NO315977B1 - Katalysatorblanding omfattende reaksjonsproduktet av en organometallforbindelse samt anvendelse derav - Google Patents
Katalysatorblanding omfattende reaksjonsproduktet av en organometallforbindelse samt anvendelse derav Download PDFInfo
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- NO315977B1 NO315977B1 NO19974166A NO974166A NO315977B1 NO 315977 B1 NO315977 B1 NO 315977B1 NO 19974166 A NO19974166 A NO 19974166A NO 974166 A NO974166 A NO 974166A NO 315977 B1 NO315977 B1 NO 315977B1
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- hydrocarbyl
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000082 organogermanium group Chemical group 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical class FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000009997 thermal pre-treatment Methods 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- CXKQHHJKHZXXPZ-UHFFFAOYSA-N triethylsilanylium Chemical compound CC[Si+](CC)CC CXKQHHJKHZXXPZ-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- KTDRTOYQXRJJTE-FIFLTTCUSA-N trimethyl-[(1e,3e)-4-trimethylsilylbuta-1,3-dienyl]silane Chemical compound C[Si](C)(C)\C=C\C=C\[Si](C)(C)C KTDRTOYQXRJJTE-FIFLTTCUSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- VOYMPSZBODLRKS-UHFFFAOYSA-N trimethylsilanylium Chemical compound C[Si+](C)C VOYMPSZBODLRKS-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- 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
- C07F17/00—Metallocenes
-
- 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
- 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
-
- 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
- C08F4/603—Component covered by group C08F4/60 with a metal or compound covered by group C08F4/44 other than an organo-aluminium compound
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61916—Component covered by group C08F4/60 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/6192—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40243795A | 1995-03-10 | 1995-03-10 | |
| PCT/US1996/002891 WO1996028480A1 (en) | 1995-03-10 | 1996-03-04 | Supported catalyst component, supported catalyst, preparation process, polymerization process, complex compounds, and their preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO974166D0 NO974166D0 (no) | 1997-09-09 |
| NO974166L NO974166L (no) | 1997-11-07 |
| NO315977B1 true NO315977B1 (no) | 2003-11-24 |
Family
ID=23591882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19974166A NO315977B1 (no) | 1995-03-10 | 1997-09-09 | Katalysatorblanding omfattende reaksjonsproduktet av en organometallforbindelse samt anvendelse derav |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5834393A (hu) |
| EP (1) | EP0856014B1 (hu) |
| JP (1) | JPH11503113A (hu) |
| KR (1) | KR100420432B1 (hu) |
| CN (1) | CN1116309C (hu) |
| AR (1) | AR001183A1 (hu) |
| AT (1) | ATE233790T1 (hu) |
| AU (1) | AU712417B2 (hu) |
| BR (1) | BR9604776A (hu) |
| CO (1) | CO4560463A1 (hu) |
| CZ (1) | CZ285397A3 (hu) |
| DE (1) | DE69626531T2 (hu) |
