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EP0771346B1 - Use of detergent mixtures - Google Patents

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Publication number
EP0771346B1
EP0771346B1 EP95943495A EP95943495A EP0771346B1 EP 0771346 B1 EP0771346 B1 EP 0771346B1 EP 95943495 A EP95943495 A EP 95943495A EP 95943495 A EP95943495 A EP 95943495A EP 0771346 B1 EP0771346 B1 EP 0771346B1
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EP
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Prior art keywords
fatty acid
alkyl
acid
carbon atoms
group containing
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EP95943495A
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German (de)
French (fr)
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EP0771346A1 (en
Inventor
Bernd Fabry
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol 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
    • C11D1/123—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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest

Definitions

  • the invention relates to the use of detergent mixtures with synergistic enhancement of Cleaning and foaming power, containing fatty acid N-alkylpolyhydroxyalkylamides and sulfosuccinates for the production of hair shampoos.
  • Fatty acid N-alkylpolyhydroxyalkylamides and in particular fatty acid N-methylglucamides are nonionic surfactants which are used, for example, for the production of hand dishwashing detergents because of their good application profile.
  • the use of these substances has been the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-A1 0285768 (Hüls).
  • French published patent application FR-A 1580491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators.
  • EP-A 0112046 discloses well foaming detergent compositions comprising dialkyl sulfosuccinates and fatty acid dialkanolamides which can be used in shampoos.
  • Preparations are also known from international patent application WO 93/21293 , which can contain N-containing surfactants, sulfosuccinates and a Diels-Alder adduct. The mixtures can also be used as shampoos.
  • fatty acid N-alkylpolyhydroxyalkylamides can also be used in combination have cleaning and foaming power with other preferably anionic surfactants, that are not always satisfactory.
  • the object of the invention was then to provide detergent mixtures based on fatty acid N-alkylpolyhydroxyalkylamides for the manufacture of hair shampoos that are available through a have improved cleaning and foaming power without this advantage due to reduced performance must be paid for in other properties relevant to application technology.
  • the fatty acid N-alkylpolyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride; they follow the formula (I) : in which R 1 CO stands for an aliphatic acyl radical with 6 to 22 carbon atoms, R 2 for an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms and [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
  • R 1 CO stands for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R 2 for an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxy
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (II) :
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (II) in which R 2 is an alkyl group and R 1 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • Sulfosuccinates which are also referred to as sulfosuccinic acid esters, are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry. They follow formula (III) in which R 3 is an alkyl and / or alkenyl radical having 6 to 22 carbon atoms, R 4 is R 3 or X, m and n independently of one another are 0 or numbers from 1 to 10 and X is an alkali or alkaline earth metal, ammonium, Alkylammonium or Glucammonium stands.
  • R 3 is an alkyl and / or alkenyl radical having 6 to 22 carbon atoms
  • R 4 is R 3 or X
  • m and n independently of one another are 0 or numbers from 1 to 10
  • X is an alkali or alkaline earth metal, ammonium, Alkylammonium or Glucammonium stands.
  • maleic acid but preferably maleic anhydride, which are esterified in the
  • the mono / diester ratio can be adjusted by varying the amount of alcohol and the temperature.
  • bisulfite is added, which is usually carried out in the solvent methanol.
  • Typical examples are sulfosuccinic acid monoesters and / or diesters in the form of their sodium salts which are derived from fatty alcohols having 8 to 18, preferably 8 to 10 or 12 to 14, carbon atoms; the fatty alcohols can be etherified with an average of 1 to 10 and preferably 1 to 5 moles of ethylene oxide and have both a conventional and preferably a narrowed homolog distribution.
  • Examples include di-n-octyl sulfosuccinate and monolauryl 3EO sulfosuccinate in the form of their sodium salts.
  • the preparation of the mixtures which are preferably aqueous and then have a solids content of 5 up to 70, preferably 25 to 50 wt .-%, is usually done by stirring aqueous Solutions, pastes or concentrates of the input materials, if necessary at a slightly elevated temperature.
  • aqueous Solutions pastes or concentrates of the input materials, if necessary at a slightly elevated temperature.
  • spray-dried powder of the two components and then paste or solutions of both ingredients together spray drying and / or subject to granulation. All of these cases are purely mechanical processes, a chemical reaction does not take place.
  • the hair shampoos can be 10 to 30% by weight on the agent - contain detergent mixtures as well as usual auxiliaries and additives.
  • the shampoos can primarily contain other anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants as auxiliaries and additives.
  • anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps , Ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcos,
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polygylcol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, alk (en) yloligoglycosides, fatty acid-N-alkylglucamides, protein hydrolysate, sorbate ester products, in particular vegetable ester ester-based sorbate products, especially vegetable-based ester esters, sorbate-based ester products (especially vegetable-based ester esters).
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • the shampoos can contain emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives.
  • emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives.
  • Superfatting agents may be used such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, the latter also serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, and electrolytes such as sodium chloride and ammonium chloride.
  • Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene, but also fatty acid monoglycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication " Cosmetic Dyes” by the Dye Commission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp . 81-106 . These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.

