WO2024046773A1 - Colorant à base d'indigo amélioré - Google Patents

Colorant à base d'indigo amélioré Download PDF

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Publication number
WO2024046773A1
WO2024046773A1 PCT/EP2023/072665 EP2023072665W WO2024046773A1 WO 2024046773 A1 WO2024046773 A1 WO 2024046773A1 EP 2023072665 W EP2023072665 W EP 2023072665W WO 2024046773 A1 WO2024046773 A1 WO 2024046773A1
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Prior art keywords
weight
indigo
oil
indigofera
agent
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PCT/EP2023/072665
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German (de)
English (en)
Inventor
Skrollan KLAAS
Nele DALLMANN
Jana Marie ROESEKE
Fabian STRASKE
Thomas Hippe
Original Assignee
Henkel Ag & Co. Kgaa
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Publication of WO2024046773A1 publication Critical patent/WO2024046773A1/fr

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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
    • A61Q5/06—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
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/45—Colour indicators, e.g. pH- or Redox indicators

Definitions

  • the invention relates to an agent and a method for coloring keratin-containing fibers, in particular human hair, using a plant powder producing indigo or indirubin and cysteine.
  • oxidation dyes These use oxidizing agents that can damage the hair structure.
  • Certain cationic direct azo dyes are also capable of enabling hair color changes with excellent fastness properties.
  • the azo dyes mentioned are synthetic dyes.
  • a growing number of consumers have a desire for hair dyes and hair coloring processes that are based on natural dyes, even if these products and processes are often inferior to the aforementioned products and processes in terms of fastness properties, opacity and variety of colors.
  • the addition of natural dyes to oxidative hair dyes is also popular.
  • the coloring cream is mixed with an aqueous preparation containing hydrogen peroxide shortly before it is applied to the hair.
  • the coloring cream predominantly contains oxidation dye precursors, for example toluene-2,5-diamine sulfate, 4-chlororesorcinol, 2-methylresorcinol, 2-amino-4-hydroxyethylaminoanisole sulfate, 4-amino-2-hydroxytoluene, 4-amino-m-cresol and m-aminophenol ;
  • the content of natural dyes is only used for shading.
  • the coloring achieved in this way is essentially a usual oxidative coloring with high fastness properties.
  • a further object was to provide means and methods for coloring keratin-containing fibers, in particular human hair, using plants that produce indigo or indirubin, with which a wider range of colorings can be achieved.
  • colorings beyond the typical indigo blue, particularly colorings with a shift to warmer color ranges, should be provided.
  • a first object of the present invention is therefore an agent for the non-oxidative coloring of keratin fibers, in particular human hair, containing water, cysteine and at least one plant powder i) producing indigo or indirubin, the agent having a pH of 2.0 to 10.0, preferably from 4.0 to 9.0, particularly preferably from 5.0 to 8.0, extremely preferably from 6.7 to less than 7.5, each measured at 20 ° C.
  • colorant according to the invention and coloring composition (A) are used synonymously in the present application.
  • Dyes preferred according to the invention are characterized in that the plant(s) producing indigo or indirubin is/are selected from at least one species of the following genera:
  • Indigofera in particular Indigofera tinctoria, Indigo suffruticosa, Indigofera articulata, Indigofera arrecta, Indigofera heterantha “Gerardiana”, Indigofera argentea or Indigofera longiracemosa;
  • Isatis especially Isatis tinctoria (woad);
  • Persicaria especially Persicaria tinctoria (dyer's knotweed);
  • Particularly preferred plants that produce indigo or indirubin are selected from the genus Indigofera and in particular from Indigofera tinctoria.
  • the plants of the genera and species mentioned above contain no or only small amounts of indigo and indirubin. Instead, the plants contain the compound indican, a precursor to indigo and indirubin.
  • the plant parts of the above-mentioned plant genera and species that are rich in indican and also contain indigo or indirubin are the leaves of these plants.
  • the plant leaves of the above-mentioned plant genera and species are dried and ground and used as plant powder.
  • Plant powders preferred according to the invention have a particle size of less than 500 pm, particularly preferably in the range of 120 pm - 200 pm, extremely preferably in the range of 150 pm - 180 pm.
