EP0703960B1 - Procede de degommage d'un corps gras et corps gras ainsi obtenu - Google Patents
Procede de degommage d'un corps gras et corps gras ainsi obtenu Download PDFInfo
- Publication number
- EP0703960B1 EP0703960B1 EP94916852A EP94916852A EP0703960B1 EP 0703960 B1 EP0703960 B1 EP 0703960B1 EP 94916852 A EP94916852 A EP 94916852A EP 94916852 A EP94916852 A EP 94916852A EP 0703960 B1 EP0703960 B1 EP 0703960B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fatty substance
- fatty
- acids
- complexing agent
- phospholipids
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/16—Refining fats or fatty oils by mechanical means
Definitions
- the present invention relates to a process for degumming a fatty substance, such as oil or fat, animal or vegetable, crude or delecithinate, as well as the fatty substance thus obtained.
- a fatty substance such as oil or fat, animal or vegetable, crude or delecithinate
- All fatty substances contain a certain number of impurities, fat soluble substances entrained when the oil cells burst, which could make it unusable for consumption. Some of these impurities have a harmful influence on the taste, the smell, the appearance of the product, its conservation.
- the purpose of refining fatty substances is eliminate free fatty acids, oxidation products, unpleasant aromas, colorings, toxic products (such as pesticides, glycosides) but also phospholipids as well as metals (such than iron, copper) present in trace amounts and generally linked to organic compounds.
- fatty substances some contain few phospholipids (e.g. palm fat, lauric and animal fats); so they can be easily rid of these substances by a dry degumming, i.e. by adding an acid to break them down and earth to fix them.
- these fatty substances can be refined by distillation neutralizing or physical refining.
- Oils obtained by pressure and / or by extraction using a solvent are very rich in phospholipids and are therefore generally refined chemically.
- a solvent for example soy, rapeseed, sunflower
- This type of refining presents several disadvantages; among other things, it generates "soapstocks", mixtures of oil and soaps, which must be treated, this which involves oil losses and additional costs.
- One of the essential purposes of this invention consists in remedying the aforementioned drawbacks existing processes, and to provide a process industrially and economically valid to obtain fatty substances such as oils or fats, animal or vegetable, raw or delecithinated, perfectly degummed to allow their physical refining, allowing including virtually completely eliminating phospholipids which they contain, and more particularly non-hydratable phospholipids, when contain, and reduce their iron content.
- the degumming process of the invention consists in mixing the fatty substance to be treated with a reactive aqueous solution of a complexing agent chosen from the group comprising citric acid, phosphoric acid, oxalic acid, tartaric acid, acids of the aminocarboxylic type, acids of polyhydroxycarboxylic type, polycarboxylic acids, the salts of these acids and mixtures of two or several of these substances and an emulsifier of the type anionic, cationic, zwitterionic, nonionic or generated in situ by partial neutralization of acids free fats present in the fatty substance, said solution allowing to extract the phospholipids contained in said fatty substance, said mixing being carried out by adding at once the aqueous solution of complexing agent and a fat emulsifier or vice versa and subjecting everything to intense agitation whose speed is between 500 and 15,000 rpm so as to form a fine emulsion.
- a complexing agent chosen from the group comprising citric acid, phosphoric acid
- the stirring speed the above is between 1200 and 10,000 rpm.
- the above mixture is a temperature of 20 to 100 ° C, advantageously from 60 to 90 ° C.
- the complexing agent is trisodium citrate or is an acid of the aminocarboxylic type, such as ethylenediaminetetraacetic acid or the disodium or trisodium salt of the latter and the emulsifier is of the anionic type and is constituted by sodium lauryl sulfate, of the nonionic type and is consisting of one or more monoglycerides or is generated in situ and is sodium and / or potassium carboxylate.
- the degumming process consists in dispersing the fatty substance in the form of fine droplets in a reactive aqueous solution of a complexing agent chosen from the group comprising citric acid, phosphoric acid, oxalic acid, tartaric acid, acids of the aminocarboxylic type, acids of polyhydroxycarboxylic type, polycarboxylic acids, the salts of these acids and mixtures of two or several of these substances and an emulsifier of the type anionic, cationic, zwitterionic, nonionic, or generated in situ by partial neutralization of acids free fats present in the fatty substance, said solution allowing to extract the phospholipids contained in said fatty substance.
- a complexing agent chosen from the group comprising citric acid, phosphoric acid, oxalic acid, tartaric acid, acids of the aminocarboxylic type, acids of polyhydroxycarboxylic type, polycarboxylic acids, the salts of these acids and mixtures of two or several of these substances and an emul
- the subject of the invention is also the degummed oils and fats, obtained according to process described above.