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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)
  • Cosmetics (AREA)

Description

Gebiet der ErfindungField of the Invention

Die Erfindung betrifft die Verwendung von Detergensgemischen mit synergistischer Verstärkung des Reinigungs- und Schaumvermögens, enthaltend Fettsäure-N-alkylpolyhydroxyalkylamide und Sulfosuccinate zur Herstellung von Haarshampoos.The invention relates to the use of detergent mixtures with synergistic enhancement of Cleaning and foaming power, containing fatty acid N-alkylpolyhydroxyalkylamides and sulfosuccinates for the production of hair shampoos.

Stand der TechnikState of the art

Fettsäure-N-alkylpolyhydroxyalkylamide und insbesondere Fettsäure-N-methylglucamide stellen nichtionische Tenside dar, die wegen ihres guten anwendungstechnischen Profils beispielsweise zur Herstellung von Handgeschirrspülmitteln eingesetzt werden. Die Verwendung dieser Stoffe ist Gegenstand einer Vielzahl von Veröffentlichungen. Aus der Europäischen Patentanmeldung EP-A1 0285768 (Hüls) ist beispielsweise ihr Einsatz als Verdickungsmittel bekannt. In der Französischen Offenlegungsschrift FR-A 1580491 (Henkel) werden wäßrige Detergensgemische auf Basis von Sulfaten und/oder Sulfonaten, Niotensiden und gegebenenfalls Seifen beschrieben, die Fettsäure-N-alkylglucamide als Schaumregulatoren enthalten. Gegenstand der Intemationalen Patentanmeldungen WO 92/06153, WO 92/06156, WO 92/06157, WO 92/06158, WO 92/06159 und WO 92/06160 (Procter & Gamble) sind Mischungen von Fettsäure-N-alkylglucamiden mit anionischen Tensiden, Tensiden mit Sulfat- und/oder Sulfonatstruktur, Ethercarbonsäuren, Ethersulfaten, Methylestersulfonaten und nichtionischen Tensiden. Die Verwendung dieser Stoffe in den unterschiedlichsten Wasch-, Spül- und Reinigungsmitteln wird in den Internationalen Patentanmeldungen WO 092/6152, WO 92/06154, WO 92/06155, WO 92/06161, WO 92106162, WO 92/06164, WO 92/06170, WO 92/06171 und WO 92/06172 (Procter & Gamble) beschrieben.Fatty acid N-alkylpolyhydroxyalkylamides and in particular fatty acid N-methylglucamides are nonionic surfactants which are used, for example, for the production of hand dishwashing detergents because of their good application profile. The use of these substances has been the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-A1 0285768 (Hüls). French published patent application FR-A 1580491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators. International patent applications WO 92/06153, WO 92/06156, WO 92/06157, WO 92/06158, WO 92/06159 and WO 92/06160 (Procter & Gamble) relate to mixtures of fatty acid N-alkylglucamides with anionic surfactants, Surfactants with a sulfate and / or sulfonate structure, ether carboxylic acids, ether sulfates, methyl ester sulfonates and nonionic surfactants. The use of these substances in a wide variety of washing, rinsing and cleaning agents is described in international patent applications WO 092/6152, WO 92/06154, WO 92/06155, WO 92/06161, WO 92106162, WO 92/06164, WO 92 / 06170, WO 92/06171 and WO 92/06172 (Procter & Gamble).