  • Further plant powders preferred according to the invention have a bulk density in the range of 0.20 - 0.60 g/cm 3 , particularly preferably in the range of 0.25 - 0.40 g/cm 3 . Further plant powders preferred according to the invention have, based on their weight, a moisture content of less than 10% by weight, preferably from 0.1 to 6.0% by weight, particularly preferably from 0.2 to 3.0% by weight. . The moisture content is determined after drying for 3 hours at 105°C.
  • the powder of the indigo or indirubin-producing plant is at least 50% by weight, preferably at least 80% by weight, particularly preferably more than 80-100% by weight. consists of the leaves of the plant.
  • the powder of the plant producing indigo or indirubin has a particle size of less than 500 pm, particularly preferably in the range of 120 pm - 200 pm, extremely preferably in the range of 150 pm - 180 pm, as well as a bulk density in the range of 0.20 - 0.60 g/cm 3 , particularly preferably in the range of 0.25 - 0.40 g/cm 3 and, based on its weight, a moisture content of less than 10% by weight, preferred from 0.1 to 6.0% by weight, particularly preferably from 0.2 to 3.0% by weight.
  • the powder of the plant producing indigo or indirubin contains the compound indican in an amount of 2 - 5% by weight, preferably 2.5 - 4.5% by weight, particularly preferably 3 - 4 .1% by weight, based on the weight of the powder.
  • Further colorants preferred according to the invention are characterized in that at least one plant powder i) producing indigo or indirubin in a total amount of 1 - 80% by weight, preferably 2 - 50% by weight, particularly preferably 3 - 25% by weight, extraordinarily preferably 4 - 15% by weight, more particularly preferably 5 - 10% by weight, more particularly preferably 6 - 7% by weight, based on the weight of the agent.
  • Further coloring agents preferred according to the invention are characterized in that powdered leaves of Indigofera tinctoria in an amount of 1 - 80% by weight, preferably 2 - 50% by weight, particularly preferably 3 - 25% by weight, extremely preferably 4 - 15 % by weight, more particularly preferably 5-10% by weight, more particularly preferably 6-7% by weight, based on the weight of the agent.
  • Cysteine as a chiral amino acid, has a stereogenic center and can occur in mirror-image form, namely in the form of L-cysteine and D-cysteine. Both L-cysteine and D-cysteine and mixtures thereof are included in the present invention. In the context of the present invention, both possible enantiomers can therefore be used equally as specific compounds or mixtures thereof, in particular as racemates. However, according to the invention, it is particularly advantageous to use the naturally occurring isomer form, here L-cysteine.
  • Colorants that are extremely preferred according to the invention are characterized in that L-cysteine is present in an amount of 0.1 - 5.0% by weight, preferably 0.5 - 3.0% by weight, particularly preferably 0.8 - 2.0 % by weight, extremely preferably 1.0 - 1.5% by weight, based on the weight of the agent.
  • Aqueous solution of cysteine reacts acidically.
  • a 1% by weight solution of L-cysteine in deionized water has a pH of 6.49 measured at 20°C. Cysteine is therefore not an alkalizing agent.
  • Powders from the leaves of Indigofera tinctoria which are preferably used according to the invention, react approximately neutrally in an aqueous dispersion, with slight deviations between a slightly acidic and a slightly alkaline pH range.
  • a 5% by weight dispersion of ground leaves of Indigofera tinctoria in deionized water has a pH of 6.6 to 7.4, preferably 6.8 to 7.2, particularly preferably 6.9 to 7.1 , each measured at 20°C.
  • the colorants according to the invention also contain water.
  • the water serves to disperse the plant powder and to dissolve the indican contained therein and to make it accessible for the reaction to form indigo and indirubin.
  • Colorants preferred according to the invention are characterized in that water is present in an amount of 19.9 - 95.0% by weight, preferably 30.0 - 90.0% by weight, particularly preferably 50.0 - 88.0% by weight. %, extremely preferably 60.0 - 85.0% by weight, based on the weight of the agent.
  • the colorants according to the invention have a pH of 2.0 to 10.0, preferably from 4.0 to 9.0, particularly preferably from 5.0 to 8.0, extremely preferably from 6.7 to less than 7.5 , each measured at 20°C.
