FI112237B - Olefiinien polymerointiin tarkoitettuja komponentteja ja katalyyttejä - Google Patents
Olefiinien polymerointiin tarkoitettuja komponentteja ja katalyyttejä Download PDFInfo
- Publication number
- FI112237B FI112237B FI944573A FI944573A FI112237B FI 112237 B FI112237 B FI 112237B FI 944573 A FI944573 A FI 944573A FI 944573 A FI944573 A FI 944573A FI 112237 B FI112237 B FI 112237B
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- FI
- Finland
- Prior art keywords
- radicals
- cycloalkyl
- alkyl
- radical
- same
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- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 20
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 11
- -1 magnesium halide Chemical class 0.000 claims abstract description 66
- 150000003254 radicals Chemical class 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 23
- 239000011777 magnesium Substances 0.000 claims abstract description 22
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 9
- 150000003609 titanium compounds Chemical class 0.000 claims abstract description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 3
- 125000005594 diketone group Chemical group 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical group [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 14
- 239000010936 titanium Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 3
- WMZURKKTJQPBOJ-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)C(C)C(=O)C(C)(C)C WMZURKKTJQPBOJ-UHFFFAOYSA-N 0.000 claims description 3
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical compound CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 claims description 3
- JKEWQMMYIOHEBI-UHFFFAOYSA-N 4-ethyl-2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)C(CC)C(=O)C(C)(C)C JKEWQMMYIOHEBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 11
- PWVBOTAIXMLNAR-UHFFFAOYSA-N 6,6,7,7-tetramethyloctane-3,5-dione Chemical compound CC(C(C)(C)C)(C(CC(CC)=O)=O)C PWVBOTAIXMLNAR-UHFFFAOYSA-N 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000011949 solid catalyst Substances 0.000 abstract description 13
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910003074 TiCl4 Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- UXRUIIASLOKITP-UHFFFAOYSA-N 3,5,5-trimethylhexane-2,4-dione Chemical compound CC(=O)C(C)C(=O)C(C)(C)C UXRUIIASLOKITP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920001384 propylene homopolymer Polymers 0.000 description 4
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 238000002083 X-ray spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003377 silicon compounds Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000012798 spherical particle Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- ZCQWHDYGRXASIN-UHFFFAOYSA-N 2,2-dimethyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)(C)C(=O)C1=CC=CC=C1 ZCQWHDYGRXASIN-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical group CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- ONGBXISBKSVVFS-UHFFFAOYSA-N 2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)C(=O)C1=CC=CC=C1 ONGBXISBKSVVFS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZEGNARRUOGCGCT-UHFFFAOYSA-N 4-ethyl-2,2,4,6-tetramethylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)(CC)C(=O)C(C)(C)C ZEGNARRUOGCGCT-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- LCLCVVVHIPPHCG-UHFFFAOYSA-N 5,5-dimethylhexane-2,4-dione Chemical compound CC(=O)CC(=O)C(C)(C)C LCLCVVVHIPPHCG-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000002681 magnesium compounds Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- OUPPKRIDJAMCCA-UHFFFAOYSA-N 1-methoxy-2-(methoxymethyl)-2,3-dimethylbutane Chemical compound COCC(C)(C(C)C)COC OUPPKRIDJAMCCA-UHFFFAOYSA-N 0.000 description 1
