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WO1993010208A1 - Melanges detergents aqueux - Google Patents

Melanges detergents aqueux Download PDF

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Publication number
WO1993010208A1
WO1993010208A1 PCT/EP1992/002569 EP9202569W WO9310208A1 WO 1993010208 A1 WO1993010208 A1 WO 1993010208A1 EP 9202569 W EP9202569 W EP 9202569W WO 9310208 A1 WO9310208 A1 WO 9310208A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
aqueous detergent
mixtures
sulfates
alkenyl
Prior art date
Application number
PCT/EP1992/002569
Other languages
German (de)
English (en)
Inventor
Bernd Fabry
Brigitte Giesen
Dimitrios Ouzounis
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1993010208A1 publication Critical patent/WO1993010208A1/fr

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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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

Definitions

  • the invention relates to aqueous detergent mixtures containing alkyl and / or alkenyl oligoglycoside sulfates, fatty alcohol sulfates or fatty alcohol ether sulfates and, where appropriate, further anionic or nonionic surfactants and the use of the aqueous detergent mixtures for the production of manual dishwashing detergents, powder detergents and fabric softeners.
  • Alkyl oligoglycoside sulfates and in particular alkyl oligoglucoside sulfates are known anionic surfactants which can be obtained, for example, by reacting glucose with sulfuric acid and fatty alcohols [US 1.951.784] and sulfating alkyl oligoglucosides in dimethylformamide with sulfur trioxide [EP 0 186 242 AI] or a sulfur trioxide-amine complex [EP 0 363 601 A2].
  • the gas sulfonation of alkenyl glycosides in inert solvents is also described in DE 39 18 135 AI.
  • alkyl oligoglycosides and alkyl oligoglycoside sulfates are suitable for the production of manual dishwashing detergents.
  • alkyl oligoglycoside sulfates can also be used in liquid detergents.
  • detergent mixtures with good skin tolerance containing alkyl oligoglycoside sulfates, amphoteric or zwitterionic surfactants and other anionic surfactants are known from international patent application WO 91/00584.
  • Alkyl oligoglycoside sulfates have the disadvantage that they have only average detergent properties as individual surfactants, but also in a mixture with alkyl oligoglycosides, which make their use in marketable surface-active products possible only to a limited extent. Even the combinations with non-ionic fatty alcohol polyglycol ethers, otherwise a proven means of improving the application properties of anionic surfactants, either lead to little or no success.
  • the object of the invention was therefore to develop detergent mixtures containing alkyl oligoglycoside sulfates which are free from the disadvantages described.
  • the invention relates to aqueous detergent mixtures comprising a) alkyl and / or alkenyl oligoglycoside sulfates b1) fatty alcohol sulfates or
  • alkyl and / or alkenyl oligoglycoside sulfates can be increased significantly if they are combined with fatty alcohol sulfates or fatty alcohol ether sulfates.
  • the detergent mixtures according to the invention show a synergistic increase in the wetting, foaming and washing capacity over a wide range of mixtures.
  • the performance can be further improved by adding further anionic or nonionic surfactants.
  • Alkyl and / or alkenyl oligoglycoside sulfates which are constituents of the aqueous detergent mixtures according to the invention follow the formula (I),
  • R 1 -O- [G] pSO 3 X (I) in the R 1 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms,
  • X represents an alkali or alkaline earth metal.
  • the substances are usually prepared by reacting the corresponding alkyl and / or alkenyl oligoglycosides with gaseous sulfur trioxide in inert solvents and subsequent neutralization with aqueous alkali metal hydroxides. If one starts from alkyl oligoglucosides, an exclusive sulfation of free hydroxyl groups on the sugar body takes place during the reaction; if the carbon chain is unsaturated, sulfonate groups may also be present due to a subordinate electrophilic addition of sulfur trioxide to the double bond.
  • Alkyl and / or alkenyl oligoglycoside sulfates which can be used with particular advantage, are derived from aldoses or ketoses. Because of their better reactivity, alkyl and / or alkenyl oligoglycoside sulfates based on reducing saccharides, the aldoses, are preferred. Among the aldoses, glucose is particularly suitable as a starting material because of its easy accessibility and technical availability. The preferred alkyl and / or alkenyl oligoglycosides are therefore the alkyl and / or alkenyl oligoglucoside sulfates.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 6 to 22, preferably 12 to 18, carbon atoms. Typical examples are capronic alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadolyl alcohol, behenyl alcohol, erucyl alcohol and natural oils, palm oil, and coconut oil, and their technical blends, palm oil based on palm oils and natural oils or beef tallow.
  • capronic alcohol caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadolyl alcohol, behenyl alcohol, erucyl alcohol and natural
  • Alkyl and / or alkenyl oligoglycoside sulfates which can be used with particular advantage in the detergent mixtures according to the invention follow the formula (I) in which R 1 for an alkyl radical having 12 to 18 carbon atoms, [G] for a glucose radical and p for numbers from 1 to 3, in particular 1.1 to 1.7.
  • the alkyl and / or alkenyl oligoglycoside sulfates are preferably used in the form of their sodium or potassium salts.
  • Fatty alcohol sulfates are also known substances which are produced on an industrial scale by sulfating primary alcohols, for example with sulfur trioxide or chlorosulfonic acid.
  • Fatty alcohol sulfates which can be used for the purposes of the invention follow the formula (II),
  • R 2 is a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and
  • X represents an alkali or alkaline earth metal.
