CA2438456A1 - Supported olefin polymerization catalysts - Google Patents
Supported olefin polymerization catalysts Download PDFInfo
- Publication number
- CA2438456A1 CA2438456A1 CA002438456A CA2438456A CA2438456A1 CA 2438456 A1 CA2438456 A1 CA 2438456A1 CA 002438456 A CA002438456 A CA 002438456A CA 2438456 A CA2438456 A CA 2438456A CA 2438456 A1 CA2438456 A1 CA 2438456A1
- Authority
- CA
- Canada
- Prior art keywords
- transition metal
- group
- hydrocarbyl
- ligand
- neutral
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002685 polymerization catalyst Substances 0.000 title claims abstract description 32
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 150000001336 alkenes Chemical class 0.000 title claims description 23
- 150000003624 transition metals Chemical class 0.000 claims abstract description 64
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 62
- 239000003446 ligand Substances 0.000 claims abstract description 57
- -1 transition metal olefin Chemical class 0.000 claims abstract description 38
- 125000000524 functional group Chemical group 0.000 claims abstract description 35
- 230000007935 neutral effect Effects 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 27
- 230000000295 complement effect Effects 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 38
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical group B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000306 component Substances 0.000 claims description 10
- 239000012948 isocyanate Chemical group 0.000 claims description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 9
- 150000002118 epoxides Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002513 isocyanates Chemical group 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000011777 magnesium Chemical group 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910000085 borane Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Chemical group 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003863 ammonium salts Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 4
- 150000008054 sulfonate salts Chemical group 0.000 claims description 4
- 150000001299 aldehydes Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical group 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical group 0.000 claims description 3
- 150000001266 acyl halides Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000003054 catalyst Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 22
- 235000010210 aluminium Nutrition 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000005977 Ethylene Substances 0.000 description 19
- 229940093470 ethylene Drugs 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 101150041968 CDC13 gene Proteins 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000003623 transition metal compounds Chemical class 0.000 description 6
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 6
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910000071 diazene Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- BEZVGIHGZPLGBL-UHFFFAOYSA-N 2,6-diacetylpyridine Chemical compound CC(=O)C1=CC=CC(C(C)=O)=N1 BEZVGIHGZPLGBL-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ROCUYUKLDLAYIX-UHFFFAOYSA-L [Cl-].[Cl-].[Fe++].CC(=Nc1c(C)c(C)c(N)c(C)c1C)c1cccc(n1)C(C)=Nc1c(C)c(C)c(N)c(C)c1C Chemical compound [Cl-].[Cl-].[Fe++].CC(=Nc1c(C)c(C)c(N)c(C)c1C)c1cccc(n1)C(C)=Nc1c(C)c(C)c(N)c(C)c1C ROCUYUKLDLAYIX-UHFFFAOYSA-L 0.000 description 3
