WO2004091556A2 - Dyeing composition for human keratinous fibers comprising a fluorescent dye and a particular sequestering agent, method and use - Google Patents

Dyeing composition for human keratinous fibers comprising a fluorescent dye and a particular sequestering agent, method and use

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Publication number
WO2004091556A2
WO2004091556A2 PCT/FR2004/000818 FR2004000818W WO2004091556A2 WO 2004091556 A2 WO2004091556 A2 WO 2004091556A2 FR 2004000818 W FR2004000818 W FR 2004000818W WO 2004091556 A2 WO2004091556 A2 WO 2004091556A2
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radical
atom
alkyl
composition
atoms
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PCT/FR2004/000818
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French (fr)
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WO2004091556A3 (en )
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Grégory Plos
Luc Gourlaouen
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L'oreal
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes
    • A61K2800/434Luminescent, Fluorescent; Optical brighteners; Photosensitizers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51Chelating agents

Abstract

The invention concerns a composition comprising at least one fluorescent dye and at least one particular sequestering agent, methods using said composition and device. The invention also concerns the use of a composition comprising at least one fluorescent dye and at least one particular sequestering agent for dyeing with lightening effect human keratinous fibers and more particularly artificially pigmented or dyed hair and dark skin.

Description

COLOR COMPOSITION FOR HUMAN KERATIN MATERIALS

HAVING FLUORESCENT DYE AND A sequestering agent

SPECIAL PROCESS AND USE

The invention relates to a composition comprising at least one fluorescent dye and at least one sequestering agent particular, as well as methods and apparatus embodying these compositions. It likewise relates to the use of a composition comprising at least one fluorescent dye and at least one sequestering agent especially for dyeing with a lightening effect human keratin substances, and in particular keratin fibers such as the pigmented or artificially colored hair and dark skin.

It is common for people with darker skin desire to lighten the skin and use for this purpose cosmetic or dermatological compositions containing bleaching agents.

The substances most commonly used as a bleaching agent are hydroquinone and its derivatives, kojic acid and its derivatives, azelaic acid, arbutin and its derivatives, alone or in combination with other active. However, these agents are not without their drawbacks. In particular, it is necessary to use them for long periods and in high amounts to obtain a whitening effect to the skin. There was no immediate effect on the application of compositions comprising them.

In addition, hydroquinone and its derivatives are used in amounts effective to see a whitening effect. In particular, hydroquinone is known for her vis-à-vis the melanocyte cytotoxicity.

Moreover, kojic acid and its derivatives have the disadvantage of being expensive and not being able, therefore, be used in large quantities in products in wide commercial distribution.

There is thus a need for cosmetic compositions for obtaining a clearer complexion, uniform, homogeneous, natural looking, these compositions having satisfactory transparency after application to the skin.

In the field of haircare, there are mainly two types of hair coloring.

The first is the semipermanent dyeing or direct dyeing that uses dyes capable to make the natural coloration of hair, a more or less pronounced change multidrug resistant shampoos. These dyes are called direct dyes and can be implemented in two ways. The colorings can be achieved by direct application to the keratin fibers of the composition containing the direct dye or by application of a mixture made extemporaneously a composition containing the direct dye with a composition containing an oxidizing bleaching agent which is preferably hydrogen peroxide. This is called lightening direct dyeing. The second is permanent dyeing or oxidation dyeing. This is achieved with so-called dye precursors "oxidation" which are colorless or weakly colored compounds which, when mixed with oxidizing products, at the time of use, can give rise, by an oxidative condensation process colored compounds and dyes. It is often necessary to combine the oxidation bases and couplers, one or more direct dyes to neutralize or the shades with too much of a red, orange or golden, or rather to accentuate these red hues, orange or golden .

Among the direct dyes available, nitrobenzene direct dyes are not sufficiently powerful, the indoamines, quinone dyes and natural dyes have low affinity for keratin fibers and consequently lead to colorations that are not strong enough with respect to various treatments to which hair may be subjected and in particular with respect to shampoos.

In addition, there is a need to obtain a lightening effect of human keratin fibers. This clarification is conventionally obtained by a process for bleaching hair melanin with an oxidizing system, generally consisting of hydrogen peroxide associated or not with persalts. This bleaching system has the disadvantage of degrading keratin fibers and impairing their cosmetic properties.

The present invention aims to solve the above mentioned problems and in particular to provide a composition which has good dye affinity to the keratin materials and in particular keratin fibers, good property of toughness with respect to external agents, and particularly vis-à-vis shampoos, and also allow to obtain lightening without impairing the treated material, especially the keratin fiber.

It was therefore found surprisingly and unexpectedly that the use of fluorescent dyes, particularly those in the orange range, in the presence of sequestering agents particular, allowed to achieve these goals.

The present invention therefore has for first object a composition comprising, in a cosmetically acceptable medium, at least one soluble fluorescent dye in said medium and at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and their monovalent or divalent salts alkali metal, alkaline earth metal, transition metal, ammonium or organic amine, alone or as mixtures; the composition not comprising, as fluorescent agent, 2- [2- (4-dialkylamino) phenyl ethenyl] -1-alkylpyridinium in which the alkyl radical of the pyridinium nucleus represents a methyl or ethyl radical, that of the benzene ring represents methyl and wherein the against ion is a halide.

A second object of the invention relates to a method for dyeing with a lightening effect, human keratin fibers, wherein the following steps are carried out: a) applying onto said fibers a composition according to the invention for a time sufficient to develop the desired coloration and lightening, b) optionally rinsed the fibers, c) optionally washed with shampoo and rinsed fibers, d) dried or allowed to dry the fibers.

Another object of the invention relates to the use of a composition comprising, in a cosmetically acceptable medium, at least one fluorescent dye soluble in said medium and at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and monovalent or divalent salts of alkali metal, alkaline earth, transition metal, ammonium or organic amine, alone or as mixtures for dyeing with a lightening effect human keratin substances.

A multi-compartment device for dyeing and lightening keratin fibers, comprising at least one compartment containing composition according to the invention and at least one other compartment containing a composition containing at least one oxidizing agent, is a final object of the invention.

The compositions of the invention enable in particular an increased fluorescence effect and higher clarification to that obtained with the fluorescent dye alone.

There is also improved toughness vis-à-vis washes or shampoos result.

But other characteristics and advantages of the present invention will become more apparent from reading the description and examples that follow.

Unless otherwise indicated, the limits of the ranges of values ​​that are given in the description, are included in these ranges.

As indicated previously, the composition according to the invention comprises at least a fluorescent dye and at least one sequestering particular agent. By fluorescent dye used in the context of the present invention a dye which is a molecule that colors by itself, and thus absorbs light in the visible spectrum and optionally of the ultraviolet (wavelengths ranging from nanometers 360-760 ) but, unlike a conventional dye converts the absorbed energy into fluorescent light of a longer wavelength emitted in the visible part of the spectrum.

A fluorescent dye according to the invention is to distinguish from an optical brightening agent. Optical brighteners generally called optical brighteners, or "brighteners" or "fluorescent brighteners" or "fluorescent brightening agents" or "fluorescent whitening agents" or "whiteners", or "fluorescent whiteners" in English terminology saxone are colorless transparent compounds, which do not stain because it does not absorb in the visible light, but only in the ultraviolet (wavelengths ranging from 200 to 400 nanometers), and transform the absorbed energy into light fluorescent larger wavelength emitted in the visible part of the spectrum; the color impression is then generated solely by purely fluorescent light predominantly blue (wavelengths ranging from 400 to 500 nanometers).

