CA2371835A1 - Stereorigid, bridged metallocene catalysts for polyolefin production - Google Patents
Stereorigid, bridged metallocene catalysts for polyolefin production Download PDFInfo
- Publication number
- CA2371835A1 CA2371835A1 CA002371835A CA2371835A CA2371835A1 CA 2371835 A1 CA2371835 A1 CA 2371835A1 CA 002371835 A CA002371835 A CA 002371835A CA 2371835 A CA2371835 A CA 2371835A CA 2371835 A1 CA2371835 A1 CA 2371835A1
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- CA
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- Prior art keywords
- use according
- polyolefin
- substituent
- hydrogen
- chosen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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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
- 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
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/15—Isotactic
-
- 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
-
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Organic Insulating Materials (AREA)
Abstract
Use of a metallocene catalyst component for the preparation of a polyolefin which comprises an isotactic or polyolefin syndiotactic/isotactic block polyolefin having a monomer length of up to C10, which component has the general formula:
R"C p R1R2R3)(C p'R1'R2')MQZ wherein Cp is a cyclopentadienyl ring substituted with at least one substituent; C p' is a substituted fluorenyl ring; R" is a structural bridge imparting stereorigidity to the component; R1 is optionally a substituent on the cyclopentadienyl ring which is distal to the bridge, which distal substituent comprises a bulky group of the formula XR*3 in which X is chosen from Group IVA, and each R* is the same or different and chosen from hydrogen or hydrocarbyl of from 1 to 20 carbon atoms, R2 is optionally a substituent on the cyclopentadienyl ring which is proximal to the bridge and positioned non-vicinal to the distal substituent and is of the formula YR#3 in which Y is chosen from group IVA, and each R# is the same or different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, R3 is optionally a substituent on the cyclopentadienyl ring which is proximal to the bridge and is a hydrogen atom or is of the formula ZR$3, in which Z is chosen from group IVA, and each R$ is the same of different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, R1' and R2' are each independently substituent groups on the fluorenyl ring, one of which is a group of the formula AR'''3, in which A is chosen from Group IVA, and each R''' is independently hydrogen or a hydrocarbyl having 1 to 20 carbon atoms and the other is hydrogen or a second group of the formula AR'''3; M is a Group IVB transition metal or vanadium; and each Q is hydrocarbyl having I to 20 carbon atoms or is a halogen.
R"C p R1R2R3)(C p'R1'R2')MQZ wherein Cp is a cyclopentadienyl ring substituted with at least one substituent; C p' is a substituted fluorenyl ring; R" is a structural bridge imparting stereorigidity to the component; R1 is optionally a substituent on the cyclopentadienyl ring which is distal to the bridge, which distal substituent comprises a bulky group of the formula XR*3 in which X is chosen from Group IVA, and each R* is the same or different and chosen from hydrogen or hydrocarbyl of from 1 to 20 carbon atoms, R2 is optionally a substituent on the cyclopentadienyl ring which is proximal to the bridge and positioned non-vicinal to the distal substituent and is of the formula YR#3 in which Y is chosen from group IVA, and each R# is the same or different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, R3 is optionally a substituent on the cyclopentadienyl ring which is proximal to the bridge and is a hydrogen atom or is of the formula ZR$3, in which Z is chosen from group IVA, and each R$ is the same of different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, R1' and R2' are each independently substituent groups on the fluorenyl ring, one of which is a group of the formula AR'''3, in which A is chosen from Group IVA, and each R''' is independently hydrogen or a hydrocarbyl having 1 to 20 carbon atoms and the other is hydrogen or a second group of the formula AR'''3; M is a Group IVB transition metal or vanadium; and each Q is hydrocarbyl having I to 20 carbon atoms or is a halogen.
Claims (31)
- Claim 1.
