CS273176B2 - Method of butadiene's homopolymer and copolymer production - Google Patents
Method of butadiene's homopolymer and copolymer production Download PDFInfo
- Publication number
- CS273176B2 CS273176B2 CS493286A CS493286A CS273176B2 CS 273176 B2 CS273176 B2 CS 273176B2 CS 493286 A CS493286 A CS 493286A CS 493286 A CS493286 A CS 493286A CS 273176 B2 CS273176 B2 CS 273176B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- component
- polymerization
- neodymium
- butadiene
- curve
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 27
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 25
- 230000003197 catalytic effect Effects 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 150000001993 dienes Chemical class 0.000 claims abstract description 5
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 3
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- -1 organic acid halides Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910052779 Neodymium Inorganic materials 0.000 claims description 4
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002798 neodymium compounds Chemical class 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 150000002910 rare earth metals Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000004707 phenolate Chemical class 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 150000005376 secondary alkyl halides Chemical class 0.000 claims description 2
- 150000005377 tertiary alkyl halides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 10
- 238000007792 addition Methods 0.000 claims 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims 2
- 150000002989 phenols Chemical class 0.000 claims 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 1
- 229910052777 Praseodymium Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
- 229910001507 metal halide Inorganic materials 0.000 claims 1
- 150000005309 metal halides Chemical class 0.000 claims 1
- 125000005608 naphthenic acid group Chemical group 0.000 claims 1
- TZNZEEADHYGQQO-UHFFFAOYSA-K neodymium(3+);triphenoxide Chemical class [Nd+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 TZNZEEADHYGQQO-UHFFFAOYSA-K 0.000 claims 1
- 150000002896 organic halogen compounds Chemical class 0.000 claims 1
- 230000010355 oscillation Effects 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims 1
- 150000002909 rare earth metal compounds Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims 1
- 238000010923 batch production Methods 0.000 abstract description 2
- 238000010924 continuous production Methods 0.000 abstract description 2
- 239000004411 aluminium Substances 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- QYEWAEAWMXRMHB-YFTUCIGFSA-N (4r)-5-[[(3s,6r,9s,12r,15s,18r,21r,22r)-3-[(2s)-butan-2-yl]-6,12-bis(hydroxymethyl)-22-methyl-9,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2s)-2-[[(3r)-3-hydroxydecanoyl]amino] Chemical compound CCCCCCC[C@@H](O)CC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]1[C@@H](C)OC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C(C)C)NC1=O QYEWAEAWMXRMHB-YFTUCIGFSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QYEWAEAWMXRMHB-UHFFFAOYSA-N 8-Angeloyl-8alpha-4,9-Muuroladiene-1,8-diol Natural products CCCCCCCC(O)CC(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC1C(C)OC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC1=O QYEWAEAWMXRMHB-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 108010067142 viscosin Proteins 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
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21377/85A IT1186747B (it) | 1985-07-01 | 1985-07-01 | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS493286A2 CS493286A2 (en) | 1990-07-12 |
| CS273176B2 true CS273176B2 (en) | 1991-03-12 |
