The present invention relates to a composition for simultaneous bleaching and dyeing of keratin fibers, comprising one or more particular heterocyclic salts, and also to a process for simultaneous bleaching and dyeing of keratin fibers using this composition.
When a person wishes to radically change hair color, in particular when he or she wishes to obtain a lighter color than his or her original color, it is often necessary to carry out bleaching and then dyeing of the hair. There are several methods for doing this.
The first method consists in using lightening products based on aqueous ammonia and on hydrogen peroxide. These products may optionally contain dyes, thereby making it possible to simultaneously lighten and dye the hair. However, the lightening performance results of these products remain limited, more particularly for applications to natural and/or dyed dark-colored hair.
The second method consists in applying to the hair lightening compositions based on peroxygenated salts, such as persulfates, and on alkaline agents, to which hydrogen peroxide has been added at the time of use, in order to obtain greater lightening. These compositions may comprise direct dyes in order to simultaneously dye and bleach the hair. However, the range of direct dyes that can be used in these compositions remains restricted since only stable direct dyes can be used in such conditions in order to obtain good color build-up and intense and chromatic colors. In order to attempt to remedy this stability problem, it has been envisioned to perform the process in two steps: a first step during which the hair is bleached using the lightening composition, and then a second step during which the hair is dyed using a composition comprising direct dyes. However, a two-step process is not satisfactory since, in addition to creating numerous manipulations, it has the drawback of being relatively long.
There is therefore a real need to develop a composition for bleaching and dyeing keratin fibers, comprising direct dyes, the composition having both good lightening properties and good dyeing properties, particularly when it is applied to dark-colored hair, and making it possible in particular to obtain good color build-up and also intense and chromatic colors. Furthermore, such a composition may comprise a wide range of direct dyes making it possible to obtain the shade sought by the user. Finally, such a composition may be used in a single-step process for simultaneous bleaching and dyeing of keratin fibers.
The applicant has discovered, surprisingly, that all of these objectives can be achieved by the composition according to the present invention.
According to a first aspect, a subject of the present invention is a composition comprising:
According to a second aspect, a subject of the present invention is a process for simultaneous bleaching and dyeing of keratin fibers, comprising the application to the keratin fibers of a composition as defined previously.
According to a third aspect, a subject of the present invention is a multi-compartment device or kit comprising:
For the purposes of the present invention, and unless otherwise indicated:
Unless otherwise indicated, when compounds are mentioned in the present application, this also includes the optical isomers thereof, the geometrical isomers thereof, the tautomers thereof, the salts thereof or the solvates thereof, alone or as a mixture.
The expressions “at least one” and “one or more” are synonymous and may be used interchangeably.
According to a first aspect, a subject of the present invention is a composition as defined previously.
The applicant has noted, surprisingly, that the addition of one or more heterocyclic salts of formula (A) to a composition comprising one or more oxidizing agents makes it possible to stabilize the direct dye(s) and to obtain a satisfactory level of lightening and also better color build-up and intense and chromatic colors.
The composition according to the invention comprises a) one or more chemical oxidizing agents chosen from hydrogen peroxide, hydrogen peroxide-generating agents other than peroxygenated salts, and mixtures thereof.
The hydrogen peroxide-generating agents other than peroxygenated salts can be chosen from urea peroxide, polymeric complexes that can release hydrogen peroxide, oxidases, and mixtures thereof.
By way of example of polymeric complexes that can release hydrogen peroxide, mention may be made of polyvinylpyrrolidone/H2O2 in particular in the form of a powder, and the other polymeric complexes described in US 5 008 093, US 3 376 110 and US 5 183 901.
Oxidases can produce hydrogen peroxide in the presence of a suitable substrate, such as for example glucose in the case of glucose oxidase or uric acid with uricase.
Particularly preferably, the composition according to the invention comprises hydrogen peroxide as chemical oxidizing agent.
According to one particular embodiment, the hydrogen peroxide and/or the hydrogen peroxide-generating agent(s) other than peroxygenated salts can be added to the composition according to the invention just before it is applied to the keratin fibers. The intermediate composition(s) comprising the hydrogen peroxide and/or the hydrogen peroxide-generating agent(s) other than peroxygenated salts can be referred to as oxidizing compositions and can also contain various additional compounds or various adjuvants conventionally used in hair-lightening compositions.
The chemical oxidizing agent(s) may be present in the composition in a total content ranging from 0.1% to 40% by weight, preferably ranging from 1% to 20% by weight, more preferentially ranging from 2% to 15% by weight, relative to the total weight of the composition.
The composition according to the invention comprises b) one or more direct dyes.
The direct dyes b) may be neutral, cationic or anionic direct dyes.
