EP1188818A1 - Procédé de préparation de mélanges d'oligoglycosides d'alkyle et/ou d'alcényle - Google Patents

Procédé de préparation de mélanges d'oligoglycosides d'alkyle et/ou d'alcényle Download PDF

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Publication number
EP1188818A1
EP1188818A1 EP01121508A EP01121508A EP1188818A1 EP 1188818 A1 EP1188818 A1 EP 1188818A1 EP 01121508 A EP01121508 A EP 01121508A EP 01121508 A EP01121508 A EP 01121508A EP 1188818 A1 EP1188818 A1 EP 1188818A1
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EP
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Prior art keywords
alkyl
alcohol
rheology
agents
mixtures
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EP01121508A
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German (de)
English (en)
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EP1188818B1 (fr
Inventor
Rainer Dr. Eskuchen
Ditmar Kischkel
Werner Dr. Leinemann
Manfred Dr. Weuthen
Michael Dr. Köhler
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BASF Personal Care and Nutrition GmbH
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Cognis Deutschland GmbH and Co KG
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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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • 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
    • 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
    • C11D1/721—End blocked ethers

Definitions

  • the invention relates to a process for the preparation of light-colored alkyl and / or alkenyl oligoglycoside mixtures and their use in detergents, dishwashing detergents and cleaning agents.
  • Alkyl oligoglucosides are important surfactants because they are compatible as nonionic compounds with a variety of other ingredients, but they have a foaming and cleaning ability that is much more similar to that of anionic surfactants. Due to their good degradability and skin tolerance, they are used in cosmetics and in detergents, dishwashing detergents and cleaning agents. They are produced from glucose and branched, unbranched, and saturated and unsaturated alcohols, which are acetalized in the presence of acidic catalysts. In order to shift the reaction equilibrium, the alcohol is generally used in a substantial excess.
  • reaction mixtures with 20 to 50% alkyl and / or alkenyl oligoglycosides and 50 to 80% alcohol are obtained, which means that the resulting glucosides must then be freed from unreacted alcohol with a high level of technical complexity before they are then mixed with water be adjusted and bleached.
  • EP 0 799 884 A2 (Unilever) relates to liquid surfactant mixtures of alkyl and / or alkenyl oligoglycosides and ethoxylated, nonionic surfactants in a weight ratio of 35:65 and 65:35 and 2 to 25% water and a process for the preparation of the surfactant mixtures. In the process, a 30% aqueous hydrogen peroxide solution at temperatures of 80 to 100 ° C is used as the bleaching agent.
  • the water content before bleaching should not be greater than 8%, since water is still introduced through the bleaching step. As part of this process, water must be added during the bleaching process and removed accordingly.
  • the surfactant mixtures of alkyl and / or alkenyl oligoglycosides and ethoxylated, nonionic surfactants contain at least 3.8% water. In contrast to this, the surfactant mixtures according to the invention are produced almost water-free, ie with water contents of less than 2% by weight.
  • German patent DE 19543990 (Henkel) discloses liquid, anhydrous precursors for the production of washing, rinsing and cleaning agents which consist of alkyl and / or alkenyl oligoglycosides and alkyl polyglycol ethers in a weight ratio of 10:90 and 90:10. Mixtures which are flowable at 40 ° C. are described and can be used in the granulation process for the production of detergents.
  • the invention has for its object to develop a process for the preparation of light-colored alkyl and / or alkenyl oligoglycoside mixtures which avoids the disadvantages mentioned, in particular to produce alkyl and / or alkenyl oligoglycoside mixtures with a low water content.
  • the invention relates to a method for producing light-colored surfactant mixtures, the Mixtures of at least alkyl and / or alkenyl oligoglycosides, rheology modifiers and contain less than 2% by weight of water. Mixtures which are preferred in the case of Temperatures from 85 to 130 ° C, especially at 90 to 120 ° C to viscosities from 10 to 1000, preferably set to 50 to 500 mPas, and then bleached.
  • the mixture can be produced without the addition of water , ie no water is added in order to obtain bleachable, pumpable and easy-to-process mixture with favorable rheological properties.
  • Mixtures which contain less than 2% by weight, preferably a maximum of 1.5% by weight, in particular a maximum of 0.5% by weight of water, based on the active substance alkyl and / or alkenyl oligoglycosides, are particularly preferred.
  • This water is introduced primarily through the bleaching agents and pH adjustment agents used.
  • the invention includes the finding that the alcohol content according to the invention improves the rheological properties of the alkyl and / or alkenyl oligoglycosides.
  • the fatty alcohol content according to the invention only enables the bleaching process.
  • the term light colored means Klett color numbers ⁇ 60, preferably ⁇ 40, in particular ⁇ 30 measured in a 1% solution of the mixture according to the invention in isopropyl alcohol.
  • alkyl and / or alkenyl oligoglycosides are used which follow the formula (I) R 1 O- [G] p in which R 1 is a branched and unbranched alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10.