Finally, the fluorescent dye used in the composition is soluble in the medium of the composition. Note that the fluorescent dye is different in that a fluorescent pigment that it is not soluble in the medium of the composition.

More particularly, the fluorescent dye used in the context of the present invention, optionally neutralized, is soluble in the medium of the composition at least 0.001 g / l, more particularly at least 0.5 g / l, preferably at least 1 g / l and in one embodiment even more preferred at least 5 g / l at a temperature between 15 and 25 ° C.

Furthermore, according to one feature of the invention, the composition does not include, as a fluorescent dye, 2- [2- (4-dialkylamino) phenyl ethenyl] -1-alkylpyridinium in which the alkyl radical of the pyridinium nucleus represents methyl, ethyl, that of the benzene nucleus represents a methyl radical and wherein the against ion is a halide.

In accordance with an embodiment more particularly of the invention, the composition does not include, as a fluorescent dye compound selected from heterocyclic fluorescent dyes monocationic azo, azomethine or methine.

The fluorescent dyes preferably used according to the present invention are dyes in the orange range. 2004/091556

Preferably, the fluorescent dyes of the invention result in a maximum of reflectance lying in the wavelength range from 500 to 650 nanometers and preferably in the wavelength range from 550-620 nanometers .

Some of the fluorescent dyes according to the present invention are compounds known per se.

Examples of fluorescent dyes that may be implemented include fluorescent dyes belonging to the following families: naphtalimides; cationic coumarins or not; xanthenodiquinolizines (such as in particular sulphorhodamines); azaxanthenes; naphtholactams; azlactones; oxazines; thiazines; dioxazines; polycationic fluorescent dyes of azo, azomethine or methine type, alone or as mixtures thereof, preferably the following families: naphthalimides; cationic coumarins or not; azaxanthenes; naphtholactams; azlactones; oxazines; thiazines; dioxazines; polycationic fluorescent dyes of azo, azomethine or methine type, alone or as mixtures.

Specifically, include among them:

- Brilliant Yellow B6GL marketed by Sandoz and following structure:

-The Basic Yellow 2, or auramine O sold by Prolabo companies Aldrich or Carlo Erba and having the following structure:

monohydrochloride of 4,4 '- (imidocarbonyl) bis (N, N-dimethylaniline) - CAS number 2465- 27-2.

We can also mention the following compounds of formula: 2004/091556

in which :

R1, R2, identical or different, represent: • a hydrogen atom; "An alkyl radical, linear or branched, comprising 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted by at least one halogen atom; "An aryl or arylalkyl radical, the aryl group containing 6 carbon atoms and the alkyl radical having 1 to 4 carbon atoms; the aryl radical being optionally substituted by one or more linear or branched alkyl radicals comprising 1 to 4 carbon atoms optionally interrupted and or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one atom halogen; o R) and R2 may optionally be linked to form a heterocycle with the nitrogen atom and may comprise one or more other heteroatoms, the heterocycle optionally being substituted with at least one linear or branched alkyl radical, preferably comprising of 1 to 4 carbon atoms and optionally being interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen atom; • R1 or R2 may optionally be engaged in a heterocycle comprising the nitrogen atom and one of the phenyl carbon atoms bearing the said nitrogen atom; R3, R4, identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 4 carbon atoms;

R5, identical or different, represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical comprising 1 to 4 carbon atoms optionally interrupted by at least one heteroatom; RQ, identical or different, represent a hydrogen atom; a halogen atom; a linear or branched alkyl radical comprising 1 to 4 carbon atoms, optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom and / or substituted with at least one halogen atom; X represents:

• an alkyl radical, linear or branched containing 1 to 14 carbon atoms, or alkenyl having 2 to 14 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted by at least one halogen atom;

• a heterocyclic radical comprising 5 or 6 members, optionally substituted by at least one linear or branched alkyl radical comprising 1 to 14 carbon atoms, optionally substituted with at least one heteroatom; by at least one aminoalkyl radical, linear or branched, comprising 1 to 4 carbon atoms, optionally substituted with at least one heteroatom; by at least one halogen atom;

• an aromatic radical or diaromatic fused or unfused, separated or not by an alkyl radical comprising 1 to 4 carbon atoms, the aryl radicals being optionally substituted by at least one halogen atom or at least one alkyl radical comprising 1 to 10 carbon atoms optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom; o a dicarbonyl radical;

• the group X possibly bearing one or more cationic charges; a being equal to 0 or 1;

Y ", identical or different, representing an organic or mineral anion; n being an integer at least equal to 2 and at most equal to the number of cationic charges present in the fluorescent compound.

Recall that heteroatoms terms, represent an oxygen or nitrogen atom. Among the groups bearing such atoms, there may be mentioned inter alia hydroxy, alkoxy, carbonyl, amino, ammonium, amido (-N-CO-), carboxyl (-0-CO- or -CO-0-).

With regard to the alkenyl groups, the latter comprises one or more unsaturated carbon-carbon bonds (-C = C-), and preferably one carbon-carbon double bond.

In this general formula, the radicals R1 and R2, identical or different, represent more particularly:

• a hydrogen atom;

• an alkyl radical having 1 to 10 carbon atoms, especially 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, optionally interrupted by an oxygen atom or optionally substituted by at least one hydroxyl, amino, ammonium , a chlorine atom or fluorine atom; benzyl, phenyl, optionally substituted by an alkyl or alkoxy radical comprising 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms; with the nitrogen atom, a heterocyclic radical of the type pyrrolo, pyrrolidino, imidazolino, imidazolo, imidazolium, pyrazolino, piperazino, morpholino, morphologic, pyrazolo, triazolo, optionally substituted with at least one linear or branched alkyl radical containing 1 to 4 carbon atoms optionally interrupted and / or substituted by a nitrogen atom and / or oxygen and / or group bearing a nitrogen and / or oxygen.

With regard to the aforesaid amino or ammonium radicals, the radicals borne by the nitrogen atom may or may not be identical and represent in particular a hydrogen atom, an alkyl radical C1-C10. preferably C1-C4, an arylalkyl radical wherein, more preferably, the aryl group comprises 6 carbon atoms and the alkyl group 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.

According to an advantageous embodiment of the invention, the radicals R1 and R2, identical or different, represent a hydrogen atom; linear alkyl or branched Cj-Cβ; alkyl, C2-C6 substituted by a hydroxyl radical; alkyl, C2-Cβ bearing an amino or ammonium group; a chloroalkyl radical C2-C6; a C2-C6 alkyl radical interrupted by an oxygen atom or a group bearing (e.g., ester); an aromatic radical such as phenyl, benzyl, 4-methylphenyl; a heterocyclic radical such as the radicals pyrrolo, pyrrolidino, imidazolo, imidazolino, imidazolium, piperazino, morphologic, morphollino, pyrazolo, triazolo, optionally substituted by at least one alkyl radical Cι-C-6 or aromatic.

