[go: up one dir, main page]

WO2025031977A1 - Procédé permettant de produire des colorants capillaires - Google Patents

Procédé permettant de produire des colorants capillaires Download PDF

Info

Publication number
WO2025031977A1
WO2025031977A1 PCT/EP2024/071987 EP2024071987W WO2025031977A1 WO 2025031977 A1 WO2025031977 A1 WO 2025031977A1 EP 2024071987 W EP2024071987 W EP 2024071987W WO 2025031977 A1 WO2025031977 A1 WO 2025031977A1
Authority
WO
WIPO (PCT)
Prior art keywords
xanthan gum
cosmetic composition
suspension
mix
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2024/071987
Other languages
English (en)
Inventor
Gunther AUGENSTEIN
Christian ADER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratoire Biosthetique Kosmetik & Co KG GmbH
Original Assignee
Laboratoire Biosthetique Kosmetik & Co KG GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratoire Biosthetique Kosmetik & Co KG GmbH filed Critical Laboratoire Biosthetique Kosmetik & Co KG GmbH
Publication of WO2025031977A1 publication Critical patent/WO2025031977A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/49—Solubiliser, Solubilising system

Definitions

  • the invention relates to a process for preparing a coloring cream for bleaching or coloring keratin fibers by introducing a novel Xanthan gum suspension as a pre-mix at any process step. Further, a Xanthan gum suspension for use in the process, a cosmetic composition comprising the Xanthan gum suspension, a kit for dyeing or bleaching keratin fibers and a ready-to-use mixture obtainable by mixing the kit components are described.
  • Oxidative dyes comprise one or more precursors of oxidative dyes, so-called primary intermediates, and one or more color coupling agents to obtain the desired shades. These compounds are small aromatic molecules being able to diffuse in the hair shaft where, once activated by atmospheric oxygen or an oxidizing agent, they further react with other precursors to form larger colored molecules.
  • compositions comprising primary intermediates and couplers are normally activated by mixing with an oxidant, commonly referred to as a "developer” or “activator.” Hydrogen peroxide is the most commonly used activator these days.
  • oxidant commonly referred to as a "developer” or “activator.” Hydrogen peroxide is the most commonly used activator these days.
  • the thus-obtained ready-to-use compositions are subsequently applied to the keratin fibers for a certain period of time, during which the dye(s) is (are) formed.
  • An important group of these specific cosmetic compositions are present in a cream-like state at the temperature of application (this is typically between 20 - 35°C).
  • the primary intermediates employed in these cosmetic compositions are usually derivatives of benzene, e.g.
  • color coupling agents are resorcinols, m-aminophenols, m-phenylenediamines, 1- naphthols, and di-, tri- and tetra-substituted pyridines.
  • the cosmetic compositions based on oxidative dyes are usually manufactured and provided as two component kits, wherein one kit component has a basic pH and comprises the primary intermediates and the color coupling agents.
  • the second kit component comprises a hydrogen peroxide composition which is usually stabilized by an amount of phosphoric acid.
  • both kit components are preferentially provided in cream- or gel-like form.
  • a ready- to-use compositions is produced by mixing both kit components either by stirring in a bowl or by shaking in a container, e.g. a bottle or a jar.
  • the ready-to-use mixture is then applied to the hair by means of a brush or another applicator tool.
  • coloring mixtures have a certain higher viscosity in order to prevent dripping during the treatment of the hair.
  • kits for oxidative coloring of hair are normally achieved by ready- to-use mixtures which are adjusted to a pH in the range of from 9.0 to 10.5.
  • the kit components are mixed directly prior to application to the hair in a ratio of from 1 :1 to 1 :3 by weight.
  • the resulting mixture is then applied to the hair by means of a brush or another applicator tool.
  • a common configuration of cosmetic compositions in a cream-like form comprises at least long chain fatty alcohols, water and one or more emulsifiers to achieve thus cream-like consistency. Thereby, the choice of the emulsifier system strongly determines the properties of the creams.
  • modem cream-like compositions which are particularly salt tolerant, comprise for instance combinations of long-chain C12 to C30 fatty alcohols and phosphate ester emulsifiers.
  • the emulsifiers are for instance: i) monoester phosphates of alkoxylated fatty alcohols, wherein the alkox- ylated fatty alcohols are composed of C12 to C22 fatty alcohols alkoxylated with from 1 to 50 moles of an alkylene oxide, wherein the number of moles of alkylene oxide is with respect to the moles of fatty alcohol; ii) diester phosphates of non-alkoxylated fatty alcohols, wherein the non- alkoxylated fatty alcohols are composed of C12-C22 fatty alcohols; iii) organic phosphate ester compound selected from mono- and diacyl or alkyl substituted polyglycerol derivatives of phosphoric acid as mentioned below.
  • phosphate ester emulsifiers are for instance Dicetyl Phosphate and Ceteth-10 Phosphate as described by US 6, 117,915A.
  • Commercial are blends of both emulsifiers and Cetearyl Alcohol, called Crodafos CES (available from Croda GmbH, 41334 Nettetal, Germany).
  • phosphate ester emulsifiers are Oleth-5 Phosphate (and) Dioleyl Phosphate called Crodafos HCE, Potassium Cetyl Phosphate (available from local distributors DSM and Croda), as well as Polyglyceryl-3 Rice Branate Phosphate, Polyglyceryl-4 Stearate Phosphate (available from Socri, via Majocchi, 13/B, 27020 Torre d’Isola, Italy), Polyglyceryl-3 Oleyl Ether Phosphate, and Polyglyceryl-4 Sorbity I Ether Olivate Phosphate.
  • compositions comprising a combination of dicetylphosphate, ceteth-10 phosphate and fatty alcohols were found to be able to absorb a wide range of ingredients such as polymers, salts and oils, even all at once, without necessarily tending towards instability.
  • these complex and salt loaded cosmetic compositions often comprise Xanthan gum and propylene glycol.
  • propylene glycol While the use of propylene glycol is approved for different applications such as solvent or plasticizer in household products, as food additive or as ingredient of personal care products and pharmaceutical preparations, there are reports that skin exposure may cause skin-sensitizing and irritations (see Lessmann, H.; Schnuch, A.; Geier, J.; liter, W.; "Skin-sensitizing and irritant properties of propylene glycol", Contact Dermatitis, 2005, 53, 247-259 or Al Jasser, M.; Mebuke, N.; de Gannes, G.; “Propylene glycol: an often unrecognized cause of allergic contact dermatitis in patients using topical corticosteroids”, Skin Therapy Lett., 2011 16(5), 5-7).
