Composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one coloring agent, and at least one fatty amine
A composition with N,N-dicarboxymethyl glutamic acid, oxidation dyes, and fatty amines addresses the limitations of existing hair coloring methods by providing intense, stable, and long-lasting coloration with improved dyeing performance.
Patent Information
- Application Number
- FR2022014667
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2022-12-29
- Publication Date
- 2025-11-28
- Estimated Expiration
- 2042-12-29
AI Technical Summary
Existing hair coloring methods, whether oxidation or direct dyeing, suffer from issues such as degradation of keratin fibers, temporary coloration, poor wash resistance, and long processing times, lacking in intensity, chromaticity, and tenacity.
A composition comprising N,N-dicarboxymethyl glutamic acid, oxidation dyes, direct dyes, and fatty amines, which provides intense, homogeneous coloration with good uptake and tenacity, and maintains stability over time.
The composition achieves powerful, long-lasting color with good distribution and stability, overcoming the limitations of existing methods by ensuring good dyeing performance and minimal viscosity or pH changes during storage.
Abstract
Description
Title of the invention: Composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one coloring agent, and at least one fatty amine
[0001] The present invention relates to a composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one coloring agent, and at least one fatty amine. technical field
[0002] For a long time, many people have sought to change the color of their hair, and in particular to cover their white hair.
[0003] Two main modes of coloring of human keratin fibers, and in particular of hair, are known.
[0004] One of these two methods is oxidation or permanent coloring. This coloring method uses one or more oxidation dye precursors, usually one or more oxidation bases possibly associated with one or more couplers.
[0005] In general, oxidation bases are chosen from among ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, in association with oxidizing products, allow access to colored species.
[0006] Often, the nuances obtained with these oxidation bases are varied by associating them with one or more couplers, the latter being chosen in particular from among the aromatic meta-diamines, the meta-aminophenols, the meta-diphenols and certain heterocyclic compounds, such as indolic compounds.
[0007] The variety of molecules involved in the oxidation bases and couplers allows for a rich palette of colors. This type of coloring also allows for permanent coloring, but the use of oxidizing agents can lead to degradation of the keratin fibers.
[0008] The second coloring method, called direct or semi-permanent coloring, involves the application of direct dyes, which are molecules with an affinity for fibers and which remain colored even in the absence of an oxidizing agent added to the compositions containing them. Given the nature of the molecules used, these remain mostly on the surface of the fiber and penetrate relatively little into the fiber, compared to the small precursor molecules of oxidation dyes.
[0009] The direct dyes generally used are chosen from among the benzene, anthraquinone, nitropyridine, azo, methicillin, azo- direct dyes Methinic, xanthenic, acridinic, azinic, or triarylmethanic dyes. The chemical species used can be nonionic, anionic (acidic dyes), or cationic (basic dyes). Direct dyes can also be natural dyes.
[0010] Hair coloring using natural direct dyes has been known since antiquity.
[0011] Compositions containing one or more natural direct dyes are applied to the keratin fibers for a time necessary to obtain the desired color, then rinsed.
[0012] However, the resulting colors, while potentially highly chromatic, are temporary or semi-permanent because desorption from the surface and / or core of the fiber results in weak dyeing power and poor wash resistance. Furthermore, these compositions require relatively long processing times, ranging from several tens of minutes to several hours (overnight), depending on the desired intensity, without any control over the outcome. The result varies depending on the fibers being dyed and the nature of the natural dye(s) used.
[0013] Thus, there is a real need to make available a coloring composition for keratin fibers, in particular human keratin fibers such as hair, which does not have the disadvantages mentioned above, that is to say, which is capable of leading to a good rise, intensity and chromaticity of the color, while having low selectivity and good tenacity and which is capable of leading to good dyeing performance, even after a period of storage, while having good qualities of use. Description of the invention
[0014] The present invention therefore relates to a composition comprising:
[0015] a) at least one compound selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and their mixtures; b) at least one coloring agent selected from oxidation dyes, direct dyes, and mixtures thereof; c) at least one compound selected from fatty amines, their salts, or mixtures thereof.
[0016] According to a preferred embodiment, the composition according to the invention is a keratin fiber coloring composition, in particular hair.
[0017] The composition according to the invention makes it possible, in particular, to produce powerful, intense, and non-selective chromatic colorations, that is to say, colorations that are homogeneous along the fiber. It also makes it possible to achieve different shades in a very wide range of colors. In addition, it allows for good color uptake and tenacity.
[0018] Furthermore, the composition according to the invention exhibits good performance qualities, notably a creamy texture and easy, even distribution throughout the hair. The composition according to the invention also exhibits good stability over time, in particular minimal or no change in its viscosity and / or pH during storage.
[0019] The expression "at least one" means one or more.
[0020] Unless otherwise indicated, the bounds of a range of values are included in that range, in particular in the expressions "between" and "ranging from ... to ...".
[0021] For the purposes of the present invention, "hair" means the hair on the head. This term does not include body hair, eyebrows, or eyelashes. N,N-Dicarboxymethyl glutamic acid
[0022] As indicated above, the composition according to the invention comprises at least one compound selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and mixtures thereof.
[0023] The salts include, in particular, salts of alkali metals, alkaline earth metals, ammonium and substituted ammonium.
[0024] Among the salts of these compounds, alkali metal salts are preferred, and in particular sodium or potassium salts.
[0025] The composition according to the invention preferably comprises tetrasodium glutamate diacetate (GLDA). For example, Akzo Nobel's Dissolvine GL38 or 45S may be used.
[0026] Advantageously, the total content of compounds selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and their mixtures varies from 0.001 to 15% by weight, preferably from 0.005 to 10% by weight, more preferably from 0.01 to 8% by weight, better from 0.05 to 5% by weight, even better from 0.075 to 2% by weight, or even from 0.1 to 1% by weight relative to the total weight of the composition.
[0027] According to a preferred embodiment, the total content of tetrasodium glutamate diacetate (GLDA) varies from 0.001 to 15% by weight, preferably from 0.005 to 10% by weight, more preferably from 0.01 to 8% by weight, better from 0.05 to 5% by weight, even better from 0.075 to 2% by weight, or even from 0.1 to 1% by weight relative to the total weight of the composition. Coloring agent
[0028] As indicated above, the composition according to the invention comprises at least one coloring agent chosen from oxidation dyes, direct dyes and their mixtures.
[0029] Oxidation dye
[0030] The composition according to the invention may include one or more oxidation dye(s).
[0031] Oxidation dyes are generally chosen from one or more oxidation bases, possibly combined with one or more coupling agents (or couplers).
[0032] By way of example, the oxidation bases are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases and corresponding addition salts.
[0033] Among the para-phenylenediamines that can be mentioned, examples include para-phenylenediamine, para-toluenediamine, 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, 4-amino-N,N-diethyl 1-3-methylaniline, N,N-bis([3-hydroxyethyl)-para-phenylenediamine, 4-N,N-bis([3-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(B-hydroxyethyl)amino-2-chloroaniline, 2-[3-hydroxyethyl-para-phenylenediamine, 2-methoxymethyl-para-phenylenediamine, 2-γ-hydroxypropyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-([3-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine,N-ethyl-N-([3-hydroxyethyl)-para-phenylenediamine, N-([3,Y-dihydroxypropyl)-para-phenylenediamine, N-(4'-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-[3-hydroxyethyloxy-para-phenylenediamine, 2-[3-acetylaminoethyloxy-para-phenylenediamine, N-(|3-methoxyethyl)-para-phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para-phenylenediamine, 2-[3-hydroxyethylamino-5-aminotoluene and 3-hydroxy-l-(4'-aminophenyl)pyrrolidine and the corresponding addition salts with an acid.
[0034] Among the aforementioned para-phenylenediamines, para-phenylenediamine, para-toluenediamine, 2-[3-hydroxyethyl-para-phenylenediamine, and para-phenylenediamine are particularly preferred. 2-Methoxymethyl-para-phenylenediamine, 2-γ-Hydroxypropyl-para-phenylenediamine, 2-Isopropyl-para-phenylenediamine, 2-[3-Hydroxyethyloxy-para-phenylenediamine, 2,6-Dimethyl-para-phenylenediamine, 2,6-Diethyl-para-phenylenediamine, 2,3-Dimethyl-para-phenylenediamine, N,N-bis([3-hydroxyethyl)-para-phenylenediamine, 2-Chloro-para-phenylenediamine and 2-[3-Acetylaminoethyloxy-para-phenylenediamine and the corresponding addition salts with an acid.
[0035] Among the bis(phenyl)alkylenediamines that can be mentioned, we find for example N,N'-bis([3-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diaminopropanol, N,N'-bis([3-hydroxyethyl)-N,N'-bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(P-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 and 1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane and the corresponding addition salts.
[0036] Among the para-aminophenols that are mentioned, we find for example para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-([3-hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol and the corresponding addition salts with an acid.
[0037] Among the ortho-aminophenols that can be mentioned, we find for example 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol and the corresponding addition salts.
[0038] Among the heterocyclic bases that can be mentioned, we find for example the derivatives of pyridine, pyrimidine and pyrazole.
[0039] Among the pyridine derivatives that can be mentioned are the compounds for example described in patents GB 1 026 978 and GB 1 153 196, for example 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine and the corresponding addition salts.
[0040] Other pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[l,5-a]pyridine oxidation bases or the corresponding addition salts described, for example, in French patent application FR 2 801 308. Examples that may be mentioned include pyrazolo[l,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[l,5-a]pyrid-3-ylamine, 2-morpholin-4-ylpyrazolo[l,5-a]pyrid-3-ylamine, 3-aminopyrazolo[l,5-a]pyridine-2-carboxylic acid, the 2-Methoxypyrazolo[l,5-a]pyrid-3-ylamine, (3-aminopyrazolo[l,5-a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[l,5-a]pyrid-5-yl)ethanol, 2-(3-aminopyrazolo[l,5-a]pyrid-7-yl)ethanol, (3-aminopyrazolo[l,5-a]pyrid-2-yl)methanol, 3,6-Diaminopyrazolo[l,5-a]pyridine, 3,4-Diaminopyrazolo[l,5-a]pyridine, pyrazolo[l,5-a]pyridine-3,7-diamine, 7-Morpholin-4-ylpyrazolo[l,5-a]pyrid-3-ylamine, pyrazolo[l,5-a]pyridine-3,5-diamine, 5-morpholin-4-ylpyrazolo[l,5-a]pyrid-3-ylamine, 2-[(3-aminopyrazolo[l,5-a]pyrid-5-yl)(2-hydroxyethyl)-amino]ethanol, 2-[(3-aminopyrazolo[l,5-a]pyrid-7-yl)(2-hydroxyethyl)amino]ethanol, 3-aminopyrazolo[l,5-a]pyridin-5-ol, 3-aminopyrazolo[l,5-a]pyridin-4-ol, 3-aminopyrazolo[l,5-a]pyridin-6-ol, 3-aminopyrazolo[l,5-a]pyridin-7-ol, 2-beta-hydroxyethoxy-3-amino-pyrazolo[l,5-a]pyridine; 2-(4-dimethylpiperazinium-l-yl)-3-amino-pyrazolo[l,5-a]pyridine; and the corresponding addition salts.
[0041] More particularly, the oxidation bases that are useful in the present invention are chosen from among the 3-aminopyrazolo-[1,5-a]-pyridines and preferably substituted at carbon atom 2 by:
[0042] a) a (di)(Ci-C6)(alkyl)amino group, said alkyl group being able to be substituted by at least one hydroxy, amino, imidazolium group;
[0043] b) a heterocycloalkyl group containing 5 to 7 members and 1 to 3 heteroatoms, optionally cationic, optionally substituted by one or more (Ci-C6)alkyl groups, such as a di(Ci-C4)alkylpiperazinium group; or
[0044] c) a (Ci-C6)alkoxy group optionally substituted by one or more hydroxy groups such as a [3-hydroxyalkoxy] group and the corresponding addition salts.
[0045] Among the pyrimidine derivatives that can be mentioned are the compounds described, for example, in patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96 / 15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine and their addition salts and their tautomeric forms, where a tautomeric equilibrium exists.
[0046] Among the pyrazole derivatives that can be mentioned are the compounds described in patents DE 3843892, DE 4133957 and patent applications WO 94 / 08969, WO 94 / 08970, FRA-2 733 749 and DE 195 43 988, such as 4,5-diamino-l-methylpyrazole, 4,5-diamino-l-([3-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-l-(4'-chlorobenzyl)pyrazole, the 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1,3-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-1-1 / 7-butyl-3-methylpyrazole, 4,5-diamino-1-([3-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-l-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5-diamino-l-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-l-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2'-aminoethyl)amino-l,3-dimethylpyrazole, 3,4,5-triaminopyrazole, l-methyl-3,4,5-triaminopyrazole, 3,5-diamino-l-methyl-4-methylaminopyrazole, 3,5-diamino-4-([3-hydroxyethyl)amino-l-methylpyrazole and the corresponding addition salts. 4,5-diamino-l-([3-methoxyethyl)pyrazole can also be used.
[0047] A 4,5-diaminopyrazole will preferably be used and even more preferably 4,5-diamino-l-([3-hydroxyethyl)pyrazole and / or a corresponding salt.
[0048] Pyrazole derivatives that may also be mentioned include diamino-N,N-dihydropyrazolopyrazolones and in particular those described in patent application FR-A-2 886 136, such as the following compounds and their corresponding addition salts: 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1H,2-a]pyrazol-1-one, 2-amino-3-ethylamino-6,7-dihydro-1H,5H-pyrazolo[1H,2-a]pyrazol-1-one, 2-amino-3-isopropylamino-6,7-dihydro-1H,5H-pyrazolo[1H,2-a]pyrazol-1-one, 2-amino-3-(pyrrolidin-l-yl)-6,7-dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l-one, 4,5-diamino-1,2-dimethyl-1,2-dihydropyrazol-3-one, 4,5-diamino-1,2-diethyl-1,2-dihydropyrazol-3-one, 4,5-diamino-1,2-di-(2-hydroxyethyl)-1,2-dihydropyrazol-3-one, 2-amino-3-(2-hydroxyethyl)amino-6,7-dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l-one, 2-amino-3-dimethylamino-6,7-dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l-one, 2,3-diamino-5,6,7,8-tetrahydro-lH,6H-pyridazino[l,2-a]pyrazol-l-one, 4-amino-1,2-diethyl-5-(pyrrolidin-1 -yl)-1,2-dihydropyrazol-3-one, 4-amino-5-(3-dimethylaminopyrrolidin-1 -yl)-1,2-diethyl-1,2-dihydropyrazol-3-one, 2,3-diamino-6-hydroxy-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one. ,
[0049] Preferably, 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one and / or a corresponding salt will be used.
[0050] Preferably, 4,5-diamino-l-([3-hydroxyethyl)pyrazole and / or 2,3-diamino-6,7-dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l-one and / or a corresponding salt will be used as heterocyclic bases.
[0051] Preferably, the oxidation base(s) is or are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the corresponding addition salts, and mixtures thereof; more preferably from 2-methoxymethyl-para-phenylenediamine, 2-[3-hydroxyethyl-para-phenylenediamine, 2-γ-hydroxypropyl)-para-phenylenediamine, and their addition salts, their solvates and / or the solvates of their salts, and mixtures thereof.
[0052] The composition according to the invention may optionally include one or more coupling agents advantageously chosen from those traditionally used in the coloring of keratin fibers.
[0053] Among these coupling agents, we can in particular mention meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based coupling agents and heterocyclic coupling agents as well as the corresponding addition salts.
[0054] Examples include 6-hydroxybenzomorpholine, 3,4-hydroxyethylmethylenedioxyaniline, 2-amino-5-ethylphenol, 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, 3-ureidoaniline, 3-ureido-1-dimethylaminobenzene, sesamol, α-naphtol, 2-methyl-1-naphtol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 2-amino-3-hydroxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 1N-(B-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(B-hydroxyethylamino)toluene, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, 2,6-dimethylpyrazolo[l,5-b]-l,2,4-triazole, 2,6-dimethyl[3,2-c]-l,2,4-triazole and 6-methylpyrazolo[l,5-a]benzimidazole,2-Methyl-5-aminophenol, 5-N-(B-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 3-amino-2-chloro-6-methylphenol, the corresponding addition salts with an acid, and the corresponding mixtures.
[0055] Preferably, the coupling agent(s) is / are selected from: 6-hydroxybenzomorpholine, its addition salts, its solvates and / or the solvates of its salts, hydroxyethyl-3,4-methylenedioxyaniline, its addition salts, its solvates and / or the solvates of its salts, 2-amino 5-ethylphenol, its addition salts, its solvates and / or the solvates of its salts and their mixtures.
[0056] In general, the addition salts of oxidation bases and coupling agents that can be used in the context of the invention are in particular chosen from addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
[0057] Furthermore, the solvates more particularly represent the hydrates of these oxidizing bases or coupling agents and / or the association of these oxidizing bases or coupling agents with a linear or branched alcohol in the C4 to C1 group, such as methanol, ethanol, isopropanol, n-propanol. Preferably, the solvates are hydrates.
[0058] The oxidation base(s) each advantageously represent 0.001% to 10% by weight relative to the total weight of the composition and preferably 0.005% to 5% by weight relative to the total weight of the composition and the ready-to-use composition.
[0059] Lc / lcs coupling agent(s), if present, each advantageously represent 0.001% to 10% by weight relative to the total weight of the composition and preferably 0.005% to 5% by weight relative to the total weight of the composition and the ready-to-use composition.
