Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions
Reexamination Certificate
1998-06-09
2001-06-26
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
C424S070110, C424S401000, C008S405000, C008S406000, C008S408000
Reexamination Certificate
active
06251378
ABSTRACT:
The present invention relates to a process for dyeing keratin fibers, and in particular human keratin fibres such as the hair, using a dye composition containing at least one oxidation dye and an oxidizing composition containing at least one oxidizing agent, the said dye composition and/or the said oxidizing composition comprising at least one ceramide type compound.
The invention also relates to the dye composition containing at least one oxidation dye and at least one ceramide-type compound used in this process.
Two main types of coloration of keratin fibres exist: direct coloration using direct dyes and/or pigments which are coloured molecules giving the fibres a temporary colour which fades after a few washes, and so-called “oxidation dyeing” coloration using oxidation dye precursors and an oxidizing agent which gives the fibres a fast colour.
In the context of oxidation dyeing, dye compositions are generally used containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds, generally known as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise, by a process of oxidative condensation, to coloured compounds and dyes.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indoline compounds.
The variety of molecules used in oxidation bases and couplers allows a wide variety of colours to be obtained.
As has been seen above, oxidation dyeing allows long-lasting dyeing of the hair; however, it is generally carried out under conditions which result in appreciable degradation of the keratin fibres. The reason for this is that the presence of an oxidizing agent and a generally very alkaline medium results in degradation of the keratin fibres, often making them coarse and brittle.
The so-called “permanent” dyeing obtained with the aid of oxidation dyes should moreover satisfy a certain number of requirements. Thus, it must allow shades to be obtained in the desired intensity and should show good fastness to external agents (light, bad weather, washing, permanent-waving, perspiration, rubbing).
The Applicant has now discovered, entirely surprisingly and unexpectedly, that the use of ceramide-type compounds in compositions for the oxidation dyeing of keratin fibres makes it possible to give these fibres a coloration which shows better resistance over time to the various external attacking factors to which the fibres may be subjected.
This discovery forms the basis of the present invention.
The subject of the present invention is thus a process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that the following are applied to these fibres:
at least one dye composition containing, in a medium which is suitable for dyeing, at least one oxidation base chosen from bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases and para-phenylenediamines of formula (I) below, and the addition salts of these compounds with an acid:
in which:
R
1
represents a hydrogen atom or a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl, C
2
-C
4
polyhydroxyalkyl, phenyl or 4′-aminophenyl radical,
R
2
represents a hydrogen atom or a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl or C
2
-C
4
polyhydroxyalkyl radical, R
3
represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, or a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl or C
1
-C
4
hydroxyalkoxy radical,
R
4
represents a hydrogen atom or a C
1
-C
4
alkyl radical;
the colour being developed at acidic, neutral or alkaline pH using an oxidizing agent which is added, only at the time of use, to the dye composition or which is present in an oxidizing composition that is applied simultaneously or sequentially in a separate manner;
the said dye composition and/or the said oxidizing composition containing at least one ceramide-type compound.
The colorations obtained according to the dye process in accordance with the invention have excellent resistance properties both with regard to atmospheric agents such as light and bad weather and with regard to perspiration and the various treatments to which the hair may be subjected (washing, permanent-waving). Furthermore, fibres thus dyed are less damaged by the oxidation dyeing process and remain softer and less brittle than when a dyeing process which does not use a ceramide-type compound is used.
According to a particularly preferred embodiment of the dyeing process according to the invention, the dye composition described above is mixed, at the time of use, with an oxidizing composition containing, in a medium which is suitable for dyeing, at least one oxidizing agent present in an amount which is sufficient to develop a coloration. The mixture obtained is then applied to the keratin fibres and is left on them for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which the fibres are rinsed, washed with shampoo, rinsed again and dried.
The ceramide-type compounds which can be used in the dye composition and/or in the oxidizing composition are known per se. They include ceramides per se, glycoceramides, pseudoceramides and neoceramides, which may be natural or synthetic.
Ceramide-type compounds are described, for example, in patent applications DE-A-4,424,530, DE-A-4,424,533, DE-A-4,402,929, DE-A-4,420,736, WO 95/23807, WO 94/07844, EP-A-0,646,572, WO 95/16665, FR-A-2,673,179, EP-A-0,227,994, WO 94/07844, WO 94/24097 and WO 94/10131, the teachings of which are included herein by way of reference.
The natural or synthetic ceramide-type compounds which can be used according to the present invention preferably correspond to the general formula (II):
in which:
R
5
denotes:
either a linear or branched, saturated or unsaturated, C
5
-C
50
hydrocarbon radical, it being possible for this radical to be substituted with one or more hydroxyl groups, this or these hydroxyl group(s) optionally being esterified with an acid R
10
COOH, R
10
being a saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated C
1
-C
35
hydrocarbon radical, it being possible for the hydroxyl group(s) of the radical R
10
to be esterified with a saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated C
1
-C
35
fatty acid,
or a radical R″—(NR—CO)—R′, in which R denotes a hydrogen atom or a mono- or polyhydroxylated, preferably monohydroxylated C
1
-C
20
hydrocarbon radical, R′ and R″ are hydrocarbon radicals in which the sum of the carbon atoms is between 9 and 30, R′ being a divalent radical,
or a radical R
11
—O—CO—(CH
2
)
p
, in which R
11
denotes a C
1
-C
20
hydrocarbon radical, p being an integer ranging from 1 to 12 inclusive;
R
6
denotes a hydrogen atom or a (glycosyl)
n
, (galactosyl)
m
, sulphogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, in which n is an integer ranging from 1 to 4 inclusive and m is an integer ranging from 1 to 8 inclusive;
R
7
denotes a hydrogen atom or a saturated or unsaturated, hydroxylated or non-hydroxylated C
1
-C
33
hydrocarbon radical, it being possible for the hydroxyl radical(s) to be esterified with an inorganic acid or with an acid R
10
COOH, R
10
having the same meanings as those indicated above, it being possible for the hydroxyl radical(s) to be etherified with a (glycosyl)
n
, (galactosyl)
m
, sulphogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, it being possible for R
7
also to be substituted with one or more C
1
-C
1
alkyl radicals; R
7
preferably denotes a C
15
-C
26
&agr;-hydroxyalkyl radical in which the hydroxyl group can optionally be esterified with a C
16
-C
30
&agr;-hydroxy acid;
R
Braida-Valerio Damarys
Laurent Florence
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal
Page Thurman K.
Seidleck Brian K.
LandOfFree
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