RU2360931C2 - Металлоценовые катализаторы, их синтез и их применение для полимеризации олефинов - Google Patents
Металлоценовые катализаторы, их синтез и их применение для полимеризации олефинов Download PDFInfo
- Publication number
- RU2360931C2 RU2360931C2 RU2007124637/04A RU2007124637A RU2360931C2 RU 2360931 C2 RU2360931 C2 RU 2360931C2 RU 2007124637/04 A RU2007124637/04 A RU 2007124637/04A RU 2007124637 A RU2007124637 A RU 2007124637A RU 2360931 C2 RU2360931 C2 RU 2360931C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- indenyl
- zirconium dichloride
- carbon atoms
- bis
- Prior art date
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- 150000001336 alkenes Chemical class 0.000 title claims abstract description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000012968 metallocene catalyst Substances 0.000 title description 68
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 309
- 239000000203 mixture Substances 0.000 claims abstract description 189
- 238000000034 method Methods 0.000 claims abstract description 165
- 239000002904 solvent Substances 0.000 claims abstract description 130
- 238000002360 preparation method Methods 0.000 claims abstract description 118
- 239000012876 carrier material Substances 0.000 claims abstract description 90
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 40
- 230000003197 catalytic effect Effects 0.000 claims abstract description 29
- 238000010438 heat treatment Methods 0.000 claims abstract description 24
- 239000002841 Lewis acid Substances 0.000 claims abstract description 21
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 21
- 150000008040 ionic compounds Chemical class 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 814
- -1 methyl radicals Chemical class 0.000 claims description 484
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 479
- 239000000243 solution Substances 0.000 claims description 326
- 239000003054 catalyst Substances 0.000 claims description 321
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 291
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 253
- 239000000377 silicon dioxide Substances 0.000 claims description 223
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 120
- 239000000725 suspension Substances 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 229910052757 nitrogen Inorganic materials 0.000 claims description 84
- 239000000843 powder Substances 0.000 claims description 82
- 150000002430 hydrocarbons Chemical class 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 56
- 125000004122 cyclic group Chemical group 0.000 claims description 56
- 238000005470 impregnation Methods 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052782 aluminium Inorganic materials 0.000 claims description 37
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 229910052710 silicon Inorganic materials 0.000 claims description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 29
- DNMINOWCGCDWKQ-UHFFFAOYSA-N 5-methylcyclopenta[b]pyrrole Chemical compound C1=NC2=CC(C)=CC2=C1 DNMINOWCGCDWKQ-UHFFFAOYSA-N 0.000 claims description 28
- 229910052796 boron Inorganic materials 0.000 claims description 28
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 229910052698 phosphorus Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 238000001035 drying Methods 0.000 claims description 25
- 239000011148 porous material Substances 0.000 claims description 25
- WUKFGBUJEPLCSN-UHFFFAOYSA-N 5-methyl-2h-cyclopenta[b]thiophene Chemical compound C1SC2=CC(C)=CC2=C1 WUKFGBUJEPLCSN-UHFFFAOYSA-N 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 229910052726 zirconium Inorganic materials 0.000 claims description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 21
- 125000005104 aryl silyl group Chemical group 0.000 claims description 21
- 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 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 20
- 238000005406 washing Methods 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- 239000005977 Ethylene Substances 0.000 claims description 18
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 16
