JP3183506B2 - 改良されたスクロース―6―エステル塩素化方法 - Google Patents
改良されたスクロース―6―エステル塩素化方法Info
- Publication number
- JP3183506B2 JP3183506B2 JP18732890A JP18732890A JP3183506B2 JP 3183506 B2 JP3183506 B2 JP 3183506B2 JP 18732890 A JP18732890 A JP 18732890A JP 18732890 A JP18732890 A JP 18732890A JP 3183506 B2 JP3183506 B2 JP 3183506B2
- Authority
- JP
- Japan
- Prior art keywords
- sucrose
- benzoate
- ester
- sucralose
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US382147 | 1989-07-18 | ||
| US07/382,147 US4980463A (en) | 1989-07-18 | 1989-07-18 | Sucrose-6-ester chlorination |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03218388A JPH03218388A (ja) | 1991-09-25 |
| JP3183506B2 true JP3183506B2 (ja) | 2001-07-09 |
Family
ID=23507711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18732890A Expired - Fee Related JP3183506B2 (ja) | 1989-07-18 | 1990-07-17 | 改良されたスクロース―6―エステル塩素化方法 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4980463A (enExample) |
| EP (1) | EP0409549B1 (enExample) |
| JP (1) | JP3183506B2 (enExample) |
| KR (1) | KR0144344B1 (enExample) |
| AR (1) | AR247401A1 (enExample) |
| AT (1) | ATE133175T1 (enExample) |
| AU (1) | AU625908B2 (enExample) |
| CA (1) | CA2021632C (enExample) |
| DE (1) | DE69024868T2 (enExample) |
| DK (1) | DK0409549T3 (enExample) |
| ES (1) | ES2088973T3 (enExample) |
| FI (1) | FI95802C (enExample) |
| GR (1) | GR1002037B (enExample) |
| IE (1) | IE69961B1 (enExample) |
| IL (1) | IL94994A (enExample) |
| MX (1) | MX164442B (enExample) |
| NO (1) | NO175532C (enExample) |
| NZ (1) | NZ234468A (enExample) |
| PE (1) | PE21591A1 (enExample) |
| PH (1) | PH26799A (enExample) |
| PT (1) | PT94719B (enExample) |
| RU (1) | RU1836377C (enExample) |
| TR (1) | TR28705A (enExample) |
| TW (1) | TW219939B (enExample) |
| YU (1) | YU47948B (enExample) |
| ZA (1) | ZA905615B (enExample) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5136031A (en) * | 1990-07-09 | 1992-08-04 | Tate & Lyle Public Limited Company | Chlorination of sugars |
| US5470969A (en) * | 1990-08-27 | 1995-11-28 | Mcneil-Ppc, Inc. | Catalyzed sucrose-6-ester process |
| GB9110931D0 (en) * | 1991-05-21 | 1991-07-10 | Tate & Lyle Plc | Process for the preparation of sucrose 6-esters |
| US5298611A (en) * | 1993-03-12 | 1994-03-29 | Mcneil-Ppc, Inc. | Sucralose pentaester production |
| WO1996001832A1 (en) | 1994-07-11 | 1996-01-25 | The United States Of America, Represented By The Secretary Of The Department Of Agriculture | Chemically synthesized sugar esters for the control of soft-bodied arthropods |
| US6608039B1 (en) | 1994-07-11 | 2003-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Chemically synthesized sugar esters for the control of soft-bodied arthropods |
| US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
| ZA958724B (en) * | 1994-10-17 | 1997-04-16 | Mcnell Ppc Inc | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
| KR100405203B1 (ko) * | 1996-05-23 | 2004-02-14 | 비앤티엔지니어링(주) | 암거배수로관 |
| IL131394A0 (en) * | 1997-02-13 | 2001-01-28 | Mcneil Ppc Inc | Chromatographic purification of chlorinated sucrose |
| EP1076661A1 (en) * | 1998-05-15 | 2001-02-21 | Rostislav G. Zhbankov | Method of preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
