Source: https://patents.google.com/patent/US20070251026A1/en
Timestamp: 2019-04-24 00:34:14+00:00

Document:
Disclosed herein is a process involving the use of at least one unsaturated fatty substance of formula (I) as defined herein as an agent for protecting color with respect to the washing of artificially dyed keratin fibers such as artificially dyed hair. Also disclosed herein is a process for protecting the color of artificially dyed keratin fibers with respect to washing, comprising applying to the fibers, before or after dyeing, at least one composition comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I). Further disclosed herein is a process for dyeing keratin fibers, comprising applying to the keratin fibers a direct or oxidation dye composition (A) for a time that is sufficient to develop the color, and following or preceding this application, applying a composition (B) comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I).
This application claims benefit of U.S. Provisional Application No. 60/792,955, filed Apr. 19, 2006, the contents of which are incorporated herein by reference. This application also claims benefit of priority under 35 U.S.C. § 119 to French Patent Application No. FR 06/51335, filed Apr. 12, 2006, the contents of which are also incorporated herein by reference.
Disclosed herein are unsaturated fatty substances of formula (I) as defined herein which can be used as agents for protecting color with respect to the washing of artificially dyed keratin fibers, for example, human keratin fibers such as the hair.
It is known practice to dye keratin fibers, for example, human keratin fibers such as the hair, with dye compositions comprising oxidation dye precursors, which are generally known as oxidation bases. These oxidation bases are colorless or weakly colored compounds, which, when combined with oxidizing products, give rise to colored compounds via a process of oxidative condensation. It is also known that the shades obtained, with these oxidation bases can be varied by combining them with couplers or coloration modifiers. The variety of molecules used as oxidation bases and couplers can allow a wide range of colors to be obtained.
It is also known practice to dye keratin fibers by direct dyeing. The process conventionally used in direct dyeing comprises applying to the keratin fibers direct dyes, which are colored and coloring molecules that have affinity for the fibers, leaving them to act, and then rinsing the fibers.
The colorations resulting therefrom may be particularly chromatic colorations, but are, however, temporary or semi-permanent since the nature of the interactions that bind the direct dyes to the keratin fiber and their desorption from the surface and/or core of the fiber are responsible for their weak dyeing power and their poor wash-fastness.
The artificial color of hair provided by a direct or oxidation dyeing treatment gradually attenuates as a result of repeated washing and leads over time to fading of the coloration of the hair. The use of commercial rinse-out and leave-in care products does not sufficiently improve the fastness of the artificial color of hair.
It is thus desirable to develop methods for protecting the artificial color of keratin fibers from the effects of repeated washing.
The present inventors have discovered, surprisingly and unexpectedly, that the use of least one unsaturated fatty substance of formula (I) as defined herein can provide protection of the artificial color of keratin fibers against washing.
As used herein, the term “human keratin fibers” means head hair, body hair such as the beard and moustache, the eyelashes, and the eyebrows.
As used herein, the term “artificially dyed keratin fibers” means keratin fibers dyed via a direct dyeing process or via an oxidation dyeing process.
As used herein, the term “washing” means at least one application onto the keratin fibers of an aqueous rinse-out composition, which can be a detergent composition such as a shampoo. This term also includes bathing, for example, in the sea or in a swimming pool.
Disclosed herein is also a process for protecting color with respect to the washing of artificially dyed keratin fibers, comprising applying to the fibers at least one composition comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein.
In at least one embodiment, the protection provided by the treatment according to the present disclosure may be long-lasting, i.e. does not require frequent reapplication of the product.
Also disclosed herein is a dyeing process comprising applying to keratin fibers, for example, human keratin fibers such as the hair, a direct or oxidation dye composition (A) for a time sufficient to develop the color, and applying a composition (B) comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein, wherein composition (B) may be applied before or after the application of composition (A).
Other characteristics, aspects, subjects and benefits of the invention will be understood more clearly upon reading the description below. All meanings and definitions of the compounds used in the present disclosure given herein are valid for all embodiments of the present disclosure.
a, b, c, d, e, and f, which may be identical or different, are equal to 0 or 1.
As used herein, the term “unsaturation” means a double or triple bond.
In at least one embodiment, the divalent radical unsaturations are in a conformation chosen from cis and trans conformations. In another embodiment, the divalent radical is in cis conformation.
In yet another embodiment, M is chosen from Na+ and K+.
q is an integer ranging from 0 to 2.
and in at least one embodiment, chosen from oleic acid and sorbitan oleate.
The cosmetically acceptable medium of the color-protecting compositions according to the present disclosure may be chosen, for example, from water and mixtures of water and at least one cosmetically acceptable organic solvent. Examples of suitable organic solvents include, but are not limited to, C1-C4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, and diethylene glycol monoethyl ether and monomethyl ether, and mixtures thereof.
The at least one solvent may be present in the composition in an amount ranging from 1% to 40% by weight, for example, from 3% to 10% by weight, relative to the total weight of the composition.
The at least one unsaturated fatty substance of formula (I) is present in the color-protecting compositions in an amount ranging from 1% to 100%, for example, from 5% to 90% by weight relative to the total weight of the composition.
According to one embodiment of the present disclosure, a composition comprising 100% by weight of at least one unsaturated fatty substance of formula (I) may be used. In this embodiment, the physiologically acceptable medium will consist of the at least one unsaturated fatty substance of formula (I).
The composition according to the present disclosure comprising the at least one agent for protecting the color of keratin fibers may also comprise at least one adjuvant chosen from various adjuvants conventionally used in hair treatment compositions, such as anionic, cationic, nonionic, amphoteric, and zwitterionic surfactants, and mixtures thereof; anionic, cationic, nonionic, amphoteric, and zwitterionic polymers, and mixtures thereof; mineral and organic thickeners, such as anionic, cationic, nonionic, and amphoteric polymeric associative thickeners; penetrants; sequestrants; fragrances; buffers; dispersants; conditioning agents, for instance, modified and unmodified, volatile and non-volatile silicones; film-forming agents; ceramides; preserving agents; and opacifiers.
According to one embodiment, the compositions according to the present disclosure may also comprise at least one agent for protecting against the effects of atmospheric agents, such as light.
The at least one agent for protecting keratin fibers against atmospheric agents may be any active agent that is useful for preventing or limiting the degradation of keratin fibers, such as the hair, caused by atmospheric attacking factors, for instance, light.
Thus, this agent for protecting keratin fibers may be chosen, for example, from organic UV-screening agents, free-radical scavengers, and antioxidants.
The organic UV-screening agents (systems for screening out UV radiation) may be chosen, for instance, from water-soluble or liposoluble, silicone or non-silicone screening agents.
