NL1003020C2 - Cyclopentadieenverbinding met een niet-coördinerend anion. - Google Patents

Cyclopentadieenverbinding met een niet-coördinerend anion. Download PDF

Info

Publication number: NL1003020C2
Authority: NL; Netherlands
Prior art keywords: group; precursor; precursor according; bound; derivative
Prior art date: 1996-05-03

Application number

NL1003020A

Other languages

English (en)

Dutch (nl)

Inventor

Rutgerus Antonie Jacob Postema

Original Assignee

Dsm Nv

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.)

1996-05-03

Filing date

1996-05-03

Publication date

1997-11-06

1996-05-03 Application filed by Dsm Nv filed Critical Dsm Nv

1996-05-03 Priority to NL1003020A priority Critical patent/NL1003020C2/nl

1997-04-28 Priority to EP97919751A priority patent/EP0896592A1/fr

1997-04-28 Priority to PCT/NL1997/000231 priority patent/WO1997042231A1/fr

1997-04-28 Priority to JP9539783A priority patent/JP2000509739A/ja

1997-04-28 Priority to AU24108/97A priority patent/AU2410897A/en

1997-11-06 Application granted granted Critical

1997-11-06 Publication of NL1003020C2 publication Critical patent/NL1003020C2/nl

Links

150000001450 anions Chemical class 0.000 title claims description 29
-1 Cyclopentadiene compound Chemical class 0.000 title description 18
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title description 3
239000002243 precursor Substances 0.000 claims description 56
125000002091 cationic group Chemical group 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 23
238000000034 method Methods 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 13
239000002168 alkylating agent Substances 0.000 claims description 13
239000003446 ligand Substances 0.000 claims description 11
229910052723 transition metal Inorganic materials 0.000 claims description 10
150000003624 transition metals Chemical class 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
230000000737 periodic effect Effects 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
239000010936 titanium Substances 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 7
239000000178 monomer Substances 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
229910052747 lanthanoid Inorganic materials 0.000 claims description 5
150000002602 lanthanoids Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
230000003213 activating effect Effects 0.000 claims description 4
230000000379 polymerizing effect Effects 0.000 claims description 4
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
150000001993 dienes Chemical class 0.000 claims description 3
229910052719 titanium Inorganic materials 0.000 claims description 3
239000004711 α-olefin Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000012018 catalyst precursor Substances 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 1
239000013589 supplement Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000002002 slurry Substances 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 12
238000006116 polymerization reaction Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 5
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
230000002411 adverse Effects 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
229910052752 metalloid Inorganic materials 0.000 description 3
150000002738 metalloids Chemical class 0.000 description 3
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 3
UXQAEOWCSOPBLF-UHFFFAOYSA-N 2,2,3,3-tetramethyloctane Chemical compound CCCCCC(C)(C)C(C)(C)C UXQAEOWCSOPBLF-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
239000012190 activator Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000003947 neutron activation analysis Methods 0.000 description 2
238000004806 packaging method and process Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 2
DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
MVECFARLYQAUNR-UHFFFAOYSA-N CCCC[Mg]CC Chemical compound CCCC[Mg]CC MVECFARLYQAUNR-UHFFFAOYSA-N 0.000 description 1
FKCNEZCYLSIGQY-UHFFFAOYSA-K CN(C)CC[Ti](Cl)(Cl)(Cl)C1C=CC=C1 Chemical compound CN(C)CC[Ti](Cl)(Cl)(Cl)C1C=CC=C1 FKCNEZCYLSIGQY-UHFFFAOYSA-K 0.000 description 1
SHSXSDIAQMURAH-UHFFFAOYSA-N C[Si](C)(C)C1=C(CC=C1)CCN(C)C Chemical compound C[Si](C)(C)C1=C(CC=C1)CCN(C)C SHSXSDIAQMURAH-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
101100237803 Mus musculus Mrln gene Proteins 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
241001104043 Syringa Species 0.000 description 1
235000004338 Syringa vulgaris Nutrition 0.000 description 1
229910010062 TiCl3 Inorganic materials 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
125000003968 arylidene group Chemical group [H]C(c)=* 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
238000010923 batch production Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
ABQPEYRVNHDPIO-UHFFFAOYSA-N bromo(dimethyl)borane Chemical compound CB(C)Br ABQPEYRVNHDPIO-UHFFFAOYSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
AGQPHHBPENBBIO-UHFFFAOYSA-M iodo(dioctyl)alumane Chemical compound [I-].CCCCCCCC[Al+]CCCCCCCC AGQPHHBPENBBIO-UHFFFAOYSA-M 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
238000005304 joining Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
DBKDYYFPDRPMPE-UHFFFAOYSA-N lithium;cyclopenta-1,3-diene Chemical compound [Li+].C=1C=C[CH-]C=1 DBKDYYFPDRPMPE-UHFFFAOYSA-N 0.000 description 1
KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical compound [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UNSDWONDAUAWPV-UHFFFAOYSA-N methylaluminum;oxane Chemical compound [Al]C.C1CCOCC1 UNSDWONDAUAWPV-UHFFFAOYSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002899 organoaluminium compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- C08F4/65908—Component covered by group C08F4/64 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
- C08F4/62—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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