- IDONYCOFOUUWLB-UHFFFAOYSA-N 1-methyl-4-[1-(4-methylphenyl)ethyl]benzene Chemical compound C=1C=C(C)C=CC=1C(C)C1=CC=C(C)C=C1 IDONYCOFOUUWLB-UHFFFAOYSA-N 0.000 description 1
- XIAHSJTUQAWUAW-UHFFFAOYSA-N 1-methyl-4-[2-(4-methylphenyl)propan-2-yl]benzene Chemical compound C1=CC(C)=CC=C1C(C)(C)C1=CC=C(C)C=C1 XIAHSJTUQAWUAW-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- DTURFDMMYCLMAD-UHFFFAOYSA-N 2,2,4,4,6,6-hexamethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)C(C)(C)C(=O)C(C)(C)C DTURFDMMYCLMAD-UHFFFAOYSA-N 0.000 description 1
- UMMFCLKKXWVNBN-UHFFFAOYSA-N 2,2,4,4,6-pentamethylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)(C)C(=O)C(C)(C)C UMMFCLKKXWVNBN-UHFFFAOYSA-N 0.000 description 1
- BZJFHTPQXQMAFZ-UHFFFAOYSA-N 2,2,4,4,6-pentamethyloctane-3,5-dione Chemical compound CCC(C)C(=O)C(C)(C)C(=O)C(C)(C)C BZJFHTPQXQMAFZ-UHFFFAOYSA-N 0.000 description 1
- DMLBDUYFEJULIU-UHFFFAOYSA-N 2,2,4,4-tetramethyloctane-3,5-dione Chemical compound CCCC(=O)C(C)(C)C(=O)C(C)(C)C DMLBDUYFEJULIU-UHFFFAOYSA-N 0.000 description 1
- QPUYYDWCNKVYMB-UHFFFAOYSA-N 2,2,4,6-tetramethyl-4-(2-methylpropyl)heptane-3,5-dione Chemical compound CC(C)CC(C)(C(=O)C(C)C)C(=O)C(C)(C)C QPUYYDWCNKVYMB-UHFFFAOYSA-N 0.000 description 1
- LRPQCIBYHJOVIH-UHFFFAOYSA-N 2,2,4,6-tetramethyl-4-phenylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)(C(=O)C(C)(C)C)C1=CC=CC=C1 LRPQCIBYHJOVIH-UHFFFAOYSA-N 0.000 description 1
- QJDDHQXLJSRKOB-UHFFFAOYSA-N 2,2,4,6-tetramethylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)C(=O)C(C)(C)C QJDDHQXLJSRKOB-UHFFFAOYSA-N 0.000 description 1
- UIXRPMGDJBNZEH-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-(3-methylbutyl)heptane-3,5-dione Chemical compound CC(C)CCC(C(=O)C(C)(C)C)C(=O)C(C)(C)C UIXRPMGDJBNZEH-UHFFFAOYSA-N 0.000 description 1
- QDLSRWSPWZFMRT-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-propylheptane-3,5-dione Chemical compound CCCC(C(=O)C(C)(C)C)C(=O)C(C)(C)C QDLSRWSPWZFMRT-UHFFFAOYSA-N 0.000 description 1
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
- LPTYFHQHAPKMHI-UHFFFAOYSA-N 2,2,6-trimethyl-4-(2-methylpropyl)octane-3,5-dione Chemical compound CCC(C)C(=O)C(CC(C)C)C(=O)C(C)(C)C LPTYFHQHAPKMHI-UHFFFAOYSA-N 0.000 description 1
- KMLCMTGKESUPKR-UHFFFAOYSA-N 2,2,6-trimethyl-4-(3-methylbutyl)heptane-3,5-dione Chemical compound CC(C)CCC(C(=O)C(C)C)C(=O)C(C)(C)C KMLCMTGKESUPKR-UHFFFAOYSA-N 0.000 description 1
- JXQVCGUTRPXJRX-UHFFFAOYSA-N 2,2,6-trimethyl-4-phenylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C(=O)C(C)(C)C)C1=CC=CC=C1 JXQVCGUTRPXJRX-UHFFFAOYSA-N 0.000 description 1
- QFQMSDZNJQVEFN-UHFFFAOYSA-N 2,2-diethyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(CC)(CC)C(=O)C1=CC=CC=C1 QFQMSDZNJQVEFN-UHFFFAOYSA-N 0.000 description 1
- JPZPMMCZXFICMY-UHFFFAOYSA-N 2,2-dimethyl-4-phenylheptane-3,5-dione Chemical compound CCC(=O)C(C(=O)C(C)(C)C)C1=CC=CC=C1 JPZPMMCZXFICMY-UHFFFAOYSA-N 0.000 description 1
- LHQYNVWJWUCTSS-UHFFFAOYSA-N 2,2-dimethylheptane-3,5-dione Chemical compound CCC(=O)CC(=O)C(C)(C)C LHQYNVWJWUCTSS-UHFFFAOYSA-N 0.000 description 1
- VPHRTPYUDQBVFU-UHFFFAOYSA-N 2,4,4,6-tetramethylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)(C)C(=O)C(C)C VPHRTPYUDQBVFU-UHFFFAOYSA-N 0.000 description 1
