KR20010034211A - 올레핀-중합-촉매로서 비스(테트라히드로-인데닐)메탈로센 - Google Patents
올레핀-중합-촉매로서 비스(테트라히드로-인데닐)메탈로센 Download PDFInfo
- Publication number
- KR20010034211A KR20010034211A KR1020007007865A KR20007007865A KR20010034211A KR 20010034211 A KR20010034211 A KR 20010034211A KR 1020007007865 A KR1020007007865 A KR 1020007007865A KR 20007007865 A KR20007007865 A KR 20007007865A KR 20010034211 A KR20010034211 A KR 20010034211A
- Authority
- KR
- South Korea
- Prior art keywords
- indenyl
- bis
- group
- tetrahydro
- metallocene
- 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.)
- Withdrawn
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- 239000003054 catalyst Substances 0.000 title claims abstract description 40
- -1 tetrahydro-indenyl Chemical group 0.000 claims abstract description 65
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 44
- 239000003446 ligand Substances 0.000 claims abstract description 21
- 150000001336 alkenes Chemical class 0.000 claims abstract description 16
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 4
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 42
- 239000005977 Ethylene Substances 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 12
- 239000004711 α-olefin Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 230000000737 periodic effect Effects 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 2
- 102000007469 Actins Human genes 0.000 claims description 2
- 108010085238 Actins Proteins 0.000 claims description 2
- 101100173447 Caenorhabditis elegans ger-1 gene Proteins 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 240000000018 Gnetum gnemon Species 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- 229920000642 polymer Polymers 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 229910007926 ZrCl Inorganic materials 0.000 description 11
- 229920000573 polyethylene Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VXQVXFCKINUPMT-UHFFFAOYSA-L [Cl-].[Cl-].C(C)C1C(=CC=2CCCCC12)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)C1C(=CC=2CCCCC12)[Zr+2] VXQVXFCKINUPMT-UHFFFAOYSA-L 0.000 description 4
- JLSINOLRGFIEQY-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C1C(=CC=2CCCCC12)[Zr+2] Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C1C(=CC=2CCCCC12)[Zr+2] JLSINOLRGFIEQY-UHFFFAOYSA-L 0.000 description 4
- XCVIPWIONKROLN-UHFFFAOYSA-L [Cl-].[Cl-].CC(C)(C)C1C2=C(CCCC2)C=C1[Zr++](=C)C1=CC2=C(CCCC2)C1C(C)(C)C Chemical compound [Cl-].[Cl-].CC(C)(C)C1C2=C(CCCC2)C=C1[Zr++](=C)C1=CC2=C(CCCC2)C1C(C)(C)C XCVIPWIONKROLN-UHFFFAOYSA-L 0.000 description 4
- NVOQCQILATWIPQ-UHFFFAOYSA-L [Cl-].[Cl-].CC1C(=CC=2CCCCC12)[Zr+2] Chemical compound [Cl-].[Cl-].CC1C(=CC=2CCCCC12)[Zr+2] NVOQCQILATWIPQ-UHFFFAOYSA-L 0.000 description 4
- HTKTWOHLEUVHGO-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C1C(=CC=2CCCCC12)[Zr+2])(C)C Chemical compound [Cl-].[Cl-].C[Si](C1C(=CC=2CCCCC12)[Zr+2])(C)C HTKTWOHLEUVHGO-UHFFFAOYSA-L 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- XBKNMGUCKSFTGE-UHFFFAOYSA-N 3-methyl-2-[(3-methyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C)=C1CC1=C(C)C2=CC=CC=C2C1 XBKNMGUCKSFTGE-UHFFFAOYSA-N 0.000 description 3
