MXPA02004322A - Catalizador de polimerizacion de olefinas bidentado o tridentado soporte heterogeneo activo. - Google Patents
Catalizador de polimerizacion de olefinas bidentado o tridentado soporte heterogeneo activo.Info
- Publication number
- MXPA02004322A MXPA02004322A MXPA02004322A MXPA02004322A MXPA02004322A MX PA02004322 A MXPA02004322 A MX PA02004322A MX PA02004322 A MXPA02004322 A MX PA02004322A MX PA02004322 A MXPA02004322 A MX PA02004322A MX PA02004322 A MXPA02004322 A MX PA02004322A
- Authority
- MX
- Mexico
- Prior art keywords
- catalyst composition
- composition according
- transition metal
- inorganic oxide
- aluminum
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 174
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 25
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 159
- -1 aluminum compound Chemical class 0.000 claims abstract description 73
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 69
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 65
- 150000003624 transition metals Chemical class 0.000 claims abstract description 65
- 229910052809 inorganic oxide Inorganic materials 0.000 claims abstract description 59
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 56
- 239000000460 chlorine Substances 0.000 claims description 326
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 81
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 57
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000007788 liquid Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000000377 silicon dioxide Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 22
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 21
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910052742 iron Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 229910052763 palladium Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000003623 transition metal compounds Chemical class 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 9
- 229910052726 zirconium Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 239000004711 α-olefin Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- KURZCZMGELAPSV-UHFFFAOYSA-N [Br].[I] Chemical compound [Br].[I] KURZCZMGELAPSV-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 239000008247 solid mixture Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 24
- 238000011065 in-situ storage Methods 0.000 abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 123
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 20
- 239000012190 activator Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 11
- 239000012041 precatalyst Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000002685 polymerization catalyst Substances 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052681 coesite Inorganic materials 0.000 description 6
- 229910052906 cristobalite Inorganic materials 0.000 description 6
- 239000002638 heterogeneous catalyst Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052682 stishovite Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 229910052905 tridymite Inorganic materials 0.000 description 6
- 230000004913 activation Effects 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 239000012967 coordination catalyst Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229960002089 ferrous chloride Drugs 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012968 metallocene catalyst Substances 0.000 description 4
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 125000005425 toluyl group Chemical group 0.000 description 3
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical group C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 2