  • a dispersion of 5% by weight of ground leaves of Indigofera tinctoria in deionized water, in which 1% by weight of L-cysterol is further dissolved, has a pH of 6.85, measured at 20 ° C, where the quantities refer to the weight of the entire aqueous preparation.
  • the desired pH of the aqueous dyeing composition (A) is adjusted using an acid or a base.
  • Preferred acids are selected from citric acid, lactic acid, gluconic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, galactaric acid (mucilic acid), tartaric acid, malic acid, sulfuric acid and phosphoric acid as well as mixtures of these acids.
  • Preferred bases are sodium hydroxide, potassium hydroxide, arginine, lysine, monoethanolamine, triethanolamine, 2-amino-2-methyl-propan-1-ol and mixtures of these bases.
  • the desired pH value of the aqueous dyeing composition (A) is determined using a buffer system selected from a mixture of a medium or weak acid with its conjugate or corresponding base (or the respective salt) and a mixture of a medium or weak base with its conjugate or corresponding acid.
  • Corresponding acid-base pairs which are preferably suitable according to the invention are those which contain the aqueous dyeing composition (A) used according to the invention in the pH range from 2.0 to 10.0, preferably from 4.0 to 9.0, particularly preferably from 5 .0 to 8.0, extremely preferably from 6.7 to less than 7.5, each measured at 20 ° C.
  • Buffer systems that are particularly preferred according to the invention for the aqueous dyeing composition (A) used according to the invention are selected from
  • ammonium salt being preferably selected from ammonium chloride, ammonium bromide, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate, ammonium carbonate, ammonium nitrate, ammonium acetate, ammonium glycolate, ammonium gluconate, ammonium tartrate.
  • Ammonium lactate as well as mixtures of these ammonium salts, particularly preferably selected from ammonium chloride, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate and ammonium carbonate, extremely preferably selected from ammonium chloride, - Mixtures of hydrogen phosphate and dihydrogen phosphate, in particular the alkali metal salts of hydrogen phosphate and dihydrogen phosphate, particularly preferably the sodium salts and/or the potassium salts of hydrogen phosphate and dihydrogen phosphate,
  • citric acid and its salts in particular the alkali metal citrates, in particular the sodium salts, in particular trisodium citrate,
  • succinic acid and its salts in particular the sodium salts, in particular sodium hydrogen succinate and disodium succinate, as well
  • malic acid and its salts in particular the sodium salts, in particular sodium hydrogen malate and disodium malate, as well
  • ammonium salt being preferably selected from ammonium chloride, ammonium bromide, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate, ammonium carbonate, ammonium nitrate, ammonium acetate, ammonium glycolate, ammonium gluconate, ammonium tartrate.
  • Ammonium lactate as well as mixtures of these ammonium salts, particularly preferably selected from ammonium chloride, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate and ammonium carbonate, extremely preferably selected from ammonium chloride.
  • buffer systems for example acetic acid/sodium acetate, are in principle also suitable according to the invention.
  • acetic acid/sodium acetate due to the smell of vinegar, such a buffer is not acceptable for the production of a cosmetic market product.
  • the aqueous coloring composition (A) for pH adjustment contains a buffer system selected from a mixture of a medium-strong or weak acid or base with its conjugated or corresponding base or corresponding acid.
  • the aqueous dyeing composition (A) contains a buffer system selected from an ammonia/ammonium salt mixture for pH adjustment in the basic range.
  • Preferred ammonium salts which contain the strongly basic see buffer the pH value of the aqueous ammonia solution to a less basic pH value, are selected from ammonium chloride, ammonium bromide, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate, ammonium carbonate, ammonium nitrate, ammonium acetate, ammonium glycolate, ammonium gluconate, ammonium tartrate .
  • Ammonium lactate as well as mixtures of these ammonium salts.
  • Ammonium chloride, ammonium hydrogen sulfate, ammonium sulfate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium phosphate, ammonium bicarbonate and ammonium carbonate are particularly preferred. Ammonium chloride is extremely preferred.
  • the aqueous dyeing composition (A) contains a buffer system for pH adjustment, selected from a hydrogen phosphate salt/dihydrogen phosphate salt mixture.
