JP2736935B2 - 金属錯体化合物 - Google Patents
金属錯体化合物Info
- Publication number
- JP2736935B2 JP2736935B2 JP2242861A JP24286190A JP2736935B2 JP 2736935 B2 JP2736935 B2 JP 2736935B2 JP 2242861 A JP2242861 A JP 2242861A JP 24286190 A JP24286190 A JP 24286190A JP 2736935 B2 JP2736935 B2 JP 2736935B2
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- alkyl
- independently
- carbon atoms
- cyclopentadienyl
- 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 - Lifetime
Links
- -1 Metal complex compound Chemical class 0.000 title description 30
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000001450 anions Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011574 phosphorus Chemical group 0.000 claims description 4
- 229910052698 phosphorus Chemical group 0.000 claims description 4
- 229910052726 zirconium Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 36
- 239000000178 monomer Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 150000001768 cations Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- JFWBIRAGFWPMTI-UHFFFAOYSA-N [Zr].[CH]1C=CC=C1 Chemical compound [Zr].[CH]1C=CC=C1 JFWBIRAGFWPMTI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methylcycloheptane Chemical compound CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- MDTDQDVMQBTXST-UHFFFAOYSA-K 2h-inden-2-ide;titanium(4+);trichloride Chemical compound Cl[Ti+](Cl)Cl.C1=CC=C2[CH-]C=CC2=C1 MDTDQDVMQBTXST-UHFFFAOYSA-K 0.000 description 1
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- 241000349731 Afzelia bipindensis Species 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- ZCXSGAGJXWOLPP-UHFFFAOYSA-N C1(C=CC=C1)[Ti](OC(C)C)(OC(C)C)OC(C)C Chemical compound C1(C=CC=C1)[Ti](OC(C)C)(OC(C)C)OC(C)C ZCXSGAGJXWOLPP-UHFFFAOYSA-N 0.000 description 1
- QFOSYUCQLUMGJY-UHFFFAOYSA-K C1(C=CC=C1)[Zr](OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C1(C=CC=C1)[Zr](OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 QFOSYUCQLUMGJY-UHFFFAOYSA-K 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000012718 coordination polymerization Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- BMTKGBCFRKGOOZ-UHFFFAOYSA-K cyclopenta-1,3-diene;zirconium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1 BMTKGBCFRKGOOZ-UHFFFAOYSA-K 0.000 description 1
