JP4169791B2 - オレフィン重合用メタロセンと触媒 - Google Patents
オレフィン重合用メタロセンと触媒 Download PDFInfo
- Publication number
- JP4169791B2 JP4169791B2 JP54117498A JP54117498A JP4169791B2 JP 4169791 B2 JP4169791 B2 JP 4169791B2 JP 54117498 A JP54117498 A JP 54117498A JP 54117498 A JP54117498 A JP 54117498A JP 4169791 B2 JP4169791 B2 JP 4169791B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- methylene
- indenyl
- group
- zirconium dichloride
- 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.)
- Expired - Fee Related
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 49
- 239000003054 catalyst Substances 0.000 title claims description 32
- 150000001336 alkenes Chemical class 0.000 title claims description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 80
- -1 2-methylindenyl Chemical group 0.000 claims description 35
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 25
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 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 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 230000004913 activation Effects 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 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 claims description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 7
- 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 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 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 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 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
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 150000001255 actinides 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 description 73
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 59
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 36
- 239000000203 mixture Substances 0.000 description 35
- 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 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 16
- 229910007928 ZrCl2 Inorganic materials 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 239000002002 slurry Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229910007926 ZrCl Inorganic materials 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000012047 saturated solution Substances 0.000 description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 6
- 125000006736 (C6-C20) aryl group Chemical group 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 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 5
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-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
- 239000004711 α-olefin Substances 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
- 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 3
- 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 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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000002244 precipitate 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- 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 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- RYWACDQLALHZQN-UHFFFAOYSA-L [Cl-].[Cl-].C1=C([Si](C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C([Si](C)(C)C)C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].C1=C([Si](C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C([Si](C)(C)C)C2=CC=CC=C21 RYWACDQLALHZQN-UHFFFAOYSA-L 0.000 description 2
- AOQACYNQTVGJFR-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C([Si](C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C([Si](C)(C)C)=C1C Chemical compound [Cl-].[Cl-].CC1=C([Si](C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C2=CC=CC=C2C([Si](C)(C)C)=C1C AOQACYNQTVGJFR-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
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011449 brick Substances 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
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 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
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere 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
- 239000012071 phase Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
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- 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
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 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
- 239000010936 titanium Substances 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- RKPWAHQNLQXPPH-UHFFFAOYSA-N tris(6-methylheptyl)alumane Chemical compound CC(C)CCCCC[Al](CCCCCC(C)C)CCCCCC(C)C RKPWAHQNLQXPPH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
-
- 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
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
- C07C2/34—Metal-hydrocarbon complexes
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—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+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97200933 | 1997-03-29 | ||
| EP97200933.6 | 1997-05-29 | ||
| EP97201986.3 | 1997-06-30 | ||
| EP97201986 | 1997-06-30 | ||
| PCT/EP1998/001931 WO1998043989A1 (en) | 1997-03-29 | 1998-03-27 | Metallocenes and catalysts for polymerization of olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2000512310A JP2000512310A (ja) | 2000-09-19 |
| JP2000512310A5 JP2000512310A5 (enExample) | 2005-11-10 |
| JP4169791B2 true JP4169791B2 (ja) | 2008-10-22 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54117498A Expired - Fee Related JP4169791B2 (ja) | 1997-03-29 | 1998-03-27 | オレフィン重合用メタロセンと触媒 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6268518B1 (enExample) |
| EP (1) | EP0914323B1 (enExample) |
| JP (1) | JP4169791B2 (enExample) |
| CN (1) | CN1226894A (enExample) |
| AU (1) | AU7758198A (enExample) |
| BR (1) | BR9804807A (enExample) |
| CA (1) | CA2257177A1 (enExample) |
| CZ (1) | CZ434598A3 (enExample) |
| DE (1) | DE69816936T2 (enExample) |
| ES (1) | ES2203965T3 (enExample) |
| HU (1) | HUP0003603A3 (enExample) |
| ID (1) | ID20561A (enExample) |
| IL (1) | IL127229A0 (enExample) |
