WO1992002604A1 - Flüssiges, fliess- und pumpfähiges tensidkonzentrat - Google Patents
Flüssiges, fliess- und pumpfähiges tensidkonzentrat Download PDFInfo
- Publication number
- WO1992002604A1 WO1992002604A1 PCT/EP1991/001436 EP9101436W WO9202604A1 WO 1992002604 A1 WO1992002604 A1 WO 1992002604A1 EP 9101436 W EP9101436 W EP 9101436W WO 9202604 A1 WO9202604 A1 WO 9202604A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- alkyl
- carbon atoms
- surfactant mixture
- stands
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/83—Mixtures of non-ionic with anionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Definitions
- the present invention relates to concentrated surfactant mixtures of alkyl glycosides, long-chain alkyl sulfates, short-chain alkyl sulfates and optionally alcohol ethoxylates as stable, flowable and pumpable liquids and their use as premixes (compounds) for the production of liquid washing and cleaning agents.
- alkyl glycosides with long-chain alkyl groups belong to the nonionic surfactants.
- the person skilled in the art also knows, for example in A.M. Schwartz, J.W. Perry, Surface Active Agents, Vol. I, Interscience Publishers, 1949, page 372, describe that surfactant mixtures generally have synergistic effects and often have better cleaning properties than would result from the sum of the values of the individual components.
- Detergents which contain alkyl glycosides in combination with at least one conventional anionic surfactant are described in European patent application EP 070074.
- Detergents that contain alkyl glycosides and anionic surfactants are also known from European patent application EP 092877.
- liquid detergents are known from European patent application EP 105556, which contain alkyl glycosides, certain other nonionic surfactants and anionic surfactants. From the international patent application WO 86/02943 alkylglycoside-containing liquid detergents are known which contain conventional anionic surfactants.
- the individual components are generally used as flowable solutions, each of which contains a substance or which, as premixes, known as compounds, consist of several substances which are customary in the finished agents.
- the components provided for the mixture into the finished agent should have the highest possible active substance content and at the same time be easy to handle, that is to say they should be as flowable and as possible be easy to pump and have the highest possible storage stability.
- Alkyl glycosides are usually obtained as highly viscous pastes.
- the object of the present invention was to develop a storage-stable, liquid, flowable and pumpable surfactant mixture from an alkylglycoside paste.
- This object is achieved by an aqueous mixture of certain amounts of alkyl glycoside, synthetic anionic surfactant in the form of a long-chain alkyl sulfate and short-chain alkyl sulfate.
- long-chain compounds are understood to mean aliphatic compounds with 12 and more carbon atoms, which can be linear or branched one or more times, so that the longest chain of carbon atoms can also be shorter than 12 .
- Short-chain connections in the context of the present invention are accordingly, irrespective of the degree of branching, those having at most 10 carbon atoms.
- the compounds according to the invention are aqueous mixtures which essentially consist of
- R is an alkyl radical with 8 to 22 carbon atoms
- G is a glycose unit and n is a number between 1 and 10
- R2 is an alkyl radical having 12 to 22 carbon atoms and X is an alkali metal or ammonium ion, and 1 to 15% by weight, preferably 2 to 10% by weight, of a short-chain alkyl sulfate of the formula III,
- R- is an alkyl radical having 6 to 10 carbon atoms and Y is an alkali or ammonium ion.
- the surfactant mixtures according to the invention preferably additionally contain 10 to 20% by weight, in particular 12 to 18% by weight, of an ethoxylated alcohol of the formula IV,
- R ⁇ is an alkyl radical having 10 to 22 carbon atoms and p is a number between 1 and 20, in particular between 3 and 10.
- alkyl glycosides suitable for the surfactant mixtures according to the invention and their preparation are described, for example, in European patent applications EP 92355, EP 301 298, EP 357969 and EP 362671 or in the US Pat. No. 3547828.
- the glycoside components ((G) n in formula I) of such alkyl glycosides are oligomers or polymers from naturally occurring aldose or ketose monomers, in particular glucose, mannose, fructose, galactose, talose, gulose , Altrose, Allose, Idose, Ribose, Arabinose, Xylose and Lyxose.
