JP2000507499A - メタロセン用共触媒 - Google Patents
メタロセン用共触媒Info
- Publication number
- JP2000507499A JP2000507499A JP9535291A JP53529197A JP2000507499A JP 2000507499 A JP2000507499 A JP 2000507499A JP 9535291 A JP9535291 A JP 9535291A JP 53529197 A JP53529197 A JP 53529197A JP 2000507499 A JP2000507499 A JP 2000507499A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- indenyl
- titanium
- dimethyl
- 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.)
- Ceased
Links
- 239000003426 co-catalyst Substances 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 239000012190 activator Substances 0.000 claims abstract description 29
- 150000001450 anions Chemical class 0.000 claims abstract description 27
- 239000012968 metallocene catalyst Substances 0.000 claims abstract description 22
- -1 pentamethyl cyclopentadienyl titanate Chemical compound 0.000 claims description 162
- YSRFHVJGXPIDGR-UHFFFAOYSA-N dimethylsilane titanium Chemical compound [Ti].C[SiH2]C YSRFHVJGXPIDGR-UHFFFAOYSA-N 0.000 claims description 122
- 239000003054 catalyst Substances 0.000 claims description 69
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 69
- 239000010936 titanium Substances 0.000 claims description 63
- 150000001408 amides Chemical class 0.000 claims description 61
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 59
- 229910052719 titanium Inorganic materials 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 39
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 35
- 230000003647 oxidation Effects 0.000 claims description 32
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052726 zirconium Inorganic materials 0.000 claims description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 22
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 150000001993 dienes Chemical class 0.000 claims description 19
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 14
- AGWKGKUGJDMKMT-UHFFFAOYSA-N 2,4,6-triphenylaniline Chemical compound NC1=C(C=2C=CC=CC=2)C=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 AGWKGKUGJDMKMT-UHFFFAOYSA-N 0.000 claims description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052723 transition metal Inorganic materials 0.000 claims description 12
- 150000003624 transition metals Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 10
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 10
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- SFPQWMKUAVIGIX-UHFFFAOYSA-N C1=CC=C2C([Ti])C=CC2=C1 Chemical compound C1=CC=C2C([Ti])C=CC2=C1 SFPQWMKUAVIGIX-UHFFFAOYSA-N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical group [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 claims description 7
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 5
- DPSOUODMTOWXTB-UHFFFAOYSA-N CC1=C(C)C(C)([Ti])C(C)=C1C Chemical compound CC1=C(C)C(C)([Ti])C(C)=C1C DPSOUODMTOWXTB-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 229910052845 zircon Inorganic materials 0.000 claims description 5
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 4
- 241000927721 Tritia Species 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 claims description 4
- ODMWVMRTMJXBPA-UHFFFAOYSA-N C1C=CC=C2C([Ti])CCC21 Chemical compound C1C=CC=C2C([Ti])CCC21 ODMWVMRTMJXBPA-UHFFFAOYSA-N 0.000 claims description 3
- 241000723368 Conium Species 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QLKINISCYVCLTE-UHFFFAOYSA-N 6-phenylhexa-2,4-dienylbenzene Chemical compound C=1C=CC=CC=1CC=CC=CCC1=CC=CC=C1 QLKINISCYVCLTE-UHFFFAOYSA-N 0.000 claims description 2
- ZCNHNDFOIRASDU-UHFFFAOYSA-N C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.C1(CCC2CC=CC=C12)[Zr+] Chemical compound C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.C1(CCC2CC=CC=C12)[Zr+] ZCNHNDFOIRASDU-UHFFFAOYSA-N 0.000 claims description 2