  • R 1 is a branched and unbranched alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • They are preferably produced by reacting glucose or dextrose monohydrate and fatty alcohol in the presence of catalysts. They can be obtained using relevant preparative organic chemistry processes.
  • EP A1 0301298, WO 90/03977 and to "Alkyl Polyglycosides, Technology, Properties and Applications" (K. Hill, VCH 1997).
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligo glucosides .
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 18 carbon atoms and from C 12-15 oxo alcohols or the mixtures.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened C 12/14 coconut alcohol with a DP of 1 to 3 are preferred.
  • aliphatic, branched and unbranched, saturated and unsaturated alcohols with a carbon chain length of 2 to 31 are used or their mixtures.
  • Branched alcohols with 11 to are particularly preferred 22 carbon atoms and a low boiling and solidification point.
  • Fatty alcohol of the formula R 2 OH (II) is preferably used, where R 1 can be equated with R 2 .
  • These fatty alcohols serve as rheology-modifying agents in the alkyl and / or alkenyl oligoglycoside mixture.
  • a method for producing the inventive light-colored surfactant mixtures are preferred, in which 6 to 30, preferably 8 to 25 and in particular 10 to 15% by weight of a rheology-modifying agent are contained.
  • the details to the weight ratio relate to the active substance content of alkyl and / or alkenyl oligoglycoside.
  • the technical synthesis mixtures comprising alkyl and / or alkenyl oligoglycosides and alcohol which, by carrying out the reaction, still free alcohol, preferably fatty alcohols of the formula (II) from 6 to 30, preferably 8 to 25, in particular 10 to 15% by weight, based on the active substance alkyl and / or alkenyl oligoglycoside.
  • the surfactant mixtures according to the invention can also be prepared by mixing with an alcohol other than the one used for the synthesis.
  • the preferred procedure is when the synthetic alcohol has an intense intrinsic odor. In this case, the synthetic alcohol is removed by distillation and replaced by a low-odor alcohol.
  • Compounds selected from the group are used as rheology-modifying agents Group formed by alcohols, alkoxylated alkanols and alkylene oxides.
  • Alcohols are used. Examples include ethanol, n-butanol, iso-propanol and glycols Ethylene, propylene and butylene based. The use of ethanol and Propylene glycol.
  • fatty alcohols of the formula (II) which , depending on the process, are already contained in the alkyl and / or alkenyl oligoglycoside mixture (see depletion) or are subsequently added to the alkyl and / or alkenyl oligoglycosides.
  • Fatty alcohols of the formula (II) are preferably used as rheology-modifying agents.
  • Fatty alcohols are to be understood as primary alcohols of the formula (II) R 2 OH in which R 2 represents an aliphatic, linear or branched hydrocarbon radical having 4 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolenyl alcohol, linoleyl alcohol, linoleyl alcohol Technical mixtures which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
  • Technical fatty alcohols with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty alcohol, are preferred.
  • the alkenyl radical R 2 can be derived from primary unsaturated alcohols.
  • unsaturated alcohols are undecen-1-ol, laurolein alcohol, myristoline alcohol, palmitolein alcohol, petroselaidinal alcohol, oleyl alcohol, elaidyl alcohol, ricinol alcohol, linoleyl alcohol, linolenyl alcohol, gadoleyl alcohol, arachidone alcohol, eruca alcohol, palmoleyl alcohol, brassoleyl alcohol, brassol alcohol alcohol, brassidyl alcohol, brassoleyl alcohol, brassidyl alcohol, brassoleyl alcohol, brassidyl alcohol, brassol alcohol alcohol, brassidyl alcohol and brassidyl alcohol and saturated fatty alcohols which were obtained by the processes described in EP 0724 555 B1 .
  • Guerbet alcohols which are branched in the 2-position with an alkyl group and are usually prepared by base-catalyzed condensation of fatty alcohols.
  • An overview of the topic is from AJ O'Lennick and RE Bilbo in Soap Cosm.Chem.Spec. April, 52 (1987) .
  • Preferred Guerbet alcohols are derived from fatty alcohols having 6 to 22 carbon atoms, such as 2-ethylhexanol, 2-butyloctanol, 2-hexyldecanol and / or 2-octyldodecanol.
  • Guerbet alcohols which are produced on the basis of C 6 -C 12 fatty alcohol mixtures, containing capron alcohol, caprylic alcohol, 2-ethylhexanol, capric alcohol and / or lauryl alcohol.
  • a typical fatty alcohol cut that is suitable as a starting material for the preferred Guerbet alcohols contains less than 5% by weight of C 6 , 50 to 60% by weight of C 8 , 35 to 45% by weight of C 10 and less than 2% by weight of C 12 .
  • Guerbet alcohols of this type are described in more detail in German Patent DE 4341794 C1 (Henkel), the teaching of which is expressly included.
  • branched fatty alcohols having 4 to 20 carbon atoms which usually carry 1 to 4 methyl or ethyl groups as branches and after Oxo process are manufactured.
  • evaporators are considered that take this into account, but preferably thin-film evaporators, falling-film evaporators or short-path evaporators and - if necessary - any combination of these components.
  • the depletion can then take place in a manner known per se, for example at temperatures in the range from 110 to 220 ° C. and reduced pressures from 0.1 to 10 mbar.
  • the surfactant mixtures according to the invention are also used alkoxylated alkanols added.
  • alkoxylated alkanols of the formula (III) as rheology-modifying agent is preferred.
  • Typical examples are fatty alcohol polyethylene glycol / polypropylene glycol ether of the formula (III) or fatty alcohol polypropylene glycol / polyethylene glycol ether of the formula (IV) .