- VCFGYRFNVFQFEH-UHFFFAOYSA-N 3-tert-butyl-2-[(3-tert-butyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C(C)(C)C)=C1CC1=C(C(C)(C)C)C2=CC=CC=C2C1 VCFGYRFNVFQFEH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
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- 229930195733 hydrocarbon Natural products 0.000 description 3
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- 238000005984 hydrogenation reaction Methods 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- XXFMGYAEXYEVTA-UHFFFAOYSA-L [Cl-].[Cl-].CC1C2=C(CCCC2)C(C)=C1[Zr++](=C)C1=C(C)C2=C(CCCC2)C1C Chemical compound [Cl-].[Cl-].CC1C2=C(CCCC2)C(C)=C1[Zr++](=C)C1=C(C)C2=C(CCCC2)C1C XXFMGYAEXYEVTA-UHFFFAOYSA-L 0.000 description 1
- OGQNCQQOCLUURR-UHFFFAOYSA-L [Cl-].[Cl-].CC1CCC(C)C2=C1CC(=C2)[Zr++](=C)C1=CC2=C(C1)C(C)CCC2C Chemical compound [Cl-].[Cl-].CC1CCC(C)C2=C1CC(=C2)[Zr++](=C)C1=CC2=C(C1)C(C)CCC2C OGQNCQQOCLUURR-UHFFFAOYSA-L 0.000 description 1
- PRLVCKKXCYYKPX-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr++](C1=CC2=C(CCCC2)C1C(C)(C)C)C1=CC2=C(CCCC2)C1C(C)(C)C Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr++](C1=CC2=C(CCCC2)C1C(C)(C)C)C1=CC2=C(CCCC2)C1C(C)(C)C PRLVCKKXCYYKPX-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RIAYWWDCGFUPJC-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[AlH]CC(C)CC(C)(C)C RIAYWWDCGFUPJC-UHFFFAOYSA-N 0.000 description 1
- UXPLEHPMOSDYLZ-UHFFFAOYSA-N bis(2-methylpropyl)-(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C UXPLEHPMOSDYLZ-UHFFFAOYSA-N 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- ISEJRLXHKSHKPM-UHFFFAOYSA-N dimethyl(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)C ISEJRLXHKSHKPM-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000001282 iso-butane Substances 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
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- NCYHQDWNMCYQHR-UHFFFAOYSA-N methyl-bis(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)CC(C)C NCYHQDWNMCYQHR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- VGONMIOMLRCRSS-UHFFFAOYSA-N tris(2,3-dimethylhexyl)alumane Chemical compound CCCC(C)C(C)C[Al](CC(C)C(C)CCC)CC(C)C(C)CCC VGONMIOMLRCRSS-UHFFFAOYSA-N 0.000 description 1
- BENYMJNPVWYYES-UHFFFAOYSA-N tris(2,3-dimethylpentyl)alumane Chemical compound CCC(C)C(C)C[Al](CC(C)C(C)CC)CC(C)C(C)CC BENYMJNPVWYYES-UHFFFAOYSA-N 0.000 description 1
- UVCGXEXDZCCTFF-UHFFFAOYSA-N tris(2,4-dimethylheptyl)alumane Chemical compound CCCC(C)CC(C)C[Al](CC(C)CC(C)CCC)CC(C)CC(C)CCC UVCGXEXDZCCTFF-UHFFFAOYSA-N 0.000 description 1
- JAFSWBPCWFKGBY-UHFFFAOYSA-N tris(2-ethyl-3-methylpentyl)alumane Chemical compound CCC(C)C(CC)C[Al](CC(CC)C(C)CC)CC(CC)C(C)CC JAFSWBPCWFKGBY-UHFFFAOYSA-N 0.000 description 1
- CFCIWEFTNUMUJY-UHFFFAOYSA-N tris(2-methylphenyl)alumane Chemical compound CC1=CC=CC=C1[Al](C=1C(=CC=CC=1)C)C1=CC=CC=C1C CFCIWEFTNUMUJY-UHFFFAOYSA-N 0.000 description 1
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 1
- VIDMRZMJMLMHSP-UHFFFAOYSA-N tris(3-methyl-2-propan-2-ylbutyl)alumane Chemical compound CC(C)C(C(C)C)C[Al](CC(C(C)C)C(C)C)CC(C(C)C)C(C)C VIDMRZMJMLMHSP-UHFFFAOYSA-N 0.000 description 1
- MLDSMTVYPPIXMZ-UHFFFAOYSA-N tris(4-methylpentyl)alumane Chemical compound CC(C)CCC[Al](CCCC(C)C)CCCC(C)C MLDSMTVYPPIXMZ-UHFFFAOYSA-N 0.000 description 1
