JP4864176B2 - ポリオレフィン製造 - Google Patents
ポリオレフィン製造 Download PDFInfo
- Publication number
- JP4864176B2 JP4864176B2 JP51283599A JP51283599A JP4864176B2 JP 4864176 B2 JP4864176 B2 JP 4864176B2 JP 51283599 A JP51283599 A JP 51283599A JP 51283599 A JP51283599 A JP 51283599A JP 4864176 B2 JP4864176 B2 JP 4864176B2
- Authority
- JP
- Japan
- Prior art keywords
- substituent
- cyclopentadienyl
- catalyst component
- formula
- fluorenyl
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- 229920000098 polyolefin Polymers 0.000 title abstract description 52
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 239000012968 metallocene catalyst Substances 0.000 claims abstract description 25
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 55
- -1 polypropylene Polymers 0.000 claims description 41
- 239000004743 Polypropylene Substances 0.000 claims description 21
- 229920001155 polypropylene Polymers 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 40
- 239000000178 monomer Substances 0.000 abstract description 22
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 150000003624 transition metals Chemical class 0.000 abstract description 4
- 229910052720 vanadium Inorganic materials 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003446 ligand Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 238000009826 distribution Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000001294 propane Substances 0.000 description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 11
- UNGLAWCETLUCRC-UHFFFAOYSA-N 3-tert-butyl-1-methyl-5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=C(C(C)(C)C)C=C1C UNGLAWCETLUCRC-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 229920001576 syndiotactic polymer Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- WXACXMWYHXOSIX-UHFFFAOYSA-N 5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC=C1 WXACXMWYHXOSIX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229910007928 ZrCl2 Inorganic materials 0.000 description 4
- SFFPDELEUCQBAZ-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C Chemical compound [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C SFFPDELEUCQBAZ-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- 238000003780 insertion Methods 0.000 description 4
- 230000037431 insertion Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- SASHQTCWYFBLSG-UHFFFAOYSA-N 1,3-dimethyl-5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=C(C)C=C1C SASHQTCWYFBLSG-UHFFFAOYSA-N 0.000 description 3
- YPEOCTSXLWIZSO-UHFFFAOYSA-N 1,3-dimethylcyclopenta-1,3-diene Chemical group CC1=CC(C)=CC1 YPEOCTSXLWIZSO-UHFFFAOYSA-N 0.000 description 3
- HDHYMLWPVAELKP-UHFFFAOYSA-N 2-methyl-5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC(C)=C1 HDHYMLWPVAELKP-UHFFFAOYSA-N 0.000 description 3
- FFEXBNSBUHRMOY-UHFFFAOYSA-N 2-tert-butyl-5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC(C(C)(C)C)=C1 FFEXBNSBUHRMOY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- BULLHRADHZGONG-UHFFFAOYSA-N [cyclopenta-2,4-dien-1-ylidene(phenyl)methyl]benzene Chemical compound C1=CC=CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 BULLHRADHZGONG-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920001585 atactic polymer Polymers 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000002234 fulvenes Chemical class 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 3
