NO323005B1 - Metallocenforbindelser, fremgangsmate ved fremstilling og anvendelse derav - Google Patents

Metallocenforbindelser, fremgangsmate ved fremstilling og anvendelse derav Download PDF

Info

Publication number: NO323005B1
Authority: NO; Norway
Prior art keywords: group; chloro; indenyl; germanium; silicon
Prior art date: 1997-02-01

Application number

NO19980412A

Other languages

English (en)

Norwegian (no)

Other versions

NO980412D0 (no

NO980412L (no

Inventor

Antonio Munoz-Escalon Lafuente

Luis Mendez Llatas

Original Assignee

Repsol Quimica Sa

Priority date (The priority date 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 date listed.)

1997-02-01

Filing date

1998-01-30

Publication date

2006-12-18

1998-01-30 Application filed by Repsol Quimica Sa filed Critical Repsol Quimica Sa

1998-01-30 Publication of NO980412D0 publication Critical patent/NO980412D0/no

1998-08-03 Publication of NO980412L publication Critical patent/NO980412L/no

2006-12-18 Publication of NO323005B1 publication Critical patent/NO323005B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 28
238000000034 method Methods 0.000 title claims description 18
230000008569 process Effects 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title description 7
-1 C8 - C20 arylalkenyl Chemical group 0.000 claims description 55
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 47
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 47
229910052710 silicon Inorganic materials 0.000 claims description 26
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 25
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 25
229910052732 germanium Inorganic materials 0.000 claims description 25
239000010703 silicon Substances 0.000 claims description 25
125000004429 atom Chemical group 0.000 claims description 24
229910052718 tin Inorganic materials 0.000 claims description 24
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 19
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 12
239000000758 substrate Substances 0.000 claims description 12
238000003786 synthesis reaction Methods 0.000 claims description 12
230000000737 periodic effect Effects 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000003446 ligand Substances 0.000 claims description 10
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052796 boron Inorganic materials 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
229910052723 transition metal Inorganic materials 0.000 claims description 7
150000003624 transition metals Chemical class 0.000 claims description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
VGRFVJMYCCLWPQ-UHFFFAOYSA-N germanium Chemical compound [Ge].[Ge] VGRFVJMYCCLWPQ-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
150000008282 halocarbons Chemical class 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000005864 Sulphur Substances 0.000 claims description 3
150000002009 diols Chemical class 0.000 claims description 3
125000006850 spacer group Chemical group 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
150000003573 thiols Chemical class 0.000 claims description 3
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 2
229920005862 polyol Polymers 0.000 claims description 2
150000003077 polyols Chemical class 0.000 claims description 2
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
230000007704 transition Effects 0.000 claims description 2
229910007161 Si(CH3)3 Inorganic materials 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 17
ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 16
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
229910052735 hafnium Inorganic materials 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 9
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 9
VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
229920000828 poly(metallocenes) Polymers 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229910001868 water Inorganic materials 0.000 description 3
239000004711 α-olefin Substances 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910008326 Si-Y Inorganic materials 0.000 description 2
229910006773 Si—Y Inorganic materials 0.000 description 2
BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 2
QFWCJRJETHTOEJ-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)[Hf+2]C1C=CC2=CC=CC=C12 Chemical compound [Cl-].[Cl-].C1(C=CC=C1)[Hf+2]C1C=CC2=CC=CC=C12 QFWCJRJETHTOEJ-UHFFFAOYSA-L 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
VMFHCJPMKUTMMQ-UHFFFAOYSA-N cyclopenta-2,4-dien-1-yl(trimethyl)silane Chemical compound C[Si](C)(C)C1C=CC=C1 VMFHCJPMKUTMMQ-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000178 monomer Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003334 secondary amides Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
229910052726 zirconium Inorganic materials 0.000 description 2
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
OZYOFBYUNKIYFO-UHFFFAOYSA-K 1,2,3,4-tetramethylcyclopentane;trichlorozirconium Chemical compound Cl[Zr](Cl)Cl.C[C]1[CH][C](C)[C](C)[C]1C OZYOFBYUNKIYFO-UHFFFAOYSA-K 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VMZFYCCXODXFLU-UHFFFAOYSA-L Cl[Ti](Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 Chemical compound Cl[Ti](Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 VMZFYCCXODXFLU-UHFFFAOYSA-L 0.000 description 1
HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical compound [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910018540 Si C Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910020997 Sn-Y Inorganic materials 0.000 description 1
229910008859 Sn—Y Inorganic materials 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
229910007928 ZrCl2 Inorganic materials 0.000 description 1
SVUKUAINDVKRRB-UHFFFAOYSA-L [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1(C(=C(C(=C1)C)C)C)C)C1C=CC=C1)Cl Chemical compound [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1(C(=C(C(=C1)C)C)C)C)C1C=CC=C1)Cl SVUKUAINDVKRRB-UHFFFAOYSA-L 0.000 description 1
IEHNHJSENBZALW-UHFFFAOYSA-L [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1)Cl Chemical compound [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1)Cl IEHNHJSENBZALW-UHFFFAOYSA-L 0.000 description 1
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LKHUTHIPODKWTB-UHFFFAOYSA-L [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)Cl Chemical compound [Cl-].[Cl-].C(C)[Si](=[Hf+2](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)Cl LKHUTHIPODKWTB-UHFFFAOYSA-L 0.000 description 1
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PWQKENPCKLTVOT-UHFFFAOYSA-L [Cl-].[Cl-].C(C)[Si](=[Ti+2](C1(C(=C(C(=C1)C)C)C)C)C1(C(=C(C(=C1)C)C)C)C)Cl Chemical compound [Cl-].[Cl-].C(C)[Si](=[Ti+2](C1(C(=C(C(=C1)C)C)C)C)C1(C(=C(C(=C1)C)C)C)C)Cl PWQKENPCKLTVOT-UHFFFAOYSA-L 0.000 description 1
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239000003426 co-catalyst Substances 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
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230000008025 crystallization Effects 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
CSEGCHWAMVIXSA-UHFFFAOYSA-L cyclopenta-1,3-diene;hafnium(4+);dichloride Chemical compound [Cl-].[Cl-].[Hf+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 CSEGCHWAMVIXSA-UHFFFAOYSA-L 0.000 description 1
IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical compound [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 1
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238000007429 general method Methods 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
150000003003 phosphines Chemical group 0.000 description 1
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QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- 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)

