Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-02-24
2002-01-01
Jones, Dameron L. (Department: 1619)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S701000, C424S450000, C514S844000, C514S845000, C514S846000, C514S847000, C514S937000, C514S944000
Reexamination Certificate
active
06335024
ABSTRACT:
The present invention relates to the use of aminoalcohol derivatives containing a urea functional group in and for the preparation of cosmetic or dermatological compositions, in particular to their use as moisturizing agents in care products for the skin or as conditioning agents in hair products.
A number of amino alcohol compounds containing a urea functional group are known in the state of the art. Some have been described in particular in U.S. Pat. No. 3,135,790 and are used as emulsifying agents in paint or lacquer formulations or as synthetic intermediates. Others, such as those described in German Patent DE 1,125,905, in particular N-methyl-N-(2,3,4,5,6-pentahydroxy-n-hexyl)-N′-n-octylurea, are used as textile additives, washing agents or crosslinking agents or as emulsifiers. Some aminoalcohol derivatives containing a urea functional group are used in U.S. Pat. No. 2,891,944 for their insecticidal properties. A description has also been given, in the article
J. Med. Chem.,
31(4), 858-863, 1988, for its activity with respect to certain cancerous cells, of 3-(3-octadecylureido)-1,2-propanediol.
The inventors have discovered, surprisingly, that specific aminoalcohol derivatives containing a urea functional group, the structure of which will be defined hereinbelow, exhibited advantageous cosmetic properties, in particular moisturizing properties with respect to the skin.
This is because it was found that, by applying these products on the skin it is possible to decrease the water loss thereof and/or to increase the attachment of eater in the stratum corneum. These compounds can thus be used as moisturizing agents, in particular for human skin.
They make it possible to retain or to restore the flexibility of the skin, its elasticity, its resistance to the movement of the body and its function of barrier to the entry of toxic substances. They can thus be used in care products for dry skin or skin predisposed towards drying.
These compounds unexpectedly exhibit a very much greater barrier activity with respect to permeability to water on the skin than their carbamate or amide homologues known in cosmetics for their moisturizing properties.
The inventors have also discovered surprisingly, that the aminoalcohol derivatives containing a urea functional group according to the invention, used in hair compositions, confer a particularly soft feed on hair and facilitate the disentangling thereof. They can be used as hair conditioning agents.
The main subject of the invention thus relates to the use of aminoalcohol derivatives containing a urea functional group, which will be defined subsequently, in and for the preparation of cosmetic or dermatological compositions.
Another subject of the invention relates to the cosmetic or dermatological compositions containing these aminoalcohol derivatives containing a urea functional group.
Another subject of the invention thus relates to the use of these aminoalcohol derivatives containing a urea functional group as moisturizing agents in and for the preparation of compositions for the care of the skin.
Another subject of the invention thus relates to the use of these aminoalcohol derivatives containing a urea functional group as hair conditioning agents in and for the preparation of hair compositions.
Other subjects will become apparent in the light of the description and examples which follow.
The aminoalcohol derivatives containing a urea functional group in accordance with the invention correspond to the following general formula (I):
in which:
R
1
represents a linear or branched, saturated or unsaturated alkyl radical having from 8 to 22 carbon atoms;
R
2
represents a hydrogen atom or a linear or branched, saturated alkyl radical having from 1 to 6 carbon atoms;
R
3
represents linear or branched, monohydroxylated or polyhydroxylated, saturated alkyl group having from 1 to 10 carbon atoms.
R
1
preferably represents a linear or branched, saturated or unsaturated, C
10
-C
18
alkyl radical.
R
2
preferably represents a hydrogen or the methyl group.
R
3
preferably represents a radical:
in which n represents an integer equal to 0 to 1, m represents an integer of between 0 and 5 and Z is a monohydroxylated or polyhydroxylated alkyl radical having from 1 to 4 carbon atoms. In particular, Z is selected from the following radicals:
The more preferential R
3
radicals are selected from:
Mention may in particular be made, among the preferred compounds corresponding to the general formula (I), of:
N-dodecylaminocarbonyl-N-methyl-D-glucamine;
N-octylaminocarbonyl-N-methyl-D-glucamine;
1-dodecyl-3-(2-hydroxy-1, 1-bis(hydroxymethyl)ethyl)urea;
N-dodecylaminocarbonyl-D-glucamine;
1-(2,3-dihydroxypropyl)-3-dodecylurea;
1-dodecyl-3-(2-hydroxy-1-hydroxymethyl-1-methylethyl)urea;
1-(2-ethylhexyl)3-(2-hydroxy-1, 1-bis(hydroxymethyl)ethyl)urea;
N-(4Z)-octadec-9-enylaminocarbonyl-N-methyl-D-glucamine.
These compounds can be obtained by reaction, in a preferably polar solvent, of an aminoalcohol of formula R
2
—NH—R
3
, in which R
2
and R
3
have the same meanings as those indicated above, with an imidazolo-alkylcarboxamide compound of formula (III):
The reaction is generally carried out in an inert atmosphere in the presence of a solvent such as methanol, at the temperature corresponding to reflux of the solvent, preferably between 40 and 50° C.
The imidazoloalkylcarboxamide compounds of formula (II) are obtained according to known synthetic methods, in particular known in the following reference:
Angewandte Chemie
, International Edition, Vol. 1, No. 7, 1962 the disclosure of which is incorporated herein by reference.
The cosmetic or dermatological compositions according to the invention are characterized in that they contain, in a cosmetically or dermatologically acceptable vehicle, at least one compound of formula (I) as defined above, with the exception of the compound N-methyl-N-(2,3,4,5,6-pentahydroxy-n-hexyl)-N′-n-octylurea.
The cosmetic or dermatological compositions according to the invention preferably comprise 0.001 to 15% by weight of compound of formula (I) with respect to the total weight of the composition.
The cosmetically acceptable vehicle used in the compositions of the invention is selected from water; organic solvents compatible with a cutaneous or hair application such as acetone, isopropanol or ethanol; triglycerides of fatty acids containing 6-24 carbon atoms, glycol ethers, polyalkylene glycol esters and volatile silicones or their mixtures.
The compositions can be provided in the form of a single-phase or multi-phase aqueous or aqueous/alcoholic lotion, of a single-phase or multi-phase gel, of an emulsion, of a cream, of a vesicular dispersion of ionic or non-ionic lipids, it being possible for the said vesicles then to act as encapsulation agent for lipophilic or hydrophilic active ingredients, of a foam or of a spray.
The compositions for the care of the skin according to the invention can be provided in the form of a lotion, gel, emulsion, cream or foam to be applied on the skin.
The hair compositions can be provided in the form of a shampoo, of a conditioner of the rinse-out or leave-in type, of perming, hair-straightening, dyeing or bleaching compositions or alternatively in the form of rinse-out compositions, to be applied before or after dyeing, perming or hair-straightening or alternatively between the two stages of a perming operation or of a hair-straightening operation.
The cosmetic or dermatological compositions can, moreover, contain conventional cosmetic additives chosen from fatty substances, organic solvents, silicones, thickeners, softeners, surfactants, anionic, cationic, non-ionic or amphoteric polymers, antifoaming agents, hair conditioning agents, such as proteins, vitamins, treating agents (agents for combatting hair loss, antidandruff agents), dyes, fragrances, preservatives or propellants.
Use may more specifically be made, as fatty substance, of an oil or wax or their mixture, fatty acids, fatty alcohols, fatty acid esters, such as C
6
-C
18
fatty acid triglycerides, petrolatum, para
Blaise Christian
Philippe Michel
Tuloup Remy
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Jones Dameron L.
L'Oreal
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