  • Suitable salts are the sodium salts and the potassium salts of hydrogen phosphate and dihydrogen phosphate.
  • pH values in the range from 7.1 to around 8.2 can be adjusted.
  • the aqueous dyeing composition (A) contains a buffer system for pH adjustment, selected from a mixture of sodium or potassium hydrogen carbonate with sodium or potassium carbonate.
  • Suitable salts are the sodium salts and the potassium salts of hydrogen carbonate and carbonate.
  • the expert can find out the appropriate amounts of buffer salts to set the desired pH value in the relevant manuals.
  • Preferred dyes and dyeing processes according to the invention are further characterized in that no hydrogen peroxide is used in them.
  • Preferred colorants and coloring processes according to the invention are further characterized in that they do not use ions and compounds of metals other than alkali metals and alkaline earth metals.
  • the content of metal ions other than alkali metal ions and alkaline earth metal ions, which are found in trace amounts in the water used, e.g. B. contained in tap water or city water is not taken into account.
  • Tap water can contain an average of 2 mg of copper ions per liter, i.e. around 0.0002% by weight of copper ions.
  • the maximum concentration of metal ions other than alkali metal ions and alkaline earth metal ions in colorants preferred according to the invention is 0.00001 - 0.002% by weight, preferably 0.0001 to 0.001% by weight, particularly preferably a maximum of 0.0007% by weight, in each case on the dye.
  • suitable according to the invention are the salts of alkali metals and alkaline earth metals, in particular the salts of sodium, potassium and magnesium, preferably the salts of sodium and potassium.
  • the salts and compounds of aluminum, the transition metals and the lanthanides are particularly undesirable.
  • the metals mentioned in their elemental form are also not used in the dyes and dyeing processes according to the invention.
  • a further subject of the present invention is a process for the non-oxidative coloring of keratin fibers, in particular human hair, which comprises the following process steps in the order given: a) providing an aqueous coloring composition (A) which contains at least one plant powder i.e.
  • indigo or indirubin and further contains cysteine and a pH of 2.0 to 10.0, preferably from 4.0 to 9.0, particularly preferably from 5.0 to 8.0, extremely preferably from 6.7 to less than 7 .5, each measured at 20 ° C, b) applying the aqueous coloring composition (A) to the keratin fibers, c) allowing it to act for a time of 30 seconds to 60 minutes, preferably 5 to 45 minutes, particularly preferably 15 to 30 minutes , d) rinsing the keratin fibers with water, e) optionally drying the keratin fibers, wherein no hydrogen peroxide and no ions and compounds of metals other than alkali metals and alkaline earth metals are used in the process.
  • an aqueous dyeing composition (A) which has a pH in the range from 2.0 to 10.0, preferably from 4.0 to 9.0, is applied to the keratin fibers to be dyed, which are preferably dry. particularly preferably from 5.0 to 8.0, extremely preferably from 6.7 to less than 7.5, each measured at 20 ° C.
  • Dyeing processes preferred according to the invention are therefore characterized in that the action leaving the coloring composition (A) with the addition of heat.
  • Dyeing processes that are particularly preferred according to the invention are characterized in that the dyeing composition (A) is allowed to take effect while supplying heat at a temperature of 25 - 60 ° C, particularly preferably at a temperature of 30 - 50 ° C, extremely preferably at a temperature of 35 - 40 °C.
  • the claimed method is preferably limited to those methods in which the keratin fibers have not been treated with an oxidizing agent for a period of up to 7 days before application of the coloring composition (A) according to the invention.
  • oxidizing agents that are usually used in hair cosmetics, but with which no hair treatment is intended according to the invention, nor even as a pretreatment, include hydrogen peroxide, persulfates, perbromates, percarbonates, perborates and percarbamides.
  • the oxygen contained in the ambient air does not represent an oxidizing agent in the context of the invention.
  • methods preferred according to the invention are limited to those methods in which the keratin fibers have not been treated with a keratin-reducing compound for a period of up to 7 days before application of the dye composition (A) according to the invention.
