WO2020189793A1 - Procédé et kit pour la coloration de fibres de kératine - Google Patents

Procédé et kit pour la coloration de fibres de kératine Download PDF

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Publication number
WO2020189793A1
WO2020189793A1 PCT/JP2020/012568 JP2020012568W WO2020189793A1 WO 2020189793 A1 WO2020189793 A1 WO 2020189793A1 JP 2020012568 W JP2020012568 W JP 2020012568W WO 2020189793 A1 WO2020189793 A1 WO 2020189793A1
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composition
keratin fibers
acid
dye
compartment
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PCT/JP2020/012568
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English (en)
Inventor
Mathilde GHAFAR
Tomotaka Michitsuji
Celine Bossard
Dhimoy ROY
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L'oreal
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Publication of WO2020189793A1 publication Critical patent/WO2020189793A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4322—Direct dyes in preparations for temporarily coloring the hair further containing an oxidizing agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a process, in particular a coloring process, for keratin fibers such as hair, and a kit used for the process.
  • oxidative bases such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidative bases are generally combined with couplers.
  • couplers are colorless or weakly colored compounds which, combined with oxidizing products, can give rise to colored compounds through an oxidative condensation process.
  • This type of coloring by oxidation makes it possible to obtain colors with very high visibility, and the ability to cover white hair in a wide variety of shades but it results in damage to the keratin fibers due to the use of oxidizing agents and alkaline agents (in particular by repeated application or by combination with other hair treatments).
  • direct dyes are in particular the following: benzene nitrates, anthraquinones, nitropyridines, azos, xanthines, acridines, azines, and triarylmethane-type or natural colorings.
  • Hair coloring using direct dyes has advantages over hair coloring using oxidative dyes: it rarely gives rise to allergy issues, it causes less damage to the hair, and it gives vivid color visibility, but has a disadvantage of less color lastingness to shampoos.
  • WO 2018/229295, WO 2018/229296, and WO 2012/113724 disclose compositions for dyeing hair including direct dyes.
  • An objective of the present invention is to provide a new process for coloring keratin fibers, such as hair, which can provide keratin fibers with improved color lastingness using a direct dye.
  • the above objective of the present invention can be achieved by a process for coloring keratin fibers, preferably hair, comprising the steps of:
  • the process may further comprise an additional step of leaving the first composition on the keratin fibers for a certain amount of time between steps (ii) and (iii), ranging from 10 seconds to 2 hours, preferably from 1 minute to one hour, more preferably from 5 minutes to 50 minutes, and in particular from 10 minutes to 40 minutes.
  • the process may further comprise an additional step of leaving the second composition on the keratin fibers for a certain amount of time between steps (iv) and (v), ranging from 10 seconds to 30 minutes, preferably from 1 minute to 20 minutes, and more preferably from 2 minutes to 10 minutes.
  • the reducing agent may be selected from thiol reducing agents, such as thioglycolic acid, thiolactic acid, glyceryl monothioglycolate, cysteamine, N-acetylcysteamine,
  • N-(mercaptoalkyl)succinimide acid derivatives alkylaminomercaptoalkylamides, the azeotropic mixture of 2-hydroxypropyl thioglyconate and of (2-hydroxy- l-methyl)ethyl thioglycolate, mercaptoalkylaminoamides, N-mercaptoalkylalkanediamides,
  • formamidinesulfmic acid derivatives and salts thereof, in particular ammonium salts, such as ammonium thioglycolate and ammonium thiolactate.
  • the reducing composition may comprise at least one alkaline agent preferably selected from inorganic ammonium salts such as ammonium carbonate, ammonium hydroxide, ammonium bicarbonate; and alkylammonium hydroxide.
  • alkaline agent preferably selected from inorganic ammonium salts such as ammonium carbonate, ammonium hydroxide, ammonium bicarbonate; and alkylammonium hydroxide.
  • the oxidizing agent may be selected from hydrogen peroxide and bromate derivatives.
  • the direct dye may be selected from acidic, basic, or neutral synthetic direct dyes such as acidic, basic, or neutral anthraquinone, nitropyridine, azo, xanthene, acridine, azine or triarylmethane direct dyes.
  • the dye composition may comprise at least one fatty material.
  • the process does not include heating the keratin fibers while the first composition or the second composition is left on the keratin fibers.
  • the pH of the first composition may range from 7.0 to 11.0, preferably from 8.0 to 10.0, and more preferably from 8.5 to 9.5.
  • the pH of the second composition may range from 2.0 to 6.0, preferably from 2.0 to 5.0, and more preferably from 2.5 to 4.0.
  • the (a) dye composition and (b) reducing composition may be mixed with the weight ratio of the dye composition to the reducing composition being from 49:1 to 1:1, preferably from 24:1 to 2:1, more preferably from 19:1 to 3:1, and in particular from 14:1 to 4:1.
  • the present invention also relates to a kit for coloring keratin fibers, such as hair, comprising: a first compartment including a dye composition comprising at least one direct dye except fluorescent disulfide, thiol and protected-thiol direct dyes ,
  • a second compartment including a reducing composition comprising at least one reducing agent
  • a third compartment including a second composition comprising at least one oxidizing agent.
  • the first compartment and the second compartment may be provided so that the dye composition in the first compartment and the reducing composition in the second
  • the first compartment and the second compartment may be provided adjacent to each other, and the third compartment may be provided together with or separately from the first compartment and the second compartment.
  • the process and composition according to the present invention can be used to color keratin fibers, preferably hair, and can provide the keratin fibers with improved color lastingness even after shampooing the keratin fibers.
  • the process according to the present invention can enhance the fiber color lastingness.
  • one aspect of the present invention is a process for coloring keratin fibers, preferably hair, comprising the steps of:
  • fluorescent disulfide, thiol and protected-thiol direct dyes with (b) at least one reducing composition comprising at least one reducing agent, to prepare a first composition;
  • Another aspect of the present invention is a kit that can be used for the process of the present invention above.
  • the process according to the present invention is a process for coloring keratin fibers, preferably hair, comprising the steps of:
  • fluorescent disulfide, thiol and protected-thiol direct dyes with (b) at least one reducing composition comprising at least one reducing agent, to prepare a first composition;
  • the process according to the present invention is intended for coloring keratin fibers such as hair, with direct dyes.
  • the process according to the present invention only two different types of compositions are applied onto the keratin fibers, i.e. the first composition and the second composition.
  • the process has a benefit in that the process time can be shortened so that other processes using three or more types of compositions are applied onto the keratin fibers.
  • the process does not comprise a step of heating keratin fibers other than the drying step in optional step (v). Therefore, steps (i) to (iv) in the process according to the present invention preferably do not include heating the keratin fibers, for example, to 70°C or more, preferably to 60°C or more, and more preferably to 50°C or more. In other words, the process according to the present invention does not include heating the keratin fibers while the first composition or the second composition is left on the keratin fibers.
  • Step (i) is a step of preparing the first composition by mixing (a) at least one dye composition and (b) at least one reducing composition.
  • the mixing ratio of the dye composition and the reducing composition is not particularly limited.
  • the weight ratio of the dye composition to the reducing composition may be from 49:1 to 1 :1, preferably from 24:1 to 2:1, more preferably from 19: 1 to 3:1, and in particular from 14: 1 to 4: 1.
  • the first composition may comprise a greater amount of the dye composition than the reducing composition.
  • the pH of the first composition may be adjusted to the desired value. It is preferable that the pH of the first composition of the present invention be from 7.0 to 11.0, preferably from 8.0 to 10.0, and more preferably from 8.5 to 9.5.
  • the process according to the present invention may further include a pre-treatment step of the keratin fibers.
  • the keratin fibers can be treated with a composition comprising at least one reducing agent.
  • the reducing agent is explained below. Therefore, the process according to the present invention may include an additional step of applying on the keratin fibers, such as hair, a composition comprising the reducing agent of the present invention prior to step (i).
