CA2277127A1 - Metallocenes and catalysts for olefin-polymerisation - Google Patents
Metallocenes and catalysts for olefin-polymerisation Download PDFInfo
- Publication number
- CA2277127A1 CA2277127A1 CA002277127A CA2277127A CA2277127A1 CA 2277127 A1 CA2277127 A1 CA 2277127A1 CA 002277127 A CA002277127 A CA 002277127A CA 2277127 A CA2277127 A CA 2277127A CA 2277127 A1 CA2277127 A1 CA 2277127A1
- Authority
- CA
- Canada
- Prior art keywords
- dihydroindeno
- methyl
- indol
- group
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 42
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 73
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 5
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 4
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- -1 C3-C20 cycloalkyl Chemical group 0.000 claims description 66
- 239000003446 ligand Substances 0.000 claims description 46
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000005977 Ethylene Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 27
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 230000000737 periodic effect Effects 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- GQVCNPBYKZHECH-UHFFFAOYSA-N 5-methyl-6h-indeno[2,1-b]indole Chemical compound C12=CC=CC=C2N(C)C2=C1C1=CC=CC=C1C2 GQVCNPBYKZHECH-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000004291 polyenes Chemical class 0.000 claims description 7
- VGBJEBOQWVWQKI-UHFFFAOYSA-N 5-methyl-6-[(5-methyl-6h-indeno[2,3-b]indol-6-yl)methyl]-6h-indeno[2,1-b]indole Chemical compound C12=CC=CC=C2N(C)C2=C1C1=CC=CC=C1C2CC1C(N(C)C=2C3=CC=CC=2)=C3C2=CC=CC=C21 VGBJEBOQWVWQKI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000013256 coordination polymer Substances 0.000 claims description 5
- 229920001198 elastomeric copolymer Polymers 0.000 claims description 5
- 229920000092 linear low density polyethylene Polymers 0.000 claims description 5
- 239000004707 linear low-density polyethylene Substances 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- ZVICTXXWUAGBDB-UHFFFAOYSA-L [Cl-].[Cl-].CN1C2=CC=CC=C2C(C2=CC=CC=C22)=C1C2[Zr+2](=C)C1C(N(C2=CC=CC=C22)C)=C2C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].CN1C2=CC=CC=C2C(C2=CC=CC=C22)=C1C2[Zr+2](=C)C1C(N(C2=CC=CC=C22)C)=C2C2=CC=CC=C21 ZVICTXXWUAGBDB-UHFFFAOYSA-L 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- BLASBYANUGPACC-UHFFFAOYSA-N 5-phenyl-6h-indeno[2,1-b]indole Chemical compound C1C2=CC=CC=C2C(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 BLASBYANUGPACC-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 150000001255 actinides Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 11
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 11
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 claims 1
- 101100173447 Caenorhabditis elegans ger-1 gene Proteins 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 155
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
- 239000000203 mixture Substances 0.000 description 93
- 239000000243 solution Substances 0.000 description 75
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 230000015572 biosynthetic process Effects 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 39