Des weiteren sei als Stand der Technik auf die Europäische Patentanmeldung EP-A 0112046 verwiesen, die gut schäumende Detergenszusammensetzungen aus Dialkylsulfosuccinaten und Fettsäuredialkanolamiden offenbart, welche in Shampoos eingesetzt werden können. Aus der internationalen Patentanmeldung WO 93/21293 sind ferner Zubereitungen bekannt, die N-haltige Tenside, Sulfosuccinate und ein Diels-Alder Addukt enthalten können. Die Mischungen können ebenfalls als Shampoos verwendet werden.Furthermore, reference is made to the state of the art to European patent application EP-A 0112046 , which discloses well foaming detergent compositions comprising dialkyl sulfosuccinates and fatty acid dialkanolamides which can be used in shampoos. Preparations are also known from international patent application WO 93/21293 , which can contain N-containing surfactants, sulfosuccinates and a Diels-Alder adduct. The mixtures can also be used as shampoos.

In der Praxis hat sich jedoch gezeigt, daß die Fettsäure-N-alkylpolyhydroxyalkylamide auch in Kombination mit anderen vorzugsweise anionischen Tensiden ein Reinigungs- und Schaumvermögen aufweisen, das nicht immer zufriedenstellend sind.In practice, however, it has been found that the fatty acid N-alkylpolyhydroxyalkylamides can also be used in combination have cleaning and foaming power with other preferably anionic surfactants, that are not always satisfactory.

Die Aufgabe der Erfindung hat somit dann bestanden, Detergensgemische auf Basis von Fettsäure-N-alkylpolyhydroxyalkylamiden zur Herstellung von Haarshampoos zur Verfügung zu stellen, die über ein verbessertes Reinigungs- und Schaumvermögen verfügen, ohne daß dieser Vorteil durch Leistungseinbußen in anderen anwendungstechnisch relevanten Eigenschaften bezahlt werden muß.The object of the invention was then to provide detergent mixtures based on fatty acid N-alkylpolyhydroxyalkylamides for the manufacture of hair shampoos that are available through a have improved cleaning and foaming power without this advantage due to reduced performance must be paid for in other properties relevant to application technology.

Beschreibung der ErfindungDescription of the invention

Gegenstand der Erfindung ist die Verwendung von Detergensgemischen, enthaltend

  • (a) Fettsäure-N-alkylpolyhydroxyalkylamide und
  • (b) Sulfosuccinate
    • im Gewichtsverhältnis 80 : 20 bis 20 :80 zur Herstellung von Haarshampoos.The invention relates to the use of detergent mixtures containing
  • (a) Fatty acid N-alkyl polyhydroxyalkylamides and
  • (b) sulfosuccinates
    • in a weight ratio of 80:20 to 20:80 for the production of hair shampoos.

    Obschon Mischungen auf Basis von Fettsäure-N-alkylpolyhydroxyalkylamiden, insbesondere Fettsäure-N-methylglucamiden und anionischen Tensiden bereits bekannt gewesen sind, wurde überraschenderweise hinsichtlich des Reinigungs- und Schaumvermögens innerhalb bestimmter Mischungsverhältnisse eine starke synergistische Wechselwirkung mit Sulfosuccinaten vom Typ der Sulfobernsteinsäuremonound -diester festgestellt. Die Erfindung schließt die Erkenntnis ein, daß auch hinsichtlich Netzvermögen und Waschleistung eine Verbesserung erzielt wird und die ökotoxikologischen Eigenschaften wenigstens auf dem Niveau der Einzelstoffe erhalten bleiben.Although mixtures based on fatty acid-N-alkylpolyhydroxyalkylamides, especially fatty acid-N-methylglucamides and anionic surfactants have been surprisingly discovered with regard to the cleaning and foaming power within certain mixing ratios a strong synergistic interaction with sulfosuccinates of the sulfosuccinic acid monound type -this found. The invention includes the knowledge that also with regard to network assets and washing performance an improvement is achieved and the ecotoxicological properties at least remain at the level of the individual substances.