  • step (i) is carried out from 1 second to 20 minutes prior to step (ii), more preferentially between 10 seconds and 5 minutes prior to step (ii).
  • the dye composition and the reducing composition are each explained in a detailed manner below.
  • the (a) dye composition of the present invention includes at least one direct dye.
  • the pH of the dye composition may preferably be from 3.0 to 7.0, preferably from 4.0 to 6.5, and more preferably from 4.5 to 6.0.
  • the dye composition can be provided in forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, a lotion, a milky lotion, a cream, a foam, a paste, a serum or the like.
  • the (a) dye composition of the present invention includes at least one direct dye except fluorescent disulfide, thiol and protected-thiol direct dyes. Two or more direct dyes except fluorescent disulfide, thiol and protected-thiol direct dyes may be used in combination. Thus, a single type of direct dye or a combination of different types of direct dyes may be used.
  • a direct dye means a colored substance which does not require the use of an oxidizing agent in order to develop its color.
  • the direct dye used in the present invention does not comprise fluorescent disulfide, thiol and protected-thiol direct dyes. Therefore, the first composition of the present invention also does not include fluorescent disulfide, thiol and protected-thiol direct dyes.
  • fluorescent disulfide direct dye here means a fluorescent direct dye comprising at least one fluorescent chromophore and at least one disulfide bond: -S-S- between two carbon atoms which indirectly bond to the chromophore of the dye.
  • fluorescent thiol direct dye here means a fluorescent direct dye comprising at least one chromophore and at least one thiol function -SY in which Y is i) a hydrogen atom; ii) an alkali metal; iii) an alkaline-earth metal; iv) an ammonium group: N + R a R b R g R d or a
  • R a R b R g R d with R a , R b , R 8 and R d , which may be identical or different, representing a hydrogen atom or a (Ci-C4)alkyl group, wherein the thiol function -SY directly ' or indirectly bonds to the chromophore of the dye.
  • fluorescent protected-thiol direct dye here means a fluorescent direct dye comprising at least one chromophore and at least one protected-thiol function -SY in which Y is a protecting group known to those skilled in the art, for instance those described in the publications“ Protective Groups in Organic Synthesis”, T.W. Greene, John Wiley & Sons ed., NY, 1981, pp. 193-217;“ Protecting Groups”, R Kocienski, Thieme, 3rd ed., 2005, Chap. 5; and IJllmann’s Encyclopedia,“ Peptide Synthesis”, pp. 4-5, 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007. al9 157, wherein said protected-thiol function directly or indirectly bonds to the chromophore of the dye.
  • direct dye means natural and/or synthetic dyes, which are soluble in the cosmetic medium, other than oxidation dyes which absorb color in the visible spectrum, i.e. which appear to be visually colored; they are dyes which will diffuse superficially on the keratin fibres.
  • natural direct dye is understood to mean any dye or dye precursor that is naturally occurring and is produced by extraction (and optionally by purification) from a plant matrix or an animal such as an insect, optionally in the presence of natural compounds such as ash or ammonia.
  • natural direct dyes mention may be made of quinone dyes (such as lawsone and juglone), alizarin, purpurin, laccaic acid, carminic acid, kermesic acid, purpurogallin,
  • indigoids such as indigo, sorghum, isatin, betanin, curcuminoids (such as curcumin), spinulosin, various types of chlorophyll and chlorophyllin, hematoxylin, hematein, brazilein, brazilin, safflower dyes (such as carthamin), flavonoids (such as rutin, quercetin, catechin, epicatechin, morin, apigenidin, and sandalwood), anthocyans (such as apigeninidin and apigenin), carotenoids, tannins, orceins, santalins and cochineal carmine.
  • indigoids such as indigo, sorghum, isatin, betanin, curcuminoids (such as curcumin), spinulosin, various types of chlorophyll and chlorophyllin, hematoxylin, hematein, brazilein, brazilin, safflower dye
  • extracts or decoctions containing natural direct dye(s) in particular henna-based extracts, curcuma longa extract, sorghum leaf-sheath extract, haematoxylon campechianum extract, green tea extract, pine bark extract, cocoa extract, and logwood extract.
  • the natural direct dye be chosen from the group consisting of
  • curcuminoids santalins, chlorophyllin, haematoxylin, haematein, brazilein, brazilin, sorghum, laccaic acid, lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigoids, isatin, spinulosin, apigenin, orcein, betanin, flavonoids, anthocyans, and extracts or decoctions containing these compounds.
  • the natural direct dyes may be preferably chosen from, for example,
  • hydroxylated quinones indigoids, hydroxyflavones, santalins A and B, isatin and its derivatives, and brasilin and its hydroxylated derivatives.
  • the hydroxylated quinones are preferably benzoquinones, naphthoquinones, and mono- or polyhydroxylated anthraquinones which are optionally substituted with groups such as alkyl, alkoxy, alkenyl, chloro, phenyl, hydroxyalkyl and carboxyl.
  • the naphthoquinones are preferably lawsone, juglone, flaviolin, naphthazarin,
  • the benzoquinones are preferably spinulosin, atromentin, aurentioglyocladin,
  • the anthraquinones are preferably alizarin, quinizarin, purpurin, carminic acid, chrysophanol, kermesic acid, rhein, aloe emodin, pseudopurpurin, quinizarincarboxylic acid, frangula emodin, 2-methylquinizarin, 1-hydroxyanthraquinone and 2-hydroxyanthraquinone.
  • the indigoids are preferably indigo, indirubin, isoindigo and Tyrian purple.
  • the hydroxyflavones are preferably quercetin and morin.
  • synthetic direct dye is understood to mean any dye or dye precursor that is produced by chemical synthesis.
  • the direct dye can be selected from the group consisting of acidic (anionic) direct dyes, basic (cationic) direct dyes, and neutral (nonionic) direct dyes.
  • Non-limiting examples of synthetic dyes include (nonionic) neutral, anionic (acidic), and cationic (basic) dyes such as azo, methine, carbonyl, azine, nitro(hetero)aryl types or tri(hetero)arylmethane direct dyes, porphyrins and phthalocyanines, alone or as mixtures.
  • dyes of the family of the carbonyls mention may be made, for example, of synthetic dyes chosen from acridone, benzoquinone, anthraquinone, naphthoquinone, benzanthrone, anthranthrone, pyranthrone, pyrazolanthrone, pyrimidinoanthrone, flavanthrone, indanthrone, flavone, (iso)violanthrone, isoindolinone, benzimidazolone, isoquinolinone, anthrapyridone, pyrazoloquinazoline, perinone, quinacridone, quinophthalone, naphthalimide, anthrapyrimidine, diketopyrrolopyrrole or coumarin dyes.
  • synthetic dyes chosen from acridone, benzoquinone, anthraquinone, naphthoquinone, benzanthrone, anthranthrone, pyran
  • dyes of the family of the cyclic azines mention may in particular be made of azine, xanthene, thioxanthene, fluorindine, acridine, (di)oxazine, (di)thiazine or pyronine dyes.
  • nitro(hetero)aromatic dyes are more particularly nitrobenzene or nitropyridine direct dyes.
  • cationic or noncationic compounds optionally comprising one or more metals or metal ions, such as, for example, alkali and alkaline earth metals, zinc and silicon.
  • nitrobenzene dyes azo, azomethine or methine direct dyes
  • azacarbocyanines such as tetraazacarbocyanines (tetraazapentamethines), quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes, or azine, xanthene, triarylmethane, indoamine, phthalocyanine and porphyrin direct dyes, alone or as mixtures.
  • these synthetic direct dyes are chosen from nitrobenzene dyes, azo, azomethine or methine direct dyes and tetraazacarbocyanines (tetraazapentamethines); alone or as mixtures.