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 37
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- 229960004132 diethyl ether Drugs 0.000 description 19
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 19
- 229910007932 ZrCl4 Inorganic materials 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 13
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
- YWOQUYASJOJVPR-UHFFFAOYSA-N 5-methyl-10h-indeno[1,2-b]indole Chemical compound C12=CC=CC=C2N(C)C2=C1CC1=CC=CC=C12 YWOQUYASJOJVPR-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 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
- GPPQBEUFCHAZTC-UHFFFAOYSA-N 5-phenyl-10h-indeno[1,2-b]indole Chemical compound C1C2=CC=CC=C2C2=C1C1=CC=CC=C1N2C1=CC=CC=C1 GPPQBEUFCHAZTC-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- 159000000002 lithium salts Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- ZOBGGGYCJDDKAC-UHFFFAOYSA-N CC(C)(C1C=CC=C1)C1C2=CC=CC=C2C=2N(C=3C=CC=CC=3C=21)C Chemical compound CC(C)(C1C=CC=C1)C1C2=CC=CC=C2C=2N(C=3C=CC=CC=3C=21)C ZOBGGGYCJDDKAC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- MRFDRWRTOBBLAU-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C2=C1N(C1=CC=CC=C21)C1=CC=CC=C1)C1C2=CC=CC=C2C2=C1N(C1=CC=CC=C21)C1=CC=CC=C1)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C2=C1N(C1=CC=CC=C21)C1=CC=CC=C1)C1C2=CC=CC=C2C2=C1N(C1=CC=CC=C21)C1=CC=CC=C1)C MRFDRWRTOBBLAU-UHFFFAOYSA-L 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical compound C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- OMRVQIJEIBASRI-UHFFFAOYSA-N 10-(2-cyclopenta-2,4-dien-1-ylpropan-2-yl)-5-phenyl-10H-indeno[1,2-b]indole Chemical compound CC(C)(C1C=CC=C1)C1C2=CC=CC=C2C=2N(C=3C=CC=CC=3C=21)C1=CC=CC=C1 OMRVQIJEIBASRI-UHFFFAOYSA-N 0.000 description 2
- KECBIZLZIASYFE-UHFFFAOYSA-N 2,3-dimethyl-4h-indeno[2,1-b]pyrrole Chemical compound C1=CC=C2C(C=C(N3C)C)=C3CC2=C1 KECBIZLZIASYFE-UHFFFAOYSA-N 0.000 description 2
- DKRFOVJORIFNRQ-UHFFFAOYSA-N 2,5-dimethyl-6h-indeno[2,1-b]indole Chemical compound C1C2=CC=CC=C2C2=C1N(C)C1=CC=C(C)C=C12 DKRFOVJORIFNRQ-UHFFFAOYSA-N 0.000 description 2
- RQAALZRRGFDNLL-UHFFFAOYSA-N 2-methyl-5,6-dihydroindeno[2,1-b]indole Chemical compound C1C2=CC=CC=C2C2=C1NC1=CC=C(C)C=C12 RQAALZRRGFDNLL-UHFFFAOYSA-N 0.000 description 2
- SLQMKNPIYMOEGB-UHFFFAOYSA-N 2-methylhexa-1,5-diene Chemical compound CC(=C)CCC=C SLQMKNPIYMOEGB-UHFFFAOYSA-N 0.000 description 2
- XAAOBNZRGNETLM-UHFFFAOYSA-N 2-tert-butyl-5,6-dihydroindeno[2,1-b]indole Chemical compound C1C2=CC=CC=C2C2=C1NC1=CC=C(C(C)(C)C)C=C12 XAAOBNZRGNETLM-UHFFFAOYSA-N 0.000 description 2
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 description 2
- BMGLVVNENOOPFC-UHFFFAOYSA-N 5,10-dihydroindeno[1,2-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C1=CC=CC=C1C2 BMGLVVNENOOPFC-UHFFFAOYSA-N 0.000 description 2
- JDTRVJYDVHSJKB-UHFFFAOYSA-N 5,6-dihydroindeno[2,1-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CC1=CC=CC=C12 JDTRVJYDVHSJKB-UHFFFAOYSA-N 0.000 description 2
- WXACXMWYHXOSIX-UHFFFAOYSA-N 5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC=C1 WXACXMWYHXOSIX-UHFFFAOYSA-N 0.000 description 2