[0060] Direct dye
[0061] The composition according to the invention may comprise at least one coloring agent selected from direct colorants. Preferably, the coloring agent(s) are selected from direct colorants.
[0062] By "direct dye," we mean colored species. These are dyes that will diffuse superficially onto the fiber.
[0063] The direct dye(s) usable according to the invention are chosen from natural direct dyes, synthetic direct dyes, and their mixtures.
[0064] Preferably, the direct dye(s) usable according to the invention are chosen from ionic direct dyes and non-ionic direct dyes, more particularly from cationic direct dyes, amphoteric direct dyes, anionic direct dyes, non-ionic direct dyes, and mixtures thereof.
[0065] Direct dyes are for example chosen from neutral, acidic or cationic benzene nitrate direct dyes, neutral (non-ionic), acidic (anionic) or cationic azo direct dyes, tetraazapentamethamine dyes, quinonic dyes and in particular neutral, acidic or cationic anthraquinone dyes, azinic direct dyes, triarylmethanic direct dyes, azomethamine direct dyes and natural direct dyes.
[0066] The cationic direct dye(s) contain at least one quantified cationic chromophore or at least one chromophore bearing a quantified or quantizable cationic group.
[0067] According to a particular embodiment of the invention, the cationic direct dyes comprise at least one quaternized cationic chromophore.
[0068] Examples of cationic direct dyes according to the invention include acridines; acridones; anthranthrones; anthrapyrimidines; anthraquinones; azines; (poly)azoic, hydrazono or hydrazones, in particular arylhydrazones; azomethines; benzantrones; benzimidazoles; benzimidazolones; benzindoles; benzoxazoles; benzopyrans; benzothiazoles; benzoquinones; bisazines; bis-isoindolines; carboxanilides; coumarins; cyanines such as azacarbocyanines, diazacarbocyanines, diazahemicyanines, hemicyanines, or tetraazacarbocyanines; diazines; diketopyrrolopyrroles; dioxazines; diphenylamines; diphenylmethanes; dithiazines; flavonoids such as flavanthones and flavones; fluorindines; formazans; indamines; indanthrones; indigoids and pseudo-indigoids; indophenols; indoanilines; isoindolines; isoindolinones; isoviolanthones; lactones; (poly)methines such as stilbene or styryl-type dimethines; naphthalimides;naphthanilides; naphtho-lactams; naphthoquinones; nitro, particularly nitro(hetero)aromatics; oxadiazoles; oxazines; perilones; perinones; perylenes; phenazines; phenoxazine; phenothiazines; phthalocyanine; polyenes / carotenoids; porphyrins; pyrantrones; pyrazolantrones; pyrazolones; pyrimidinoantrones; pyronines; quinacridones; quinolines; quinophthalones; squaranes; tetrazoliums; thiazines, thioindigo; thiopyronines; triarylmethanes, or xanthenes.
[0069] For cationic azo dyes, particular mention can be made of those derived from the cationic dyes described in the Kirk-Othmer Encyclopedia of Chemical Technology, “Dyes, Azo”, J. Wiley & sons, updated on 19 / 04 / 2010.
[0070] Among the azo dyes that can be used according to the invention, cationic azo dyes described in patent applications WO 95 / 15144, WO 95 / 01772 and EP 714954 can be mentioned.
[0071] According to a preferred embodiment of the invention, the direct dye(s) are chosen from among the cationic dyes called "basic dyes".
[0072] Among the azo dyes described in the Colour Index International, 3rd edition, the following compounds may be cited, in particular:
[0073] -Basic Red 22
[0074] -Basic Red 76
[0075] -Basic Yellow 57
[0076] -Basic Brown 16
[0077] -Basic Brown 17
[0078] Among the cationic quinone dyes, those mentioned in the aforementioned Colour Index International are suitable, and among these, the following dyes may be cited, among others:
[0079] -Basic Blue 22
[0080] -Basic Blue 99.
[0081] Among the suitable azinic dyes are those listed in the Colour Index International and, for example, the following dyes:
[0082] -Basic Blue 17
[0083] -Basic Red 2.
[0084] Among the cationic triarylmethane dyes that can be used according to the invention, the following dyes may be mentioned, in addition to those listed in the Colour Index:
[0085] -Basic Green 1
[0086] -Basic Violet 3
[0087] -Basic Violet 14
[0088] -Basic Blue 7
[0089] -Basic Blue 26.
[0090] Cationic dyes can also be cited in documents US 5888252, EP 1133975, WO 03 / 029359, EP 860636, WO 95 / 01772, WO 95 / 15144, EP 714954. Also cited are those listed in the encyclopedia "The chemistry of synthetic dye" by K. VENKATARAMAN, 1952, Academy Press, volumes 1 to 7, in the "Kirk-Othmer" encyclopedia "Chemical technology", chapter "Dyes and Dye intermediate", 1993, Wiley and Sons, and in various chapters of the encyclopedia "ULLMANN'S ENCYCLOPEDIA of Industrial Chemistry", 7th edition, Wiley and Sons.
[0091] Preferably, cationic direct dyes are chosen from those derived from azo and hydrazono type dyes.
[0092] According to a particular embodiment, the direct dyes are cationic azoic dyes, described in EP 850636, FR 2788433, EP 920856, WO 9948465, FR 2757385, EP 85063, WO 850638, WO 9948433 9744004, FR 2570946, FR 2285851, DE 2538363, FR 2189006, FR 1560664, FR 1540423, FR 1567219, FR 1516943, FR 1212, 228 DE 4137005, WO 0166646, US 5708151, WO 9501772, WO 515144, GB 1195386, US 3524842, US 5879413, EP 1062940, EP 113938, DE 61387, DE 2527638, FR 2275462, GB 1974-27645, Acta Histochem. (1978), 61(1), 48-52 ; Cytology (1968), 10(3), 403-5 ; Zh. Obshch. Khim. (1970), 40(1), 195-202 ; Ann. Say. (Rome) (1975), 65(5-6), 305-14 ; Journal of the Chinese Chemical Society (Taipei) (1998), 45(1), 209-211 ; Rev. Rome. Say. (1988), 33(4), 377-83 ; Text. Nothing. J. (1984), 54(2), 105-7 ; Say. Ind. (Milan) (1974), 56(9), 600-3 ; Khim. Technol. (1979), 22(5), 548-53 ; Word. Monatsh. Chem. (1975), 106(3), 643-8 ; MRL Bull. Nothing. Dev.(1992), 6(2), 21-7; Lihua Jianyan, Huaxue Fence (1993), 29(4), 233-4; Dyes Pigm. (1992), 19(1), 69-79; Dyes Pigm. (1989), 11(3), 163-72. .
[0093] Preferably, the cationic direct dye(s) comprise a quaternary ammonium group, more preferably the cationic charge is endocyclic.
[0094] These cationic radicals are, for example, a cationic radical:
[0095] - with an exocyclic charge (di / tri)(Ci-C8)alkylammonium, or
[0096] - with endocyclic charge such as comprising a selected cationic heteroaryl group among: acridinium, benzimidazolium, benzobistriazolium, benzopyrazolium, benzopy-ridazinium, benzoquinolium, benzothiazolium, benzotriazolium, benzoxazolium, bi-pyridinium, bis-tetrazolium, dihydrothiazolium, imidazopyridinium, imidazolium, indolium, isoquinolium, naphthoimidazolium, naphthooxazolium, naphthopyrazolium, oxadiazolium, oxazolium, oxazolopyridinium, oxonium, phenazinium, phe-nooxazolium, pyrazinium, pyrazolium, pyrazoyltriazolium, pyridinium, pyridinoimi-dazolium, pyrrolium, pyrylium, quinolium, tetrazolium, thiadiazolium, thiazolium, thiazolopyridinium, thiazoylimidazolium, thiopyrylium, triazolium or xanthylium.
[0097] Examples include hydrazono cationic dyes of formula (C-II) and (C-III), azo dyes of formula (C-IV) and (C-V), as well as their optical, geometric, tautomeric isomers, their salts of organic or mineral acids or bases, and their solvates such as hydrates:
[0098] Hét+-C(Ra)=NN(Rb)-Ar, Q (C-II)
[0099] Hét+-N(Ra)-N=C(Rb)-Ar, Q (C-III)
[0100] Het+-N=N-Ar, Q (C-IV)
[0101] Ar+-N=N-Ar”, Q (CV),
[0102] formulas (C-II) to (CV) wherein:
[0103] * Het+ represents a cationic heteroaryl radical, preferentially with a ca charge endocyclic tionic such as imidazolium, indolium, or pyridinium, possibly preferentially substituted by at least one (CrC8)alkyl group such as methyl;
[0104] * Ar+ represents an aryl radical, such as phenyl or naphthyl, with a cationic charge exocyclic preferentially ammonium particularly tri(Ci-C8)alkyl-ammonium such as trimethylammonium;
[0105] * Ar represents an aryl group, in particular phenyl, possibly substituted, preferably by one or more electron-donating groups such as i) (CrC8)alkyl possibly substituted, ii) (CrC8)alkoxy possibly substituted, iii) (di)(Ci-C8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxyl group, iv) aryl(Ci-C8)alkylamino, v) N-(Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino possibly substituted or else Ar represents a julolidine group;
[0106] * Ar” represents a (hetero)aryl group, possibly substituted such that phenyl or pyrazolyl possibly substituted, preferably by one or more (Cl-C8)alkyl, hydroxyl, (di)(Cl-C8)(alkyl)amino, (Cl-C8)alkoxy or phenyl groups;
[0107] * Ra and Rb, identical or different, representing a hydrogen atom or a (Ci-C8)alkyl group possibly substituted, preferably by a hydroxyl group;
[0108] * or the substituent Ra with a substituent of Het+ and / or Rb with a substituent Ar together with the atoms that bear them form a (hetero)cycloalkyl; particularly Ra and Rb, representing a hydrogen atom or a (CrC4)alkyl group possibly substituted by a hydroxyl group;
[0109] * Q- represents an organic or mineral anionic counterion such as a halide or an alkyl sulfate.
[0110] In particular, one may cite the endo-cyclic cationic direct dyes of azo and hydrazono of formula (C-II) to (CV) as defined above; more particularly the endocyclic cationic direct dyes of formula (C-II) to (CV) described in patent applications WO 95 / 15144, WO 95 / 01772 and EP-714954.
[0111] Preferably, the following direct dyes may be mentioned: P (C-II-1), (C-IV-1),
[0112] formulas (C-II-1) and (C-IV-1) wherein:
[0113] - R1 represents a (Ci-C4)alkyl group such as methyl;
[0114] - R2 and R3, whether identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group such as methyl; and
[0115] - R4 represents a hydrogen atom or an electron-donating group such as (Ci - C8)alkyl possibly substituted, (CrC8)alkoxy possibly substituted, (di)(CrC8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxyl group; particularly R4 is a hydrogen atom,
[0116] - Z represents a CH group or a nitrogen atom, preferably CH,
[0117] - Q is an anionic counterion as defined previously, particularly ha logenide such as chloride or an alkylsulfate such as methylsulfate or mesytyl.
[0118] In particular, colorants of formula (C-II-1) and (C-IV-1) are selected from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or their derivatives: Basic Yellow 87,
[0119] with Q' an anionic counter ion as defined above, particularly a halide such as chloride or an alkyl sulfate such as methyl sulfate or mesytyl.
[0120] According to a particular embodiment of the invention, the direct dyes are fluorescent, that is to say they contain at least one fluorescent chromophore as defined above.
[0121] Examples of fluorescent dyes include radicals derived from the dyes acridines, acridones, benzantrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyranes, benzothiazoles, coumarins, difluoro{2-[(2H-pyrrol-2-ylidene-kN)methyl]-1H-pyrrolato-kN]bores (BODIPY®), diketopyrrolo-pyrroles, fluorindines, (poly)methines (in particular cyanines and styryls / hemicyanines), naphthalimides, naphthanilides, naphthylamine (such as dansyls), oxadiazoles, oxazines, perilones, perinones, perylenes, polyenes / carotenoids, squaranes, stilbenes, xanthenes.
[0122] Reference may also be made to the fluorescent dyes described in documents EP 1133975, WO 03 / 029359, EP 860636, WO 95 / 01772, WO 95 / 15144, EP 714954 and those listed in the encyclopedia "The chemistry of synthetic dye" by K. VEN-KATARAMAN, 1952, Academy press vol 1 to 7, in the "Kirk-Othmer" encyclopedia "Chemical technology", chapter "Dyes and Dye intermediate", 1993, Wiley and sons, and in various chapters of the encyclopedia "ULLMANN's ENCYCLOPEDIA of Industrial chemistry" 7th edition, Wiley and sons, in The Handbook — A Guide to Fluorescent Probes and Labeling Technologies, 1st Ed Molecular Probes / Invitrogen -Oregon 2005 distributed by the Internet or in previous printed editions.
[0123] According to one embodiment of the invention, the cationic dye(s) are fluorescent and comprise at least one quaternary ammonium radical such as those of the following (C-VI) formula, as well as their optical, geometric, tautomeric isomers, their salts of organic or mineral acids or bases, and their solvates such as hydrates:
[0124] W+-[C(Rc)=C(Rd)]m-Ar, Q (C-VI),
[0125] formula (C-VI) wherein:
[0126] * W+ represents a cationic heterocyclic or heteroaryl group, particularly including a quaternary ammonium possibly substituted by one or more (Ci-C8)alkyl groups possibly substituted in particular by one or more hydroxyl groups;
[0127] * Ar representing an aryl group such as phenyl or naphthyl, possibly preferentially substituted by i) one or more halogen atoms, such as chlorine, fluorine; ii) one or more (CrC8)alkyl groups, preferably in C1-4 such as methyl; iii) one or more hydroxyl groups; iv) one or more (CrC8)alkoxy groups such as methoxy; v) one or more hydroxy(CrC8)alkyl groups such as hydroxyethyl; vi) one or more amino or (di)(C1-8)alkylamino groups, preferably with the alkyl portion in C1-4 optionally substituted by one or more hydroxyl groups such as (di)hydroxyethylamino; vii) by one or more acylamino groups; viii) one or more heterocycloalkyl groups such as pyperazinyl, pyperidinyl or 5- or 6-membered heteroaryl groups such as pyrrolidinyl, pyridinyl and imidazolinyl;
[0128] * m' represents an integer between 1 and 4 inclusive, particularly m equals 1 or 2; more preferably 1;
[0129] * Rc, Rd, whether identical or different, represent a hydrogen atom or a (CrC8)alkyl group possibly substituted, preferably in CrC4, or else Rc contiguous to W+ and / or Rd contiguous to Ar form with the atoms which bear them a (hetero)cycloalkyl, particularly Rc is contiguous to W+ and form a (hetero)cycloalkyl such as cyclohexyl;
[0130] * Q is an organic or mineral anionic counter-ion as defined above.
[0131] Among cationic direct dyes, we can also mention ca- dyes
[0132] triarylmethane ions. Preferably, the triarylmethane cationic direct dye(s) according to the invention are chosen from the following cationic dyes of formulas (C-VII) and (C-VII'): (C-VII),
[0133]
[0134]
[0135]
[0136] as well as its addition salts with an acid or a base, organic or mineral, its geometric, optical, tautomeric isomers, and its mesomeric forms, its solvates such as hydrates, formulas (C-VII) and (C-VII') preceding in which: * Rb R2, R3 and R4, identical or different, represent a hydrogen atom or a (Ci-C6)alkyl group, possibly substituted, preferably by a hydroxyl group; aryl such as phenyl, aryl(Ci-C4)alkyl such as benzyl, heteroaryl, heteroaryl(Ci-C4)alkyl, or two groups Ri and R2, and / or R3 and R4, borne by the same nitrogen atom, together with the nitrogen atom bearing them form a heterocycloalkyl group, possibly substituted, such as morpholino, piparazino, piperidino, preferably Rh. R2, R3 and Ri, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, * R5, R6, R7, Rs, R9, Rio, Ru, R12, Rb, Ru, Rb and Ri6, whether identical or different, represent a hydrogen atom, a halogen atom, or a group selected from i) hydroxyl, ii) thiol, iii) amino, iv) (di)(Cl-C4)(alkyl)amino, v) (di)arylamino such as (di)phenylamino, vi) nitro, vii) acylamino (-NR-C(O)R') in which the R radical is a hydrogen atom, a CrC4 alkyl radical possibly bearing at least one hydroxyl group, and the R' radical is a CrC2 alkyl radical; viii) carbamoyl ((R)2 NC(O)-) in which the R radicals, whether identical or not, represent a hydrogen atom, a C1-C4 alkyl radical possibly bearing at least one hydroxyl group; ix) carboxylic acid or ester, (-OC(O)R') or
[0137] (-C(O)OR'), in which the radical R' is a hydrogen atom, or a C1-C4 alkyl possibly bearing at least one hydroxyl group and the radical R' is a Ci-C2 alkyl radical; x) alkyl possibly substituted in particular by a hydroxy group; xi) alkylsulfonylamino (R'SO2-NR-) in which the radical R represents a hydrogen atom, an alkyl radical in CrC4 possibly bearing at least one hydroxyl group and the radical R' represents an alkyl radical in CrC4, a phenyl radical; xii) aminosulfonyl ((R)2N-SO2 ) in which the radicals R, identical or not, represent a hydrogen atom, an alkyl radical in CrC4 possibly bearing at least one hydroxyl group, xiii) (CrC4)alkoxy, and xiv) (Ci-C4)alkylthio;
[0138] * Or two radicals carried by two adjacent carbon atoms R5 and R6 and / or R7 and R8, and / or R9 and Rio and / or Ru and R[2 and / or Rn and R[4 and / or Ri5 and Ri6 together with the carbon atoms that bear them form a condensed 6-membered aryl or heteroaryl ring, preferably benzo, said ring possibly being further substituted, preferably an unsubstituted benzo ring;
[0139] * Q represents an anionic counter ion to achieve electroneutrality, of preference chosen from among halides such as chloride, bromide, and phosphate.
