JP4537587B2 - オレフィンの重合用成分および触媒 - Google Patents
オレフィンの重合用成分および触媒 Download PDFInfo
- Publication number
- JP4537587B2 JP4537587B2 JP2000605641A JP2000605641A JP4537587B2 JP 4537587 B2 JP4537587 B2 JP 4537587B2 JP 2000605641 A JP2000605641 A JP 2000605641A JP 2000605641 A JP2000605641 A JP 2000605641A JP 4537587 B2 JP4537587 B2 JP 4537587B2
- Authority
- JP
- Japan
- Prior art keywords
- glutaric acid
- ester
- catalyst component
- polymerization
- hydrogen
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 24
- 239000003054 catalyst Substances 0.000 title claims abstract description 23
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 14
- -1 diisopropyl beta-methyl glutarate Chemical compound 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 239000011949 solid catalyst Substances 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 14
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000010936 titanium Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- IOXXIAGQWNGBRO-UHFFFAOYSA-N dipropan-2-yl 3-methylpentanedioate Chemical compound CC(C)OC(=O)CC(C)CC(=O)OC(C)C IOXXIAGQWNGBRO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003609 titanium compounds Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 7
- 239000008096 xylene Substances 0.000 abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 5
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000011777 magnesium Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000011282 treatment Methods 0.000 description 9
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000011147 magnesium chloride Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- 150000003377 silicon compounds Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- 238000004438 BET method Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- XUKURXLOIDOIMG-UHFFFAOYSA-N bis(2-methylpropyl) 2-methylpentanedioate Chemical compound CC(C)COC(=O)CCC(C)C(=O)OCC(C)C XUKURXLOIDOIMG-UHFFFAOYSA-N 0.000 description 2
- SZKROOFLACXITG-UHFFFAOYSA-N bis(2-methylpropyl) 3-methylpentanedioate Chemical compound CC(C)COC(=O)CC(C)CC(=O)OCC(C)C SZKROOFLACXITG-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 2
- GLADVNXLFJLYNQ-UHFFFAOYSA-N diethyl 3-tert-butyl-3-methylpentanedioate Chemical compound CCOC(=O)CC(C)(C(C)(C)C)CC(=O)OCC GLADVNXLFJLYNQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- VFIOZKTXVHLWRA-UHFFFAOYSA-N (2-ethylpiperidin-1-yl)-dimethoxy-(1,1,1-trifluoropropan-2-yl)silane Chemical compound CCC1CCCCN1[Si](OC)(OC)C(C)C(F)(F)F VFIOZKTXVHLWRA-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- UVGKQRAGAYVWQV-UHFFFAOYSA-N 2,3-dimethylbutan-2-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C(C)C UVGKQRAGAYVWQV-UHFFFAOYSA-N 0.000 description 1
