AU7758198A - Metallocenes and catalysts for polymerization of olefins - Google Patents
Metallocenes and catalysts for polymerization of olefinsInfo
- Publication number
- AU7758198A AU7758198A AU77581/98A AU7758198A AU7758198A AU 7758198 A AU7758198 A AU 7758198A AU 77581/98 A AU77581/98 A AU 77581/98A AU 7758198 A AU7758198 A AU 7758198A AU 7758198 A AU7758198 A AU 7758198A
- Authority
- AU
- Australia
- Prior art keywords
- indenyl
- bis
- bridged metallocene
- metallocene compound
- formula
- 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.)
- Abandoned
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 53
- 239000003054 catalyst Substances 0.000 title claims description 33
- 150000001336 alkenes Chemical class 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- -1 trimethylgermyl Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000003213 activating effect Effects 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- IPBTZXODRJJQBJ-UHFFFAOYSA-N 3-tert-butyl-1-[(3-tert-butyl-1h-inden-1-yl)methyl]-1h-indene Chemical compound C12=CC=CC=C2C(C(C)(C)C)=CC1CC1C2=CC=CC=C2C(C(C)(C)C)=C1 IPBTZXODRJJQBJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- KNRYBQYJVYZOQB-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC(C(=CC=C2C)C)=C2C1[Zr+2](=C)C1C(C(C)=CC=C2C)=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC(C(=CC=C2C)C)=C2C1[Zr+2](=C)C1C(C(C)=CC=C2C)=C2C=C1 KNRYBQYJVYZOQB-UHFFFAOYSA-L 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000001255 actinides Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000003606 oligomerizing effect Effects 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 35
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 238000003756 stirring Methods 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000000725 suspension Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- 229910007928 ZrCl2 Inorganic materials 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910007926 ZrCl Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 8
- 239000012266 salt solution Substances 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 7
- 229910007932 ZrCl4 Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- OWVPYASHRHSCCZ-UHFFFAOYSA-N 1-tert-butyl-3-[(3-tert-butyl-3h-inden-1-yl)methyl]-1h-indene Chemical compound C12=CC=CC=C2C(C(C)(C)C)C=C1CC1=CC(C(C)(C)C)C2=CC=CC=C12 OWVPYASHRHSCCZ-UHFFFAOYSA-N 0.000 description 6
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 5
- NSRZYYSOHCRQHF-UHFFFAOYSA-N 1-(1h-inden-1-ylmethyl)-1h-indene Chemical compound C1=CC2=CC=CC=C2C1CC1C2=CC=CC=C2C=C1 NSRZYYSOHCRQHF-UHFFFAOYSA-N 0.000 description 4
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 4
- UWTTZMZSVRJQKB-UHFFFAOYSA-N 1-[(4,7-dimethyl-1h-inden-1-yl)methyl]-4,7-dimethyl-1h-indene Chemical compound C1=CC(C(=CC=C2C)C)=C2C1CC1C(C(C)=CC=C2C)=C2C=C1 UWTTZMZSVRJQKB-UHFFFAOYSA-N 0.000 description 3
- IHHBPJRQKRVWAY-UHFFFAOYSA-N 1-tert-butyl-1h-indene Chemical compound C1=CC=C2C(C(C)(C)C)C=CC2=C1 IHHBPJRQKRVWAY-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- PZGQHYRHSBWJIB-UHFFFAOYSA-N 2-methyl-1-[(2-methyl-1h-inden-1-yl)methyl]-1h-indene Chemical compound CC1=CC2=CC=CC=C2C1CC1C2=CC=CC=C2C=C1C PZGQHYRHSBWJIB-UHFFFAOYSA-N 0.000 description 3
- TWCMJDBVDHQWAG-UHFFFAOYSA-N 4,6-dimethyl-3-phenyl-1h-indene Chemical compound C1=2C(C)=CC(C)=CC=2CC=C1C1=CC=CC=C1 TWCMJDBVDHQWAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- MWROANXKQLDDCZ-UHFFFAOYSA-L [Cl-].[Cl-].C1=C(C(C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C(C(C)(C)C)C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].C1=C(C(C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C(C(C)(C)C)C2=CC=CC=C21 MWROANXKQLDDCZ-UHFFFAOYSA-L 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- INLAOWRXBOUVSB-UHFFFAOYSA-N trimethyl-[3-[(3-trimethylsilyl-3h-inden-1-yl)methyl]-1h-inden-1-yl]silane Chemical compound C12=CC=CC=C2C([Si](C)(C)C)C=C1CC1=CC([Si](C)(C)C)C2=CC=CC=C12 INLAOWRXBOUVSB-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VFFBKGZIWQZXIP-UHFFFAOYSA-N 2-[(5,7-dimethyl-1-phenyl-1h-inden-2-yl)methyl]-5,7-dimethyl-1-phenyl-1h-indene Chemical compound C=1C=CC=CC=1C1C=2C(C)=CC(C)=CC=2C=C1CC1=CC2=CC(C)=CC(C)=C2C1C1=CC=CC=C1 VFFBKGZIWQZXIP-UHFFFAOYSA-N 0.000 description 2