Preferably, Ri and R2, identical or different, represent a hydrogen atom, a linear or branched alkyl radical C -CQ such as methyl, ethyl, n-butyl, n-propyl; 2-hydroxyethyl; a radical alkyltrimethylammonium or aikyltriéthylammonium, the alkyl radical being linear C2-C6 alkyl; a (di) alkylméthylamino or (di) alkyléthylamino, the alkyl radical being linear C2-C6 alkyl; - CH2CH2CI; - (CH 2) n OCH 3 or - (CH2) n-OCH2CH3 with n integer ranging from 2 to 6; -CH2CH2-OCOCH 3; -CH2CH2COOCH3. Preferably the radicals R1 and R2, identical or different, preferably identical, represent a methyl radical, an ethyl radical.

The radicals R and R2, identical or different, may also represent a heterocyclic radical of the type pyrrolidino, 3-amino pyrrolidino, 3- (dimethyl) amino, pyrrolidino, 3- (trimethyl) amino, pyrrolidino, 2,5-dimethylpyrrolo, 1H -imidazole, 4-methyl piperazino, 4-benzyl-piperazino, morphologic, 3,5- (tert-butyl) -1H-pyrazolo, 1H-pyrazolo, 1H-1, 2,4-triazolo. Ri and R2, identical or different, may also represent be linked to form a heterocyclic ring of formulas (I) and (II):

wherein R 'represents a hydrogen atom, an alkyl radical in C1-C3 alkyl, -CH2CH2OH, -CH2CH2OCH3.

According to a more particular embodiment of the invention, R5, identical or different, represent a hydrogen atom, a fluorine or chlorine atom, a linear or branched alkyl radical comprising 1 to 4 carbon atoms optionally interrupted by an atom of oxygen or nitrogen. It is specified that the substituent R 5, if it is different from hydrogen, is preferably in position (s) 3 and / or 5 with respect to the ring carbon bearing the nitrogen substituted with the Ri and R2 groups, and preferably in position 3 relative to that carbon.

Advantageously, the radicals R 5, identical or different, represent a hydrogen atom; a linear or branched alkyl C1-C4; -O-R51 with R51 representing a linear alkyl C1-C4; -R52-O-CH3 with R52 representing a linear alkyl, C2-C3; -R53 - N (R54) 2 wherein R53 represents a linear alkyl radical C2-C3, R54, identical or different, represent a hydrogen atom or a methyl radical.

Preferably R5, identical or different, represent hydrogen, methyl, methoxy, and preferably, R5 represents a hydrogen atom.

According to a particular embodiment, the RQ radicals, identical or different, represent a hydrogen atom; a linear or branched alkyl C1-C4; -X with X being a chlorine, bromine or fluorine atom; -R61-0-R62 R61 ave c is a linear alkyl and C2-C3 Rβ2 represents methyl; -R63 _ N (R64) 2 with Rβ3 representing a linear alkyl, C2-C3, Rβ4, identical or different, represent a hydrogen atom or a methyl radical, -N (R65) 2 wherein R65, identical or different , represent a hydrogen atom, a linear alkyl, C2-C3; -NHCO RQQ with RQQ representing an alkyl radical in C1-C2, a chloroalkyl radical in C1-C2, a radical -R67 -R67-NH2 or-NH (CH3) or -R67-N (CH3) 2 or -R67-N + (CH3) 3 or -R67-N + (CH2CH3) 3 with R67 representing an alkyl radical in C1-C2.

It is specified that the substituent RQ, if different from hydrogen, is preferably in position 2 and / or 4 relative to the nitrogen atom of the pyridinium ring, preferably in position 4 with respect to said nitrogen atom. More particularly, these radicals R 6, identical or different, represent a hydrogen atom or a methyl or ethyl radical, and preferably, RQ represents a hydrogen atom.

As regards the radicals R3, R4, which may be identical or not, represent preferably a hydrogen atom, an alkyl radical comprising 1 to 4 carbon atoms, especially methyl. Preferably, R3 and R4 each represent a hydrogen atom.

As noted above, X is:

• an alkyl radical, linear or branched containing 1 to 14 carbon atoms, or alkenyl having 2 to 14 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom, at least one group bearing at least one heteroatom and or by at least one halogen atom; • a heterocyclic radical comprising 5 or 6 members, optionally substituted by at least one linear or branched alkyl radical comprising 1 to 14 carbon atoms, with at least one aminoalkyl radical, linear or branched, comprising 1 to 4 carbon atoms, optionally substituted by at least one heteroatom; by at least one halogen atom; o an aromatic or diaromatic radical fused or unfused, separated or not by an alkyl radical comprising 1 to 4 carbon atoms, the aryl radicals being optionally substituted by at least one halogen atom or at least one alkyl radical comprising 1 to 10 carbon atoms optionally substituted and / or interrupted with at least one heteroatom and / or group comprising at least one heteroatom;

• a dicarbonyl radical.

In addition, it is indicated that the group X may carry one or more cationic charges.

Thus, X can be an alkyl radical, linear or branched, comprising 1 to 14 carbon atoms, or alkenyl having 2 to 14 carbon atoms, and may be substituted and / or interrupted by one or more oxygen atoms and / or nitrogen, and / or by one or more groups bearing at least one heteroatom and / or by fluorine, chlorine. Among the groups of this type, mention may be mentioned hydroxyl, alkoxy (in particular alkyl type R radical in C1-C4), amino, ammonium, amido, carbonyl, carboxyl (-COO-, -O-CO -) with a particular type of alkyloxy radical.

Note that the nitrogen atom, if present, may be in a quaternized form or not. In this case, the one or two other radicals borne by the quaternized nitrogen atom or not, are identical or different and may be a hydrogen atom, an alkyl radical in C1-C4, preferably methyl.

According to another variant, the group X is a heterocyclic radical comprising 5 or 6 ring members, of the type imidazolo, pyrazolo, triazino, pyridino, optionally substituted with at least one linear or branched alkyl radical comprising 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms; by at least one aminoalkyl radical, linear or branched, comprising 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, optionally substituted by a group comprising at least one heteroatom (preferably a hydroxyl group) or by a halogen. Note that the amino group is preferably bonded to the heterocycle.

According to another possibility, the group X represents an aromatic radical (preferably containing 6 carbon atoms) or diaromatic condensed or not (comprising in particular from 10 to 12 carbon atoms), separated or not by an alkyl radical containing 1 to 4 carbon atoms, the aryl radicals being optionally substituted by at least at least one halogen atom and / or at least one alkyl radical comprising 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, optionally interrupted by at least one oxygen and / or nitrogen atom and / or group comprising at least one heteroatom (such as carbonyl, carboxyl, amido, amino, ammonium).

It should be noted that the aromatic radical, preferably phenyl, is connected to the groups CR3R4 via bonds in positions 1, 2; 1, 3 or 1, 4, preferably in positions 1 and 3 and 1.4. If the phenyl radical linked via bonds in positions 1,4 bears one or two substituents, this or these are preferably located in 1,4-position relative to one of the groups CR3R4. If the phenyl radical linked via bonds in positions 1 and 3, carries one or two substituents, this or these latter are preferably located at position 1 and / or 3 relative to one of the groups CR3R4.