  • D represents a nitrogen atom or the -CH group
  • Ri and R 2 which are identical or different, represent a hydrogen atom; a C1-C4 alkyl radical which can be substituted by a -CN, -OH or -NH 2 radical or can form, with a carbon atom of the benzene ring, an optionally oxygen-comprising or nitrogen-comprising heterocycle which can be substituted by one or more C 1 -C 4 alkyl radicals; or a 4'-aminophenyl radical,
  • R 3 and R’ 3 which are identical or different, represent a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a cyano radical, a C1-C4 alkyl radical, a C 1 -C 4 alkoxy radical or an acetyloxy radical,
  • X represents an anion, preferably chosen from chloride, methyl sulphate and acetate,
  • A represents a group chosen from the following structures:
  • R 5 represents a hydrogen atom, a C 1 -C 4 alkoxy radical or a halogen atom, such as bromine, chlorine, iodine or fluorine,
  • R 6 represents a hydrogen atom or a C 1 -C 4 alkyl radical or forms with a carbon atom in the benzene ring, a heterocycle which optionally comprises oxygen and/or is optionally substituted by one or more C 1 -C 4 alkyl groups,
  • R 7 represents a hydrogen atom or a halogen atom, such as bromine, chlorine, iodine or fluorine,
  • X represents a cosmetically acceptable anion preferably chosen from chloride, methyl sulphate and acetate,
  • E represents a group chosen from the following structures:
  • R’ represents a C 1 -C 4 alkyl radical
  • R’ represents a C 1 -C 4 alkyl radical.
  • the synthetic direct dye may be selected from fluorescent dyes. Two or more types of fluorescent dyes may be used in combination.
  • the fluorescent dyes according to the present invention contain one or more colored and fluorescent cliromophores.
  • these fluorescent dyes when applied to dark hair, may also make it possible to lighten the hair without damaging it.
  • fluorescent dyes is understood to mean fluorescent compounds and optical brighteners.
  • the fluorescent dye is soluble in the medium of the composition.
  • Fluorescent dyes are fluorescent compounds which absorb visible radiation, for example, wavelengths ranging from 400 to 800 nm, and which are capable of re-emitting light in the visible region at a higher wavelength.
  • the fluorescent dyes useful for the present invention re-emit orange-colored fluorescent light. They exhibit, for instance, a maximum re-emission wavelength ranging from 500 to 700 nm.
  • Non-limiting examples of fluorescent dyes include compounds known in the art, for example, those described in Ullmann's Encyclopedia of Industrial Chemistry, Release 2004, 7th edition, “Fluorescent Dyes” chapter.
  • optical brighteners of the present disclosure also known under the name “brighteners”, or “fluorescent brighteners”, or “fluorescent brightening agents” or “FWA”, or “fluorescent whitening agents”, or “whiteners”, or “fluorescent whiteners”, are colorless transparent compounds as they do not absorb in visible light but only in ultraviolet light (wavelengths ranging from 200 to 400 nanometers) and convert the energy absorbed into fluorescent light of higher wavelength emitted in the visible part of the spectrum, generally in the blue and/or green, that is to say in wavelengths ranging from 400 to 550 nanometers.
  • Optical brighteners are known in the art, for example, they are described in Ullmann's Encyclopedia of Industrial Chemistry (2002), “Optical Brighteners” and Kirk-Othmer Encyclopedia of Chemical Technology (1995): “Fluorescent Whitening Agents”.
  • Soluble fluorescent compounds that may especially be mentioned include those belonging to the following families: naphthalimides, coumarins, xanthenes and in particular
  • xanthenodiquinolizines and azaxanthenes naphtholactams; azlactones; oxazines; thiazines; dioxazines; azo compounds; azomethines; methines; pyrazines; stilbenes; ketopyrroles; and pyrenes.
  • the direct dye may be selected from the group consisting of acidic direct dyes, basic direct dyes and neutral direct dyes, which covers all possible types of direct dyes, such as so-called nitro dyes and HC dyes.
  • Acidic direct dyes have an anionic moiety in their chemical structure.
  • Basic direct dyes have a cationic moiety in their chemical structure.
  • Neutral direct dyes are nonionic.
  • the direct dye comprises at least one acidic direct dye.
  • anionic direct dyes are commonly known as " acidic direct dyes” for their affinity with alkaline substances (see, for example, “ Industrial Dyes, Chemistry, Properties, Application”, Klaus Hunger Ed. Wiley-VCH Verlag GmbH & Co KGaA, Weinheim 2003).
  • Anionic or acid dyes are known in the literature (see, for example, “ Ullman Encyclopedia of Industrial Chemistry”, Azo Dyes, 2005 Wiley-YCH Verlag GmbH & Co. KGaA, Weinheim
  • the preferred anionic dyes of the formula of the present invention are chosen from acidic nitro direct dyes, acidic azo dyes, acidic azine dyes, acidic triarylmethane dyes, acidic indoamine dyes, acidic anthraquinone dyes, anionic styryl dyes, and indigoids and acidic natural dyes; each of these dyes containing at least one sulfonate, phosphonate or carboxylate group bearing a cationic counterion X + , where X + represents an organic or mineral cationic counter ion preferably chosen from alkali and alkaline-earth metals, such as Na + and K +
  • Preferred acid dyes may be chosen from:
  • R.7, RS, R9, RIO, R'7, R'S, R'9 and R'io which may be identical or different, represent a hydrogen atom or a group chosen from:
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • R”-S(0) 2 - with R” representing a hydrogen atom or an alkyl, aryl, (di)(alkyl)amino or aryl(alkyl)amino group; preferably a phenylamino or phenyl group;
  • R’ S(0) 2 -X’- with R’” representing an alkyl or optionally substituted aryl group, X’ as defined previously;
  • aryl(alkyl)amino optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (0) 2 S(0 )-, X + and iv) alkoxy with X + ;
  • heteroaryl preferably a benzothiazolyl group
  • cycloalkyl especially cyclohexyl
  • Ar-N N- with Ar representing an optionally substituted aryl group, preferably a phenyl optionally substituted with one or more alkyl, (0)2S(0 )-, X + or phenylamino groups;
  • R7 with Rs or Rs with R9 or R9 with Rio together form a fused benzo group A’; and R’7 with R’s or R’s with R’9 or R’9 with R’10 together form a fused benzo group B’; with A’ and B’ optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (0)2S(0 )-, X + ; iv) hydroxyl; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X’-; viii) R°-X’-C(X)-; ix)
  • W represents a sigma bond s, an oxygen or sulfur atom, or a divalent radical i) -NR- with R as defined previously, or ii) methylene -C(R a )(Rb)- with R a and Rb, which may be identical or different, representing a hydrogen atom or an aryl group, or alternatively R a and R b form, together with the carbon atom that bears them, a spiro cycloalkyl; preferably W represents a sulfur atom or R a and R b together form a cyclohexyl;
  • formulae (II) and (IF) comprise at least one sulfonate (0)2S(0 )-, X + or phosphonate (0)P(0 2 ) 2X + or carboxylate (O)C(O )-, X + radical on one of the rings A, A', B, B' or C with X + as defined previously;
  • dyes of formula (II) 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 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Food Red 17, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, 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
  • dyes of formula (II*) mention may be made of Acid Red 111, Acid Red 134, and Acid Yellow 38;
  • R 22 , R23, R24, R25, R26 and R27 which may be identical or different, represent a hydrogen or halogen atom or a group chosen from:
  • aryloxy or arylthio optionally substituted, preferably substituted with one or more groups chosen from alkyl and (0) 2 S(0 )-, X + with X + as defined previously;
  • aryl(alkyl)amino optionally substituted with one or more groups chosen from alkyl and (0) 2 S(0 )-, X + with X + as defined previously;
  • Z represents a hydrogen atom or a group NR28R29 with R28 and R29, which may be identical or different, representing a hydrogen atom or a group chosen from:
  • polyhydroxyalkyl such as hydroxyethyl
  • aryl optionally substituted with one or more groups, particularly i) alkyl such as methyl, «-dodecyl, «-butyl; ii) (0) 2 S(0 ‘ )-, X + with X + as defined previously; iii) R°-C(X)-X’-, R°-X’-C(X)-, R°-X’-C(X)-X”- with R°, X, X’ and X” as defined previously, preferably R° represents an alkyl group;
  • cycloakyl especially cyclohexyl
  • Z represents a group chosen from hydroxyl and NR’2sR’29 with R’28 and R’29, which may be identical or different, representing the same atoms or groups as R28 and R29 as defined previously;
  • formulae (III) and (IIG) comprise at least one sulfonate group (0) 2 S(0 )-, X + with X + as defined previously;
  • dyes of formula (III) 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,
  • HC Blue 16 which is a cationic anthraquinone dye, Acid Green 25, Acid Green 41, Acid
  • R.61 represents a hydrogen or halogen atom or an alkyl group
  • R.62, R63 and R.64 which may be identical or different, represent a hydrogen atom or a group (0) 2 S(0 ‘ )-, X + with X + as defined previously;
  • R.61 with R62, or Rei with R64 together form a benzo group optionally substituted with one or more groups (0) 2 S(0 ‘ )-, X + with X + as defined previously;
  • G represents an oxygen or sulfur atom or a group NR e with R e representing a hydrogen atom or an alkyl group; particularly G represents an oxygen atom;
  • formula (IV) comprises at least one sulfonate group (0) 2 S(0 )-, X + with X + as defined previously;
  • dyes of formula (IV) mention may be made of Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5:
  • the triarylmethane direct dye(s) according to the present invention are catonic dyes of formulae (Va) and (V'a) below:
  • Ri, R 2 , R 3 and R 4 which may be identical or different, represent a hydrogen atom or one of the following groups: (Ci-C 6 )alkyl which is optionally substituted, preferably with a hydroxyl group; aryl such as phenyl, aryl(Ci-C 4 )alkyl such as benzyl, heteroaryl,
  • heteroaryl(Ci-C 4 )alkyl or else two groups Ri, and R 2 , and/or R3 and R 4 , borne by the same nitrogen atom form, together with the nitrogen atom which bears them, an optionally substituted heterocycloalkyl group such as morpholino, piperazino or piperidino, preferably Ri, R 2 , R 3 and R 4 , which may be identical or different, represent a hydrogen atom or a (Ci-C 4 )alkyl group;
  • R 5 and R6 and/or R7 and Rs and/or R 9 and Rio and/or Rn and R 12 and/or R 13 and R 14 and/or R 15 and Ri6 form, together with the carbon atoms which bear them, an aryl or heteroaryl, preferably benzo, 6-membered fused ring, said ring possibly also being optionally substituted, preferably an unsubstituted benzo ring;
  • Q represents an anionic counterion as defined previously, for achieving electron neutrality of the molecule, preferably chosen from halides such as chloride or bromide, and phosphate;
  • the cationic dye comprises one or more anionic substituents such as COOR or SO3R with R denoting a hydrogen or a cation, it is understood that there are then more cationic substituents than anionic substituents, such that the overall resulting charge of the cationic dye.
  • anionic substituents such as COOR or SO3R with R denoting a hydrogen or a cation
  • triarylmethane structure is cationic, counterbalanced by Q .
  • the direct dye(s) a) of the present invention are chosen from formulae (Va) and (V'a) such as from HC Blue 15, which is a neutral triarylmethane direct dye,
  • the direct dye(s) a) is (are) chosen from the triarylmethane dyes of formula (Va) or (V'a), in which, taken alone or separately,
  • Ri, R 2 , R 3 and R4 represent a hydrogen atom or a (Ci-C4)alkyl group such as methyl or ethyl;
  • R5, R6, R7, R8, R3 ⁇ 4 RIO, Rn, R12, R13, R14, R15, and Ri6 represent a hydrogen atom, a halogen atom, such as chlorine, or a (Ci-C4)alkyl group such as methyl or ethyl, an amino group, a (di)(Ci-C4)(alkyl)amino group and, preferably, at least one of the R9, Rio, R 11 or R 12 groups represents a hydrogen atom, a halogen atom (Cl), or an amino group, or a
  • the direct dye(s) of triaylmethane structure are 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, Basic Blue 77 (also called HC Blue 15), and mixtures thereof.
  • the acidic direct dye be selected from the group consisting of Yellow 5, Orange 4, EXT. Violet 2, Acid Black 1 and Acid Violet 43 (Cl 60730).
  • the direct dye comprise at least one basic direct dye.
  • the basic direct dyes which can be used in the present invention, can include, but are not limited to, Basic Blue 3, Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 41, Basic Blue 99, Basic Brown 4, Basic Brown 16, Basic Brown 17, Basic Green 1, Basic Green 4, Basic Orange 1, Basic Orange 2, Basic Red 1, Basic Red 2, Basic Red 22, Basic Red 46, Basic Red 76, Basic Red 118, Basic Violet 1, Basic Violet 3, Basic Violet 4, Basic Violet 10, Basic Violet 11, Basic Violet 14, Basic Violet 16, Basic Yellow 11, Basic Yellow 28, and Basic Yellow 57.
  • the direct dye comprise at least one neutral (nonionic) direct dye.
  • the neutral (nonionic) direct dyes which can be used in the present invention, can include, but are not limited to, nitro dyes, such as 4-amino-3-nitrophenol, 2-amino-5-nitrophenol, 2-nitro-5 -glyceryl methylaniline, 3 -methylamino-4-nitrophenoxy ethanol,
  • HC dyes such as HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 9, Yellow 10, HC Red 1, HC Red 3, HC Red 7, HC Red 10, HC Red 7, HC Red 11, HC Blue 2, HC Blue 12, HC Blue 14, HC Orange 1, HC Orange 2, HC Violet 1, HC Violet 2, and disperse dyes.
  • the examples of the disperse dyes may include, but are not limited to, Disperse Black 9, Disperse Blue 1, Disperse Blue 3, Disperse Blue 7, Disperse Brown 4, Disperse Orange 3, Disperse Red 11, Disperse Red 15, Disperse Red 17, Disperse Violet 1, Disperse Violet 4, and Disperse Violet 15.
  • the direct dye is selected from acidic, basic, or neutral synthetic direct dyes such as acidic, basic, or neutral anthraquinone, nitropyridine, azo, xanthene, acridine, azine or triarylmethane direct dyes.
  • the direct dye(s) may be included in the dye composition of the present invention in an amount of 0.001% by weight or more, preferably 0.01% by weight or more, and more preferably 0.05% by weight or more; 10% by weight or less, preferably 5% by weight or less, and more preferably 1% by weight or less, relative to the total weight of the composition.
  • the direct dye(s) may be included in the first composition of the present invention in an amount of 0.001% by weight or more, preferably 0.01% by weight or more, and more preferably 0.05% by weight or more; 10% by weight or less, preferably 5% by weight or less, and more preferably 1% by weight or less, relative to the total weight of the composition.
  • the dye composition of the present invention can include at least one fatty material. Two or more fatty materials may be used in combination. Thus, a single type of fatty material or a combination of different types of fatty materials may be used.
  • fatty material means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably 1% and even more preferentially 0.1%).
  • the fatty material may be in the form of a liquid or a solid.
  • “liquid” and“solid” mean that the fatty material is in the form of a liquid or a paste (non-solid) or solid, respectively, at ambient temperature (25°C) under atmospheric pressure (760 mmHg or 10 5 Pa). It is preferable that the fatty material comprise at least one fatty material in the form of a paste or a solid, preferably in the form of a solid, at ambient temperature and under atmospheric pressure.
  • the fatty material may be selected from the group consisting of oils of animal or plant origin, mineral oils, synthetic glycerides, esters of fatty alcohols and/or fatty acids other than animal or plant oils and synthetic glycerides, fatty alcohols, fatty acids, silicone oils and aliphatic hydrocarbons. These fatty materials may be volatile or non-volatile.