[0140] When the cationic dye includes 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, so that the overall resulting charge of the triarylmethane structure is cationic.
[0141] According to a preferred embodiment, the triarylmethane dye(s) of the invention is / are selected from those of formula (C-VII) or (C-VII'), wherein, taken together or separately,
[0142] - Rb R2, R3 and Re represent a hydrogen atom or a (CrC4)alkyl group such whether methyl or ethyl,
[0143] - R5, R6, R7, R8, R9, Rio, Ru, Ri2, Ri3, Ri4, Rb and R6, represent an atom of hydrogen, halogen, 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 groups R9, R10, Rn or Rn represents an atom of hydrogen, halogen (Cl), or an amino group, or a (CrC4)(alkyl)amino or (di)(CrC4)(alkyl)amino group, preferably in the para position of the phenyl group.
[0144] Preferably, the direct triarylmethane structure dye(s) 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.
[0145] The composition according to the invention may comprise one or more anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as "acid" direct dyes because of their affinity for alkali substances. Anionic direct dyes are understood to mean any direct dye having in its structure at least one CO2R or SO3R substituent, where R designates a hydrogen atom or a cation from a metal or an amine, or an ammonium ion. The anionic dyes may be selected from among acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethane dyes, acidic indoamine dyes, acidic anthraquinone dyes, acidic indigoid dyes, and acidic natural dyes.
[0146] According to the invention, the anionic direct dye(s) may be selected, alone or in mixture, from the following anionic direct dyes of formulas (A-II), (A-IT), (A-III), (A-nr), (A-IV), (A-IV'), (AV), (A-V'), (A-VI), (A-VII), (A-VIII) and (A-IX)
[0147] a) Diaryl anionic azo dyes of formula (A-II) or (A-II'):
[0148] formulas (A-II) and (A-II') wherein:
[0149] * R7, R8, R9, Rio, R'7, R'8, R'9 and R'1O, whether identical or different, represent an atom of hydrogen or a group chosen from:
[0150] - alkyl;
[0151] - alkoxy, alkyIthio;
[0152] - hydroxy, mercapto;
[0153] - nitro, nitroso;
[0154] - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X”- with R° representing an atom of hydrogen, an alkyl or aryl group; X, X' and X”, identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group;
[0155] - (O)2S(O )-, M+ with M+ representing a hydrogen atom or a counterion ca tionic;
[0156] - (O)CO -, M+ with M+ as defined above;
[0157] - R”-S(O)2-, with R” representing a hydrogen atom, an alkyl group, a aryl group, (di)(alkyl)amino, aryl(alkyl)amino; preferably a phenylamino or phenyl group;
[0158] - R'”-S(O)2-X'- with R”' representing an alkyl group, possibly aryl substituted, X' as defined previously;
[0159] - (di)(alkyl)amino;
[0160] - aryl(alkyl)amino optionally substituted by one or more selected groups among i) nitro; ii) nitroso; iii) (O)2S(O )-, M+ and iv) alkoxy with M+ as defined previously;
[0161] - heteroaryl possibly substituted; preferably a benzo- group thiazolyl;
[0162] - cycloalkyl; in particular cyclohexyl,
[0163] - Ar-N=N- with Ar representing a possibly substituted aryl group; pre preferentially a phenyl possibly substituted by one or more alkyl groups, (O)2S(O )-, M+ or phenylamino;
[0164] - or two contiguous groups R7 with R8 or R8 with R9 or R9 with Rio together form a fused group benzo A'; and R'7 with R'8 or R'8 with R'9 or R'9 with R'1O together form a fused group benzo B'; with A' and B' possibly substituted by one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2S(O-)-, M+; iv) hydroxy; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X'-; vüi) R°-X'-C(X)-; ix) R°-X'-C(X)-X”-; x) Ar-N=N- and xi) aryl(alkyl)amino possibly substituted; with M+, R°, X, X', X” and Ar as defined above;
[0165] * W represents a sigma bond, an oxygen atom, a sulfur atom, or a radical divalent i) -NR- with R as defined above, or ii) methylene -C(Ra)(Rb)- with Ra and Rb, identical or different, representing a hydrogen atom or an aryl group, or Ra and Rb together with the carbon atom bearing them form a spiro cycloalkyl; preferably W represents a sulfur atom or Ra and Rb together form a cyclohexyl;
[0166] it being understood that the formulas (A-II) and (A-IT) comprise at least one sulfonate radical (O)2S(O )-, M+ or one carboxylate radical (O)CO -, M+ on one of the rings A, A', B, B' or C; preferably sodium sulfonate;
[0167] A titre d’exemple de colorants de formule (A-II), on peut citer : Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2 ; Food yellow 3 ou sunset yellow;
[0168] et à titre d’exemple de colorants de formule (A-IF), on peut citer : Acid Red 111, Acid Red 134, Acid yellow 38 ;
[0169] b) les colorants azo anioniques pyrrazolone de formule (A-III) et (A-IIF) :
[0170] formulas (A-III) and (A-III') wherein:
[0171] * Rn, Rn and Rn, whether identical or different, represent a hydrogen atom, halogen, an alkyl group or -(O)2S(O ), M+ with M+ as defined previously;
[0172] * Ru represents a hydrogen atom, an alkyl group or a - group C(O)O , M+ with M+ as defined previously;
[0173] * R15 represents a hydrogen atom;
[0174] * Ri6 represents an oxo group in which case R'i6 is absent, or else R[5 with R[6 together form a double bond;
[0175] * Rn and Ri8, whether identical or different, represent a hydrogen atom, or a group chosen from:
[0176] - (O)2S(O )-, M+ with M+ as defined previously;
[0177] - Ar-OS(O)2- with Ar representing an aryl group possibly substituted; preferably a phenyl possibly substituted by one or more alkyl groups;
[0178] * R19 and R2q together form either a double bond or a benzo D' group, possibly substituted;
[0179] * R'16, R'19 and R'2O, whether identical or different, represent a hydrogen atom or an alkyl group, or hydroxy;
[0180] * R2i represents a hydrogen atom, an alkyl group, or alkoxy;
[0181] * Ra and Rb, whether identical or different, are as defined above, preferably Ra represents a hydrogen atom and Rb represents an aryl group;
[0182] * Y represents either a hydroxy group or an oxo group;
[0183] * represents a single bond when Y is an oxo group; and re presents a double bond when Y represents a hydroxy group;
[0184] provided that the formulas (A-III) and (A-III') comprise at least one sulfonate radical (O)2S(O )-, M+ or one carboxylate radical -C(O)O, M+ on one of the rings D or E; preferably sodium sulfonate;
[0185] Examples of colorants of formula (A-III) include: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and examples of colorants of formula (A-III') include: Acid Yellow 17;
[0186] c) the anthraquinone dyes of formula (A-IV) and (A-IV'):
[0187] formulas (A-IV) and (A-IV) in which:
[0188] * R22, R23, R24, R25, R26 and R27, whether identical or different, represent an atom of hydrogen, halogen, or a group chosen from:
[0189] - alkyl;
[0190] - hydroxy, mercapto;
[0191] - alkoxy, alkylthio;
[0192] - aryloxy or arylthio, possibly substituted, preferably substituted by a or several groups chosen from alkyl and (O)2S(O )-, M+ with M+ as defined previously;
[0193] - aryl(alkyl)amino optionally substituted by one or more selected groups among alkyl and (O)2S(O )-, M+ with M+ as defined previously;
[0194] - (di)(alkyl)amino;
[0195] - (di)(hydroxyalkyl)amino
[0196] - (O)2S(O )-, M+ with M+ as defined previously;
[0197] * Z' represents a hydrogen atom or an NR28R29 group with R28 and R29, identical or different, represent a hydrogen atom or a group chosen from:
[0198] - alkyl;
[0199] - polyhydroxyalkyl such as hydroxyethyl;
[0200] - aryl possibly substituted by one or more particularly i) groups alkyl such as methyl, n-dodecyl, n-butyl; ii) (O)2S(O )-, M+ with M+ 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;
[0201] - cycloalkyl; in particular cyclohexyl;
[0202] * Z, represents a group selected from hydroxy and NR'28R'29 with R'28 and R'29, identical or different, represent the same atoms or groups as R28 and R29 as defined previously;
[0203] it being understood that the formulas (A-IV) and (A-IV') comprise at least one sulfonate radical (O)2S(O )-, M+ or one carboxylate radical -C(O)O, M+; preferably sodium sulfonate;
[0204] As an example of dyes of formula (A-IV), we can cite: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT purple No. 2;
[0205] and as an example of colorants of formula (A-IV') we can cite: Acid Black 48;
[0206] d) Nitrated dyes of formula (AV), and (A-V'):
[0207] formulas (AV) and (A-V') wherein:
[0208] * R3o, R3i and R32, whether identical or different, represent a hydrogen atom, halogen, or a group selected from:
[0209] - alkyl;
[0210] - alkoxy possibly substituted by one or more hydroxy groups, alkylthio possibly substituted by one or more hydroxy groups;
[0211] - hydroxy, mercapto;
[0212] - nitro, nitroso;
[0213] - polyhalogenoalkyl;
[0214] - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X”- with R° ; X, X' and X” as defined previously;
[0215] - (O)2S(O )-, M+ with M+ as defined previously;
[0216] - (O)CO -, M+ with M+ as defined above;
[0217] - (di)(alkyl)amino;
[0218] - (di)(hydroxyalkyl)amino;
[0219] - heterocycloalkyl such as piperidino, piperazino or morpholino;
[0220] particularly R30, R3i and R32 represent a hydrogen atom;
[0221] * Rc and Rd, whether identical or different, represent a hydrogen atom or a alkyl group;
[0222] * W is as defined above; W particularly represents a grouping -NH-;
[0223] * ALK represents a divalent alkylene group, linear or branched, in C1-C6; particularly ALK represents a grouping -CH2-CH2-;
[0224] * n equals 1 or 2;
[0225] * p represents an integer between 1 and 5 inclusive;
[0226] * q represents an integer between 1 and 4 inclusive;
[0227] * u is equal to 0 or 1;
[0228] * when n equals 1, J represents a nitro or nitroso group; particularly nitro;
[0229] * when n equals 2, J represents an oxygen atom, a sulfur atom, or a divalent radical —S(O)m— with m representing an integer 1 or 2; preferably J represents a radical -SO2-;
[0230] * M' represents a hydrogen atom or a cationic counter-ion;
[0231] * . ' - „ ' " present or absent represents a benzo group,
[0232] possibly substituted by one or more R30 groupings as defined above;
[0233] it being understood that the formulas (AV) and (A-V') comprise at least one sulfonate radical (O)2S(O )-, M+ or one carboxylate radical -C(O)O, M+; preferably sodium sulfonate;
[0234] As an example of colorants of formula (AV) we can cite: Acid Brown 13; Acid Orange 3; examples of dyes with the formula (A-V') include: Acid Yellow 1, Sodium salt of 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2(4'-N,N(2"-hydroxyethyl)amino-2'-nitro)aniline ethanesulfonic acid, 4-β-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C yellow 7;
[0235] e) triarylmethane dyes of formula (A-VI):
[0236] formula (A-VI) in which:
[0237] * R33, R34, R35 and R36, whether identical or different, represent a hydrogen atom or a group chosen from alkyl, possibly substituted aryl and possibly substituted arylalkyl; particularly an alkyl and benzyl group possibly substituted by an (O)mS(O )-, M+ group with M+ and m as defined above;
[0238] * R37, R38, R39, R40, R41, R42, R43 and R44, whether identical or different, represent an atom of hydrogen or a group chosen from:
[0239] - alkyl;
[0240] - alkoxy, alkylthio;
[0241] - (di)(alkyl)amino;
[0242] - hydroxy, mercapto;
[0243] - nitro, nitroso;
[0244] - R°-C(X)-X' -, R°-X' -C(X)-, R°-X' -C(X)-X' ' - with R° representing an atom of hydrogen, an alkyl or aryl group; X, X' and X”, identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group;
[0245] - (O)2S(O )-, M+ with M+ representing a hydrogen atom or a Ca- counterion tionic;
[0246] - (O)CO -, M+ with M+ as defined above;
[0247] - or two contiguous groups R41 with R42 or R42 with R^ or R4i with R44 together form a fused benzo group: I'; with I' possibly substituted by one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2 S(O )-, M+; iv) hydroxy; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X'-; viii) R°-X'-C(X)-; ix) R°-X'-C(X)-X”-; with M+, R°, X, X', X” as defined above;
[0248] particularly R37 to R40 represent a hydrogen atom, and R4[ to R44, identical or different, represent a hydroxy group or (O)2S(O )-, M+ ; and when R4I with R^ together form a benzo group, it is preferentially substituted by an (O)2S(O )- group;
[0249] provided that at least one of the rings G, H, I or I' comprises at least one sulfonate radical (O)2S(O )- or one carboxylate radical -C(O)O; preferably sulfonate.
[0250] Examples of colorants of formula (A-VI) include: Acid Blue 1; Acid Blue 3; Acid Blue 7; Acid Blue 9; Acid Violet 49; Acid green 3; Acid green 5; Acid Green 50;
[0251] f) xanthene-derived dyes of formula (A-VII): (A-VII)
[0252] formula (A-VII) wherein:
[0253] * R45, R46, R47 and R48, whether identical or different, represent a hydrogen atom or an atom of halogen;
[0254] * R49, R50, R5i and R52, whether identical or different, represent a hydrogen atom, halogen, or a group selected from:
[0255] - alkyl;
[0256] - alkoxy, alkylthio;
[0257] - hydroxy, mercapto;
[0258] - nitro, nitroso;
[0259] - (O)2S(O )-, M+ with M+ representing a hydrogen atom or a counterion ca tionic;
[0260] - (O)CO -, M+ with M+ as defined above;
[0261] particularly R53, R54, R55 and R^ represent a hydrogen or halogen atom
[0262] * G represents an oxygen atom, a sulfur atom, or an NRe group with Re such that defined previously; in particular G represents an oxygen atom;
[0263] * L represents an alkoxide O, M+; a thioalkoxide S, M+ or an NRf group, with Rf representing a hydrogen atom or an alkyl group, and M+ as defined previously; M+ is particularly sodium or potassium;
[0264] * L' represents an oxygen atom, sulfur atom, or ammonium group: N+Rf Rg, with Rf and Rg, identical or different, representing a hydrogen atom, an alkyl group, possibly substituted aryl; L' particularly represents an oxygen atom or a phenylamino group possibly substituted by one or more alkyl groups or (O)mS(O )-, M+ with m and M+ as defined previously;
[0265] * Q and Q', identical or different, represent an oxygen or sulfur atom; in particular Q and Q' represent an oxygen atom;
[0266] * M+ is as defined previously.
[0267] Examples of colorants of formula (A-VII) include: Acid Yellow 73; Acid Red 51; Acid Red 52; Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9;
[0268] g) dyes derived from indole of formula (A-VIII):
[0269] formula (A-VIII) in which:
[0270] * R53, R54, R55, R56, R57, R58, R59 and R60, whether identical or different, represent an atom of hydrogen or a group chosen from:
[0271] -alkyl;
[0272] - alkoxy, alkylthio;
[0273] - hydroxy, mercapto;
[0274] - nitro, nitroso;
[0275] - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X' ' - with R° representing an atom of hydrogen, an alkyl or aryl group; X, X' and X”, identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group;
[0276] - (O)2S(O )-, M+ with M+ representing a hydrogen atom or a counterion ca tionic;
[0277] - (O)CO -, M+ with M+ as defined above;
[0278] * G represents an oxygen atom, a sulfur atom, or an NRe group with Re such that defined previously; in particular G represents an oxygen atom;
[0279] * R; and Rh, identical or different, represent a hydrogen atom or a alkyl group;
[0280] it being understood that the formula (A-VIII) comprises at least one sulfonate radical (O)2S(O )-, M+ or one carboxylate radical -C(O)O , M+; preferably sodium sulfonate;
[0281] As an example of colorants of formula (A-VIII), we can cite: Acid Blue 74.
[0282] h) quinoline-derived dyes of formula (A-IX):
[0283] formula (A-IX) in which:
[0284] * R6i represents a hydrogen atom, a halogen atom or an alkyl group;
[0285] * R62, Res, and R64, whether identical or different, represent a hydrogen atom or a group (O)2S(O )-, M+ with M+ representing a hydrogen atom or a cationic counter-ion;
[0286] * or R6i with R62, or R6i with R64, together form a benzo group possibly substituted by one or more (O)2S(O )-, M+ groups with M+ representing a hydrogen atom or a cationic counter-ion;
[0287] it being understood that the formula (A-IX) comprises at least one sulfonate radical (O)2S(O )-, M+ preferably sodium sulfonate.
[0288] Examples of colorants of formula (A-IX) include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.
