EP0689420A1

EP0689420A1 - Detergent mixtures with improved avivage properties

Info

Publication number: EP0689420A1
Application number: EP94911888A
Authority: EP
Inventors: Hermann Hensen; Holger Tesmann; Jörg KAHRE; Reinhard Müller; Wolfhard Scholz
Original assignee: Henkel AG and Co KGaA
Current assignee: Henkel AG and Co KGaA
Priority date: 1993-03-24
Filing date: 1994-03-15
Publication date: 1996-01-03
Also published as: JPH08508021A; WO1994021226A1; DE4309568A1

Abstract

Detergent mixtures containing a) polyhydroxy fatty acid amides of formula (I) in which R<1>CO stands for an aliphatic acyl group with 6-22 carbon atoms, R<2> for hydrogen, an alkyl group or an hydroxyalkyl group with 1-4 carbon atoms and [Z] for a linear or branched polyhydroxyalkyl group with 3-10 carbon atoms and 3-10 hydroxyl groups, b) monomer cationic surfactants and, as needed, c) oily substances, improve the wet and dry combability of hair and are suited for producing aqueous hair treatment agents.

Description

Detergent mixture with improved softening properties

Field of the Invention

The invention relates to detergent mixtures containing polyhydroxyfatty acid amides, monomeric cationic surfactants and, where appropriate, oil bodies, hair treatment compositions which contain these mixtures and the use of the mixtures for the production of hair treatment compositions.

State of the art

Modern hair treatment and hair care products usually contain polymeric cationic surfactants, the task of which is to improve the combability of the strands of hair and to provide an antistatic finish. The effectiveness of the cationic polymers is usually improved in a synergistic manner by the selection of further surfactant components.

For example, JP-A 01/144 497 (Shiseido) discloses hair shampoos which, in addition to cationic polymers and quaternary ammonium compounds, contain alkyl polyglucosides and anionic surfactants. In DE-A 30 18 600 (L'Oreal) a hair shampoo is proposed in Example 16, which besides cationic starch also contains alkyl polyglucosides and saponins. Finally, EP-AI 0 337 354 relates to mild surfactant mixtures containing alkyl polyglucosides and cationic polymers.

The synergistic effect of cation polymers and alkyl polyglucosides is thus well known from the literature. For ecological reasons, however, there is a need among manufacturers of cosmetic products to exchange polymeric cationic surfactants for corresponding monomeric substances which have more advantageous biodegradation behavior. When using monomeric cationic surfactants together with alkyl polyglucosides in the known formulations of the prior art, however, it can be observed that there is no synergistic improvement in combability; in many cases, the application properties are even more negatively influenced.

The object of the invention was therefore to provide new detergent mixtures based on monomeric cationic surfactants, which have an advantageous hair conditioner and also have a high dermatological and ecotoxicological compatibility.

Description of the invention

The invention relates to detergent mixtures with improved softening properties, containing a) polyhydroxy fatty acid amides of the formula (I)

R2

I R1_C0-N- [Z] (I)

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 [ZJ for a linear or branched polyhydroxyalkyl radical with 3 to 10 carbon atoms and 3 to 10 Hydroxyl groups,

b) monomeric cationic surfactants and optionally

c) oil body.

Surprisingly, it has been found that mixtures of polyhydroxy fatty acid amides, in particular fatty acid N-alkylglucamides, and monomeric cationic surfactants show excellent hair conditioner and this effect can be significantly increased by the use of oil bodies. The mixtures are particularly kind to the skin and readily biodegradable.

Polydroxy fatty acid amides

The polyhydroxy fatty acid amides 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 a fatty acid chloride can be obtained. With regard to the processes for their preparation, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798, as well as international patent application WO 92/06984.

The detergent mixtures according to the invention preferably contain polyhydroxy fatty acid amides of the formula (I) in which R ^ O is an acyl radical having 12 to 22 carbon atoms, R ^{2 is} hydrogen or a methyl group, and [Z] is a reduced glucose radical. The preferred polyhydroxy fatty acid amides are therefore fatty acid N-alkylglucamides, as represented by the formula (II):

R ² OH OH OH

I I I I

R ¹ CO-N-CH2-CH-CH-CH-CH-CT2θH (II)

I.