- KXAQKVGRILQGNM-UHFFFAOYSA-N 2-ethoxy-1-[1-(2-ethoxyacetyl)cyclopentyl]ethanone Chemical compound CCOCC(=O)C1(C(=O)COCC)CCCC1 KXAQKVGRILQGNM-UHFFFAOYSA-N 0.000 description 1
- PBBVQPMWCFJZJC-UHFFFAOYSA-N 2-ethoxy-1-[9-(2-ethoxyacetyl)fluoren-9-yl]ethanone Chemical compound C1=CC=C2C(C(=O)COCC)(C(=O)COCC)C3=CC=CC=C3C2=C1 PBBVQPMWCFJZJC-UHFFFAOYSA-N 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- ZBGXPVZJWPWGTH-UHFFFAOYSA-N CCCCC(CCC)(CC(=O)OCC(C)C)CC(=O)OCC(C)C Chemical compound CCCCC(CCC)(CC(=O)OCC(C)C)CC(=O)OCC(C)C ZBGXPVZJWPWGTH-UHFFFAOYSA-N 0.000 description 1
- VWQOAYDUANAVEN-UHFFFAOYSA-N CCCCC(CCC)(CC(=O)OCC)CC(=O)OCC Chemical compound CCCCC(CCC)(CC(=O)OCC)CC(=O)OCC VWQOAYDUANAVEN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DZUWTYQOXPUFGF-UHFFFAOYSA-N bis(2-methylpropyl) 2,4-dimethyl-3-phenylpentanedioate Chemical compound CC(C)COC(=O)C(C)C(C(C)C(=O)OCC(C)C)C1=CC=CC=C1 DZUWTYQOXPUFGF-UHFFFAOYSA-N 0.000 description 1
- DBDAZOSEXTWIFO-UHFFFAOYSA-N bis(2-methylpropyl) 2-ethyl-3-propan-2-ylpentanedioate Chemical compound CC(C)COC(=O)C(CC)C(C(C)C)CC(=O)OCC(C)C DBDAZOSEXTWIFO-UHFFFAOYSA-N 0.000 description 1
- VCVNYSQNDPZGRH-UHFFFAOYSA-N bis(2-methylpropyl) 2-methyl-3,3-bis(2-methylpropyl)pentanedioate Chemical compound CC(C)COC(=O)CC(CC(C)C)(CC(C)C)C(C)C(=O)OCC(C)C VCVNYSQNDPZGRH-UHFFFAOYSA-N 0.000 description 1
- ZCAAFLFWSVJZID-UHFFFAOYSA-N bis(2-methylpropyl) 2-methyl-3-phenylpentanedioate Chemical compound CC(C)COC(=O)CC(C(C)C(=O)OCC(C)C)C1=CC=CC=C1 ZCAAFLFWSVJZID-UHFFFAOYSA-N 0.000 description 1
- KVAWCEXIADXCNH-UHFFFAOYSA-N bis(2-methylpropyl) 3,3-bis(2-methylpropyl)pentanedioate Chemical compound CC(C)COC(=O)CC(CC(C)C)(CC(C)C)CC(=O)OCC(C)C KVAWCEXIADXCNH-UHFFFAOYSA-N 0.000 description 1
- ILCMXRLWVFOKMZ-UHFFFAOYSA-N bis(2-methylpropyl) 3,3-di(propan-2-yl)pentanedioate Chemical compound CC(C)COC(=O)CC(C(C)C)(C(C)C)CC(=O)OCC(C)C ILCMXRLWVFOKMZ-UHFFFAOYSA-N 0.000 description 1
- COLRABYNXANJRY-UHFFFAOYSA-N bis(2-methylpropyl) 3,3-diethylpentanedioate Chemical compound CC(C)COC(=O)CC(CC)(CC)CC(=O)OCC(C)C COLRABYNXANJRY-UHFFFAOYSA-N 0.000 description 1
- OSVDFYVHWKMVJL-UHFFFAOYSA-N bis(2-methylpropyl) 3,3-dimethylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(C)CC(=O)OCC(C)C OSVDFYVHWKMVJL-UHFFFAOYSA-N 0.000 description 1
- VKLUSDSQTRAAFL-UHFFFAOYSA-N bis(2-methylpropyl) 3-(2-methylpropyl)pentanedioate Chemical compound CC(C)COC(=O)CC(CC(C)C)CC(=O)OCC(C)C VKLUSDSQTRAAFL-UHFFFAOYSA-N 0.000 description 1
- WQJNDNHGWDZBCV-UHFFFAOYSA-N bis(2-methylpropyl) 3-butyl-3-ethylpentanedioate Chemical compound CC(C)COC(=O)CC(CC)(CCCC)CC(=O)OCC(C)C WQJNDNHGWDZBCV-UHFFFAOYSA-N 0.000 description 1
- XFUVNIZXZFJPJX-UHFFFAOYSA-N bis(2-methylpropyl) 3-butyl-3-methylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(CCCC)CC(=O)OCC(C)C XFUVNIZXZFJPJX-UHFFFAOYSA-N 0.000 description 1