  • Xanthan Gum may be added in a premixed form to the other components.
  • aqueous premixes of Xanthan gum for hair cosmetic composition is described in EP 2 979 683 B1.
  • aqueous concentrates of Xanthan gum are not convenient considering that these mixtures are extremely viscous and therefore hardly manageable.
  • Xanthan gum premixes are used. Another advantage is that the Xanthan gum/propylene glycol mixtures do not thicken as rapidly as, e.g., Xanthan gum/glycerol mixtures. However, this does not completely eliminate the disadvantages of using propylene glycol.
  • This object is solved by a process with the features of claim 1 .
  • the process for preparing a coloring cream for bleaching or coloring keratin fibers wherein a premix is admixed at any step in the manufacture of this cream.
  • This pre-mix is a suspension of Xanthan gum in at least one non-ionic emulsifier of the formula
  • suspensions of Xanthan gum in at least one non-ionic emulsifier of formula (I) or formula (II) allowed the preparation of stable cosmetic compositions for bleaching or coloring keratin fibers such as human hair using Xanthan gum as stabilizing agent and thickener, particularly for a coloring cream.
  • the coloring cream contains further at least one fatty alcohol with an alkyl chain featuring 12 to 30 C-atoms. While fatty alcohols provide thickening and stabilization, xanthan gum increases the viscosity of the aqueous phase and contributes to preventing the coalescence of droplets.
  • the non-ionic emulsifiers improve the formation and stability of the emulsion.
  • the combination of fatty alcohol, xanthan gum, and a non-ionic emulsifier results in a synergistic effect for a stable and viscous emulsion with enhanced texture and increased shelf life. This effect is particularly high when the fatty alcohol is already added to the premix as it stabilizes the pre-mix and prevents clumping.
  • the fatty alcohol is added in an amount of 3 to 50 wt.-%, which leads to a particularly high stability of the suspension.
  • the non-ionic emulsifiers of formula (I) and formula (II) are liquid at 20 to 25°C, which allows easy suspending Xanthan gum at ambient temperature. Surprisingly, it was found that according to Griffin’s HLB scale (hydrophilic-lipophilic balance) these non-ionic emulsifiers fall in the general range of between 6.0 and 10.0 and thus, are pronounced water-in-oil emulsifiers (W/O-emulsifiers) or wetting agents. However, such water-in-oil emulsifiers are not obvious coemulsifiers of oil-in-water compositions such as cosmetic hair compositions, especially when the latter are based on phosphate ester emulsifiers. Particular suitable suspensions are obtained with non-ionic emulsifiers of formula (I) and/or (II) having an HLB value between 6.0 and 8.0.
  • the Xanthan gum suspension is prepared by addition of Xanthan gum to the at least one non-ionic emulsifier under stirring.
  • the suspension is prepared at ambient temperature. Therefore, only readily available low-cost equipment and a minimum of effort are required to obtain the Xanthan gum suspension.
  • the suspension may not only be prepared immediately prior to the preparation of the cosmetic composition but also multiple hours or days in advance since the suspension's properties were found to remain unchanged even after storing periods of up to a week and longer.
  • the coloring cream comprises preferably a non-ionic emulsifier selected from polyoxyethylene alkyl ethers with an alkyl chain featuring 14 to 30 C- atoms and at least 20, preferably 20 to 100 ethylene oxide units and/or one or more anionic emulsifiers.
  • a non-ionic emulsifier selected from polyoxyethylene alkyl ethers with an alkyl chain featuring 14 to 30 C- atoms and at least 20, preferably 20 to 100 ethylene oxide units and/or one or more anionic emulsifiers.
  • the one or more anionic emulsifiers are selected from alkoxylated fatty alcohol phosphate monoesters, wherein the alkoxylated fatty alcohols are composed of fatty alcohols featuring an alkyl chain of 12 to 22 C-atoms and are alkoxylated with 1 to 50 units of an alkylene oxide, non-alkoxylated fatty alcohol phosphate diesters, wherein the non-alkoxylated fatty alcohols are composed of fatty alcohols featuring an alkyl chain of 12 to 22 C-atoms, organic phosphate ester compounds selected from mono- and diacyl or -alkyl substituted polyglycerol derivatives of phosphoric acid or mixtures thereof.
  • Particularly stable cosmetic compositions that may comprise a broad variety of different neutral or ionic, hydrophilc or lipophilic compounds without being prone to syneresis, are obtained in combination with the inventive Xanthan gum suspension.
  • Particularly preferred organic phosphate ester compounds are oleth-5 phosphate (and) dioleyl phosphate referred to as "Crodafos HCE", potassium cetyl phosphate (available from local distributors DSM and Croda GmbH), as well as plyglyceryl-3 rice branate phosphate, plyglyceryl-4 stearate phosphate (available from Socri, via Majocchi, 13/B, 27020 Torre d’Isola, Italy), polyglyceryl-3 oleyl ether phosphate, and polyglyceryl-4 sorbityl ether olivate phosphate among others.
  • hydrophilic compounds may be included in (overall) hydrophilic components and lipophilic compounds in (overall) lipophilic components.
  • an aqueous solution comprising a buffering agent and/or a base is admixed in any order.
  • the pH value of the resulting cosmetic composition can be adapted to a desired value since the composition's (coloration) performance greatly depends on its pH value.
  • the charge state of other constituents and consequently their solubility may be changed by adapting the pH value accordingly.
  • the ratio of the individual components is selected such that the concentration of the individual compounds falls into the respective concentration ranges provided below.
  • the pre-mix is admixed with water in a first process step.
  • the aqueous component which may account for the major constituent of the resulting cosmetic composition in terms of weight, may be present as base to which the further components are consecutively added.
  • the early addition of the Xanthan suspension may facilitate the admixing of the further components, despite a beginning increase in viscosity due to the hydration of Xanthan in presence of water.
