Drug – bio-affecting and body treating compositions – Topical body preparation containing solid synthetic organic...
Reexamination Certificate
2000-12-14
2003-12-02
Padmanabhan, Sreeni (Department: 1617)
Drug, bio-affecting and body treating compositions
Topical body preparation containing solid synthetic organic...
C424S401000, C424S070170, C514S506000, C514S625000, C514S880000
Reexamination Certificate
active
06656458
ABSTRACT:
The present invention relates to the use of polyamino acid derivatives in a cosmetic composition to strengthen and care for keratin fibres, in particular the hair.
The present invention also relates to a “direct” or “in-situ” treatment process to strengthen and care for keratin fibres.
The expression “direct process” means the treatment of the fibres by applying to them a cosmetic composition containing, in a cosmetically acceptable vehicle, at least one pre-synthesized polyamino acid derivative.
The expression “in-situ process” means the treatment of the fibres using precursors which generate a polyamino acid derivative in these fibres.
Different classes of polyamino acids have been described, and their use is well known and widely practised, in particular for their moisturizing properties.
In this respect, Japanese patent application JP-07/041 467 discloses a class of polyamino acids of high molecular weight consisting essentially of cysteine, as well as to the process for preparing these polyamino acids.
A class of polyamino acids characterized by the presence of thiol and/or disulphide functions has also been disclosed in Japanese patent application JP-06/248 072. These polyamino acids react with the thiol linkages of keratin, thus forming disulphide bridges, which makes it possible to increase the sheen and coloration qualities of the hair.
Another class of polyamino acids has been disclosed in Japanese patent application JP-04/198 114, these compounds consisting essentially of amino acids containing neutral and acidic chains, and are generally used as moisturizing agents.
Finally, French patent application FR-2 533 209 discloses amphipathic lipopeptides consisting of a hydrophilic peptide chain and a hydrophobic chain of 8 to 24 carbon atoms, as well as to their use as emulsifiers for immiscible media or for producing liquid crystals.
After numerous studies carried out on various classes of polyamino acids, it has been found, surprisingly and unexpectedly, that one particular class of polyamino acid derivatives has considerable properties in terms of strengthening keratin fibres, resulting from the formation of a substantial deposit of polypeptide material on the surface of the keratin fibres.
The use of these polyamino acid derivatives in cosmetic hair compositions moreover makes it possible to improve the hold and volume of the hair.
One subject of the present invention is thus the use, in a cosmetic composition for strengthening keratin fibres, of at least one polyamino acid derivative of general formula (I) below:
in which:
X is —O—, —S— or —NR
3
—
R
1
represents:
(i) a hydrogen atom, and preferably
(ii) a linear or branched, saturated or unsaturated, C
1
-C
40
alkyl radical, optionally substituted with at least one hydroxyl or a radical
and/or optionally interrupted with at least one hetero atom chosen from N, O or Si, r′ and r″, which may be identical or different, being a hydrogen atom or a C
1
-C
6
alkyl radical,
R
2
represents a hydrogen atom or a C
1
-C
8
alkyl, —CH
2
C
6
H
5
, —CH
2
C
6
H
5
p—OH, —CH
2
OH, —CHOH—CH
3
or —(CH
2
)
t
—NH
2
radical, t being 3 to 5,
R
3
represents a hydrogen atom or a C
1
-C
6
alkyl radical,
R
4
represents a hydrogen atom, —NH
2
, —OH, —SH, —CHOHCH
3
, —CONH
2
,
—C
6
H
5
or —C
6
H
5
p—OH, and
n is an average number greater than 1 such that the molecular weight of the polyamino acid derivative is between 200 and 200,000, the repeating unit being either identical for the same derivative, or different, R
2
and/or R
3
then taking at least one of the other meanings given for these radicals,
or of a salt of the said polyamino acid derivative.
According to one preferred embodiment, the radical R
1
is other than a hydrogen atom.
The polyamino acids of formula (I) are known in certain cases and novel in other cases.