By way of non-limiting example, the organic UV-screening agents may be chosen from dibenzoylmethane derivatives; anthranilates; cinnamic derivatives; salicylic derivatives; camphor derivatives; benzophenone derivatives; β,β-diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzazolyl derivatives as described, for instance, in European Patent No. 0 669 323 and U.S. Pat. No. 2,463,264; p-aminobenzoic acid (PABA) derivatives; benzoxazole derivatives as described, for example, in European Patent Application Nos. 0 832 642, 1 027 883, and 1 300 137 and German Patent Application No. 101 62 844; screening polymers and screening silicones such as those described in International Patent Application Publication No. WO 93/04665; dimers derived from α-alkylstyrene, such as those described in German Patent Application No. 198 55 649; 4,4-diarylbutadienes such as those described in European Patent Application Nos. 0 967 200, 1 008 586, 1 133 980, and 0 133 981, and German Patent Application Nos. 197 46 654 and 197 55 649, and mixtures thereof.
Dipropylene glycol salicylate sold, for instance, under the name “Dipsal” by Scher, and TEA salicylate sold, for example, under the name “Neo Heliopan TS” by Haarmann and Reimer.
Octocrylene sold, for instance, under the trade name “Uvinul N539” by BASF, and Etocrylene sold, for example, under the trade name “Uvinul N35” by BASF.
Polyacrylamidomethylbenzylidenecamphor sold, for instance, under the name “Mexoryl SW” by Chimex.
Disodium phenyl dibenzimidazole tetrasulfonate sold, for instance, under the trade name “Neo Heliopan AP” by Haarmann and Reimer.
Methylenebis(benzotriazolyl)tetramethylbutylphenol sold, for instance, in solid form under the trade name “MIXXIM BB/100” by Fairmount Chemical, or in micronized form as an aqueous dispersion under the trade name “Tinosorb M” by Ciba Specialty Chemicals.
Menthyl anthranilate sold, for instance, under the trade name “Neo Heliopan MA” by Haarmann and Reimer.
2,4-bis[5-(1-dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine sold, for example, under the name Uvasorb K2A by Sigma 3V.
Free-radical scavengers that may be used in the composition according to the present disclosure include, by way of non-limiting example, besides certain antipollution agents mentioned above, vitamin E and derivatives thereof such as tocopheryl acetate; bioflavonoids; coenzyme Q10, and ubiquinone; certain enzymes, for instarice, catalase, superoxide dismutase and wheatgerm extracts containing it, lactoperoxidase, glutathione peroxidase, and quinone reductases; glutathione; benzylidenecamphor; benzylcyclanones; substituted naphthalenones; pidolates; phytanetriol; gamma-oryzanol; guanosine; lignans; and melatonin.
In at least one embodiment, the antioxidants may be chosen from phenols such as BHA (tert-butyl-4-hydroxyanisole), BHT (2,6-di-tert-butyl-p-cresol), and TBHQ (tert-butylhydroquinone), polyphenols such as proanthocyanidol oligomers and flavonoids, hindered amines known under the generic term HALS (Hindered Amine Light Stabilizer) such as tetraminopiperidine, erythorbic acid, polyamines such as spermine, cysteine, glutathione, superoxide dismutase, and lactoferrin.
According to another embodiment, the at least one agent for protecting keratin fibers against atmospheric attacking factors such as light will be chosen from organic UV-screening agents.
The at least one agent for protecting keratin fibers against atmospheric attacking factors such as light may be present in the composition in an amount ranging from 0.2% to 20% by weight relative to the total weight of the composition.
According to one embodiment, the compositions according to the present disclosure comprise at least one aromatic alcohol and at least one aromatic dicarboxylic acid.
As used herein, the term “aromatic alcohol” means any compound that is liquid at room temperature and atmospheric pressure, comprising at least one ring chosen from benzene and naphthalene rings and at least one alcohol functional group (OH) directly linked to the ring or linked to at least one substituent of the ring. In at least one embodiment, the alcohol functional group can be on a substituent of the at least one ring chosen from benzene and naphthalene rings.
In at least one embodiment, the at least one aromatic alcohol is benzyl alcohol.
The at least one aromatic alcohol may be present in the composition in an amount ranging from 0.01% to 50% by weight, for example, from 0.1% to 30% by weight, or from 1% to 20% by weight, relative to the total weight of the composition. According to one embodiment, the at least one aromatic alcohol is present in the composition in an amount greater than 1% by weight.
The compositions according to the present disclosure may further comprise at least one optionally salified aromatic carboxylic acid.
As used herein, the term “aromatic carboxylic acid” means any compound comprising at least one ring chosen from benzene and naphthalene rings and at least one carboxylic acid functional group (COOH), in free or salified form, directly linked to the ring or linked to at least one substituent of the ring. In at least one embodiment, the acid functional group may be directly linked to the at least one ring chosen from benzene and naphthalene rings.
The aromatic carboxylic acid salts may be chosen, for example, from alkali metal (e.g, sodium and potassium) salts, alkaline-earth metal (e.g., calcium and magnesium) salts, organic amine salts, and ammonium salts.
According to one embodiment, the at least one aromatic carboxylic acid is benzoic acid.
The at least one optionally salified carboxylic aromatic acid may be present in the composition in an amount ranging from 0.001% to 30% by weight, for example, from 0.01% to 20% by weight, or from 0.1% to 10% by weight, relative to the total weight of the composition.
The compositions according to the present disclosure may further comprise at least one conditioning agent.
As used herein, the term “conditioning agent” means any agent whose function is to improve the cosmetic properties of the hair, for instance, the softness, disentangling, feel, smoothness, and/or static electricity.
The conditioning agents may be chosen, for example, from synthetic oils such as polyolefins, animal and plant oils, fluoro oils, perfluoro oils, natural waxes, synthetic waxes, silicones, non-polysaccharide cationic polymers, ceramide compounds, cationic surfactants, fatty amines, saturated fatty acids, esters of fatty acids other than those of the present disclosure, and mixtures thereof.
those of hydrogenated or non-hydrogenated polybutene type, for instance, those of hydrogenated or non-hydrogenated polyisobutene type.
Isobutylene oligomers with a molecular weight of less than 1,000 and mixtures thereof with polyisobutylenes with a molecular weight of greater than 1,000, for example, ranging from 1,000 to 15,000, may also be used.
those of hydrogenated or non-hydrogenated polydecene type.
The animal and plant oils may be chosen, for instance, from sunflower oil, corn oil, soybean oil, avocado oil, jojoba oil, marrow oil, grapeseed oil, sesame oil, hazelnut oil, fish oils, glyceryl tricaprocaprylate, and plant and animal oils of formula R9COOR10, wherein R9 is chosen from higher fatty acid residues comprising from 7 to 29 carbon atoms and R10 is chosen from linear and branched hydrocarbon-based chains comprising from 3 to 30 carbon atoms, such as alkyl and alkenyl chains, for example, purcellin oil.
In at least one embodiment, natural and synthetic essential oils such as eucalyptus oil, lavandin oil, lavender oil, vetiver oil, Litsea cubeba oil, lemon oil, sandalwood oil, rosemary oil, camomile oil, savory oil, nutmeg oil, cinnamon oil, hyssop oil, caraway oil, orange oil, geraniol oil, cade oil, and bergamot oil may be used.