- BTJYGWDQLGTPOV-UHFFFAOYSA-N 6-[(2,5-dimethyl-6h-indeno[2,3-b]indol-6-yl)methyl]-2,5-dimethyl-6h-indeno[2,1-b]indole Chemical compound C12=CC=CC=C2C(C2=CC(C)=CC=C2N2C)=C2C1CC1C2=CC=CC=C2C2=C1N(C)C1=CC=C(C)C=C12 BTJYGWDQLGTPOV-UHFFFAOYSA-N 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical class 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 1
- 238000013022 venting Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97119778.5 | 1997-11-12 | ||
| EP97119778 | 1997-11-12 | ||
| PCT/EP1998/007034 WO1999024446A1 (en) | 1997-11-12 | 1998-11-04 | Metallocenes and catalysts for olefin-polymerisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2277127A1 true CA2277127A1 (en) | 1999-05-20 |
Family
ID=8227611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002277127A Abandoned CA2277127A1 (en) | 1997-11-12 | 1998-11-04 | Metallocenes and catalysts for olefin-polymerisation |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6451724B1 (enExample) |
| EP (1) | EP0952978B1 (enExample) |
| JP (1) | JP4540755B2 (enExample) |
| KR (1) | KR100583931B1 (enExample) |
| CN (1) | CN1231487C (enExample) |
| AR (1) | AR016150A1 (enExample) |
| AU (1) | AU1870999A (enExample) |
| BR (1) | BR9807103A (enExample) |
| CA (1) | CA2277127A1 (enExample) |
| DE (1) | DE69810894T2 (enExample) |
| ES (1) | ES2190131T3 (enExample) |
| HU (1) | HUP0001331A2 (enExample) |
| ID (1) | ID22914A (enExample) |
| IL (1) | IL130713A0 (enExample) |
| MY (1) | MY132919A (enExample) |
| NO (1) | NO993398L (enExample) |
| PL (1) | PL334470A1 (enExample) |
| TR (1) | TR199901908T1 (enExample) |
| WO (1) | WO1999024446A1 (enExample) |
| ZA (1) | ZA9810179B (enExample) |
Families Citing this family (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100583931B1 (ko) * | 1997-11-12 | 2006-05-26 | 바셀 테크놀로지 캄파니 비이브이 | 메탈로센 및 올레핀 중합용 촉매 |
| DE19903306A1 (de) * | 1999-01-28 | 2000-08-03 | Targor Gmbh | Organometallverbindung, Katalysatorsystem enthaltend diese Organometallverbindung und seine Verwendung |
| EP1214364B1 (en) | 1999-09-22 | 2003-07-16 | Basell Polyolefine GmbH | Catalyst system and process for the polymerization of olefins |
| US6232260B1 (en) * | 1999-10-14 | 2001-05-15 | Equistar Chemicals, L.P. | Single-site catalysts for olefin polymerization |
| US6444833B1 (en) * | 1999-12-15 | 2002-09-03 | Basell Technology Company Bv | Metallocene compounds, process for their preparation and their use in catalytic systems for the polymerization of olefins |
| CN100457787C (zh) * | 2000-01-18 | 2009-02-04 | 巴塞尔技术有限公司 | 制备基本上无定形的基于丙烯的聚合物的方法 |
| EP1173445B1 (en) | 2000-02-24 | 2004-06-09 | Basell Polyolefine GmbH | Organometallic compound useful as cocatalyst for polymerizing olefins |
| US6476165B1 (en) | 2000-03-08 | 2002-11-05 | Equistar Chemicals, Lp | Olefin polymerization process using fatty amine additives and boron-modified supported catalyst |
| EP1355958A2 (en) | 2000-12-22 | 2003-10-29 | Basell Poliolefine Italia S.p.A. | Process for the preparation of porous polymers and polymers obtainable thereof |
| WO2002051877A2 (en) | 2000-12-22 | 2002-07-04 | Basell Polyolefine Gmbh | Catalyst components for the polymerization of olefins |
| US6414162B1 (en) | 2001-04-05 | 2002-07-02 | Equistar Chemicals, Lp | Bimetallic catalysts for olefin polymerization |
