CA2488052C - Polymerization catalyst activators, method of preparing, and their use in polymerization processes - Google Patents
Polymerization catalyst activators, method of preparing, and their use in polymerization processes Download PDFInfo
- Publication number
- CA2488052C CA2488052C CA2488052A CA2488052A CA2488052C CA 2488052 C CA2488052 C CA 2488052C CA 2488052 A CA2488052 A CA 2488052A CA 2488052 A CA2488052 A CA 2488052A CA 2488052 C CA2488052 C CA 2488052C
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- Canada
- Prior art keywords
- group
- toluene
- silica
- slurry
- catalyst system
- Prior art date
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- 239000012190 activator Substances 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 39
- 239000002685 polymerization catalyst Substances 0.000 title claims abstract description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 337
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 153
- 239000003054 catalyst Substances 0.000 claims abstract description 127
- 239000000463 material Substances 0.000 claims abstract description 45
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 28
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 27
- 239000002002 slurry Substances 0.000 claims description 163
- -1 aluminum alkyl compound Chemical class 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000005842 heteroatom Chemical group 0.000 claims description 46
- 230000008569 process Effects 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 45
- 125000004429 atom Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- DTNBMVQXEVNTLO-UHFFFAOYSA-N 4,5,6,7-tetrafluoro-1h-indole Chemical compound FC1=C(F)C(F)=C2NC=CC2=C1F DTNBMVQXEVNTLO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 21
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
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- 239000000460 chlorine Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
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- 125000001041 indolyl group Chemical group 0.000 claims description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 claims description 2
- BMJOPWQYDZAFDZ-UHFFFAOYSA-N 3,4-difluoro-1h-pyrrole Chemical class FC1=CNC=C1F BMJOPWQYDZAFDZ-UHFFFAOYSA-N 0.000 claims description 2
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- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical class CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
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- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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- 239000003446 ligand Substances 0.000 description 101
- 239000000243 solution Substances 0.000 description 65
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- 239000003921 oil Substances 0.000 description 36
- 229910052751 metal Inorganic materials 0.000 description 35
- 239000002184 metal Substances 0.000 description 35
- 239000012968 metallocene catalyst Substances 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 229940078552 o-xylene Drugs 0.000 description 31
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 26
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- 125000004122 cyclic group Chemical group 0.000 description 23
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- 229910052796 boron Inorganic materials 0.000 description 15
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- 150000003624 transition metals Chemical class 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 241000543375 Sideroxylon Species 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 11
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical group C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 229910052732 germanium Inorganic materials 0.000 description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 8
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000001354 calcination Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
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- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 229910052768 actinide Inorganic materials 0.000 description 4
- 150000001255 actinides Chemical class 0.000 description 4
- 150000005840 aryl radicals Chemical group 0.000 description 4
- 125000004803 chlorobenzyl group Chemical group 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- C08F4/642—Component covered by group C08F4/64 with an organo-aluminium compound