The waxes may be chosen from natural (animal and plant) and synthetic substances that are solid at room temperature (20°-25° C.). The waxes are also insoluble in water, soluble in oils, and are capable of forming a water-repellent film.
A suitable definition of waxes may be found, for example, in P. D. Dorgan, Drug and Cosmetic Industry, December 1983, pp. 30-33.
The at least one wax may be chosen, for example, from carnauba wax, candelilla wax, alfalfa wax, paraffin wax, ozokerite, plant waxes such as olive tree wax, rice wax, hydrogenated jojoba wax, absolute waxes of flowers such as the essential wax of blackcurrant flower sold by the company Bertin (France), animal waxes such as beeswaxes, and modified beeswaxes (cerabellina). Other examples of waxes and waxy starting materials which can be used according to the present disclosure include, but are not limited to, marine waxes such as the product sold by the company Sophim under the reference M82, and polyethylene waxes and polyolefin waxes in general.
According to one embodiment, the at least one conditioning agent may be chosen from cationic polymers and silicones.
Non-saccharide cationic polymers that may be used in accordance with the present disclosure may be chosen from those known in the art as improving the cosmetic properties of hair treated with detergent compositions, for example, those described in European Patent Application No. 0 337 354 and French Patent Application Nos. 2 270 846, 2 383 660, 2 598 611, 2 470 596, and 2 519 863.
The cationic polymers may be chosen from those comprising units comprising at least one group chosen from primary, secondary, tertiary, and/or quaternary amine groups that either may form part of the main polymer chain or may be borne by a side substituent directly attached thereto.
The cationic polymers may, in at least one embodiment, have a number-average molecular mass ranging from 500 to 5×106, for example, from 103 to 3×106.
Non-limiting examples of suitable cationic polymers include polyamine polymers, polyamino amide polymers, and polyquaternary ammonium polymers, which are known in the art.
X is chosen from anions derived from acids chosen from mineral and organic acids, such as methosulfate anions and halides such as chloride and bromide.
(2) Polymers comprising at least one entity chosen from piperazinyl units and divalent alkylene and hydroxyalkylene radicals comprising straight or branched chains, optionally interrupted by at least one entity chosen from oxygen, sulphur, and nitrogen atoms, aromatic rings, and heterocyclic rings, as well as the oxidation and/or quaternization products of these polymers. Such polymers are described, for example, in French Patent Nos. 2 162 025 and 2 280 361.
(3) Water-soluble polyamino amides prepared by polycondensation of an acidic compound with a polyamine; these polyamino amides may optionally be crosslinked with at least one agent chosen from epihalohydrins, diepoxides, dianhydrides, unsaturated dianhydrides, bis-unsaturated derivatives, bis-halohydrins, bis-azetidiniums, bis-haloacyldiamines, bis-alkyl halides, and oligomers resulting from the reaction of a difunctional compound which is reactive with an agent chosen from bis-halohydrins, bis-azetidiniums, bis-haloacyldiamines, bis-alkyl halides, epihalohydrins, diepoxides, and bis-unsaturated derivatives; the crosslinking agent being used in an amount ranging from 0.025 to 0.35 mol per amine group of the polyamino amide; these polyamino amides possibly being alkylated or, if they contain at least one tertiary amine functional group, they may be quaternized. Such polymers are described, for example, in French Patent Nos. 2 252 840 and 2 368 508.
(4) The polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents, for example, adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers wherein the alkyl radical comprises from 1 to 4 carbon atoms and, in at least one embodiment, is chosen from methyl, ethyl, and propyl. Such polymers are described, for example, in French Patent No. 1 583 363.
Non-limiting examples of these derivatives include, but are not limited to, the adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the names Cartaretine F, F4, and F8 by the company Sandoz.
Y− is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate, and phosphate. These polymers are described, for example, in French Patent No. 2 080 759 and its Certificate of Addition 2 190 406.
In at least one embodiment, R10 and R11, which may be identical or different, are chosen from alkyl groups comprising from 1 to 4 carbon atoms.
Examples of such polymers include, but are not limited to, the dimethyldiallylammonium chloride homopolymer sold under the name Merquat 100 by the company Nalco (and its homologues of low weight-average molecular mass) and the copolymers of diallyldimethylammonium chloride and of acrylamide, sold under the name Merquat 550.
In at least one embodiment, X− is an anion chosen from chloride and bromide.
In another embodiment, these polymers can have a number-average molecular mass ranging from 1,000 to 100,000.
Polymers of this type are described, for example, in French Patent Nos. 2 320 330, 2 270 846, 2 316 271, 2 336 434, and 2 413 907 and U.S. Pat. Nos. 2,273,780, 2,375,853, 2,388,614, 2,454,547, 3,206,462, 2,261,002, 2,271,378, 3,874,870, 4,001,432, 3,929,990, 3,966,904, 4,005,193, 4,025,617, 4,025,627, 4,025,653, 4,026,945, and 4,027,020.
wherein R18, R19, R20, and R21, which may be identical or different, are chosen from alkyl and hydroxyalkyl radicals comprising from 1 to 4 carbon atoms, r and s are integers ranging from 2 to 20, and X− is an anion derived from a mineral or organic acid.
In another embodiment, in formula (a), R18, R19, R20, and R21 are methyl radicals, r=3, s=6, and X═Cl; this compound is referred to as hexadimethrine chloride according to the INCI nomenclature (CTFA).
A is a divalent radical and, in at least one embodiment, —CH2—CH2—O—CH2—CH2—.
Examples of suitable commercial products corresponding to these polymers include, but are not limited to, Mirapol® A 15, Mirapol® AD1, Mirapol® AZ1 and Mirapol® 175 sold by the company Miranol.
(10) Crosslinked methacryloyloxy(C1-C4)alkyltri(C1-C4)alkylammonium salt polymers such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo- or copolymerization being followed by crosslinking with a compound containing olefinic unsaturation, for example, methylenebisacrylamide. According to one embodiment, a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of the copolymer in mineral oil may be used. This dispersion is sold under the name Salcare® SC 92 by the company Ciba. According to another embodiment, a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer containing about 50% by weight of the homopolymer in mineral oil or in a liquid ester can also be used. These dispersions are sold under the names Salcare® SC 95 and Salcare® SC 96 by the company Ciba.
Other examples of cationic polymers that can be used in accordance with the present disclosure include, but are not limited to, cationic proteins, cationic protein hydrolysates, polyalkyleneimines, such as polyethyleneimines, polymers comprising at least one unit chosen from vinylpyridine units and vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes, and chitin derivatives.
According to at least one embodiment, the cationic polymers may be chosen from cationic cyclopolymers, for example, the dimethyldiallylammonium chloride homopolymers and copolymers sold under the names Merquat 100, Merquat 550, and Merquat S by the company Nalco, quaternary vinylpyrrolidone and vinylimidazole polymers, and mixtures thereof.
Examples of silicones that may be used in accordance with the present disclosure include, but are not limited to, polyorganosiloxanes that are insoluble in the composition and that may be in the form of oils, waxes, resins, or gums.