- 229920001580 isotactic polymer Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- NWFVDKHZNWEXAD-UHFFFAOYSA-N 1-tert-butylcyclopenta-1,3-diene Chemical compound CC(C)(C)C1=CC=CC1 NWFVDKHZNWEXAD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical compound C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- BTYYMHCITNDCIE-UHFFFAOYSA-N [(3-methylcyclopenta-2,4-dien-1-ylidene)-phenylmethyl]benzene Chemical compound C1=CC(C)=CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 BTYYMHCITNDCIE-UHFFFAOYSA-N 0.000 description 2
- KSFWLENEFREVLY-UHFFFAOYSA-N [(3-tert-butylcyclopenta-2,4-dien-1-ylidene)-phenylmethyl]benzene Chemical group C1=CC(C(C)(C)C)=CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 KSFWLENEFREVLY-UHFFFAOYSA-N 0.000 description 2
- CXVLEBKAGHPEOL-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C CXVLEBKAGHPEOL-UHFFFAOYSA-L 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000006467 substitution reaction Methods 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
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- ATPNEAQEWYMEJG-UHFFFAOYSA-N 1-propyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(CCC)=CC=C2 ATPNEAQEWYMEJG-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZQAVYZUJEOUXBV-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-yl-1-(2,2-diphenylpropyl)-9H-fluorene Chemical group C1(=CC=CC=C1)C(CC1=C(C=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1)(C)C1=CC=CC=C1 ZQAVYZUJEOUXBV-UHFFFAOYSA-N 0.000 description 1
- DCCWRGRZJDNVSH-UHFFFAOYSA-N 3,6-ditert-butyl-1-(2,2-diphenylpropyl)-2-(3-methylcyclopenta-2,4-dien-1-yl)-9H-fluorene Chemical group C1(=CC=CC=C1)C(CC1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C)(C)C1=CC=CC=C1 DCCWRGRZJDNVSH-UHFFFAOYSA-N 0.000 description 1
- IRPBPEMAIMPOLM-UHFFFAOYSA-N 3,6-ditert-butyl-1-propyl-9H-fluorene Chemical compound C(C)(C)(C)C=1C=C(C=2CC3=CC=C(C=C3C2C1)C(C)(C)C)CCC IRPBPEMAIMPOLM-UHFFFAOYSA-N 0.000 description 1
- STCFWWRQQWHBIB-UHFFFAOYSA-N 3,6-ditert-butyl-2-cyclopenta-2,4-dien-1-yl-1-(2,2-diphenylpropyl)-9H-fluorene Chemical compound C1(=CC=CC=C1)C(CC1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=CC=C1)(C)C1=CC=CC=C1 STCFWWRQQWHBIB-UHFFFAOYSA-N 0.000 description 1
- CHCCBPDEADMNCI-UHFFFAOYSA-N 3-Methyl-2-cyclopenten-1-one Chemical compound CC1=CC(=O)CC1 CHCCBPDEADMNCI-UHFFFAOYSA-N 0.000 description 1
- FSJVREFHLVPDCB-UHFFFAOYSA-N 3-tert-butyl-1-methylcyclopenta-1,3-diene Chemical compound CC1=CC(C(C)(C)C)=CC1 FSJVREFHLVPDCB-UHFFFAOYSA-N 0.000 description 1
- GKQLEZIWGSTOGT-UHFFFAOYSA-N 6,6-dimethylhepta-2,4-diene Chemical group CC=CC=CC(C)(C)C GKQLEZIWGSTOGT-UHFFFAOYSA-N 0.000 description 1
- 0 CC1C(C(C)(C)C)=CC(C)[C@@](C)*1C Chemical compound CC1C(C(C)(C)C)=CC(C)[C@@](C)*1C 0.000 description 1
- VPEOMMCDLUHYDJ-UHFFFAOYSA-N C[Si](C1=CC(C=C1)[Zr]C1C2=CC=CC=C2C=2C=CC=CC1=2)(C)C Chemical compound C[Si](C1=CC(C=C1)[Zr]C1C2=CC=CC=C2C=2C=CC=CC1=2)(C)C VPEOMMCDLUHYDJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- YGCRGDSKOISQCD-UHFFFAOYSA-N [3-(1-benzhydryl-3,6-ditert-butyl-9H-fluoren-2-yl)cyclopenta-1,4-dien-1-yl]-trimethylsilane Chemical compound C1(=CC=CC=C1)C(C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C)C1=CC=CC=C1 YGCRGDSKOISQCD-UHFFFAOYSA-N 0.000 description 1
- AMCKLLAQXYZTFK-UHFFFAOYSA-N [3-[3,6-ditert-butyl-1-(2,2-diphenylpropyl)-9H-fluoren-2-yl]cyclopenta-1,4-dien-1-yl]-trimethylsilane Chemical group C1(=CC=CC=C1)C(CC1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C)(C)C1=CC=CC=C1 AMCKLLAQXYZTFK-UHFFFAOYSA-N 0.000 description 1
- SBBYPXXDIWCGAY-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C Chemical compound [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C SBBYPXXDIWCGAY-UHFFFAOYSA-L 0.000 description 1
