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WO2019122332A1 - Procédé en plusieurs étapes pour teinter des fibres de kératine à l'aide d'une poudre de plantes produisant de l'indigo, et pour un traitement de colorant alcalin - Google Patents

Procédé en plusieurs étapes pour teinter des fibres de kératine à l'aide d'une poudre de plantes produisant de l'indigo, et pour un traitement de colorant alcalin Download PDF

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Publication number
WO2019122332A1
WO2019122332A1 PCT/EP2018/086590 EP2018086590W WO2019122332A1 WO 2019122332 A1 WO2019122332 A1 WO 2019122332A1 EP 2018086590 W EP2018086590 W EP 2018086590W WO 2019122332 A1 WO2019122332 A1 WO 2019122332A1
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Leila Hercouet
Françoise ALBOUY
Boris Lalleman
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LOreal SA
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LOreal SA
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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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]
    • A61K8/9789—Magnoliopsida [dicotyledons]

Definitions

  • the invention relates to (I) a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, in which said fibres are treated in several steps, comprising at least one step E1 ) of dyeing said fibres using a cosmetic dye composition A comprising indigo- producing plant powder i) and optionally henna ii); at least one step E2) of post-treatment of said fibres using an aqueous cosmetic composition B whose pH is greater than 5, preferably greater than 7, comprising one or more alkaline agents iii) and one or more particular natural dyes, other than henna and indigoids ; it being understood that composition A is applied first to the keratin fibres; and that composition B is applied to the keratin fibres after the application of composition A, and (II) to the use of a composition B comprising one or more particular alkaline agents iii) and at least one particular natural dye, other than henna and indigoids, for accelerating the stabilization
  • colourings using indigo and henna are generally evolutive over time in terms of colour, they have a characteristic yellow/green colouring on the day of application (relatively unaesthetic "raw" colour, which dyeing consumers appreciate little) which change towards the desired colourings after a few hours (48 hours to 1 week) and may change colour over time (appearance of violet-red tints generally after 2 to 3 weeks).
  • colourings using indigo and henna are generally evolutive over time in terms of colour, they have a characteristic yellow/green colouring on the day of application (relatively unaesthetic "raw" colour, which dyeing consumers appreciate little) which change towards the desired colourings after a few hours (48 hours to 1 week) and may change colour over time (appearance of violet-red tints generally after 2 to 3 weeks).
  • the first known as oxidation dyeing or permanent dyeing, consists in using one or more oxidation dye precursors, more particularly one or more oxidation bases optionally combined with one or more couplers.
  • oxidation bases are selected from ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, can give rise via a process of oxidative condensation to coloured species, which remain trapped within the fibre.
  • Couplers are chosen in particular from aromatic meta- diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
  • the second dyeing method comprises the application of direct dyes, which are coloured and colouring molecules that have affinity for fibres. Given the nature of the molecules used, they tend rather to remain on the surface of the fibre and penetrate relatively little into the fibre, when compared with the small molecules of oxidation dye precursors.
  • the main advantages of this type of dyeing are that it does not require any oxidizing agent, which limits the degradation of the fibres, and that it does not use any dyes that have particular reactivity, resulting in limitation of the intolerance risks.
  • the first hair dyes were semi-permanent.
  • One of the most widely-known natural dyes is indigo (see Ullmann's Encyclopedia of Industrial Chemistry, "Hair preparation", point 5.2.3, 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; 10.1002/14356007.a12 571.pub2).
  • Indigo continues to be used in female beauty enhancement for dyeing the hair or the nails, or for dyeing fabrics (jeans), leather, silk, wool, etc.
  • Indigo [482-89-3] is a natural blue dye, and its isomer indirubin is red.
  • Their empirical formula is: C16H10N2O2; and their chemical structures are the following:
  • isatin may give indigotin or indirubin (Maugard et al., 2001 ).
  • the presence of these two isomers accounts for the violet colour of indigo that is more or less pronounced as a function of the respective proportion in the hair of the two isomers formed in the hair (violet to purple if the amount of indirubin increases).
  • Indigo is derived from indican and may be prepared from various plants known as indigo- producing plants such as Indigofera tinctoria, Indigo suffruticosa, Polygonum tinctorium etc. (see Kirk-Othmer Encyclopedia of Chemical Technology, updated on 17/04/2009, DOI: 10.1002/0471238961.0425051903150618. a01.pub2).
  • the indigo-producing plants are generally chopped and soaked in hot water, heated, fermented and oxidized in the open air to liberate the purple-blue coloured indigo (see Chem. Rev. 201 1 , 111 , 2537-2561 , pages 2537- 2561 ).
  • Indigo is the result of the hydrolysis and then oxidization of indican (glycosyl precursor).
  • the problem is that dyeing using the indigo leaf is difficult because the kinetics of colour buildup in keratin fibres is variable. Furthermore, the dyeing process is unstable. Indigo affords a blue colouring on grey hair, and a "cold" colour of ash to violet type on chestnut-brown hair. However, the dyeing process using indigo is difficult to control due to the competing reaction for the formation of indirubin (which also involves an oxidation step with intermediate formation of yellow-coloured isatin) giving complementary yellow to violet tints to chestnut-brown hair over time.
  • the colourings resulting from mixtures of indigo and henna are thus generally evolutive over time in terms of colour, they have a characteristic yellow/green colouring on the day of application (relatively unaesthetic "raw" colour, which dye consumers appreciate little) which changes towards the desired colourings after a few hours (48 hours to 1 week) and may change colour over time (appearance of violet-red tints generally after 2 to 3 weeks). There is thus a need to stabilize this colouring to obtain an aesthetic colouring on the day of application (for example brown free of yellow/green tints) which changes little over time (no colour change).
  • the dyes generally used in direct dyeing are dyes such as nitrobenzene, anthraquinone, nitropyridine, azo, methine, azomethine, xanthene, acridine, azine or triarylmethane direct dyes (see, for example, EP 0 806 199).
  • This option has the drawback for natural product users, or for proponents of "natural/organic" products, that the colouring is partly performed using synthetic dyes.
  • the tint provided on the day of application does not prevent the colour change over time (evolution of the yellow tint that is still present in the fibre, although masked, towards red).
  • the indigo molecule is insoluble in water whereas henna is itself soluble, this leads to substantial inhomogeneities in colour buildup between the root and the end (selectivity) when the two dyes are in admixture.