OH

Preferably used as polyhydroxy fatty acid amides are fatty acid N-alkylglucamides of the formula (II) in which R ^{2 represents} hydrogen or a methyl group and R ^ -CO represents the acyl radical of lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid , Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachinic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures. Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent ones are particularly preferred Acylation with lauric acid or Ci2 / 14 ^-K ° cos fatty acid or a corresponding derivative can be obtained.

Monomeric cationic surfactants

Examples of suitable monomeric cationic surfactants are quaternary ammonium compounds (QAC) of the formula (III)

R5

1 ⁺

[R ³ -NR ⁴ ] X- (III)

I R6

in the R ^ for an optionally hydroxy-substituted alkyl and / or alkenyl radical with 6 to 22 carbon atoms, R ⁴ for R3 or an alkyl radical with 1 to 5 carbon atoms and R5 and R *> independently of one another for alkyl radicals with 1 to 5 carbon atoms and X represents halogen, alkyl sulfate or alkyl phosphate.

The QAC are known substances which can be obtained by the relevant preparative organic chemistry processes. One method for their preparation consists, for example, in quaternizing tertiary amines with methyl chloride or dimethyl sulfate.

Typical examples of QAV suitable for the purposes of the invention are stearyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride (Dehyquart ( ^R) A, Henkel), dicetyldimethylammonium chloride or 2-hydrσxycetyl-2-hydroxyethyldimethylammonium chloride (Dehyquart ^(R) E, Henkel). Those QAV are preferably used in which R ^ for an optionally hydroxyl-substituted alkyl radical with 16 to 18 carbon atoms, R ^{4 represents} R ^, a methyl or hydroxyethyl group, R5 and R> represents a methyl group and X represents chloride or methyl sulfate.

Another group in the sense of the invention of suitable monomeric cationic surfactants are the ester sulfates of the formula (IV)

R8

1 ⁺ [R ⁷ CO- [EO] _x -OCH2CH2-N-CH2CH2θ- [EO] _x -COR ⁷ ] T "(IV)

I CH ₂ CH2θ- [EO] _z H

in the R ⁷ CO for an aliphatic, optionally hydroxy-substituted acyl radical having 12 to 22 carbon atoms and 0 or 1 double bond, R ^ for a methyl group or a polyethylene glycol ether chain with 1 to 5 ethylene oxide units, x, y and z for 0 or in Sum of numbers from 1 to 5 and Y stands for halogen, alkyl sulfate or alkyl phosphate.

Ester quats are technical mixtures of optionally ethoxylated mono- and difatty acid triethanolamine esters which are quaternized with ethylene oxide, alkyl halides, dialkyl sulfates or dialkyl phosphates. They are also known substances. Ester quats are preferably used which are derived from palm, coconut or tallow fatty acids with an iodine number in the range from 0 to 40 and have a degree of esterification from 1.5 to 1.9. The degree of ethoxylation can be 0 or 1 to 5, preferably 1 to 3. Esterquats of the formula (IV) in which R8 stands for a methyl group or a polyethylene glycol chain with 1 to 3 ethylene oxide units and Y for chloride or methyl sulfate are particularly suitable for technical reasons. A methyl-quaternized dipalm, dicocoate or ditallow fatty acid triethanolamine ester (Dehyquart ( ^R ) AU36, Pulcra / Barcelona) is particularly preferred.

oil body

Suitable oil bodies are, for example, fatty oils, fatty acid esters, Guerbet alcohols, dialkylcyclohexanes, dialkyl ethers, paraffinic hydrocarbons and silicone oils.

Fatty oils are to be understood as synthetic, but preferably natural triglycerides which contain a high proportion of unsaturated fatty acids and have an iodine number in the range from 100 to 170. Typical examples are rapeseed and sunflower oil from new cultivation, peanut oil, cottonseed oil, coriander oil, olive oil, meadowfoam oil, avocado oil, almond oil and nut oil.