- CBTMCEAIZXYKPS-UHFFFAOYSA-N bis(2-methylpropyl) 3-butyl-3-phenylpentanedioate Chemical compound CC(C)COC(=O)CC(CCCC)(CC(=O)OCC(C)C)C1=CC=CC=C1 CBTMCEAIZXYKPS-UHFFFAOYSA-N 0.000 description 1
- QBGPCJRPSRFFQK-UHFFFAOYSA-N bis(2-methylpropyl) 3-ethyl-3-(2-methylbutyl)pentanedioate Chemical compound CC(C)COC(=O)CC(CC)(CC(C)CC)CC(=O)OCC(C)C QBGPCJRPSRFFQK-UHFFFAOYSA-N 0.000 description 1
- COVRCJXUHDWJLU-UHFFFAOYSA-N bis(2-methylpropyl) 3-ethyl-3-methylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(CC)CC(=O)OCC(C)C COVRCJXUHDWJLU-UHFFFAOYSA-N 0.000 description 1
- SWOQHXMPKYETNY-UHFFFAOYSA-N bis(2-methylpropyl) 3-ethylpentanedioate Chemical compound CC(C)COC(=O)CC(CC)CC(=O)OCC(C)C SWOQHXMPKYETNY-UHFFFAOYSA-N 0.000 description 1
- LLCWNYZFFVWWLX-UHFFFAOYSA-N bis(2-methylpropyl) 3-methyl-3-(2-methylpropyl)pentanedioate Chemical compound CC(C)COC(=O)CC(C)(CC(C)C)CC(=O)OCC(C)C LLCWNYZFFVWWLX-UHFFFAOYSA-N 0.000 description 1
- VHZWYFAQXQZXKS-UHFFFAOYSA-N bis(2-methylpropyl) 3-methyl-3-phenylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(CC(=O)OCC(C)C)c1ccccc1 VHZWYFAQXQZXKS-UHFFFAOYSA-N 0.000 description 1
- HFYCFKOYMDLIRJ-UHFFFAOYSA-N bis(2-methylpropyl) 3-methyl-3-propan-2-ylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(C(C)C)CC(=O)OCC(C)C HFYCFKOYMDLIRJ-UHFFFAOYSA-N 0.000 description 1
- GSYXSCWMXBNRIR-UHFFFAOYSA-N bis(2-methylpropyl) 3-phenyl-3-propylpentanedioate Chemical compound CC(C)COC(=O)CC(CCC)(CC(=O)OCC(C)C)C1=CC=CC=C1 GSYXSCWMXBNRIR-UHFFFAOYSA-N 0.000 description 1
- HYLPEFVHIQLPGJ-UHFFFAOYSA-N bis(2-methylpropyl) 3-phenylpentanedioate Chemical compound CC(C)COC(=O)CC(CC(=O)OCC(C)C)C1=CC=CC=C1 HYLPEFVHIQLPGJ-UHFFFAOYSA-N 0.000 description 1
- RARMGMGGCVSHER-UHFFFAOYSA-N bis(2-methylpropyl) 3-propan-2-ylpentanedioate Chemical compound CC(C)COC(=O)CC(C(C)C)CC(=O)OCC(C)C RARMGMGGCVSHER-UHFFFAOYSA-N 0.000 description 1
- LGDKRVZNHOICQW-UHFFFAOYSA-N bis(2-methylpropyl) 3-tert-butyl-3-methylpentanedioate Chemical compound CC(C)COC(=O)CC(C)(C(C)(C)C)CC(=O)OCC(C)C LGDKRVZNHOICQW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- DXHKBVSWFIZEQJ-UHFFFAOYSA-N diethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate Chemical compound CCOC(=O)C1CCC(C)(C(=O)OCC)C1(C)C DXHKBVSWFIZEQJ-UHFFFAOYSA-N 0.000 description 1
- BTLDCJCPJNNUCE-UHFFFAOYSA-N diethyl 2,2-dimethyl-3-phenylpentanedioate Chemical compound CCOC(=O)CC(C(C)(C)C(=O)OCC)C1=CC=CC=C1 BTLDCJCPJNNUCE-UHFFFAOYSA-N 0.000 description 1
- FFINSFBXMLLIGO-UHFFFAOYSA-N diethyl 2-ethyl-3-propan-2-ylpentanedioate Chemical compound CCOC(=O)CC(C(C)C)C(CC)C(=O)OCC FFINSFBXMLLIGO-UHFFFAOYSA-N 0.000 description 1
- TZNJEVFTVMKVOV-UHFFFAOYSA-N diethyl 2-methyl-3,3-bis(2-methylpropyl)pentanedioate Chemical compound CCOC(=O)CC(CC(C)C)(CC(C)C)C(C)C(=O)OCC TZNJEVFTVMKVOV-UHFFFAOYSA-N 0.000 description 1