  • step E1 of dyeing said fibres using a cosmetic dye composition A comprising indigo-producing plant powder i) and optionally henna ii);
  • step E2 of treating said fibres using an aqueous cosmetic composition B whose pH is greater than 5 and preferably greater than 7 and comprising one or more alkaline agents iii) and one or more natural dyes chosen from:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted alkoxy group or an optionally substituted acyloxy group;
  • R 11 , R 12 , R 13 , Ri 6 , R 19 and R 20 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical
  • R M , R15, R17 and Ris which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a Ci-C 4 alkoxy radical;
  • composition A is applied first to the keratin fibres; and that composition B is applied to the keratin fibres after the application of composition A;
  • composition B preferably involving at least one rinsing step and/or one washing step between the dyeing step using composition A and the treatment step involving the application of composition B.
  • the dyeing process involves a step of dyeing keratin fibres via the application of a dye composition A to the fibres, comprising indigo-producing plant powder and optionally henna, and a step of treating with an aqueous composition B whose pH is greater than 5, better still greater than 7, comprising one or more alkaline agents and at least one natural dye such as defined previously, the dyeing step preferably being performed first, and the treatment step being performed as a post-treatment.
  • a subject of the invention is also the use of an aqueous composition B whose pH is greater than 5, better still greater than 7, comprising one or more alkaline agents and one or more natural dyes chosen from:
  • dyes of chromene or chroman type chosen from the dyes of formulae (III) and (IV) as defined previously, preferably chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood); santalins, santarubins (sandalwood); and mixtures thereof, preferably chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood) and mixtures thereof; preferentially from haematoxylin and/or brazilin;
  • the keratin fibre dyeing process according to the invention has the advantage of dyeing said fibres, especially human keratin fibres, in particular the hair, with natural dyeing results with no yellow/green tints, and/or powerful, chromatic colourings that are resistant to washing, perspiration, sebum and light and that are furthermore long lasting without becoming impaired.
  • the colourings obtained using the process are uniform from the root to the end of a fibre (little colour selectivity).
  • the treated keratin fibres show very good cosmetic properties; in particular, their integrity is respected.
  • compositions used according to the invention are cosmetic compositions, i.e. they are cosmetically acceptable and are thus suitable for use for application to keratin fibres, especially for application to human keratin fibres such as the hair.
  • composition A is obtained by mixing, just before use, indigo-producing plant powder i) and optionally henna ii) with an aqueous composition to obtain a ready-to-use dye composition A, preferably in the form of a poultice.
  • composition A is an aqueous composition.
  • the dye composition A according to the invention comprises indigo-producing plant powder and/or an indigo-producing plant dye extract.
  • Indigofera such as Indigofera tinctoria, Indigo suffraticosa, Indigofera articulata,
  • Isatis such as Isatis tinctoria
  • Persicaria such as Polygonum tinctorium (Persicaria tinctoria);
  • Calanthe such as Calanthe veratrifolia
  • Baphicacanthus such as Baphicacanthus cusia.
  • the indigo-producing plant is of the genus Indigofera and more particularly is Indigofera tinctoria, suffructicosa or Indigofera argentade, preferably Indigofera tinctoria.
  • Use may be made of all or part (in particular the leaves especially for Indigofera tinctoria) of the indigo-producing plant.
  • the indigo-producing plant powder may be screened to obtain particles with upper limit sizes corresponding to the orifices or mesh sizes of the screen particularly between 35 and 80 mesh (US).
  • the size of the indigo-producing plant powder particles is fine.
  • a particle size of less than or equal to 500 pm is more particularly intended.
  • the powder is constituted of fine particles with sizes inclusively between 50 and 300 pm and more particularly between 10 and 200 pm.
  • said indigo-producing plant particles preferentially have a moisture content of between 0 and 10% by weight relative to the total weight of the powders.
  • the indigo-producing plant extract according to the invention is a product of maceration in solvents, generally organic solvents, of all or part (in particular the leaves especially for Indigofera tinctoria) of the indigo-producing plant.
  • the indigo-producing plant powder according to the invention is a natural product originating from indigo-producing plants, reduced by grinding or other mechanical means into fine particles.
  • an indigo-producing plant powder is used.
  • composition A is in the form of a solid, preferably pulverulent, preferably anhydrous composition.
  • the indigo-producing plant powder is preferably present in composition A in a content ranging from 10% to 99% by weight, relative to the total weight of composition A, more particularly ranging from 20% to 90% by weight, preferentially ranging from 20% to 80% by weight.
  • composition A is obtained by mixing just before use (i.e.
  • the indigo-producing plant powder and/or extract i) and optionally henna ii) with water or with an aqueous composition to obtain a ready- to-use dye composition A, preferably in the form of a poultice.
  • the indigo-producing plant powder and/or extract is present in composition A preferably in a content ranging from 0.5% to 50% by weight, relative to the total weight of composition A, when composition A is aqueous, more particularly ranging from 1 % to 40% by weight, preferentially ranging from 5% to 30% by weight.
  • composition A when it is ready-to-use, comprises water.
  • ready-to-use refers to a composition that is ready to be applied directly to the keratin fibres.
  • composition A of the invention may also contain one or more surfactants, preferably anionic or nonionic surfactants.
  • the ready-to-use composition A applied to the keratin fibres according to the process of the invention is preferably obtained from mixing between the indigo-producing plant powder and/or extract i) in compact or loose form, optionally henna ii), and an aqueous composition, preferably water.
  • the ready-to-use composition A applied to the keratin fibres according to the process of the invention is in the form of a poultice.
  • the ready-to-use dye composition A comprises a water content ranging from 10% to 99% by weight, more particularly from 20% to 90% by weight and better still from 40% to 85% by weight relative to the weight of ready-to-use composition A.
  • the indigo-producing plant powder or extract i), optionally the henna ii) and optionally the additional compounds as described previously are mixed with an aqueous composition comprising water, to obtain a poultice of creamy and pleasant consistency corresponding to the ready-to-use composition A.
  • the indigo-producing plant powder is compact, it is crumbled into the aqueous composition, and the compact composition is preferentially crumbled into water.
  • the dye composition A) according to the invention preferably comprises henna ii).
  • henna refers to a henna plant powder and/or a henna plant dye extract, preferably from a henna plant such as Lawsonia alba or Lawsonia inermis.
  • the henna plant powder and/or dye extract especially comprises lawsone and/or a glucosyl precursor thereof.
  • the henna used according to the present invention is in powder form. It is understood that the henna powder and the indigo-producing plant powder are different from an extract. Specifically, an extract is a product of maceration in solvents, generally organic solvents, whereas the powder according to the invention is a natural product originating from henna or indigo-producing plants, reduced by grinding or other mechanical means, in fine particles.
  • the henna used in the invention is red henna ( Lawsonia inermis, alba). Lawsone [83-72-7] (Cl Natural Orange 6; Cl 75420), also known as isojuglone, may be found in henna shrubs ( Lawsonia alba, Lawsonia inermis).
