JP2002530285A - オレフィン−重合−触媒成分としてのメチレン橋架けメタロセン - Google Patents
オレフィン−重合−触媒成分としてのメチレン橋架けメタロセンInfo
- Publication number
- JP2002530285A JP2002530285A JP2000582402A JP2000582402A JP2002530285A JP 2002530285 A JP2002530285 A JP 2002530285A JP 2000582402 A JP2000582402 A JP 2000582402A JP 2000582402 A JP2000582402 A JP 2000582402A JP 2002530285 A JP2002530285 A JP 2002530285A
- Authority
- JP
- Japan
- Prior art keywords
- methylene
- indenyl
- group
- bis
- 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.)
- Pending
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- 239000003446 ligand Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001255 actinides Chemical class 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 76
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 50
- -1 diphenylphosphino Chemical group 0.000 claims description 48
- 238000006116 polymerization reaction Methods 0.000 claims description 41
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 38
- 239000005977 Ethylene Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 36
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 13
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 9
- 239000004711 α-olefin Substances 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 230000003213 activating effect Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000007848 Bronsted acid Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002685 polymerization catalyst Substances 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 229910052723 transition metal Inorganic materials 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 3
- 229910052768 actinide Inorganic materials 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 57
- 238000003786 synthesis reaction Methods 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 37
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000003756 stirring Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 23
- 239000000725 suspension Substances 0.000 description 23
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- 229910007926 ZrCl Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 14
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 238000000605 extraction Methods 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 9
- 238000012937 correction Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- VBDPXNNRCIXHFT-UHFFFAOYSA-N 2-(1h-inden-2-ylmethyl)-1h-indene Chemical compound C1=CC=C2CC(CC=3CC4=CC=CC=C4C=3)=CC2=C1 VBDPXNNRCIXHFT-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 7
- XZARRWQFNYUZBC-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C(C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C(C)(C)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C(C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C(C)(C)C)=CC2=C1 XZARRWQFNYUZBC-UHFFFAOYSA-L 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XBKNMGUCKSFTGE-UHFFFAOYSA-N 3-methyl-2-[(3-methyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C)=C1CC1=C(C)C2=CC=CC=C2C1 XBKNMGUCKSFTGE-UHFFFAOYSA-N 0.000 description 5
- VCFGYRFNVFQFEH-UHFFFAOYSA-N 3-tert-butyl-2-[(3-tert-butyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C(C)(C)C)=C1CC1=C(C(C)(C)C)C2=CC=CC=C2C1 VCFGYRFNVFQFEH-UHFFFAOYSA-N 0.000 description 5