Organopolysiloxanes are defined, for example, in Walter Noll's “Chemistry and Technology of Silicones” (1968) Academic Press. They can be volatile or non-volatile.
(i) cyclic silicones comprising from 3 to 7, for example, from 4 to 5 silicon atoms. These compounds include, for example, octamethylcyclotetrasiloxane, such as the products sold under the names Volatile Silicone 7207 by Union Carbide and Silbione 70045 V 2 by Rhodia Chimie, decamethylcyclopentasiloxane, such as the products sold under the names Volatile Silicone 7158 by Union Carbide and Silbione 70045 V 5 by Rhodia Chimie, and mixtures thereof.
According to at least one embodiment, the silicones are chosen from non-volatile silicones, such as polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, polyorganosiloxanes modified with organofunctional groups, and mixtures thereof.
In another embodiment, the silicones may be chosen from polyalkylsiloxanes, such as polydimethylsiloxanes comprising trimethylsilyl end groups having a viscosity ranging from 5×10−6 to 2.5 m2/s at 25° C., for example, from 1×10−5 to 1 m2/s. The viscosity of the silicones may be measured, for example, at 25° C. according to ASTM standard 445 Appendix C.
the Viscasil oils from General Electric and certain oils of the SF series (e.g., SF 96, and SF 18) from General Electric.
The polydimethylsiloxanes may also be chosen, for example, from those comprising dimethylsilanol end groups (Dimethiconol according to the CTFA name) such as the oils of the 48 series from the company Rhodia Chimie.
Other examples of polyalkylsiloxanes falling within this category include, but are hot limited to, the products sold under the names Abil Wax 9800 and 9801 by the company Goldschmidt, which are poly(C1-C20)alkylsiloxanes.
According to at least one embodiment, the polyalkylarylsiloxanes may be chosen from linear and/or branched polydimethylmethylphenylsiloxanes and polydimethyldiphenylsiloxanes having a viscosity ranging from 1×10−5 to 5×10−2 m2/s at 25° C.
The silicone gums that may be used in accordance with the present disclosure include, for example, polydiorganosiloxanes with high number-average molecular masses ranging from 200,000 to 1,000,000, used alone or as a mixture in a solvent. This solvent can be chosen, for instance, from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, and mixtures thereof.
mixtures of two PDMSs with different viscosities, for instance, of a PDMS gum and a PDMS oil, such as the product SF 1236 from the company General Electric. The product SF 1236 is a mixture of an SE 30 gum defined above, having a viscosity of 20 m2 s, and an SF 96 oil, with a viscosity of 5×10−6 m2/s. In at least one embodiment, this product contains 15% SE 30 gum and 85% SF 96 oil.
R2SiO2/2, R3SiO1/2, RSiO3/2, and SiO4/2, wherein R is chosen from hydrocarbon-based groups comprising from 1 to 16 carbon atoms and phenyl groups. According to at least one embodiment, R may be chosen from C1-C4 lower alkyl radicals, such as methyl, and phenyl radicals.
Commercial products corresponding to these resins include, but are not limited to, the product sold under the name Dow Corning 593, those sold under the names Silicone Fluid SS 4230 and SS 4267 by the company General Electric, which are silicones of dimethyl/trimethyl siloxane structure, and the trimethyl siloxysilicate type resins sold, for example, under the names X22-4914, X21-5034, and X21-5037 by the company Shin-Etsu.
The organomodified silicones that can be used in accordance with the present disclosure include silicones as defined above and comprising in their structure at least one organofunctional group attached via a hydrocarbon-based radical.
hydroxyacylamino groups, such as the polyorganosiloxanes described in European Patent Application No. 342 834, and the product Q2-8413 from the company Dow Corning.
According to one embodiment, the silicones may be chosen from those comprising a polysiloxane portion and a portion comprising a non-silicone organic chain, one of the two portions constituting the main chain of the polymer, the other being grafted onto the main chain. These polymers are described, for example, in European Patent Application Nos. 0 412 704, 0 412 707, 0 640 105, and 0 582 152, International Patent Application Publication Nos. WO 95/00578 and WO 93/23009, and U.S. Pat. Nos. 4,693,935, 4,728,571, and 4,972,037. These polymers may be chosen from anionic and nonionic polymers.
Other examples of grafted silicone polymers include, but are not limited to, polydimethylsiloxanes (PDMS) onto which are grafted, via a connecting chain unit of thiopropylene type, mixed polymer units of poly(meth)acrylic acid type and of polyalkyl (meth)acrylate type and polydimethylsiloxanes (PDMS) onto which are grafted, via a connecting chain unit of thiopropylene type, polymer units of polyisobutyl(meth)acrylate type.
According to the present disclosure, the silicones disclosed herein may be used in a form chosen from emulsions, nanoemulsions, and microemulsions.
Crotein Q in which the quaternary ammonium groups contain at least one alkyl group comprising from 1 to 18 carbon atoms.
According to the present disclosure, the compounds of ceramide type may be chosen, for instance, from natural and synthetic ceramides, glycoceramides, pseudoceramides, and/or neoceramides.
Suitable ceramide compounds are described, for example, in German Patent Application Nos. 4 424 530, 4 424 533, 4 402 929, and 4 420 736, International Patent Application Publication Nos. WO 95/23807, WO 94/07844, WO 95/16665, WO 94/07844, WO 94/24097, and WO 94/10131, European Patent Application Nos. 0 646 572 and 0 227 994, and French Patent Application No. 2 673 179, all of which are incorporated herein by reference in their entireties.
The at least one conditioning agent may also be chosen from cationic surfactants, such as optionally polyoxyalkylenated primary, secondary, and tertiary fatty amine salts; quaternary ammonium salts; imidazoline derivatives; and amine oxides of cationic nature.
quaternary ammonium salts comprising at least one ester functional group.
with the provisos that the sum x+y+z ranges from 1 to 15, that when x is 0, then R47 denotes R51, and that when z is 0, then R49 denotes R53.
According to one embodiment, the R46 alkyl radicals may be chosen from linear and branched radicals and, in at least one other embodiment, linear radicals.
According to another embodiment, R46 may be chosen from methyl, ethyl, hydroxyethyl, and dihydroxypropyl radicals and, in at least one embodiment, methyl and ethyl radicals.
According to yet another embodiment, the sum x+y+z may range from 1 to 10.
In a further embodiment, when R47 is a hydrocarbon-based radical R51, it may be long and comprise from 12 to 22 carbon atoms, or short and comprise from 1 to 3 carbon atoms.
According to a still further embodiment, when R49 is a hydrocarbon-based radical R53, it may comprise from 1 to 3 carbon atoms.
In another embodiment, R48, R50, and R52, which may be identical or different, can be chosen from linear and branched, saturated and unsaturated C11-C21 hydrocarbon-based radicals and, in at least one embodiment, linear and branched, saturated and unsaturated, C11-C21 alkyl and alkenyl radicals.
According to yet another embodiment, x and z, which may be identical or different, can be equal to 0 or 1.
In a further embodiment, y may be equal to 1.