[0289] More specifically, the coloring composition comprises one or more anionic direct dyes selected, alone or in mixture, from the following anionic direct dyes:
[0290] [Tables 1] (C.L 45380) Acid Red 87 (A-VII) (C.L 10316) Sel de sodium de l’acide 2,4-dinitro-l-naphtol-7-sulfonique (A-V’) (C.L 10383) Acid Orange 3 (A-V) (C.L 13015) Acid Yellow 9 / Food Yellow 2 (A-II) (C.L 14780) / Direct Red 45 / Food Red 13 (A-II) (C.L 13711) Acid Black 52 (A-II) (C.L 13065) Acid Yellow 36 (A-II) (C.L 14700) Sel de sodium de l’acide l-hydroxy-2-(2',4'-xylyl-5-sufonatoazo)-naphtalène-4-sulfonique / Food Red 1 (A-II) (C.L 14720) Acid Red 14 / Food Red 3 / Mordant Blue 79 (A-II) (C. 1. 14805) Sel de sodium de l’acide 4-hydroxy-3-[(2-métoxy-5-. ni-trophényl)diaza]-6-(phénylamino)naphtalène-2-sulfonique / Acid Brown 4 (A-II) (C.L 15510) Acid Orange 7 / Pigment Orange 17 / Solvent Orange 49 (A-II) (C.L 15985) Food Yellow 3 / Pigment Yellow 104 (A-II) (C.L 16185) Acid Red 27 / Food Red 9 (A-II) (C.L 16230) Acid Orange 10 / Food Orange 4 (A-II) (C.L 16250) Acid Red 44 (A-II) (C.L 17200) Acid Red 33 / Food Red 12 (A-II) (C.L 15685) Acid Red 184 (A-II) (C.L 19125) Acid Violet 3 (A-II) (CL 18055) Sodium salt of l-hydroxy-2-(4'-acetamidophenylazo)-8-acetamido-naphthalene-3,6-disulfonic acid / Acid Violet 7 / Food Red 11 (A-II) (CL 18130) Acid Red 135 (A-II) (CL 19130) Acid Yellow 27(A-III) (CL 19140) Acid Yellow 23 / Food Yellow 4 (A-III) (CL 20170) 4'-(sulfonato-2,4"-dimethyl)-bis-(2,6-phenylazo)-l,3-dihydroxy. Benzene / Acid Orange 24 (A-II) (CL 20470) Sodium salt of l-amino-2-(4'-nitrophenylazo)-7-phenylazo-8-hydroxy-naphthalene-3,6-disulfonic acid / Acid Black 1 (A-II) (CL 23266) (4-((4-methylphenyl)sulfonyloxy)-phenylazo)2,2'-dimethyl-4-((2-hydroxy-5,8-disulfonat o)naphtylazo)biphenyl / Acid Red 111 (A-II') (CL 27755) Food Black 2 (A-II) (CL 25440) l-(4'-sulfonatophenylazo)-4-((2"-hydroxy-3"-acetylamino-6",8"-disulfonato)naphtylazo)-6-sulfonatonaphthalene (salt tetrasodium) / Food Black 1 (A-II) (CL 42090) Acid Blue 9 (A-VI) (CL 60730) Acid Violet 43 (A-IV) (CL 61570) Acid Green 25 (A-IV) (CL 62045) Sodium salt of l-amino-4-cyclohexylamino-9,10-anthraquinone 2-sulfonic acid / Acid Blue 62 (A-IV) (CL 62105) Acid Blue 78 (A-IV) (C.L 14710) Sodium salt of 4-hydroxy-3((2-methoxyphenyl)-azo)-1-naphthalene sulfonic acid / Acid Red 4 (A-II) 2-piperidino-5-nitrobenzene sulfonic acid (V') 2(4'-N,N(2"-hydroxyethyl)amino-2'-nitro)aniline ethane sulfonic acid (A-V') 4-[3-hydroxyethylamino-3-nitrobenzene sulfonic acid (A-V') (CL 42640) Acid Violet 49 (A-VI) (CL 42080) Acid Blue 7 (A-VI) (CL 58005) Sodium salt of 1,2-dihydroxy-3-sulfo-anthraquinone / Mordant Red 3 (A-IV) (CL 62055) Sodium salt of acid l-amino-9,10-dihydro-9,10-dioxo-4-(phenylamino) 2-anthracene sulfonic acid / Acid Blue 25 (A-IV) (CL 14710) Sodium salt of the acid. 4-hydroxy-3-((2-methoxyphenyl)-azo)-l-naphthalene sulfonic acid / Acid Red 4 (A-II)
[0291] Most of these dyes are described in particular in the Color Index published by The Society of Dyers and Colorists, PO Box 244, Perkin House, 82 Grattan Road, Bradford, Yorkshire, BD1 2JBN England.
[0292] The anionic colorants most particularly preferred are the colorants designated in the Color Index under the code CI 58005 (monosodium salt of 1,2-dihydroxy-9,10-anthraquinone-3-sulfonic acid), CI 60730 (monosodium salt of 2-[(9,10-dihydro-4-hydroxy-9,10-dioxo-l-anthracenyl)-amino]-5-methylbenzene sulfonic acid), CI 15510 (monosodium salt of the acid 4-[(2-hydroxy-l-naphthalenyl)-azo]-benzene sulfonic acid), CI 15985 (disodium salt of 6-hydroxy-5-[(4-sulfophenyl)-azo]-2-naphthalene sulfonic acid), CI 17200 (disodium salt of 5-amino-4-hydroxy-3-(phenylazo)-2,7-naphthalene disulfonic acid), CI 20470 (disodium salt of l-amino-2-(4'-nitrophenylazo)-7-phenylazo-8-hydroxy-3,6-naphthalene disulfonic acid), CI 42090 (disodium salt of N-ethyl-N-[4-[[4-[ethyl[3-sulfophenyl)-methyl]-amino]-phenyl](2-sulfophenyl)-methylene e]-2,5-cyclohexadien-l-ylidene]-3-sulfobenzenemethanaminium hydroxide, internal salt), CI 61570 (disodium salt of acid 2,2'-[(9,10-dihydro-9,10-dioxo-l,4-anthracenediyl)-diimino]-bis-[5-methyl]-benzene sulfonic acid.
[0293] Compounds corresponding to the mesomeric, tautomeric forms of (A-II) to (A-IX) structures can also be used.
[0294] Among the natural direct dyes that can be used according to the invention, mention may be made of hennotannic acid, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orcein. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, may also be used.
[0295] Preferably, the coloring agent is chosen from direct dyes, more preferably said direct dye(s) are chosen from ionic direct dyes and non-ionic direct dyes, more particularly from cationic direct dyes, amphoteric direct dyes, anionic direct dyes, non-ionic direct dyes, and mixtures thereof.
[0296] Advantageously, the coloring agent is chosen from among direct dyes, more preferably chosen from azo direct dyes, direct dyes hydrazono, aryl nitrate direct dyes, triarylmethane direct dyes, quinone direct dyes and in particular anthraquinones, and mixtures thereof.
[0297] Advantageously, the total content of the colouring agent(s), preferably of the direct colour(s), ranges from 0.001 to 20% by weight, preferably from 0.005 to 15% by weight, more preferably from 0.01 to 10% by weight, better from 0.05 to 5%, even better from 0.1 to 3% by weight, relative to the total weight of the composition. Fatty amine
[0298] As indicated above, the composition according to the invention comprises at least one compound selected from fatty amines, their salts, or mixtures thereof.
[0299] The term “fatty amine” means a compound comprising at least one primary, secondary or tertiary amine function, possibly (poly)oxyalkylated, or their salts and comprising at least one C6-C30 hydrocarbon chain, preferably C8-C30.
[0300] Preferably, the useful fatty amines according to the invention are not (poly)oxyalkylated.
[0301] Among the fatty amines, we can mention stearylamine, stearyldimethylamine, distearylamine.
[0302] Fatty amines can also be cited as examples of amidoamines. The amidoamines according to the invention can be selected from among the fatty amidoamines, the fatty chain being able to be borne by the amine group or by the amido group.
[0303] Amidoamine is understood to mean a compound comprising at least one amide function and at least one primary, secondary or tertiary amine function.
[0304] Fatty amidoamine is understood to be an amidoamine comprising at least one C6-C30 hydrocarbon chain. Preferably, the fatty amidoamines useful according to the invention are not quantified.
[0305] Preferably, the fatty amidoamines useful according to the invention are not (poly)oxyalkylated.
[0306] Preferably, the fatty amidoamines are chosen from (Ci0-C30)alkylamido(Ci-C8)alkyl (di)(Ci-C6)alkyl amines and their salts, better from (Ci4-C26)alkylamido(Ci-C6)alkyl (di)(Ci-C4)alkyl amines and their salts, preferably from (Ci6-C24)alkylamido(C2-C4)alkyl (di)(CrC2)alkyl amines and their salts; more preferably still from (Ci8-C22)alkylamido(C2-C4)alkyl (di)(CrC2)alkyl amine and their salts.
[0307] Among the useful fatty amidoamines according to the invention, we can mention the amidoamines of the following formula (A): RCONHR”N(R')2 (A)
[0308] in which:
[0309] - R represents a monovalent linear or branched hydrocarbon radical, saturated or unsaturated and substituted or unsubstituted, having from 5 to 29 carbon atoms, preferably from 7 to 23 carbon atoms, and in particular a C5-C29 alkyl radical, preferably C7-C23, linear or branched, or a C5-C29 alkenyl radical, preferably C7-C23, linear or branched;
[0310] - R” represents a divalent hydrocarbon radical having less than 6 atoms of carbon, preferably 2 to 4 carbon atoms, better 3 carbon atoms; and
[0311] - R', identical or different, represent a monovalent hydrocarbon radical having less than 6 carbon atoms, preferably 1 to 4 carbon atoms, linear or branched, saturated or unsaturated and substituted or unsubstituted, preferably a methyl radical.
[0312] Examples of fatty amidoamines that may be used include, alone or in mixtures: oleamidopropyl dimethylamine, stearamidopropyl dimethylamine, particularly that marketed by INOLEX CHEMICAL COMPANY under the name LEXAMINE S13, isostearamidopropyl dimethylamine, stearamidoethyl dimethylamine, lauramidopropyl dimethylamine, myristamidopropyl dimethylamine, behenamidopropyl dimethylamine, dilinoleamidopropyl dimethylamine, palmitamidopropyl dimethylamine, ricinoleamindopropyl dimethylamine, soyamidopropyl dimethylamine, avocadoamidopropyl dimethylamine, cocamidopropyl dimethylamine, minkamidopropyl dimethylamine, oatamidopropyl dimethylamine, sesamidopropyl dimethylamine, tallamidopropyl dimethylamine, and olivamidopropyl dimethylamine, palmitamidopropyl dimethylamine, stearamidoethyldiethylamine, brassicamidopropyl dimethylamine and their salts.
[0313] Preferably, fatty amidoamines are selected from, alone or in mixtures, as well as their salts,
[0314] - brassicamidopropyl dimethylamine of formula RC(O)-N(H)-(CH2)3-N(CH3)2;
[0315] wherein RC(O) is a fatty acid derived from brassica campestris seed oil (rapeseed oil), with a majority of behenyl group (C22);
[0316] - stearamidopropyl dimethylamine of formula CH3-(CH2)i6-C(O)-N(H)-(CH2)3 - N(CH3)2;
[0317] - behenamidopropyl dimethylamine of formula CH3-(CH2)2o-C(0)-N(H)-(CH2)3 - N(CH3)2;
[0318] - oleamidopropyl dimethylamine.
[0319] Advantageously, the fatty amines are chosen from fatty amidoamines, their salts and mixtures thereof, preferably from amidoamines of formula (A).
[0320] Preferably, the amidoamines of formula (A) are selected from brassicamidopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl dimethylamine, oleamidopropyl dimethylamine, and mixtures thereof.
[0321] According to a preferred embodiment, the compound(s) selected from fatty amines, their salts, and mixtures thereof are selected from fatty amidoamines, their salts and mixtures thereof, preferably from (Cio-C30)alkylamido(Ci-C8)alkyl (di)(Ci-C6)alkyl amines and their salts, more preferably from (Ci4-C26)alkylamido(Ci-C6)alkyl (di)(Ci-C4)alkyl amines and their salts, more preferably still from (Ci6-C24)alkylamido(C2-C4)alkyl (di)(Ci-C2)alkyl amines and their salts; better still from (Ci8-C22)alkylamido(C2-C4)alkyl (di)(Ci-C2)alkyl amines and their salts.
[0322] According to a particularly preferred embodiment, the compound or compounds chosen from fatty amines, their salts, and mixtures thereof are chosen from brassicami-dopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl di-methylamine, oleamidopropyl dimethylamine, and mixtures thereof.
[0323] Advantageously, the total content of the compound(s) selected from fatty amines, their salts, and mixtures thereof shall be from 0.01 to 6% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 1.5 to 3% by weight relative to the total weight of the composition.
[0324] Advantageously, the total content of the compound(s) selected from the (Ci0-C30)alkylamido(Ci-C8)alkyl (di)(Ci-C6)alkyl amines and their salts ranges from 0.01 to 6% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 1.5 to 3% by weight relative to the total weight of the composition.
[0325] Advantageously, the total content of the compound(s) selected from among the amidoamines of formula (A) ranges from 0.01 to 6% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 1.5 to 3% by weight relative to the total weight of the composition. Non-silicone fats
[0326] The composition according to the invention may further comprise at least one non-siliconized fatty substance other than the fatty amines described above.
[0327] The term "fatty substance" means an organic compound insoluble in water at 25°C and atmospheric pressure (1.013 x 10⁵ Pa) (solubility less than 5% by weight, and preferably less than 1% by weight, and even more preferably less than 0.1% by weight). Fatty substances have in their structure at least one hydrocarbon chain comprising at least 6 carbon atoms and / or a chain of at least two siloxane groups. In addition, fatty substances are generally soluble in organic solvents under the same conditions of temperature and pressure, such as, for example, chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), petrolatum, or decamethylcyclopentasiloxane.
[0328] The non-siliconized fats usable in the present invention, other than fatty amines, are neither (poly)oxyalkylated nor (poly)glycerolated.
[0329] The term "non-siliconized fat" means a fat that does not contain Si-O bonds and the term "siliconized fat" means a fat that contains at least one Si-O bond.
[0330] Preferably, the non-siliconized fat(s) according to the invention, other than fatty amines, are different from fatty acids.
[0331] The non-siliconized fats useful according to the invention may be liquid non-siliconized fats (or oils) and / or solid non-siliconized fats and / or pasty non-siliconized fats. A liquid fat is defined as a fat having a melting point less than or equal to 25°C at atmospheric pressure (1.013 x 10⁵ Pa), and a solid fat is defined as a fat having a melting point greater than 25°C at atmospheric pressure (1.013 x 10⁵ Pa).
[0332] For the purposes of the present invention, the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (differential scanning calorimetry or DSC) as described in ISO 11357-3; 1999. The melting point can be measured using a differential scanning calorimeter (DSC), for example, the calorimeter sold under the name "MDSC 2920" by TA Instruments. In the present application, all melting points are determined at atmospheric pressure (1.013 x 10⁵ Pa).
[0333] More particularly, the liquid non-siliconized fat(s) may be chosen from liquid hydrocarbons in the range of C6 to Ci6, liquid hydrocarbons comprising more than 16 carbon atoms, non-siliconized oils of animal origin, triglyceride-type oils of vegetable or synthetic origin, fluorinated oils, liquid fatty alcohols, liquid esters of fatty acids and / or fatty alcohols other than triglycerides and mixtures thereof.
[0334] It is recalled that alcohols, esters and fatty acids more particularly have at least one hydrocarbon group, linear or branched, saturated or unsaturated, comprising from 6 to 40, preferably from 8 to 30 carbon atoms, possibly substituted, in particular by one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or not.
[0335] With regard to liquid hydrocarbons in the C6 to C16 range, these may be linear, branched, possibly cyclic, and are preferably chosen from among the alkanes. By way of example, hexane, cyclohexane, undecane, dodecane, isododecane, tridecane, isoparaffins such as isohexadecane, isodecane, and mixtures thereof may be cited.
[0336] Liquid hydrocarbons comprising more than 16 carbon atoms may be linear or branched, of mineral or synthetic origin, and are preferably chosen from paraffin or petrolatum (or mineral oil), polydecenes, hydrogenated polyisobutene such as Parleam®, and mixtures thereof.
[0337] Perhydrosqualene is an example of hydrocarbon oils of animal origin.
[0338] Triglyceride oils of vegetable or synthetic origin are preferably chosen from among liquid triglycerides of fatty acids comprising 6 to 30 carbon atoms such as triglycerides of heptanoic or octanoic acid or, for example, sunflower, corn, soybean, pumpkin, grapeseed, sesame, hazelnut, apricot, macadamia, arara, castor, avocado oils, caprylic / capric acid triglycerides such as those sold by Stea-rineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel, jojoba oil, shea butter oil, and mixtures thereof.
[0339] As regards fluorinated oils, these can be chosen from per-fluoromethylcyclopentane and perfluoro-1,3-dimethylcyclohexane, sold under the names "FLUTEC® PCI" and "FLUTEC® PC3" by BNFL Fluorochemicals; perfluoro-1,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names "PF 5050®" and "PF 5060®" by 3M, or bromoperfluorooctyl sold under the name "FORALKYL®" by Atochem; no-nafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives, such as 4-trifluoromethyl perfluoromorpholine sold under the name "PF 5052®" by 3M.
[0340] Liquid fatty alcohols suitable for implementing the invention are particularly selected from saturated or unsaturated, linear or branched alcohols, preferably unsaturated or branched, having from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms. These fatty alcohols are neither oxyalkylated nor glycerolated. Examples include octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, isostearyl alcohol, oleic alcohol, linolenic alcohol, ricinoleic alcohol, undecylenic alcohol, or linoleic alcohol, and mixtures thereof. Preferably, oleic alcohol is used.