- GZBCWKZYMSWKPU-UHFFFAOYSA-L [Cl-].[Cl-].[Fe++].CC(=Nc1c(C)cc(CCCO)cc1C)c1cccc(n1)C(C)=Nc1c(C)cc(CCCO)cc1C Chemical compound [Cl-].[Cl-].[Fe++].CC(=Nc1c(C)cc(CCCO)cc1C)c1cccc(n1)C(C)=Nc1c(C)cc(CCCO)cc1C GZBCWKZYMSWKPU-UHFFFAOYSA-L 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- NOYGIWGLGIJFAB-UHFFFAOYSA-N 3-[4-[1-[6-[n-[4-(3-hydroxypropyl)-2,6-dimethylphenyl]-c-methylcarbonimidoyl]pyridin-2-yl]ethylideneamino]-3,5-dimethylphenyl]propan-1-ol Chemical compound C=1C=CC(C(C)=NC=2C(=CC(CCCO)=CC=2C)C)=NC=1C(C)=NC1=C(C)C=C(CCCO)C=C1C NOYGIWGLGIJFAB-UHFFFAOYSA-N 0.000 description 2
- WBXNKNVEBYLKJS-UHFFFAOYSA-L 4-[1-[6-[N-(4-hydroxy-2-methylphenyl)-C-methylcarbonimidoyl]pyridin-2-yl]ethylideneamino]-3-methylphenol iron(2+) dichloride Chemical compound [Cl-].[Cl-].[Fe++].CC(=Nc1ccc(O)cc1C)c1cccc(n1)C(C)=Nc1ccc(O)cc1C WBXNKNVEBYLKJS-UHFFFAOYSA-L 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000005538 phosphinite group Chemical group 0.000 description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- XTFSHUFLNZNTBL-UHFFFAOYSA-N 2,3,4,5-tetramethylcyclohexa-1,5-diene-1,4-diamine Chemical compound CC1C(C)=C(N)C=C(C)C1(C)N XTFSHUFLNZNTBL-UHFFFAOYSA-N 0.000 description 1
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 1
- OMHOXRVODFQGCA-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylphenyl)methyl]-2,6-dimethylaniline Chemical compound CC1=C(N)C(C)=CC(CC=2C=C(C)C(N)=C(C)C=2)=C1 OMHOXRVODFQGCA-UHFFFAOYSA-N 0.000 description 1
- SVYQKCAEBJCTQE-UHFFFAOYSA-N 4-[1-[6-[n-(4-amino-2,3,5,6-tetramethylphenyl)-c-methylcarbonimidoyl]pyridin-2-yl]ethylideneamino]-2,3,5,6-tetramethylaniline Chemical compound C=1C=CC(C(C)=NC=2C(=C(C)C(N)=C(C)C=2C)C)=NC=1C(C)=NC1=C(C)C(C)=C(N)C(C)=C1C SVYQKCAEBJCTQE-UHFFFAOYSA-N 0.000 description 1
- QGLAYJCJLHNIGJ-UHFFFAOYSA-N 4-bromo-2,6-dimethylaniline Chemical compound CC1=CC(Br)=CC(C)=C1N QGLAYJCJLHNIGJ-UHFFFAOYSA-N 0.000 description 1
- GONFBOIJNUKKST-UHFFFAOYSA-N 5-ethylsulfanyl-2h-tetrazole Chemical compound CCSC=1N=NNN=1 GONFBOIJNUKKST-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SFKCQEMKYOVMSF-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C(=CC(=C1)CCO)C1=CC=CC=C1)N=C(C)C(C)=NC1=C(C=C(C=C1C1=CC=CC=C1)CCO)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C1=C(C(=CC(=C1)CCO)C1=CC=CC=C1)N=C(C)C(C)=NC1=C(C=C(C=C1C1=CC=CC=C1)CCO)C1=CC=CC=C1 SFKCQEMKYOVMSF-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 241000286904 Leptothecata Species 0.000 description 1
- GMTHNTGGQGNMQP-UHFFFAOYSA-N NC=1C(=CC(=CC1)O)C.OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C Chemical compound NC=1C(=CC(=CC1)O)C.OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C GMTHNTGGQGNMQP-UHFFFAOYSA-N 0.000 description 1
- PLNGNKPYKVFISQ-UHFFFAOYSA-L OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C.[Fe](Cl)Cl.OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C Chemical compound OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C.[Fe](Cl)Cl.OC1=CC(=C(C=C1)N=C(C)C1=NC(=CC=C1)C(C)=NC1=C(C=C(C=C1)O)C)C PLNGNKPYKVFISQ-UHFFFAOYSA-L 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- DBYVFGSEJWZZCZ-UHFFFAOYSA-N borinothioic acid Chemical compound SB DBYVFGSEJWZZCZ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 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
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- SEDJKFXXCVUAQN-UHFFFAOYSA-N oxomethylideneboron Chemical compound [B]=C=O SEDJKFXXCVUAQN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052990 silicon hydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27920701P | 2001-03-28 | 2001-03-28 | |
| US60/279,207 | 2001-03-28 | ||
| US30798501P | 2001-07-26 | 2001-07-26 | |
| US60/307,985 | 2001-07-26 | ||
| PCT/US2002/010044 WO2002079276A2 (en) | 2001-03-28 | 2002-03-28 | Supported olefin polymerization catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2438456A1 true CA2438456A1 (en) | 2002-10-10 |
Family
