DE69816936T2 - Metallocene und katalysatoren zur polymerisation von olefinen - Google Patents
Metallocene und katalysatoren zur polymerisation von olefinen Download PDFInfo
- Publication number
- DE69816936T2 DE69816936T2 DE69816936T DE69816936T DE69816936T2 DE 69816936 T2 DE69816936 T2 DE 69816936T2 DE 69816936 T DE69816936 T DE 69816936T DE 69816936 T DE69816936 T DE 69816936T DE 69816936 T2 DE69816936 T2 DE 69816936T2
- Authority
- DE
- Germany
- Prior art keywords
- olefins
- polymerization
- groups
- hydrogen
- alkyl
- 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
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- 238000006116 polymerization reaction Methods 0.000 title claims description 34
- 239000003054 catalyst Substances 0.000 title claims description 31
- 150000001336 alkenes Chemical class 0.000 title claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 46
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 21
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
- 230000003213 activating effect Effects 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 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
- 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
- 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 description 2
- -1 dimethylsilanediyl group Chemical group 0.000 description 29
- 239000000243 solution Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 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
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 5
- 229910007926 ZrCl Inorganic materials 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 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 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 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
- 239000001993 wax Substances 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- 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 3
- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 2
- USVQDQRLYYGLPV-UHFFFAOYSA-N 2-(2,4,4-trimethylpentyl)oxaluminane Chemical compound CC(C)(C)CC(C)C[Al]1CCCCO1 USVQDQRLYYGLPV-UHFFFAOYSA-N 0.000 description 1
- YNLMKGLRHLDEIQ-UHFFFAOYSA-N 2-(2-methylpentyl)oxaluminane Chemical compound CCCC(C)C[Al]1CCCCO1 YNLMKGLRHLDEIQ-UHFFFAOYSA-N 0.000 description 1
- NMXLXQGHBSPIDR-UHFFFAOYSA-N 2-(2-methylpropyl)oxaluminane Chemical compound CC(C)C[Al]1CCCCO1 NMXLXQGHBSPIDR-UHFFFAOYSA-N 0.000 description 1
- VDBSCMJCMSNQQB-UHFFFAOYSA-N 2-methylpropyl-bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C VDBSCMJCMSNQQB-UHFFFAOYSA-N 0.000 description 1
- HEZSFHRGYPJCQY-UHFFFAOYSA-N 2-methylpropyl-bis(2-phenylpropyl)alumane Chemical compound C=1C=CC=CC=1C(C)C[Al](CC(C)C)CC(C)C1=CC=CC=C1 HEZSFHRGYPJCQY-UHFFFAOYSA-N 0.000 description 1
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 1
- DKLQZDIAQKGVTA-UHFFFAOYSA-N 4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC=C2 DKLQZDIAQKGVTA-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KNGQEWZNQLLQPZ-UHFFFAOYSA-L CC(C)=[Hf](Cl)(Cl)(C1C=CC=C1)C1=CC=CC2=C1CC1=CC=CC=C21 Chemical compound CC(C)=[Hf](Cl)(Cl)(C1C=CC=C1)C1=CC=CC2=C1CC1=CC=CC=C21 KNGQEWZNQLLQPZ-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- TVLQXPNNQCAJRL-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC(C(=CC=C2)C(C)C)=C2C1[Zr+2](=C)C1C(C=CC=C2C(C)C)=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC(C(=CC=C2)C(C)C)=C2C1[Zr+2](=C)C1C(C=CC=C2C(C)C)=C2C=C1 TVLQXPNNQCAJRL-UHFFFAOYSA-L 0.000 description 1
- SPQNXAWVYUWPBJ-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2](=C)C1C=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2](=C)C1C=CC2=C1C=CC=C2C1=CC=CC=C1 SPQNXAWVYUWPBJ-UHFFFAOYSA-L 0.000 description 1
- IGSPQDBOJOXEJJ-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Hf+2](=C)C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Hf+2](=C)C1C2=CC=CC=C2C=C1 IGSPQDBOJOXEJJ-UHFFFAOYSA-L 0.000 description 1