  • the fatty material is selected from the group consisting of oils of animal or plant origin, synthetic glycerides, fatty esters other than animal or plant oils and synthetic glycerides, fatty alcohols, fatty acids, silicone oils, and aliphatic hydrocarbons. More preferably, the (b) fatty material is selected from fatty alcohols, aliphatic hydrocarbons, preferably mineral oils, and mixtures thereof.
  • aliphatic hydrocarbons examples include, for example, linear or branched hydrocarbons such as mineral oil (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, polydecenes, hydrogenated polyisobutenes such as Parleam, and decene/butene copolymer; and mixtures thereof.
  • aliphatic hydrocarbons mention may also be made of linear or branched, or possibly cyclic C 6 -Ci 6 lower alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane and isoparaffins such as isohexadecane, isodecane, and C13-C14 isoparaffin.
  • caprylic/capric acid triglycerides for instance those sold by the company, Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company, Dynamit Nobel.
  • silicone oils mention may be made of, for example, linear
  • organopolysiloxanes such as dimethylpolysiloxanes, methylphenylpolysiloxanes,
  • methylhydrogenpolysiloxanes and the like; cyclic organopolysiloxanes such as
  • dodecamethylcyclohexasiloxane and the like; and mixtures thereof.
  • plant oils mention may be made of, for example, linseed oil, camellia oil, macadamia nut oil, sunflower oil, apricot oil, soybean oil, arara oil, hazelnut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, almond oil, grapeseed oil, sesame oil, peanut oil, and mixtures thereof.
  • animal oils mention may be made of, for example, squalene, perhydrosqualene and squalane.
  • esters of a fatty acid and/or of a fatty alcohol which are advantageously different from the animal or plant oils as well as the synthetic glycerides mentioned above, mention may be made especially of esters of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched C1-C26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 -C 15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate;
  • composition may also comprise, as fatty esters, sugar esters and diesters of C6-C30 and preferably C 12 -C 22 fatty acids.
  • sugar esters means oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which contain at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fructose, maltose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be selected especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 and preferably C 12 -C 22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters may be selected, for example, from oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleo-palmitate, oleo-stearate and palmito-stearate mixed esters.
  • the fatty material may include at least one fatty alcohol, and two or more fatty alcohols may be used.
  • fatty alcohol here means any saturated or unsaturated, linear or branched C8-C30 fatty alcohol, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
  • C12-C22 fatty alcohols for example, are used. Mention may be made among these of lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, myristyl alcohol, arachidonyl alcohol and erucyl alcohol, and mixtures thereof.
  • cetyl alcohol, stearyl alcohol or a mixture thereof (e.g., cetearyl alcohol), as well as myristyl alcohol can be used as a solid fatty material.
  • isostearyl alcohol can be used as a liquid fatty material.
  • the fatty material may be a wax.
  • “wax” means that the fatty material is substantially in the form of a solid at room temperature (25 °C) under atmospheric pressure (760 mmHg), and has a melting point generally of 35°C or more.
  • waxy fatty material waxes generally used in cosmetics can be used alone or in combinations thereof.
  • the fatty material(s) may be included in the dye composition of the present invention in an amount of 1% by weight or more, preferably 2% by weight or more, more preferably 3% by weight or more, and even more preferably 4% by weight or more; 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the fatty material(s) may be included in the first composition of the present invention in an amount of 1% by weight or more, preferably 2% by weight or more, more preferably 3% by weight or more, and even more preferably 4% by weight or more; 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the dye composition of the present invention may also comprise at least one additional ingredient.
  • the additional ingredient(s) may be selected from the group consisting of water; organic solvents, in particular water-soluble organic solvents; cationic, anionic, nonionic or amphoteric surfactants; thickeners; cationic, anionic, nonionic or amphoteric polymers;
  • the dye composition of the present invention typically comprises water.
  • the amount of water in the dye composition may be from 50% by weight or more, preferably 60% by weight or more, more preferably 70% by weight or more, and even more preferably 80% by weight or more; 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less, relative to the total weight of the composition.
  • the dye composition of the present invention may include one or two or more of thickeners which may be anionic, cationic, amphoteric or nonionic associative or non-associative polymers, such as sugars, in particular cellulose-based polymers, for example hydroxyethyl cellulose; and associative polyurethanes, such as polyurethane-39.
  • thickeners which may be anionic, cationic, amphoteric or nonionic associative or non-associative polymers, such as sugars, in particular cellulose-based polymers, for example hydroxyethyl cellulose; and associative polyurethanes, such as polyurethane-39.
  • the amount of the thickener(s) in the dye composition may be from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, and more preferably from 0.5 to 10% by weight, relative to the total weight of the composition.
  • the dye composition of the present invention may comprise one or two or more of cationic, anionic, nonionic or amphoteric surfactants.
  • the cationic surfactants may be selected from quaternary ammonium and diammonium salts, such as cetrimonium chloride.
  • the nonionic surfactants may be selected from polyethoxylated fatty alcohols or polyglycerolated fatty alcohols, such as the adducts of ethylene oxide with stearyl alcohol, especially those containing from 2 to 20 oxyethylene units (Steareth-2 to Steareth-20, as the CTFA names).
  • the amount of the surfactant(s) in the dye composition may be from 0.1 to 20% by weight, preferably from 0.2 to 15% by weight, and more preferably from 0.5 to 10% by weight, relative to the total weight of the composition.
  • the (b) reducing composition of the present invention includes at least one reducing agent.
  • the (b) reducing composition comprises at least one alkaline agent to adjust its pH.
  • the pH of the reducing composition may be adjusted to the desired value using the alkaline agent(s) and/or acidic agent(s) commonly used in the field of cosmetics.
  • the pH of the reducing composition of the present invention be from 8.0 to 12.0, preferably from 8.5 to 11.0, and more preferably from 9.0 to 10.0.
  • the reducing composition can be provided in forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, a lotion, a milky lotion, a cream, a foam, a paste, a serum or the like.
  • the emulsion forms is preferably for reducing the smell.
  • the second composition comprises at least one reducing agent.
  • a single type of reducing agent may be used, or two or more different types of reducing agents may be used in combination.
  • any conventional reducing agents in the field of cosmetics may be used.
  • the reducing agent may be selected from thiol reducing agents and non-thiol reducing agents.
  • The“thiol reducing agent” here means a reducing agent with at least one thiol group.
  • the thiol reducing agent may preferably be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol
  • monothioglycolate thiolactic acid and derivatives thereof, in particular esters thereof such as glycerol monothiolactate; 3-mercaptopropionic acid and derivatives thereof, in particular esters thereof such as glycerol 3-mercaptopropionate and ethyleneglycol
  • cysteamine and derivatives thereof in particular C acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine; mono-thioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl esters; thioglycerine and derivatives thereof, in particular s-alkyl derivatives, and salts thereof; mercaptosuccinic acid and derivatives thereof, such as 2,3-dimercaptosuccinic acid, N-(mercaptoalkyl)succinamic acid derivatives, N-(mercaptoalkyl)succinimide acid derivatives, and
  • N-(mercaptoalkyl)succinamic acid derivatives N-mercaptoalkylalkanediamides
  • salts mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amine salts; alkaline metal salts such as sodium and potassium salts; and, alkaline earth metal salts, for example magnesium and calcium salts, amine salts and amino alcohol salts.
  • alkaline metal salts such as sodium and potassium salts
  • alkaline earth metal salts for example magnesium and calcium salts, amine salts and amino alcohol salts.
  • primary-, secondary- or tertiary-amine for example,
  • thiol reducing agent examples include, but are not limited to, sugar N-mercapto alkyl amides such as N-(mercapto-2-ethyl)gluconamide, b-mercaptopropionic acid and derivatives thereof; thiomalic acid; pantetheine; N-(mercaptoalkyl)(o-hydroxyalkyl amides such as those described in European Patent Application No. 0 354 835 and N-mono- or
  • N,N-dialkylmercapto 4-butyramides such as those described in European Patent Application No. 0 368 763; aminomercaptoalkyl amides such as those described in European Patent Application No. 0 432 000 and alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (2/3) hydroxy-2 propyl thioglycolate; the hydroxy-2 methyl- 1 ethyl thioglycolate-based mixture (67/33) described in French Patent Application No. 2 679 448; and the azeotropic mixture of 2-hydroxypropyl thioglyconate and of (2-hydroxy-l-methyl)ethyl thioglycolate.