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- KWGLTIIXZWOTRQ-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C Chemical compound [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)[Si](C)(C)C KWGLTIIXZWOTRQ-UHFFFAOYSA-L 0.000 description 1
- JLJVWKXUHRWHLL-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1C)C Chemical compound [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1C)C JLJVWKXUHRWHLL-UHFFFAOYSA-L 0.000 description 1
- VLDPTMBJTPIMHL-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C(C)(C)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=CC=C1 VLDPTMBJTPIMHL-UHFFFAOYSA-L 0.000 description 1
- NXFSPKRQHGRAAL-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)[Zr+2](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C(C)(C)[Zr+2](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 NXFSPKRQHGRAAL-UHFFFAOYSA-L 0.000 description 1
- XIFYCIQJEHGEIL-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C XIFYCIQJEHGEIL-UHFFFAOYSA-L 0.000 description 1
- FTTQVBWFWBCVSY-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C(C)(C)C Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=C(C=C1)C(C)(C)C FTTQVBWFWBCVSY-UHFFFAOYSA-L 0.000 description 1
- CIKNIKRDPZSBKL-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr+2]C1=C(C(=CC=2C3=CC(=CC=C3CC1=2)C(C)(C)C)C(C)(C)C)C1C=CC=C1 CIKNIKRDPZSBKL-UHFFFAOYSA-L 0.000 description 1
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 1
- IBXOUIJJTMLHBU-UHFFFAOYSA-L [Cl-].[Cl-].[Zr+2].C(C)(C)=CC(C)(C)C1=CC(C(=C1)C)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound [Cl-].[Cl-].[Zr+2].C(C)(C)=CC(C)(C)C1=CC(C(=C1)C)C1=CC=CC=2C3=CC=CC=C3CC12 IBXOUIJJTMLHBU-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- IDAPTOGYAAQMGT-UHFFFAOYSA-N diphenylmethylbenzene borate Chemical compound [O-]B([O-])[O-].C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 IDAPTOGYAAQMGT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000007613 slurry method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Images
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
-
- 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
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1999/001094 WO2000049029A1 (en) | 1999-02-19 | 1999-02-19 | Polyolefin production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002510358A JP2002510358A (ja) | 2002-04-02 |
| JP2002510358A5 JP2002510358A5 (zh) | 2006-06-22 |
| JP4864176B2 true JP4864176B2 (ja) | 2012-02-01 |
Family
ID=8167219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51283599A Expired - Fee Related JP4864176B2 (ja) | 1999-02-19 | 1999-02-19 | ポリオレフィン製造 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP4864176B2 (zh) |
| KR (1) | KR100663788B1 (zh) |
| CN (1) | CN1152056C (zh) |
| AT (1) | ATE271071T1 (zh) |
| AU (2) | AU3141199A (zh) |
| BR (1) | BR0008312B1 (zh) |
| CA (1) | CA2371835C (zh) |
| DE (1) | DE60012166T2 (zh) |
| ES (1) | ES2223460T3 (zh) |
| RU (1) | RU2244721C2 (zh) |
| WO (2) | WO2000049029A1 (zh) |
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 |
| EP1138687B1 (en) * | 1999-10-08 | 2007-04-11 | Mitsui Chemicals, Inc. | Metallocenes, their preparation, olefin polymerisation catalysts and a process for producing polyolefins |
| EP1179553B1 (en) * | 2000-08-07 | 2005-06-08 | Total Petrochemicals Research Feluy | Polyolefin production |
| JP5000070B2 (ja) * | 2001-03-15 | 2012-08-15 | 三井化学株式会社 | ポリプロピレン樹脂組成物からなる自動車部品 |