[0341] With regard to liquid esters of fatty acids and / or fatty alcohols, other than the triglycerides mentioned above, one may mention in particular the esters of saturated or unsaturated mono- or poly-aliphatic acids, linear in Cl to C26 or branched in C3 to C26 and of saturated or unsaturated mono- or poly-aliphatic alcohols, linear in Cl to C26 or branched in C3 to C26, the total number of carbons of the esters being greater than or equal to 6, more advantageously greater than or equal to 10.
[0342] According to a preferred embodiment, liquid esters of fatty acids and / or fatty alcohols other than triglycerides are selected from liquid esters of fatty acids and fatty alcohols, preferably selected from esters of linear monoalcohols, more preferably selected from coco caprylate, coco caprate, and mixtures thereof.
[0343] Preferably, for monoalcohol esters, at least one of the alcohol or acid is branched.
[0344] Among the monoesters, the following may be mentioned: dihydroabietyl behenate; octyldodecyl behenate; isocetyl behenate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; isostearyl octanoate; isocetyl octanoate; octyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methyl acetyl ricinoleate; octyl isononanoate; 2-ethylhexyl isononate; octyldodecyl erucate; oleyl erucate; ethyl and isopropyl palmitates, such as ethyl-2-hexyl palmitate, 2-octyldecyl palmitate; alkyl myristates such as 2-octyldodecyl isopropyl myristate; isobutyl stearate; 2-hexyldecyl laurate, and mixtures thereof.
[0345] Preferably among monoesters of monoacids and monoalcohols, ethyl and isopropyl palmitates, alkyl myristates such as isopropyl or ethyl myristate, isocetyl stearate, ethyl-2-hexyl isononanoate, isodecyl neopentanoate, isostearyl neopentanoate; and mixtures thereof shall be used.
[0346] Esters of di- or tricarboxylic acids in C4 to C22 and of alcohols in Cl to C22 and esters of mono-, di-, or tricarboxylic acids and di-, tri-, tetra- or pentahydroxy alcohols in C2 to C26 can also be used.
[0347] Examples include: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; din-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisotearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisanonate; polyethylene glycol distearates, and mixtures thereof.
[0348] The composition may also include, as a fatty acid ester, esters and diesters of sugars of fatty acids in the C6 to C30 range, preferably in the C12 to C22 range. It should be noted that the term "sugar" means oxygenated hydrocarbon compounds possessing several alcohol functional groups, with or without aldehyde or ketone functional groups, and comprising at least four carbon atoms. These sugars may be monosaccharides, oligosaccharides, or polysaccharides other than the anionic polysaccharides described above.
[0349] Suitable sugars may be cited for example sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose, and their derivatives in particular alkylated, such as methylated derivatives like methylglucose.
[0350] Sugar and fatty acid esters may be selected in particular from the group comprising the esters or mixtures of sugar esters described above and fatty acids in the range of C6 to C30, preferably C12 to C22, linear or branched, saturated or unsaturated. If unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or not.
[0351] Esters can also be selected from mono-, di-, tri- and tetra-esters, polyesters and their mixtures.
[0352] These esters may be, for example, oleate, laurate, palmitate, myristate, behenate, cocoate, stearate, linoleate, linolenate, caprate, arachidonate, or mixtures thereof, such as mixed oleo-palmitate, oleo-stearate, palmito-stearate esters.
[0353] In particular, mono- and di- esters are used, and in particular mono- or di- oleate, stearate, behenate, oleopalmitate, linoleate, linolenate, oleostearate, of sucrose, glucose or methylglucose, and mixtures thereof.
[0354] One can cite as an example the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.
[0355] Preferably, the composition according to the invention comprises a liquid ester of monoacid and monoalcohol.
[0356] According to one embodiment, the non-siliconized fats useful according to the invention are chosen from liquid fats, preferably from liquid hydrocarbons in C6 to Ci6, vegetable oils, liquid hydrocarbons containing more than 16 carbon atoms, liquid fatty alcohols, liquid esters of fatty acids and / or fatty alcohols other than triglycerides and their mixtures.
[0357] Solid fats preferably have a viscosity greater than 2 Pa.s, measured at 25°C and at a shear rate of 1 s1.
[0358] The solid fat(s) are preferably chosen from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, waxes, ceramides and mixtures thereof.
[0359] By "fatty alcohol" is meant a long-chain aliphatic alcohol comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, and comprising at least one hydroxyl group OH. These fatty alcohols are neither oxyalkylated nor glycerolated.
[0360] Solid fatty alcohols may be saturated or unsaturated, linear or branched, and comprise from 8 to 40 carbon atoms, preferably from 10 to 30 carbon atoms. Preferably, solid fatty alcohols have an R-OH structure with R designating a linear alkyl group, possibly substituted by one or more hydroxy groups, comprising 8 to 40, preferably 10 to 30 carbon atoms, better 10 to 30, or even 12 to 24 atoms, even better 14 to 22 carbon atoms.
[0361] The solid fatty alcohols that may be used are preferably chosen from saturated or unsaturated, linear or branched (mono)alcohols, preferably linear and saturated, comprising 8 to 40 carbon atoms, better 10 to 30, or even 12 to 24 atoms, even better 14 to 22 carbon atoms.
[0362] The solid fatty alcohols that may be used may be selected from, alone or in mixture: myristic or myristyl alcohol (or 1-tetradecanol); cetyl alcohol (or 1-hexadecanol); stearyl alcohol (or 1-octadecanol); arachidyl alcohol (or 1-eicosanol); behenyl alcohol (or 1-docosanol); lignoceryl alcohol (or 1-tetracosanol); ceryl alcohol (or 1-hexacosanol); montanylic alcohol (or 1-octacosanol); myricyl alcohol (or 1-triacontanol).
[0363] Preferably, the solid fatty alcohol is chosen from cetyl alcohol, stearyl alcohol, behenyl alcohol, myristic alcohol, arachidic alcohol and mixtures thereof, such as cetylstearyl or cetearyl alcohol.
[0364] In a particularly preferred manner, the solid fatty alcohol is chosen from cetyl alcohol, stearyl alcohol, their mixtures, such as cetylstearyl or cetearyl alcohol.
[0365] The solid fatty acid and / or fatty alcohol esters that may be used are preferably selected from esters derived from C9-C26 carboxylic fatty acids and / or C9-C26 fatty alcohols.
[0366] Preferably, these solid fatty acid esters are esters of saturated linear or branched carboxylic acids comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms and more particularly from 12 to 24 carbon atoms, and of saturated linear or branched monoalcohols comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms and more particularly from 12 to 24 carbon atoms. The saturated carboxylic acids may optionally be hydroxylated, and are preferably monocarboxylic acids.
[0367] Esters of di- or tricarboxylic acids in C4-C22 and of alcohols in C1-C22 and esters of mono-, di- or tricarboxylic acids and of di-, tri-, tetra- or pentahydroxylated alcohols in C2-C26 can also be used.
[0368] Examples include octyldodecyl behenate, isocetyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, hexyl stearate, octyl stearate, myristyle stearate, cetyl stearate, stearyl stearate, octyl pelargonate, cetyl myristate, myristyle myristate, stearyl myristate, diethyl sebacate, sebacate diisopropyl, düsopropyl adipate, din-propyl adipate, dioctyl adipate, dioctyl maleate, octyl palmitate, myristyle palmitate, cetyl palmitate, stearyl palmitate, and mixtures thereof.
[0369] Preferably, the solid fatty acid and / or fatty alcohol esters are selected from C9-C26 alkyl palmitates, in particular myristyle, cetyl, stearyl palmitates; C9-C26 alkyl myristates such as cetyl myristate, stearyl myristate and myristyle myristate; C9-C26 alkyl stearates, in particular myristyle, cetyl and stearyl stearates; and mixtures thereof.
[0370] A wax, as defined in the present invention, is a lipophilic compound, solid at 25°C and atmospheric pressure, with a reversible solid / liquid phase change, a melting point above approximately 40°C and up to 200°C, and an anisotropic crystalline structure in the solid state. Generally, the size of the wax crystals is such that they diffract and / or scatter light, giving the composition a cloudy, more or less opaque appearance. By heating the wax to its melting point, it can be made miscible with oils and form a microscopically homogeneous mixture, but by lowering the temperature of the mixture to room temperature, the wax recrystallizes, a phenomenon detectable both microscopically and macroscopically (opalescence).
[0371] In particular, the waxes suitable for the invention can be chosen from waxes of animal, vegetable, mineral origin, non-siliconized synthetic waxes and mixtures thereof.
[0372] Examples include hydrocarbon waxes, such as beeswax, particularly of biological origin, lanolin wax, and Chinese insect waxes; rice bran wax, carnauba wax, candelilla wax, ouricury wax, alfa wax, berry wax, shellac wax, Japanese wax and sumac wax; Montan wax, orange and lemon waxes, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, waxes obtained by Fisher-Tropsch synthesis and waxy copolymers, as well as their esters.
[0373] We can also mention microcrystalline waxes in C20 to C60, such as Microwax HW.
[0374] We can also mention PM 500 polyethylene wax marketed under the reference Permalen 50-L polyethylene.
[0375] We can also mention waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched fatty chains, from C8 to C32. Among these, we can notably mention isomerized jojoba oil, such as partially hydrogenated isomerized trans jojoba oil, in particular that manufactured or marketed by the company Desert Whale under the trade name Iso-Jojoba-50®, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil, and di-(trimethyloi-1,1,1 propane tetrastearate), in particular that sold under the name Hest 2T-4S® by the company HETERENE.
[0376] Waxes obtained by hydrogenation of esterified castor oil with cetyl alcohol, such as those sold under the names Phytowax ricin 16L64® and 22L73® by the company SOPHIM, can also be used.
[0377] As a wax, a C20 to C40 alkyl (hydroxystearyloxy)stearate (the alkyl group comprising 20 to 40 carbon atoms) can also be used, alone or in a mixture. Such a wax is notably sold under the names "Kester Wax K 82 P®", "Hydroxypolyester K 82 P®" and "Kester Wax K 80 P®" by the company KOSTER KEUNEN.
[0378] It is also possible to use microwaxes in the compositions of the invention;Examples include carnauba microwaxes, such as the one marketed under the name MicroCare 350® by MICRO POWDERS; synthetic wax microwaxes, such as the one marketed under the name MicroEase 114S® by MICRO POWDERS; microwaxes made from a mixture of carnauba wax and polyethylene wax, such as those marketed under the names Micro Care 300® and 310® by MICRO POWDERS; microwaxes made from a mixture of carnauba wax and synthetic wax, such as the one marketed under the name Micro Care 325® by MICRO POWDERS; polyethylene microwaxes, such as those marketed under the names Micropoly 200®, 220®, 220L® and 250S® by MICRO POWDERS; and polytetrafluoroethylene microwaxes, such as those marketed under the names Microslip 519® and 519 L® by the company MICRO POWDERS. ;
[0379] Waxes are preferably chosen from mineral waxes such as paraffin wax, petroleum jelly, lignite or ozokerite; vegetable waxes such as cocoa butter or waxes from cork or sugar cane fibers, olive wax, rice wax, hydrogenated jojoba wax, Ouricoury wax, carnauba wax, candelilla wax, esparto grass wax, or absolute flower waxes such as blackcurrant flower essential wax sold by the BERTIN company (France); waxes of animal origin such as beeswax or modified beeswax (cerabellina), spermaceti, lanolin wax and lanolin derivatives; microcrystalline waxes; and mixtures thereof.
[0380] Ceramides or ceramide analogues such as glycoceramides, which can be used in compositions according to the invention, are known; in particular, ceramides of classes I, II, III and V according to the DAWNING classification may be mentioned.
[0381] Ceramides or their analogues that may be used preferably correspond to the following formula: R3CH(OH)CH(CH2OR2)(NHCOR1), in which:
[0382] R1 designates an alkyl group, linear or branched, saturated or unsaturated, derived from fatty acids in Ci4-C30, this group being able to be substituted by a hydroxyl group in the alpha position, or a hydroxyl group in the omega position esterified by a saturated or unsaturated fatty acid in Ci6-C30;
[0383] R2 denotes a hydrogen atom, a (glycosyl)n group, a (galactosyl)m group or a sulfogalactosyl group, in which n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 8;
[0384] R3 designates a hydrocarbon group in Ci5-C26, saturated or unsaturated in the alpha position, this group being able to be substituted by one or more alkyl groups in CrCi4; it being understood that in the case of natural ceramides or glycoceramides, R3 may also designate an alpha-hydroxyalkyl group in Ci5-C26, the hydroxyl group being optionally esterified by an alpha-hydroxy acid in Ci6-C30.
[0385] The ceramides most particularly preferred are the compounds for which R1 designates a saturated or unsaturated alkyl derived from fatty acids in Ci6-C22; R2 designates a hydrogen atom and R3 designates a linear group saturated in Ci5.
[0386] Preferably, ceramides are used in which R1 designates a saturated or unsaturated alkyl group derived from fatty acids in Ci4-C30; R2 designates a galactosyl or sulfogalactosyl group; and R3 designates a -CH=CH-(CH2)i2-CH3 group.
[0387] Compounds can also be used in which R1 designates a saturated or unsaturated alkyl radical derived from fatty acids in C[2-C22]; R2 designates a galactosyl or sulfogalactosyl radical and R3 designates a hydrocarbon radical in C[2-C22], saturated or unsaturated and preferably a -CH=CH-(CH2)i2-CH3 group.
[0388] As particularly preferred compounds, we may also mention 2-N-linoleoylamino-octadecane-l,3-diol; 2-N-oleoylamino-octadecane-l,3-diol; 2-N-palmitoylamino-octadecane-l,3-diol; 2-N-stearoylamino-octadecane-l,3-diol; 2-N-behenoylamino-octadecane-l,3-diol; 2-N-[2-hydroxy-palmitoyl]-amino-octadecane-l,3-diol; 2-N-stearoyl amino-octadecane-1,3,4-triol, and in particular N-stearoyl phytosphingosine; 2-N-palmitoylamino-hexadecane-1,3-diol; N-linoleoyldihydrosphingosine; N-oleoyldihydrosphingosine; N-palmitoyldihydrosphingosine; N-stearoyldihydrosphingosine; and N-behenoyldihydrosphingosine; N-docosanoyl N-methyl-D-glucamine; N-(2-hydroxyethyl)-N-(3-cetyloxy-2-hydroxypropyl) cetyl acid amide; and bis-(N-hydroxyethyl N-cetyl)malonamide; and mixtures thereof. Preferably, N-oleoyldihydrosphingosine shall be used.
[0389] Non-siliconized solid fats are preferably selected from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, and mixtures thereof, pre preferentially among solid fatty alcohols, and their mixtures, in particular among cetyl alcohol, stearyl alcohol and their mixtures such as cetyl-stearyl or cetearyl alcohol.
[0390] Butters can also be used.
[0391] For the purposes of this invention, "butter" (also referred to as "pasty fat") means a lipophilic fatty compound with a reversible solid / liquid phase change, comprising, at a temperature of 25°C and atmospheric pressure (760 mm Hg), a liquid fraction and a solid fraction. Preferably, the butter(s) according to the invention have a melting point above 25°C and a melting point below 60°C.
[0392] Preferably the particular butter(s) are of vegetable origin such as those described in Ullmann's Encyclopedia of Industrial Chemistry (“Fats and Fatty Oils”, A. Thomas, Published Online: 15 JUN 2000, DOI: 10.1002 / 14356007.al0_173, point 13.2.2.2. Shea Butter, Borneo Tallow, and Related Fats (Vegetable Butters)).
[0393] We can mention in particular shea butter, Nilotica Shea butter (Butyrospermum parkii), Galam butter (Butyrospermum parkii), Borneo butter or fat (tengkawang tallow) (Shorea stenoptera), Shorea butter, Illipe butter, Madhuca or Bassia Madhuca longifolia butter, mowrah butter (Madhuca Latifolia), Katiau butter (Madhuca mottleyana), Phulwara butter (M.butyracea), mango butter (Mangifera indica), Murumuru butter (Astrocaryum murumuru), Kokum butter (Garcinia Indica), Ucuuba butter (Virola sebifera), Tucuma butter, Painya (Kpangnan) butter (Pentadesma butyracea), coffee butter (Coffea arabica), apricot butter (Prunus Armeniaca), macadamia butter (Macadamia Ternifolia), grape seed butter (Vitis vinifera), avocado butter (Persea gratissima), olive butter (Olea europaea), sweet almond butter (Prunus amygdalus dulcis) and cocoa butter, sunflower butter.
[0394] Shea butter is an example of a preferred butter.
[0395] As is known, shea butter is extracted from the fruits (also called "almonds" or "nuts") of the Butyrospemim Parkii tree. Each fruit contains between 45 and 55% fat, which is usually extracted and refined.
[0396] Advantageously, the composition according to the invention comprises at least one non-siliconized fat other than fatty amines, preferably selected from solid fats, liquid fats, butters, and mixtures thereof, more preferably from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, vegetable oils, liquid esters of fatty acids and / or fatty alcohols other than triglycerides, butters of vegetable origin and mixtures thereof, such as cetyl alcohol, stearyl alcohol and mixtures thereof, such as cetylstearyl alcohol, cetearyl alcohol and mixtures thereof, cetyl esters, isopropyl myristate, sunflower oil, avocado oil, shea butter, and mixtures thereof.