| ES (1) | ES2188751T3 (hu) |
| HU (1) | HUP9801224A3 (hu) |
| IL (1) | IL117408A0 (hu) |
| NO (1) | NO315977B1 (hu) |
| PL (1) | PL186697B1 (hu) |
| RU (1) | RU2160283C2 (hu) |
| TR (1) | TR199700932T1 (hu) |
| TW (1) | TW372240B (hu) |
| WO (1) | WO1996028480A1 (hu) |
| ZA (1) | ZA961910B (hu) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5384299A (en) * | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| ATE171957T1 (de) * | 1994-06-03 | 1998-10-15 | Pcd Polymere Ag | Katalysatorträger, geträgerte metallocenkatalysatoren und deren verwendung für die herstellung von polyolefinen |
| US5972823A (en) * | 1994-08-03 | 1999-10-26 | Exxon Chemical Patents Inc | Supported ionic catalyst composition |
| US6143686A (en) * | 1994-08-03 | 2000-11-07 | Exxon Chemical Patents, Inc. | Supported ionic catalyst compositions |
| DE4431838A1 (de) * | 1994-09-07 | 1996-03-14 | Basf Ag | Geträgerte Metallocen-Katalysatorsysteme |
| US6506866B2 (en) * | 1994-11-17 | 2003-01-14 | Dow Global Technologies Inc. | Ethylene copolymer compositions |
| US7153909B2 (en) | 1994-11-17 | 2006-12-26 | Dow Global Technologies Inc. | High density ethylene homopolymers and blend compositions |
| US5939347A (en) * | 1995-01-25 | 1999-08-17 | W.R. Grace & Co. -Conn. | Supported catalytic activator |
| US5885924A (en) * | 1995-06-07 | 1999-03-23 | W. R. Grace & Co.-Conn. | Halogenated supports and supported activators |
| DE69610992T2 (de) * | 1995-11-27 | 2001-06-07 | The Dow Chemical Co., Midland | Trägerkatalysator, enthaltend einen davon gebundenen kationenbildenden aktivator |
| DE19606166A1 (de) * | 1996-02-20 | 1997-08-21 | Basf Ag | Verfahren zur Herstellung von Polymerisaten von Alkenen durch Suspensionspolymerisation |
| JPH09309926A (ja) * | 1996-05-17 | 1997-12-02 | Dow Chem Co:The | エチレン共重合体の製造方法 |
| DE19622207A1 (de) | 1996-06-03 | 1997-12-04 | Hoechst Ag | Chemische Verbindung |
| ATE202365T1 (de) * | 1996-08-13 | 2001-07-15 | Basell Polyolefine Gmbh | Geträgertes katalysatorsystem, verfahren zu seiner herstellung und seine verwendung zur polymerisation von olefinen |
| DE59712644D1 (de) * | 1996-08-13 | 2006-06-14 | Basell Polyolefine Gmbh | Geträgerte chemische Verbindung |
| US5783512A (en) * | 1996-12-18 | 1998-07-21 | The Dow Chemical Company | Catalyst component dispersion comprising an ionic compound and solid addition polymerization catalysts containing the same |
| DE19703478A1 (de) * | 1997-01-31 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung eines Matallocen-Katalysatorsystems |
| EP0971962B1 (en) * | 1997-04-04 | 2004-02-11 | BP Chemicals Limited | Catalyst system for high yield synthesis of polyolefins |
| US6228795B1 (en) * | 1997-06-05 | 2001-05-08 | Exxon Chemical Patents, Inc. | Polymeric supported catalysts |
| WO1998055518A1 (en) * | 1997-06-05 | 1998-12-10 | Exxon Chemical Patents Inc. | Polymeric supported catalysts for olefin polymerization |
| TR200000397T2 (tr) | 1997-08-15 | 2000-06-21 | The Dow Chemical Company | Esas itibariyle türdeş olan doğrusal olefin polimeri bileşimlerinden üretilen filmler. |