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 16
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 230000000737 periodic effect Effects 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 14
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 13
- 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 description 12
- YNSOSPOWYQTGQP-UHFFFAOYSA-N 5-methyl-2h-cyclopenta[b]furan Chemical compound C1OC2=CC(C)=CC2=C1 YNSOSPOWYQTGQP-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 230000004913 activation Effects 0.000 claims description 12
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- FLNSMWIFPVKXPV-UHFFFAOYSA-N 2,5-dimethyl-2h-cyclopenta[b]thiophene Chemical compound CC1=CC2=CC(C)SC2=C1 FLNSMWIFPVKXPV-UHFFFAOYSA-N 0.000 claims description 10
- 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 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 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 description 10
- 239000002245 particle Substances 0.000 claims description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 230000004580 weight loss Effects 0.000 claims description 10
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229910052735 hafnium Inorganic materials 0.000 claims description 9
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 238000001354 calcination Methods 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- VZENYRLLQMKOTD-UHFFFAOYSA-N 5-methyl-1h-cyclopenta[c]thiophene Chemical compound S1CC2=CC(C)=CC2=C1 VZENYRLLQMKOTD-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 6
- 229940031826 phenolate Drugs 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 238000009736 wetting Methods 0.000 claims description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- FJTIXNPQMYWPRB-UHFFFAOYSA-N 2,5-dimethylcyclopenta[b]pyrrole Chemical compound CC1=NC2=CC(C)=CC2=C1 FJTIXNPQMYWPRB-UHFFFAOYSA-N 0.000 claims description 4
- RMNKHKYRLLFLPT-UHFFFAOYSA-N 5-methylcyclopenta[c]pyrrole Chemical compound N1=CC2=CC(C)=CC2=C1 RMNKHKYRLLFLPT-UHFFFAOYSA-N 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- VGRFVJMYCCLWPQ-UHFFFAOYSA-N germanium Chemical compound [Ge].[Ge] VGRFVJMYCCLWPQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002484 inorganic compounds Chemical class 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 2
- BGGKSZPSSRGVTP-UHFFFAOYSA-L 2-methyl-1h-inden-1-ide;zirconium(4+);dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C1=CC=C2[CH-]C(C)=CC2=C1.C1=CC=C2[CH-]C(C)=CC2=C1 BGGKSZPSSRGVTP-UHFFFAOYSA-L 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- TUVNTOZFUMXLAJ-UHFFFAOYSA-N 5-methyl-1h-cyclopenta[c]furan Chemical compound O1CC2=CC(C)=CC2=C1 TUVNTOZFUMXLAJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- VUFCANOMBNFAOI-UHFFFAOYSA-L 5-methyl-2H-cyclopenta[b]thiophene zirconium(2+) dichloride Chemical compound [Cl-].[Cl-].[Zr+2].C1SC2=CC(C)=CC2=C1.C1SC2=CC(C)=CC2=C1 VUFCANOMBNFAOI-UHFFFAOYSA-L 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910018516 Al—O Inorganic materials 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 230000002860 competitive effect Effects 0.000 description 1
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- GSQKXUNYYCYYKT-UHFFFAOYSA-N cyclo-trialuminium Chemical compound [Al]1[Al]=[Al]1 GSQKXUNYYCYYKT-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- NRAYZPGATNMOSB-UHFFFAOYSA-N dichloro(dihexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)CCCCCC NRAYZPGATNMOSB-UHFFFAOYSA-N 0.000 description 1
- YUYHCACQLHNZLS-UHFFFAOYSA-N dichloro-cyclohexyl-methylsilane Chemical compound C[Si](Cl)(Cl)C1CCCCC1 YUYHCACQLHNZLS-UHFFFAOYSA-N 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- GNVPGBIHGALKRR-UHFFFAOYSA-N dichloro-methyl-propylsilane Chemical compound CCC[Si](C)(Cl)Cl GNVPGBIHGALKRR-UHFFFAOYSA-N 0.000 description 1
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
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- 238000010981 drying operation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- JBAFGPYYLLXEKL-UHFFFAOYSA-N ethene;hexa-1,4-diene;prop-1-ene Chemical compound C=C.CC=C.CC=CCC=C JBAFGPYYLLXEKL-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical compound C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- QDEZCOQKJSRQNN-UHFFFAOYSA-N ethenyl-dimethyl-phenylsilane Chemical compound C=C[Si](C)(C)C1=CC=CC=C1 QDEZCOQKJSRQNN-UHFFFAOYSA-N 0.000 description 1