Use of a metallocene catalyst component for the prepation of a polyolefin which comprises an isotactic polyolefin or syndiotactic/sotactic block polyolefin having a monomer length of up to C10, which component has the general formula:
R"(C p R1R2R3)(C p R1R2)MQ2 Wherein C p is a cyclopentadienyl ring substituted with at feast one substituent; C p' is a substituted fluorenyl ring; R" is a structural bridge imparting stereorigidity to the component; R1 is hydrogen or a substituent on the cyclopentadienyl ring which is distal to the bridge, which distal substituent comprises a bulky group of the formula XR"3 in which X is chosen from Group IVA, and each R* is the same or different and chosen from hydrogen or hydrocarbyl of from 1 to 20 carbon atoms, R2 is hydrogen or a substituent on the cyclopentadienly ring which is proximal to the bridge and positioned non-vicinal to the distal substituent and is of the formula YR#3 in which Y is chosen from group IVA, and each R# is the same or different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, R3 is hydrogen or a substituent on the cyclopentadienly ring which is proximal to the bridge and is a hydrogen atom or is of the formula ZR$3, in which Z is chosen from group NA, and each R$ is the same or different and chosen from hydrogen or hydrocarbyl of 1 to 7 carbon atoms, with the proviso that at least one of R1, R2 or R3 is not hydrogen; R1' and R2' are each independently substituent groups on the fluorenyl ring, one of which is a group of the formula AR'''3, in which A is chosen from Group IVA, and each R''' is independently hydrogen or a hydrocarbyl having 1 to 20 carbon atoms and the other is hydrogen or a second group of the formula AR'''3; M is a Group IVB transition metal or vanadium; and each Q is hydrocarbyl having 1 to 20 carbon atoms or is a halogen. - 2. Use according to claim 1, wherein R1' and R2' are at positions 3 and 6 on the fluorenyl ring.
- 3. ose according to claim 1 or claim 2, wherein A is carbon or silicon.
- 4. Use according to claim 3, wherein AR'''3 is hydrocarbyl having from 1 to 24 carbon atoms.
- 5. Use according to claim Q, wherein: AR''' 3 is C (CH3)3.
- 6. Use according to claim 2, wherein AR''' 3 is Si(CH3)3.
- 7. Use according to any one of the preceding claims, wherein R1' and R2' are the same.
- 8. Use according to any one of the preceding claims, wherein R" is alkylidene having 1 to 20 carbon atoms, a dialkyl germanium or silicon or siloxane, alkyl phosphine or amine.
- 9. Use according to claim 8, wherein R" is isopropylidene, dimethylsilanediyl or diphenylmethylidene.
- 10. Use according to any one of the preceding claims, wherein M is zirconium or titanium.
- 11. Use according to any one of the preceding claims, wherein Q is halogen.
- 12. Use according to any one of the preceding claims, wherein R1 is C(CH3)3, C(CH3)2Ph, CPh3 or Si(CH3)3.
- 13. Use according to claim 12, wherein R1 is C(CH3)3.
- 14. Use according to any one of the preceding claims, wherein Y is carbon.
- 15. Use according to any one of the preceding claims, wherein 2 is carbon.
- 16. Use according to any preceding claim, wherein R2 is CH3.
- 17. Use according to any one of the preceding claims, wherein R3 is CH3.
- 18. Use according to any one of the preceding claims, wherein the metallocene catalyst component comprises isopropylidene-3-t-butyl-5-methyl-cyclopentadienyl 3,6 di t-butyl fluorenyl ZrCl2.
- 19. Use according to any one of the preceding claims, wherein the metallocene catalyst component comprises (i) a catalyst component according to any one of the preceding claims; and (ii) a regioisomer thereof in which R2 is proximal to the bridge and positioned vicinal to the distal substituent.
- 20. Use according to any one of claims 1 to 17, wherein the metallocene catalyst component comprises isopropylidene-(3-t-butyl-5-methyl cyclopentadienyl-3,6 di t-butyl fluorenyl) ZrCl2 and isopropylidene-(3-t-butyl-2-methyl cyclopentadienyl-3,6 di t-butyl fluorenyl) ZrCl2.
- 21. Use according to any one of the preceding claims, wherein the catalyst component is part of a catalyst system which further comprises an aluminium- or boron-containing co-catalyst capable of activating the catalyst component.
- 22. Use according to claim 17, wherein the catalyst system further comprises an inert support.
- 23. Use according to any one of claims 1 to 13, wherein R1 is a substituent on the cyclopentadienyl ring and the polyolefin is a syndiotactic/isotactic block polyolefin.
- 24. Use according to any one of claims 1 to 17, wherein R1 and R2 are both substituents on the cyclopentadienyl ring and the polyolefin is an isotactic polyolefin.
- 25. Use according to claim 19 or claim 20, wherein the polyolefin comprises an isotactic polyolefin having a multimodal molecular weight distribution.
- 26. A process for preparing polyolefins having a monomer length of up to C10, which comprises contacting a catalyst system as defined in claim 21 or claim 22 with at least one olefin in a reaction zone under polymerisation conditions to Corm an isotactic polyolefin or a syndiotactic/isotactic block polyolefin.