The direct dyes b) may be neutral, cationic or anionic direct dyes chosen from: acridines; acridones; anthranthrones; anthrapyrimidines; anthraquinones; azines; (poly)azos or azo, hydrazono or hydrazones, in particular arylhydrazones; azomethines; benzanthrones; benzimidazoles; benzimidazolones; benzindoles; benzoxazoles; benzopyrans; benzothiazoles; benzoquinones; bis-isoindolines; carboxanilides; coumarins; cyanines, such as (di)azacarbocyanines, (di)azahemicyanines, hemicyanines or tetraazacarbocyanines; (di)azines; bis-azines; (di)oxazines; (di)thiazines; (di)phenylamines; (di)phenylmethanes; (di)ketopyrrolopyrroles; flavonoids, such as flavanthrones and flavones; fluorindines; formazans; indamines; indanthrones; indigoids, thioindigoids and pseudoindigoids; indophenols; indoanilines; isoindolines; isoindolinones; isoviolanthrones; lactones; (poly)methines, such as dimethines of stilbene or styryl types; naphthalimides; naphthanilides; naphtholactams; naphthoquinones; nitro, notably nitro(hetero)aromatics; oxadiazoles; oxazines; perilones; perinones; perylenes; phenazines; phenoxazines; phenothiazines; phthalocyanine; polyenes/carotenoids; porphyrins; pyranthrones; pyrazolanthrones; pyrazolones; pyrimidinoanthrones; pyronines; quinacridones; quinolines; quinophthalones; squaranes; tetrazolines; thiazines; thiopyronines; triarylmethanes or xanthenes and natural direct dyes. Preferably, the direct dyes b) are chosen from anthraquinones, (poly)azos, azomethines and stilbenes, more preferentially from anthraquinones.
The direct dyes b) can be chosen in particular from neutral, cationic or anionic nitrobenzene direct dyes, neutral, cationic or anionic azo direct dyes, neutral, cationic or anionic tetraazapentamethine dyes, cationic or anionic quinone dyes and in particular neutral, cationic or anionic anthraquinone dyes, neutral, cationic or anionic azine direct dyes, neutral, cationic or anionic triarylmethane direct dyes, neutral, cationic or anionic azomethine direct dyes and natural direct dyes. Preferably, the direct dyes are chosen from neutral or anionic anthraquinone dyes and stilbenes.
By way of neutral, anionic or cationic direct dyes that can be used in the present invention, mention may be made of the following dyes: acridines; acridones; anthranthrones; anthrapyrimidines; anthraquinones; azines; (poly)azos, hydrazono or hydrazones, in particular arylhydrazones; azomethines; benzanthrones; benzimidazoles; benzimidazolones; benzindoles; benzoxazoles; benzopyrans; benzothiazoles; benzoquinones; bisazines; bis-isoindolines; carboxanilides; coumarins; cyanines, such as azacarbocyanines, diazacarbocyanines, diazahemicyanines, hemicyanines or tetraazacarbocyanines; diazines; diketopyrrolopyrroles; dioxazines; diphenylamines; diphenylmethanes; dithiazines; flavonoids, such as flavanthrones and flavones; fluorindines; formazans; indamines; indanthrones; indigoids and pseudoindigoids; indophenols; indoanilines; isoindolines; isoindolinones; isoviolanthrones; lactones; (poly)methines, such as dimethines of stilbene or styryl types; naphthalimides; naphthanilides; naphtholactams; naphthoquinones; nitro, notably nitro(hetero)aromatics; oxadiazoles; oxazines; perilones; perinones; perylenes; phenazines; phenoxazine; phenothiazines; phthalocyanine; polyenes/carotenoids; porphyrins; pyranthrones; pyrazolanthrones; pyrazolones; pyrimidinoanthrones; pyronines; quinacridones; quinolines; quinophthalones; squaranes; tetrazole; thiazines; thioindigo; thiopyronines; triarylmethanes or xanthenes.
The direct dyes b) may be neutral direct dyes, preferably chosen from the hydrazono dyes of formulae (IIIa) and (III′a), the azo and styryl dyes (IVa), the diazo and distyryl dyes (IV′a) and (IV″a), the anthraquinone dyes (Va) and the azomethine dyes (VIa) and (VI′a) below, and mixtures thereof:
formulae (IIIa), (III′a), (IVa), (IV′a), (IV″a), (Va), (VIa) and (VI′a) wherein:
The direct dyes b) of formula (IV″a) are preferably of formula (IV‴a)
Formula (IV‴a) wherein:
The direct dyes of formula (IV″a) may be derived from curcumin, demethoxycurcumin and bis-demethoxycurcumin.
Preferably, the direct dyes b) are chosen from the direct dyes of formulae (IV″a) and (IV‴a) and mixtures thereof as defined previously.
According to one particularly preferred embodiment, the direct dyes b) are neutral direct dyes chosen from the following compounds (A) to (G) and mixtures thereof:
preferably from the compounds (E), (F) and (G) and mixtures thereof, more preferentially from the compounds (E) and (G) and mixtures thereof.
The direct dyes b) can be chosen from direct dyes which are cationic or commonly referred to as “basic dyes” for their affinity with acidic substances comprising in particular in their structure at least one endocyclic or exocyclic, cationic or cationizable group.
As cationic azo dyes that can be used in the present invention, mention may be made particularly of the cationic dyes described in Kirk-Othmer’s Encyclopedia of Chemical Technology, “Dyes, Azo”, J. Wiley & Sons, updated on Apr. 19, 2010.
