WO1996029982A1 - Cosmetic and/or pharmaceutical preparations - Google Patents

Cosmetic and/or pharmaceutical preparations Download PDF

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Publication number
WO1996029982A1
WO1996029982A1 PCT/EP1996/001215 EP9601215W WO9629982A1 WO 1996029982 A1 WO1996029982 A1 WO 1996029982A1 EP 9601215 W EP9601215 W EP 9601215W WO 9629982 A1 WO9629982 A1 WO 9629982A1
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Prior art keywords
alkyl
alcohol
carbon atoms
sulfates
cosmetic
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PCT/EP1996/001215
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German (de)
French (fr)
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Bernd Fabry
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1996029982A1 publication Critical patent/WO1996029982A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the invention relates to preparations with improved foaming power, containing alkyl glycosides and secondary 2,3-alkyl sulfates.
  • Alkyl oligoglycosides in particular alkyl oligoglucosides, are nonionic surfactants which are becoming increasingly important due to their excellent detergent properties and high ecotoxicological compatibility.
  • the production and use of these substances have recently been described in a number of review articles, of which the publications by H.Hensen in Skin Care Forum, 1, (Oct. 1992), D.Balzer and N.Ripke in Seifenöle- Fette waxes 118, 894 (1992) and B.Brancq in soap oils Fette waxes 118, 905 (1992) should be mentioned.
  • Alkyl oligoglucosides are characterized by a foam strength that is otherwise only typical of anionic surfactants. This foam development can be done by combining it with others preferably anionic surfactants can be increased in a synergistic manner.
  • EP-B1 0070074 Procter & Gamble
  • foaming detergent mixtures containing alkyl glycosides and anionic surfactants with a carboxylate, sulfate and / or sulfonate structure such as primary alkyl sulfates and alkyl ether sulfates are claimed.
  • the foaming power in particular the foam stability in hard water and with high fat content, is unsatisfactory for a large number of applications.
  • the object of the invention was to provide new detergent mixtures which are characterized by improved foaming power and at least equally good skin tolerance.
  • the invention relates to cosmetic and / or pharmaceutical preparations containing a) alkyl and alkenyl oligoglycosides of the general formula (I),
  • Alkyl and alkenyl oligoglycosides are known substances that can be obtained by the relevant methods of preparative organic chemistry.
  • 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 oligoglucosides.
  • the index number p in the general formula (I) gives the degree of oligomerization (DP degree), ie the distribution of mono and oligoglycosides and stands for a number between 1 and 10. While p must always be an integer in a given compound, the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number. Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 1.6 and in particular between 1.2 and 1.5.
  • 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, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as those obtained in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • Alkyl oligoglucosides of chain length C 8 -C 10 (DP - 1.1 to 1.3) are preferred, which are obtained as a preliminary step in the separation of technical C 8 -C 18 coconut fatty alcohol by distillation and with a proportion of less than 6% by weight.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, Pe troselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl 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 1.1 to 1.6 are preferred.
  • Secondary alkyl sulfates are known anionic surfactants which are obtained in the prior art by adding sulfuric acid to olefins of a suitable chain length. Another method is to epoxidize olefins and then open the oxirane rings with sulfur trioxide. In the subsequent neutralization, however, certain proportions of hydroxysulfates or alkenesulfates can also arise. Processes for the preparation of secondary alkyl sulfates are described, for example, in the publications DE-OS 1568741 (Henkel), WO 93/24452 and EP-A 0466243 (Shell) and WO 94/24245 (Procter & Gamble).
  • Typical examples of secondary 2,3-alkyl sulfates are addition products of sulfuric acid onto technical olefin cuts with 12 to 14 carbon atoms in the form of their sodium and / or magnesium salts.
  • the agents according to the invention can contain the alkyl and / or alkenyl oligoglucosides and the secondary 2,3-alkyl sulfates in a weight ratio of 1:99 to 99: 1, preferably 10:90 to 90:10 and in particular 80:20 to 50:50.