    Fettsäure-N-alkylpolyhydroxyalkylamideFatty acid N-alkyl polyhydroxyalkylamides

    Bei den Fettsäure-N-alkylpolyhydroxyalkylamiden handelt es sich um bekannte Stoffe, die üblicherweise durch reduktive Aminierung eines reduzierenden Zuckers mit einem Alkylamin oder einem Alkanolamin und nachfolgende Acylierung mit einer Fettsäure, einem Fettsäurealkylester oder einem Fettsäurechlorid erhalten werden können; sie folgen der Formel (I):

    Figure 00030001
    in der R1CO für einen aliphatischen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für einen Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen und [Z] für einen linearen oder verzweigten Polyhydroxyalkylrest mit 3 bis 12 Kohlenstoffatomen und 3 bis 10 Hydroxylgruppen steht.
    Hinsichtlich der Verfahren zu ihrer Herstellung sei auf die US-Patentschriften US 1,985,424, US 2,016,962 und US 2703798 sowie die Internationale Patentanmeldung WO 92/06984 verwiesen. Eine Übersicht zu diesem Thema von H.Kelkenberg findet sich in Tens.Surf.Det. 25 8 (1988). Vorzugsweise leiten sich die Fettsäure-N-alkylpolyhydroxyalkylamide von reduzierenden Zuckern mit 5 oder 6 Kohlenstoffatomen, insbesondere von der Glucose ab. Die bevorzugten Fettsäure-N-alkylpolyhydroxyalkylamide stellen daher Fettsäure-N-alkylglucamide dar, wie sie durch die Formel (II) wiedergegeben werden:
    Figure 00030002
    Vorzugsweise werden als Fettsäure-N-alkylpolyhydroxyalkylamide Glucamide der Formel (II) eingesetzt, in der R2 für eine Alkylgruppe steht und R1CO für den Acylrest der Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Arachinsäure, Gadoleinsäure, Behensäure oder Erucasäure bzw. derer technischer Mischungen steht. Besonders bevorzugt sind Fettsäure-N-alkylglucamide der Formel (II), die durch reduktive Aminierung von Glucose mit Methylamin und anschließende Acylierung mit Laurinsäure oder C12/14-Kokosfettsäure bzw. einem entsprechenden Derivat erhalten werden. Weiterhin können sich die Polyhydroxyalkylamide auch von Maltose und Palatinose ableiten.The fatty acid N-alkylpolyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride; they follow the formula (I) :
    Figure 00030001
    in which R 1 CO stands for an aliphatic acyl radical with 6 to 22 carbon atoms, R 2 for an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms and [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
    With regard to the processes for their production, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2707098 and international patent application WO 92/06984. An overview of this topic by H.Kelkenberg can be found in Tens.Surf.Det. 25 8 (1988). The fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose. The preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (II) :
    Figure 00030002
    The fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (II) in which R 2 is an alkyl group and R 1 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures. Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred. Furthermore, the polyhydroxyalkylamides can also be derived from maltose and palatinose.

    SulfosuccinateSulfosuccinates

    Sulfosuccinate, die auch als Sulfobernsteinsäureester bezeichnet werden, stellen bekannte anionische Tenside dar, die nach den einschlägigen Methoden der präparativen organischen Chemie erhalten werden können. Sie folgen der Formel (III),

