JP2004538344A - 担持オレフィン重合触媒 - Google Patents
担持オレフィン重合触媒 Download PDFInfo
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- JP2004538344A JP2004538344A JP2002577899A JP2002577899A JP2004538344A JP 2004538344 A JP2004538344 A JP 2004538344A JP 2002577899 A JP2002577899 A JP 2002577899A JP 2002577899 A JP2002577899 A JP 2002577899A JP 2004538344 A JP2004538344 A JP 2004538344A
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- Prior art keywords
- transition metal
- group
- reactive group
- hydrocarbyl
- neutral
- Prior art date
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- 239000002685 polymerization catalyst Substances 0.000 title claims abstract description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 150000001336 alkenes Chemical class 0.000 title claims description 22
- 150000003624 transition metals Chemical class 0.000 claims abstract description 64
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 61
- 239000003446 ligand Substances 0.000 claims abstract description 60
- -1 transition metal olefin Chemical class 0.000 claims abstract description 39
- 125000000524 functional group Chemical group 0.000 claims abstract description 36
- 230000007935 neutral effect Effects 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 29
- 230000000295 complement effect Effects 0.000 claims abstract description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 40
- 239000007787 solid Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052782 aluminium Inorganic materials 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical group B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 239000011777 magnesium Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000085 borane Inorganic materials 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical group 0.000 claims description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Chemical group 0.000 claims description 4
- 150000001299 aldehydes Chemical class 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
- 150000002576 ketones Chemical group 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
- 150000008054 sulfonate salts Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 238000011068 loading method Methods 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- 239000005977 Ethylene Substances 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000012071 phase Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 229910004298 SiO 2 Inorganic materials 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229920000642 polymer Polymers 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 150000003623 transition metal compounds Chemical class 0.000 description 6
- 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 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910000071 diazene Inorganic materials 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
- 239000002245 particle Substances 0.000 description 5
- 125000001424 substituent group Chemical group 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
- ZOLHJKXYRQTXFY-UHFFFAOYSA-N 3-(4-amino-3,5-dimethylphenyl)propan-1-ol Chemical compound CC1=CC(CCCO)=CC(C)=C1N ZOLHJKXYRQTXFY-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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 group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Chemical group 0.000 description 4
- 238000002360 preparation method Methods 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring 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
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012018 catalyst precursor 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
- 239000005457 ice water Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 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
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-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
- 239000002002 slurry Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- 0 *C(c1nc(C(*)=N*)c(*)c(*)c1*)=N* Chemical compound *C(c1nc(C(*)=N*)c(*)c(*)c1*)=N* 0.000 description 1
- 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
- LUZUUEKZAUBXHK-UHFFFAOYSA-N 2-(4-amino-3,5-dibromophenyl)ethanol Chemical compound NC1=C(Br)C=C(CCO)C=C1Br LUZUUEKZAUBXHK-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
- VXCYWALUEFUWAJ-UHFFFAOYSA-N 3-(4-amino-3,5-dimethylphenyl)prop-2-en-1-ol Chemical compound CC1=CC(C=CCO)=CC(C)=C1N VXCYWALUEFUWAJ-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
- 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 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052906 cristobalite Inorganic materials 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
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000004678 hydrides Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 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
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 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
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage 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
- 229910052905 tridymite Inorganic materials 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
- 239000004711 α-olefin Substances 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27920701P | 2001-03-28 | 2001-03-28 | |
| US30798501P | 2001-07-26 | 2001-07-26 | |
| PCT/US2002/010044 WO2002079276A2 (en) | 2001-03-28 | 2002-03-28 | Supported olefin polymerization catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004538344A true JP2004538344A (ja) | 2004-12-24 |
| JP2004538344A5 JP2004538344A5 (enExample) | 2005-12-22 |
Family
ID=26959523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002577899A Pending JP2004538344A (ja) | 2001-03-28 | 2002-03-28 | 担持オレフィン重合触媒 |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008531835A (ja) * | 2005-03-04 | 2008-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 担持オレフィン重合触媒 |
| JP2020021656A (ja) * | 2018-08-01 | 2020-02-06 | 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 |
Families Citing this family (31)
| 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 |
| 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 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001261731A (ja) * | 2000-03-13 | 2001-09-26 | Repsol Quimica Sa | 二座ジイミノニッケルおよびパラジウム錯体およびこれから得られた重合触媒 |
| JP2001302679A (ja) * | 2000-03-13 | 2001-10-31 | Repsol Quimica Sa | ジイミノ化合物 |
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| 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 |
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001261731A (ja) * | 2000-03-13 | 2001-09-26 | Repsol Quimica Sa | 二座ジイミノニッケルおよびパラジウム錯体およびこれから得られた重合触媒 |
| JP2001302679A (ja) * | 2000-03-13 | 2001-10-31 | Repsol Quimica Sa | ジイミノ化合物 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008531835A (ja) * | 2005-03-04 | 2008-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 担持オレフィン重合触媒 |
| JP2020021656A (ja) * | 2018-08-01 | 2020-02-06 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1253478C (zh) | 2006-04-26 |
| US20020187892A1 (en) | 2002-12-12 |
| CA2438456A1 (en) | 2002-10-10 |
| 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 |
| 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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