| AU753943B2 (en) | 1997-08-29 | 2002-10-31 | Dow Global Technologies Inc. | Homogeneous filled polymer composite |
| CA2245326C (en) * | 1997-09-29 | 2005-04-05 | Elf Atochem North America, Inc. | Heterogeneous organotin catalysts |
| KR20010032116A (ko) | 1997-12-01 | 2001-04-16 | 보 구스타프쏜 | 수분 흡수 장치 |
| US6444603B1 (en) * | 1997-12-22 | 2002-09-03 | Mitsui Chemicals, Inc. | Catalyst component for ethylenically unsaturated monomer polymerization, catalyst for ethylenically unsaturated monomer polymerization, and process for ethylenically unsaturated monomer polymerization using said catalyst |
| ES2237911T3 (es) | 1998-03-04 | 2005-08-01 | Exxonmobil Chemical Patents Inc. | Aniones no coordinantes para polimerizacion de olefinas. |
| US6177375B1 (en) * | 1998-03-09 | 2001-01-23 | Pq Corporation | High activity olefin polymerization catalysts |
| EP1090045B1 (en) | 1998-06-12 | 2004-04-28 | Univation Technologies LLC | Olefin polymerization process using activated lewis acid-base complexes |
| US6329312B1 (en) * | 1998-06-19 | 2001-12-11 | Phillips Petroleum Company | Metallocycle metallocenes and their use |
| EP1097175B1 (en) | 1998-07-16 | 2007-02-28 | Univation Technologies LLC | Aluminum-based lewis acid cocatalysts for olefin polymerization |
| AU5806599A (en) * | 1998-09-04 | 2000-03-27 | Dow Chemical Company, The | Long chain branched ethylene homopolymer made by a slurry process and blends thereof |
| US6159888A (en) * | 1998-09-09 | 2000-12-12 | Phillips Petroleum Company | Polymerization catalyst systems, their preparation, and use |
| CN1240726C (zh) * | 1998-09-16 | 2006-02-08 | 陶氏环球技术公司 | 淤浆聚合法及聚合物组合物 |
| US6184171B1 (en) * | 1998-10-05 | 2001-02-06 | W.R. Grace & Co. -Conn | Supported bidentate and tridentate catalyst compositions and olefin polymerization using same |
| CN1125834C (zh) * | 1998-10-23 | 2003-10-29 | 埃克森美孚化学专利公司 | 使用桥接二茂铪的烯烃共聚方法 |
| US6300433B1 (en) | 1998-10-23 | 2001-10-09 | Exxonmobil Chemical Patents Inc. | Olefin copolymerization process with bridged hafnocenes |
| RU2232766C2 (ru) * | 1998-10-23 | 2004-07-20 | Эксонмобил Кемикэл Пейтентс Инк. | Связанные мостиками металлоцены, способ полимеризации |
| US6486088B1 (en) | 1998-10-23 | 2002-11-26 | Exxonmobil Chemical Patents Inc. | High activity carbenium-activated polymerization catalysts |
| US6054623A (en) * | 1998-12-18 | 2000-04-25 | Alliedsignal Inc. | Hydroxythiol grignard reaction synthesis |
| US6465385B1 (en) | 1999-02-12 | 2002-10-15 | Sunoco, Inc. (R&M) | Zwitterionic polymerization catalyst |
| JP2002542348A (ja) | 1999-04-20 | 2002-12-10 | ビーピー ケミカルズ リミテッド | 遅延活性支持オレフィン重合触媒組成物、並びにその作成および使用方法 |
| WO2001005852A1 (en) * | 1999-07-15 | 2001-01-25 | The Dow Chemical Company | High density ethylene homopolymers and blend compositions |
| KR100336618B1 (ko) * | 1999-09-28 | 2002-05-16 | 박호군 | 아민기가 치환된 유기실란을 포함한 신규의 메탈로센 화합물 |
| ES2320407T3 (es) | 1999-10-05 | 2009-05-22 | Mallinckrodt Inc. | Fuente de monoxido de carbono para la preparacion de complejos de metal de trasnsicion y carbonilo. |
