JP2940684B2 - オレフィン重合用固体状触媒成分およびこの触媒成分を用いたオレフィンの重合方法 - Google Patents
オレフィン重合用固体状触媒成分およびこの触媒成分を用いたオレフィンの重合方法Info
- Publication number
- JP2940684B2 JP2940684B2 JP1340909A JP34090989A JP2940684B2 JP 2940684 B2 JP2940684 B2 JP 2940684B2 JP 1340909 A JP1340909 A JP 1340909A JP 34090989 A JP34090989 A JP 34090989A JP 2940684 B2 JP2940684 B2 JP 2940684B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst component
- olefin
- solid
- catalyst
- titanium
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 146
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 100
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000011949 solid catalyst Substances 0.000 title claims abstract description 31
- 230000000379 polymerizing effect Effects 0.000 title claims description 9
- 239000010936 titanium Substances 0.000 claims abstract description 114
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 96
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 90
- 239000002245 particle Substances 0.000 claims abstract description 71
- 239000007787 solid Substances 0.000 claims abstract description 71
- 229920000098 polyolefin Polymers 0.000 claims abstract description 53
- 239000004711 α-olefin Substances 0.000 claims abstract description 40
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 38
- -1 ether compound Chemical class 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 31
- 239000011777 magnesium Substances 0.000 claims description 27
- 229910052749 magnesium Inorganic materials 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 24
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 18
- 239000005977 Ethylene Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
- 238000007334 copolymerization reaction Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 31
- 150000002902 organometallic compounds Chemical class 0.000 abstract description 14
- 238000009826 distribution Methods 0.000 abstract description 10
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000002681 magnesium compounds Chemical class 0.000 description 40
- 150000003609 titanium compounds Chemical class 0.000 description 27
- 229920001577 copolymer Polymers 0.000 description 21
- 150000002430 hydrocarbons Chemical group 0.000 description 19
- 230000001603 reducing effect Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 125000005234 alkyl aluminium group Chemical group 0.000 description 9
- 230000000737 periodic effect Effects 0.000 description 9
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 8
- 150000003377 silicon compounds Chemical class 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying 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
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 4
- 238000012685 gas phase polymerization Methods 0.000 description 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000003961 organosilicon compounds Chemical class 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YZBOVSFWWNVKRJ-UHFFFAOYSA-N Monobutylphthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(O)=O YZBOVSFWWNVKRJ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- KQAHMVLQCSALSX-UHFFFAOYSA-N decyl(trimethoxy)silane Chemical compound CCCCCCCCCC[Si](OC)(OC)OC KQAHMVLQCSALSX-UHFFFAOYSA-N 0.000 description 2
- BSALDGPEFGOAJZ-UHFFFAOYSA-N dibutyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OCCCC)C(C(=O)OCCCC)=CC=C21 BSALDGPEFGOAJZ-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZVMRWPHIZSSUKP-UHFFFAOYSA-N dicyclohexyl(dimethoxy)silane Chemical compound C1CCCCC1[Si](OC)(OC)C1CCCCC1 ZVMRWPHIZSSUKP-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 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 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- SZIZIGBTHTUEBU-UHFFFAOYSA-N dimethoxy-bis(4-methylphenyl)silane Chemical compound C=1C=C(C)C=CC=1[Si](OC)(OC)C1=CC=C(C)C=C1 SZIZIGBTHTUEBU-UHFFFAOYSA-N 0.000 description 2
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 2
