KERATIN FIBER DYE COMPOSITION
The keratin fiber dye composition with N,N-dicarboxymethylglutamic acid, creatine, and alkaline agents addresses the issue of metal ion-induced hair damage by effectively chelating ions, preserving the hair's structure and improving formulation ease.
Patent Information
- Authority / Receiving Office
- FR · FR
- Patent Type
- Utility models
- Current Assignee / Owner
- LOREAL SA
- Filing Date
- 2024-12-10
- Publication Date
- 2026-05-15
AI Technical Summary
Existing hair dyeing products are ineffective in removing metal ions that destabilize keratin structures, leading to hair damage and weakened strength, and current chelating agents have limited solubility and formulation issues.
A keratin fiber dye composition comprising N,N-dicarboxymethylglutamic acid, organic amines like creatine, oxidative dyes, and alkaline agents, which effectively chelate metal ions, protecting the hair from damage and improving formulation ease.
The composition effectively prevents hair damage by stabilizing keratin structures, maintaining the integrity of the cuticle, and is easily formulated into hair dye products.
Abstract
Description
Title of the invention: KERATIN FIBER DYE COMPOSITION technical field
[0001] The present invention relates to a composition. In particular, the present invention relates to a keratin fiber dye composition. The present invention also relates to a method for dyeing keratin fibers. STATE OF THE ART
[0002] In the field of dyeing keratin fibers, such as hair, continuous efforts are being made to improve product performance. It is known that the presence of metal ions (e.g., Fe, Cu, etc.) will destabilize keratin structures by binding to the exposed positive charges of the protein chain, thereby damaging the hair and weakening its strength and smooth texture.
[0003] To meet this challenge, various approaches have been explored in the field. Some hair dyeing and bleaching products contain chelating agents to remove metal ions so that the hair can return to a healthy state. However, some chelating agents are ineffective, and some have limited solubility, which demonstrates a limitation in formulation, particularly for the manufacturing process.
[0004] Thus, it is desired that hair dyeing products include more effective chelating agents, which can be easily formulated in the products, and that the products can protect the hair from damage caused by metal ions. Summary of the invention
[0005] An object of the present invention is therefore to develop dye compositions for keratinous materials, which include more effective chelating agents which can be easily formulated in the compositions, and which can protect keratinous materials from damage caused by metal ions.
[0006] Thus, according to a first aspect, the present invention proposes a composition, preferably a keratin fiber dye, comprising: i. at least one compound selected from N,N-dicarboxymethylglutamic acid, its salts and their combinations; ii. at least one organic amine chosen from creatine, its derivatives and their combinations; iii. at least one oxidative dye; and iv. at least one alkaline agent.
[0007] The inventors have discovered that the composition according to the present invention can be easily formulated and can protect keratinous materials from damage caused by metal ions, thus substantially preserving the integrity of the cuticle of keratinous materials.
[0008] According to a second aspect, the present invention proposes a method for dyeing keratin fibers comprising applying the composition according to the present invention to the keratin fibers.
[0009] Other subjects and features, aspects and advantages of the present invention will be presented in the following description and will partly emerge from the description, or may be learned through practice of the present invention. DETAILED DESCRIPTION OF THE INVENTION
[0010] As used herein, unless otherwise indicated, the limits of a range of values are included in that range, in particular in the expressions "between... and..." and "from... to...".
[0011] As used herein, the term "including" should be interpreted as encompassing all the features specifically mentioned as well as optional, additional, unspecified features.
[0012] As used herein, the use of the term "comprising" also discloses the embodiment in which no features other than the features specifically mentioned are present (i.e., "consisting of").
[0013] Unless otherwise defined, all technical and scientific terms used herein have the meaning commonly accepted by a person skilled in the art of the present invention. Where the definition of a term in this description conflicts with the meaning commonly accepted by a person skilled in the art of the present invention, the definition described herein shall prevail.
[0014] Unless otherwise specified, all numerical values expressing a quantity of ingredients and the like used in the description and claims shall be understood as modified by the term "approximately". Accordingly, unless otherwise stated, the numerical values and parameters described herein are approximate values that may be changed according to the desired performance obtained, as required.
