JPH0134447B2 - - Google Patents
Info
- Publication number
- JPH0134447B2 JPH0134447B2 JP13845582A JP13845582A JPH0134447B2 JP H0134447 B2 JPH0134447 B2 JP H0134447B2 JP 13845582 A JP13845582 A JP 13845582A JP 13845582 A JP13845582 A JP 13845582A JP H0134447 B2 JPH0134447 B2 JP H0134447B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerization
- titanium
- hours
- general formula
- compound
- 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
- 239000003054 catalyst Substances 0.000 claims description 42
- 239000011777 magnesium Substances 0.000 claims description 22
- 150000003609 titanium compounds Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052749 magnesium Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 13
- 150000003682 vanadium compounds Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229920000098 polyolefin Polymers 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 110
- -1 magnesium halide Chemical class 0.000 description 33
- 239000010936 titanium Substances 0.000 description 32
- 238000006116 polymerization reaction Methods 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 25
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 23
- 239000011949 solid catalyst Substances 0.000 description 23
- 230000005484 gravity Effects 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
- 239000005977 Ethylene Substances 0.000 description 15
- 238000000498 ball milling Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 229910052719 titanium Inorganic materials 0.000 description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 14
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 229920001038 ethylene copolymer Polymers 0.000 description 11
- 238000012685 gas phase polymerization Methods 0.000 description 11
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 229910001220 stainless steel Inorganic materials 0.000 description 10
- 239000010935 stainless steel Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 150000002902 organometallic compounds Chemical class 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000037048 polymerization activity Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- PELBZXLLQLEQAU-UHFFFAOYSA-N chloro-diethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)OCC PELBZXLLQLEQAU-UHFFFAOYSA-N 0.000 description 2
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LTEDQKPGOZDGRZ-UHFFFAOYSA-L propan-2-olate;titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl.CC(C)[O-].CC(C)[O-] LTEDQKPGOZDGRZ-UHFFFAOYSA-L 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
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- BDBNCVOMHKVOST-UHFFFAOYSA-K CCCCCO[Ti](Cl)(Cl)Cl Chemical compound CCCCCO[Ti](Cl)(Cl)Cl BDBNCVOMHKVOST-UHFFFAOYSA-K 0.000 description 1
- JGACQGUYAONLLA-UHFFFAOYSA-M CCO[Ti]Cl Chemical compound CCO[Ti]Cl JGACQGUYAONLLA-UHFFFAOYSA-M 0.000 description 1
- ZALOHOLPKHYYAX-UHFFFAOYSA-L CO[Ti](Cl)(Cl)OC Chemical compound CO[Ti](Cl)(Cl)OC ZALOHOLPKHYYAX-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CIXIHOJSRJAUJX-UHFFFAOYSA-N bromo-diethoxy-methylsilane Chemical compound CCO[Si](C)(Br)OCC CIXIHOJSRJAUJX-UHFFFAOYSA-N 0.000 description 1
- DEFMLLQRTVNBOF-UHFFFAOYSA-K butan-1-olate;trichlorotitanium(1+) Chemical compound [Cl-].[Cl-].[Cl-].CCCCO[Ti+3] DEFMLLQRTVNBOF-UHFFFAOYSA-K 0.000 description 1
- LQJIYGHLYACICO-UHFFFAOYSA-N butan-2-yl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C(C)CC LQJIYGHLYACICO-UHFFFAOYSA-N 0.000 description 1
