DE4309568A1 - Detergent mixtures with improved softening properties - Google Patents

Description

Field of the Invention

The invention relates to detergent mixtures containing polyhy droxy fatty acid amides, monomeric cationic surfactants and counterv if necessary, oil body, hair treatment agent that this Ge contain mixtures as well as the use of the mixtures for the manufacture provision of hair treatment products.

State of the art

Modern hair treatment and hair care products contain in usually polymeric cationic surfactants, the task of which is to improve the combability of the strands of hair and for a to provide antistatic equipment. The effectiveness of the cat ionpolymers is usually selected by selecting others Improved surfactant components in a synergistic way.

For example, from JP-A 01/144 497 (Shiseido) Hair shampoos known in addition to cationic polymers and quaternary ammonium compounds alkyl polyglucosides and anio niche surfactants. In DE-A 30 18 600 (L′Oreal) a hair shampoo is proposed in Example 16, which in addition to  cationic starch also alkyl polyglucosides and saponins contains. Finally, subject matter of EP-A1 0 337 354 are mil de Surfactant mixtures containing alkyl polyglucosides and katio African polymers.

The synergistic effect of cation polymers and alkyl poly Glucosiden is thus well known from the literature. From eco logical reasons exist however with the manufacturers kosme tical products a need, polymeric cationic surfactants to be exchanged for corresponding monomeric substances that have a more favorable biodegradation behavior. When using monomeric cationic surfactants together with Alkyl polyglucosides in the known formulations of However, it is observed in the prior art that a syner there is no improvement in combability; in many Cases are even more likely to have a negative impact on the achieved technical properties.

The object of the invention was therefore to create new ones Detergent mixtures based on monomeric cationic To provide surfactants that are beneficial Hair conditioner and also have a high dermatological and have ecotoxicological tolerance.

Description of the invention

The invention relates to detergent mixtures with verbes containing finishing properties, containing

• a) polyhydroxy fatty acid amides of the formula (I) in which R ¹ CO is an aliphatic acyl radical having 6 to 22 carbon atoms, R ^{2 is} hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 to 10 Hydroxyl groups,
• b) monomeric cationic surfactants and optionally
• c) Oil body.

Surprisingly, it was found that mixtures of Polyhydroxy fatty acid amides, especially fatty acid N-alkyl glucamides, and monomeric cationic surfactants show hair relief and this effect is reflected in the Using oil bodies can significantly increase. The mixtures are particularly skin-friendly and slightly organic logically degradable.

Polyhydroxy fatty acid amides

The polyhydroxy fatty acid amides are known te substances, usually 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. Regarding the procedure too their manufacture is based on US Pat. No. 1,985 424, US 2,016,962 and US 2,703,798 and the International Patent application WO 92/06984 referenced.

The detergent mixtures according to the invention preferably contain mixtures of polyhydroxy fatty acid amides of the formula (I) in which R ¹ CO represents an acyl radical having 12 to 22 carbon atoms, R ^{2 represents} hydrogen or a methyl group, and [Z] represents a reduced glucose radical. The preferred polyhydroxy fatty acid amides are therefore fatty acid N-alkylglucamides as represented by the formula (II):

Preferably used as polyhydroxy fatty acid amides are fatty acid N-alkylglucamides of the formula (II) in which R ^{2 is} hydrogen or a methyl group and R ¹ CO is the acyl radical of lauric acid, myristic acid, palmitic acid, palm oleic acid, stearic acid, isostearic acid, oleic acid, elaidin acid, petroselinic 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 (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C _12/14 coconut fatty acid or a corresponding derivative are particularly preferred.

Monomeric cationic surfactants

Quar, for example, comes as monomeric cationic surfactants tary ammonium compounds (QAV) of the formula (III) into consideration

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

The QAV are known substances that according to the relevant procedures in preparative organic chemistry can be obtained. A method of making them consists, for example, of tertiary amines with methylchlo quaternize rid or dimethyl sulfate.