  • the sequence of admixing the Xanthan suspension to other cream components does not significantly affect the properties of the final cosmetic composition, emphasizing that components may be mixed in any order. In this context, it should be emphasized that this effect does not generally occur with the addition as a Xanthan mixture, but specifically with the addition as a suspension.
  • the introduction of the pre-mix occurs at a temperature between 35 and 95 °C, preferably between 65 to 85 °C, particularly preferred 70 to 80 °C, with stirring. It was found that elevated temperatures facilitate homogenization of the mixture. Thereby, higher temperatures, especially the respective preferred temperature ranges, are particularly suited.
  • the temperature should be adjusted such that evaporation is prevented or limited during the mixing of the components. Therefore, individual components may be added at different temperatures. In this aspect, it is particularly preferred to add an aqueous ammonia solution, preferably at a temperature range between 25 and 50°C to avoid excessive evaporation. Additionally or alternatively, evaporation may be reduced or prevented by using a closed and/or pressurized reaction system.
  • stirring may be effected by any suitable means in dependency of respective reaction system used.
  • Suitable stirrers may be for example propeller stirrers, discoidal stirrers, impeller stirrers, rigid paddle or rigid blade stirrers.
  • Homogeni- zation may further be improved by utilizing ultrasonic waves or high-shear mixers.
  • the pre-mix is admixed sequentially, and the resulting mixture is further homogenized by stirring for an additional 1 to 20 minutes depending on the batch size, preferably 5 to 10 minutes after each sequential mixing step.
  • a mixing step ends once a component has been fully added to the mixture. Further homogenization improves the cosmetic composition's quality since locally high concentrations of individual components in the composition are avoided.
  • the temperature of the (intermediate) mixture or cosmetic composition, respectively may be adjusted to the desired range during this homogenization period.
  • the process is conducted batchwise.
  • a batchwise preparation greatly facilitates the process control, in particular homogenization.
  • any suitable mixing vessel may be employed.
  • the mixing vessel comprises means for heating and cooling, stirring and homogenizing to improve the process control as described above.
  • the invention further relates to a suspension comprising Xanthan gum and at least one non-ionic emulsifier of the formula
  • the Xanthan gum suspension may not only comprise a single non-ionic emulsifier of formula (I) or (II) as suspension medium but also a mixture of the non- ionic emulsifiers of formula (I) and/or (II).
  • the Xanthan gum suspension consists solely of Xanthan gum and the respective non-ionic emulsifier or mixture of non-ionic emulsifiers of formula (I) and/or (II), i.e. , the suspension comprises no further constituents, in particularly not propylene glycol or other glycols.
  • the suspensions were found to be most convenient in terms of mid- to long-term stability.
  • the Xanthan gum amount in the suspension may be 10 to 50 wt.-%, preferably 20 to 30 wt.-% based on the total weight of the suspension. Within this concentration range useful suspensions are obtained. If the suspended Xanthan gum settles over time, the settled particles may simply be resuspended by stirring and/or shaking prior to use.
  • the invention further relates to a cosmetic composition comprising water, at least one fatty alcohol with an alkyl chain featuring 12 to 30 C-atoms that further comprises a previously formed suspension of Xanthan gum and at least one non-ionic emulsifier of the formula
  • said composition further contains at least one fatty alcohol with an alkyl chain featuring 12 to 30 C-atoms.
  • Xanthan gum is present in a concentration between 0.1 to 5.0 wt.-%, preferably 0.5 to 2.5 wt.-% based on the total weight of the cosmetic composition. Xanthan gum not only allows adjusting the cosmetic composition's consistency but also prevents efficiently from syneresis.
  • the at least one non-ionic emulsifier according to the formula (I) or formula (II) is present in a concentration between 0.1 to 5.0 wt.-%, 1 .0 to 3.0 wt.-% based on the total weight of the cosmetic composition.
  • non-ionic emulsifiers of formula (I) or formula (II) replace propylene glycol as suspension medium in the Xanthan gum suspension
  • propylene glycol and other glycols may be present as further constituents of the cosmetic composition for bleaching or coloring keratin fibers in a preferred embodiment in a concentration of 0.1 to 10 wt.-%, preferably 0.5 to 2.5 wt.-%, of the total weight of the cosmetic composition.
  • the cosmetic composition comprises a non-ionic emulsifier selected from polyoxyethylene alkyl ethers with an alkyl chain featuring 14 to 30 C-atoms and at least 20, preferably 20 to 100 ethylene oxide units and/or one or more anionic emulsifiers as described above.
  • a non-ionic emulsifier selected from polyoxyethylene alkyl ethers with an alkyl chain featuring 14 to 30 C-atoms and at least 20, preferably 20 to 100 ethylene oxide units and/or one or more anionic emulsifiers as described above.
  • the at least one fatty alcohol with an alkyl chain featuring 12 to 30 C- atoms accounts for 3 to 50 wt.-%, preferably 5 to 25 wt.-% of the total weight of cosmetic composition.
  • further emulsifiers such as a non-ionic emulsifier selected from polyoxyethylene alkyl ethers with an alkyl chain featuring 14 to 30 C- atoms and at least 20 and/or one or more anionic emulsifiers are present, the given concentration ranges apply to the sum of the emulsifiers. Thereby, particularly stable cosmetic compositions are obtained.
  • water is present in a concentration of between 10 to 90 wt.-%, preferably between 30 to 80 wt.-%, most preferably 50 to 70 wt.-% of the total weight of the cosmetic composition.
  • a cosmetic composition of the current invention optionally comprises at least one oxidative dye precursor and/or at least one direct dye.
  • Suitable primary intermediates for use in hair dyeing compositions include, but are not limited to: toluene-2,5-diamine, p-phenylenediamine, N-phenyl-p- phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2- hydroxyethyl-p-phenylenediamine, hydroxypropyl-bis-(N-hydroxyethyl-p- phenylenediamine), 2-methoxymethyl-p-phenylenediamine, 2-(1 ,2- dihydroxyethyl)-p-phenylenediamine, 2,2’-(2-(4- aminophenylamino)ethylazanediyl)diethanol, 2-(2,5-diamino-4- methoxyphenyl)propane-1 ,3-diol, 2-(7-amino-2H-benzo[b][1 ,4]oxazin-4