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- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
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- NEMUVWSQFWIZKP-UHFFFAOYSA-N n-methyl-n-trichlorosilylmethanamine Chemical compound CN(C)[Si](Cl)(Cl)Cl NEMUVWSQFWIZKP-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
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- 230000037048 polymerization activity Effects 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-O thiolan-1-ium Chemical compound C1CC[SH+]C1 RAOIDOHSFRTOEL-UHFFFAOYSA-O 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
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- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 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
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Classifications
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- 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
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/655—Pretreating with metals or metal-containing compounds with aluminium or compounds thereof
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of titanium, zirconium or hafnium
-
- 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
- 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
- C08F4/02—Carriers therefor
-
- 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
-
- 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
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/001,272 | 2004-12-01 | ||
| US11/001,272 US7169864B2 (en) | 2004-12-01 | 2004-12-01 | Metallocene catalysts, their synthesis and their use for the polymerization of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007124637A RU2007124637A (ru) | 2009-01-10 |
| RU2360931C2 true RU2360931C2 (ru) | 2009-07-10 |
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Family Applications (1)
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| RU2007124637/04A RU2360931C2 (ru) | 2004-12-01 | 2005-12-01 | Металлоценовые катализаторы, их синтез и их применение для полимеризации олефинов |
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| Country | Link |
|---|---|
| US (3) | US7169864B2 (https=) |
| EP (1) | EP1828266B1 (https=) |
| JP (2) | JP5311827B2 (https=) |
| KR (1) | KR101354477B1 (https=) |
| CN (2) | CN103012623B (https=) |
| AR (2) | AR052985A1 (https=) |
| BR (1) | BRPI0518701B8 (https=) |
| ES (1) | ES2548726T3 (https=) |
| MX (1) | MX2007006313A (https=) |
| RU (1) | RU2360931C2 (https=) |
| SG (1) | SG158099A1 (https=) |
| WO (1) | WO2006060544A1 (https=) |
| ZA (1) | ZA200704403B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2805112C2 (ru) * | 2018-11-06 | 2023-10-11 | Дау Глоубл Текнолоджиз Ллк | Способ полимеризации олефинов с применением неметаллоценового предкатализатора, растворимого в алканах |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| WO2009054833A2 (en) | 2007-10-25 | 2009-04-30 | 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 |
| ATE547439T1 (de) | 2007-10-25 | 2012-03-15 | Lummus Novolen Technology Gmbh | Racemoselektive synthese von ansa-metallocen- verbindungen, ansa-metallocen-verbindungen, diese enthaltende katalysatoren, verfahren zur herstellung eines olefinpolymers durch verwendung der katalysatoren und olefinhomopolymere und - copolymere |
| BRPI0722162A2 (pt) * | 2007-10-25 | 2014-03-18 | Lummus Novolen Technology Gmbh | Compostos de metaloceno, catalisadores compreendendo os mesmos, processo para produzir um polímero de olefina pelo uso de catalisadores, e homo-e copolímeros de olefina. |
| 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 |
| US8076429B2 (en) * | 2009-03-11 | 2011-12-13 | Lummus Novolen Technology Gmbh | Supertransparent high impact strength random block copolymer |
| KR101050791B1 (ko) * | 2009-10-19 | 2011-07-20 | 주식회사 엘지화학 | 혼성 담지 메탈로센 촉매의 제조방법 및 이를 이용하여 제조된 혼성 담지 메탈로센 촉매 |