  • the agents according to the invention are distinguished by a particularly advantageous foaming power, especially in the presence of water hardness and sebum.
  • the preparations can be, for example, hair shampoos, shower gels, foam baths, hair rinses, lotions and the like, which contain further auxiliaries and additives, such as, for example, co-surfactants, emulsifiers, superfatting agents, cationic polymers, silicone compounds, thickeners, biogenic active ingredients, film formers, Preservatives, dyes and fragrances included.
  • the preparations according to the invention can contain further anionic, nonionic, cationic, amphoteric and / or zwitterionic co-surfactants.
  • anionic surfactants are alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, o-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, Gly cerine ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates.
  • the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, fatty acid N-alkylglucamides, polyol fatty acid esters, sugar esters, sorbitan esters and polysorbates. If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. In terms of structure and manufacture these substances are on relevant reviews, for example J.Falbe (ed.), “Surfactants in Consumer Products”, Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), “Catalysts, Surfactants and Mineral Oil Additives” , Thieme Verlag, Stuttgart, 1978, pp. 123-217.
  • Suitable emulsifiers are both known W / O and O / W emulsifiers such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters or polyglycerol poly ricinoleates or polyglycerol poly 12-hydroxystearates.
  • Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone, vinylimidazole polymers such as, for example, LUVICUAT (BASF AG, Ludwidshafts / FRG), condensation products of polyglycols and amines, and quaternized hydroxylated collagen polyimide peptides such as lauryl hydrolyzate collagen polypeptides (R) L, Grünau GmbH), polyethyleneimine, cationic silicone polymers such as amidomethicone or DOW CORNING 929, Dow Corning Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (CARTARETINE (R) , Sandoz / CH), polyaminopolyamides as described, for example, in the FR-A 2252840 and their crosslinked water-soluble
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl-modified silicone compounds.
  • 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- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as, for example, fatty alcohol distribution with fatty alcohols such as fatty alcohol or alkyl oligoglucosides and electrolytes such as table salt and ammonium chloride.
  • 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- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such
  • Biogenic active substances are understood to mean, for example, plant extracts 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, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, 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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Abstract

The invention concerns cosmetic and/or pharmaceutical preparations having improved foaming power and containing: a) alkyloligoglycosides and alkenyloligoglycosides of general formula (I) R1O-[G]p in which R1 stands for a C¿4? to C22 alkyl and/or alkenyl group, G stands for a C5 or C6 carbohydrate group, and p stands for numbers from 1 to 10; and b) secondary C12 to C22 2,3-alkylsulphates in the form of their alkali and/or alkaline earth salts.

Description

Kosmetische und/oder pharmazeutische Zubereitungen  Cosmetic and / or pharmaceutical preparations
Gebiet der Erfindung Field of the Invention
Die Erfindung betrifft Zubereitungen mit verbessertem Schaumvermögen, enthaltend Alkylglykoside und sekundäre 2,3-Alkylsulfate. The invention relates to preparations with improved foaming power, containing alkyl glycosides and secondary 2,3-alkyl sulfates.
Stand der Technik State of the art
Alkyloligoglykoside, insbesondere Alkyloligoglucoside stellen nichtionische Tenside dar, die infolge ihrer ausgezeichneten Detergenseigenschaften und hohen ökotoxikologischen Verträglichkeit zunehmend an Bedeutung gewinnen. Herstellung und Verwendung dieser Stoffe sind gerade in letzter Zeit in einer Reihe von Übersichtsartikeln dargestellt worden, von denen stellvertretend die Veröffentlichungen von H.Hensen in Skin Care Forum, 1, (Okt.1992), D.Balzer und N.Ripke in Seifenöle-Fette-Wachse 118, 894 (1992) und B.Brancq in Seifen-Öle-Fette-Wachse 118, 905 (1992) genannt werden sollen. Alkyl oligoglycosides, in particular alkyl oligoglucosides, are nonionic surfactants which are becoming increasingly important due to their excellent detergent properties and high ecotoxicological compatibility. The production and use of these substances have recently been described in a number of review articles, of which the publications by H.Hensen in Skin Care Forum, 1, (Oct. 1992), D.Balzer and N.Ripke in Seifenöle- Fette waxes 118, 894 (1992) and B.Brancq in soap oils Fette waxes 118, 905 (1992) should be mentioned.