- XWQLYVIMMBLXPY-UHFFFAOYSA-N butan-2-yloxysilane Chemical compound CCC(C)O[SiH3] XWQLYVIMMBLXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- SZZPLIQXDJWGIS-UHFFFAOYSA-N butoxy(trichloro)silane Chemical compound CCCCO[Si](Cl)(Cl)Cl SZZPLIQXDJWGIS-UHFFFAOYSA-N 0.000 description 1
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 1
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZETBTPGRMAEVIT-UHFFFAOYSA-N chloro(propan-2-yloxy)silane Chemical compound C(C)(C)O[SiH2]Cl ZETBTPGRMAEVIT-UHFFFAOYSA-N 0.000 description 1
- JEZFASCUIZYYEV-UHFFFAOYSA-N chloro(triethoxy)silane Chemical compound CCO[Si](Cl)(OCC)OCC JEZFASCUIZYYEV-UHFFFAOYSA-N 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 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
- ASBBMDURLGJWNN-UHFFFAOYSA-N chloro-diethoxy-ethylsilane Chemical compound CCO[Si](Cl)(CC)OCC ASBBMDURLGJWNN-UHFFFAOYSA-N 0.000 description 1
- GYQKYMDXABOCBE-UHFFFAOYSA-N chloro-dimethoxy-methylsilane Chemical compound CO[Si](C)(Cl)OC GYQKYMDXABOCBE-UHFFFAOYSA-N 0.000 description 1
- RYNOURCVJXQRTJ-UHFFFAOYSA-N chloro-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)Cl RYNOURCVJXQRTJ-UHFFFAOYSA-N 0.000 description 1
- GUGYPJFYIYFMQD-UHFFFAOYSA-N chloro-ethoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(OCC)C1=CC=CC=C1 GUGYPJFYIYFMQD-UHFFFAOYSA-N 0.000 description 1
- XZOKYDWIQYKBFQ-UHFFFAOYSA-N chloro-ethyl-dimethoxysilane Chemical compound CC[Si](Cl)(OC)OC XZOKYDWIQYKBFQ-UHFFFAOYSA-N 0.000 description 1
- QDPOZPYHNZVONG-UHFFFAOYSA-N chloro-ethyl-diphenoxysilane Chemical compound C=1C=CC=CC=1O[Si](Cl)(CC)OC1=CC=CC=C1 QDPOZPYHNZVONG-UHFFFAOYSA-N 0.000 description 1
- CBSOVONSZGCIHR-UHFFFAOYSA-N chloro-methyl-diphenoxysilane Chemical compound C=1C=CC=CC=1O[Si](Cl)(C)OC1=CC=CC=C1 CBSOVONSZGCIHR-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HRYDYCUCHYGDBK-UHFFFAOYSA-N dibutoxy(dichloro)silane Chemical compound CCCCO[Si](Cl)(Cl)OCCCC HRYDYCUCHYGDBK-UHFFFAOYSA-N 0.000 description 1
- UFCXHBIETZKGHB-UHFFFAOYSA-N dichloro(diethoxy)silane Chemical compound CCO[Si](Cl)(Cl)OCC UFCXHBIETZKGHB-UHFFFAOYSA-N 0.000 description 1
- QEHKWLKYFXJVLL-UHFFFAOYSA-N dichloro(dimethoxy)silane Chemical compound CO[Si](Cl)(Cl)OC QEHKWLKYFXJVLL-UHFFFAOYSA-N 0.000 description 1
- OJYGKMYJXWXXPF-UHFFFAOYSA-N dichloro-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](Cl)(Cl)OC(C)C OJYGKMYJXWXXPF-UHFFFAOYSA-N 0.000 description 1
- AXTPGQHJFRSSQJ-UHFFFAOYSA-N dichloro-ethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)Cl AXTPGQHJFRSSQJ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- UFWOWQYGXPYINE-UHFFFAOYSA-N diethyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](CC)(CC)OC1=CC=CC=C1 UFWOWQYGXPYINE-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- SWLVAJXQIOKFSJ-UHFFFAOYSA-N dimethyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](C)(C)OC1=CC=CC=C1 SWLVAJXQIOKFSJ-UHFFFAOYSA-N 0.000 description 1
- BPXCAJONOPIXJI-UHFFFAOYSA-N dimethyl-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(C)OC(C)C BPXCAJONOPIXJI-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- UHSDHNXHBQDMMH-UHFFFAOYSA-L ethanolate;titanium(4+);dichloride Chemical compound CCO[Ti](Cl)(Cl)OCC UHSDHNXHBQDMMH-UHFFFAOYSA-L 0.000 description 1
- RMTCVMQBBYEAPC-UHFFFAOYSA-K ethanolate;titanium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].CCO[Ti+3] RMTCVMQBBYEAPC-UHFFFAOYSA-K 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DFJDZTPFNSXNAX-UHFFFAOYSA-N ethoxy(triethyl)silane Chemical compound CCO[Si](CC)(CC)CC DFJDZTPFNSXNAX-UHFFFAOYSA-N 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- HGWSCXYVBZYYDK-UHFFFAOYSA-N ethyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CC)OC1=CC=CC=C1 HGWSCXYVBZYYDK-UHFFFAOYSA-N 0.000 description 1