  • Typical examples are the sulfates of Capronalkohols, Caprylalkohols, capric alcohol, lauryl alcohol, Myristylalkohols, cetyl alcohol, Palmoleylalkohols, stearyl alcohol, oleyl alcohol, Elaidylalkohols, Petroselinylalkohols, Arachylalkohols, Gadoleylalkohols, behenyl alcohol and Erucylalkohols and their technical mixtures, such as for example in the high-pressure hydrogenation of technical fatty acid methyl ester based palm oil, palm kernel oil, coconut oil, turnip oil, sunflower oil, olive oil or beef tallow.
  • Fatty alcohol sulfates which can also be used in the context of the invention, are derived from oxo alcohols which are accessible by hydrogenation of aldehydes from Roelen's oxosynthesis and have a proportion of 5 to 25% by weight of branched species.
  • Saturated fatty alcohol sulfates with 12 to 18 carbon atoms in the form of their sodium or potassium salts are preferably used.
  • Fatty alcohol ether sulfates are produced on an industrial scale by sulfating fatty alcohol polyglycol ethers with sulfur trioxide or chlorosulfonic acid and follow the formula (III),
  • R 3 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms
  • n for numbers from 1 to 10 and
  • X represents an alkali or alkaline earth metal
  • Typical examples are the sulfation products of adducts of 1 to 10 moles of ethylene oxide with 1 mole of caprone alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol and technical alcohol, erucyl alcohol, gadyl alcohol, gadyl alcohol, gadyl alcohol .
  • Sulfates of adducts of 2 to 7 moles of ethylene oxide with saturated coconut oil alcohols having 12 to 18 carbon atoms in the form of their sodium or potassium salts are preferred.
  • Alkyl and / or alkenyl oligoglycosides which are suitable as further optional constituents of the aqueous ditergen mixtures according to the invention are to be understood as acetals of glycoses with fatty alcohols which follow the formula (IV)
  • R 4 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms
  • p represents a number from 1 to 10.
  • Typical examples are lauryl oligoglucoside, myristyl oligoglucoside, cetyloligoglucoside, stearyl oligoglucoside, oleyl oligoglucoside, behenyl oligoglucoside and erucyl oligoglucoside as well as their technical mixtures, whose average degree of oligomerization p is in the range from 1.1 to 3.0.
  • Preferred is the use of alkyl oligoglycosides of the formula (IV) in which R 4 is an alkyl radical having 12 to 18 carbon atoms, [G] is a glucose radical and p is a number from 1.1 to 1.7.
  • alkyl sulfosuccinates which follow the formula (V)
  • R 5 and R 6 are independently linear or branched
  • X represents an alkali or alkaline earth metal.
  • Alkyl sulfosuccinates are usually prepared by adding sodium bisulfite to maleic acid ester. Typical examples are the sulfitation products of maleic acid di-octyl ester or maleic acid di-2-ethylhexyl ester. Products of the formula (V) in which R 5 and R 6 are alkyl radicals having 8 to 12 carbon atoms and X is sodium or potassium are preferred.
  • aqueous detergent mixtures according to the invention can contain the individual components in the following amounts: Alkyl and / or alkenyl oligoglycoside sulfates 2 to 50%
  • Aqueous detergent mixtures with particularly advantageous performance properties contain the alkyl and / or alkenyl oligoglycoside sulfates in amounts of 5 to 15% by weight, the fatty alcohol sulfates or fatty alcohol ether sulfates in amounts of 10 to 50% by weight and optionally the alkyl and / or Alkenyl oligoglycosides or the alkyl sulfosuccinates in amounts of 60 to 80% by weight.
  • the aqueous detergent mixtures can be prepared by simple mechanical mixing of the aqueous solutions of the components, if appropriate at elevated temperatures of 30 to 50 ° C; a chemical reaction does not take place here.
  • detergent mixtures containing alkyl oligoglycoside sulfates and fatty alcohol sulfates can also be prepared in situ by subjecting mixtures of alkyl oligoglycosides and fatty alcohols, such as are produced as an intermediate in the production of alkyl oligoglycosides, to cosulfation.
  • mixtures of alkyl oligoglycosides and fatty alcohols such as are produced as an intermediate in the production of alkyl oligoglycosides, to cosulfation.
  • German patent application DE 40 06 841 A1 The detergent mixtures according to the invention show a pronounced foaming, wetting and cleaning ability, give textiles a pleasant soft feel and are completely biodegradable.
  • Another object of the invention therefore relates to the use of aqueous detergent mixtures of the composition mentioned for the production of surface-active agents, in particular manual dishwashing detergents, powder detergents and fabric softening agents, in which they are present in amounts of 0.1 to 25, preferably 1 to 10% by weight. based on the funds - may be included.
  • T1 C 12/14 coconut alkyl oligoglucoside sulfate Na salt
  • T2) C 12/14 coconut fatty alcohol sulfate Na salt
  • Anionic surfactant content 33.8% by weight
  • inorganic sulfate 1.1% by weight
  • the anionic surfactant content as well as the unsulfonated contents were determined according to the DGF standard methods, Stuttgart 1959 - 1984, H-III-10 and G-III-6b. II. Assessment of dish washing capacity
  • the determination of the dishwashing capacity was carried out with the aid of the dish test [Fette, Seifen, Anstrichmitt., 74, 163 (1972)].
  • the plates with the beef tallow dirt (“RiTa”) were then rinsed at 45 ° C, the plates with the mixed soiling (“Mino”) at 50 ° C with tap water with a hardness of 16 ° d.
  • the test mixtures were used with a dosage of 0.15 (“RiTa”) or 0.12 g / 1 water (“Mino”). The rinsing attempt was terminated as soon as the foam cover tore open on the surface and the fleet underneath became visible.
  • the investigation of the washing ability was carried out in a launderometer on a dust-skin fat stain (A) or a lipstick stain (B) on polyester-cotton (refined) fabric.
  • the lightening of the washed tissue was assessed by photometric reflectance measurement using an Elrepho RFC-3/24 device against a barium sulfate standard, the reflectance of which was set at 100%. The information is given in% remission (% -R).