Mention may also be made of the cationic azo dyes described in patent applications WO 95/15144, WO 95/01772 and EP 714954.
Mention may also be made of the cationic azo dyes described in the Color Index International, 3rd edition, in particular of the following compounds: Basic Red 22; Basic Red 76; Basic Yellow 57; Basic Brown 16; Basic Brown 17.
Among the cationic quinone dyes, those mentioned in the Color Index International, 3rd edition, are suitable and, among these, mention may be made, inter alia, of the following dyes: Basic Blue 22; Basic Blue 99.
Among the azine dyes that are suitable, mention may be made of those listed in the Color Index International, 3rd edition, and for example of the following dyes: Basic Blue 17, Basic Red 2.
Among the cationic triarylmethane dyes that can be used according to the invention, mention may be made, in addition to those listed in the Color Index International, 3rd edition, of the following dyes: Basic Green 1, Basic Violet 3, Basic Violet 14, Basic Blue 7, Basic Blue 26.
Mention may also be made of the direct dyes described in documents US 5 888 252, EP 1 133 975, WO 03/029 359, EP 860 636, WO 95/01772, WO 95/15144 and EP 714 954. Mention may also be made of those listed in the encyclopedia “The Chemistry of Synthetic Dyes” by K. Venkataraman, 1952, Academic Press, vol. 1 to 7, in “Kirk-Othmer’s Encyclopedia of Chemical Technology”, in the chapter “Dyes and Dye Intermediates”, 1993, Wiley and Sons, and in various chapters of “Ullmann’s Encyclopedia of Industrial Chemistry”, 7th edition, Wiley and Sons.
Preferably, the cationic direct dyes are chosen from those resulting from dyes of azo and hydrazono type.
The cationic direct dyes may be cationic azo dyes, as described in EP 850 636,FR 2 788 433,, EP 920 856,WO 99/48465,FR 2 757 385,EP 850 637,EP 918 053,WO 97/44004,FR 2 570 946,FR 2 285 851,DE 2 538 363,FR 2 189 006,FR 1 560 664,FR 1 540 423,FR 1 567 219,FR 1 516 943,FR 1 221 122,DE 4 220 388,DE 4 137 005, WO 01/66646, US 5 708 151, WO 95/01772, WO 515 144, GB 1 195 386, US 3 524 842, US 5 879 413, EP 1 062 940, EP 1 133 976, GB 738 585, DE 2 527 638FR 2 275 462, GB 1974-27645, Acta Histochem. (1978), 61(1), 48-52; Tsitologiya (1968), 10(3), 403-5; Zh. Obshch. Khim., (1970), 40(1), 195-202; Ann. Chim. (Rome) (1975), 65(5-6), 305-14; Journal of the Chinese Chemical Society (Taipei) (1998), 45(1), 209-211; Rev. Roum. Chim. (1988), 33(4), 377-83; Text. Res. J. (1984), 54(2), 105-7; Chim. Ind. (Milan) (1974), 56(9), 600-3; Khim. Tekhnol. (1979), 22(5), 548-53; Ger. Monatsh. Chem. (1975), 106(3), 643-8; MRL Bull. Res. Dev. (1992), 6(2), 21-7; Lihua Jianyan, Huaxue Fence (1993), 29(4), 233-4; Dyes Pigm. (1992), 19(1), 69-79; Dyes Pigm. (1989), 11(3), 163-72.
Preferably, the cationic direct dyes comprise a quaternary ammonium group; more preferentially, the cationic charge is endocyclic. These cationic groups are, for example, a cationic group:
Mention may be made of the hydrazono cationic direct dyes of formulae (IIb) and (IIIb) and the azo dyes of formulae (IVb) and (Vb) below:
formulae (IIb) to (Vb) wherein:
In particular, mention may be made of the azo and hydrazono direct dyes bearing an endocyclic cationic charge of formulae (IIb) to (Vb) as defined previously. More particularly, mention may be made of the cationic direct dyes of formulae (IIb) to (Vb) bearing an endocyclic cationic charge described in patent applications WO 95/15144, WO 95/01772 and EP 714 954.
Preferably, mention may be made of the following direct dyes:
formulae (II-1) and (IV-1) wherein:
In particular, the dyes of formulae (II-1) and (IV-1) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof:
with Q′ being an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesityl.
The direct dyes b) can be chosen from fluorescent direct dyes.
By way of example of fluorescent dyes that may be used in the present invention, mention may be made of neutral, anionic or cationic dyes chosen from the following dyes: acridines, acridones, benzanthrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyrans, benzothiazoles, coumarins, difluoro{2-[(2H-pyrrol-2-ylidene-kN)methyl]-1H-pyrrolato-kN}borons (BODIPY®), diketopyrrolopyrroles, fluorindines, (poly)methines (in particular cyanines and styryls/hemicyanines), naphthalimides, naphthanilides, naphthylamine (such as dansyls), oxadiazoles, oxazines, perilones, perinones, perylenes, polyenes/carotenoids, squaranes, stilbenes, xanthenes.
