DE60202524T2 - Katalysatorsystem für die polymerisierung von olefinen - Google Patents
Katalysatorsystem für die polymerisierung von olefinen Download PDFInfo
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- DE60202524T2 DE60202524T2 DE60202524T DE60202524T DE60202524T2 DE 60202524 T2 DE60202524 T2 DE 60202524T2 DE 60202524 T DE60202524 T DE 60202524T DE 60202524 T DE60202524 T DE 60202524T DE 60202524 T2 DE60202524 T2 DE 60202524T2
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 34
- 239000003054 catalyst Substances 0.000 title claims description 38
- -1 transition metal organometallic compound Chemical class 0.000 claims abstract description 109
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000002841 Lewis acid Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 11
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 21
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 20
- 150000001336 alkenes Chemical class 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 230000000737 periodic effect Effects 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001255 actinides Chemical group 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 238000009877 rendering Methods 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000003623 transition metal compounds Chemical class 0.000 claims 1
- 239000004711 α-olefin Substances 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 229910052726 zirconium Inorganic materials 0.000 description 50
- 239000007983 Tris buffer Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
- 239000000460 chlorine Substances 0.000 description 43
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 43
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229930192474 thiophene Natural products 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000012190 activator Substances 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KHSYDHMWELMAHM-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5-(2,3,4,5-tetrafluorophenyl)benzene Chemical group FC1=C(F)C(F)=CC(C=2C(=C(F)C(F)=C(F)C=2)F)=C1F KHSYDHMWELMAHM-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
- LLWIHPJMYMZACK-UHFFFAOYSA-N 1,2,3,5-tetrafluoro-4-(2,3,4,6-tetrafluorophenyl)benzene Chemical group FC1=C(F)C(F)=CC(F)=C1C1=C(F)C=C(F)C(F)=C1F LLWIHPJMYMZACK-UHFFFAOYSA-N 0.000 description 3
- QWCHHUZAAGRHDB-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3-(2,3,5,6-tetrafluorophenyl)benzene Chemical group FC1=CC(F)=C(F)C(C=2C(=C(F)C=C(F)C=2F)F)=C1F QWCHHUZAAGRHDB-UHFFFAOYSA-N 0.000 description 3
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- XRPDDDRNQJNHLQ-UHFFFAOYSA-N 2-ethyl-1h-pyrrole Chemical compound CCC1=CC=CN1 XRPDDDRNQJNHLQ-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- ZOICEQJZAWJHSI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boron Chemical compound [B]C1=C(F)C(F)=C(F)C(F)=C1F ZOICEQJZAWJHSI-UHFFFAOYSA-N 0.000 description 2
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 229920001198 elastomeric copolymer Polymers 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011630 iodine Chemical group 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 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 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- HKVFGFGPRISDFM-UHFFFAOYSA-N tris(2,3,3-trimethylbutyl)alumane Chemical compound CC(C)(C)C(C)C[Al](CC(C)C(C)(C)C)CC(C)C(C)(C)C HKVFGFGPRISDFM-UHFFFAOYSA-N 0.000 description 2
- SSEXLBWMXFFGTD-UHFFFAOYSA-N tris(2,3-dimethylbutyl)alumane Chemical compound CC(C)C(C)C[Al](CC(C)C(C)C)CC(C)C(C)C SSEXLBWMXFFGTD-UHFFFAOYSA-N 0.000 description 2
- WUGMXCQCNQHHDC-UHFFFAOYSA-N tris(2,3-dimethylheptyl)alumane Chemical compound CCCCC(C)C(C)C[Al](CC(C)C(C)CCCC)CC(C)C(C)CCCC WUGMXCQCNQHHDC-UHFFFAOYSA-N 0.000 description 2
- VGONMIOMLRCRSS-UHFFFAOYSA-N tris(2,3-dimethylhexyl)alumane Chemical compound CCCC(C)C(C)C[Al](CC(C)C(C)CCC)CC(C)C(C)CCC VGONMIOMLRCRSS-UHFFFAOYSA-N 0.000 description 2
