WO1995028143A1

WO1995028143A1 - Hair and body care products

Info

Publication number: WO1995028143A1
Application number: PCT/EP1995/001310
Authority: WO
Inventors: Jörg KAHRE; Hermann Hensen; Rolf Wachter; Holger Tesmann; Herbert Lepper; Uwe LÜDDEMANN
Original assignee: Henkel Kommanditgesellschaft Auf Aktien
Priority date: 1994-04-18
Filing date: 1995-04-10
Publication date: 1995-10-26
Also published as: JPH09511996A; DE4413434A1

Abstract

Proposed are new hair and body care products containing (a1) alkyl and/or alcenyl oligoglycosides and/or (a2) fatty acid-N-alkyl polyhydroxy alkyl amides and (b) lecithins.

Description

Hair and body care products

Area of Erfi ιri τιc

The invention relates to new hair and body care products containing selected sugar surfactants and lecithins.

Status of τer? R <v

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.

Although cosmetic agents based on alkyl oligoglucosides or fatty acid N-alkyl glucides can be regarded as extremely skin-friendly, their use often has the subjective impression of a dull, sticky, dry or degreasing feeling on the hair and skin. The object of the invention was to provide hair and body care compositions based on the sugar surfactants mentioned which are free from the disadvantages described.

Description of the invention

The invention relates to hair and body care products containing

al) alkyl and / or alkenyl oligoglycosides and / or a2) fatty acid N-alkyl polyhydroxyalkylamides and

b) lecithins.

Surprisingly, it was found that the addition of even small amounts of lecithins to the sugar sugars mentioned gives a more pleasant feeling on the skin and gives the hair a more brilliant shine and a softer feel.

Alkyl and / or alkenyl oligonucleosides

Alkyl and alkenyl oligoglycosides follow the formula (I),

_R l__0- [G] _p (I)

in which R stands for an alkyl and / or alkenyl residue with 4 to 22 carbon atoms, G stands for a sugar residue with 5 or 6 carbon atoms and p stands for numbers from 1 to 10, and len known substances that can be obtained by the relevant methods of preparative organic chemistry. Representative of the extensive literature, reference is made here to the documents EP-Al-0 301 298 and WO 90/3977.

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. H. the distribution of mono- and oligoglycosides is present and stands for a number between 1 and 10. While p must always be an integer in a given compound and can in particular assume the values p = 1 to 6, the value p is for a specific alkyl oligoglycoside an analytically calculated quantity, 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 an application 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, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as those used for example in the hydrogenation of technical fatty acid methyl esters or in the course the hydrogenation of aldehydes from Roelen's oxosynthesis. Preference is given to alkyl oligoglucosides of chain length of Cg-Cio (DP = 1 to 3), which are obtained as first runnings in the separation of technical Cg-Cι_8 coconut oil fatty alcohol and be contaminated with a content of less than 6 wt .-% Ci2 ^-A lkohol can as well as alkyl oligoglucosides based on technical Ctj / 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 hydrogenated Cτ2 / 14 coconut alcohol with a DP of 1 to 3 are preferred.

Fatty acid N-alkyl polydroxyalkylamides

Fatty acid N-alkyl polyhydroxyalkylamides follow the formula

R3

I.

R ² CO-N- [Z] (II)

in the R2C0 for an aliphatic acyl radical having 6 to 22 carbon atoms, R ^ for hydrogen, an alkyl or - 5 -

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.

The fatty acid N-alkyl polyhydroxyalkylamides are known substances which are usually 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 one

Fatty acid chloride can be obtained. With regard to the processes for their preparation, reference is made to US Pat. Nos. 1 985 424, DS 2 016 962 and US 2703 798 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-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (III):

R3 OH OH OH

I I I I

R ² CO-N-CH2-CH-CH-CH-CH-CH2θH (III)

I OH

Glucamides of the formula (III) in which R3 is preferably used as fatty acid N-alkylpolyhydroxyalkylamides Is hydrogen or an amine group and R ² CO represents the acyl residue of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid - Acid or erucic acid or their technical mixtures. Fatty acid N-alkyl-glucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or Ci2 / 14 ^-κ ° cos fatty acid or a corresponding derivative are particularly preferred. Furthermore, the polyhydroxyalkylamides can also be derived from maltose and palatinose.