[0015] As used herein, the expression "at least one" used in this description is equivalent to the expression "one or more".
[0016] In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.
[0017] The expression "keratin fibres" here refers to fibres containing keratin as the main constituent element, and examples of them include hair, eyelashes, eyebrows, and the like.
[0018] According to the first aspect, the composition of the present invention comprises: i. at least one compound selected from N,N-dicarboxymethylglutamic acid, its salts and their combinations; ii. at least one organic amine chosen from creatine, its derivatives and their combinations; iii. at least one oxidative dye; and iv. at least one alkaline agent. N,N-Dicarboxymethylglutamic acid and its salts
[0019] The composition of the present invention comprises at least one compound selected from N,N-dicarboxymethylglutamic acid, its salts and their combinations.
[0020] The inventors discovered that N,N-dicarboxymethylglutamic acid, its salts, and their combinations include a natural amino acid-derived structure in the molecule, and is biodegradable and offers high solubility over a wide pH range without compromising the performance of heavy metal chelating ions. Furthermore, the inventors also discovered that it does not sensitize human skin.
[0021] The salts include, in particular, alkali metal salts, alkaline earth metal salts, ammonium salts and substituted ammonium salts.
[0022] Among the salts of these compounds, alkali metal salts, and in particular sodium or potassium salts, are preferred.
[0023] Preferably, the composition according to the present invention comprises at least one compound selected from the alkali metal salts of N,N-dicarboxymethylglutamic acid.
[0024] More preferably, the composition according to the present invention comprises at least one compound selected from sodium salts and potassium salts of N,N-dicarboxymethylglutamic acid.
[0025] More preferably, the composition according to the present invention comprises tetrasodium glutamate diacetate (GLDA). For example, AkzoNobel's Dissolvine GL38, 47S or 45S may be used.
[0026] Advantageously, the compound chosen from N,N-dicarboxymethylglutamic acid, its salts and their combinations is present in the composition according to the present invention in an amount ranging from 0.01% by weight to 10% by weight, preferably ranging from 0.02% by weight to 5% by weight, more preferably ranging from 0.05% by weight to 2% by weight, relative to the total weight of the composition. Creatine and its derivatives
[0027] The composition of the present invention comprises at least one organic amine selected from creatine, its derivatives and their combinations.
[0028] Preferably, the organic amine is chosen from creatine, compounds of formula (I), and their combinations: RI ®
[0029] in which
[0030] - M is a salt-forming cation, such as sodium, potassium, ammonium or the triethanolamine;
[0031] - RI is chosen from hydrogen, -CH3, -CH(CH3)2, -CH2CH(CH3)2, - CH(CH3)CH2CH3, -CH2C2H4OH, -CH2OH, -CH(OH)CH3, -(CH2)4NH2, -(CH2)3NHCH(NH2)2, -(CH2)2C(O)OH, and -(CH2)2C(O)O M+.
[0032] Preferably, in formula (I), M is sodium or potassium, RI is chosen from hydrogen, -CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH2C2H4OH, -CH2OH and -CH(OH)CH3.
[0033] More preferably, the composition according to the present invention comprises creatine.
[0034] Advantageously, organic famine selected from creatine, its derivatives, and their combinations is present in the composition of the present invention in an amount ranging from 0.0001% by weight to 10% by weight, preferably from 0.0005% by weight to 5% by weight, and more preferably from 0.001% by weight to 3% by weight, relative to the total weight of the composition. Oxidative dyes
[0035] The composition of the present invention comprises at least one oxidative dye.
[0036] Preferably, the oxidative dye comprises one or more oxidation bases, optionally combined with one or more couplers.
[0037] Oxidation bases can be chosen in particular from p-phenylenediamines, bis(phenyl)alkylenediamines, p-aminophenols, o-aminophenols, heterocyclic bases, and their addition salts, and mixtures thereof.