| DE19924770A1 (de) * | 1999-05-29 | 2000-12-21 | Buna Sow Leuna Olefinverb Gmbh | Verfahren zur Herstellung von Polyetherpolyolen aus Polysacchariden und deren Verwendung für die Herstellung von PUR-Schäumen |
| US6500973B2 (en) | 2000-06-02 | 2002-12-31 | Eastman Chemical Company | Extractive solution crystallization of chemical compounds |
| DE60133011T2 (de) * | 2000-08-25 | 2009-03-19 | Eastman Chemical Co., Kingsport | Verfahren zur herstellung von disaccharid und trisaccharid c6-c12 fettsäure-estern mit hohem alpha gehalt und materialien davon |
| US6667397B2 (en) * | 2000-08-25 | 2003-12-23 | Eastman Chemical Company | Methods of preparing disaccharide and trisaccharide C6-C12 fatty acid esters with high alpha content and materials therefrom |
| BR0115482B1 (pt) * | 2000-11-17 | 2013-02-19 | sacralose cristalina, seu processo de cristalizaÇço e seu produto. | |
| US7049435B2 (en) | 2002-03-08 | 2006-05-23 | Tate & Lyle Public Limited Company | Extractive methods for purifying sucralose |
| US6998480B2 (en) | 2002-03-08 | 2006-02-14 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield |
| US20040170735A2 (en) * | 2002-04-05 | 2004-09-02 | Mcneil-Ppc, Inc. | Methods and compositions for altering the sweetness delivery profile of sucralose |
| US6890581B2 (en) * | 2002-04-05 | 2005-05-10 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation |
| US20040086605A1 (en) * | 2002-10-30 | 2004-05-06 | Sox Thomas E. | Composition for delivering a high intensity sweetener |
| US6943248B2 (en) * | 2003-04-30 | 2005-09-13 | Tate & Lyle Public Limited Company | Crystalline form of sucralose, and method for producing it |
| CN1176094C (zh) * | 2003-05-23 | 2004-11-17 | 广东省食品工业研究所 | 一种三氯蔗糖的合成方法 |
| WO2005087020A1 (en) * | 2004-03-05 | 2005-09-22 | Richmond Chemical Corporation | High-intensity sweetener-polyol compositions |
| MXPA06010665A (es) * | 2004-03-19 | 2007-03-28 | Pharmed Medicare Pvt Ltd | Un proceso mejorado para producir sacarosa clorada. |
| US20050214425A1 (en) * | 2004-03-23 | 2005-09-29 | Roma Vazirani | Sugar substitute prepared with nutritive and high-intensity sweeteners |
| WO2006061856A2 (en) * | 2004-12-10 | 2006-06-15 | Pharmed Medicare Private Limited | Improved process for purificaton of 6 acetyl 4,1’,6’ trichlorogalactosucrose and 4,1’,6’ trichlorogalactosucrose by chromatography on silanized silica gel |
| WO2006061854A2 (en) * | 2004-12-10 | 2006-06-15 | Pharmed Medicare Private Limited | CONTROL OF pH BY DIRECT ADDITION OF CARBONATES AND BICARBONATES DURING CONCENTRATION OF ORGANIC SOLVENT EXTRACTS OF 6- ACETYL- 4,1 ‘, 6' TRICHLOROGALACTOSUCROSE AND 4,1 ‘, 6' TRICHLOROGALACTOSUCROSE |
| WO2006061855A2 (en) * | 2004-12-10 | 2006-06-15 | Pharmed Medicare Private Limited | Salts assisted selective extraction of 6-acetyl-4.1', 6' trichlorogalactosucrose and 4, 1 ', 6' trichlorogalactosucrose from aqueous reaction mixture |
| CN101175762A (zh) * | 2005-01-03 | 2008-05-07 | 法马德医疗保险私人有限公司 | 通过氯化试剂的共-加入进行蔗糖-6-酯的氯化 |
| US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
| US20080163867A1 (en) * | 2005-02-22 | 2008-07-10 | Molecular Separation Process in Various Steps of Process for Production of Chlorinated Sugars, Their Precursors and Derivatives | |