In a still further embodiment, n, p, and r, which may be identical or different, can be equal to 2 or 3 and, in at least one embodiment, equal to 2.
According to another embodiment, the anion X− can be chosen from halides (e.g., chloride, bromide, and iodide), and alkyl sulfates, such as methyl sulfate. In yet another embodiment, the anion X− can be chosen from methanesulfonate, phosphate, nitrate, tosylate, anions derived from an organic acid, such as acetate and lactate, and any other anion that is compatible with the ammonium comprising an ester functional group.
According to a further embodiment, the anion X− can be chosen from chloride and methyl sulfate.
R48, R50, and R52, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C13-C17 hydrocarbon-based radicals, for example, linear and branched, saturated and unsaturated C13-C17 alkyl and alkenyl radicals.
According to one embodiment, the hydrocarbon-based radicals are linear.
Further non-limiting examples include the compounds of formula (XVI) such as diacyloxyethyldimethylammonium salts, diacyloxyethylhydroxyethylmethylammonium salts, monoacyloxyethyldihydroxyethylmethylammonium salts, triacyloxyethylmethylammonium salts, monoacyloxyethylhydroxyethyldimethylammonium salts, and mixtures thereof. In at least one embodiment, these salts may be chosen from chloride and methyl sulfate salts. According to another embodiment, the acyl radicals can comprise from 14 to 18 carbon atoms and can be obtained from a plant oil such as palm oil and sunflower oil. When the compound contains several acyl radicals, these radicals may be identical or different.
These products can be obtained, for example, by direct esterification of an amine chosen from triethanolamine, triisopropanolamine, alkyldiethanolamines, and alkyldiisopropanolamines, which are optionally oxyalkylenated, with fatty acids or with fatty acid mixtures of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification is followed by a quaternization using an alkylating agent such as alkyl halides (e.g., methyl and ethyl halides), dialkyl sulfates (e.g., dimethyl and diethyl sulfates), methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin, and glycerol chlorohydrin.
According to another embodiment, the ammonium salts comprising at least one ester functional group that are described in U.S. Pat. Nos. 4,874,554 and 4,137,180 may also be used.
In a further embodiment, the quaternary ammonium salts may be chosen from those of formula (XV), for example, tetraalkylammonium chlorides such as dialkyldimethylammonium chlorides and alkyltrimethylammonium chlorides, in which the alkyl radical comprises from 12 to 22 carbon atoms, for instance, behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, and benzyldimethylstearylammonium chloride; and the stearamidopropyldimethyl(myristyl acetate)ammonium chloride sold under the name Ceraphyl 70 by the company Van Dyk.
In at least one embodiment, the fatty acids may be chosen, for example, from myristic acid, palmitic acid, stearic acid, behenic acid, and isostearic acid.
According to another embodiment, the fatty acid esters may be chosen from carboxylic acid esters, such as mono-, di-, tri-, and tetracarboxylic esters.
Examples of monocarboxylic acid esters include, but are not limited to, linear or branched, saturated or unsaturated C1-C26 aliphatic acid monoesters of linear or branched, saturated or unsaturated, C1-C26 aliphatic alcohols, the total carbon number of these esters being greater than or equal to 10.
Non-limiting examples of monoesters include dihydroabietyl behenate; octyidodecyl behenate; isocetyl behenate; cetyl lactate; C12-C15 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; octyl isononanoate; 2-ethylhexyl isononate; octyl palmitate; octyl pelargonate; octyl stearate; octyidodecyl erucate; oleyl erucate; ethyl and isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyidecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, and 2-octyidodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isostearyl neopentanoate, and isodecyl neopentanoate.
According to one embodiment, C4-C22 di- and tricarboxylic acid esters of C1-C22 alcohols and mono-, di-, and tricarboxylic acid esters of C2-C26 di-, tri-, tetra-, and pentahydroxy alcohols may also be used.
Examples of such esters include, but are not limited to: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecylstearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; and trioleyl citrate.
The fluoro oils may be chosen, for example, from the perfluoropolyethers described in European Patent Application No. 0 486 135 and the fluorohydrocarbon compounds described in International Patent Application Publication No. WO 93/11103, which are incorporated herein by reference in their entireties.
The fluoro oils may also be chosen, for instance, from fluorocarbons such as fluoroamines, for example perfluorotributylamine, fluorohydrocarbons, for example perfluorodecahydronaphthalene, fluoro esters, and fluoro ethers.
The fluorohydrocarbon compounds, may also be chosen from fluorine-containing fatty acid esters such as the product sold under the name Nofable FO by the company Nippon Oil.
It is to be understood that the compositions of the present disclosure may also include mixtures of any of the conditioning agents described above.
The at least one conditioning agent may be present in the composition in an amount ranging from 0.001% to 20% by weight, for example, from 0.01% to 10% by weight, or from 0.1% to 3% by weight, relative to the total weight of the final composition.
The compositions for protecting the color of keratin fibers according to the present disclosure may be in a form chosen from aqueous and aqueous-alcoholic haircare lotions, gels, milks, creams, emulsions, and mousses.
The compositions for protecting the color of keratin fibers may be packaged in various forms, for instance, in vaporizers, pump-dispenser bottles, and in aerosol containers in order to apply the composition in vaporized form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer, or a mousse for treating the hair.
The pH of the composition for protecting the color of keratin fibers can range from 1 to 11, for example, from 2 to 6, and may be adjusted to the desired value via at least one acidifying or basifying agent that are known in the art for compositions applied to keratin fibers.
wherein R58 is a propylene residue optionally substituted with at least one entity chosen from hydroxyl groups and C1-C4 alkyl radicals; and R54, R55, R56, and R57, which may be identical or different, are chosen from hydrogen, C1-C4 alkyl radicals, and C1-C4 hydroxyalkyl radicals.
Non-limiting examples of acidifying agents include, mineral and organic acids, for instance, hydrochloric acid, orthophosphoric acid, carboxylic acids, for instance, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
Disclosed herein is a process for protecting the color of artificially dyed keratin fibers with respect to washing, comprising applying to the fibers, before or after dyeing, at least one composition comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein.
In at least one embodiment, the composition comprising the at least one unsaturated fatty substance of formula (I) is applied to the fibers after the dyeing step.
The process may further comprise rinsing and/or washing with shampoo before and/or after the application of the composition containing the at least one unsaturated fatty substance of formula (I).
The process according to the present disclosure may also include total or partial drying of the keratin fibers with a hairdryer.
According to one embodiment, the process for protecting the color of the keratin fibers may comprise a step of heating the composition comprising the at least one unsaturated fatty substance of formula (I), which may then be applied directly to the keratin fibers. The temperature may be, for example, less than or equal to 70° C.
According to another embodiment, the process for protecting the color of the keratin fibers may comprise a step of heating the keratin fibers after application of the composition comprising the at least one unsaturated fatty substance of formula (I).
The heating of the keratin fibers may be performed, for example, using an iron, a liquid water/steam mixture, and/or by means of a heating hood.
