JPH0222086B2 - - Google Patents
Info
- Publication number
- JPH0222086B2 JPH0222086B2 JP55076775A JP7677580A JPH0222086B2 JP H0222086 B2 JPH0222086 B2 JP H0222086B2 JP 55076775 A JP55076775 A JP 55076775A JP 7677580 A JP7677580 A JP 7677580A JP H0222086 B2 JPH0222086 B2 JP H0222086B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- organoaluminum
- mmol
- compounds
- polymerization
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 aluminum halide Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 229910052719 titanium Inorganic materials 0.000 claims description 16
- 239000010936 titanium Substances 0.000 claims description 16
- 150000001491 aromatic compounds Chemical class 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000004711 α-olefin Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 238000012721 stereospecific polymerization Methods 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 24
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 15
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 15
- 239000012190 activator Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 5
- 230000037048 polymerization activity Effects 0.000 description 5
- 230000000707 stereoselective effect Effects 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000013081 microcrystal Substances 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- DMBVHCBMTZRQTO-UHFFFAOYSA-N 1,3-bis(2-methylpentan-2-yl)naphthalen-2-ol Chemical compound C1=CC=C2C(C(C)(C)CCC)=C(O)C(C(C)(C)CCC)=CC2=C1 DMBVHCBMTZRQTO-UHFFFAOYSA-N 0.000 description 1
- NSQZPDNLHKKWHY-UHFFFAOYSA-N 1,3-bis(2-methylpentan-2-yl)phenanthren-2-ol Chemical compound C1=CC=C2C(C=C(C(=C3C(C)(C)CCC)O)C(C)(C)CCC)=C3C=CC2=C1 NSQZPDNLHKKWHY-UHFFFAOYSA-N 0.000 description 1
- YRZOMIQAOVISEV-UHFFFAOYSA-N 1,3-ditert-butylanthracen-2-ol Chemical compound C1=CC=C2C=C(C(=C(C(C(C)(C)C)=C3)O)C(C)(C)C)C3=CC2=C1 YRZOMIQAOVISEV-UHFFFAOYSA-N 0.000 description 1
- DDEWZZFCOPRPHZ-UHFFFAOYSA-N 2,4-ditert-butyl-3-[(2,6-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1CC1=C(C(C)(C)C)C=CC(O)=C1C(C)(C)C DDEWZZFCOPRPHZ-UHFFFAOYSA-N 0.000 description 1
- YSFPRMZFDMFZGS-UHFFFAOYSA-N 2,4-ditert-butyl-3-[2-(2,6-ditert-butyl-3-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C1=C(C(C)(C)C)C=CC(O)=C1C(C)(C)C YSFPRMZFDMFZGS-UHFFFAOYSA-N 0.000 description 1
- RCALTZPFYQMVGL-UHFFFAOYSA-N 2,6-dicyclohexyl-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1C1CCCCC1 RCALTZPFYQMVGL-UHFFFAOYSA-N 0.000 description 1
- KSPSGLZRAWUOKJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-propan-2-ylphenol Chemical compound CC(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KSPSGLZRAWUOKJ-UHFFFAOYSA-N 0.000 description 1
- JAJCQYUAORSGHI-UHFFFAOYSA-N 2,8-ditert-butylnaphthalen-1-ol Chemical compound C1=CC=C(C(C)(C)C)C2=C(O)C(C(C)(C)C)=CC=C21 JAJCQYUAORSGHI-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- YVXZDHMHPCFGGQ-UHFFFAOYSA-N 3-[2,3-bis[3-hydroxy-2,6-bis(2-methylpentan-2-yl)phenyl]phenyl]-2,4-bis(2-methylpentan-2-yl)phenol Chemical compound CCCC(C)(C)C1=CC=C(O)C(C(C)(C)CCC)=C1C1=CC=CC(C=2C(=C(O)C=CC=2C(C)(C)CCC)C(C)(C)CCC)=C1C1=C(C(C)(C)CCC)C=CC(O)=C1C(C)(C)CCC YVXZDHMHPCFGGQ-UHFFFAOYSA-N 0.000 description 1
- HQGFVBPXFOPSAY-UHFFFAOYSA-N 3-[3,5-bis(2,6-ditert-butyl-3-hydroxyphenyl)-2,4,6-trimethylphenyl]-2,4-ditert-butylphenol Chemical compound CC1=C(C=2C(=C(O)C=CC=2C(C)(C)C)C(C)(C)C)C(C)=C(C=2C(=C(O)C=CC=2C(C)(C)C)C(C)(C)C)C(C)=C1C1=C(C(C)(C)C)C=CC(O)=C1C(C)(C)C HQGFVBPXFOPSAY-UHFFFAOYSA-N 0.000 description 1
- SFBGCRIRFDMPLI-UHFFFAOYSA-L 3-methylbutylaluminum(2+);dichloride Chemical compound [Cl-].[Cl-].CC(C)CC[Al+2] SFBGCRIRFDMPLI-UHFFFAOYSA-L 0.000 description 1
- OLKXWPLHZNRKNZ-UHFFFAOYSA-N 4-butyl-2,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCCCC1=CC(C(C)(C)CC)=C(O)C(C(C)(C)CC)=C1 OLKXWPLHZNRKNZ-UHFFFAOYSA-N 0.000 description 1