  • the reducing agent be selected from the group consisting of thioglycolic acid, thiolactic acid, glyceryl monothioglycolate, cysteamine, N-acetylcysteamine,
  • N-(mercaptoalkyl)succinimide acid derivatives alkylaminomercaptoalkylamides, the azeotropic mixture of 2-hydroxypropyl thioglyconate and of (2-hydroxy- l-methyl)ethyl thioglycolate, mercaptoalkylaminoamides, N-mercaptoalkylalkanediamides, formamidinesulfmic acid derivatives, and salts thereof, in particular ammonium salts, such as ammonium thioglycolate and ammonium thiolactate.
  • The“non-thiol reducing agent” here means a reducing agent with no thiol group.
  • the non-thiol reducing agent may preferably be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides. More preferably, the non-thiol reducing agent may be selected from ammonium sulfites and bisulfites as well as metal sulfites and bisulfites, more preferably alkali metal or alkali earth metal sulfites and bisulfites, and more preferably sodium sulfites and bisulfites.
  • sulfinates As the sulfinates, mention may be made of sulfmic acid salts, and benzenesulfinic acid salts such as sodium salts thereof.
  • the sulfmic acid derivatives as described in FR-A-2814948 can also be used.
  • a preferred sulfinate compound is 2-hydroxy-2-sulfinatoacetic acid, disodium salt.
  • the phosphine(s) can be chosen from the compounds of formula (I) below:
  • L is a linker that represents a covalent bond or a divalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from an oxygen atom, a sulfur atom, a nitrogen atom and a silicon atom;
  • n is an integer equal to 0 or 1 ;
  • q is an integer equal to 1 or 2;
  • p is an integer equal to 0 or 1 ;
  • R 31 , R 32 and R 33 which may be identical or different, represent:
  • a monovalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from a sulfur atom, an oxygen atom, a nitrogen atom, a phosphorus atom and a silicon atom, optionally substituted with one or more radicals chosen from:
  • an aromatic or heteroaromatic ring which is unsubstituted or substituted with one or more radicals chosen from a halogen atom, a hydroxyl radical, an alkoxy radical and a mono- or di(alkyl)amino radical,
  • a radical that increases the solubility of the phosphine in water such as sulfonate, sulfmate, phosphonate or carboxylate radicals,
  • the substituents are chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, mono- or dialkylamino, mono- or
  • radical p-methoxyphenyl is a substituted aryl radical.
  • the radicals R 31 , R 32 and R 33 do not simultaneously represent a hydrogen atom.
  • At least one of the radicals R 31 , R 32 and R 33 denotes, as a hydrocarbon-based radical, an optionally substituted alkyl radical.
  • phosphines that are useful in the context of the present invention may be optionally salified with strong mineral acids, for instance HC1, HBr, H2SO4 or HBF4 or organic acids, for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.
  • strong mineral acids for instance HC1, HBr, H2SO4 or HBF4
  • organic acids for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) chosen from monophosphines.
  • q is then preferably equal to 1.
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) diphosphines.
  • phosphine(s) is (are) of formula (I), q is then preferably equal to 2.
  • p is equal to 0 and the linker L is a covalent bond or a divalent radical chosen from a binaphthylene radical; a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N-methyl-N'-methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • a binaphthylene radical a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N-methyl-N'-methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • Preferred non-thiol-based reducing agents are chosen from sulfites, bisulfites and phosphines.
  • the reducing agent may be included in the reducing composition of the present invention in an amount of 1% by weight or more, preferably 3% by weight or more, and more preferably 5% by weight or more; 30% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less, relative to the total weight of the composition.
  • the reducing agent may be included in the first composition of the present invention in an amount of 0.1% by weight or more, preferably 0.3% by weight or more, and more preferably 0.5% by weight or more; 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.
  • the reducing composition of the present invention may further comprise at least one alkaline agent.
  • Two or more alkaline agents may be used in combination.
  • a single type of alkaline agent or a combination of different types of alkaline agents may be used.
  • the alkaline agent may be an inorganic alkaline agent. It may be possible that the inorganic alkaline agent be selected from the group consisting of ammonia; alkaline metal hydroxides; alkaline earth metal hydroxides; alkaline metal phosphates and monohydrogenophosphates such as sodium phosphate or sodium monohydrogenophosphate. However, it is preferable that the (c) alkaline agent not be ammonia because of the odor thereof. Thus, it is preferable that the inorganic alkaline agent be selected from inorganic ammonium salts such as ammonium carbonate, ammonium hydroxide, and ammonium bicarbonate; and
  • alkylammonium hydroxides such as tetramethylammonium hydroxide.
  • inorganic alkaline metal hydroxides mention may be made of sodium hydroxide and potassium hydroxide.
  • alkaline earth metal hydroxides mention may be made of calcium hydroxide and magnesium hydroxide.
  • sodium hydroxide is preferable.
  • the alkaline agent may be an organic alkaline agent. It is preferable that the organic alkaline agent be selected from the group consisting of monoamines and derivatives thereof; diamines and derivatives thereof; polyamines and derivatives thereof; basic amino acids and derivatives thereof; oligomers of basic amino acids and derivatives thereof; polymers of basic amino acids and derivatives thereof; urea and derivatives thereof; and guanidine and derivatives thereof.
  • alkanolamines such as mono-, di- and tri-ethanolamine, and isopropanolamine; urea, guanidine and their derivatives; basic amino acids such as lysine, ornithine or arginine; and diamines such as those described in the structure below: wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C1-C4 alkyl radical, and Ri, R2, R3 and R4 independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Arginine, urea and monoethanolamine are preferable.
  • the alkaline agent can be included so that the pH of the reducing composition can range from 8.0 to 12.0, preferably from 8.5 to 11.0, and more preferably from 9.0 to 10.0.
  • the reducing composition includes at least two alkaline agents different from one another; in particular, one of the alkaline agents is a bicarbonate, more particularly an ammonium bicarbonate, and the other one is a hydroxide more particularly an ammonium hydroxide.
  • the reducing composition of the present invention may also comprise at least one additional ingredient.
  • the additional ingredient(s) may be selected from the group consisting of water; organic solvents, in particular water-soluble organic solvents; fatty materials; cationic, anionic, nonionic or amphoteric surfactants; thickeners; cationic, anionic, nonionic or amphoteric polymers; penetrating agents; agents for combating hair loss; anti-dandruff agents;
  • associative-type or not, natural or synthetic thickeners for fatty materials suspending agents; chelating or sequestering agents, such as EDTA; opacifying agents; dyes other than direct dyes; fragrances; preserving agents, such as chlorhexidine digluconate and phenoxyethanol; stabilizers; and mixtures thereof.
  • the reducing composition of the present invention typically comprises water.
  • the amount of water in the reducing composition may be 40% by weight or more, preferably 50% by weight or more, and more preferably 55% by weight or more; 90% by weight or less, preferably 80% by weight or less, and more preferably 70% by weight or less, relative to the total weight of the composition.
  • the reducing composition of the present invention may comprise one or two or more of cationic, anionic, nonionic or amphoteric surfactants.
  • the nonionic surfactants may be selected from polyethoxylated fatty alcohols or polyglycerolated fatty alcohols, such as the adducts of ethylene oxide with oleyl alcohol, especially those containing from 10 to 30 oxyethylene units (Oleth-10 to Oleth-30, for example Oleth-20, as the CTFA names).
  • the amount of the surfactant(s) in the reducing composition may be from 0.1 to 15% by weight, preferably from 1 to 10% by weight, and more preferably from 2 to 5% by weight, relative to the total weight of the composition.