The use of the fatty acid N-alkylpolyhydroxyalkylamides is also the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-AI 0 285 768 (Hüls). French published patent application FR-A 1 580 491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, beefs which contain fatty acid N-alkylglucamides as foam regulators.

Subject of the international patent applications WO 92/6153; 6156; 6157; 6158; 6159 and 6160 (Procter & Gamble) are mixtures of fatty acid N-alkylglucamides with anionic surfactants, surfactants with a sulfate and / or sulfonate structure, ether carboxylic acids, ether sulfates, methyl ester sulfonates and nonionic surfactants. The use of these substances in a wide variety of washing, rinsing and cleaning agents is described in international patent applications WO 92/6152; 6154; 6155; 6161; 6162; 6164; 6170; 6171 and 6172 (Procter & Gamble).

lecithins

Lecithins or phosphadylcholines are glycerophospholipids which are formed from glycerol, fatty acids, phosphoric acid and preferably choline by esterification. They have a general structure according to formula (IV)

OCOR ⁴ O

I.

R ⁴ OC-OCH ₂ -CH-CH2θ-P-0-X (IV)

I o-

in which R ⁴ C0 and R ^ CO independently of one another for aliphatic acyl radicals having 12 to 22 carbon atoms and 0 and / or 1 to 4 double bonds and X for hydrogen, an R ^ CO radical or preferably a CH2CH2N ⁺ (CH3) 3 radical stand.

The naturally occurring lecithins and the closely related kephalins, to which the invention also extends, are 1,2-diacyl-sn-glycerol-3-phosphoric acids and have an o-configuration. In the case of β-lecithins, on the other hand, the phosphoric acid residue esterified with choline is bound to the central hydroxyl group of a glyceride. For the purposes of the invention, technical lecithins, preferably soybean lecithins of the formula (I), are used which are largely homologous mixtures based on fatty acids with 16 to 18 carbons. Lengenatoms, more precisely, represent palmitic acid, palmoleic acid, stearic acid, oleic acid, linoleic acid and linolenic acid. An overview of this topic can be found by M.Schneider in Fat Sei. Technol. 9 ±, 524 (1992).

The agents according to the invention can contain components a) and b) in a weight ratio of 90: 10 to 99: 1, preferably 95: 5 to 92: 8.

Hair and body care products

The agents according to the invention can contain minor amounts of further surfactants compatible with the other ingredients. Typical examples are fatty alcohol polyglycol ether sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid sarcosinates, fatty acid taurides, ether carboxylic acids, alkyl amido betaines or protein fatty acid condensates as well as to a certain extent also cationic surfactants, for example quaternary ammonium compounds, ester quaternates and also cation. The proportion of surfactant in the agents according to the invention is typically 1 to 30% by weight, calculated as solids.

Suitable oil bodies are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, lenstoffatomen preferably 8 to 10 Koh¬, esters of linear C-C20 ~ ^fatty äuren with li¬-linear Cg C2fj fatty alcohols, esters of branched CSS CISS carboxylic acids with linear C ^ 5-Ci8 fatty alcohols, esters of linear Cirj-Cig fatty acids ^with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with dihydric alcohols and / or Guerbet alcohols, triglycerides based on Cg-Cirj fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes and / or dialkyl ethers.

Also suitable as auxiliaries and additives are emulsifiers, such as alkoxylated fatty alcohols, polyglycerol fatty acid esters or sorbitan esters.

Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides can be used as overfat 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, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrro - lidon and electrolytes such as table salt and ammonium chloride. Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid. Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters. Suitable dyes for cosmetic purposes and Approved substances are used, such as those compiled in the publication "Cosmetic Colorants" of the Dye Combination of the German Research Association, published in Chem Verlag, 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 solids content of the funds, i.e. the content of surfactants and other auxiliaries and ingredients can make up 5 to 50% by weight.

Industrial applicability

The hair and body care products according to the invention impart a pleasant feeling of smoothness and give hair a brilliant shine and a soft feel. Typical examples of agents to which the essence of the invention extends are bubble baths, shower gels, hair shampoos, hair conditioners, hair conditioners and the like.

It should be pointed out that all range information is not to be understood in principle as discrete values, but rather as approximate information. This means that the effects described can still be perceived outside the specified limits, but no longer reach the high level of the scope of the invention in every respect. Examples

The application properties of formulations containing alkyl oligoglucosides with and without the addition of lecithin were examined in the so-called "half-side test". The properties of a hair shampoo for pre-wash and main wash and then in wet and dried hair are assessed by a panel consisting of 10 people with grades from 1 (excellent) to 4 (poor). The recipes are shown in Table 1; Rl and R2 are according to the invention, R3 is used for comparison. All percentages are% by weight (water ad 100%).

Table 1 Recipes used

Components Rl R2 R3%%%

Texapon ^(R ) NSO 32.0 32.0 32.0 Plantaren ^(R) 1200 5.7 5.9 6.0 Soy Lecithin 0.3 0.1

There were hair shampoos containing Ci2 / _l 4 ~ ^κ ° kosfett alcohol 2E0 sulfate sodium salt (Texapon ( ^R ) NSO) and Ci2 / 16 ~ alkyl oligoglucoside (Plantaren ( ^R ) APG 1200) - both sales products of Henkel KGaA, Düsseldorf - used. The results of the application tests are shown in Table 2. Noticeable differences exist from a difference of +/- 0.2. Table 2 Results of the half-side test

Phase parameters R1 R2 R3

Prewash foaming 2.6 2.0 2.6

Foam volume 3.8 3.6 3.8

Foam stability 2.6 2.0 2.6

Fine bubble 2.7 2.0 2.6

Creamy / skin feeling 2.9 2.9 3.1

Foam main wash 2.2 2.0 2.0

Foam volume 3.3 2.7 3.3

Foam stability 2.0 2.0 2.0

Fine bubble 2.0 2.0 2.0

Creamy / skin feeling 3.0 3.0 3.0

Rinsing assessment 2.5 2.7 2.7 Wet hair combability 3.2 2.92 3.2

Handle 3.7 3.5 3.7

Combability assessment 2.0 2.0 2.0 dry hair style 3.5 3.5 3.6

Antistatic / charging 3.6 3.5 3.6

Handle 2.7 2.3 3.0

Gloss 3.1 3.0 3.7

Claims

1. Hair and body care products containing

b) lecithins.

2. Composition according to claim 1, characterized in that they contain alkyl and / or alkenyl oligoglycosides of the formula (I),

^Rl 0- [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.

3. Composition according to claims 1 and 2, characterized gekennzeich¬ net that they contain fatty acid N-alkylpolyhydroxyalkylamides of the formula (II)

R3

IR ² CO-N- [Z] (II)

in the R2CO for an aliphatic acyl radical with 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 having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.

4. Composition according to claims 1 to 3, characterized gekennzeich¬ net that they contain lecithins of formula (IV),

OCOR ⁴ O

IR ⁴ OC-OCH2-CH-CH2θ-P-0-X (IV)

I o-

in which R ⁴ CO and R CO independently of one another for aliphatic acyl residues with 12 to 22 carbon atoms and 0 and / or 1 to 4 double bonds and X for hydrogen, an R ⁴ CO residue or a CH2CH2 ⁺ (CH3) 3 ~ residue stand.

5. Composition according to claims 1 to 4, characterized gekennzeich¬ net that they contain the components a) and b) in the ratio by weight 90: 10 to 99: 1.