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical compound [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- IBMIFJZXMKTKTG-UHFFFAOYSA-L methylidenetitanium(2+);dichloride Chemical compound Cl[Ti](Cl)=C IBMIFJZXMKTKTG-UHFFFAOYSA-L 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- ORUFTXBRVJTAFU-UHFFFAOYSA-N tris(4-fluorophenyl) borate Chemical compound C1=CC(F)=CC=C1OB(OC=1C=CC(F)=CC=1)OC1=CC=C(F)C=C1 ORUFTXBRVJTAFU-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- 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
- 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
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/6192—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
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- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
金属錯体を非配位性の相溶性アニオンを含むブレンステ
ツド酸の塩と反応させることによつて製造した若干のビ
ス(シクロペンタジエニル)金属化合物が記載されてい
る。このEP特許はこのような錯体がオレフイン重合触媒
として有利に使用される事実を開示している。
かわらず、付加重合用の更に効率で有用な触媒を製造す
ることが望ましい。本発明はこの課題を解決するもので
あり、重合触媒として高度に活性であり且つ広範囲の種
類のモノマーおよびモノマー混合物の重合を望ましく可
能にするある種の改良された金属錯体含有化合物を提供
するものである。
れば、次式 CpMXn+A- 〔式中、Mはチタンまたはジルコニウムであり;Cpは式 〔R′はそれぞれの場合独立に水素、ハロゲンまたは20
以下の炭素原子をもつアルキル、アリールもしくはハロ
アルキル、シリル基およびそれらの組合せからえらばれ
た基であり; R″はR′であるか又は式 〔Yは窒素またはリンであり;Rはそれぞれの場合独立
に10以下の炭素原子もしくはケイ素原子をもつアルキ
ル、アリール、シリルまたはそれらの組合せであり;mは
1〜4の整数である〕のYを介してMに共有結合してい
る2価の基である〕 で示されるシクロペンタジエニルもしくは置換シクロペ
ンタジエニル基であり; Xはそれぞれの場合独立にハロゲンまたは20以下の炭
素原子をもつアルキル、アリール、アリールオキシまた
はアルコキシであり; nは1または2であり;そして A-は〔BQ4〕− 〔Bは原子価が3の状態のホウ素であり;そしてQはそ
れぞれの場合独立にハイドライド、ハロゲンまたは20個
以下の炭素原子をもつジアルキルアミド、アルコキサイ
ド、アリールオキサイド、ヒドロカルビルもしくは置換
ヒドロカルビル基であって但しQハライドは1個以下で
ある〕 である〕 に相当するモノシクロペンタジエニルまたは置換モノシ
クロペンタジエニル金属錯体含有化合物が今や提供され
る。
フイルム,シート,押出し発泡およびその他の用途に使
用されるポリマーを製造するのに有用である。これらの
化合物はまた水素化反応、接触クラツキングおよびその
他の工業プロセスに使用することもできる。
不活性非プロトン性溶媒中で混合し、そして所望ならば
生成物を回収することによつて製造することができる。
少なくとも1種の置換分を含む、且つその原子価より1