- RKPWAHQNLQXPPH-UHFFFAOYSA-N tris(6-methylheptyl)alumane Chemical compound CC(C)CCCCC[Al](CCCCCC(C)C)CCCCCC(C)C RKPWAHQNLQXPPH-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- 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
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203905 | 1998-11-18 | ||
| EP98203905.9 | 1998-11-18 | ||
| PCT/EP1999/008647 WO2000029416A1 (en) | 1998-11-18 | 1999-11-10 | Bis(tetrahydro-indenyl) metallocenes as olefin-polymerisation-catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010034211A true KR20010034211A (ko) | 2001-04-25 |
Family
ID=8234357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007007865A Withdrawn KR20010034211A (ko) | 1998-11-18 | 1999-11-10 | 올레핀-중합-촉매로서 비스(테트라히드로-인데닐)메탈로센 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6541584B1 (enExample) |
| EP (1) | EP1047702B1 (enExample) |
| JP (1) | JP2002530286A (enExample) |
| KR (1) | KR20010034211A (enExample) |
| CN (1) | CN1291986A (enExample) |
| AR (1) | AR021311A1 (enExample) |
| AU (1) | AU1270500A (enExample) |
| BR (1) | BR9910192A (enExample) |
| CA (1) | CA2317588A1 (enExample) |
| DE (1) | DE69905011T2 (enExample) |
| ES (1) | ES2189516T3 (enExample) |
| HU (1) | HUP0101157A2 (enExample) |
| IL (1) | IL137036A0 (enExample) |
| WO (1) | WO2000029416A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1318436B1 (it) * | 2000-03-31 | 2003-08-25 | Enichem Spa | Ciclopentadieni sostituiti policiclici e metodo per la loropreparazione. |
| CA2411712C (en) * | 2000-06-30 | 2011-01-25 | Dow Global Technologies Inc. | Polycyclic, fused ring compounds, metal complexes and polymerization process |
| EP1444739B1 (en) * | 2001-11-16 | 2009-11-04 | CDT Oxford Limited | Light emitting device and compounds for use therein |
| EP1464657A1 (en) * | 2003-03-06 | 2004-10-06 | ATOFINA Research | Hydrogenated metallocene catalyst |
| US6958377B2 (en) * | 2003-10-15 | 2005-10-25 | Equistar Chemicals, Lp | Olefin polymerization process |
| EP1674523A1 (en) * | 2004-12-22 | 2006-06-28 | Total Petrochemicals Research Feluy | Caps and closures |
| EP1721913A1 (en) * | 2005-05-09 | 2006-11-15 | Total Petrochemicals Research Feluy | Microwave-promoted creation of catalytic species |
| JP5635234B2 (ja) | 2005-07-19 | 2014-12-03 | エクソンモービル・ケミカル・パテンツ・インク | ポリαオレフィン組成物およびこれを生成するためのプロセス |
| US7592395B2 (en) * | 2006-08-01 | 2009-09-22 | Exxonmobil Chemical Patents Inc. | Multimodal polyethylene for use in single piece beverage bottle caps and closures |
| EP2199078A1 (en) * | 2008-12-22 | 2010-06-23 | Total Petrochemicals Research Feluy | Polyethylene and poly(hydroxy carboxylic acid) multilayer films |
| CN102464748B (zh) * | 2010-11-16 | 2013-07-03 | 中国石油化工股份有限公司 | 一种丙烯共聚物大分子单体及其制备方法 |
| US9365788B2 (en) * | 2011-10-10 | 2016-06-14 | Exxonmobil Chemical Patents Inc. | Process to produce improved poly alpha olefin compositions |
| CN104093730A (zh) * | 2011-12-19 | 2014-10-08 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| EP2800754B1 (en) * | 2011-12-19 | 2017-06-28 | Saudi Basic Industries Corporation (Sabic) | Process for the preparation of metallocene complexes |
