WO2025003345A1 - Composition comprising a particular base ammonium bicarbonate and fatty acid - Google Patents
Composition comprising a particular base ammonium bicarbonate and fatty acid Download PDFInfo
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- WO2025003345A1 WO2025003345A1 PCT/EP2024/068160 EP2024068160W WO2025003345A1 WO 2025003345 A1 WO2025003345 A1 WO 2025003345A1 EP 2024068160 W EP2024068160 W EP 2024068160W WO 2025003345 A1 WO2025003345 A1 WO 2025003345A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
Definitions
- the invention relates to a composition comprising at least one particular base ammonium bicarbonate and fatty acid.
- the invention also relates to a process for dyeing keratin fibres, notably the hair, using this composition.
- the invention relates to the use of such a composition for dyeing keratin fibres, and notably the hair.
- non-permanent, semi-permanent or direct dyeing which does not use the oxidative condensation process and withstands four or five shampoo washes; it consists in dyeing keratin fibres with dye compositions containing direct dyes;
- oxidation dye precursors such as ortho- or para-phenylenediamines, ortho- or para-aminophenols, or heterocyclic compounds such as pyrazoles, pyrazolinones or pyrazolopyridines.
- oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds via a process of oxidative condensation.
- the dyeing power obtained may not be entirely satisfactory, or may even be weak, and lead to a limited range of colours.
- the colourings may also be insufficiently fast with respect to external agents such as light, shampoo washing or perspiration, and may also be too selective, i.e. the difference in colouring is too great along the same keratin fibre that is differently sensitized between its end and its root.
- compositions for dyeing keratin fibres in particular human keratin fibres such as the hair, which is more environmentally friendly and which is capable of producing good colour build-up, intensity and chromaticity, while at the same time having low selectivity and good fastness, notably good resistance to shampoo washing, and which is capable of delivering good dyeing performance, even after a period of storage, while at the same time having good application qualities and retaining good sensory performance notably in terms of sheen, smoothness, suppleness, straightening and disentangling of keratin fibres such as the hair.
- composition comprising:
- - at least one base chosen from: 2- ⁇ -hydroxyethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof;
- the composition according to the invention is a composition for dyeing keratin fibres, notably the hair.
- composition according to the invention may notably lead to chromatic, powerful, intense and sparingly selective colourings, i.e. colourings that are uniform along the length of the fibre.
- composition according to the invention has good resistance to shampoo washing and also good stability over time, notably little or no change in its viscosity during storage.
- composition according to the invention has good application qualities, notably in terms of texture, ease of application, adhesion to the hair and lengthening.
- composition according to the invention can also afford good cosmetic qualities, notably in terms of sheen, smoothness and suppleness, and a more natural feel, while at the same time preserving the integrity of the fibre.
- composition according to the invention can also provide keratin fibres with cosmetic compositions which do not have a strong ammonia odour.
- a subject of the invention is also a process for dyeing the hair using the composition of the invention.
- a subject of the invention is also a kit comprising, in a first compartment, a composition as defined previously and, in a second compartment, an oxidizing composition comprising at least one chemical oxidizing agent.
- chemical oxidizing agent means an oxidizing agent other than atmospheric oxygen.
- composition according to the invention comprises at least one particular oxidation base.
- the oxidation bases may be present in the form of salts, solvates and/or solvates of salts.
- composition according to the invention comprises at least one oxidation base chosen from 2- ⁇ -hydroxyethyl-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof.
- oxidation base chosen from 2- ⁇ -hydroxyethyl-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine, the addition salts thereof, the
- the addition salts when they are present in the composition according to the invention, are notably chosen from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and the addition salts with a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates
- a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- the total content of oxidation base(s) chosen from 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine, 2-methoxymethyl-para-phenylenediamine, an addition salt thereof, solvates thereof, and/or solvates of the salts thereof and mixtures thereof preferably ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, even better still from 0.1% to 3% by weight relative to the total weight of the composition.
- the total content of oxidation base chosen from 2- ⁇ -hydroxyethyl-para-phenylenediamine, an addition salt thereof, solvates thereof and/or solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferably from 0.005% to 15% by weight, more preferentially from 0.01% to 10% by weight, better still from 0.05% to 5%, even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of oxidation base chosen from 2-( ⁇ -hydroxypropyl)-para-phenylenediamine, an addition salt thereof, solvates thereof and/or solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferably from 0.005% to 15% by weight, more preferentially from 0.01% to 10% by weight, better still from 0.05% to 5%, even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of oxidation base chosen from 2-methoxymethyl-para-phenylenediamine, an addition salt thereof, solvates thereof and/or solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferably from 0.005% to 15% by weight, more preferentially from 0.01% to 10% by weight, better still from 0.05% to 5%, even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- composition according to the invention may optionally also comprise one or more additional oxidation bases, other than 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and 2-methoxymethyl-para-phenylenediamine, addition salts thereof, solvates thereof and solvates of salts thereof, chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, addition salts thereof, solvates thereof and solvates of salts thereof.
- additional oxidation bases other than 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and 2-methoxymethyl-para-phenylenediamine, addition salts thereof, solvates thereof and solvates of salts thereof, chosen from para-phenylenediamines, bis(phenyl)al
- para-phenylenediamines that may be mentioned are, for example, 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-3-methylaniline, N,N-bis( ⁇ -hydroxyethyl)-para-phenylenediamine, 4-N,N-bis( ⁇ -hydroxyethyl)amino-2-methylaniline, 4-N,N-bis( ⁇ -hydroxyethyl)a
- bis(phenyl)alkylenediamines that may be mentioned, for example, are N,N’-bis( ⁇ -hydroxyethyl)-N,N’-bis(4’-aminophenyl)-1,3-diaminopropanol, N,N’-bis( ⁇ -hydroxyethyl)-N,N’-bis(4’-aminophenyl)ethylenediamine, N,N’-bis(4-aminophenyl)tetramethylenediamine, N,N’-bis( ⁇ -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
- para-aminophenols that are mentioned are, 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-( ⁇ -hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the corresponding addition salts, the solvates and solvates of the salts.
- ortho-aminophenols that may be mentioned, for example, are 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the corresponding addition salts, the solvates and the solvates of the salts.
- heterocyclic bases that may be mentioned, for example, are pyridine, pyrimidine and pyrazole derivatives.
- pyridine derivatives that may be mentioned 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, and the corresponding addition salts, the solvates and the solvates of the salts.
- pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[1,5-a]pyridine oxidation bases or the corresponding addition salts described, for example, in patent application FR 2 801 308.
- Examples that may be mentioned include pyrazolo[1,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[1,5-a]pyrid-3-ylamine, 2-(morpholin-4-yl)pyrazolo[1,5-a]pyrid-3-ylamine, 3-aminopyrazolo[1,5-a]pyridine-2-carboxylic acid, 2-methoxypyrazolo[1,5-a]pyrid-3-ylamine, (3-aminopyrazolo[1,5-a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[1,5-a]pyrid-5-yl)ethanol, 2-(3-aminopyrazolo[1,5
- oxidation bases that are useful in the present invention are chosen from 3-aminopyrazolo[1,5-a]pyridines and preferably substituted on carbon atom 2 with:
- pyrimidine derivatives that may 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 the addition salts thereof, the solvates and the solvates of the salts thereof, and the tautomeric forms thereof, when a tautomeric equilibrium exists.
- pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-( ⁇ -hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4’-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-methylpyr
- a 4,5-diaminopyrazole will preferably be used and even more preferentially 4,5-diamino-1-( ⁇ -hydroxyethyl)pyrazole and/or a corresponding salt, a solvate and/or a solvate of a salt.
- pyrazole derivatives that may also be mentioned comprise diamino-N,N-dihydropyrazolopyrazolones and in particular those described in patent application FR-A-2 886 136, such as the following compounds and the corresponding 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-(pyrrolidin-1-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 4,5-diamino-1,2-dimethyl-1,2-dihydr
- Use will preferably be made of 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one and/or a corresponding salt, solvate and/or solvate of a salt.
- Use will preferably be made, as heterocyclic bases, of 4,5-diamino-1-( ⁇ -hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one and/or 2- ⁇ -hydroxyethoxy-3-aminopyrazolo[1,5-a]pyridine and/or a corresponding salt, solvate and/or solvate of a salt.
- the addition salts of the additional oxidation bases present in the composition according to the invention are notably chosen from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, methanesulfonates, phosphates and acetates, and the addition salts with a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, methanesulfonates, phosphates and acetates
- a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- the solvates of the additional oxidation bases more particularly represent the hydrates of said oxidation bases and/or the combination of said oxidation bases with a linear or branched C 1 to C 4 alcohol such as methanol, ethanol, isopropanol or n-propanol.
- the solvates are hydrates.
- composition according to the invention is free of oxidation bases chosen from para-phenylenediamine, para-toluenediamine, addition salts thereof, solvates thereof and solvates of the salts thereof.
- composition according to the invention comprises ammonium bicarbonate.
- the total content of ammonium bicarbonate preferably ranges from 0.01% to 20% by weight, preferentially from 0.05% to 15% by weight, more preferentially from 0.1% to 10% by weight, even more preferentially from 0.4% to 5% by weight, better still from 0.5% to 4% by weight, and better still from 1% to 3% by weight, relative to the total weight of the composition.
- composition according to the invention may comprise one (or more) alkaline agent(s) in addition to ammonium bicarbonate.
- composition according to the invention comprises one (or more) additional alkaline agent(s).
- the additional alkaline agent(s) may be chosen from organic alkaline agents and inorganic alkaline agents.
- the organic alkaline agent(s) are chosen from organic amines, the pKb of which at 25°C is less than 12, more preferentially less than 10 and even more advantageously less than 6. It should be noted that it is the pKb corresponding to the function which has the highest basicity.
- the organic amines do not comprise any alkyl or alkenyl fatty chains comprising more than ten carbon atoms.
- the organic alkaline agent(s) are preferably chosen from alkanolamines, in particular mono-, di- or tri-hydroxy(C1-C6)alkylamines, such as 2-amino-2-methylpropanol, monoethanolamine, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids, polyamines, and mixtures thereof.
- alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C1-C8 alkyl groups bearing one or more hydroxyl radicals.
- MAA monoethanolamine
- diethanolamine triethanolamine
- monoisopropanolamine diisopropanolamine
- N,N-dimethylethanolamine 2-amino-2-methyl-1-propanol
- triisopropanolamine 2-amino-2-methyl-1,3-propanediol
- 3-amino-1,2-propanediol 3-dimethylamino-1,2-propanediol
- tris(hydroxymethylamino)methane tris(hydroxymethylamino)methane.
- amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and include at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions.
- the amino acids may be in neutral or ionic form.
- amino acids that may be used in the present invention, mention may notably be made of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
- ammonium hydroxide also known as aqueous ammonia
- mineral hydroxides such as aqueous ammonia
- silicates such as aqueous ammonia
- metasilicates such as phosphates or hydrogen phosphates
- alkali metal silicates or metasilicates such as sodium silicate and sodium metasilicate.
- mineral hydroxides use will preferably be made of sodium hydroxide, potassium hydroxide or mixtures thereof, preferably sodium hydroxide.
- the additional alkaline agent(s) are chosen from ammonium hydroxide, alkanolamines, alkali metal silicates and metasilicates, mineral hydroxides and mixtures thereof, more preferentially chosen from ammonium hydroxide, alkanolamines and mixtures thereof, better still chosen from ammonium hydroxide, monoethanolamine and mixtures thereof.
- the additional alkaline agent is ammonium hydroxide.
- the total content of the additional alkaline agent(s) ranges from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, more preferentially from 0.5% to 10% by weight and even more preferentially from 1% to 7% by weight, relative to the total weight of the composition.
- composition according to the invention comprises one or more fatty acids.
- fatty acid means a long-chain carboxylic acid, notably a linear or branched, saturated or unsaturated alkyl chain, comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferentially from 10 to 30 carbon atoms and better still from 14 to 22 carbon atoms.
- the fatty acids include at least one carboxylic acid group and a linear or branched, saturated or unsaturated, in particular saturated, alkyl chain comprising from 10 to 30 carbon atoms, in particular from 14 to 22 carbon atoms.
- the fatty acids according to the invention are chosen from compounds having the structure R-C(O)OH in which R represents a linear or branched, saturated or unsaturated, in particular saturated, alkyl group comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, preferentially from 12 to 24 carbon atoms, better still from 14 to 20 carbon atoms.
- the fatty acids present in the composition are neither oxyalkylenated nor glycerolated.
- the fatty acids may be chosen from solid fatty acids and liquid fatty acids, and mixtures thereof.
- solid fatty acid means a fatty acid with a melting point of greater than 25°C, preferably greater than or equal to 28°C, more preferentially greater than or equal to 30°C at atmospheric pressure (1.013 ⁇ 10 5 Pa).
- the solid fatty acids used in the present invention are notably chosen from myristic acid, cetylic acid, stearylic acid, palmitic acid, arachidic acid, stearic acid, lauric acid, behenic acid, 12-hydroxystearic acid, and mixtures thereof, preferably chosen from palmitic acid, lauric acid, myristic acid, stearic acid, and mixtures thereof, better still from palmitic acid, myristic acid, stearic acid, and mixtures thereof.
- liquid fatty acid means a fatty acid with a melting point of less than or equal to 25°C, preferably less than or equal to 20°C at atmospheric pressure (1.013 ⁇ 10 5 Pa).
- the liquid fatty acid(s) according to the invention may be chosen from oleic acid, linoleic acid, arachidonic acid, and mixtures thereof, preferentially oleic acid.
- the fatty acid(s) present in the composition according to the invention are chosen from fatty acids including at least one carboxylic acid group and a linear or branched, saturated or unsaturated alkyl chain comprising from 10 to 30 carbon atoms, in particular from 14 to 22 carbon atoms.
- the fatty acid(s) present in the composition according to the invention are chosen from solid fatty acids, preferably chosen from palmitic acid, lauric acid, myristic acid, stearic acid and mixtures thereof, preferentially from palmitic acid, lauric acid, myristic acid, stearic acid and mixtures thereof.
- the fatty acid(s) are chosen from myristic acid, palmitic acid, stearic acid, and mixtures thereof.
- the fatty acid(s), which are preferably solid, are generally present in a total content ranging from 0.01% to 10% by weight, preferably from 0.05% to 5%, preferentially from 0.1% to 1% by weight, better still from 0.2% to 0.5% by weight relative to the total weight of the composition.
- composition according to the invention may comprise one or more fatty substances other than fatty acids.
- the composition according to the invention comprises one or more fatty substances other than fatty acids.
- fatty substance means an organic compound that is insoluble in water at 25°C and at atmospheric pressure (1.013 ⁇ 10 5 Pa) (solubility of less than 5% by weight, preferably less than 1% by weight, even more preferentially less than 0.1% by weight). They bear in their structure at least one hydrocarbon-based chain including at least 6 carbon atoms and/or a sequence of at least two siloxane groups.