NO19980412A 1997-02-01 1998-01-30 Metallocenforbindelser, fremgangsmate ved fremstilling og anvendelse derav NO323005B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES9700200		1997-02-01

Publications (3)

Publication Number	Publication Date
NO980412D0 NO980412D0 (no)	1998-01-30
NO980412L NO980412L (no)	1998-08-03
NO323005B1 true NO323005B1 (no)	2006-12-18

Family

ID=8298074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19980412A NO323005B1 (no)	1997-02-01	1998-01-30	Metallocenforbindelser, fremgangsmate ved fremstilling og anvendelse derav

Country Status (8)

Country	Link
US (1)	US6018064A (ja)
EP (1)	EP0856518B1 (ja)
JP (1)	JP3390133B2 (ja)
AT (1)	ATE236914T1 (ja)
DE (1)	DE69813058T2 (ja)
ES (1)	ES2192760T3 (ja)
NO (1)	NO323005B1 (ja)
PT (1)	PT856518E (ja)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2154017T3 (es) *	1996-10-31	2001-03-16	Repsol Quimica Sa	Sistemas cataliticos para la polimerizacion y copolimerizacion de alfa-olefinas.
EP0856524A1 (en)	1997-02-01	1998-08-05	Repsol Quimica S.A.	Heterogeneous catalyst components for olefins polymerization, preparation process and use thereof
US7148173B2 (en)	1998-04-27	2006-12-12	Repsol Quimica, S.A.	Catalytic systems for the polymerization and copolymerization of alpha-olefins
DE69904982T2 (de) *	1998-04-29	2004-01-08	Repsol Quimica S.A.	Funktionalisierte Metallocene, deren Herstellung und deren Verwendung
ES2216473T3 (es) *	1998-04-29	2004-10-16	Repsol Quimica S.A.	Preparacion y uso de componentes de catalizador heterogeneos para polimerizacion de olefinas.
US6706827B1 (en) *	1998-06-08	2004-03-16	Samsung Atofina Co. Ltd.	Metallocene catalysts for olefin or styrene polymerization and polymerization method using the metallocene catalysts
US6291610B1 (en)	1998-12-18	2001-09-18	Univation Technologies, Llc	Haloaryl containing group 13 substituents on bridged metallocene polyolefin catalysts
KR100690345B1 (ko) *	2004-09-03	2007-03-09	주식회사 엘지화학	담지 메탈로센 촉매, 그 제조방법 및 이를 이용한폴리올레핀의 제조방법
CN106008767A (zh) *	2016-05-23	2016-10-12	北京化工大学	醇氧亚甲基桥联双金属半茂催化剂及制备方法与应用
CN106046208B (zh) *	2016-05-23	2019-03-29	北京化工大学	硅羟氧基桥联的双金属半茂催化剂及制备方法与应用
WO2018182984A1 (en) *	2017-03-28	2018-10-04	Exxonmobil Chemical Patents Inc.	Metallocene compounds
US10968290B2 (en)	2017-03-28	2021-04-06	Exxonmobil Chemical Patents Inc.	Metallocene-catalyzed polyalpha-olefins

