CS277432B6 - Catalyst for the production of stereo-regular olefin polymer - Google Patents
Catalyst for the production of stereo-regular olefin polymer Download PDFInfo
- Publication number
- CS277432B6 CS277432B6 CS887281A CS728188A CS277432B6 CS 277432 B6 CS277432 B6 CS 277432B6 CS 887281 A CS887281 A CS 887281A CS 728188 A CS728188 A CS 728188A CS 277432 B6 CS277432 B6 CS 277432B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methylcyclopentadienyl
- cyclopentadienyl
- zirconium
- mmol
- polymerization
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- 229920000098 polyolefin Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 14
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 7
- 239000010703 silicon Substances 0.000 claims abstract description 7
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 5
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 2
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical class [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 44
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 abstract description 10
- 150000001336 alkenes Chemical class 0.000 abstract description 9
- 125000001424 substituent group Chemical group 0.000 abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 8
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 2
- -1 polypropylene Polymers 0.000 description 89
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 35
- 239000004743 Polypropylene Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 229920001155 polypropylene Polymers 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- 239000007788 liquid Substances 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- 239000011521 glass Substances 0.000 description 22
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 19
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 19
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 238000001228 spectrum Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 229910001873 dinitrogen Inorganic materials 0.000 description 11
- 239000011261 inert gas Substances 0.000 description 11
- 238000002329 infrared spectrum Methods 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- 150000002363 hafnium compounds Chemical class 0.000 description 10
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 9
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910007926 ZrCl Inorganic materials 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- NZDLIIBVQQCHBI-UHFFFAOYSA-L Cl[Zr]Cl.CC1=C[CH]C=C1 Chemical compound Cl[Zr]Cl.CC1=C[CH]C=C1 NZDLIIBVQQCHBI-UHFFFAOYSA-L 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RPBTVVXHHNXNDO-UHFFFAOYSA-L [Cl-].[Cl-].CC1(C=CC=C1)[Hf+2] Chemical compound [Cl-].[Cl-].CC1(C=CC=C1)[Hf+2] RPBTVVXHHNXNDO-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YMFKMVZJYPJIJF-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1(C=CC=C1)C Chemical compound [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1(C=CC=C1)C YMFKMVZJYPJIJF-UHFFFAOYSA-L 0.000 description 3
- GKDQSRVSFOWIFX-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Hf+2](C1(C=CC=C1)C)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C[SiH](C)[Hf+2](C1(C=CC=C1)C)C1C=CC=C1 GKDQSRVSFOWIFX-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VSIJJRQENVJPHZ-UHFFFAOYSA-M CC(C=C1)=CC1[Zr+](C1C=C(C)C=C1)[SiH](C)C.[Cl-] Chemical compound CC(C=C1)=CC1[Zr+](C1C=C(C)C=C1)[SiH](C)C.[Cl-] VSIJJRQENVJPHZ-UHFFFAOYSA-M 0.000 description 2
- YYOHSEOBMBTBOR-UHFFFAOYSA-L C[SiH](C)[Zr](Cl)(Cl)(C1C=CC=C1C(C)(C)C)C1C=CC=C1C(C)(C)C Chemical compound C[SiH](C)[Zr](Cl)(Cl)(C1C=CC=C1C(C)(C)C)C1C=CC=C1C(C)(C)C YYOHSEOBMBTBOR-UHFFFAOYSA-L 0.000 description 2
- GTRVWZVVNDDEGX-UHFFFAOYSA-L C[SiH]C.CC1=CC(C=C1)[Hf](Cl)(Cl)C1C=CC(C)=C1 Chemical compound C[SiH]C.CC1=CC(C=C1)[Hf](Cl)(Cl)C1C=CC(C)=C1 GTRVWZVVNDDEGX-UHFFFAOYSA-L 0.000 description 2
- FKOZSEFAYSVZLJ-UHFFFAOYSA-L C[SiH]C.CC1=CC(C=C1)[Zr](Cl)(Cl)C1C=CC(C)=C1 Chemical compound C[SiH]C.CC1=CC(C=C1)[Zr](Cl)(Cl)C1C=CC(C)=C1 FKOZSEFAYSVZLJ-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- AZDFVBATATYLOR-UHFFFAOYSA-L [Cl-].[Cl-].C[GeH](C)[Zr+2](C1(C=CC=C1)C)C1(C=CC=C1)C Chemical compound [Cl-].[Cl-].C[GeH](C)[Zr+2](C1(C=CC=C1)C)C1(C=CC=C1)C AZDFVBATATYLOR-UHFFFAOYSA-L 0.000 description 2