つ少ない配位数を通常もつカチオンを形成しうる、チタ
ンまたはジルコニウムのモノ(シクロペンタジエニル)
誘導体である少なくとも1種の第1成分;および (b)ブロンステツド酸および非配位性の相溶性アニオ
ンから成る塩である少なくとも1種の第2成分。
であり、第2成分の非配位性の相溶性アニオンはA-に相
当するものである。
特に好ましい金属錯体化合物は式 〔Cp*はMにη5結合様式で結合した2価のシクロペン
タジェニルまたは置換シクロペンタジェニル基であり; Yは窒素またはリンであり;Rはそれぞれの場合独立
に10以下の炭素原子もしくはケイ素原子をもつアルキ
ル、アリール、シリルまたはそれらの組合せであり;mは
1〜4の整数である〕のYを介してMに共有結合してい
る2価の基であり、X,nおよびA-は前記のとおりであ
る〕に相当する化合物である。
ジエニル金属成分(第一成分)の好適な例は、ヒドロカ
ルビル置換モノシクロペンタジエニル金属化合物、たと
えばシクロペンタジエニルジルコニウムトリメチル,シ
クロペンタジエニルジルコニウムトリエチル,シクロペ
ンタジエニルジルコニウムトリプロピル,シクロペンタ
ジエニルチタントリメチル,シクロペンタジエニルチタ
ントリフエニル,など;ヒドロカルビル置換化合物たと
えばシクロペンタジエニルチタントリイソプロポキサイ
ド,シクロペンタジエニルジルコニウムトリフエノキサ
イドなど;ハロ置換化合物たとえばシクロペンタジエニ
ルジルコニウムトリクロライド,インデニルチタントリ
クロライド,など;および置換基の混合物を含む化合物
たとえばシクロペンタジエニルチタンイソプロポキサイ
ドジメチル,ペンタメチルシクロペンタジエニルジルコ
ニウムメチルジクロライド,(t−ブチルアミド)(テ
トラメチル−η5−シクロペンタジエニル)−1,2−エ
ンタジイルジルコニウムジクロライド,(t−ブチルア
ミド)(テトラメチル−η5−シクロペンタジエニル)
−1,2−エタンジイルチタンジクロライド,(メチルア
ミド)(テトラメチル−η5−シクロペンタジエニル)
−1,2−エタンジイルジルコニウムジクロライド,(メ
チルアミド)(テトラメチル−η5−シクロペンタジエ
ニル)−1,2−エタンジイルチタンジクロライド,(エ
チルアミド)(テトラメチル−η5−シクロペンタジエ
ニル)・メチレンチタンジクロライド,(t−ブチルア
ミド)ジベンジル(テトラメチル−η5−シクロペンタ
ジエニル)シランジルコニウムジベンジル,(ベンジル
アミド)ジメチル(テトラメチル−η5−シクロペンタ
ジエニル)シランチタンジクロライド,(フエニルホス
フイド)ジメチル(テトラメチル−η5−シクロペンタ
ジエニル)シランジルコニウムジベンジルなどである。
ンタジエニル環の金属原子と置換分との間に共有結合を
含む化合物の例である。好ましい置換分は金属原子にδ
縮合しうる置換分である。このような化合物は対応する
金属クロライドを置換シクロペンタジエニル基(たとえ
ばシクロペンタジエニル・アルカンジイル,シクロペン
タジエニル・シランアミド,またはシクロペンタジエニ
ル・ホスフイド化合物)のジリチウム塩と混合すること
によつて容易に製造することができる。この反応は通常
の合成法を使用して不活性液体(たとえばテトラヒドロ
フラン,C5-10アルカン,トルエンなど)中で行なわれ
る。
は次の一般式によつて表わすことができる。
テツド酸であり;Bは原子価3の状態のホウ素であり;そ
してQは前記定義のとおりである。
ホウ素化合物の例は次のとおりであるが、これらに限定
されない: トリアルキル置換アンモニウム塩たとえばトリエチル
アンモニウムテトラフエニルボレート,トリプロピルア
ンモニウムテトラフエニルボレート,トリ(n−ブチ
ル)アンモニウムテトラフエニルボレート,トリメチル
アンモニウムテトラ(p−トリルボレート),トリブチ
ルアンモニウムテトラキス−ペンタフルオロフエニルボ
レート,トリプロピルアンモニウムテトラキス−2,4−
ジメチルフエニルボレート,トリブチルアンモニウムテ
トラキス−3,5−ジメチルフエニルボレート,トリエチ
ルアンモニウムテトラキス−(3,5−ジ−トリフルオロ
メチルフエニル)ボレートなど。また、N,N−ジアルキ
ルアニリニウム塩たとえばN,N−ジエチルアニリニウム
テトラフエニルボレート,N,N−2,4,6−ペンタメチルア
ニリニウムテトラフエニルボレートなど;ジアルキルア
ンモニウム塩たとえばジ−(i−プロピル)アンモニウ
ムテトラキスペンタフルオロフエニルボレート,ジシク
ロヘキシルアンモニウムテトラフエニルボレートなど;
およびトリアリールホスホニウム塩たとえばトリフエニ
ルホスホニウムテトラフエニルボレート,トリ(メチル
フエニル)ホスホニウムテトラキス−ペンタフルオロフ