- BENYMJNPVWYYES-UHFFFAOYSA-N tris(2,3-dimethylpentyl)alumane Chemical compound CCC(C)C(C)C[Al](CC(C)C(C)CC)CC(C)C(C)CC BENYMJNPVWYYES-UHFFFAOYSA-N 0.000 description 2
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 2
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- IEKMPJDJWCSGKX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8,9,9-decafluorofluorene Chemical compound FC1(F)C2=C(F)C(F)=C(F)C(F)=C2C2=C1C(F)=C(F)C(F)=C2F IEKMPJDJWCSGKX-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 1
- FSWNZCWHTXTQBY-UHFFFAOYSA-N 4,6-dimethylhept-1-ene Chemical compound CC(C)CC(C)CC=C FSWNZCWHTXTQBY-UHFFFAOYSA-N 0.000 description 1
- PGFVYIIJNFGCFU-UHFFFAOYSA-N 5H-benzo[b][1]benzoborole Chemical class C1=CC=C2BC3=CC=CC=C3C2=C1 PGFVYIIJNFGCFU-UHFFFAOYSA-N 0.000 description 1
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- LPCCJAWIWJAPDZ-UHFFFAOYSA-N C[SiH](C)[Ti](C)C Chemical compound C[SiH](C)[Ti](C)C LPCCJAWIWJAPDZ-UHFFFAOYSA-N 0.000 description 1
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- 238000004639 Schlenk technique Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
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- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-O methyl(phenyl)azanium Chemical compound C[NH2+]C1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-O 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- HKABSXHXKCTVGW-UHFFFAOYSA-N n,2,4,6-tetramethylaniline Chemical compound CNC1=C(C)C=C(C)C=C1C HKABSXHXKCTVGW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical class CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- JMNFGPITPHPZOF-UHFFFAOYSA-N tris[3-(2,3,4,5,6-pentafluorophenyl)-1H-indol-2-yl] borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(C1=CC=CC=C1N1)=C1OB(OC1=C(C2=CC=CC=C2N1)C=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(C=2C(=C(F)C(F)=C(F)C=2F)F)C2=CC=CC=C2N1 JMNFGPITPHPZOF-UHFFFAOYSA-N 0.000 description 1
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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201904 | 2001-05-21 | ||
| EP01201904 | 2001-05-21 | ||
| PCT/EP2002/005087 WO2002102811A1 (en) | 2001-05-21 | 2002-05-07 | Catalyst system for the polymerization of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60202524D1 DE60202524D1 (de) | 2005-02-10 |
| DE60202524T2 true DE60202524T2 (de) | 2005-06-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60202524T Expired - Fee Related DE60202524T2 (de) | 2001-05-21 | 2002-05-07 | Katalysatorsystem für die polymerisierung von olefinen |
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|---|---|
| US (1) | US7417006B2 (https=) |
| EP (1) | EP1392705B1 (https=) |
| JP (1) | JP4173803B2 (https=) |
| AT (1) | ATE286505T1 (https=) |
| DE (1) | DE60202524T2 (https=) |
| WO (1) | WO2002102811A1 (https=) |
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| JP4332029B2 (ja) * | 2001-06-12 | 2009-09-16 | バーゼル・ポリオレフィン・ゲーエムベーハー | １−ブテンの重合方法 |
| WO2002100908A1 (en) * | 2001-06-12 | 2002-12-19 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| EP1406969A1 (en) * | 2001-07-17 | 2004-04-14 | Basell Polyolefine GmbH | Multistep process for the (co)polymerization of olefins |
| US6703338B2 (en) | 2002-06-28 | 2004-03-09 | Univation Technologies, Llc | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
| US6989341B2 (en) | 2002-01-28 | 2006-01-24 | Univation Technologies, Llc | Halogen substituted catalyst system for olefin polymerization |
| DE60329523D1 (de) * | 2002-12-04 | 2009-11-12 | Basell Polyolefine Gmbh | 1-Buten-Copolymere und Herstellungsverfahren dafür |
| US7589160B2 (en) * | 2002-12-04 | 2009-09-15 | Basell Polyolefine Gmbh | Process for preparing 1-butene polymers |
| US7220695B2 (en) | 2004-01-07 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Supported activator |
| US7741417B2 (en) | 2004-01-07 | 2010-06-22 | Exxonmobil Chemical Patents Inc. | Preparation of polymerization catalyst activators utilizing indole-modified silica supports |