- ZCXSGAGJXWOLPP-UHFFFAOYSA-N C1(C=CC=C1)[Ti](OC(C)C)(OC(C)C)OC(C)C Chemical compound C1(C=CC=C1)[Ti](OC(C)C)(OC(C)C)OC(C)C ZCXSGAGJXWOLPP-UHFFFAOYSA-N 0.000 claims description 2
- CTPZHZZBJQTXRG-UHFFFAOYSA-N CC([O-])C.CC([O-])C.CC([O-])C.CC1=C(C(=C(C1([Ti+3])C)C)C)C Chemical compound CC([O-])C.CC([O-])C.CC([O-])C.CC1=C(C(=C(C1([Ti+3])C)C)C)C CTPZHZZBJQTXRG-UHFFFAOYSA-N 0.000 claims description 2
- VLDNTHDOFNRZLK-UHFFFAOYSA-N CCl.C[SiH](C)[Zr](C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound CCl.C[SiH](C)[Zr](C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12 VLDNTHDOFNRZLK-UHFFFAOYSA-N 0.000 claims description 2
- NEHOLHBKMCQNRG-UHFFFAOYSA-N CP(C)C.[Ti] Chemical compound CP(C)C.[Ti] NEHOLHBKMCQNRG-UHFFFAOYSA-N 0.000 claims description 2
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 claims description 2
- DFSWNYUWLQKNQP-UHFFFAOYSA-N [Ti].CC=CC=C Chemical compound [Ti].CC=CC=C DFSWNYUWLQKNQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 2
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 2
- TYHLKBYIOROTTQ-UHFFFAOYSA-N (2,3-dimethyl-1H-inden-1-yl)-dimethylsilane 2-methylbuta-1,3-diene titanium(4+) Chemical compound C=CC(C)=C.[Ti+4].CC=1C(C2=CC=CC=C2C1C)[SiH](C)C TYHLKBYIOROTTQ-UHFFFAOYSA-N 0.000 claims 1
- YSAXEHWHSLANOM-UHFFFAOYSA-N 2-methyl-1h-indene Chemical compound C1=CC=C2CC(C)=CC2=C1 YSAXEHWHSLANOM-UHFFFAOYSA-N 0.000 claims 1
- XTUHKYWLZCEKEL-UHFFFAOYSA-N C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.[Ti+2].C[SiH2]C Chemical compound C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.[Ti+2].C[SiH2]C XTUHKYWLZCEKEL-UHFFFAOYSA-N 0.000 claims 1
- XCWLXYUJTUJRHA-UHFFFAOYSA-N C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.[Ti].C[SiH2]C Chemical compound C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.[Ti].C[SiH2]C XCWLXYUJTUJRHA-UHFFFAOYSA-N 0.000 claims 1
- VHNNPTGLWYHNHE-UHFFFAOYSA-N C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 Chemical compound C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 VHNNPTGLWYHNHE-UHFFFAOYSA-N 0.000 claims 1
- KFCDSBRUXVHFBC-UHFFFAOYSA-N C1C2=CC=CC=C2C(CCC2)=C1C2[Zr]([SiH](C)C)C1C(CC=2C3=CC=CC=2)=C3CCC1 Chemical compound C1C2=CC=CC=C2C(CCC2)=C1C2[Zr]([SiH](C)C)C1C(CC=2C3=CC=CC=2)=C3CCC1 KFCDSBRUXVHFBC-UHFFFAOYSA-N 0.000 claims 1
- JONGYRSDAVAGFI-UHFFFAOYSA-N C=CC=C.[Ti+4].CC=1C(C2=CC=CC=C2C1)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] Chemical compound C=CC=C.[Ti+4].CC=1C(C2=CC=CC=C2C1)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] JONGYRSDAVAGFI-UHFFFAOYSA-N 0.000 claims 1
- HFGUGMYBUUSUNH-UHFFFAOYSA-N C=CC=CC.[Ti+2].CC=1C(C2=CC=CC=C2C1C)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] Chemical compound C=CC=CC.[Ti+2].CC=1C(C2=CC=CC=C2C1C)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] HFGUGMYBUUSUNH-UHFFFAOYSA-N 0.000 claims 1
- NBYHTEJSGXAORC-UHFFFAOYSA-N CC(=C)C(=C)C.[Ti+4].CC=1C(C2=CC=CC=C2C1C)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] Chemical compound CC(=C)C(=C)C.[Ti+4].CC=1C(C2=CC=CC=C2C1C)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] NBYHTEJSGXAORC-UHFFFAOYSA-N 0.000 claims 1
- XCGJNHKXUJMCSH-UHFFFAOYSA-N CC=CC=CC.[Ti+2].CC=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)[SiH](C)C Chemical compound CC=CC=CC.[Ti+2].CC=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)[SiH](C)C XCGJNHKXUJMCSH-UHFFFAOYSA-N 0.000 claims 1
- NTHSNQGGPIGYJF-UHFFFAOYSA-N CC[O-].CC1=C(C(=C(C1(C)[Zr+2]C1(C(=C(C(=C1C)C)C)C)C)C)C)C.CC[O-] Chemical compound CC[O-].CC1=C(C(=C(C1(C)[Zr+2]C1(C(=C(C(=C1C)C)C)C)C)C)C)C.CC[O-] NTHSNQGGPIGYJF-UHFFFAOYSA-N 0.000 claims 1
- NXNNTBTYTUJMHX-UHFFFAOYSA-N C[Si](C)(C)C1(C=CC=C1)[Zr]C1(C=CC=C1)[Si](C)(C)C Chemical compound C[Si](C)(C)C1(C=CC=C1)[Zr]C1(C=CC=C1)[Si](C)(C)C NXNNTBTYTUJMHX-UHFFFAOYSA-N 0.000 claims 1