- RXUVSUWTUYNHFP-UHFFFAOYSA-N 4-methoxy-2,6-di(propan-2-yl)phenol Chemical compound COC1=CC(C(C)C)=C(O)C(C(C)C)=C1 RXUVSUWTUYNHFP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JKFJJYOIWGFQGI-UHFFFAOYSA-M bromo-bis(2-methylpropyl)alumane Chemical compound [Br-].CC(C)C[Al+]CC(C)C JKFJJYOIWGFQGI-UHFFFAOYSA-M 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- GJDATTLXPMXFQF-UHFFFAOYSA-M chloro(dicyclohexyl)alumane Chemical compound [Cl-].C1CCCCC1[Al+]C1CCCCC1 GJDATTLXPMXFQF-UHFFFAOYSA-M 0.000 description 1
- ISFMCQATCMRFPY-UHFFFAOYSA-M chloro(diphenyl)alumane Chemical compound [Cl-].C=1C=CC=CC=1[Al+]C1=CC=CC=C1 ISFMCQATCMRFPY-UHFFFAOYSA-M 0.000 description 1
- LKRBKNPREDAJJQ-UHFFFAOYSA-M chloro-di(propan-2-yl)alumane Chemical compound [Cl-].CC(C)[Al+]C(C)C LKRBKNPREDAJJQ-UHFFFAOYSA-M 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- LNIBDQJJKYIJRE-UHFFFAOYSA-M dibutyl(phenoxy)alumane Chemical compound [O-]C1=CC=CC=C1.CCCC[Al+]CCCC LNIBDQJJKYIJRE-UHFFFAOYSA-M 0.000 description 1
- UZVQWTNJZQZICK-UHFFFAOYSA-L dichloro(2-methylpropoxy)alumane Chemical compound [Cl-].[Cl-].CC(C)CO[Al+2] UZVQWTNJZQZICK-UHFFFAOYSA-L 0.000 description 1
- NPEFICOHWIZPMC-UHFFFAOYSA-L dichloroalumanylium;ethanolate Chemical compound [Cl-].[Cl-].CCO[Al+2] NPEFICOHWIZPMC-UHFFFAOYSA-L 0.000 description 1
- MVGUIMCFFQICHB-UHFFFAOYSA-N diethyl(phenyl)alumane Chemical compound CC[Al](CC)C1=CC=CC=C1 MVGUIMCFFQICHB-UHFFFAOYSA-N 0.000 description 1
- KEIUPWWAAXLGMG-UHFFFAOYSA-M dihexylalumanylium;iodide Chemical compound [I-].CCCCCC[Al+]CCCCCC KEIUPWWAAXLGMG-UHFFFAOYSA-M 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LQQFUXQFANOCNZ-UHFFFAOYSA-N hexyl-di(propan-2-yl)alumane Chemical compound CCCCCC[Al](C(C)C)C(C)C LQQFUXQFANOCNZ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XKUUSJWNAAMDIV-UHFFFAOYSA-L methoxyaluminum(2+);dibromide Chemical compound [Br-].[Br-].CO[Al+2] XKUUSJWNAAMDIV-UHFFFAOYSA-L 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- XZVMVRCDNQBHBW-UHFFFAOYSA-K phenoxyaluminum(2+);diiodide Chemical compound [I-].[I-].[Al+2]OC1=CC=CC=C1 XZVMVRCDNQBHBW-UHFFFAOYSA-K 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- FBAHXJYOIKNAAZ-UHFFFAOYSA-L propan-2-ylaluminum(2+);diiodide Chemical compound [I-].[I-].CC(C)[Al+2] FBAHXJYOIKNAAZ-UHFFFAOYSA-L 0.000 description 1
- VKBFQELXJIPDFJ-UHFFFAOYSA-L propylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCC[Al+2] VKBFQELXJIPDFJ-UHFFFAOYSA-L 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
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Claims (1)
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ã®ç¯å²ç¬¬ïŒãïŒé ã®ããããã«èšèŒã®æ¹æ³ã
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7920181 | 1979-06-11 |
Publications (2)
| Publication Number | Publication Date |
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| JPS562303A JPS562303A (en) | 1981-01-12 |
| JPH0222086B2 true JPH0222086B2 (ja) | 1990-05-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7677580A Granted JPS562303A (en) | 1979-06-11 | 1980-06-09 | Alphaaolefin stereospecific polymerization and catalysts therefor |
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| US (1) | US4478989A (ja) |
| EP (1) | EP0021478B1 (ja) |
| JP (1) | JPS562303A (ja) |
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| BR (1) | BR8003556A (ja) |
| CA (1) | CA1152056A (ja) |
| DE (1) | DE3070879D1 (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1152056A (en) * | 1979-06-11 | 1983-08-16 | Brian L. Goodall | Process for the stereospecific polymerization of an alpha-olefin and an alpha-olefin polymerization catalyst system |
| US4529780A (en) * | 1981-11-19 | 1985-07-16 | Northern Petrochemical Company | Process for polymerizing alpha olefins with phenolic compound containing catalysts |