- 238000012674 dispersion polymerization Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229960004029 silicic acid Drugs 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical group C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- IFXGRVXPSNHLNW-UHFFFAOYSA-N 1-ethenylcyclobutene Chemical group C=CC1=CCC1 IFXGRVXPSNHLNW-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- QKVZCFPSKXSEOZ-UHFFFAOYSA-N butan-1-olate;ditert-butylalumanylium Chemical compound CCCC[O-].CC(C)(C)[Al+]C(C)(C)C QKVZCFPSKXSEOZ-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LKRBKNPREDAJJQ-UHFFFAOYSA-M chloro-di(propan-2-yl)alumane Chemical compound [Cl-].CC(C)[Al+]C(C)C LKRBKNPREDAJJQ-UHFFFAOYSA-M 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HRLHOWWCFUKTIY-UHFFFAOYSA-L dichloroalumanylium Chemical compound Cl[Al+]Cl HRLHOWWCFUKTIY-UHFFFAOYSA-L 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- DLRHRQTUCJTIIV-UHFFFAOYSA-N diethoxy(ethyl)alumane Chemical compound CC[O-].CC[O-].CC[Al+2] DLRHRQTUCJTIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XGAIERUWZADBAO-UHFFFAOYSA-N ethoxy-bis(2-methylpropyl)alumane Chemical compound CCO[Al](CC(C)C)CC(C)C XGAIERUWZADBAO-UHFFFAOYSA-N 0.000 description 1
- UYONORMOFAZUJY-UHFFFAOYSA-N ethoxy-di(propan-2-yl)alumane Chemical compound CC[O-].CC(C)[Al+]C(C)C UYONORMOFAZUJY-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- CSYSULGPHGCBQD-UHFFFAOYSA-N s-ethylisothiouronium diethylphosphate Chemical compound CCSC(N)=N.CCOP(O)(=O)OCC CSYSULGPHGCBQD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/602—Component covered by group C08F4/60 with an organo-aluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43180399A | 1999-11-01 | 1999-11-01 | |
| PCT/US2000/028920 WO2001032723A1 (en) | 1999-11-01 | 2000-10-19 | Active, heterogeneous supported bi- or tri-dentate olefin polymerisation catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02004322A true MXPA02004322A (es) | 2002-11-07 |
Family
ID=23713487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02004322A MXPA02004322A (es) | 1999-11-01 | 2000-10-19 | Catalizador de polimerizacion de olefinas bidentado o tridentado soporte heterogeneo activo. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7291575B2 (https=) |
| EP (1) | EP1237954B1 (https=) |
| JP (2) | JP5258077B2 (https=) |
| KR (1) | KR100710963B1 (https=) |
| CN (1) | CN1178964C (https=) |
| AT (1) | ATE315053T1 (https=) |
| AU (1) | AU1096001A (https=) |
| BR (1) | BR0015192B1 (https=) |
| CA (1) | CA2389587C (https=) |
| DE (1) | DE60025386T2 (https=) |
| MX (1) | MXPA02004322A (https=) |
| SG (1) | SG97961A1 (https=) |
| WO (1) | WO2001032723A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1426385B1 (en) | 2001-07-23 | 2012-08-22 | Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences | Catalyst for polymerization or copolymerization of olefins, preparation and use of the same |
| CN101687776B (zh) * | 2007-07-04 | 2015-07-01 | 三井化学株式会社 | 过渡金属配位化合物、含有该化合物的烯烃聚合用催化剂以及在该催化剂存在下进行的烯烃聚合物的制造方法 |
| EP2489431B1 (en) | 2011-02-16 | 2013-05-01 | Linde AG | Method for preparing a catalyst composition for oligomerization of ethylene and respective catalyst composition pre-formation unit |
| KR102578006B1 (ko) | 2015-05-11 | 2023-09-12 | 더블유.알. 그레이스 앤드 캄파니-콘. | 개질된 점토, 지지된 메탈로센 중합 촉매의 제조 방법, 제조된 촉매, 및 이의 용도 |
| US10940460B2 (en) | 2015-05-11 | 2021-03-09 | W. R. Grace & Co.-Conn. | Process to produce modified clay, modified clay produced and use thereof |
| KR102472153B1 (ko) * | 2016-12-30 | 2022-11-28 | 사빅 글로벌 테크놀러지스 비.브이. | 선택적인 1-헥센 제조용 균질 촉매의 제조 방법 |
| US11285469B2 (en) | 2016-12-30 | 2022-03-29 | Sabic Global Technologies B.V. | Method for preparation of a catalyst solution for selective 1-hexene production |
| WO2020128668A1 (en) * | 2018-12-17 | 2020-06-25 | King Abdullah University Of Science And Technology | Heterogenized ru amine or imine catalysts for hydrogen generation from formic acid |
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| US4234453A (en) * | 1976-09-20 | 1980-11-18 | National Petro Chemicals Corporation | Olefin polymerization catalyst |
| US4367992A (en) * | 1980-08-07 | 1983-01-11 | Westinghouse Electric Corp. | Broaching machine |
| US4375406A (en) * | 1981-01-21 | 1983-03-01 | Chevron Research Company | Fibrous clay compositions containing precalcined oxides |
| US4629712A (en) * | 1984-08-17 | 1986-12-16 | Michigan State University | Delaminated clay materials |
| US4637992A (en) | 1984-12-17 | 1987-01-20 | Shell Oil Company | Intercalated clay compositions |
| US4716205A (en) * | 1985-10-15 | 1987-12-29 | E. I. Du Pont De Nemours And Company | Nickel-catalyzed polymerization of ethylene |
