SK279451B6 - Kompozícia obsahujúca polydién alebo kopolymér dié - Google Patents
Kompozícia obsahujúca polydién alebo kopolymér dié Download PDFInfo
- Publication number
- SK279451B6 SK279451B6 SK1500-91A SK150091A SK279451B6 SK 279451 B6 SK279451 B6 SK 279451B6 SK 150091 A SK150091 A SK 150091A SK 279451 B6 SK279451 B6 SK 279451B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- group
- phenol
- composition
- polydiene
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000003381 stabilizer Substances 0.000 title claims abstract description 29
- 229920001577 copolymer Polymers 0.000 title claims abstract description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- -1 n-octyl Chemical group 0.000 claims description 32
- 229920001971 elastomer Polymers 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000806 elastomer Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 description 15
- 239000005060 rubber Substances 0.000 description 13
- 230000032683 aging Effects 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 229920000126 latex Polymers 0.000 description 8
- 239000004816 latex Substances 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 2
- ZYJXQDCMXTWHIV-UHFFFAOYSA-N 2-tert-butyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(CSCCCCCCCC)=C(O)C(C(C)(C)C)=C1 ZYJXQDCMXTWHIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 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
- NYNRDINGKLPEGU-UHFFFAOYSA-N 2,4-bis[(dimethylamino)methyl]-6-methylphenol Chemical compound CN(C)CC1=CC(C)=C(O)C(CN(C)C)=C1 NYNRDINGKLPEGU-UHFFFAOYSA-N 0.000 description 1
- ZFQSDRHCQNFDGT-UHFFFAOYSA-N 2-methyl-6-(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC=CC(C)=C1O ZFQSDRHCQNFDGT-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- OKZHFXLJYUIQNL-UHFFFAOYSA-N 4-tert-butyl-2-methyl-6-(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C(C)(C)C)=CC(C)=C1O OKZHFXLJYUIQNL-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006173 natural rubber latex Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000010089 rubber coagulation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH173190 | 1990-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK279451B6 true SK279451B6 (sk) | 1998-11-04 |
Family
ID=4217279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1500-91A SK279451B6 (sk) | 1990-05-22 | 1991-05-21 | Kompozícia obsahujúca polydién alebo kopolymér dié |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5116894A (ja) |
| JP (1) | JP2984864B2 (ja) |
| KR (1) | KR0168058B1 (ja) |
| BE (1) | BE1005881A3 (ja) |
| BR (1) | BR9102075A (ja) |
| CA (1) | CA2042859C (ja) |
| CZ (1) | CZ281892B6 (ja) |
| DE (1) | DE4116549A1 (ja) |
| ES (1) | ES2046923B1 (ja) |
| FR (1) | FR2662445B1 (ja) |
| GB (1) | GB2244275B (ja) |
| IT (1) | IT1247955B (ja) |
| NL (1) | NL194506C (ja) |
| RU (1) | RU2031909C1 (ja) |
| SK (1) | SK279451B6 (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59109031D1 (de) * | 1990-06-07 | 1998-09-03 | Ciba Geigy Ag | Verfahren zur Herstellung von Polyurethanstoffen unter Verwendung von spezifischen Stabilisatorsystemen |
| TW222293B (ja) * | 1991-12-06 | 1994-04-11 | Ciba Geigy Ag | |
| US20090203817A1 (en) * | 2006-04-13 | 2009-08-13 | Stretanski Joseph A | Stabilized spandex compositions |
| JP5843878B2 (ja) | 2010-11-16 | 2016-01-13 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリマー用安定剤組成物 |
| CA2940970C (en) * | 2014-02-28 | 2019-03-19 | Exxonmobil Chemical Patents Inc. | Mooney viscosity stable brominated elastomers |
| CN106905206B (zh) * | 2017-03-03 | 2018-08-14 | 湘潭大学 | 2-甲基-4,6-双(正辛基硫甲基)苯酚的制备 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240749A (en) * | 1961-04-11 | 1966-03-15 | Geigy Chem Corp | Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby |
| US3255191A (en) * | 1964-04-21 | 1966-06-07 | Geigy Chem Corp | Substituted 1, 3, 5-triazines |