  • Suitable couplers are selected from the group consisting of; resorcinol, 4- chlororesorcinol, 2-chlororesorcinol, 2-methylresorcinol, 4,6-dichlorobenzene- 1 ,3-diol, 2, 4-dimethylbenzene-1 ,3-diol, m-aminophenol, 4-amino-2- hydroxytoluene, 2-methyl-5-hydroxyethylaminophenol, 3-amino-2,6- dimethylphenol, 3-amino-2,4-dichlorophenol, 5-amino-6-chloro-o-cresol, 5- amino-4-chloro-o-cresol, 6-hydroxybenzomorpholine, 2-amino-5-phenylphenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 2-amino-5-ethoxyphenol, 5- methyl-2-(methylamino)phenol, 2,4-diaminophenoxyethanol, 2-amino-4- hydroxye
  • these cosmetic compositions for the oxidative dyeing of keratin fibers comprise primary intermediates and couplers from 0.1 to 10.0 wt.-%, preferably from 0.3 to 6.0 wt.-%, more preferably from 0.5 to 4.0 wt.- % by weight.
  • the stated quantities refer to the total amount of primary intermediates and couplers,
  • the hair dyeing compositions of the present invention may also comprise compatible direct dyes, in an amount sufficient to provide additional coloring, particularly with regard to intensity.
  • an amount in the cosmetic compositions will range from 0.05 to 4 wt.-%, by weight of the direct dyes relative to the total weight of the composition.
  • Acid dyes such as Acid Yellow 1 , Acid Orange 3, Acid Black 1 , Acid Black 52, Acid Orange 7, Acid Red 33, Acid Yellow 23, Acid Blue 9, Acid Violet 43, HC Blue 16, Acid Blue 62, Acid Blue 25, Acid Red 4;Basic Dyes such as Basic Brown 17, Basic Red 118, Basic Orange 69, Basic Red 76, Basic Brown 16, Basic Yellow 57, Basic Violet 14, Basic Blue 7, Basic Blue 26, Basic Red 2, Basic Blue 99, Basic Yellow 29, Basic Red 51 , Basic Orange 31 , Basic Yellow 87, 4-(3-(4-am ino-9, 10-dioxo-9, 10-dihydroanthracen-1 -ylam ino)propyl)-4- methylmorpholin-4-ium-methylsulfate, (E)-1 -(2-(4-(4,5-dimethylthiazol-2- yl)diazenyl)phenyl)(ethyl)amino)ethyl)-3-methyl-1 H-imidazol-3-iumchloride, (E)- 4-(
  • Disperse Dyes such as Disperse Red 17, Disperse Violet 1 , Disperse Red 15, Disperse Black 9, Disperse Blue 3, Disperse Blue 23, Disperse Blue 377;
  • Nitro Dyes such as 1 -(2-(4-nitrophenylamino)ethyl)urea, 2-(4-methyl-2- nitrophenylamino)ethanol, 4-nitrobenzene-1 ,2-diamine, 2-nitrobenzene-1 ,4- diamine, Picramic acid, HC Red No. 13, 2,2’-(2-nitro-1 ,4- phenylene)bis(azanediyl)diethanol, HC Yellow No. 5, HC Red No. 7, HC Blue No.2, HC Yellow No. 4, HC Yellow No. 2, HC Orange No. 1 , HC Red No. 1 , 2-(4- amino-2-chloro-5-nitrophenylamino)ethanol, HC Red No.
  • the cosmetic compositions according to the current invention comprise at least one further compound selected from the group of pH modifiers, buffering agents, chelants, thickeners and conditioning agents. These compounds may be used to further adapt the cosmetic composition to the respective purpose.
  • the pH modifier and/or buffering agent may be present in an amount that is sufficiently effective to adjust the pH of the cosmetic composition to fall within a range from 3 to 13, preferably from 6 to 12, more preferably from 9 to 11.
  • For dyeing compositions best coloration results are achieved under alkaline conditions, i.e. , at a pH value of 8 to 12, preferably 9 to 11 .
  • any alkalizing agent known in the art may be used as pH modifier and/or buffering agent.
  • Preferred compounds are ammonia, alkanolamines such as monoethanolamine, diethanolamine, triethanolamine, monopropanolamine, dipropanolamine, tripropanolamine, 2-amino-2-methyl-1 ,3-propanediol, 2-amino- 2-methyl-1 -propanol, and 2-amino-2-hydroxymethyl-1 ,3-propanediol, amino acids and salts thereof, guanidinium salts, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal and ammonium carbonates, and mixtures thereof. Particularly preferred are ammonia and/or alkanolamines as well as alkali salts of amino acids.
  • the cosmetic compositions in particular cosmetic compositions for oxidative dyeing of keratin fibers, comprise from 0.1 to 10 wt.-%, preferably from 0.5 to 6 wt.-%, more preferably from 1.0 to 4.0 wt.-% of the total weight of the cosmetic composition.
  • one or more thickeners may be present in an amount sufficient to provide the cosmetic composition with a viscosity so that it can be readily applied to the hair without unduly dripping off the hair and causing mess.
  • an amount will be at least 0.05 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 0.75 wt.-% of the total weight of the composition.
  • Preferred upper limits may be 5.0 wt.-%, preferably 2.0 wt.-%, more preferably 1 .0 wt.-% of the total weight of the composition.
  • the thickener may be present in any of the components.
  • Preferred are salt tolerant thickeners including but not limited to: guar, hydroxypropyl guar, scleroglucan, methylcellulose, ethylcellulose (available as AQUACOTETM), hydroxyethyl cellulose (available as NATROSOLTM), carboxymethyl cellulose, hydroxypropylmethyl cellulose, microcrystalline cellulose, hydroxybutylmethyl cellulose, hydroxypropyl cellulose (available as KLUCELTM), hydroxyethyl ethyl cellulose, cetyl hydroxyethyl cellulose (available as NATROSOLTM Plus 330), N-vinylpyrollidone (available as POVIDONETM), acrylates/Ceteth-20 Itaconate copolymer (available as STRUCTURETM 3001 ), hydroxypropyl starch phosphate (available as STRUCTURETM ZEA), polyethoxylated urethanes or polycarbamyl polyglycol ester (e.g.,
  • PEG-150/Decyl/SMDI copolymer available as ACULYNTM 44
  • PEG-150/Stearyl/SMDI copolymer available as ACULYNTM 46
  • acrylatesBeheneth-25 Methacrylate Copolymer available as ACULYNTM 28
  • acrylates/vinyl neodecanoatecrosspolymer available as ACULYNTM 38
  • acrylates/Steareth-20 methacrylate crosspolymer available as ACULYNTM 88
  • PEG-150 Distearate available as ACULYNTM 60
  • trihydroxystearin available as THIXCINTM
  • acrylates copolymer e.g.
  • ACULYNTM 33 or hydro- phobically modified acrylate copolymers (e.g. Acrylates/Steareth-20 Methacrylate Copolymer (available as ACULYNTM 22), non-ionic amphophilic polymers comprising at least one fatty chain and at least one hydrophilic unit selected from polyether urethanes comprising at least one fatty chain.
  • hydro- phobically modified acrylate copolymers e.g. Acrylates/Steareth-20 Methacrylate Copolymer (available as ACULYNTM 22)
  • non-ionic amphophilic polymers comprising at least one fatty chain and at least one hydrophilic unit selected from polyether urethanes comprising at least one fatty chain.
  • the cosmetic compositions are present in a gel-like, cream-like or foam-like state at the temperature of application, which is typically between 20 to 35°C.