  • the henna is in powder form.
  • the henna powder may be screened to obtain particles with upper limit sizes corresponding to the orifices or mesh sizes of the screen particularly between 35 and 80 mesh (US).
  • the size of the henna powder particles is fine. According to the invention, a particle size of less than or equal to 500 pm is more particularly intended.
  • the powder is constituted of fine particles with sizes inclusively between 10 and 300 pm and more particularly between 50 and 250 pm. It is understood that said henna particles preferentially have a moisture content of between 0 and 10% by weight, relative to the total weight of the powders.
  • said henna particles are derived from henna leaves.
  • composition A is in the form of a solid, preferably pulverulent, preferably anhydrous composition.
  • henna is preferably present in composition A in a content ranging from 5% to 99% by weight, relative to the total weight of composition A, more particularly ranging from 10% to 60% by weight, preferentially ranging from 15% to 40% by weight, in particular when composition A is anhydrous.
  • composition A is obtained by mixing just before use (i.e. extemporaneously) the indigo- producing plant powder i) and henna ii) (when it is present) with water or with an aqueous composition to obtain a ready-to-use dye composition A, preferably in the form of a poultice.
  • henna is present in composition A preferably in a content ranging from 0.1 % to 30% by weight, relative to the total weight of composition A, when composition A is aqueous, more particularly ranging from 0.15% to 20% by weight, preferentially ranging from 0.2% to 10% by weight.
  • the indigo- producing plant powder and/or extract i) and henna ii) are present in composition A in a i)/ii) weight ratio ranging from 0.1 % to 95, preferably from 0.5 to 50 and better still from 1 to 10.
  • Composition B is a composition of Composition B:
  • Composition B used according to the invention is an aqueous composition whose pH is greater than 5. It preferably ranges from 5 to 12.
  • the pH of composition B is greater than 7.
  • the pH of composition B is greater than or equal to 7.5, and preferably less than or equal to 12.
  • the pH of composition B ranges from 7.5 to 1 1 .5 and preferably from 7.5 to 10.
  • Composition B used in the process according to the invention as post-treatment comprises one or more alkaline agents iii).
  • alkaline agent and “basifying agent” are used interchangeably.
  • the basifying agent is a Bronsted, Lowry or Lewis base. It may be mineral or organic.
  • said alkaline agent(s) are chosen from iii-i) (bi)carbonates, iii-ii) aqueous ammonia, iii-iii) alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, iii-iv) oxyethylenated and/or oxypropylenated ethylenediamines, iii-v) mineral or organic hydroxides, iii-vi) alkali metal silicates such as sodium metasilicates, iii-vii), amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and iii-viii) the compounds of formula (XI) below:
  • W is a divalent (Ci-C 8 )alkylene radical optionally substituted with at least one hydroxyl group or at least one (Ci-C 4 )alkyl radical and/or optionally interrupted with at least one heteroatom, such as oxygen or sulfur, or with a group -N(R e )-;
  • R a , R t> , R c , R d and R e which may be identical or different, represent a hydrogen atom or a (Ci-C 4 )alkyl or hydroxy(Ci-C 4 )alkyl radical; preferably, W represents a propylene radical.
  • the mineral or organic hydroxides are preferably chosen from a) hydroxides of an alkali metal, b) hydroxides of an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide, c) hydroxides of a transition metal, such as hydroxides of metals from groups III, IV, V and VI, d) hydroxides of lanthanides or actinides, quaternary ammonium hydroxides and guanidinium hydroxide, and mixtures thereof.
  • the hydroxide may be formed in situ, for instance guanidine hydroxide, formed by reacting calcium hydroxide with guanidine carbonate.
  • b)bicarbonates also known as hydrogen carbonates, of the following formulae: ⁇ R’ + , HCO3 , with R’ representing a hydrogen atom, an alkali metal, an ammonium group R” 4 N + - or a phosphonium group R” 4 P + -, where R”, which may be identical or different, represent a hydrogen atom or an optionally substituted (Ci-C 6 )alkyl group, such as hydroxyethyl, and, when R’ represents a hydrogen atom, the hydrogen carbonate is then known as dihydrogen carbonate (CO2, H2O); and
  • the basifying agent is chosen from alkali metal or alkaline-earth metal (bi)carbonates and amino acids such as arginine, lysine, ornithine, citrulline and histidine; preferentially alkali metal (bi)carbonates and amino acids.
  • alkali metal or alkaline-earth metal (bi)carbonates and amino acids such as arginine, lysine, ornithine, citrulline and histidine; preferentially alkali metal (bi)carbonates and amino acids.
  • the (bi)carbonate(s) are chosen from Na, K, Mg and Ca carbonates or hydrogen carbonates and mixtures thereof, and in particular Na hydrogen carbonate.
  • the amino acid(s) are chosen from arginine, glycinate, serine and/or proline, preferably arginine.
  • the basifying agent(s) iii) are chosen from amino acids, such as arginine, alkanolamines such as monoethanolamine, and (bi)carbonates, in particular alkali metal or alkaline-earth metal (bi)carbonates, alone or as mixtures. They are preferentially together during the dyeing process.
  • the basifying agent(s) as defined previously preferably represent from 0.001% to 10% by weight relative to the weight of composition B, more particularly from 0.005% to 8% by weight relative to the weight of composition B.
  • the basifying agent(s) iii) are present in the aqueous composition B in a concentration inclusively between 0.1 M and 1 M, such as 0.5 M.
  • composition B Natural dyes present in composition B:
  • Composition B used according to the invention comprises one or more particular natural dyes other than henna and the indigoids described previously.
  • composition B The natural dye(s) iv) used in composition B are chosen from:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted alkoxy group or an optionally substituted acyloxy group;
  • R11 , R12, R13, Ri6, R19 and R20 which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical
  • R14, R15, R17 and Ris which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a C1-C4 alkoxy radical; iv-ii) sappanins and protosappanins (sappan wood); iv-vii) and mixtures thereof.
  • the natural dye(s) according to the invention may or may not be salified. They may also be in aglycone form (without bonded sugars) or in the form of glycosylated compounds.
  • glycosyl radical means a radical derived from a monosaccharide or polysaccharide.
  • the natural dyes according to the invention may be in the form of powders or liquids.
  • the natural dyes of the invention are in the form of powders.
  • the natural dyes of the invention are in the form of powders.
  • the natural dyes used according to the invention in composition B have an absorption wavelength lTM 3c of between 625 and 750 nm or between 300 and 470 nm, and better still between 625 and 750 nm.
  • the dyes of the invention are dyes which absorb in the red range, i.e. at an absorption wavelength which is within the range particularly between 300 and 470 nm, or in the violet range between 625 and 750 nm of red-oranges, preferably reds.