Typical examples of QAVs suitable for the purposes of the invention are stearyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride (Dehyquart® A, Henkel), dicetyldimethylammonium chloride or 2-hydroxycetyl-2-hydroxyethyldimethylammonium chloride (Dehyquart®), in which those are used R ^{3 represents} an optionally hydroxy-substituted alkyl radical having 16 to 18 carbon atoms, R ^{4 represents} R ³ , a methyl or hydroxyethyl group, R ⁵ and R ^{6 represents} a methyl group and X represents chloride or methyl sulfate.

Another group in the sense of the invention suitable mono mer cationic surfactants represent the ester quats of the formula (IV) represents

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 ⁸ for a methyl group or a poly ethylene glycol ether chain with 1 to 5 ethylene oxide units, x, y and z for 0 or in total for Numbers from 1 to 5 and Y represents halogen, alkyl sulfate or alkyl phosphate.

Esterquats represent technical mixtures of if necessary ethoxylated mono- and difatty acid triethanolamine esters, those with ethylene oxide, alkyl halides, dialkyl sulfates or Dialkyl phosphates are quaternized. It also deals with them known substances.  

Esterquats 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 R ^{8 represents} a methyl group or a polyethylene glycol chain having 1 to 3 ethylene oxide units and Y represents chloride or methyl sulfate are particularly suitable for reasons of application technology. A methylquaternized dipalm, dicoconut or ditallow fatty acid triethanolamine ester (Dehyquart® AU36, Pulcra / Barcelona) is particularly preferred.

Oil body

For example, fatty oils, fatty acid esters, Guerbet alcohols, dialkylcyclohexanes, dialkyl ethers, paraffin hydrocarbons and silicone oils.

Fat oils include synthetic, but preferably na Understand natural triglycerides that make up a high percentage contain unsaturated fatty acids and an iodine number in the loading range from 100 to 170. Typical examples are Rapeseed and sunflower oil of new breed, peanut oil, cotton seed oil, coriander oil, olive oil, meadowfoam oil, avocado oil, man del oil and nut oil.

Compounds of the formula (V) are used as fatty acid esters costume,

R ⁹ CO-OR ¹⁰ (V)

in which R ⁹ CO is an aliphatic, linear or branched, optionally hydroxy-substituted acyl radical having 6 to 22 carbon atoms and R ^{10 is} an alkyl and / or alkylene radical having 1 to 22 carbon atoms.

Typical examples are esters of fatty acids selected from the group nolsäure of caproic acid, caprylic acid, isononanoic acid, caprylic acid, undecanoic acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, Li, linolenic acid, elaeostearic , Ricinoleic acid, 12-hydroxystearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures are formed with alcohols, selected from the group consisting of methanol, ethanol, n-propanol, i-proponal, butanol, pentanol, hexanol , Heptanol, octanol, 2-ethylhexanol, Ca prinal alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, ricinolyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures. It is particularly preferred to use esters of isononanoic acid and C _16/18 fatty acids with i-propyl alcohol or cetylstearyl alcohol.

Guerbet alcohols include compounds of the formula (VI) understand,

in which z stands for numbers from 6 to 12.

These are primary, branched alcohols that in a known manner by base-catalyzed dimerization of Fatty alcohols are made. Provide typical examples 2-hexyldecanol, 2-octyldodecanol and 2-decyltetradecanol.

The dialkylcyclohexanes are known Substances by relevant procedures of the preparative organic chemistry can be obtained. An example too their production is, for example, dialkylaro maten (ortho- / meta- / para-xylene) from the BTX fraction of the Submitting petroleum to catalytic hydrogenation.

The dialkylcyclohexanes in question follow the For mel (VII)

R ¹¹ - [C] -R ¹² (VII)

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

Dialkyl ethers include compounds of the formula (VIII) understand,

R ¹³ -OR ¹⁴ (VIII)

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 which can be obtained by the relevant processes in preparative organic chemistry. Processes for their preparation, for example by condensation of fatty alcohols in the presence of p-toluenesulfonic acid, are known, for example, from Bull. Soc. Chim. France, 333 (1949), DE-A1 40 39 950 (Hoechst) and DE-A1 41 03 489 (Henkel) are known. From an application point of view, symmetrical dialkyl ethers are preferred which have 6 to 12 carbon atoms in the alkyl radicals. Dialkyl ethers of the formula (VIII), in which R ¹³ and R ^{14 represent} octyl and / or 2-ethylhexyl radicals, have a particularly rapid spreading capacity. The di alkyl ethers which are particularly preferred for the purposes of the invention are thus di-n-octyl ether and di-2-ethylhexyl ether.

