ES2057917T3 - Produccion de lactida a partir de la deshidratacion de un producto acuoso de acido lactico. - Google Patents
Produccion de lactida a partir de la deshidratacion de un producto acuoso de acido lactico.Info
- Publication number
- ES2057917T3 ES2057917T3 ES91917931T ES91917931T ES2057917T3 ES 2057917 T3 ES2057917 T3 ES 2057917T3 ES 91917931 T ES91917931 T ES 91917931T ES 91917931 T ES91917931 T ES 91917931T ES 2057917 T3 ES2057917 T3 ES 2057917T3
- Authority
- ES
- Spain
- Prior art keywords
- lactic acid
- product
- lactide
- aqueous
- feed
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/19—Details relating to the geometry of the reactor
- B01J2219/194—Details relating to the geometry of the reactor round
- B01J2219/1941—Details relating to the geometry of the reactor round circular or disk-shaped
- B01J2219/1942—Details relating to the geometry of the reactor round circular or disk-shaped spherical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Fodder In General (AREA)
- Medicinal Preparation (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Freezing, Cooling And Drying Of Foods (AREA)
Abstract
LA PRESENTE INVENCION SE REFIERE A UN METODO PARA LA PRODUCCION DE L-LACTIDOS (LD) A PARTIR DE UN ACIDO L-LACTICO ACUOSO. EL PRODUCTO DE ACIDO LACTICO ACUOSO UTILIZADO CON ESTE OBJETIVO CONSTA DE UNA MEZCLA ACUOSA DE UNO O MAS DE ENTRE EL ACIDO LACTICO, UN DIMERO DE ACIDO LACTICO Y UN TRIMERO DE ACIDO LACTICO ENCONTRANDOSE PRESENTE, OPCIONALMENTE, UN LD. EL ACIDO L-LACTICO ES LA CONFIGURACION DEL PRODUCTO PREFERENTE PARA LA PRODUCCION DE L-LACTIDOS Y SE HA DE ENTENDER ASI INCLUSO SI EL SIMBOLO DE CONFIGURACION NO SE UTILIZA A LO LARGO DE TODA ESTA APLICACION. SE TRATA EL PRODUCTO DE ACIDO LACTICO ACUOSO PARA RETIRAR EL AGUA DEL MISMO HASTA QUE SE ALCANCE UN GRADO DE POLIMERIZACION (DP) QUE NO SEA SUSTANCIALMENTE MAYOR DE 2 APROXIMADAMENTE. A CONTINUACION SE DEJA EL TRATAMIENTO PARA PRODUCIR UN PRODUCTO DE LD BRUTO. A CONTINUACION SE SEPARA EL LD DEL PRODUCTO DE LD BRUTO. UN TRATAMIENTO PREFERENTE CONSISTE EN CALENTAR EL PRODUCTO A UNA TEMPERATURA ELEVADA PARA ELIMINAR EL AGUA. EL LD SE PUEDE SEPARAR DEL PRODUCTO DE LD BRUTO SEGUN UNA SERIE DE TECNICAS DIVERSAS PARA ASI PRODUCIR UN PRODUCTO CON UN CONTENIDO MUY BAJO DE LD. ESTE PRODUCTO CON UN CONTENIDO MUY BAJO DE LD, SE PUEDE AUMENTAR OPCIONALMENTE CON ACIDO LACTICO ACUOSO ADICIONAL Y/O CON AGUA Y DESPUES PUEDE SER READMITIDO EN EL PROCESO PARA LA PRODUCCION DE UN LACTIDO ADICIONAL. ESTE PROCESO CICLICO O DE RECICLADO DE LA PRESENTE INVENCION PERMITE QUE SE PUEDAN LLEVAR A CABO CONVERSIONES DE LACTIDOS MUY ELEVADAS.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/584,126 US5274127A (en) | 1990-09-18 | 1990-09-18 | Lactide production from dehydration of aqueous lactic acid feed |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2057917T3 true ES2057917T3 (es) | 1994-10-16 |
Family
ID=24336030
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES91917931T Expired - Lifetime ES2057917T3 (es) | 1990-09-18 | 1991-09-18 | Produccion de lactida a partir de la deshidratacion de un producto acuoso de acido lactico. |
Country Status (22)
Country | Link |
---|---|
US (1) | US5274127A (es) |