Mention may also be made of the fluorescent dyes described in documents EP 1 133 975, WO 03/029 359, EP 860 636, WO 95/01772, WO 95/15144 and EP 714 954 and those listed in the encyclopedia “The Chemistry of Synthetic Dyes” by K. Venkataraman, 1952, Academic Press, vol. 1 to 7, in “Kirk-Othmer’s Encyclopedia of Chemical Technology”, in the chapter “Dyes and Dye Intermediates”, 1993, Wiley and Sons, and in various chapters of “Ullmann’s Encyclopedia of Industrial Chemistry”, 7th edition, Wiley and Sons, and in “The Handbook - A Guide to Fluorescent Probes and Labeling Technologies”, 10th Ed., Molecular Probes/Invitrogen - Oregon 2005, circulated on the Internet or in the preceding printed editions.
According to a preferred variant, the fluorescent dye(s) are cationic polymethines and comprise at least one quaternary ammonium group, such as those of formula (Vb) below: W+-[C(Rc)=C(Rd)m′-Ar, Q- formula (Vb) wherein:
The direct dyes b) can be chosen from anionic direct dyes or dyes commonly referred to as “acidic” direct dyes on account of their affinity with alkaline substances.
The term “anionic direct dyes” is intended to mean any direct dye comprising in its structure at least one CO2R or SO3R substituent with R denoting a hydrogen atom or a cation originating from a metal or from an amine, or an ammonium ion. The anionic dyes can be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid triarylmethane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and acid natural dyes.
Preferably, the anionic direct dyes are acidic anthraquinones.
The direct dyes b) can be anionic direct dyes preferably chosen from the dyes of formulae (III), (III′), (IV), (IV′), (V), (V′), (VI), (VI′), (VII), (VIII), (IX) and (X) below, and mixtures thereof:
As examples of dyes of formula (III), mention may be made of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment Red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3, Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2, Food Yellow 3 or Sunset Yellow;
As examples of dyes of formula (IV), mention may be made of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and as examples of dyes of formula (IV′), mention may be made of: Acid Yellow 17;
As examples of dyes of formula (V), mention may be made of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT violet No. 2;
As examples of dyes of formula (VI), mention may be made of: Acid Brown 13 and Acid Orange 3; as examples of dyes of formula (VI′), mention may be made of: Acid Yellow 1, sodium salt of 2,4-dinitro-1-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2-(4′-N,N-(2″-hydroxyethyl)amino-2′-nitro)anilineethanesulfonic acid, 4-β-hydroxyethylamino-3-nitrobenzenesulfonic acid; Ext. D&C Yellow 7;
As examples of dyes of formula (VII), mention may be made of: Acid Blue 1, Acid Blue 3, Acid Blue 7, Acid Blue 9, Acid Violet 49, Acid Green 3, Acid Green 5 and Acid Green 50.
As examples of dyes of formula (VIII), mention may be made of: Acid Yellow 73, Acid Red 51, Acid Red 52, Acid Red 87, Acid Red 92, Acid Red 95 and Acid Violet 9;
As examples of dyes of formula (IX), mention may be made of: Acid Blue 74.
More particularly, the dyes of formulae (III) to (VIII) that are useful in the invention are chosen from: Acid Red 87 (VIII) (C.I. 45380); Sodium salt of 2,4-dinitro-1-naphthol-7-sulfonic acid (VI’) (C.I. 10316); Acid Orange 3 (VI) (C.I. 10383); Acid Yellow 9/Food Yellow 2 (III) (C.I. 13015); Direct Red 45/Food Red 13 (III) (C.I. 14780); Acid Black 52 (III) (C.I. 13711); Acid Yellow 36 (III) (C.I. 13065); Sodium salt of 1-hydroxy-2-(2′,4′-xylyl-5-sulfonatoazo)naphthalene-4-sulfonic acid/Food Red 1 (III) (C.I. 14700); Acid Red 14/Food Red 3/Mordant Blue 79 (III) (C.I. 14720); Sodium salt of 4-hydroxy-3-[(2-methoxy-5-nitrophenyl)diaza]-6-(phenylamino)naphthalene-2-sulfonic acid/Acid Brown 4 (III) (C. I. 14805); Acid Orange 7/Pigment Orange 17/Solvent Orange 49 (III) (C.I. 15510); Food Yellow 3/Pigment Yellow 104 (III) (C.I. 15985); Acid Red 27/Food Red 9 (III) (C.I. 16185); Acid Orange 10/Food Orange 4 (III) (C.I. 16230); Acid Red 44 (III) (C.I. 16250); Acid Red 33/Food Red 12 (III) (C.I. 17200); Acid