US7855263B2 (en) | 2005-02-03 | 2010-12-21 | Basell Polyolefine Gmbh | Process for producing thermoformed articles |
| PL1858907T3 (pl) | 2005-03-18 | 2009-04-30 | Basell Polyolefine Gmbh | Metalocenowe związki |
| US7803887B2 (en) * | 2005-03-18 | 2010-09-28 | Basell Polyolefine Gmbh | Metallocene compounds |
| WO2006100258A1 (en) | 2005-03-23 | 2006-09-28 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| AU2006226366A1 (en) * | 2005-03-23 | 2006-09-28 | Basell Polyolefine Gmbh | Process for the polymerizatio of olefins |
| EP1877453A1 (en) | 2005-05-03 | 2008-01-16 | Basell Polyolefine GmbH | Process for the polymerization of alpha olefins |
| WO2006120177A2 (en) | 2005-05-11 | 2006-11-16 | Basell Poliolefine Itatia S.R.L. | Polymerization process for preparing polyolefin blends |
| US8051611B2 (en) * | 2005-06-24 | 2011-11-08 | Dryvit Systems, Inc. | Exterior insulation and finish system and method and tool for installing same |
| WO2007045590A1 (en) | 2005-10-21 | 2007-04-26 | Basell Polyolefine Gmbh | Polypropylene for injection molding |
| WO2007045603A1 (en) * | 2005-10-21 | 2007-04-26 | Basell Polyolefine Gmbh | Propylene polymers |
| EP1940888B1 (en) * | 2005-10-21 | 2010-06-02 | Basell Polyolefine GmbH | Polypropylene random copolymers having high melt flow rates for injection molding and melt brown applications |
| KR101364329B1 (ko) * | 2006-02-02 | 2014-02-18 | 바젤 폴리올레핀 게엠베하 | 프로필렌 용융 취입 수지, 이로부터 제조된 프로필렌 용융 취입 수지 섬유 및 부직포, 및 이의 제조 방법 |
| CA2643339A1 (en) * | 2006-02-23 | 2007-08-30 | Basell Poliolefine Italia S.R.L. | Propylene polymers for injection molding applications |
| US8785575B2 (en) * | 2006-04-21 | 2014-07-22 | Basell Polyolefine Gmbh | Process for the preparation of ethylene propylene copolymers |
| WO2007122098A1 (en) | 2006-04-21 | 2007-11-01 | Basell Polyolefine Gmbh | Process for the preparation of ethylene copolymers |
| US8022005B2 (en) * | 2007-11-08 | 2011-09-20 | Exxonmobil Chemical Patents Inc. | Halogen substituted heterocyclic heteroatom containing ligands-alumoxane activation of metallocenes |
| US9321854B2 (en) | 2013-10-29 | 2016-04-26 | Exxonmobil Chemical Patents Inc. | Aluminum alkyl with C5 cyclic and pendent olefin polymerization catalyst |
| US10676547B2 (en) | 2015-08-31 | 2020-06-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins on clays |
| US10618988B2 (en) | 2015-08-31 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| US11041029B2 (en) | 2015-08-31 | 2021-06-22 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins for polyolefin reactions |
| US10059788B2 (en) | 2016-04-29 | 2018-08-28 | Exxonmobil Chemical Patents Inc. | Organoaluminum activators on clays |
| US10562987B2 (en) | 2016-06-30 | 2020-02-18 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| US10626200B2 (en) | 2017-02-28 | 2020-04-21 | Exxonmobil Chemical Patents Inc. | Branched EPDM polymers produced via use of vinyl transfer agents and processes for production thereof |
| WO2018160278A1 (en) | 2017-03-01 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324800A (en) | 1983-06-06 | 1994-06-28 | Exxon Chemical Patents Inc. | Process and catalyst for polyolefin density and molecular weight control |
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| US5384299A (en) * | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| US5055438A (en) | 1989-09-13 | 1991-10-08 | Exxon Chemical Patents, Inc. | Olefin polymerization catalysts |
| WO1991002012A1 (en) | 1989-08-03 | 1991-02-21 | Exxon Chemical Patents Inc. | Very high molecular weight polyethylene |
| NZ235032A (en) | 1989-08-31 | 1993-04-28 | Dow Chemical Co | Constrained geometry complexes of titanium, zirconium or hafnium comprising a substituted cyclopentadiene ligand; use as olefin polymerisation catalyst component |
