IL127322A - Aminosilane compounds and catalyst for alpha-olefin polymer containing them - Google Patents
Aminosilane compounds and catalyst for alpha-olefin polymer containing themInfo
- Publication number
- IL127322A IL127322A IL12732298A IL12732298A IL127322A IL 127322 A IL127322 A IL 127322A IL 12732298 A IL12732298 A IL 12732298A IL 12732298 A IL12732298 A IL 12732298A IL 127322 A IL127322 A IL 127322A
- Authority
- IL
- Israel
- Prior art keywords
- branched
- aminosilane
- linear
- alkyl
- substituted
- Prior art date
Links
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000003054 catalyst Substances 0.000 title claims description 22
- 238000006116 polymerization reaction Methods 0.000 title claims description 16
- 239000004711 α-olefin Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 7
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- -1 3,3,3-trifluoro-propyl Chemical group 0.000 claims description 36
- 239000011777 magnesium Substances 0.000 claims description 28
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 29
- 238000002390 rotary evaporation Methods 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 20
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 20
- 238000004821 distillation Methods 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- UUTBSNFHBOVJLI-UHFFFAOYSA-N 2-(3-methylphenyl)pyrrolidine Chemical compound CC1=CC=CC(C2NCCC2)=C1 UUTBSNFHBOVJLI-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011949 solid catalyst Substances 0.000 description 4
- WVFLUUDVJHXQDX-UHFFFAOYSA-N trimethyl(piperidin-2-yl)silane Chemical compound C[Si](C)(C)C1CCCCN1 WVFLUUDVJHXQDX-UHFFFAOYSA-N 0.000 description 4
- YKFXSWPGGIAPSM-UHFFFAOYSA-N 2-(3-methylphenyl)piperidine Chemical compound CC1=CC=CC(C2NCCCC2)=C1 YKFXSWPGGIAPSM-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- HODIIHKVZSUTGR-UHFFFAOYSA-N tert-butyl(piperidin-1-yl)carbamic acid Chemical compound CC(C)(C)N(C(O)=O)N1CCCCC1 HODIIHKVZSUTGR-UHFFFAOYSA-N 0.000 description 3
- ATAKCZSQWBOMHH-UHFFFAOYSA-N tert-butyl(pyrrolidin-1-yl)carbamic acid Chemical compound CC(C)(C)N(C(O)=O)N1CCCC1 ATAKCZSQWBOMHH-UHFFFAOYSA-N 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 2
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229920001384 propylene homopolymer Polymers 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- HRKQEHYUHWEITH-UHFFFAOYSA-N tert-butyl-[2-(3-methylphenyl)piperidin-1-yl]carbamic acid Chemical compound CC1=CC=CC(C2N(CCCC2)N(C(O)=O)C(C)(C)C)=C1 HRKQEHYUHWEITH-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- KQRWBDURMARJQV-UHFFFAOYSA-N trimethyl(pyrrolidin-2-yl)silane Chemical compound C[Si](C)(C)C1CCCN1 KQRWBDURMARJQV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SDGKUVSVPIIUCF-KNVOCYPGSA-N (2r,6s)-2,6-dimethylpiperidine Chemical compound C[C@H]1CCC[C@@H](C)N1 SDGKUVSVPIIUCF-KNVOCYPGSA-N 0.000 description 1
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LBUPWCHXRSTTNO-UHFFFAOYSA-N 2,2-dimethylpiperidine Chemical compound CC1(C)CCCCN1 LBUPWCHXRSTTNO-UHFFFAOYSA-N 0.000 description 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical compound [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- RAYBZPINKIHRAG-UHFFFAOYSA-N dimethoxy-(4-methylpiperidin-1-yl)-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](OC)(OC)N1CCC(C)CC1 RAYBZPINKIHRAG-UHFFFAOYSA-N 0.000 description 1