エニルボレート,トリ(ジメチルフエニル)ホスホニウ
ムテトラフエニルボレートなど;も好適である。
成分の大部分と組合せられて活性なオレフイン重合触媒
を生じるけれども、第1成分から始めに生成した金属カ
チオンまたはそれらの分解生成物が比較的安定な触媒で
あるということが連続重合操作にとつて重要である。ま
たアンモニウム塩を使用する場合、第2化合物のアニオ
ンが加水分解に対して安定であることも重要である。更
に、第2成分の酸性度が第1成分に対して十分であつ
て、必要なプロトン移動を促進させることも重要であ
る。逆に、金属錯体の塩基性度も必要なプロトン移動を
促進するに十分でなければならない。若干のメタローセ
ン(非金属性)化合物はブロンステツド酸以外のすべて
との反応に対して耐性があり、従つて第2成分のすべて
と本発明の触媒を形成する第1成分として好適ではな
い。最も好ましいモノシクロペンタジエニル金属化合物
は水溶液によつて加水分解しうる化合物である。
と第2成分との組合せに関して、活性触媒の製造のため
に組合せられるこれら2成分はアニオン断片とくにアリ
ール基または弗素もしくは水素原子が金属カチオンに移
動して触媒的に不活性な種を形成するのを避けるように
えらばれるべきであることに注目すべきである。これ
は、シクロペンタジエニル炭素上の置換分ならびにアニ
オンの芳香族炭素環上の置換分から生ずる立体障害によ
つて行なうことができる。従つてパーヒドロカルビル置
換シクロペンタジエニル基を含む第1成分は非置換シク
ロペンタジエニル基を第1成分がなしうるよりも広い範
囲の第2成分と共に有効に使用することができる。然し
ながら、シクロペンタジエニル基上の置換分の量と大き
さが減少するにつれて、劣化に対してより耐性のあるア
ニオンを含む第2成分たとえばフエニル環のオルソ位に
置換分をもつものを用いてより有効な触媒がえられる。
アニオンを劣化に対してより耐性にする別の手段はアニ
オン中のフツ素置換基特に完全弗素置換基によつて与え
られる。弗素置換安定性アニオンは次いでより広い範囲
の第1成分と共に使用することができる。
おいて好適な溶媒中で上記2成分を混合することによつ
て製造される。この触媒を使用して2〜約18個の炭素原
子をもつα−オレフインおよび/またはアセチレン性不
飽和モノマーおよび/または約4〜約18個の炭素原子を
もつジオレフインを単独でまたは組合せにおいて重合さ
せることができる。この触媒はまたα−オレフイン,ジ
オレフインおよび/またはアセチレン性不飽和モノマー
を他の不飽和モノマーと組合せて重合させるためにも使
用することができる。好ましい態様において、この触媒
はビニル芳香族モノマーとビニル芳香族モノマー以外の
オレフインとのコポリマーとくにスチレンとエチレンま
たはプロピレンとのコポリマーを製造するのに使用され
る。一般に、重合は当業技術において周知の条件におい
て行なうことができる。触媒成分を重合プロセスに直接
に添加し、そして好適な溶媒または希釈剤(凝縮モノマ
ーを包含する)を重合プロセス中に使用するならば、触
媒系はその場で生成することがもちろん理解されるであ
ろう。然しながら、触媒はこれを重合工程に加える前に
好適な溶媒中別の工程で製造するのが好ましい。触媒は
発火性の種を含んではならないけれども、触媒成分は水
分と酸素の双方に敏感であり、不活性雰囲気(たとえば
窒素,アルゴンまたはヘリウム)中で取扱い及び搬送す
べきである。
不活性非プロトン性溶媒もしくは希釈剤中で製造され
る。好適な溶媒または希釈剤としてオレフイン,ジオレ
フインおよびアセチレン性不飽和モノマーの重合におい
て溶媒として有用であることの知られている従来技術に
周知のすべての溶媒をあげることができる。然し好適な
溶媒として次のものをあげることができるが、必ずしも
これらに限定されない:直鎖または枝分かれ鎖の炭化水
素たとえばイソブタン,ブタン,ペンタン,ヘキサン,
ヘプタン,オクタンなど;環状および脂環状炭化水素た
とえばシクロヘキサン,シクロペンタン,メチルシクロ
ペンタン,メチルシクロヘプタンなど;ならびに芳香族
およびアルキル置換芳香族化合物たとえばベンゼン,ト
ルエン,キシレンなど。好適な溶媒はまた液状オレフイ
ン類をも包含する。これらはモノマーまたはコモノマー
としても働き、例としてエチレン,プロピレン,ブタジ
エン,シクロペンテン,1−ヘキセン,3−メチル−1−ペ
ンテン,4−メチル−1−ペンテン,1,4−ヘキサジエン,1
−オクテン,1−デセン,スチレンなどがあげられる。
も、本発明の改良触媒の製造に使用する2成分を好適な
溶媒または希釈剤中で混合するとき、第2成分(酸性部
分)のカチオンの一部または全部は第1成分の置換基