- QUKQBVKXVORGGM-UHFFFAOYSA-N 2,4,6-trimethyl-4-(2-methylpropyl)heptane-3,5-dione Chemical compound CC(C)CC(C)(C(=O)C(C)C)C(=O)C(C)C QUKQBVKXVORGGM-UHFFFAOYSA-N 0.000 description 1
- YPUJUOLQUJCQMD-UHFFFAOYSA-N 2,4,6-trimethyl-4-propan-2-ylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)(C(C)C)C(=O)C(C)C YPUJUOLQUJCQMD-UHFFFAOYSA-N 0.000 description 1
- RKCGTASEIZWCPO-UHFFFAOYSA-N 2,4-dimethyl-4-(2-methylpropyl)heptane-3,5-dione Chemical compound CCC(=O)C(C)(CC(C)C)C(=O)C(C)C RKCGTASEIZWCPO-UHFFFAOYSA-N 0.000 description 1
- SKLUIKVWRYQVHG-UHFFFAOYSA-N 2,6-dimethyl-4-propan-2-ylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C(C)C)C(=O)C(C)C SKLUIKVWRYQVHG-UHFFFAOYSA-N 0.000 description 1
- BSELJBOMYPMBNL-UHFFFAOYSA-N 2-acetyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(C(=O)C)CCC2=C1 BSELJBOMYPMBNL-UHFFFAOYSA-N 0.000 description 1
- DQQGIZNULRZOOC-UHFFFAOYSA-N 2-benzyl-2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)C=1C=CC=CC=1)(C)CC1=CC=CC=C1 DQQGIZNULRZOOC-UHFFFAOYSA-N 0.000 description 1
- MGMZIFGPURRRPX-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)(CC)C(=O)C1=CC=CC=C1 MGMZIFGPURRRPX-UHFFFAOYSA-N 0.000 description 1
- GWJNVYCFUDHJNC-UHFFFAOYSA-N 2-methyl-1,3-diphenyl-2-propan-2-ylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)(C(C)C)C(=O)C1=CC=CC=C1 GWJNVYCFUDHJNC-UHFFFAOYSA-N 0.000 description 1
- HIPWXOWHGQIKOV-UHFFFAOYSA-N 2-methyl-2-(2-methylpropyl)-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)(CC(C)C)C(=O)C1=CC=CC=C1 HIPWXOWHGQIKOV-UHFFFAOYSA-N 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
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- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YWDBSCORAARPPF-VWUMJDOOSA-N tixocortol Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CS)[C@@H]4[C@@H]3CCC2=C1 YWDBSCORAARPPF-VWUMJDOOSA-N 0.000 description 1
- 229960004631 tixocortol Drugs 0.000 description 1
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- NNIUGFWCIDVDCZ-UHFFFAOYSA-N undecane-5,7-dione Chemical compound CCCCC(=O)CC(=O)CCCC NNIUGFWCIDVDCZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0204—Ethers
-
- 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
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- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/12—Ketones containing more than one keto group
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
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- 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
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- 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
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- 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
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- C08F4/646—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/647—Catalysts containing a specific non-metal or metal-free compound
- C08F4/649—Catalysts containing a specific non-metal or metal-free compound organic
- C08F4/6494—Catalysts containing a specific non-metal or metal-free compound organic containing oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
- C08F4/6543—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof halides of magnesium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI932102A IT1270842B (it) | 1993-10-01 | 1993-10-01 | Componenti e catalizzatori per la polimerizzazione di olefine |
| ITMI932102 | 1993-10-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944573A0 FI944573A0 (fi) | 1994-09-30 |
| FI944573A FI944573A (fi) | 1995-04-02 |
| FI112237B true FI112237B (fi) | 2003-11-14 |
Family
