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WO1996029982A1 - Preparations cosmetiques et/ou pharmaceutiques - Google Patents

Preparations cosmetiques et/ou pharmaceutiques 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
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alcohol
carbon atoms
sulfates
cosmetic
Prior art date
Application number
PCT/EP1996/001215
Other languages
German (de)
English (en)
Inventor
Bernd Fabry
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 WO1996029982A1 publication Critical patent/WO1996029982A1/fr

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Classifications

    • 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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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des préparations cosmétiques et/ou pharmaceutiques à pouvoir moussant amélioré, qui contiennent: a) des alkyloligoglycosides et des alcényloligoglycosides de la formule générale (I) R10-[G]p dans laquelle R1 désigne un reste alkyle et/ou alcényle ayant entre 4 et 22 atomes de carbone, G désigne un reste hydrate de carbone ayant entre 5 et 6 atomes de carbone et p vaut entre 1 et 10; et b) des 2,3-alkylsulfates secondaires ayant entre 12 et 22 atomes de carbone sous la forme de leurs sels alcalins et/ou alcalino-terreux.
PCT/EP1996/001215 1995-03-30 1996-03-21 Preparations cosmetiques et/ou pharmaceutiques WO1996029982A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1995111637 DE19511637A1 (de) 1995-03-30 1995-03-30 Kosmetische und/oder pharmazeutische Zubereitungen
DE19511637.2 1995-03-30

Publications (1)

Publication Number Publication Date
WO1996029982A1 true WO1996029982A1 (fr) 1996-10-03

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PCT/EP1996/001215 WO1996029982A1 (fr) 1995-03-30 1996-03-21 Preparations cosmetiques et/ou pharmaceutiques

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WO (1) WO1996029982A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2780278B1 (fr) * 1998-06-24 2001-01-19 Oreal Composition conditionnante et detergente et utilisation
DE19855955B4 (de) * 1998-12-04 2004-08-05 Cognis Deutschland Gmbh & Co. Kg Verfahren zur Herstellung von Amidesterquats
DE19922229A1 (de) * 1999-05-14 2000-11-16 Cognis Deutschland Gmbh Kosmetische und/oder pharmazeutische Zubereitungen
DE10154628A1 (de) * 2001-09-25 2003-04-10 Beiersdorf Ag Verwendung von Alkylglucosiden zum Erzielen oder Erhöhen der Selektivität von Reinigungszubereitungen
FR3016884B1 (fr) * 2014-01-24 2019-08-09 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Nouveau procede d'amelioration des proprietes moussantes d'une formulation de nettoyage a usage topique, nouvelles compositions de nettoyage a usage topique et leur utilisation pour nettoyer la peau, les cheveux, le cuir chevelu et les muqueuses

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0070074A2 (fr) * 1981-07-13 1983-01-19 THE PROCTER & GAMBLE COMPANY Compositions moussantes contenant des agents tensio-actifs
WO1993008250A1 (fr) * 1991-10-15 1993-04-29 Henkel Kommanditgesellschaft Auf Aktien Preparations tensioactives visqueuses aqueuses
WO1994024241A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Compositions detersives contenant du magnesium se presentant sous forme de liquide stable, de gel ou sous d'autres formes et presentant des tensioactifs a base de sulfates d'alkyle (2,3) secondaires
DE4331297A1 (de) * 1993-09-15 1995-03-16 Henkel Kgaa Stückseifen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0070074A2 (fr) * 1981-07-13 1983-01-19 THE PROCTER & GAMBLE COMPANY Compositions moussantes contenant des agents tensio-actifs
WO1993008250A1 (fr) * 1991-10-15 1993-04-29 Henkel Kommanditgesellschaft Auf Aktien Preparations tensioactives visqueuses aqueuses
WO1994024241A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Compositions detersives contenant du magnesium se presentant sous forme de liquide stable, de gel ou sous d'autres formes et presentant des tensioactifs a base de sulfates d'alkyle (2,3) secondaires
DE4331297A1 (de) * 1993-09-15 1995-03-16 Henkel Kgaa Stückseifen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
D. BALZER, N. RIPKE: "Alkylpolyglucoside - Herstellung und Verwendung", SEIFEN, ÖLE, FETTE, WACHSE-JOURNAL, vol. 118, no. 15, 1992, pages 894 - 904, XP000301747 *

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