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1995027741A1 (en) *	1994-04-11	1995-10-19	Mitsui Petrochemical Industries, Ltd.	Process for producing propylene polymer composition, and propylene polymer composition
DE19527652A1 (de) *	1995-07-28	1997-01-30	Hoechst Ag	Metallocenverbindung
ES2120868B1 (es) *	1995-08-03	2000-09-16	Repsol Quimica Sa	Sistema de catalizadores hetereogeneos tipo metalogeno, para procesos de obtencion de poliolefinas.
IT1283010B1 (it) *	1996-05-15	1998-04-03	Enichem Spa	Complesso metallocenico supportato e procedimento per la sua prepa- razione

1998
- 1998-01-29 PT PT98500022T patent/PT856518E/pt unknown
- 1998-01-29 AT AT98500022T patent/ATE236914T1/de not_active IP Right Cessation
- 1998-01-29 ES ES98500022T patent/ES2192760T3/es not_active Expired - Lifetime
- 1998-01-29 EP EP98500022A patent/EP0856518B1/en not_active Expired - Lifetime
- 1998-01-29 DE DE69813058T patent/DE69813058T2/de not_active Expired - Fee Related
- 1998-01-30 NO NO19980412A patent/NO323005B1/no unknown
- 1998-01-30 US US09/016,210 patent/US6018064A/en not_active Expired - Fee Related
- 1998-01-30 JP JP01933798A patent/JP3390133B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO980412D0 (no)	1998-01-30
ES2192760T3 (es)	2003-10-16
US6018064A (en)	2000-01-25
PT856518E (pt)	2003-08-29
NO980412L (no)	1998-08-03
JPH10226693A (ja)	1998-08-25
EP0856518A1 (en)	1998-08-05
ATE236914T1 (de)	2003-04-15
DE69813058T2 (de)	2004-02-19
EP0856518B1 (en)	2003-04-09
JP3390133B2 (ja)	2003-03-24
DE69813058D1 (de)	2003-05-15

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US20060142147A1 (en)	2006-06-29	Catalysts compositions for the polymerization and copolymerization of alpha-olefins
EP3218385A1 (en)	2017-09-20	Metallocenes and their use as polymerization catalysts
JP3815814B2 (ja)	2006-08-30	橋状メタロセン化合物の製造法
CA2263185A1 (en)	1999-09-04	Organometallic compounds
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US7629481B2 (en)	2009-12-08	Ansa-metallocene compound, process of preparing the same, and process of preparing polyolefin using the same
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US5726332A (en)	1998-03-10	Synthesis of novel organometallics and their use in olefin polymerization
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JP2002529555A (ja)	2002-09-10	橋かけペンタジエニル−フルオレニル遷移金属錯体を使用するｅｐ（ｄ）ｍの製造方法
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JPH09183809A (ja)	1997-07-15	オレフィン系重合体の製造方法
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KR101233924B1 (ko)	2013-02-15	폴리(1-부텐) 제조용 촉매 및 이를 이용한 폴리(1-부텐) 제조방법