| US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
| US20060247180A1 (en) * | 2005-04-29 | 2006-11-02 | Bergey James L | Purgative composition and uses thereof |
| AU2006277556A1 (en) * | 2005-05-04 | 2007-02-15 | V.B. Medicare Private Limited | Generation of Phosphorus Oxychloride as by-product from Phosphorus Pentachloride and DMF and its use for chlorination reaction by converting into Vilsmeier-Haack reagent. |
| GB2442619B (en) * | 2005-05-04 | 2010-05-26 | Pharmed Medicare Pvt Ltd | Chlorination of sucrose acylates using triphosgene |
| US20060276639A1 (en) * | 2005-06-01 | 2006-12-07 | Healthy Brands, Llc | Conversion of sucralose-6-ester to sucralose |
| CN102124017A (zh) * | 2005-06-01 | 2011-07-13 | V.B.医疗保险私人有限公司 | 利用溶剂萃取法纯化氯化蔗糖衍生物的方法 |
| US20100160625A1 (en) * | 2005-09-22 | 2010-06-24 | Rakesh Ratnam | Novel Preparation of 6-O-Acyl Chlorosucrose from Anhydrous Cholorinated Reaction Mass |
| US20070100139A1 (en) * | 2005-10-31 | 2007-05-03 | Healthy Brands, Llc | Methods for chlorinating sucrose-6-ester |
| US7741477B2 (en) * | 2006-01-10 | 2010-06-22 | Alembic Limited | Process for purification of sucralose |
| JP2009528342A (ja) * | 2006-02-28 | 2009-08-06 | ヴイ ビー メディケア プライヴェート リミテッド | 塩化チオニルを使用する糖類を塩素化するための新規塩素化試薬及び新規方法 |
| CN100418976C (zh) * | 2006-04-03 | 2008-09-17 | 广州科宏食品添加物有限公司 | 一种三氯蔗糖的制备方法 |
| CN100402541C (zh) * | 2006-06-15 | 2008-07-16 | 浙江工业大学 | 一种三氯蔗糖-6-乙酯的合成方法 |
| CN101092438A (zh) * | 2006-06-22 | 2007-12-26 | 南京莱因医药科技有限公司 | 6-o-苯甲酰三氯半乳型蔗糖四乙酯的制备方法 |
| BRPI0621844A2 (pt) * | 2006-07-06 | 2013-03-19 | Alembic Ltd | processo aperfeiÇoado para a preparaÇço de sucralose de alta pureza |
| CN100420697C (zh) * | 2006-08-30 | 2008-09-24 | 河北苏科瑞科技有限公司 | 一种制备蔗糖-6-有机酸酯的方法 |
| US20080103295A1 (en) * | 2006-10-25 | 2008-05-01 | David Losan Ho | Process for the preparation of sucrose-6-ester by esterification in the presence of solid superacid catalyst |
| US8258291B2 (en) * | 2006-10-25 | 2012-09-04 | Mamtek International Limited | Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC) |
| GB0702857D0 (en) * | 2007-01-19 | 2007-03-28 | Tate & Lyle Plc | Improved sucralose production method |
| US20080227971A1 (en) * | 2007-01-19 | 2008-09-18 | Leinhos Duane A | Deacylation of sucralose-6-acylates |
| CN101260127B (zh) * | 2007-03-06 | 2011-04-20 | 盐城捷康三氯蔗糖制造有限公司 | 由三氯蔗糖-6-乙酯脱乙酰基合成三氯蔗糖的方法 |
| US20080300392A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
| US20080300401A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
| AR070082A1 (es) * | 2008-01-04 | 2010-03-10 | Tate & Lyle Technology Ltd | Metodo para la produccion de sucralosa |
| US7932380B2 (en) * | 2008-03-06 | 2011-04-26 | Wanhe International (Group) Co. Ltd. | Process for the preparation of sucralose |
| US8557976B2 (en) * | 2008-03-13 | 2013-10-15 | Tate & Lyle Technology Limited | Microbial consortia and methods for their use |
| JP2011517445A (ja) * | 2008-03-20 | 2011-06-09 | テート アンド ライル テクノロジー リミテッド | 第三級アミド溶媒からの酸の除去 |
| US8436157B2 (en) * | 2008-03-26 | 2013-05-07 | Tate & Lyle Technology Limited | Method for the production of sucralose |
| US8497367B2 (en) * | 2008-04-03 | 2013-07-30 | Tate & Lyle Technology Limited | Sucralose purification process |