  • the keratin fibers are preferably dried after rinsing out the coloring composition (A). Drying can take place without the active supply of heat. However, drying can also be carried out with the addition of heat at a temperature of 25 - 120 ° C, particularly preferably at a temperature of 30 - 80 ° C, extremely preferably at a temperature of 35 - 60 ° C. Heat is preferably supplied using a heat lamp, a drying rod, a drying hood, a straightener or a hairdryer.
  • a further feature of the dyeing process according to the invention is that the dyeing composition (A) is left there after application to the keratin fibers for a time of 30 seconds to 60 minutes, preferably 5 to 45 minutes, particularly preferably 20 to 35 minutes, extremely preferably 25 to 30 Allow to take effect for minutes.
  • the keratin fibers are rinsed with water to wash out the coloring composition (S).
  • the keratin fibers can be dried after this rinsing step. Drying can be done with an absorbent cloth, such as a towel. Towel-dried hair can optionally dried partially or completely with a hairdryer or another heat source. It is also possible to let the keratin fibers air dry.
  • oxidation dye precursors are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(1,2-dihydroxyethyl)phenol, 4-amino-2-(diethylaminomethyl )phenol, 2-(2,5-diaminophenyl)ethanol, 2-(1,2-dihydroxyethyl)-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, N-(4 -Amino-3-methylphenyl)-N-[3-(1H-imidazole-
  • 2-Hydroxy-4-aminophenoxyethanol 5-amino-4-chloro-2-methylphenol, 5-(2-hydroxyethyl)-amino-2-methyl-phenol, 2,4-dichloro-3-aminophenol, 2-aminophenol, 3-Phenylenediamine, 2-(2,4-diaminophenoxy)ethanol, 1,3-bis(2,4-diaminophenoxy)propane, 1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene, 1,3- Bis(2,4-di-aminophenyl)propane, 2, 6-bis(2'-hydroxyethylamino)-1-methylbenzene, 2-( ⁇ 3-[(2-hydroxyethyl)amino]-4-methoxy-5-methylphenyl ⁇ amino)ethanol, 2-( ⁇ 3-[(2-Hydroxyethyl)amino]-2-methoxy-5-methylphenyl ⁇ amino
  • the coloring compositions (A) according to the invention and those preferred according to the invention can optionally contain further additives in order to optimize the application properties of these compositions.
  • Preferred additives are, in particular, thickeners which ensure that the coloring composition (A) remains better on the hair during use.
  • Coloring compositions (A) which are particularly preferred according to the invention contain at least one or more hydrophilic thickeners, which are preferably selected from polysaccharides which can be chemically and/or physically modified. According to the invention, compounds from the group of polysaccharides are particularly preferred as hydrophilic thickeners, since the basic structures of the polysaccharides are of natural origin and biodegradable.
  • Preferred hydrophilic polysaccharide thickeners are selected from celluloses, cellulose ethers of C1-C4 alcohols, cellulose esters, xanthan gum, alginic acids (as well as their corresponding physiologically tolerated salts, the alginates), agar agar (with the polysaccharide agarose present in agar agar as the main component) , starch fractions and starch derivatives such as amylose, amylopectin and dextrins, karaya gum, Locust bean gum, gum arabic, pectins, dextrans and guar gum as well as mixtures thereof.
  • Cellulose ethers of C1-C4 alcohols and cellulose esters preferred according to the invention are selected from methylcelluloses, ethylcelluloses, hydroxyalkylcelluloses (such as hydroxyethylcellulose), methylhydroxyalkylcelluloses and carboxymethylcelluloses (such as those with the INCI name cellulose gum) and their physiologically tolerated salts.
  • xanthan gum is included as a hydrophilic thickener for reliable viscosity adjustment and residue-free application on keratin fibers and the scalp.
  • carboxymethylcellulose preferably carboxymethylcellulose with the INCI name Cellulose Gum
  • carboxymethyl cellulose can be included as the only hydrophilic thickener. A combination of carboxymethyl cellulose and hydroxyethyl cellulose is particularly preferred.
  • a combination of carboxymethylcellulose and xanthan gum may also be preferred according to the invention.
  • Dyeing compositions (A) which are particularly preferred according to the invention contain at least one hydrophilic thickener in a total amount of 0.1 to 5% by weight, preferably from 0.5 to 4% by weight, more preferably from 1 to 3.5% by weight. and very particularly preferably from 1.2 to 2% by weight, based in each case on the weight of the respective coloring composition (A).
