WO2020002690A1 - Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de dihydroxyisoquinolinium - Google Patents

Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de dihydroxyisoquinolinium Download PDF

Info

Publication number
WO2020002690A1
WO2020002690A1 PCT/EP2019/067493 EP2019067493W WO2020002690A1 WO 2020002690 A1 WO2020002690 A1 WO 2020002690A1 EP 2019067493 W EP2019067493 W EP 2019067493W WO 2020002690 A1 WO2020002690 A1 WO 2020002690A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
chosen
linear
alkyl radical
branched
Prior art date
Application number
PCT/EP2019/067493
Other languages
English (en)
Inventor
Leïla Hercouet
Maxime POURRET
Simon DONCK
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Publication of WO2020002690A1 publication Critical patent/WO2020002690A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—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
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to a method for stripping the artificial colour from human keratin fibres such as the hair, using a composition comprising one or more dihydroxyisoquinolinium salts, and also to the use of a composition comprising one or more dihydroxyisoquinolinium salts for stripping the artificial colour from human keratin fibres such as the hair.
  • oxidation dye precursors which are generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols, or heterocyclic compounds such as pyrazoles, pyrazolinones or pyrazolo-pyridines.
  • oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • oxidation bases may be varied by combining them with couplers or colour modifiers, the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta- diphenols and certain heterocyclic compounds such as indole or pyridine compounds.
  • couplers or colour modifiers the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta- diphenols and certain heterocyclic compounds such as indole or pyridine compounds.
  • couplers or colour modifiers the variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained.
  • the second type of dyeing is "semi-permanent” dyeing or direct dyeing, which consists in applying, to the keratin fibres, direct dyes, which are coloured and colouring molecules that have affinity for said fibres, in leaving them on for a time, and then in rinsing them off.
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo, xanthene, acridine, azine and triarylmethane direct dyes, and natural dyes.
  • oxidation dyes may be used in combination with direct dyes.
  • direct dye means natural and/or synthetic dyes, other than oxidation dyes. They are dyes that will superficially diffuse on the fibre and dye the fibres by themselves.
  • the direct dye(s) may be natural or synthetic, cationic, anionic or non-ionic direct dyes.
  • natural dyes or “dyes of natural origin” is intended to mean dyes derived from natural materials (plant, mineral or animal origin), for instance extracts, ground material and decoctions, which have a greater or smaller concentration of dyes.
  • the natural dyes may be chosen especially from spinulosin, orceins, polyphenols or ortho-diphenols (also known as ODPs in the rest of the description) and all extracts rich in ODPs, curcumin, indole derivatives such as isatin or indole-2, 3- dione, indigoids including indigo, phthalocyanines and porphyrins in particular complexed to a metal, glycosyl or non-glycosyl iridoids, chromene dyes, anthraquinone and naphthoquinone dyes such as lawsone or henna, juglone, spinulosin, chromene or chroman dyes, such as neoflavanols and neoflavanones, flavanols; and anthocyanidols.
  • Use may also be made of extracts or decoctions containing these natural dyes and especially plant extracts or poultices containing said dye
  • the user may be led to partially or totally destroy the dyes thus formed or introduced into or onto the hair. Stripping of the artificial colour of the keratin fibres is then performed.
  • artificial colour is intended to mean a colour obtained by means of the two types of dyeing described above.
  • This stripping is generally performed via methods using oxidizing or reducing systems.
  • the prior art stripping techniques which use peroxygenated reagents such as persulfates, perborates or percarbonates of ammonium or of alkali metals, that are combined at the time of use with an aqueous composition of hydrogen peroxide, are often very aggressive and modify the chemical structure of keratin. This results in poor cosmetic properties of the hair, such as difficulty in