If the radical is diaromatic, it is preferably not condensed, and comprises two phenyl radicals separated or not by a single bond (ie a carbon of each of the two cycles) or an alkyl radical, preferably of CH2 or C ( CH 3) 2 preferably, the aromatic radicals do not bear a substituent. It should be noted that said diaromatic radical is linked to the groups CR3R4 via bonds in positions 4,4 '.

Examples of suitable X moieties which may be mentioned especially linear or branched alkyl radicals comprising 1 to 13 carbon atoms such as methylene, ethylene, propylene, isopropylene, n-butylene, pentylene, hexylene; 2- hydroxypropylene, 2-hydroxy-n-butylene; alkylene radical C1-C13, substituted or interrupted by one or more nitrogen atoms and / or oxygen and / or group bearing at least one heteroatom (hyroxyle, amino, ammonium, carbonyl, carboxyl, for example) such that -CH2CH2OCH2CH2-. 1,6-dideoxy-d-mannitol, -CH 2 N + (CH3) 2CH2-, -CH2CH2N + (CH3) 2- (CH2) 6N + (CH3) 2-CH2CH2-, -CO-CO-, 3,3 diméthylpentylène, 2-acétoxyéthylène the butylènel, 2,3,4 tetraol; -CH = CH-; aromatic or diaromatic radical substituted by one or more alkyl radicals, with one or more groups bearing at least one heteroatom and / or by one or more halogen atoms, such as 1, 4-phenylene, 1, 3-phenylene , 1, 2-phenylene, 2,6-fluorobenzene, 4,4'-biphenylene, 1, 3- (5-methyl benzene), 1, 2-bis (2-methoxy) benzene, bis (4-hydroxyphenyl) methane, 3,4 benzoate, 1, 4-bis (amido methyl) phenyl; heterocyclic type radicals such as pyridine, or derivative such as 2,6-bispyridine, imidazole, imidazolium, triazine.

X represents, according to a more particular embodiment of the invention, a linear or branched alkyl radical C1-C13; -CH2CH (OH) CH2-; -CH2CH (CI) CH2-; OCOCH2- -CH2CH2-; -CH2CH2COOCH2-; -Ra-O-Rb- with Ra being a linear alkyl C 2 -C 6 and Rb represents a linear alkyl C1-C2; - Rc-N (Rd) -Re- with Rc representing an alkyl, C2-Cg, Rd representing a hydrogen atom, an alkyl radical in C1-C2, and Re is alkyl Ci-Ce; - R-N + (R) 2-Rh- with Rf is a linear alkyl, C2-C9, Rg, preferably identical, represent an alkyl radical in C1-C2, Rh represents a linear alkyl radical C- | - G6; CO-CO-.

X may further represent an imidazole radical optionally substituted with at least one alkyl radical comprising 1 to 14 carbon atoms, more particularly 1 to 10 carbon atoms, preferably 1 to 4, and for example the divalent radicals of following formula :

wherein Ri and Rj, identical or different, represent a linear alkyl radical Ci-Cβ

X may likewise be selected from divalent radicals derived from the following triazine

CH 2 CH 2

OH

Alternatively, X may represent the following aromatic divalent radicals:

In the general formula of these fluorescent compounds, Y "represents an organic or inorganic anion. If there are several Y- anions, the latter may or may not be identical.

Among the mineral anion include without limitation being implied anions from halogens, such as chlorides preferably iodides, sulfates or hydrogen sulfates, nitrates, phosphates, hydrogen phosphates, dihydrogen phosphates, carbonate, bicarbonate.

Among the organic origin anions include anions derived from mono- or polycarboxylic acid salts, sulfonic, sulfuric, saturated or not, aromatic or not, optionally substituted by at least one hydroxyl, amino, or atoms 'halogen. As non-limiting examples, suitable acetates, hydroxyactétates, aminoacetates, (tri) chloroacetates, benzoxyactétates, propionates and derivatives having a chlorine atom, fumarates, oxalates, acrylates, malonates, succinates, lactates, tartrates, glycolates citrates, benzoates and derivatives bearing a methyl or amino, alkyl sulfates, tosylates, benzenesulfonates, toluenesulfonates, etc.

Preferably, the one or more anions Y, identical or different, are selected from chlorine, sulfate, methosulfate, ethosulfate.

Finally, the number n, integer, is at least equal to 2 and at most equal to the number of cationic charges present in the fluorescent compound.

Any fluorescent compounds which have just been detailed are symmetrical compounds.

These compounds can be synthesized by reacting in a first step of α-picoline with a reagent comprising two leaving groups which may be selected from halogen atoms, preferably bromine, optionally chlorine, or type groups tolylsulfonyl or méthylesulfonyle.

This first step may take place in the presence of a solvent, although it is not required, such as dimethylformamide.

The number of moles of α-picoline is neighbor generally 2 moles to a reagent comprising the leaving groups.

In addition, the reaction is usually implemented at reflux of the reagent and / or solvent if present. The product of this first step is then contacted with a corresponding aldehyde of formula

wherein Ri, R2 and RQ have the same meanings as indicated above. Again, the reaction may be effected in the presence of a suitable solvent, preferably at reflux.

Note that the R and R 2 of the aldehyde may have the meaning given in the detailed formula before. It is also possible to implement an aldehyde to which said radicals are hydrogen atoms and perform in accordance with conventional methods, the substitution of these hydrogen atoms by suitable groups as described in the general formula when the second step is completed.

particular reference may be made to the syntheses as described in US 4,256,458.

The fluorescent dye present in the composition according to the invention preferably represent from 0.01 to 20% by weight, more preferably from 0.05 to 10% by weight, and preferably 0.1 to 5% by weight, of the total weight of the composition.

As mentioned previously, the composition further comprises at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and their alkali metal salts, alkaline earth metal, transition metal, ammonium or organic amine, alone or in mixtures.

Examples of monovalent cations include alkali metal cations such as sodium, potassium.

Mention may also be monovalent cations derived from organic amines such as primary amines, secondary or tertiary amines, or alkanolamines. Said amines contain one or more radicals, identical or different, of alkyl type, linear or branched C1-C20, optionally comprising a heteroatom such as oxygen. Also suitable are quaternary ammonium cations derived from, comprising in particular four radicals, identical or not, corresponding to the definition given above. As examples of divalent cations include divalent cations of alkaline earth metals such as calcium, magnesium, transition metals (metals having a sublayer incomplete d), particularly in oxidation state II, as the divalent cation of cobalt, iron, manganese, zinc, copper.

More particularly, sequestering agents like hydroxycarboxylic correspond to the formula (A) below: R- (CHOH) 4 -C0 2 X, wherein R is CH 2 OH or C0 2 X and X represents hydrogen or a monovalent or divalent cation. This formula encompasses all enantiomers and all diastereoisomers thereof.

As to the sequestrants of polycarboxylic type, they correspond more particularly to compounds of formula (B): R-N (Y) (CH (R ') C02X), wherein Y represents a hydrogen atom or CH (R ') Cθ2X; R represents a hydrogen atom or a group (a) -CH (Cθ2X) - (CH2) 2 NC0 X, (b) - (CH 2) n OH, (c) -CH (R ") X C0 2, (d) - (CH2) nN (COR ') - CH 2 C0 2 X, (e) - (CH 2) nN (CH2C0 2 X) CH2C02X and (f) - (CH2) n NH-CH (Cθ2X) CH2Cθ2X wherein R 'represents a hydrogen atom or a group CH2CO2X; R "represents a linear or branched alkyl C1-C30 or cyclic C3-C30, n is an integer between 1 and 5, X represents a hydrogen atom or a monovalent or divalent cation as defined under of formula (A).