  • the coloring compositions (A) according to the invention contain, based on their weight, 0.1 to 3% by weight, preferably 0.5 to 2.5% by weight, more preferably 1.2% by weight up to 2.0% by weight, xanthan gum.
  • the dyeing compositions (A) according to the invention contain, based on their weight, 0.1 to 4% by weight, preferably 1 to 2.8% by weight, of carboxymethyl cellulose.
  • the dyeing compositions (A) according to the invention contain, based on their weight, 0.1 to 3% by weight, preferably 0.5 to 2.5% by weight, more preferably 1.2% by weight up to 2.0% by weight, hydroxyethyl cellulose.
  • Dyeing compositions (A) which are particularly preferred according to the invention contain at least one organic solvent which has a phenyl group in the molecule.
  • This solvent is preferably selected from phenoxyethanol, benzyl alcohol and mixtures thereof. It was surprisingly found that such aromatic solvents can have a positive effect on the dyeing results of the dyeing process according to the invention; this was particularly observed when the coloring composition (A) contains such an aromatic solvent.
  • the coloring compositions (A) preferred according to the invention contain, based on their weight, 0.1 to 3% by weight, preferably 0.5 to 2.5% by weight, more preferably 0.8 to 1.0% by weight, of at least one organic solvent that has a phenyl group in the molecule.
  • the dyeing compositions (A) according to the invention contain, based on their weight, 0.1 to 3% by weight, preferably 0.5 to 2.5% by weight, more preferably 0.8 up to 1.0% by weight of at least one organic solvent selected from phenoxyethanol, benzyl alcohol and mixtures thereof.
  • Dyeing compositions (A) which are particularly preferred according to the invention are characterized in that they contain at least one aliphatic solvent selected from Ci-C4 alkanols and C2-C4 polyols, in particular selected from ethanol, isopropanol, n-propanol, ethylene glycol, 1,2 -propanediol, glycerol and 1,3-butylene glycol, as well as mixtures of these solvents, but only in a total amount of 0.01 - 8% by weight, preferably 0.1 - 6% by weight, particularly preferably 0.5 - 4 % by weight, based in each case on the weight of the coloring composition (A).
  • Ci-C4 alkanols and C2-C4 polyols in particular selected from ethanol, isopropanol, n-propanol, ethylene glycol, 1,2 -propanediol, glycerol and 1,3-butylene glycol, as well as mixtures of these solvent
  • coloring compositions (A) which are particularly preferred according to the invention are characterized in that they do not contain any aliphatic solvent selected from Ci-C4 alkanols and C2-C4 polyols.
  • coloring compositions (A) which are particularly preferred according to the invention are characterized in that they contain at least one perfume oil which contains at least one fragrance compound or fragrance compound.
  • a fragrance in the sense of the present application corresponds to the usual professional definition, as can be found in the R ⁇ MPP Chemie Lexikon, as of December 2007.
  • a fragrance is a chemical compound with smell and/or taste that excites the receptors of the hair cells of the olfactory system (appropriate stimulus).
  • the physical and chemical properties required for this are a low molecular weight of a maximum of 300 g/mol, a high vapor pressure, minimal water and high lipid solubility as well as weak polarity and the presence of at least one osmophoric group in the molecule.
  • fragrances according to the invention In order to differentiate volatile, low-molecular substances that are not usually viewed and used as fragrances but primarily as solvents, such as ethanol, propanol, isopropanol and acetone, from fragrances according to the invention, fragrances according to the invention have a molecular weight of 74 up to 300 g/mol, contain at least one osmophoric group in the molecule and have an odor and/or taste, that is, they excite the receptors of the hair cells of the olfactory system.
  • fragrance and fragrance compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethyl benzyl carbinyl acetate (DMBCA), phenyl ethyl acetate, benzyl acetate, ethyl methyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate, benzyl salicylate, cyclohexyl salicylate, Florama t, melusate and jasmecyclate.