(X)の1つと結合する。その結果として、中性化合物
XHが放出され、この中性化合物は溶液中にとどまるか、
あるいはガスとして放出される。この点に関して、第1
成分中のXがハイドライドであるならば水素ガスが発生
することに注目すべきである。同様に、Xがメチル基で
あるならば、メタンがガスとして発生する。Xがアルコ
キサイドであるならば、アルコールが生成する。
1成分の置換基が放出されるとき、触媒製造に使用する
第2成分中に始めから含まれている非配位性のアニオン
は第1成分から生成する金属カチオンまたはその分解生
成物の電荷を均衡させる。この金属カチオンおよび非配
位性アニオンは、触媒が1種またはそれ以上のオレフイ
ン,ジオレフインおよび/またはアセチレン性不飽和モ
ノマーの単独と或いは1種またはそれ以上の他のモノマ
ーまたは別の中性ルイス塩基と接触せしめられるまで、
結合されたまゝでいる。上記の如く、第2成分中に含ま
れるアニオンはモノマーによる迅速な置換を可能にして
重合を促進するに十分に可動性でなければならない。
いホウ素含有化合物を第2成分として使用するとき、下
記に示す一般式を参照することによつて表わすことがで
きる。
定性および生成速度は、溶媒の選択,えらばれた〔L−
H〕+の酸性度,特定のL,アニオン,反応完了時の温
度,およびえらばれた金属の特定のモノシクロペンタジ
エニル誘導体に応じて変化する。一般に、始めに生成す
るイオン対は活性重合触媒であり、α−オレフイン,ジ
オレフインおよびアセチレン性不飽和モノマーのいづれ
か単独または他のモノマーとの組合せを重合させる。然
しながら、ある場合には、始めの金属カチオンは分解し
て活性重合触媒を生じる。
成分と混合して活性触媒とくに活性重合触媒を生成す
る。然しながら、実際の活性触媒種はその分離と爾後の
確認を可能にするように十分に安定であるとは必ずしも
限らない。その上、および生成する初期金属カチオンの
多くは比較的安定であるけれども、初期に生成する金属
カチオンは多くの場合分解して1種またはそれ以上の他
の触媒的に活性な種になる。
ネシウム基材の化合物のような共触媒を含むチグラ−・
ナツタ触媒により生成するポリマー中に一般に見出され
る痕跡量の金属を含まないポリマー生成物を生成するよ
うにえらばれる。本発明の触媒により生成するポリマー
は、金属アルキル(たとえばアルミニウムアルキル)ま
たはアルミノキサンを含むより通常のチグラ−・ナツタ
型触媒により生成するポリマーよりも広い範囲の用途を
もつ。この触媒は均一触媒として又は好適な担体(たと
えばアルミナまたはシリカ)に担持させた触媒として使
用することができる。
ルシクロペンタジエンであり、Mはチタンまたはジルコ
ニウムであり、nは2であり、XはC1 〜 4アルキルまた
はアルコキサイドであり、Aはテトラキス・ペンタフル
オロフエニルボレートである。
上のC2〜C8α−オレフイン特にエチレンまたはプロピレ
ン、最も好ましくはエチレンを0℃〜200℃好ましくは2
5℃〜100℃の範囲の温度において、大気圧〜1000psig
(7MPa)好ましくは15〜500psig(0.1〜3.5MPa)の範囲
の圧力で重合させるのに使用される。本発明の最も好ま
しい態様において、触媒はエチレンを均一重合させるた
めに又はエチレンとC3〜C8α−オレフイン(スチレンを
包含する)と共重合させてコポリマーを作るために使用
される。この好ましい態様および最も好ましい態様の双
方において、モノマーは約1〜約60分の範囲の通常の保
持時間のあいだ重合条件に保持され、触媒はモノマー1
モル当り約10-7−約10-1モルの範囲の濃度で使用され
る。
記の実施例を参照することによつて更になお明らかにな
るであろう。然しながら、これらの実施例は本発明を具
体的に説明するためにのみ提示するものであつて、本発
明を限定するものと解すべきではない。
サイドジメチルおよびトリエチルアンモニウムテトラキ
ス・ペンタフルオロフエニルボレート 室温の乾燥ボツクスにおいて、33mgのペンタメチルシ
クロペンタジエニルチタンイソプロポキサイドジメチル
〔CpTi(O−i−Pr)Me2〕(0.12ミリモル)を1mlのベ
ンゼンと混合し、生成溶液をピペツトで250mlの3ツ口
フラスコに入れた。栓,真空ライン用のアダプタ,およ
び固体添加ロートを取付けた。添加ロートに80mg(0.10
ミリモル)のトリエチルアンモニウムテトラキス・ペン
タフルオロフエニルボレート(〔HNEt3〕+〔B(C
6F5)4〕−)を充てんした。添加ロートに栓をして装
置を真空ラインに取付けた。ベンゼンを真空下にフラス
コから除き、75mlの新しいベンゼンを真空下−78℃のフ
ラスコに留出させた。室温に加温後、溶液を1気圧(0.