Suitable fatty acid esters are compounds of the formula (V),

R ⁹ CO-OR ¹⁰ (V) in which R ^ CO stands for an aliphatic, linear or branched, optionally hydroxy-substituted acyl radical having 6 to 22 carbon atoms and R ¹ ^ for an alkyl and / or alkylene radical with 1 to 22 carbon atoms.

Typical Beiεpiel εind esters of fatty acids, auεgewählt auε the group of Capronεäure, Caprylεäure, Iεononanεäure, caprylic acid, undecanoic acid, Laurinεäure, isotridecanoic acid, myristic acid, Palmitinεäure, palmitoleic acid, stearic acid, isostearic acid, oleic acid, nolsäure elaidic acid, petroselinic acid, Li, linolenic acid, elaeostearic , Ricinoleic acid, 12-hydroxystearic acid, arachinic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, with alcohols, selected from the group consisting of methanol, ethanol, n-propanol, i-proponal, butanol, pentanol , Hexanol, heptanol, octanol, 2-ethylhexanol, capinal alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, ricinolyl alcohol, behenyl alcohol and erucyl alcohol ε and mixtures of these are formed technically. It is particularly preferred to use esters of isononanoic acid and Ciß / ig-fatty acids with i-propyl alcohol or cetylstearyl alcohol.

Guerbet alcohols are compounds of the formula (VI)

CH2OH

I.

CH ₃ CH ₂ (CH2) _Z CH- (CH2) _Z _2CH2CH3 (VT) in which z stands for numbers from 6 to 12.

These are primary, branched alcohols which are prepared in a known manner by base-catalyzed dimerization of fatty alcohols. Typical examples are 2-hexyldecanol, 2-0ctyldodecanol and 2-decyltetradecanol.

The dialkylcyclohexanes are known substances that can be obtained by relevant processes in preparative organic chemistry. An example of their preparation consists, for example, in subjecting dialkyl aromatics (ortho / meta / para-xylene) from the BTX fraction of the petroleum to a catalytic hydrogenation.

The dialkylcyclohexanes in question follow the formula (VII)

R ¹³ - [C] -R ¹² (VII)

in which R ¹¹ and R ² independently of one another are alkyl radicals having 1 to 12 carbon atoms and [C] is a cyclohexyl radical. Typical examples are dimethylcyclohexane, diethylcyclohexane, methylethylcyclohexane, dipropylcyclohexane, di-n-butylcyclohexane, di-tert.butylcyclohexane, di-2-ethylhexylcyclohexane and in particular di-n-octylcylohexane.

Dialkylethers are compounds of the formula (VTII)

_R 13_o-R ¹⁴ (VTII) in which R ¹³ _and R ¹⁴ independently of one another represent alkyl radicals having 6 to 22 carbon atoms.

These are also known substances that can be obtained by the relevant methods of preparative organic chemistry. Processes for their preparation, for example by condensation of fatty alcohols in the presence of p-toluenesulfonic acid, are described, for example, in Bull.Soc. Chim.France, 333 (1949), DE-Al 40 39 950 (Hoechst) and DE-Al 41 03 489 (Henkel) are known. From the point of view of application technology, symmetrical dialkyl ethers are preferred which have 6 to 12 carbon atoms in the alkyl radicals. Dialkyl ethers of the formula (VTII), in which R ¹³ _and R ^{14 represent} octyl and / or 2-ethylhexyl radicals, have a particular spreading capacity. The preferred di-alkyl ethers in the sense of the invention are thus di-n-octyl ether and di-2-ethylhexyl ether.

Paraffin hydrocarbons are to be understood as known technical alkane mixtures, as are usually used as oil bodies in cosmetic products. These are preferably thin liquid paraffins which have a density of 0.81 to 0.875.