| US6579957B2 (en) | 2001-04-11 | 2003-06-17 | Equistar Chemicals, Lp | Single-site catalysts based on anionic thiopyran dioxide ligands |
| ATE409180T1 (de) * | 2001-05-15 | 2008-10-15 | Basell Polyolefine Gmbh | Synthese von zyklopentadien derivaten |
| US6541583B2 (en) * | 2001-05-17 | 2003-04-01 | Equistar Chemicals, Lp | Polypropylene preparation |
| WO2002102811A1 (en) | 2001-05-21 | 2002-12-27 | Basell Polyolefine Gmbh | Catalyst system for the polymerization of olefins |
| US6759361B2 (en) * | 2001-06-04 | 2004-07-06 | Equistar Chemicals, Lp | Aluminoboronate activators for single-site olefin polymerization catalysts |
| US6583242B2 (en) | 2001-08-02 | 2003-06-24 | Equistar Chemicals, Lp | Supported olefin polymerization catalysts |
| US6440889B1 (en) * | 2001-08-15 | 2002-08-27 | Equistar Chemicals, Lp | Amine elimination process for making single-site catalysts |
| EP1430088B1 (de) | 2001-09-14 | 2008-10-22 | Basell Polyolefine GmbH | Verfahren zur polymerisation von olefinen |
| DE10145453A1 (de) | 2001-09-14 | 2003-06-05 | Basell Polyolefine Gmbh | Monocyclopentadienylkomplexe mit einem kondensierten Heterocyclus |
| JP2005510590A (ja) | 2001-11-27 | 2005-04-21 | バセル ポリオレフィン ジーエムビーエイチ | ポリマー組成物の処理の方法 |
| JP4062929B2 (ja) | 2002-02-08 | 2008-03-19 | 住友化学株式会社 | 遷移金属錯体、配位子、オレフィン重合用触媒およびオレフィン重合体の製造方法 |
| US6908972B2 (en) | 2002-04-16 | 2005-06-21 | Equistar Chemicals, Lp | Method for making polyolefins |
| US6756455B2 (en) | 2002-05-31 | 2004-06-29 | Equistar Chemicals, Lp | High-temperature solution process for polyolefin manufacture |
| US6630547B1 (en) | 2002-06-11 | 2003-10-07 | Equistar Chemicals, Lp | Use of silanes to control molecular weight in olefin polymerizations |
| WO2004003072A1 (en) * | 2002-06-26 | 2004-01-08 | Basell Poliolefine Italia S.P.A. | Impact-resistant polyolefin compositions |
| US7700690B2 (en) * | 2002-06-26 | 2010-04-20 | Basell Poliolefine Italia S.R.L. | Impact-resistant polyolefin compositions |
| US6737487B2 (en) * | 2002-07-30 | 2004-05-18 | Equistar Chemicals, Lp | Polyolefin block copolymers |
| US6559251B1 (en) | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| WO2004013194A2 (en) | 2002-08-02 | 2004-02-12 | Equistar Chemicals, Lp | Catalysts and process for making polyolefins |
| US6765074B2 (en) | 2002-09-27 | 2004-07-20 | Equistar Chemicals, Lp | Olefin polymerization process |
| US6841500B2 (en) * | 2002-12-03 | 2005-01-11 | Equistar Chemicals, Lp | Bimetallic indenoindolyl catalysts |
| US6683150B1 (en) * | 2002-12-19 | 2004-01-27 | Equistar Chemicals, Lp | High molecular weight polypropylene process |
| US20040176241A1 (en) * | 2003-03-04 | 2004-09-09 | Sandor Nagy | Benzoindenoindolyl metal catalysts for olefin polymerization |
| US6693155B1 (en) | 2003-03-05 | 2004-02-17 | Equistar Chemicals, Lp | Propylene polymerization process |
| JP4616248B2 (ja) | 2003-04-17 | 2011-01-19 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | 気相オレフィン重合方法 |
| US6794468B1 (en) | 2003-05-12 | 2004-09-21 | Equistar Chemicals, Lp | Olefin polymerization process |
| US6995216B2 (en) | 2003-06-16 | 2006-02-07 | Equistar Chemicals, Lp | Process for manufacturing single-site polyolefins |
