JP2008522013A5 - - Google Patents
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- Publication number
- JP2008522013A5 JP2008522013A5 JP2007544500A JP2007544500A JP2008522013A5 JP 2008522013 A5 JP2008522013 A5 JP 2008522013A5 JP 2007544500 A JP2007544500 A JP 2007544500A JP 2007544500 A JP2007544500 A JP 2007544500A JP 2008522013 A5 JP2008522013 A5 JP 2008522013A5
- Authority
- JP
- Japan
- Prior art keywords
- indenyl
- phenyl
- methyl
- zirconium dichloride
- group
- 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.)
- Granted
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- -1 tetrahydroindenyl Chemical group 0.000 claims 182
- 125000004432 carbon atom Chemical group C* 0.000 claims 137
- 238000000034 method Methods 0.000 claims 84
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims 82
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 67
- 125000000217 alkyl group Chemical group 0.000 claims 49
- 239000000203 mixture Substances 0.000 claims 41
- 125000003118 aryl group Chemical group 0.000 claims 40
- 239000000463 material Substances 0.000 claims 38
- 239000012876 carrier material Substances 0.000 claims 35
- 239000003054 catalyst Substances 0.000 claims 33
- 239000002904 solvent Substances 0.000 claims 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 30
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 29
- 125000004122 cyclic group Chemical group 0.000 claims 26
- 150000002430 hydrocarbons Chemical group 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 229910052782 aluminium Inorganic materials 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 239000000377 silicon dioxide Substances 0.000 claims 15
- DNMINOWCGCDWKQ-UHFFFAOYSA-N 5-methylcyclopenta[b]pyrrole Chemical compound C1=NC2=CC(C)=CC2=C1 DNMINOWCGCDWKQ-UHFFFAOYSA-N 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 14
- 239000000460 chlorine Substances 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 229910052710 silicon Inorganic materials 0.000 claims 14
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 229910052796 boron Inorganic materials 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims 13
- WUKFGBUJEPLCSN-UHFFFAOYSA-N 5-methyl-2h-cyclopenta[b]thiophene Chemical compound C1SC2=CC(C)=CC2=C1 WUKFGBUJEPLCSN-UHFFFAOYSA-N 0.000 claims 12
- 150000001336 alkenes Chemical class 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000005104 aryl silyl group Chemical group 0.000 claims 11
- 125000004104 aryloxy group Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 10
- 229910052726 zirconium Inorganic materials 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 9
- 238000010438 heat treatment Methods 0.000 claims 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 9
- 238000005406 washing Methods 0.000 claims 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 8
- 238000001035 drying Methods 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 239000007983 Tris buffer Substances 0.000 claims 7
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 229910052698 phosphorus Inorganic materials 0.000 claims 7
- YNSOSPOWYQTGQP-UHFFFAOYSA-N 5-methyl-2h-cyclopenta[b]furan Chemical compound C1OC2=CC(C)=CC2=C1 YNSOSPOWYQTGQP-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 5
- FLNSMWIFPVKXPV-UHFFFAOYSA-N 2,5-dimethyl-2h-cyclopenta[b]thiophene Chemical compound CC1=CC2=CC(C)SC2=C1 FLNSMWIFPVKXPV-UHFFFAOYSA-N 0.000 claims 5