The heating iron that may be used in accordance with the present disclosure may be a heating iron conventionally used in the field of haircare, for example, crimping irons and smoothing irons. For example, irons that are useful for implementation of the process of the present disclosure may include, but are not limited to, flat and round irons, such as those described in U.S. Pat. Nos. 4,103,145, 4,308,878, 5,983,903, 5,957,140, and 5,494,058. The iron may be applied by successive separate touches of a few seconds, or by gradually moving or sliding it along the locks. In at least one embodiment, there may be a pause between the application of the color-protecting composition and the application of the heating iron to the keratin fibers. The pause can range from 30 seconds to 60 minutes, for example, from 1 to 30 minutes. The temperature can range, for example, from 60° C. to 120° C.
The liquid water/steam mixture that is useful in accordance with the present disclosure can have a temperature of at least 35° C., for example, greater than or equal to 40° C., or ranging from 40° C. to 75° C.
The liquid water/steam mixture can be in the form of a mist. The mixture may also comprise at least one other gas such as oxygen and nitrogen, mixtures of gases such as air, and other vaporizable compounds.
According to one embodiment, the liquid water/steam mixture is placed in contact with the fiber for a time ranging from 1 second to 1 hour, for example, from 5 minutes to 15 minutes. The application of the mixture may be repeated several times on the same fiber, each operation being performed for a time as indicated above. According to another embodiment, the composition containing the at least one compound of formula (I) is first applied to the hair and these locks thus impregnated are then subjected to the action of the liquid water/steam mixture under the conditions mentioned above, and the locks thus treated are then cooled, for example, by sending over or through them a stream of air chosen from cold air and ambient temperature air.
The liquid water/steam mixture used according to the present disclosure may be produced using any apparatus known in the art and intended for this purpose. In at least one embodiment, an apparatus comprising at least one steam generator directly connected to a hood that diffuses the liquid water/steam mixture onto the keratin fibers, for example, human hair, is used. A non-limiting example of an apparatus of this type is that sold under the name Micromist® by the company Takara Belmont.
Further disclosed herein is a dyeing process comprising applying to human keratin fibers such as the hair, a direct or oxidation dye composition (A) for a time that is sufficient to develop the color, and applying a composition (B) containing, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined previously, wherein composition (B) may be applied before or after application of composition (A).
The application of composition (A) may be followed by rinsing and/or drying of the keratin fibers.
The application of the composition (B) may be followed by rinsing and/or drying of the keratin fibers. Composition (B) may be preheated under the same conditions defined above. The application of composition (B) may be followed by heating of the keratin fibers under the same conditions defined above.
In at least one embodiment, composition (B) may be applied after applying the direct or oxidation dye composition (A). Composition (B), comprising the at least one unsaturated fatty substance of formula (I) may be applied immediately after dyeing, or after a delay. As used herein, the term “after a delay” means an application that takes place from a few hours up to several days (from 1 to 15 days) after dyeing. According to one embodiment, composition (B) may be applied immediately after dyeing the keratin fibers; and the application of the composition may be repeated between two colorations.
The nature and concentration of the dyes present in the dye composition (A) is not critical and may be chosen according to the general knowledge available in the art.
In the case of lightening direct dyeing operations, the dye compositions (A) result from the mixing, at the time of use, a dye composition (A1) containing at least one direct dye and a composition (A2) containing at least one oxidizing agent.
In the case of oxidation dyeing, the dye compositions (A) result from the mixing, at the time of use, a dye composition (A3) containing at least one oxidation base and optionally at least one coupler and/or a direct dye, and a composition (A4) containing at least one oxidizing agent.
The direct dyes may be chosen from compounds that absorb light radiation in the visible range (400-750 nm). They may be further chosen from nonionic, anionic, and cationic dyes.
Non-limiting examples of direct dyes include nitrobenzene dyes, and azo dyes, anthraquinone dyes, naphthoquinone dyes, benzoquinone dyes, phenothiazine dyes, indigoid dyes, xanthene dyes, phenanthridine dyes, phthalocyanin dyes, triarylmethane-based dyes, and mixtures thereof.
Suitable nitrobenzene dyes include red and orange compounds, such as 1-hydroxy-3-nitro-4-N-(γ-hydroxypropyl)aminobenzene, N-(β-hydroxyethyl)amino-3-nitro-4-aminobenzene, 1-amino-3-methyl-4-N-(β-hydroxyethyl)amino-6-nitrobenzene, 1-hydroxy-3-nitro-4-N-(β-hydroxyethyl)aminobenzene, 1,4-diamino-2-nitrobenzene, 1-amino-2-nitro-4-methylaminobenzene, N-(β-hydroxyethyl)-2-nitro-para-phenylenediamine, 1-amino-2-nitro-4-(β-hydroxyethyl)amino-5-chlorobenzene, 2-nitro-4-aminodiphenylamine, 1-amino-3-nitro-6-hydroxybenzene, 1-(β-aminoethyl)amino-2-nitro-4-(β-hydroxyethyloxy)benzene, 1-(β,γ-dihydroxypropyl)oxy-3-nitro-4-(β-hydroxyethyl)aminobenzene, 1-hydroxy-3-nitro-4-aminobenzene, 1-hydroxy-2-amino-4,6-dinitrobenzene, 1-methoxy-3-nitro-4-(β-hydroxyethyl)aminobenzene, 2-nitro-4′-hydroxydiphenylamine, 1-amino-2-nitro-4-hydroxy-5-methylbenzene, and mixtures thereof.
The nitrobenzene direct dyes may also include yellow and green-yellow dyes, for instance 1-β-hydroxyethyloxy-3-methylamino-4-nitrobenzene, 1-methylamino-2-nitro-5-(β,γ-dihydroxypropyl)oxybenzene, 1-(β-hydroxyethyl)amino-2-methoxy-4-nitrobenzene, 1-(β-aminoethyl)amino-2-nitro-5-methoxybenzene, 1,3-bis(β-hydroxyethyl)amino-4-nitro-6-chlorobenzene, 1-amino-2-nitro-6-methylbenzene, 1-(β-hydroxyethyl)amino-2-hydroxy-4-nitrobenzene, N-(β-hydroxyethyl)-2-nitro-4-trifluoromethylaniline, 4-(β-hydroxyethyl)amino-3-nitrobenzenesulfonic acid, 4-ethylamino-3-nitrobenzoic acid, 4-(β-hydroxyethyl)amino-3-nitrochlorobenzene, 4-(β-hydroxyethyl)amino-3-nitromethylbenzene, 4-(β,γ-dihydroxypropyl)amino-3-nitrotrifluoromethylbenzene, 1-(β-ureidoethyl)amino-4-nitrobenzene, 1,3-diamino-4-nitrobenzene, 1-hydroxy-2-amino-5-nitrobenzene, 1-amino-2-[tris(hydroxymethyl)methyl]amino-5-nitrobenzene, 1-(β-hydroxyethyl)amino-2-nitrobenzene, and 4-(β-hydroxyethyl)amino-3-nitrobenzamide.