- the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or decamethylcyclopentasiloxane.
- the fatty substances that may be used in the present invention are neither (poly)oxyalkylenated nor (poly)glycerolated.
- the fatty substances that are useful according to the invention are non-silicone fatty substances.
- non-silicone fatty substance refers to a fatty substance not containing any Si-O bonds and the term “silicone fatty substance” refers to a fatty substance containing at least one Si-O bond.
- the fatty substances that are useful according to the invention may be liquid fatty substances (or oils) and/or solid fatty substances.
- liquid fatty substance means a fatty substance with a melting point of less than or equal to 25°C at atmospheric pressure (1.013 ⁇ 10 5 Pa) and the term “solid fatty substance” means a fatty substance with a melting point of greater than 25°C at atmospheric pressure (1.013 ⁇ 10 5 Pa).
- the melting point corresponds to the temperature of the most endothermic peak observed on thermal analysis (differential scanning calorimetry or DSC) as described in the standard ISO 11357-3; 1999.
- the melting point may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name MDSC 2920 by the company TA Instruments.
- DSC differential scanning calorimeter
- all the melting points are determined at atmospheric pressure (1.013 ⁇ 10 5 Pa).
- liquid fatty substance(s) may be chosen from liquid hydrocarbons comprising more than 6 carbon atoms, non-silicone oils of animal origin, oils of triglyceride type of plant or synthetic origin, fluoro oils, liquid fatty alcohols, liquid esters of fatty acid and/or of fatty alcohol other than triglycerides, and mixtures thereof.
- the fatty alcohols and esters more particularly contain at least one saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 40 and better still from 8 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
- the liquid hydrocarbons comprising more than 6 carbon atoms may be chosen from C 6 to C 16 liquid hydrocarbons, which may be linear, branched, optionally cyclic, and preferably saturated. Mention may be made of hexane, cyclohexane, undecane, dodecane, isododecane, tridecane or isoparaffins, such as isohexadecane or isodecane, and mixtures thereof.
- the liquid hydrocarbons comprising more than 6 carbon atoms may also be chosen from linear or branched liquid hydrocarbons comprising more than 16 carbon atoms, which are of mineral or synthetic origin, and are preferably chosen from liquid paraffins or liquid petroleum jelly (or mineral oil), polydecenes, hydrogenated polyisobutene such as Parleam®, and mixtures thereof.
- the liquid hydrocarbons comprising more than 6 carbon atoms may also be chosen from mixtures of alkanes containing from 8 to 28 carbon atoms, more particularly from 15 to 28 carbon atoms; mention may be made of mixtures having, for example, the following INCI names: C15-19 Alkane, C18-C21 Alkane, C21-C28 Alkane, for instance the products Gemseal 40, Gemseal 60 and Gemseal 120 sold by Total, Emogreen L19 sold by SEPPIC and Emogreen L15 sold by SEPPIC, more particularly Emogreen L19 sold by SEPPIC.
- a hydrocarbon-based oil of animal origin that may be mentioned is perhydrosqualene.
- the triglyceride oils of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides including from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stéarinerie Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil, and mixtures thereof.
- liquid fatty acid triglycerides including from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil
- the liquid fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols, preferably unsaturated or branched alcohols, including from 6 to 40 carbon atoms and preferably from 8 to 30 carbon atoms. These fatty alcohols are neither oxyalkylenated nor glycerolated.
- Examples that may be mentioned include octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, isostearyl alcohol, oleyl alcohol, linolenyl alcohol, ricinoleyl alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof.
- oleyl alcohol will be used.
- liquid fatty acid and/or fatty alcohol esters other than the triglycerides mentioned previously, mention may be made notably of esters of saturated or unsaturated, linear C1 to C26 or branched C3 to C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear C1 to C26 or branched C3 to C26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
- esters of monoalcohols Preferably, for the esters of monoalcohols, at least one from among the alcohol and the acid is branched.
- 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
- Esters of C4 to C22 dicarboxylic or tricarboxylic acids and of C1 to C22 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of C2 to C26 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
- composition may also comprise, as fatty ester, sugar esters and diesters of C6 to C30 and preferably C12 to C22 fatty acids.
- sugar esters refers to oxygen-bearing hydrocarbon-based compounds bearing several alcohol functions, with or without aldehyde or ketone functions, and which include at least 4 carbon atoms.
- sugars may be monosaccharides, oligosaccharides or polysaccharides other than the anionic polysaccharides described previously.
- suitable sugars include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, notably alkyl derivatives, such as methyl derivatives, for instance methylglucose.
- the sugar esters of fatty acids may be chosen notably from the group comprising the esters or mixtures of esters of sugars described above and of linear or branched, saturated or unsaturated C6 to C30 and preferably C12 to C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
- the esters may also be chosen from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
- esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates, arachidonates or mixtures thereof notably such as the mixed oleo-palmitate, oleo-stearate and palmito-stearate esters.
- monoesters and diesters and notably sucrose, glucose or methylglucose mono- or di-oleates, -stearates, -behenates, -oleopalmitates, -linoleates, -linolenates and -oleostearates, and mixtures thereof.
- liquid ester of a monoacid and of a monoalcohol Preferably, use will be made of a liquid ester of a monoacid and of a monoalcohol.
- the fatty substances other than fatty acids are chosen from liquid fatty substances, preferably from liquid hydrocarbons comprising more than 6 carbon atoms, plant oils, liquid fatty alcohols and liquid fatty esters and mixtures thereof, more preferentially from liquid hydrocarbons comprising more than 6 carbon atoms, better still from liquid paraffin or liquid petroleum jelly (or mineral oil), mixtures of alkanes containing from 8 to 28 carbon atoms, more particularly from 15 to 28 carbon atoms, and mixtures thereof, even better still from mixtures of alkanes containing from 8 to 28 carbon atoms, more particularly from 15 to 28 carbon atoms.
- the solid fatty substances preferably have a viscosity of greater than 2 Pa.s, measured at 25°C and at a shear rate of 1 s -1 .
- the solid fatty substance(s) are preferably chosen from solid fatty alcohols, solid fatty acid and/or fatty alcohol esters, waxes, ceramides and mixtures thereof.
- fatty alcohol means 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 oxyalkylenated nor glycerolated.
- the solid fatty alcohols that may be used may be chosen, alone or as a mixture, from: 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); montanyl alcohol (or 1-octacosanol); myricyl alcohol (or 1-triacontanol).
- the solid fatty alcohol is chosen from cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, arachidyl alcohol, and mixtures thereof, such as cetylstearyl alcohol or cetearyl alcohol.
- the solid fatty alcohol is chosen from cetyl alcohol, stearyl alcohol and mixtures thereof such as cetylstearyl alcohol or cetearyl alcohol.
- the solid esters of a fatty acid and/or of a fatty alcohol that may be used are preferably chosen from esters derived from a C9-C26 carboxylic fatty acid and/or from a C9-C26 fatty alcohol.
- a wax is a lipophilic compound, which is solid at 25°C and atmospheric pressure, with a reversible solid/liquid change of state, having a melting point greater than about 40°C, which may be up to 200°C, and having in the solid state anisotropic crystal organization.
- the size of the wax crystals is such that the crystals diffract and/or scatter light, giving the composition that comprises them a more or less opaque cloudy appearance.