| US6809209B2 (en) | 2000-04-07 | 2004-10-26 | Exxonmobil Chemical Patents Inc. | Nitrogen-containing group-13 anionic compounds for olefin polymerization |
| CA2412606A1 (en) * | 2000-06-23 | 2002-01-03 | Exxonmobil Chemical Patents Inc. | Siloxy substituted cocatalyst activators for olefin polymerization |
| US6541410B1 (en) | 2000-06-23 | 2003-04-01 | Exxonmobil Chemical Patents Inc. | Siloxy substituted cocatalyst activators for olefin polymerization |
| EP1303543A1 (en) * | 2000-07-17 | 2003-04-23 | Univation Technologies LLC | A catalyst system and its use in a polymerization process |
| DE10047461A1 (de) * | 2000-09-21 | 2002-04-11 | Basf Ag | Aminosäurekomplexe und ihre Verwendung zur Herstellung von Olefinpolymerisaten |
| US6852659B1 (en) * | 2000-11-16 | 2005-02-08 | Univation Technologies, Llc | Method for preparing a catalyst composition and its use in a polymerization process |
| BR0115359A (pt) * | 2000-11-17 | 2003-08-26 | Univation Tech Llc | Método para a preparação de uma composição catalisadora e seu uso em um processo de polimerização |
| CA2430852A1 (en) * | 2000-12-06 | 2002-06-13 | Omlidon Technologies Llc | Melt-processible, wear resistant polyethylene |
| US20040241251A1 (en) * | 2001-05-04 | 2004-12-02 | Thiele Sven K H | Random or block co-or terpolymers produced by using of metal complex catalysts |
| JP2005504853A (ja) | 2001-06-15 | 2005-02-17 | ダウ グローバル テクノロジーズ インコーポレイティド | アルファ−オレフィンをベースとした枝分れポリマー |
| EP1417260B1 (en) | 2001-08-17 | 2005-08-03 | Dow Global Technologies Inc. | Bimodal polyethylene composition and articles made therefrom |
| KR20050034609A (ko) * | 2001-10-12 | 2005-04-14 | 다우 글로벌 테크놀로지스 인크. | 금속 착물 조성물 및 폴리디엔을 제조하기 위한촉매로서의 이의 용도 |
| JP2003128720A (ja) * | 2001-10-19 | 2003-05-08 | Sunallomer Ltd | オレフィン重合用固体助触媒成分、オレフィン重合用触媒およびイオン含有化合物 |
| JP4384496B2 (ja) | 2002-01-29 | 2009-12-16 | プラス オーソペディクス アーゲー | 超高分子ポリエチレンの焼結方法 |
| WO2004018530A1 (en) * | 2002-08-20 | 2004-03-04 | Bp Chemicals Limited | Supported polymerisation catalysts |
| AU2003253004A1 (en) * | 2002-08-20 | 2004-03-11 | Bp Chemicals Limited | Supported polymerisation catalysts |
| TWI300782B (en) * | 2002-08-29 | 2008-09-11 | Ineos Europe Ltd | Supported polymerisation catalysts |
| TWI315314B (en) * | 2002-08-29 | 2009-10-01 | Ineos Europe Ltd | Polymerisation process |
| KR101113341B1 (ko) | 2002-10-15 | 2012-09-27 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 올레핀 중합용 다중 촉매 시스템 및 이로부터 제조된중합체 |
| US7700707B2 (en) | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| KR101092349B1 (ko) * | 2003-02-21 | 2011-12-09 | 다우 글로벌 테크놀로지스 엘엘씨 | 공액 올레핀의 단독중합법 또는 공중합법 |
| JP2006519899A (ja) * | 2003-03-06 | 2006-08-31 | バセル ポリオレフィン ジーエムビーエイチ | オレフィンの重合のための触媒系 |
| GB0329348D0 (en) * | 2003-12-18 | 2004-01-21 | Bp Chem Int Ltd | Polymerisation process |
| JP2008509277A (ja) * | 2004-08-09 | 2008-03-27 | ダウ グローバル テクノロジーズ インコーポレイティド | ポリマーの製造のための担持ビス（ヒドロキシアリールアリールオキシ）触媒 |
| US7323523B2 (en) | 2004-12-07 | 2008-01-29 | Nova Chemicals (International) S.A. | Adjusting polymer characteristics through process control |