- UBWRPKIGXGLXBY-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2CC([Zr+2](C=3CC4=CC=CC=C4C=3)=C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2CC([Zr+2](C=3CC4=CC=CC=C4C=3)=C)=CC2=C1 UBWRPKIGXGLXBY-UHFFFAOYSA-L 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- VLZCLFQHRXRCFF-UHFFFAOYSA-N 2-[(4,7-dimethyl-1h-inden-2-yl)methyl]-4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC(CC1=CC=3C(C)=CC=C(C=3C1)C)=C2 VLZCLFQHRXRCFF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- 241000349731 Afzelia bipindensis Species 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- BSRUXPIXXVJQRG-UHFFFAOYSA-N [2-[(3-diphenylphosphanyl-1h-inden-2-yl)methyl]-3h-inden-1-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C=1C2=CC=CC=C2CC=1CC(CC1=CC=CC=C11)=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BSRUXPIXXVJQRG-UHFFFAOYSA-N 0.000 description 3
- JWBWPEWZKRDMBC-UHFFFAOYSA-L [Cl-].[Cl-].C=1C2=CC=CC=C2C(C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C2=CC=CC=C2C(C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1C1=CC=CC=C1 JWBWPEWZKRDMBC-UHFFFAOYSA-L 0.000 description 3
- UVPDGFZJZYLLEK-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC=C(C)C2=C1CC([Zr+2](=C)C1=CC=3C(C)=CC=C(C=3C1)C)=C2 Chemical compound [Cl-].[Cl-].CC1=CC=C(C)C2=C1CC([Zr+2](=C)C1=CC=3C(C)=CC=C(C=3C1)C)=C2 UVPDGFZJZYLLEK-UHFFFAOYSA-L 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- JZVSOQUJGPAPJK-UHFFFAOYSA-N trimethyl-[3-methyl-2-[(3-methyl-1-trimethylsilyl-1h-inden-2-yl)methyl]-1h-inden-1-yl]silane Chemical compound C[Si](C)(C)C1C2=CC=CC=C2C(C)=C1CC1=C(C)C2=CC=CC=C2C1[Si](C)(C)C JZVSOQUJGPAPJK-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 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
- WBZVXZGPXBXMSC-UHFFFAOYSA-N 2,5,6,6-tetrakis(2-methylpropyl)oxaluminane Chemical compound CC(C)CC1CC[Al](CC(C)C)OC1(CC(C)C)CC(C)C WBZVXZGPXBXMSC-UHFFFAOYSA-N 0.000 description 2
- COOKKJGOGWACMY-UHFFFAOYSA-N 3-methyl-1h-indene Chemical compound C1=CC=C2C(C)=CCC2=C1 COOKKJGOGWACMY-UHFFFAOYSA-N 0.000 description 2
- LOWMZVPYBMDIBG-UHFFFAOYSA-N 3-phenyl-2-[(3-phenyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C=1C=CC=CC=1C=1C2=CC=CC=C2CC=1CC(CC1=CC=CC=C11)=C1C1=CC=CC=C1 LOWMZVPYBMDIBG-UHFFFAOYSA-N 0.000 description 2
- QKTNNHZEFGFOQG-UHFFFAOYSA-N 3-tert-butyl-1h-indene Chemical compound C1=CC=C2C(C(C)(C)C)=CCC2=C1 QKTNNHZEFGFOQG-UHFFFAOYSA-N 0.000 description 2
- DKLQZDIAQKGVTA-UHFFFAOYSA-N 4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC=C2 DKLQZDIAQKGVTA-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241001274216 Naso Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- QXZCNXSTDKFSRH-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C)=CC2=C1 QXZCNXSTDKFSRH-UHFFFAOYSA-L 0.000 description 2
- WFKQLHXTJWZRFU-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 WFKQLHXTJWZRFU-UHFFFAOYSA-L 0.000 description 2
- JJXHBJJGFYFIPM-UHFFFAOYSA-L [Cl-].[Cl-].C=1C2=CC=CC=C2C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C2=CC=CC=C2C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JJXHBJJGFYFIPM-UHFFFAOYSA-L 0.000 description 2
- WWDINEUJECJJSF-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C1C(=C(C2=CC=CC=C12)C)[Zr+2])(C)C Chemical compound [Cl-].[Cl-].C[Si](C1C(=C(C2=CC=CC=C12)C)[Zr+2])(C)C WWDINEUJECJJSF-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZMMRKRFMSDTOLV-UHFFFAOYSA-N cyclopenta-1,3-diene zirconium Chemical compound [Zr].C1C=CC=C1.C1C=CC=C1 ZMMRKRFMSDTOLV-UHFFFAOYSA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
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- 239000001301 oxygen Substances 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
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- 125000004434 sulfur atom Chemical group 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
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- PXORBAGTGTXORO-UHFFFAOYSA-N 1-phenyl-1h-indene Chemical compound C1=CC2=CC=CC=C2C1C1=CC=CC=C1 PXORBAGTGTXORO-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