| JP4897670B2 (ja) | 2004-05-04 | 2012-03-14 | バーゼル・ポリオレフィン・ゲーエムベーハー | アタクチック１−ブテンポリマー類の製造方法 |
| RU2007118505A (ru) * | 2004-10-18 | 2008-11-27 | Базелль Полиолефин Италия С.Р.Л. (It) | (со)полимеры бутена-1 с низкой изотактичностью |
| ATE501183T1 (de) * | 2004-10-21 | 2011-03-15 | Basell Polyolefine Gmbh | 1-buten-polymer und herstellungsverfahren dafür |
| EP1655314A1 (en) * | 2004-11-09 | 2006-05-10 | Basell Polyolefine GmbH | Process for the preparation of 1-butene/propylene copolymers |
| EP1814922A1 (en) * | 2004-11-22 | 2007-08-08 | Basell Polyolefine GmbH | Propylene based terpolymers |
| JP2008523231A (ja) * | 2004-12-13 | 2008-07-03 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | ポリオレフィン繊維 |
| ATE502080T1 (de) * | 2005-02-03 | 2011-04-15 | Basell Polyolefine Gmbh | Verfahren zur herstellung von warmgeformten artikeln |
| EP1858934B1 (en) | 2005-03-18 | 2013-04-24 | Basell Polyolefine GmbH | Metallocene compounds |
| KR101293405B1 (ko) | 2005-03-18 | 2013-08-05 | 바젤 폴리올레핀 게엠베하 | 메탈로센 화합물 |
| WO2006100258A1 (en) * | 2005-03-23 | 2006-09-28 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7728086B2 (en) | 2005-03-23 | 2010-06-01 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7964679B2 (en) | 2005-05-03 | 2011-06-21 | Basell Poliolefine Italia S.R.L. | Process for the polymerization of alpha olefins |
| EP1879959B1 (en) | 2005-05-11 | 2011-07-06 | Basell Poliolefine Italia S.r.l. | Polymerization process for preparing polyolefin blends |
| US8051611B2 (en) * | 2005-06-24 | 2011-11-08 | Dryvit Systems, Inc. | Exterior insulation and finish system and method and tool for installing same |
| CN101291986B (zh) | 2005-10-21 | 2011-12-14 | 巴塞尔聚烯烃股份有限公司 | 用于注射模塑的聚丙烯 |
| ATE469928T1 (de) * | 2005-10-21 | 2010-06-15 | Basell Polyolefine Gmbh | Statistische polypropylencopolymere mit hohen schmelzflussraten für spritzguss- und schmelzblasanwendungen |
| EP1940889B1 (en) * | 2005-10-21 | 2010-06-02 | Basell Polyolefine GmbH | Propylene polymers |
| US20090017710A1 (en) * | 2006-02-02 | 2009-01-15 | Basell Polyolefine Gmbh | Propylene Melt Blown Resins, Propylene Melt Blown Resin Fibers and Non-Woven Fabric Made From the Same, and Methods of Making the Same |
| US8343602B2 (en) * | 2006-02-23 | 2013-01-01 | Basell Poliolefine Italia, s.r.l. | Propylene polymers for injection molding applications |
| EP2010580B1 (en) | 2006-04-21 | 2016-07-13 | Basell Polyolefine GmbH | Process for the preparation of ethylene copolymers |
| WO2007122097A1 (en) * | 2006-04-21 | 2007-11-01 | Basell Polyolefine Gmbh | Process for the preparation of ethylene propylene copolymers |
| US8022005B2 (en) * | 2007-11-08 | 2011-09-20 | Exxonmobil Chemical Patents Inc. | Halogen substituted heterocyclic heteroatom containing ligands-alumoxane activation of metallocenes |
| US9321854B2 (en) | 2013-10-29 | 2016-04-26 | Exxonmobil Chemical Patents Inc. | Aluminum alkyl with C5 cyclic and pendent olefin polymerization catalyst |
| US10618988B2 (en) | 2015-08-31 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| CN107922527A (zh) | 2015-08-31 | 2018-04-17 | 埃克森美孚化学专利公司 | 用于聚烯烃反应的具有悬垂烯烃的铝烷基 |
| EP3344385A4 (en) | 2015-08-31 | 2019-08-14 | ExxonMobil Chemical Patents Inc. | ALUMINUM ALKYLE WITH HANGING OLEFINS ON SOUND |
| US10059788B2 (en) | 2016-04-29 | 2018-08-28 | Exxonmobil Chemical Patents Inc. | Organoaluminum activators on clays |
| US10562987B2 (en) | 2016-06-30 | 2020-02-18 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| US10626200B2 (en) | 2017-02-28 | 2020-04-21 | Exxonmobil Chemical Patents Inc. | Branched EPDM polymers produced via use of vinyl transfer agents and processes for production thereof |
| US10676551B2 (en) | 2017-03-01 | 2020-06-09 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