| US6998451B2 (en) * | 2003-07-01 | 2006-02-14 | Equistar Chemicals, Lp | Olefin polymerization process |
| EP1648946B1 (en) | 2003-07-04 | 2015-07-15 | Basell Polyolefine GmbH | Olefin polymerization process |
| US6933353B2 (en) * | 2003-07-07 | 2005-08-23 | Equistar Chemicals, Lp | Olefin polymerization process |
| US6818713B1 (en) | 2003-08-11 | 2004-11-16 | Equistar Chemicals, Lp | Process for making polyethylene |
| US6939930B2 (en) | 2003-09-09 | 2005-09-06 | Equistar Chemicals, Lp | Hydrosilane additives for increased polyolefin molecular weight |
| US6958377B2 (en) * | 2003-10-15 | 2005-10-25 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7220695B2 (en) * | 2004-01-07 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Supported activator |
| US7741417B2 (en) * | 2004-01-07 | 2010-06-22 | Exxonmobil Chemical Patents Inc. | Preparation of polymerization catalyst activators utilizing indole-modified silica supports |
| EP1564226A1 (en) | 2004-02-16 | 2005-08-17 | Stichting Dutch Polymer Institute | Titanocene-based catalyst system |
| CN101001892A (zh) | 2004-03-12 | 2007-07-18 | 巴塞尔聚烯烃股份有限公司 | 用于烯烃聚合的催化剂体系 |
| EP1723184A1 (en) | 2004-03-12 | 2006-11-22 | Basell Polyolefine GmbH | Process for polymerizing 1-hexene or higher alpha-olefins |
| DE602005023844D1 (de) | 2004-03-12 | 2010-11-11 | Basell Polyolefine Gmbh | Verfahren zur polymerisation von 1-hexen oder höheren alpha-olefinen |
| US6995220B2 (en) | 2004-04-29 | 2006-02-07 | Equistar Chemicals, Lp | Ethylene polymerization process |
| DE102004027332A1 (de) * | 2004-06-04 | 2005-12-22 | Basell Polyolefine Gmbh | Übergangsmetallverbindung, Ligandsystem, Katalysatorsystem und Verfahren zur Herstellung von Polyolefinen |
| JP5006783B2 (ja) * | 2004-07-13 | 2012-08-22 | バーゼル・ポリオレフィン・ゲーエムベーハー | メタロセン化合物、それらの調製で使用される配位子、１−ブテンポリマーの調製法、およびその方法から得られる１−ブテンポリマー |
| US6967231B1 (en) | 2004-09-23 | 2005-11-22 | Equistar Chemicals, Lp | Olefin polymerization process |
| EP1655314A1 (en) | 2004-11-09 | 2006-05-10 | Basell Polyolefine GmbH | Process for the preparation of 1-butene/propylene copolymers |
| KR20070093058A (ko) | 2004-11-22 | 2007-09-17 | 바젤 폴리올레핀 게엠베하 | 프로필렌 기재 삼중합체 |
| JP2008523231A (ja) * | 2004-12-13 | 2008-07-03 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | ポリオレフィン繊維 |
| JP2008525651A (ja) * | 2004-12-23 | 2008-07-17 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | 弾性を有する繊維 |
| US7196147B2 (en) * | 2005-07-01 | 2007-03-27 | Equistar Chemicals, Lp | Olefin polymerization process with improved operability and polymer properties |
| US7230056B2 (en) | 2005-07-01 | 2007-06-12 | Equistar Chemicals, Lp | Catalyst preparation method |
| US7538173B2 (en) | 2005-11-21 | 2009-05-26 | Equistar Chemicals Lp | Polyolefin compositions |
| DE102005061326A1 (de) * | 2005-12-20 | 2007-06-21 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Metallocenen aus recycelten, substituierten Cyclopentadienylderivaten |
| US7423098B2 (en) * | 2006-01-17 | 2008-09-09 | Equistar Chemicals, Lp | Polyethylene process |
| US8003739B2 (en) * | 2007-10-17 | 2011-08-23 | Fina Technology, Inc. | Multi-component catalyst systems and polymerization processes for forming in-situ heterophasic copolymers and/or varying the xylene solubles content of polyolefins |