EP (1) | EP0552226B1 (es) |
JP (1) | JPH06504762A (es) |
KR (1) | KR0171432B1 (es) |
CN (1) | CN1061222A (es) |
AT (1) | ATE109141T1 (es) |
AU (1) | AU653179B2 (es) |
BR (1) | BR9106855A (es) |
CA (1) | CA2091691A1 (es) |
DE (1) | DE69103159T2 (es) |
DK (1) | DK0552226T3 (es) |
ES (1) | ES2057917T3 (es) |
FI (1) | FI95697C (es) |
HK (1) | HK175595A (es) |
IE (1) | IE62721B1 (es) |
IL (1) | IL99519A0 (es) |
MX (1) | MX9101131A (es) |
MY (1) | MY107225A (es) |
NZ (1) | NZ239824A (es) |
PT (1) | PT98998A (es) |
WO (1) | WO1992005167A1 (es) |
ZA (1) | ZA917410B (es) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5767222A (en) * | 1988-08-08 | 1998-06-16 | Chronopol, Inc. | Degradable polydioxaneone-based materials |
US5444113A (en) * | 1988-08-08 | 1995-08-22 | Ecopol, Llc | End use applications of biodegradable polymers |
US5319107A (en) * | 1990-09-18 | 1994-06-07 | Biopak Technology, Ltd. | Method to produce cyclic esters |
US5332839A (en) * | 1990-09-18 | 1994-07-26 | Biopak Technology, Ltd. | Catalytic production of lactide directly from lactic acid |
US5326887A (en) * | 1991-02-27 | 1994-07-05 | E. I. Du Pont De Nemours And Company | Process for the preparation of 1,4-dioxane-2,5-diones |
US5247059A (en) * | 1992-01-24 | 1993-09-21 | Cargill, Incorporated | Continuous process for the manufacture of a purified lactide from esters of lactic acid |
US6005067A (en) * | 1992-01-24 | 1999-12-21 | Cargill Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
US5142023A (en) * | 1992-01-24 | 1992-08-25 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
US5258488A (en) * | 1992-01-24 | 1993-11-02 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
US5247058A (en) * | 1992-01-24 | 1993-09-21 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
US6326458B1 (en) | 1992-01-24 | 2001-12-04 | Cargill, Inc. | Continuous process for the manufacture of lactide and lactide polymers |
US5686630A (en) * | 1993-09-29 | 1997-11-11 | Chronopol, Inc. | Purifying cyclic esters by aqueous solvent extraction |
US5420304A (en) * | 1992-03-19 | 1995-05-30 | Biopak Technology, Ltd. | Method to produce cyclic esters |
ES2123668T3 (es) * | 1992-10-02 | 1999-01-16 | Cargill Inc | Papel que tiene un recubrimiento de polimero de lactida estable en estado fundido y procedimiento para su fabricacion. |
DE69330046T2 (de) | 1992-10-02 | 2001-11-15 | Cargill Inc | Schmelzstabiles lactidpolymergewebe und verfahren zu seiner herstellung |
US5338822A (en) * | 1992-10-02 | 1994-08-16 | Cargill, Incorporated | Melt-stable lactide polymer composition and process for manufacture thereof |
US6005068A (en) | 1992-10-02 | 1999-12-21 | Cargill Incorporated | Melt-stable amorphous lactide polymer film and process for manufacture thereof |
JPH07165753A (ja) * | 1993-12-08 | 1995-06-27 | Musashino Kagaku Kenkyusho:Kk | ラクチドの精製方法 |
JPH10109983A (ja) * | 1996-10-04 | 1998-04-28 | Mitsubishi Gas Chem Co Inc | 環状エステルの製造方法および精製方法 |
US5900266A (en) * | 1997-05-29 | 1999-05-04 | The Curators Of The University Of Missouri | Heat-treated lactic and/or glycolic acid compositions and methods of use |