- RCWLYACRLACMBS-UHFFFAOYSA-N diethyl 2-methyl-3-phenylpentanedioate Chemical compound CCOC(=O)CC(C(C)C(=O)OCC)C1=CC=CC=C1 RCWLYACRLACMBS-UHFFFAOYSA-N 0.000 description 1
- WLPDFMHODWPRDJ-UHFFFAOYSA-N diethyl 3,3-bis(2-methylpropyl)pentanedioate Chemical compound CCOC(=O)CC(CC(C)C)(CC(C)C)CC(=O)OCC WLPDFMHODWPRDJ-UHFFFAOYSA-N 0.000 description 1
- WUVWZBXGFSPIMT-UHFFFAOYSA-N diethyl 3,3-di(propan-2-yl)pentanedioate Chemical compound CCOC(=O)CC(C(C)C)(C(C)C)CC(=O)OCC WUVWZBXGFSPIMT-UHFFFAOYSA-N 0.000 description 1
- HPBLUGODTPKVOI-UHFFFAOYSA-N diethyl 3,3-diethylpentanedioate Chemical compound CCOC(=O)CC(CC)(CC)CC(=O)OCC HPBLUGODTPKVOI-UHFFFAOYSA-N 0.000 description 1
- WKLBAFKOKJVNMN-UHFFFAOYSA-N diethyl 3,3-dimethylpentanedioate Chemical compound CCOC(=O)CC(C)(C)CC(=O)OCC WKLBAFKOKJVNMN-UHFFFAOYSA-N 0.000 description 1
- RZRAIVZRSCFWAP-UHFFFAOYSA-N diethyl 3,3-diphenylpentanedioate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)(CC(=O)OCC)C1=CC=CC=C1 RZRAIVZRSCFWAP-UHFFFAOYSA-N 0.000 description 1
- VIYRHXNXDQLXFH-UHFFFAOYSA-N diethyl 3-(2-methylpropyl)pentanedioate Chemical compound CCOC(=O)CC(CC(C)C)CC(=O)OCC VIYRHXNXDQLXFH-UHFFFAOYSA-N 0.000 description 1
- ZYGHIHZXDXJIMD-UHFFFAOYSA-N diethyl 3-(3,3,3-trifluoropropyl)pentanedioate Chemical compound CCOC(=O)CC(CCC(F)(F)F)CC(=O)OCC ZYGHIHZXDXJIMD-UHFFFAOYSA-N 0.000 description 1
- STPALKIJJSAYDG-UHFFFAOYSA-N diethyl 3-(cyclohexylmethyl)pentanedioate Chemical compound CCOC(=O)CC(CC(=O)OCC)CC1CCCCC1 STPALKIJJSAYDG-UHFFFAOYSA-N 0.000 description 1
- ICGZMYFTSCIERP-UHFFFAOYSA-N diethyl 3-butyl-3-ethylpentanedioate Chemical compound CCOC(=O)CC(CC)(CCCC)CC(=O)OCC ICGZMYFTSCIERP-UHFFFAOYSA-N 0.000 description 1
- PMEULZQDXVXNLR-UHFFFAOYSA-N diethyl 3-butyl-3-methylpentanedioate Chemical compound CCOC(=O)CC(C)(CCCC)CC(=O)OCC PMEULZQDXVXNLR-UHFFFAOYSA-N 0.000 description 1
- DBVNHTIMKHVFMX-UHFFFAOYSA-N diethyl 3-ethyl-3-(2-methylbutyl)pentanedioate Chemical compound CCOC(=O)CC(CC)(CC(C)CC)CC(=O)OCC DBVNHTIMKHVFMX-UHFFFAOYSA-N 0.000 description 1
- FLDRVUFUVFCBEU-UHFFFAOYSA-N diethyl 3-ethyl-3-methylpentanedioate Chemical compound CCOC(=O)CC(C)(CC)CC(=O)OCC FLDRVUFUVFCBEU-UHFFFAOYSA-N 0.000 description 1
- UFGHTNILKVQENH-UHFFFAOYSA-N diethyl 3-ethylpentanedioate Chemical compound CCOC(=O)CC(CC)CC(=O)OCC UFGHTNILKVQENH-UHFFFAOYSA-N 0.000 description 1
- HWRXSDZZXQITJD-UHFFFAOYSA-N diethyl 3-methyl-3-(2-methylpropyl)pentanedioate Chemical compound CCOC(=O)CC(C)(CC(C)C)CC(=O)OCC HWRXSDZZXQITJD-UHFFFAOYSA-N 0.000 description 1
- RLMRCBAKOXQRHC-UHFFFAOYSA-N diethyl 3-methyl-3-phenylpentanedioate Chemical compound CCOC(=O)CC(C)(CC(=O)OCC)C1=CC=CC=C1 RLMRCBAKOXQRHC-UHFFFAOYSA-N 0.000 description 1