-
- 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
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- 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
-
- 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
- C08F210/02—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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—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
- 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
-
- 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
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
-
- 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
- C08F4/6592—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
- C08F4/65922—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 containing at least two cyclopentadienyl rings, fused or not
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
- Tires In General (AREA)
- Disintegrating Or Milling (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
- Indole Compounds (AREA)
- Polyethers (AREA)
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| US10/186,361 | 2002-06-28 | ||
| US10/186,361 US6703338B2 (en) | 2002-06-28 | 2002-06-28 | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
| PCT/US2003/017165 WO2004003031A2 (en) | 2002-06-28 | 2003-05-29 | Polymerization catalyst activators, method of preparing and their use in polymerization processes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2488052A1 CA2488052A1 (en) | 2004-01-08 |
| CA2488052C true CA2488052C (en) | 2010-08-03 |
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| CA002488043A Expired - Fee Related CA2488043C (en) | 2002-06-28 | 2003-06-26 | Halogen substituted catalyst system for olefin polymerization |
| CA002489240A Expired - Fee Related CA2489240C (en) | 2002-06-28 | 2003-06-26 | Heterocyclic nitrogen-containing activators and catalyst systems for olefin polymerization |
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| CA002488043A Expired - Fee Related CA2488043C (en) | 2002-06-28 | 2003-06-26 | Halogen substituted catalyst system for olefin polymerization |
| CA002489240A Expired - Fee Related CA2489240C (en) | 2002-06-28 | 2003-06-26 | Heterocyclic nitrogen-containing activators and catalyst systems for olefin polymerization |
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| RU (1) | RU2293088C2 (enExample) |
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| TW (1) | TWI280252B (enExample) |
| WO (3) | WO2004003031A2 (enExample) |
| ZA (1) | ZA200409750B (enExample) |
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| US6274684B1 (en) * | 1999-10-22 | 2001-08-14 | Univation Technologies, Llc | Catalyst composition, method of polymerization, and polymer therefrom |
| US6841504B2 (en) * | 2002-01-28 | 2005-01-11 | Univation Technologies, Llc | Polymerization catalyst activator and its use in a polymerization process |
| US6559251B1 (en) * | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| US7220695B2 (en) * | 2004-01-07 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Supported activator |
| US7741417B2 (en) * | 2004-01-07 | 2010-06-22 | Exxonmobil Chemical Patents Inc. | Preparation of polymerization catalyst activators utilizing indole-modified silica supports |
| EP2217627A1 (en) * | 2007-11-08 | 2010-08-18 | ExxonMobil Chemical Patents Inc. | Halogen substituted heterocyclic heteroatom containing ligands-alumoxane activation of metallocenes |
| US8022005B2 (en) * | 2007-11-08 | 2011-09-20 | Exxonmobil Chemical Patents Inc. | Halogen substituted heterocyclic heteroatom containing ligands-alumoxane activation of metallocenes |
| US8524846B1 (en) | 2009-07-02 | 2013-09-03 | The University Of Toledo | Trianionic ligand precursor compounds and uses thereof in constrained geometry catalysts |
| EP2882810B1 (en) | 2012-08-03 | 2018-01-17 | ExxonMobil Chemical Patents Inc. | Catalysts comprising salan ligands |
| EP2880097B1 (en) | 2012-08-03 | 2023-10-18 | ExxonMobil Chemical Patents Inc. | Process to prepare a vinyl terminated polyethylene with long chain branching |
| US9382349B2 (en) | 2012-08-03 | 2016-07-05 | Exxonmobil Chemical Patents Inc. | Polyalphaolefins prepared using modified Salan catalyst compounds |
| EP2880096B1 (en) | 2012-08-03 | 2018-01-03 | ExxonMobil Chemical Patents Inc. | Process for preparing polyalphaolefins using modified salan catalyst compounds and polyalphaolefins prepared therewith |