| US7638584B2 (en) * | 2006-06-20 | 2009-12-29 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7638586B2 (en) | 2006-09-26 | 2009-12-29 | Equistar Chemicals, Lp | Olefin polymerization process |
| US8475898B2 (en) | 2007-08-29 | 2013-07-02 | Equistar Chemicals, Lp | Polyolefin resin blends for crack-resistant pipe |
| US7781549B2 (en) * | 2007-09-04 | 2010-08-24 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7666961B2 (en) * | 2007-09-04 | 2010-02-23 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7655740B2 (en) * | 2007-09-04 | 2010-02-02 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7723451B2 (en) * | 2007-09-04 | 2010-05-25 | Equistar Chemicals, Lp | Olefin polymerization process |
| US8022005B2 (en) | 2007-11-08 | 2011-09-20 | Exxonmobil Chemical Patents Inc. | Halogen substituted heterocyclic heteroatom containing ligands-alumoxane activation of metallocenes |
| EP2231724B1 (en) | 2007-12-18 | 2011-08-10 | Basell Polyolefine GmbH | Gas-phase process for the polymerization of alpha-olefins |
| KR101580849B1 (ko) * | 2008-02-29 | 2015-12-30 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 폴리올레핀 조성물 |
| US7776974B2 (en) * | 2008-04-30 | 2010-08-17 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7671151B2 (en) * | 2008-05-21 | 2010-03-02 | Equistar Chemicals, Lp | Olefin polymerization process |
| US7816478B2 (en) | 2008-09-03 | 2010-10-19 | Equistar Chemicals, Lp | Polyethylene thick film and process for preparing polyethylene |
| US20100129924A1 (en) * | 2008-11-21 | 2010-05-27 | Sandor Nagy | Quality assurance method for olefin polymerization catalysts |
| DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
| KR101623485B1 (ko) * | 2013-08-01 | 2016-05-23 | 주식회사 엘지화학 | 메탈로센 화합물, 이를 포함하는 촉매 조성물 및 이를 이용하는 올레핀계 중합체의 제조방법 |
| CN104558058B (zh) * | 2013-10-12 | 2017-08-08 | 中国科学院长春应用化学研究所 | 茂金属配合物及其制备方法、催化剂组合物 |
| KR101644113B1 (ko) * | 2013-10-18 | 2016-07-29 | 주식회사 엘지화학 | 혼성 담지 메탈로센 촉매 |
| US9321854B2 (en) | 2013-10-29 | 2016-04-26 | Exxonmobil Chemical Patents Inc. | Aluminum alkyl with C5 cyclic and pendent olefin polymerization catalyst |
| KR20150058083A (ko) * | 2013-11-20 | 2015-05-28 | 주식회사 동진쎄미켐 | 신규한 발광 화합물 및 이를 포함하는 유기발광소자 |
| KR101705340B1 (ko) | 2014-06-03 | 2017-02-09 | 주식회사 엘지화학 | 폴리올레핀의 제조 방법 및 이로부터 제조된 폴리올레핀 |
| KR101703274B1 (ko) | 2014-08-12 | 2017-02-22 | 주식회사 엘지화학 | 메탈로센 화합물, 이를 포함하는 촉매 조성물 및 이를 이용한 올레핀 중합체의 제조방법 |
| WO2016024818A1 (ko) * | 2014-08-12 | 2016-02-18 | 주식회사 엘지화학 | 메탈로센 화합물， 이를 포함하는 촉매 조성물 및 이를 이용한 올레핀 중합체의 제조방법 |
| KR101784463B1 (ko) | 2014-10-06 | 2017-10-11 | 주식회사 엘지화학 | 리간드 화합물, 메탈로센 화합물 및 이를 이용하는 올레핀계 중합체의 제조방법 |
| CN105814101B (zh) | 2014-10-13 | 2018-03-02 | 株式会社Lg化学 | 具有优良可加工性和耐环境应力开裂性的乙烯/1‑己烯或乙烯/1‑丁烯共聚物 |
| US9796795B2 (en) | 2015-01-14 | 2017-10-24 | Exxonmobil Chemical Patents Inc. | Tetrahydroindacenyl catalyst composition, catalyst system, and processes for use thereof |
| CN106661072B (zh) | 2015-01-28 | 2021-03-12 | Lg化学株式会社 | 金属茂化合物、包含其的催化剂组合物以及使用其制备基于烯烃的聚合物的方法 |
| JP6450393B2 (ja) | 2015-01-28 | 2019-01-09 | エルジー・ケム・リミテッド | メタロセン化合物、これを含む触媒組成物、およびこれを用いるポリオレフィンの製造方法 |