ID=11366974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI944573A FI112237B (fi) | 1993-10-01 | 1994-09-30 | Olefiinien polymerointiin tarkoitettuja komponentteja ja katalyyttejä |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5468704A (zh) |
| EP (1) | EP0646605B1 (zh) |
| JP (2) | JP3688308B2 (zh) |
| KR (2) | KR100347974B1 (zh) |
| CN (2) | CN1054139C (zh) |
| AT (1) | ATE180793T1 (zh) |
| AU (1) | AU677422B2 (zh) |
| BR (1) | BR9403967A (zh) |
| CA (1) | CA2133352A1 (zh) |
| DE (1) | DE69418808T2 (zh) |
| DK (1) | DK0646605T3 (zh) |
| ES (1) | ES2133459T3 (zh) |
| FI (1) | FI112237B (zh) |
| IT (1) | IT1270842B (zh) |
| TW (1) | TW264486B (zh) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU706739B2 (en) * | 1994-05-12 | 1999-06-24 | Showa Denko Kabushiki Kaisha | A method for the production of propylene-based polymers, catalyst component or polymerization and method for its production |
| US6184328B1 (en) | 1994-09-07 | 2001-02-06 | Showa Denko Kabushiki Kaisha | Propylene-based polymer, method for its production, composition thereof, catalyst component for polymerization, and method for its production |
| AU690907B2 (en) * | 1994-05-12 | 1998-05-07 | Showa Denko Kabushiki Kaisha | Propylene polymer, process for producing the same, composition thereof, polymerization catalyst component, and process for producing the same |
| IT1274253B (it) * | 1995-02-21 | 1997-07-15 | Himont Inc | Processo per la preparazione di componenti catalitici solidi per la polimerizzazione di olefine |
| CN1063188C (zh) * | 1996-12-17 | 2001-03-14 | 中国科学院化学研究所 | 一种合成间规聚苯乙烯催化剂体系及其制法 |
| IE980775A1 (en) * | 1998-09-17 | 2000-03-22 | Loctite R & D Ltd | Auto-oxidation systems for air-activatable polymerisable compositions |
| SG96207A1 (en) | 2000-03-30 | 2003-05-23 | Sumitomo Chemical Co | Process for producing catalyst for olefin polymerization and process for producing olefin polymer |
| CN100362026C (zh) * | 2000-03-30 | 2008-01-16 | 住友化学株式会社 | 烯烃聚合用催化剂的制备方法和烯烃聚合物的制备方法 |
| CN1318457C (zh) * | 2004-09-02 | 2007-05-30 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分和催化剂 |
| CN100338018C (zh) * | 2004-10-29 | 2007-09-19 | 中国石油化工股份有限公司 | 一种环戊酯类化合物及其合成方法和应用 |
| CN101139407B (zh) * | 2006-09-07 | 2010-10-06 | 北京金鼎科化工科技有限公司 | 一种用于乙烯聚合或共聚合的催化剂前体及其制备方法 |
| CN101412775B (zh) * | 2007-10-15 | 2010-12-22 | 北京金鼎科化工科技有限公司 | 一种用于丙烯聚合或共聚合的催化剂前体及其制备方法 |
| EP2070954A1 (en) * | 2007-12-14 | 2009-06-17 | Total Petrochemicals Research Feluy | Process for the production of a propylene polymer having a broad molecular weight distribution and a low ash content |
| EP2093315A1 (en) * | 2008-02-22 | 2009-08-26 | Total Petrochemicals Research Feluy | Fibres and nonwoven prepared from polypropylene having a large dispersity index |
| CN101671410B (zh) * | 2008-09-11 | 2011-12-28 | 中国石油化工股份有限公司 | 用于烯烃聚合的催化剂组分及其催化剂 |
| EP2679609A1 (en) | 2012-06-28 | 2014-01-01 | Lummus Novolen Technology Gmbh | Sterically demanding dialkoxydialkylsilanes as external donors for ziegler catalysts for the polymerization of propylene |
| CN105330774B (zh) * | 2014-06-24 | 2017-10-03 | 中国石油化工股份有限公司 | 一种宽立构规整度分布聚丙烯的制备方法及得到的聚丙烯 |
| CN105330772A (zh) * | 2014-06-24 | 2016-02-17 | 中国石油化工股份有限公司 | 一种聚丙烯立构规整度调节剂及其应用 |
| KR101699590B1 (ko) | 2014-11-28 | 2017-01-24 | 한화토탈 주식회사 | 프로필렌 중합용 고체촉매 및 이를 이용한 폴리프로필렌 제조 방법 |
| CN108059689B (zh) * | 2016-11-09 | 2020-05-08 | 中国石油天然气股份有限公司 | 烯烃聚合前催化剂组合物及其制备方法、烯烃聚合催化剂组合物 |
| WO2018161854A1 (zh) | 2017-03-10 | 2018-09-13 | 北京利和知信科技有限公司 | 用于烯烃聚合的固体催化剂组分、催化剂及其应用 |
| CN110950983B (zh) * | 2018-09-26 | 2022-01-04 | 中国石油化工股份有限公司 | 用于烯烃聚合的催化剂组分、催化剂及烯烃聚合方法 |