- GQROXQUXLNYHQM-UHFFFAOYSA-N ClCC1=CC=CC=C1.C1=CC2=CC=CC=C2C1[Zr]([SiH](C)C)C1C2=CC=CC=C2C=C1 Chemical compound ClCC1=CC=CC=C1.C1=CC2=CC=CC=C2C1[Zr]([SiH](C)C)C1C2=CC=CC=C2C=C1 GQROXQUXLNYHQM-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- ZAGHKONXGGSVDV-UHFFFAOYSA-N butylcyclopentane Chemical compound CCCCC1CCCC1 ZAGHKONXGGSVDV-UHFFFAOYSA-N 0.000 claims 1
- CJZOEXPVZABSEX-UHFFFAOYSA-N chloromethane;zirconium Chemical compound [Zr].ClC CJZOEXPVZABSEX-UHFFFAOYSA-N 0.000 claims 1
- ASBGGHMVAMBCOR-UHFFFAOYSA-N ethanolate;zirconium(4+) Chemical compound [Zr+4].CC[O-].CC[O-].CC[O-].CC[O-] ASBGGHMVAMBCOR-UHFFFAOYSA-N 0.000 claims 1
- ZKWONARDNQWFKT-UHFFFAOYSA-N methanolate;titanium(2+) Chemical compound CO[Ti]OC ZKWONARDNQWFKT-UHFFFAOYSA-N 0.000 claims 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 39
- 238000006243 chemical reaction Methods 0.000 abstract description 32
- 238000005516 engineering process Methods 0.000 abstract description 17
- 230000004913 activation Effects 0.000 abstract description 9
- 238000006758 bulk electrolysis reaction Methods 0.000 abstract description 5
- 230000002427 irreversible effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 28
- 239000003446 ligand Substances 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- 239000002184 metal Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 15
- 239000002002 slurry Substances 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 241000894007 species Species 0.000 description 14
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 125000000129 anionic group Chemical group 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical class C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 9
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 9
- 238000003780 insertion Methods 0.000 description 9
- 230000037431 insertion Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 9
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
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- HTAFHRVDRIULFN-UHFFFAOYSA-N methylsilane titanium Chemical compound [Ti].C[SiH3] HTAFHRVDRIULFN-UHFFFAOYSA-N 0.000 description 1
- CYQYCASVINMDFD-UHFFFAOYSA-N n,n-ditert-butyl-2-methylpropan-2-amine Chemical class CC(C)(C)N(C(C)(C)C)C(C)(C)C CYQYCASVINMDFD-UHFFFAOYSA-N 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
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- 230000000171 quenching effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
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- 239000010979 ruby Substances 0.000 description 1
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- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 150000003440 styrenes Chemical class 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical class FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- MJOXZELXZLIYPI-UHFFFAOYSA-N titanium(2+) Chemical compound [Ti+2] MJOXZELXZLIYPI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- KTDRTOYQXRJJTE-FIFLTTCUSA-N trimethyl-[(1e,3e)-4-trimethylsilylbuta-1,3-dienyl]silane Chemical compound C[Si](C)(C)\C=C\C=C\[Si](C)(C)C KTDRTOYQXRJJTE-FIFLTTCUSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/603—Component covered by group C08F4/60 with a metal or compound covered by group C08F4/44 other than an organo-aluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61916—Component covered by group C08F4/60 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/6192—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1474596P | 1996-03-29 | 1996-03-29 | |
| US60/014,745 | 1996-03-29 | ||