| AR071134A1 (es) * | 2008-04-03 | 2010-05-26 | Tate & Lyle Technology Ltd | Cristalizacion de sucralosa a partir de chorros que contienen sucralosa |
| TW200946683A (en) * | 2008-04-03 | 2009-11-16 | Tate & Lyle Technology Ltd | A process for the purification of aqueous feed streams containing sucralose extraction efficiency |
| US20090299055A1 (en) * | 2008-04-03 | 2009-12-03 | Tate & Lyle Technology Limited | Purification of Sucralose Containing Feed Streams for Sucralose Crystallization |
| US20090259036A1 (en) * | 2008-04-03 | 2009-10-15 | Tate & Lyle Technology Limited | Extraction of less polar impurities from sucralose containing aqueous feed streams |
| US7862744B2 (en) * | 2008-07-23 | 2011-01-04 | Mamtek International Limited | Methods and systems for preparing materials for sucralose production |
| US20100022765A1 (en) * | 2008-07-23 | 2010-01-28 | David Losan Ho | Methods for extracting and purifying sucralose intermediate |
| GB2468936B (en) | 2009-03-27 | 2011-09-07 | Mohamad Rami Radwan Jaber | Chlorination of sucrose-6-esters |
| GB2469157B (en) * | 2009-03-30 | 2011-07-06 | John Kerr | Process for removing dimethylamine during sucralose production |
| GB2469158B (en) | 2009-03-31 | 2011-09-28 | Peter J Seaberg | Base-assisted formation of tin-sucrose adducts |
| GB2471348B (en) * | 2009-06-22 | 2011-12-14 | Tate & Lyle Technology Ltd | A method for producing sucralose-6-acylate |
| GB2474311B (en) | 2009-10-12 | 2012-10-17 | Tate & Lyle Technology Ltd | Low temperature, single solvent process for the production of sucrose-6-ester |
| GB2474310B (en) | 2009-10-12 | 2012-02-29 | Tate & Lyle Technology Ltd | Process for the production of sucrose-6-ester |
| PL2609120T3 (pl) * | 2010-08-25 | 2016-03-31 | Davuluri Ramamohan Rao | Ulepszony sposób wytwarzania sugammadeksu |
| AU2011332011B2 (en) * | 2010-11-23 | 2017-01-12 | Lexington Pharmaceuticals Laboratories, Llc | Low temperature chlorination of carbohydrates |
| GB201110520D0 (en) | 2011-05-10 | 2011-08-03 | Tate & Lyle Technology Ltd | Extraction of carboxylic acids with tin compounds |
| JP5679447B2 (ja) * | 2011-06-20 | 2015-03-04 | 第一工業製薬株式会社 | ショ糖ベンゾエート組成物の製造方法 |
| US8884004B2 (en) | 2011-09-02 | 2014-11-11 | Divi's Laboratories, Ltd. | Process for the preparation of sucralose |
| ES2574261T3 (es) * | 2011-10-14 | 2016-06-16 | Lexington Pharmaceuticals Laboratories, Llc | Cloración de carbohidratos y derivados de carbohidratos |
| CN102964396B (zh) * | 2012-10-26 | 2015-11-18 | 溧阳维信生物科技有限公司 | 一种三氯蔗糖-6-乙酯重结晶的方法 |
| JP6109531B2 (ja) * | 2012-11-02 | 2017-04-05 | 第一工業製薬株式会社 | 溶媒の除去方法 |
| CN103145772A (zh) * | 2013-03-26 | 2013-06-12 | 山东金城柯瑞化学有限公司 | 三氯蔗糖的制备方法 |
| US10227367B2 (en) | 2013-12-16 | 2019-03-12 | Tate & Lyle Technology Limited | Chlorination of sucrose-6-esters |
| US10081651B2 (en) | 2014-08-08 | 2018-09-25 | Tate & Lyle Technology Limited | Chlorination of sucrose-6-esters |
| CN104387427A (zh) * | 2014-10-30 | 2015-03-04 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖的生产方法 |
| GB2536480B (en) | 2015-03-17 | 2019-09-04 | Tate & Lyle Tech Ltd | DMF Distillation |
| CN105131050B (zh) * | 2015-07-22 | 2018-07-31 | 青岛科技大学 | 一种氯化剂的制备方法及其制备三氯蔗糖的方法 |
| CN105859802B (zh) * | 2016-05-14 | 2019-02-12 | 广西科技大学 | 一种三氯蔗糖的结晶和纯化方法 |
| GB2551591B (en) | 2016-06-23 | 2019-08-07 | Tate & Lyle Tech Ltd | Liquid-liquid extraction of DMF |