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- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- RIAYWWDCGFUPJC-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[AlH]CC(C)CC(C)(C)C RIAYWWDCGFUPJC-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
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001993 dienes Chemical class 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
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001282 iso-butane Substances 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
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013519 translation 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RQHQKLNZXIIKLE-UHFFFAOYSA-N trimethyl-[2-[(1-trimethylsilyl-1h-inden-2-yl)methyl]-1h-inden-1-yl]silane Chemical compound C1=CC=C2C([Si](C)(C)C)C(CC=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 RQHQKLNZXIIKLE-UHFFFAOYSA-N 0.000 description 1
- VJJYNHGCCSVYLS-UHFFFAOYSA-N trimethyl-[2-[(3-trimethylsilyl-1h-inden-2-yl)methyl]-3h-inden-1-yl]silane Chemical compound C1C2=CC=CC=C2C([Si](C)(C)C)=C1CC1=C([Si](C)(C)C)C2=CC=CC=C2C1 VJJYNHGCCSVYLS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- HKVFGFGPRISDFM-UHFFFAOYSA-N tris(2,3,3-trimethylbutyl)alumane Chemical compound CC(C)(C)C(C)C[Al](CC(C)C(C)(C)C)CC(C)C(C)(C)C HKVFGFGPRISDFM-UHFFFAOYSA-N 0.000 description 1
- VGONMIOMLRCRSS-UHFFFAOYSA-N tris(2,3-dimethylhexyl)alumane Chemical compound CCCC(C)C(C)C[Al](CC(C)C(C)CCC)CC(C)C(C)CCC VGONMIOMLRCRSS-UHFFFAOYSA-N 0.000 description 1
- BENYMJNPVWYYES-UHFFFAOYSA-N tris(2,3-dimethylpentyl)alumane Chemical compound CCC(C)C(C)C[Al](CC(C)C(C)CC)CC(C)C(C)CC BENYMJNPVWYYES-UHFFFAOYSA-N 0.000 description 1
- UVCGXEXDZCCTFF-UHFFFAOYSA-N tris(2,4-dimethylheptyl)alumane Chemical compound CCCC(C)CC(C)C[Al](CC(C)CC(C)CCC)CC(C)CC(C)CCC UVCGXEXDZCCTFF-UHFFFAOYSA-N 0.000 description 1
- FEJNOSHLGDRZDX-UHFFFAOYSA-N tris(2-ethyl-3-methylbutyl)alumane Chemical compound CCC(C(C)C)C[Al](CC(CC)C(C)C)CC(CC)C(C)C FEJNOSHLGDRZDX-UHFFFAOYSA-N 0.000 description 1
- JAFSWBPCWFKGBY-UHFFFAOYSA-N tris(2-ethyl-3-methylpentyl)alumane Chemical compound CCC(C)C(CC)C[Al](CC(CC)C(C)CC)CC(CC)C(C)CC JAFSWBPCWFKGBY-UHFFFAOYSA-N 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
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 1
- VIDMRZMJMLMHSP-UHFFFAOYSA-N tris(3-methyl-2-propan-2-ylbutyl)alumane Chemical compound CC(C)C(C(C)C)C[Al](CC(C(C)C)C(C)C)CC(C(C)C)C(C)C VIDMRZMJMLMHSP-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
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
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- 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
- 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
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| PCT/EP1999/008646 WO2000029415A1 (en) | 1998-11-18 | 1999-11-10 | Methylene bridged metallocenes as olefin-polymerization-catalyst components |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014224188A (ja) * | 2013-05-16 | 2014-12-04 | 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 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6559251B1 (en) * | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| WO2010022878A1 (en) * | 2008-08-25 | 2010-03-04 | Basell Polyolefine Gmbh | Preparation of ansa metallocene compounds |
| KR20140075589A (ko) | 2012-12-11 | 2014-06-19 | 주식회사 엘지화학 | 신규한 리간드 화합물, 이의 제조방법, 전이금속 화합물, 및 이의 제조방법 |
| EP2910559B1 (en) | 2012-12-11 | 2017-09-13 | LG Chem, Ltd. | Novel ligand compound and production method for same, and transition metal compound comprising the novel ligand compound and production method for same |