- DNEALSBZVPVHDR-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Hf+2](C1(C=CC=C1)C(C)(C)C)C1(C=CC=C1)C(C)(C)C Chemical compound [Cl-].[Cl-].C[SiH](C)[Hf+2](C1(C=CC=C1)C(C)(C)C)C1(C=CC=C1)C(C)(C)C DNEALSBZVPVHDR-UHFFFAOYSA-L 0.000 description 2
- PSFNFDOBYMQUFP-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C(C)(C)C)C1(C=CC=C1)C Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C(C)(C)C)C1(C=CC=C1)C PSFNFDOBYMQUFP-UHFFFAOYSA-L 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- AQMBOQOGGFNOQY-UHFFFAOYSA-N bis(1-tert-butylcyclopenta-2,4-dien-1-yl)-dimethylsilane Chemical compound C[Si](C1(C=CC=C1)C(C)(C)C)(C1(C=CC=C1)C(C)(C)C)C AQMBOQOGGFNOQY-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 2
- ZSTDXJKXCSBXIC-UHFFFAOYSA-N cyclopenta-2,4-dien-1-yl-dimethyl-(1-methylcyclopenta-2,4-dien-1-yl)silane Chemical compound C[Si](C1(C=CC=C1)C)(C1C=CC=C1)C ZSTDXJKXCSBXIC-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- MQISDUPKURIRCC-UHFFFAOYSA-N dimethyl-bis(1-methylcyclopenta-2,4-dien-1-yl)silane Chemical compound C[Si](C1(C=CC=C1)C)(C1(C=CC=C1)C)C MQISDUPKURIRCC-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 150000003376 silicon Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229920000576 tactic polymer Polymers 0.000 description 2
- 150000003755 zirconium compounds Chemical class 0.000 description 2
- TZZOMQMRUILQEH-UHFFFAOYSA-N (1-methylcyclopenta-2,4-dien-1-yl)silane Chemical compound CC1([SiH3])C=CC=C1 TZZOMQMRUILQEH-UHFFFAOYSA-N 0.000 description 1
- CDCWUNWTCULXLK-UHFFFAOYSA-N (1-tert-butylcyclopenta-2,4-dien-1-yl)-cyclopenta-2,4-dien-1-yl-dimethylsilane Chemical compound C[Si](C1(C=CC=C1)C(C)(C)C)(C1C=CC=C1)C CDCWUNWTCULXLK-UHFFFAOYSA-N 0.000 description 1
- UBIJLMVQVUIGAW-UHFFFAOYSA-N (1-tert-butylcyclopenta-2,4-dien-1-yl)-dimethyl-(1-methylcyclopenta-2,4-dien-1-yl)silane Chemical compound C[Si](C1(C=CC=C1)C(C)(C)C)(C1(C=CC=C1)C)C UBIJLMVQVUIGAW-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CSPRGONDJQVAEM-UHFFFAOYSA-L CC(C)(C)C1(C=CC=C1)[Zr](Cl)Cl Chemical compound CC(C)(C)C1(C=CC=C1)[Zr](Cl)Cl CSPRGONDJQVAEM-UHFFFAOYSA-L 0.000 description 1
- MCFXTPMUTCQFOV-UHFFFAOYSA-K CC1(C=CC=C1)[Zr](Cl)(Cl)Cl Chemical compound CC1(C=CC=C1)[Zr](Cl)(Cl)Cl MCFXTPMUTCQFOV-UHFFFAOYSA-K 0.000 description 1
- CGULVHSDGKXYNG-UHFFFAOYSA-M C[SiH](C)[Zr](Cl)(C1C=CC=C1)C1C=CC=C1 Chemical compound C[SiH](C)[Zr](Cl)(C1C=CC=C1)C1C=CC=C1 CGULVHSDGKXYNG-UHFFFAOYSA-M 0.000 description 1
- LRNMBBIXYQKUEP-UHFFFAOYSA-L C[SiH]C.CC1=CC(C=C1)[Ti](Cl)(Cl)C1C=CC(C)=C1 Chemical compound C[SiH]C.CC1=CC(C=C1)[Ti](Cl)(Cl)C1C=CC(C)=C1 LRNMBBIXYQKUEP-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- JLVVTRBFNOFBGM-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)[Hf+2]C1(C=CC=C1)C Chemical compound [Cl-].[Cl-].C1(C=CC=C1)[Hf+2]C1(C=CC=C1)C JLVVTRBFNOFBGM-UHFFFAOYSA-L 0.000 description 1
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- IWAJAKKGPHCYIN-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1(C=CC=C1)C Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1(C=CC=C1)C IWAJAKKGPHCYIN-UHFFFAOYSA-L 0.000 description 1
- UGDRGJGYMBHHEY-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1(C=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1(C=CC=C1)C1=CC=CC=C1 UGDRGJGYMBHHEY-UHFFFAOYSA-L 0.000 description 1
- QRJKTMDNVYJPSM-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)C1=CC=CC=C1)C1C=CC=C1 QRJKTMDNVYJPSM-UHFFFAOYSA-L 0.000 description 1
- XFQZNVWMUORYNL-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)CC)C1(C=CC=C1)CC Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C=CC=C1)CC)C1(C=CC=C1)CC XFQZNVWMUORYNL-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- WCQBWUGBAFMQMH-UHFFFAOYSA-N dimethyl-bis(1-methylcyclopenta-2,4-dien-1-yl)germane Chemical compound C[Ge](C1(C=CC=C1)C)(C1(C=CC=C1)C)C WCQBWUGBAFMQMH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 229920001580 isotactic polymer Polymers 0.000 description 1