  • the natural dyes used according to the present invention are polyphenols (and/or polyphenol-rich extracts).
  • polyphenol(s) means one or more compounds comprising one or more aromatic rings bearing several hydroxyl functions.
  • the natural dye(s) iv) are chosen from the dyes iv-i) of chroman/chromene type of formula (III) or (IV) as defined above.
  • alkyl radicals mentioned in the preceding definitions of the substituents are saturated and linear or branched hydrocarbon-based radicals, generally C1-C20, particularly C1-C10, preferably C1-C6 hydrocarbon-based radicals, such as methyl, ethyl, propyl, butyl, pentyl and hexyl.
  • the alkoxy radicals are alkyl-oxy radicals with the alkyl radicals as defined above and preferably the alkoxy radicals are C 1 -C 10 alkoxy radicals, such as methoxy, ethoxy, propoxy and butoxy.
  • the alkyl or alkoxy radicals when they are substituted, may be substituted with at least one substituent borne by at least one carbon atom chosen from: i) a halogen atom or ii) a hydroxyl group; iii) a C 1 -C 2 alkoxy group; iv) a C 1 -C 10 alkoxycarbonyl group; v) a (poly)hydroxy(C 2 -C 4 )alkoxy group; vi) an amino group; vii) a 5- or 6-membered heterocycloalkyl group; viii) an optionally cationic 5- or 6-membered heteroaryl group, preferably imidazolium, optionally substituted with a (Ci-C 4 )alkyl radical, preferably methyl; ix) an amino radical substituted with one or two identical or different C 1 -C 6 alkyl radicals optionally bearing at least: a) one hydroxyl group,
  • the alkyl or alkoxy radicals of formula (III) are unsubstituted.
  • the dyes of formula (III) comprise a radical R 6 representing a hydroxyl group.
  • Another particular embodiment of the invention relates to the dye(s) of formula (III) for which the radical Ri represents a hydrogen atom or a hydroxyl group.
  • the dye(s) of the invention a) are of formula (III) and chosen from haematoxylin, haematein, brazilin and brazilein; preferentially haematoxylin and brazilin:
  • Brazilein is a conjugated form of a chroman compound of formula (A2).
  • the tautomeric structures (Ilia) and (lllb) illustrated above are found in the scheme below.
  • haematoxylin/haematein and brazilin/brazilein type examples that may be mentioned include haematoxylin (Natural Black 1 according to the INCI name) and brazilin (Natural Red 24 according to the INCI name), dyes of the indochroman family, which are commercially available.
  • haematoxylin Natural Black 1 according to the INCI name
  • brazilin Natural Red 24 according to the INCI name
  • dyes of the indochroman family which are commercially available.
  • the latter dyes may exist in an oxidized form and may be obtained synthetically or by extraction of plants known to be rich in these dyes.
  • the dye(s) of natural origin of the invention may be used in the form of extracts.
  • Use may be made of the following plant extracts (genus and species): Haematoxylon campechianum, extract of oxidized logwood ( Haematoxylon campechianum ) brasiletto ( Haematoxylum brasiletto, rich in brazilin and protosappanin), Quebracho ( Schinopsis lorentzii) Caesalpinia echinata, Caesalpinia sappan, Caesalpinia spinosa, and Caesalpina brasi lien sis.
  • the dyes are of formula (IV), preferably those for which Rn and R1 3 represent an alkyl radical, preferably methyl.
  • R12, R1 6 , R1 9 and R2 0 denote, independently of each other, a hydrogen atom or an alkyl radical, preferably methyl.
  • R-u and R 17 denote, independently of each other, a hydrogen atom or an alkoxy radical, preferably methoxy.
  • R 18 and R 15 denote, independently of each other, a hydrogen atom, a hydroxyl radical or an alkoxy radical, preferably methoxy.
  • a first particularly preferred family of dyes of natural origin of the invention that are suitable for use in the present invention is that of the dyes corresponding to formula (IV) above for which R12, R15, R16, R17, R19 and R20 each represent a hydrogen atom.
  • Rn and R13 each represent a methyl radical and R-u represents a methoxy radical.
  • dyes of the invention of this first family are those for which R-is represents a methoxy radical (santalin B) or a hydroxyl radical (santalin A).
  • a second particularly preferred family of dyes that are suitable for use in the present invention is that of the dyes corresponding to the formula (IV) above for which:
  • R 11 and R 13 each represent a methyl radical
  • R 17 represents a methoxy radical
  • a preferred dye of this second family is that for which, in addition, R 19 represents a methyl radical, R20, R12, RI 4 , Ris and R16 each represent a hydrogen atom and R15 represents a hydroxyl radical (santarubin A).
  • a second preferred dye of this second family is that for which Rie, R 20 , R 12 , R-u and R 16 represent a hydrogen atom, R 15 represents a methoxy radical and R 19 represents a methyl radical (santarubin B).
  • a third preferred family of dyes of this second family is that for which R20, R12, R-u, R15, R16 and R19 represent hydrogen and Ris represents a hydroxyl radical (santarubin C).
  • the advantageous dye(s) of this second family are those for which R 15 represents a methoxy radical, Ris and R14 represent a hydrogen atom and R20, R12, R16 and R19 represent a methyl radical (tetra-O-methylsantarubin).
  • the dye(s) of formula (IV) may be used in the form of extracts.
  • Use may be made of plant extracts of red woods, bringing together generally the species of red woods from Asia and West Africa of the genus Pterocarpus and of the genus Baphia.
  • These woods are, for example, Pterocarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or else Baphia nitida.
  • These woods may also be called padauk, sandalwood, narra wood, camwood or else barwood.
  • extracts that may be used, containing dyes of formula (IV), in the present invention may be obtained, for example, from red sandalwood ( Pterocarpus santalinus) by aqueous basic extraction, such as the product sold under the trade name Santal Concentre SL 709C by COPIAA, or else by means of solvent extraction of sandalwood powder, such as the product sold under the trade name Santal Poudre SL PP by COPIAA. Mention may also be made of the aqueous/alcoholic extract of powdered red sandalwood from Alban Muller.
  • Extracts also suitable for the present invention may be obtained from woods such as camwood (Baphia nitida) or barwood ( Pterocarpus soyauxii, Pterocarpus erinaceus ): the latter is thus split up and then ground: a conventional alcoholic extraction or an extraction by percolation is subsequently performed on this ground material in order to collect a pulverulent extract that is particularly suitable for the implementation of the present invention.
  • camwood Baphia nitida
  • barwood Pterocarpus soyauxii, Pterocarpus erinaceus
  • the dye(s) of formulae (III) and (IV) of the invention may be salts of acids or bases that are cosmetically acceptable.