- BDZLBTVSWMLOPQ-UHFFFAOYSA-N dimethoxy-[2-(3-methylphenyl)piperidin-1-yl]-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](OC)(OC)N1CCCCC1C1=CC=CC(C)=C1 BDZLBTVSWMLOPQ-UHFFFAOYSA-N 0.000 description 1
- MPUXYTVBUPCGLW-UHFFFAOYSA-N dimethoxy-[2-(3-methylphenyl)pyrrolidin-1-yl]-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](OC)(OC)N1CCCC1C1=CC=CC(C)=C1 MPUXYTVBUPCGLW-UHFFFAOYSA-N 0.000 description 1
- DOODELBMKSEMGZ-UHFFFAOYSA-N dimethoxy-pyrrolidin-1-yl-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](OC)(OC)N1CCCC1 DOODELBMKSEMGZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
- 238000004476 mid-IR spectroscopy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IPFFIGLTTCGSDM-UHFFFAOYSA-N tert-butyl-(2-trimethylsilylpiperidin-1-yl)carbamic acid Chemical compound CC(C)(C)N(C(O)=O)N1CCCCC1[Si](C)(C)C IPFFIGLTTCGSDM-UHFFFAOYSA-N 0.000 description 1
- JQGKNBQEZJSAND-UHFFFAOYSA-N tert-butyl-(2-trimethylsilylpyrrolidin-1-yl)carbamic acid Chemical compound CC(C)(C)N(C(O)=O)N1CCCC1[Si](C)(C)C JQGKNBQEZJSAND-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C08F4/646—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64
- C08F4/6465—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64 containing silicium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (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 |
|---|---|---|---|
| US08/996,854 US6130180A (en) | 1997-12-23 | 1997-12-23 | Catalyst for the polymerization of alpha-olefins containing substituted amino silane compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL127322A0 IL127322A0 (en) | 1999-09-22 |
| IL127322A true IL127322A (en) | 2001-04-30 |
Family
ID=25543375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12732298A IL127322A (en) | 1997-12-23 | 1998-11-30 | Aminosilane compounds and catalyst for alpha-olefin polymer containing them |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6130180A (de) |
| EP (1) | EP0926164B1 (de) |
| JP (1) | JP4174114B2 (de) |
| KR (1) | KR19990063295A (de) |
| AR (1) | AR017947A1 (de) |
| AU (1) | AU739416B2 (de) |
| BR (1) | BR9805616A (de) |
| CA (1) | CA2255892A1 (de) |
| CZ (1) | CZ395598A3 (de) |
| DE (1) | DE69821890T2 (de) |
| ES (1) | ES2212206T3 (de) |
| HU (1) | HUP9802980A3 (de) |
| ID (1) | ID21553A (de) |
| IL (1) | IL127322A (de) |
| NO (1) | NO986047L (de) |
| PL (1) | PL330462A1 (de) |
| SK (1) | SK176098A3 (de) |
| TW (1) | TW499442B (de) |
| ZA (1) | ZA9811789B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100371312B1 (ko) * | 1999-01-13 | 2003-02-07 | 시벤토, 인크. | 알킬(아미노)디알콕시실란의 제조 방법 |
| DE19957384A1 (de) | 1999-11-29 | 2001-05-31 | Targor Gmbh | Hochmolekulares Polypropylen mit breiter Molekulargewichtsverteilung und geringer isotaktischer Sequenzlänge |
| KR101150579B1 (ko) * | 2010-01-22 | 2012-05-30 | 삼성토탈 주식회사 | 프로필렌 중합 및 공중합 방법 |
| CN106632758B (zh) * | 2015-10-29 | 2019-09-27 | 中国石油化工股份有限公司 | 乙烯聚合用固体催化剂组分及其制备与应用 |