| NO (1) | NO985579L (enExample) |
| PL (1) | PL330222A1 (enExample) |
| WO (1) | WO1998043989A1 (enExample) |
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 |
| DE19882607B4 (de) * | 1997-08-12 | 2009-04-02 | Chisso Corp. | Polypropylen, Verfahren zur Herstellung desselben und Anwendungen davon |
| WO1999036427A1 (en) | 1998-01-14 | 1999-07-22 | Montell Technology Company B.V. | Process for the preparation of metallocene compounds |
| JP2002505713A (ja) | 1998-04-21 | 2002-02-19 | モンテル テクノロジー カンパニー ビーブイ | α−オレフィンとのエチレンコポリマーの製造方法 |
| ATE257490T1 (de) * | 1998-04-27 | 2004-01-15 | Repsol Quimica Sa | Katalysatorsysteme für die polymerisation und copolymerisation von alpha-olefinen |
| ATE264344T1 (de) * | 1998-04-29 | 2004-04-15 | Repsol Quimica Sa | Verfahren und verwendung von heterogenen katalysatorbestandteilen für die olefinpolymerisation |
| HUP0101144A2 (hu) * | 1998-11-20 | 2001-07-30 | Montell Technology Company B.V. | Hidas szerkezetű metallocének, előállításuk és alkalmazásuk katalitikus rendszerekben |
| DE19922020A1 (de) * | 1999-05-12 | 2000-11-16 | Targor Gmbh | Übergangsmetallverbindung, Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
| DE60003936T2 (de) | 1999-09-22 | 2004-05-13 | Basell Polyolefine Gmbh | Katalysatorsystem unf verfahren zur polymerisierung von olefine |
| RU2243229C2 (ru) * | 1999-12-28 | 2004-12-27 | Базелль Текнолоджи Компани Б.В. | Металлоценовое соединение, лиганд, способы получения лиганда, катализатор, способ получения полимера альфа-олефинов, гомополимер пропилена, сополимер пропилена |
| DE60108062T2 (de) | 2000-05-24 | 2005-06-02 | Basell Polyolefine Gmbh | Propylenpolymere und verfahren zur ihrer herstellung |
| WO2003057705A1 (en) * | 2002-01-08 | 2003-07-17 | Basell Polyolefine Gmbh | Preparation of silicon-bridged metallocene compounds |
| 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 |
| US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
| US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
| US8283428B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymacromonomer and process for production thereof |
| US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
| US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
| 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 |
| US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
| US8426659B2 (en) | 2011-03-25 | 2013-04-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8669326B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Amine functionalized polyolefin and methods for preparation thereof |
| 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 |
| 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 |
| US8501894B2 (en) | 2011-03-25 | 2013-08-06 | Exxonmobil Chemical Patents Inc. | Hydrosilyation of vinyl macromers with metallocenes |
| WO2012134719A2 (en) * | 2011-03-25 | 2012-10-04 | Exxonmobil Chemical Patents Inc. | Novel catalysts and methods of use thereof to produce vinyl terminated polymers |
| US8785562B2 (en) | 2011-03-25 | 2014-07-22 | Exxonmobil Chemical Patents Inc. | Amphiphilic block polymers prepared by alkene metathesis |
| US8455597B2 (en) | 2011-03-25 | 2013-06-04 | Exxonmobil Chemical Patents Inc. | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| US8669330B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Olefin triblock polymers via ring-opening metathesis polymerization |
| 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 |
| EP3245258B1 (en) | 2015-01-06 | 2019-09-11 | Scg Chemicals Co. Ltd. | Sio2-layered double hydroxide microspheres and methods of making them |
| WO2016110699A2 (en) | 2015-01-06 | 2016-07-14 | Scg Chemicals Co., Ltd. | Sio2-layered double hydroxide microspheres and their use as catalyst supports in ethylene polymerisation |
| GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
| WO2018172212A1 (en) * | 2017-03-20 | 2018-09-27 | Lanxess Organometallics Gmbh | Process for producing isopropylidene bis(cyclopentadienyl)zirconium dichloride |
| CA3069266C (en) * | 2017-08-02 | 2023-06-20 | Total Research & Technology Feluy | Dual catalyst composition |
| CN115485311B (zh) | 2020-02-24 | 2024-12-06 | 埃克森美孚化学专利公司 | 用于生产乙烯叉基封端的聚α-烯烃的柄型-双(茚-2-基)催化剂 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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
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- 1998-03-27 CA CA002257177A patent/CA2257177A1/en not_active Abandoned
- 1998-03-27 CZ CZ984345A patent/CZ434598A3/cs unknown
- 1998-03-27 AU AU77581/98A patent/AU7758198A/en not_active Abandoned
- 1998-03-27 DE DE69816936T patent/DE69816936T2/de not_active Expired - Fee Related
- 1998-03-27 ID IDW980142D patent/ID20561A/id unknown
- 1998-03-27 WO PCT/EP1998/001931 patent/WO1998043989A1/en not_active Ceased
- 1998-03-27 BR BR9804807A patent/BR9804807A/pt not_active IP Right Cessation
- 1998-03-27 CN CN98800685A patent/CN1226894A/zh active Pending
- 1998-03-27 HU HU0003603A patent/HUP0003603A3/hu unknown
- 1998-03-27 EP EP98925462A patent/EP0914323B1/en not_active Expired - Lifetime
- 1998-03-27 IL IL12722998A patent/IL127229A0/xx unknown
- 1998-03-27 PL PL98330222A patent/PL330222A1/xx unknown
- 1998-03-27 ES ES98925462T patent/ES2203965T3/es not_active Expired - Lifetime
- 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 |
|---|---|
| HUP0003603A2 (hu) | 2001-02-28 |
| NO985579D0 (no) | 1998-11-27 |
| CZ434598A3 (cs) | 1999-08-11 |
| HUP0003603A3 (en) | 2002-03-28 |
| CN1226894A (zh) | 1999-08-25 |
| ID20561A (id) | 1999-01-14 |
| DE69816936D1 (de) | 2003-09-11 |
| WO1998043989A1 (en) | 1998-10-08 |
| BR9804807A (pt) | 1999-08-17 |
| US6268518B1 (en) | 2001-07-31 |
| DE69816936T2 (de) | 2004-05-19 |
| JP2000512310A (ja) | 2000-09-19 |
| AU7758198A (en) | 1998-10-22 |
| CA2257177A1 (en) | 1998-10-08 |
| EP0914323A1 (en) | 1999-05-12 |
| ES2203965T3 (es) | 2004-04-16 |
| PL330222A1 (en) | 1999-05-10 |
| IL127229A0 (en) | 1999-09-22 |
| NO985579L (no) | 1999-01-28 |
| EP0914323B1 (en) | 2003-08-06 |
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