[0038] Among the p-phenylenediamines, examples that can be cited include p-phenylenediamine, p-tolylenediamine, 2-chloro-p-phenylenediamine, 2-methyl-p-phenylenediamine (CI 76042), 3-methyl-p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, 4-methyl-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-Dimethyl-p-phenylenediamine, 2,6-Diethyl-p-phenylenediamine, 2,5-Dimethyl-p-phenylenediamine, V,V-Dimethyl-p-phenylenediamine, V,V-Diethyl-p-phenylenediamine, MAMipropyl-p-phenylenediamine, 4-Amino-V,V-Diethyl-3-methylaniline, 2V,2V-Bis(2-Hydroxyethyl)-p-phenylenediamine, 4-Al,Al-Bis(-Hydroxyethyl)amino-2-methylaniline, 4-V,V-Bis(-Hydroxyethyl)amino-2-chloroaniline, 2-Hydroxyethyl-p-phenylenediamine, 2-Fluoro-p-phenylenediamine, 2-Isopropyl-p-phenylenediamine, A4(-Hydroxypropyl)-p-phenylenediamine, 2-Hydroxymethyl-p-phenylenediamine MAMimethyl-3-methyl-p-phenylenediamine, TV,7V-(ethyl / l-hydroxyethyl)-p-phenylenediamine, V-dihydroxypropyl-p-phcnylcncdiaminc, A4(4'-ammophenyl)-p-phenylenediamine, V-phcnyl-p-phcnylcncdiaminc, 2-hydroxyethyloxy-p-phenylenediamine, 2-acetylaminoethyloxy-p-phenylenediamine, A4(-methoxyethyl)-p-phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-p-phenylenediamine, 2-hydroxyethylamino-5-aminotoluene and 3-hydroxy-l-(4'-aminophenyl)pyrrolidine,and their salts of addition with an acid.
[0039] Among the p-phenylenediamines mentioned above, p-phenylenediamine, p-tolylenediamine, 2-isopropyl-p-phenylenediamine, 2-hydroxyethyl-p-phenylenediamine, 2-hydroxyethyloxy-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, N,N-bis(-hydroxyethyl)-p-phenylenediamine, 2-chloro-p-phenylenediamine and 2-acetylaminoethyloxy-p-phenylenediamine, and their addition salts with an acid, are particularly preferred.
[0040] Among the bis(phenyl)alkylenediamines, examples that can be cited include N,2V'-bis(-hydroxyethyl)-2V,2V'-bis(4'-aminophenyl)-1,3-diaminopropanol, N,V-bis(-hydroxyethyl)-2V,2V-bis(4'-aminophenyl)ethylenediamine, 2V,iV'-bis(4-aminophenyl)tetramethylenediamine, 2V,iV'-bis(-hydroxyethyl)-2V,2V'-bis(4-aminophenyl)tetramethylenediamine, 2V,iV'-bis(4-methylaminophenyl)tetramethylenediamine, MA^'-bis(ethyl)-A^A^'-bis(4'-amino-3'-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane and their addition salts.
[0041] Among the p-aminophenols, examples that can be cited include p-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-(-hydroxyethyl-aminomethyl)phenol and 4-amino-2-fluorophenol, and their addition salts with an acid.
[0042] Among the o-aminophenols, examples that can be cited include 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and their addition salts.
[0043] Among heterocyclic bases, examples that can be cited include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
[0044] Among the pyridine derivatives that can be cited are the compounds described, for example, 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, as well as their addition salts.
[0045] Other pyridine oxidation bases that are useful in the present disclosure are the 3-aminopyrazolo[l,5-a]pyridine oxidation bases or their addition salts described, for example, in patent application FR 2 801 308. Examples that can be cited include pyrazolo[l,5-a]pyrid-3-ylamine, 2-(acetylamino)pyrazolo[l,5-a]pyrid-3-ylamine, 2-(morpholin-4-yl)pyrazolo[l,5-a]pyrid-3-ylamine, 3-aminopyrazolo[l,5-a]pyridine-2-carboxylic acid, 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-yl)pyrazolo[l,5-a]pyrid-3-ylamine, pyrazolo[l,5-a]pyridine-3,5-diamine, 5-(morpholin-4-yl)pyrazolo[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 and their addition salts.