| US4701432A (en) * | 1985-11-15 | 1987-10-20 | Exxon Chemical Patents Inc. | Supported polymerization catalyst |
| US4761391A (en) * | 1986-06-30 | 1988-08-02 | Union Oil Company Of California | Delaminated clays and their use in hydrocarbon conversion processes |
| US4995964A (en) * | 1987-03-05 | 1991-02-26 | Uop | Midbarrel hydrocracking process employing rare earth pillared clays |
| US5008228A (en) * | 1988-03-29 | 1991-04-16 | Exxon Chemical Patents Inc. | Method for preparing a silica gel supported metallocene-alumoxane catalyst |
| US4904631A (en) * | 1988-11-08 | 1990-02-27 | Exxon Chemical Patents, Inc. | Supported vanadium catalyst for polymerization of olefins and a process of preparing and using the same |
| US4981825A (en) * | 1989-09-12 | 1991-01-01 | Board Of Trustees Operating Michigan State University | Dried metal oxide and clay particle compositions and method for the preparation thereof |
| US5824297A (en) | 1990-06-25 | 1998-10-20 | Oncogene Science, Inc. | Tissue-derived tumor growth inhibitors, methods of preparation and uses thereof |
| US5038811A (en) * | 1990-11-26 | 1991-08-13 | Yvonne Johnson | Self-opening cuff for crutch |
| TW218884B (https=) | 1991-05-01 | 1994-01-11 | Mitsubishi Kakoki Kk | |
| US5399636A (en) * | 1993-06-11 | 1995-03-21 | Phillips Petroleum Company | Metallocenes and processes therefor and therewith |
| US5852148A (en) * | 1991-07-10 | 1998-12-22 | Minnesota Mining & Manufacturing Company | Perfluoroalkyl halides and derivatives |
| US5438027A (en) * | 1991-12-13 | 1995-08-01 | Phillips Petroleum Company | Chromium compounds and uses thereof |
| US5240894A (en) * | 1992-05-18 | 1993-08-31 | Exxon Chemical Patents Inc. | Method for making and using a supported metallocene catalyst system |
| US5238892A (en) * | 1992-06-15 | 1993-08-24 | Exxon Chemical Patents Inc. | Supported catalyst for 1-olefin(s) (co)polymerization |
| NL9201482A (nl) * | 1992-08-20 | 1994-03-16 | Dsm Nv | Epoxidatie Katalysator. |
| JP3289058B2 (ja) * | 1992-09-11 | 2002-06-04 | 工業技術院長 | 酵素を用いたエステル製造方法 |
| US5403799A (en) * | 1992-12-21 | 1995-04-04 | W. R. Grace & Co.-Conn. | Process upset-resistant inorganic supports for bioremediation |
| US5395808A (en) | 1992-12-21 | 1995-03-07 | W. R. Grace & Co.-Conn. | Inorganic supports for bioremediation |
| US5403809A (en) * | 1992-12-21 | 1995-04-04 | W. R. Grace & Co.-Conn. | Composite inorganic supports containing carbon for bioremediation |
| DE69410668D1 (de) * | 1993-03-23 | 1998-07-09 | Asahi Chemical Ind | Olefinpolymerisationkatalysator mit mehrzähnigem Ligand |
| US5395805A (en) * | 1993-03-25 | 1995-03-07 | Regents Of The University Of California | Method for making monolithic metal oxide aerogels |
| EP0658576B1 (en) * | 1993-12-17 | 1998-07-29 | Tosoh Corporation | Olefin polymerization catalyst and olefin polymerization process |
| US5629253A (en) * | 1994-04-26 | 1997-05-13 | Exxon Chemical Patents, Inc. | Polymerization catalyst systems, their production and use |
| US5707913A (en) * | 1994-06-15 | 1998-01-13 | Basf Aktiengesellschaft | Amidinato catalyst systems for the polymerization of olefins |
| US5661097A (en) * | 1994-08-12 | 1997-08-26 | The Dow Chemical Company | Supported olefin polymerization catalyst |
| US5529965A (en) * | 1994-10-28 | 1996-06-25 | Exxon Chemical Patents Inc. | Polymerization catalyst systems, their production and use |
| US5880241A (en) * | 1995-01-24 | 1999-03-09 | E. I. Du Pont De Nemours And Company | Olefin polymers |
| DE69611554T2 (de) * | 1995-02-20 | 2001-07-05 | Tosoh Corp., Shinnanyo | Katalysator für die Polymerisation von Olefinen und Verfahren zur Herstellung von Olefinpolymerisaten |
| US5637660A (en) * | 1995-04-17 | 1997-06-10 | Lyondell Petrochemical Company | Polymerization of α-olefins with transition metal catalysts based on bidentate ligands containing pyridine or quinoline moiety |
| DE69701909T2 (de) * | 1996-02-23 | 2000-08-17 | Tosoh Corp., Shinnanyo | Olefinpolymerisationskatalysator auf Basis von organometallischen Komplexen und Verfahren zur Herstellung von Polyolefinen mit diesem Katalysator |