| US5239022A (en) | 1990-11-12 | 1993-08-24 | Hoechst Aktiengesellschaft | Process for the preparation of a syndiotactic polyolefin |
| US5243001A (en) | 1990-11-12 | 1993-09-07 | Hoechst Aktiengesellschaft | Process for the preparation of a high molecular weight olefin polymer |
| ES2091273T3 (es) | 1990-11-12 | 1996-11-01 | Hoechst Ag | Procedimiento para la preparacion de un polimero olefinico de alto peso molecular. |
| EP0485820B1 (de) | 1990-11-12 | 1996-08-21 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung eines Olefinpolymers |
| ES2071888T3 (es) | 1990-11-12 | 1995-07-01 | Hoechst Ag | Bisindenilmetalocenos sustituidos en posicion 2, procedimiento para su preparacion y su utilizacion como catalizadores en la polimerizacion de olefinas. |
| HUT74312A (en) | 1993-06-24 | 1996-12-30 | Dow Chemical Co | Titanium or zirconium complexes, process for producing thereof, polymerization catalysts containing thereof and polymerization process |
| IT1272923B (it) | 1995-01-23 | 1997-07-01 | Spherilene Srl | Composti metallocenici,procedimento per la loro preparazione,e loro utilizzo in catalizzatori per la polimerizzazione delle olefine |
| NZ303800A (en) | 1995-01-24 | 2000-05-26 | Univ North Carolina | Olefin polymers and block polymers, preparation, use, catalysts and catalyst intermediates |
| JPH11503063A (ja) | 1995-03-08 | 1999-03-23 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | 触媒組成物における架橋ビスアミド第４族金属化合物 |
| US5714556A (en) | 1995-06-30 | 1998-02-03 | E. I. Dupont De Nemours And Company | Olefin polymerization process |
| AU733813B2 (en) | 1996-11-15 | 2001-05-24 | Montell Technology Company B.V. | Heterocyclic metallocenes and polymerization catalysts |
| WO1998040374A2 (en) | 1997-03-10 | 1998-09-17 | Eastman Chemical Company | Olefin polymerization catalysts containing group 8-10 transition metals, bidentate ligands, processes employing such catalysts and polymers obtained therefrom |
| US6559252B1 (en) | 1997-10-29 | 2003-05-06 | Basell Technology Company Bv | Catalysts and processes for the polymerization of olefins |
| AU1870999A (en) | 1997-11-12 | 1999-05-31 | Montell Technology Company B.V. | Metallocenes and catalysts for olefin-polymerisation |
| EP1056752B1 (en) * | 1998-02-20 | 2003-06-25 | Dow Global Technologies Inc. | Catalyst activators comprising expanded anions |
| WO1999058539A1 (en) | 1998-05-08 | 1999-11-18 | Montell Technology Company B.V. | Metallocenes, ligands and olefin polymerization |
| US6486277B1 (en) | 1998-12-12 | 2002-11-26 | Targor Gmbh | Zwitterionic transition metal compound which contains boron |
| CA2370799A1 (en) * | 2000-02-24 | 2001-08-30 | Basell Technology Company Bv | Organometallic compound useful as cocatalyst for polymerizing olefins |
| JP2006508903A (ja) * | 2002-07-09 | 2006-03-16 | バセル ポリオレフィン ジーエムビーエイチ | オレフィン重合用触媒系 |
-
2002
- 2002-05-07 WO PCT/EP2002/005087 patent/WO2002102811A1/en not_active Ceased
- 2002-05-07 US US10/478,346 patent/US7417006B2/en not_active Expired - Fee Related
- 2002-05-07 AT AT02738045T patent/ATE286505T1/de not_active IP Right Cessation
- 2002-05-07 DE DE60202524T patent/DE60202524T2/de not_active Expired - Fee Related
- 2002-05-07 JP JP2003506283A patent/JP4173803B2/ja not_active Expired - Fee Related
- 2002-05-07 EP EP02738045A patent/EP1392705B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60202524D1 (de) | 2005-02-10 |
| ATE286505T1 (de) | 2005-01-15 |
| DE60202524T2 (de) | 2005-06-30 |
| JP2004533467A (ja) | 2004-11-04 |
| US20040132612A1 (en) | 2004-07-08 |
| US7417006B2 (en) | 2008-08-26 |
| WO2002102811A1 (en) | 2002-12-27 |
| EP1392705B1 (en) | 2005-01-05 |
| EP1392705A1 (en) | 2004-03-03 |
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