  • Typical cream-like compositions in particular freshly produced and highly salt- loaded cream compositions, have a viscosity below the target viscosity. Upon standing, the viscosity gradually increases until reaching a certain plateau corresponding to the desired target viscosity. This process takes normally up to a few days depending on the specific composition and salt load.
  • the cosmetic compositions of the present invention may comprise chelants in an amount sufficient to reduce the amount of metal ions available to interact with other formulation components.
  • Suitable chelants for use herein include but are not limited to: etylenediaminetet- raacetic acid (EDTA), diethylenetriamine-N,N’,N"-polyacids, diethylenetriaminepentaacetic acid (DTPA), diethylenetriaminepenta(methylene phosphonic acid) (DTPMP), diamine-N,N’-dipolyacid, monoaminemonoamide-N,N’-dipolyacid, and N,N’-bis(2-hydroxybenzyl)ethylenediamine-N,N’-diacetic acid chelants (EDDS (ethylenediaminedisuccinic acid)), carboxylic acids (preferably aminocarboxylic acids), phosphonic acids (preferably aminophosphonic acids) and polyphosphoric acids, their salts and derivatives.
  • EDTA etylenediaminetet- raacetic acid
  • DTPA diethylenetriaminepentaacetic acid
  • DTPMP diethylenetriamine
  • chelants are present in a concentration between 0.15 to 2.0 wt.-%, preferably at least 0.25 to 1 .0 wt.-% of the total weight of the composition.
  • the cosmetic composition comprises at least one conditioning agent.
  • Suitable conditioning agents are preferably selected from silicone materials, aminosilicones, polymeric resins, polyol carboxylic acid esters, cationic polymers such as compounds being commercially available under the name “Polyquaternium”, cationic surfactants such as compounds being commercially available under the name “Quaternium” as well as quaternary surfactants such as Behentrimonium chloride and/or Behentrimonium methosulfate, Cetrimonium chloride, Stearalkonium chloride, insoluble oils and oil derived materials and mixtures thereof. Additional materials include mineral oils and other oils such as squalane and squalene, glycerin and sorbitol.
  • Preferred conditioning agents are cationic polymers.
  • the cosmetic compositions are used in combination with a composition comprising at least on conditioning agent, i.e. , without admixing the conditioning agent to the cosmetic composition during its preparation process.
  • the conditioning agent may be present in a concentration of between 0.05 to 20.0 wt.-%, preferably of between 0.1 to 15.0 wt.-%, more preferably of between 0.2 to 10.0 wt.-%, most preferably of between 0.2 to 2.0 wt.-% of the total weight of the composition.
  • the invention further relates to a kit for dyeing or bleaching keratin fibers, comprising at least two separate kit components, wherein the first kit component comprises a cosmetic composition as described above and the second kit component comprises an oxidizing agent.
  • a cosmetic composition based on oxidative dyes as a first kit component and a second kit component comprising an oxidizing agent, i.e., the activator or developer, is required to prevent a premature formation of the final dye due to a reaction oxidative dye precursors in presence of an oxidant.
  • the second kit component comprises an aqueous solution of hydrogen peroxide or its addition compounds of urea, melamine, sodium borate or sodium carbonate as oxidant.
  • concentration of respective oxidant is between 2 to 12 wt.-%, preferably 6 to 9 wt.-% of the total weight of the second kit component.
  • the kit may further comprise at least one conditioning agent as described above as a separate third kit component.
  • the conditioning agent may be present in a concentration of between 0.05 to 20.0 wt.-%, preferably of between 0.1 to 15.0wt.-%, more preferably of between 0.2 to 10.0 wt.-%, most preferably of between 0.2 to 2.0 wt.-% of the total weight of the third kit component.
  • the present invention also relates to a ready-to-use composition obtainable by mixing the at least the first and second kit component.
  • the oxidant comprised in the second kit component activates the oxidative dye precursors in the first component such that the corresponding dye is formed.
  • the ready-to-use composition comprises the first and second kit component in a ratio of between 1 :1 and 1 :3 by weight.
  • the ready-to-use composition has a pH value of 8.0 to 11.0, preferably of 9.0 to 10.5, since optimum results in the oxidative coloring of keratin fibers are achieved in this pH range.
  • the oxidant is present in the ready-to-use compositionin a concentration of between 0.1 to 12 wt.-%, preferably of between 0.5 to 10.0wt.-%, more preferably of between 1 .0 to 8.0 wt.-% of the total weight of the ready-to-use composition.
  • the ready-to-use composition may further comprise at least one conditioning agent in an effective concentration.
  • Said conditioning agent may be comprised in the first kit component and/or the third kit component.
  • the at least one conditioning agent is present in the ready-to-use composition in a concentration of between 0.05 to 20.0 wt.-%, preferably of between 0.1 to 15.0 wt.-%, more preferably of between 0.2 to 10.0 wt.-%, most preferably of between 0.2 to 2.0 wt.-% of the total weight of the ready-to-use composition.
  • a third kit component comprising at least one conditioning agent may be used separately from the ready-to-use composition, i.e., in a step preceding and/or following the application of the ready-to-use composition.
  • the invention further relates to a process for coloring or bleaching keratin fibers, comprising the steps of providing keratin fibers and applying the ready-to-use composition as described above on the keratin fibers.
  • the ready-to-use composition is prepared immediately before use, i.e., its application to the keratin fibers, by mixing of at least the first and second kit component.
  • the keratin fibers may be rinsed with water and/or shampooed prior and/after the application of the ready-to-use composition.
  • the ready-to-use composition is applied to the hair in an amount that is sufficient for e.g. the hair dyeing treatment, preferably in an amount of between about 60 to 200 grams.
  • the ready-to-use composition at a temperature of 20 to 35 °C.
  • the application time may be chosen such that the dyeing result is sufficient, i.e., between 2 to 90 min, preferably between 30 to 45 min.
  • the third kit component comprising at least one conditioning agent is applied after the application of the ready-to-use composition, preferably after an intermediate rinsing and/or shampooing step.