- the oligomers consisting of such glycosidically linked monomers are characterized not only by the type of sugar they contain, but also by their number, the so-called degree of oligomerization.
- the degree of oligomerization (n in formula I) generally assumes fractional numerical values as the quantity to be determined analytically; it is between 1 and 10, for the alkyl glycosides preferably used below 1.5, in particular between 1.2 and 1.4.
- the preferred monomer building block is glucose because of its good availability.
- the alkyl glycosides can contain small amounts, for example 1 to 2%, of unconverted free long-chain alcohol, which does not have a disadvantageous effect on the properties of the surfactant mixtures produced therewith.
- Long-chain alkyl sulfates suitable for use in the surfactant mixtures according to the invention are the sulfation products of linear or branched chain alcohols.
- the derivatives of fatty alcohols with 12 to 22 carbon atoms, in particular with 12 to 15 carbon atoms, are particularly suitable.
- Such alkyl sulfates have long been known as effective anionic surfactants.
- Suitable short-chain alkyl sulfates are the sulfation products of linear or branched chain alcohols with 6 to 10 carbon atoms, preferably the derivatives of linear alcohols with 8 to 10 carbon atoms. Such alkyl sulfates are known to have little or no surfactant activity.
- the alkyl sulfates can be prepared in a known manner by reacting the corresponding long- or short-chain alcohol component with a customary sulfation reagent, in particular sulfur trioxide or chlorosulfonic acid, and subsequent neutralization, preferably with alkali, ammonium or alkyl- or hydroxyalkyl-substituted ammonium bases, be manufactured.
- a customary sulfation reagent in particular sulfur trioxide or chlorosulfonic acid
- the ethoxylates suitable for use in the compounds according to the invention are derivatives of linear or branched-chain alcohols having 10 to 22 carbon atoms, preferably 12 to 16 carbon atoms.
- the ethoxylation The degree of alcohol (p in formula IV) is between 1 and 20, preferably between 3 and 10. They can be prepared in a known manner by reacting the corresponding alcohols with ethylene oxide.
- the preparation of the surfactant mixtures according to the invention presents no difficulties. It can be done easily by simply mixing the individual components, which may be present as such or preferably in aqueous solution.
- the mixtures according to the invention are notable for their low viscosities, their easy flowability and pumpability and their high storage stability.
- the viscosity of the compounds according to the invention is generally from 20 mPa.s to 7000 Pa.s. They generally have basic pH values, for example from 9.8 to 10.5, but can be adjusted to largely neutral to weakly acidic pH values by adding conventional acids, in particular citric acid, without losing their advantageous properties .
- the compounds according to the invention are stable over a longer period of time, at least 30 days, at temperatures from about 1 ° C. to about 45 ° C.
- Another unexpected advantage of the compounds according to the invention is that the improvement in the rheological properties of the surfactant alkyl sulfate-alkyl glycoside pastes is achieved by the addition of compounds which, despite their low surface activity, have the properties of the alkyl glycosyls relevant for use in end products. Do not negatively affect sidpastes, such as cleaning and foaming power.
- the compounds according to the invention can be used, directly or after dilution with water, for technical applications, for example as flotation aids or drilling fluids. However, they are preferably used as premixes for the production of liquid detergents and cleaning agents, which include, in particular, mild detergents, wool detergents and dishwashing detergents, but also shampoos. Such agents can be prepared in a simple manner by diluting the compounds with water to the desired active substance concentration. The addition of other constituents customary in such compositions, in particular buildersubstances.
- punches such as zeolites and phyllosilicates, corrosion inhibitors, bleaching agents, bleach activators, optical brighteners, enzymes, graying inhibitors, antimicrobial agents, water-miscible solvents, abrasives, foam stabilizers, preservatives, pH regulators, colorants and fragrances and additional surfactants , is possible.
- the surfactant mixtures M1 to H7 according to the invention characterized in Table 1 below by their composition and the compositions VI and V2 used in comparative experiments were prepared.
- the surfactant mixtures Hl to M7 according to the invention had pH values of 9.8 to 10.5, and their pH values in 8.5% by weight aqueous solution were 8.5 to 9.9.