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  • 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)

Abstract

Des mélanges détergents aqueux renfermant a) un alkyl- et/ou un alcényloligoglucosidesulfate, b1) un sulfate d'alcool gras, ou b2) un éther-sulfate d'alcool gras et, le cas échéant, c1) un alkyl- et/ou un alcényloligoglucoside, ou c2) un alkylsulfosuccinate, se caractérisent par des propriétés synergiques de moussage, de mouillabilité, de lavage et d'avivage et conviennent pour la fabrication de détergents pour le lavage manuel de la vaisselle, de détergents en poudre et d'adoucissants.
PCT/EP1992/002569 1991-11-18 1992-11-09 Melanges detergents aqueux WO1993010208A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914137893 DE4137893A1 (de) 1991-11-18 1991-11-18 Waessrige detergensgemische
DEP4137893.8 1991-11-18

Publications (1)

Publication Number Publication Date
WO1993010208A1 true WO1993010208A1 (fr) 1993-05-27

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Family Applications (1)

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PCT/EP1992/002569 WO1993010208A1 (fr) 1991-11-18 1992-11-09 Melanges detergents aqueux

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DE (1) DE4137893A1 (fr)
WO (1) WO1993010208A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999010463A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Detergents aqueux pour laver la vaisselle a la main
WO2009007166A1 (fr) * 2007-07-09 2009-01-15 Henkel Ag & Co. Kgaa Détergents ou de nettoyants contenant des tensioactifs à base de matières premières renouvelables
DE102013218616A1 (de) 2013-09-17 2015-03-19 Henkel Ag & Co. Kgaa Verwendung von Alkyl-/Alkenyl-Oligoglykosidderivaten zur Textilbehandlung
DE102014223885A1 (de) 2014-11-24 2016-05-25 Henkel Ag & Co. Kgaa Flüssigwaschmittel enthaltend Zitronensäure und Niotensid
DE102015201702A1 (de) 2015-01-30 2016-08-04 Henkel Ag & Co. Kgaa Saures Flüssigkompaktwaschmittel enthaltend Hydroxycarbonsäure, Niotensid und Enzym
DE102015201698A1 (de) 2015-01-30 2016-08-04 Henkel Ag & Co. Kgaa Saures Flüssigkompaktwaschmittel enthaltend Hydroxycarbonsäure, Niotensid und a-Amylase
DE102015215591A1 (de) 2015-08-14 2017-02-16 Henkel Ag & Co. Kgaa Wasserarme, zweiphasige Flüssigwaschmittel mit saurem pH-Wert