| PCT/US1997/004247 WO1997036937A1 (en) | 1996-03-29 | 1997-03-20 | Metallocene cocatalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000507499A true JP2000507499A (ja) | 2000-06-20 |
| JP2000507499A5 JP2000507499A5 (enExample) | 2004-12-09 |
Family
ID=21767441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9535291A Ceased JP2000507499A (ja) | 1996-03-29 | 1997-03-20 | メタロセン用共触媒 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6255246B1 (enExample) |
| EP (1) | EP0889911B1 (enExample) |
| JP (1) | JP2000507499A (enExample) |
| KR (1) | KR20000005128A (enExample) |
| CN (1) | CN1216996A (enExample) |
| DE (1) | DE69703438T2 (enExample) |
| ES (1) | ES2152653T3 (enExample) |
| WO (1) | WO1997036937A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3320619B2 (ja) | 1996-10-02 | 2002-09-03 | 三井化学株式会社 | 新規メタロセン化合物とそれを用いたオレフィンまたはジエンの重合方法 |
| JP2007526250A (ja) * | 2004-02-04 | 2007-09-13 | プラクスエア・テクノロジー・インコーポレイテッド | 核形成密度が高い有機金属化合物 |
| KR20140007450A (ko) * | 2011-03-09 | 2014-01-17 | 알베마를 코포레이션 | 카보양이온 물질을 내포하는 알루미녹산 촉매 활성화제, 및 폴리올레핀 촉매에서 이의 용도 |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036937A1 (en) * | 1996-03-29 | 1997-10-09 | The Dow Chemical Company | Metallocene cocatalyst |
| US6114270A (en) * | 1998-08-07 | 2000-09-05 | Equistar Chemicals, L.P. | Polymerization-stable anionic ancillary ligand containing alkylimido catalysts and method of using the same |
| CN100340568C (zh) * | 1998-11-25 | 2007-10-03 | 塔戈尔股份有限公司 | 茂金属一卤化物 |
| US6803431B1 (en) | 1999-03-29 | 2004-10-12 | Basf Aktiengesellschaft | Method for the polymerization of olefins |
| DE19935592A1 (de) | 1999-08-02 | 2001-02-08 | Elenac Gmbh | Imidochromverbindungen in Katalysatorsystemen für die Olefinpolymerisation |
| PL200524B1 (pl) | 1999-08-13 | 2009-01-30 | Basell Polyolefine Gmbh | Zastosowanie kopolimerów etylenu z α-olefinami C₃ -C₉ oraz zastosowanie kompleksów monoindenylo- lub monofluorenylochromowych |
| KR100786742B1 (ko) * | 1999-10-08 | 2007-12-18 | 미쓰이 가가쿠 가부시키가이샤 | 폴리올레핀 |
| CN101434668B (zh) | 1999-10-08 | 2012-02-22 | 三井化学株式会社 | 聚烯烃 |
| SG83223A1 (en) * | 1999-12-27 | 2001-09-18 | Sumitomo Chemical Co | Modified particles, catalyst for olefin polymerization using the same, and process of producing olefin polymer |
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- 1997-03-20 CN CN97194226A patent/CN1216996A/zh active Pending
- 1997-03-20 EP EP97909048A patent/EP0889911B1/en not_active Expired - Lifetime
- 1997-03-20 KR KR1019980707774A patent/KR20000005128A/ko not_active Ceased
- 1997-03-20 DE DE69703438T patent/DE69703438T2/de not_active Expired - Fee Related
- 1997-03-20 ES ES97909048T patent/ES2152653T3/es not_active Expired - Lifetime
- 1997-03-20 JP JP9535291A patent/JP2000507499A/ja not_active Ceased
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2000
- 2000-01-18 US US09/487,399 patent/US6255246B1/en not_active Expired - Fee Related
-
2001
- 2001-02-20 US US09/789,411 patent/US6365779B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3320619B2 (ja) | 1996-10-02 | 2002-09-03 | 三井化学株式会社 | 新規メタロセン化合物とそれを用いたオレフィンまたはジエンの重合方法 |
| JP2007526250A (ja) * | 2004-02-04 | 2007-09-13 | プラクスエア・テクノロジー・インコーポレイテッド | 核形成密度が高い有機金属化合物 |
| KR20140007450A (ko) * | 2011-03-09 | 2014-01-17 | 알베마를 코포레이션 | 카보양이온 물질을 내포하는 알루미녹산 촉매 활성화제, 및 폴리올레핀 촉매에서 이의 용도 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0889911B1 (en) | 2000-11-02 |
| ES2152653T3 (es) | 2001-02-01 |
| WO1997036937A1 (en) | 1997-10-09 |
| US20010007044A1 (en) | 2001-07-05 |
| US6365779B2 (en) | 2002-04-02 |
| EP0889911A1 (en) | 1999-01-13 |
| DE69703438D1 (de) | 2000-12-07 |
| DE69703438T2 (de) | 2001-03-08 |
| US6255246B1 (en) | 2001-07-03 |
| KR20000005128A (ko) | 2000-01-25 |
| CN1216996A (zh) | 1999-05-19 |
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