- QGGVOYKCUWHUHK-UHFFFAOYSA-N diethyl 3-phenyl-3-propylpentanedioate Chemical compound CCOC(=O)CC(CCC)(CC(=O)OCC)C1=CC=CC=C1 QGGVOYKCUWHUHK-UHFFFAOYSA-N 0.000 description 1
- GSDRMAHJAKQAOZ-UHFFFAOYSA-N diethyl 3-phenylpentanedioate Chemical compound CCOC(=O)CC(CC(=O)OCC)C1=CC=CC=C1 GSDRMAHJAKQAOZ-UHFFFAOYSA-N 0.000 description 1
- VXHFAMSEJYNPMD-UHFFFAOYSA-N diethyl 3-propan-2-ylpentanedioate Chemical compound CCOC(=O)CC(C(C)C)CC(=O)OCC VXHFAMSEJYNPMD-UHFFFAOYSA-N 0.000 description 1
- WASGQQQMQHZYNB-UHFFFAOYSA-N diethyl 3-propylpentanedioate Chemical compound CCOC(=O)CC(CCC)CC(=O)OCC WASGQQQMQHZYNB-UHFFFAOYSA-N 0.000 description 1
- ANBMJAKRRFOULQ-UHFFFAOYSA-N diethyl 3-tert-butylpentanedioate Chemical compound CCOC(=O)CC(C(C)(C)C)CC(=O)OCC ANBMJAKRRFOULQ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012798 spherical particle 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
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- NETBVGNWMHLXRP-UHFFFAOYSA-N tert-butyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(C)(C)C NETBVGNWMHLXRP-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000011911 α-alkylation Methods 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
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99200767.4 | 1999-03-15 | ||
| EP99200767 | 1999-03-15 | ||
| PCT/EP2000/002047 WO2000055215A1 (en) | 1999-03-15 | 2000-03-08 | Components and catalysts for the polymerization of olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002539298A JP2002539298A (ja) | 2002-11-19 |
| JP2002539298A5 JP2002539298A5 (https=) | 2007-04-19 |
| JP4537587B2 true JP4537587B2 (ja) | 2010-09-01 |
Family
ID=8239980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000605641A Expired - Fee Related JP4537587B2 (ja) | 1999-03-15 | 2000-03-08 | オレフィンの重合用成分および触媒 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6541582B1 (https=) |
| EP (1) | EP1082359B1 (https=) |
| JP (1) | JP4537587B2 (https=) |
| KR (1) | KR20010043615A (https=) |
| CN (1) | CN1306544A (https=) |
| AT (1) | ATE333474T1 (https=) |
| AU (1) | AU3165900A (https=) |
| BR (1) | BR0006002A (https=) |
| CA (1) | CA2331732A1 (https=) |
| DE (1) | DE60029399T2 (https=) |
| ES (1) | ES2267504T3 (https=) |
| HU (1) | HUP0102374A2 (https=) |
| IL (1) | IL139427A0 (https=) |
| MX (1) | MXPA00011193A (https=) |
| WO (1) | WO2000055215A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040014504A (ko) * | 2001-04-23 | 2004-02-14 | 이데미쓰세끼유가가꾸가부시끼가이샤 | 올레핀 중합용 고체 촉매성분 |
| CN1169845C (zh) * | 2002-02-07 | 2004-10-06 | 中国石油化工股份有限公司 | 用于烯烃聚合的固体催化剂组分和含该催化剂组分的催化剂及其应用 |
| ES2289295T3 (es) * | 2002-06-13 | 2008-02-01 | Basell Poliolefine Italia S.R.L. | Componentes cataliticos ziegler natta para la polimerizacion de olefinas. |
| JP5530054B2 (ja) * | 2005-01-19 | 2014-06-25 | 三井化学株式会社 | オレフィン重合体製造用固体状チタン触媒成分、オレフィン重合用触媒およびオレフィン重合体の製造方法 |