| EP1693388A1 (en) * | 2005-02-21 | 2006-08-23 | Innovene Europe Limited | Polymerisation catalysts |
| US7531602B2 (en) * | 2005-10-05 | 2009-05-12 | Nova Chemicals (International) S.A. | Polymer blends |
| WO2008052574A1 (en) * | 2006-10-30 | 2008-05-08 | Plus Orthopedics Ag | Processes comprising crosslinking polyethylene or using crosslinked polyethylene |
| CA2588352A1 (en) * | 2007-05-11 | 2008-11-11 | Nova Chemicals Corporation | Method to estimate pent values |
| US20080289274A1 (en) * | 2007-05-22 | 2008-11-27 | Nova Chemicals (International) S.A | Half panel |
| EP2025403A1 (en) * | 2007-07-24 | 2009-02-18 | Total Petrochemicals Research Feluy | Preparation of activating supports |
| WO2009018506A1 (en) * | 2007-08-01 | 2009-02-05 | Albemarle Corporation | Processes for making catalyst activators |
| CA2605044C (en) * | 2007-10-01 | 2014-12-02 | Nova Chemicals Corporation | Polymerization process using a mixed catalyst system |
| EP2172490A1 (en) | 2008-10-03 | 2010-04-07 | Ineos Europe Limited | Controlled polymerisation process |
| RU2549541C2 (ru) | 2009-07-28 | 2015-04-27 | Юнивейшн Текнолоджиз, Ллк | Способ полимеризации с использованием нанесенного катализатора с затрудненной геометрией |
| EP2357035A1 (en) | 2010-01-13 | 2011-08-17 | Ineos Europe Limited | Polymer powder storage and/or transport and/or degassing vessels |
| EP2383298A1 (en) | 2010-04-30 | 2011-11-02 | Ineos Europe Limited | Polymerization process |
| EP2383301A1 (en) | 2010-04-30 | 2011-11-02 | Ineos Europe Limited | Polymerization process |
| CA2713042C (en) | 2010-08-11 | 2017-10-24 | Nova Chemicals Corporation | Method of controlling polymer architecture |
| WO2012072417A1 (en) | 2010-11-29 | 2012-06-07 | Ineos Commercial Services Uk Limited | Polymerisation control process |
| US8383740B1 (en) | 2011-08-12 | 2013-02-26 | Ineos Usa Llc | Horizontal agitator |
| WO2013056979A1 (en) | 2011-10-17 | 2013-04-25 | Ineos Europe Ag | Polymer degassing process control |
| US9822195B2 (en) | 2012-02-29 | 2017-11-21 | Trinseo Europe Gmbh | Process for producing diene polymers |
| CN109369830A (zh) * | 2012-07-11 | 2019-02-22 | 亚培烯科技（杭州）有限公司 | 固体活化剂体系及其制备方法 |
| CA2783494C (en) | 2012-07-23 | 2019-07-30 | Nova Chemicals Corporation | Adjusting polymer composition |
| JP2015051936A (ja) * | 2013-09-06 | 2015-03-19 | 株式会社日本触媒 | ホウ素化合物の製造方法 |
| US20160215112A1 (en) | 2015-01-23 | 2016-07-28 | Nova Chemicals (International) S.A. | Enhanced foam resin |
| CN106336423A (zh) * | 2015-07-09 | 2017-01-18 | 中国石油化工科技开发有限公司 | 一类高热稳定性全氟芳基硼酸盐化合物及其制备 |
| EP3480031A1 (en) | 2017-11-03 | 2019-05-08 | Trinseo Europe GmbH | Polymer blend |
| WO2021025903A1 (en) * | 2019-08-02 | 2021-02-11 | Exxonmobil Chemical Patents Inc. | Non-coordinating anion type activators for use with polyolefin polymerization catalysts |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542119A (en) * | 1984-04-11 | 1985-09-17 | Sun Tech, Inc. | Hydroformylation catalyst and process |
