WO1997002013A1 - Cosmetic products - Google Patents

Abstract

Novel cosmetic products are proposed, containing the following: (a1) alkyl- and/or alkenyl oligoglycosides; and/or (a2) fatty acid-N-alkylpolyhydroxyalkyl amides; and (b) hydrophobised oligopeptides, the weight ratio of (a) to (b) being between 99.5 : 0.5 and 98 : 2. These products are characterised by advantageous viscosity, synergistically improved foaming characteristics and a pleasant feel on the skin.

Description

 Cosmetic products

Field of the Invention

The invention relates to cosmetic compositions containing selected sugar surfactants, to which small amounts of hydrophobic oligopeptides are added.

State of the art

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 same applies to another group of sugar surfactants, the fatty acid N-alkylpolyhydroxyalkylamides, in particular the fatty acid N-alkylglucamides.

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.

A large number of combinations of the sugar surfactants mentioned, in particular the alkyl oligoglucosides, with other surfactants are known from the prior art literature (e.g. EP-B 0070074). An overview of B.Fabry can be found in Skin-Care-Forum, May (1995).

International patent application WO 91/14761 (Henkel) relates to liquid personal cleansers containing mixtures of alkyl oligoglucosides and protein degradation products and, if appropriate, betaine surfactants. WO 91/05802 (Henkel) also discloses hair treatment compositions which, in addition to alkyl oligoglucosides, contain vegetable protein hydrolyzates and cationic surfactants of the esterquat type. However, the above-described problem, the simultaneous improvement in the foaming power, the viscosity and the skin feel, are also unsatisfactory for solving the teachings of this prior art.

The object of the present invention was therefore to provide cosmetic agents, preferably based on alkyl To provide 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. Finally, a further object of the invention was to develop highly effective additives which develop these properties even when very small amounts are added.

Description of the invention

The invention relates to cosmetic compositions containing

(al) alkyl and / or alkenyl oligoglycosides and / or (a2) fatty acid N-alkyl polyhydroxyalkylamides and (b) hydrophobized oligopeptides

in the weight ratio (a): (b) from 99.5: 0.5 to 98: 2 and preferably 99: 1 to 98: 2.

Surprisingly, it was found that the addition of defined, very small amounts of 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

Alkyl and alkenyl oligoglycosides are known substances which follow the formula (I)

Rlθ- [G] _p (I)

in which 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. As a representative of the extensive literature, reference is made here to the documents EP-A 0301298 and WO 90/03977.

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) indicates the degree of oligomerization (DP degree), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10. While p in a given compound must always be an integer and here, above all, can assume the values p = 1 to 6, 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 3.0 are preferably used. From application From an nutritional point of view, preference is given to alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.

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. Alkyl oligoglucosides of chain length ^C 8 ^-C 10 ( ^{Dp ~} * ^to 3) are preferred, which are obtained as a preliminary step in the separation of technical Cg-Cig coconut fatty alcohol by distillation and are contaminated with a proportion of less than 6% by weight of Ci2 alcohol can as well as alkyl oligoglucosides based on technical Cg / n-oxo alcohols (DP = 1 to 3).

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

Fatty acid N-alkyl polyhydroxyalkylamides follow the formula

R3

IR ² CO-N- [Z] (II)

in the 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 and [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. With regard to the processes for their production, reference is made to US Pat. Nos. US 1985424, US 2016962 and US 2703798 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 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):

R ³ OH OH OH III

R ² CO-N-CH ₂ -CH-CH-CH-CH-CH2 ^OH (III)

I OH

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. 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. Furthermore, the polyhydroxyalkylamides can also be derived from maltose and palatinose.

Hydrophobicized oligopeptides

Examples of 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, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, behenyl alcohol, high pressure alcohol, behenyl alcohol, behenyl alcohol technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols. Technical fatty alcohols with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty alcohol are preferred. 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.

Industrial applicability

The addition of the 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. In addition, the agents according to the invention impart a pleasant feeling on the skin. Cosmetic products

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-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 e Ammonium salt polymers such as MIRAP0L ( ^R ) A-15, MIRAP0L ( ^R ) AD-1, MIRAP0L ( ^R ) AZ-1 from Miranol / US.

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.

Examples

I. Surfactants used

^A1 ) Cg / i6-alkyl oligoglucoside (Plantaren ^(R ) 2000) A2) coconut fatty acid-N-methylglucamide

Bl) Wheat protein hydrolyzate ethyl ester (Gluadin ( ^R ) AE)

B2) reaction product of polyaspartic acid (molar mass approx.

20,000) with aminoethylmorpholine B3) reaction product of polyaspartic acid (molar mass approx.

2,000) with aminoethylmorpholine

If trade names are mentioned, they are sales products from Henkel KGaA, Düsseldorf / FRG.

II. Foaming power

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:

Table 1: Foaming power and skin feel

Legend: HGf = skin feeling nb = not determined

Claims

claims 1. Containing cosmetic products (al) alkyl and / or alkenyl oligoglycosides and / or (a2) fatty acid N-alkyl polyhydroxyalkylamides and (b) hydrophobized oligopeptides in the weight ratio (a): (b) from 99.5: 0.5 to 98: 2. Composition according to claim 1, characterized in that they contain alkyl and / or alkenyl oligoglycosides of the formula (I), ^Rl O- [G] _p (I) in which R1 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. 3. Composition according to claims 1 and 2, characterized gekennzeich¬ net that they contain fatty acid N-alkylpolyhydroxyalkylamides of the formula (II) R3 I. R ² CO-N- [Z] (II) in which R ^{2 is} C0 for an aliphatic acyl radical having 6 to 22 carbon atoms, R3 for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms and [Z] represents a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups. Agents make claims 1 to 3, characterized gekennzeich¬ net that they contain as hydrophobized oligopeptides esterification products of vegetable protein hydrolyzates with an average molecular weight of 100 to 100,000 Daltons with alcohols with 1 to 4 carbon atoms. Agents make claims 1 to 3, characterized gekennzeich¬ net that they contain as hydrophobized oligopeptide reaction products polyaspartic acids with fatty alcohols with 6 to 22 carbon atoms or amines with 1 to 22 carbon atoms.