- BAROMXHJOWFTJY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C(=CC=C2C)C)=C2C1[Zr+2](=C)C1C(C(C)=CC=C2C)=C2C=C1C Chemical compound [Cl-].[Cl-].CC1=CC(C(=CC=C2C)C)=C2C1[Zr+2](=C)C1C(C(C)=CC=C2C)=C2C=C1C BAROMXHJOWFTJY-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- DSDJNWYBXQXLRZ-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)aluminum Chemical compound CC(C)(C)CC(C)C[Al]CC(C)CC(C)(C)C DSDJNWYBXQXLRZ-UHFFFAOYSA-N 0.000 description 1
- UXPLEHPMOSDYLZ-UHFFFAOYSA-N bis(2-methylpropyl)-(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C UXPLEHPMOSDYLZ-UHFFFAOYSA-N 0.000 description 1
- 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
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 238000007872 degassing Methods 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
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003250 fulvenyl group Chemical class C1(=CC=CC1=C)* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 238000013022 venting Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 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
-
- 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 | 1997-03-29 | ||
| EP97201986 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69816936D1 DE69816936D1 (de) | 2003-09-11 |
| DE69816936T2 true DE69816936T2 (de) | 2004-05-19 |
Family
ID=26146301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69816936T Expired - Fee Related DE69816936T2 (de) | 1997-03-29 | 1998-03-27 | Metallocene und katalysatoren zur polymerisation von olefinen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6268518B1 (OSRAM) |
| EP (1) | EP0914323B1 (OSRAM) |
| JP (1) | JP4169791B2 (OSRAM) |
| CN (1) | CN1226894A (OSRAM) |
| AU (1) | AU7758198A (OSRAM) |
| BR (1) | BR9804807A (OSRAM) |
| CA (1) | CA2257177A1 (OSRAM) |
| CZ (1) | CZ434598A3 (OSRAM) |
| DE (1) | DE69816936T2 (OSRAM) |
| ES (1) | ES2203965T3 (OSRAM) |
| HU (1) | HUP0003603A3 (OSRAM) |
| ID (1) | ID20561A (OSRAM) |
| IL (1) | IL127229A0 (OSRAM) |
| NO (1) | NO985579L (OSRAM) |
| PL (1) | PL330222A1 (OSRAM) |
| WO (1) | WO1998043989A1 (OSRAM) |
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 |
| WO1999007747A1 (en) * | 1997-08-12 | 1999-02-18 | Chisso Corporation | Process for the preparation of olefin (co)polymers, olefin copolymers, and application thereof |
| WO1999036427A1 (en) | 1998-01-14 | 1999-07-22 | Montell Technology Company B.V. | Process for the preparation of metallocene compounds |
| KR20010014072A (ko) | 1998-04-21 | 2001-02-26 | 간디 지오프레이 에이치. | 에틸렌과 알파-올레핀의 공중합체의 제조 방법 |
| DE69914012T2 (de) * | 1998-04-27 | 2004-12-09 | Repsol Quimica S.A. | Katalysatorsysteme für die Polymerisation und Copolymerisation von Alpha-Olefinen |
| DE69916358T2 (de) * | 1998-04-29 | 2005-04-21 | Repsol Quimica Sa | Verfahren und Verwendung von heterogenen Katalysatorbestandteilen für die Olefinpolymerisation |
| ATE300549T1 (de) * | 1998-11-20 | 2005-08-15 | Basell Polyolefine Gmbh | Verbrückte metallocene, herstellung und verwendung als olefinpolymerisationskatalysator |
| DE19922020A1 (de) * | 1999-05-12 | 2000-11-16 | Targor Gmbh | Übergangsmetallverbindung, Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
| JP2003510381A (ja) | 1999-09-22 | 2003-03-18 | バセル テクノロジー カンパニー ビー．ブイ． | オレフィンの重合用触媒系および方法 |
| EP1854804B1 (en) * | 1999-12-28 | 2011-05-04 | Basell Polyolefine GmbH | Heterocyclic metallocene compounds and use thereof in catalyst systems for producing olefin polymers |
| EP1222216B1 (en) * | 2000-05-24 | 2004-12-29 | Basell Polyolefine GmbH | Propylene polymers and process for the preparation thereof |
| 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 |
| US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
| US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
| US8283428B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymacromonomer and process for production thereof |
