NO318716B1 - Katalysatorsystem for polymerisering - Google Patents
Katalysatorsystem for polymerisering Download PDFInfo
- Publication number
- NO318716B1 NO318716B1 NO19975049A NO975049A NO318716B1 NO 318716 B1 NO318716 B1 NO 318716B1 NO 19975049 A NO19975049 A NO 19975049A NO 975049 A NO975049 A NO 975049A NO 318716 B1 NO318716 B1 NO 318716B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- catalyst component
- accordance
- alkyl
- groups
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 35
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 30
- 239000000725 suspension Substances 0.000 claims abstract description 36
- -1 C3-C20 cycloalkyl Chemical group 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 13
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims abstract description 13
- 230000000737 periodic effect Effects 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 9
- 239000007789 gas Substances 0.000 claims abstract description 9
- 239000004711 α-olefin Substances 0.000 claims abstract description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052796 boron Inorganic materials 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 229910052768 actinide Inorganic materials 0.000 claims abstract description 3
- 150000001255 actinides Chemical class 0.000 claims abstract description 3
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 3
- 125000000962 organic group Chemical group 0.000 claims abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 239000007787 solid Substances 0.000 claims description 29
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000005977 Ethylene Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 18
- 239000000377 silicon dioxide Substances 0.000 claims description 18
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229910052726 zirconium Inorganic materials 0.000 claims description 11
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011949 solid catalyst Substances 0.000 claims description 7
- 239000003426 co-catalyst Substances 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001639 boron compounds Chemical class 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims 2
- 229910003480 inorganic solid Inorganic materials 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 125000005234 alkyl aluminium group Chemical group 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 11
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- UCNUZZGQYQIHEH-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](OCCCC1(C=CC=C1)[Zr+2]C1(C=CC=C1)CCCO[Si](C)(C)C)(C)C Chemical compound [Cl-].[Cl-].C[Si](OCCCC1(C=CC=C1)[Zr+2]C1(C=CC=C1)CCCO[Si](C)(C)C)(C)C UCNUZZGQYQIHEH-UHFFFAOYSA-L 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002638 heterogeneous catalyst Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- VHZDCIQTNWJAQO-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)C=1C(C=CC=1)(CCCO[Si](C)(C)C)[Zr+2] Chemical compound [Cl-].[Cl-].C1(C=CC=C1)C=1C(C=CC=1)(CCCO[Si](C)(C)C)[Zr+2] VHZDCIQTNWJAQO-UHFFFAOYSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
- 229910000105 potassium hydride Inorganic materials 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- VUBBQUQAQNIJTB-UHFFFAOYSA-N 2-cyclopenta-1,3-dien-1-ylethoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCC1=CC=CC1 VUBBQUQAQNIJTB-UHFFFAOYSA-N 0.000 description 3
