CZ283113B6 - Způsob výroby polyalkenylových derivátů látek na bázi nenasycených dikarboxylových kyselin - Google Patents
Způsob výroby polyalkenylových derivátů látek na bázi nenasycených dikarboxylových kyselin Download PDFInfo
- Publication number
- CZ283113B6 CZ283113B6 CS923389A CS338992A CZ283113B6 CZ 283113 B6 CZ283113 B6 CZ 283113B6 CS 923389 A CS923389 A CS 923389A CS 338992 A CS338992 A CS 338992A CZ 283113 B6 CZ283113 B6 CZ 283113B6
- Authority
- CZ
- Czechia
- Prior art keywords
- acid
- weight
- carbon atoms
- polyalkene
- dicarboxylic acid
- Prior art date
Links
- 239000000126 substance Substances 0.000 title claims abstract description 16
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 229920000098 polyolefin Polymers 0.000 claims abstract description 25
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 45
- 229920002367 Polyisobutene Polymers 0.000 claims description 37
- 239000000376 reactant Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000005673 monoalkenes Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 125000001142 dicarboxylic acid group Chemical group 0.000 abstract description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000013049 sediment Substances 0.000 description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- -1 alkene hydrocarbon Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 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
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SASYHUDIOGGZCN-ARJAWSKDSA-N (z)-2-ethylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C\C(O)=O SASYHUDIOGGZCN-ARJAWSKDSA-N 0.000 description 1
- PAHUTFPWSUWSCR-BHPSOXLSSA-N (z)-2-methylbut-2-enedioic acid Chemical compound OC(=O)C(/C)=C\C(O)=O.OC(=O)C(/C)=C\C(O)=O PAHUTFPWSUWSCR-BHPSOXLSSA-N 0.000 description 1
- GIEGKXINITVUOO-UHFFFAOYSA-N 2-methylidenebutanedioic acid Chemical compound OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O GIEGKXINITVUOO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 229920002859 polyalkenylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical group 0.000 description 1
- 239000012808 vapor phase Substances 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91310579 | 1991-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ338992A3 CZ338992A3 (en) | 1993-09-15 |
| CZ283113B6 true CZ283113B6 (cs) | 1998-01-14 |
Family
ID=8208471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS923389A CZ283113B6 (cs) | 1991-11-15 | 1992-11-13 | Způsob výroby polyalkenylových derivátů látek na bázi nenasycených dikarboxylových kyselin |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0542380A1 (enExample) |
| JP (1) | JPH05230131A (enExample) |
| KR (1) | KR930009978A (enExample) |
| CN (1) | CN1072417A (enExample) |
| AU (1) | AU653650B2 (enExample) |
| BR (1) | BR9204418A (enExample) |
| CA (1) | CA2082913A1 (enExample) |
| CZ (1) | CZ283113B6 (enExample) |
| HU (1) | HU214192B (enExample) |
| TW (1) | TW242630B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69310644T2 (de) * | 1992-09-11 | 1997-09-04 | Shell Int Research | Benzinzusammensetzungen |
| DE4319671A1 (de) * | 1993-06-14 | 1994-12-15 | Basf Ag | Verfahren zur Herstellung von Polyisobutylbernsteinsäureanhydriden |
| US5777025A (en) * | 1996-02-09 | 1998-07-07 | Exxon Chemical Patents Inc. | Process for preparing polyalkenyl substituted C4 to C10 dicarboxylic acid producing materials |
| US5891953A (en) * | 1996-02-09 | 1999-04-06 | Exxon Chemical Patents Inc | Process for preparing polyalkenyl substituted mono- and dicarboxylic acid producing materials (PT-1302) |
| AU2968697A (en) * | 1996-06-10 | 1998-01-07 | Bp Chemicals Limited | Substituted carboxylated derivatives |
| US6156850A (en) * | 1998-09-16 | 2000-12-05 | Chevron Chemical Company Llc | Process for making polyalkenyl derivative of an unsaturated acidic reagent |
| US6107450A (en) * | 1998-12-15 | 2000-08-22 | Chevron Chemical Company Llc | Polyalkylene succinimides and post-treated derivatives thereof |
| US6451920B1 (en) * | 1999-11-09 | 2002-09-17 | Chevron Chemical Company Llc | Process for making polyalkylene/maleic anhydride copolymer |
| CN1102570C (zh) * | 2000-03-23 | 2003-03-05 | 中国石油化工集团公司 | 低浊度烯基丁二酸酐的制备方法 |
| EP1294776A2 (en) * | 2000-05-18 | 2003-03-26 | The Lubrizol Corporation | Process for reacting large hydrophobic molecules with small hydrophilic molecules |
| US7884058B2 (en) | 2003-09-30 | 2011-02-08 | Chevron Oronite Company Llc | Stable colloidal suspensions and lubricating oil compositions containing same |
| US7875576B2 (en) | 2004-07-29 | 2011-01-25 | Chevron Oronite Company Llc | Lubricating oil composition for internal combustion engines |
| EP1757673B1 (en) | 2005-08-23 | 2020-04-15 | Chevron Oronite Company LLC | Lubricating oil composition for internal combustion engines |