According to a particular embodiment, n is equal to 2.

Among the sequestering compounds used are particularly suitable: Formula (A): gluconic acid, mucic acid (or galactaric acid), glucaric acid, mannaric acid, salts thereof, mixtures thereof; Formula (B):

• compounds comprising four carboxylic acid functional groups or salts thereof, when R represents a hydrogen atom and R 'is -CH 2 -C0 2 X, or when R represents the group -CH (C0 2 X) - (CH 2 ) 2 -C0 2 X and R 'represents a hydrogen atom;

• compounds comprising three carboxylic acid functional groups or salts thereof, when R represents the group -CH (CH 3) -C0 2 X and R 'represents a hydrogen atom or when R represents a group - (CH 2) 2 -N (COR ') - CH 2 -C0 2 X and R'. represents a hydrogen atom the methylglycine diacetic acid, N-lauroyl-N, N ', N'-tri-acetic éthylènedia ine, the iminodisuccinic acid, N, N-dicarboxymethyl L-glutamic acid, ethylenediamine N, N 'disuccinic acid, salts thereof, mixtures thereof, are preferred examples of compounds of formula (B).

It should be noted that by mixing means the mixture of several acids, one of several salts of an acid or more of them, or one of an acid and one or more salts thereof.

Preferably, the polycarboxylic acids used are of formula (B) wherein R represents a hydrogen atom or a group selected from groups (a) to (d) and (f).

The sequestering agent content is preferably 0.0001 to 20% by weight based on the weight of the composition, more particularly from 0.001 to 10% by weight relative to the weight of the composition, preferably between 0.01 and 5% by weight based on the weight of the composition.

The cosmetically acceptable medium is generally composed of water or of a mixture of water and one or more common organic solvents. Among suitable solvents, there may be mentioned more particularly, alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl ethers, monoethyl and monobutyl ethers, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol and diethylene glycol alkyl ethers such as monoethyl ether or monobutyl ether, or further polyols such as glycerol. May also be used as solvent polyethylene glycols and polypropylene glycols, and mixtures of all these compounds.

The usual solvents described above, if present, usually represent

I to 40% by weight, more preferably from 5 to 30% by weight, based on the total weight of the composition.

The pH of the composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately.

It can be adjusted to the desired value using acidifying or basifying agents.

Among the acidifying agents, mention may be made, by way of example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, acetic acid.

Among the basifying agents, mention may, by way of example, are aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine and derivatives thereof, sodium or potassium hydroxides and the compounds of formula (C) below:

R 1 \ / R 3

NWN

R 2 R

2 (C) wherein W is a propylene residue optionally substituted with a hydroxyl group or an alkyl C1-C6; Ri, R2, R3 and R4, identical or different, represent a hydrogen atom, an alkyl radical in C1-C6 hydroxyalkyl or -C

C6.

The composition according to the invention may also comprise various adjuvants conventionally used, such as anionic, cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, hair dyes, polymers, inorganic thickening agents, antioxidants , penetrating agents, fragrances, buffers, dispersants, conditioning agents such as, for example, cations, silicones, film-forming agents, preserving agents, stabilizing agents.

When one or more surfactants are present, preferably nonionic, anionic or amphoteric, their content is 0.01 to 30% by weight based on the weight of the composition.

Of course, the man of the art care to select this or these optional additional compounds such that the advantageous properties intrinsically associated with the composition according to the invention are not, or not substantially, impaired by the additions considered.

The composition according to the invention may be in various forms, such as in the form of liquids, shampoos, creams, gels, or in any other suitable shape.

A particularly preferred form of the present invention, the composition is in the form of a coloring shampoo and lightening comprising, in a cosmetically acceptable aqueous medium.

The composition according to the invention may likewise include at least one oxidizing agent. The latter can be selected for example from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as persulfates and perborales, and enzymes such as peroxidases and oxidoreductases containing two or four electrons. The use of hydrogen peroxide or enzymes is particularly preferred.

The invention also relates to the use, for dyeing with a lightening effect of human keratin substances, of a composition comprising, in a cosmetically acceptable medium, at least one fluorescent dye soluble in said medium, and at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and their monovalent or divalent salts of alkali metal, alkaline earth, transition metal, organic amine or ammonium, alone or in mixtures.

Within the framework of this use, the fluorescent compound may be chosen from fluorescent compounds belonging to the following families: naphthalimides; cationic coumarins or not; xanthenodiquinolizines (such as in particular sulphorhodamines); azaxanthenes; naphtholactams; azlactones; oxazines; thiazines; dioxazines; fluorescent dyes monocationic or polycationic of azo, azomethine or methine type, alone or as mixtures. For more particular compounds include compounds of formulas F1, F2 and F3 already detailed before.

One can still use the compounds of structure (F4) below:

wherein R represents a methyl or ethyl radical; R 'represents a methyl radical and X an anion of the chloride, iodide, sulfate, methosulfate, acetate, perchlorate. Examples of such compound include the Photosensitiving Dye NK-557 sold by the company Ubichem, for which R represents an ethyl radical, R 'represents a methyl radical and X- iodide.

All that has been described previously on the nature and contents of the various additives present in the composition remains valid and will not be repeated in this section.

According to the present invention, the term human keratin materials, the skin, hair, nails, eyelashes, and eyebrows, especially dark skin and pigmented or artificially colored hair.

Within the meaning of the invention, by means dark skin, a skin whose luminance L * in the CIEL L * a * b * is less than or equal to 45 and preferably less than or equal to 40, given also that L * = 0 is equivalent to black and L * = 100 white. The skin types corresponding to this luminance are African skin, African American skin, the Spanish-American skin, Indian skin and North African skin. For the purposes of the invention, the term pigmented or artificially colored hair, hair whose tone height is less than or equal to 6 (dark blond) and preferably less than or equal to 4 (chestnut).

The lightening of the hair is evaluated by the "pitch" which characterizes the degree or level of lightening. The notion of "tone" is based on the classification of natural shades, one tone separating each shade from the one that follows or immediately preceding it. This definition and the classification of natural shades are well known to hair styling professionals and published in the book "Science of hair treatments" Charles ZVIAK 1988 Ed.Masson, pp.215 and 278. the heights tone range from 1 (black) to 10 (light blonde), one unit corresponding to one tone; the higher the number, the higher the grade is clear another object of the present invention therefore relates to a method for coloring effect. lightening human keratin fibers, consisting in implementing the following steps: a) applying to the keratin fibers, for a time sufficient to develop the coloration and lightening Sirés, the composition according to the invention, b) said fibers are optionally rinsed, c) optionally washed with shampoo and rinsed the fibers, d) dried or allowed to dry the fibers.

The present invention further relates to a method for dyeing with a lightening effect, a dark skin which comprises applying to the skin, the composition which has just been described, and drying or allowing to dry the skin. Preferably, this composition is not carried out in the presence of an oxidizing agent

All that has been described above regarding the various components of the composition remains valid and may be made thereto.

In particular, the methods of the invention are suitable for treating human keratin fibers and especially the hair, pigmented or artificially colored, or dark skin.