    Figure 00030003
    in der R3 für einen Alkyl- und/oder Alkenylrest mit 6 bis 22 Kohlenstoffatomen, R4 für R3 oder X, m und n unabhängig voneinander für 0 oder Zahlen von 1 bis 10 und X für ein Alkali- oder Erdalkalimetall, Ammonium, Alkylammonium oder Glucammonium steht. Zu ihrer Herstellung geht man üblicherweise von Maleinsäure, vorzugsweise aber Maleinsäureanhydrid aus, die im ersten Schritt mit gegebenenfalls ethoxylierten primären Alkoholen verestert werden. An dieser Stelle kann durch Variation von Alkoholmenge und Temperatur das Mono-/Diester-Verhältnis eingestellt werden. Im zweiten Schritt erfolgt die Anlagerung von Bisulfit, die üblicherweise im Lösungsmittel Methanol durchgeführt wird. Neuere Übersichten zu Herstellung und Verwendung von Sulfosuccinaten sind beispielsweise von T.Schoenberg in Cosm.Toil. 104, 105 (1989), J.A.Milne in R.Soc.Chem.(lnd.Appl.Surf.II) 77, 77 (1990) sowie W.Hreczuch et al. in J.Am.Oil.Chem.Soc. 70 707 (1993) erschienen. Typische Beispiele sind Sulfobernsteinsäuremono- und/oder -diester in Form ihrer Natriumsalze, die sich von Fettalkoholen mit 8 bis 18, vorzugsweise 8 bis 10 bzw. 12 bis 14 Kohlenstoffatomen ableiten; die Fettalkohole können dabei mit durchschnittlich 1 bis 10 und vorzugsweise 1 bis 5 Mol Ethylenoxid verethert sein und dabei sowohl eine konventionelle als auch vorzugsweise eine eingeengte Homologenverteilung aufweisen. Exemplarisch genannt seien Di-n-octylsulfosuccinat und Monolauryl-3EO-sulfosuccinat in Form ihrer Natriumsalze.Sulfosuccinates, which are also referred to as sulfosuccinic acid esters, are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry. They follow formula (III)
    Figure 00030003
    in which R 3 is an alkyl and / or alkenyl radical having 6 to 22 carbon atoms, R 4 is R 3 or X, m and n independently of one another are 0 or numbers from 1 to 10 and X is an alkali or alkaline earth metal, ammonium, Alkylammonium or Glucammonium stands. For their preparation, one usually starts from maleic acid, but preferably maleic anhydride, which are esterified in the first step with optionally ethoxylated primary alcohols. At this point, the mono / diester ratio can be adjusted by varying the amount of alcohol and the temperature. In the second step, bisulfite is added, which is usually carried out in the solvent methanol. Recent reviews on the production and use of sulfosuccinates are, for example, from T.Schoenberg in Cosm.Toil. 104, 105 (1989) , JAMilne in R.Soc.Chem. (Ind.Appl.Surf.II) 77, 77 (1990) and W.Hreczuch et al. in J.Am.Oil.Chem.Soc. 70 707 (1993) appeared. Typical examples are sulfosuccinic acid monoesters and / or diesters in the form of their sodium salts which are derived from fatty alcohols having 8 to 18, preferably 8 to 10 or 12 to 14, carbon atoms; the fatty alcohols can be etherified with an average of 1 to 10 and preferably 1 to 5 moles of ethylene oxide and have both a conventional and preferably a narrowed homolog distribution. Examples include di-n-octyl sulfosuccinate and monolauryl 3EO sulfosuccinate in the form of their sodium salts.

    DetergensgemischeDetergent mixtures

    Die Herstellung der Mischungen, die vorzugsweise wäßrig sind und dann einen Feststoffgehalt von 5 bis 70, vorzugsweise 25 bis 50 Gew.-% aufweisen, erfolgt in der Regel durch Verrühren wäßriger Lösungen, Pasten oder Konzentrate der Einsatzstoffe, falls erforderlich bei leicht erhöhter Temperatur. Es ist jedoch ebenfalls möglich, sprühgetrocknete Pulver der beiden Komponenten zu vermischen und anschließend anzupasten oder Lösungen beider Inhaltsstoffe gemeinsam einer Sprühtrocknung und/ oder Granulation zu unterwerfen. In allen diesen Fällen handelt es sich um rein mechanische Verfahren, eine chemische Reaktion findet nicht statt.The preparation of the mixtures, which are preferably aqueous and then have a solids content of 5 up to 70, preferably 25 to 50 wt .-%, is usually done by stirring aqueous Solutions, pastes or concentrates of the input materials, if necessary at a slightly elevated temperature. However, it is also possible to mix spray-dried powder of the two components and then paste or solutions of both ingredients together spray drying and / or subject to granulation. All of these cases are purely mechanical processes, a chemical reaction does not take place.

    Gewerbliche AnwendbarkeitIndustrial applicability

    Im Sinne der erfindungsgemäßen Verwendung können die Haarshampoos 10 bis 30 Gew.-% - bezogen auf das Mittel - Detergensgemische so- wie übliche Hilfs- und Zusatzstoffe enthalten.For the purposes of the use according to the invention, the hair shampoos can be 10 to 30% by weight on the agent - contain detergent mixtures as well as usual auxiliaries and additives.