Finally, the term silicon oil encompasses the group of polyorganosiloxanes in which silicon atoms are linked in a chain and / or network manner via oxygen atoms and the remaining valences are saturated by alkyl groups. Typical examples of silicone oils which can be used as suitable oil bodies are cosmetics in perfume. .62, 232 (1986). The polyhydroxy fatty acid amides and the monomeric cationic surfactants can usually be used in a weight ratio of 1: 3 to 3: 1, preferably 1: 2 to 2: 1. The same ratios are also recommended for the use of polyhydroxy fatty acid amides and oil bodies.

Aqueous hair treatment agents

Another object of the invention relates to aqueous hair treatment compositions containing

15 to 30% by weight of polyhydroxy fatty acid amides,

40 to 70% by weight of monomeric cationic surfactants and

15 to 30 wt .-% oil body

- in each case based on the proportion of solids - and, if appropriate, further customary auxiliaries and additives.

In this context, hair treatment agents are in particular hair rinses and hair shampoos as well as "two-in-one" combinations of both products, which give the hair combability and shine and are also intended to reduce the anti-static charge.

Auxiliaries and additives

In addition to the polyhydroxy fatty acid amides, the cationic surfactants and, if appropriate, the oil bodies, the detergent mixtures according to the invention and the harbor treatment agents can also be used in minor amounts of other surfactants. Typical examples are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, ether carboxylic acids, alkyl amido betaines or protein fatty acid condensates.

As auxiliaries and additives, emulsifiers such as alkoxylated fatty alcohols or sorbitan esters are also suitable. Substances such as polyethoxylated lanolin derivatives, lecithin derivatives 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, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone and also polyvinyl alcohol and ammonium chloride. Biogenic active substances are, for example, plant extracts, protein hydrolyzates and vitamin complexes. Common film formers are, for example, 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 dietearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters. Substances suitable and approved for cosmetic purposes can be used as dyes, as described, for example, in the publication "Cosmetic Dyes" of the Dye Commission of the German Research Foundation. shaft, 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 make up 0 to 50, preferably 5 to 40,% by weight, based on the solids content of the overall mixture.

Industrial applicability

The detergent mixtures according to the invention improve the wet and dry combability of hair, reduce the electrostatic charge, give hair a pleasant soft feel and a silky shine. The invention thus offers for the first time a teaching according to which hair treatment agents with satisfactory properties can be produced on the basis of monomeric cationic surfactants and polyhydroxy fatty acid amides.

Another object of the invention therefore relates to the use of the detergent mixtures according to the invention for the production of aqueous hair treatment compositions in which they are present in amounts of 1 to 100, preferably 5 to 70% by weight, based on the solids content of the compositions can.

The following examples are intended to explain the subject matter of the invention in more detail without restricting it. Examples

I. Substances used

XI. Ci2 / i4 lauric acid N-methylglucamide

Yl. Cetyl trimethyl ammonium chloride

Dehyquart ( ^R ) E, Fa.Henkel KGaA, Düsseldorf / FRG Y2. 2-hydroxycetyl-2-hydroxyethyldimethylammonium chloride

Dehyquart ( ^R ) A, Fa.Henkel KGaA, Düsseldorf / FRG Y3. Dipalm fatty acid triethanolamine esters, methyl quaternized

Methyl sulfate salt

Dehyquart ( ^R ) AU36, Pulcra SA, Barcelona / ES)

ZI. Paraffin oil

Z2. 2-0ctyldodecanol

Z3. Isopropyl palmitic acid

Z4. Dioctylcyclohexane

Z5. almond oil

Z6. Bavarian oil

Z7. Isononanoic acid cetyl / esteryl esters

Z8. Di-n-octyl ether

Emulsifier: cetylstearyl alcohol

Lanette ^(R) 0, Fa.Henkel KGaA, Düsseldorf / FRG

Preservative: Phenonip mixture phenoxyethanol / parabens II. Recipes

Formulations A to K are according to the invention, formulations U and V are used for comparison.