| CN111295399B (zh) | 2017-11-06 | 2022-09-06 | 埃克森美孚化学专利公司 | 基于丙烯的抗冲共聚物及生产方法和设备 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180636A (en) * | 1976-06-24 | 1979-12-25 | Showa Denko Kabushiki Kaisha | Process for polymerizing or co-polymerizing propylene |
| US4242479A (en) * | 1976-12-23 | 1980-12-30 | Showa Yuka Kabushiki Kaisha | Process for producing an improved ethylenic polymer |
| US4347160A (en) * | 1980-06-27 | 1982-08-31 | Stauffer Chemical Company | Titanium halide catalyst system |
| IT1209255B (it) * | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
| US4352917A (en) * | 1980-09-18 | 1982-10-05 | Sws Silicones Corporation | Hydrophilic coatings for textile materials |
| US4491669A (en) * | 1980-11-12 | 1985-01-01 | Petrarch Systems Inc. | Mixed alkoxyaminosilanes, methods of making same and vulcanizing silicons prepared therefrom |
| JPS57153005A (en) * | 1981-03-19 | 1982-09-21 | Ube Ind Ltd | Polymerization of alpha-olefin |
| US4530912A (en) * | 1981-06-04 | 1985-07-23 | Chemplex Company | Polymerization catalyst and method |
| EP0072129B2 (de) * | 1981-08-07 | 1990-02-28 | Imperial Chemical Industries Plc | Übergangsmetallzusammensetzung auf einem Träger aufgebracht |
| US4382019A (en) * | 1981-09-10 | 1983-05-03 | Stauffer Chemical Company | Purified catalyst support |
| US4442276A (en) * | 1982-02-12 | 1984-04-10 | Mitsui Petrochemical Industries, Ltd. | Process for polymerizing or copolymerizing olefins |
| IT1190683B (it) * | 1982-02-12 | 1988-02-24 | Montedison Spa | Componenti e catalizzatori per la polimerizzazione di olefine |
| IT1190682B (it) * | 1982-02-12 | 1988-02-24 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine |
| IT1190681B (it) * | 1982-02-12 | 1988-02-24 | Montedison Spa | Componenti e catalizzatori per la polimerizzazione di olefine |
| US4560671A (en) * | 1983-07-01 | 1985-12-24 | Union Carbide Corporation | Olefin polymerization catalysts adapted for gas phase processes |
| US4581342A (en) * | 1984-11-26 | 1986-04-08 | Standard Oil Company (Indiana) | Supported olefin polymerization catalyst |
| US4657882A (en) * | 1984-11-26 | 1987-04-14 | Amoco Corporation | Supported olefin polymerization catalyst produced from a magnesium alkyl/organophosphoryl complex |
| CA1336596C (en) * | 1989-07-26 | 1995-08-08 | Constantine A. Stewart | Organosilane compounds |
| US5102842A (en) * | 1990-08-23 | 1992-04-07 | Himont Incorporated | Catalyst for the polymerization of alpha-olefins containing trifluoropropyl substituted silane compounds |
| JP2837973B2 (ja) * | 1991-07-04 | 1998-12-16 | 沖電気工業株式会社 | トナー残量検知機構 |
| US5401566A (en) * | 1993-08-26 | 1995-03-28 | Wacker Silicones Corporation | Coated fabrics for air bags |
| JP3361579B2 (ja) * | 1993-10-15 | 2003-01-07 | 昭和電工株式会社 | オレフィン重合用触媒およびオレフィン重合体の製造法 |
| JP3426664B2 (ja) * | 1993-10-21 | 2003-07-14 | 昭和電工株式会社 | オレフィン重合用固体触媒成分、オレフィン重合用触媒及びオレフィンの重合方法 |
| ES2107109T3 (es) * | 1993-12-16 | 1997-11-16 | Montell North America Inc | Resinas de homopolimeros de propileno que tienen un alto contenido de estereobloques. |
| JP3431971B2 (ja) * | 1993-12-21 | 2003-07-28 | 三井化学株式会社 | オレフィン重合用電子供与体、これを含むオレフィン重合触媒 |