US6326042B1 (en) | 1997-05-29 | 2001-12-04 | The Curators Of The University Of Missouri | Antimicrobial use of heat-treated lactic and/or glycolic acid compositions for treatment of ground meats |
US6313319B1 (en) | 1998-09-25 | 2001-11-06 | Shimadzu Corporation | Method for purifying lactide and lactide for food additives |
WO2001042333A2 (en) | 1999-12-13 | 2001-06-14 | Michigan State University | Process for the preparation of polymers of dimeric cyclic esters |
CN100545159C (zh) * | 2005-12-19 | 2009-09-30 | 奇美实业股份有限公司 | α-羟基有机酸环酯类化合物的制造方法 |
US7723461B1 (en) | 2005-12-22 | 2010-05-25 | Tetramer Technologies, Llc | Polymeric materials from renewable resources |
JP5409596B2 (ja) | 2007-03-30 | 2014-02-05 | ラキュアー エービー | 婦人科の障害の治療における乳酸オリゴマーの使用 |
EP2072508A1 (fr) | 2007-12-19 | 2009-06-24 | Galactic S.A. | Procédé d'obtention de lactide |
CN101434594B (zh) * | 2008-12-19 | 2012-05-02 | 河北科技大学 | 混合溶剂法制备丙交酯的方法 |
KR101154029B1 (ko) | 2009-05-20 | 2012-06-07 | 한국화학연구원 | 젖산에스테르로부터 락타이드의 직접 전환용 촉매 및 이를 이용한 락타이드의 제조방법 |
US8383851B2 (en) * | 2010-09-15 | 2013-02-26 | Caravan Ingredients Inc. | Lactylate synthesis methods using dilactides |
BR112013010169B1 (pt) | 2010-10-28 | 2021-11-16 | Total Raffinage Marketing | Microrganismo monascus ruber, seu uso na produção de ácido láctico e método para produzir uma composição a um rendimento elevado, que compreende um ácido láctico |
KR20140053129A (ko) * | 2011-07-15 | 2014-05-07 | 플라시카 리미티드 | 분리방법 |
WO2013160485A1 (de) | 2012-04-28 | 2013-10-31 | Uhde Inventa-Fischer Gmbh | Verfahren zur kontinuierlichen herstellung von lactid direkt aus konzentrierter milchsäure |
KR101428340B1 (ko) | 2012-12-31 | 2014-08-07 | 현대자동차주식회사 | 이온성 용매를 이용한 락타이드 제조법 |
KR101704563B1 (ko) | 2015-10-12 | 2017-02-08 | 한국화학연구원 | 락타이드 정제공정을 이용한 락타이드 제조방법 및 제조장치 |
CN107118200B (zh) | 2016-02-24 | 2020-02-28 | 香港纺织及成衣研发中心有限公司 | 一种利用乳酸催化合成丙交酯的方法 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA863673A (en) * | 1971-02-16 | K. Schneider Allan | Absorbable suture | |
DE53074C (de) * | Frau A. LA GUAYRA MAYO in Great Falls, Cty Cascade, und W. HUDNALL in Helena, Cty Lewisand Clark, V. St. A | Verstellbare Säumvorrichtung für Nähmaschinen | ||
DE221786C (es) * | ||||
DE267826C (de) * | 1912-12-28 | 1913-12-02 | Chemische Werke | Verfahren zur Darstellung von lactid |
US1095205A (en) * | 1913-05-15 | 1914-05-05 | Chemische Werke Vorm Dr Heinrich Byk | Manufacture of lactid. |
US1594843A (en) * | 1921-08-19 | 1926-08-03 | Du Pont | Purification of lactic acid |
US1995970A (en) * | 1931-04-04 | 1935-03-26 | Du Pont | Polymeric lactide resin |
US2163268A (en) * | 1933-12-12 | 1939-06-20 | Du Pont | Method for making cyclic esters |
US2174491A (en) * | 1938-06-28 | 1939-09-26 | Paul D Watson | Method of making lactic acid resinous products |
US2189572A (en) * | 1938-09-01 | 1940-02-06 | Paul D Watson | Process for fractionating resinous products |
US2703316A (en) * | 1951-06-05 | 1955-03-01 | Du Pont | Polymers of high melting lactide |
US2668162A (en) * | 1952-03-20 | 1954-02-02 | Du Pont | Preparation of high molecular weight polyhydroxyacetic ester |
US2758987A (en) * | 1952-06-05 | 1956-08-14 | Du Pont | Optically active homopolymers containing but one antipodal species of an alpha-monohydroxy monocarboxylic acid |