- the present invention proposes to erase fatty substances, such as oils or fats, animal or vegetable, crude or delecithinates, by bringing the fatty substance to be treated into contact with a reactive aqueous solution of a complexing agent and an emulsifier making it possible to hydrate not only the hydratable phospholipids but above all and in particular the non-hydratable phospholipids, if the latter contains them.
- a reactive aqueous solution of a complexing agent and an emulsifier making it possible to hydrate not only the hydratable phospholipids but above all and in particular the non-hydratable phospholipids, if the latter contains them.
- non-hydratable phospholipids such as phosphatidic acid and phosphatidyl ethanolamine associated with bivalent and trivalent metals (Ca ++ , Mg ++ , Fe + + or Fe +++ ) is a difficult reaction.
- the oil or fat to be degummed and the aqueous solution of complexing agent and emulsifier are mixed by adding the aqueous solution to the oil or fat at once or vice versa and subjecting the whole to intense agitation, the speed of which is between 500 and 15,000 revolutions / minute and advantageously between 1,200 and 10,000 revolutions / minute, for a duration generally of 10 seconds to 5 minutes.
- the purpose of this intense mixture is in fact to disperse the aqueous phase containing the reactants brought into contact (complexing and emulsifying agent) intensively in the oil or the fat so as to form a fine emulsion.
- the mixture of fatty substances / aqueous solution of the reactants brought into contact is generally carried out at a temperature of the order of 20 to 100 ° C., but a temperature between 60 and 90 ° C. is advantageously used.
- the aqueous phase thus formed is added or not with a sodium chloride solution whose concentration varies between 0.1 and 10% and is then separated by decantation or centrifugation so as to obtain a degummed fatty substance essentially free of phospholipids.
- the degummed fatty substance is then either dried and then treated with bleaching earth or treated directly without drying.
- the total content of phospholipids, expressed in the form of phosphorus, after degumming is much less than 10 ppm.
- the complexing agents have a much higher affinity constant for the bivalent cations than for the monovalent cations; therefore, they preferentially displace and complex the cations Ca ++ , Mg ++ , Fe ++ , Fe +++ .
- the phosphatidic acid and the phosphatidyl ethanolamine thus released are therefore easily hydrated in sodium form.
- This complexation reaction of bivalent or trivalent cations (Mg, Ca, Fe) by the complexing agent requires the prior dissociation of the bivalent phospholipidecation complex.
- a complexing agent chosen from the group comprising citric acid, phosphoric acid, oxalic acid, tartaric acid, acids of the aminocarboxylic type, acids of the polyhydroxycarboxylic type. , polycarboxylic acids, the salts of these acids and mixtures of two or more of these substances and of an emulsifier of the anionic, cationic, zwitterionic, nonionic type or generated in situ by partial neutralization of the free fatty acids present in the body fatty and, as has just been specified, the use of intense stirring and a temperature preferably of at least 60 ° C., advantageously from 60 to 90 ° C.
- Examples of preferred complexing agents used in the context of the present invention are trisodium citrate or acids of the aminocarboxylic type, such as ethylenediaminetetraacetic acid or the disodium and trisodium salts thereof.
- the complexing agent will be used at least in stoichiometric amount relative to the amount of non-hydratable phospholipids or total cations (Mg, Ca, Fe) present in the fatty substance to be treated.
- the emulsifier for its part, is of the anionic, cationic, zwitterionic or nonionic type.
- the anionic emulsifier such as sodium lauryl sulfate, is particularly suitable.
- the emulsifier can also be generated in situ by partial neutralization of the free fatty acids present in the fatty substance.
- Emulsifiers produced in this way are, for example, sodium and potassium carboxylates.
- non-ionic emulsifiers non-limiting examples will be mentioned monoglycerides and their mixtures.
- the amount of water in the solution mixture aqueous-fatty substance can vary between 0.1% and 99% in weight according to the separation conditions used.
- the reaction normally takes place between 10 seconds and 5 minutes but can be shortened or last longer if you modifies one of the parameters, for example the quantity of water used, reaction temperature, type of reagents brought together.
- Degumming soybean oils as well than rapeseed, cotton, peanut, sunflower, corn has been successfully produced using the method of the invention.
- the process of the invention is particularly suitable for degumming fatty substances containing phospholipids essentially formed of phospholipids not hydratable but also suitable for degumming fatty substances poor in non-hydratable phospholipids so as to better eliminate certain gums or mucilages.