| JPH083215A (ja) * | 1994-04-22 | 1996-01-09 | Ube Ind Ltd | α−オレフィンの重合方法 |
| JPH08120021A (ja) * | 1994-05-24 | 1996-05-14 | Ube Ind Ltd | α−オレフィンの重合方法 |
| JPH08100019A (ja) * | 1994-09-29 | 1996-04-16 | Mitsubishi Chem Corp | オレフィン重合用触媒 |
| JPH08157519A (ja) * | 1994-12-01 | 1996-06-18 | Mitsubishi Chem Corp | オレフィン重合用触媒 |
| JPH08301920A (ja) * | 1995-05-02 | 1996-11-19 | Ube Ind Ltd | α−オレフィンの重合方法 |
| JPH0940714A (ja) * | 1995-07-28 | 1997-02-10 | Ube Ind Ltd | アミノアルコキシシラン |
| JPH0959312A (ja) * | 1995-08-25 | 1997-03-04 | Ube Ind Ltd | プロピレン共重合体の製造方法 |
| JPH09278819A (ja) * | 1996-04-17 | 1997-10-28 | Mitsui Petrochem Ind Ltd | オレフィン重合用触媒およびこれを用いるオレフィンの重合方法 |
| CA2204464A1 (en) * | 1996-11-06 | 1998-11-05 | Ube Industries Limited | Process for polymerization of .alpha.-olefin |
-
1997
- 1997-12-23 US US08/996,854 patent/US6130180A/en not_active Expired - Fee Related
-
1998
- 1998-11-30 IL IL12732298A patent/IL127322A/en active IP Right Grant
- 1998-12-02 CZ CZ983955A patent/CZ395598A3/cs unknown
- 1998-12-07 CA CA002255892A patent/CA2255892A1/en not_active Abandoned
- 1998-12-18 SK SK1760-98A patent/SK176098A3/sk unknown
- 1998-12-19 EP EP98124145A patent/EP0926164B1/de not_active Expired - Lifetime
- 1998-12-19 DE DE69821890T patent/DE69821890T2/de not_active Expired - Lifetime
- 1998-12-19 ES ES98124145T patent/ES2212206T3/es not_active Expired - Lifetime
- 1998-12-21 HU HU9802980A patent/HUP9802980A3/hu unknown
- 1998-12-21 PL PL98330462A patent/PL330462A1/xx unknown
- 1998-12-22 KR KR1019980057008A patent/KR19990063295A/ko not_active Application Discontinuation
- 1998-12-22 TW TW087121445A patent/TW499442B/zh active
- 1998-12-22 ZA ZA9811789A patent/ZA9811789B/xx unknown
- 1998-12-22 BR BR9805616-6A patent/BR9805616A/pt not_active Application Discontinuation
- 1998-12-22 AU AU98122/98A patent/AU739416B2/en not_active Ceased
- 1998-12-22 NO NO986047A patent/NO986047L/no not_active Application Discontinuation
- 1998-12-22 AR ARP980106587A patent/AR017947A1/es unknown
- 1998-12-23 ID IDP981684A patent/ID21553A/id unknown
- 1998-12-24 JP JP36744998A patent/JP4174114B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ID21553A (id) | 1999-06-24 |
| AU739416B2 (en) | 2001-10-11 |
| AU9812298A (en) | 1999-07-15 |
| KR19990063295A (ko) | 1999-07-26 |
| EP0926164B1 (de) | 2004-02-25 |
| ES2212206T3 (es) | 2004-07-16 |
| BR9805616A (pt) | 1999-12-21 |
| EP0926164A2 (de) | 1999-06-30 |
| DE69821890T2 (de) | 2004-12-16 |
| JP4174114B2 (ja) | 2008-10-29 |
| DE69821890D1 (de) | 2004-04-01 |
| TW499442B (en) | 2002-08-21 |
| NO986047L (no) | 1999-06-24 |
| HUP9802980A2 (hu) | 1999-10-28 |
| CZ395598A3 (cs) | 1999-08-11 |
| PL330462A1 (en) | 1999-07-05 |
| HU9802980D0 (en) | 1999-02-01 |
| SK176098A3 (en) | 2000-03-13 |
| JPH11246618A (ja) | 1999-09-14 |
| EP0926164A3 (de) | 2001-02-28 |
| CA2255892A1 (en) | 1999-06-23 |
| US6130180A (en) | 2000-10-10 |
| HUP9802980A3 (en) | 2001-06-28 |
| ZA9811789B (en) | 1999-06-29 |
| NO986047D0 (no) | 1998-12-22 |
| AR017947A1 (es) | 2001-10-24 |
| IL127322A0 (en) | 1999-09-22 |
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| FF | Patent granted | ||
| KB | Patent renewed |