In particular, fibers which can advantageously be treated by the process according to the invention have a tone height is less than or equal to 6

(Dark blond) and preferably less than or equal to 4 (brown). In addition, a dark skin can be treated in accordance with the invention has a lightness L * in the CIEL L * a * b * less than or equal to 45 and preferably less than or equal to 40.

According to a first embodiment of the invention, the dyeing process with a lightening effect of the fibers is carried out with a composition containing no oxidizing agent.

According to a second embodiment of the invention, the dyeing process with a lightening effect of the fibers is carried out with a composition comprising an oxidizing agent.

According to a first variant of these dyeing processes according to the invention, is applied to the fibers, and especially hair, at least one composition as defined above for a sufficient time to develop the desired coloration and lightening, after which they are rinsed, optionally washed with shampoo, rinsed again and dried. According to a second variant of these dyeing methods in accordance with the invention, applied to the fibers, and in particular the hair at least one composition as defined above without final rinsing.

According to a third coloration process variant according to the invention, the dyeing process includes a preliminary step consisting in separately storing, on the one hand, a composition according to the invention and, on the other hand, a composition comprising in a cosmetically acceptable medium, at least one oxidizing agent, and then in mixing them together at the time of use before applying this mixture to the keratin fibers, and in particular the hair, for a time sufficient to develop the desired coloring , after which the fibers are rinsed, optionally washed with shampoo, rinsed again and dried.

The time required to develop the coloration and obtaining of the lightening effect on the fibers, especially the hair, is from about 5 to 60 minutes and more particularly from about 5 to 40 minutes.

The temperature required to develop the coloration and to obtain the lightening effect is usually between room temperature (15-25 ° C) and 80 ° C and more particularly between 15 and 40 ° C.

Another object of the invention is a multi-compartment device for dyeing with a lightening effect of the keratin fibers and especially the hair, comprising at least one compartment containing a composition according to the invention and at least one other compartment containing a composition comprising at least one oxidizing agent. This device may be equipped with a means for delivering the fibers on the desired mixture, such as the devices described in patent FR 2,586,913.

It should be noted that the composition according to the invention, if it is used for treating keratinous fibers, such as chestnut hair for example, allows to achieve the following results:

If one measures the reflectance of the hair when it is irradiated with visible light in the wavelength range from 400 to 700 nanometers, and the reflectance curves comparing a function of the length wave, hair treated with the composition of the invention and non-treated hair, it is found that the reflectance curve corresponding to the treated hair in a wavelength range from 500 to 700 nanometers, is greater than that corresponding to the untreated hair. This means that in the wavelength range from 500 to 700 nanometers and preferably from 540 to 700 nanometers, there is at least a range where the reflectance curve corresponding to the treated hair is higher than the reflectance curve corresponding to the untreated hair. The term "upper", a difference of at least 0.05% reflectance and preferably at least 0.1%.

However, it is clear that there may be in the wavelength range from 500 to 700 nanometers and preferably from 540 to 700 nanometers, one or more tracks where the reflectance curve corresponding to the treated fibers is either superimposable is less than the reflectance curve corresponding to untreated fibers.

Preferably, the wavelength at which the difference is maximum between the reflectance curve of the treated hair and of the untreated hair is in the wavelength range from 500 to 650 nanometers, and preferably in the wavelength range of 550-620 nanometers.

In addition, and preferably, the composition according to the invention is capable of thinning hair and skin in a shade which, in the CIEL L * a * b * b * has a variable greater than or equal to 6, with a ratio of b * / a * absolute value, greater than 1.2 according to the selection test described below. The selection of test composition is applied to keratin fibers brown, more particularly the hair, at a rate of 10 grams of composition to 1 gram of brown fibers. The composition is spread so as to cover all the fibers. The composition is allowed to act for 20 minutes at room temperature (20-25 ° C). The fibers are then rinsed with water and then washed with a shampoo based on lauryl sulfate. They are then dried. then were measured speclrocolorimétriques fiber characteristics to determine the coordinates L * a * b *.

In the CIEL L * a * b *, a * and b * indicate two color axis, a * axis indicates the green / red (+ a * is red, -a * is green) and b * l axis of blue / yellow (+ b * is yellow, and -b * is blue); near-zero values ​​for a * and b * correspond to gray shades.

The following examples are intended to illustrate the invention without limiting its scope.

EXAMPLES

fluorescent compound

Reacting 93 g of 2-picoline with 120 g of 1, 6-dibromohexane in dimethylformamide at 110 ° C for 5 hours. The precipitate product and filtered. Are dissolved 109 g of the product obtained above in methanol and 82.82 g of p-dimethylaminobenzaldehyde was added in twice in the presence of pyrrolidine. then left for 30 minutes. The product is recovered in precipitated form.

mass spectroscopy analysis: 266.

Elemental analysis: C: 62.43%; H: 6.40%; Br: 23.07%; N: 8.09%. The formula is as follows C36H44N4.2Br.

compositions

Coloring

Each composition is applied to a natural lock of brown hair (tone height 4) with an exposure time of 20 minutes.

The lock was then rinsed and dried under a hood for 30 minutes.

This gives a net effect of lightening hair.