| CN110950985B (zh) * | 2018-09-26 | 2022-01-04 | 中国石油化工股份有限公司 | 一种用于烯烃聚合的催化剂组分、催化剂及烯烃聚合方法 |
| DK3750456T3 (da) | 2019-06-14 | 2021-06-07 | Sky Light As | Fleksibelt element til formning af engangsbestik |
| WO2022045231A1 (ja) | 2020-08-26 | 2022-03-03 | 三井化学株式会社 | エステル化合物 |
| WO2022138635A1 (ja) | 2020-12-21 | 2022-06-30 | 三井化学株式会社 | エステル化合物 |
| CN116041577A (zh) | 2021-10-28 | 2023-05-02 | 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8002599A (nl) * | 1980-05-07 | 1981-12-01 | Stamicarbon | Werkwijze voor de bereiding van een polymerisatiekatalysator en bereiding van etheenpolymeren daarmee. |
| US4540680A (en) * | 1980-11-24 | 1985-09-10 | National Distillers And Chemical Corporation | Intermetallic compounds of polymeric transition metal oxide alkoxides and catalytic use thereof |
| IT1190683B (it) * | 1982-02-12 | 1988-02-24 | Montedison Spa | Componenti e catalizzatori per la polimerizzazione di olefine |
| JPH0686490B2 (ja) * | 1985-04-05 | 1994-11-02 | 三菱油化株式会社 | オレフイン重合体の製造法 |
| IT1227258B (it) * | 1988-09-30 | 1991-03-28 | Himont Inc | Componenti e catalizzatori per la polimerizzazione di olefine |
| JP2805344B2 (ja) * | 1989-07-11 | 1998-09-30 | 昭和電工株式会社 | オレフィン重合触媒の製造方法およびオレフィンの重合方法 |
| IT1241093B (it) * | 1990-03-30 | 1993-12-29 | Himont Inc | Componenti e catalizzatori per la polimerizzazione di olefine |
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1993
- 1993-10-01 IT ITMI932102A patent/IT1270842B/it active IP Right Grant
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1994
- 1994-05-25 TW TW083104729A patent/TW264486B/zh active
- 1994-09-29 AU AU74350/94A patent/AU677422B2/en not_active Ceased
- 1994-09-30 FI FI944573A patent/FI112237B/fi not_active IP Right Cessation
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- 1994-09-30 DE DE69418808T patent/DE69418808T2/de not_active Expired - Lifetime
- 1994-09-30 AT AT94115455T patent/ATE180793T1/de not_active IP Right Cessation
- 1994-09-30 BR BR9403967A patent/BR9403967A/pt not_active IP Right Cessation
- 1994-09-30 CN CN94117900A patent/CN1054139C/zh not_active Expired - Fee Related
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1999
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2001
- 2001-12-24 KR KR1020010084218A patent/KR100368786B1/ko not_active IP Right Cessation
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2005
- 2005-03-11 JP JP2005069165A patent/JP3847768B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3847768B2 (ja) | 2006-11-22 |
| EP0646605A1 (en) | 1995-04-05 |
| JPH07233209A (ja) | 1995-09-05 |
| AU677422B2 (en) | 1997-04-24 |
| IT1270842B (it) | 1997-05-13 |
| TW264486B (zh) | 1995-12-01 |
| DK0646605T3 (da) | 1999-06-23 |
| CN1105671A (zh) | 1995-07-26 |
| FI944573A (fi) | 1995-04-02 |
| CA2133352A1 (en) | 1995-04-02 |
| ATE180793T1 (de) | 1999-06-15 |
| FI944573A0 (fi) | 1994-09-30 |
| EP0646605B1 (en) | 1999-06-02 |
| CN1257061A (zh) | 2000-06-21 |
| CN1054139C (zh) | 2000-07-05 |
| DE69418808D1 (de) | 1999-07-08 |
| CN1138743C (zh) | 2004-02-18 |
| JP2005226076A (ja) | 2005-08-25 |
| ITMI932102A0 (it) | 1993-10-01 |
| US5468704A (en) | 1995-11-21 |
| KR100368786B1 (ko) | 2003-01-24 |
| BR9403967A (pt) | 1995-06-27 |
| DE69418808T2 (de) | 1999-10-07 |
| JP3688308B2 (ja) | 2005-08-24 |
| ITMI932102A1 (it) | 1995-04-01 |
| AU7435094A (en) | 1995-04-13 |
| ES2133459T3 (es) | 1999-09-16 |
| KR950011480A (ko) | 1995-05-15 |
| KR100347974B1 (ko) | 2002-11-22 |
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