Cosmetic agents for hair and skin treatment

An agent for treatment of hair and skin, containing a quarternary ammonium compound of the formula ##STR1## in which R.sub.1 and R.sub.2 may be identical or different and denote C.sub.8 -C.sub.22 -alkyl or C.sub.8 -C.sub.22 -alkenyl, R.sub.3 denotes C.sub.1 -C.sub.3 -alkyl, x denotes a number from 1 to 3, and A.sup..crclbar. denotes the anion of C.sub.2 -C.sub.6 -carboxylic acid, which may contain 1 to 3 hydroxyl groups, or the hydrogen phosphate anion.

DESCRIPTION 
Human hair is damaged by changing exogenic influences. Damage to the hair 
structure can take place physically, for example through combing, brushing 
and back-combing, or during hair washing. Further damage is observed on 
bleaching, coloring or perming. Microbiological influences can also 
adversely affect the hair structure. In order to minimize these 
influences, it is usual to use hair-treatment agents in the form of hair 
rinses or conditioners. In addition, the combability of wet and dry hair 
is substantially improved and, at the same time, static charge is 
decreased when these preparations are used. These cosmetic agents for hair 
treatment can be used in aqueous or aqueousalcoholic solution or in the 
form of emulsions and/or suspensions. 
It is known that cationic compounds, generally quarternary ammonium 
compounds, are highly suitable for the preparation of such cosmetic agents 
for hair treatment. These surfactants have a high substantivity to hair, 
and the mono- or multimolecular film produced gives the cosmetic 
properties desired. The cationic surfactants most used for the preparation 
of hair-treatment agents belong to the group comprising the 
alkyltrimethylammonium chlorides or bromides, the dialkyldimethylammonium 
chlorides or the alkyldimethylbenzylammonium chlorides. 
In addition, water-soluble, cationic polymers are also employed, alone or 
together with the abovementioned quarternary ammonium compounds. 
However, the majority of these cationic surfactants used have a number of 
disadvantages, such as, for example, too poor combability of wet hair, 
build-up or accumulation on the hair, unfavorable dermatological or 
toxicological properties and formulation problems, i.e. insufficient 
increase in consistency. 
Surprisingly, it has now been found that agents which do not have these 
disadvantages can be prepared using the oxypropylated quarternary ammonium 
compounds shown below. The invention therefore relates to agents for 
treatment of hair and also for skin containing a quarternary ammonium 
compound of the formula 
##STR2## 
in which R.sub.1 and R.sub.2 may be identical or different and denote 
C.sub.8 -C.sub.22 -alkyl or C.sub.8 -C.sub.22 -alkenyl, R.sub.3 denotes 
C.sub.1 -C.sub.3 alkyl, x denotes a number from 1 to 3 and A.sup..crclbar. 
denotes the anion of a C.sub.2 -C.sub.6 -carboxylic acid which may 
contain 1 to 3 hydroxyl groups, or the hydrogen phosphate anion. 
In a preferred fashion R.sub.1 and R.sub.2 denote C.sub.12 -C.sub.18 
-alkyl, R.sub.3 denotes methyl, x denotes a number from 1.5 to 2.5, and 
A.sup..crclbar. denotes the anion of lactic acid, citric acid or tartaric 
acid. The quarternary ammonium compounds of the formula above can be 
prepared analogously to the process described in U.S. Pat. No. 4,409,109. 
Using these oxypropylated quarternary ammonium compounds, agents for 
treatment of hair can be prepared which, besides these, contain the 
components which are conventionally used, such as thickeners, fat 
components, preservatives, perfume oils, colorants, light screens and 
other cosmetic active compounds, emulsified or dispersed in water or 
dissolved in alcohols. The quarternary ammonium compounds described have 
the following advantages when used in conditioning hair rinses, hair 
fixatives or wave sets. 
1. Improvement in wet combability 
Combability of wet hair is tested invivo on at least 6 test subjects 
having, if possible, previously damaged hair. 
The test is carried out by washing the hair of the test subjects twice in a 
usual fashion under standardized conditions and subsequently drying 
gently. The hair of the subjects is parted in the center of the head and 
treated in each case with 10 ml of an aqueous solution containing the 
quarternary ammonium compounds in a concentration of 0.1%. The solution is 
allowed to act for 5 minutes at room temperature. The hair is subsequently 
rinsed for 2 minutes with hand-hot tap water, and, in accordance with 
practice, the excess of water is removed from the hair using hand towels. 
Using 2 identical combs, the sides to be compared are combed synchronously 
and the resistance which occurs is determined. It was shown that, when 
using the substances according to the invention, very good combability of 
wet human hair is produced compared to commercially available quarternary 
ammonium compounds. 
The combability of subsequently dried hair is also very good. The same 
applies to the so-called styling properties of the hair (see table 1) 
TABLE 1 
______________________________________ 
Combability 
Wet Dry Antistatic 
Feel of 
hair hair behavior the hair 
______________________________________ 
Cetyltrimethylammonium 
3 3 4 2 
chloride (comparison) 
Stearyldimethylbenzyl- 
2 3 2 3 
ammonium chloride 
(comparison) 
Distearylmethylpoly- 
4 4 3-4 4 
(oxypropyl)ammonium 
lactate (according to 
the invention) 
Without quarternary 
0 1 1 1 
ammonium 
______________________________________ 
4 = very good 
3 = good 
2 = moderate 
1 = poor 
0 = very poor 
2. Foaming behavior during use 
A further advantage of oxypropylated quarternary ammonium compounds is 
their freedom from foaming in aqueous dilution. This is of particular 
advantage when used in hair conditioners, since considerable foam 
formation gives the consumer the impression of the presence of residual 
amounts of shampoo, which in turn leads to time-consuming and annoying 
increased rinsing out of the hair treatment after its use. When the 
oxypropylated quarternary ammonium compounds are used, no foaming action 
is observed, in contrast to the cetyltrimethylammonium chloride which is 
usually used in practice. 
The foaming behavior can also be determined in vitro using the so-called 
foam-beating method in accordance with DIN 53 902. An aqueous solution 
containing 0.1% of the active substance and having a water hardness of 356 
ppm of CaCO.sub.3 is beaten 25 times at 20.degree. C. under standardized 
conditions. The volume of foam produced in a cetyltrimethylammonium 
chloride solution in this test is 740 cm.sup.3 whereas the oxypropylated 
quarternary ammonium compounds exhibit no foaming action. 
3. Simple formulation 
The preferred form of hair-treatment agents is a dispersion containing the 
quarternary ammonium compounds and additional thickeners, such as, for 
example, cetyl alcohol and/or stearyl alcohol. Through the use of these 
thickeners, a practical viscosity is achieved which, on the one hand, 
simplifies measuring out and, on the other hand, makes possible a better 
distribution on the hair. The incorporation of these substances is 
technologically complicated and the final viscosity in some cases only 
reaches a maximum after a relatively long time. 
In the case of the oxypropylated quarternary ammonium compounds according 
to the invention, it has been found that it is possible to produce medium 
to high-viscosity hair rinses without additional thickeners being 
necessary. For example, the following viscosities were measured as a 
function of the concentration at 20.degree. C. using a Brookfield 
viscometer: 
______________________________________ 
1% of active substance dissolved in water: 
1140 mPas 
2% of active substance dissolved in water: 
2050 mPas 
3% of active substance dissolved in water: 
2180 mPas 
5% of active substance dissolved in water: 
2810 mPas 
______________________________________ 
The oxypropylated quarternary ammonium compounds to be used according to 
the invention can be incorporated into the hair rinses in a fashion which 
is known per se. In these, 0.5-10% of the oxypropylated quarternary 
ammonium compounds alone or in combination with other quarternary ammonium 
compounds, are dispersed in water or water/alcohol mixtures together with 
the colorants, perfumes, hair-cosmetic active compounds and preservatives 
which are conventionally used. 
The substances according to the invention can also be incorporated into 
cosmetic preparations for hair which are not rinsed out with water after 
use. This concerns, for example, hair tonics, which can contain about 0.05 
to 0.1% of the oxypropylated quarternary ammonium compounds mentioned, or 
hair fixatives, wave sets in liquid, creme-form preparations, or as 
aerosols containing about 0.1 to 1% of these compounds. 
In principle, it is also possible to use the substances according to the 
invention for the preparation of cosmetic emulsions for skin care. Through 
the substantive character of the substances, improved skin feel is 
achieved after use and, simultaneously, a stabilizing action in the 
finished preparations is achieved due to the emulsifying action.