  • fatty alcohol polyethylene glycol / polypropylene glycol ethers of the formula (III), which are optionally end-capped, are used as rheology-modifying agents, R 3 O (CH 2 CH 2 O) n [CH 2 (CH 3 ) CHO] m R 4 used, in which R 3 is an alkyl and / or alkylene radical having 8 to 22 C atoms, R 4 is H or an alkyl radical having 1 to 8 C atoms, n is a number from 1 to 40, preferably 1 to 30 , in particular 1 to 15, and m represents 0 or a number from 1 to 10.
  • R 3 is an aliphatic, saturated, straight-chain or branched alkyl radical having 8 to 16 carbon atoms
  • n is a number from 1 to 10
  • m represents 0
  • R 4 represents hydrogen.
  • These are addition products of 1 to 10 moles of ethylene oxide with monofunctional alcohols.
  • the alcohols described above, such as fatty alcohols, oxo alcohols and Guerbet alcohols, are suitable as alcohols.
  • Suitable representatives of non-end-capped representatives are those of the formula (III) in which R 3 is an aliphatic, saturated, straight-chain or branched alkyl radical having 8 to 16 carbon atoms, n is a number from 2 to 7, m is a number of 3 to 7 and R 4 represents hydrogen.
  • R 3 is an aliphatic, saturated, straight-chain or branched alkyl radical having 8 to 16 carbon atoms
  • n is a number from 2 to 7
  • m is a number of 3 to 7
  • R 4 represents hydrogen.
  • alkylene oxides as rheology-modifying agents.
  • bleaching agents are preferred in the process according to the invention Hydrogen peroxide, in particular in the form of a 30 to 35% aqueous solution, is used. Also preferred is bleaching with organic peracids, e.g. -Dodecanedioic. Bleaching with chlorine bleach is also possible.
  • the pH is adjusted by adding alkali, preferably sodium hydroxide solution during the bleaching process preferably to values between 6 and 12, in particular 7 to 10 set. A sample is taken for the indirect determination of the pH. The pH will then determined in a 20% solution of the surfactant mixture according to the invention in 15% isopropanol.
  • alkali preferably sodium hydroxide solution during the bleaching process preferably to values between 6 and 12, in particular 7 to 10 set.
  • a sample is taken for the indirect determination of the pH.
  • the pH will then determined in a 20% solution of the surfactant mixture according to the invention in 15% isopropanol.
  • the invention furthermore relates to compositions comprising alkyl and / or alkenyl oligoglycosides, rheology-modifying compositions and a maximum of 1.5, preferably 1.0 and in particular 0.5,% by weight of water.
  • the agents contain 6 to 30% by weight of alcohols, preferably preferably fatty alcohol (based on the active substance alkyl and / or alkenyl oligoglycoside).
  • the agents according to the invention can preferably contain bleaching agents which can be added either as a result of the process or separately. Also preferred are agents which have viscosities of 10 to 1000 mPas at temperatures of 85 to 130, preferably 90 to 120 ° C.
  • Mixtures are also the subject of the application, which are characterized in that they are 6 to 30, preferably 8 to 25, in particular 10 to 15% by weight of fatty alcohol (based on active substance Contain alkyl and / or alkenyl oligoglycoside), a viscosity of 10 to 1000, preferably 50 to 500 mPas and a color number ⁇ 60, preferably ⁇ 40, in particular ⁇ 30 according to Klett, measured in one 1% solution of the mixture according to the invention in isopropyl alcohol.
  • fatty alcohol based on active substance Contain alkyl and / or alkenyl oligoglycoside
  • a viscosity 10 to 1000, preferably 50 to 500 mPas and a color number ⁇ 60, preferably ⁇ 40, in particular ⁇ 30 according to Klett, measured in one 1% solution of the mixture according to the invention in isopropyl alcohol.
  • the process according to the invention gives highly concentrated, anhydrous, light-colored alkyl and / or alkenyl oligoglycoside mixtures which can be easily and inexpensively preferably incorporated into detergents, dishwashing detergents and cleaning agents, for example by applying them to a solid detergent ingredient.
  • This can be done by spray drying but also in a mixer or a fluidized bed, drying and granulating at the same time.
  • Express reference is made to the as yet unpublished German application DE 10019405 , the teaching of which, in particular that of pages 5 to 22, is to be included here.
  • the application therefore also relates to the use of the surfactant mixtures according to the invention in detergents, dishwashing detergents, formatting agents and cleaning agents.
  • Liquid and gel detergents, dishwashing detergents and cleaning agents can preferably be formulated.
  • the surfactant mixtures can also contain bleaching agents, which in water-free formulations then represent a stable bleaching system which develops its bleaching action in the later washing or cleaning process.
  • bleach-free surfactant mixtures Another great advantage of the surfactant mixtures according to the invention is that they can be made up into finished products in an anhydrous manner, ie with a water content of less than 2% by weight. Because of the absence of water, stabilization to prevent contamination is not necessary in these products, even in the neutral range.
  • surfactant mixtures according to the invention containing alkyl and / or alkenyl oligoglycosides and fatty alcohol is that they are less water-attracting than pure alkyl and / or alkenyl oligoglycosides. For this reason, these mixtures, for example in the form of granules, show less tendency to clump when stored.
  • Examples E1 to E3 according to the invention are comparative examples V1 to V2 compared.
  • the table shows that the viscosity of the surfactant mixtures according to the invention also increasing fatty alcohol content decreases and the bleaching temperature can be correspondingly lower.