- ZDXHKIMLSJNMAY-UHFFFAOYSA-N 3-cyclopenta-1,3-dien-1-ylpropoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCCC1=CC=CC1 ZDXHKIMLSJNMAY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 3
- OLYNYVUFUXQFTF-UHFFFAOYSA-N (3,3-dimethyl-2-silylcyclopenta-1,4-dien-1-yl)oxy-trimethylsilane Chemical compound CC1(C=CC(=C1[SiH3])O[Si](C)(C)C)C OLYNYVUFUXQFTF-UHFFFAOYSA-N 0.000 description 2
- QKSJDOOUAJHQRY-UHFFFAOYSA-N 2-bromoethoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCBr QKSJDOOUAJHQRY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- BMTKGBCFRKGOOZ-UHFFFAOYSA-K cyclopenta-1,3-diene;zirconium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1 BMTKGBCFRKGOOZ-UHFFFAOYSA-K 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- JMTIZNLZWVOKMT-UHFFFAOYSA-N potassium;2-cyclopenta-2,4-dien-1-ylethoxy(trimethyl)silane Chemical compound [K+].C[Si](C)(C)OCC[C-]1C=CC=C1 JMTIZNLZWVOKMT-UHFFFAOYSA-N 0.000 description 2
- LJVRHCSFTTZNLP-UHFFFAOYSA-N potassium;3-cyclopenta-2,4-dien-1-ylpropoxy(trimethyl)silane Chemical compound [K+].C[Si](C)(C)OCCC[C-]1C=CC=C1 LJVRHCSFTTZNLP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- GMFWZZGXWMXYMQ-UHFFFAOYSA-N 3-bromopropoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCCBr GMFWZZGXWMXYMQ-UHFFFAOYSA-N 0.000 description 1
- 241000349731 Afzelia bipindensis Species 0.000 description 1
- FAZHVGWCLRMQGR-UHFFFAOYSA-N CC=1C(=C([C-](C=1)[SiH3])O[Si](C)(C)C)C.[K+] Chemical compound CC=1C(=C([C-](C=1)[SiH3])O[Si](C)(C)C)C.[K+] FAZHVGWCLRMQGR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- CGDUUYFJIPWALL-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1(C=CC=C1)[SiH2]O[Si](C(C)C)(C)C Chemical compound [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1(C=CC=C1)[SiH2]O[Si](C(C)C)(C)C CGDUUYFJIPWALL-UHFFFAOYSA-L 0.000 description 1
- LLTKSDFRCHYOBQ-UHFFFAOYSA-L [Cl-].[Cl-].CC([Si](O[SiH2]C1(C=CC=C1)[Zr+2]C1(C=CC=C1)[SiH2]O[Si](C)(C)C(C)C)(C)C)C Chemical compound [Cl-].[Cl-].CC([Si](O[SiH2]C1(C=CC=C1)[Zr+2]C1(C=CC=C1)[SiH2]O[Si](C)(C)C(C)C)(C)C)C LLTKSDFRCHYOBQ-UHFFFAOYSA-L 0.000 description 1
- PYACWPXZQGXHNN-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](OCCC1(C=CC=C1)[Zr+2]C1(C=CC=C1)CCO[Si](C)(C)C)(C)C Chemical compound [Cl-].[Cl-].C[Si](OCCC1(C=CC=C1)[Zr+2]C1(C=CC=C1)CCO[Si](C)(C)C)(C)C PYACWPXZQGXHNN-UHFFFAOYSA-L 0.000 description 1
- BDOLYWJSTMUXJP-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](OCCC1(C=CC=C1)[Zr+2]C1C=CC=C1)(C)C Chemical compound [Cl-].[Cl-].C[Si](OCCC1(C=CC=C1)[Zr+2]C1C=CC=C1)(C)C BDOLYWJSTMUXJP-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HLZBYIVAMXUYBW-UHFFFAOYSA-N chloro-cyclopenta-2,4-dien-1-yl-dimethylsilane Chemical compound C[Si](C)(Cl)C1C=CC=C1 HLZBYIVAMXUYBW-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- NUUNDIOOYFEMQN-UHFFFAOYSA-N cyclopenta-1,3-diene;sodium Chemical compound [Na].C1C=CC=C1 NUUNDIOOYFEMQN-UHFFFAOYSA-N 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- FNEVSQCMUJGYPB-UHFFFAOYSA-N lithium;2-cyclopenta-2,4-dien-1-ylethoxy(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)OCC[C-]1C=CC=C1 FNEVSQCMUJGYPB-UHFFFAOYSA-N 0.000 description 1