| CN101323650B (zh) | 2007-06-13 | 2010-11-03 | 中国石油天然气股份有限公司 | 一种烯烃聚合催化剂及其制备方法和应用 |
| US7893003B2 (en) | 2007-08-24 | 2011-02-22 | Dow Global Technologies Inc. | Catalyst composition with mixed selectivity control agent and method |
| CN101848946B (zh) | 2007-08-24 | 2013-06-12 | 陶氏环球技术有限责任公司 | 气相聚合方法 |
| EP2206731B1 (en) * | 2007-11-01 | 2013-08-28 | Mitsui Chemicals, Inc. | Solid titanium catalyst component, olefin polymerization catalyst, and olefin polymerization method |
| SG194361A1 (en) * | 2007-11-27 | 2013-11-29 | Mitsui Chemicals Inc | Solid titanium catalyst component, olefin polymerization catalyst, and olefin polymerization process |
| JP5740159B2 (ja) * | 2007-12-21 | 2015-06-24 | ダブリュー・アール・グレイス・アンド・カンパニー−コネチカット | 二座内部供与体を有する自己制限性触媒組成物 |
| US8247341B2 (en) * | 2009-04-17 | 2012-08-21 | Dow Global Technologies Llc | Procatalyst composition with silyl glutarate and method |
| BR112013025014A2 (pt) | 2011-04-01 | 2017-01-17 | Basell Poliolefine Srl | componentes de catalisador para a polimerização de olefinas e catalisadores obtidos a partir destes |
| CN102746426A (zh) | 2011-04-22 | 2012-10-24 | 中国石油天然气股份有限公司 | 一种烯烃聚合催化剂及其制备和应用 |
| EP2757114A1 (en) | 2013-01-18 | 2014-07-23 | Basell Poliolefine Italia S.r.l. | Catalyst components for the polymerization of olefins |
| WO2017042058A1 (en) * | 2015-09-11 | 2017-03-16 | Basell Poliolefine Italia S.R.L. | Process for the preparation of catalyst components for the polymerization of olefins |
| FI3517555T3 (fi) | 2016-09-23 | 2024-12-30 | China Petroleum & Chem Corp | Katalyyttikomponentti käytettäväksi olefiinipolymeroinnissa, katalyytti ja niiden käyttöjä |
| JP7178992B2 (ja) | 2016-09-23 | 2022-11-28 | 中国石油化工股▲ふん▼有限公司 | オレフィン重合用の触媒成分、触媒およびその応用 |
| EP3625273B1 (en) * | 2017-05-18 | 2021-05-05 | Borealis AG | Heterophasic polyolefin composition with excellent optical properties |
| JP7106241B2 (ja) * | 2019-01-09 | 2022-07-26 | 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 | オレフィンの重合用触媒成分 |
| EP4185463B1 (en) | 2020-07-24 | 2024-10-02 | Basell Poliolefine Italia S.r.l. | Polyolefin composition for roofing applications |
| EP4192688B1 (en) | 2020-08-07 | 2024-08-21 | Basell Poliolefine Italia S.r.l. | Soft and flexible polyolefin composition |
| US20240059885A1 (en) | 2020-12-14 | 2024-02-22 | Basell Poliolefine Italia S.R.L. | Ultrasoft polyolefin composition |
| WO2022167182A1 (en) | 2021-02-08 | 2022-08-11 | Basell Poliolefine Italia S.R.L. | Polyolefin composition for functional films |
| CN116041577B (zh) | 2021-10-28 | 2024-12-06 | 中国石油化工股份有限公司 | 烯烃聚合催化剂组分、催化剂体系及应用和烯烃聚合方法 |
| EP4422867B1 (en) | 2021-10-28 | 2025-11-19 | Basell Polyolefine GmbH | Reinforced polypropylene composition |
| US20250059362A1 (en) | 2021-12-23 | 2025-02-20 | Basell Poliolefine Italia S.R.L. | Soft polyolefin composition |