ID=26959523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002438456A Abandoned CA2438456A1 (en) | 2001-03-28 | 2002-03-28 | Supported olefin polymerization catalysts |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6900153B2 (enExample) |
| EP (1) | EP1379562B1 (enExample) |
| JP (1) | JP2004538344A (enExample) |
| KR (2) | KR20090026820A (enExample) |
| CN (1) | CN1253478C (enExample) |
| BR (1) | BR0208642A (enExample) |
| CA (1) | CA2438456A1 (enExample) |
| DE (1) | DE60222107T2 (enExample) |
| MX (1) | MXPA03008813A (enExample) |
| WO (1) | WO2002079276A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1559728A1 (en) * | 2004-01-28 | 2005-08-03 | Total Petrochemicals Research Feluy | Grafting of transition metal complexes on supports |
| US20050187418A1 (en) | 2004-02-19 | 2005-08-25 | Small Brooke L. | Olefin oligomerization |
| US7384886B2 (en) | 2004-02-20 | 2008-06-10 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
| US20070043181A1 (en) | 2005-08-19 | 2007-02-22 | Knudsen Ronald D | Methods of preparation of an olefin oligomerization catalyst |
| US20050187098A1 (en) | 2004-02-20 | 2005-08-25 | Knudsen Ronald D. | Methods of preparation of an olefin oligomerization catalyst |
| US9550841B2 (en) | 2004-02-20 | 2017-01-24 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
| DE102004020524A1 (de) | 2004-04-26 | 2005-11-10 | Basell Polyolefine Gmbh | Polyethylen und Katalysatorzusammensetzung zu dessen Herstellung |
| EP1758848A1 (en) * | 2004-04-27 | 2007-03-07 | University Of North Carolina At Chapel Hill | Separation of unsymmetrical diimines by liquid chromatography |
| EP1773895B1 (en) | 2004-07-09 | 2011-12-28 | E.I. Du Pont De Nemours And Company | Catalysts for olefin polymerization or oligomerization |
| EP1856164A1 (en) * | 2005-03-04 | 2007-11-21 | E.I. Dupont De Nemours And Company | Supported olefin polymerization catalysts |
| US7268096B2 (en) | 2005-07-21 | 2007-09-11 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| SG182996A1 (en) * | 2005-07-21 | 2012-08-30 | Chevron Phillips Chemical Co | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| US7727926B2 (en) | 2005-07-21 | 2010-06-01 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and method of using in oligomerization and polymerization |
| US7271121B2 (en) * | 2005-07-21 | 2007-09-18 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| DE102006001959A1 (de) | 2006-01-13 | 2007-07-19 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von unsymmetrischen Bis(imino)verbindungen |
| CA2620852A1 (en) * | 2007-02-28 | 2008-08-28 | Rohm And Haas Company | A porous linear polymer composition and method of making same |
| DE102007017903A1 (de) * | 2007-04-13 | 2008-10-16 | Basell Polyolefine Gmbh | Polyethylen und Katalysatorzusammensetzung und Verfahren zu dessen Herstellung |
| CN100560613C (zh) * | 2007-11-15 | 2009-11-18 | 中国石油天然气股份有限公司 | 一种烯烃聚合催化剂的制备方法 |
| US7902415B2 (en) | 2007-12-21 | 2011-03-08 | Chevron Phillips Chemical Company Lp | Processes for dimerizing or isomerizing olefins |
| EP2222724A1 (en) * | 2007-12-21 | 2010-09-01 | Basell Polyolefine GmbH | Catalyst sytem for olefin polymerization comprising phenantroline-comprising iron complexes |
| CN101845104B (zh) * | 2010-05-21 | 2012-03-21 | 北京化工大学 | 烯烃聚合催化剂及其制备方法 |
| RU2598023C2 (ru) | 2011-05-13 | 2016-09-20 | Юнивейшн Текнолоджиз, Ллк | Полученные распылительной сушкой каталитические композиции и способы полимеризации, в которых они применяются |
| US9586872B2 (en) | 2011-12-30 | 2017-03-07 | Chevron Phillips Chemical Company Lp | Olefin oligomerization methods |
| US20180155263A1 (en) * | 2014-09-17 | 2018-06-07 | Novoform Technologies Llc | Methods and catalysts for converting methane to methanol |