  • the acids may be mineral or organic.
  • the acid is hydrochloric acid, which results in chlorides.
  • the bases may be mineral or organic.
  • the bases are alkaline hydroxides, such as sodium hydroxide, resulting in sodium salts.
  • the extracts are obtained by extracting the various plant parts, for instance the root, the wood, the bark or the leaves.
  • the natural dye(s) iv) are chosen from dyes of chroman/chromene type preferably of formula (III) or (IV) as defined above, preferably chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood); santalins, santarubins (sandalwood); and mixtures thereof.
  • the natural dye(s) iv) are chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood), and mixtures thereof, preferentially from haematoxylin and/or brazilin.
  • the natural dye(s) iv) are chosen from the dyes iv-ii) chosen from sappanins and protosappanins (sappan wood).
  • composition B Preferably, the natural dye(s) iv) used in composition B according to the present invention are chosen from:
  • dyes of chromene/chroman type of formula (III) or (IV) as defined above chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood); santalins, santarubins (sandalwood); and mixtures thereof, better still chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood) and mixtures thereof; even better still from haematoxylin and/or brazilin;
  • composition B Preferably, the natural dye(s) iv) used in composition B according to the present invention are chosen from:
  • dyes of chroman/chromene type chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood) and mixtures thereof; better still from haematoxylin and/or brazilin.
  • the natural dyes iv) in composition B are chosen from:
  • the natural dye(s) iv) used according to the present invention are polyphenols chosen from:
  • dyes of chromene/chroman type of formula (III) or (IV) as defined above preferably chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood); santalins, santarubins (sandalwood); and mixtures thereof, better still chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood) and mixtures thereof; even better still from haematoxylin and/or brazilin; sappanins and protosappanins (sappan wood);
  • the natural dye(s) iv) used according to the invention are ortho- diphenols (ODPs) (and/or ODP-rich extracts). Use may also be made of extracts or decoctions containing these natural dyes and especially poultices or extracts based on these dyes.
  • ODP(s) means one or more compounds comprising one or more aromatic rings, at least one of which is a benzene ring, substituted with at least two hydroxyl (OH) groups borne by two adjacent carbon atoms of said benzene group which is present in the structure of the ortho-diphenol(s).
  • the aromatic ring is more particularly a fused aryl or fused heteroaromatic ring, i.e. a ring optionally comprising one or more heteroatoms, such as benzene, naphthalene, tetrahydronaphthalene, indane, indene, anthracene, phenanthrene, indole, isoindole, indoline, isoindoline, benzofuran, dihydrobenzofuran, chroman, isochroman, chromene, isochromene, quinoline, tetrahydroquinoline and isoquinoline, said aromatic ring including at least two hydroxyl groups borne by two adjacent carbon atoms of the aromatic ring.
  • the aromatic ring of the ortho-diphenol derivatives according to the invention is a benzene ring.
  • fused ring means that at least two saturated or unsaturated and heterocyclic or non-heterocyclic rings have a common bond, i.e. that at least one ring is positioned alongside another ring.
  • the natural dye(s) iv) are chosen from ortho-diphenol(s) or ODP(s).
  • the natural dye(s) iv) used according to the present invention are ortho-diphenols chosen from:
  • dyes of chromene/chroman type of formula (III) or (IV) as defined above preferably chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood); santalins, santarubins (sandalwood); and mixtures thereof, better still chosen from haematoxylin, haematein (campeachy wood), brazilin, brazilein (Brazil wood) and mixtures thereof; even better still from haematoxylin and/or brazilin; sappanins and protosappanins (sappan wood);
  • the “pure” natural dye(s) iv) are present in composition B in a total amount ranging from 0.05% to 25% by weight relative to the total weight of the dye composition, in particular ranging from 0.1 % to 10% by weight relative to the total weight of the dye composition, preferentially from 0.5% to 5% by weight relative to the total weight of composition B.
  • the content in composition B containing the extract(s) iv) per se is preferably between 0.1 % and 20% by weight, relative to the weight of composition B, more preferentially from 0.5% to 5% by weight.
  • Compositions A and/or B as defined previously may comprise one or more organic solvents.
  • Preferred organic solvents include C1-C4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, hexylene glycol, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol.
  • the organic solvents are present in proportions preferably of between 0.1 % and 20% by weight approximately and even more preferentially between 0.5% and 10% by weight approximately, relative to the total weight of the composition under consideration.
  • compositions A and/or B as defined previously may comprise one or more identical or different oils.
  • o/T means a "fatty substance” that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg); the viscosity at 25°C is preferably less than 1200 cps and better still less than 500 cps (defined, for example, from the Newtonian plateau determined using an ARG2 rheometer from TA Instruments equipped with a spindle with cone-plate geometry 60 mm in diameter and with an angle of 2 degrees over a shear stress range of from 0.1 Pa to 100 Pa).
  • fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %). They bear in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms 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.
  • non-silicone o/ means an oil not containing any silicon (Si) atoms and the term “silicone o/T means an oil containing at least one silicon atom.
  • the oils are chosen from non-silicone oils and in particular O Q -O-I Q hydrocarbons or hydrocarbons containing more than 16 carbon atoms and in particular alkanes; oils of animal origin; triglyceride oils of plant origin; essential oils; fluoro oils or glycerides of synthetic origin, fatty alcohols; fatty acid and/or fatty alcohol esters other than triglycerides, fatty acid amides and silicone oils.
  • the oils are not oxyalkylenated or glycerolated ethers.
  • the oils do not comprise any C2-C3 oxyalkylene units or any glycerolated units.
  • the oils are not fatty acids which, in salified form, give water-soluble soaps.
  • the oils that may be used as second ingredient b) in composition A or B in accordance with the invention may be silicones.
  • the silicones may be volatile or non-volatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity from 5x10 6 to 2.5 m 2 /s at 25°C, and preferably 1 x10 5 to 1 m 2 /s.
  • the silicone is chosen from polydialkylsiloxanes, especially polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMSs polydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those with a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane, sold especially under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereof.
  • Non-volatile polydialkylsiloxanes are preferably used.
  • silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes bearing trimethylsilyl end groups.
  • the viscosity of the silicones is measured at 25°C according to ASTM standard 445 Appendix C.
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm 2 /s;
  • CTFA dimethiconol
  • Compositions A and/or B as defined previously may comprise one or more oils, chosen from fatty alcohols, fatty acid amides and fatty acid esters in the form of oils.
  • fatty alcohols, esters and acids more particularly bear at least one linear or branched, saturated or unsaturated hydrocarbon-based group comprising 6 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.