Tab. 1. : Composition of the examined recipes All figures as% by weight

Legend: K = component

All formulations also contain 3% by weight of emulsifier, 0.3% by weight of preservative and ad 100% by weight of water. III. Dry and wet combability tests

a) Dry combability

The dry combability was examined with approval of the electrostatic charge. A relative air humidity of 20% was set. The conditioning time was 12 h at 30 ° C. The measurement was carried out by tapping the load on a double Faraday cage after performing 10 combs. The error in the measurements was 2.5% on average, the statistical safety was at least 99.9%. The results of the combing work are shown in Table 2.

b) wet combability

Wet combability was investigated on brown hair (Alkinco # 6634, strand length 12 cm, strand mass 1 g). After the zero measurement, the strands were impregnated with 100 ml of the formulations A to J or U, V and W. After an exposure time of 5 min, the strands were rinsed out under running water (1 l / min, 38 ° C.) for 1 min. The strands were measured again and compared with the zero measurement. The error in the measurements was 2% on average, the statistical certainty was at least 99%. The results are also shown in Table 2. Tab. 2: Dry and wet combability

Legend:

Claims

Containing detergent mixtures with improved softening properties

a) polyhydroxy fatty acid amides of the formula (I)

R2

I.

R1_CO-N- [Z] (I)

in which R ^{1 is} C0 for an aliphatic acyl radical with 6 to 22 carbon atoms, R ² 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 10 carbon atoms atoms and 3 to 10 hydroxyl groups,

b) monomeric cationic surfactants and optionally

c) oil body.

Detergent mixtures according to Claim 1, characterized in that they contain polyhydroxyfatty acid amides of the formula (I) in which R ^ CO is an acyl radical having 12 to 22 carbon atoms, R ^{2 is a} hydrogen or methyl group, and [Z] is one reduced glucose residue.

Detergent mixtures according to Claims 1 and 2, characterized in that they contain quaternary ammonium compounds of the formula (III) as cationic surfactants, R5

1 ⁺

[R ³ -NR ⁴ ] X- (III)

I R6

in which R ^{3 represents} an optionally hydroxy-substituted alkyl and / or alkenyl radical with 6 to 22 carbon atoms, R ⁴ for R ³ or an alkyl radical with 1 to 5 carbon atoms and R5 and R ^ independently of one another for alkyl radicals with 1 to 5 Carbon atoms and X represents halogen, alkyl sulfate or alkyl phosphate.

Detergent mixtures according to Claims 1 and 2, characterized in that they contain alε cationic surfactants Ester¬ quats of the formula (III),

R ^β

1 ⁺ [R ⁷ CO- [EO] _x -OCT2CT2-N-CH ₂ CH2θ- [EO] _x -COR ⁷ ] Y ~ (IV)

I CH ₂ CH2θ- [EO] ₂ H

in the R CO for an aliphatic, optionally hydroxy-substituted acyl radical having 12 to 22 carbon atoms with 0 or 1 double bond, R & for a methyl group or a polyethylene glycol ether chain with 1 to 5 ethylene oxide units, x, y and z for 0 or in Sum of numbers from 1 to 5 and Y stands for halogen, alkyl sulfate or alkyl phosphate. 5. Detergent mixtures according to claims 1 to 4, characterized in that they contain oil bodies selected from the group consisting of fatty oils, fatty acid esters, Guerbet alcohols, dialkyl ethers, dialkylcyclohexanes, paraffin hydrocarbons and silicone oils.

6. Detergentsgemiεche according to claims 1 to 5, characterized in that they contain the polyhydroxyfatty acid amides and the monomeric cationic tenεides in a weight ratio of 1: 3 to 3: 1.

7. Detergentsgemiεche according to claims 1 to 6, characterized in that they contain the polyhydroxyfatty acid amides and the oil bodies in a weight ratio of 1: 3 to 3: 1.

8. Aqueous hair treatment compositions containing

15 to 30% by weight of polyhydroxy fatty acid amides,

40 to 70% by weight of monomeric cationic surfactants and

15 to 30 wt .-% oil body

- in each case based on the solids content - and, if appropriate, emulsifiers, preservatives and other customary auxiliaries.

9. Use of detergent mixtures according to claims 1 to 7 for the production of aqueous hair treatment agents.