  • Viscosity data provided below was determined by means of a Brookfield viscometer, spindle B-LV-64 with "rpm 1" for ready-to-use compositions and "rpm 2" for cosmetic (tint) compositions at a temperature of 21 °C. The measurements were conducted as per the standard manufacturer's instructions.
  • Example 1 Storage and usability of Xanthan gum suspensions Suspensions of Xanthan gum were prepared by addition of Xanthan gum (6.0 g) to respective suspension medium (20.0 g) under stirring (see Tables 1.1 and 1.2)
  • Xanthan gum suspensions on basis of a non-ionic emulsifier of formula (I) or (II) exhibit excellent short- and long-term properties, whereby no significant differences were observed within the series of the inventive compositions. Even after standing for a day at room temperature, after which the suspension in propylene glycol had already become very viscous and difficult to handle, the inventive suspensions were still easily stirrable allowing to obtain a homogeneous suspension for further use.
  • Xanthan gum suspensions in propylene glycol are not suitable for extended storage times and have to be prepared immediately prior to a production batch.
  • inventive suspensions can be used for at least one week after preparation, during which the suspensions do not noticeably thicken and can be easily stirred to obtain homogeneous suspensions before adding the required amounts to new production batches.
  • Example 2 Preparation of a cosmetic composition - Addition of the Xanthan gum suspension to the initial manufacturing step
  • Step 1
  • Step 2 Water (250.0 g) is placed in a separate beaker. With stirring, the Xanthan gum suspension (26.0 g) from Step 1 is added followed by the addition of Crodafos CES (60.0 g), Ceteareth-25 (2.0 g), Stearyl alcohol (20.0 g), Cetearyl alcohol 50:50 (30.0 g), a 1 :1 mixture of Lauryl alcohol and Myristyl alcohol (40.0 g) and an aqueous sodium hydroxide solution (30% in water, 10.0 g). Then the mixture is heated to 75-80°C, homogenized for 2 min and allowed to cool to 50°C. Total weight: 438.0 g.
  • composition contains one or more dyes and/or additional non-coloring ingredients, their weight is compensated by reducing the amount of water.
  • Total weight eight 532.0 g
  • Step 3 While stirring, the solution from Step 3 is added to the dispersion of Step 2. The obtained mixture is maintained at 40°C for 10 minutes, then an aqueous Ammonia solution (28% in water, 30.0 g) is carefully added, followed by homogenization to obtain the final tint composition. Total weight: 1000 g.
  • Example 3 Manufacturing process - Addition of the Xanthan gum suspension to the last manufacturing step Step 1 :
  • Crodafos CES (60.0 g), Ceteareth-25 (2.0 g), Stearyl alcohol (20.0 g), Cetearyl alcohol 50:50 (30.0 g), and a mixture of Lauryl alcohol and Myristyl alcohol 50:50 (40.0 g) are added, followed by the addition of an aqueous sodium hydroxide solution (30% in water, 10.0 g). Then the mixture is heated to 75-80°C, homogenized by stirring for 2 min and allowed to cool to 50°C. Total weight: 412.0 g.
  • composition contains one or more dyes and/or additional non-coloring ingredients, their weight is compensated for by reducing the amount of water.
  • Total weight 532.0 g.
  • Example 4 Tint compositions I Compositions based on cetearyl alcohol, di-cetyl phosphate and ceteth-10 phosphate have been selected as model compositions as these are able to absorb various hydrophilic and lipophilic substances and thus, are particularly prone to syneresis if not stabilized by Xanthan gum.
  • Table 4.1 Tint compositions
  • a suspension of Xanthan gum in propylene glycol was used in comparative Example 4.0, which defines the reference value.
  • propylene glycol was replaced by the respective non-ionic emulsifiers of formula (I) or (II) as indicated in Table 4.1 , namely Laureth-3, Laureth-9, Oleth-3 and Oleth-5.
  • Table 5.1 Standard developer composition with hydrogen peroxide as oxidation agent The resulting pH value of both developer compositions is 3.0.
  • the viscosities of the inventive Examples 5.1 to 5.4 are in the same order of magnitude as the reference value Example 5.0, whereby nonionic emulsifiers of formula (I) or (II) featuring longer chains lead to alower the final viscosity.
  • the obtained ready-to-use compositions are applied onto light-blond human hair. After remaining on the hair for 30 minutes, the hair was rinsed with lukewarm water and dried.
  • the comparative compositions with propylene glycol and the inventive compositions gave identical dark blonde results.
  • the obtained perfect shade match demonstrates that Xanthan gum propylene glycol suspensions may be readily replaced by Xanthan gum suspension on basis of the inventive non-ionic emulsifier of formula (I) or formula (II) without affecting the resulting coloration.
  • Example 2 The above shade examples were prepared according to the method of Example 2. In comparison to the tint compositions of Example 4, the different dye composition is used, while the dye base itself was kept constant. The remainder to 100 % was water.
  • the ready-to-use compositions are obtained by mixing the tints of Example 6 (see Table 6.1 ) in a ratio of 1 :1.5 with the developer composition of Example 5.12.
  • the viscosities of the thus-obtained ready-to-use compositions were measured immediately after their preparation.
  • the ready-to-use compositions were then applied onto 50% human grey hair. After remaining on the hair for 30 minutes, the hair was rinsed with lukewarm water and dried.
  • the comparative composition with propylene glycol and the inventive comprising a non-ionic emulsifier of formula (I) or (II) gave identical dark blonde results, confirming that the inventive compositions do not cause a variation in the obtained coloration.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention se rapporte à un procédé de préparation d'une crème colorante pour la décoloration ou la coloration de fibres kératiniques, un prémélange étant introduit dans l'une quelconque des étapes du procédé. Ledit prémélange comprend une suspension de gomme xanthane dans au moins un émulsifiant non ionique de formule CH3-(CH2)11-[O-CH2-CH2]n-OH, (I) ou CH3-(CH2)7-C2H2-(CH2)8-[O-CH2-CH2]m-OH, (II) avec n = 2 à 9, de préférence n = 2 à 4 et m = 2 à 5, et au moins un alcool gras comportant une chaîne alkyle comprenant 12 à 30 atomes de C est ajouté avant ou conjointement avec le prémélange ou dans toute autre étape du procédé.
PCT/EP2024/071987 2023-08-07 2024-08-02 Procédé permettant de produire des colorants capillaires Pending WO2025031977A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102023120913 2023-08-07
DE102023120913.2 2023-08-07