| US3245992A (en) * | 1965-07-20 | 1966-04-12 | Geigy Chem Corp | Phenoxy-, phenylthio-and phenylamino-1, 3, 5-triazines |
| US3250772A (en) * | 1965-07-20 | 1966-05-10 | Geigy Chem Corp | Sulfur-substituted 1, 3, 5-triazines |
| US3557050A (en) * | 1967-03-08 | 1971-01-19 | Daikin Ind Ltd | Stabilized vinyl fluoride polymers |
| US3903173A (en) * | 1967-03-17 | 1975-09-02 | Ciba Geigy Ag | Lower alkylthiomethylene containing phenols |
| DE1593821B1 (de) * | 1967-03-17 | 1971-08-05 | Advance Prod Gmbh | Verfahren zur Herstellung von Dialkylhydroxybenzylsulfiden |
| JPS534091B1 (ja) * | 1967-04-03 | 1978-02-14 | ||
| US3594448A (en) * | 1969-04-16 | 1971-07-20 | Allied Chem | Filament comprising a polymer blend of polyester and polyamide containing a sterically hindered phenolic compound |
| US3660352A (en) * | 1970-06-04 | 1972-05-02 | American Cyanamid Co | Hindered phenol sulfide antioxidants for polymers |
| JPS56141338A (en) * | 1980-04-04 | 1981-11-05 | Hitachi Cable Ltd | Crosslinked polyolefin composition |
| EP0107617B1 (de) * | 1982-09-30 | 1986-04-23 | Ciba-Geigy Ag | Schlagzähes Polystyrol |
| DE3571608D1 (en) * | 1984-06-12 | 1989-08-24 | Ciba Geigy Ag | O,p-bifunctionalised, o'-substituted phenols |
| JPS61159442A (ja) * | 1984-12-29 | 1986-07-19 | Mitsubishi Plastics Ind Ltd | スチレン系樹脂収縮フイルム |
| ES2014433B3 (es) * | 1985-11-13 | 1990-07-16 | Ciba-Geigy Ag | Fenoles sustituidos, como estabilizadores. |
| EP0238140A2 (en) * | 1986-03-19 | 1987-09-23 | Akzo N.V. | Polyester resin composition with excellent heat resistance |
| EP0273013B2 (de) * | 1986-12-24 | 1996-07-24 | Ciba-Geigy Ag | Substituierte Phenole als Stabilisatoren |
| US4707300A (en) * | 1987-03-09 | 1987-11-17 | The Goodyear Tire & Rubber Company | Autosynergistic phenolic antioxidant reaction product |
-
1991
- 1991-05-10 KR KR1019910007550A patent/KR0168058B1/ko not_active IP Right Cessation
- 1991-05-16 US US07/701,265 patent/US5116894A/en not_active Expired - Lifetime
- 1991-05-16 BE BE9100457A patent/BE1005881A3/fr not_active IP Right Cessation
- 1991-05-17 CA CA002042859A patent/CA2042859C/en not_active Expired - Lifetime
- 1991-05-20 JP JP3144003A patent/JP2984864B2/ja not_active Expired - Lifetime
- 1991-05-20 GB GB9110848A patent/GB2244275B/en not_active Expired - Lifetime
- 1991-05-21 CZ CS911500A patent/CZ281892B6/cs not_active IP Right Cessation
- 1991-05-21 IT ITMI911394A patent/IT1247955B/it active IP Right Grant
- 1991-05-21 FR FR9106085A patent/FR2662445B1/fr not_active Expired - Lifetime
- 1991-05-21 ES ES09101224A patent/ES2046923B1/es not_active Expired - Fee Related
- 1991-05-21 SK SK1500-91A patent/SK279451B6/sk not_active IP Right Cessation
- 1991-05-21 DE DE4116549A patent/DE4116549A1/de not_active Ceased
- 1991-05-21 RU SU914895372A patent/RU2031909C1/ru not_active IP Right Cessation
- 1991-05-21 NL NL9100876A patent/NL194506C/nl not_active IP Right Cessation
- 1991-05-21 BR BR919102075A patent/BR9102075A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2046923B1 (es) | 1994-09-01 |
| DE4116549A1 (de) | 1991-11-28 |
| NL9100876A (nl) | 1991-12-16 |
| GB9110848D0 (en) | 1991-07-10 |
| BR9102075A (pt) | 1991-12-24 |
| CZ281892B6 (cs) | 1997-03-12 |
| BE1005881A3 (fr) | 1994-03-01 |
| ITMI911394A1 (it) | 1992-11-21 |
| IT1247955B (it) | 1995-01-05 |
| JP2984864B2 (ja) | 1999-11-29 |
| KR0168058B1 (ko) | 1999-03-20 |
| CA2042859A1 (en) | 1991-11-23 |
| FR2662445A1 (fr) | 1991-11-29 |
| CA2042859C (en) | 2002-11-05 |
| NL194506B (nl) | 2002-02-01 |
| CS9101500A2 (en) | 1991-12-17 |
| FR2662445B1 (fr) | 1995-05-12 |
| US5116894A (en) | 1992-05-26 |
| RU2031909C1 (ru) | 1995-03-27 |
| GB2244275A (en) | 1991-11-27 |
| JPH04227942A (ja) | 1992-08-18 |
| ITMI911394A0 (it) | 1991-05-21 |
| GB2244275B (en) | 1992-12-16 |
| NL194506C (nl) | 2002-06-04 |
| ES2046923A1 (es) | 1994-02-01 |
| KR910020080A (ko) | 1991-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20110521 |