    TensideSurfactants

    Die Shampoos können als Hilfs- und Zusatzstoffe in erster Linie weitere anionische, nichtionische, kationische, amphotere und/oder zwitterionische Tenside enthalten. Typische Beispiele für anionische Tenside sind Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, α-Methylestersulfonate, Sulfofettsäuren, Alkylsulfate, Fettalkoholethersulfate, Glycerinethersulfate, Hydroxymischethersulfate, Monoglycerid(ether)sulfate, Fettsäureamid(ether)sulfate, Mono- und Dialkylsulfosuccinamate, Sulfotriglyceride, Amidseifen, Ethercarbonsäuren und deren Salze, Fettsäureisethionate, Fettsäuresarcosinate, Fettsäuretauride, Acyllactylate, Alkyloligoglucosidsulfate, Proteinfettsäurekondensate (insbesondere pflanzliche Produkte auf Sojabasis) und Alkyl(ether)phosphate. Sofern die anionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typische Beispiele für nichtionische Tenside sind Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolygylcolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Alk(en)yloligoglykoside, Fettsäure-N-alkylglucamide, Proteinhydrolysate (insbesondere pflanzliche Produkte auf Sojabasis) Polyolfettsäureester, Zuckerester, Sorbitanester und Polysorbate. Sofern die nichtionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typische Beispiele für kationische Tenside sind quartäre Ammoniumverbindungen und Esterquats, insbesondere quaternierte Fettsäuretrialkanolaminester-Salze. Typische Beispiele für amphotere bzw. zwitterionische Tenside sind Alkylbetaine, Alkylamidobetaine, Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine. Bei den genannten Tensiden handelt es sich ausschließlich um bekannte Verbindungen. Hinsichtlich Struktur und Herstellung dieser Stoffe sei auf einschlägige Übersichtsarbeiten beispielsweise J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, S.54.124 oder J.Falbe (ed.), "Katalysatoren, Tenside und Mineralöladditive", Thieme Verlag, Stuttgart, 1978, S.123-217 verwiesen.The shampoos can primarily contain other anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants as auxiliaries and additives. Typical examples of anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, α-methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps , Ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, acyl lactylates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on soy) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polygylcol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, alk (en) yloligoglycosides, fatty acid-N-alkylglucamides, protein hydrolysate, sorbate ester products, in particular vegetable ester ester-based sorbate products, especially vegetable-based ester esters, sorbate-based ester products (especially vegetable-based ester esters). If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, relevant reviews are available, for example, from J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, p. 54.124 or J.Falbe (ed.), "Catalysts, surfactants and Mineralöladditive ", Thieme Verlag, Stuttgart, 1978, pp . 123-217 .

    Weitere Hilfs- und ZusatzstoffeOther auxiliaries and additives

    Des weiteren können die Shampoos als Hilfs- und Zusatzstoffe Emulgatoren wie etwa alkoxylierte Fettalkohole oder Sorbitanester enthalten. Als Überfettungsmittel können Substanzen wie beispielsweise polyethoxylierte Lanolinderivate, Lecithinderivate und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen. Geeignete Verdickungsmittel sind beispielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmonound -diester von Fettsäuren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon sowie Elektrolyte wie Kochsalz und Ammoniumchlorid. Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte, Eiweißhydrolysate und Vitaminkomplexe zu verstehen. Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quaterniertes Chitosan, Polyvinylpyrrolidon, VinylpyrrolidonVinylacetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Cellulose-Derivate und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, Formaldehydlösung, Parabene, Pentadiol oder Sorbinsäure. Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycoldistearat, aber auch Fettsäuremonoglycolester in Betracht. Als Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosmetische Färbemittel" der Farbstoffkommission der Deutschen Forschungsgemeinschaft, veröffentlicht im Verlag Chemie, Weinheim, 1984, S.81-106 zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentrationen von 0,001 bis 0,1 Gew.-%, bezogen auf die gesamte Mischung, eingesetzt. Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 50, vorzugsweise 5 bis 40 Gew.-% - bezogen auf die Mittel - betragen. Furthermore, the shampoos can contain emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives. Superfatting agents may be used such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, the latter also serving as foam stabilizers. Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, and electrolytes such as sodium chloride and ammonium chloride. Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid. Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene, but also fatty acid monoglycol esters. The dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication " Cosmetic Dyes" by the Dye Commission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp . 81-106 . These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole. The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.