  • DMBCA dimethyl benzyl carbinyl acetate
  • benzyl ethyl acetate benzyl acetate
  • ethyl methyl phenyl glycinate allyl cyclohexyl propionate
  • fragrance and fragrance compounds of the ether type are benzyl ethyl ether and Ambroxan
  • examples of fragrance and fragrance compounds of the aldehyde type are the linear alkanals with 8 - 18 carbon atoms, citral, citronellal, citronellyloxy-acetaldehyde, cyclamenaldehyde, lilial and bourgeonal
  • examples of fragrance and fragrance compounds of the ketone type are the Jonone, alpha-isomethyl ionone and methyl cedryl ketone
  • examples of fragrance and fragrance compounds of the alcohol type are anethole, citronellol, eugenol, geraniol, linalool, phenylethyl alcohol and terpineol
  • examples of fragrance and fragrance compounds of the terpene type are limonene and pinene.
  • fragrance and fragrance compounds are pine, citrus, jasmine, patchouly, rose, ylang-ylang oil, clary sage oil, chamomile oil, clove oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, Labdanum oil, orange blossom oil, neroli oil, orange peel oil and sandalwood oil, as well as essential oils such as angelica root oil, anise oil, arnica blossom oil, basil oil, bay oil, bergamot oil, champaca blossom oil, noble fir oil, fine fir cone oil, elemi oil, eucalyptus oil, fennel oil, spruce needle oil, geranium oil, ginger grass oil, guaiac wood oil, gurjun balsam oil, helichrysum oil , Ho oil, ginger oil, iris oil, kajeput oil, calamus oil, chamomile oil, camphor oil, kanaga oil, cardam
  • fragrance and fragrance compounds are ambrettolide, a-amylcinnamaldehyde, anethole, anisaldehyde, anise alcohol, anisole, anthranilic acid methyl ester, acetophenone, benzyl acetone, benzaldehyde, benzoic acid ethyl ester, benzophenone, benzyl alcohol, benzyl acetate, benzyl benzoate, benzyl formate, benzyl valerianate, borneol, bornyl acetate, a- Bromstyrene, N-Decylalhyde, N-Dodecylalhyde, Eugenol, Eugenolmethyl ether, eucalyptol, Farnesol, fennchon, fenchlacetate, Geranylacetate, Geranyl formiat, heliotropin, heptincarboxicemethylester, heptaldehy
  • fragrances include alkyl isothiocyanates (alkyl mustard oils), butanedione, limonene, linalool, linayl acetate and propionate, menthol, menthone, methyl-n-heptenone, phellandrene, phenylacetaldehyde, terpinyl acetate, citral and citronellal.
  • Mixtures of different fragrances are preferably used, which together produce an appealing scent.
  • Suitable perfume oils can also contain natural fragrance mixtures, such as those made from plants or animal sources, e.g. pine, citrus, jasmine, rose, lily or ylang-ylang oil.
  • Essential oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, for example sage oil, chamomile oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, laudanum oil, clove oil, iso-eugenol, thyme oil, bergamot oil , geranium oil and rose oil.
  • Coloring compositions (A) which are extremely preferred according to the invention are characterized in that they contain at least one fragrance in a total amount of 0.01 - 5% by weight, preferably 0.1 - 3% by weight, particularly preferably 0.5 - 2% by weight. -%, extremely preferably 1 - 1.5% by weight, each based on the weight of the coloring composition (A).
  • Indigo Powder (Indigofera tinctoria L.) powdered leaves of Indigofera tinctoria pH value of the 5% by weight dispersion in water: 6.8 to 7.2 (20°C)
  • the hair strands were rinsed under running deionized water for 30 seconds while combing 20 times (20°C).
  • the color difference also referred to as dE or AE, can be easily determined colorimetrically using a colorimeter with which the colors in the L*,a*,b* color space are measured, for example with a colorimeter from Datacolor, type Spectraflash SF 600.
  • the L*,a*,b* color space refers to the CIELAB color space.
  • the L value stands for the brightness of the color (black-white axis); the larger the value for L, the lighter the color.
  • the a value represents the red-green axis of the system; the larger this value is, the more the color is shifted towards red.
  • the b value represents the yellow-blue axis of the system; the larger this value is, the more the color is shifted towards yellow.
  • the color shift AE i.e. the color difference between two (hair) colors for which an L*,a*,b* value combination was determined, is calculated according to the following formula:
  • a D65 bulb and a diffuse/8° optical configuration were used for the spectrophotometer measurements.