Red 184 (III) (C.I. 15685); Acid Violet 3 (III) (C.I. 19125); Sodium salt of 1-hydroxy-2-(4′-acetamidophenylazo)-8-acetamidonaphthalene-3,6-disulfonic acid/Acid Violet 7/Food Red 11 (III) (C.I. 18055); Acid Red 135 (III) (C.I. 18130); Acid Yellow 27 (IV) (C.I. 19130); Acid Yellow 23/Food Yellow 4 (IV) (C.I. 19140); 4′-(sulfonato-2”,4″-dimethyl)-bis-(2,6-phenylazo)-1,3-dihydroxybenzene/Acid Orange 24 (III) (C.I. 20170); Sodium salt of 1-amino-2-(4′-nitrophenylazo)-7-phenylazo-8-hydroxynaphthalene-3,6-disulfonic acid/Acid Black 1 (III) (C.I. 20470); (4-((4-methylphenyl)sulfonyloxy)phenylazo)-2,2′-dimethyl-4-((2-hydroxy-5,8-disulfonato)naphthylazo)biphenyl/Acid Red 111 (III′) (C.I. 23266); Food Black 2 (III) (C.I. 27755); 1-(4′-sulfonatophenylazo)-4-((2″-hydroxy-3″-acetylamino-6”,8″-disulfonato)naphthylazo)-6-sulfonatonaphthalene (tetrasodium salt)/Food Black 1 (III) (C.I. 25440); Acid Blue 9 (VII) (C.I. 42090); Acid Violet 43 (V) (C.I. 60730); Acid Green 25 (V) (C.I. 61570); Sodium salt of 1-amino-4-cyclohexylamino-9,10-anthraquinone-2-sulfonic acid/Acid Blue 62 (V) (C.I. 62045); Acid Blue 78 (V) (C.I. 62105); Sodium salt of 4-hydroxy-3-((2-methoxyphenyl)azo)-1-naphthalenesulfonic acid/Acid Red 4 (III) (C.I. 14710); 2-Piperidino 5-nitrobenzenesulfonic acid (VI′); 2(4′-N,N(2″-hydroxyethyl)amino-2′-nitro)anilineethanesulfonic acid (VI′); 4-β-hydroxyethylamino-3-nitrobenzenesulfonic acid (VI’); Acid Violet 49 (VII) (C.I. 42640); Acid Blue 7 (VII) (C.I. 42080); Sodium salt of 1,2-dihydroxy-3-sulfoanthraquinone/Mordant Red 3 (V) (C.I. 58005); Sodium salt of 1-amino-9,10-dihydro-9,10-dioxo-4-(phenylamino) 2-anthracenesulfonic acid/Acid Blue 25 (V) (C.I. 62055); Sodium salt of 4-hydroxy-3-((2-methoxyphenyl)azo)-1-naphthalenesulfonic acid/Acid Red 4 (III) (C.I. 14710).
Most of these dyes are described in particular in the Color Index published by The Society of Dyers and Colorists, P.O. Box 244, Perkin House, 82 Grattan Road, Bradford, Yorkshire, BD1 2JBN England.
The anionic dyes that are most particularly preferred are the dyes designated in the Color Index under the code C.I. 58005 (monosodium salt of 1,2-dihydroxy-9,10-anthraquinone-3-sulfonic acid), C.I. 60730 (monosodium salt of 2-[(9,10-dihydro-4-hydroxy-9,10-dioxo-1-anthracenyl)amino]-5-methylbenzenesulfonic acid), C.I. 15510 (monosodium salt of 4-[(2-hydroxy-1-naphthalenyl)azo]benzenesulfonic acid), C.I. 15985 (disodium salt of 6-hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonic acid), C.I. 17200 (disodium salt of 5-amino-4-hydroxy-3-(phenylazo)-2,7-naphthalenedisulfonic acid), C.I. 20470 (disodium salt of 1-amino-2-(4′-nitrophenylazo)-7-phenylazo-8-hydroxy-3,6-naphthalenedisulfonic acid), C.I. 42090 (disodium salt of N-ethyl-N-[4-[[4-[ethyl(3-sulfophenyl)methyl]amino]phenyl](2-sulfophenyl)methylene]-2,5-cyclohexadien-1-ylidene]-3-sulfobenzenemethanaminium hydroxide, inner salt), C.I. 61570 (disodium salt of 2,2′-[(9,10-dihydro-9,10-dioxo-1,4-anthracenediyl)diimino]-bis-[5-methyl]benzenesulfonic acid).
Use may also be made of compounds corresponding to the mesomeric or tautomeric forms of structures (III) to (X).
The direct dyes b) can be chosen from natural direct dyes.
Among the natural direct dyes that may be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin, orceins, brazilin, brazilein, hematein and hematoxylin. Extracts or decoctions containing these natural dyes and in particular henna-based poultices or extracts can also be used.
According to one preferred embodiment, the direct dyes b) are chosen from the triarylmethane direct dyes of formulae (IIa1) and (IIa2) below, and mixtures thereof:
wherein:
The direct dye(s) b) can preferably be chosen from Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 4, Basic Violet 14, Basic Blue 1, Basic Blue 7, Basic Blue 26, Basic Green 1 and HC Blue 15, and mixtures thereof.
More preferentially, the direct dye b) is HC Blue 15.
The direct dye(s) b) may be present in the composition in a total content ranging from 0.001% to 10% by weight, preferably from 0.05% to 5% by weight, more preferentially from 0.1% to 3% by weight, relative to the total weight of the composition.