- the degumming is carried out discontinuously or continuously, followed separation by decantation or centrifugation. A washing with water, after degumming the fatty substance, is beneficial but absolutely not necessary.
- Fats such as oil
- Fats can also be dispersed as fine droplets in an aqueous solution containing the chemical reagents.
- This technique described in the Belgian patent n ° 595.219 uses a column fitted with a dust jacket and a distribution system in which the body fat or oil is injected continuously in a form extremely divided. An infinite number is thus formed droplets of oil slowly rising against the current in the aqueous solution. These droplets of oil after coalescence at the top of the column are continuously separated by decantation or centrifugation.
- the reaction can be carried out in a counter-current extractor or in a column pulsed for liquid / liquid extraction.
- the dispersion will be also at a temperature between 20 and 100 ° C and advantageously between 60 and 90 ° C.
- complexing agents and emulsifiers we will use the same as those illustrated previously.
- the emulsion thus obtained is broken up by addition of 10 ml of a saturated chloride solution sodium or centrifuged directly at 5,000 rpm.
- the phosphorus content determined by the calorimetric phosphorus determination method is 6 ppm.
- the cation content determined by atomic absorption according to the IUPAC 2.631 method is given in ppm.
- CATION BEFORE TREATMENT AFTER TREATMENT Magnesium 18 0.2 Calcium 46 1 Iron 0.55 0.04
- 300 g of delecithinated soybean oil are heated to 75 ° C in a beaker.
- 900 ml of a solution aqueous compound of ethylenediaminetetraacetate salt di- or trisodium 5 millimolar and lauryl sulfate 1.7 millimolar sodium are also heated to 75 ° C.
- the aqueous solution is added all at once to the oil.
- the emulsion thus obtained is broken up by addition of 400 ml of a saturated chloride solution sodium or centrifuged directly at 5,000 rpm.
- the phosphorus content determined by the colorimetric phosphorus determination method is 6 ppm.
- the determined cation content by atomic absorption according to the IUPAC method 2.631 is given in ppm.
- 900 ml of an aqueous solution composed of 10 millimolar trisodium citrate and lauryl sulfate of 1.7 millimolar sodium are also heated to 75 ° C.
- the aqueous solution is added all at once to oil.
- the emulsion thus obtained is broken up by addition of 10 ml of a saturated chloride solution sodium or centrifuged directly at 5,000 rpm.
- Example 1 According to the conditions described in the Example 1, the test was carried out in the presence of different emulsifiers with a concentration of 1.7 millimolar remains constant.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI9430150T SI0703960T1 (en) | 1993-06-18 | 1994-06-16 | Method of degumming a fatty substance and fatty body so obtained |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE9300627 | 1993-06-18 | ||
BE9300627A BE1007151A3 (fr) | 1993-06-18 | 1993-06-18 | Procede de degommage d'un corps gras et corps gras ainsi obtenu. |
PCT/BE1994/000041 WO1995000609A1 (fr) | 1993-06-18 | 1994-06-16 | Procede de degommage d'un corps gras et corps gras ainsi obtenu |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0703960A1 EP0703960A1 (fr) | 1996-04-03 |
EP0703960B1 true EP0703960B1 (fr) | 1998-04-08 |
Family
ID=3887117
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94916852A Expired - Lifetime EP0703960B1 (fr) | 1993-06-18 | 1994-06-16 | Procede de degommage d'un corps gras et corps gras ainsi obtenu |