[0046] Among the pyrimidine derivatives that may be cited are the compounds described, for example, in patents DE 2 359 399; JP 88-169 571; JP 05-63 124; EP 0 770 375, or patent application WO 96 / 15 765, 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.
[0047] Among the pyrazole derivatives that may be cited are the compounds described in patents DE 3 843 892 and DE 4 133 957 and patent applications WO 94 / 08 969, WO 94 / 08 970, FR-A-2 733 749 and DE 195 43 988, for example 4,5-diamino-l-methylpyrazole, 4,5-diamino-l-(2-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-l-(4'-chlorobenzyl)pyrazole, 4,5-diamino-l,3-dimethylpyrazole, 4,5-diamino-3-methyl-l-phenylpyrazole, 4,5-diamino-l-methyl-3-phenylpyrazole, 4-amino-l,3-dimethyl-5-hydrazinopyrazole, l-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-l-methylpyrazole, 4,5- diamino-l-tert-butyl-3-methylpyrazole, 4,5-diamino-l-(2-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-l-ethyl-3-methylpyrazole, 4,5-diamino-l-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5-diamino-l-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-l-methylpyrazole, 4,5-diamino-3-hydroxymethyl-l-isopropylpyrazole, 4,5-diamino-3-methyl-l-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 and 3,5-Diamino-4-(-hydroxyethyl)amino-l-methylpyrazole, and their addition salts. 4,5-Diamino-1-(2-methylethyl)pyrazole can also be used.
[0048] Preferably, a 4,5-diaminopyrazole, and more preferably a 4,5-diamino-l-(2-hydroxyethyl)pyrazole and / or one of its salts are used.
[0049] Pyrazole derivatives that may also be cited include diamino-A / IV-dihydropyrazolopyrazolones and in particular those described in patent application FR-A-2 886 136, such as the following compounds and their addition salts: 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 2-amino-3-ethylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 2-amino-3-isopropylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 2-amino-3-(pyrrolidine-1-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-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-bis(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-(pyrrolidine-1-yl)-1,2-dihydropyrazol-3-one,4-amino-5-(3-dimethylaminopyrrolidine-1 -yl)-1,2-diethyl-1,2-dihydropyrazol-3-one or 2,3-diamino-6-hydroxy-6,7-dihydro-1H,5H-pyrazolo[l,2-a]pyrazol-l-one. ,
[0050] Preferably, 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one and / or one of its salts will be used.
[0051] The heterocyclic bases that will be preferentially used include 4,5-diamino-l-(2-hydroxyethyl)pyrazole and / or 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[l,2-a]pyrazol-l-one and / or one of their salts.
[0052] Preferably, the oxidation base is chosen from p-phenylenediamine, p-aminophenol, 2-methoxymethyl-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, and their addition salts, and mixtures thereof.
[0053] The oxidative dye may also include one or more couplers, which may be chosen from those conventionally used for dyeing keratin fibers.
[0054] Among these couplers, we can mention in particular m-phenylenediamines, m-aminophenols, m-diphenols, naphthalene-based couplers, heterocyclic couplers, as well as their addition salts, and their mixtures.
[0055] Examples that can be cited include 1,3-dihydroxybenzene, 1,3-Dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-Diamino-l-(2-hydroxyethyloxy)benzene, 2-amino-4-([3-hydroxyethylamino)-l-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-l-dimethylaminobenzene, sesamol, l-[>-hydroxyethylamino-3,4-methylenedioxybenzene, -naphtol, 2-methyl-l-naphtol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-A-methylindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine, lA-([3-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis([3-hydroxyethylamino)toluene, 6-Hydroxyindoline, hydroxyethyl-3,4-methylenedioxyaniline, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, 2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole, 2,6-dimethyl[3,2-c]-1,2,4-triazole and 6-methylpyrazolo[1,5-a]benzimidazole, their acid addition salts, and mixtures thereof, such as their hydrochloride or dichloride, for example, dichloride of 1-[3-hydroxyethyloxy-2,4-diaminobenzene (2,4-Diaminophenoxyethanol HCl), hydroxyethyl-3,4-methylenedioxyaniline HCl.