| CN105985368B (zh) * | 2015-02-06 | 2020-03-10 | 中国石油天然气股份有限公司 | 含杂原子的π-配体的茂金属络合物及其制备方法、其催化剂体系和催化剂体系的应用 |
| CN105985383B (zh) * | 2015-02-06 | 2019-09-03 | 中国石油天然气股份有限公司 | 含杂原子的π-配体的茂金属络合物及其制备方法、其催化剂体系和催化剂体系的应用 |
| JP6735292B2 (ja) * | 2015-02-06 | 2020-08-05 | 中国石油▲天▼然▲気▼股▲ふん▼有限公司 | ヘテロ原子含有π−配位子のメタロセン錯体及びその製造方法、その触媒系及び触媒系の応用 |
| CN107636029B (zh) | 2015-04-20 | 2020-05-22 | 埃克森美孚化学专利公司 | 包含氟化载体的催化剂组合物及其使用方法 |
| CN107636028A (zh) | 2015-04-20 | 2018-01-26 | 埃克森美孚化学专利公司 | 包含氟化物化的载体的催化剂组合物及其使用方法 |
| US10351647B2 (en) | 2015-05-29 | 2019-07-16 | Exxonmobil Chemical Patents Inc. | Polymerization process using bridged metallocene compounds supported on organoaluminum treated layered silicate supports |
| WO2017039995A1 (en) | 2015-08-31 | 2017-03-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins for polyolefin reactions |
| WO2017039994A1 (en) | 2015-08-31 | 2017-03-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins on clays |
| US10618988B2 (en) | 2015-08-31 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| US10059788B2 (en) | 2016-04-29 | 2018-08-28 | Exxonmobil Chemical Patents Inc. | Organoaluminum activators on clays |
| US9803037B1 (en) | 2016-05-03 | 2017-10-31 | Exxonmobil Chemical Patents Inc. | Tetrahydro-as-indacenyl catalyst composition, catalyst system, and processes for use thereof |
| US10562987B2 (en) | 2016-06-30 | 2020-02-18 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| KR102072697B1 (ko) | 2016-12-09 | 2020-02-03 | 주식회사 엘지화학 | 가공성 및 기계적 물성이 우수한 에틸렌/1-헥센 공중합체 |
| US10626200B2 (en) | 2017-02-28 | 2020-04-21 | Exxonmobil Chemical Patents Inc. | Branched EPDM polymers produced via use of vinyl transfer agents and processes for production thereof |
| WO2018160278A1 (en) | 2017-03-01 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
| CN107325034A (zh) * | 2017-06-23 | 2017-11-07 | 浙江华海药业股份有限公司 | 一种制备罗匹尼罗二聚物的方法 |
| US11518824B2 (en) | 2017-10-11 | 2022-12-06 | Basell Polyolefine Gmbh | Supported catalyst system |
| US10703838B2 (en) | 2017-10-31 | 2020-07-07 | Exxonmobil Chemical Patents Inc. | Mixed catalyst systems with four metallocenes on a single support |
| WO2019203676A1 (en) * | 2018-04-16 | 2019-10-24 | Arlanxeo Netherlands B.V. | Metal complex comprising amidine and indole fused cyclopentadienyl ligands |
| CN114599692B (zh) * | 2020-09-29 | 2024-02-02 | 株式会社Lg化学 | 具有改善的柔韧性和可加工性的乙烯/1-己烯共聚物 |
| CN116425774A (zh) * | 2021-12-30 | 2023-07-14 | 中国石油天然气股份有限公司 | 一种稀土金属配合物及其制备方法和应用 |
| CN115400797B (zh) * | 2022-08-19 | 2024-09-27 | 中国科学院山西煤炭化学研究所 | 含杂原子的茂金属催化剂体系及催化α-烯烃齐聚的方法 |
| CN119431465B (zh) * | 2023-08-01 | 2025-12-02 | 中国石油化工股份有限公司 | 茂金属化合物、催化剂组合物、烯烃聚合方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714148A (en) * | 1968-10-15 | 1973-01-30 | Sumitomo Chemical Co | Process for preparing dibenzazocine derivatives and salts thereof |
| DE3007725A1 (de) | 1980-02-29 | 1981-09-17 | Hansjörg Prof. Dr. 2000 Hamburg Sinn | Verfahren zur herstellung von polyethylen, polypropylen und copolymeren |
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| IT1256259B (it) | 1992-12-30 | 1995-11-29 | Montecatini Tecnologie Srl | Composti mettallocenici aventi leganti di tipo fluorenilico |