    BeispieleExamples

    Die Untersuchung des Schaumvermögens erfolgte gemäß Ross- Miles-Test DIN 53901, Teil 2) in einer 1 Gew.-%igen wäßrigen Lösung (Wasserhärte 16°d, Temperatur 20°C). Die Ergebnisse zu Basisschaum und Schaumzerfall sind in Tabelle 1 (erfindungsgemäße Beispiele) und Tabelle 2 (Vergleichsbeispiele) zusammengefaßt (Prozentangaben als Gew.-%). Eine Beispielrezeptur ist in Tabelle 3 enthalten. Basisschaum und Schaumzerfall Zusammensetzung/Performance 1 2 3 4 5 6 7 8 C 12/14-Kokosfettsäure-N-methylglucamid 80 70 60 50 40 30 25 20 Sulfobernsteinsäuremono-n-octylester-Dinatriumsalz 20 30 40 50 60 70 75 80 Schaumhöhe - Basisschaum 620 630 640 650 680 680 680 510 - nach 5 min 500 520 530 560 580 580 580 560 Basisschaum und Schaumzerfall Zusammensetzung/Performance V1 V2 V3 V4 V5 V6 V7 V8 V9 C 12/14-Kokosfettsäure-N-methylglucamid 100 - - - - 40 40 40 - Sulfobernsteinsäuremono-n-octylester-Dinatriumsalz - 100 - - - - - - 60 Dodecylbenzolsulfonat-Natriumsalz - - 100 - - 60 - - 40 Talgfettsäuremethylestersulfonat-Natriumsalz - - - 100 - - 60 - - C12114-Kokosalkyl+7EO-ethercarbonsäure-Natriumsalz - - - - 100 - - 60 - Schaumhöhe - Basisschaum 450 500 600 550 550 500 475 475 500 - nach 5 min 325 400 280 210 350 300 180 300 400 Haarshampoo-Rezeptur Sodium Laureth Sulfate (Texapon K 14S) 15,0 Kokosfettsäure-N-methylglucamid 3,0 Sodium Laureth Sulfosuccinate (Texapon SB3) 12,0 Hydrolyzed Collagen (Nutrilan L) 3,0 Wasser 77,0 The foaming power was examined in accordance with the Ross Miles Test DIN 53901, part 2) in a 1% strength by weight aqueous solution (water hardness 16 ° d, temperature 20 ° C.). The results for base foam and foam breakdown are summarized in Table 1 (examples according to the invention) and Table 2 (comparative examples) (percentages as% by weight). An example recipe is included in Table 3. Base foam and foam breakdown Composition / performance 1 2nd 3rd 4th 5 6 7 8th C 12/14 coconut fatty acid N-methylglucamide 80 70 60 50 40 30th 25th 20th Mono-n-octyl sulfosuccinate disodium salt 20th 30th 40 50 60 70 75 80 Foam height - base foam 620 630 640 650 680 680 680 510 - after 5 min 500 520 530 560 580 580 580 560 Base foam and foam breakdown Composition / performance V1 V2 V3 V4 V5 V6 V7 V8 V9 C 12/14 coconut fatty acid N-methylglucamide 100 - - - - 40 40 40 - Mono-n-octyl sulfosuccinate disodium salt - 100 - - - - - - 60 Dodecylbenzenesulfonate sodium salt - - 100 - - 60 - - 40 Tallow fatty acid methyl ester sulfonate sodium salt - - - 100 - - 60 - - C12114 cocoalkyl + 7EO ether carboxylic acid sodium salt - - - - 100 - - 60 - Foam height - base foam 450 500 600 550 550 500 475 475 500 - after 5 min 325 400 280 210 350 300 180 300 400 Hair shampoo recipe Sodium Laureth Sulfate (Texapon K 14S) 15.0 Coconut fatty acid N-methylglucamide 3.0 Sodium Laureth Sulfosuccinate (Texapon SB3) 12.0 Hydrolyzed Collagen (Nutrilan L) 3.0 water 77.0