- ZGEGEMSWVWZKKD-UHFFFAOYSA-N 5-methyl-1-phenyl-2h-cyclopenta[b]pyrrole Chemical compound C12=CC(C)=CC2=CCN1C1=CC=CC=C1 ZGEGEMSWVWZKKD-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 5
- 229910052751 metal Inorganic materials 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- 239000000178 monomer Substances 0.000 claims 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 5
- 230000000737 periodic effect Effects 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 239000000725 suspension Substances 0.000 claims 5
- 125000003944 tolyl group Chemical group 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 4
- 239000002841 Lewis acid Substances 0.000 claims 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052735 hafnium Inorganic materials 0.000 claims 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 150000007517 lewis acids Chemical class 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- VZENYRLLQMKOTD-UHFFFAOYSA-N 5-methyl-1h-cyclopenta[c]thiophene Chemical compound S1CC2=CC(C)=CC2=C1 VZENYRLLQMKOTD-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 3
- 125000003828 azulenyl group Chemical group 0.000 claims 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
- 150000008040 ionic compounds Chemical class 0.000 claims 3
- 239000011777 magnesium Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 3
- 229940031826 phenolate Drugs 0.000 claims 3
- 239000012047 saturated solution Substances 0.000 claims 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 3
- 239000011800 void material Substances 0.000 claims 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims 2
- FJTIXNPQMYWPRB-UHFFFAOYSA-N 2,5-dimethylcyclopenta[b]pyrrole Chemical compound CC1=NC2=CC(C)=CC2=C1 FJTIXNPQMYWPRB-UHFFFAOYSA-N 0.000 claims 2
- RMNKHKYRLLFLPT-UHFFFAOYSA-N 5-methylcyclopenta[c]pyrrole Chemical compound N1=CC2=CC(C)=CC2=C1 RMNKHKYRLLFLPT-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- PATLRDHGHBZQMP-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(CC)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(CC)=CC2=C1C=CC=C2C1=CC=CC=C1 PATLRDHGHBZQMP-UHFFFAOYSA-L 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 2
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 claims 2
- 229910052732 germanium Inorganic materials 0.000 claims 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 2
- 150000002484 inorganic compounds Chemical class 0.000 claims 2
- 229910010272 inorganic material Inorganic materials 0.000 claims 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 238000002791 soaking Methods 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229910052718 tin Inorganic materials 0.000 claims 2
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- TUVNTOZFUMXLAJ-UHFFFAOYSA-N 5-methyl-1h-cyclopenta[c]furan Chemical compound O1CC2=CC(C)=CC2=C1 TUVNTOZFUMXLAJ-UHFFFAOYSA-N 0.000 claims 1
- OEGDPPCJMHJLGR-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-cyclopenta[c]pyrrole Chemical compound C1C2=CC(C)=CC2=CN1C1=CC=CC=C1 OEGDPPCJMHJLGR-UHFFFAOYSA-N 0.000 claims 1
- JEVOMMOUGUDSDA-UHFFFAOYSA-L 5-methylcyclopenta[b]pyrrole;zirconium(2+);dichloride Chemical compound [Cl-].[Cl-].[Zr+2].C1=CC2=CC(C)=CC2=N1 JEVOMMOUGUDSDA-UHFFFAOYSA-L 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910018516 Al—O Inorganic materials 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KGCYJJMECYZPFT-UHFFFAOYSA-L CC(C)C1=CC=CC2=C1C=C(C)C2[Zr](Cl)Cl Chemical compound CC(C)C1=CC=CC2=C1C=C(C)C2[Zr](Cl)Cl KGCYJJMECYZPFT-UHFFFAOYSA-L 0.000 claims 1