The use of the oxypropylated quarternary ammonium compounds is illustrated 
further in the examples below. Unless otherwise stated, all quantities 
refer to the weight. 
EXAMPLE 1 
Hair rinses 
3.0% of distearylmethylpoly-(oxypropyl).sub.2-3 ammonium lactate 
1.5% of cetyl/stearyl alcohol+3 moles of ethylene oxide 
3.0% of cetyl alcohol 
0.3% of perfume oil 
water to 100% 
EXAMPLE 2 
Hair treatment agent without thickener 
3.0% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
0.2% of perfume oil 
water to 100% 
EXAMPLE 3 
Wave set 
0.2% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
15% of isopropyl alcohol 
0.2% of polyvinylpyrrolidone 
0.1% of perfume oil 
water to 100% 
EXAMPLE 4 
Hair after-treatment agent 
2.0% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
1.0% of pentaoxyethylammonium lactate 
3.5% of cetyl alcohol 
water to 100% 
EXAMPLE 5 
Hair rinse 
2.5% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
0.5% of behenyltrimethylammonium chloride 
3.0% of cetyl alcohol 
water to 100% 
EXAMPLE 6 
Hair after-treatment agent in aerosol form 
0.1% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
0.1% of cetyltrimethylammonium bromide 
0.7% of cetyl/stearyl alcohol 
water to 100% 
The above mixture is transferred in a known fashion into aerosol containers 
along with a propellant. 
EXAMPLE 7 
Liquid skin-care agent 
1.0% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
3.0% of tetraethylene glycol polyglyceryl distearate 
10.0% of paraffin oil 
10.0% of isopropyl palmitate 
0.1% of perfume oil 
water to 100% 
EXAMPLE 8 
Skin-care agent in creme form 
2.0% of distearylmethylpoly(oxypropyl).sub.2-3 ammonium lactate 
6.0% of tetraethylene glycol polyglyceryl distearate 
15.0% of paraffin oil 
5.0% of isopropyl myristate 
water to 100%