| PL276385A1 (en) * | 1987-01-30 | 1989-07-24 | Exxon Chemical Patents Inc | Method for polymerization of olefines,diolefins and acetylene unsaturated compounds |
| US5055438A (en) * | 1989-09-13 | 1991-10-08 | Exxon Chemical Patents, Inc. | Olefin polymerization catalysts |
| FR2616785B1 (fr) * | 1987-06-19 | 1989-10-06 | Solvay | Composes guanidiniques comprenant un ion tetraphenylborate substitue et procede d'obtention de ces composes et utilisation des composes lors de la synthese peptidique |
| US5015749A (en) * | 1987-08-31 | 1991-05-14 | The Dow Chemical Company | Preparation of polyhydrocarbyl-aluminoxanes |
| 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 |
| US5057475A (en) * | 1989-09-13 | 1991-10-15 | Exxon Chemical Patents Inc. | Mono-Cp heteroatom containing group IVB transition metal complexes with MAO: supported catalyst for olefin polymerization |
| US5064802A (en) * | 1989-09-14 | 1991-11-12 | The Dow Chemical Company | Metal complex compounds |
| US5387568A (en) * | 1989-10-30 | 1995-02-07 | Fina Technology, Inc. | Preparation of metallocene catalysts for polymerization of olefins |
| ES2072598T3 (es) * | 1990-01-02 | 1995-07-16 | Exxon Chemical Patents Inc | Catalizadores ionicos de metaloceno soportados para la polimerizacion de olefinas. |
| PL166690B1 (pl) * | 1990-06-04 | 1995-06-30 | Exxon Chemical Patents Inc | Sposób wytwarzania polimerów olefin PL |
| JP3225463B2 (ja) * | 1991-01-18 | 2001-11-05 | ザ ダウ ケミカル カンパニー | シリカ支持遷移金属触媒 |
| US5206197A (en) * | 1991-03-04 | 1993-04-27 | The Dow Chemical Company | Catalyst composition for preparation of syndiotactic vinyl aromatic polymers |
| EP0614468B1 (en) * | 1991-11-25 | 1997-09-17 | Exxon Chemical Patents Inc. | Polyonic transition metal catalyst composition |
| US5374696A (en) * | 1992-03-26 | 1994-12-20 | The Dow Chemical Company | Addition polymerization process using stabilized reduced metal catalysts |
| US5330948A (en) * | 1992-03-31 | 1994-07-19 | Northwestern University | Homogeneous catalysts for stereoregular olefin polymerization |
| US5296433A (en) * | 1992-04-14 | 1994-03-22 | Minnesota Mining And Manufacturing Company | Tris(pentafluorophenyl)borane complexes and catalysts derived therefrom |
| JPH07509753A (ja) * | 1992-08-05 | 1995-10-26 | エクソン・ケミカル・パテンツ・インク | エチレンとｃ↓７乃至ｃ↓１↓０オレフィンの気相重合 |
| ES2167336T3 (es) * | 1992-08-05 | 2002-05-16 | Exxonmobil Chem Patents Inc | Catalizadores ionicos soportados de metal de transicion para la polimerizacion de olefinas. |
| US5354721A (en) * | 1993-06-22 | 1994-10-11 | Phillips Petroleum Company | Organo-aluminoxy product and use |
| JP2736938B2 (ja) * | 1993-06-24 | 1998-04-08 | ザ ダウ ケミカル カンパニー | チタン（▲ｉｉ▼）またはジルコニウム（▲ｉｉ▼）錯体およびそれからなる付加重合触媒 |
| US5412131A (en) * | 1993-07-09 | 1995-05-02 | Albemarle Corporation | Teritary amino-aluminoxane halides |
| US5447895A (en) * | 1994-03-10 | 1995-09-05 | Northwestern University | Sterically shielded diboron-containing metallocene olefin polymerization catalysts |