- QKTNNHZEFGFOQG-UHFFFAOYSA-N 3-tert-butyl-1h-indene Chemical compound C1=CC=C2C(C(C)(C)C)=CCC2=C1 QKTNNHZEFGFOQG-UHFFFAOYSA-N 0.000 description 2
- NXOHUHPRFMGJSZ-UHFFFAOYSA-N 5,7-dimethyl-2,3-dihydroinden-1-one Chemical compound CC1=CC(C)=CC2=C1C(=O)CC2 NXOHUHPRFMGJSZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- POHDBLASMHADAW-UHFFFAOYSA-L [Cl-].[Cl-].C1=2C(C)=CC(C)=CC=2C([Zr+2](=C)C2C3=C(C(=CC(C)=C3)C)C(=C2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1=2C(C)=CC(C)=CC=2C([Zr+2](=C)C2C3=C(C(=CC(C)=C3)C)C(=C2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 POHDBLASMHADAW-UHFFFAOYSA-L 0.000 description 2
- ZUGAYUSVYHLKDE-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C=C1 ZUGAYUSVYHLKDE-UHFFFAOYSA-L 0.000 description 2
- MOMFNNODEDMKRW-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C=C1C Chemical compound [Cl-].[Cl-].CC1=CC2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C=C1C MOMFNNODEDMKRW-UHFFFAOYSA-L 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
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- KILPPHWPVWEKTE-UHFFFAOYSA-N bis(2-methylpropyl)-(2-phenylpropyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)C1=CC=CC=C1 KILPPHWPVWEKTE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 238000012512 characterization method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- ISEJRLXHKSHKPM-UHFFFAOYSA-N dimethyl(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)C ISEJRLXHKSHKPM-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
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- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
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- 239000011888 foil Substances 0.000 description 1
- 125000003250 fulvenyl group Chemical class C1(=CC=CC1=C)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- SPRIOUNJHPCKPV-UHFFFAOYSA-N hydridoaluminium Chemical compound [AlH] SPRIOUNJHPCKPV-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- NIXOIRLDFIPNLJ-UHFFFAOYSA-M magnesium;benzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=[C-]C=C1 NIXOIRLDFIPNLJ-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NCYHQDWNMCYQHR-UHFFFAOYSA-N methyl-bis(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)CC(C)C NCYHQDWNMCYQHR-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CFCIWEFTNUMUJY-UHFFFAOYSA-N tris(2-methylphenyl)alumane Chemical compound CC1=CC=CC=C1[Al](C=1C(=CC=CC=1)C)C1=CC=CC=C1C CFCIWEFTNUMUJY-UHFFFAOYSA-N 0.000 description 1
- MLDSMTVYPPIXMZ-UHFFFAOYSA-N tris(4-methylpentyl)alumane Chemical compound CC(C)CCC[Al](CCCC(C)C)CCCC(C)C MLDSMTVYPPIXMZ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/867—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an aldehyde or a ketone
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
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- 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
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
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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
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97200933 | 1997-03-29 | ||
| EP97201986 | 1997-06-30 | ||
| PCT/EP1998/001931 WO1998043989A1 (en) | 1997-03-29 | 1998-03-27 | Metallocenes and catalysts for polymerization of olefins |
Publications (1)
| Publication Number | Publication Date |
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| AU7758198A true AU7758198A (en) | 1998-10-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU77581/98A Abandoned AU7758198A (en) | 1997-03-29 | 1998-03-27 | Metallocenes and catalysts for polymerization of olefins |
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| US (1) | US6268518B1 (https=) |
| EP (1) | EP0914323B1 (https=) |
| JP (1) | JP4169791B2 (https=) |
| CN (1) | CN1226894A (https=) |
