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WO1997002013A1 - Produits cosmetiques - Google Patents

Produits cosmetiques Download PDF

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Publication number
WO1997002013A1
WO1997002013A1 PCT/EP1996/002731 EP9602731W WO9702013A1 WO 1997002013 A1 WO1997002013 A1 WO 1997002013A1 EP 9602731 W EP9602731 W EP 9602731W WO 9702013 A1 WO9702013 A1 WO 9702013A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
carbon atoms
alcohol
fatty acid
radical
Prior art date
Application number
PCT/EP1996/002731
Other languages
German (de)
English (en)
Inventor
Jörg KAHRE
Hermann Hensen
Holger Tesmann
Rolf Wachter
Andreas Ferencz
Herbert Fischer
Celia Sander
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 WO1997002013A1 publication Critical patent/WO1997002013A1/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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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
    • 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
    • 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

Definitions

  • the invention relates to cosmetic compositions containing selected sugar surfactants, to which small amounts of hydrophobic oligopeptides are added.
  • Alkyl and / or alkenyl oligoglycosides and preferably alkyl oligoglucosides are nonionic surfactants based on renewable raw materials, which are becoming increasingly important for the production of surface-active agents owing to their excellent application properties and their particular eco-toxicological compatibility.
  • the sugar surfactants mentioned are nonionic in nature, but behave in many ways like anionic surfactants. For example, they have a strong foam capacity, but are less sensitive to water hardness and fat levels. sitiv. In addition, the sugar surfactants mentioned are sometimes difficult to thicken and do not always have a satisfactory skin feel. With regard to the development of hair and body care products, however, there is an advantageous need in the market for products such as, for example, hair shampoos or shower gels which are distinguished by a strong and stable foam both in hard water and in the presence of body fat have high viscosity and also impart a pleasantly soft skin feel.
  • the object of the present invention was therefore to provide cosmetic agents, preferably based on alkyl
  • cosmetic agents preferably based on alkyl
  • oligoglucosides and / or fatty acid N-alkylglucamides which are characterized by an improved foaming capacity, a higher foam stability, in particular also in hard water and in the presence of body fat, have an advantageously high viscosity and also have a convey a pleasantly soft feeling on the skin.
  • a further object of the invention was to develop highly effective additives which develop these properties even when very small amounts are added.
  • the invention relates to cosmetic compositions containing
  • hydrophobized oligopeptides can significantly improve the viscosity, the feeling on the skin and, in particular, the foaming power and foam stability of sugar surfactants of the alkyl oligoglucoside and fatty acid N-alkylglucamide type.
  • Alkyl and / or alkenyl oligosolvosides can significantly improve the viscosity, the feeling on the skin and, in particular, the foaming power and foam stability of sugar surfactants of the alkyl oligoglucoside and fatty acid N-alkylglucamide type.
  • Alkyl and alkenyl oligoglycosides are known substances which follow the formula (I)
  • R 1 stands 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 for numbers from 1 to 10, and which are obtained by the relevant methods of preparative organic chemistry can be.
  • 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 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, capronalcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened Ci2 / 14 _K ° kos alcohol with a DP of 1 to 3 are preferred. Fatty acid N-alkylpolyroxyalkylamides
  • R ⁇ CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R ⁇ for hydrogen, 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 hydroxyl groups stands.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • a reducing sugar with ammonia
  • an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • US Pat. Nos. US 1985424, US 2016962 and US 2703798 and international patent application WO 92/0698 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 with 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkyl polyhydroxyalkylamides are therefore fatty acid re-N-alkylglucamides, as represented by the formula (III):
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides used are glucamides of the formula (III) in which R3 is hydrogen or an alkyl group and R ⁇ 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, petroseline acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • R3 is hydrogen or an alkyl group
  • R ⁇ 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, petroseline acid