[0056] Preferably, the coupler is chosen from m-aminophenol, 6-hydroxybenzomorpholine, rhydroxyethyl-3,4-methylenedioxyaniline, 2,4-diaminophenoxyethanol, and their addition salts, and mixtures thereof.
[0057] In general, the addition salts of the oxidation bases and of the couplers that can be used in the context of the invention are in particular chosen from among the addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
[0058] Advantageously, the oxidative dye is present in the composition of the present invention in an amount ranging from 0.1% by weight to 15% by weight, preferably from 0.25% by weight to 12% by weight, more preferably from 0.4% by weight to 10% by weight, relative to the total weight of the composition. Alkaline agents
[0059] The composition according to the present invention comprises at least one alkali metal.
[0060] The alkali metal(s) may, in particular, be chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25 °C of less than 12, in particular less than 10, and even more advantageously less than 6; and the salts of the previously mentioned organic amines with acids such as carbonic acid or hydrochloric acid. The pKb mentioned here will be the pKb corresponding to the function of greatest basicity.
[0061] Preferably, the alkali agent is chosen from alkanolamines, comprising in particular a primary, secondary or tertiary amine function, and one or more linear or branched CrC8 alkyl groups bearing one or more hydroxyl radicals; oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and compounds corresponding to the following formula (II): Rx^ zRz(H) zNW-Nv Ry Rt
[0062] wherein W is a Ci-C6 alkylene residue optionally substituted by a hydroxyl group or a Ci-C6 alkyl radical; Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or a Cr C6 alkyl, Ci-C6 hydroxyalkyl or Ci-C6 aminoalkyl radical.
[0063] Preferably, the composition according to the present invention comprises at least one alkaline agent selected from alkanolamines such as ethanolamine.
[0064] Advantageously, the alkaline agent is present in the composition according to the present invention in an amount ranging from 0.1% by weight to 30% by weight, preferably from 0.5% by weight to 25% by weight, more preferably from 1% by weight to 20% by weight, relative to the total weight of the composition. Aqueous phase
[0065] The composition of the present invention may further comprise an aqueous phase.
[0066] Said aqueous phase is preferably present in an amount ranging from 50% by weight to 99% by weight, more preferably from 70% by weight to 95% by weight, relative to the total weight of the composition.
[0067] The aqueous phase comprises water.
[0068] Water is preferably present in the composition of the present invention in an amount ranging from 50% by weight to 99% by weight, preferably from 60% by weight to 95% by weight, relative to the total weight of the composition.
[0069] Optionally, the aqueous phase comprises one or more water-miscible organic solvents (at an ambient temperature of 25 °C) such as, for example, monoalcohols having from 2 to 6 carbon atoms such as ethanol, isopropanol; polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferably having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; glycol ethers (having in particular 3 with 16 carbon atoms) such as mono-, di- or tri-propylene glycol (Ci-C4)alkyl ethers, mono-, di- or tri-ethylene glycol (C1-C4) alkyl ethers, and mixtures thereof.
[0070] Advantageously, the composition of the present invention comprises from 0.5% by weight to 40% by weight, preferably from 1% by weight to 20% by weight of an organic solvent miscible with water mentioned above, in particular glycerin, relative to the total weight of the composition. Fatty phase
[0071] The composition of the present invention may further comprise a fatty phase.
[0072] The fatty phase comprises at least one fatty substance.
[0073] As used herein, the term "fatty substance" refers to an organic compound that is insoluble in water at ordinary temperature (25 °C) and atmospheric pressure (1.013*105 Pa) (solubility less than 5% by weight, preferably less than 1% by weight and even more preferably less than 0.1% by weight).
[0074] Preferably, the fatty phase comprises at least one fatty substance, which is solid at room temperature (25 °C) and atmospheric pressure (l.013*105 Pa).
[0075] More preferably, the fatty phase comprises at least one fatty alcohol wax, such as cetearyl alcohol.