| US5643847A (en) * | 1994-08-03 | 1997-07-01 | Exxon Chemical Patents Inc. | Supported ionic catalyst composition |
| US5721183A (en) * | 1995-03-10 | 1998-02-24 | The Dow Chemical Company | Catalyst system comprising amine or phosphine adducts of tris(organyl)borane compounds |
| US5587439A (en) * | 1995-05-12 | 1996-12-24 | Quantum Chemical Corporation | Polymer supported catalyst for olefin polymerization |
-
1996
- 1996-03-04 AU AU53574/96A patent/AU712417B2/en not_active Ceased
- 1996-03-04 TR TR97/00932T patent/TR199700932T1/xx unknown
- 1996-03-04 KR KR1019970706329A patent/KR100420432B1/ko not_active IP Right Cessation
- 1996-03-04 RU RU97116729/04A patent/RU2160283C2/ru not_active IP Right Cessation
- 1996-03-04 JP JP8527670A patent/JPH11503113A/ja not_active Ceased
- 1996-03-04 CN CN96193227A patent/CN1116309C/zh not_active Expired - Fee Related
- 1996-03-04 AT AT96910361T patent/ATE233790T1/de not_active IP Right Cessation
- 1996-03-04 BR BR9604776A patent/BR9604776A/pt not_active IP Right Cessation
- 1996-03-04 US US08/610,647 patent/US5834393A/en not_active Expired - Fee Related
- 1996-03-04 CZ CZ972853A patent/CZ285397A3/cs unknown
- 1996-03-04 ES ES96910361T patent/ES2188751T3/es not_active Expired - Lifetime
- 1996-03-04 EP EP96910361A patent/EP0856014B1/en not_active Expired - Lifetime
- 1996-03-04 WO PCT/US1996/002891 patent/WO1996028480A1/en active IP Right Grant
- 1996-03-04 DE DE69626531T patent/DE69626531T2/de not_active Expired - Fee Related
- 1996-03-04 PL PL96322177A patent/PL186697B1/pl unknown
- 1996-03-04 HU HU9801224A patent/HUP9801224A3/hu unknown
- 1996-03-08 ZA ZA9601910A patent/ZA961910B/xx unknown
- 1996-03-08 CO CO96011520A patent/CO4560463A1/es unknown
- 1996-03-08 IL IL11740896A patent/IL117408A0/xx unknown
- 1996-03-08 AR AR33567996A patent/AR001183A1/es unknown
- 1996-03-27 TW TW085103688A patent/TW372240B/zh active
-
1997
- 1997-09-09 NO NO19974166A patent/NO315977B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR199700932T1 (xx) | 1998-01-21 |
| HUP9801224A2 (hu) | 1998-08-28 |
| PL322177A1 (en) | 1998-01-19 |
| ES2188751T3 (es) | 2003-07-01 |
| DE69626531D1 (de) | 2003-04-10 |
| AR001183A1 (es) | 1997-09-24 |
| KR19980702921A (ko) | 1998-09-05 |
| MX9706874A (es) | 1997-11-29 |
| IL117408A0 (en) | 1996-07-23 |
| AU5357496A (en) | 1996-10-02 |
| NO974166L (no) | 1997-11-07 |
| ATE233790T1 (de) | 2003-03-15 |
| TW372240B (en) | 1999-10-21 |
| EP0856014B1 (en) | 2003-03-05 |
| WO1996028480A1 (en) | 1996-09-19 |
| CN1116309C (zh) | 2003-07-30 |
| NO974166D0 (no) | 1997-09-09 |
| AU712417B2 (en) | 1999-11-04 |
| BR9604776A (pt) | 1998-06-23 |
| EP0856014A1 (en) | 1998-08-05 |
| CO4560463A1 (es) | 1998-02-10 |
| JPH11503113A (ja) | 1999-03-23 |
| PL186697B1 (pl) | 2004-02-27 |
| DE69626531T2 (de) | 2004-01-15 |
| US5834393A (en) | 1998-11-10 |
| ZA961910B (en) | 1997-09-08 |
| HUP9801224A3 (en) | 1998-11-30 |
| CZ285397A3 (cs) | 1998-02-18 |
| CN1181091A (zh) | 1998-05-06 |
| KR100420432B1 (ko) | 2004-07-23 |
| RU2160283C2 (ru) | 2000-12-10 |
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