| US20250304730A1 (en) | 2022-05-06 | 2025-10-02 | Basell Poliolefine Italia S.R.L. | Plastic material and shaped article obtained therefrom |
| WO2023247227A1 (en) | 2022-06-20 | 2023-12-28 | Basell Poliolefine Italia S.R.L. | Multilayer film |
| JP2025521958A (ja) | 2022-08-03 | 2025-07-10 | 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 | ヒートシールフィルム用ポリプロピレン組成物 |
| KR20250129692A (ko) | 2022-12-19 | 2025-08-29 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 착색 열가소성 조성물 |
| WO2025168499A1 (en) | 2024-02-07 | 2025-08-14 | Basell Poliolefine Italia S.R.L. | Translucent polypropylene-based material for additive manufacturing |
| WO2025228762A1 (en) | 2024-04-30 | 2025-11-06 | Basell Poliolefine Italia S.R.L. | Polyolefin composition for painted articles |
| WO2026017674A1 (en) | 2024-07-17 | 2026-01-22 | Basell Poliolefine Italia S.R.L. | Propylene polymer |
| WO2026041323A1 (en) | 2024-08-19 | 2026-02-26 | Basell Poliolefine Italia S.R.L. | Polypropylene composition having good thermal and optical properties |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK133012C (da) | 1968-11-21 | 1976-08-09 | Montedison Spa | Katalysator til polymerisation af alkener |
| YU35844B (en) * | 1968-11-25 | 1981-08-31 | Montedison Spa | Process for obtaining catalysts for the polymerization of olefines |
| GB1603724A (en) | 1977-05-25 | 1981-11-25 | Montedison Spa | Components and catalysts for the polymerisation of alpha-olefins |
| IT1096661B (it) | 1978-06-13 | 1985-08-26 | Montedison Spa | Procedimento per la preparazione di prodotti in forma sferoidale solidi a temperatura ambiente |
| IT1098272B (it) | 1978-08-22 | 1985-09-07 | Montedison Spa | Componenti,di catalizzatori e catalizzatori per la polimerizzazione delle alfa-olefine |
| IT1209255B (it) | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
| JPS58138711A (ja) | 1982-02-12 | 1983-08-17 | Mitsui Petrochem Ind Ltd | オレフインの重合方法 |
| JPS58138706A (ja) | 1982-02-12 | 1983-08-17 | Mitsui Petrochem Ind Ltd | オレフイン系重合体の製造方法 |
| JPS59207904A (ja) * | 1983-05-11 | 1984-11-26 | Mitsui Petrochem Ind Ltd | オレフイン重合体の製造方法 |
| IT1227259B (it) * | 1988-09-30 | 1991-03-28 | Himont Inc | Catalizzatori per la polimerizzazione di olefine. |
| IT1230134B (it) | 1989-04-28 | 1991-10-14 | Himont Inc | Componenti e catalizzatori per la polimerizzazione di olefine. |
| CA2040336C (en) | 1990-04-13 | 1998-01-20 | Mamoru Kioka | Solid titanium catalyst component for olefin polymerization, olefin polymerization catalyst, prepolymerized polyolefin-containing catalyst and method of olefin polymerization |
| IT1262934B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
| IT1262935B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
| JP3306119B2 (ja) * | 1992-09-01 | 2002-07-24 | 出光石油化学株式会社 | オレフィン重合体の製造方法 |