1MPa)のエチレンで覆つた。固体の(〔HNEt3〕+〔B
(C6F5)4〕−)を室温で加え、溶液が黄色に変つたこ
とを観察した。20分後に溶液は黒色であり、ポリエチレ
ンの沈殿が観察された。1時間後に、ポリマーをメタノ
ールで沈殿させ、収集し、メタノールで洗浄し、真空下
で一夜乾燥し、0.49gのポリマーを得た。
よびトリエチルアンモニウムテトラキス・ペンタフルオ
ロフエニルボレート ペンタメチルシクロペンタジエニルチタントリメチル
およびトリエチルアンモニウム・ペンタフルオロフエニ
ルボレートを使用して実施例1の反応条件を実質的にく
りかえした。反応はトルエン中で約10時間室温において
続けた。メタンガスおよびアンモニアの副生物が観察さ
れた。約45℃に1時間加熱後、溶媒を真空下で除去し黒
色固体をえた。この固体を石油エーテルで3回洗浄し、
減圧下に乾燥した。回収した生成物は所望のペンタメチ
ルシクロペンタジエニル・チタンジメチルテトラキス・
ペンタフルオロフエニルボレートであると確信された。
このものは周知のチグラー・ナツタ重合条件下でオレフ
インを重合させるのに使用することができる。
シクロペンタジエニル)シランチタンジメチルおよびト
リエチルアンモニウムテトラキス・ペンタフルオロフエ
ニルボレート 25mlフラスコに275mgの(t−ブチルアミド)(ジメ
チル)(η5−テトラメチルシクロペンタジエニル)シ
ランチタンジクロライド(0.75ミリモル)を充てんし、
これに小さいフリツトガラスを取付けた。このフリツト
を真空にし、15mlのジエチルエーテルをフラスコに真空
で移した。−78℃において、1.1mlのMeLi(ヘキサン中
1.4M,1.54ミリモル,2.05当量)を注射器を使用してサイ
ドアーム・バルブから添加した。調整変化は観察されな
かつた。5分後に内容物を取出し、溶液を室温に加温し
た。1時間後、この溶液は暗緑色で不透明であつた。ジ
エチルエーテルを追出して10mlのヘキサンで置換した。
この溶液を25℃で10分間撹拌してから過した。固体を
約2mlにまで減少させ、溶液を−78℃に冷却し、フリツ
ト冷却フリツプから暗オリーブ色の固体を集めた。減圧
下に30分間乾燥した後に、固体の(t−ブチルアミド)
ジメチル(テトラメチル−η5−シクロペンタジエニ
ル)シランチタンジメチルを単離した(138mg,56%)。
ブチルアミド)ジメチル(テトラメチル−η5−シクロ
ペンタジエニル)シランチタンジメチルを充てんした。
このフラスコに栓,真空ラインアダプターおよび固体添
加ロートを取付けた。この添加ロートに77mgの〔HNE
t3〕+〔B(C6H5)4〕−を充てんし、栓をした。この
フラスコを真空にし、50mlのベンゼンを固体上に留出さ
せた。この溶液を25℃に加温し、1気圧(0.1MPa)のエ
チレンで覆つた。次いで固体〔HNEt3〕+〔B(C6F5)
4〕−を加え、黄色溶液を得た。1時間後、粘稠黄色溶
液は依然としてエチレンを吸収しつつあつた。生成する
ゼラチン状混合物をメタノールで急冷して白色沈殿をえ
た。この沈殿を過し、メタノールで2回洗浄し、真空
乾燥して0.56gのポリエチレンを得た。
ン溶媒を、次いで表Iに同定される適量のコモノマーを
満たした。反応器を適温に加熱し、次いでエチレンで加
圧した。水素を用いた場合は次いで75mlの供給容器から
反応器へ膨張させた。数分後、トルエン溶液中の触媒と
共触媒の混合物を転移配管を通して反応器に加え、次い
で5mlのトルエンで転移配管を洗った。反応器を開けて
メタノールと抗酸化剤を加えて反応を停止した。ポリマ
ーを減圧下に一定重量まで乾燥した。結果を表Iに示
す。用いたのは次の触媒と共触媒である。
5−シクロペンタジエニル)シランチタンジメチル II.(タートブチルアミド)ジメチル(テトラメチル−
η5−シクロペンタジエニル)シランジルコニウムメチ
ル 共触媒 A.ジメチルアニリニウム テトラキスパーフルオロフェ
ニルボレート B.トリエチルアンモニウム テトラキスパーフルオロフ
ェニルボレート C.トリエチルアンモニウム メチルトリスパーフルオロ
フェニルボレート D.トリエチルアンモニウム アリルトリスパーフルオロ
フェニルボレート E.トリエチルアンモニウム n−ブチルトリスパーフル
オロフェニルボレート F.トリエチルアンモニウム ベンジルトリスパーフルオ
ロフェニルボレート 結果は表Iに含まれる。
Claims (11)
- 【請求項1】次式 CpMXn+A- 〔式中、Mはチタンまたはジルコニウムであり;Cpは式 〔R′はそれぞれの場合独立に水素、ハロゲンまたは20
以下の炭素原子をもつアルキル、アリールもしくはハロ