| IT1273420B (it) | 1994-04-06 | 1997-07-08 | Spherilene Srl | Composti metallocenici, procedimento per la preparazione e loro utilizzo in catalizzatori per la polimerizzazione delle olefine |
| ID22443A (id) | 1996-11-15 | 1999-10-14 | Montelll Technology Co Bv | Metallosena heterosiklik dan polimerisasi katalis |
| US6451938B1 (en) | 1997-02-25 | 2002-09-17 | Exxon Mobil Chemical Patents Inc. | Polymerization catalyst system comprising heterocyclic fused cyclopentadienide ligands |
| KR100583931B1 (ko) * | 1997-11-12 | 2006-05-26 | 바셀 테크놀로지 캄파니 비이브이 | 메탈로센 및 올레핀 중합용 촉매 |
| US6232260B1 (en) * | 1999-10-14 | 2001-05-15 | Equistar Chemicals, L.P. | Single-site catalysts for olefin polymerization |
-
1998
- 1998-11-04 KR KR1019997006194A patent/KR100583931B1/ko not_active Expired - Fee Related
- 1998-11-04 WO PCT/EP1998/007034 patent/WO1999024446A1/en not_active Ceased
- 1998-11-04 ES ES98963411T patent/ES2190131T3/es not_active Expired - Lifetime
- 1998-11-04 EP EP98963411A patent/EP0952978B1/en not_active Expired - Lifetime
- 1998-11-04 IL IL13071398A patent/IL130713A0/xx unknown
- 1998-11-04 AU AU18709/99A patent/AU1870999A/en not_active Abandoned
- 1998-11-04 JP JP52542799A patent/JP4540755B2/ja not_active Expired - Lifetime
- 1998-11-04 DE DE69810894T patent/DE69810894T2/de not_active Expired - Lifetime
- 1998-11-04 HU HU0001331A patent/HUP0001331A2/hu unknown
- 1998-11-04 BR BR9807103-3A patent/BR9807103A/pt not_active Application Discontinuation
- 1998-11-04 ID IDW990856A patent/ID22914A/id unknown
- 1998-11-04 CN CNB988031299A patent/CN1231487C/zh not_active Expired - Fee Related
- 1998-11-04 US US09/341,438 patent/US6451724B1/en not_active Expired - Lifetime
- 1998-11-04 PL PL98334470A patent/PL334470A1/xx unknown
- 1998-11-04 CA CA002277127A patent/CA2277127A1/en not_active Abandoned
- 1998-11-04 TR TR1999/01908T patent/TR199901908T1/xx unknown
- 1998-11-06 ZA ZA9810179A patent/ZA9810179B/xx unknown
- 1998-11-10 MY MYPI98005097A patent/MY132919A/en unknown
- 1998-11-11 AR ARP980105685A patent/AR016150A1/es unknown
-
1999
- 1999-07-09 NO NO993398A patent/NO993398L/no not_active Application Discontinuation
-
2002
- 2002-05-02 US US10/139,407 patent/US20030148877A1/en not_active Abandoned
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| BR9807103A (pt) | 2000-05-16 |
| TR199901908T1 (xx) | 2000-02-21 |
| NO993398D0 (no) | 1999-07-09 |
| AR016150A1 (es) | 2001-06-20 |
| JP2001508083A (ja) | 2001-06-19 |
| ZA9810179B (en) | 1999-05-07 |
| US6451724B1 (en) | 2002-09-17 |
| IL130713A0 (en) | 2000-06-01 |
| MY132919A (en) | 2007-10-31 |
| KR100583931B1 (ko) | 2006-05-26 |
| PL334470A1 (en) | 2000-02-28 |
| JP4540755B2 (ja) | 2010-09-08 |
| DE69810894D1 (de) | 2003-02-27 |
| US20030148877A1 (en) | 2003-08-07 |
| EP0952978A1 (en) | 1999-11-03 |
| KR20000069979A (ko) | 2000-11-25 |
| AU1870999A (en) | 1999-05-31 |
| WO1999024446A1 (en) | 1999-05-20 |
| HUP0001331A2 (hu) | 2000-08-28 |
| NO993398L (no) | 1999-09-09 |
| CN1249756A (zh) | 2000-04-05 |
| DE69810894T2 (de) | 2003-11-13 |
| EP0952978B1 (en) | 2003-01-22 |
| CN1231487C (zh) | 2005-12-14 |
| ID22914A (id) | 1999-12-16 |
| ES2190131T3 (es) | 2003-07-16 |
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