Alkyloligoglucoside zeichnen sich durch eine Schaumstärke aus, die sonst nur für anionische Tenside typisch ist. Diese Schaumentwicklung kann durch Kombination mit anderen, vor zugsweise anionischen Tensiden noch in synergistischer Weise gesteigert werden. Aus der Vielzahl von Veröffentlichungen zu diesem Thema sei stellvertretend und wegen seiner grundsätzlichen Bedeutung auf das europäische Patent EP-B1 0070074 (Procter & Gamble) verwiesen, in dem schäumende Detergensgemische, enthaltend Alkylglykoside und anionische Tenside mit Carboxylat-, Sulfat- und/oder SulfonatStruktur wie beispielsweise primäre Alkylsulfate und Alkylethersul f ate beansprucht werden . Für eine Vielzahl von Anwendungen ist das Schaumvermögen, insbesondere die Schaumstabilität in hartem Wasser und bei großer Fettbelastung jedoch nicht zufriedenstellend. Alkyl oligoglucosides are characterized by a foam strength that is otherwise only typical of anionic surfactants. This foam development can be done by combining it with others preferably anionic surfactants can be increased in a synergistic manner. From the large number of publications on this subject, and because of its fundamental importance, reference should be made to the European patent EP-B1 0070074 (Procter & Gamble), in which foaming detergent mixtures containing alkyl glycosides and anionic surfactants with a carboxylate, sulfate and / or sulfonate structure such as primary alkyl sulfates and alkyl ether sulfates are claimed. However, the foaming power, in particular the foam stability in hard water and with high fat content, is unsatisfactory for a large number of applications.
Demzufolge hat die Aufgabe der Erfindung darin bestanden, neue Detergensgemische zur Verfügung zu stellen, die sich durch ein verbessertes Schaumvermögen bei mindestens gleich guter Hautverträglichkeit auszeichnen. Accordingly, the object of the invention was to provide new detergent mixtures which are characterized by improved foaming power and at least equally good skin tolerance.
Beschreibung der Erfindung Description of the invention
Gegenstand der Erfindung sind kosmetische und/oder pharmazeutische Zubereitungen, enthaltend a) Alkyl- und Alkenyloligoglykoside der allgemeinen Formel (I), The invention relates to cosmetic and / or pharmaceutical preparations containing a) alkyl and alkenyl oligoglycosides of the general formula (I),
R1O-[G]p (I) in der R1 für einen Alkyl- und/oder Alkenylrest mit 4 bis 22 Kohlenstoffatomen, G für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen und p für Zahlen von 1 bis 10 steht, und b) sekundäre 2,3-Alkylsulfate mit 12 bis 22 Kohlenstoffatomen in Form ihrer Alkali- und/oder Erdalkalisalze. R 1 O- [G] p (I) in R 1 for an alkyl and / or alkenyl radical with 4 to 22 carbon atoms, G for a sugar radical with 5 or 6 carbon atoms and p represents numbers from 1 to 10, and b) secondary 2,3-alkyl sulfates with 12 to 22 carbon atoms in the form of their alkali and / or alkaline earth metal salts.