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072632A (en) * 1972-04-06 1978-02-07 Lever Brothers Company Dishwashing compositions
EP0112044A1 (fr) * 1982-11-16 1984-06-27 Unilever N.V. Compositions détergentes
US4483787A (en) * 1983-12-28 1984-11-20 The Procter & Gamble Company Concentrated aqueous detergent compositions
WO1988001640A1 (fr) * 1986-09-05 1988-03-10 A.E. Staley Manufacturing Company Derives ioniques de mono et polyglycosides d'alkyle
EP0363601A2 (fr) * 1988-10-13 1990-04-18 Hüls Aktiengesellschaft Procédé de sulfatation d'alkylglycosides
DE3918135A1 (de) * 1989-06-03 1990-12-13 Henkel Kgaa Sulfierte alkenylglykoside als tenside
WO1991004313A1 (fr) * 1989-09-14 1991-04-04 Henkel Corporation Compositions tensio-actives anioniques et amphoteres a viscosite reduite
WO1991013896A1 (fr) * 1990-03-05 1991-09-19 Henkel Kommanditgesellschaft Auf Aktien Procede de sulfonation de melanges contenant des glucosides d'alkyle
WO1991015192A1 (fr) * 1990-04-04 1991-10-17 Henkel Kommanditgesellschaft Auf Aktien Melanges tensioactifs aqueux a bonne compatibilite dermique

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072632A (en) * 1972-04-06 1978-02-07 Lever Brothers Company Dishwashing compositions
EP0112044A1 (fr) * 1982-11-16 1984-06-27 Unilever N.V. Compositions détergentes
US4483787A (en) * 1983-12-28 1984-11-20 The Procter & Gamble Company Concentrated aqueous detergent compositions
WO1988001640A1 (fr) * 1986-09-05 1988-03-10 A.E. Staley Manufacturing Company Derives ioniques de mono et polyglycosides d'alkyle
EP0363601A2 (fr) * 1988-10-13 1990-04-18 Hüls Aktiengesellschaft Procédé de sulfatation d'alkylglycosides
DE3918135A1 (de) * 1989-06-03 1990-12-13 Henkel Kgaa Sulfierte alkenylglykoside als tenside
WO1991004313A1 (fr) * 1989-09-14 1991-04-04 Henkel Corporation Compositions tensio-actives anioniques et amphoteres a viscosite reduite
WO1991013896A1 (fr) * 1990-03-05 1991-09-19 Henkel Kommanditgesellschaft Auf Aktien Procede de sulfonation de melanges contenant des glucosides d'alkyle
WO1991015192A1 (fr) * 1990-04-04 1991-10-17 Henkel Kommanditgesellschaft Auf Aktien Melanges tensioactifs aqueux a bonne compatibilite dermique

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999010463A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Detergents aqueux pour laver la vaisselle a la main
WO2009007166A1 (fr) * 2007-07-09 2009-01-15 Henkel Ag & Co. Kgaa Détergents ou de nettoyants contenant des tensioactifs à base de matières premières renouvelables
DE102013218616A1 (de) 2013-09-17 2015-03-19 Henkel Ag & Co. Kgaa Verwendung von Alkyl-/Alkenyl-Oligoglykosidderivaten zur Textilbehandlung
WO2015039973A1 (fr) * 2013-09-17 2015-03-26 Henkel Ag & Co. Kgaa Utilisation de dérivés d'alkyle /alcényl-oligoglycosides pour le traitement textile
DE102014223885A1 (de) 2014-11-24 2016-05-25 Henkel Ag & Co. Kgaa Flüssigwaschmittel enthaltend Zitronensäure und Niotensid
DE102015201702A1 (de) 2015-01-30 2016-08-04 Henkel Ag & Co. Kgaa Saures Flüssigkompaktwaschmittel enthaltend Hydroxycarbonsäure, Niotensid und Enzym
DE102015201698A1 (de) 2015-01-30 2016-08-04 Henkel Ag & Co. Kgaa Saures Flüssigkompaktwaschmittel enthaltend Hydroxycarbonsäure, Niotensid und a-Amylase
US10329517B2 (en) 2015-01-30 2019-06-25 Henkel Ag & Co. Kgaa Acid liquid compact washing agent including hydroxycarboxylic acid, non-ionic surfactant, and an-amylase
US10577562B2 (en) 2015-01-30 2020-03-03 Henkel Ag & Co. Kgaa Acid liquid compact washing agent including hydroxycarboxylic acid, non-ionic surfactant, and an enzyme
DE102015215591A1 (de) 2015-08-14 2017-02-16 Henkel Ag & Co. Kgaa Wasserarme, zweiphasige Flüssigwaschmittel mit saurem pH-Wert

Also Published As

Publication number Publication date
DE4137893A1 (de) 1993-05-19

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