| US5852146A (en) | 1996-06-27 | 1998-12-22 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst for the production of olefin polymers |
| IL129929A0 (en) | 1996-12-17 | 2000-02-29 | Du Pont | Polymerization of ethylene with specific iron or cobalt complexes novel pyridinebis (imines) and novel complexes of pyridinebis(imines) with iron and cobalt |
| US5807800A (en) * | 1997-02-11 | 1998-09-15 | Fina Technology, Inc. | Process for producing stereospecific polymers |
| US6103658A (en) * | 1997-03-10 | 2000-08-15 | Eastman Chemical Company | Olefin polymerization catalysts containing group 8-10 transition metals, processes employing such catalysts and polymers obtained therefrom |
| AU8062898A (en) * | 1997-06-09 | 1998-12-30 | E.I. Du Pont De Nemours And Company | Polymerization of olefins |
| DE19746280A1 (de) * | 1997-10-20 | 1999-04-22 | Basf Ag | Verfahren zur Herstellung von geträgerten Übergangsmetallkatalysatoren |
| US6228792B1 (en) * | 1998-02-27 | 2001-05-08 | W. R. Grace & Co.-Conn. | Donor-modified olefin polymerization catalysts |
| US6521561B1 (en) * | 1998-05-01 | 2003-02-18 | President And Fellows Of Harvard College | Main-group metal based asymmetric catalysts and applications thereof |
| US6117959A (en) * | 1998-09-02 | 2000-09-12 | Eastman Chemical Company | Polyolefin catalysts |
| US6184171B1 (en) * | 1998-10-05 | 2001-02-06 | W.R. Grace & Co. -Conn | Supported bidentate and tridentate catalyst compositions and olefin polymerization using same |
| US6559090B1 (en) * | 1999-11-01 | 2003-05-06 | W. R. Grace & Co.-Conn. | Metallocene and constrained geometry catalyst systems employing agglomerated metal oxide/clay support-activator and method of their preparation |
| US6399535B1 (en) * | 1999-11-01 | 2002-06-04 | W. R. Grace & Co.-Conn. | Coordination catalyst systems employing agglomerated metal oxide/clay support-activator and method of their preparation |
| US6710007B2 (en) * | 2001-01-26 | 2004-03-23 | E. I. Du Pont De Nemours And Company | Polymerization of olefinic compounds |
| EP1399491B1 (en) * | 2001-04-30 | 2006-08-23 | W.R. Grace & Co.-Conn. | Supported dual transition metal catalyst systems |
-
2000
- 2000-10-19 JP JP2001535421A patent/JP5258077B2/ja not_active Expired - Fee Related
- 2000-10-19 CA CA2389587A patent/CA2389587C/en not_active Expired - Fee Related
- 2000-10-19 AU AU10960/01A patent/AU1096001A/en not_active Abandoned
- 2000-10-19 EP EP00972276A patent/EP1237954B1/en not_active Expired - Lifetime
- 2000-10-19 CN CNB008180296A patent/CN1178964C/zh not_active Expired - Fee Related
- 2000-10-19 BR BRPI0015192-0A patent/BR0015192B1/pt not_active IP Right Cessation
- 2000-10-19 KR KR1020027005582A patent/KR100710963B1/ko not_active Expired - Fee Related
- 2000-10-19 AT AT00972276T patent/ATE315053T1/de not_active IP Right Cessation
- 2000-10-19 DE DE60025386T patent/DE60025386T2/de not_active Expired - Lifetime
- 2000-10-19 WO PCT/US2000/028920 patent/WO2001032723A1/en not_active Ceased
- 2000-10-19 MX MXPA02004322A patent/MXPA02004322A/es active IP Right Grant
- 2000-10-27 SG SG200006183A patent/SG97961A1/en unknown
-
2003
- 2003-08-05 US US10/633,509 patent/US7291575B2/en not_active Expired - Fee Related
-
2011
- 2011-02-28 JP JP2011041986A patent/JP2011149025A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020091051A (ko) | 2002-12-05 |
| WO2001032723A1 (en) | 2001-05-10 |
| JP2011149025A (ja) | 2011-08-04 |
| JP5258077B2 (ja) | 2013-08-07 |
| BR0015192B1 (pt) | 2010-11-03 |
| US7291575B2 (en) | 2007-11-06 |
| EP1237954B1 (en) | 2006-01-04 |
| CA2389587A1 (en) | 2001-05-10 |
| JP2003513165A (ja) | 2003-04-08 |
| DE60025386T2 (de) | 2006-09-21 |
| CA2389587C (en) | 2010-05-25 |
| KR100710963B1 (ko) | 2007-04-24 |
| EP1237954A1 (en) | 2002-09-11 |
| BR0015192A (pt) | 2003-06-17 |
| CN1414982A (zh) | 2003-04-30 |
| SG97961A1 (en) | 2003-08-20 |
| CN1178964C (zh) | 2004-12-08 |
| AU1096001A (en) | 2001-05-14 |
| US20040029719A1 (en) | 2004-02-12 |
| ATE315053T1 (de) | 2006-02-15 |
| DE60025386D1 (de) | 2006-03-30 |
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| FG | Grant or registration |