  • Fatty acid N-alkylglucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C12 / 14 ⁇ coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • hydrophobicized oligopeptides are esterification products of vegetable protein hydrolyzates with an average molecular weight of 100 to 100,000 Dalton with alcohols with 1 to 4 carbon atoms in question.
  • Typical examples are esters of degradation products of animal or vegetable proteins, for example collagen, elastin or keratin and preferably almond and potato protein and in particular wheat and soy protein with methanol or ethanol.
  • the average molecular weight of the oligopeptides is preferably 1,000 to 25,000 daltons, the degree of esterification is 5 to 95, preferably 10 to 75 and in particular 20 to 50% of theory.
  • the use of ethyl esters based on soy or wheat protein hydrolyzates with an average molecular weight of 1,000 to 25,000 daltons and a degree of esterification of 30 to 50% of theory is particularly preferred.
  • a second group of suitable hydrophobized oligopeptides are reaction products of polyaspartic acids
  • Fatty alcohols with 6 to 22 carbon atoms or amines preferably primary and / or secondary amines with 1 to 22 and in particular 2 to 12 carbon atoms.
  • Polyaspartic acids are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made, for example, to German patent applications DE-Al 4305368, DE-Al 4310503, DE-Al 4319044, DE-Al 4322410 (Bayer) and DE-Al 4322191 (BASF).
  • the polyaspartic acids which usually also have an average molecular weight in the range from 100 to 100,000 and preferably 1,000 to 25,000 daltons, can be esterified with fatty alcohols or fatty amines amidated in a manner known per se.
  • Suitable fatty alcohols are, for example, capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, iso- tridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, alaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol and technical grade alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behen
  • Suitable amines are methylamine, dimethylamine, ethylamine, diethylamine, propylamine, dipropylamine, butylamine, dibutylamine, methylethylamine, ethylpropylamine, dimethylhalopropylamine, laurylamine and, in particular, aminoethylmorpholine.
  • the degree of esterification or amidation of the polyaspartic acid derivatives can be in the range from 5 to 95%, preferably 10 to 75% and in particular 20 to 50% of theory.
  • hydrophobized oligopeptides to the selected sugar surfactants leads to the setting of an advantageously high viscosity, a synergistic improvement in the base foam and the foam resistance.
  • the agents according to the invention impart a pleasant feeling on the skin.
  • the agents according to the invention can contain further surfactants that are compatible with the other ingredients.
  • Typical examples are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid ethionates, fatty acid sarcosinates, fatty acid aurides, fatty acid glutamates, fatty acid aspartates, ether carboxylic acids, alkylamido betaine, protein hydrolysate and / or protein hydrolysate and / or.
  • the cosmetic agents such as hair shampoos, hair lotions or foam baths, can contain, as further auxiliaries and additives, emulsifiers, superfatting agents, thickeners, cation polymers, silicone compounds, biogenic agents, film formers, preservatives, dyes and fragrances.
  • Suitable emulsifiers are both known W / 0 and 0 / W emulsifiers such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters, polyglycerol polyricinoleates 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 thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, Alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, as well as higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for example, fatty alcohol ethoxylates with a restricted homolog distribution or alkyl oligoglucosaltides and electrolyte oligoglucosides Ammonium chloride.
  • 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, such as collated polypeptides Lauryldimonium hydroxypropyl hydrolyzed collagen (Lame- quat (R) L, Grunau GmbH), polyethyleneimine, cationic Sili ⁇ conpolymere such as amodimethicone or DOW CORNING 929, Dow Corning Co./US, copolymers of adipic acid and dimethylamino hydroxypropyldiethylentrimamin (Cartaretine (R) , Sandoz / CH), polyaminopolyamides as described for example in FR-A 2252840 and their crosslinked water
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones as well as amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl-modified silicone compounds.
  • 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, polyvinyl pyrrolidone, vinyl pyrrolidone-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 those which are approved and suitable for cosmetic purposes, for example as compiled 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.
  • the foaming power was determined according to the whipped foam method according to DIN 53 902 (1 g AS / 1, 15 ° d, 0.1 g sebum, 20 ° C).
  • the base foam and the foam height were determined after 20 min.
  • the skin feeling was determined subjectively by a panel consisting of 6 experienced test subjects. (+) Stands for "pleasantly soft” and (-) for "dull and dry”. The results are summarized in Table 1:

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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)

Abstract

L'invention concerne de nouveaux produits cosmétiques contenant: (a1) des alkyloligoglycosides et/ou des alcényloligoglycosides et/ou (a2) des N-alkylpolyhydroxyalkylamides d'acides gras et (b) des oligopeptides rendus hydrophobes, selon un rapport pondéral (a) : (b) de 99,5 : 0,5 à 98 : 2. Ces produits se caractérisent par une viscosité avantageuse, par un pouvoir moussant amélioré de façon synergique, ainsi que par un contact agréable pour la peau.
PCT/EP1996/002731 1995-07-01 1996-06-24 Produits cosmetiques WO1997002013A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1995124097 DE19524097A1 (de) 1995-07-01 1995-07-01 Kosmetische Mittel
DE19524097.9 1995-07-01

Publications (1)

Publication Number Publication Date
WO1997002013A1 true WO1997002013A1 (fr) 1997-01-23

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ID=7765820

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002731 WO1997002013A1 (fr) 1995-07-01 1996-06-24 Produits cosmetiques

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WO (1) WO1997002013A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0884344A3 (fr) * 1997-06-11 1999-11-17 Th. Goldschmidt AG Préparations de tensio-actifs doux avec des dérivés de copolymères d'acide polyaspartique pour nettoyage ou cosmétique
EP0884380A3 (fr) * 1997-06-11 1999-11-17 Th. Goldschmidt AG Préparations de tensio-actifs doux exempt d'alkylglycoside comprenant des dérivés d'acide polyaspartique modifié hydrophobes
DE19822601A1 (de) * 1998-05-20 1999-11-25 Goldschmidt Ag Th Hydrophob modifizierte Polyasparaginsäurederivate in O/W-Emulisonen
DE19822603A1 (de) 1998-05-20 1999-11-25 Goldschmidt Ag Th Pigmentpasten enthaltend hydrophob modifizierte Polyasparaginsäurederivate
DE19822600C2 (de) * 1998-05-20 2003-08-21 Goldschmidt Ag Th Copolymere, hydrophob modifizierte Polyasparaginsäureester mit erhöhter Molekularmasse

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991014761A1 (fr) * 1990-03-26 1991-10-03 Henkel Kommanditgesellschaft Auf Aktien Produits de lavage liquides pour le corps
DE4309567A1 (de) * 1993-03-24 1994-09-29 Henkel Kgaa Detergensgemische
WO1995005802A1 (fr) * 1993-08-20 1995-03-02 Henkel Kommanditgesellschaft Auf Aktien Melanges detersifs
DE4413434A1 (de) * 1994-04-18 1995-10-19 Henkel Kgaa Haar- und Körperpflegemittel
DE4435383C1 (de) * 1994-10-04 1995-11-09 Henkel Kgaa Kosmetische Mittel
DE4438115A1 (de) * 1994-10-26 1996-05-02 Henkel Kgaa Haarbehandlungsmittel

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991014761A1 (fr) * 1990-03-26 1991-10-03 Henkel Kommanditgesellschaft Auf Aktien Produits de lavage liquides pour le corps
DE4309567A1 (de) * 1993-03-24 1994-09-29 Henkel Kgaa Detergensgemische
WO1995005802A1 (fr) * 1993-08-20 1995-03-02 Henkel Kommanditgesellschaft Auf Aktien Melanges detersifs
DE4413434A1 (de) * 1994-04-18 1995-10-19 Henkel Kgaa Haar- und Körperpflegemittel
DE4435383C1 (de) * 1994-10-04 1995-11-09 Henkel Kgaa Kosmetische Mittel
DE4438115A1 (de) * 1994-10-26 1996-05-02 Henkel Kgaa Haarbehandlungsmittel

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