[0397] Preferably, the composition according to the invention comprises one or more liquid non-siliconized fats other than fatty amines, preferably chosen from vegetable oils, liquid esters of fatty acids and / or fatty alcohols other than triglycerides, and mixtures thereof.
[0398] Preferably, the composition according to the invention comprises one or more solid non-siliconized fats other than fatty amines, preferably chosen from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, and mixtures thereof.
[0399] Preferably, the composition according to the invention comprises one or more liquid non-siliconized fats other than fatty amines, preferably chosen from vegetable oils, liquid esters of fatty acids and / or fatty alcohols other than triglycerides, and mixtures thereof, and one or more solid non-siliconized fats other than fatty amines, preferably chosen from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, and mixtures thereof.
[0400] Advantageously, the total content of the non-siliconized fat(s), other than fatty amines, ranges from 0.1 to 35% by weight, preferably from 1 to 30% by weight, more preferably from 2 to 25% by weight, better from 5 to 20% by weight, better still from 8 to 15% by weight relative to the total weight of the composition.
[0401] In a particular embodiment, when the composition according to the invention comprises one or more solid and / or liquid and / or pasty non-siliconized fats other than fatty amines, their total content is preferably from 0.1 to 35% by weight, preferably from 1 to 30% by weight, more preferably from 2 to 25% by weight, better from 5 to 20% by weight, better still from 8 to 15% by weight relative to the total weight of the composition. Cationic polymer
[0402] The composition according to the invention may further comprise at least one cationic polymer, preferably chosen from cationic polysaccharides.
[0403] A "cationic polymer" is defined as any polymer comprising cationic groups and / or groups ionizable into cationic groups. Preferably, the cationic polymer is hydrophilic or amphiphilic. Preferred cationic polymers are chosen from those containing motifs with primary, secondary, tertiary, and / or quaternary amine groups that may either be part of the main polymer chain or be attached to a side substituent directly linked thereto.
[0404] The cationic polymers that may be used preferably have a weight-average molar mass (Mw) of between approximately 500 and 5.106, preferably between approximately 103 and 3.106.
[0405] Among cationic polysaccharides, cationic celluloses and galactomannan gums may be mentioned. More particularly, cellulose ether derivatives containing quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and cationic galactomannan gums may be mentioned.
[0406] Cellulose ether derivatives containing quaternary ammonium groups are described in particular in FR1492597, and examples include polymers marketed under the names "UCARE POLYMER JR" (JR 400 LT, JR 125, JR 30M) or "LR" (LR 400, LR 30M) by AMERCHOL. These polymers are also defined in the CTFA dictionary as quaternary ammonium compounds of hydroxyethylcellulose that have reacted with an epoxide substituted with a tri-methylammonium group.
[0407] Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described, in particular, in US patent 4131576, and examples include hydroxyalkylcelluloses, such as hydroxymethyl-, hydroxyethyl-, or hydroxypropyl celluloses grafted, in particular, with a salt of methacryloylethyl trimethylammonium, methacrylamidopropyl trimethylammonium, or dimethyl diallylammonium. The marketed products meeting this definition are, more specifically, the products sold under the names "Celquat L 200" and "Celquat H 100" by the National Starch Company.
[0408] Cationic galactomannan gums are described in particular in patents US3589578 and US4031307, and examples include guar gums containing trialkylammonium cationic groups. For instance, guar gums modified with a salt (e.g., a chloride) of 2,3-epoxypropyl trimethylammonium are used. Such products are marketed, notably under the names JAGUAR C13 S, JAGUAR C 15, JAGUAR C 17, or JAGUAR C162 by the company RHODIA.
[0409] According to a preferred embodiment, the cationic polymer(s) are preferably chosen from cationic polysaccharides, more preferably chosen from cationic galactomannan gums, better, chosen from cationic guar gums.
[0410] Advantageously, when present, the total content of the cationic polymer(s) ranges from 0.0001 to 5% by weight, preferably from 0.001 to 3% by weight, more preferably from 0.01 to 2% by weight, better from 0.05 to 1% by weight relative to the total weight of the composition. Cationic surfactant
[0411] The composition according to the invention may further comprise at least one surfactant cationic, unlike the fatty amines described previously.
[0412] A "cationic surfactant" is defined as a surfactant that is positively charged when contained in the compositions according to the invention. This surfactant may carry one or more permanent positive charges or contain one or more cationizable functional groups within the compositions according to the invention.
[0413] Preferably, the cationic surfactant(s) are chosen from quaternary ammonium salts, and mixtures thereof.
[0414] Quaternary ammonium salts include, for example:
[0415] - those corresponding to the following general formula (X):
[0416] wherein the groups R8 to Ru, which may be identical or different, represent an aliphatic group, linear or branched, comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups R8 to Rn comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms. The aliphatic groups may comprise heteroatoms such as, in particular, oxygen, nitrogen, sulfur, and halogens.
[0417] The aliphatic groups are for example chosen from the alkyl groups in Ci-C30, alkoxy in CrC3o, polyoxyalkylene (C2-C6), alkylamide in CrC3o, alkyl(Ci2-C22)amidoalkyl(C2-C6), alkyl(Ci2-C22)acetate, and hydroxyalkyl in Ci-C30, X is an anion chosen from the group of halides, phosphates, acetates, lactates, alkyl(Ci-C4)sulfates, alkyl(Ci-C4)- or alkyl(Ci-C4)aryl-sulfonates.
[0418] Among quaternary ammonium salts of formula (X), preference is given on the one hand to tetraalkylammonium chlorides such as, for example, dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises about 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides or, on the other hand, to palmitylamidopropyltrimethylammonium chloride or to stearamidopropyldimethyl(myristylacetate)ammonium chloride marketed under the name CERAPHYL® 70 by the company VAN DYK;
[0419] - quaternary ammonium salts of imidazoline, such as for example those of The following formula (XI): * (XI),
[0420] in which R represents an alkenyl or alkyl group comprising 8 to 30 carbon atoms, for example derived from tallow fatty acids, Rn represents a hydrogen atom, a Ci-C4 alkyl group or an alkenyl or alkyl group comprising 8 to 30 carbon atoms, Ru represents a Ci-C4 alkyl group, Ri5 represents a hydrogen atom, a CrC4 alkyl group, X is an anion selected from the group of halides, phosphates, acetates, lactates, alkyl(CrC4)sulfates, alkyl(CrC4)- or alkyl(Ci-C4)aryl-sulfonates.
[0421] Preferably, Rn and Rn denote a mixture of alkenyl or alkyl groups comprising 12 to 21 carbon atoms, for example derived from tallow fatty acids, R[4 denotes a methyl group, R[5 denotes a hydrogen atom. Such a product is, for example, marketed under the name REWOQUAT® W 75 by the company REWO;
[0422] - quaternary di- or triammonium salts in particular of formula (XII) next: r -i 2. Ru R1S ri R^—N—(CH 4 — N—R^, 2X ' । -ï । ^5 FU do
[0423] wherein R[6] denotes an alkyl group comprising about 16 to 30 carbon atoms optionally hydroxylated and / or interrupted by one or more oxygen atoms, Rn is selected from hydrogen or an alkyl group comprising 1 to 4 carbon atoms or a -(CH2)3-N+(Ri6a)(Ri7a)(Ri8a), Rj6a, Rj7a, Ri8a, Ris, Ri% R2o and R2i, identical or different, are selected from hydrogen or an alkyl group comprising 1 to 4 carbon atoms, and X is an anion selected from the group of halides, acetates, phosphates, nitrates, alkyl(Ci-C4)sulfates, alkyl(Ci-C4)- or alkyl(Ci-C4)aryl-sulfonates, in particular methyl sulfate and ethyl sulfate.
[0424] Such compounds are for example Finquat CT-P offered by FINETEX (Quaternium 89), Finquat CT offered by FINETEX (Quaternium 75);
[0425] - quaternary ammonium salts containing one or more ester functions, such that, for example, those of the following formula (XIII): ---R._ (XIII), , N “ «24 c--(O—C,HÆ(QHy— M—Q) —X ' | ' " - -FU
[0426] wherein: R22 is selected from Ci-C6 alkyl groups and Ci-C6 hydroxyalkyl or dihydroxyalkyl groups; R23 is selected from: the -C(O)R26 group, linear or branched, saturated or unsaturated Ci-C22 hydrocarbon groups R27, the hydrogen atom; R25 is selected from: the -C(O)R28 group, linear or branched, saturated or unsaturated Ci-C6 hydrocarbon groups R29, the hydrogen atom; R24, R26 and R28, identical or different, are selected from linear or branched, saturated or unsaturated C7-C2i hydrocarbon groups; r, s and t, identical or different, are integers from 2 to 6; rl and tl, whether identical or different, are worth 0 or 1;r2 + rl = 2 r and tl + t2 = 2 t, y is an integer from 1 to 10, x and z, identical or different, are integers from 0 to 10, X is a simple or complex anion, organic or inorganic, provided that the sum x + y + z is from 1 to 15, that when x is 0 then R23 designates R27 and that when z is 0 then R25 designates R29. ;
[0427] The R22 alkyl groups can be linear or branched and more particularly linear.
[0428] Preferably, R22 designates a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
[0429] Advantageously, the sum x + y + z is worth from 1 to 10.
[0430] When R23 is a hydrocarbon R27 group, it can be long and have 12 to 22 carbon atoms, or short and have 1 to 3 carbon atoms.
[0431] When R25 is a hydrocarbon R29 group, it preferably has 1 to 3 carbon atoms.
[0432] Advantageously, R24, R26 and R28, identical or different, are chosen from Cn-C2i hydrocarbon groups, linear or branched, saturated or unsaturated, and more particularly from Cn-C2i alkyl and alkenyl groups, linear or branched, saturated or unsaturated.
[0433] Preferably, x and z, whether identical or different, are equal to 0 or 1.
[0434] Advantageously, y is equal to 1.
[0435] Preferably, r, s and t, whether identical or different, are equal to 2 or 3, and even more particularly are equal to 2.
[0436] The anion X is preferably a halide, preferably a chloride, bromide or Iodide, an alkyl(Ci-C4)sulfate, alkyl(Ci-C4)- or alkyl(Ci-C4)aryl-sulfonate. However, methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid such as acetate or lactate, or any other compatible anion may be used. with ammonium with ester function.
[0437] Anion X is more particularly chloride, methylsulfate or ethylsulfate.
[0438] In the composition according to the invention, ammonium salts of formula (XIII) are used in particular, wherein: R22 denotes a methyl or ethyl group, x and y are equal to 1, z is equal to 0 or 1, r, s and t are equal to 2; R23 is chosen from: the -C(O)R26 group, methyl, ethyl or C14-C22 hydrocarbon groups, the hydrogen atom, R25 is chosen from: the -C(O)R28 group, the hydrogen atom, R24, R26 and R28, identical or different, are chosen from C13-C17 hydrocarbon groups, linear or branched, saturated or unsaturated, and preferably from C13-C17 alkyl and alkenyl groups, linear or branched, saturated or unsaturated.
[0439] Advantageously, hydrocarbon groups are linear.
[0440] Examples of compounds with formula (XIII) include salts, particularly diacyloxyethyldimethylammonium chloride or methylsulfate, diacyloxyethylhydroxyethyl methylammonium chloride, monoacyloxyethyldihydroxyethylmethylammonium chloride, triacyloxyethylmethylammonium chloride, monoacyloxyethylhydroxyethyl dimethylammonium chloride, and mixtures thereof. The acyl groups preferably have 14 to 18 carbon atoms and are more particularly derived from a vegetable oil such as palm or sunflower oil. When the compound contains several acyl groups, these may be identical or different.
[0441] These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine, optionally oxyalkylated with fatty acids or mixtures of fatty acids of vegetable or animal origin, or by transesterification of their methyl esters. This esterification is followed by quaternization with an alkylating agent, such as an alkyl halide, preferably methyl or ethyl, a dialkyl sulfate, preferably methyl or ethyl, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol. Such compounds are marketed for example under the names DEHYQUART® by the company HENKEL, STEPANQUAT® by the company STEPAN, NOXAMIUM® by the company CECA, REWOQUAT® WE 18 by the company REWO-WITCO.
[0442] The composition according to the invention may contain, for example, a mixture of quaternary ammonium mono-, di- and triester salts with a majority by weight of diester salts.
[0443] Ammonium salts containing at least one ester function described in US-A-4874554 and US-A-4137180 patents can also be used.
[0444] Behenoylhydroxypropyltrimethyl- chloride can also be used Ammonium, for example, offered by the company KAO under the name Quartamin BTC 131.
[0445] Other examples include distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate.
[0446] Among the quaternary ammonium salts containing at least one usable ester function, dipalmitoylethylhydroxyethyl-methyl-lammonium salts are preferred, in particular dipalmitoylethylhydroxyethyl-lammonium methosulfate.
[0447] Preferably, ammonium salts containing at least one ester function contain two ester functions.
[0448] Advantageously, the cationic surfactant(s) are chosen from quaternary ammonium salts, preferably from those corresponding to the general formula (X), those corresponding to the general formula (XIII) and mixtures thereof.
[0449] Preferably, quaternary ammonium salts corresponding to the general formula (X) are chosen from tetraalkylammonium chlorides, such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises from 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides and mixtures thereof.
[0450] Examples of quaternary ammonium salts corresponding to the general formula (XIII) may be distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate, distea-roylethylhydroxyethylammonium methosulfate, and mixtures thereof.
[0451] According to a particularly preferred embodiment, the quaternary ammonium salts are selected from tetraalkylammonium chlorides, such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides, dipalmitoylethylhydroxyethyl-methyl-lammonium salts, in particular dipalmitoylethylhydroxyethyl-lammonium methosulfate, and mixtures thereof.
[0452] Advantageously, the total content of the cationic surfactant(s) other than the fatty amines previously described ranges from 0.01 to 15% by weight, preferably from 0.1 to 10% by weight, more preferably from 0.5 to 8% by weight, better from 1 to 6% by weight relative to the total weight of the composition. Silicone
[0453] The composition according to the invention may further comprise at least one silicone, which can be chosen from non-amine silicones, amino silicones, and their mixtures.
[0454] The silicone(s) are preferably chosen from among the amino silicones.
[0455] The composition according to the invention may therefore comprise one or more non-amine silicones, which may be solid or liquid, preferably liquid (at 25°C, 1 atm), volatile or non-volatile.
[0456] The non-amine silicones that may be used may be soluble or insoluble in the composition according to the invention; they may be in the form of oil, wax, resin or gum; silicone oils and gums are preferred.
[0457] Silicones are described in detail in particular in Walter NOLL's book "Chemistry and Technology of Silicones" (1968), Academy Press.
[0458] Volatile silicones can be selected from those having a boiling point between 60 and 260°C (at atmospheric pressure), in particular from
[0459] i) cyclic polydialkylsiloxanes comprising 3 to 7 silicon atoms, preferably 4 to 5, such as: - octamethylcyclotetrasiloxane (D4) and decamethylcyclopentasiloxane (D5). Examples include products marketed under the name "VOLATILE SILICONE 7207" by UNION CARBIDE or "SILBIONE 70045 V 2" by RHODIA, "VOLATILE SILICONE 7158" by UNION CARBIDE, "SILBIONE 70045 V 5" by RHODIA. - cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type with the following chemical structure: j Q ... Q- --------------Q „ Q ■ CH:. *----------------------------------1 CH, with D: -Si-O — with 0': -Si -O..... CH, CgK, One example is "VOLATILE SILICONE FZ 3109" marketed by the company UNION CARBIDE. - mixtures of cyclic silicones with silicon-derived organic compounds, such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilyl-pentaerythritol (50 / 50) and the mixture of octamethylcyclotetrasiloxane and oxy-l,l'-(hexa-2,2,2',2',3,3'-trimethylsilyloxy) bis-neopentane;
[0460] ii) linear polydialkylsiloxanes having 2 to 9 silicon atoms, which generally have a viscosity less than or equal to 5.10 6m2 / s at 25°C, such as decametethyltetrasiloxane. Other silicones falling into this class are described in the article published in Cosmetics and toiletries, Vol. 91, Jan. 76, p. 27-32 - TODD & BYERS "Volatile Silicone fluids for cosmetics"; one can cite the product marketed under the name "SH 200" by the company TORAY SILICONE.
[0461] Among non-volatile silicones, one can cite, alone or in mixture, polydialkyl-siloxanes and in particular polydimethylsiloxanes (PDMS or dimethicone), poly-diarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, as well as non-amino organopolysiloxanes (or organomodified polysiloxanes, or organomodified silicones) which are polysiloxanes having in their structure one or more non-amino organofunctional groups, generally fixed by means of a hydrocarbon group, and preferably chosen from aryl groups, alkoxy groups and polyoxyethylenated and / or polyoxypropylenated groups.
[0462] Organomodified silicones may be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organofunctional groups mentioned above. Polyalkylarylsiloxanes are particularly selected from among polydimethyl / methylphenylsiloxanes, linear and / or branched polydimethyl / diphenylsiloxanes.