Publications (1)

Publication Number Publication Date
WO2025031977A1 true WO2025031977A1 (fr) 2025-02-13

Family

ID=92258694

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/071987 Pending WO2025031977A1 (fr) 2023-08-07 2024-08-02 Procédé permettant de produire des colorants capillaires

Country Status (1)

Country Link
WO (1) WO2025031977A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0594811B1 (fr) 1992-05-18 1996-06-12 Wella Aktiengesellschaft Colorant d'oxydation pour cheveux, un agent-support sous forme de creme, et procede de coloration des cheveux
US6117915A (en) 1994-11-04 2000-09-12 Croda, Inc. Fatty alcohol phosphate ester emulsifier compositions
US20130167861A1 (en) * 2011-12-30 2013-07-04 L'oreal S.A. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
EP2979683A1 (fr) * 2014-07-30 2016-02-03 HCT - Hair Cosmetic Technology AG Colorants permanents pour cheveux basés sur un support de type crémeux et une combinaison de tris(hydroxyméthyl)aminomethane, au moins un acide aminé et une teinture oxydative
WO2021254909A1 (fr) * 2020-06-17 2021-12-23 Henkel Ag & Co. Kgaa Composant d'alcalisation épaissi pour produit capillaire de coloration par oxydation
US20230000756A1 (en) * 2021-06-30 2023-01-05 L'oreal Compositions and methods for styling hair