Paraffinic hydrocarbons are known technical ones To understand alkane mixtures, as they are usually known as Ölkör can be used in cosmetic products. Preferably these are low-viscosity paraffins, the one Have a density of 0.81 to 0.875.

The term silicone oil finally includes the group of Polyorganosiloxanes, in which silicon atoms have oxygen atoms connected in a chain and / or network and the rest Valences are saturated by alkyl groups. Typical case games for silicone oils that use as a suitable oil body can be found in perfume cosmetics. 67, 232 (1986) lists.  

Usually the polyhydroxy fatty acid amides and monomeric cationic surfactants in a weight ratio of 1: 3 up to 3: 1, preferably 1: 2 to 2: 1. The same conditions are also recommended for use of polyhydroxy fatty acid amides and oil bodies.

Aqueous hair treatment products

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

15 to 30% by weight of polyhydroxy fatty acid amides,
40 to 70 wt .-% monomeric cationic surfactants and
15 to 30 wt .-% oil body

- each based on the solids content - as well as given if other usual auxiliaries and additives.

In this context, hair treatment agents are ins special hair rinses and shampoos as well as "two-in-one" - Combinations of both products to understand the hair Combability and shine as well as the antistatic appearance should lower the charge.

Auxiliaries and additives

In addition to the polyhydroxy fatty acid amides, the cationic ten Siden and optionally the oil bodies can the Invention contemporary detergent mixtures and the hair treatment agents in  minor amounts of other surfactants. Typical Examples are fatty alcohol polyglycol ether sulfates, monogly cerid sulfates, ether carboxylic acids, alkyl amido betaines or Protein fatty acid condensates.

Emulsifiers also come as auxiliaries and additives such as alkoxylated fatty alcohols or sorbitan esters in Be dress. Substances such as in the case of for example polyethoxylated lanolin derivatives, Lecithinderi vate and fatty acid alkanolamides are used, the the latter also serve as foam stabilizers. Ge suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and Tylosen, carboxymethyl cellulose and hydroxyethyl cellulose, also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and Polyvi nylpyrrolidone and electrolytes such as table salt and ammonium chloride. Biogenic active ingredients are, for example Plant extracts, protein hydrolyzates and vitamin complexes too understand. Common film formers are, for example Polyvinyl pyrrolidone, vinyl pyrrolidone-vinyl acetate copolyme risate, polymers of the acrylic acid series, quaternary cellulose Derivatives and similar compounds. As a preservative are suitable, for example, phenoxyethanol, formaldehyde solution, Parabens, pentadiol or sorbic acid. As a pearlescent agent come, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters in Be dress. As dyes can be used for cosmetic purposes suitable and approved substances are used, such as for example in the publication "Cosmetic Dyes with tel "by the Dye Commission of the German Research Foundation  shaft, published by Verlag Chemie, Weinheim, 1984, Pp. 81-106 are compiled. These dyes are used Lichlich in concentrations of 0.001 to 0.1 wt .-%, be pulled on the entire mixture, used.

The total proportion of auxiliaries and additives can be 0 to 50, preferably 5 to 40 wt .-% based on the solids content make up the overall mix.

Industrial applicability

The detergent mixtures according to the invention improve the wet and combability of hair, reduce the electro static charge, give hair a pleasant softness grip and a silky sheen. The invention thus offers for the first time an apprenticeship, according to which hair treatment agents with satisfactory properties based on monomers cationic surfactants and polyhydroxy fatty acid amides can put.

Another object of the invention therefore relates to the Ver use of the detergent mixtures according to the invention for the manufacture treatment of aqueous hair treatment agents, in which they in Amounts of 1 to 100, preferably 5 to 70 wt .-% - based on the solids content of the agents - may be included.