Überraschenderweise wurde gefunden, daß Abmischungen von Alkylglucosiden mit sekundären 2,3-Alkylsulfaten eine sehr gute dermatologische Verträglichkeit und gegenüber einer Kombination mit primären Alkylsulfaten ein verbessertes Schaumvermögen sowohl hinsichtlich des Basisschaums als auch der Schaumstabilität in Gegenwart von Wasserhärte und Sebum aufeisen. Surprisingly, it was found that mixtures of alkyl glucosides with secondary 2,3-alkyl sulfates have very good dermatological compatibility and, compared to a combination with primary alkyl sulfates, have improved foaming capacity with regard to both the base foam and the foam stability in the presence of water hardness and sebum.
Alkyl- und/oder Alkenyloligoglykoside Alkyl and / or alkenyl oligoglycosides
Alkyl- und Alkenyloligoglykoside stellen bekannte Stoffe dar, die nach den einschlägigen Verfahren der präparativen organischen Chemie erhalten werden können. Stellvertretend für das umfangreiche Schrifttum sei hier auf die Schriften EP-A1 0301298 und WO 90/03977 verwiesen. Alkyl and alkenyl oligoglycosides are known substances that can be obtained by the relevant methods of preparative organic chemistry. As representative of the extensive literature, reference is made here to the documents EP-A1 0301298 and WO 90/03977.
Die Alkyl- und/oder Alkenyloligoglykoside können sich von Aldosen bzw. Ketosen mit 5 oder 6 Kohlenstoffatomen, vorzugsweise der Glucose ableiten. Die bevorzugten Alkyl- und/oder Alkenyloligoglykoside sind somit Alkyl- und/oder Alkenyloligoglucoside. 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 oligoglucosides.
Die Indexzahl p in der allgemeinen Formel (I) gibt den Oligomerisierungsgrad (DP-Grad), d. h. die Verteilung von Mono und Oligoglykosiden an und steht für eine Zahl zwischen 1 und 10. Während p in einer gegebenen Verbindung stets ganzzahlig sein muß, ist der Wert p für ein bestimmtes Alkyloligoglykosid eine analytisch ermittelte rechnerische Größe, die meistens eine gebrochene Zahl darstellt. Vorzugsweise werden Alkyl- und/oder Alkenyloligoglykoside mit einem mittleren Oligomerisierungsgrad p von 1,1 bis 3 eingesetzt. Aus anwendungstechnischer Sicht sind solche Alkyl- und/oder Alkenyloligoglykoside bevorzugt, deren Oligomerisierungsgrad kleiner als 1,6 ist und insbesondere zwischen 1,2 und 1,5 liegt. The index number p in the general formula (I) gives the degree of oligomerization (DP degree), ie the distribution of mono and oligoglycosides and stands for a number between 1 and 10. While p must always be an integer in a given compound, the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number. Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 1.6 and in particular between 1.2 and 1.5.
Der Alkyl- bzw. Alkenylrest R1 kann sich von primären Alkoholen mit 4 bis 11, vorzugsweise 8 bis 10 Kohlenstoffatomen ableiten. Typische Beispiele sind Butanol, Capronalkohol, Caprylalkohol, Caprinalkohol und Undecylalkohol sowie deren technische Mischungen, wie sie beispielsweise bei der Hydrierung von technischen Fettsäuremethylestern oder im Verlauf der Hydrierung von Aldehyden aus der Roelen' sehen Oxosynthese anfallen. Bevorzugt sind Alkyloligoglucoside der Kettenlänge C8-C10 (DP - 1,1 bis 1,3), die als Vorlauf bei der destillativen Auftrennung von technischem C8-C18-Kokosfettalkohol anfallen und mit einem Anteil von weniger als 6 Gew.-% C12-Alkohol verunreinigt sein können sowie Alkyloligoglucoside auf Basis technischer C9/11-Oxoalkohole (DP = 1,1 bis 1,3). 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, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as those obtained in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis. Alkyl oligoglucosides of chain length C 8 -C 10 (DP - 1.1 to 1.3) are preferred, which are obtained as a preliminary step in the separation of technical C 8 -C 18 coconut fatty alcohol by distillation and with a proportion of less than 6% by weight. % C 12 alcohol may be contaminated and alkyl oligoglucosides based on technical C 9/11 oxo alcohols (DP = 1.1 to 1.3).