アルキル、シリル基およびそれらの組合せからえらばれ
た基であり; R″はR′であるか又は式 〔Yは窒素またはリンであり;Rはそれぞれの場合独立
に10以下の炭素原子もしくはケイ素原子をもつアルキ
ル、アリール、シリルまたはそれらの組合せであり;mは
1〜4の整数である〕のYを介してMに共有結合してい
る2価の基である〕 で示されるシクロペンタジエニルもしくは置換シクロペ
ンタジエニル基であり; Xはそれぞれの場合独立にハロゲンまたは20以下の炭素
原子をもつアルキル、アリール、アリールオキシまたは
アルコキシであり; nは1または2であり;そして A-は〔BQ4〕− 〔Bは原子価が3の状態のホウ素であり;そしてQはそ
れぞれの場合独立にハイドライド、ハロゲンまたは20個
以下の炭素原子をもつジアルキルアミド、アルコキサイ
ド、アリールオキサイド、ヒドロカルビルもしくは置換
ヒドロカルビル基であって但しQハライドは1個以下で
ある〕 である〕 に相当するモノシクロペンタジエニルまたは置換モノシ
クロペンタジエニル金属錯体含有化合物。 - 【請求項2】R″が式 〔Yは窒素またはリンであり;Rはそれぞれの場合独立
に10以下の炭素原子もしくはケイ素原子をもつアルキ
ル、アリール、シリルまたはそれらの組合せであり;mは
1〜4の整数である〕のYを介してMに共有結合してい
る2価の基であり;nが1である請求項1記載の化合物。 - 【請求項3】R″がR′であり、nが2である請求項1
記載の化合物。 - 【請求項4】R′の炭素原子が10以下である請求項1〜
3のいずれか1項記載の化合物。 - 【請求項5】R′がメチルである請求項1〜4のいずれ
か1項記載の化合物。 - 【請求項6】Mがチタンである請求項1〜5のいずれか
1項記載の化合物。 - 【請求項7】Cpがペンタメチルシクロペンタジェニルで
あり、Xが炭素原子1〜4のアルキルまたはアルコキシ
である請求項3記載の化合物。 - 【請求項8】A-がフルオロ置換アニオンである請求項1
〜7のいずれか1項記載の化合物。 - 【請求項9】A-がパーフルオロ置換アニオンである請求
項8記載の化合物。 - 【請求項10】A-がテトラキス(ペンタフルオロフェニ
ル)ボレートである請求項9記載の化合物。 - 【請求項11】(タートブチルアミド)ジメチル(テト
ラメチル−η5−シクロペンタジェニル)シランチタン
メチルテトラキス(ペンタフルオロフェニル)ボレート
である請求項1記載の化合物。
Applications Claiming Priority (4)
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US40716989A | 1989-09-14 | 1989-09-14 | |
US407169 | 1989-09-14 | ||
US07/547,728 US5064802A (en) | 1989-09-14 | 1990-07-03 | Metal complex compounds |
US547728 | 1990-07-03 |
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JPH03139504A JPH03139504A (ja) | 1991-06-13 |
JP2736935B2 true JP2736935B2 (ja) | 1998-04-08 |
Family
ID=27019786
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Application Number | Title | Priority Date | Filing Date |
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JP2242861A Expired - Lifetime JP2736935B2 (ja) | 1989-09-14 | 1990-09-14 | 金属錯体化合物 |
JP9217230A Expired - Lifetime JP3010349B2 (ja) | 1989-09-14 | 1997-08-12 | 付加重合触媒及び付加重合方法 |
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US (2) | US5064802A (ja) |
EP (2) | EP0765882A3 (ja) |
JP (2) | JP2736935B2 (ja) |
KR (1) | KR0168048B1 (ja) |