- Table 2 Viscosities of 20 ° C coolant viscosity according to Höler
- Samples of the mixtures Hl to H7 according to the invention were stored at 1 ° C. or 10 ° C. for 30 days without a change in their consistency being found. When stored at 40 ° C for 30 days, slight cloudiness occurred in some cases, which disappeared again when cooled to room temperature. If the compounds according to the invention were adjusted to pH values of 6.0 to 8.8 by adding small amounts of citric acid, which did not significantly change their viscosity, they could be stored at temperatures up to 45 ° C. without a change in consistency.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Cosmetics (AREA)
- Table Devices Or Equipment (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR919106754A BR9106754A (pt) | 1990-08-08 | 1991-07-31 | Concentrado de tensoativos,fluido,escovavel e bombeavel |
DE59102082T DE59102082D1 (de) | 1990-08-08 | 1991-07-31 | Flüssiges, fliess- und pumpfähiges tensidkonzentrat. |
EP91913983A EP0542801B1 (de) | 1990-08-08 | 1991-07-31 | Flüssiges, fliess- und pumpfähiges tensidkonzentrat |
RU9193004849A RU2056458C1 (ru) | 1990-08-08 | 1991-07-31 | Водная поверхностно-активная композиция и ее использование для получения жидких детергентов |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4025065.2 | 1990-08-08 | ||
DE4025065A DE4025065A1 (de) | 1990-08-08 | 1990-08-08 | Fluessiges, giess- und pumpfaehiges tensidkonzentrat |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992002604A1 true WO1992002604A1 (de) | 1992-02-20 |
Family
ID=6411812
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1991/001436 WO1992002604A1 (de) | 1990-08-08 | 1991-07-31 | Flüssiges, fliess- und pumpfähiges tensidkonzentrat |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0542801B1 (de) |
JP (1) | JPH05509347A (de) |
CN (1) | CN1058804A (de) |
AT (1) | ATE107956T1 (de) |
BR (1) | BR9106754A (de) |
DE (2) | DE4025065A1 (de) |
ES (1) | ES2055994T3 (de) |
MX (1) | MX9100568A (de) |
RU (1) | RU2056458C1 (de) |
WO (1) | WO1992002604A1 (de) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021742A1 (de) * | 1991-05-29 | 1992-12-10 | Henkel Kommanditgesellschaft Auf Aktien | Flüssige, giess- und pumpfähige tensidzubereitung |
WO1993021197A1 (de) * | 1992-04-21 | 1993-10-28 | Basf Aktiengesellschaft | Verfahren zur herstellung von alkylglykosiden und ihre verwendung |
EP0574086A2 (de) * | 1992-06-08 | 1993-12-15 | Colgate-Palmolive Company | Alkylsulfate als Viskositätsmodifizierungsmittel in anionischen Tensidzusammensetzungen |
WO1994010272A1 (en) * | 1992-11-03 | 1994-05-11 | The Procter & Gamble Company | Cleaning with short-chain surfactants |
WO1994010279A1 (de) * | 1992-10-29 | 1994-05-11 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG WÄssRIGER LÖSUNGEN ANIONISCHER TENSIDE MIT VERBESSERTER KÄLTESTABILITÄT |
EP0616026A1 (de) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Konzentrierte Reinigungszusammensetzungen |
EP0616027A1 (de) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Konzentrierte Reinigungszusammensetzungen |
TR26094A (tr) * | 1990-10-12 | 1994-12-15 | Saint Gobain Isover | Fenol recinesi, recinenin hazirlanma yöntemi ve bu recineyi iceren mineral lif tutkallama bilesimi |
TR26594A (tr) * | 1991-12-07 | 1995-03-15 | Hoechst Ag | MODIFIYE EDILMIS BIR ELYAF MALZEMESININ üRETILMESINE MAHSUS USUL VE MODIFIYE EDILMIS ELYAF MALZEMESININ ANIYONIK TEKSTIL BOYAR MADDELERIYLE BOYANMASINA MAHSUS USUL. |