- the waxes that are suitable for use in the invention may be chosen from waxes of animal, plant or mineral origin, non-silicone synthetic waxes, and mixtures thereof.
- hydrocarbon-based waxes for instance beeswax, notably of organic origin, lanolin wax and Chinese insect waxes; rice bran wax, carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumac wax; montan wax, orange wax and lemon wax, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, the waxes obtained by Fischer-Tropsch synthesis and waxy copolymers, and also esters thereof.
- beeswax notably of organic origin, lanolin wax and Chinese insect waxes
- rice bran wax carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumac wax
- montan wax orange wax and lemon wax
- microcrystalline waxes microcrystalline waxes
- polyethylene waxes the waxes obtained
- C20 to C60 microcrystalline waxes such as Microwax HW.
- waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched C8-C32 fatty chains may also be made of the waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched C8-C32 fatty chains.
- isomerized jojoba oil such as trans-isomerized partially hydrogenated jojoba oil, notably the product manufactured or sold by the company Desert Whale under the commercial reference Iso-Jojoba-50®, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut kernel oil, hydrogenated lanolin oil and bis(1,1,1-trimethylolpropane) tetrastearate, notably the product sold under the name Hest 2T-4S® by the company Heterene.
- the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol such as those sold under the names Phytowax Castor 16L64® and 22L73® by the company Sophim, may also be used.
- a wax that may also be used is a C20 to C40 alkyl (hydroxystearyloxy)stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or as a mixture.
- 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.
- microwaxes in the compositions of the invention; mention may notably be made of carnauba microwaxes, such as the product sold under the name MicroCare 350® by the company Micro Powders, synthetic-wax microwaxes, such as the product sold under the name MicroEase 114S® by the company Micro Powders, microwaxes constituted of a mixture of carnauba wax and polyethylene wax, such as the products sold under the names Micro Care 300® and 310® by the company Micro Powders, microwaxes constituted of a mixture of carnauba wax and of synthetic wax, such as the product sold under the name Micro Care 325® by the company Micro Powders, polyethylene microwaxes, such as the products sold under the names Micropoly 200®, 220®, 220L® and 250S® by the company Micro Powders, and polytetrafluoroethylene microwaxes, such as the products sold under the names Microslip 519® and 519 L® by the company Micro Powders.
- the waxes are preferably chosen from mineral waxes, for instance paraffin wax, petroleum jelly wax, lignite wax or ozokerite; plant waxes, for instance cocoa butter or cork fibre or sugar cane waxes, olive tree wax, rice wax, hydrogenated jojoba wax, ouricury wax, carnauba wax, candelilla wax, esparto grass wax, or absolute waxes of flowers, such as the essential wax of blackcurrant blossom sold by the company Bertin (France); waxes of animal origin, for instance beeswaxes or modified beeswaxes (cera bellina), spermaceti, lanolin wax and lanolin derivatives; microcrystalline waxes; and mixtures thereof, preferentially from plant waxes such as carnauba wax and candelilla wax, and more preferentially candelilla wax (INCI name: Euphorbia cerifera wax).
- the solid fatty substances are preferably chosen from solid fatty alcohols, waxes and mixtures
- the fatty substance(s), other than fatty acids are chosen from liquid hydrocarbons comprising more than 6 carbon atoms, plant oils, fatty alcohols, liquid fatty esters, waxes and mixtures thereof, more preferentially from solid fatty alcohols, plant waxes, mixtures of alkanes containing from 8 to 28 carbon atoms, and mixtures thereof, better still chosen from C15-19 Alkane (INCI name), cetearyl alcohol, candelilla wax and mixtures thereof.
- the total content of the fatty substance(s) other than fatty acids preferably ranges from 5% to 35% by weight, more preferentially from 7% to 30% by weight and better still from 8% to 25% by weight relative to the total weight of the composition.
- the total content of the solid fatty substance(s) other than fatty acids preferably ranges from 5% to 30% by weight, more preferentially from 6% to 25% by weight and better still from 7% to 20% by weight, relative to the total weight of the composition.
- the composition according to the invention comprises one or more hydrocarbons comprising more than 6 carbon atoms, the total content of the hydrocarbon(s) comprising more than 6 carbon atoms preferably ranging from 0.01% to 15% by weight, more preferentially from 0.05% to 10% by weight, better still from 0.1% to 5% by weight, and even better still from 0.5% to 4% by weight relative to the total weight of the composition.
- composition according to the invention may also comprise at least one oxidation coupler.
- composition according to the invention comprises one or more couplers.
- couplers that are useful according to the invention, mention may be made in particular of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based coupling agents and heterocyclic coupling agents, and also the corresponding addition salts, the solvates and solvates of the salts thereof.
- the coupler(s) are chosen from: 6-hydroxybenzomorpholine, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, hydroxyethyl-3,4-methylenedioxyaniline, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, 2-amino-5-ethylphenol, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, and mixtures thereof.
- addition salts of the couplers that may be used in the context of the invention are chosen in particular from addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and the addition salts with a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates
- a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
- the solvates more particularly represent the hydrates of these couplers and/or the combination of these couplers with a linear or branched C1 to C4 alcohol such as methanol, ethanol, isopropanol or n-propanol.
- a linear or branched C1 to C4 alcohol such as methanol, ethanol, isopropanol or n-propanol.
- the solvates are hydrates.
- the composition according to the invention is free of oxidation couplers chosen from resorcinol, 2-methylresorcinol, 4-chlororesorcinol, addition salts thereof, solvates thereof and the solvates of the salts thereof.
- the total content of the coupler(s), salts thereof, solvates thereof, and solvates of the salts thereof, present in the composition according to the invention ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of the couplers chosen from 6-hydroxybenzomorpholine, hydroxyethyl-3,4-methylenedioxyaniline, 2-amino-5-ethylphenol and also the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of the couplers chosen from 6-hydroxybenzomorpholine, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of the couplers chosen from hydroxyethyl-3,4-methylenedioxyaniline, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- the total content of the couplers chosen from 2-amino-5-ethylphenol, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof preferably ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of the composition.
- composition according to the present invention may comprise one (or more) additional surfactant(s), in general other than the fatty acids.
- the composition comprises one (or more) additional surfactant(s).
- anionic surfactants other than fatty acids, nonionic surfactants, cationic surfactants, amphoteric surfactants and/or mixtures thereof.
- the additional surfactants are nonionic surfactants.
- nonionic surfactants examples include the following nonionic surfactants:
- the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
- the number of moles of ethylene oxide and/or propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100, better still from 2 to 50 and even better still from 2 to 40; the number of moles of glycerol ranges notably from 1 to 50 and better still from 1 to 10.
- glycerolated nonionic surfactants use is preferably made of monoglycerolated or polyglycerolated C8 to C40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
- Examples of compounds of this type include lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleocetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
- glycerolated alcohols it is more particularly preferred to use a C8 to C10 alcohol containing 1 mol of glycerol, a C10 to C12 alcohol containing 1 mol of glycerol, and a C12 alcohol containing 1.5 mol of glycerol.
- nonionic surfactant(s) used in the composition according to the invention are chosen from:
- the additional surfactants are preferably chosen from nonionic surfactants, more preferentially chosen from saturated or unsaturated, linear or branched, oxyethylenated or oxypropylenated, C8 to C40 alcohols comprising from 1 to 100 mol of ethylene or propylene oxide, preferably from 2 to 50, more particularly from 2 to 40 mol, and including at least one C8-C20 alkyl chain.