  • these compounds may represent an ester of a C1-C10 alcohol and of a C6-C30 fatty acid such as R-C(0)-0-R' with R representing a linear or branched C6-C30 alkyl or linear or branched C6-C30 alkenyl group, comprising one or two unsaturations, and R representing a linear or branched C1-C10 alkyl group.
  • R represents a linear C10-C20 alkyl group and R' represents a C1-C6 alkyl group that is preferably branched, such as isopropyl myristate.
  • the ingredient ii) represents one or more amides of a C6-C30 fatty acid and of a primary or secondary, preferably primary, C1-C10 amine, such as those of formula R”-C(0)-N(R a )-R”’ with R” representing a linear or branched C6-C30 alkyl or a linear or branched C6-C30 alkenyl group, comprising one or two unsaturations, which may be substituted with one or more hydroxyl groups, or (di)(Ci-C 6 )(alkyl)amino, and R’” representing a linear or branched C1-C10 alkyl group, R a representing a hydrogen atom or an alkyl group as defined for R’”.
  • R representing a linear or branched C6-C30 alkyl or a linear or branched C6-C30 alkenyl group, comprising one or two unsaturations, which may be substituted with one or more hydroxyl groups, or
  • R represents a C14-C20 alkenyl group
  • Ra represents a hydrogen atom
  • R’ represents a C1 -C6 alkyl group optionally substituted with (di)(C1 -C4)(alkyl)amino such as oleylamidopropyldimethylamine.
  • C6-C16 alkanes they are linear or branched, and possibly cyclic. Examples that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
  • the linear or branched hydrocarbons containing more than 16 carbon atoms may be chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam ® , squalane, squalene, and mixtures thereof.
  • hydrocarbons mention may be made of the refined vegetable perhydrosqualene sold under the name Fitoderm by the company Cognis; the vegetable squalane sold, for example, under the name Squalive by the company Biosynthis.
  • liquid fatty acid triglycerides containing 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 oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearinerie Dubois or those sold under the names Miglyol ® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
  • liquid fatty acid triglycerides containing 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 oil, hazelnut oil,
  • fluoro oils mention may be made of perfluoromethylcyclopentane and perfluoro-1 ,3-dimethylcyclohexane, sold under the names Flutec ® PC1 and Flutec ® PC3 by the company BNFL Fluorochemicals; perfluoro-1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050 ® and PF 5060 ® by the company 3M, or bromoperfluorooctyl sold under the name Foralkyl ® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-(trifluoromethyl)perfluoromorpholine sold under the name PF 5052 ® by the company 3M.
  • Flutec ® PC1 and Flutec ® PC3 by
  • the oil(s) of the invention are non-silicone oils.
  • non-silicone o/ means an oil not containing any silicon (Si) atoms and the term “silicone o/T means an oil containing at least one silicon atom.
  • the oil(s) are chosen from O Q -O-I Q alkanes, hydrocarbons containing more than 16 carbon atoms, polydecenes, liquid esters of a fatty acid and/or of a fatty alcohol, and liquid fatty alcohols, or mixtures thereof.
  • oils are chosen from liquid petroleum jelly, C6-C16 alkanes, polydecenes and hydrocarbons containing more than 16 carbon atoms.
  • the oil(s) are chosen from mineral oils such as liquid petroleum jelly, squalane and squalene.
  • the oils are chosen from oils of natural origin, more particularly oils of plant origin, preferentially chosen from jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, corn oil, argan oil, soybean oil, marrow oil, grapeseed oil, linseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, coriander oil, almond oil, castor oil, avocado oil, shea butter oil and also rapeseed oil, borage oil, evening primrose oil, pomegranate oil, mango oil, palm oil, cottonseed oil and coconut kernel oil, and mixtures thereof.
  • compositions A and/or B may contain one or more oils of plant origin preferably chosen from avocado oil, olive oil, coconut oil, coconut kernel oil, argan oil and sunflower oil; more preferentially, the oil(s) of the invention are chosen from coconut kernel oils, and mixtures thereof.
  • oils of plant origin preferably chosen from avocado oil, olive oil, coconut oil, coconut kernel oil, argan oil and sunflower oil; more preferentially, the oil(s) of the invention are chosen from coconut kernel oils, and mixtures thereof.
  • compositions A and/or B may contain one or more oils chosen from C6-C16 hydrocarbons or hydrocarbons containing more than 16 carbon atoms, and in particular alkanes; preferably from:
  • C6-C16 hydrocarbons the latter being linear, branched, and optionally cyclic, preferably chosen from hexane, dodecane, isoparaffins such as isohexadecane and isodecane, and mixtures thereof;
  • hydrocarbons containing more than 16 carbon atoms preferably chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam ® , hemisqualane, squalane and squalene, and mixtures thereof;
  • Compositions A and/or B used in the process of the invention preferably comprise one or more oils in an amount inclusively between 1 % and 80% by weight, more particularly between 2% and 50% by weight, preferentially between 3% and 40% by weight and more preferentially between 2% and 25% by weight, relative to the total weight of said compositions.
  • compositions A and/or B used in the process of the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, amphoteric or nonionic surfactants, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance ceramides, film-forming agents, preserving agents, opacifiers and mineral or organic thickeners such as clays.
  • adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, amphoteric or nonionic surfactants, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance ceramides, film-forming agents
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the composition, and preferably between 0.1 % and 20% by weight relative to the weight of the composition under consideration.
  • Compositions A and/or B used in the dyeing process of the invention may also contain one or more additional direct dyes, in particular synthetic dyes or dyes of natural origin, other than the indigo-producing plant powder i) and henna ii) and the natural dyes iv) as described previously.
  • additional direct dyes in particular synthetic dyes or dyes of natural origin, other than the indigo-producing plant powder i) and henna ii) and the natural dyes iv) as described previously.
  • the synthetic direct dyes are preferably chosen from those conventionally used in direct dyeing, among which may be mentioned all the commonly used aromatic and/or non-aromatic dyes, such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane or indoamine direct dyes, methines, styryls, porphyrins, metalloporphyrins, phthalocyanines, methine cyanines and fluorescent dyes.
  • aromatic and/or non-aromatic dyes such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane or in
  • the natural direct dyes other than indigo i) and henna ii) are chosen from condensed, gallic or ellagic tannins, naphthoquinones (juglone, lawsone), anthraquinones (emodin, alizarin, carminic acid, laccaic acid, kermesic acid, etc.), isatin, curcumin, spinulosin, polyphenols such as flavonoids, isoflavonoids, pterocarpans, neoflavones or orceins.
  • These natural dyes may be added in the form of defined compounds, extracts or plant parts.