- MYEJNNDSIXAGNK-UHFFFAOYSA-N ethyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](CC)(OC(C)C)OC(C)C MYEJNNDSIXAGNK-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 1
- QZCOACXZLDQHLQ-UHFFFAOYSA-M methanolate titanium(4+) chloride Chemical compound [Cl-].[Ti+4].[O-]C.[O-]C.[O-]C QZCOACXZLDQHLQ-UHFFFAOYSA-M 0.000 description 1
- OKENUZUGNVCOMC-UHFFFAOYSA-K methanolate titanium(4+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].CO[Ti+3] OKENUZUGNVCOMC-UHFFFAOYSA-K 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- YBDVCHQBVBVFMI-UHFFFAOYSA-N methyl(trioctadecoxy)silane Chemical compound CCCCCCCCCCCCCCCCCCO[Si](C)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC YBDVCHQBVBVFMI-UHFFFAOYSA-N 0.000 description 1
- YXDIGQPBWGIANP-UHFFFAOYSA-N methyl(trioctoxy)silane Chemical compound CCCCCCCCO[Si](C)(OCCCCCCCC)OCCCCCCCC YXDIGQPBWGIANP-UHFFFAOYSA-N 0.000 description 1
- QRBAVICMCJULJS-UHFFFAOYSA-N methyl(tripentoxy)silane Chemical compound CCCCCO[Si](C)(OCCCCC)OCCCCC QRBAVICMCJULJS-UHFFFAOYSA-N 0.000 description 1
- DRXHEPWCWBIQFJ-UHFFFAOYSA-N methyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C)OC1=CC=CC=C1 DRXHEPWCWBIQFJ-UHFFFAOYSA-N 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FLALGSYYVIWTFQ-UHFFFAOYSA-K propan-2-olate;titanium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].CC(C)O[Ti+3] FLALGSYYVIWTFQ-UHFFFAOYSA-K 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- BIEFSHWAGDHEIT-UHFFFAOYSA-J tetrabromovanadium Chemical compound [V+4].[Br-].[Br-].[Br-].[Br-] BIEFSHWAGDHEIT-UHFFFAOYSA-J 0.000 description 1
- JYHZWKLCYKMFOD-UHFFFAOYSA-J tetraiodovanadium Chemical compound [V+4].[I-].[I-].[I-].[I-] JYHZWKLCYKMFOD-UHFFFAOYSA-J 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- OTFBCBZYTKQAAB-UHFFFAOYSA-N tri(butan-2-yloxy)-chlorosilane Chemical compound CCC(C)O[Si](Cl)(OC(C)CC)OC(C)CC OTFBCBZYTKQAAB-UHFFFAOYSA-N 0.000 description 1
- RYFIHIMBHQWVNQ-UHFFFAOYSA-N tributoxy(chloro)silane Chemical compound CCCCO[Si](Cl)(OCCCC)OCCCC RYFIHIMBHQWVNQ-UHFFFAOYSA-N 0.000 description 1
- SELBPKHVKHQTIB-UHFFFAOYSA-N trichloro(ethoxy)silane Chemical compound CCO[Si](Cl)(Cl)Cl SELBPKHVKHQTIB-UHFFFAOYSA-N 0.000 description 1
- IORQPMCLCHBYMP-UHFFFAOYSA-N trichloro(methoxy)silane Chemical compound CO[Si](Cl)(Cl)Cl IORQPMCLCHBYMP-UHFFFAOYSA-N 0.000 description 1
- SRDRYKVQYGJKAG-UHFFFAOYSA-N trichloro(octadecoxy)silane Chemical compound CCCCCCCCCCCCCCCCCCO[Si](Cl)(Cl)Cl SRDRYKVQYGJKAG-UHFFFAOYSA-N 0.000 description 1
- CYISGNYTBILXBP-UHFFFAOYSA-N trichloro(octoxy)silane Chemical compound CCCCCCCCO[Si](Cl)(Cl)Cl CYISGNYTBILXBP-UHFFFAOYSA-N 0.000 description 1
- XPVVHUWRWLLSNV-UHFFFAOYSA-N trichloro(pentoxy)silane Chemical compound CCCCCO[Si](Cl)(Cl)Cl XPVVHUWRWLLSNV-UHFFFAOYSA-N 0.000 description 1
- PSTJTDIVYUMKRX-UHFFFAOYSA-N trichloro(propan-2-yloxy)silane Chemical compound CC(C)O[Si](Cl)(Cl)Cl PSTJTDIVYUMKRX-UHFFFAOYSA-N 0.000 description 1
- NBEWDNKFGHANIY-UHFFFAOYSA-N trichloro-(4-methylphenoxy)silane Chemical compound CC1=CC=C(O[Si](Cl)(Cl)Cl)C=C1 NBEWDNKFGHANIY-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- RKABSDHUZWSRHX-UHFFFAOYSA-N triethyl(phenoxy)silane Chemical compound CC[Si](CC)(CC)OC1=CC=CC=C1 RKABSDHUZWSRHX-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- NNLPAMPVXAPWKG-UHFFFAOYSA-N trimethyl(1-methylethoxy)silane Chemical compound CC(C)O[Si](C)(C)C NNLPAMPVXAPWKG-UHFFFAOYSA-N 0.000 description 1
- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WXKZSTUKHWTJCF-UHFFFAOYSA-N zinc;ethanolate Chemical compound [Zn+2].CC[O-].CC[O-] WXKZSTUKHWTJCF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13845582A JPS5930803A (ja) | 1982-08-11 | 1982-08-11 | ポリオレフインの製造方法 |
| FR8313174A FR2531717B1 (fr) | 1982-08-11 | 1983-08-10 | Procede catalytique pour la fabrication de polyolefines |
| DE19833328883 DE3328883A1 (de) | 1982-08-11 | 1983-08-10 | Verfahren zur herstellung von polyolefinen |
| CA000434306A CA1208400A (en) | 1982-08-11 | 1983-08-10 | Process for preparing polyolefins |
| GB08321669A GB2126593B (en) | 1982-08-11 | 1983-08-11 | Olefin polymerisation catalysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13845582A JPS5930803A (ja) | 1982-08-11 | 1982-08-11 | ポリオレフインの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5930803A JPS5930803A (ja) | 1984-02-18 |
| JPH0134447B2 true JPH0134447B2 (ko) | 1989-07-19 |
Family
ID=15222408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13845582A Granted JPS5930803A (ja) | 1982-08-11 | 1982-08-11 | ポリオレフインの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5930803A (ko) |
| CA (1) | CA1208400A (ko) |
| DE (1) | DE3328883A1 (ko) |
| FR (1) | FR2531717B1 (ko) |
| GB (1) | GB2126593B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1219996A (en) * | 1982-11-10 | 1987-03-31 | Kazuo Matsuura | Process for preparing polyolefins |
| US4525555A (en) * | 1983-01-14 | 1985-06-25 | Nippon Oil Company, Limited | Process for preparing polyolefins |
| JPH0735410B2 (ja) * | 1986-01-31 | 1995-04-19 | 三菱油化株式会社 | オレフィンの立体規則性重合用触媒 |
| JPH0762284B2 (ja) * | 1986-10-20 | 1995-07-05 | 日本エクスラン工業株式会社 | 難燃性アクリル繊維の製造方法 |
| EP0376145B1 (en) * | 1988-12-26 | 1994-03-23 | Tosoh Corporation | Method for producing a stereoregular polyolefin |
| CA2049373A1 (en) * | 1990-09-07 | 1992-03-08 | Brian J. Pellon | Process for the production of amorphous elastomeric propylene homopolymers |
| KR100334167B1 (ko) * | 1997-05-08 | 2002-11-22 | 삼성종합화학주식회사 | 알파-올레핀중합방법 |
| KR100334163B1 (ko) * | 1998-12-04 | 2002-10-25 | 삼성종합화학주식회사 | 올레핀중합또는공중합방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5161589A (en) * | 1974-11-26 | 1976-05-28 | Mitsui Toatsu Chemicals | Echirenno jugohoho |
| JPS5695909A (en) * | 1979-12-28 | 1981-08-03 | Nippon Oil Co Ltd | Preparation of polyolefin |
| IT1209255B (it) * | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
| AU546911B2 (en) * | 1981-03-25 | 1985-09-26 | Nippon Oil Company Limited | Olefin polymerizing catalyst |
| JPS57182304A (en) * | 1981-05-07 | 1982-11-10 | Nippon Oil Co Ltd | Production of polyolefin |
| JPS5811509A (ja) * | 1981-07-11 | 1983-01-22 | Nippon Oil Co Ltd | ポリオレフインの製造方法 |
| DE3231582C2 (de) * | 1981-08-25 | 1993-10-14 | Nippon Oil Co Ltd | Verfahren zur Herstellung von Polyolefinen |
-
1982
- 1982-08-11 JP JP13845582A patent/JPS5930803A/ja active Granted
-
1983
- 1983-08-10 FR FR8313174A patent/FR2531717B1/fr not_active Expired
- 1983-08-10 CA CA000434306A patent/CA1208400A/en not_active Expired
- 1983-08-10 DE DE19833328883 patent/DE3328883A1/de not_active Withdrawn
- 1983-08-11 GB GB08321669A patent/GB2126593B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8321669D0 (en) | 1983-09-14 |
| CA1208400A (en) | 1986-07-22 |
| JPS5930803A (ja) | 1984-02-18 |
| FR2531717B1 (fr) | 1987-01-09 |
| FR2531717A1 (fr) | 1984-02-17 |
| GB2126593A (en) | 1984-03-28 |
| GB2126593B (en) | 1986-01-08 |
| DE3328883A1 (de) | 1984-02-16 |
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