- the additional surfactant(s) represent from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, more preferentially from 0.5% to 10% by weight, better still from 0.8% to 6% by weight and even better still from 1% to 5% by weight relative to the total weight of the composition.
- composition according to the invention may comprise at least one sequestrant (or chelating agent).
- a “sequestrant” (or “chelating agent”) is well known to those skilled in the art and refers to a compound or a mixture of compounds that are capable of forming a chelate with a metal ion.
- a chelate is an inorganic complex in which a compound (the sequestrant or chelating agent) is coordinated to a metal ion, i.e. it forms one or more bonds with the metal ion (formation of a ring including the metal ion).
- a sequestrant (or chelating agent) generally comprises at least two electron-donating atoms which enable the formation of bonds with the metal ion.
- the sequestrant(s) may be chosen from carboxylic acids, preferably aminocarboxylic acids, phosphonic acids, preferably aminophosphonic acids, polyphosphoric acids, preferably linear polyphosphoric acids, salts thereof, and derivatives thereof.
- the salts are notably alkali metal, alkaline-earth metal, ammonium and substituted ammonium salts.
- chelating agents based on polyphosphoric acid sodium tripolyphosphate (STP), tetrasodium diphosphate, hexametaphosphoric acid, sodium metaphosphate, phytic acid.
- STP sodium tripolyphosphate
- tetrasodium diphosphate tetrasodium diphosphate
- hexametaphosphoric acid sodium metaphosphate
- phytic acid sodium tripolyphosphate
- the sequestrants are preferably chosen from diethylenetriaminepentaacetic acid (DTPA) and salts thereof, diethylenediaminetetraacetic acid (EDTA) and salts thereof, ethylenediaminedisuccinic acid (EDDS) and salts thereof, etidronic acid and salts thereof, N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof, and mixtures thereof.
- DTPA diethylenetriaminepentaacetic acid
- EDTA diethylenediaminetetraacetic acid
- EDDS ethylenediaminedisuccinic acid
- etidronic acid and salts thereof etidronic acid and salts thereof, N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof, and mixtures thereof.
- the sequestrant(s) are chosen from N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof, and mixtures thereof.
- GLDA N,N-dicarboxymethylglutamic acid
- the alkali metal salts and notably the sodium or potassium salts are preferred.
- the total content of the sequestrant(s) preferably ranges from 0.001% to 15% by weight, preferentially from 0.005% to 10% by weight, more preferentially from 0.01% to 8% by weight, better still from 0.05% to 5% by weight, even better still from 0.1% to 2% by weight relative to the total weight of the composition.
- composition according to the invention comprises:
- - at least one oxidation base chosen from: 2- ⁇ -hydroxyethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof;
- fatty substance other than fatty acids preferably chosen from liquid hydrocarbons comprising more than 6 carbon atoms, plant oils, liquid fatty alcohols, liquid fatty esters and waxes, and mixtures thereof;
- At least one coupler preferably chosen from 6-hydroxybenzomorpholine, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, hydroxyethyl-3,4-methylenedioxyaniline, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, 2-amino-5-ethylphenol, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, and mixtures thereof;
- At least one additional surfactant preferably chosen from nonionic surfactants, more preferentially chosen from saturated or unsaturated, linear or branched, oxyethylenated or oxypropylenated, C8 to C40 alcohols comprising from 1 to 100 mol of ethylene or propylene oxide, preferably from 2 to 50, more particularly from 2 to 40 mol, and including at least one C8-C20 alkyl chain.
- - at least one sequestrant preferably chosen from N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof.
- composition according to the invention may also comprise at least one organic solvent.
- organic solvents examples include linear or branched C 2 -C 4 alkanols, such as ethanol, propanol and isopropanol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, glycerol, 1,3-propanediol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, and also aromatic alcohols or ethers, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
- linear or branched C 2 -C 4 alkanols such as ethanol, propanol and isopropanol
- polyols and polyol ethers for instance 2-butoxyethanol, propylene glycol, glycerol, 1,3-propanediol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether,
- the organic solvent(s) are chosen from polyols, more preferentially chosen from propylene glycol, glycerol, propane-1,3-diol, and mixtures thereof.
- the organic solvent(s) may be present in a total amount ranging from 0.01% to 30% by weight, preferably from 0.1% to 25% by weight, better still from 0.5% to 20% by weight, even better still from 1% to 15% by weight relative to the total weight of the composition.
- composition according to the invention is preferably an aqueous composition.
- the composition preferably comprises water in an amount of greater than or equal to 5% by weight, preferably greater than or equal to 10% by weight, and better still greater than or equal to 15% by weight, relative to the total weight of the composition.
- composition according to the invention may also comprise one or more nonionic polyoxyalkylenated fatty alcohol ethers of formula (I) below:
- R denotes a linear or branched, saturated or unsaturated C10-C30 hydrocarbon-based radical
- R’ denotes a linear or branched, saturated or unsaturated C10-C30 hydrocarbon-based radical, which may be substituted with a hydroxyl radical, said hydroxyl preferably being beta to the ether function,
- n is an integer between 1 and 100 inclusive
- Alk represents a linear or branched, preferably linear, (C1-C6)alkylene group such as ethylene or propylene, preferably ethylene.
- the radical Alk of formula (I) represents a –CH2-CH2- group.
- the nonionic ether of a polyoxyalkylenated fatty alcohol of formula (I) is such that R and R', independently of each other, denote a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, C12-C20 and preferably C14-C18 hydrocarbon-based radical; R' possibly being substituted with at least one hydroxyl radical, said hydroxyl radical preferably being beta to the ether function, and n denotes an integer greater than or equal to 20, for example ranging from 20 to 100 and preferably from 40 to 80.
- R and R' denote an alkyl radical.
- the nonionic ether of a polyoxyalkylenated fatty alcohol of formula (I) is such that: R denotes a C16-C18 alkyl radical, which is preferably linear, and R' denotes a C14 alkyl radical, which is preferably linear, substituted with an OH group, said hydroxyl radical preferably being beta to the ether function, and n is equal to 60.
- the nonionic compound of formula (I) has the following formula
- Such a compound is known, for example, in the CTFA dictionary under the name Ceteareth 60 myristyl glycol or Hydrogenated talloweth 60 myristyl glycol.
- a ceteareth 60 myristyl glycol is sold, for example, by the company Akzo under the trade name Elfacos GT 282 S.
- the nonionic polyoxyalkylenated fatty alcohol ether(s) (I) are preferably present in a content ranging from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight, preferentially from 0.075% to 2% by weight, better still from 0.01% to 1% by weight relative to the total weight of the composition.
- composition according to the invention may optionally comprise one or more additives, other than the compounds described previously, and among which mention may be made of cationic, anionic, nonionic or amphoteric polymers or mixtures thereof, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, plasticizers, solubilizers, opacifiers or nacreous agents, antioxidants, hydroxy acids, and fragrances.
- additives other than the compounds described previously, and among which mention may be made of cationic, anionic, nonionic or amphoteric polymers or mixtures thereof, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, plasticizers, solubilizers, opacifiers or nacreous agents, antioxidants, hydroxy acids, and fragrances.
- the above additives may generally be present in an amount, for each of them, of between 0 and 20% by weight relative to the total weight of the composition.
- composition according to the invention does not comprise any cationic polymers.
- the composition according to the invention also comprises one or more chemical oxidizing agents as described below. According to this embodiment, the composition is a ready-to-use composition.
- the pH of the ready-to-use composition is between 8 and 11 and preferentially between 9 and 10.5.