| AU (1) | AU7758198A (https=) |
| BR (1) | BR9804807A (https=) |
| CA (1) | CA2257177A1 (https=) |
| CZ (1) | CZ434598A3 (https=) |
| DE (1) | DE69816936T2 (https=) |
| ES (1) | ES2203965T3 (https=) |
| HU (1) | HUP0003603A3 (https=) |
| ID (1) | ID20561A (https=) |
| IL (1) | IL127229A0 (https=) |
| NO (1) | NO985579L (https=) |
| PL (1) | PL330222A1 (https=) |
| WO (1) | WO1998043989A1 (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19637669A1 (de) * | 1996-09-16 | 1998-03-19 | Hoechst Ag | Verfahren zur Herstellung einer methylenverbrückten Biscyclopentadienylverbindung |
| DE69703728T2 (de) * | 1996-10-31 | 2001-06-28 | Repsol Quimica S.A., Madrid | Katalysatorsysteme für die Polymerisation und Copolymerisation von Alpha-Olefinen |
| TW434267B (en) * | 1997-08-12 | 2001-05-16 | Chisso Corp | A process for producing olefin polymers as well as olefin polymers and applications thereof |
| DE69903388T2 (de) | 1998-01-14 | 2003-06-18 | Basell Polyolefine Gmbh | Verfahren zur herstellung von metallocenen |
| CN1272852A (zh) | 1998-04-21 | 2000-11-08 | 蒙特尔技术有限公司 | 乙烯与α－烯烃共聚物的制备方法 |
| PT953581E (pt) * | 1998-04-27 | 2004-07-30 | Repsol Quimica Sa | Sistemas cataliticos para a polimerizacao e a copolimerizacao de alfa-olefinas |
| ES2216473T3 (es) * | 1998-04-29 | 2004-10-16 | Repsol Quimica S.A. | Preparacion y uso de componentes de catalizador heterogeneos para polimerizacion de olefinas. |
| KR20010034199A (ko) * | 1998-11-20 | 2001-04-25 | 간디 지오프레이 에이치. | 다리화 메탈로센, 제조, 촉매계 내에서의 용도 |
| DE19922020A1 (de) * | 1999-05-12 | 2000-11-16 | Targor Gmbh | Übergangsmetallverbindung, Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
| BR0014616A (pt) | 1999-09-22 | 2002-06-18 | Basell Technology Co Bv | Sistema catalìtico e processo para a polimerização de olefinas |
| JP4358470B2 (ja) * | 1999-12-28 | 2009-11-04 | バセル テクノロジー カンパニー ビー．ブイ． | メタロセン化合物、リガンド、触媒、ポリマーの製造方法及びプロピレンホモポリマー |
| DE60108062T2 (de) * | 2000-05-24 | 2005-06-02 | Basell Polyolefine Gmbh | Propylenpolymere und verfahren zur ihrer herstellung |
| JP4417719B2 (ja) * | 2002-01-08 | 2010-02-17 | バーゼル・ポリオレフィン・ゲーエムベーハー | シリコン橋状メタロセン化合物の製造 |
| US7176158B2 (en) * | 2002-10-25 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Polymerization catalyst composition |
| US20040102311A1 (en) * | 2002-11-21 | 2004-05-27 | Abbas Razavi | Bridged metallocene catalyst component, method of making, polyolefin catalyst having C1, C2, or Cs symmetry, methods of making, methods of polymerizing, olefins and products made thereof |
| JP5283984B2 (ja) * | 2008-06-18 | 2013-09-04 | 三井化学株式会社 | 遷移金属化合物の製造方法 |
| US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
| US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
| US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
| US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
| US8283428B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymacromonomer and process for production thereof |
| US8435911B2 (en) * | 2008-10-16 | 2013-05-07 | Basell Polyolefine Gmbh | Hybrid catalyst composition for polymerization of olefins |
| GB0918736D0 (en) | 2009-10-26 | 2009-12-09 | Isis Innovation | Catalysts |
| CN102286124B (zh) * | 2010-06-18 | 2013-05-01 | 中国石油化工股份有限公司 | 一种含高烯丙基端基的聚丙烯制备方法 |
| CN102464748B (zh) * | 2010-11-16 | 2013-07-03 | 中国石油化工股份有限公司 | 一种丙烯共聚物大分子单体及其制备方法 |
| US8841397B2 (en) | 2011-03-25 | 2014-09-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8399724B2 (en) | 2011-03-25 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin copolymers and methods to produce thereof |
| US8455597B2 (en) | 2011-03-25 | 2013-06-04 | Exxonmobil Chemical Patents Inc. | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| US8426659B2 (en) | 2011-03-25 | 2013-04-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8501894B2 (en) | 2011-03-25 | 2013-08-06 | Exxonmobil Chemical Patents Inc. | Hydrosilyation of vinyl macromers with metallocenes |
| US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
| US8669326B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Amine functionalized polyolefin and methods for preparation thereof |