    Claims (5)

    1. The use of detergent mixtures containing
      (a) fatty acid-N-alkyl polyhydroxyalkyl amides and
      (b) sulfosuccinates
      in a ratio by weight of 80:20 to 20:80 for the production of hair shampoos.
    2. The use claimed in claim 1, characterized in that fatty acid-N-alkyl polyhydroxyalkyl amides corresponding to formula (I):
      Figure 00090001
      in which R1CO is an aliphatic acyl group containing 6 to 22 carbon atoms, R2 is an alkyl or hydroxyalkyl group containing 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl group containing 3 to 12 carbon atoms and 3 to 10 hydroxyl groups, are used.
    3. The use claimed in claims 1 and 2, characterized in that fatty acid-N-alkyl glucamides are used as component (a).
    4. The use claimed in claims 1 to 3, characterized in that sulfosuccinates corresponding to formula (III):
      Figure 00090002
      in which R3 is an alkyl and/or alkenyl group containing 6 to 22 carbon atoms, R4 has the same meaning as R3 or X, m and n independently of one another stand for 0 or numbers of 1 to 10 and X is an alkali metal or alkaline earth metal, ammonium, alkylammonium or glucammonium, are used as component (b).
    5. The use claimed in claims 1 to 4, characterized in that components (a) and (b) are used in a ratio by weight of 50:50 to 25:75
    EP95943495A 1994-07-19 1995-07-10 Use of detergent mixtures Expired - Lifetime EP0771346B1 (en)

    Applications Claiming Priority (3)

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    DE4425449A DE4425449A1 (en) 1994-07-19 1994-07-19 Detergent mixtures with improved cleaning performance
    DE4425449 1994-07-19
    PCT/EP1995/002677 WO1996002620A1 (en) 1994-07-19 1995-07-10 Detergent mixtures with improved washing power

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    EP0771346A1 EP0771346A1 (en) 1997-05-07
    EP0771346B1 true EP0771346B1 (en) 1999-10-20

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    GB9800850D0 (en) * 1998-01-15 1998-03-11 Courtaulds Plc Methods of manufacturing and collecting cellulosic particles
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    NZ206211A (en) * 1982-11-16 1986-04-11 Unilever Plc Foaming liquid detergent compositions containing sulphosuccinic acid esters
    ATE135736T1 (en) * 1990-09-28 1996-04-15 Procter & Gamble DETERGENT CONTAINING ALKYL SULFATE AND POLYHYDROXYFATTY ACID AMIDE SURFACTANT
    DE4301358C2 (en) * 1992-01-30 1995-08-10 Hermann Scheler Packaging-free detergent, especially body and / or textile detergent
    GB9207799D0 (en) * 1992-04-09 1992-05-27 Procter & Gamble Aqueous compositions
    EP0572723A1 (en) * 1992-06-02 1993-12-08 The Procter & Gamble Company Structured liquid detergent compositions
    DE4224714A1 (en) * 1992-07-27 1994-02-03 Henkel Kgaa Foaming detergent mixtures
    US5545354A (en) * 1992-09-01 1996-08-13 The Procter & Gamble Company Liquid or gel dishwashing detergent containing a polyhydroxy fatty acid amide, calcium ions and an alkylpolyethoxypolycarboxylate
    AU5171393A (en) * 1992-10-13 1994-05-09 Procter & Gamble Company, The Liquid or gel dishwashing detergent composition containing polyhydroxy fatty acid amide and certain elements
    DE4238211C2 (en) * 1992-11-12 1997-11-13 Henkel Kgaa Use of detergent mixtures containing cationic sugar surfactants and other surfactants for the production of softeners
    DE4315810A1 (en) * 1993-05-12 1994-11-17 Henkel Kgaa Aqueous detergent mixtures
    WO1995003782A1 (en) * 1993-07-28 1995-02-09 Ici Australia Operations Proprietary Limited Pearlescent based concentrate for personal care products

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    EP0771346A1 (en) 1997-05-07

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