- UUWSRCCLPJWBMN-UHFFFAOYSA-N lithium;3-cyclopenta-2,4-dien-1-ylpropoxy(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)OCCC[C-]1C=CC=C1 UUWSRCCLPJWBMN-UHFFFAOYSA-N 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- UNSDWONDAUAWPV-UHFFFAOYSA-N methylaluminum;oxane Chemical class [Al]C.C1CCOCC1 UNSDWONDAUAWPV-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 description 1
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C08F110/02—Ethene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—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
- C08F4/61922—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 containing at least two cyclopentadienyl rings, fused or not
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9602310 | 1996-10-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975049D0 NO975049D0 (no) | 1997-10-31 |
| NO975049L NO975049L (no) | 1998-05-04 |
| NO318716B1 true NO318716B1 (no) | 2005-05-02 |
Family
ID=8296555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19975049A NO318716B1 (no) | 1996-10-31 | 1997-10-31 | Katalysatorsystem for polymerisering |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20030195109A1 (de) |
| EP (1) | EP0839836B1 (de) |
| JP (1) | JP3955140B2 (de) |
| AT (1) | ATE198210T1 (de) |
| DE (1) | DE69703728T2 (de) |
| ES (1) | ES2154017T3 (de) |
| NO (1) | NO318716B1 (de) |
| PT (1) | PT839836E (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1283010B1 (it) * | 1996-05-15 | 1998-04-03 | Enichem Spa | Complesso metallocenico supportato e procedimento per la sua prepa- razione |
| DE69703728T2 (de) | 1996-10-31 | 2001-06-28 | Repsol Quimica Sa | Katalysatorsysteme für die Polymerisation und Copolymerisation von Alpha-Olefinen |
| EP0953581B1 (de) * | 1998-04-27 | 2004-01-07 | Repsol Quimica S.A. | Katalysatorsysteme für die Polymerisation und Copolymerisation von Alpha-Olefinen |
| ES2211013T3 (es) | 1998-04-27 | 2004-07-01 | Repsol Quimica S.A. | Sistemas cataliticos para la polimerizacion y copolimerizacion de alfa-olefinas. |
| DE69916358T2 (de) * | 1998-04-29 | 2005-04-21 | Repsol Quimica Sa | Verfahren und Verwendung von heterogenen Katalysatorbestandteilen für die Olefinpolymerisation |
| PT955306E (pt) * | 1998-04-29 | 2003-06-30 | Repsol Quimica Sa | Compostos metaloceno funcionalizados processo de sintese e utilizacao |
| KR100367463B1 (ko) * | 1999-03-03 | 2003-01-14 | 주식회사 엘지화학 | 메탈로센 화합물 및 이를 이용한 올레핀 중합 |
| US7247595B2 (en) | 1999-06-22 | 2007-07-24 | Lg Chem, Ltd. | Supported metallocene catalyst and olefin polymerization using the same |
| KR100354290B1 (ko) * | 1999-06-22 | 2002-09-28 | 주식회사 엘지화학 | 담지 메탈로센 촉매 및 이를 이용한 올레핀 중합 |
| US7041618B2 (en) * | 1999-06-22 | 2006-05-09 | Lg Chemical Ltd. | Supported metallocene catalyst and olefin polymerization using the same |
| EP1095944B1 (de) | 1999-10-26 | 2004-03-17 | Repsol Quimica S.A. | Durch ein Kohlenstoffatom verbundene Biscyclopentadienylverbindungen und darmit hergestellte Metallocene |
| US6723675B1 (en) * | 2000-05-25 | 2004-04-20 | Univation Technologies, Llc | Catalyst for the production of olefin polymers |
| US6632770B2 (en) * | 2000-12-22 | 2003-10-14 | Univation Technologies, Llc | Catalyst system and its use in a polymerization process |
| ES2217104T3 (es) | 2001-01-18 | 2004-11-01 | Repsol Quimica S.A. | Catalizadores de la polimerizacion de olefinas. |