[0076] Advantageously, the fatty phase is present in an amount ranging from 1% by weight to 40% by weight, more preferably from 2% by weight to 25% by weight, relative to the total weight of the composition. cosmetic active ingredients
[0077] Optionally, the composition of the present invention includes one or more additional active ingredients for dyeing and / or caring for keratin fibers.
[0078] A person skilled in the art can select the quantity of additional active ingredients according to the desired objective. Additional adjuvants
[0079] The composition according to the present invention may also include additional adjuvants, such as perfumes, preservatives, surfactants (for example oleic acid and coco-glucoside), antioxidants (for example ascorbic acid and sodium metabisulfite), thickeners (for example xanthan gum), etc.
[0080] Preferably, the composition according to the present invention comprises one or more adjuvants selected from surfactants, antioxidants, thickeners, and their combinations.
[0081] A person skilled in the art can choose the quantity of additional adjuvants so as not to have a negative impact on the final use of the composition according to the present invention.
[0082] According to a preferred embodiment, the present invention proposes a composition, preferably a keratin fiber dye, comprising, relative to the total weight of the composition:
[0083] (i) from 0.05% by weight to 2% by weight of at least one compound selected from the acid N,N-dicarboxymethylglutamic acid, one of its sodium salts, one of its potassium salts and their combinations;
[0084] (ii) from 0.001 wt% to 3 wt% of at least one organic amine selected from creatine, compounds of formula (I), and their combinations:
[0085] in which
[0086] - M is sodium or potassium, RI is chosen from hydrogen, -CH3, -CH(CH3 )2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH2C2H4OH, -CH2OH, and -CH(OH)CH3;
[0087] (iii) from 0.4% by weight to 10% by weight of at least one oxidative dye selected from oxidation bases and couplers; and
[0088] (iv) from 1% by weight to 20% by weight of at least one alkaline agent selected from the alkanolamines. Preparation and use
[0089] The composition according to the present invention can be prepared by a routine practice.
[0090] The composition of the present invention can be used to dye keratin fibers, in particular hair.
[0091] According to the second aspect, the present invention proposes a method for caring for keratin fibers comprising applying the composition according to the present invention to the keratin fibers.
[0092] In particular, the keratin fiber corresponds to hair. EXAMPLES
[0093] The following examples are given by way of non-limiting illustrations of the present invention.
[0094] The main raw materials used, their trade names and suppliers are listed in Table 1.
[0095] [Tables 1] INCI Name Trade Name Supplier Creatine (Creatine) TEGO COSMO C100 EVONIK GOLDSCHM IDT Tetrasodium glutamate diacetate (Tetrasodium glutamate diacetate) DISSOLVINE GL-47-S AKZO NOBEL (NOU RYON) Ethylenediamine tetraacetic acid (Ethylenediamine tetraacetic acid) EDETA BS BASF Cetearyl alcohol (Cetearyl alcohol) NAFOL 1618EN (RSPO / MB) SASOL Xanthan gum (Xanthan gum) XANTHAN GUM FNC S JUNGBUNZLAUER Coco-glucoside PLANTACARE 818 UP BASF 6-Hydroxybenzomorpholine 3,4-DIHYDRO-2H-1,4-BENZOXAZIN-6-OL(IMEXINE OV) ZHEJIANG DRAGON TECHNOLOGY Inventive Example 1 and Comparative Examples 1-3
[0096] The compositions of inventive example (E1.) 1 and comparative examples (CE1.) 1 to 3 were prepared with the components listed in Table 2 (the contents are expressed as percentages by weight relative to the total weight of each composition, unless otherwise indicated):
[0097] [Tables2] Phase Components El. 1 EC. 1 EC. 2 EC. 3 A Tetrasodium glutamate diacetate 0.2 0.2 0 0.2 Cetearyl alcohol 17.5 17.5 17.5 17.5 Xanthan gum 0.2 0.2 0.2 0.2 Oleic acid 3 3 3 3 Coco-glucoside 2 2 2 2 Water QS100 QS100 QS100 QS100 Al Ethanolamine 12 12 12 12 A2 Ethylenediaminetetraacetic acid 0 0 0.2 0 B Glycerin 10 10 10 10 C Creatine 1 0 1 0 Alanine 0 0 0 1 Ascorbic acid 0.25 0.25 0.25 0.25 Sodium metabisulfite 0.7 0.7 0.7 0.7 6-Hydroxybenzomorpholine 0.7 0.7 0.7 0.7 2,4-Diaminophenoxyethanol HCl 0.2 0.2 0.2 0.2 N,N-bis(2-hydroxyethyl)-p-phenylenediamine sulfate 0.3 0.3 0.3 0.3 m-Aminophenol 0.1 0.1 0.1 0.1 p-Phenylenediamine 0.8 0.8 0.8 0.8 Hydroxyethyl-3,4-methylenedioxyaniline HCl 0.8 0.8 0.8 0.8
[0098] The composition of inventive example 1 represents a composition according to the present invention.