| CN106957380B (zh) * | 2016-01-12 | 2019-06-28 | 中国石油化工股份有限公司 | 一种用于乙烯聚合的催化剂组分的制备方法 |
| EP3440118A1 (en) * | 2016-05-20 | 2019-02-13 | Chevron Phillips Chemical Company LP | Low pressure process for preparing low-density polyethylene |
| US9944661B2 (en) | 2016-08-09 | 2018-04-17 | Chevron Phillips Chemical Company Lp | Olefin hydroboration |
| CN107118288B (zh) * | 2017-05-25 | 2019-10-18 | 江苏奥克化学有限公司 | 一种负载型后过渡金属催化剂及其制备方法 |
| JP7180861B2 (ja) * | 2018-08-01 | 2022-11-30 | 国立大学法人北陸先端科学技術大学院大学 | 電解液、リチウムイオン２次電池、化合物 |
| US20220098034A1 (en) * | 2018-12-17 | 2022-03-31 | King Abdullah University Of Science And Technology | Heterogeneous catalysts for hydrogen generation from formic acid |
| CN112094303B (zh) * | 2020-11-02 | 2021-03-26 | 江苏欣诺科催化剂有限公司 | 固载型金属有机配合物及其制备方法和应用 |
| CN112588319A (zh) * | 2020-12-22 | 2021-04-02 | 重庆极泽生物科技有限公司 | 硅烷的应用以及其催化下牛磺熊去氧胆酸的合成 |
| EP4493598A1 (en) * | 2022-03-14 | 2025-01-22 | ExxonMobil Chemical Patents Inc. | Metal-containing bis(imino) per-substituted aryl compounds and methods thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6030917A (en) * | 1996-07-23 | 2000-02-29 | Symyx Technologies, Inc. | Combinatorial synthesis and analysis of organometallic compounds and catalysts |
| 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 |
| 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 |
| ID24448A (id) | 1997-09-05 | 2000-07-20 | Bp Chemical Ltd | Katalis-katalis polimerisasi |
| GB9725455D0 (en) | 1997-12-02 | 1998-01-28 | Univ Warwick | Supported polymerisation catalyst |
| EP0953580B1 (en) | 1998-04-29 | 2004-04-14 | Repsol Quimica S.A. | Preparation and use of heterogeneous catalyst components for olefins polymerization |
| US6197714B1 (en) | 1999-03-23 | 2001-03-06 | Cryovac, Inc. | Supported catalysts and olefin polymerization processes utilizing same |
| US6197715B1 (en) * | 1999-03-23 | 2001-03-06 | Cryovac, Inc. | Supported catalysts and olefin polymerization processes utilizing same |
| ATE251184T1 (de) * | 2000-03-13 | 2003-10-15 | Repsol Quimica Sa | Zweizähnige nickel- und palladium-komplexe und polymerisationskatalysatoren |
| ATE273312T1 (de) * | 2000-03-13 | 2004-08-15 | Repsol Quimica Sa | Diiminverbindungen |
-
2002
- 2002-03-27 US US10/108,938 patent/US6900153B2/en not_active Expired - Fee Related
- 2002-03-28 DE DE60222107T patent/DE60222107T2/de not_active Expired - Lifetime
- 2002-03-28 JP JP2002577899A patent/JP2004538344A/ja active Pending
- 2002-03-28 KR KR1020097002453A patent/KR20090026820A/ko not_active Withdrawn
- 2002-03-28 MX MXPA03008813A patent/MXPA03008813A/es unknown
- 2002-03-28 EP EP02723711A patent/EP1379562B1/en not_active Expired - Lifetime
- 2002-03-28 CA CA002438456A patent/CA2438456A1/en not_active Abandoned
- 2002-03-28 WO PCT/US2002/010044 patent/WO2002079276A2/en not_active Ceased
- 2002-03-28 BR BR0208642-5A patent/BR0208642A/pt not_active IP Right Cessation
- 2002-03-28 KR KR1020037012547A patent/KR100890700B1/ko not_active Expired - Fee Related
- 2002-03-28 CN CNB028075587A patent/CN1253478C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1253478C (zh) | 2006-04-26 |
| US20020187892A1 (en) | 2002-12-12 |
| DE60222107D1 (de) | 2007-10-11 |
| WO2002079276A2 (en) | 2002-10-10 |
| DE60222107T2 (de) | 2008-05-29 |
| WO2002079276A3 (en) | 2003-03-13 |
| MXPA03008813A (es) | 2004-04-18 |
| JP2004538344A (ja) | 2004-12-24 |
| EP1379562A2 (en) | 2004-01-14 |
| KR100890700B1 (ko) | 2009-03-27 |
| CN1527849A (zh) | 2004-09-08 |
| BR0208642A (pt) | 2004-03-09 |
| KR20090026820A (ko) | 2009-03-13 |
| EP1379562B1 (en) | 2007-08-29 |
| KR20030088477A (ko) | 2003-11-19 |
| US6900153B2 (en) | 2005-05-31 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |