NO794002L - Katalysator og fremgangsmaate til polymerisering av alfa-alkener ved anvendelse av katalysatoren - Google Patents
Katalysator og fremgangsmaate til polymerisering av alfa-alkener ved anvendelse av katalysatorenInfo
- Publication number
- NO794002L NO794002L NO794002A NO794002A NO794002L NO 794002 L NO794002 L NO 794002L NO 794002 A NO794002 A NO 794002A NO 794002 A NO794002 A NO 794002A NO 794002 L NO794002 L NO 794002L
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- mgcl2
- stated
- ethylanisate
- ticl4
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 166
- 238000000034 method Methods 0.000 title claims description 14
- 150000001336 alkenes Chemical class 0.000 title claims description 7
- 230000000379 polymerizing effect Effects 0.000 title 1
- -1 magnesium halide Chemical class 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000011777 magnesium Substances 0.000 claims abstract description 20
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 20
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003609 titanium compounds Chemical class 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 94
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 44
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 44
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 42
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 claims description 40
- 238000006116 polymerization reaction Methods 0.000 claims description 40
- 238000000227 grinding Methods 0.000 claims description 27
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 15
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052748 manganese Inorganic materials 0.000 claims description 14
- 239000011572 manganese Substances 0.000 claims description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 14
- 239000010936 titanium Chemical group 0.000 claims description 14
- 229910052719 titanium Inorganic materials 0.000 claims description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002131 composite material Substances 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 6
- 229910010068 TiCl2 Inorganic materials 0.000 claims description 5
- 125000002370 organoaluminium group Chemical group 0.000 claims description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 5
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims description 5
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 4
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 claims description 4
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 4
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 4
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 claims description 4
- 229940061334 2-phenylphenol Drugs 0.000 claims description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005973 Carvone Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229950011260 betanaphthol Drugs 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- WPGPCDVQHXOMQP-UHFFFAOYSA-N carvotanacetone Natural products CC(C)C1CC=C(C)C(=O)C1 WPGPCDVQHXOMQP-UHFFFAOYSA-N 0.000 claims description 3
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000001283 organosilanols Chemical class 0.000 claims description 3
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 3
- 150000008301 phosphite esters Chemical class 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000007586 terpenes Nutrition 0.000 claims description 3
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 claims description 3
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 claims description 2
- VPGIYLLXBOUILV-UHFFFAOYSA-N 2-benzylthiophene Chemical compound C=1C=CC=CC=1CC1=CC=CS1 VPGIYLLXBOUILV-UHFFFAOYSA-N 0.000 claims description 2
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 150000008365 aromatic ketones Chemical class 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- AZOCECCLWFDTAP-RKDXNWHRSA-N dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 229910052726 zirconium Chemical group 0.000 claims description 2
- 239000011236 particulate material Substances 0.000 claims 3
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- KMWSGKPLIWNTEF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-benzodioxaphosphole 2-oxide Chemical compound C1=CC=C2OP(Cl)(=O)OC2=C1 KMWSGKPLIWNTEF-UHFFFAOYSA-N 0.000 claims 1
- YFGZERWVKXLASC-UHFFFAOYSA-N 2-cyclohexylphenol;2,6-ditert-butyl-4-methylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YFGZERWVKXLASC-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ZSIAANIILFGLQH-UHFFFAOYSA-N C1(=CC=CC=C1)[ClH]P(=O)(Cl)[ClH]C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[ClH]P(=O)(Cl)[ClH]C1=CC=CC=C1 ZSIAANIILFGLQH-UHFFFAOYSA-N 0.000 claims 1
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 229920002102 polyvinyl toluene Polymers 0.000 claims 1
- 238000003801 milling Methods 0.000 abstract description 2
- 239000002671 adjuvant Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000004711 α-olefin Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 62
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 53
- 238000002474 experimental method Methods 0.000 description 46
- 235000011147 magnesium chloride Nutrition 0.000 description 31
- 239000000654 additive Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 239000003085 diluting agent Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- 235000010216 calcium carbonate Nutrition 0.000 description 5
- 239000001282 iso-butane Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 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
- 238000010422 painting Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- YPWLZGITFNGGKW-UHFFFAOYSA-N 2-phenanthrol Chemical compound C1=CC=C2C3=CC=C(O)C=C3C=CC2=C1 YPWLZGITFNGGKW-UHFFFAOYSA-N 0.000 description 2
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JLSSWDFCYXSLQX-UHFFFAOYSA-N ethyl 4-cyanobenzoate Chemical compound CCOC(=O)C1=CC=C(C#N)C=C1 JLSSWDFCYXSLQX-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- QNTSFZXGLAHYLC-UHFFFAOYSA-N methyl 4-acetylbenzoate Chemical compound COC(=O)C1=CC=C(C(C)=O)C=C1 QNTSFZXGLAHYLC-UHFFFAOYSA-N 0.000 description 2
- YOJAHJGBFDPSDI-UHFFFAOYSA-N methyl 4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1 YOJAHJGBFDPSDI-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002899 organoaluminium compounds Chemical class 0.000 description 2
- STNJZGLLOVUVMN-UHFFFAOYSA-N propan-2-yl 4-formylbenzoate Chemical compound CC(C)OC(=O)C1=CC=C(C=O)C=C1 STNJZGLLOVUVMN-UHFFFAOYSA-N 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- HQABVXLIIXTKBK-UHFFFAOYSA-N 1-bis(7-phenylnaphthalen-1-yl)phosphoryl-7-phenylnaphthalene Chemical compound C=1C=CC2=CC=C(C=3C=CC=CC=3)C=C2C=1P(C=1C2=CC(=CC=C2C=CC=1)C=1C=CC=CC=1)(=O)C(C1=C2)=CC=CC1=CC=C2C1=CC=CC=C1 HQABVXLIIXTKBK-UHFFFAOYSA-N 0.000 description 1
- GYGISEPATDGSPS-UHFFFAOYSA-N 1-didecylphosphoryldecane Chemical compound CCCCCCCCCCP(=O)(CCCCCCCCCC)CCCCCCCCCC GYGISEPATDGSPS-UHFFFAOYSA-N 0.000 description 1
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- CMOJGEQZTCYQET-UHFFFAOYSA-N phenyl(thiophen-3-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C=1C=CSC=1 CMOJGEQZTCYQET-UHFFFAOYSA-N 0.000 description 1
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- FNZVPOPUGCLHJA-UHFFFAOYSA-N tri(icosyl)alumane Chemical compound CCCCCCCCCCCCCCCCCCCC[Al](CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC FNZVPOPUGCLHJA-UHFFFAOYSA-N 0.000 description 1
- VHAHQCUPIDGTHM-UHFFFAOYSA-N trianthracen-9-yl phosphite Chemical compound C1=CC=C2C(OP(OC=3C4=CC=CC=C4C=C4C=CC=CC4=3)OC=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C(C=CC=C3)C3=CC2=C1 VHAHQCUPIDGTHM-UHFFFAOYSA-N 0.000 description 1
- NKLIVVJLUBFSTE-UHFFFAOYSA-N tribenzyl(hydroxy)silane Chemical compound C=1C=CC=CC=1C[Si](CC=1C=CC=CC=1)(O)CC1=CC=CC=C1 NKLIVVJLUBFSTE-UHFFFAOYSA-N 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- GTBVJMPLFBELEF-UHFFFAOYSA-N tricosyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCOP(O)(O)=O GTBVJMPLFBELEF-UHFFFAOYSA-N 0.000 description 1
- KJRFUNVEVHXEDX-UHFFFAOYSA-N tricycloheptyl phosphate Chemical compound C1CCCCCC1OP(OC1CCCCCC1)(=O)OC1CCCCCC1 KJRFUNVEVHXEDX-UHFFFAOYSA-N 0.000 description 1
- OTDMXUXDQQULPU-UHFFFAOYSA-N tricyclohexyl(hydroxy)silane Chemical compound C1CCCCC1[Si](C1CCCCC1)(O)C1CCCCC1 OTDMXUXDQQULPU-UHFFFAOYSA-N 0.000 description 1
- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-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
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- ADQGXUHCBBVRGM-UHFFFAOYSA-N trinaphthalen-1-yl phosphite Chemical compound C1=CC=C2C(OP(OC=3C4=CC=CC=C4C=CC=3)OC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ADQGXUHCBBVRGM-UHFFFAOYSA-N 0.000 description 1
- KNNDIEXPXVNILT-UHFFFAOYSA-N trinaphthalen-2-yl borate Chemical compound C1=CC=CC2=CC(OB(OC=3C=C4C=CC=CC4=CC=3)OC=3C=C4C=CC=CC4=CC=3)=CC=C21 KNNDIEXPXVNILT-UHFFFAOYSA-N 0.000 description 1
- YIVQLLZRHJPWTH-UHFFFAOYSA-N triphenanthren-4-yl phosphite Chemical compound C1=CC=CC2=C3C(OP(OC=4C5=C6C=CC=CC6=CC=C5C=CC=4)OC=4C5=C6C=CC=CC6=CC=C5C=CC=4)=CC=CC3=CC=C21 YIVQLLZRHJPWTH-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 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
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
- IHSYFQSCIGRGBO-UHFFFAOYSA-N tris(3,5-diethylphenyl) phosphate Chemical compound CCC1=CC(CC)=CC(OP(=O)(OC=2C=C(CC)C=C(CC)C=2)OC=2C=C(CC)C=C(CC)C=2)=C1 IHSYFQSCIGRGBO-UHFFFAOYSA-N 0.000 description 1
- OELFNIKNQUPSDJ-UHFFFAOYSA-N tris(3,5-diheptylphenyl)-hydroxysilane Chemical compound CCCCCCCC1=CC(CCCCCCC)=CC([Si](O)(C=2C=C(CCCCCCC)C=C(CCCCCCC)C=2)C=2C=C(CCCCCCC)C=C(CCCCCCC)C=2)=C1 OELFNIKNQUPSDJ-UHFFFAOYSA-N 0.000 description 1
- PLVBRNQYWJUYMC-UHFFFAOYSA-N tris(3-cyclobutylphenyl) phosphite Chemical compound C1CCC1C1=CC=CC(OP(OC=2C=C(C=CC=2)C2CCC2)OC=2C=C(C=CC=2)C2CCC2)=C1 PLVBRNQYWJUYMC-UHFFFAOYSA-N 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 1
- QNGUUQFOJUJBRU-UHFFFAOYSA-N tris(4-naphthalen-2-ylphenyl) phosphite Chemical compound C1=CC=CC2=CC(C3=CC=C(C=C3)OP(OC=3C=CC(=CC=3)C=3C=C4C=CC=CC4=CC=3)OC=3C=CC(=CC=3)C=3C=C4C=CC=CC4=CC=3)=CC=C21 QNGUUQFOJUJBRU-UHFFFAOYSA-N 0.000 description 1
- ONAGBAZFIRSZHF-UHFFFAOYSA-N tris(4-pentylnaphthalen-1-yl) phosphite Chemical compound C12=CC=CC=C2C(CCCCC)=CC=C1OP(OC=1C2=CC=CC=C2C(CCCCC)=CC=1)OC1=CC=C(CCCCC)C2=CC=CC=C12 ONAGBAZFIRSZHF-UHFFFAOYSA-N 0.000 description 1
- VAURMQDVZLSKAA-UHFFFAOYSA-N tris(4-propan-2-ylphenyl) phosphite Chemical compound C1=CC(C(C)C)=CC=C1OP(OC=1C=CC(=CC=1)C(C)C)OC1=CC=C(C(C)C)C=C1 VAURMQDVZLSKAA-UHFFFAOYSA-N 0.000 description 1
- RKSVIKCZKBKYNQ-UHFFFAOYSA-N tris(5-decylphenanthren-2-yl) phosphite Chemical compound C1=C2C=CC3=CC=CC(CCCCCCCCCC)=C3C2=CC=C1OP(OC=1C=C2C(C3=C(CCCCCCCCCC)C=CC=C3C=C2)=CC=1)OC1=CC2=CC=C3C=CC=C(CCCCCCCCCC)C3=C2C=C1 RKSVIKCZKBKYNQ-UHFFFAOYSA-N 0.000 description 1
- OCWODPBASKRIFT-UHFFFAOYSA-N tris(6-cycloheptylnaphthalen-2-yl) phosphite Chemical compound C1CCCCCC1C1=CC=C(C=C(OP(OC=2C=C3C=CC(=CC3=CC=2)C2CCCCCC2)OC=2C=C3C=CC(=CC3=CC=2)C2CCCCCC2)C=C2)C2=C1 OCWODPBASKRIFT-UHFFFAOYSA-N 0.000 description 1
- NBPZCUCIKOQELK-UHFFFAOYSA-N tris(7-phenylphenanthren-1-yl) phosphite Chemical compound C=1C=CC(C2=CC=C(C=C2C=C2)C=3C=CC=CC=3)=C2C=1OP(OC=1C2=C(C3=CC=C(C=C3C=C2)C=2C=CC=CC=2)C=CC=1)OC1=CC=CC(C2=CC=3)=C1C=CC2=CC=3C1=CC=CC=C1 NBPZCUCIKOQELK-UHFFFAOYSA-N 0.000 description 1
- TYCVNFYGWNZRAM-UHFFFAOYSA-N tritert-butyl(hydroxy)silane Chemical compound CC(C)(C)[Si](O)(C(C)(C)C)C(C)(C)C TYCVNFYGWNZRAM-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000005303 weighing Methods 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
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/968,156 US4243552A (en) | 1978-12-11 | 1978-12-11 | Polymerization catalyst and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO794002L true NO794002L (no) | 1980-06-12 |
Family
ID=25513828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO794002A NO794002L (no) | 1978-12-11 | 1979-12-07 | Katalysator og fremgangsmaate til polymerisering av alfa-alkener ved anvendelse av katalysatoren |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4243552A (de) |
| EP (2) | EP0012397B1 (de) |
| JP (2) | JPS5580405A (de) |
| AT (1) | ATE6262T1 (de) |
| AU (1) | AU516128B2 (de) |
| CA (1) | CA1132129A (de) |
| DE (1) | DE2966689D1 (de) |
| ES (1) | ES486715A1 (de) |
| GB (2) | GB2037786B (de) |
| NO (1) | NO794002L (de) |
| SG (1) | SG31384G (de) |
| ZA (1) | ZA796177B (de) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362648A (en) * | 1979-01-15 | 1982-12-07 | Phillips Petroleum Company | Polymerization of olefins |
| JPS55102606A (en) * | 1979-01-30 | 1980-08-06 | Mitsui Toatsu Chem Inc | Polymerization of alpha-olefin |
| JPS5610504A (en) * | 1979-07-05 | 1981-02-03 | Idemitsu Kosan Co Ltd | Production of titanium catalyst component for olefin polymerization |
| US4379898A (en) * | 1979-07-06 | 1983-04-12 | Phillips Petroleum Company | Polymerization catalysts |
| US4332697A (en) * | 1979-12-31 | 1982-06-01 | Toho Titanium Co., Ltd. | Process for the preparation of catalyst component for the polymerization of α-olefins |
| US4347158A (en) * | 1980-05-02 | 1982-08-31 | Dart Industries, Inc. | Supported high efficiency polyolefin catalyst component and methods of making and using the same |
| US4347160A (en) * | 1980-06-27 | 1982-08-31 | Stauffer Chemical Company | Titanium halide catalyst system |
| US4325836A (en) * | 1980-07-18 | 1982-04-20 | Stauffer Chemical Company | Novel titanium halide containing catalyst |
| IT1209255B (it) * | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
| US4394291A (en) * | 1981-03-04 | 1983-07-19 | Phillips Petroleum Company | Polyolefin polymerization process and catalyst |
| US4442277A (en) * | 1981-03-09 | 1984-04-10 | Phillips Petroleum Company | Process and catalyst for olefin polymerization |
| US4491652A (en) * | 1981-05-13 | 1985-01-01 | Uniroyal, Inc. | Sequentially prepared thermoplastic elastomer and method of preparing same |
| JPS5819307A (ja) * | 1981-07-27 | 1983-02-04 | Mitsubishi Petrochem Co Ltd | オレフイン重合体の製造方法 |
| US4382019A (en) * | 1981-09-10 | 1983-05-03 | Stauffer Chemical Company | Purified catalyst support |
| JPS58138706A (ja) * | 1982-02-12 | 1983-08-17 | Mitsui Petrochem Ind Ltd | オレフイン系重合体の製造方法 |
| US4455386A (en) * | 1982-03-29 | 1984-06-19 | Chemplex Company | Polymerization catalyst |
| US4510299A (en) * | 1982-03-29 | 1985-04-09 | Chemplex Company | Polymerization method |
| US4555496A (en) * | 1982-08-20 | 1985-11-26 | Phillips Petroleum Company | Supported polyolefin catalyst components and methods of making and using the same |
| US4525467A (en) * | 1984-01-16 | 1985-06-25 | Exxon Research & Engineering Co. | High efficiency polymerization catalyst component for use in the polymerization of propylene and higher alpha-olefins |
| US4582816A (en) * | 1985-02-21 | 1986-04-15 | Phillips Petroleum Company | Catalysts, method of preparation and polymerization processes therewith |
| US5547675A (en) * | 1989-09-13 | 1996-08-20 | Exxon Chemical Patents Inc. | Modified monocyclopentadienyl transition metal/alumoxane catalyst system for polymerization of olefins |
| JP5710186B2 (ja) * | 2010-09-10 | 2015-04-30 | 株式会社Adeka | 安定化ポリマーの製造方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA920299A (en) * | 1968-08-01 | 1973-01-30 | Mitsui Petrochemical Industries | Process for the polymerization and/or copolymerization of olefins with use of ziegler-type catalytsts supported on carrier |
| NL162664B (nl) | 1969-06-20 | 1980-01-15 | Montedison Spa | Werkwijze om een katalysator te bereiden voor de poly- merisatie van alkenen-1. |
| NL7114641A (de) | 1970-10-29 | 1972-05-03 | ||
| JPS4933957B1 (de) * | 1970-12-25 | 1974-09-11 | ||
| US4107413A (en) * | 1971-06-25 | 1978-08-15 | Montedison S.P.A. | Process for the stereoregular polymerization of alpha olefins |
| NL160286C (de) | 1971-06-25 | |||
| US4013823A (en) * | 1972-06-09 | 1977-03-22 | The B. F. Goodrich Company | Process for preparing elastomeric copolymers of ethylene and higher alpha-olefins |
| US3953414A (en) * | 1972-09-13 | 1976-04-27 | Montecatini Edison S.P.A., | Catalysts for the polymerization of olefins to spherically shaped polymers |
| US4107415A (en) * | 1972-09-26 | 1978-08-15 | Montecatini Edison S.P.A. | Process for the stereospecific polymerization of alpha-olefins |
| GB1489599A (en) | 1973-10-09 | 1977-10-19 | Nippon Oil Co Ltd | Process for preparing polyolefins and catalyst and catalyst component therefor |
| IT1052079B (it) * | 1975-01-10 | 1981-06-20 | Nippon Oil Co Ltd | Procedimento per la produzione di poliolefine |
| IT1054410B (it) * | 1975-11-21 | 1981-11-10 | Mitsui Petrochemical Ind | Catalizzatori per la polimerizzazione delle alfa olefine |
| JPS52104593A (en) * | 1976-03-01 | 1977-09-02 | Mitsui Petrochem Ind Ltd | Polymerization of olefins |
| US4107412A (en) * | 1976-11-24 | 1978-08-15 | Phillips Petroleum Company | Olefin polymerization process and catalyst therefor |
| US4130503A (en) * | 1977-12-23 | 1978-12-19 | Phillips Petroleum Company | Phosphite in MgX2 supported TiX3 /AlCl3 catalyst system |
-
1978
- 1978-12-11 US US05/968,156 patent/US4243552A/en not_active Expired - Lifetime
-
1979
- 1979-11-16 ZA ZA00796177A patent/ZA796177B/xx unknown
- 1979-11-20 CA CA340,199A patent/CA1132129A/en not_active Expired
- 1979-11-21 AU AU53078/79A patent/AU516128B2/en not_active Ceased
- 1979-12-05 JP JP15695379A patent/JPS5580405A/ja active Pending
- 1979-12-07 NO NO794002A patent/NO794002L/no unknown
- 1979-12-07 EP EP79105010A patent/EP0012397B1/de not_active Expired
- 1979-12-07 DE DE7979105010T patent/DE2966689D1/de not_active Expired
- 1979-12-07 AT AT79105010T patent/ATE6262T1/de not_active IP Right Cessation
- 1979-12-07 EP EP82106589A patent/EP0070039A3/de not_active Withdrawn
- 1979-12-10 ES ES486715A patent/ES486715A1/es not_active Expired
- 1979-12-11 GB GB7942667A patent/GB2037786B/en not_active Expired
-
1982
- 1982-10-08 GB GB08228874A patent/GB2115826B/en not_active Expired
-
1983
- 1983-12-01 JP JP58227805A patent/JPS59131605A/ja active Pending
-
1984
- 1984-04-18 SG SG313/84A patent/SG31384G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0012397B1 (de) | 1984-02-15 |
| ES486715A1 (es) | 1980-09-16 |
| AU516128B2 (en) | 1981-05-21 |
| GB2115826B (en) | 1984-02-01 |
| US4243552A (en) | 1981-01-06 |
| EP0070039A2 (de) | 1983-01-19 |
| GB2037786B (en) | 1983-10-12 |
| CA1132129A (en) | 1982-09-21 |
| ATE6262T1 (de) | 1984-03-15 |
| JPS59131605A (ja) | 1984-07-28 |
| DE2966689D1 (en) | 1984-03-22 |
| GB2115826A (en) | 1983-09-14 |
| SG31384G (en) | 1985-02-15 |
| GB2037786A (en) | 1980-07-16 |
| AU5307879A (en) | 1980-06-19 |
| EP0012397A1 (de) | 1980-06-25 |
| ZA796177B (en) | 1980-11-26 |
| JPS5580405A (en) | 1980-06-17 |
| EP0070039A3 (de) | 1983-06-01 |
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