| EP2688916A4 (en) * | 2011-03-25 | 2014-10-22 | Exxonmobil Chem Patents Inc | NOVEL CATALYSTS AND METHOD OF USE THEREOF FOR PRODUCING VINYL-DERMED POLYMERS |
| US8940839B2 (en) | 2011-03-25 | 2015-01-27 | Exxonmobil Chemical Patents Inc. | Diblock copolymers prepared by cross metathesis |
| US8623974B2 (en) | 2011-03-25 | 2014-01-07 | Exxonmobil Chemical Patents Inc. | Branched vinyl terminated polymers and methods for production thereof |
| US8669330B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Olefin triblock polymers via ring-opening metathesis polymerization |
| US8785562B2 (en) | 2011-03-25 | 2014-07-22 | Exxonmobil Chemical Patents Inc. | Amphiphilic block polymers prepared by alkene metathesis |
| US8604148B2 (en) | 2011-11-29 | 2013-12-10 | Exxonmobil Chemical Patents Inc. | Functionalization of vinyl terminated polymers by ring opening cross metathesis |
| US8796376B2 (en) | 2012-03-26 | 2014-08-05 | Exxonmobil Chemical Patents Inc. | Functionalized polymers and oligomers |
| JP6326202B2 (ja) * | 2013-05-16 | 2018-05-16 | 三井化学株式会社 | オレフィン重合用固体触媒成分およびそれを用いたオレフィン系重合体の製造方法 |
| GB201407000D0 (en) | 2014-04-17 | 2014-06-04 | Isis Innovation | Catalysts |
| PL3245258T3 (pl) | 2015-01-06 | 2020-01-31 | Scg Chemicals Co., Ltd. | MIKROSFERY SiO₂ Z WARSTWOWYM PODWÓJNYM WODOROTLENKIEM I SPOSOBY ICH OTRZYMYWANIA |
| CN107108799B (zh) | 2015-01-06 | 2020-07-21 | Scg化学有限公司 | SiO2层状双氢氧化物微球及其作为乙烯聚合中的催化剂载体的用途 |
| GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
| US11566037B2 (en) | 2017-03-20 | 2023-01-31 | Lanxess Organometallics Gmbh | Process for producing isopropylidene bis(cyclopentadienyl)zirconium dichloride |
| EP3661982B1 (en) * | 2017-08-02 | 2021-12-01 | Total Research & Technology Feluy | Dual catalyst composition |
| WO2021173361A1 (en) | 2020-02-24 | 2021-09-02 | Exxonmobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929693A1 (de) * | 1989-09-07 | 1991-03-14 | Hoechst Ag | Verfahren zur herstellung eines polyolefinwachses |
| JP3216662B2 (ja) * | 1992-10-08 | 2001-10-09 | 出光興産株式会社 | スチレン系重合体の製造方法 |
| DE4422157A1 (de) * | 1994-06-24 | 1996-01-04 | Hoechst Ag | Verfahren zur Herstellung von Cycloolefincopolymeren |
| IT1272923B (it) * | 1995-01-23 | 1997-07-01 | Spherilene Srl | Composti metallocenici,procedimento per la loro preparazione,e loro utilizzo in catalizzatori per la polimerizzazione delle olefine |
| DE19523595A1 (de) | 1995-06-30 | 1997-01-02 | Hoechst Ag | Verfahren zur Herstellung einer kohlenstoffverbrückten Biscyclopentadienverbindung |
| DE19637669A1 (de) * | 1996-09-16 | 1998-03-19 | Hoechst Ag | Verfahren zur Herstellung einer methylenverbrückten Biscyclopentadienylverbindung |
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- 1998-03-27 ID IDW980142D patent/ID20561A/id unknown
- 1998-03-27 AU AU77581/98A patent/AU7758198A/en not_active Abandoned
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- 1998-03-27 JP JP54117498A patent/JP4169791B2/ja not_active Expired - Fee Related
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- 1998-03-30 US US09/050,607 patent/US6268518B1/en not_active Expired - Fee Related
- 1998-11-27 NO NO985579A patent/NO985579L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
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| EP0914323A1 (en) | 1999-05-12 |
| CA2257177A1 (en) | 1998-10-08 |
| IL127229A0 (en) | 1999-09-22 |
| ES2203965T3 (es) | 2004-04-16 |
| HUP0003603A3 (en) | 2002-03-28 |
| DE69816936T2 (de) | 2004-05-19 |
| HUP0003603A2 (hu) | 2001-02-28 |
| WO1998043989A1 (en) | 1998-10-08 |
| CZ434598A3 (cs) | 1999-08-11 |
| US6268518B1 (en) | 2001-07-31 |
| NO985579D0 (no) | 1998-11-27 |
| EP0914323B1 (en) | 2003-08-06 |
| JP4169791B2 (ja) | 2008-10-22 |
| ID20561A (id) | 1999-01-14 |
| NO985579L (no) | 1999-01-28 |
| PL330222A1 (en) | 1999-05-10 |
| CN1226894A (zh) | 1999-08-25 |
| DE69816936D1 (de) | 2003-09-11 |
| BR9804807A (pt) | 1999-08-17 |
| JP2000512310A (ja) | 2000-09-19 |
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