NL1003020A 1996-05-03 1996-05-03 Cyclopentadieenverbinding met een niet-coördinerend anion. NL1003020C2 (nl)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
NL1003020A NL1003020C2 (nl)	1996-05-03	1996-05-03	Cyclopentadieenverbinding met een niet-coördinerend anion.
EP97919751A EP0896592A1 (fr)	1996-05-03	1997-04-28	Compose de cyclopentadiene a anion non coordinateur
PCT/NL1997/000231 WO1997042231A1 (fr)	1996-05-03	1997-04-28	Compose de cyclopentadiene a anion non coordinateur
JP9539783A JP2000509739A (ja)	1996-05-03	1997-04-28	非配位アニオンを有するシクロペンタジエン化合物
AU24108/97A AU2410897A (en)	1996-05-03	1997-04-28	Cyclopentadiene compound with a non-coordinating anion

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1003020A NL1003020C2 (nl)	1996-05-03	1996-05-03	Cyclopentadieenverbinding met een niet-coördinerend anion.
NL1003020		1996-05-03

Publications (1)

Publication Number	Publication Date
NL1003020C2 true NL1003020C2 (nl)	1997-11-06

Family

ID=19762792

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1003020A NL1003020C2 (nl)	1996-05-03	1996-05-03	Cyclopentadieenverbinding met een niet-coördinerend anion.

Country Status (5)

Country	Link
EP (1)	EP0896592A1 (fr)
JP (1)	JP2000509739A (fr)
AU (1)	AU2410897A (fr)
NL (1)	NL1003020C2 (fr)
WO (1)	WO1997042231A1 (fr)

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WO1991014713A1 (fr) *	1990-03-20	1991-10-03	Exxon Chemical Patents Inc.	Systeme catalytique a productivite amelioree
US5198401A (en) *	1987-01-30	1993-03-30	Exxon Chemical Patents Inc.	Ionic metallocene catalyst compositions
EP0672689A1 (fr) *	1990-06-22	1995-09-20	Exxon Chemical Patents Inc.	Catalyseurs à base de métallocène monocyclopentadienylique dépourvus d'aluminium destinés à la polymérisation d'oléfines
WO1995029940A1 (fr) *	1994-04-28	1995-11-09	Exxon Chemical Patents Inc.	Catalyseurs cationiques et procede d'utilisation de ces catalyseurs

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DE19506557A1 (de) *	1995-02-24	1996-08-29	Basf Ag	Metallocenkomplexe mit kationischer Brücke

1996
- 1996-05-03 NL NL1003020A patent/NL1003020C2/nl not_active IP Right Cessation
1997
- 1997-04-28 WO PCT/NL1997/000231 patent/WO1997042231A1/fr not_active Ceased
- 1997-04-28 EP EP97919751A patent/EP0896592A1/fr not_active Withdrawn
- 1997-04-28 AU AU24108/97A patent/AU2410897A/en not_active Abandoned
- 1997-04-28 JP JP9539783A patent/JP2000509739A/ja active Pending

Patent Citations (4)

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Publication number	Priority date	Publication date	Assignee	Title
US5198401A (en) *	1987-01-30	1993-03-30	Exxon Chemical Patents Inc.	Ionic metallocene catalyst compositions
WO1991014713A1 (fr) *	1990-03-20	1991-10-03	Exxon Chemical Patents Inc.	Systeme catalytique a productivite amelioree
EP0672689A1 (fr) *	1990-06-22	1995-09-20	Exxon Chemical Patents Inc.	Catalyseurs à base de métallocène monocyclopentadienylique dépourvus d'aluminium destinés à la polymérisation d'oléfines
WO1995029940A1 (fr) *	1994-04-28	1995-11-09	Exxon Chemical Patents Inc.	Catalyseurs cationiques et procede d'utilisation de ces catalyseurs

Also Published As

Publication number	Publication date
AU2410897A (en)	1997-11-26
WO1997042231A1 (fr)	1997-11-13
JP2000509739A (ja)	2000-08-02
EP0896592A1 (fr)	1999-02-17

Legal Events

Date	Code	Title	Description
1998-01-05	PD2B	A search report has been drawn up
2001-02-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20001201

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