- IPKKHRVROFYTEK-UHFFFAOYSA-N dipentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC IPKKHRVROFYTEK-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
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- NMJKIRUDPFBRHW-UHFFFAOYSA-N titanium Chemical compound [Ti].[Ti] NMJKIRUDPFBRHW-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PTCWADDVLPYBBZ-UHFFFAOYSA-N tricyclopentylmethoxysilane Chemical compound C1CCCC1C(C1CCCC1)(O[SiH3])C1CCCC1 PTCWADDVLPYBBZ-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- IOPAQHDEQBHWEB-UHFFFAOYSA-N trimethoxy-(2-methylcyclopentyl)silane Chemical compound CO[Si](OC)(OC)C1CCCC1C IOPAQHDEQBHWEB-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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 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
- C08F4/00—Polymerisation catalysts
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1340909A JP2940684B2 (ja) | 1989-12-29 | 1989-12-29 | オレフィン重合用固体状触媒成分およびこの触媒成分を用いたオレフィンの重合方法 |
| TW079110903A TW201763B (en:Method) | 1989-12-29 | 1990-12-27 | |
| MYPI90002271A MY105326A (en) | 1989-12-29 | 1990-12-27 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same. |
| US07/634,737 US5153158A (en) | 1989-12-29 | 1990-12-27 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| CA002033404A CA2033404C (en) | 1989-12-29 | 1990-12-28 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| PL90300678A PL167905B1 (pl) | 1989-12-29 | 1990-12-28 | Sposób polimeryzacji a-olefin w obecnosci katalizatora PL PL PL |
| ES90125706T ES2031800T3 (es) | 1989-12-29 | 1990-12-28 | Componentes de catalizador solido para polimerizacion de olefinas y procedimiento de polimerizacion de olefina utilizando los mismos. |
| PL90288512A PL167899B1 (pl) | 1989-12-29 | 1990-12-28 | Sposób wytwarzania stalego skladnika katalizatora do polimeryzacji olefin PL PL PL |
| AT90125706T ATE151782T1 (de) | 1989-12-29 | 1990-12-28 | Fester katalysatorbestandteil für olefinpolymerisation und olefinpolymerisationsverfahren unter anwendung derselben |
| PL90300679A PL167913B1 (pl) | 1989-12-29 | 1990-12-28 | Sposób wytwarzania katalizatora polimeryzacji olefin PL PL PL |
| DE199090125706T DE435332T1 (de) | 1989-12-29 | 1990-12-28 | Fester katalysatorbestandteil fuer olefinpolymerisation und olefinpolymerisationsverfahren unter anwendung derselben. |
| EP90125706A EP0435332B2 (en) | 1989-12-29 | 1990-12-28 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| DK90125706.3T DK0435332T3 (da) | 1989-12-29 | 1990-12-28 | Fast katalysatorkomponent til olefinpolymerisation og fremgangsmåde til polymerisation af olefin under anvendelse deraf |
| SU904894186A RU2092495C1 (ru) | 1989-12-29 | 1990-12-28 | Твердый компонент катализатора полимеризации альфа-олефинов, катализатор полимеризации альфа-олефинов и способ получения полиолефинов |
| DE69030489T DE69030489T3 (de) | 1989-12-29 | 1990-12-28 | Fester Katalysatorbestandteil für Olefinpolymerisation und Olefinpolymerisationsverfahren unter Anwendung derselben |
| CS906942A CZ283582B6 (cs) | 1989-12-29 | 1990-12-29 | Pevné katalyzátorové komponenty pro polymeraci olefinů a způsoby polymerace za použití těchto komponent |
| CN90110256A CN1038685C (zh) | 1989-12-29 | 1990-12-29 | 用于烯烃聚合的固体催化剂及其组分 |
| KR1019900022415A KR940010963B1 (ko) | 1989-12-29 | 1990-12-29 | 올레핀 중합용 고체촉매성분 및 그를 사용한 올레핀 중합방법 |
| US07/885,824 US5247032A (en) | 1989-12-29 | 1992-05-20 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| GR92300075T GR920300075T1 (en) | 1989-12-29 | 1992-10-08 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| GR970400965T GR3023309T3 (en) | 1989-12-29 | 1997-05-02 | Solid catalyst components for olefin polymerization and processes for the polymerization of olefin using same |
| CN97113747A CN1174204A (zh) | 1989-12-29 | 1997-07-04 | 用于烯烃聚合作用的固体催化剂的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1340909A JP2940684B2 (ja) | 1989-12-29 | 1989-12-29 | オレフィン重合用固体状触媒成分およびこの触媒成分を用いたオレフィンの重合方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03203908A JPH03203908A (ja) | 1991-09-05 |
| JP2940684B2 true JP2940684B2 (ja) | 1999-08-25 |
Family
ID=18341422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1340909A Expired - Lifetime JP2940684B2 (ja) | 1989-12-29 | 1989-12-29 | オレフィン重合用固体状触媒成分およびこの触媒成分を用いたオレフィンの重合方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5153158A (en:Method) |
| EP (1) | EP0435332B2 (en:Method) |
| JP (1) | JP2940684B2 (en:Method) |
| KR (1) | KR940010963B1 (en:Method) |
| CN (2) | CN1038685C (en:Method) |
| AT (1) | ATE151782T1 (en:Method) |
| CA (1) | CA2033404C (en:Method) |
| CZ (1) | CZ283582B6 (en:Method) |
| DE (2) | DE435332T1 (en:Method) |
| DK (1) | DK0435332T3 (en:Method) |
| ES (1) | ES2031800T3 (en:Method) |
| GR (2) | GR920300075T1 (en:Method) |
| MY (1) | MY105326A (en:Method) |
| PL (3) | PL167905B1 (en:Method) |
| RU (1) | RU2092495C1 (en:Method) |
| TW (1) | TW201763B (en:Method) |
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| KR970007238B1 (ko) * | 1989-12-28 | 1997-05-07 | 이데미쯔 세끼유가가꾸 가부시끼가이샤 | 올레핀 중합용 촉매성분 및 폴리올레핀의 제조방법 |
| IT1246614B (it) | 1991-06-03 | 1994-11-24 | Himont Inc | Procedimento per la polimerizzazione in fase gas delle olefine |
| US6291384B1 (en) | 1991-11-06 | 2001-09-18 | Mobil Oil Corporation | High activity catalyst prepared with alkoxysilanes |
| US5470812A (en) * | 1991-11-06 | 1995-11-28 | Mobil Oil Corporation | High activity polyethylene catalysts prepared with alkoxysilane reagents |
| US5939348A (en) * | 1991-11-06 | 1999-08-17 | Mobil Oil Corporation | Catalyst for the manufacture of polythylene with a narrow molecular weight distribution |
| FR2689133A1 (fr) * | 1992-03-27 | 1993-10-01 | Atochem Elf Sa | Catalyseur de polymérisation des oléfines, son procédé d'obtention. |
| US5308818A (en) * | 1992-06-08 | 1994-05-03 | Fina Technology, Inc. | Catalyst system for the polymerization of olefins |
| JP3156213B2 (ja) * | 1993-02-23 | 2001-04-16 | 日石三菱株式会社 | ポリオレフィンの製造方法 |
| US5376743A (en) * | 1993-03-11 | 1994-12-27 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the production of sticky polymers |
| US5518973A (en) * | 1993-10-15 | 1996-05-21 | Exxon Chemical Patents Inc. | Titanium trichloride catalyst system for polymerizing olefins |
| CA2174766C (en) * | 1993-11-18 | 2005-06-21 | Robert Ivan Mink | A catalyst composition for the copolymerization of ethylene |
| TW412546B (en) * | 1994-05-19 | 2000-11-21 | Mitsui Petrochemical Ind | Solid titanium catalyst component for olefin polymerization, process for preparation of the same, olefin polymerization catalyst and process for olefin polymerization |
| US6034189A (en) * | 1994-05-19 | 2000-03-07 | Mitsui Petrochemical Industries, Ltd. | Solid titanium catalyst component for olefin polymerization, process for preparation of the same, olefin polymerization catalyst and process for olefin polymerization |
| IT1275867B1 (it) * | 1995-03-07 | 1997-10-24 | Enichem Elastomers | Procedimento per l'ottenimento di copolimeri elastomerici etilene- propilene ad alta purezza e distribuzione dei pesi molecolari |
| US5849655A (en) * | 1996-12-20 | 1998-12-15 | Fina Technology, Inc. | Polyolefin catalyst for polymerization of propylene and a method of making and using thereof |
| US5948720A (en) * | 1997-01-07 | 1999-09-07 | Huntsman Polymers Corporation | Catalyst for the production of flexible polyolefin compositions, methods for making and using same, and products thereof |
| US6100351A (en) * | 1997-01-07 | 2000-08-08 | Huntsman Polymers Corporation | Olefin polymerization process and products thereof |
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| US4326988A (en) * | 1980-08-12 | 1982-04-27 | Phillips Petroleum Company | Catalyst, method of producing the catalyst, and polymerization process employing the catalyst |
| US4325837A (en) * | 1980-08-12 | 1982-04-20 | Phillips Petroleum Company | Catalyst, method of producing the catalyst, and polymerization process employing the catalyst |