- the composition according to the invention does not comprise any chemical oxidizing agents.
- the composition is preferably intended for mixing with one or more chemical oxidizing agents.
- the pH of the composition not containing any chemical oxidizing agents is between 8 and 13, preferentially between 9 and 12.
- the pH of the composition not containing any chemical oxidizing agents is between 7 and 10 and the pH of the ready-to-use composition is between 6 and 9.
- the present invention also relates to a process for dyeing keratin fibres, preferably the hair, which comprises the application to said keratin fibres of an effective amount of a composition as defined previously, in the presence of an oxidizing agent.
- the composition may be applied to wet or dry keratin fibres.
- the keratin fibres are optionally rinsed with water, optionally washed with a shampoo and then rinsed with water, before being dried or left to dry.
- the process according to the invention comprises a step of mixing the previously described composition, which does not comprise any chemical oxidizing agents, with an oxidizing composition comprising at least one chemical oxidizing agent.
- This mixing step is preferably performed at the time of use, just before applying to the hair the composition resulting from the mixing.
- the ready-to-use composition preferably results from the mixing of at least two compositions:
- composition comprising:
- - at least one oxidation base chosen from 2- ⁇ -hydroxyethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof;
- an oxidizing composition comprising one or more chemical oxidizing agents, preferably hydrogen peroxide.
- the process for dyeing keratin fibres, preferably the hair, according to the invention comprises the step of applying to the keratin fibres a composition resulting from the mixing, at the time of use, of at least two compositions:
- composition comprising:
- - at least one oxidation base chosen from: 2- ⁇ -hydroxyethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-( ⁇ -hydroxypropyl)-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine and the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof;
- fatty substance other than fatty acids preferably chosen from liquid hydrocarbons comprising more than 6 carbon atoms, plant oils, liquid fatty alcohols, liquid fatty esters and waxes, and mixtures thereof;
- At least one additional surfactant preferably chosen from nonionic surfactants, more preferentially chosen from saturated or unsaturated, linear or branched, oxyethylenated or oxypropylenated, C8 to C40 alcohols comprising from 1 to 100 mol of ethylene or propylene oxide, preferably from 2 to 50, more particularly from 2 to 40 mol, and including at least one C8-C20 alkyl chain.
- - at least one sequestrant preferably chosen from N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof;
- an oxidizing composition comprising one or more chemical oxidizing agents.
- the chemical oxidizing agent(s) are chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and percarbonates of alkali metals or alkaline-earth metals, and mixtures thereof.
- the oxidizing agent is preferably chosen from hydrogen peroxide.
- the oxidizing composition is preferably an aqueous composition.
- it comprises more than 5% by weight of water, preferably more than 10% by weight of water and even more advantageously more than 20% by weight of water relative to the total weight of the oxidizing composition.
- the oxidizing composition may also comprise one or more organic solvents chosen from those listed previously; these solvents more particularly representing, when they are present, from 1% to 40% by weight and preferably from 5% to 30% by weight relative to the weight of the oxidizing composition.
- the oxidizing composition also preferably comprises one or more acidifying agents.
- the acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
- the oxidizing composition may also comprise fatty substances such as those described previously, preferably chosen from fatty alcohols, liquid hydrocarbons comprising more than 6 carbon atoms and mixtures thereof, surfactants and polymers.
- the pH of the oxidizing composition when it is aqueous, is less than 7, preferably ranging from 1.5 to 4.
- the oxidizing composition comprises hydrogen peroxide as oxidizing agent, in aqueous solution, the concentration of which ranges, more particularly, from 0.1% to 50%, more particularly between 0.5% and 20% and even more preferentially between 1% and 15% by weight, relative to the weight of the oxidizing composition.
- Another subject of the invention is a multi-compartment device, preferably comprising two compartments, for dyeing keratin fibres, preferably the hair, comprising at least a first compartment containing the dye composition according to the invention and at least a second compartment containing an oxidizing composition as described above.
- compositions of the device according to the invention are packaged in separate compartments, optionally accompanied by suitable application means, which may be identical or different, such as fine brushes, coarse brushes or sponges.
- the device mentioned above may also be equipped with a means for dispensing the desired mixture onto the hair, for instance the devices described in patent FR 2 586 913.
- the present invention relates to the use of a composition as described above, for dyeing keratin fibres, and in particular the hair.
- the dye composition A was prepared from the ingredients whose contents are indicated in the table below (% active material):
- Nonionic surfactant 2.45 Fatty acid(s)* 0.3
- Propylene glycol 2.00 Candelilla wax 0.1 Tetrasodium glutamate diacetate 0.24
- Antioxidant 1.0 Hydroxyethyl-p-phenylenediamine sulfate 1.0 N,N-Bis(2-hydroxyethyl)-p-phenyldiamine sulfate 0.17 m-Aminophenol 0.174 Hydroxybenzomorpholine 0.16 2,4-Diaminophenoxyethanol HCl 0.022 2-Amino-3-hydroxypyridine 0.21 Hydroxyethyl-3,4-methylenedioxyaniline HCl 0.22 Water/Aqua qs 100
- composition A is mixed with 1.5 times its weight of oxidizing agent O.
- the mixture is applied to locks of natural grey hair at a rate of 5 g of mixture per 1 g of hair.
- the hair is rinsed, washed with a standard shampoo and dried.
- the result obtained is a beautiful, luminous brown with intense highlights, with good coverage of grey hair and uniform colouring from root to tip.
- composition according to the invention affords good sensory performance.
- compositions A and B were prepared from the ingredients whose contents are indicated in the table below (% active material):
- a invention B comparative AMMONIUM BICARBONATE 2.50 2.50 AMMONIUM HYDROXIDE 3.29 3.29 SOLVENT 2.00 2.00 NON IONIQUE SURFACTANT 2.45 2.45 TETRASODIUM GLUTAMATE DIACETATE 0.24 0.24 FATTY ACID(S)* 0.5 - CETEARYL ALCOHOL 16 16 C15-19 ALKANE 2 2 m-AMINOPHENOL 0.17 0.17 2,4-DIAMINOPHENOXYETHANOL HCL 0.02 0.02 ANTIOXYDANT 1.00 1.00 CANDELILLA WAX 0.10 0.10 N,N-BIS(2-HYDROXYETHYL)-p-PHENYLENEDIAMINE SULFATE 0.17 0.17 HYDROXYETHYL-p-PHENYLENEDIAMINE SULFATE 1.00 1.00 HYDROXYBENZOMORPHOLINE 0.16 0.16 2-AMINO-3-HYDROXYPYRI
- each of the dye compositions A and B is mixed with 1.5 times its weight of oxidizing agent O (comprising hydrogen 6% by weight of hydrogen peroxide relative to the total weight of the oxidizing agent).
- Each of the mixtures is then applied to locks of permanent waved grey (PWG) hair containing 90% white hairs and highly sensitized hair (SA40), at a rate of 5 g of mixture/g of hair.
- PWG permanent waved grey
- SA40 highly sensitized hair
- the hair is rinsed, washed with a standard shampoo and dried.
- the colorimetric measurements were performed using a Konica Minolta 3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included) in the CIELab system.
- the dyeing selectivity is the variation of the colour between permanent waved grey (PWG) hair and highly sensitized hair (SA40).
- PWG permanent waved grey
- SA40 highly sensitized hair
- the selectivity enables evaluation of the colour homogeneity along the entire length of the hair fibre.