Claims

Composition, characterized in that it comprises, in a cosmetically acceptable medium, at least one fluorescent dye soluble in said medium, and at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and their monovalent metal salts or divalent alkali, alkaline earth, transition metal, organic amine or ammonium, alone or in mixtures; the composition not comprising, as fluorescent agent, 2- [2- (4-dialkylamino) phenyl ethenyl] -1-alkylpyridinium in which the alkyl radical of the pyridinium nucleus represents a methyl or ethyl radical, that of the benzene ring represents methyl and wherein the against ion is a halide.
Composition according to any one of the preceding claims, characterized in that the fluorescent dye leads to a reflectance maximum being in the wavelength range from 500 to 650 nanometers and preferably in the range of length of wavelength ranging from 550-620 nanometers.
Composition of any one of the preceding claims, characterized in that the fluorescent dye is chosen from fluorescent compounds belonging to the following families: naphthalimides; cationic coumarins or not; xanthenodiquinolizines; azaxanthenes; naphtholactams; azlactones; oxazines; thiazines; dioxazines; polycationic fluorescent dyes of azo, azomethine or methine type, alone or as mixtures.
4. The composition of any one of the preceding claims, characterized in that the fluorescent compound has the following formula:
in which :
R1, R2, identical or different, represent:
• a hydrogen atom;
• an alkyl radical, linear or branched, comprising 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and or substituted by at least one halogen atom; o an aryl or arylalkyl radical, the aryl group containing 6 carbon atoms and the alkyl radical having 1 to 4 carbon atoms; the aryl radical being optionally substituted by one or more linear or branched alkyl radicals comprising 1 to 4 carbon atoms optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen; o Ri and R2 may optionally be linked to form a heterocycle with the nitrogen atom and may comprise one or more other heteroatoms, the heterocycle optionally being substituted with at least one linear or branched alkyl radical, preferably comprising 1 to 4 carbon atoms and optionally being interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen atom;
• R1 or R2 may optionally be engaged in a heterocycle comprising the nitrogen atom and one of the phenyl carbon atoms bearing the said nitrogen atom;
R3, R4, identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 4 carbon atoms;
R5, identical or different, represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical comprising 1 to 4 carbon atoms optionally interrupted by at least one heteroatom;
R6, identical or different, represent a hydrogen atom; a halogen atom; a linear or branched alkyl radical comprising 1 to 4 carbon atoms, optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom and / or substituted with at least one halogen atom;
X represents: • an alkyl radical, linear or branched containing 1 to 14 carbon atoms, or alkenyl having 2 to 14 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen atom;
• a heterocyclic radical comprising 5 or 6 members, optionally substituted by at least one linear or branched alkyl radical comprising 1 to 14 carbon atoms, optionally substituted with at least one heteroatom; by at least one aminoalkyl radical, linear or branched, comprising 1 to 4 carbon atoms, optionally substituted with at least one heteroatom; by at least one halogen atom; • an aromatic radical or diaromatic fused or unfused, separated or not by an alkyl radical comprising 1 to 4 carbon atoms, the aryl radicals being optionally substituted by at least one halogen atom or at least one alkyl radical comprising 1 to 10 carbon atoms optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom;
• a dicarbonyl radical;
• the group X possibly bearing one or more cationic charges; a being equal to 0 or 1;
Y ", identical or different, representing an organic or mineral anion; n being an integer at least equal to 2 and at most equal to the number of cationic charges present in the fluorescent compound.
5. Composition according to any one of the preceding claims, characterized in that the fluorescent dye are present in a weight concentration of between 0.01 and 20% by weight, more particularly between 0.05 to 10% by weight , preferably between 0.1 to 5% by weight, based on the total weight of the composition.
6. Composition according to any one of the preceding claims, characterized in that the sequestering agent of hydroxycarboxylic type corresponds to the formula
(A) below: R- (CHOH) 4 -C0 2 X, wherein R is CH 2 OH or C0 2 X and X represents hydrogen or a monovalent or divalent cation.
7. The composition the preceding claim, characterized in that the sequestering agent is selected from gluconic acid, mucic acid, glucaric acid, mannaric acid, salts thereof, mixtures thereof.
. Composition according to any one of claims 1 to 5, characterized in that the sequestering agent of polycarboxylic kind correspond to the formula (B): R-N (Y) (CH (R ') Cθ2X), wherein Y represents a hydrogen or CH (R ') Cθ2X; R represents a hydrogen atom or a group (a)
-CH (C0 2 X) - (CH2) 2 NC0 X, (b) - (CH 2) n OH, (c) -CH (R ") X C0 2, (d) - (CH 2) n -N (COR ') - CH 2 C0 2 X, (e) - (CH 2) nN (CH2C02X) CH2C0 2 X and (f) - (CH 2) n NH- CH (Cθ2X) CH2Cθ2X, wherein R' is a hydrogen atom or a group CH2CO2X; R "represents a linear or branched alkyl C1-C30 or cyclic C3-C30, n is an integer between 1 and 5, and preferably is 2, X represents a hydrogen atom or a monovalent cation or divalent.
9. The composition the preceding claim, characterized in that the sequestering agent is selected from:
• compounds comprising four carboxylic acid functional groups or salts thereof, when R represents a hydrogen atom and R 'is -CH 2 - C0 2 X, or when R represents the group -CH (C0 2 X) - (CH 2) 2 -C0 2 X and R 'represents a hydrogen atom; o compounds comprising three carboxylic acid functional groups or salts thereof, when R represents the group -CH (CH 3) -C0 2 X and R 'represents a hydrogen atom or when R represents a group - (CH 2) 2 - N (0C0R ") - CH 2 -C0 2 X and R 'represents a hydrogen atom.
10. The composition of one of claims 8 or 9, characterized in that the sequestering agent is selected from methylglycine diacetic acid, N-lauroyl-N, N ', N'-tri-acetic ethylenediamine, l 'iminodisuccinic acid, N, N-dicarboxymethyl L-glutamic acid, ethylenediamine N, N' disuccinic acid, salts thereof, mixtures thereof.
11. Composition according to one of the preceding claims, characterized in that the sequestering agent content is 0.0001 to 20% by weight based on the weight of the composition, more preferably from 0.001 to 10% by weight based on the weight of the composition, preferably between 0.01 and 5% by weight based on the weight of the composition.
12. Composition according to one of the preceding claims, characterized in that it comprises at least one nonionic, anionic or amphoteric.
13. Composition according to the preceding claim, characterized in that the surfactant content represents 0.01 to 30% by weight relative to the total weight of the composition.
14. Composition, characterized in that it comprises the composition according to one of claims 1 to 13, and at least one oxidizing agent.
15. Composition according to the preceding claim, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, bromates of alkali metals, persalts such as perborates and persulphates, and enzymes such as peroxidases and oxidoreductases containing two or four electrons, and preferably hydrogen peroxide.
16. A process for coloring with a lightening effect, human keratin fibers, characterized in that the implement is put the steps of: a) applying onto said fibers a composition as defined according to any one of claims 1 to 15 for a sufficient time to develop the desired coloration and lightening, b) optionally rinsed the fibers, c) optionally washed with shampoo and rinsed fibers, d) dried or allowed to dry the fibers.
17. The method of claim 16, characterized in that it comprises a preliminary step consisting in separately storing, on the one hand, a composition according to one of claims 1 to 13, and on the other hand, a composition containing, in a cosmetically acceptable medium, at least one oxidizing agent, and then in mixing them together at the time of use before applying this mixture to the fibers for a time sufficient to develop the desired coloration, after which the rinsed , optionally washed with shampoo, rinsed again and dried.
18. A method according to any one of claims 16 or 17, characterized in that the composition is applied to hair having a tone height of less than or equal to 6 and preferably less than or equal to 4.
19. A method according to one of claims 16 to 18, characterized in that the human keratin fibers are artificially colored or pigmented.
20. A process for coloring with a lightening effect, a dark skin, characterized in that one applies to the skin a composition according to any one of claims 1 to 13, then dry or the skin is allowed to dry.
21. Multi-compartment device for dyeing and lightening keratin fibers, comprising at least one compartment containing a composition according to one of claims 1 to 13, and at least one other compartment containing a composition containing at least one oxidizing agent .
22. Use for dyeing with lightening effect of keratin materials, of a composition comprising, in a cosmetically acceptable medium, at least one fluorescent dye soluble in said medium, and at least one complexing agent selected from hydroxycarboxylic acids, polycarboxylic acids, and their monovalent or divalent salts of alkali metal, alkaline earth, transition metal, organic amine or ammonium, alone or in mixtures.
23. Use according to the preceding claim, characterized in that the fluorescent dye leads to a reflectance maximum being in the wavelength range from 500 to 650 nanometers and preferably in the wavelength range of 550-620 nanometers.
24. Use according to any one of claims 22 or 23, characterized in that the fluorescent dye is chosen from fluorescent compounds belonging to the following families: naphthalimides; cationic coumarins or not; xanthenodiquinolizines; azaxanthenes; naphtholactams; azlactones; oxazines; thiazines; dioxazines; fluorescent dyes monocationic or polycationic of azo, azomethine or methine type, alone or as mixtures.
25. Use according to any one of claims 22 to 24, characterized in that the fluorescent dye is selected from the group formed by dyes having the following structures:
in which :
R1, R2, identical or different, represent: a hydrogen atom;
• an alkyl radical, linear or branched, comprising 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted by at least one halogen atom; o an aryl or arylalkyl radical, the aryl group containing 6 carbon atoms and the alkyl radical having 1 to 4 carbon atoms; the aryl radical being optionally substituted by one or more linear or branched alkyl radicals comprising 1 to 4 carbon atoms optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and or substituted by at least one atom halogen;
• R1 and R2 may optionally be linked to form a heterocycle with the nitrogen atom and may comprise one or more other heteroatoms, the heterocycle being optionally substituted with at least one linear or branched alkyl radical, preferably comprising 1 to 4 carbon atoms and optionally being interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen atom;
• R1 or R2 may optionally be engaged in a heterocycle comprising the nitrogen atom and one of the phenyl carbon atoms bearing the said nitrogen atom;
R3, R4, identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 4 carbon atoms; R5, identical or different, represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical comprising 1 to 4 carbon atoms optionally interrupted by at least one heteroatom; R6, identical or different, represent a hydrogen atom; a halogen atom; a linear or branched alkyl radical comprising 1 to 4 carbon atoms, optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom and / or substituted with at least one halogen atom; X represents "an alkyl radical linear or branched containing 1 to 14 carbon atoms, or alkenyl having 2 to 14 carbon atoms, optionally interrupted and / or substituted with at least one heteroatom and / or group comprising at least one heteroatom and / or substituted with at least one halogen atom;
• a heterocyclic radical comprising 5 or 6 members, optionally substituted by at least one linear or branched alkyl radical comprising 1 to 14 carbon atoms, optionally substituted with at least one heteroatom; by at least one aminoalkyl radical, linear or branched, comprising 1 to 4 carbon atoms, optionally substituted with at least one heteroatom; by at least one halogen atom; o an aromatic or diaromatic radical fused or unfused, separated or not by an alkyl radical comprising 1 to 4 carbon atoms, the aryl radicals being optionally substituted by at least one halogen atom or at least one alkyl radical comprising 1 to 10 carbon atoms optionally substituted and / or interrupted with at least one heteroatom and / or group bearing at least one heteroatom;
• a dicarbonyl radical;
• the group X possibly bearing one or more cationic charges; a being equal to 0 or 1;
Y ", identical or different, representing an organic or mineral anion; n being an integer at least equal to 2 and at most equal to the number of cationic charges present in the fluorescent compound;
wherein R represents a methyl or ethyl radical; R 'represents a methyl radical and X an anion of the chloride, iodide, sulfate, methosulfate, acetate, perchlorate ..
26. Use according to any one of claims 22 to 25, characterized in that the keratin materials are pigmented or dyed keratin fibers artificially, in particular the hair, or dark skin.
27. Use according to claim 26, characterized in that the hair has a tone height of less than or equal to 6 and preferably less than or equal to 4.
PCT/FR2004/000818 2003-04-01 2004-04-01 Dyeing composition for human keratinous fibers comprising a fluorescent dye and a particular sequestering agent, method and use WO2004091556A3 (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2870727A1 (en) * 2004-05-28 2005-12-02 Oreal Composition, useful for the treatment (coloring) of human keratinous fibers comprises a compound (ethylenediamine-N,N'-disuccinic acid) and a direct dye
WO2007110541A2 (en) * 2006-03-24 2007-10-04 L'oreal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising a condensed cycle, with an internal cationic charge, and method for lightening keratin materials using said colorant
WO2007110536A2 (en) * 2006-03-24 2007-10-04 L'oréal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising an ortho-pyridinium group with an uninterrupted alkylene chain and an internal cationic charge, and method for lightening keratin materials using said colorant
WO2007110538A2 (en) * 2006-03-24 2007-10-04 L'oréal Dyeing composition containing a masked thiol fluorescent colorant comprising a dimethylamino group, with an internal cationic charge, and method for lightening keratin materials using said colorant and disulphide colorants
FR2912136A1 (en) * 2007-02-05 2008-08-08 Oreal New pyridinium-substituted cationic thiol derivative fluorescent dye compounds, useful for dyeing keratin fibers, especially for lightening dark human hair
FR2921376A1 (en) * 2007-09-21 2009-03-27 Oreal Consists styryl tetrahydroquinolinium thiol / disulfide, METHOD OF LIGHTENING KERATIN MATERIALS from this dye
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7727287B2 (en) 2007-09-21 2010-06-01 L'oreal S.A. Hemicyanin styryl thiol/disulfide dye, composition comprising hemicyanin styryl thoil/disulfide dye, and method for lightening keratin materials using hemicyanin styryl thiol/disulfide dye
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity

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FR2870727A1 (en) * 2004-05-28 2005-12-02 Oreal Composition, useful for the treatment (coloring) of human keratinous fibers comprises a compound (ethylenediamine-N,N'-disuccinic acid) and a direct dye
WO2007110541A2 (en) * 2006-03-24 2007-10-04 L'oreal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising a condensed cycle, with an internal cationic charge, and method for lightening keratin materials using said colorant
WO2007110536A2 (en) * 2006-03-24 2007-10-04 L'oréal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising an ortho-pyridinium group with an uninterrupted alkylene chain and an internal cationic charge, and method for lightening keratin materials using said colorant
WO2007110538A2 (en) * 2006-03-24 2007-10-04 L'oréal Dyeing composition containing a masked thiol fluorescent colorant comprising a dimethylamino group, with an internal cationic charge, and method for lightening keratin materials using said colorant and disulphide colorants
WO2007110536A3 (en) * 2006-03-24 2008-05-15 Oreal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising an ortho-pyridinium group with an uninterrupted alkylene chain and an internal cationic charge, and method for lightening keratin materials using said colorant
WO2007110541A3 (en) * 2006-03-24 2008-08-07 Oreal Dyeing composition containing a thiol/disulphide fluorescent colorant comprising a condensed cycle, with an internal cationic charge, and method for lightening keratin materials using said colorant
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
WO2007110538A3 (en) * 2006-03-24 2008-10-09 Nicolas Daubresse Dyeing composition containing a masked thiol fluorescent colorant comprising a dimethylamino group, with an internal cationic charge, and method for lightening keratin materials using said colorant and disulphide colorants
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity
FR2912136A1 (en) * 2007-02-05 2008-08-08 Oreal New pyridinium-substituted cationic thiol derivative fluorescent dye compounds, useful for dyeing keratin fibers, especially for lightening dark human hair
EP2075289A1 (en) * 2007-09-21 2009-07-01 L'Oréal Styryl tetrahydroquinolinium thiol/disulfide compound, process for lightening keratin materials using this dye
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7727287B2 (en) 2007-09-21 2010-06-01 L'oreal S.A. Hemicyanin styryl thiol/disulfide dye, composition comprising hemicyanin styryl thoil/disulfide dye, and method for lightening keratin materials using hemicyanin styryl thiol/disulfide dye
US7744657B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Styrl tetrahydroquinolinium thiol/disulfide dye compound and method for lightening keratin materials using the same
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye
FR2921376A1 (en) * 2007-09-21 2009-03-27 Oreal Consists styryl tetrahydroquinolinium thiol / disulfide, METHOD OF LIGHTENING KERATIN MATERIALS from this dye

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