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EP01121508A 2000-09-19 2001-09-08 Procédé de préparation de mélanges d'oligoglycosides d'alkyle et/ou d'alcényle Expired - Lifetime EP1188818B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10046250A DE10046250A1 (de) 2000-09-19 2000-09-19 Verfahren zur Herstellung von hellfarbigen Alkyl-und/oder Alkenyloligoglycosid-Mischungen und deren Verwendung in Wasch-, Spül-und Reinigungsmittel
DE10046250 2000-09-19

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EP1188818A1 true EP1188818A1 (fr) 2002-03-20
EP1188818B1 EP1188818B1 (fr) 2004-02-18

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EP01121508A Expired - Lifetime EP1188818B1 (fr) 2000-09-19 2001-09-08 Procédé de préparation de mélanges d'oligoglycosides d'alkyle et/ou d'alcényle

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US (1) US6903066B2 (fr)
EP (1) EP1188818B1 (fr)
DE (2) DE10046250A1 (fr)
ES (1) ES2215829T3 (fr)

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US6903066B2 (en) * 2000-09-19 2005-06-07 Cognis Deutschland Gmbh & Co. Kg Processes for preparing light-colored alk(en)yl oligoglycoside mixtures

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EP2336280A1 (fr) * 2009-12-05 2011-06-22 Cognis IP Management GmbH Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage
GB2541930A (en) * 2015-09-04 2017-03-08 Cosmetic Warriors Ltd Composition
KR20180066109A (ko) 2015-10-07 2018-06-18 엘리멘티스 스페셜티즈, 인크. 습윤제 및 소포제

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WO1997010324A1 (fr) * 1995-09-15 1997-03-20 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de granules tensioactifs de sucre sans eau ni poussiere
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WO1997010324A1 (fr) * 1995-09-15 1997-03-20 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de granules tensioactifs de sucre sans eau ni poussiere
DE19543990A1 (de) * 1995-11-25 1997-05-28 Henkel Kgaa Flüssige Vorprodukte für Wasch-, Spül- und Reinigungsmittel
EP0799884A2 (fr) * 1996-04-02 1997-10-08 Unilever Plc Mélanges de tensioactifs, procédés pour leur préparation et composition détergentes sous forme de particules les contenant
WO2000050560A1 (fr) * 1999-02-22 2000-08-31 Cognis Corporation Melanges a haute activite et faible viscosite de polyglycosides d'alkyle et d'ethoxy alcools

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6903066B2 (en) * 2000-09-19 2005-06-07 Cognis Deutschland Gmbh & Co. Kg Processes for preparing light-colored alk(en)yl oligoglycoside mixtures

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US20020123453A1 (en) 2002-09-05
US6903066B2 (en) 2005-06-07
DE10046250A1 (de) 2002-03-28
EP1188818B1 (fr) 2004-02-18
ES2215829T3 (es) 2004-10-16
DE50101495D1 (de) 2004-03-25

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