| MX2023003704A (es) | 2020-09-30 | 2023-05-09 | Anhui Jinhe Ind Co Ltd | Método de purificación de sucralosa. |
| CN113699196A (zh) * | 2021-08-17 | 2021-11-26 | 安徽金禾实业股份有限公司 | 一种蔗糖-6-乙酸酯的无水酶法催化合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435440A (en) * | 1976-01-08 | 1984-03-06 | Tate & Lyle Limited | Sweeteners |
| EP0010409A1 (en) * | 1978-10-18 | 1980-04-30 | TATE & LYLE PATENT HOLDINGS LIMITED | Bittering agents |
| US4324888A (en) * | 1979-03-09 | 1982-04-13 | Talres Development (N.A.) N.V. | Process for the preparation of chlorodeoxysugars |
| EP0031651B1 (en) * | 1979-12-20 | 1983-03-23 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
| US4291158A (en) * | 1980-01-28 | 1981-09-22 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
| US4345933A (en) * | 1980-01-28 | 1982-08-24 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
| ATE9355T1 (de) * | 1980-07-08 | 1984-09-15 | Tate & Lyle Public Limited Company | Verfahren zur herstellung von 4,1',6'-trichlor4,1',6'-trideoxygalactosucrose (tgs). |
| IE55619B1 (en) * | 1982-09-13 | 1990-11-21 | Tate & Lyle Plc | 6-derivatives of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
| GB8316790D0 (en) * | 1983-06-21 | 1983-07-27 | Tate & Lyle Plc | Chemical process |
| GB8622345D0 (en) * | 1986-09-17 | 1986-10-22 | Tate & Lyle Plc | Sucrose derivatives |
-
1989
- 1989-07-18 US US07/382,147 patent/US4980463A/en not_active Expired - Lifetime
-
1990
- 1990-07-06 IL IL9499490A patent/IL94994A/en unknown
- 1990-07-06 PH PH40800A patent/PH26799A/en unknown
- 1990-07-11 NZ NZ234468A patent/NZ234468A/en unknown
- 1990-07-12 GR GR900100537A patent/GR1002037B/el not_active IP Right Cessation
- 1990-07-16 PE PE1990172224A patent/PE21591A1/es not_active Application Discontinuation
- 1990-07-16 CA CA002021632A patent/CA2021632C/en not_active Expired - Lifetime
- 1990-07-17 AR AR90317395A patent/AR247401A1/es active
- 1990-07-17 RU SU4830726A patent/RU1836377C/ru active
- 1990-07-17 FI FI903603A patent/FI95802C/fi not_active IP Right Cessation
- 1990-07-17 AU AU59069/90A patent/AU625908B2/en not_active Expired
- 1990-07-17 DE DE69024868T patent/DE69024868T2/de not_active Expired - Lifetime
- 1990-07-17 EP EP90307784A patent/EP0409549B1/en not_active Expired - Lifetime
- 1990-07-17 PT PT94719A patent/PT94719B/pt not_active IP Right Cessation
- 1990-07-17 ZA ZA905615A patent/ZA905615B/xx unknown
- 1990-07-17 IE IE260390A patent/IE69961B1/en not_active IP Right Cessation
- 1990-07-17 JP JP18732890A patent/JP3183506B2/ja not_active Expired - Fee Related
- 1990-07-17 DK DK90307784.0T patent/DK0409549T3/da active
- 1990-07-17 AT AT90307784T patent/ATE133175T1/de not_active IP Right Cessation
- 1990-07-17 NO NO903190A patent/NO175532C/no not_active IP Right Cessation
- 1990-07-17 ES ES90307784T patent/ES2088973T3/es not_active Expired - Lifetime
- 1990-07-18 YU YU141190A patent/YU47948B/sh unknown
- 1990-07-18 KR KR1019900010857A patent/KR0144344B1/ko not_active Expired - Fee Related
- 1990-07-18 TR TR00678/90A patent/TR28705A/xx unknown
- 1990-07-18 MX MX21634A patent/MX164442B/es unknown
- 1990-07-26 TW TW079106171A patent/TW219939B/zh active
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