| US7488789B2 (en) | 2003-03-28 | 2009-02-10 | Mitsui Chemicals, Inc. | Propylene copolymer, polypropylene composition, and uses thereof, transition metal compounds and catalyst 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 |
| ES2347452T3 (es) * | 2004-08-30 | 2010-10-29 | Mitsui Chemicals, Inc. | Proceso para producir un polimero de propileno. |
| EP1900744A4 (en) * | 2005-05-25 | 2010-10-20 | Mitsui Chemicals Inc | TRANSITION METAL COMPOUND, OLEFIN POLYMERIZATION CATALYST, AND PROCESS FOR PRODUCING OLEFIN POLYMER |
| EP1734059A1 (en) * | 2005-06-13 | 2006-12-20 | Total Petrochemicals Research Feluy | Carbon-bridged cyclopentadienyl-fluorenyl ligands |
| EP1734058A1 (en) * | 2005-06-13 | 2006-12-20 | Total Petrochemicals Research Feluy | Ethylene and alpha-olefins polymerisation catalyst system based on fluorenyl ligand |
| JPWO2008059974A1 (ja) | 2006-11-17 | 2010-03-04 | 三井化学株式会社 | シンジオタクティックプロピレン系重合体の製造方法 |
| US10370465B2 (en) | 2007-01-18 | 2019-08-06 | Prime Polymer Co., Ltd. | Propylene homopolymer for stress-resistant molded article, composition containing the polymer, and stress-resistant molded articles 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 (zh) * | 2014-12-03 | 2018-12-14 | 亚培烯科技（杭州）有限公司 | 一种茂金属线性低密度聚乙烯催化剂及其制备方法和应用 |
| CN115677879B (zh) * | 2021-07-31 | 2024-07-30 | 华为技术有限公司 | 环烯烃共聚物制备用催化剂、环烯烃共聚物的制备方法、环烯烃共聚物及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69024442T2 (de) * | 1989-04-18 | 1996-08-01 | Mitsui Toatsu Chemicals | Syndiotaktische polypropylen-harzzusammensetzung |
| 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 (ja) * | 1995-06-02 | 1996-12-10 | Chisso Corp | 高立体規則性ポリプロピレン |
| ATE225359T1 (de) * | 1995-12-18 | 2002-10-15 | Basell Polyolefine Gmbh | Verfahren zur abreicherung von nebenprodukten in produktgemischen |
| EP0824112B1 (de) * | 1996-08-13 | 2006-05-10 | Basell Polyolefine GmbH | Geträgerte chemische Verbindung |
| 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/ja not_active Expired - Fee Related
-
2000
- 2000-02-18 RU RU2001124801/04A patent/RU2244721C2/ru not_active IP Right Cessation
- 2000-02-18 AT AT00906358T patent/ATE271071T1/de not_active IP Right Cessation
- 2000-02-18 ES ES00906358T patent/ES2223460T3/es not_active Expired - Lifetime
- 2000-02-18 KR KR1020017010519A patent/KR100663788B1/ko not_active IP Right Cessation
- 2000-02-18 BR BRPI0008312-7A patent/BR0008312B1/pt not_active IP Right Cessation
- 2000-02-18 CA CA2371835A patent/CA2371835C/en not_active Expired - Fee Related
- 2000-02-18 CN CNB008059535A patent/CN1152056C/zh not_active Expired - Fee Related
- 2000-02-18 AU AU28062/00A patent/AU2806200A/en not_active Abandoned
- 2000-02-18 DE DE60012166T patent/DE60012166T2/de not_active Expired - Lifetime
- 2000-02-18 WO PCT/EP2000/001378 patent/WO2000049056A1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020002471A (ko) | 2002-01-09 |
| DE60012166T2 (de) | 2005-09-08 |
| CN1346373A (zh) | 2002-04-24 |
| BR0008312B1 (pt) | 2011-06-14 |
| RU2244721C2 (ru) | 2005-01-20 |
| WO2000049029A1 (en) | 2000-08-24 |
| AU3141199A (en) | 2000-09-04 |
| BR0008312A (pt) | 2002-01-22 |
| ATE271071T1 (de) | 2004-07-15 |
| CA2371835C (en) | 2010-07-27 |
| WO2000049056A1 (en) | 2000-08-24 |
| DE60012166D1 (de) | 2004-08-19 |
| ES2223460T3 (es) | 2005-03-01 |
| CA2371835A1 (en) | 2000-08-24 |
| AU2806200A (en) | 2000-09-04 |
| JP2002510358A (ja) | 2002-04-02 |
| CN1152056C (zh) | 2004-06-02 |
| KR100663788B1 (ko) | 2007-01-03 |
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