- the selectivity is measured by:
- L* represents the intensity and a* and b* represent the chromaticity of the dyed permanent waved grey (PWG) hair
- L0* represents the intensity and a0* and b0* represent the chromaticity of the dyed highly sensitized hair (SA40.
- SA40 highly sensitized hair
- the A+O mixture according to the invention has a ⁇ E value lower than that obtained with the comparative B+O mixture.
- the mixture according to the invention leads to lower selectivity, therefore it affords locks of hair with improved selectivity relative to those treated with the comparative mixture B+O, and consequently improved colour homogeneity from the root to the tip of the hair.
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Abstract
Description
- at least one fatty acid.
- at least one fatty acid; and
| A | |
| Ammonium hydroxide | 3.29 |
| Ammonium bicarbonate | 2.5 |
| Nonionic surfactant | 2.45 |
| Fatty acid(s)* | 0.3 |
| Cetearyl alcohol | 16 |
| C15-19 alkane | 2.00 |
| Propylene glycol | 2.00 |
| Candelilla wax | 0.1 |
| Tetrasodium glutamate diacetate | 0.24 |
| Antioxidant | 1.0 |
| Hydroxyethyl-p-phenylenediamine sulfate | 1.0 |
| N,N-Bis(2-hydroxyethyl)-p-phenyldiamine sulfate | 0.17 |
| m-Aminophenol | 0.174 |
| Hydroxybenzomorpholine | 0.16 |
| 2,4-Diaminophenoxyethanol HCl | 0.022 |
| 2-Amino-3-hydroxypyridine | 0.21 |
| Hydroxyethyl-3,4-methylenedioxyaniline HCl | 0.22 |
| Water/Aqua | qs 100 |
| A invention | B comparative | |
| AMMONIUM BICARBONATE | 2.50 | 2.50 |
| AMMONIUM HYDROXIDE | 3.29 | 3.29 |
| SOLVENT | 2.00 | 2.00 |
| NON IONIQUE SURFACTANT | 2.45 | 2.45 |
| TETRASODIUM GLUTAMATE DIACETATE | 0.24 | 0.24 |
| FATTY ACID(S)* | 0.5 | - |
| CETEARYL ALCOHOL | 16 | 16 |
| C15-19 ALKANE | 2 | 2 |
| m-AMINOPHENOL | 0.17 | 0.17 |
| 2,4-DIAMINOPHENOXYETHANOL HCL | 0.02 | 0.02 |
| ANTIOXYDANT | 1.00 | 1.00 |
| CANDELILLA WAX | 0.10 | 0.10 |
| N,N-BIS(2-HYDROXYETHYL)-p-PHENYLENEDIAMINE SULFATE | 0.17 | 0.17 |
| HYDROXYETHYL-p-PHENYLENEDIAMINE SULFATE | 1.00 | 1.00 |
| HYDROXYBENZOMORPHOLINE | 0.16 | 0.16 |
| 2-AMINO-3-HYDROXYPYRIDINE | 0.21 | 0.21 |
| HYDROXYETHYL-3,4-METHYLENEDIOXYANILINE HCL | 0.22 | 0.22 |
| WATER | QS 100 | QS 100 |
| Hair | L* | a* | b* | ΔE | |
| A + O (inv) | PWG | 20.9 | 3.87 | 3.06 | 1.63 |
| SA40 | 19.54 | 3.36 | 2.33 | ||
| B + O (comp) | PWG | 23.84 | 4.08 | 3.71 | 3.85 |
| SA40 | 20.25 | 3.35 | 2.54 |
Claims (18)
- Composition comprising:
- at least one oxidation base chosen from 2-β-hydroxyethyl-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-(γ-hydroxypropyl)-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine, the addition salts thereof, the solvates thereof and/or the solvates of salts thereof, and mixtures thereof;
- ammonium bicarbonate
- at least one fatty acid. - Composition according to the preceding claim, in which the total content of oxidation base chosen from 2-β-hydroxyethyl-para-phenylenediamine, the addition salts thereof, solvates thereof and/or solvates of salts thereof, 2-(γ-hydroxypropyl)-para-phenylenediamine, the addition salts thereof, solvates thereof and/or solvates of salts thereof, 2-methoxymethyl-para-phenylenediamine, the addition salts thereof, solvates thereof and/or solvates of salts thereof and mixtures thereof, ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, better still from 0.01% to 10% by weight, even better still from 0.05% to 5% by weight, even better still from 0.1% to 3% by weight relative to the total weight of the composition.
- Composition according to either of the preceding claims, in which the total content of ammonium bicarbonate ranges from 0.01% to 20% by weight, preferably from 0.05% to 15% by weight, preferentially from 0.1% to 10% by weight, more preferentially from 0.4% to 5% by weight, better still from 0.5% to 4% by weight, and even better still from 1% to 3% by weight, relative to the total weight of the composition.
- Composition according to any one of the preceding claims, comprising at least one additional alkaline agent, preferably chosen from ammonium hydroxide, alkanolamines, alkali metal silicates and metasilicates, mineral hydroxides and mixtures thereof, more preferentially chosen from ammonium hydroxide, alkanolamines and mixtures thereof, better still chosen from ammonium hydroxide, monoethanolamine and mixtures thereof.
- Composition according to any one of the preceding claims, in which the at least one fatty acid is(are) chosen from fatty acids including at least one carboxylic acid group and a linear or branched, saturated or unsaturated alkyl chain comprising from 10 to 30 carbon atoms, in particular from 14 to 22 carbon atoms, preferably chosen from solid fatty acids, even more preferentially chosen from palmitic acid, lauric acid, myristic acid, stearic acid and mixtures thereof, better still from palmitic acid, myristic acid, stearic acid and mixtures thereof.
- Composition according to any one of the preceding claims, in which the total content of the fatty acid(s) ranges from 0.01% to 10% by weight, more preferentially from 0.05% to 5% by weight, better still from 0.1% to 1% by weight, even better still from 0.2% to 0.5% by weight, relative to the total weight of the composition.
- Composition according to any one of the preceding claims, comprising at least one fatty substance other than fatty acids, preferably chosen from hydrocarbons comprising more than 6 carbon atoms, plant oils, liquid fatty alcohols, liquid fatty esters and waxes, and mixtures thereof, more preferentially from solid fatty alcohols, mixtures of alkanes containing from 8 to 28 carbon atoms, plant waxes, better still from cetearyl alcohol, C15-19 Alkane (INCI name), candelilla wax and mixtures thereof.
- Composition according to any one of the preceding claims, in which the total content of the fatty substance(s) other than fatty acids ranges from 5% to 35% by weight, more preferentially from 7% to 30% by weight and better still from 8% to 25% by weight relative to the total weight of the composition.
- Composition according to any one of the preceding claims, comprising at least one additional oxidation base other than the oxidation bases as defined in Claim 1.
- Composition according to any one of the preceding claims, comprising at least one coupler, preferably chosen from 6-hydroxybenzomorpholine, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, hydroxyethyl-3,4-methylenedioxyaniline, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, 2-amino-5-ethylphenol, the addition salts thereof, the solvates thereof and/or the solvates of the salts thereof, and mixtures thereof.
- Composition according to any one of the preceding claims, not comprising any oxidation couplers chosen from resorcinol, 2-methylresorcinol, 4-chlororesorcinol, addition salts thereof, solvates thereof and the solvates of the salts thereof.
- Composition according to any one of the preceding claims, comprising at least one additional surfactant, the surfactant(s) other than fatty acids preferably being chosen from nonionic surfactants, more preferentially chosen from saturated or unsaturated, linear or branched, oxyethylenated or oxypropylenated, C8 to C40 alcohols comprising from 1 to 100 mol of ethylene or propylene oxide, preferably from 2 to 50, more particularly from 2 to 40 mol, and including at least one C8-C20 alkyl chain.