The process for preparing them consists of a polycondensation reaction between at least one N-carboxyanhydride or formula:
in which:
R
2
and R
3
have the same meanings as those given above for formula (I), and a nucleophilic compound of formula (III):
R
1
—XH (III)
in which R
1
and X have the same meanings as those given above for formula (I).
The N-carboxyanhydrides of formula (II) are prepared by the usual methods, by reacting a D and/or L-&agr;-amino acid with phosgene in an inert solvent such as dioxane or tetrahydrofuran (THF).
The polycondensation reaction is generally carried out at a temperature of between about 0° C. and 120° C. in an inert solvent chosen from benzene, toluene, chlorobenzene, dichloroethane, dimethylacetamide (DMAC), dimethylformamide (DMF), methyl ethyl ketone (MEK), aliphatic ethers such as ethyl ether, isopropyl ether and tert-butyl methyl ether, and cyclic ethers such as tetrahydrofuran and dioxane. However, the reaction solvent can optionally be water.
The formation of a more or less pronounced evolution of CO
2
can be observed from the start of the reaction.
After optionally cooling the reaction medium, the solvent is evaporated off and the polyamino acid derivative obtained is then dried under vacuum.
Depending on the purity obtained, a purification step such as a precipitation or a crystallization of the crude product obtained can be carried out.
In the process for preparing the polyamino acid derivative as described above, the nucleophilic compound acts as an initiator for the polycondensation reaction.
According to one preferred embodiment, the molar amount of the nucleophilic compound of formula (III) is ½-{fraction (1/3000)}, preferably ⅕-{fraction (1/2000)} per mole of the N-carboxyanhydride of formula (II).
Among the N-carboxyanhydrides of formula (II) which may be mentioned in particular are:
glycine N-carboxyanhydride,
sarcosine N-carboxyanhydride,
threonine N-carboxyanhydride,
serine N-carboxyanhydride,
valine N-carboxyanhydride,
norvaline N-carboxyanhydride,
isoleucine N-carboxyanhydride,
leucine N-carboxyanhydride,
norleucine N-carboxyanhydride,
lysine N-carboxyanhydride,
phenylalanine N-carboxyanhydride,
tyrosine N-carboxyanhydride, and
the above N-carboxyanhydrides optionally in protected form.
Among the nucleophilic compounds of formula (III) which may be mentioned in particular are amines such as 2-aminoactadecane-1,3-diol, 2-octyldodecylamine, hexylamine, oleylamine, glucamine, lysine, arginine, histidine and glutamine, alcohols in alkoxide form such as sodium methoxide, and thiols such as cysteine.
The compositions according to the invention can be in various forms and can contain the polyamino acid derivative in a proportion generally of between 0.001% and 30% and preferably between 0.01% and 15% by weight relative to the total weight of the composition.
According to a first embodiment of the compositions according to the invention, they are in the form of a shampoo or a pre- or post-shampoo care composition for strengthening keratin fibres.
The cosmetically acceptable vehicle for these compositions is either an aqueous medium or an aqueous-alcoholic medium containing an alcohol such as ethanol or isopropanol.
The compositions in the form of a shampoo also contain at least one anionic, nonionic, zwitterionic, amphoteric or cationic surfactant.
The proportion of surfactant is generally between 0.01% and 50% by weight, but preferably between 0.05% and 30% by weight, relative to the total weight of the composition.
When a surfactant of the nonionic type is used, it is generally used in a proportion of between 0.1% and 40% by weight, and preferably between 1% and 20% by weight, relative to the total weight of the composition.
On account of the weaker detergent power of the surfactants of cationic type, they are used more particularly in the pre- or post-shampoo care compositions.
The surfactants which can be used in the compositions according to this embodiment are well known in the prior art and have been described in particular in patent FR-2 728 163.
These pre- or post-shampoo care compositions can also contain a conditioner.
As conditioners which can be used in the compositions according to the inven
Blaise Christian
Philippe Michel
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Padmanabhan Sreeni
Wells Lauren Q.
LandOfFree
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