The composition according to the invention comprises c) one or more heterocyclic salts of formula (A):
wherein:
Preferably, the salt(s) of formula (A) are chosen from those of formula (I) below:
Formula (I) wherein:
According to one particular embodiment, the salt(s) of formula (I) are such that R′1 represents a hydrogen atom or a linear or branched, saturated or unsaturated C1-C8 hydrocarbon-based group optionally substituted with one or more groups chosen from hydroxyl, (C1-C2)alkoxy, —SO3H, —SO3- and phenyl; preferably, R′1 represents a hydrogen atom or a saturated, linear or branched, more preferentially linear, C1-C6 hydrocarbon-based group; even more preferentially, R′1 represents a methyl group.
According to one particular embodiment, the salts of formula (I) are such that R2 represents a linear or branched, saturated C1-C6 hydrocarbon-based group such as methyl, and preferably n is 1 and R2 is in position 2.
According to one preferred embodiment of the invention, the salt(s) of formula (A) are chosen from the compounds 1 to 27 below, and mixtures thereof:
with Y- representing an anionic counterion; preferably from the compounds 2, 3, 4, 5 and 25, and mixtures thereof, more preferentially from the compounds 2, 4, 5 and 25, and mixtures thereof, even more preferentially from the compounds 4 and mixtures thereof.
According to one preferred embodiment of the invention, the salt(s) of formula (A) are such that Y- represents an anionic counterion chosen from i) halides such as chloride or bromide, ii) hydrogen sulfates, iii) (bis)(poly)halo(C1-C12)(alkyl)sulfonylimides such as bis(trifluoromethylsulfonyl)imide and bis(fluorosulfonyl)imide, iv) (C1-C12)alkyl sulfates, v) (poly)halophosphates such as hexafluorophosphate, vi) (C1-C12)(alkyl)phosphates such as phosphate, vii) (poly)haloborates such as tetrafluoroborate, viii) carbonate, ix) bicarbonate, x) (C1-C12)alkyl carbonates, xi) dicyanamide, xii) nitrate, xiii) thiocyanate, xiv) formate, xv) (C1-C12)alkyl carboxylates of which the (C1-C12)alkyl group can be substituted with one or more halogen atoms or groups chosen from hydroxyl, (C1-C6)(di)(alkyl)amino, phenyl, imidazole, (C1-C4)alkylcarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonylamino, guanidine, thiol, —SO3H, (C1-C8)alkoxy such as trifluoroacetate; xvi) (C1-C20)alkene carboxylates of which the (C1-C20)alkene group can have one or more double bonds and can be substituted with one or more hydroxyl groups; xvii) (C6-C12)arylcarboxylates of which the aryl group can be substituted with one or more halogen atoms or groups chosen from hydroxyl, (C1-C6)(di)(alkyl)amino, phenyl, imidazole, (C1-C4)alkylcarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonylamino, guanidine, thiol, —SO3H, (C1-C8)alkoxy; xviii) (C1-C12)alkylsulfonates of which the (C1-C12)alkyl group can be substituted with one or more halogen atoms or groups chosen from hydroxyl, (C1-C6)(di)(alkyl)amino, phenyl, imidazole, (C1-C4)alkylcarbonyle, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonylamino, guanidine, thiol, —SO3H, (C1-C8)alkoxy such as triflate, in particular (C1-C6)alkylsulfonates such as methylsulfonate or mesylate; and xix) (C6-C12)arylsulfonates of which the aryl group can be substituted with one or more halogen atoms or groups chosen from hydroxyl, (C1-C6)(di)(alkyl)amino, phenyl, imidazole, (C1-C4)alkylcarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonylamino, guanidine, thiol, —SO3H, (C1-C8)alkoxy such as benzenesulfonate and toluenesulfonate or tosylate; preferably Y- represents an anionic counterion chosen from:
more preferentially, Y- represents an anionic counterion chosen from:
even more preferentially Y- represents an anionic counterion chosen from:
According to one particularly preferred embodiment, the salt(s) of formula (A) are chosen from the compounds 4a, 4b, 4c and 4d below, and mixtures thereof:
The salt(s) of formula (A) can be present in the composition in a total content ranging from 1% to 99.5% by weight, preferably from 3% to 90% by weight, more preferentially from 5% to 80% by weight, even more preferentially from 5% to 60% by weight, most preferentially from 5% to 50% by weight, and better still from 5% to 40% by weight relative to the total weight of the composition.
The composition according to the present invention preferably comprises d) one or more peroxygenated salts. The peroxygenated salts are preferably chosen from persulfates, perborates or percarbonates of alkali metals or alkaline-earth metals or of ammonium, and mixtures thereof, more preferentially from sodium, potassium or ammonium persulfates, and mixtures thereof.
The peroxygenated salt(s) d) are preferably present in the composition in a total content ranging from 0.1% to 50% by weight, preferably ranging from 1% to 25% by weight, relative to the total weight of the composition.