Family
ID=11180895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS493286A CS273176B2 (en) | 1985-07-01 | 1986-06-30 | Method of butadiene's homopolymer and copolymer production |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4699960A (pl) |
| EP (1) | EP0207558B1 (pl) |
| JP (1) | JPH0730135B2 (pl) |
| KR (1) | KR890002925B1 (pl) |
| CN (1) | CN1005413B (pl) |
| AU (1) | AU588329B2 (pl) |
| BR (1) | BR8603229A (pl) |
| CA (1) | CA1277093C (pl) |
| CS (1) | CS273176B2 (pl) |
| DD (1) | DD248128A5 (pl) |
| DE (1) | DE3678047D1 (pl) |
| EG (1) | EG18915A (pl) |
| ES (1) | ES8708238A1 (pl) |
| IE (1) | IE58948B1 (pl) |
| IN (1) | IN167543B (pl) |
| IT (1) | IT1186747B (pl) |
| PL (1) | PL147478B3 (pl) |
| PT (1) | PT82887B (pl) |
| TR (1) | TR23851A (pl) |
| YU (1) | YU46011B (pl) |
| ZA (1) | ZA864520B (pl) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1230756B (it) * | 1989-02-17 | 1991-10-29 | Enichem Elastomers | Metodo per la preparazione di polibutadiene a lavorabilita' migliorata. |
| DE4413900A1 (de) * | 1994-04-21 | 1995-10-26 | Htw Dresden | Anordnung zur Gütesteuerung von Lasern |
| US5500396A (en) * | 1995-02-09 | 1996-03-19 | Phillips Petroleum Company | Process to make small, discrete, spherical adducts |
| US6001478A (en) * | 1997-08-08 | 1999-12-14 | Union Carbide Chemicals & Plastics Technology Corporation | Resin particle produced by diene polymerization with rare earth and transition metal catalysts |
| DE19746266A1 (de) | 1997-10-20 | 1999-04-22 | Bayer Ag | Katalysator auf Basis von Verbindungen der seltenen Erdmetalle für die Polymerisation von ungesättigten organischen Verbindungen |
| KR100365581B1 (ko) * | 1999-02-25 | 2003-01-15 | 금호석유화학 주식회사 | 높은 1,4-시스 함량을 갖는 폴리부타디엔의 제조방법 |
| US6255420B1 (en) | 1999-11-22 | 2001-07-03 | Union Carbide Chemicals & Plastics Technology Corporation | Start-up process for gas phase production of polybutadiene |
| DE60213380T2 (de) * | 2001-02-28 | 2007-08-23 | Bridgestone Corp. | Kontinuierliches verfahren zur herstellung von engeren molekulargewichtverteilungen konjugierten dien-polymeren und dadurch hergestellten produkten |
| DE10115106A1 (de) | 2001-03-27 | 2002-10-10 | Bayer Ag | Blockcopolymerisat auf Basis von konjugierten Diolefinen und polaren Monomeren |
| US6871751B2 (en) * | 2001-10-19 | 2005-03-29 | The Goodyear Tire & Rubber Company | Rubber for baby bottle nipples, pacifiers, & syringe plungers |
| US9226876B2 (en) * | 2001-10-19 | 2016-01-05 | The Goodyear Tire & Rubber Company | Rubber for baby bottle nipples, pacifiers, and syringe plungers |
| US6780948B2 (en) | 2002-03-28 | 2004-08-24 | The Goodyear Tire & Rubber Company | Synthesis of polyisoprene with neodymium catalyst |
| US7094849B2 (en) * | 2003-12-15 | 2006-08-22 | Bridgestone Corporation | Bulk polymerization process for producing polydienes |
| US7091150B2 (en) * | 2003-12-19 | 2006-08-15 | The Goodyear Tire & Rubber Company | Synthetic polyisoprene rubber |
| JP5111101B2 (ja) | 2004-03-02 | 2012-12-26 | 株式会社ブリヂストン | バルク重合プロセス |
| FR2892121B1 (fr) * | 2005-10-19 | 2008-01-04 | Michelin Soc Tech | Procede de preparation en continu d'un systeme catalytique pour polymeriser un diene conjugue, et installation pour sa mise en oeuvre. |
| US7807763B2 (en) * | 2008-04-07 | 2010-10-05 | Bridgestone Corporation | Method for bulk polymerization |
| US8701728B2 (en) | 2009-10-14 | 2014-04-22 | Bridgestone Corporation | Processes for preparation of cyclic and acyclic diene copolymer and rubber composition |
| RU2523799C1 (ru) | 2011-12-20 | 2014-07-27 | Чайна Петролеум Энд Кемикал Корпорейшн | Добавка и способ для обрыва полимеризации и/или снижения вязкости раствора полимера |