- YZYMXOBVMCYLAX-UHFFFAOYSA-L CC1=CC2=C(C)C=CC=C2C1[Zr](Cl)Cl Chemical compound CC1=CC2=C(C)C=CC=C2C1[Zr](Cl)Cl YZYMXOBVMCYLAX-UHFFFAOYSA-L 0.000 claims 1
- BFHSWVQLQPQWIG-UHFFFAOYSA-L CCCCCCC1=CC2=C(C=CC=C2C1[Zr](Cl)Cl)C1=CC=CC=C1 Chemical compound CCCCCCC1=CC2=C(C=CC=C2C1[Zr](Cl)Cl)C1=CC=CC=C1 BFHSWVQLQPQWIG-UHFFFAOYSA-L 0.000 claims 1
- WIMIFQHIJHYWGI-UHFFFAOYSA-N CNC.CNC.[Zr] Chemical compound CNC.CNC.[Zr] WIMIFQHIJHYWGI-UHFFFAOYSA-N 0.000 claims 1
- 229910020366 ClO 4 Inorganic materials 0.000 claims 1
- SXNCBONZDLIJPE-UHFFFAOYSA-L Cl[Zr](Cl)C1C(C)=CC2=C1C=CC=C2C1=CC=C(C(C)(C)C)C=C1 Chemical compound Cl[Zr](Cl)C1C(C)=CC2=C1C=CC=C2C1=CC=C(C(C)(C)C)C=C1 SXNCBONZDLIJPE-UHFFFAOYSA-L 0.000 claims 1
- PKEMXXKAKPLNMX-UHFFFAOYSA-L Cl[Zr](Cl)C1C(CC)=CC2=C1C=CC=C2C1=CC=C(C(C)(C)C)C=C1 Chemical compound Cl[Zr](Cl)C1C(CC)=CC2=C1C=CC=C2C1=CC=C(C(C)(C)C)C=C1 PKEMXXKAKPLNMX-UHFFFAOYSA-L 0.000 claims 1
- WMEGFCWWJNZIHG-UHFFFAOYSA-L Cl[Zr]Cl.CC(C)C1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 Chemical compound Cl[Zr]Cl.CC(C)C1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 WMEGFCWWJNZIHG-UHFFFAOYSA-L 0.000 claims 1
- YVHWPOYETXHSEU-UHFFFAOYSA-L Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C(C)(C)C Chemical compound Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C(C)(C)C YVHWPOYETXHSEU-UHFFFAOYSA-L 0.000 claims 1
- AWFSRWFKARHLSN-UHFFFAOYSA-L Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=C(C=CC=C1)C(C)(C)C Chemical compound Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=C(C=CC=C1)C(C)(C)C AWFSRWFKARHLSN-UHFFFAOYSA-L 0.000 claims 1
- FMGOUPKPZQOBMW-UHFFFAOYSA-L Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 Chemical compound Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 FMGOUPKPZQOBMW-UHFFFAOYSA-L 0.000 claims 1
- ZAILCADIBBSTGU-UHFFFAOYSA-L Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C=C1)C(F)(F)F Chemical compound Cl[Zr]Cl.CC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C=C1)C(F)(F)F ZAILCADIBBSTGU-UHFFFAOYSA-L 0.000 claims 1
- JJCTXWWOUATGBR-UHFFFAOYSA-L Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 Chemical compound Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(C)C=C1 JJCTXWWOUATGBR-UHFFFAOYSA-L 0.000 claims 1
- UEKRIGNLXPDUQV-UHFFFAOYSA-L Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(CC)C=C1 Chemical compound Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=C(CC)C=C1 UEKRIGNLXPDUQV-UHFFFAOYSA-L 0.000 claims 1
- WCTFZZBNZFWOOA-UHFFFAOYSA-L Cl[Zr]Cl.CCC1=CC=C(C=C1)C1=C2C=C(C)[CH]C2=CC=C1 Chemical compound Cl[Zr]Cl.CCC1=CC=C(C=C1)C1=C2C=C(C)[CH]C2=CC=C1 WCTFZZBNZFWOOA-UHFFFAOYSA-L 0.000 claims 1
- CKTRUSVYRRPJMB-UHFFFAOYSA-L Cl[Zr]Cl.CCC1=CC=C(C=C1)C1=C2C=C([CH]C2=CC=C1)C(C)C Chemical compound Cl[Zr]Cl.CCC1=CC=C(C=C1)C1=C2C=C([CH]C2=CC=C1)C(C)C CKTRUSVYRRPJMB-UHFFFAOYSA-L 0.000 claims 1
- VYVYMXAPWFNNGI-UHFFFAOYSA-L Cl[Zr]Cl.CCCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.CCCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC=C1 VYVYMXAPWFNNGI-UHFFFAOYSA-L 0.000 claims 1
- YYMSCIYYMLMSPC-UHFFFAOYSA-L Cl[Zr]Cl.CCCCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.CCCCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC=C1 YYMSCIYYMLMSPC-UHFFFAOYSA-L 0.000 claims 1
- DZETZMSAJDMAKS-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 DZETZMSAJDMAKS-UHFFFAOYSA-L 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- 229910018068 Li 2 O Inorganic materials 0.000 claims 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910018286 SbF 6 Inorganic materials 0.000 claims 1