  • Said defined compounds from extracts or from plant parts are preferably in the form of powders, in particular fine powders whose particles have sizes identical to that of the indigo- producing plant powder as defined previously.
  • the natural or synthetic direct dye(s) other than the indigo- producing plant powder i) and henna ii) used in the process of the invention particularly represent from 0.001 % to 10% by weight relative to the total weight of the ready-to-use composition and even more preferentially from 0.05% to 5% by weight relative to the total weight of the composition under consideration.
  • the compositions of the invention do not contain any synthetic direct dyes, i.e. dyes that do not occur in nature.
  • Composition A used in the process of the invention may also comprise one or more oxidation bases and/or one or more couplers conventionally used for dyeing keratin fibres.
  • oxidation bases mention may be made of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho- aminophenols and heterocyclic bases, and the addition salts thereof.
  • couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • the oxidation base(s) present in the composition(s) are each generally present in an amount of between 0.001 % and 10% by weight of the total weight of the dye composition(s).
  • the dyeing process of the invention does not use any oxidation dyes.
  • the pH of the ready-to-use composition A after mixing with the aqueous composition, preferably with water, containing the ingredients i) and ii), ranges from 2 to 9, preferably from 3 to 7 and better still from 4 to 6.5.
  • the pH of the ready-to-use composition A may be adjusted to the desired value by means of acidifying or basifying agent(s) usually used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidic agents that may be used in the compositions of the invention, mention may be made of mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid or sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids; the acid is preferably an organic acid such as citric acid.
  • hydrochloric acid for instance hydrochloric acid, orthophosphoric acid or sulfuric acid
  • carboxylic acids for instance acetic acid, tartaric acid, citric acid and lactic acid
  • sulfonic acids the acid is preferably an organic acid such as citric acid.
  • the dyeing process uses one or more surfactants.
  • the surfactant(s) are chosen from anionic and nonionic surfactants.
  • the dyeing process according to the invention involves two different compositions A and B used during two different steps E1 ) and E2), via their application to keratin fibres.
  • composition A is applied first to the keratin fibres; and composition B is applied to the keratin fibres after the application of composition A; the process preferably involves at least one rinsing step, and/or a washing step between the dyeing step involving composition A and the treatment step involving the application of composition B.
  • the dyeing process according to the invention involves the following steps: - the first step consists in preparing composition A as defined previously, in particular in the form of a poultice as defined previously comprising water, using indigo-producing plant powder and/or extract i) and optionally henna ii);
  • the ready-to-use composition A as defined previously is then applied to the keratin fibres and is left on said fibres preferably for a minimum time of 30 minutes, preferentially a time ranging from 10 minutes to 12 hours, better still ranging from 15 minutes to 75 minutes and better still from 15 to 60 minutes;
  • aqueous composition B whose pH is greater than 5, better still greater than 7, comprising one or more alkaline agents and one or more natural dyes iv) chosen from:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted alkoxy group or an optionally substituted acyloxy group;
  • R11 , R12, R13, Ri6, R19 and R20 which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical
  • R14, R15, R17 and Ris which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a C1-C4 alkoxy radical; iv-ii) sappanins and protosappanins (sappan wood);
  • the keratin fibres are rinsed with water until the poultice has disappeared, and/or washed in the presence of a shampoo; preferably, according to this third step, the fibres are rinsed with water without being shampooed;
  • the keratin fibres may then be either dried or left wet, preferably left wet.
  • composition B Preferably, after application of composition B, the keratin fibres are washed and/or rinsed.
  • composition B as defined previously is applied first to the keratin fibres, and the ready-to-use composition A as defined previously is then applied to the keratin fibres and is left to stand on said fibres preferably as defined previously.
  • the fibres are also preferably rinsed as described previously.
  • the keratin fibres are washed and/or rinsed.
  • the ready-to-use composition A preferably comprises water and is in the form of a poultice; it may also comprise one or more oils, and/or one or more organic solvents and cosmetic additives, mixed with the indigo-producing plant powder i) and optionally with the henna ii).
  • the indigo-producing plant powder i) and optionally the henna is mixed with or crumbled into an aqueous composition, preferably water, at a temperature below 100°C, in particular between 25°C and 70°C and better still between 25°C and 50°C.
  • the temperature of application of composition A ranges from room temperature (15°C to 25°C) to 50°C and more particularly from 25°C to 40°C.
  • the head of hair may advantageously be subjected to a heat treatment by heating at a temperature ranging from 30°C to 150°C and better still from 30°C to 60°C.
  • this operation may be performed using a hairstyling hood, a hairdryer, an infrared ray dispenser and other standard heating appliances.
  • a particular embodiment of the invention relates to a dyeing process which is performed at room temperature (25° C).
  • the evaluation of the colouring obtained on the keratin fibres may be performed visually or with a spectrocolorimeter in the CIE L * a * b * system, for example using a Minolta CM 2000 spectrocolorimeter (illuminant D65, angle 10°, specular component included).
  • L * represents the lightness of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.
  • the smaller the value of L * the darker and more powerful the colouring.
  • the colour buildup corresponds to the variation in colouring between the locks of hair before and after the treatment or dyeing are defined by (DE * ) according to the following equation:
  • L * , a * and b * represent the values measured on locks of hair after dyeing and l_o*, a o * and bo* represent the values measured on locks of undyed hair.
  • DE* value the higher the DE* value, the better is the buildup of the colour.
  • the colour difference DE * between the colour at TO and the colour after 3 weeks represents the stability of the colour of the hair and is calculated by means of the following equation:
  • Lo * , a o * and bo * represent the colorimetric coordinates measured on locks of hair at TO immediately after performing the process and L3 S * , a3 s * and b * 3 S represent the colorimetric coordinates 3 weeks after performing the process.
  • a colouring for which the DE * three weeks after dyeing is less than 2 is considered as stable over time.
  • compositions were prepared:
  • the percentages are indicated on a weight basis relative to 100 g of composition.
  • the following dye composition is prepared by mixing, at the time of use, the natural dye powder with water at 50°C so as to make the following poultice:
  • the described ingredients i) and ii) are dissolved or dispersed in the relative amounts described in the table below in water at 50°C in a bowl. The whole is homogenized with a spoon or spatula.
  • the poultice obtained is very creamy, and is applied to locks of natural hair containing 90% white hairs, at a rate of 10 g of composition per 1 g of hair.
  • the locks are left to stand for 60 minutes at 33°C under cellophane.
  • compositions B1 , B2 and B3 are then applied at a rate of 5 g of composition per gram of hair and left to stand for 15 minutes at 40°C under cellophane, comparatively with reference locks which have not undergone any post-treatment.
  • all the locks are then rinsed and washed with Ultra Doux camomile shampoo, and then dried.