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| US5324800A (en) | 1983-06-06 | 1994-06-28 | Exxon Chemical Patents Inc. | Process and catalyst for polyolefin density and molecular weight control |
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| US5055438A (en) | 1989-09-13 | 1991-10-08 | Exxon Chemical Patents, Inc. | Olefin polymerization catalysts |
| US5384299A (en) | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| IL95278A0 (en) | 1989-08-03 | 1991-06-30 | Exxon Chemical Patents Inc | Very high molecular weight polyethylene |
| 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 |
| ES2071888T3 (es) | 1990-11-12 | 1995-07-01 | Hoechst Ag | Bisindenilmetalocenos sustituidos en posicion 2, procedimiento para su preparacion y su utilizacion como catalizadores en la polimerizacion de olefinas. |
| US5239022A (en) | 1990-11-12 | 1993-08-24 | Hoechst Aktiengesellschaft | Process for the preparation of a syndiotactic polyolefin |
| EP0485822B1 (de) | 1990-11-12 | 1996-07-03 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung eines hochmolekularen Olefinpolymers |
| US5243001A (en) | 1990-11-12 | 1993-09-07 | Hoechst Aktiengesellschaft | Process for the preparation of a high molecular weight olefin polymer |
| EP0722956B1 (de) | 1990-11-12 | 2001-08-16 | Basell Polyolefine GmbH | Verfahren zur Herstellung eines Olefinpolymers |
| 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 |
| IT1272923B (it) | 1995-01-23 | 1997-07-01 | Spherilene Srl | Composti metallocenici,procedimento per la loro preparazione,e loro utilizzo in catalizzatori per la polimerizzazione delle olefine |
| KR100418168B1 (ko) | 1995-01-24 | 2004-02-14 | 이.아이,듀우판드네모아앤드캄파니 | 중합 방법 |
| KR19980702645A (ko) | 1995-03-08 | 1998-08-05 | 알베르투스 빌헬무스 요아네스 쩨스트라텐 | 촉매 조성물내 브리지된 비스-아미도 4족 금속 화합물 |
| US5714556A (en) | 1995-06-30 | 1998-02-03 | E. I. Dupont De Nemours And Company | Olefin polymerization process |
| PL188107B1 (pl) | 1996-11-15 | 2004-12-31 | Montell Technology Company Bv | Metalocen, układ katalityczny do polimeryzacji, kationowe metaloceny, ligand oraz sposób polimeryzacji |
| JP2002514252A (ja) | 1997-03-10 | 2002-05-14 | イーストマン ケミカル カンパニー | 第８〜１０族遷移金属を含むオレフィン重合触媒、二座配位子、このような触媒の使用方法及びそれから得られるポリマー |
| US6559252B1 (en) | 1997-10-29 | 2003-05-06 | Basell Technology Company Bv | Catalysts and processes for the polymerization of olefins |
| AU1870999A (en) | 1997-11-12 | 1999-05-31 | Montell Technology Company B.V. | Metallocenes and catalysts for olefin-polymerisation |
| AU749065B2 (en) | 1998-02-20 | 2002-06-20 | Dow Chemical Company, The | Catalyst activators comprising expanded anions |
| KR20010021604A (ko) | 1998-05-08 | 2001-03-15 | 간디 지오프레이 에이치. | 메탈로센, 리간드 및 올레핀 중합 방법 |
| ES2217859T3 (es) * | 1998-12-12 | 2004-11-01 | Basell Polyolefine Gmbh | Compuesto de metal de transicion zwitterionico, neutro. |
| DE60103702T2 (de) * | 2000-02-24 | 2005-06-23 | Basell Polyolefine Gmbh | Organometallische Verbindungen die als Cokatalysator bei der Polymerisation von Olefinen verwendet ist |
| CN100532400C (zh) * | 2002-07-09 | 2009-08-26 | 巴塞尔聚烯烃股份有限公司 | 用于烯烃聚合的催化剂体系 |
-
2002
- 2002-05-07 US US10/478,346 patent/US7417006B2/en not_active Expired - Fee Related
- 2002-05-07 AT AT02738045T patent/ATE286505T1/de not_active IP Right Cessation
- 2002-05-07 DE DE60202524T patent/DE60202524T2/de not_active Expired - Fee Related
- 2002-05-07 WO PCT/EP2002/005087 patent/WO2002102811A1/en not_active Ceased
- 2002-05-07 EP EP02738045A patent/EP1392705B1/en not_active Expired - Lifetime
- 2002-05-07 JP JP2003506283A patent/JP4173803B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1392705B1 (en) | 2005-01-05 |
| WO2002102811A1 (en) | 2002-12-27 |
| JP4173803B2 (ja) | 2008-10-29 |
| JP2004533467A (ja) | 2004-11-04 |
| DE60202524D1 (de) | 2005-02-10 |
| ATE286505T1 (de) | 2005-01-15 |
| US7417006B2 (en) | 2008-08-26 |
| EP1392705A1 (en) | 2004-03-03 |
| US20040132612A1 (en) | 2004-07-08 |
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