Der Alkyl- bzw. Alkenylrest R1 kann sich ferner auch von primären Alkoholen mit 12 bis 22, vorzugsweise 12 bis 14 Kohlenstoffatomen ableiten. Typische Beispiele sind Laurylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Pe troselinylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol, sowie deren technische Gemische, die wie oben beschrieben erhalten werden können. Bevorzugt sind Alkyloligoglucoside auf Basis von gehärtetem C12/14-Kokosalkohol mit einem DP von 1,1 bis 1,6. The alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, Pe troselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl 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 1.1 to 1.6 are preferred.
Sekundäre 2,3-Alkylsulfate Secondary 2,3-alkyl sulfates
Sekundäre Alkylsulfate stellen bekannte anionische Tenside dar, die man nach dem Stand der Technik durch Anlagerung von Schwefelsäure an Olefine geeigneter Kettenlänge erhält. Eine weitere Methode besteht darin, Olefine zu epoxidieren und die Oxiranringe anschließend mit Schwefeltrioxid zu öffnen. Bei der nachfolgenden Neutralisation können jedoch auch gewisse Anteile an Hydroxysulfaten bzw. Alkensulfaten entstehen. Verfahren zur Herstellung von sekundären Alkylsulfaten sind beispielsweise in den Druckschriften DE-OS 1568741 (Henkel), WO 93/24452 und EP-A 0466243 (Shell) sowie WO 94/24245 (Procter & Gamble) beschrieben. Der Einsatz von sekundären 2,3-Alkyl- sulfaten in Wasch- und Reinigungsmitteln ist Gegenstand der folgenden Internationalen Patentanmeldungen WO 94/24238, WO 94/24239, WO 94/24240, WO 94/24241, WO 94/24242, WO 94/24243, WO 94/24244, WO 94/24246 (Procter & Gamble). Secondary alkyl sulfates are known anionic surfactants which are obtained in the prior art by adding sulfuric acid to olefins of a suitable chain length. Another method is to epoxidize olefins and then open the oxirane rings with sulfur trioxide. In the subsequent neutralization, however, certain proportions of hydroxysulfates or alkenesulfates can also arise. Processes for the preparation of secondary alkyl sulfates are described, for example, in the publications DE-OS 1568741 (Henkel), WO 93/24452 and EP-A 0466243 (Shell) and WO 94/24245 (Procter & Gamble). The use of secondary 2,3-alkyl sulfates in detergents and cleaning agents is the subject of the following international patent applications WO 94/24238, WO 94/24239, WO 94/24240, WO 94/24241, WO 94/24242, WO 94 / 24243, WO 94/24244, WO 94/24246 (Procter & Gamble).
Typische Beispiele für sekundäre 2,3-Alkylsulfate, sind Anlagerungsprodukte von Schwefelsäure an technische Olefin- schnitte mit 12 bis 14 Kohlenstoffatomen in Form ihrer Natrium- und/oder Magnesiumsalze. Die erfindungsgemäßen Mittel können die Alkyl- und/oder Alkenyloligoglucoside und die sekundären 2,3-Alkylsulfate im Gewichtsverhältnis 1 : 99 bis 99 : 1, vorzugsweise 10 : 90 bis 90 : 10 und insbesondere 80 : 20 bis 50 : 50 enthalten. Typical examples of secondary 2,3-alkyl sulfates are addition products of sulfuric acid onto technical olefin cuts with 12 to 14 carbon atoms in the form of their sodium and / or magnesium salts. The agents according to the invention can contain the alkyl and / or alkenyl oligoglucosides and the secondary 2,3-alkyl sulfates in a weight ratio of 1:99 to 99: 1, preferably 10:90 to 90:10 and in particular 80:20 to 50:50.