  • the colour of the locks was evaluated in the CIE L * a * b * system, using a Minolta CM 3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included).
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.
  • the colour buildup corresponds to the variation in colouring between the locks of hair before and immediately after performing the process are defined by (DE * ) according to the following equation:
  • L * , a * and b * represent the values measured on locks of hair after dyeing and Lo * , a o * and bo * represent the values measured on locks of undyed hair.
  • Lo * , a o * and b o * represent the colorimetric coordinates measured on locks of hair at TO immediately after performing the process and L 3W * , a 3w * and b * 3w represent the colorimetric coordinates three weeks after performing the process.
  • the post-treatment of the invention makes it possible to obtain a more intense and more aesthetic brown colouring (higher red or lower yellow components) from the end of the dyeing process, when compared with the comparative post- treatments B1 and B2 or with the process without post-treatments, with a higher colour buildup and intensity.
  • This colouring obtained according to the process of the invention is moreover stable over time (DET 3 weeks -To ⁇ 2).
  • the process of the invention makes it possible to obtain an aesthetic colouring from the day of application and to stabilize the colouring containing indigo from the day of application of the dyeing treatment. Without post-treatment, an aesthetic colouring is only obtained several days after the application. With an alkaline post-treatment other than that of the invention, no aesthetic colouring is obtained, either at TO or after three weeks.
  • the process of the invention thus makes it possible to accelerate the revelation of the colouring using indigo and optionally henna to obtain the final dyeing result from the day of application and to avoid unaesthetic intermediate tints.
  • Dyeing step The following dye composition was prepared by mixing, at the time of use, the natural dye powders with water at 50°C so as to make the following poultice:
  • This mixture is applied to a pair of locks of natural and permanent-waved Caucasian hair containing 90% white hairs, at a bath ratio of 10 g per 1 g of lock.
  • the locks are left to stand for 60 minutes at 33°C under cellophane.
  • each of the post-treatment compositions B5, B6 and B7 is then applied at a rate of 5 g of composition per gram of hair and left to stand for 15 minutes at 40°C under cellophane, comparatively with reference locks dyed with composition C2 which have not undergone any post-treatment.
  • the poultice dyes the hair in an unaesthetic green- yellow
  • composition B6 intensifies the green colouring
  • the alkaline post-treatment without dye partially neutralizes the green of the colouring, but the shade remains unaesthetic
  • composition B7 The alkaline post-treatment of the invention in the presence of haematoxylin (composition B7) makes it possible to intensify the colour (in terms of colour buildup and/or lightness) and to neutralize the unaesthetic green tint.

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Abstract

L'invention concerne (I) un procédé de teinture de fibres de kératine, en particulier des fibres de kératine humaines telles que les cheveux, dans lequel lesdites fibres sont traitées en plusieurs étapes, comprenant au moins une étape E1) de teinture desdites fibres à l'aide d'une composition de colorant cosmétique A comprenant de la poudre de plantes produisant de l'indigo i) et éventuellement du henné ii); au moins une étape E2) de post-traitement desdites fibres à l'aide d'une composition cosmétique aqueuse B dont le pH est supérieur à 5, de préférence supérieur à 7, comprenant un ou plusieurs agents alcalins iii) et un ou plusieurs colorants naturels particuliers; étant entendu que, de préférence, la composition A est appliquée en premier sur les fibres kératiniques; et cette composition B est appliquée sur les fibres kératiniques après l'application de la composition A, et (II) l'utilisation d'une composition aqueuse B comprenant un ou plusieurs agents alcalins particuliers iii) et au moins un colorant naturel particulier, pour accélérer la stabilisation dans le temps de la couleur de fibres teintées avec de la poudre et/ou de l'extrait de plants produisant de l'indigo et éventuellement du henné et pour améliorer l'intensité de couleur et/ou l'accumulation de couleur et/ou la persistance de couleur.
PCT/EP2018/086590 2017-12-22 2018-12-21 Procédé en plusieurs étapes pour teinter des fibres de kératine à l'aide d'une poudre de plantes produisant de l'indigo, et pour un traitement de colorant alcalin Ceased WO2019122332A1 (fr)

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FR1762947 2017-12-22
FR1762947A FR3075614B1 (fr) 2017-12-22 2017-12-22 Procede de coloration des fibres keratiniques en plusieurs etapes a partir de poudre de plante(s) indigofere(s), et de traitement colorant alcalin

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FR3104435B1 (fr) * 2019-12-13 2022-11-18 Oreal Procédé de coloration des fibres kératiniques à partir de poudre et/ou extrait de plantes indigofères et de l’arginine
DE102022205252A1 (de) * 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Zweistufiges Färbeverfahren zur verbesserten Haarfärbung mit Naturfarbstoffen
DE102022205250A1 (de) * 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Zweistufiges Färbeverfahren zur Verbesserung der Intensität von Färbungen mit Naturfarbstoffen

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EP0806199A2 (fr) 1996-05-09 1997-11-12 Wella Aktiengesellschaft Composition et procédé de teinture des fibres kératiniques
DE20100721U1 (de) * 2001-01-16 2001-04-12 Wella Ag, 64295 Darmstadt Mittel zum Färben keratinischer Fasern
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
FR2949196A1 (fr) * 2009-08-21 2011-02-25 Oreal Procede de coloration capillaire mettant en oeuvre un colorant chromenique ou chromanique
WO2016146225A1 (fr) * 2015-03-17 2016-09-22 Barroero Patricia Procede de coloration capillaire mettant en oeuvre des pigments naturels
FR3037237A1 (fr) * 2015-06-12 2016-12-16 Oreal Procede de coloration capillaire mettant en œuvre une etape de coloration a partir d'un colorant, et d'un sel de titane et une etape de revelation a partir d'agent alcalin comportant au plus une fonction amine

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EP0806199A2 (fr) 1996-05-09 1997-11-12 Wella Aktiengesellschaft Composition et procédé de teinture des fibres kératiniques
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
DE20100721U1 (de) * 2001-01-16 2001-04-12 Wella Ag, 64295 Darmstadt Mittel zum Färben keratinischer Fasern
FR2949196A1 (fr) * 2009-08-21 2011-02-25 Oreal Procede de coloration capillaire mettant en oeuvre un colorant chromenique ou chromanique
WO2016146225A1 (fr) * 2015-03-17 2016-09-22 Barroero Patricia Procede de coloration capillaire mettant en oeuvre des pigments naturels
FR3037237A1 (fr) * 2015-06-12 2016-12-16 Oreal Procede de coloration capillaire mettant en œuvre une etape de coloration a partir d'un colorant, et d'un sel de titane et une etape de revelation a partir d'agent alcalin comportant au plus une fonction amine

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