EP0720642A1 (de) * | 1993-09-20 | 1996-07-10 | The Procter & Gamble Company | Verdickte wässrige waschmittelzusammensetzung mit verbesserter reinigungsleistung |
US5737471A (en) * | 1995-05-19 | 1998-04-07 | Bridgestone Corporation | Optical waveguide tube |
US5866530A (en) * | 1995-11-25 | 1999-02-02 | Henkel Kommanditgesellschaft Auf Aktien | Non-aqueous liquid mixtures of alkyl polyglycoside and alkyl polyalkylene glycol ether useful in various detergent applications |
WO1999019441A1 (en) * | 1997-10-14 | 1999-04-22 | The Procter & Gamble Company | Cleaning and disinfecting compositions |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4344991A1 (de) * | 1993-12-30 | 1995-07-06 | Huels Chemische Werke Ag | Verfahren zur Umwandlung hexagonal flüssig-kristalliner wäßriger Tensidphasen |
DE69429256T2 (de) * | 1994-07-18 | 2002-08-08 | Procter & Gamble | Eine stabile konzentrierte Vormischung und ihre Verwendung zur Herstellung von wässrigen Waschmittelzusammensetzungen |
DE19908563C2 (de) * | 1999-02-27 | 2002-11-14 | Cognis Deutschland Gmbh | Reinigungsmittel für harte Oberflächen |
SG11201510594YA (en) * | 2013-07-03 | 2016-01-28 | Basf Se | Mixtures of compounds, their preparation, and uses |
CN105062705A (zh) * | 2015-08-14 | 2015-11-18 | 浙江赞宇科技股份有限公司 | 一种无水乙氧基化烷基硫酸盐浓缩物及其制备方法与装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0070074A2 (de) * | 1981-07-13 | 1983-01-19 | THE PROCTER & GAMBLE COMPANY | Schäumende, oberflächenaktive Verbindungen enthaltende Zusammensetzungen |
US4483787A (en) * | 1983-12-28 | 1984-11-20 | The Procter & Gamble Company | Concentrated aqueous detergent compositions |
EP0370312A2 (de) * | 1988-11-17 | 1990-05-30 | Henkel Kommanditgesellschaft auf Aktien | Wasch- und Reinigungsmittel, enthaltend ein Tensidgemisch aus Alkylglykosiden und Aniontensiden |
-
1990
- 1990-08-08 DE DE4025065A patent/DE4025065A1/de not_active Withdrawn
-
1991
- 1991-07-31 JP JP3513139A patent/JPH05509347A/ja active Pending
- 1991-07-31 ES ES91913983T patent/ES2055994T3/es not_active Expired - Lifetime
- 1991-07-31 DE DE59102082T patent/DE59102082D1/de not_active Expired - Fee Related
- 1991-07-31 WO PCT/EP1991/001436 patent/WO1992002604A1/de active IP Right Grant
- 1991-07-31 RU RU9193004849A patent/RU2056458C1/ru active
- 1991-07-31 BR BR919106754A patent/BR9106754A/pt not_active Application Discontinuation
- 1991-07-31 EP EP91913983A patent/EP0542801B1/de not_active Expired - Lifetime
- 1991-07-31 AT AT91913983T patent/ATE107956T1/de not_active IP Right Cessation
- 1991-08-07 MX MX9100568A patent/MX9100568A/es unknown
- 1991-08-07 CN CN91105417A patent/CN1058804A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0070074A2 (de) * | 1981-07-13 | 1983-01-19 | THE PROCTER & GAMBLE COMPANY | Schäumende, oberflächenaktive Verbindungen enthaltende Zusammensetzungen |
US4483787A (en) * | 1983-12-28 | 1984-11-20 | The Procter & Gamble Company | Concentrated aqueous detergent compositions |
EP0370312A2 (de) * | 1988-11-17 | 1990-05-30 | Henkel Kommanditgesellschaft auf Aktien | Wasch- und Reinigungsmittel, enthaltend ein Tensidgemisch aus Alkylglykosiden und Aniontensiden |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TR26094A (tr) * | 1990-10-12 | 1994-12-15 | Saint Gobain Isover | Fenol recinesi, recinenin hazirlanma yöntemi ve bu recineyi iceren mineral lif tutkallama bilesimi |