Gewerbliche Anwendbarkeit Industrial applicability
Die erfindungsgemäßen Mittel zeichnen sich bei ausgezeichneter hautkosmetischer Verträglichkeit durch ein besonders vorteilhaftes Schaumvermögen gerade auch in Anwesenheit von Wasserhärte und Sebum aus. Bei den Zubereitungen kann es sich beispielsweise um Haarshampoos, Duschgele, Schaumbäder, Haarspülungen, Lotionen und dergleichen handeln, die weitere Hilfs- und Zusatzstoffe, wie beispielsweise Co-Tenside, Emulgatoren, Überfettungsmittel, kationische Polymere, Siliconverbindungen, Verdickungsmittel, biogene Wirkstoffe, Filmbildner, Konservierungsmittel, Färb- und Duftstoffe enthalten. With excellent skin-cosmetic compatibility, the agents according to the invention are distinguished by a particularly advantageous foaming power, especially in the presence of water hardness and sebum. The preparations can be, for example, hair shampoos, shower gels, foam baths, hair rinses, lotions and the like, which contain further auxiliaries and additives, such as, for example, co-surfactants, emulsifiers, superfatting agents, cationic polymers, silicone compounds, thickeners, biogenic active ingredients, film formers, Preservatives, dyes and fragrances included.
Tenside Surfactants
Die erfindungsgemäßen Zubereitungen können weitere anionischen, nichtionischen, kationischen, amphoteren und/oder zwitterionischen Co-Tenside enthalten. The preparations according to the invention can contain further anionic, nonionic, cationic, amphoteric and / or zwitterionic co-surfactants.
Typische Beispiele für anionische Tenside sind Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, oc-Methylestersulfonate, Sulfofettsäuren, Alkylsulfate, Fettalkoholethersulfate, Gly cerinethersulfate, Hydroxymischethersulfate, Monoglycerid(ether)sulfate, Fettsäureamid(ether)sulfate, Mono- und Dialkylsulfosuccinate. Mono- und Dialkylsulfosuccinamate, Sulfotriglyceride, Amidseifen, Ethercarbonsäuren und deren Salze, Fettsäureisethionate, Fettsäuresarcosinate, Fettsäuretauride, Acyllactylate, Acylglutamate, Alkyloligoglucosidsulfate und Alkyl(ether)phosphate. Sofern die anionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typical examples of anionic surfactants are alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, o-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, Gly cerine ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates. Mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, acyl lactylates, acyl glutamates, alkyl oligoglucoside sulfates and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
Typische Beispiele für nichtionische Tenside sind Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolygylcolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Fettsäure-N-alkylglucamide, Polyolfettsäureester, Zuckerester, Sorbitanester und Polysorbate. Sofern die nichtionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, fatty acid N-alkylglucamides, polyol fatty acid esters, sugar esters, sorbitan esters and polysorbates. If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
Typische Beispiele für kationische Tenside sind guartäre Ammoniumverbindungen und Esterquats, insbesondere quaternierte Fettsäuretrialkanolaminester-Salze. Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
Typische Beispiele für amphotere bzw. zwitterionische Tenside sind Alkylbetaine, Alkylamidobetaine, Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
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 surfactants mentioned are exclusively known compounds. In terms of structure and manufacture these substances are on relevant reviews, for example J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, Surfactants and Mineral Oil Additives" , Thieme Verlag, Stuttgart, 1978, pp. 123-217.
Als Emulgatoren kommen sowohl bekannte W/O- als auch O/W-Emulgatoren wie beispielsweise gehärtetes und ethoxyliertes Ricinusöl, Polyglycerinfettsäureester oder Polyglycerinpoly- ricinoleate bzw. Polyglycerinpoly-12-hydroxystearate in Frage. Suitable emulsifiers are both known W / O and O / W emulsifiers such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters or polyglycerol poly ricinoleates or polyglycerol poly 12-hydroxystearates.