Country Status (18)
Country | Link |
---|---|
US (1) | US6015915A (ja) |
EP (1) | EP0703960B1 (ja) |
JP (1) | JPH09501453A (ja) |
CN (1) | CN1054395C (ja) |
AT (1) | ATE164880T1 (ja) |
AU (1) | AU675544B2 (ja) |
BE (1) | BE1007151A3 (ja) |
BG (1) | BG62212B1 (ja) |
CA (1) | CA2164840C (ja) |
DE (1) | DE69409520T2 (ja) |
DK (1) | DK0703960T3 (ja) |
ES (1) | ES2116596T3 (ja) |
HU (1) | HU220380B (ja) |
NZ (1) | NZ266746A (ja) |
RU (1) | RU2122013C1 (ja) |
SG (1) | SG45243A1 (ja) |
UA (1) | UA61872C2 (ja) |
WO (1) | WO1995000609A1 (ja) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1087339C (zh) * | 1997-07-09 | 2002-07-10 | 结晶及脱胶公司 | 从脂肪物质中除去金属以及粘合在所述金属上的树胶的方法 |
DE10257215B4 (de) * | 2002-12-07 | 2005-12-22 | Lurgi Ag | Verfahren zur Verbesserung der Langzeitstabilität von Biodiesel |
WO2007126594A2 (en) * | 2006-03-31 | 2007-11-08 | Archer-Daniels-Midland Company | Light-color plant oils and related methods |
JP5378001B2 (ja) | 2009-02-17 | 2013-12-25 | 花王株式会社 | 脂肪酸アルキルエステルの精製方法 |
GB0904787D0 (en) | 2009-03-20 | 2009-05-06 | Desmet Ballestra Engineering Sa | Improved enzymatic oil recuperation process |
DE102010048367A1 (de) | 2010-10-13 | 2012-04-19 | Süd-Chemie AG | Verfahren zur Entfernung von Phosphor-haltigen Verbindungen aus Triglycerid-haltigen Zusammensetzungen |
GB201019639D0 (en) * | 2010-11-19 | 2010-12-29 | Loders Croklaan Bv | Method |
DE102010055969A1 (de) | 2010-12-23 | 2012-06-28 | Süd-Chemie AG | Verfahren zur Aufreinigung von organischen Flüssigkeiten |
ES2641363T3 (es) * | 2013-04-15 | 2017-11-08 | Alfa Laval Corporate Ab | Desacidificación de grasas y aceites |
CN104277913B (zh) * | 2014-10-20 | 2017-06-23 | 河南工业大学 | 一种芝麻油中凝絮物脱除方法 |
US9340749B1 (en) | 2015-05-06 | 2016-05-17 | Arisdyne Systems, Inc. | Method for degumming triglyceride oils |
CA2984883C (en) * | 2015-05-06 | 2022-04-05 | Arisdyne Systems, Inc. | Method for degumming triglyceride oils |
CN105062670A (zh) * | 2015-08-21 | 2015-11-18 | 崇州市白头甘泉工业油脂厂 | 一种油脂的精炼方法 |
WO2017066027A1 (en) | 2015-10-14 | 2017-04-20 | Arisdyne Systems, Inc. | Method for reducing neutral oil losses during neutralization step |
CN107011991B (zh) * | 2017-04-12 | 2021-04-13 | 西北大学 | 一种油脂的阳离子树脂脱磷方法 |
CN106987312B (zh) * | 2017-04-12 | 2021-04-13 | 西北大学 | 一种油脂同时脱磷脱酸的方法 |
US10344246B2 (en) | 2017-05-24 | 2019-07-09 | Arisyne Systems, Inc. | Oil degumming systems |
WO2019157334A1 (en) | 2018-02-09 | 2019-08-15 | Poet Research, Inc. | Methods of refining a grain oil composition to make one or more grain oil products, and related systems |
CA3182639A1 (en) | 2018-06-11 | 2019-12-19 | Poet Research, Inc. | Methods of refining a grain oil composition feedstock, and related systems, compositions and uses |
WO2022026913A1 (en) * | 2020-07-31 | 2022-02-03 | Reg Synthetic Fuels, Llc | Method for the pretreatment of a biofuel feedstock |
EP4192964A1 (en) | 2020-08-06 | 2023-06-14 | POET Research, Inc. | Endogenous lipase for metal reduction in distillers corn oil |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR518593A (fr) * | 1917-06-29 | 1921-05-27 | Elektro Osmose Ag | Procédé d'épuration des graisses et huiles |
GB687843A (en) * | 1948-03-17 | 1953-02-25 | Frederick Charles Bersworth | Methods of treating and processing animal and vegetable oils |
FR1388567A (fr) * | 1964-04-17 | 1965-02-05 | Procédé de raffinage des graisses et des huiles | |
SU897841A1 (ru) * | 1980-02-18 | 1982-01-15 | Всесоюзный Научно-Исследовательский Институт Жиров | Способ рафинации масел и жиров |
SU1244170A1 (ru) * | 1984-02-20 | 1986-07-15 | Всесоюзный Научно-Исследовательский Институт Жиров | Способ рафинации масел и жиров |