CN (1) | CN1028369C (ja) |
BR (1) | BR9004695A (ja) |
CA (1) | CA2025332C (ja) |
DE (1) | DE69031413T3 (ja) |
ES (1) | ES2106021T5 (ja) |
FI (1) | FI100104B (ja) |
GE (1) | GEP19991571B (ja) |
HK (1) | HK1001919A1 (ja) |
HU (1) | HU218602B (ja) |
IL (1) | IL95598A (ja) |
NO (1) | NO302702B1 (ja) |
NZ (1) | NZ235215A (ja) |
RO (1) | RO106411B1 (ja) |
RU (1) | RU2095363C1 (ja) |
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YU (1) | YU47114B (ja) |
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JPS62187708A (ja) * | 1985-11-11 | 1987-08-17 | Idemitsu Kosan Co Ltd | スチレン系重合体の製造法 |
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JPH0780930B2 (ja) * | 1985-12-26 | 1995-08-30 | 三井石油化学工業株式会社 | α−オレフインの重合方法 |
PL276385A1 (en) * | 1987-01-30 | 1989-07-24 | Exxon Chemical Patents Inc | Method for polymerization of olefines,diolefins and acetylene unsaturated compounds |
IL85097A (en) * | 1987-01-30 | 1992-02-16 | Exxon Chemical Patents Inc | Catalysts based on derivatives of a bis(cyclopentadienyl)group ivb metal compound,their preparation and their use in polymerization processes |
US5055438A (en) * | 1989-09-13 | 1991-10-08 | Exxon Chemical Patents, Inc. | Olefin polymerization catalysts |
JPH01501487A (ja) * | 1987-06-17 | 1989-05-25 | ザ ダウ ケミカル カンパニー | シンジオタクチックポリスチレンの製造のための触媒および方法 |
JPH0757767B2 (ja) * | 1988-01-19 | 1995-06-21 | 出光興産株式会社 | スチレン系重合体の製造方法及び触媒 |
JP2796972B2 (ja) * | 1988-10-19 | 1998-09-10 | 旭化成工業株式会社 | 立体規則性芳香族ビニル重合体の製法 |
PL286365A1 (en) * | 1989-08-03 | 1991-04-22 | Exxon Chemical Patents Inc | Method of polymerizing especially ethylene any polymerization catalyst and method of obtaining same |
CA2024830A1 (en) * | 1989-09-29 | 1991-03-30 | Richard E. Campbell, Jr. | Process for preparation of syndiotactic vinyl aromatic polymers |
DE551277T1 (de) † | 1990-06-22 | 1996-10-10 | Exxon Chemical Patents Inc., Linden, N.J. | Aluminiumfreie monocyclopentadienyl-metallocenkatalysatoren für olefinpolymerisation. |
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