| US8952114B2 (en) | 2012-08-03 | 2015-02-10 | Exxonmobil Chemical Patents Inc. | Halogenated catalysts comprising Salan ligands |
| WO2014022010A2 (en) | 2012-08-03 | 2014-02-06 | Exxonmobil Chemical Patents Inc. | Non-symmetric catalysts comprising salan ligands |
| US9120879B2 (en) | 2012-11-02 | 2015-09-01 | Exxonmobil Chemical Patents Inc. | Supported Salan catalysts |
| SG11201506868UA (en) | 2013-03-13 | 2015-09-29 | Exxonmobil Chem Patents Inc | Diphenylamine salan catalyst |
| CN105992774B (zh) | 2013-06-20 | 2018-08-24 | 埃克森美孚化学专利公司 | Salenol催化剂 |
| CN105392776B (zh) * | 2013-06-20 | 2019-02-12 | 埃克森美孚化学专利公司 | 硫代-Salalen催化剂 |
| US9200100B2 (en) | 2013-06-20 | 2015-12-01 | Exxonmobil Chemical Patents Inc. | Long-bridged salen catalyst |
| US9290589B2 (en) | 2013-12-13 | 2016-03-22 | Exxonmobil Chemical Patents Inc. | Cyclopentadienyl-substituted salan catalysts |
| 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 |
| US10351647B2 (en) | 2015-05-29 | 2019-07-16 | Exxonmobil Chemical Patents Inc. | Polymerization process using bridged metallocene compounds supported on organoaluminum treated layered silicate supports |
| ES2784359T5 (es) | 2015-07-31 | 2024-04-04 | Cargill Inc | Método para preparar fibras de cítricos con características de unión de agua optimizadas |
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| US6841504B2 (en) * | 2002-01-28 | 2005-01-11 | Univation Technologies, Llc | Polymerization catalyst activator and its use in a polymerization process |
-
2002
- 2002-06-28 US US10/186,361 patent/US6703338B2/en not_active Expired - Fee Related
-
2003
- 2003-05-29 AU AU2003238849A patent/AU2003238849B2/en not_active Ceased
- 2003-05-29 RU RU2005102068/04A patent/RU2293088C2/ru not_active IP Right Cessation
- 2003-05-29 CA CA2488052A patent/CA2488052C/en not_active Expired - Fee Related
- 2003-05-29 MX MXPA05000067A patent/MXPA05000067A/es active IP Right Grant
- 2003-05-29 SG SG2006090062A patent/SG173215A1/en unknown
- 2003-05-29 KR KR1020047019815A patent/KR100713748B1/ko not_active Expired - Fee Related
- 2003-05-29 PL PL03373380A patent/PL373380A1/xx unknown
- 2003-05-29 EP EP03734308.4A patent/EP1517930B1/en not_active Expired - Lifetime
- 2003-05-29 BR BR0305256-7A patent/BR0305256A/pt not_active Application Discontinuation
- 2003-05-29 WO PCT/US2003/017165 patent/WO2004003031A2/en not_active Ceased
- 2003-05-29 CN CN038126850A patent/CN1659193B/zh not_active Expired - Fee Related
- 2003-05-29 CZ CZ20041151A patent/CZ20041151A3/cs unknown
- 2003-05-29 JP JP2004517607A patent/JP4361862B2/ja not_active Expired - Fee Related
- 2003-06-23 TW TW092117000A patent/TWI280252B/zh not_active IP Right Cessation
- 2003-06-26 CN CNB038151561A patent/CN1302029C/zh not_active Expired - Fee Related
- 2003-06-26 BR BRPI0312210-7A patent/BR0312210A/pt unknown
- 2003-06-26 AT AT03742245T patent/ATE506381T1/de not_active IP Right Cessation
- 2003-06-26 EP EP03742270A patent/EP1517932A2/en not_active Withdrawn
- 2003-06-26 CN CNB038151197A patent/CN100339403C/zh not_active Expired - Fee Related
- 2003-06-26 BR BR0312263-8A patent/BR0312263A/pt not_active IP Right Cessation
- 2003-06-26 DE DE60336812T patent/DE60336812D1/de not_active Expired - Lifetime
- 2003-06-26 CN CN200710102101XA patent/CN101054388B/zh not_active Expired - Fee Related
- 2003-06-26 CA CA002488043A patent/CA2488043C/en not_active Expired - Fee Related
- 2003-06-26 WO PCT/US2003/020320 patent/WO2004003032A2/en not_active Ceased
- 2003-06-26 MY MYPI20032414A patent/MY137541A/en unknown
- 2003-06-26 WO PCT/US2003/020199 patent/WO2004003037A1/en not_active Ceased
- 2003-06-26 AU AU2003280428A patent/AU2003280428A1/en not_active Abandoned
- 2003-06-26 EP EP03742245A patent/EP1517931B1/en not_active Expired - Lifetime
- 2003-06-26 CA CA002489240A patent/CA2489240C/en not_active Expired - Fee Related
- 2003-06-26 AU AU2003280424A patent/AU2003280424A1/en not_active Abandoned
- 2003-06-26 JP JP2004517894A patent/JP2005530907A/ja not_active Withdrawn
- 2003-06-26 JP JP2004517963A patent/JP2005531670A/ja not_active Withdrawn
- 2003-12-12 US US10/734,871 patent/US6858689B2/en not_active Expired - Fee Related
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2004
- 2004-02-27 NO NO20040872A patent/NO20040872L/no not_active Application Discontinuation
- 2004-12-01 ZA ZA200409750A patent/ZA200409750B/en unknown
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