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0594811B1 (fr) 1992-05-18 1996-06-12 Wella Aktiengesellschaft Colorant d'oxydation pour cheveux, un agent-support sous forme de creme, et procede de coloration des cheveux
US6117915A (en) 1994-11-04 2000-09-12 Croda, Inc. Fatty alcohol phosphate ester emulsifier compositions
US20130167861A1 (en) * 2011-12-30 2013-07-04 L'oreal S.A. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
EP2979683A1 (fr) * 2014-07-30 2016-02-03 HCT - Hair Cosmetic Technology AG Colorants permanents pour cheveux basés sur un support de type crémeux et une combinaison de tris(hydroxyméthyl)aminomethane, au moins un acide aminé et une teinture oxydative
EP2979683B1 (fr) 2014-07-30 2019-07-24 HCT - Hair Cosmetic Technology AG Colorants permanents pour cheveux basés sur un support de type crémeux et une combinaison de tris(hydroxyméthyl)aminomethane, au moins un acide aminé et une teinture oxydative
WO2021254909A1 (fr) * 2020-06-17 2021-12-23 Henkel Ag & Co. Kgaa Composant d'alcalisation épaissi pour produit capillaire de coloration par oxydation
US20230000756A1 (en) * 2021-06-30 2023-01-05 L'oreal Compositions and methods for styling hair

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
AL JASSER, M.MEBUKE, N.DE GANNES, G.: "Propylene glycol: an often unrecognized cause of allergic contact dermatitis in patients using topical corticosteroids", SKIN THERAPY LETT., vol. 16, no. 5, 2011, pages 5 - 7
DATABASE GNPD [online] MINTEL; 25 November 2013 (2013-11-25), ANONYMOUS: "Californian and Traditional Highlight Kit", XP093221030, retrieved from https://www.gnpd.com/sinatra/recordpage/2240957/ Database accession no. 2240957 *
DATABASE GNPD [online] MINTEL; 26 April 2011 (2011-04-26), ANONYMOUS: "Hair Color", XP093221029, retrieved from https://www.gnpd.com/sinatra/recordpage/1541409/ Database accession no. 1541409 *
DATABASE GNPD [online] MINTEL; 30 July 2010 (2010-07-30), ANONYMOUS: "Resistant Cream Hair Colorant", XP093221043, retrieved from https://www.gnpd.com/sinatra/recordpage/1365629/ Database accession no. 1365629 *
DATABASE GNPD [online] MINTEL; 5 August 2014 (2014-08-05), ANONYMOUS: "Cream Hair Coloring", XP093221042, retrieved from https://www.gnpd.com/sinatra/recordpage/2584323/ Database accession no. 2584323 *
DATABASE GNPD [online] MINTEL; 7 July 2015 (2015-07-07), ANONYMOUS: "Professional White Bleach White Scented Bleaching Powder", XP093221041, retrieved from https://www.gnpd.com/sinatra/recordpage/3297681/ Database accession no. 3297681 *
DATABASE GNPD [online] MINTEL; 8 December 2021 (2021-12-08), ANONYMOUS: "Hair Mascara Express Touch", XP093221055, retrieved from https://www.gnpd.com/sinatra/recordpage/9220288/ Database accession no. 9220288 *
LESSMANN, H.SCHNUCH, A.GEIER, J.UTER, W: "Skin-sensitizing and irritant properties of propylene glycol", CONTACT DERMATITIS, vol. 53, 2005, pages 247 - 259

Similar Documents

Publication Publication Date Title
US8444709B2 (en) Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a 2-aminophenol and derivatives thereof
US8444714B2 (en) Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof
JP6433124B2 (ja) １−ヘキシル／ヘプチル−４，５−ジアミノピラゾール及びベンゾ［１，３］ジオキソール−５−イルアミン及びこれらの誘導体を含む、酸化染色組成物
JP2017206521A (ja) １−ヘキシル／へプチル−４，５−ジアミノピラゾール及びｍ−アミノフェノール及びその誘導体を含む酸化染色組成物
JP2016074719A (ja) １−ヘキシル／ヘプチル−４，５−ジアミノピラゾール及びナフタレン−１−オール及びこれらの誘導体を含む酸化染色組成物
JP5932838B2 (ja) 非アンモニアアルカリ化剤を含む染毛組成物
JP5937105B2 (ja) 染毛組成物を調製する方法
JP6448144B2 (ja) 毛髪処理組成物、そのキット及び方法
JP2019055998A (ja) 毛髪処理組成物、キット及びその方法
JP2015507014A (ja) １−ヘキシル−１ｈ−ピラゾール−４，５−ジアミンヘミサルフェート及びその染色組成物中での使用
WO2025031977A1 (fr) Procédé permettant de produire des colorants capillaires
EP2830579B1 (fr) Compositions de colorant capillaire comportant du 3-amino-2,6-diméthylphénol , procédés et nécessaires comportant les compositions
US6224856B1 (en) Means and method for tinting keratin fibers, particularly human hair
CA2754959A1 (fr) Derives 5-amino-1,2,3,4-tetrahydroquinoline et 4,5-diamino-pyrazole pour la coloration oxydative des fibres de keratine
CA2754962A1 (fr) Derive 5-hydroxy-quinoline pour la coloration oxydative des fibres de keratine

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24752040

Country of ref document: EP

Kind code of ref document: A1