| EP1803771B1 (en) | 2005-12-28 | 2017-12-06 | Bridgestone Corporation | A rubber composition having good wet-traction properties and a low aromatic-oil content |
| JP4046136B2 (ja) | 2006-02-20 | 2008-02-13 | ダイキン工業株式会社 | 冷凍装置 |
| US7700673B2 (en) | 2006-12-22 | 2010-04-20 | Bridgestone Corporation | Reduced oil rubber compositions including N-substituted polyalkylene succinimide derivates and methods for preparing such compositions |
| ES2381316T3 (es) | 2007-12-31 | 2012-05-25 | Bridgestone Corporation | Jabones de metal incorporados a composiciones de caucho y el método para incorporar tales jabones en composiciones de caucho |
| JP2011526327A (ja) | 2008-06-26 | 2011-10-06 | 株式会社ブリヂストン | 金属で官能化されたポリイソブチレン誘導体を含むゴム組成物及びかかる組成物の調製方法 |
| US8153566B2 (en) | 2008-09-30 | 2012-04-10 | Cherron Oronite Company LLC | Lubricating oil compositions |
| US8389609B2 (en) | 2009-07-01 | 2013-03-05 | Bridgestone Corporation | Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions |
| US9803060B2 (en) | 2009-09-10 | 2017-10-31 | Bridgestone Corporation | Compositions and method for making hollow nanoparticles from metal soaps |
| US8901050B2 (en) | 2010-03-31 | 2014-12-02 | Chevron Oronite Company Llc | Method for improving copper corrosion performance |
| US8933001B2 (en) | 2010-03-31 | 2015-01-13 | Chevron Oronite Company Llc | Method for improving fluorocarbon elastomer seal compatibility |
| US8802755B2 (en) | 2011-01-18 | 2014-08-12 | Bridgestone Corporation | Rubber compositions including metal phosphate esters |
| CN104995248B (zh) | 2012-11-02 | 2017-12-08 | 株式会社普利司通 | 包含金属羧酸盐的橡胶组合物和其制备方法 |
| CA2863895C (en) | 2013-09-23 | 2021-11-09 | Chevron Japan Ltd. | A fuel economy engine oil composition |
| CN103601845B (zh) * | 2013-11-04 | 2015-11-11 | 上海金兆节能科技有限公司 | 聚异丁烯丁烯二酸酯及其制备方法和用该聚酯制备微量润滑油 |
| US9528074B2 (en) | 2015-02-13 | 2016-12-27 | Chevron Oronite Technology B.V. | Lubricating oil compositions with enhanced piston cleanliness |
| US9528071B2 (en) | 2015-02-13 | 2016-12-27 | Chevron Oronite Technology B.V. | Lubricating oil compositions with enhanced piston cleanliness |
| US20160281020A1 (en) | 2015-03-23 | 2016-09-29 | Chevron Japan Ltd. | Lubricating oil compositions for construstion machines |
| US9499765B2 (en) | 2015-03-23 | 2016-11-22 | Chevron Japan Ltd. | Lubricating oil compositions for construction machines |
| CN109415559B (zh) * | 2016-06-15 | 2021-09-10 | 巴斯夫欧洲公司 | 用于聚酰胺的基于聚异丁烯的抗冲改性剂 |
| US10604719B2 (en) | 2018-02-22 | 2020-03-31 | Chevron Japan Ltd. | Lubricating oils for automatic transmissions |
| CN118715310A (zh) | 2022-01-25 | 2024-09-27 | 雪佛龙日本有限公司 | 润滑油组合物 |
| AU2024257198A1 (en) | 2023-04-17 | 2025-10-30 | Chevron Oronite Company Llc | Friction modifier for wet clutch |
| AU2024257381A1 (en) | 2023-04-17 | 2025-11-06 | Chevron Oronite Company Llc | Friction modifier for automatic transmission fluid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008168A (en) * | 1973-05-10 | 1977-02-15 | Standard Oil Company (Indiana) | Polybutene composition containing halogen-containing additives and use thereof |
| EP0014288B1 (en) * | 1978-12-07 | 1983-06-08 | Exxon Research And Engineering Company | Process for producing oil soluble derivatives of unsaturated c4-c10 dicarboxylic acid materials |
| US4235786A (en) * | 1979-10-01 | 1980-11-25 | Exxon Research & Engineering Co. | Process for producing oil-soluble derivatives of unsaturated C4 -C.sub. |
| US4652600A (en) * | 1985-09-20 | 1987-03-24 | Exxon Research And Engineering Company | Sulfomaleation of polyolefins (C-1966) |
-
1992
- 1992-10-22 TW TW081108425A patent/TW242630B/zh active
- 1992-11-12 KR KR1019920021217A patent/KR930009978A/ko not_active Ceased
- 1992-11-12 EP EP92203484A patent/EP0542380A1/en not_active Ceased
- 1992-11-13 JP JP4303778A patent/JPH05230131A/ja active Pending
- 1992-11-13 CN CN92113005A patent/CN1072417A/zh active Pending
- 1992-11-13 CA CA002082913A patent/CA2082913A1/en not_active Abandoned
- 1992-11-13 CZ CS923389A patent/CZ283113B6/cs not_active IP Right Cessation
- 1992-11-13 AU AU28364/92A patent/AU653650B2/en not_active Ceased
- 1992-11-13 HU HU9203565A patent/HU214192B/hu not_active IP Right Cessation
- 1992-11-16 BR BR929204418A patent/BR9204418A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9204418A (pt) | 1993-05-18 |
| JPH05230131A (ja) | 1993-09-07 |
| HU9203565D0 (en) | 1993-03-29 |
| CZ338992A3 (en) | 1993-09-15 |
| KR930009978A (ko) | 1993-06-21 |
| CN1072417A (zh) | 1993-05-26 |
| CA2082913A1 (en) | 1993-05-16 |
| HU214192B (hu) | 1998-01-28 |
| EP0542380A1 (en) | 1993-05-19 |
| HUT63639A (en) | 1993-09-28 |
| AU653650B2 (en) | 1994-10-06 |
| AU2836492A (en) | 1993-05-20 |
| TW242630B (enExample) | 1995-03-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20001113 |