| CN103509060B (zh) * | 2012-06-27 | 2016-08-10 | 大林产业株式会社 | 茂金属化合物、包含茂金属化合物的催化剂组合物以及使用茂金属化合物的烯烃聚合方法 |
| US9932423B2 (en) | 2015-09-24 | 2018-04-03 | Exxonmobil Chemical Patents Inc. | Hydrogenation of annulated cyclopentadienyl metal complexes and metallocene catalysts comprising such |
| CN108473520B (zh) | 2016-01-05 | 2021-07-23 | Sabic环球技术有限责任公司 | 包含金属茂络合物和助催化剂的催化剂 |
| EP3312201B1 (en) | 2016-01-27 | 2019-12-25 | LG Chem, Ltd. | Supported hybrid catalyst and method for preparing olefin polymer using the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3840772A1 (de) | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
| ES2071888T3 (es) | 1990-11-12 | 1995-07-01 | Hoechst Ag | Bisindenilmetalocenos sustituidos en posicion 2, procedimiento para su preparacion y su utilizacion como catalizadores en la polimerizacion de olefinas. |
| EP0485821B1 (de) | 1990-11-12 | 1996-06-12 | Hoechst Aktiengesellschaft | Metallocene mit Liganden aus 2-substituierten Indenylderivaten, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
| DE4121368A1 (de) * | 1991-06-28 | 1993-01-07 | Hoechst Ag | Katalysator und verfahren zur herstellung von hochmolekularen polyolefinen |
| NL9201970A (nl) | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| IT1276084B1 (it) * | 1995-11-07 | 1997-10-24 | Enichem Spa | Ciclopentadienil derivati pontati e procedimento per la loro preparazione |
| IT1290856B1 (it) * | 1996-12-19 | 1998-12-14 | Enichem Spa | Metalloceni, loro preparazione ed uso nella polimerizzazione di alfa-olefine |
-
1999
- 1999-11-10 JP JP2000582403A patent/JP2002530286A/ja active Pending
- 1999-11-10 ES ES99955972T patent/ES2189516T3/es not_active Expired - Lifetime
- 1999-11-10 HU HU0101157A patent/HUP0101157A2/hu unknown
- 1999-11-10 WO PCT/EP1999/008647 patent/WO2000029416A1/en not_active Ceased
- 1999-11-10 BR BR9910192-0A patent/BR9910192A/pt not_active Application Discontinuation
- 1999-11-10 EP EP99955972A patent/EP1047702B1/en not_active Expired - Lifetime
- 1999-11-10 AU AU12705/00A patent/AU1270500A/en not_active Abandoned
- 1999-11-10 DE DE69905011T patent/DE69905011T2/de not_active Expired - Fee Related
- 1999-11-10 CN CN99803373A patent/CN1291986A/zh active Pending
- 1999-11-10 IL IL13703699A patent/IL137036A0/xx unknown
- 1999-11-10 CA CA002317588A patent/CA2317588A1/en not_active Abandoned
- 1999-11-10 KR KR1020007007865A patent/KR20010034211A/ko not_active Withdrawn
- 1999-11-10 US US09/600,350 patent/US6541584B1/en not_active Expired - Fee Related
- 1999-11-18 AR ARP990105861A patent/AR021311A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR9910192A (pt) | 2001-05-22 |
| CN1291986A (zh) | 2001-04-18 |
| IL137036A0 (en) | 2001-06-14 |
| US6541584B1 (en) | 2003-04-01 |
| DE69905011T2 (de) | 2003-11-06 |
| DE69905011D1 (de) | 2003-02-27 |
| WO2000029416A1 (en) | 2000-05-25 |
| EP1047702B1 (en) | 2003-01-22 |
| AU1270500A (en) | 2000-06-05 |
| CA2317588A1 (en) | 2000-05-25 |
| HUP0101157A2 (hu) | 2001-07-30 |
| AR021311A1 (es) | 2002-07-17 |
| JP2002530286A (ja) | 2002-09-17 |
| ES2189516T3 (es) | 2003-07-01 |
| EP1047702A1 (en) | 2000-11-02 |
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