| EP0107871B1 (en) * | 1982-10-27 | 1986-10-15 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of polyisoprene |
| FR2604439B1 (fr) * | 1986-09-26 | 1989-07-28 | Solvay | Solide catalytique utilisable pour la polymerisation stereospecifique des alpha-olefines, procede pour le preparer et procede pour polymeriser des alpha-olefines en sa presence |
| US5780379A (en) * | 1987-09-25 | 1998-07-14 | Solvay Polyolefins Europe-Belgium (Societe Anonyme) | Process for the stereospecific polymerization of alpha-olefins and catalyst system which can be employed for this polymerization |
| JPH0791327B2 (ja) * | 1988-03-24 | 1995-10-04 | åºå èç£æ ªåŒäŒç€Ÿ | ã¹ãã¬ã³ç³»éåäœã®è£œé æ¹æ³ãšãã®è§Šåª |
| USH860H (en) | 1989-01-26 | 1990-12-04 | Shell Oil Company | Method for polymerizing alpha olefins |
| BE1003968A3 (fr) * | 1990-11-08 | 1992-07-28 | Solvay | Solide catalytique utilisable pour la polymerisation stereospecifique des alpha-olefines, procede pour le preparer et procede pour polymeriser des alpha-olefines en sa presence |
| USH1254H (en) | 1992-04-17 | 1993-11-02 | Shell Oil Company | Polymerization process for butene-1 and alpha-olefin monomers |
| US5939346A (en) * | 1992-11-02 | 1999-08-17 | Akzo Nobel N.V. | Catalyst system comprising an aryloxyaluminoxane containing an electron withdrawing group |
| US6465383B2 (en) | 2000-01-12 | 2002-10-15 | Eastman Chemical Company | Procatalysts, catalyst systems, and use in olefin polymerization |
| US6696380B2 (en) | 2000-01-12 | 2004-02-24 | Darryl Stephen Williams | Procatalysts, catalyst systems, and use in olefin polymerization |
| WO2001051526A1 (en) | 2000-01-12 | 2001-07-19 | Eastman Chemical Company | Procatalysts comprising bidentate ligands, catalyst systems, and use in olefin polymerization |
| KR102533991B1 (ko) * | 2014-12-31 | 2023-05-19 | ë€ì° êžë¡ë² í í¬ëë¡ì§ì€ ìììš | íŽëŠ¬ì¬ë í ì¡°ì±ë¬Œ ë° ê·ž ì ì¡°ë°©ë² |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445443A (en) * | 1964-03-24 | 1969-05-20 | Mitsui Petrochemical Ind | Process for the preparation of polyolefins with a transition metal halide-organo aluminum compound catalyst |
| GB1278516A (en) * | 1968-09-19 | 1972-06-21 | Mitsui Petrochemical Ind | STABILISED alpha-MONOOLEFIN POLYMERS |
| FR2212346B1 (ja) * | 1972-12-28 | 1978-12-01 | Nippon Oil Co Ltd | |
| IT1039828B (it) * | 1975-07-09 | 1979-12-10 | Montedison Spa | Componenti di catalizzatori perla polimerizzazione di olefine e catalizzatori da essi ottenuti |
| JPS5218784A (en) * | 1975-08-05 | 1977-02-12 | Nippon Oil Co Ltd | Process for preparing polyolefins |
| US4069169A (en) * | 1975-11-24 | 1978-01-17 | Mitsui Petrochemical Industries Ltd. | Process for preparation of catalyst component supported on high performance carrier |
| CA1152056A (en) * | 1979-06-11 | 1983-08-16 | Brian L. Goodall | Process for the stereospecific polymerization of an alpha-olefin and an alpha-olefin polymerization catalyst system |
-
1980
- 1980-04-09 CA CA000349406A patent/CA1152056A/en not_active Expired
- 1980-05-28 DE DE8080200502T patent/DE3070879D1/de not_active Expired
- 1980-05-28 EP EP80200502A patent/EP0021478B1/en not_active Expired
- 1980-06-09 JP JP7677580A patent/JPS562303A/ja active Granted
- 1980-06-09 AU AU59142/80A patent/AU533552B2/en not_active Ceased
- 1980-06-09 BR BR8003556A patent/BR8003556A/pt unknown
-
1983
- 1983-10-26 US US06/545,574 patent/US4478989A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU5914280A (en) | 1980-12-18 |
| US4478989A (en) | 1984-10-23 |
| EP0021478A1 (en) | 1981-01-07 |
| JPS562303A (en) | 1981-01-12 |
| DE3070879D1 (en) | 1985-08-22 |
| EP0021478B1 (en) | 1985-07-17 |
| AU533552B2 (en) | 1983-12-01 |
| BR8003556A (pt) | 1981-01-05 |
| CA1152056A (en) | 1983-08-16 |
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