| US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
| US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
| 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 |
| US8940839B2 (en) | 2011-03-25 | 2015-01-27 | Exxonmobil Chemical Patents Inc. | Diblock copolymers prepared by cross metathesis |
| US8399724B2 (en) | 2011-03-25 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin copolymers and methods to produce thereof |
| US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
| US8841397B2 (en) | 2011-03-25 | 2014-09-23 | 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 |
| US8669330B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Olefin triblock polymers via ring-opening metathesis polymerization |
| US8426659B2 (en) | 2011-03-25 | 2013-04-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8623974B2 (en) | 2011-03-25 | 2014-01-07 | Exxonmobil Chemical Patents Inc. | Branched vinyl terminated polymers and methods for production thereof |
| US8785562B2 (en) | 2011-03-25 | 2014-07-22 | Exxonmobil Chemical Patents Inc. | Amphiphilic block polymers prepared by alkene metathesis |
| US8669326B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Amine functionalized polyolefin and methods for preparation thereof |
| US8455597B2 (en) | 2011-03-25 | 2013-06-04 | Exxonmobil Chemical Patents Inc. | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| EP2688916A4 (en) * | 2011-03-25 | 2014-10-22 | Exxonmobil Chem Patents Inc | NOVEL CATALYSTS AND METHOD OF USE THEREOF FOR PRODUCING VINYL-DERMED POLYMERS |
| 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 |
| KR20170102956A (ko) | 2015-01-06 | 2017-09-12 | 에스씨지 케미컬스 컴퍼니, 리미티드. | SiO2-층상 이중 수산화물 마이크로스피어 및 에틸렌 중합 반응에서의 촉매 지지체로의 이들의 용도 |
| CN107107025A (zh) | 2015-01-06 | 2017-08-29 | Scg化学有限公司 | SiO2层状双氢氧化物微球及它们的制备方法 |
| 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 |
| PL3661983T3 (pl) * | 2017-08-02 | 2022-05-30 | Total Research & Technology Feluy | Kompozycja podwójnego katalizatora |
| 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
- 1998-03-27 ES ES98925462T patent/ES2203965T3/es not_active Expired - Lifetime
- 1998-03-27 WO PCT/EP1998/001931 patent/WO1998043989A1/en not_active Ceased
- 1998-03-27 IL IL12722998A patent/IL127229A0/xx unknown
- 1998-03-27 AU AU77581/98A patent/AU7758198A/en not_active Abandoned
- 1998-03-27 CA CA002257177A patent/CA2257177A1/en not_active Abandoned
- 1998-03-27 CN CN98800685A patent/CN1226894A/zh active Pending
- 1998-03-27 CZ CZ984345A patent/CZ434598A3/cs unknown
- 1998-03-27 EP EP98925462A patent/EP0914323B1/en not_active Expired - Lifetime
- 1998-03-27 BR BR9804807A patent/BR9804807A/pt not_active IP Right Cessation
- 1998-03-27 JP JP54117498A patent/JP4169791B2/ja not_active Expired - Fee Related
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- 1998-03-27 PL PL98330222A patent/PL330222A1/xx unknown
- 1998-03-27 DE DE69816936T patent/DE69816936T2/de not_active Expired - Fee Related
- 1998-03-27 HU HU0003603A patent/HUP0003603A3/hu unknown
- 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
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| CA2257177A1 (en) | 1998-10-08 |
| AU7758198A (en) | 1998-10-22 |
| NO985579L (no) | 1999-01-28 |
| ID20561A (id) | 1999-01-14 |
| EP0914323A1 (en) | 1999-05-12 |
| US6268518B1 (en) | 2001-07-31 |
| CZ434598A3 (cs) | 1999-08-11 |
| WO1998043989A1 (en) | 1998-10-08 |
| PL330222A1 (en) | 1999-05-10 |
| CN1226894A (zh) | 1999-08-25 |
| EP0914323B1 (en) | 2003-08-06 |
| JP4169791B2 (ja) | 2008-10-22 |
| IL127229A0 (en) | 1999-09-22 |
| NO985579D0 (no) | 1998-11-27 |
| HUP0003603A2 (hu) | 2001-02-28 |
| HUP0003603A3 (en) | 2002-03-28 |
| ES2203965T3 (es) | 2004-04-16 |
| BR9804807A (pt) | 1999-08-17 |
| JP2000512310A (ja) | 2000-09-19 |
| DE69816936D1 (de) | 2003-09-11 |
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