| BR112012013675A2 (pt) | 2009-12-07 | 2016-04-19 | Univation Tech Llc | métodos para a produção de carga estática de um catalisador e métodos para o uso do catalisador para produzir poliolefinas |
| EP2516484A1 (en) * | 2009-12-22 | 2012-10-31 | Borealis AG | Preparation of polypropylene in the presence of a single-site catalyst |
| EP2536767B1 (en) | 2010-02-18 | 2015-05-06 | Univation Technologies, LLC | Methods for operating a polymerization reactor |
| KR20130026531A (ko) | 2010-02-22 | 2013-03-13 | 유니베이션 테크놀로지즈, 엘엘씨 | 폴리올레핀 생산물을 생산하기 위한 촉매 시스템 및 이의 사용 방법 |
| US9029486B2 (en) | 2010-03-08 | 2015-05-12 | Lg Chem, Ltd. | Supported metallocene catalyst, method for preparing the same and method for preparing polyolefin using the same |
| BR112012025925B1 (pt) | 2010-04-13 | 2020-03-17 | Univation Technologies, Llc | Mistura polimérica e filme |
| EP2738183A1 (en) | 2010-05-07 | 2014-06-04 | Borealis AG | Preparation of a solid catalyst system |
| EP2402353B1 (en) | 2010-07-01 | 2018-04-25 | Borealis AG | Group 4 metallocenes useful as catalysts for the polymerization of olefins |
| ES2565438T3 (es) | 2010-07-01 | 2016-04-04 | Borealis Ag | Proceso para la polimerización de olefinas usando metalocenos del grupo 4 como catalizadores |
| EP2593217B1 (en) | 2010-07-16 | 2014-07-02 | Univation Technologies, LLC | Systems and methods for measuring particle accumulation on reactor surfaces |
| WO2012009215A1 (en) | 2010-07-16 | 2012-01-19 | Univation Technologies, Llc | Systems and methods for measuring static charge on particulates |
| WO2012015898A1 (en) | 2010-07-28 | 2012-02-02 | Univation Technologies, Llc | Systems and methods for measuring velocity of a particle/fluid mixture |
| WO2012055797A1 (en) | 2010-10-28 | 2012-05-03 | Lummus Novolen Technology Gmbh | Nonwoven and yarn polypropylene with additivation |
| US20120116034A1 (en) | 2010-11-08 | 2012-05-10 | Dow Global Technologies, Inc. | Solution polymerization process and procatalyst carrier systems useful therein |
| CN103228682B (zh) | 2010-11-30 | 2015-07-22 | 尤尼威蒂恩技术有限责任公司 | 用经萃取的金属羧酸盐聚合烯烃的方法 |
| MY161763A (en) | 2010-11-30 | 2017-05-15 | Univation Tech Llc | Catalyst composition having improved flow characteristics and methods of making and using the same |
| CN103298842B (zh) | 2010-12-17 | 2016-08-31 | 尤尼威蒂恩技术有限责任公司 | 从聚烯烃吹扫气体产物回收烃的系统以及方法 |
| CN103347905B (zh) | 2010-12-22 | 2015-12-16 | 尤尼威蒂恩技术有限责任公司 | 用于聚烯烃聚合方法的添加剂 |
| EP2655431A1 (en) | 2010-12-22 | 2013-10-30 | Borealis AG | Bridged metallocene catalysts |
| RU2598023C2 (ru) | 2011-05-13 | 2016-09-20 | Юнивейшн Текнолоджиз, Ллк | Полученные распылительной сушкой каталитические композиции и способы полимеризации, в которых они применяются |
| WO2013028283A1 (en) | 2011-08-19 | 2013-02-28 | Univation Technologies, Llc | Catalyst systems and methods for using same to produce polyolefin products |
| KR101485567B1 (ko) * | 2011-09-07 | 2015-01-23 | 주식회사 엘지화학 | 담지 메탈로센 촉매의 제조방법 및 이를 이용하여 제조된 담지 메탈로센 촉매 |
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- 2005-12-01 RU RU2007124637/04A patent/RU2360931C2/ru active
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Also Published As
| Publication number | Publication date |
|---|---|
| AR084818A2 (es) | 2013-06-26 |
| RU2007124637A (ru) | 2009-01-10 |
| EP1828266B1 (en) | 2015-07-22 |
| BRPI0518701B1 (pt) | 2018-09-25 |
| MX2007006313A (es) | 2007-11-23 |
| CN103012623A (zh) | 2013-04-03 |
| JP5311827B2 (ja) | 2013-10-09 |
| ES2548726T3 (es) | 2015-10-20 |
| KR101354477B1 (ko) | 2014-01-24 |
| US20080287286A1 (en) | 2008-11-20 |
| CN101124252A (zh) | 2008-02-13 |
| AR052985A1 (es) | 2007-04-18 |
| US20060116490A1 (en) | 2006-06-01 |
| US20070082806A1 (en) | 2007-04-12 |
| KR20070092217A (ko) | 2007-09-12 |
| CN101124252B (zh) | 2011-10-05 |
| WO2006060544A1 (en) | 2006-06-08 |
| ZA200704403B (en) | 2008-09-25 |
| BRPI0518701A2 (pt) | 2008-12-02 |
| JP2008522013A (ja) | 2008-06-26 |
| CN103012623B (zh) | 2015-09-16 |
| SG158099A1 (en) | 2010-01-29 |
| BRPI0518701B8 (pt) | 2023-01-24 |
| US7169864B2 (en) | 2007-01-30 |
| EP1828266A1 (en) | 2007-09-05 |
| JP2011231328A (ja) | 2011-11-17 |
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