[0463] Among organomodified silicones, organopolysiloxanes comprising: - polyoxyethyleney and / or polyoxypropylene groups possibly containing C6-C24 alkyl groups such as dimethicone copolyols, and in particular those marketed by DOW CORNING under the name DC 1248 or SILWET® L 722, L 7500, L 77, L 711 oils from UNION CARBIDE; or alkyl(Ci2)-methicone copolyols, and in particular those marketed by DOW CORNING under the name Q2-5200; - thiol groups, such as the products marketed under the names "GP 72 A" and "GP 71" from GENESEE; - alkoxylated groups, such as the product marketed under the name "SILICONE COPOLYMER F-755" by SWS SILICONES and ABIL WAX® 2428, 2434 and 2440 by the company GOLDSCHMIDT; - hydroxylated groups, such as polyorganosiloxanes with a hydroxyalkyl function; - acyloxyalkyl groups such as the polyorganosiloxanes described in US patent A-4957732. - anionic groups of the carboxylic acid type, such as those described in EP186507, or of the alkyl-carboxylic type, such as product X-22-3701E from SHIN-ETSU; or of the 2-hydroxyalkylsulfonate type or 2-hydroxyalkylthiosulfate, such as the products marketed by the company GOLDSCHMIDT under the names "ABIL® S201" and "ABIL® S255".
[0464] Silicones can also be selected from polydialkylsiloxanes, the main examples of which are polydimethylsiloxanes with trimethylsilyl terminal groups (CTFA: dimethicone). Examples of these polydialkylsiloxanes include the following commercial products: - SILBIONE® oils from series 47 and 70 047 or MIRASIL® oils marketed by RHODIA such as, for example, oil 70 047 V 500 000; - the MIRASIL® series oils marketed by the RHODIA company; - oils from the 200 series of DOW CORNING such as DC200 with a viscosity of 60,000 mm2 / s; - VISCASIL® oils from GENERAL ELECTRIC and certain oils from the SF series (SF 96, SF 18) from GENERAL ELECTRIC.
[0465] We can also mention polydimethylsiloxanes with terminal dimethylsilanol groups (CTFA: dimethiconol) such as the oils of the 48 series of the RHODIA company.
[0466] In this class of polydialkylsiloxanes, we can also mention the products marketed under the names "ABIL WAX® 9800 and 9801" by the company GOLDSCHMIDT which are polydialkyl (C1-C20) siloxanes.
[0467] Products more particularly usable according to the invention are mixtures such as: - mixtures formed from a chain-end hydroxylated polydimethylsiloxane, or dimethiconol (CTFA) and a cyclic polydimethylsiloxane also called cyclomethicone (CTFA) such as the product Q2-1401 marketed by DOW CORNING. Polyalkylarylsiloxanes are particularly chosen from among polydimethyl / methylphenylsiloxanes, linear and / or branched polydimethyl / diphenylsiloxanes with viscosities ranging from 1.105 to 5.10 2m2 / s at 25°C. Among these polyalkylarylsiloxanes, we can mention the products marketed under the following names: - SILBIONE® oils from the 70 641 series by RHODIA; - the oils from the RHODORSIL® 70 633 and 763 series from RHODIA; - DOW CORNING 556 COSMETIC GRAD FLUID oil from DOW CORNING;
[0468] - BAYER's PK series silicones such as product PK20;
[0469] - BAYER's PN and PH series silicones, such as the PN1000 and PH1000 products - certain oils from the SF series of GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, SF 1265.
[0470] The non-amine silicones most particularly preferred according to the invention are the trimethylsiloxanes with terminal trimethylsilyl groups (CTFA: dimethicone).
[0471] The composition according to the invention may comprise one or more amino silicones.
[0472] Aminated silicone means any silicone comprising at least one primary, secondary, tertiary amine or one quaternary ammonium group.
[0473] Amino silicones that can be used according to the present invention can be volatile or non-volatile, cyclic, linear or branched, and preferably have a viscosity ranging from 5*106 to 2.5 m2 / s at 25°C, for example from 1*105 to 1 m2 / s.
[0474] Preferably, the amino silicone(s) are chosen from, alone or in mixtures, the following compounds:
[0475] a) polysiloxanes corresponding to formula (I): in which x' and y' are integers such that the average molecular mass by weight (Mw) is between 5000 and 500000 g / mol;
[0476] b) Amino silicones conforming to formula (II): R'aG3a-Si(OSiG2)n-(OSiGbR'2b)mO-SiG3a-R'a (II) in which: - G, identical or different, denotes a hydrogen atom, a phenyl group, OH, alkyl group in CrC8, for example methyl or alkoxy group in CrC8, for example methoxy, - a, a' identical or different, denote 0 or an integer from 1 to 3, in particular 0, provided that at least one of a or a' is equal to zero, - b denotes 0 or 1, in particular 1, - m and n are numbers such that the sum (n + m) varies from 1 to 2000, in particular from 50 to 150, n being able to designate a number from 0 to 1999, and in particular from 49 to 149, and m being able to designate a number from 1 to 2000, and in particular from 1 to 10; and - R', identical or different, denotes a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group possibly quaternized chosen from the groups: -NR”-QN(R”)2, -N(R”)2, -N+(R”)3 A, -N+ H(R”)2 A, -N+H2(R”) A, -NR”-Q-N+(R”)H2 A, -NR”-Q-N+(R”)2H A and -NR”-QN+(R”)3 A, in which R”, identical or different, denotes hydrogen, phenyl, benzyl, or a monovalent saturated hydrocarbon radical, for example a C1-C20 alkyl radical; Q denotes a group of formula CrH2r, linear or branched, r being an integer from 2 to 6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide or iodide.
[0477] Preferably, the amino silicones of formula (II) may be selected from:
[0478] (i) “trimethylsilylamodimethicone” silicones conforming to formula (III): in which m and n are numbers such that the sum (n + m) varies from 1 to 2000, preferably from 20 to 1000, in particular from 50 to 600, better from 50 to 150; n can represent a number from 0 to 1999, and in particular from 49 to 149 and m can represent a number from 1 to 2000, and in particular from 1 to 10.
[0479] (ii) silicones of the following formula (IV): in which: - m and n are numbers such that the sum (n + m) varies from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200; n denoting a number from 0 to 999 and in particular from 49 to 249 and more particularly from 125 to 175 and m denoting a number from 1 to 1000, in particular from 1 to 10, more particularly from 1 to 5; and - Rb R2, R2, identical or different, represent a hydroxy or alkoxy radical in Ci-C4, at least one of the radicals Ri to R3 designating an alkoxy radical. Preferably, the alkoxy radical is a methoxy radical. The hydroxy / alkoxy molar ratio preferably ranges from 0.2:1 to 0.4:1 and preferably from 0.25:1 to 0.35:1 and more particularly is equal to 0.3:1.
[0480] The average molecular mass by weight (Mw) of these silicones will preferably be 2000 to 1,000,000 g / mol, more particularly from 3500 to 200,000 g / mol.
[0481] (iii) silicones of the following formula (V): in which: - p and q are numbers such that the sum (p + q) varies from 1 to 1000, in particular from 50 to 350, and more particularly from 150 to 250; p denoting a number from 0 to 999, and in particular from 49 to 349, and more particularly from 159 to 239, and q denoting a number from 1 to 1000, in particular from 1 to 10, and more particularly from 1 to 5; and - Rb R2, different, represent a hydroxy or alkoxy radical in Ci-C4, at least one of the radicals Ri or R2 designating an alkoxy radical. Preferably, the alkoxy radical is a methoxy radical. The hydroxy / alkoxy molar ratio generally ranges from 1:0.8 to 1:1.1 and preferably from 1:0.9 to 1:1 and more particularly is equal to 1:0.95. The average molecular mass by weight (Mw) of silicone is preferably from 2000 to 200000 g / mol, more preferably from 5000 to 100000 g / mol and in particular from 10000 to 50000 g / mol.
[0482] Commercial products containing structural (IV) or (V) silicones may include in their composition one or more other amino silicones with a structure different from the (IV) or (V) formulations. A product containing structural (IV) amino silicones is offered by WACKER under the name BELSIL® ADM 652. A product containing structural (V) amino silicones is offered by WACKER under the name Fluid WR 1300®. Another product containing structural (XIV) amino silicones is offered by WACKER under the name Belsil ADM LOG 1®.
[0483] When these amino silicones are used, a particularly interesting embodiment is their use as an oil-in-water emulsion. The oil-in-water emulsion may comprise one or more surfactants. The surfactants may be of any nature, but preferably cationic and / or nonionic. The average number size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometers. Preferably, in particular, as silicones For amine-based formula (V), microemulsions with an average particle size ranging from 5 nm to 60 nm (inclusive) and more particularly from 10 nm to 50 nm (inclusive) are used. Thus, according to the invention, the amine-based silicone microemulsions of formula (V) offered under the names FINISH CT 96 E® or SLM 28020® by WACKER can be used.
[0484] (iv) silicones of the following formula (VI): in which: - m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n denoting a number from 0 to 1999 and in particular from 49 to 149 and m denoting a number from 1 to 2000, and in particular from 1 to 10; and - A denotes a linear or branched alkylene radical, preferably linear, having 4 with 8 carbon atoms and preferably 4 carbon atoms. The average molecular mass by weight (Mw) of these amino silicones preferably ranges from 2000 to 1000000 g / mol and more particularly from 3500 to 200000 g / mol. One silicone that meets this formula is, for example, DOW CORNING's XIAMETER MEM 8299 EMULSION.
[0485] (v) silicones of the following formula (VII): in which: - m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10; and - A designates a linear or branched alkylene radical having from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched. The average molecular mass by weight (Mw) of these amino silicones ranges from
[0486] Preferably between 500 and 1,000,000 g / mol, and more specifically between 1,000 and 200,000 g / mol. A silicone meeting this specification is, for example, Dow Corning's DC2-8566 Amino Fluid. c) Amino silicones conforming to formula (VIII):
[0487] in which: - R5 represents a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, and in particular an alkyl radical in CrCi8, or alkenyl in C2-Ci8, for example methyl; - R6 represents a divalent hydrocarbon radical, in particular a C1-C18 alkylene radical or a divalent CrCi8 alkyleneoxy radical, for example CrC8 linked to Si by a SiC bond; - Q is an anion such as a halide ion, in particular chloride or a salt of organic acid, in particular acetate; - r represents an average statistical value ranging from 2 to 20, specifically from 2 to 8; and - s represents an average statistical value ranging from 20 to 200, in particular from 20 to 50. d) Quaternary ammonium silicones of formula (IX): in which: - R7, identical or different, represent a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, and in particular an alkyl radical in Ci-Ci8, an alkenyl radical in C2-Ci8 or a ring comprising 5 or 6 carbon atoms, for example methyl; - R6 represents a divalent hydrocarbon radical, in particular an alkylene radical in CrCi8 or a divalent alkyleneoxy radical in CrCi8, for example in CrC8 linked to Si by a SiC bond; - R8, whether identical or different, represents a hydrogen atom, a hy radical
[0488] monovalent drocarbon having from 1 to 18 carbon atoms, and in particular an alkyl radical in CrCi8, an alkenyl radical in C2-Ci8, a -R6-NHCOR7 radical; - X is an anion such as a halide ion, in particular chloride, or a salt of an organic acid, in particular acetate; and - r represents an average statistical value ranging from 2 to 200, in particular from 5 to 100. These silicones are described for example in application EP-A-0530974; in particular, the silicone with INCI name QUATERNIUM 80 can be mentioned. Silicones falling into this class are the silicones marketed by the company GOLDSCHMIDT under the names ABIL QUAT 3270, ABIL QUAT 3272, ABIL QUAT 3474. e) Amino silicones of formula (X):
[0489] (X) in which: - Ri, R2, R3 and R4, whether identical or different, denote a C1-C4 alkyl radical or a phenyl group, - R5 designates a C1-C4 alkyl radical or a hydroxyl group, - n is an integer ranging from 1 to 5, - m is an integer ranging from 1 to 5, and - x is chosen such that the amine index varies from 0.01 to 1 meq / g. f) multiblock polyoxyalkylened amine silicones, of type (AB)n, A being a polysiloxane block and B being a polyoxyalkylened block comprising at least one amine group. These silicones are preferably made up of repeating units of the following general formulas: [-(SiMe2O)xSiMe2-RN(R”)-R'-O(C2H4O)a(C3H6O)b-R'-N(H)-R-] or [-(SiMe2O)xSiMe2-RN(R' ' )-R' -O(C2H4O)a(C3H6O)b-] in which: - a is an integer greater than or equal to 1, preferably from 5 to 200, more particularly from 10 to 100; - b is an integer between 0 and 200, preferably from 4 to 100, more particularly between 5 and 30; - x is an integer ranging from 1 to 10000, more specifically from 10 to 5000; - R' ' is a hydrogen atom or a methyl; - R, identical or different, represent a linear or branched C2-Ci2 hydrocarbon divalent radical, possibly containing one or more heteroatoms such as oxygen; preferably, R, identical or different, denote an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a CH2CH2CH2OCH2CH(OH)CH2- radical; preferably R denote a CH2CH2CH2OCH2CH(OH)CH2- radical; and - R', identical or different, represent a linear or branched C2-Ci2 hydrocarbon divalent radical, possibly comprising one or more heteroatoms such as oxygen; preferably, R', identical or different, denote an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a CH2CH2CH2OCH2CH(OH)CH2- radical; preferably R' denote -CH(CH3 )-CH2-,
[0490] The siloxane blocks preferably represent between 50 and 95 mole percent of the total weight of the silicone, more particularly between 70 and 85 mole percent.
[0491] The amine content is preferably between 0.02 and 0.5 meq / g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
[0492] The average molecular mass by weight (Mw) of silicone is preferably between 5000 and 1000000 g / mol, more particularly between 10000 and 200000 g / mol. Examples include silicones marketed under the names Silsoft A-843 or Silsoft A+ by Momentive.
[0493] g) Amino silicones of formulas (XI) and (XII): HR i (I m HH, (XI) in which: - R, R' and R”, whether identical or different, denote an alkyl group in C1-C4 or a hydroxyl group, - A denotes a C3 alkylene radical; and - m and n are numbers such that the average molecular mass by weight of the compound is between 5000 and 500000. oy ch,; m— tonj cy CH,, y ÇH, V "" V "" CX """^4 TO HH S " ~ HH., _ x OTI in which: - x and y are numbers ranging from 1 to 5000; preferably x ranges from 10 to 2000, and more preferably from 100 to 1000; preferably y ranges from 1 to 100; - Ri and R2, identical or different, preferably identical, denote an alkyl group, linear or branched, saturated or unsaturated, comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, and more preferably from 12 to 20 carbon atoms; and - A denotes a linear or branched alkylene radical having from 2 to 8 carbon atoms. Preferably, A comprises from 3 to 6 carbon atoms, more preferably 4 carbon atoms; preferably A is branched. The following divalent groups may be cited in particular: -CH2CH2CH2- and -CH2CH(CH3)CH2-.
[0494] Preferably, Ri and R2 are independent saturated linear alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and in particular 12 to 20 carbon atoms; particular examples include dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; and preferably, Ri and R2, whether identical or different, are selected from the hexadecyl (cetyl) and octadecyl (stearyl) groups.
[0495] Preferably, in silicone of formula (XII), there is:
[0496] - x ranging from 10 to 2,000, and in particular from 100 to 1,000;
[0497] - ranging from 1 to 100;
[0498] - A comprising from 3 to 6 carbon atoms and in particular 4 carbon atoms; of Preferably, A is branched; and more particularly, A is chosen from the following divalent groups: -CH2CH2CH2 and -CH2CH(CH3)CH2-; and
[0499] - Ri and R2 being independently saturated linear alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms, and particularly 12 to 20 carbon atoms; chosen especially from the dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups; preferably, Ri and R2, identical or different, being chosen from the groups
[0500] hexadecyl (cetyl) and octadecyl (stearyl). A preferred silicone formulation (XII) is bis-cetearylamodimethicone. A notable example is the amino silicone sold under the name SILSOFT AX by Momentive. (h) polysiloxanes, and in particular polydimethylsiloxanes, comprising primary amine groups at one end of the chain or on the side chains, such as those of formula (XIV), (XV) or (XVI): (XV) In formula (XIV), the values of n and m are such that the average molecular mass by weight of the amino silicon is between 1000 and 55000. Examples of formula (XIV) amino silicones include products sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by Gelest and KF-8015 by Shin Etsu. In formula (XV), the value of n is such that the average molecular mass by weight of the amino silicon is between 500 and 3000. As an example of formula (XV) amine silicones, we can cite the products sold under the names MCR-A11 and MCR-A12 by the company Gelest. In formula (XVI), the values of n and m are such that the average molecular mass by weight of the amino silicon is between 500 and 50000. Examples of formula (XVI) amino silicones include aminopropyl phenyl trimethicone sold under the name DC 2-2078 Fluid by Dow Corning.
[0501] The cosmetic composition according to the invention may also include as silicone, an amino silicone corresponding to the formula (XVIII) below: in which: - n is a number between 1 and 1000, preferably between 10 and 500, better between 25 and 100, even better between 50 and 80; - m is a number between 1 and 200, preferably between 1 and 100, better between 1 and 10 and even better between 1 and 5; - R'”, identical or different, preferably identical, are linear or branched alkyl radicals, saturated or unsaturated, comprising from 8 to 30 carbon atoms, preferably 10 to 24 carbon atoms, in particular 12 to 18 carbon atoms; said radicals may optionally be substituted by one or more hydroxyl groups OH; - R' is a linear or branched alkylene divalent radical, having from 1 to 6 carbon atoms, in particular from 2 to 5 carbon atoms; - R' ' is a linear or branched alkylene divalent radical, having from 1 to 6 carbon atoms, in particular from 1 to 5 carbon atoms. Preferably, the identical or different R's are saturated linear alkyl radicals comprising 8 to 30 carbon atoms, preferably 10 to 24 carbon atoms, in particular 12 to 18 carbon atoms; in particular dodecyl, C13, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl radicals may be mentioned; preferably the identical or different Rs are chosen from among the saturated linear alkyl radicals having 12 to 16 carbon atoms, in particular C13, C14, Cl5, alone or in mixture, and better represent a mixture of C13, C14 and C15. Preferably, the R's are identical. Preferably, R' is a linear or branched divalent alkylene radical, preferably branched, comprising 1 to 6 carbon atoms, in particular 2 to 5 carbon atoms; in particular a radical -CH2-CH2-CH2-, -CH2-CH(CH3)-CH2- or -CH2-CH2-CH(CH3)-. Preferably, R'' is a linear divalent alkylene radical comprising 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms; in particular a -CH2-CH2- radical.