WO1992021742A1 (de) * | 1991-05-29 | 1992-12-10 | Henkel Kommanditgesellschaft Auf Aktien | Flüssige, giess- und pumpfähige tensidzubereitung |
US5523016A (en) * | 1991-05-29 | 1996-06-04 | Henkel Kommanditgesellschaft Auf Aktien | Liquid pourable and pumpable surfactant preparation |
TR26594A (tr) * | 1991-12-07 | 1995-03-15 | Hoechst Ag | MODIFIYE EDILMIS BIR ELYAF MALZEMESININ üRETILMESINE MAHSUS USUL VE MODIFIYE EDILMIS ELYAF MALZEMESININ ANIYONIK TEKSTIL BOYAR MADDELERIYLE BOYANMASINA MAHSUS USUL. |
WO1993021197A1 (de) * | 1992-04-21 | 1993-10-28 | Basf Aktiengesellschaft | Verfahren zur herstellung von alkylglykosiden und ihre verwendung |
EP0574086A2 (de) * | 1992-06-08 | 1993-12-15 | Colgate-Palmolive Company | Alkylsulfate als Viskositätsmodifizierungsmittel in anionischen Tensidzusammensetzungen |
EP0574086A3 (en) * | 1992-06-08 | 1994-09-21 | Colgate Palmolive Co | Alkyl sulfates as viscosity modifiers in anionic surfactant compositions |
US5599787A (en) * | 1992-10-29 | 1997-02-04 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous anionic surfactant solutions stable at low temperature comprising glycoside and alkoxylated nonionic surfactant mixtures and processes of making same |
WO1994010279A1 (de) * | 1992-10-29 | 1994-05-11 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG WÄssRIGER LÖSUNGEN ANIONISCHER TENSIDE MIT VERBESSERTER KÄLTESTABILITÄT |
WO1994010272A1 (en) * | 1992-11-03 | 1994-05-11 | The Procter & Gamble Company | Cleaning with short-chain surfactants |
US6180583B1 (en) | 1992-11-03 | 2001-01-30 | The Procter & Gamble Company | Cleaning compositions containing short-chain surfactants |
TR28396A (tr) * | 1992-11-03 | 1996-05-30 | Procter & Gamble | Kisa zincirli yüzey aktif cisimleriyle temizlik. |
EP0616026A1 (de) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Konzentrierte Reinigungszusammensetzungen |
EP0616027A1 (de) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Konzentrierte Reinigungszusammensetzungen |
EP0720642A1 (de) * | 1993-09-20 | 1996-07-10 | The Procter & Gamble Company | Verdickte wässrige waschmittelzusammensetzung mit verbesserter reinigungsleistung |
EP0720642A4 (de) * | 1993-09-20 | 1998-01-28 | Procter & Gamble | Verdickte wässrige waschmittelzusammensetzung mit verbesserter reinigungsleistung |
US5737471A (en) * | 1995-05-19 | 1998-04-07 | Bridgestone Corporation | Optical waveguide tube |
US5866530A (en) * | 1995-11-25 | 1999-02-02 | Henkel Kommanditgesellschaft Auf Aktien | Non-aqueous liquid mixtures of alkyl polyglycoside and alkyl polyalkylene glycol ether useful in various detergent applications |
WO1999019441A1 (en) * | 1997-10-14 | 1999-04-22 | The Procter & Gamble Company | Cleaning and disinfecting compositions |
EP0916718A1 (de) * | 1997-10-14 | 1999-05-19 | The Procter & Gamble Company | Reinigungs- und Desinfektionsmittel |
US6537955B1 (en) | 1997-10-14 | 2003-03-25 | The Procter & Gamble Company | Cleaning and disinfecting compositions comprising C6- C7 alkyl sulfate |
Also Published As
Publication number | Publication date |
---|---|
ATE107956T1 (de) | 1994-07-15 |
BR9106754A (pt) | 1993-06-29 |
DE4025065A1 (de) | 1992-02-13 |
MX9100568A (es) | 1992-04-01 |
JPH05509347A (ja) | 1993-12-22 |
EP0542801B1 (de) | 1994-06-29 |
ES2055994T3 (es) | 1994-09-01 |
RU2056458C1 (ru) | 1996-03-20 |
CN1058804A (zh) | 1992-02-19 |
EP0542801A1 (de) | 1993-05-26 |
DE59102082D1 (de) | 1994-08-04 |
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