US2768973A (en) * | 1954-11-30 | 1956-10-30 | Du Pont | Preparation of glycolaldehyde by hydrolysis of 4-chloro-2-oxodioxolane |
US3322791A (en) * | 1963-09-26 | 1967-05-30 | Ethicon Inc | Preparation of optically active lactides |
DE1194142B (de) * | 1963-11-19 | 1965-06-03 | Bayer Ag | Verfahren zum UV-Stabilisieren von Polycarbonaten |
BE674355A (es) * | 1964-12-28 | 1966-06-27 | ||
US3457280A (en) * | 1967-06-12 | 1969-07-22 | American Cyanamid Co | Alpha-glycolide and methods for the isolation thereof |
US3435008A (en) * | 1967-08-22 | 1969-03-25 | American Cyanamid Co | Method for preparation of isomerically pure beta-glycolide and polymerization method for glycolide compositions employing partial hydrolyzate of said beta-glycolide |
US3597450A (en) * | 1969-11-05 | 1971-08-03 | American Cyanamid Co | Preparation of glycolide polymerizable into polyglycolic acid of consistently high molecular weight |
US3736646A (en) * | 1971-10-18 | 1973-06-05 | American Cyanamid Co | Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures |
US3867190A (en) * | 1971-10-18 | 1975-02-18 | American Cyanamid Co | Reducing capillarity of polyglycolic acid sutures |
US4033938A (en) * | 1974-01-21 | 1977-07-05 | American Cyanamid Company | Polymers of unsymmetrically substituted 1,4-dioxane-2,5-diones |
US3960152A (en) * | 1974-01-21 | 1976-06-01 | American Cyanamid Company | Surgical sutures of unsymmetrically substituted 1,4-dioxane-2,5-diones |
EP0261572A1 (de) * | 1986-09-20 | 1988-03-30 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Lactid |
DE3708915C2 (de) * | 1987-03-19 | 1996-04-04 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Lactid |
DE3632103A1 (de) * | 1986-09-20 | 1988-03-24 | Boehringer Ingelheim Kg | Verfahren zur herstellung von lactid |
EP0264926B1 (de) * | 1986-10-24 | 1992-04-08 | Boehringer Ingelheim Kg | Verfahren zur Herstellung und Reinigung thermolabiler Verbindungen |
ES2052551T3 (es) * | 1986-12-19 | 1994-07-16 | Akzo Nv | Metodo para preparar poli(acido lactico) o copolimeros de poli(acido lactico) por polimeracion de la lactida. |
US4835293A (en) * | 1987-02-24 | 1989-05-30 | E. I. Du Pont De Nemours And Company | Atmospheric pressure process for preparing pure cyclic esters |
NL8702563A (nl) * | 1987-10-28 | 1989-05-16 | Cca Biochem B V | Polymeer lactide, werkwijze voor het bereiden van een dergelijk polymeer lactide, alsmede een samenstelling, die een dergelijk polymeer lactide bevat. |
US5068418A (en) * | 1989-05-08 | 1991-11-26 | Uop | Separation of lactic acid from fermentation broth with an anionic polymeric absorbent |
US5075115A (en) * | 1990-04-02 | 1991-12-24 | Fmc Corporation | Process for polymerizing poly(lactic acid) |
DE69127284D1 (de) * | 1990-05-03 | 1997-09-18 | Du Pont | Verfahren zur schnellen herstellung cyclischer ester |
US5091544A (en) * | 1990-05-08 | 1992-02-25 | E. I. Du Pont De Nemours And Company | Process for rapid conversion of oligomers to cyclic esters |
US5043458A (en) * | 1990-05-03 | 1991-08-27 | E. I. Du Pont De Nemours And Company | One-step continuous process for preparing cyclic esters |
US5023349A (en) * | 1990-05-08 | 1991-06-11 | E. I. Du Pont De Nemours And Company | Continuous process for rapid conversion of oligomers to cyclic esters |