| WO2016105931A1 (en) | 2014-12-23 | 2016-06-30 | Bridgestone Americas Tire Operations, Llc | Oil-containing rubber compositions and related methods |
| JP6717840B2 (ja) | 2015-01-28 | 2020-07-08 | 株式会社ブリヂストン | 熟成ランタニド系触媒系及びシス−１，４−ポリジエンの調製における同触媒系の使用 |
| CN114085303B (zh) * | 2021-12-21 | 2022-12-02 | 青岛科技大学 | 一种催化体系及其应用、间同1,2-聚丁二烯的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB950221A (en) * | 1960-12-19 | 1964-02-19 | Phillips Petroleum Co | Improvements in or relating to butadiene polymers |
| IT1085663B (it) * | 1977-08-01 | 1985-05-28 | Snam Progetti | Procedimento per la polimerizzazione e copolimerizzazione di diolefine e mezzi adatti allo scopo |
| CA1223396A (en) * | 1981-06-29 | 1987-06-23 | Tooru Shibata | Process for producing conjugated diene polymer |
| IT1151543B (it) * | 1982-04-15 | 1986-12-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| IT1151542B (it) * | 1982-04-15 | 1986-12-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| IT1164238B (it) * | 1983-05-25 | 1987-04-08 | Anic Spa | Procedimento per la polimerizzazione del butadiene |
-
1985
- 1985-07-01 IT IT21377/85A patent/IT1186747B/it active
-
1986
- 1986-06-17 ZA ZA864520A patent/ZA864520B/xx unknown
- 1986-06-17 IN IN470/MAS/86A patent/IN167543B/en unknown
- 1986-06-19 AU AU58865/86A patent/AU588329B2/en not_active Ceased
- 1986-06-20 DE DE8686201076T patent/DE3678047D1/de not_active Expired - Lifetime
- 1986-06-20 EP EP86201076A patent/EP0207558B1/en not_active Expired - Lifetime
- 1986-06-24 US US06/878,036 patent/US4699960A/en not_active Expired - Lifetime
- 1986-06-25 ES ES556948A patent/ES8708238A1/es not_active Expired
- 1986-06-27 KR KR1019860005189A patent/KR890002925B1/ko not_active Expired
- 1986-06-30 CS CS493286A patent/CS273176B2/cs not_active IP Right Cessation
- 1986-06-30 IE IE175486A patent/IE58948B1/en not_active IP Right Cessation
- 1986-06-30 CN CN86104504.1A patent/CN1005413B/zh not_active Expired
- 1986-06-30 CA CA000512808A patent/CA1277093C/en not_active Expired - Fee Related
- 1986-06-30 DD DD86291924A patent/DD248128A5/de not_active IP Right Cessation
- 1986-07-01 EG EG40486A patent/EG18915A/xx active
- 1986-07-01 JP JP61154913A patent/JPH0730135B2/ja not_active Expired - Fee Related
- 1986-07-01 YU YU114986A patent/YU46011B/sh unknown
- 1986-07-01 PT PT82887A patent/PT82887B/pt unknown
- 1986-07-01 PL PL1986260391A patent/PL147478B3/pl unknown
- 1986-07-01 BR BR8603229A patent/BR8603229A/pt not_active IP Right Cessation
- 1986-07-01 TR TR34786A patent/TR23851A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4699960A (en) | 1987-10-13 |
| KR870001241A (ko) | 1987-03-12 |
| TR23851A (tr) | 1990-10-15 |
| ZA864520B (en) | 1987-02-25 |
| ES8708238A1 (es) | 1987-10-01 |
| PT82887B (pt) | 1989-01-30 |
| IE861754L (en) | 1987-01-01 |
| DD248128A5 (de) | 1987-07-29 |
| EG18915A (en) | 1994-10-30 |
| IT8521377A0 (it) | 1985-07-01 |
| CA1277093C (en) | 1990-11-27 |
| CN1005413B (zh) | 1989-10-11 |
| DE3678047D1 (de) | 1991-04-18 |
| CN86104504A (zh) | 1987-02-18 |
| IT1186747B (it) | 1987-12-16 |
| EP0207558B1 (en) | 1991-03-13 |
| PL147478B3 (en) | 1989-06-30 |
| ES556948A0 (es) | 1987-10-01 |
| JPS6213411A (ja) | 1987-01-22 |
| PT82887A (en) | 1986-08-01 |
| YU46011B (sh) | 1992-12-21 |
| IE58948B1 (en) | 1993-12-01 |
| AU588329B2 (en) | 1989-09-14 |
| IN167543B (pl) | 1990-11-10 |
| KR890002925B1 (ko) | 1989-08-12 |
| BR8603229A (pt) | 1987-02-24 |
| EP0207558A1 (en) | 1987-01-07 |
| JPH0730135B2 (ja) | 1995-04-05 |
| AU5886586A (en) | 1987-01-08 |
| YU114986A (en) | 1987-10-31 |
| CS493286A2 (en) | 1990-07-12 |
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| Date | Code | Title | Description |
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| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20010630 |