| US11155659B2 (en) * | 2017-04-04 | 2021-10-26 | Sabic Global Technologies B.V. | Dimethyl-silyl-bridged-1-substituted-2-indenyl metallocene complexes for olefin polymerization |
| CN110650965B (zh) | 2017-04-04 | 2022-10-04 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二烃基-甲硅烷基-桥连-1,3二取代-2-茚基茂金属络合物 |
| EP3743431B1 (en) | 2018-01-24 | 2025-04-16 | SABIC Global Technologies B.V. | 1,2-phenylene bridged 1-indenyl-2-indenyl metallocene complexes for olefin polymerisation |
| US11613593B2 (en) | 2020-02-24 | 2023-03-28 | Exxonmobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3840772A1 (de) | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
| DE59104869D1 (de) | 1990-11-12 | 1995-04-13 | Hoechst Ag | 2-Substituierte Bisindenylmetallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren bei der Olefinpolymerisation. |
| AU660808B2 (en) | 1992-06-18 | 1995-07-06 | Montell Technology Company B.V. | Catalysts for the polymerization of olefins |
| NL9201970A (nl) | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| IT1273661B (it) | 1994-07-20 | 1997-07-09 | Spherilene Srl | Catalizzatori per la polimerizzazione delle olefine |
| IT1272924B (it) | 1995-01-23 | 1997-07-01 | Spherilene Srl | Procedimento per la preparazione di composti ciclopentadienilici e composti cosi' ottenibili |
| DE19637669A1 (de) | 1996-09-16 | 1998-03-19 | Hoechst Ag | Verfahren zur Herstellung einer methylenverbrückten Biscyclopentadienylverbindung |
| WO1998043931A1 (en) * | 1997-03-29 | 1998-10-08 | Montell Technology Company B.V. | Process for preparing cyclopentadienyl compounds |
| US6559252B1 (en) | 1997-10-29 | 2003-05-06 | Basell Technology Company Bv | Catalysts and processes for the polymerization of olefins |
| CN1243763C (zh) | 1998-01-14 | 2006-03-01 | 蒙特尔技术有限公司 | 茂金属化合物的制备方法 |
| EP1214364B1 (en) | 1999-09-22 | 2003-07-16 | Basell Polyolefine GmbH | Catalyst system and process for the polymerization of olefins |
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1999
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- 1999-11-10 EP EP99972216A patent/EP1131328B1/en not_active Expired - Lifetime
- 1999-11-10 WO PCT/EP1999/008646 patent/WO2000029415A1/en not_active Ceased
- 1999-11-10 AU AU13822/00A patent/AU1382200A/en not_active Abandoned
- 1999-11-10 KR KR1020017006322A patent/KR20010101034A/ko not_active Withdrawn
- 1999-11-10 ES ES99972216T patent/ES2197714T3/es not_active Expired - Lifetime
- 1999-11-10 BR BR9916740-9A patent/BR9916740A/pt not_active Application Discontinuation
- 1999-11-10 US US09/831,960 patent/US6693156B1/en not_active Expired - Fee Related
- 1999-11-10 CA CA002350542A patent/CA2350542A1/en not_active Abandoned
- 1999-11-10 JP JP2000582402A patent/JP2002530285A/ja active Pending
- 1999-11-10 IL IL14297999A patent/IL142979A0/xx unknown
- 1999-11-18 AR ARP990105862A patent/AR021312A1/es unknown
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2003
- 2003-12-16 US US10/737,097 patent/US6872863B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014224188A (ja) * | 2013-05-16 | 2014-12-04 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6693156B1 (en) | 2004-02-17 |
| DE69907721D1 (de) | 2003-06-12 |
| US6872863B2 (en) | 2005-03-29 |
| EP1131328A1 (en) | 2001-09-12 |
| IL142979A0 (en) | 2002-04-21 |
| DE69907721T2 (de) | 2004-02-26 |
| AR021312A1 (es) | 2002-07-17 |
| WO2000029415A1 (en) | 2000-05-25 |
| AU1382200A (en) | 2000-06-05 |
| BR9916740A (pt) | 2001-08-21 |
| EP1131328B1 (en) | 2003-05-07 |
| CA2350542A1 (en) | 2000-05-25 |
| US20040147695A1 (en) | 2004-07-29 |
| KR20010101034A (ko) | 2001-11-14 |
| ES2197714T3 (es) | 2004-01-01 |
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