- 27. A process according to claim 26, wherein the olefin is propylene.
- 28. A process according to claim 26, wherein two or more olefins are present in the reaction zone to produce a polyolefin copolymer.
- 29. An isotactic polyolefin having a monomer length of up to C10 a,d a pentad distribution comprising at least 87 % mmmm as measured by 13C NMR, wherein the amount of 2-1 and 1-3 monomer insertions in the polyolefin is undetectable and wherein the weight average molecular weight is at least 450.000.
- 30. A polyolefin according to claim 29, wherein the pentad distribution comprises at least 95% mmmm as measured by 13C
nmr. - 31. A polyolefin according to claim 29 or claim 30, which comprises a polypropylene.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP1999/001094 WO2000049029A1 (en) | 1999-02-19 | 1999-02-19 | Polyolefin production |
EPPCT/EP99/01094 | 1999-02-19 | ||
PCT/EP2000/001378 WO2000049056A1 (en) | 1999-02-19 | 2000-02-18 | Polyolefin production |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2371835A1 true CA2371835A1 (en) | 2000-08-24 |
CA2371835C CA2371835C (en) | 2010-07-27 |
Family
ID=8167219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2371835A Expired - Fee Related CA2371835C (en) | 1999-02-19 | 2000-02-18 | Stereorigid, bridged metallocene catalysts for polyolefin production |
Country Status (11)
Country | Link |
---|---|
JP (1) | JP4864176B2 (en) |
KR (1) | KR100663788B1 (en) |
CN (1) | CN1152056C (en) |
AT (1) | ATE271071T1 (en) |
AU (2) | AU3141199A (en) |
BR (1) | BR0008312B1 (en) |
CA (1) | CA2371835C (en) |
DE (1) | DE60012166T2 (en) |
ES (1) | ES2223460T3 (en) |
RU (1) | RU2244721C2 (en) |
WO (2) | WO2000049029A1 (en) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6469188B1 (en) | 1999-01-20 | 2002-10-22 | California Institute Of Technology | Catalyst system for the polymerization of alkenes to polyolefins |
DE60034308T2 (en) * | 1999-10-08 | 2007-12-20 | Mitsui Chemicals, Inc. | Metallocenes, a process for their preparation, olefin polymerization catalyst, and a process for the preparation of polyolefins |
DE60020694T2 (en) * | 2000-08-07 | 2006-05-04 | Total Petrochemicals Research Feluy, Seneffe | polyolefin |
KR100500519B1 (en) * | 2001-03-15 | 2005-07-12 | 미쓰이 가가쿠 가부시키가이샤 | Automotive part made of polypropylene resin composition |
CN101423526B (en) * | 2003-03-28 | 2012-06-06 | 三井化学株式会社 | Propylene copolymer, polypropylene composition, use thereof, transition metal compounds, and catalysts for olefin polymerization |
EP1493760A1 (en) * | 2003-07-04 | 2005-01-05 | Total Petrochemicals Research Feluy | Styrene copolymerisation process |
EP1493759A1 (en) * | 2003-07-04 | 2005-01-05 | Total Petrochemicals Research Feluy | Polymerisation process |
EP1493778A1 (en) * | 2003-07-04 | 2005-01-05 | Total Petrochemicals Research Feluy | Polyolefin production |
EP1496070A1 (en) * | 2003-07-09 | 2005-01-12 | Total Petrochemicals Research Feluy | A polyolefin having internal double bonds and a method for making the same |
JP4823910B2 (en) * | 2004-08-30 | 2011-11-24 | 三井化学株式会社 | Propylene polymer production method |
WO2006126610A1 (en) * | 2005-05-25 | 2006-11-30 | Mitsui Chemicals, Inc. | Transition metal compound, olefin polymerization catalyst, and process for producing olefin polymer |
EP1734058A1 (en) * | 2005-06-13 | 2006-12-20 | Total Petrochemicals Research Feluy | Ethylene and alpha-olefins polymerisation catalyst system based on fluorenyl ligand |
EP1734059A1 (en) * | 2005-06-13 | 2006-12-20 | Total Petrochemicals Research Feluy | Carbon-bridged cyclopentadienyl-fluorenyl ligands |