The composition according to the present invention preferably comprises e) one or more alkaline agents. The alkaline agents are preferably chosen from aqueous ammonia, alkanolamines such as monoethanolamine, urea, ammonium salts such as ammonium chloride, ammonium sulfate, ammonium phosphate or ammonium nitrate, and silicates, phosphates or carbonates of alkali metals or alkaline-earth metals, such as lithium, sodium, potassium, magnesium, calcium and barium, and mixtures thereof. Preferably, the alkaline agent(s) are chosen from aqueous ammonia, monoethanolamine, and silicates, such as sodium silicate, and mixtures thereof.
The alkaline agent(s) e) are preferably present in the composition in a total content ranging from 0.01% to 40% by weight, preferably from 0.1% to 30% by weight, relative to the total weight of the composition.
The composition according to the invention is a cosmetic composition, i.e. it is in a cosmetic medium.
The term “cosmetic medium” is intended to mean a medium that is suitable for dyeing keratin fibers, also known as a dye support, which is a cosmetic medium generally formed from water or from a mixture of water and one or more organic solvents or from a mixture of organic solvents.
The composition preferably comprises water in a content ranging from 5% to 99% by weight, more preferentially ranging from 5% to 95% by weight, relative to the total weight of the composition.
The term “organic solvent” is intended to mean an organic substance that is capable of dissolving another substance without chemically modifying it.
Mention may be made, as organic solvent, for example, of lower C2-C4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers, such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and diethylene glycol monomethyl ether, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
The organic solvents are present in proportions preferably ranging from 0.1% to 40% by weight, more preferentially from 1% to 30% by weight, even more preferentially from 1% to 25% by weight, relative to the total weight of the composition.
According to one preferred embodiment, the composition according to the invention comprises:
According to another preferred embodiment, the composition according to the invention comprises:
The pH of the composition according to the invention is preferably from 3 to 12, more preferentially from 5 to 11, even more preferentially from 8 to 10.5.
The pH of this composition may be adjusted with acidifying or alkaline agents conventionally used in cosmetics.
Among the acidifying agents, examples that may be mentioned include organic or mineral acids.
The term “mineral acid” is intended to mean any acid derived from a mineral compound. Among the mineral acids, mention may be made of hydrochloric acid, orthophosphoric acid, sulfuric acid, sulfonic acids and nitric acid.
The term “organic acid” is intended to mean any acid derived from an organic compound. Among the organic acids, mention may be made of acetic acid, tartaric acid, citric acid, lactic acid and sulfonic acids.
Use may notably be made of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.
Among the alkaline agents, examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines, such as monoethanolamine, diethanolamine and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (B) below:
Formula (B) wherein W is a (C1-C6)alkylene group optionally substituted with one or more hydroxyl groups; Ra, Rb, Rc and Rd, which may be identical or different, represent a hydrogen atom or a (C1-C4)alkyl group optionally substituted with one or hydroxyl groups. Preferably, the pH modifiers may be chosen from alkaline agents, such as aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine or an alkaline hydroxide, such as 2-amino-2-methyl-1-propanol, or else acidifying agents, such as phosphoric acid or hydrochloric acid.
The composition according to the invention may be in liquid form, in the form of a serum, in thickened form, in particular a gel, a cream, a wax or a paste, or in foam form.
The composition according to the invention may also comprise one or more additional compounds chosen from nonionic, anionic, cationic or amphoteric surfactants, cationic, anionic, nonionic or zwitterionic, associative or nonassociative thickening polymers of natural or synthetic origin, silicones in the form of oil, gums or resins or non-silicone plant, mineral or synthetic oils, UV-screening agents, fillers, such as nacres and metal oxides such as titanium dioxides, clays, fragrances, peptizers, vitamins and preserving agents.
According to a second aspect, a subject of the present invention is a process for simultaneous bleaching and dyeing of keratin fibers, comprising the application to the keratin fibers of a composition as defined previously.
The composition may be applied to wet or dry keratin fibers.
Preferably, the application to the keratin fibers of the composition according to the invention is carried out at ambient temperature, i.e. at a temperature of between 25° C. and 30° C.
The process can comprise a step consisting in leaving the composition on the keratin fibers for a time ranging from 5 min to 60 min.
According to one advantageous variant of the invention, after application of the composition or after the leave-on time, if present, has elapsed, the keratin fibers are rinsed, optionally shampooed, and then left to dry or dried, for example at a temperature of greater than or equal to 30° C.
According to one particular embodiment, this temperature is greater than 40° C. According to one particular embodiment, this temperature is greater than 45° C. and less than 220° C.
Preferably, if the keratin fibers are dried, they are dried, in addition to a supply of heat, with a flow of air.
During the drying, a mechanical action may be exerted on the fibers, such as combing, brushing or running the fingers through. This operation may similarly be carried out once the keratin fibers have dried, naturally or otherwise.
The drying step may be carried out with a drying device such as a hood, a hairdryer or a Climazon.
The drying step can be carried out with a hood or a hairdryer, the drying temperature ranging from 40° C. to 110° C., preferably from 50° C. to 90° C.
Once the drying is complete, final rinsing or shampooing may optionally be performed. The composition is applied to the wet or dry keratin fibers, preferably with a weight ratio of the amount of composition applied relative to the amount of hair ranging from 0.1 to 10, and more particularly ranging from 0.2 to 7.5.