  • the spectral reflectance data for each sample from 380 nm to 700 nm was converted into colorimetric data using DCI Color software. Reflectance measurements were determined for each hair sample, with the average of 4 measurements recorded.
  • AE color difference between the undyed strand and the dyed strand (with indigo-cysteine or with indigo without cysteine) was calculated according to the following formula: Lv, av, bv: Colorimetric values for colored strands (indigo and cysteine or indigo without cysteine)
  • cysteine initially shows only a small influence with a small red shift.
  • cysteine-containing indigo dye shows a clear red shift on the red-green axis (a value) and a shift back to blue on the yellow-blue axis (b value).
  • the strands treated with cysteine are significantly more red in color and show a significantly less pronounced shade of blue.
  • Table 3 L*, a*, b*, AE values of the indigo dyes with cysteine
  • Table 4 Coloring composition according to the invention (A-2); Indigo leaves from another batch
  • Indigo Powder (Jndigofera tinctoria L.) powdered leaves of Indigofera tinctoria pH value of the 5% by weight dispersion in water: 6.8 to 7.2 (20°C)
  • the dyeing composition was prepared and dyed at room temperature (20-25°C) as described for A-1.
  • the liquor ratio was 50 g of dye per 1 g of hair (50:1).
  • the hair strands were rinsed under running deionized water for 30 seconds while combing 20 times (20°C).
  • cysteine On the red-green axis (a value), cysteine also causes a stronger red shift.
  • the cysteine-treated strand shows a less pronounced shade of blue than the control strand.
  • the strand treated with cysteine darkens, it is still lighter, has a significantly stronger red color and shows a less pronounced shade of blue than the control strand.
  • Table 6 summarizes color measurements on other colorants that were prepared like compositions A-1 and A-2 according to the invention and colored on strands of hair.
  • the pH value of the dye was adjusted to pH 7.4 with sodium hydroxide solution.
  • the coloring was not carried out at room temperature, but at 35°C.
  • the color difference AE refers to the comparison of indigo with cysteine under “conventional” conditions (unaffected pH and coloring at room temperature) and the sample listed.
  • cysteine-treated strands darken, become more red, and show a less pronounced shade of blue than the control strands.

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Abstract

L'invention concerne un produit et un procédé de coloration de fibres de kératine, en particulier de cheveux humains, à l'aide d'une poudre de plante produisant de l'indigo ou de l'indirubine et de la cystéine.
PCT/EP2023/072665 2022-09-01 2023-08-17 Colorant à base d'indigo amélioré WO2024046773A1 (fr)

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DE102022209085.3A DE102022209085A1 (de) 2022-09-01 2022-09-01 Verbessertes Indigo-basiertes Färbemittel

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10360204A1 (de) * 2003-12-20 2005-07-28 Wella Ag Mittel und Verfahren zum Färben von Keratinfasern
JP4287719B2 (ja) * 2003-08-28 2009-07-01 リアル化学株式会社 染毛剤およびそれを用いた染毛方法
WO2015082482A1 (fr) 2013-12-06 2015-06-11 L'oreal Procédé de coloration de matériaux kératiniques en utilisant une poudre de plantes produisant de l'indigo et un (des) agent(s) alcalins
FR3127885A1 (fr) * 2021-10-11 2023-04-14 L'oreal Procédé de coloration des fibres kératiniques à partir de proline et de poudre et/ou extrait colorant de plantes indigofères

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4287719B2 (ja) * 2003-08-28 2009-07-01 リアル化学株式会社 染毛剤およびそれを用いた染毛方法
DE10360204A1 (de) * 2003-12-20 2005-07-28 Wella Ag Mittel und Verfahren zum Färben von Keratinfasern
WO2015082482A1 (fr) 2013-12-06 2015-06-11 L'oreal Procédé de coloration de matériaux kératiniques en utilisant une poudre de plantes produisant de l'indigo et un (des) agent(s) alcalins
FR3127885A1 (fr) * 2021-10-11 2023-04-14 L'oreal Procédé de coloration des fibres kératiniques à partir de proline et de poudre et/ou extrait colorant de plantes indigofères

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