| FR2824066B1 (fr) | 2001-04-30 | 2004-02-06 | Atofina | Composante catalytique solide de type metallocene et son procede d'obtention |
| KR100690345B1 (ko) * | 2004-09-03 | 2007-03-09 | 주식회사 엘지화학 | 담지 메탈로센 촉매, 그 제조방법 및 이를 이용한폴리올레핀의 제조방법 |
| KR101703274B1 (ko) * | 2014-08-12 | 2017-02-22 | 주식회사 엘지화학 | 메탈로센 화합물, 이를 포함하는 촉매 조성물 및 이를 이용한 올레핀 중합체의 제조방법 |
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| DE1022382B (de) | 1956-04-12 | 1958-01-09 | Hoechst Ag | Verfahren zur Polymerisation von niederen Olefinen |
| US3440237A (en) | 1958-05-22 | 1969-04-22 | Monsanto Co | Production of polyethylene with water-modified ziegler catalyst |
| US3184416A (en) | 1958-05-22 | 1965-05-18 | Monsanto Co | Production of ziegler polymerization catalysts |
| GB1527598A (en) | 1974-11-12 | 1978-10-04 | Dow Corning Ltd | Catalysts and carriers therefor |
| DE2608863A1 (de) | 1976-03-04 | 1977-09-08 | Basf Ag | Verfahren zum herstellen von polyaethylen |
| SU956003A1 (ru) | 1977-01-20 | 1982-09-07 | Институт нефтехимического синтеза им.А.В.Топчиева | Мембранный катализатор дл гидрировани органических соединений |
| SU828471A1 (ru) | 1978-07-19 | 1983-11-30 | Ленинградский Ордена Трудового Красного Знамени Технологический Институт Им.Ленсовета | Способ приготовлени катализатора дл алкилировани фенола |
| GB2092017B (en) | 1981-01-30 | 1985-05-22 | Inst Neftechimicheskogo Sintez | Membrane catalyst for hydrogenation of organic compounds and method of preparing the same |
| DE3127133A1 (de) | 1981-07-09 | 1983-01-27 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von polyolefinen und deren copolymerisaten |
| CA1268754A (en) | 1985-06-21 | 1990-05-08 | Howard Curtis Welborn, Jr. | Supported polymerization catalyst |
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| US5391789A (en) | 1991-08-08 | 1995-02-21 | Hoechst Aktiengesellschaft | Bridged, chiral metallocenes, processes for their preparation and their use as catalysts |
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| TW294669B (de) * | 1992-06-27 | 1997-01-01 | Hoechst Ag | |
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| KR0151873B1 (ko) * | 1994-10-13 | 1998-10-15 | 김영욱 | 메탈로센 화합물, 이의 제조방법 및 이를 촉매로 이용한 고분자의 제조방법 |
| IT1272939B (it) | 1995-02-01 | 1997-07-01 | Enichem Spa | Catalizzatore metallocenico supportato per la (co)polimerizzazione delle olefine |
| US5731253A (en) | 1995-07-27 | 1998-03-24 | Albemarle Corporation | Hydrocarbylsilloxy - aluminoxane compositions |
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| ES2120868B1 (es) * | 1995-08-03 | 2000-09-16 | Repsol Quimica Sa | Sistema de catalizadores hetereogeneos tipo metalogeno, para procesos de obtencion de poliolefinas. |
| BR9611772A (pt) | 1995-11-27 | 1999-02-23 | Dow Chemical Co | Suporte para uso na preparação de catalisadores para polimerizações por adição catalisador suportado e processo de polimerização por adição |
| FI104826B (fi) * | 1996-01-30 | 2000-04-14 | Borealis As | Heteroatomilla substituoituja metalloseeniyhdisteitä olefiinipolymerointikatalyytti-systeemejä varten ja menetelmä niiden valmistamiseksi |
| US5780659A (en) | 1996-03-29 | 1998-07-14 | Phillips Petroleum Company | Substituted indenyl unbridged metallocenes |