- Composition according to any one of the preceding claims, comprising at least one sequestrant, preferably chosen from diethylenetriaminepentaacetic acid (DTPA) and salts thereof, diethylenediaminetetraacetic acid (EDTA) and salts thereof, ethylenediaminedisuccinic acid (EDDS) and salts thereof, etidronic acid and salts thereof, N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof, and mixtures thereof, more preferentially from N,N-dicarboxymethylglutamic acid (GLDA) and salts thereof, and mixtures thereof.
- Composition according to any one of the preceding claims, not comprising any chemical oxidizing agent.
- Composition according to any one of Claims 1 to 13, comprising at least one chemical oxidizing agent, preferably hydrogen peroxide.
- Process for dyeing keratin fibres, preferably the hair, comprising the application to the keratin fibres of the composition as defined according to Claim 14.
- Process according to Claim 15, comprising the application to the fibres of a mixture of:
a) a composition according to any one of Claims 1 to 14,
b) an oxidizing composition comprising one or more chemical oxidizing agents, preferably hydrogen peroxide. - Multi-compartment device, preferably a two-compartment device, for dyeing keratin fibres, preferably the hair, comprising at least a first compartment containing a composition as defined according to any one of Claims 1 to 14 and at least a second compartment containing an oxidizing composition comprising one or more chemical oxidizing agents, preferably hydrogen peroxide.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202480042636.4A CN121398784A (en) | 2023-06-30 | 2024-06-27 | Composition comprising specific base ammonium bicarbonate and fatty acid |
| EP24737909.2A EP4734917A1 (en) | 2023-06-30 | 2024-06-27 | Composition comprising a particular base ammonium bicarbonate and fatty acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FRFR2306939 | 2023-06-30 | ||
| FR2306939A FR3150429A1 (en) | 2023-06-30 | 2023-06-30 | Composition comprising a particular base and ammonium bicarbonate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2025003345A1 true WO2025003345A1 (en) | 2025-01-02 |
Family
ID=88291034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2024/068160 Ceased WO2025003345A1 (en) | 2023-06-30 | 2024-06-27 | Composition comprising a particular base ammonium bicarbonate and fatty acid |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP4734917A1 (en) |
| CN (1) | CN121398784A (en) |
| FR (1) | FR3150429A1 (en) |
| WO (1) | WO2025003345A1 (en) |
Citations (21)
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|---|---|---|---|---|
| GB1026978A (en) | 1962-03-30 | 1966-04-20 | Schwarzkopf Verwaltung G M B H | Method of dyeing hair |
| GB1153196A (en) | 1965-07-07 | 1969-05-29 | Schwarzkopf Verwaltung G M B H | Method of Dyeing Hair |
| DE2359399A1 (en) | 1973-11-29 | 1975-06-12 | Henkel & Cie Gmbh | Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes |
| FR2586913A1 (en) | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
| DE3843892A1 (en) | 1988-12-24 | 1990-06-28 | Wella Ag | OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES |
| JPH0563124A (en) | 1991-09-03 | 1993-03-12 | Mitsubishi Electric Corp | Hybrid integrated circuit device |
| DE4133957A1 (en) | 1991-10-14 | 1993-04-15 | Wella Ag | HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES |
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| WO1996015765A1 (en) | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
| FR2733749A1 (en) | 1995-05-05 | 1996-11-08 | Oreal | COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF |
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| JP2013169571A (en) | 2012-02-21 | 2013-09-02 | Nippon Steel & Sumitomo Metal Corp | Method of manufacturing forged steel roll |
| US20150283053A1 (en) * | 2014-04-02 | 2015-10-08 | The Procter & Gamble Company | Hair Colouring Compositions, Kits, Method, and Use Thereof |
| FR3124707A1 (en) * | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, propane-1,3-diol, at least one alkaline agent and at least one fatty substance. |
| FR3124708A1 (en) * | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol. |
| FR3130152A1 (en) * | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising two particular oxidation coloring precursors and a phosphoric surfactant. |
| FR3130151A1 (en) * | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising a particular oxidation coloring precursor, an oxyalkylenated fatty alcohol and a polysaccharide. |
-
2023
- 2023-06-30 FR FR2306939A patent/FR3150429A1/en active Pending
-
2024
- 2024-06-27 CN CN202480042636.4A patent/CN121398784A/en active Pending
- 2024-06-27 WO PCT/EP2024/068160 patent/WO2025003345A1/en not_active Ceased
- 2024-06-27 EP EP24737909.2A patent/EP4734917A1/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1026978A (en) | 1962-03-30 | 1966-04-20 | Schwarzkopf Verwaltung G M B H | Method of dyeing hair |
| GB1153196A (en) | 1965-07-07 | 1969-05-29 | Schwarzkopf Verwaltung G M B H | Method of Dyeing Hair |
| DE2359399A1 (en) | 1973-11-29 | 1975-06-12 | Henkel & Cie Gmbh | Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes |
| FR2586913A1 (en) | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
| DE3843892A1 (en) | 1988-12-24 | 1990-06-28 | Wella Ag | OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES |
| JPH0563124A (en) | 1991-09-03 | 1993-03-12 | Mitsubishi Electric Corp | Hybrid integrated circuit device |
| DE4133957A1 (en) | 1991-10-14 | 1993-04-15 | Wella Ag | HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES |
| WO1994008969A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives |
| WO1994008970A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production |
| WO1996015765A1 (en) | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
| FR2733749A1 (en) | 1995-05-05 | 1996-11-08 | Oreal | COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF |
| EP0770375A1 (en) | 1995-10-21 | 1997-05-02 | GOLDWELL GmbH | Hair dyeing composition |
| DE19543988A1 (en) | 1995-11-25 | 1997-05-28 | Wella Ag | Oxidative hair dye composition |
| FR2801308A1 (en) | 1999-11-19 | 2001-05-25 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING 3-AMINO PYRAZOLO- [1, (- a] -PYRIDINES, DYEING PROCESS, NOVEL 3-AMINO PYRAZOLO- [1,5-a] -PYRIDINES |
| FR2886136A1 (en) | 2005-05-31 | 2006-12-01 | Oreal | COMPOSITION FOR DYING KERATIN FIBERS COMPRISING AT LEAST ONE DIAMINO-N, N-DIHYDRO-PYRAZOLONE DERIVATIVE AND A CATIONIC OXIDATION DYE |
| JP2013169571A (en) | 2012-02-21 | 2013-09-02 | Nippon Steel & Sumitomo Metal Corp | Method of manufacturing forged steel roll |
| US20150283053A1 (en) * | 2014-04-02 | 2015-10-08 | The Procter & Gamble Company | Hair Colouring Compositions, Kits, Method, and Use Thereof |
| FR3124707A1 (en) * | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, propane-1,3-diol, at least one alkaline agent and at least one fatty substance. |
| FR3124708A1 (en) * | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol. |
| FR3130152A1 (en) * | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising two particular oxidation coloring precursors and a phosphoric surfactant. |
| FR3130151A1 (en) * | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising a particular oxidation coloring precursor, an oxyalkylenated fatty alcohol and a polysaccharide. |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4734917A1 (en) | 2026-05-06 |
| FR3150429A1 (en) | 2025-01-03 |
| CN121398784A (en) | 2026-01-23 |
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