R5 and R7, which may be identical or different, are chosen from β-hydroxyethyl radicals, β-hydroxypropyl radicals, γ-hydroxypropyl radicals, and β,γ-dihydroxypropyl radicals, wherein at least one of the radicals R6, R7, or R5 is a γ-hydroxypropyl radical and R6 and R7 are not simultaneously β-hydroxyethyl radicals when R5 is a γ-hydroxypropyl radical, such as those described in French patent FR 2 692 572.
As described herein, azo dyes are compounds comprising in their structure at least one —N═N— sequence not included in a ring; methine dyes are compounds comprising in their structure at least one —C═C— sequence not included in a ring; and azomethine dyes are compounds comprising in their structure at least one —C═N— sequence not included in a ring.
wherein A is chosen from oxygen and nitrogen.
The direct dyes may also be chosen, by non-limiting example, from basic dyes such as those listed in the Color Index, 3rd edition, under the names Basic Brown 16, Basic Brown 17, Basic Yellow 57, Basic Red 76, Basic Violet 10, Basic Blue 26, and Basic Blue 99; the acidic direct dyes listed in the Color Index, 3rd edition, under the names Acid Orange 7, Acid Orange 24, Acid Yellow 36, Acid Red 33, Acid Red 184, Acid Black 2, Acid Violet 43, and Acid Blue 62; and cationic direct dyes such as those described in International Patent Application Publication Nos. WO 95/01772 and WO 95/15144 and European Patent Application No. 0 714 954, which are incorporated herein by reference in their entireties, such as Basic Red 51, Basic Orange 31, and Basic Yellow 87.
When present, the at least one direct dye may be present in the composition in an amount ranging from 0.0005% to 12% by weight relative to the total weight of the composition, for example, from 0.005% to 6% by weight relative to the total weight of the composition.
The oxidation bases may be chosen from the oxidation bases conventionally used in oxidation dyeing, such as, by way of non-limiting example, para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols, and heterocyclic bases.
Examples of suitable para-phenylenediamines include, but are not limited to, para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, N,N-diethyl-4-amino-3-methylaniline, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 4-N,N-bis(β-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(β-hydroxy-ethyl)amino-2-chloroaniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N-ethyl-N-(β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylenediamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetyl-aminoethyloxy-para-phenylenediamine and N-(β-methoxyethyl)-para-phenylenediamine, and the acid addition salts thereof.
According to one embodiment, the para-phenylenediamines may be chosen from para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2-β-hydroxyethyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2-β-acetylaminoethyloxy-para-phenylenediamine, and the acid addition salts thereof.
Suitable bis(phenyl)alkylenediamines include, for example, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4-methylaminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and the acid addition salts thereof.
Non-limiting examples of para-aminophenols include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, and the acid addition salts thereof.
Examples of ortho-aminophenols include, but are not limited to 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and the acid addition salts thereof.
Non-limiting examples of pyridine derivatives include the compounds described, for example, in British Patent Nos. 1 026 978 and 1 153 196, such as 2,5-di-aminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and the acid addition salts thereof.
Examples of pyrimidine derivatives include, but are not limited to, the compounds described in German Patent No. 2 359 399; Japanese Patent Application No. 88-169 571; Japanese Patent No. 05-163 124; European Patent Application No. 0 770 375, and International Patent Application Publication No. WO 96/15765, such as 2,4,5,6-tetraminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in French Patent Application No. 2 750 048, for example, pyrazolo[1,5-a]pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo[1,5-a]-pyrimidine-3,7-diamine; pyrazolo[1,5-a]pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; 3-aminopyrazolo[1,5-a]pyrimidin-7-ol; 3-aminopyrazolo[1,5-a]pyrimidin-5-ol; 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]-pyrimidine, the acid addition salts thereof, and the tautomeric forms thereof, when a tautomeric equilibrium exists.
Suitable pyrazole derivatives include, for example, the compounds described in German Patent Nos. 3 843 892, 4 133 957, and 195 43 988, International Patent Application Publication Nos. WO 94/08969 and WO 94/08970, and French Patent No. 2 733 749, such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3, 4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, and the acid addition salts thereof.
When present, the at least one oxidation base may be present in the composition in an amount ranging from 0.0005% to 12% by weight relative to the total weight of the dye composition, for example, from 0.005% to 6% by weight relative to the total weight of the dye composition.
The oxidation dye compositions in accordance with the present disclosure may also comprise at least one coupler and/or at least one direct dye, for example, to modify the shades or to enrich them with tints.
The at least one coupler that can be used in the oxidation dye compositions according to the present disclosure may be chosen from the couplers conventionally used in oxidation dyeing, for example, meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthols, and heterocyclic couplers, for instance, indole derivatives, indoline derivatives, pyridine derivatives, indazole derivatives, pyrazolo[1,5-b]-1,2,4-triazole derivatives, pyrazolo[3,2-c]-1,2,4-triazole derivatives, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, 1,3-benzodioxole derivatives, pyrazolones, and the acid addition salts thereof.
According to one embodiment, the at least one coupler may be chosen from 2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(β-hydroxyethyloxy)benzene, 2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, α-naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine, 1-N(β-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(β-hydroxyethyleneamino)toluene, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, and the acid addition salts thereof.
When present, the at least one coupler may be present in the composition in an amount ranging from 0.0001% to 10% by weight relative to the total weight of the dye composition, for example, from 0.005% to 5% by weight relative to the total weight of the dye composition.
The dye composition in accordance with the present disclosure may also comprise at least one adjuvant chosen from various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric, and zwitterionic surfactants and mixtures thereof; anionic, cationic, nonionic, amphoteric, and zwitterionic polymers and mixtures thereof; mineral and organic thickeners; antioxidants; penetrants; sequestrants; fragrances; buffers; dispersants; conditioning agents, for instance, silicones; film-forming agents; preserving agents; and opacifiers.
It is to be understood that a person skilled in the art will take care to select the at least one optional additional compound such that the beneficial properties intrinsically associated with the dye composition in accordance with the present disclosure are not, or are not substantially, adversely affected by the envisaged addition.
The dye composition according to the present disclosure may be in various forms, such as liquids, creams, and gels, or in any other form that is suitable for dyeing keratin fibers such as human hair.
The nature of the at least one oxidizing agent used in the lightening direct dyeing operation (direct dyeing with an oxidizing agent) or in the oxidation dyeing operation is not critical and may be chosen in accordance with general knowledge available in the art.
In at least one embodiment, the at least one oxidizing agent may be chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, ferricyanides, and persalts such as perborates and persulfates. Redox enzymes such as laccases, peroxidases, and two-electron oxidoreductases (such as uricase) may also be used, where appropriate in the presence of the respective donor or cofactor thereof.
According to one embodiment, the process of the present disclosure may be used on hair that has been sensitized by hair treatments other than those mentioned previously in the present disclosure.
Also disclosed herein is also a multi-component dyeing kit comprising at least one first component comprising a direct dye composition (A) and at least one second component comprising a composition (B) containing, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein.
