Cosmetics of lipophilic derivatives of amino deoxyalditols,...

Details Cosmetics of lipophilic derivatives of amino deoxyalditols,... Cosmetics of lipophilic derivatives of amino deoxyalditols,...

1998-12-01

2001-04-03

Hollinden, Gary E. (Department: 1619)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S061000, C424S064000, C424S450000, C424S701000, C424S706000, C424S707000

Reexamination Certificate

active

06210691

ABSTRACT:

The subject of the present invention is the use in cosmetics of lipophilic derivatives of amino deoxyalditols, and cosmetic compositions containing one or more of these derivatives.
It is known that mammalian hairs contain a certain number of lipid compounds the structure and distribution of which are not yet fully defined. Along with apolar lipids secreted by the sebaceous glands and for a long time considered to be the only lipids present on the hairs, the presence of other, polar lipids has been demonstrated; among these are cholesterol sulfate, fatty acids and fatty alcohols. These polar compounds have long evaded the investigations of researchers, probably due to their very low solubility in the usual extraction solvents, based on chloroform, methanol and hexane. Their extraction is so difficult that it is even suspected by some that (for some of them) they are covalently bonded to the cell surfaces (P. W. WERTZ. Lipids 23 No. 9 (1988) 878-881).
In man, frequent washing, wear, climatic aggressions and certain cosmetic treatments to which the hair, the eyelashes and the beard are subjected are responsible for the decrease in the esthetic properties of the hairs in general.
It was thus seen to be necessary in the cosmetics field, and in particular for compositions for treating the hair, to repair the damage suffered by the provision of polar lipid products which, on account of their very low solubility in water, will not be removed during washing, even more so since their strong polarity will allow them to become associated with the very structure of the hair, this case not being possible with weakly polar or non-polar compounds of waxy type which are often recommended for improving the condition of the hair.
Certain compounds obtained by extraction from animal or plant tissues have already been recommended for this type of application. In particular, products such as ceramides have been described in the document EP-A-278 505. However, the difficulty in obtaining them in industrial amounts with a sufficient degree of purity makes the use of these compounds unattractive.
Document WO 92/05764 describes shampoo compositions containing at least 1% by weight of a surface-active agent chosen from polyhydroxylated fatty acid amides corresponding to the formula:
in which R
1
represents hydrogen, a C
1
-C
4
carbon/hydrogen-based radical, 2-hydroxyethyl, 2-hydroxypropyl or mixtures thereof, and preferably the methyl radical; R
2
is a C
5
-C
31
carbon/hydrogen-based residue, preferably a C
7
-C
19
straight-chain alkyl or alkenyl, even better a C
9
-C
17
straight-chain alkyl or alkenyl, and most particularly a C
11
-C
15
straight-chain alkyl or alkenyl, or mixtures thereof; and Z is a polyhydroxylated carbon-based residue having a linear carbon/hydrogen-based chain with at least 3 hydroxyls attached to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) of the latter. The polyhydroxylated fatty acid amides used as surface-active agents in the shampoo compositions of document WO 92/05764 must, on account of their detergent properties, have an acceptable solubility in water, and it is consequently recommended to use polyhydroxylated fatty acid amides having C
12
-C
18
R
2
substituents, which give materials having the best compromise between the ease of manufacture, the solubility in water and the detergent activity.
It was thus seen to be necessary to search for fully defined synthetic compounds which are solid at the temperatures of use, in order to restructure the hairs without giving them an undesirable oily appearance, and which furthermore are insoluble in water alone but may be placed on the hair using a formula which is essentially aqueous. After being placed on the hair, these compounds will have to provide excellent properties thereto, such as untangling, shine, liveliness and pleasant feel.
The Applicant has found that compounds corresponding particularly well to the above set of criteria were lipophilic derivatives of amino deoxyalditols and more particularly nonionic compounds of linear polyol type combined with a long fatty chain, the two sequences of these amphiphilic compounds being linked by functional groups which are themselves highly polar, of amide or carbamate type.
Furthermore, these compounds proved to be advantageous in the formulation of compositions for buccodental and body hygiene.
Consequently, one subject of the present invention is the use of the above derivatives in cosmetic compositions.
The subject of the invention is also the cosmetic compositions containing such compounds, as well as their application for treating keratinous substances such as the skin or the hair, and for buccodental hygiene.
The subject of the invention is also novel lipophilic derivatives of amino deoxyalditols, of carbamate type, which may be used in the compositions according to the invention.
Other subjects of the invention will become apparent on reading the description and the examples which follow.
The lipophilic derivatives of amino deoxyalditols used in accordance with the invention in cosmetic compositions, in particular for treating the skin, the hair or for buccodental hygiene, are characterized in that they correspond to the general formula:
in which R
1
is a saturated linear C
14
-C
40
aliphatic radical;
R
2
is a hydrogen atom or a linear C
1
-C
6
alkyl radical;
X is an oxygen atom or a methylene radical; and
n is an integer from 1 to 5, with the proviso that when X is a methylene radical R
1
is a saturated linear C
19
-C
39
aliphatic radical.
Some of the compounds corresponding to the general formula (I) above are known. In particular, U.S. Pat. Nos. 1,985,424 and 2,703,798 describe amides corresponding to this general formula. However, the only compounds described correspond to short or medium-length lipophilic chains limited to 18 carbon atoms.
U.S. Pat. No. 2,040,997 describes carbamates corresponding to the formula (I) above. These carbamates correspond to the general formula
in which R is an aliphatic radical containing polyhydroxy substitutions, X is a hydrogen atom or an alkyl radical and A is an aliphatic hydrocarbon radical having 8 or more carbon atoms. A preferably represents a straight-chain alkyl group having 10 to 20 carbon atoms. The carbamates used as synthetic intermediates are illustrated only by the sole dodecyl compound.
In the formula (I) above, and when X represents an oxygen atom, R
1
represents a saturated linear C
14
-C
40
, preferably a C
14
-C
32
and even better a C
16
-C
22
, aliphatic radical. When X represents a methylene radical, R
1
represents a saturated linear C
19
-C
39
, preferably a C
21
-C
29
, aliphatic radical; R
2
represents a hydrogen atom or a linear C
1
to C
6
alkyl radical, preferably methyl; and n is an integer from 1 to 5 and preferably equal to 4.
Among the recommended derivatives of formula (I) there may be mentioned
1-[docosanoyl-methyl-amino]-1-deoxy-D-glucitol,
[hexadecyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol,
1-[octadecyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol,
1-[docosyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol, and
1-[tetracosanoyl-methyl-amino]-1-deoxy-D-glucitol.
There may also be mentioned the amides derived from mixtures of fatty acids or the carbamates derived from a mixture of fatty alcohols; fatty alcohols or acids may be obtained by synthesis or by extraction from natural, plant or animal waxes.
As an example, octacosanol extracted from rice seeds or from wheat and sold by the company NIPPON OILS is a mixture of C
26
-C
36
alcohols. Mixtures of C
22
- and C
24
- rich acids may be obtained, inter alia, from rice wax, carnauba wax or beeswax.
The processes for preparing the derivatives of formula (I) above are well known to those skilled in the art. It is possible, for example, to prepare the amides corresponding to the formula (I) by the method described by E. K. Hildreth, Biochem J. 207 (1982) 363.
According to this method, a mixed anhydride is prepared in a first phase by reacting an acid o

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