- 239000011980 kaminsky catalyst Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 229940078552 o-xylene Drugs 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- OWWGDUYHXDZPKI-UHFFFAOYSA-N zirconium dihydrochloride Chemical compound Cl.Cl.[Zr] OWWGDUYHXDZPKI-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
-
- 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
- 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
- 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
-
- 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
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62282538A JP2587251B2 (ja) | 1987-11-09 | 1987-11-09 | 立体規則性オレフィン重合体製造用触媒 |
JP63151666A JPH0720973B2 (ja) | 1988-06-20 | 1988-06-20 | 橋架け構造のビス置換シクロペンタジエニル配位子を有するハフニウム化合物 |
JP63151665A JPH0713075B2 (ja) | 1988-06-20 | 1988-06-20 | 橋架け構造のビス置換シクロペンタジエニル配位子を有するジルコニウム化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CS728188A3 CS728188A3 (en) | 1992-08-12 |
CS277432B6 true CS277432B6 (en) | 1993-03-17 |
Family
ID=27320148
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS887281A CS277432B6 (en) | 1987-11-09 | 1988-11-04 | Catalyst for the production of stereo-regular olefin polymer |
Country Status (9)
Country | Link |
---|---|
US (1) | US4931417A (de) |
EP (1) | EP0316155B1 (de) |
KR (1) | KR0137477B1 (de) |
AT (1) | ATE133966T1 (de) |
AU (1) | AU603268B2 (de) |
CA (1) | CA1326676C (de) |
CS (1) | CS277432B6 (de) |
DE (1) | DE3854987T2 (de) |
LV (1) | LV10213B (de) |
Families Citing this family (113)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3640948A1 (de) * | 1986-11-29 | 1988-06-01 | Hoechst Ag | Verfahren zur herstellung eines 1-olefin-stereoblockpolymers |
DE3640924A1 (de) * | 1986-11-29 | 1988-06-01 | Hoechst Ag | 1-olefin-stereoblockpolymer und verfahren zu seiner herstellung |
US5055438A (en) * | 1989-09-13 | 1991-10-08 | Exxon Chemical Patents, Inc. | Olefin polymerization catalysts |
DE3726067A1 (de) | 1987-08-06 | 1989-02-16 | Hoechst Ag | Verfahren zur herstellung von 1-olefinpolymeren |
US5120867A (en) * | 1988-03-21 | 1992-06-09 | Welborn Jr Howard C | Silicon-bridged transition metal compounds |
IL89525A0 (en) * | 1988-03-21 | 1989-09-10 | Exxon Chemical Patents Inc | Silicon-bridged transition metal compounds |
US5017714A (en) * | 1988-03-21 | 1991-05-21 | Exxon Chemical Patents Inc. | Silicon-bridged transition metal compounds |
US4892851A (en) * | 1988-07-15 | 1990-01-09 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
US5225500A (en) * | 1988-07-15 | 1993-07-06 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
DE3826075A1 (de) | 1988-07-30 | 1990-02-01 | Hoechst Ag | 1-olefin-isoblockpolymer und verfahren zu seiner herstellung |
IT1237398B (it) * | 1989-01-31 | 1993-06-01 | Ausimont Srl | Catalizzatori per la polimerizzazione di olefine. |
DE3916553A1 (de) | 1989-05-20 | 1990-11-22 | Hoechst Ag | Syndio- isoblockpolymer und verfahren zu seiner herstellung |
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-
1988
- 1988-11-02 US US07/266,065 patent/US4931417A/en not_active Expired - Lifetime
- 1988-11-04 CS CS887281A patent/CS277432B6/cs not_active IP Right Cessation
- 1988-11-04 AU AU24765/88A patent/AU603268B2/en not_active Ceased
- 1988-11-08 CA CA000582530A patent/CA1326676C/en not_active Expired - Fee Related
- 1988-11-08 KR KR1019880014639A patent/KR0137477B1/ko not_active IP Right Cessation
- 1988-11-09 DE DE3854987T patent/DE3854987T2/de not_active Expired - Fee Related
- 1988-11-09 EP EP88310549A patent/EP0316155B1/de not_active Expired - Lifetime
- 1988-11-09 AT AT88310549T patent/ATE133966T1/de not_active IP Right Cessation
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1992
- 1992-11-25 LV LVP-92-216A patent/LV10213B/lv unknown
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CS728188A3 (en) | 1992-08-12 |
AU603268B2 (en) | 1990-11-08 |
LV10213A (lv) | 1994-10-20 |
ATE133966T1 (de) | 1996-02-15 |
US4931417A (en) | 1990-06-05 |
EP0316155A2 (de) | 1989-05-17 |
DE3854987T2 (de) | 1996-09-12 |
AU2476588A (en) | 1989-05-11 |
LV10213B (en) | 1995-08-20 |
DE3854987D1 (de) | 1996-03-21 |
KR0137477B1 (ko) | 1998-05-01 |
EP0316155B1 (de) | 1996-02-07 |
CA1326676C (en) | 1994-02-01 |
KR890008153A (ko) | 1989-07-10 |
EP0316155A3 (de) | 1991-07-24 |
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