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

Examples I. Substances used

X1. C _12/14 lauric acid N-methylglucamide
Y1. Cetyl trimethyl ammonium chloride
Dehyquart® E, Henkel KGaA, Düsseldorf / FRG
Y2. 2-hydroxycetyl-2-hydroxyethyldimethylammonium chloride
Dehyquart® A, Henkel KGaA, Düsseldorf / FRG
Y3. Dipalm fatty acid triethanolamine ester, methyl-quaternized methyl sulfate salt
Dehyquart® AU36, Pulcra SA, Barcelona / ES)
Z1. Paraffin oil
Z2. 2-octyldodecanol
Z3. Isopropyl palmitic acid
Z4. Dioctylcyclohexane
Z5. almond oil
Z6. Baysilon oil
Z7. Isononanoic acid cetyl / stearyl ester
Z8. Di-n-octyl ether
- Emulsifier: cetylstearyl alcohol
Lanette® O, 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.

Table 1

Composition of the examined recipes

All figures as% by weight

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 approved by the elek trostatic charge examined. It became a right relative humidity of 20%. The con ditioning time was 12 h at 30 ° C. The measurement was carried out on the charge tap on a double Faraday cage after 10 combs. Of the Error in the measurements was 2.5% on average statistical certainty was at least 99.9%. The Results of the combing work are shown in Tab. 2.

b) wet combability

Wet combability was demonstrated on brown hair (Alkinco # 6634, strand length 12 cm, strand mass 1 g) under is looking for. After the zero measurement, the strands were 100 ml of formulations A to J or U, V and W soaked. After a contact time of 5 minutes, the strands were 1 min rinsed under running water (1 l / min, 38 ° C). The strands were measured again and with the zero measurement compared. The error in the measurements was on average 2%, statistical security was included at least 99%. The results are also in Tab. 2 shown.  

Table 2

Dry and wet combability

Claims (9)

1. Containing detergent mixtures with improved softening properties

• a) polyhydroxy fatty acid amides of the formula (I) in which R ¹ CO is an aliphatic acyl radical having 6 to 22 carbon atoms, R ^{2 is} hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 up to 10 hydroxyl groups,
• b) monomeric cationic surfactants and optionally
• c) Oil body.

2. Detergent mixtures according to claim 1, characterized in that they contain polyhydroxy fatty acid amides of the formula (I) in which R ¹ CO is an acyl radical having 12 to 22 carbon atoms, R ^{2 is} hydrogen or a methyl group, and [Z] is for one reduced glucose residue. 3. Detergent mixtures according to claims 1 and 2, characterized in that they contain quaternary ammonium compounds of the formula (III) as cationic surfactants, in which R ³ for an optionally hydroxy-substituted alkyl and / or alkenyl radical having 6 to 22 carbon atoms, R ⁴ for R ³ or an alkyl radical with 1 to 5 carbon atoms and R ⁵ and R ⁶ independently of one another for alkyl radicals with 1 to 5 carbon atoms and X represents halogen, alkyl sulfate or alkyl phosphate. 4. Detergent mixtures according to claims 1 and 2, characterized in that they contain ester quats of the formula (III) as cationic surfactants, in the R ⁷ CO for an aliphatic, optionally hydroxy-substituted acyl radical having 12 to 22 carbon atoms with 0 or 1 double bond, R ⁸ 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 total represents numbers from 1 to 5 and Y represents halogen, alkyl sulfate or alkyl phosphate. 5. Detergent mixtures according to claims 1 to 4, characterized characterized in that they contain oil bodies from the group consisting of fatty oils, fatty acid esters, Guerbet alcohols, dialkyl ethers, dialkylcyclohexanes, Paraffinic hydrocarbons and silicone oils are formed becomes. 6. Detergent mixtures according to claims 1 to 5, characterized characterized in that they are the polyhydroxy fatty acid amides and the monomeric cationic surfactants by weight Ratio 1: 3 to 3: 1 included. 7. Detergent mixtures according to claims 1 to 6, characterized characterized in that they are the polyhydroxy fatty acid amides and the oil bodies in a weight ratio of 1: 3 to 3: 1 contain. 8. Aqueous hair treatment compositions containing
15 to 30% by weight of polyhydroxy fatty acid amides,
40 to 70 wt .-% monomeric cationic surfactants and
15 to 30 wt .-% oil body
- each 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 with teln.