| US4410671A (en) * | 1980-08-12 | 1983-10-18 | Phillips Petroleum Company | Catalyst, method of producing the catalyst, and polymerization process employing the catalyst |
| JPS5898315A (ja) * | 1981-12-07 | 1983-06-11 | Chisso Corp | ポリオレフイン共重合体の粉体流動性改良法 |
| DE3366573D1 (en) * | 1982-06-24 | 1986-11-06 | Bp Chimie Sa | Process for the polymerization and copolymerization of alpha-olefins in a fluidized bed |
| FR2541683B1 (fr) * | 1983-02-28 | 1986-05-09 | Ato Chimie | Procede pour la preparation d'un solide hydrocarbone actif utilisable pour polymeriser des olefines, et procede de synthese d'un polymere ou copolymere olefinique faisant appel audit solide hydrocarbone actif comme systeme |
| CA1284549C (en) † | 1986-09-26 | 1991-05-28 | Fathi David Hussein | Process for the polymerization of propylene |
| EP0279153B1 (en) † | 1987-02-02 | 1994-03-30 | Fina Technology, Inc. | Process for increasing the efficiency of a pre-polymerized catalyst |
| FR2629461B1 (fr) * | 1988-03-31 | 1993-05-07 | Bp Chimie Sa | Catalyseur de (co)polymerisation du propylene, supporte sur des particules spheriques de chlorure de magnesium et enrobe par du polypropylene, et procedes de preparation |
| FR2651234B1 (fr) * | 1989-08-29 | 1993-03-12 | Bp Chem Int Ltd | Procede de fabrication en phase gazeuse de copolymeres du propylene a l'aide d'un systeme catalytique de haute activite. |
-
1989
- 1989-12-29 JP JP1340909A patent/JP2940684B2/ja not_active Expired - Lifetime
-
1990
- 1990-12-27 MY MYPI90002271A patent/MY105326A/en unknown
- 1990-12-27 US US07/634,737 patent/US5153158A/en not_active Expired - Lifetime
- 1990-12-27 TW TW079110903A patent/TW201763B/zh active
- 1990-12-28 DK DK90125706.3T patent/DK0435332T3/da active
- 1990-12-28 ES ES90125706T patent/ES2031800T3/es not_active Expired - Lifetime
- 1990-12-28 PL PL90300678A patent/PL167905B1/pl unknown
- 1990-12-28 DE DE199090125706T patent/DE435332T1/de active Pending
- 1990-12-28 CA CA002033404A patent/CA2033404C/en not_active Expired - Fee Related
- 1990-12-28 EP EP90125706A patent/EP0435332B2/en not_active Expired - Lifetime
- 1990-12-28 RU SU904894186A patent/RU2092495C1/ru not_active IP Right Cessation
- 1990-12-28 DE DE69030489T patent/DE69030489T3/de not_active Expired - Lifetime
- 1990-12-28 PL PL90300679A patent/PL167913B1/pl unknown
- 1990-12-28 PL PL90288512A patent/PL167899B1/pl unknown
- 1990-12-28 AT AT90125706T patent/ATE151782T1/de not_active IP Right Cessation
- 1990-12-29 CZ CS906942A patent/CZ283582B6/cs not_active IP Right Cessation
- 1990-12-29 KR KR1019900022415A patent/KR940010963B1/ko not_active Expired - Fee Related
- 1990-12-29 CN CN90110256A patent/CN1038685C/zh not_active Expired - Lifetime
-
1992
- 1992-10-08 GR GR92300075T patent/GR920300075T1/el unknown
-
1997
- 1997-05-02 GR GR970400965T patent/GR3023309T3/el unknown
- 1997-07-04 CN CN97113747A patent/CN1174204A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0435332A3 (en) | 1992-02-26 |
| US5153158A (en) | 1992-10-06 |
| CA2033404C (en) | 1995-09-05 |
| JPH03203908A (ja) | 1991-09-05 |
| TW201763B (en:Method) | 1993-03-11 |
| CZ694290A3 (en) | 1996-07-17 |
| CA2033404A1 (en) | 1991-06-30 |
| EP0435332B1 (en) | 1997-04-16 |
| KR940010963B1 (ko) | 1994-11-21 |
| PL167913B1 (pl) | 1995-12-30 |
| GR3023309T3 (en) | 1997-08-29 |
| ES2031800T3 (es) | 1997-09-16 |
| ATE151782T1 (de) | 1997-05-15 |
| KR910011920A (ko) | 1991-08-07 |
| PL167899B1 (pl) | 1995-12-30 |
| DE435332T1 (de) | 1992-09-03 |
| MY105326A (en) | 1994-09-30 |
| GR920300075T1 (en) | 1992-10-08 |
| DE69030489D1 (de) | 1997-05-22 |
| DK0435332T3 (da) | 1997-05-12 |
| EP0435332B2 (en) | 2005-08-10 |
| RU2092495C1 (ru) | 1997-10-10 |
| DE69030489T3 (de) | 2006-03-16 |
| CZ283582B6 (cs) | 1998-05-13 |
| CN1174204A (zh) | 1998-02-25 |
| CN1038685C (zh) | 1998-06-10 |
| EP0435332A2 (en) | 1991-07-03 |
| CN1052870A (zh) | 1991-07-10 |
| DE69030489T2 (de) | 1997-09-04 |
| ES2031800T1 (es) | 1993-01-01 |
| PL288512A1 (en) | 1991-09-09 |
| PL167905B1 (pl) | 1995-12-30 |
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