US4866044A (en) * | 1985-07-09 | 1989-09-12 | Takeda Chemical Industries, Ltd. | Solubilized composition of poorly-soluble pharmaceutical product |
JPS6227665A (ja) * | 1985-07-29 | 1987-02-05 | Seitai Kinou Riyou Kagakuhin Shinseizou Gijutsu Kenkyu Kumiai | 脂質測定法 |
BR8703598A (pt) * | 1987-07-13 | 1989-01-24 | Brasil Pesquisa Agropec | Processo de degomagem de oleos brutos de soja com alto conteudo de fosfatidios nao-hidrataveis |
FR2633936B1 (fr) * | 1988-07-05 | 1991-04-12 | Sanofi Sa | Procede d'extraction du cholesterol contenu dans une matiere grasse d'origine animale |
BE1003488A3 (fr) * | 1989-03-14 | 1992-04-07 | Corman N Sa | Procede de reduction de la teneur en cholesterol et en acides gras libres de la matiere grasse d'origine animale et matiere grasse ainsi obtenue. |
DE69012682T2 (de) * | 1989-06-12 | 1995-04-06 | Merck & Co Inc | Verfahren zur Entfernung von bakteriellen Endotoxinen aus gram-negativen Polysacchariden. |
US4968518A (en) * | 1989-08-14 | 1990-11-06 | Klenz, Inc. | Process for the treatment of frying and/or cooking oil |
SU1717621A1 (ru) * | 1990-01-30 | 1992-03-07 | Ташкентский Политехнический Институт Им.А.Р.Бируни | Способ рафинации серосодержащих растительных масел в мисцелле |
-
1993
- 1993-06-18 BE BE9300627A patent/BE1007151A3/fr not_active IP Right Cessation
-
1994
- 1994-06-16 EP EP94916852A patent/EP0703960B1/fr not_active Expired - Lifetime
- 1994-06-16 HU HU9503629A patent/HU220380B/hu not_active IP Right Cessation
- 1994-06-16 CN CN94192792A patent/CN1054395C/zh not_active Expired - Fee Related
- 1994-06-16 ES ES94916852T patent/ES2116596T3/es not_active Expired - Lifetime
- 1994-06-16 NZ NZ266746A patent/NZ266746A/en unknown
- 1994-06-16 US US08/564,182 patent/US6015915A/en not_active Expired - Fee Related
- 1994-06-16 AU AU68392/94A patent/AU675544B2/en not_active Ceased
- 1994-06-16 AT AT94916852T patent/ATE164880T1/de not_active IP Right Cessation
- 1994-06-16 CA CA002164840A patent/CA2164840C/fr not_active Expired - Fee Related
- 1994-06-16 RU RU96101059A patent/RU2122013C1/ru not_active IP Right Cessation
- 1994-06-16 DK DK94916852T patent/DK0703960T3/da active
- 1994-06-16 DE DE69409520T patent/DE69409520T2/de not_active Expired - Fee Related
- 1994-06-16 UA UA96010218A patent/UA61872C2/uk unknown
- 1994-06-16 WO PCT/BE1994/000041 patent/WO1995000609A1/fr active IP Right Grant
- 1994-06-16 SG SG1996001891A patent/SG45243A1/en unknown
- 1994-06-16 JP JP7502258A patent/JPH09501453A/ja active Pending
-
1996
- 1996-01-11 BG BG100280A patent/BG62212B1/bg unknown
Also Published As
Publication number | Publication date |
---|---|
DK0703960T3 (da) | 1999-01-18 |
AU675544B2 (en) | 1997-02-06 |
DE69409520D1 (de) | 1998-05-14 |
EP0703960A1 (fr) | 1996-04-03 |
WO1995000609A1 (fr) | 1995-01-05 |
BE1007151A3 (fr) | 1995-04-11 |
SG45243A1 (en) | 1998-01-16 |
HUT75502A (en) | 1997-05-28 |
ATE164880T1 (de) | 1998-04-15 |
HU9503629D0 (en) | 1996-02-28 |
AU6839294A (en) | 1995-01-17 |
CA2164840C (fr) | 2005-06-14 |
HU220380B (hu) | 2002-01-28 |
CA2164840A1 (fr) | 1995-01-05 |
RU2122013C1 (ru) | 1998-11-20 |
ES2116596T3 (es) | 1998-07-16 |
BG100280A (bg) | 1996-07-31 |
US6015915A (en) | 2000-01-18 |
UA61872C2 (en) | 2003-12-15 |
BG62212B1 (bg) | 1999-05-31 |
DE69409520T2 (de) | 1998-10-29 |
NZ266746A (en) | 1996-08-27 |
JPH09501453A (ja) | 1997-02-10 |
CN1127564A (zh) | 1996-07-24 |
CN1054395C (zh) | 2000-07-12 |
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Legal Events
Date | Code | Title | Description |
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