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- LEVWWZUWLYPFGL-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=C(C=CC=C1)C(C)(C)C)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=C(C=CC=C1)C(C)(C)C)[Zr+2] LEVWWZUWLYPFGL-UHFFFAOYSA-L 0.000 claims 1
- IVTACAWWRYQSNC-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)C(F)(F)F)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)C(F)(F)F)[Zr+2] IVTACAWWRYQSNC-UHFFFAOYSA-L 0.000 claims 1
- DPSBFFDEMXVKOE-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)OC)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)OC)[Zr+2] DPSBFFDEMXVKOE-UHFFFAOYSA-L 0.000 claims 1
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- VNMCULJCUSFIFG-UHFFFAOYSA-L [Cl-].[Cl-].C(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)OC)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=C(C=C1)OC)[Zr+2] VNMCULJCUSFIFG-UHFFFAOYSA-L 0.000 claims 1
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- FYQDMYPABUUNKK-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(C2=CC=C(C(=C2C=1)C(C)C)C(C)C)[Zr+2] Chemical compound [Cl-].[Cl-].CC=1C(C2=CC=C(C(=C2C=1)C(C)C)C(C)C)[Zr+2] FYQDMYPABUUNKK-UHFFFAOYSA-L 0.000 claims 1
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- IJCKEISURUTHFS-UHFFFAOYSA-L [Cl-].[Cl-].CCC1=CC=CC2=C1C=C(C)C2[Zr+2] Chemical compound [Cl-].[Cl-].CCC1=CC=CC2=C1C=C(C)C2[Zr+2] IJCKEISURUTHFS-UHFFFAOYSA-L 0.000 claims 1
- SGYIGJWYLFOUDT-UHFFFAOYSA-L [Cl-].[Cl-].[Zr+2]C1C(C(C)C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].[Zr+2]C1C(C(C)C)=CC2=C1C=CC=C2C1=CC=CC=C1 SGYIGJWYLFOUDT-UHFFFAOYSA-L 0.000 claims 1
- OBPUCSCMGVCWPN-UHFFFAOYSA-L [Cl-].[Cl-].[Zr+2]C1C(C)=CC2=C1C=C(C)C=C2C Chemical compound [Cl-].[Cl-].[Zr+2]C1C(C)=CC2=C1C=C(C)C=C2C OBPUCSCMGVCWPN-UHFFFAOYSA-L 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- 229910000085 borane Inorganic materials 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- DMFUOMWPVRRXTM-UHFFFAOYSA-L dichlorozirconium;5-methyl-2h-cyclopenta[b]thiophene Chemical compound Cl[Zr]Cl.C1SC2=CC(C)=CC2=C1 DMFUOMWPVRRXTM-UHFFFAOYSA-L 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001339 silanediyl group Chemical group [H][Si]([H])(*)* 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 claims 1
- HPKBFHDRGPIYAG-UHFFFAOYSA-N tris(2,4,6-trifluorophenyl)borane Chemical compound FC1=CC(F)=CC(F)=C1B(C=1C(=CC(F)=CC=1F)F)C1=C(F)C=C(F)C=C1F HPKBFHDRGPIYAG-UHFFFAOYSA-N 0.000 claims 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-UHFFFAOYSA-N 0.000 claims 1
- LKNHGIFPRLUGEG-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 LKNHGIFPRLUGEG-UHFFFAOYSA-N 0.000 claims 1
- AGOOAFIKKUZTEB-UHFFFAOYSA-N tris(3,5-difluorophenyl)borane Chemical compound FC1=CC(F)=CC(B(C=2C=C(F)C=C(F)C=2)C=2C=C(F)C=C(F)C=2)=C1 AGOOAFIKKUZTEB-UHFFFAOYSA-N 0.000 claims 1
- OHSAEOPCBBOWPU-UHFFFAOYSA-N tris(3,5-dimethylphenyl)borane Chemical compound CC1=CC(C)=CC(B(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 OHSAEOPCBBOWPU-UHFFFAOYSA-N 0.000 claims 1
- YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 claims 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims 1
- OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 claims 1
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| US7169864B2 (en) * | 2004-12-01 | 2007-01-30 | Novolen Technology Holdings, C.V. | Metallocene catalysts, their synthesis and their use for the polymerization of olefins |