| FI961511A (fi) | 1996-04-03 | 1997-10-04 | Mikrokemia Oy | Menetelmä olefiinien polymerointikatalyyttien valmistamiseksi |
| ES2129323B1 (es) | 1996-04-18 | 2000-09-16 | Repsol Quimica Sa | Procedimiento para la obtencion de un sistema catalitico para la polimerizacion de alpha-olefinas en suspension en fase gas a bajas y altas temperaturas o en masa a altas presiones y altas o bajas temperaturas |
| IT1283010B1 (it) | 1996-05-15 | 1998-04-03 | Enichem Spa | Complesso metallocenico supportato e procedimento per la sua prepa- razione |
| US5747404A (en) | 1996-05-28 | 1998-05-05 | Lyondell Petrochemical Company | Polysiloxane supported metallocene catalysts |
| EP0837068A3 (de) * | 1996-10-15 | 2002-04-17 | Basell Polyolefine GmbH | Stereorigide Metallocenverbindung |
| EP0839834B1 (de) * | 1996-10-30 | 2001-06-13 | Repsol Quimica S.A. | Katalysatorsysteme für die (Co)Polymerisation von Alpha-Olefinen |
| DE69726821T2 (de) * | 1996-10-30 | 2004-10-21 | Repsol Quimica Sa | Katalysatorsysteme für die Polymerisation und die Copolymerisation von Alpha-Olefinen |
| DE69703728T2 (de) | 1996-10-31 | 2001-06-28 | Repsol Quimica Sa | Katalysatorsysteme für die Polymerisation und Copolymerisation von Alpha-Olefinen |
| PT856518E (pt) * | 1997-02-01 | 2003-08-29 | Repsol Quimica Sa | Compostos de metaloceno e respectivos processo de sintese e utilizacao |
| ID20561A (id) | 1997-03-29 | 1999-01-14 | Montell Technology Company Bv | Metalosena dan katalis untuk polimerisasi olefin |
| US5892079A (en) | 1997-10-17 | 1999-04-06 | Sri International | Metallocene catalysts and associated methods of preparation and use |
| ES2211013T3 (es) | 1998-04-27 | 2004-07-01 | Repsol Quimica S.A. | Sistemas cataliticos para la polimerizacion y copolimerizacion de alfa-olefinas. |
| DE69916358T2 (de) | 1998-04-29 | 2005-04-21 | Repsol Quimica Sa | Verfahren und Verwendung von heterogenen Katalysatorbestandteilen für die Olefinpolymerisation |
| PT955306E (pt) | 1998-04-29 | 2003-06-30 | Repsol Quimica Sa | Compostos metaloceno funcionalizados processo de sintese e utilizacao |
-
1997
- 1997-10-31 DE DE69703728T patent/DE69703728T2/de not_active Expired - Fee Related
- 1997-10-31 JP JP33625597A patent/JP3955140B2/ja not_active Expired - Fee Related
- 1997-10-31 NO NO19975049A patent/NO318716B1/no not_active IP Right Cessation
- 1997-10-31 US US08/961,956 patent/US20030195109A1/en not_active Abandoned
- 1997-10-31 AT AT97500187T patent/ATE198210T1/de not_active IP Right Cessation
- 1997-10-31 EP EP97500187A patent/EP0839836B1/de not_active Expired - Lifetime
- 1997-10-31 ES ES97500187T patent/ES2154017T3/es not_active Expired - Lifetime
- 1997-10-31 PT PT97500187T patent/PT839836E/pt unknown
-
2004
- 2004-07-16 US US10/893,754 patent/US7211538B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2154017T3 (es) | 2001-03-16 |
| US7211538B2 (en) | 2007-05-01 |
| PT839836E (pt) | 2001-06-29 |
| US20050065019A1 (en) | 2005-03-24 |
| DE69703728D1 (de) | 2001-01-25 |
| US20030195109A1 (en) | 2003-10-16 |
| JP3955140B2 (ja) | 2007-08-08 |
| NO975049D0 (no) | 1997-10-31 |
| EP0839836B1 (de) | 2000-12-20 |
| JPH10226709A (ja) | 1998-08-25 |
| EP0839836A1 (de) | 1998-05-06 |
| DE69703728T2 (de) | 2001-06-28 |
| ATE198210T1 (de) | 2001-01-15 |
| NO975049L (no) | 1998-05-04 |
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