[0502] Advantageously, when the composition according to the invention comprises at least one silicone selected from among the amino silicones, said amino silicone is preferably selected from the silicones of formula (II), more preferably from the silicones of formula (VI) and mixtures thereof.
[0503] When the composition includes at least one silicone, the total content of the silicone(s) preferably shall be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and better from 0.5 to 5% by weight relative to the total weight of the composition.
[0504] When the composition includes at least one amino silicone, the total content of the amino silicone(s) will preferably be from 0.01 to 15% by weight, more preferably from 0.05 to 10% by weight, and better from 0.5 to 5% by weight, relative to the total weight of the composition. Non-cationic polysaccharide
[0505] The composition according to the invention may further comprise at least one non-cationic polysaccharide. In other words, said non-cationic polysaccharide is different from the cationic polymers described above. Preferably, said non-cationic polysaccharide(s) are selected from among non-ionic polysaccharides.
[0506] Non-ionic polysaccharides are preferably selected from, alone or in mixture, celluloses, starches, galactomannans, and their non-ionic derivatives, in particular their ethers or esters.
[0507] These polymers can be modified by physical or chemical means. Physical treatment may be indicated by temperature; and chemical treatment may be indicated by esterification, etherification, amidation, and oxidation reactions, insofar as these treatments lead to non-ionic polymers.
[0508] Examples of galactomannans that may be used include non-ionic guar gums that can be modified by C1-C6 (poly)hydroxylakyl groups, in particular hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
[0509] These guar gums are well known from the prior art and can, for example, be prepared by reacting corresponding alkene oxides such as, for example, propylene oxides with guar gum in order to obtain a guar gum modified by hydroxypropyl groups.
[0510] The degree of hydroxyalkylation preferably varies from 0.4 to 1.2 and corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl groups present on guar gum.
[0511] Such non-ionic guar gums possibly modified by hydroxyalkyl groups are for example sold under the trade names JAGUAR HP8, JAGUAR HP60, JAGUAR HP120, Jaguar HP105 SGI and Jaguar HP8 SGI by the company RHODIA CHIMIE.
[0512] The starch molecules usable in the present invention may be of botanical origin from cereals or tubers. Thus, the starches are, for example, selected from corn, rice, cassava, barley, potato, wheat, sorghum, and pea starches. The starches may be modified chemically or physically, in particular by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidation, and heat treatments.
[0513] Starch molecules can be derived from all plant starch sources, such as maize, potato, oats, rice, tapioca, sorghum, barley, or wheat. Hydrolysates of the starches mentioned above can also be used. The starch is preferably derived from potato.
[0514] Non-ionic polysaccharides can also be cellulosic polymers without a C10-C30 fatty chain in their structure.
[0515] By "cellulosic" polymer, according to the invention, any polysaccharide compound having in its structure chains of glucose residues joined by [3-1,4] bonds; cellulosic polymers can be unsubstituted celluloses, and / or derivatives of non-ionic celluloses.
[0516] Thus, the cellulosic polymers usable according to the invention can be chosen from unsubstituted celluloses, including in microcrystalline form, and cellulose ethers. Among these cellulosic polymers, a distinction is made between cellulose ethers, cellulose esters, and cellulose ester-ethers.
[0517] Among the non-ionic cellulose ethers, examples include (Cl-C4)alkylcelluloses such as methylcelluloses and ethylcelluloses (e.g., Ethocel Standard 100 Premium from DOW CHEMICAL); (poly)hydroxy(Cl-C4)alkylcelluloses such as hydroxymethylcelluloses, hydroxyethylcelluloses (e.g., Natrosol 250 HHR offered by AQUALON) and hydroxypropylcelluloses (e.g., Klucel EF from AQUALON); mixed (poly)hydroxy(Cl-C4)alkyl-(Cl-C4)alkylcelluloses such as hydroxypropyl methylcelluloses (e.g., Methocel E4M from DOW CHEMICAL), hydroxyethyl methylcelluloses, hydroxyethyl ethylcelluloses (e.g., Bermocoll E 481 FQ from AKZO NOBEL) and hydroxybutyl methylcelluloses.
[0518] Preferably, the non-ionic polysaccharides are chosen from, alone or in mixture, celluloses, galactomannans, and their non-ionic derivatives, in particular their ethers; and even better among, alone or in mixture, non-ionic guar gums possibly modified by C1-C6 (poly)hydroxylakyl groups, in particular hydroxypropyl; and / or celluloses, substituted or unsubstituted, and cellulose ethers such as (Cl-C4)alkylcelluloses, and (poly)hydroxy(Cl-C4)alkylcelluloses, such as hydroxyethylcellulose.
[0519] Preferably, non-ionic polysaccharides are chosen from cellulose ethers such as (Cl-C4)alkylcelluloses, and (poly)hydroxy(Cl-C4)alkylcelluloses such as hydroxyethylcellulose, and mixtures thereof.
[0520] When the composition includes at least one non-cationic polysaccharide, the total content of the non-cationic polysaccharide(s) shall advantageously be from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, more preferably from 0.1 to 2% by weight relative to the total weight of the composition.
[0521] The composition according to the invention is preferably aqueous, the water content preferably ranging from 50 to 95% by weight, more preferably from 60 to 94% by weight, even more preferably from 75 to 93% by weight, better from 80 to 92% by weight relative to the total weight of the composition.
[0522] When the composition is aqueous, the pH can vary from 2 to 7, preferably from 3 to 5. Additives
[0523] The composition according to the invention may contain any adjuvant or additive usually used, different from the compounds as described above.
[0524] Among the additives that may be contained in the composition according to the invention, we can mention anionic, non-ionic, amphoteric polymers or mixtures thereof, other than the polysaccharides described above, anti-dandruff agents, anti-seborrheic agents, anti-hair loss and / or hair regrowth agents, vitamins and pro-vitamins including panthenol, sunscreens, mineral or organic pigments, plasticizers, solubilizers, opacifiers or pearlescent agents, antioxidants, hydroxy acids, perfumes, preservatives.
[0525] Of course, a person skilled in the art will take care to choose this or these possible complementary compounds in such a way that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the envisaged addition(s).
[0526] The above additives may generally be present in quantities of each of them between 0 and 20% by weight, relative to the total weight of the ready-to-use composition. Process
[0527] The present invention also relates to a method for coloring keratin fibers, preferably hair, which includes applying to said keratin fibers the composition according to the invention as defined above.
[0528] The composition can be applied to dry or wet keratin fibers. After treatment, the keratin fibers may be rinsed with water, or possibly washed with shampoo followed by rinsing with water, before being dried or left to dry.
[0529] Preferably, at the end of the treatment, the keratin fibers are rinsed, preferably they do not undergo washing after this rinsing step.
[0530] Preferably the composition according to the invention is carried out at a temperature between 10 °C and 100 °C, better between 15 °C and 40 °C.
[0531] The composition can then be left in place for a period usually ranging from 1 minute to 2 hours, preferably from 5 minutes to 1 hour 30 minutes, better from 10 minutes to 1 hour.
[0532] Advantageously, after application of the coloring composition, the hair can be subjected to heat treatment. In practice, this operation can be carried out using a hair dryer, a hair dryer, an infrared heater, and other conventional heating devices.
[0533] The temperature during the process is classically between ambient temperature (between 15 to 25 °C) and 80 °C, preferably between ambient temperature and 60 °C.
[0534] At the end of the treatment, the human keratin fibres are possibly rinsed with water, possibly undergo washing with shampoo followed by rinsing with water, before being dried (mechanically with a towel, or absorbent paper, or by heat) or left to dry.
[0535] The present invention finally relates to the use of the composition according to the invention as described above for the coloring of keratin fibers, and in particular of hair.
[0536] The present invention will now be described more specifically by means of examples, which are in no way limiting to the scope of the invention. However, the examples allow for the support of specific features, variants, and preferred embodiments of the invention. EXAMPLES
[0537] In the following examples, all quantities are given as mass percentage of active material (AM) relative to the total weight of the composition (unless otherwise stated). Example
[0538] The compositions Al and A2 as described in Table 2 below were prepared.
[0539] [Tables2] Compositions A1 (invention) A2 (comparative) Benzyl alcohol 0.3 0.3 Isopropyl myristate 2.0 2.0 Cetyl esters (1) 1.5 1.5 Basic Yellow 87 0.03 0.03 Basic Brown 17 0.12 0.12 Basic Red 51 0.004 0.004 Basic Orange 31 0.003 0.003 Cetearyl alcohol 6.0 6.0 Butyrospermum parkii butter 1.0 1.0 Stearamidopropyl dimethylamine 2.4 2.4 Sunflower (Helianthus annuus) oil 1.0 1.0 Avocado (Persea gratissima) oil 0.01 0.01 Tartaric acid 0.42 0.42 Tetrasodium glutamate diacetate 0.24 - Preservatives Qs Qs Water Qsp 100 Qsp 100
[0540] (1) sold by the company CRODA under the trade name SP CRODAMOL MS MBAL-PA-(SG) Protocol
[0541] Each of the compositions A1 and A2 was applied to bleached hair strands at a rate of 5 g of composition per gram of strand. The strands were then placed on a plate heated to 27°C for 10 minutes. Afterward, the strands were rinsed and then dried. Results
[0542] The colorimetric measurements were carried out using a KONICA MINOLTA-3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included) in the CIELab system.
[0543] Chromaticity is calculated according to the equation: C* = +(b*r
[0544] Chromaticity is measured by the values a* and b*, a* representing the red / green axis and b* the yellow / blue axis.
[0545] The higher the value of the chromaticity C*, the more chromatic the color of the treated keratin fibers.
[0546] The results are summarized in Table 3 below:
[0547] [Tables3] Compositions Al (invention) A2 (comparative) a* 41.45 37.32 b* 43.40 42.02 C* 60.01 56.20
[0548] Hair strands treated with composition Al according to the invention exhibit a higher C* value than those treated with the comparative composition A2. In other words, composition Al according to the invention makes it possible to obtain hair strands with improved chromaticity compared to those treated with the comparative composition A2.
Claims
Demands
1. Cosmetic composition comprising: - at least one compound selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and mixtures thereof; - at least one colouring agent selected from oxidation colourings, direct colourings and mixtures thereof; - at least one compound selected from fatty amines, their salts, and mixtures thereof, which are not (poly)oxyalkylated.
2. Composition according to claim 1, characterized in that the compound(s) selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and mixtures thereof are selected from alkali metal salts, preferably tetrasodium glutamate diacetate.
3. Composition according to any one of the preceding claims, characterized in that the total content of the compound(s) selected from N,N-dicarboxymethyl glutamic acid, its salts, its solvates, the solvates of its salts and mixtures thereof ranges from 0.001 to 15% by weight, more preferably from 0.005 to 10% by weight, better from 0.01 to 8% by weight, even better from 0.05 to 5% by weight, or even from 0.075 to 2% by weight, or even from 0.1 to 1% by weight, relative to the total weight of the composition.
4. Composition according to any one of the preceding claims, characterized in that the coloring agent(s) is or are selected from direct dyes, preferably selected from azo direct dyes, hydrazono direct dyes, aryl nitrate direct dyes, triarylmethane direct dyes, quinone direct dyes and in particular anthraquinones, and mixtures thereof.
5. Composition according to any one of the preceding claims, characterized in that the total content of the colouring agent(s), preferably of the direct colouring agent(s), ranges from 0.001 to 20% by weight, preferably from 0.005 to 15% by weight, more preferably from 0.01 to 10% by weight, better from 0.05 to 5%, even better from 0.1 to 3% by weight, relative to the total weight of the composition.
6. Composition according to any one of the preceding claims, characterized in that the compound(s) selected from fatty amines, their salts, and mixtures thereof are selected from amidoamines of formula (A) following: RCONHR”N(R')2 (A) in which: R represents a linear or branched monovalent hydrocarbon radical, saturated or unsaturated and substituted or unsubstituted, having from 5 to 29 carbon atoms, preferably from 7 to 23 carbon atoms, and in particular a linear or branched C5-C29 alkyl radical, preferably a linear or branched C7-C23 alkyl radical, or a linear or branched C5-C29 alkenyl radical, preferably a linear or branched C7-C23 alkenyl radical; R'' represents a divalent hydrocarbon radical having fewer than 6 carbon atoms, preferably 2 to 4 carbon atoms, better 3 carbon atoms; and R', identical or different, represents a linear or branched monovalent hydrocarbon radical having fewer than 6 carbon atoms, preferably from 1 to 4 carbon atoms, saturated or unsaturated and substituted or unsubstituted, preferably a methyl radical; and their mixtures.
7. Composition according to any one of the preceding claims, characterized in that the compound(s) selected from fatty amines, their salts, and mixtures thereof are selected from brassicamidopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl dimethylamine, oleamidopropyl dimethylamine, and mixtures thereof.
8. Composition according to any one of the preceding claims, characterized in that the total content of the compound(s) selected from fatty amines, their salts, and mixtures thereof ranges from 0.01 to 6% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 1.5 to 3% by weight relative to the total weight of the composition.
9. Composition according to any one of the preceding claims, characterized in that it further comprises at least one non-siliconized fat other than fatty amines, preferably selected from solid fats, liquid fats, butters, and mixtures thereof, more preferably from solid fatty alcohols, solid esters of fatty acids and / or fatty alcohols, vegetable oils, liquid esters of fatty acids and / or fatty alcohols other than triglycerides, butters of vegetable origin and mixtures thereof.
10. Composition according to the preceding claim, characterized in that the total content of the non-siliconized fat(s) other than fatty amines ranges from 0.1 to 35% by weight, preferably from 1 to 30% by weight, more preferably from 2 to 25% by weight, better from 5 to 20% by weight. weight, or better yet 8 to 15% by weight relative to the total weight of the composition.
11. Composition according to any one of the preceding claims, characterized in that it further comprises at least one cationic polymer, preferably selected from cationic polysaccharides, more preferably from cationic galactomannan gums, better from cationic guar gums.
12. A composition according to any one of the preceding claims, characterized in that it further comprises at least one cationic surfactant other than said compound(s) selected from fatty amines, their salts, and mixtures thereof, preferably selected from quaternary ammonium salts, preferably from: - quaternary ammonium salts of the following formula (X): in which: The R8 to Ru groups, which may be identical or different, represent an aliphatic group, linear or branched, comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or al-kylaryl, at least one of the R8 to Ru groups comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms and X is an anion chosen from the group of halides, phosphates, acetates, lactates, alkyl(Ci-C4)sulfates, alkyl(Ci-C4)- or alkyl(Ci-C4)aryl-sulfonates; - quaternary ammonium salts of the following formula (XIII): ov p 11 I* Rj—C--Η|„ R., (XIII), in which: R22 is chosen from among the Ci-C6 alkyl groups and the Ci-C6 hydroxyalkyl or dihydroxyalkyl groups; R23 is chosen from: the -C(O)R26 group, the CrC22 hydrocarbon R27 groups, linear or branched, saturated or unsaturated, the atom of hydrogen; R25 is chosen from: the -C(O)R28 group, the R29 hydrocarbon groups in Ci-C6, linear or branched, saturated or unsaturated, the hydrogen atom; R24, R26 and R28, identical or different, are chosen from the C7-C2i hydrocarbon groups, linear or branched, saturated or unsaturated; r, s and t, identical or different, are integers ranging from 2 to 6; rl and tl, identical or different, are 0 or 1; r2 + rl = 2 r and tl + t2 = 2 t, y is an integer from 1 to 10, x and z, identical or different, are integers from 0 to 10, X is a simple or complex anion, organic or inorganic, provided that the sum x + y + z is from 1 to 15, that when x is 0 then R23 designates R27 and that when z is 0 then R25 designates R29; - and their mixtures; more preferentially among tetraalkylammonium chlorides, such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group comprises 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides, dipalmitoylethylhydroxyethylmethylammonium salts, in particular dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.
13. Composition according to any one of the preceding claims, characterized in that it further comprises at least one silicone, preferably selected from amino silicones, more preferably selected from silicones of the following formula (VI) and mixtures thereof: in which: - m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n denoting a number from 0 to 1999 and in particular from 49 to 149 and m denoting a number from 1 to 2000, and in particular from 1 to 10; and - A denotes a linear or branched alkylene radical, preferably linear, having from 4 to 8 carbon atoms, preferably 4 carbon atoms.
14. Composition according to any one of the preceding claims, characterized in that it further comprises at least one polysaccharide other than cationic polymers, preferably selected from non-ionic polysaccharides, more preferably from cellulose ethers, such as (Cl-C4)alkylcelluloses and (poly)hydroxy(Cl-C4)alkylcelluloses, and mixtures thereof.
15. A method for coloring keratin fibers, preferably hair, comprising applying to said fibers the composition as defined in any one of the preceding claims.
16. Use of the composition as defined in any one of claims 1 to 14 for coloring keratin fibers, preferably hair.