  • Step (ii) is a step of applying the first composition obtained in step (i) onto the keratin fibers.
  • the application of the first composition may be performed by any means, such as a brush and a comb.
  • Step (iii) is a step of rinsing the keratin fibers in order to remove the first composition from the keratin fibers.
  • the rinse of the keratin fibers may be performed by any means, for example, washing the keratin fiber under running water.
  • the temperature of the water for rinsing is not particularly limited, for example, the temperature of the water is between 10°C to 50°C.
  • steps (ii) and (iii) of leaving the first composition on the keratin fibers for a certain amount of time may be an additional step between steps (ii) and (iii) of leaving the first composition on the keratin fibers for a certain amount of time in order to facilitate the penetration of the first composition into the keratin fibers and to achieve the desired alternation in color.
  • the process according to the present invention further comprises an additional step of leaving the first composition on the keratin fibers for a certain amount of time between steps (ii) and (iii).
  • the leave-on time of the first composition on the keratin fibers can be from 10 seconds to 2 hours, preferably from 1 minute to one hour, more preferably from 5 minutes to 50 minutes, and in particular from 10 minutes to 40 minutes.
  • the keratin fibers be wrapped during the optional leave-on step of the first composition on keratin fibers.
  • the keratin fibers can be wrapped with aluminum foil. Therefore, the process according to the present invention can include an additional step of wrapping the keratin fibers with, for example, aluminum foil after the first composition is applied onto the keratin fibers.
  • step (iii) There also may be an additional step after rinsing the keratin fiber to dry the keratin fibers in the step (iii).
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair drier.
  • the step (iii) does not comprise the step of drying keratin fibers after rinsing the keratin fibers.
  • Step (iv) is a step of applying onto the keratin fibers the second composition comprising at least one oxidizing agent.
  • the application of the second composition may be performed by any means, such as a brush and a comb.
  • the second composition is applied onto wet keratin fibers, such as wet hair.
  • the pH of the second composition according to the present invention be from 2.0 to 6.0, preferably from 2.0 to 5.0, and more preferably from 2.5 to 4.0.
  • the second composition can be provided in forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, a lotion, a milky lotion, a cream, a foam, a paste, a serum or the like.
  • the second composition of the present invention comprises at least one oxidizing agent.
  • a single type of oxidizing agent may be used, or two or more different types of oxidizing agents may be used in combination.
  • the oxidizing agent may be chosen from hydrogen peroxide, peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis, i.e. hydrogen
  • the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates and ferricyanides and persalts such as perborates persulphates, peracids and percarbonates of alkali metals or alkaline-earth metals.
  • At least one oxidase enzyme chosen from, for example, laccases, peroxidases and 2-electron oxidoreductases such as uricase may also be used as the oxidizing agent, where appropriate in the presence of the respective donor or co-factor thereof.
  • the oxidizing agent is hydrogen peroxide, such as an aqueous hydrogen peroxide solution.
  • the hydrogen peroxide concentration may range from 0.15 wt% to 12 wt% such as from 0.6 wt% to 9 wt% relative to the total weight of the oxidizing agent.
  • the concentration of compounds capable of forming hydrogen peroxide by hydrolysis may range from 0.1 wt% to 25 wt% relative to the total weight of the oxidizing agent.
  • the aqueous solution may comprise at least one hydrogen peroxide stabilizer, which may be chosen from, for example, alkali metal and alkaline-earth metal pyrophosphates, alkali metal and alkaline-earth metal stannates, phenacetin and salts of acids and of oxyquinoline, for example, oxyquinoline sulphate.
  • at least one stannate optionally in combination with at least one pyrophosphate is used.
  • the oxidizing agent in the form of an aqueous hydrogen peroxide solution, the
  • concentration of the hydrogen peroxide stabilizer may range from 0.0001 wt% to 5 wt% such as from 0.01 wt% to 2 wt% relative to the total weight of the oxidizing agent.
  • the oxidizing agent in the form of an aqueous hydrogen peroxide solution, the
  • concentration ratio of the hydrogen peroxide to the possible at least one stabilizer may range from 0.05:1 to 1,000:1, such as from 0.1 :1 to 500:1 and further such as from 1 :1 to 200:1.
  • the oxidizing agent may be included in the second composition of the present invention in an amount of 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more; 5% by weight or less, preferably 3% by weight or less, and more preferably 1% by weight or less, relative to the total weight of the composition. (Other Ingredients)
  • the second composition of the present invention may also comprise at least one additional ingredient.
  • the additional ingredient(s) may be selected from the group consisting of water; organic solvents, in particular water-soluble organic solvents; fatty materials; cationic, anionic, nonionic or amphoteric surfactants; thickeners; cationic, anionic, nonionic or amphoteric polymers; penetrating agents; agents for combating hair loss; anti-dandruff agents;
  • associative-type or not, natural or synthetic thickeners for fatty materials comprising suspending agents; chelating or sequestering agents, such as tetrasodium etidronate and tetrasodium
  • pyrophosphate such as sodium salicylate; opacifying agents; dyes other than direct dyes; fragrances; pH adjusting agents of alkaline agent(s) or acidic agent(s); anti-oxidant or preserving agents; stabilizers; and mixtures thereof.
  • the second composition of the present invention typically comprises water.
  • the amount of water in the second composition may be 60% by weight or more, preferably 70% by weight or more, more preferably 80% by weight or more, and even more preferably 90% by weight or more; 99% by weight or less, preferably 97% by weight or less, and more preferably 95% by weight or less, relative to the total weight of the composition.
  • the pH of the second composition may be adjusted to the desired value using alkaline agent(s) and/or acidic agent(s) commonly used in the field of cosmetics.
  • the pH of the second composition of the present invention be from 2.0 to 6.0, preferably from 2.0 to 5.0, and more preferably from 2.5 to 4.0, using an acidic agent.
  • acidic agents mention may be made of any inorganic or organic acids commonly used in cosmetic products such as citric acid, lactic acid, phosphoric acid or hydrochloric acid (HC1).
  • the second composition of the present invention may include one or two or more of cationic, anionic, nonionic or amphoteric polymers.
  • the second composition comprises cationic polymers, in particular polymeric quaternary ammonium salts.
  • cationic polymers in particular polymeric quaternary ammonium salts.
  • CFAname Polyquaternium products
  • Polyquaternium-6 such as the product Salcare SC 30 sold by BASF and the product Merquat 100 sold by Nalco
  • non-associative cationic polymers such as methacryloylethyl trimethyl ammonium chloride homopolymer, INCI name:
  • the amount of the polymer(s) in the second composition may be from 0.1 to 20% by weight, preferably from 1 to 15% by weight, and more preferably from 3 to 10% by weight, relative to the total weight of the composition.
  • Step (v) is an optional step of rinsing the keratin fibers in order to remove the second composition from the keratin fibers.
  • the keratin fibers may be rinsed preferably with water and then dried.
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair drier.
  • the process according to the present invention further comprises an additional step of leaving the second composition on the keratin fibers for a certain amount of time.
  • the leave-on time of the second composition on the keratin fibers can be from 10 seconds to 30 minutes, preferably from 1 minute to 20 minutes, and more preferably from 2 minutes to 10 minutes.
  • the present invention also relates to a kit which is intended to be used to carry out the coloring process according to the present invention.
  • the kit according to the present invention relates to a kit for coloring keratin fibers, preferably hair, comprising:
  • a first compartment including the dye composition comprising at least one direct dye except fluorescent disulfide, thiol and protected-thiol direct dyes,
  • a second compartment including the reducing composition comprising at least one reducing agent
  • a third compartment including the second composition comprising at least one oxidizing agent.
  • the dye composition, the reducing composition, and the second composition used in the kit are the same as those explained in the descriptions for the process above.
  • compartment may be provided so that the dye composition in the first compartment and the reducing composition in the second compartment are mixed within the kit to prepare the first composition of the present invention explained above.