[0099] The composition of comparative example 1 does not include (ii) at least one organic amine selected from creatine, its derivatives and their combinations.
[0100] The composition of comparative example 2 comprises ethylenediaminetetraacetic acid instead of (i) at least one compound selected from N,N-dicarboxymethylglutamic acid, its salts and their combinations.
[0101] The composition of comparative example 3 includes alanine instead of (ii) at least one organic amine selected from creatine, its salts and their combinations.
[0102] Preparation procedure:
[0103] The compositions of inventive example 1 and comparative examples 1 and 3 were prepared as follows: 1. Mixing the components of Phase A at 65 °C in a tank under agitation at 150 rpm for 30 minutes to obtain a uniform mixture; 2. Adding the Al phase component to the tank with stirring to obtain another uniform mixture; 3. Addition of the phase B component to the tank with agitation at 1500 rpm to emulsify at 65 °C; 4. Cooling the mixture to 35°C within 30 minutes; 5. Addition of phase C components to the tank at 35°C under agitation at 500 rpm to obtain a uniform mixture; 6. then cool the mixture with stirring at 500 rpm at room temperature to obtain the compositions.
[0104] The composition of comparative example 2 was prepared as follows: 1. Mixing the components of Phase A at 65 °C in a tank under agitation at 150 rpm for 30 minutes to obtain a uniform mixture; 2. Adding the Al phase component to the tank with stirring to obtain another uniform mixture; 3. addition of the component of phase A2 into the uniform mixture obtained in 2); 4. Addition of the phase B component to the tank with agitation at 1500 rpm to emulsify at 65 °C; 5. Cooling the mixture to 35°C within 30 minutes; 6. Addition of phase C components to the tank at 35 °C under stirring at 500 rpm to obtain a uniform mixture; 7. then cool the mixture with stirring at 500 rpm at room temperature to obtain the composition.
[0105] As demonstrated in the procedure, tetrasodium glutamate diacetate offers an easier product formulation than ethylenediaminetetraacetic acid, as it does not require separate addition after the alkaline agent.
[0106] Evaluation:
[0107] The level of hair damage during the application of the compositions of inventive example 1 and comparative examples 1 to 3 was evaluated as follows.
[0108] Strands of natural black Chinese hair were colored 5 times with each composition of inventive example 1 and comparative examples 1 to 3, then the microstructure of the hair, in particular the state of hair damage caused by the oxidative hair staining in terms of cuticle integrity was observed using a scanning electron microscope immediately after staining.
[0109] The scores were given according to the following standard:
[0110] 5: the cuticles are intact, no damage;
[0111] 4: the cuticles are slightly raised or damaged;
[0112] 3: The cuticles are slightly raised or damaged, with slight loss of cuticles;
[0113] 2: the cuticles are damaged, a loss of cuticles is observed and the cortex is not protected;
[0114] 1: the cuticles are severely damaged, there are almost no cuticles left.
[0115] The higher the score, the less the cuticle has been damaged.
[0116] Cuticle integrity scores are summarized in Table 3.
[0117] [Tables3] Properties El. 1 EC. 1 EC. 2 EC. 3 Cuticle Integrity Score 5 2 1 3
[0118] It can be seen from Table 3 that the composition of inventive example 1 can effectively prevent hair damage.
Claims
1.
2.