According to a third aspect, a subject of the present invention is a multi-compartment device or kit, comprising:
In the embodiments according to which the composition of the invention comprises d) one or more peroxygenated salts and/or e) one or more alkaline agents, they may be present in the composition contained in the second or the third compartment.
The technical features defined previously regarding the various ingredients of the composition according to the present invention also apply to the ingredients of the kit.
The examples that follow will allow the invention to be understood more clearly, without, however, being limiting in nature.
The following compositions were prepared and then applied according to the application protocol described below:
In a trough, 10 g of composition 1, 2 or 3 are applied to a lock of 1 g of Caucasian hair with a tone depth of 4 (TD4) for 50 min at a temperature of 33° C. The lock of hair is then rinsed, shampooed and dried.
The color build-up (ΔE*) was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3610A colorimeter, (illuminant D65). In this L* a* b* system, L* represents the intensity of the color, a* indicates the shade of the color on the green/red color axis and b* indicates the shade of the color on the blue/yellow color axis. The lower the value of L*, the darker or more intense the color. The higher the value of a*, the redder the shade, and the higher the value of b*, the bluer the shade.
In the table below, the value of ΔE* is calculated from the L*a*b* values according to the following equation:
In the equation, L*, a* and b* represent the values measured on the locks after treatment by means of the protocol above, and L0*, a0* and b0* represent the values measured on control locks treated with composition 1.
The higher the value of ΔE*, the better the build-up of the dye.
The results of the measurements are indicated in the following table:
It is seen from the above results that the color build-up is significantly improved by the presence of a salt of formula (A) according to the present invention.
The following compositions were prepared and then applied according to the application protocol described below:
In a trough, 10 g of composition 4, 5 or 6 are applied to a lock of 1 g of TD4 Caucasian hair for 50 min at a temperature of 33° C. The lock of hair is then rinsed, shampooed and dried.
The color build-up (ΔE*) was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3610A colorimeter, (illuminant D65). In this L* a* b* system, L* represents the intensity of the color, a* indicates the shade of the color on the green/red color axis and b* indicates the shade of the color on the blue/yellow color axis. The lower the value of L*, the darker or more intense the color. The higher the value of a*, the redder the shade, and the higher the value of b*, the bluer the shade.
In the table below, the value of ΔE* is calculated from the L*a*b* values according to the following equation:
In the equation, L*, a* and b* represent the values measured on the locks after treatment by means of the protocol above, and L0*, a0* and b0* represent the values measured on control locks treated with composition 4.
The higher the value of ΔE*, the better the build-up of the dye.
The results of the measurements are indicated in the following table:
It is seen from the above results that the color build-up is significantly improved by the presence of a salt of formula (A) according to the present invention.
The following compositions were prepared and then applied according to the application protocol described below:
In a trough, 10 g of composition 7, 8 or 9 are applied to a lock of 1 g of 90% white natural Caucasian hair for 50 min at a temperature of 33° C. The lock of hair is then rinsed, shampooed and dried.
The color build-up (ΔE*) was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3610A colorimeter, (illuminant D65). In this L* a* b* system, L* represents the intensity of the color, a* indicates the shade of the color on the green/red color axis and b* indicates the shade of the color on the blue/yellow color axis. The lower the value of L*, the darker or more intense the color. The higher the value of a*, the redder the shade, and the higher the value of b*, the bluer the shade.
In the table below, the value of ΔE* is calculated from the L*a*b* values according to the following equation:
In the equation, L*, a* and b* represent the values measured on the locks after treatment by means of the protocol above, and L0*, a0* and b0* represent the values measured on control locks treated with composition 7.
The higher the value of ΔE*, the better the build-up of the dye.
The results of the measurements are indicated in the following table:
It is seen from the above results that the color build-up is significantly improved by the presence of a salt of formula (A) according to the present invention.
The following compositions were prepared and then applied according to the application protocol described below:
In a trough, 10 g of composition 10, 11 or 12 are applied to a lock of 1 g of 90% white natural Caucasian hair for 50 min at a temperature of 33° C. The lock of hair is then rinsed, shampooed and dried.
The color build-up (ΔE*) was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3610A colorimeter, (illuminant D65). In this L* a* b* system, L* represents the intensity of the color, a* indicates the shade of the color on the green/red color axis and b* indicates the shade of the color on the blue/yellow color axis. The lower the value of L*, the darker or more intense the color. The higher the value of a*, the redder the shade, and the higher the value of b*, the bluer the shade.
In the table below, the value of ΔE* is calculated from the L*a*b* values according to the following equation:
In the equation, L*, a* and b* represent the values measured on the locks after treatment by means of the protocol above, and L0*, a0* and b0* represent the values measured on control locks treated with composition 10.
The higher the value of ΔE*, the better the build-up of the dye.
The results of the measurements are indicated in the following table:
It is seen from the above results that the color build-up is significantly improved by the presence of a salt of formula (A) according to the present invention.
Number | Date | Country | Kind |
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2006566 | Jun 2020 | FR | national |
Filing Document | Filing Date | Country | Kind |
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PCT/EP2021/066705 | 6/18/2021 | WO |