WO2008059974A1 (en) | 2006-11-17 | 2008-05-22 | Mitsui Chemicals, Inc. | Method for producing syndiotactic propylene polymer |
JP5390194B2 (en) * | 2007-01-18 | 2014-01-15 | 株式会社プライムポリマー | Propylene homopolymer for stress-resistant molded article, composition containing the polymer, and stress-resistant molded article obtained therefrom |
US8119553B2 (en) * | 2007-09-28 | 2012-02-21 | Chevron Phillips Chemical Company Lp | Polymerization catalysts for producing polymers with low melt elasticity |
CN105330771B (en) * | 2014-12-03 | 2018-12-14 | 亚培烯科技(杭州)有限公司 | A kind of metallocene linear-low density polyethylene catalyst and its preparation method and application |
CN115677879B (en) * | 2021-07-31 | 2024-07-30 | 华为技术有限公司 | Catalyst for preparing cycloolefin copolymer, preparation method of cycloolefin copolymer, cycloolefin copolymer and application of cycloolefin copolymer |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69024442T2 (en) * | 1989-04-18 | 1996-08-01 | Mitsui Toatsu Chemicals | SYNDIOTACTIC POLYPROPYLENE RESIN COMPOSITION |
EP0487278B1 (en) * | 1990-11-20 | 1996-01-31 | Mitsubishi Chemical Corporation | Functionalized olefin polymers |
US5710222A (en) * | 1992-06-22 | 1998-01-20 | Fina Technology, Inc. | Method for controlling the melting points and molecular weights of syndiotactic polyolefins using metallocene catalyst systems |
JPH08325327A (en) * | 1995-06-02 | 1996-12-10 | Chisso Corp | Highly stereoregular polypropylene |
DE59609748D1 (en) * | 1995-12-18 | 2002-11-07 | Basell Polyolefine Gmbh | Process for the depletion of by-products in product mixtures |
EP0824112B1 (en) * | 1996-08-13 | 2006-05-10 | Basell Polyolefine GmbH | Supported chemical compound |
EP0881236A1 (en) * | 1997-05-26 | 1998-12-02 | Fina Research S.A. | Metallocene catalyst component for use in producing isotactic polyolefins |
-
1999
- 1999-02-19 AU AU31411/99A patent/AU3141199A/en not_active Abandoned
- 1999-02-19 WO PCT/EP1999/001094 patent/WO2000049029A1/en active Application Filing
- 1999-02-19 JP JP51283599A patent/JP4864176B2/en not_active Expired - Fee Related
-
2000
- 2000-02-18 KR KR1020017010519A patent/KR100663788B1/en not_active IP Right Cessation
- 2000-02-18 ES ES00906358T patent/ES2223460T3/en not_active Expired - Lifetime
- 2000-02-18 RU RU2001124801/04A patent/RU2244721C2/en not_active IP Right Cessation
- 2000-02-18 CN CNB008059535A patent/CN1152056C/en not_active Expired - Fee Related
- 2000-02-18 WO PCT/EP2000/001378 patent/WO2000049056A1/en active IP Right Grant
- 2000-02-18 AT AT00906358T patent/ATE271071T1/en not_active IP Right Cessation
- 2000-02-18 BR BRPI0008312-7A patent/BR0008312B1/en not_active IP Right Cessation
- 2000-02-18 AU AU28062/00A patent/AU2806200A/en not_active Abandoned
- 2000-02-18 CA CA2371835A patent/CA2371835C/en not_active Expired - Fee Related
- 2000-02-18 DE DE60012166T patent/DE60012166T2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE60012166T2 (en) | 2005-09-08 |
JP4864176B2 (en) | 2012-02-01 |
DE60012166D1 (en) | 2004-08-19 |
WO2000049029A1 (en) | 2000-08-24 |
BR0008312A (en) | 2002-01-22 |
AU3141199A (en) | 2000-09-04 |
ATE271071T1 (en) | 2004-07-15 |
KR20020002471A (en) | 2002-01-09 |
BR0008312B1 (en) | 2011-06-14 |
CN1152056C (en) | 2004-06-02 |
CN1346373A (en) | 2002-04-24 |
KR100663788B1 (en) | 2007-01-03 |
ES2223460T3 (en) | 2005-03-01 |
WO2000049056A1 (en) | 2000-08-24 |
AU2806200A (en) | 2000-09-04 |
JP2002510358A (en) | 2002-04-02 |
RU2244721C2 (en) | 2005-01-20 |
CA2371835C (en) | 2010-07-27 |
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EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20150218 |