US5023350A (en) * | 1990-05-24 | 1991-06-11 | E. I. Du Pont De Nemours And Company | Process for the purification of cyclic esters |
US5138074A (en) * | 1990-06-28 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Continuous catalyzed vapor phase dimeric cyclic ester process |
US5332839A (en) * | 1990-09-18 | 1994-07-26 | Biopak Technology, Ltd. | Catalytic production of lactide directly from lactic acid |
US5089632A (en) * | 1991-01-30 | 1992-02-18 | E. I. Du Pont De Nemours And Company | Process for preparing cyclic esters using a fluorocarbon |
-
1990
- 1990-09-18 US US07/584,126 patent/US5274127A/en not_active Expired - Fee Related
-
1991
- 1991-09-17 IE IE327291A patent/IE62721B1/en not_active IP Right Cessation
- 1991-09-17 ZA ZA917410A patent/ZA917410B/xx unknown
- 1991-09-17 NZ NZ239824A patent/NZ239824A/xx unknown
- 1991-09-18 WO PCT/US1991/006774 patent/WO1992005167A1/en active IP Right Grant
- 1991-09-18 DE DE69103159T patent/DE69103159T2/de not_active Expired - Fee Related
- 1991-09-18 CN CN91108029A patent/CN1061222A/zh active Pending
- 1991-09-18 AT AT91917931T patent/ATE109141T1/de not_active IP Right Cessation
- 1991-09-18 DK DK91917931.7T patent/DK0552226T3/da active
- 1991-09-18 KR KR1019930700809A patent/KR0171432B1/ko not_active IP Right Cessation
- 1991-09-18 MX MX9101131A patent/MX9101131A/es not_active IP Right Cessation
- 1991-09-18 MY MYPI91001692A patent/MY107225A/en unknown
- 1991-09-18 JP JP3516738A patent/JPH06504762A/ja active Pending
- 1991-09-18 EP EP91917931A patent/EP0552226B1/en not_active Expired - Lifetime
- 1991-09-18 CA CA002091691A patent/CA2091691A1/en not_active Abandoned
- 1991-09-18 ES ES91917931T patent/ES2057917T3/es not_active Expired - Lifetime
- 1991-09-18 AU AU87292/91A patent/AU653179B2/en not_active Ceased
- 1991-09-18 PT PT98998A patent/PT98998A/pt not_active Application Discontinuation
- 1991-09-18 BR BR919106855A patent/BR9106855A/pt not_active Application Discontinuation
- 1991-09-19 IL IL99519A patent/IL99519A0/xx unknown
-
1993
- 1993-03-17 FI FI931185A patent/FI95697C/fi not_active IP Right Cessation
-
1995
- 1995-11-16 HK HK175595A patent/HK175595A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FI95697C (fi) | 1996-03-11 |
DK0552226T3 (da) | 1994-09-12 |
FI931185A0 (fi) | 1993-03-17 |
ATE109141T1 (de) | 1994-08-15 |
CN1061222A (zh) | 1992-05-20 |
AU8729291A (en) | 1992-04-15 |
NZ239824A (en) | 1993-01-27 |
WO1992005167A1 (en) | 1992-04-02 |
ZA917410B (en) | 1992-05-27 |
IL99519A0 (en) | 1992-08-18 |
CA2091691A1 (en) | 1992-03-19 |
HK175595A (en) | 1995-11-24 |
US5274127A (en) | 1993-12-28 |
KR0171432B1 (ko) | 1999-02-01 |
MX9101131A (es) | 1992-05-04 |
IE62721B1 (en) | 1995-02-22 |
DE69103159T2 (de) | 1994-11-03 |
FI931185A (fi) | 1993-03-17 |
AU653179B2 (en) | 1994-09-22 |
PT98998A (pt) | 1992-07-31 |
DE69103159D1 (de) | 1994-09-01 |
EP0552226B1 (en) | 1994-07-27 |
BR9106855A (pt) | 1993-08-24 |
KR930702331A (ko) | 1993-09-08 |
EP0552226A1 (en) | 1993-07-28 |
IE913272A1 (en) | 1992-02-25 |
FI95697B (fi) | 1995-11-30 |
JPH06504762A (ja) | 1994-06-02 |
MY107225A (en) | 1995-10-31 |
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