| IT1256648B (it) | 1992-12-11 | 1995-12-12 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione delle olefine |
| US5459116A (en) * | 1993-05-07 | 1995-10-17 | Samsung General Chemicals Co., Ltd. | Highly active catalyst for the polymerization of olefins and method for the preparation of the same |
| JPH09165414A (ja) * | 1995-10-11 | 1997-06-24 | Mitsui Petrochem Ind Ltd | 固体状チタン触媒成分とそのオレフィン重合触媒への利用 |
| DE69821710T2 (de) | 1997-03-29 | 2005-01-13 | Basell Poliolefine Italia S.P.A. | Magnesiumdihalogenid/alkohol addukte, verfahren zu ihrer herstellung und damit hergestellte katalysatorbestandteile |
| JPH1160625A (ja) * | 1997-08-22 | 1999-03-02 | Idemitsu Petrochem Co Ltd | オレフィン重合用固体触媒成分、オレフィン重合用触 媒及びオレフィン重合体の製造方法 |
| JPH11158210A (ja) * | 1997-11-28 | 1999-06-15 | Mitsui Chem Inc | オレフィン重合用固体状チタン触媒成分、これを含むオレフィン重合用触媒およびオレフィンの重合方法 |
| JPH11199628A (ja) * | 1998-01-09 | 1999-07-27 | Idemitsu Petrochem Co Ltd | オレフィン重合用固体触媒成分、オレフィン重合用触 媒およびオレフィン重合体の製造方法 |
-
2000
- 2000-03-08 JP JP2000605641A patent/JP4537587B2/ja not_active Expired - Fee Related
- 2000-03-08 CA CA002331732A patent/CA2331732A1/en not_active Abandoned
- 2000-03-08 IL IL13942700A patent/IL139427A0/xx unknown
- 2000-03-08 DE DE60029399T patent/DE60029399T2/de not_active Expired - Lifetime
- 2000-03-08 MX MXPA00011193A patent/MXPA00011193A/es unknown
- 2000-03-08 EP EP00909346A patent/EP1082359B1/en not_active Expired - Lifetime
- 2000-03-08 WO PCT/EP2000/002047 patent/WO2000055215A1/en not_active Ceased
- 2000-03-08 ES ES00909346T patent/ES2267504T3/es not_active Expired - Lifetime
- 2000-03-08 AU AU31659/00A patent/AU3165900A/en not_active Abandoned
- 2000-03-08 US US09/700,382 patent/US6541582B1/en not_active Expired - Lifetime
- 2000-03-08 AT AT00909346T patent/ATE333474T1/de not_active IP Right Cessation
- 2000-03-08 CN CN00800872A patent/CN1306544A/zh active Pending
- 2000-03-08 BR BR0006002-0A patent/BR0006002A/pt not_active Application Discontinuation
- 2000-03-08 KR KR1020007012765A patent/KR20010043615A/ko not_active Withdrawn
- 2000-03-08 HU HU0102374A patent/HUP0102374A2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0102374A2 (hu) | 2001-12-28 |
| DE60029399T2 (de) | 2007-07-19 |
| IL139427A0 (en) | 2001-11-25 |
| ATE333474T1 (de) | 2006-08-15 |
| WO2000055215A1 (en) | 2000-09-21 |
| AU3165900A (en) | 2000-10-04 |
| CA2331732A1 (en) | 2000-09-21 |
| EP1082359B1 (en) | 2006-07-19 |
| US6541582B1 (en) | 2003-04-01 |
| DE60029399D1 (de) | 2006-08-31 |
| MXPA00011193A (es) | 2003-05-19 |
| KR20010043615A (ko) | 2001-05-25 |
| ES2267504T3 (es) | 2007-03-16 |
| BR0006002A (pt) | 2001-03-06 |
| CN1306544A (zh) | 2001-08-01 |
| EP1082359A1 (en) | 2001-03-14 |
| JP2002539298A (ja) | 2002-11-19 |
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