Als Überfettungsmittel können Substanzen wie beispielsweise polyethoxylierte Lanolinderivate, Lecithinderivate, Polyolfettsäureester, Monoglyceride und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen. Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
Geeignete kationische Polymere sind beispielsweise kationischen Cellulosederivate, kationischen Stärke, Copolymere von Diallylammoniumsalzen und Acrylamiden, quaternierte Vinylpyrrolidon Vinylimidazol-Polymere wie z.B. LUVICUAT (BASF AG, Ludwidshaften/FRG), Kondensationsprodukte von Polyglycolen und Aminen, quaternierte Kollagenpolypeptide wie beispielsweise Lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat(R) L, Grünau GmbH), Polyethylenimin, kationische Siliconpolymere wie z.B. Amidomethicone oder DOW CORNING 929, Dow Corning Co./US, Copolymere der Adipinsäure und Dimethylaminohydroxypropyldiethylentrimamin (CARTARETINE( R), Sandoz/CH), Polyaminopolyamide wie z.B. beschrieben in der FR-A 2252840 sowie deren vernetzte wasserlöslichen Polymere, kationische Chitinderivate wie beispielsweise quaterniertes Chitosan, gegebenenfalls mikrokristallin verteilt, kationischer GuarGum wie z.B. JAGUAR(R) C-B-S, JAGUAR(R) C-17, JAGUAR(R) C-16 der Celanese/US, quaternierte Ammoniumsalz-Polymere wie z.B. MIRAPOL(R) A-15, MIRAPOL(R) AD-1, MIRAPOL(R) AZ-1 der Miranol/US. Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone, vinylimidazole polymers such as, for example, LUVICUAT (BASF AG, Ludwidshafts / FRG), condensation products of polyglycols and amines, and quaternized hydroxylated collagen polyimide peptides such as lauryl hydrolyzate collagen polypeptides (R) L, Grünau GmbH), polyethyleneimine, cationic silicone polymers such as amidomethicone or DOW CORNING 929, Dow Corning Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (CARTARETINE (R) , Sandoz / CH), polyaminopolyamides as described, for example, in the FR-A 2252840 and their crosslinked water-soluble polymers, cationic Chitin derivatives such as quaternized chitosan, optionally microcrystalline, cationic guar gum such as JAGUAR (R) CBS, JAGUAR (R) C-17, JAGUAR (R) C-16 from Celanese / US, quaternized ammonium salt polymers such as MIRAPOL (R) A-15, MIRAPOL (R) AD-1, MIRAPOL (R) AZ-1 from Miranol / US.
Geeignete Siliconverbindungen sind beispielsweise Dimethylpolysiloxane, Methylphenylpolysiloxane, cyclische Silicore sowie Amino-, Fettsäure-, Alkohol-, Polyether-, Epoxy-, Fluorund/oder Alkyl-modifizierte Siliconverbindungen. Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl-modified silicone compounds.
Geeignete Verdickungsmittel sind beispielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmono- und -diester von Fettsäuren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon, Tenside wie beispielsweise Fettalkoholethoxylate mit eingeengter Homologenverteilung oder Alkyloligoglucoside sowie Elektrolyte wie Kochsalz und Ammoniumchlorid. 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- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as, for example, fatty alcohol distribution with fatty alcohols such as fatty alcohol or alkyl oligoglucosides and electrolytes such as table salt and ammonium chloride.
Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte und Vitaminkomplexe zu verstehen. Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quaterniertes Chitosan, Polyvinylpyrrolidon, Vinylpyrrolidon-Vinyl-acetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Cellulose-Derivate, Kollagen, Hyaluronsäure bzw. deren Salze und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, Formaldehydlösung, Parabene, Pentandiol oder Sorbinsäure. 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, collagen, hyaluronic acid or its salts and similar compounds. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycoldistearat, aber auch Fettsäure- monoglycolester in Betracht. Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
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. 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.
Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 50, vorzugsweise 5 bis 40 Gew.-% - bezogen auf die Mittel - betragen. The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
Beispiele Examples
I. Eingesetzte Tenside I. Surfactants used
A1) Cg/i6-Alkyloligoglucosid A1) Cg / i6 alkyl oligoglucoside
(PLANTAREN(R) APG 2000, Henkel KGaA, Düsseldorf/FRG) (PLANTAREN (R) APG 2000, Henkel KGaA, Düsseldorf / FRG)
B1) Sekundäres C12-Alkylsulfat-Natriumsalz B1) C 12 secondary alkyl sulfate sodium salt
B2) Primäres Laurylsulfat-Natriumsalz B2) Primary lauryl sulfate sodium salt
B3 ) Natriumlaurylethersulfat B3) sodium lauryl ether sulfate
(TEXAPON(R) NSO, Henkel KGaA, Düsseldorf/FRG) (TEXAPON (R) NSO, Henkel KGaA, Düsseldorf / FRG)
II. Scha wavermögen II. Sleeping power
Die Untersuchung des Schaumvermögens erfolgte gemäß Götte nach DIN 53902, Teil 1 (1 g AS/1 bei 15°d mit 0,1 g Sebum nach Bey. Die Ergebnisse zu Basisschaum und Schaumzerfall sind in Tabelle 1 zusammengefaßt( Prozentangaben als Gew-%): The foaming power was examined in accordance with Götte in accordance with DIN 53902, Part 1 (1 g AS / 1 at 15 ° d with 0.1 g Sebum according to Bey. The results for base foam and foam breakdown are summarized in Table 1 (percentages as% by weight) :
Figure imgf000014_0001
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Figure imgf000015_0001
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Figure imgf000017_0001
Figure imgf000018_0001
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Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000018_0001
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Figure imgf000021_0001
Figure imgf000021_0001

Claims

Patentansprüche claims
1. Kosmetische und/oder pharmazeutische Zubereitungen, enthaltend a) Alkyl- und Alkenyloligoglykoside der allgemeinen Formel (I), 1. Cosmetic and / or pharmaceutical preparations containing a) alkyl and alkenyl oligoglycosides of the general formula (I),
R1O-[G]p (I) in der R1 für einen Alkyl- und/oder Alkenylrest mit 4 bis 22 Kohlenstoffatomen, G für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen und p für Zahlen von 1 bis 10 steht, und b) sekundäre 2,3-Alkylsulfate mit 12 bis 22 Kohlenstoffatomen in Form ihrer Alkali- und/oder Erdalkalisalze. R 1 O- [G] p (I) in which R 1 is an 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, and b ) Secondary 2,3-alkyl sulfates with 12 to 22 carbon atoms in the form of their alkali and / or alkaline earth metal salts.
2. Detergensgemische nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß sie die Alkyl- und/oder Alkenyloligoglucoside und die sekundären 2,3-Alkylsulfate im Gewichtsverhältnis 1 : 99 bis 99 : 1 enthalten. 2. Detergent mixtures according to claims 1 to 5, characterized in that they contain the alkyl and / or alkenyl oligoglucosides and the secondary 2,3-alkyl sulfates in a weight ratio of 1:99 to 99: 1.
3. Zubereitungen nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, daß sie weiterhin anionische, nichtionische, kationische und/oder amphothere bzw. zwitterionische Tenside enthalten. 3. Preparations according to claims 1 and 2, characterized in that they further contain anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.
4. Zubereitungen nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß, daß sie weiterhin kationische Polymere und/oder Siliconverbindungen enthalten. 4. Preparations according to claims 1 to 3, characterized in that they also contain cationic polymers and / or silicone compounds.
PCT/EP1996/001215 1995-03-30 1996-03-21 Cosmetic and/or pharmaceutical preparations WO1996029982A1 (en)

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