3. Demands Composition of keratin fiber dye, comprising: (i) at least one compound selected from N,N-dicarboxymethylglutamic acid, its salts and their combinations; (ii) at least one organic amine selected from creatine, its derivatives and their combinations; (iii) at least one oxidative dye; and (iv) at least one alkaline agent. Composition according to claim 1, wherein the compound selected from N,N-dicarboxymethylglutamic acid, its salts and combinations thereof is selected from alkali metal salts of N,N-dicarboxymethylglutamic acid, preferably selected from sodium salts and potassium salts of N,N-dicarboxymethylglutamic acid, more preferably the composition comprises tetrasodium glutamate diacetate. Composition according to any one of claims 1 and 2, wherein the organic amine is selected from creatine, compounds of formula (I) and their combinations:
4.
5. in which - M is a salt-forming cation, such as sodium, potassium, ammonium, or triethanolamine; - RI is chosen from hydrogen, -CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH2C2H4OH, -CH2OH, -CH(OH)CH3, -(CH2)4NH2, -(CH2)3NHCH(NH2)2, -(CH2)2C(O)OH, and -(CH2)2C(O)O m+. Composition according to any one of claims 1 to 3, wherein the oxidative dye comprises one or more oxidation bases, optionally combined with one or more couplers. Composition according to claim 4, wherein: the oxidation base is chosen from p-phenylenediamines, bis(phenyl)alkylenediamines, p-aminophenols, o-aminophenols, heterocyclic bases, and their addition salts, and mixtures thereof, and preferably from p-phenylenediamine, p-aminophenol, 2-methoxymethyl-p-phenylenediamine, MA-bis / 2-hydroxyethyl-p-phenylenediamine, and their addition salts, and mixtures thereof, and / or the coupler is chosen from m-phenylenediamines, m-aminophenols, m-diphenols, naphthalene-based couplers, heterocyclic couplers, as well as their addition salts, and mixtures thereof, and preferably from m-aminophenol, 6-hydroxybenzomorpholine, hydroxyethyl 1,3,4-methylenedioxyaniline, 2,4-diaminophenoxyethanol, and their addition salts, and their mixtures.
6. Composition according to any one of claims 1 to 5, wherein the alkali agent is selected from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25 °C less than 12; and salts of organic amines, preferably the alkali agent is selected from alkanolamines, comprising in particular a primary, secondary or tertiary amine function, and one or more linear or branched CrC8 alkyl groups bearing one or more hydroxyl radicals; oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and compounds corresponding to the following formula (II): Rx^ / Rz(II) xN WN R / Rt in which W is a Ci-C6 alkylene residue optionally substituted by a hydroxyl group or a Ci-C6 alkyl radical;Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or a Ci-C6 alkyl, Ci-C6 hydroxyalkyl or Ci-C6 aminoalkyl radical.
7. Composition according to any one of claims 1 to 6, further comprising an aqueous phase, preferably in an amount from 50% by weight to 99% by weight, more preferably from 70% by weight to 95% by weight, relative to the total weight of the composition
8.
9. Composition according to any one of claims 1 to 7, further comprising a fat phase, preferably in an amount from 1% by weight to 40% by weight, more preferably from 2% by weight to 25% by weight, relative to the total weight of the composition. Composition according to claim 1, comprising, in relation to the total weight of the composition: (i) from 0.05% by weight to 2% by weight of at least one compound selected from N,N-dicarboxymethylglutamic acid, one of its sodium salts, one of its potassium salts and their combinations; (ii) from 0.001 wt% to 3 wt% of at least one organic amine selected from creatine, compounds of formula (I), and combinations thereof: MM RI ®
10. in which M is sodium or potassium, RI is chosen from hydrogen, -CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -ch2c2h4oh, -CH2OH, and -CH(OH)CH3; (iii) from 0.4% by weight to 10% by weight of at least one oxidative dye selected from oxidation bases and couplers; and (iv) from 1% by weight to 20% by weight of at least one alkaline agent selected from alkanolamines. A method for dyeing keratin fibers comprising applying the composition according to any one of claims 1 to 9 to keratin fibers.