  • the first compartment and the second compartment are provided so as to be connectable each other within the kit in order to mix the dye composition and the reducing composition to prepare the first composition of the present invention.
  • kit to carry out steps (i) and (ii) of the process according to the present invention by, for example, connecting the first compartment and the second compartment to mix the dye composition and the reducing composition to prepare the first composition, and then dispensing or discharging the first composition from the kit followed by applying the first composition onto keratin fibers such as hair.
  • kit to carry out step (iv) of the process according to the present invention by, for example, dispensing or discharging the second composition from the third compartment followed by applying the second composition onto keratin fibers such as hair.
  • the first compartment and the second compartment may be provided adjacent to each other so that they can be connected easily to mix the dye composition and the reducing composition in order to prepare the first composition.
  • the third compartment can be provided together with or separately from the first
  • Dye Compositions 1 to 3 were prepared by the following protocol. First,
  • hydroxyethylcellulose was dissolved in hot deionized water at 60°C for 10 minutes and then polyurethane-39 was added while stirring and the mixture was left for 10 minutes to prepare a water phase.
  • cetearyl alcohol, steareth-20 and cetrimonium chloride were added and heated to a temperature of 75 °C. After these ingredients were well melted, they were added to the water phase previously prepared and an emulsification was performed by stirring the mixture for 10 minutes. The mixture was then cooled down until reaching 40°C.
  • Chlorhexidine digluconate, phenoxyethanol, fragrance, and dyes (HC Blue 15 for Dye Compositions 1 and 3 and E1C Blue 16 for Dye Composition 2) were added with the rest of water. The mixture was maintained while stirring until the temperature reached room temperature.
  • Reducing Compositions 1 to 3 were prepared by the following protocol. First, in a beaker, EDTA and deionized water were added under magnetic stirring. After homogenization, ammonium hydroxide was added and then reducing agent (ammonium thioglycolate for Reducing Composition 1, ammonium thiolactate for Reducing Composition 2, and cysteamine for Reducing Composition 3) and ammonium bicarbonate were added. In another beaker, oleth-20 and fragrance were melted. This mixture was added to the first one still under magnetic stirring. After the mixture was well homogeneous, the pH was adjusted to 9.2 by adding ammonium hydroxide. The formulations of Reducing Compositions 1 to 3 are summarized in Table 2 below. The numerical values for the amounts of the ingredients shown in Table 2 are all based on“% by weight” as active raw materials.
  • the Second Composition was prepared by the following protocol. Tetrasodium etidronate, sodium salicylate, and tetrasodium pyrophosphate were added into deionized water and mixed at room temperature. After all of these ingredients were well homogenized, 2 polymers (Polyquaterniunr6, Polyquaternium-37 (and) Mineral Oil (and) PPG l Trideceth-6) were added respectively. After homogenization, hydrogen peroxide was added and the pH was adjusted to 2.8 ⁇ 0.2 by addition of phosphoric acid.
  • composition of the Second Composition is summarized in Table 3 below.
  • the numerical values for the amounts of the ingredients shown in Table 3 are all based on“% by weight” as active raw materials.
  • a 100% Chinese white hair swatch (1 g, 20 cm) was washed with a conventional shampoo, rinsed with running tap water at 40°C, and then dried.
  • Dye Composition 1 was mixed with Reducing Composition 1 just before the application, respecting the mixing a weight ratio of 9: 1 , to prepare a first composition. After the first composition was well homogenized, it was measured to have a pH of 8.8. 3g of the first composition were applied with a brush on the dried swatch and the swatch was left to stand for about 30 minutes at room temperature without heat. At 15 minutes, the swatch was turned on the other side on a plate.
  • the coloring process was conducted in the same manner as Example 1 , except for using Reducing Composition 2 instead of Reducing Composition 1.
  • the pH of the first composition was the same as that of Example 1 (8.8).
  • the coloring process was conducted in the same manner as Example 1 , except for using Reducing Composition 3 instead of Reducing Composition 1.
  • the pH of the first composition was the same as that of Example 1 (8.8).
  • Example 1 The coloring process was conducted in the same manner as Example 1 , except for using Dye Composition 2 instead of Dye Composition 1.
  • the pfl of the first composition was the same as that of Example 1 (8.8).
  • Dye Composition 3 was used instead of Dye Composition 1 and no reducing composition was used for the coloring process according to Example 1.
  • Dye Composition 3 was directly applied to the swatch.
  • the pH of Dye Composition 3 was adjusted so as to be the same as that of the first composition according to Examples 1 to 4 (8.8), for a comparison.
  • the dye composition and the reducing composition were applied sequentially.
  • a base cream composition which does not include any dye, was mixed with Reducing Composition 1 just before the application, maintaining the mixing weight ratio of 9: 1.
  • the formulation of the base cream composition is shown in the following Table 4.
  • 3g of the mixture were applied with a brush on the dried swatch and left to stand for 30 minutes at room temperature without heat.
  • the swatch was reversed on the other side on a plate.
  • the swatch was then rinsed with running tap water at 40°C, and 3g of Dye Composition 1 were applied with a brush on the wet swatch. The swatch was left to stand for 30 minutes at room temperature without heat on the plate. At 15 minutes, the swatch was reversed on the other side on the plate.
  • the swatch was then rinsed with running tap water at 40°C, and 2g of the Second
  • Composition was applied with a brush on the wet swatch. The swatch was left to stand for 5 minutes. The swatch was then rinsed with running tap water at 40°C and dried. Table 4
  • Each of the colored Chinese 100% white hair swatches in accordance with Examples 1 to 4 and Comparative Examples 1 to 4 was rinsed 40 times with running tap water at 40°C and dried gently while being combed.
  • the difference in color of the colored swatch before and after the coloring process was measured by measuring the colorimetric values (L*, a* b*, lightness / green-red / blue-yellow) using a Konica Minolta Spectrophotometer CM-3600A.
  • DE * between the swatch before and after the treatment of the coloring process under AL Vb system was calculated. The larger DE * is, the better the color property is.
  • Each of the colored Chinese 100% white hair swatches in accordance with Examples 1 to 4 and Comparative Examples 1 to 4 was rinsed 40 times with running tap water at 40°C, and then was shampooed 20 times.
  • the shampoo composition contained 9mol% of betaine and 15mol% of SLS/0.4mL for lg hair swatch.
  • the swatch was then rinsed 30 times under running tap water at 40°C and dried gently while being combed. This process was repeated 29 more cycles.
  • the difference in color of the colored swatch before and after shampooing for 30 cycles was measured by measuring the colorimetric values (L* (lightness), a* (green-red), b* (blue-yellow), and h (hue angle)) using a Konica Minolta Spectrophotometer CM-3600A.
  • DE * and Ah were calculated.
  • the process according to the present invention can significantly improve long-lastingness of coloring on the keratin fibers.

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Abstract

La présente invention concerne un procédé de coloration de fibres de kératine, préférablement des cheveux, comprenant les étapes suivantes : (i) le mélange (a) d'au moins une composition de coloration comprenant au moins un colorant direct à l'exception du disulfure fluorescent, du thiol et des colorants thiol protégés et (b) d'au moins une composition de réduction comprenant au moins un agent réducteur, pour préparer une première composition ; (ii) l'application de la première composition sur les fibres de kératine ; (iii) le rinçage des fibres de kératine ; (iv) l'application sur la fibre de kératine d'une seconde composition comprenant au moins un agent oxydant ; et (v) le rinçage et le séchage éventuels des fibres de kératine. La présente invention permet d'obtenir des fibres de kératine qui présentent une durabilité de couleur améliorée.
PCT/JP2020/012568 2019-03-20 2020-03-13 Procédé et kit pour la coloration de fibres de kératine WO2020189793A1 (fr)

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WO2018229296A1 (fr) 2017-06-16 2018-12-20 L'oreal Procédé de coloration des matières kératiniques mettant en oeuvre au moins un colorant bleu, violet ou vert et au moins un colorant fluorescent disulfure, thiol ou thiol protégé
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