Further disclosed herein is a multi-component dyeing kit comprising at least one first component comprising a composition (A1) comprising at least one direct dye, at least one second component comprising a composition (A2) comprising at least one oxidizing agent, and at least one third component comprising a composition (B) comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein.
Still further disclosed herein is a multi-component dyeing kit comprising at least one first component comprising a composition (A3) comprising at least one oxidation base and optionally at least one coupler and/or at least one direct dye, at least one second component comprising a composition (A4) comprising at least one oxidizing agent, and a third component comprising a composition (B) comprising, in a cosmetically acceptable medium, at least one unsaturated fatty substance of formula (I) as defined herein.
At the time of use, an oxidation dye composition for a support, Recital®, containing 6×10−4 mol % of p-phenylenediamine and 6×10−4 mol % of 4-amino-2-hydroxytoluene, was mixed weight-for-weight with aqueous hydrogen peroxide solution (professional L'Oréal 20-volumes 6% aqueous hydrogen peroxide solution).
The mixture was then applied to locks of permanent-waved hair containing 90% white hairs, at a rate of 10 g of dye mixture/g of lock. The leave-on time was 15 minutes on each side of the lock. The locks were then rinsed with water, and then washed with DOP Camomile shampoo and dried.
Next, the treated locks were then left to stand for 30 minutes at 45° C.
The treated locks were then washed twice with DOP Camomile® shampoo so as to remove the residual surface oil.
Untreated locks (references) also underwent these two shampoo washes. The locks were then dried under a hood for 10 minutes at 60° C.
A shampoo-fastness test was performed on the above locks with a DOP Camomile® shampoo. 10 successive shampoo washes were performed, with intermediate drying.
The degradation of the color after washing the treated and untreated locks was evaluated visually relative to unwashed dyed locks.
These evaluations were accompanied by spectrocolorimetric monitoring. Measurements were taken using a Minolta CM2022 spectrocolorimeter, for up to 10 washes.
The protection is then expressed as a difference in ΔE between the treated and untreated locks. (Positive difference=gain in color protection, negative difference=loss in protection, significant difference with a gain ΔE=2).
After 10 shampoo washes, substantial degradation of the coloration of the untreated dyed locks was observed (loss of ΔE=12.98).
It was observed, surprisingly, that after 10 shampoo washes, only the locks A, B, and C that had been treated with fatty substances of the present disclosure provide a significant color protection compared with the untreated locks.
These results were confirmed by the calorimetric measurements, which indicate a significant gain in ΔE relative to the untreated lock as shown in the table below.
q is equal to 0, 1, or 2.
4. The process of claim 3, wherein the at least one unsaturated fatty substance of formula (I) is chosen from oleic acid, sorbitan oleate, and linoleic acid.
5. The process of claim 1, wherein the composition is applied to the fibers after dyeing.
6. The process of claim 1, wherein the cosmetically acceptable medium is chosen from water and mixtures of water and at least one cosmetically acceptable organic solvent.
7. The process of claim 6, wherein the at least one organic solvent is chosen from C1-C4 lower alkanols; polyols, and polyol ethers.
9. The process of claim 8, wherein the at least on organic solvent is present in the composition in an amount ranging from 3% to 30% by weight relative to the total weight of the composition.
10. The process of claim 1, wherein the at least one unsaturated fatty substance of formula (I) is present in the composition in an amount ranging from 1% to 100% by weight relative to the total weight of the composition.
11. The process of claim 1, wherein the at least one unsaturated fatty substance of formula (I) is present in the composition in an amount ranging from 5% to 90% by weight relative to the total weight of the composition.
12. The process of claim 10, wherein the composition comprises 100% by weight of the at least one unsaturated fatty substance of formula (I).
13. The process of claim 1, wherein the composition further comprises at least one additive chosen from anionic, cationic, nonionic, amphoteric, and zwitterionic surfactants; anionic, cationic, nonionic, amphoteric, and zwitterionic polymers; mineral and organic thickeners; penetrants; sequestrants; fragrances; buffers; dispersants; conditioning agents; film-forming agents; ceramides; preserving agents; and opacifiers.
14. The process of claim 1, wherein the composition further comprises at least one agent for protecting against the effects of atmospheric agents.
15. The process of 14, wherein the at least one agent for protecting against the effects of atmospheric agents is chosen from organic UV-screening agents, free-radical scavengers, and antioxidants.
16. The process of claim 1, wherein the composition further comprises at least one aromatic alcohol and at least one aromatic carboxylic acid.
17. The process of claim 1, wherein the composition further comprises at least one conditioning agent.
18. The process of claim 17, wherein the at least one conditioning agent is present in the composition in an amount ranging from 0.001% to 20% by weight relative to the total weight of the composition.
19. The process of claim 18, wherein the at least one conditioning agent is present in the composition in an amount ranging from 0.1% to 3% by weight relative to the total weight of the composition.
20. The process of claim 1, wherein the composition is in a form chosen from aqueous lotions, aqueous-alcoholic lotions, oils, gels, milks, creams, emulsions, and mousses.
21. The process of claim 1, wherein the composition is packaged in a container chosen from vaporizers, pump-dispenser bottles, and aerosol containers.
22. The process of claim 1, wherein the pH of the composition ranges from 1 to 11.
23. The process of claim 22, wherein the pH of the composition ranges from 2 to 6.
24. The process claim 1, further comprising rinsing and/or washing with shampoo before and/or after applying the composition to the keratin fibers.
25. The process of claim 1, further comprising total or partial drying of the keratin fibers with a hairdryer.
26. The process of claim 1, further comprising heating the composition before applying it to the keratin fibers.
27. The process of claim 1, further comprising heating the keratin fibers after application of the composition.
28. The process of claim 27, wherein the heating of the keratin fibers is performed using an iron, a liquid water/steam mixture, and/or a heating hood.
wherein composition (B) is applied to the fibers before or after the application of composition (A).
30. The process of claim 29, wherein the application of composition (A) is followed by rinsing and/or drying of the keratin fibers.
31. The process of claim 29, wherein the application of composition (B) is followed by rinsing and/or drying of the keratin fibers and/or by heating of the keratin fibers.
32. The process of claim 29, wherein composition (B) is preheated.
33. The process of claim 29, wherein composition (B) is applied after applying the direct or oxidation dye composition (A), either immediately or after a delay, and the application of composition (B) is optionally repeated between two colorations.
34. The process of claim 29, wherein the dye composition (A) results from the mixing, at the time of use, of a dye composition (A1) comprising at least one direct dye, and a composition (A2) comprising at least one oxidizing agent.
35. The process of claim 29, wherein the dye composition (A) results from the mixing, at the time of use, of a dye composition (A3) comprising at least one oxidation base and optionally at least one coupler and/or at least one direct dye, and a composition (A4) comprising at least one oxidizing agent.

References: Application No. 60
 § 119
 Application No. 101
 Application No. 198
 Application No. 0
 Application No. 342
 Application No. 2
 Application No. 0
 Application No. 0
 Application No. 88
 Application No. 0
 Application No. 2