| US8034886B2 (en) | 2005-11-04 | 2011-10-11 | Ticona Gmbh | Process for manufacturing high to ultra high molecular weight polymers using novel bridged metallocene catalysts |
| US7598329B2 (en) * | 2005-11-04 | 2009-10-06 | Ticona Gmbh | Process for manufacturing ultra high molecular weight polymers using novel bridged metallocene catalysts |
| DE102005052654A1 (de) * | 2005-11-04 | 2007-05-16 | Ticona Gmbh | Verfahren zur Herstellung von ultrahochmolekularen Polymeren unter Verwendung von speziellen verbrückten Metallocen-Katalysatoren |
| US7683002B2 (en) * | 2006-04-04 | 2010-03-23 | Fina Technology, Inc. | Transition metal catalyst and formation thereof |
| US20070299222A1 (en) * | 2006-04-04 | 2007-12-27 | Fina Technology, Inc. | Transition metal catalysts and formation thereof |
| EP1930348A1 (en) * | 2006-12-05 | 2008-06-11 | Ineos Manufacturing France SAS | Supported catalyst system |
| US8299287B2 (en) * | 2007-10-25 | 2012-10-30 | Lammus Novolen Technology GmbH | Metallocene compounds, catalysts comprising them, process for producing an olefin polymer by use of the catalysts, and olefin homo- and copolymers |
| EP2235071A2 (en) | 2007-10-25 | 2010-10-06 | Novolen Technology Holdings, C.V. | Metallocene compounds, catalysts comprising them, process for producing an olefin polymer by use of the catalysts, and olefin homo and copolymers |
| KR101278336B1 (ko) | 2007-10-25 | 2013-06-25 | 루머스 노보렌 테크놀로지 게엠베하 | 안사-메탈로센 화합물의 라세모선택적 합성, 안사-메탈로센 화합물, 이를 포함하는 촉매, 그 촉매를 이용한 올레핀 폴리머 제조 공정, 그리고 올레핀 호모- 및 코폴리머 |
| TW200936619A (en) | 2007-11-15 | 2009-09-01 | Univation Tech Llc | Polymerization catalysts, methods of making, methods of using, and polyolefin products made therefrom |
| KR101271055B1 (ko) * | 2008-03-28 | 2013-06-04 | 에스케이종합화학 주식회사 | 메탈로센 담지촉매 조성물 및 이를 이용한 폴리올레핀의제조방법 |
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-
2004
- 2004-12-01 US US11/001,272 patent/US7169864B2/en not_active Expired - Lifetime
-
2005
- 2005-11-30 AR ARP050105020A patent/AR052985A1/es active IP Right Grant
- 2005-12-01 MX MX2007006313A patent/MX2007006313A/es active IP Right Grant
- 2005-12-01 EP EP05852607.0A patent/EP1828266B1/en not_active Expired - Lifetime
- 2005-12-01 ES ES05852607.0T patent/ES2548726T3/es not_active Expired - Lifetime
- 2005-12-01 JP JP2007544500A patent/JP5311827B2/ja not_active Expired - Fee Related
- 2005-12-01 KR KR1020077012546A patent/KR101354477B1/ko not_active Expired - Fee Related
- 2005-12-01 CN CN2005800473108A patent/CN101124252B/zh not_active Expired - Lifetime
- 2005-12-01 RU RU2007124637/04A patent/RU2360931C2/ru active
- 2005-12-01 BR BRPI0518701A patent/BRPI0518701B8/pt not_active IP Right Cessation
- 2005-12-01 CN CN201110285770.1A patent/CN103012623B/zh not_active Expired - Lifetime
- 2005-12-01 SG SG200907972-4A patent/SG158099A1/en unknown
- 2005-12-01 WO PCT/US2005/043421 patent/WO2006060544A1/en not_active Ceased
-
2006
- 2006-12-06 US US11/634,653 patent/US20070082806A1/en not_active Abandoned
-
2007
- 2007-05-29 ZA ZA200704403A patent/ZA200704403B/xx unknown
- 2007-10-31 US US11/980,837 patent/US20080287286A1/en not_active Abandoned
-
2011
- 2011-06-08 JP JP2011128714A patent/JP2011231328A/ja not_active Withdrawn
-
2012
- 2012-01-10 AR ARP120100076A patent/AR084818A2/es unknown
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