  • This fibre degradation is particularly undesirable since it irreversibly deteriorates the physicochemical properties of the hair. Said hair becomes more porous and consequently more difficult to dry, it exhibits a greater sensitivity to various other hair treatments such as dyeing or permanent-waving, and it experiences an unfavourable modification of its mechanical properties and its surface properties, which results for example in a decrease in the tensile breaking strength or an increase in the coefficient of friction. There is thus a real need to provide a method which makes it possible to overcome these drawbacks.
  • dihydroxyisoquinolinium salts for stripping the artificial colour from human keratin fibres, preferably the hair, makes it possible to overcome the drawbacks described above.
  • a subject of the invention is thus a method for stripping the artificial colour from human keratin fibres such as the hair, which comprises applying to said artificially dyed fibres, a composition comprising one or more dihydroxyisoquinolinium salts as defined below by formulae (I) and (II).
  • Another subject of the invention is a method implementing: - a step of dyeing human keratin fibres such as the hair using a dye composition comprising one or more dyes chosen from oxidation dyes and/or direct dyes,
  • a subject of the invention is the use of a composition comprising one or more dihydroxyisoquinolinium salts as defined below, for stripping the artificial colour from human keratin fibres such as the hair.
  • the expression“stripping the artificial colour from human keratin fibres such as the hair” is intended to mean removing the artificial colour from human keratin fibres such as the hair, previously dyed using an oxidation dyeing and/or direct dyeing composition.
  • the stripping method differs from a method for bleaching or lightening keratin fibres such as the hair which aims to degrade the melanin pigments of the hair.
  • R1 represents: a linear or branched, unsubstituted C1-C12 alkyl radical
  • ⁇ a saturated or unsaturated, optionally aromatic, 5- or 6-membered heterocycle, optionally substituted with one or more radicals, which may be identical or different, chosen from:
  • o a linear or branched C1-C6 alkyl radical, o a linear or branched C1-C6 hydroxyalkyl radical, o a C1-C6 alkoxy radical, o a hydroxyl radical, o an amino radical -NR10R11, o a pyrrolidine, piperidine or morpholine radical, o an ammonium radical NTRaRbRc in which R a , Rb and R c denote, independently of one another, a linear or branched C1-C6 alkyl radical or a C1-C6 hydroxyalkyl radical,
  • ⁇ a saturated or unsaturated, optionally aromatic, 5- or 6-membered cationic heterocycle optionally substituted with one or more radicals, which may be identical or different, chosen from a linear or branched C1-C6 alkyl radical, a C1-C6 hydroxyalkyl radical, a C1-C6 alkoxy radical, a hydroxyl radical and an amino radical - NR10R11,
  • R a , Rb and Rc denote, independently of one another, a linear or branched C1-C6 alkyl radical or a C1-C6 hydroxyalkyl radical
  • R2, R3, R4, R5, R6, R7, Re and R9 represent, independently of one another, a radical chosen from:
  • R10 and Rn which may be identical or different, denote a hydrogen atom or a linear or branched C1-C6 alkyl radical,
  • R12 and R13 which may be identical or different, denote a linear or branched C1-C6 alkyl radical, substituted with a hydroxyl group;
  • R’l, R’2, R’S, R’S, R’e, R’7, R’8, R’9, R’lO, R"I , R"2, R"3, R"5, R" 6 , R'V, R"8, R"9 and R"io represent, independently of one another, a radical chosen from:
  • C1-C6 alkyl radical optionally substituted with one or more groups, which may be identical or different, chosen from hydroxyl, C1-C6 alkoxy, cyano and amino -NR’aR’b groups,
  • R and R m 4 represent, independently of one another: - a C1-C6 alkyl radical optionally substituted with one or more groups, which may be identical or different, chosen from hydroxyl, amino -NR’aR’b, C1- C6 alkoxy, cyano, aminocarbonyl -CONH2 and carboxyl -CO2H groups,
  • divalent radical L representing a linear or branched, saturated or unsaturated C1 -C15 alkylene radical, optionally substituted with one or more hydroxyl groups and/or interrupted with one or more non-adjacent heteroatoms chosen from oxygen, nitrogen and sulfur atoms, or
  • R’i represents one of the radicals R’1 to R’10 and R"j represents one of the radicals R"i to R"io; i and j denoting an integer ranging from 1 to 10,
  • R’ a and R’b represent, independently of one another, a hydrogen atom or a linear or branched, saturated or unsaturated C1-C6 alkyl radical,
  • An- denotes an anion or a mixture of anions ensuring the electrical neutrality of the compounds of formula (I) or (II).
  • anion or a mixture of anions ensuring the electrical neutrality of the compounds of formula (I) or (II) is intended to mean more particularly an anion or an anionic group chosen from: i) a halide such as a chloride or a bromide; ii) a nitrate; iii) a sulfonate including C1 -C6 alkylsulfonates: Alk-S(0)20 _ such as methylsulfonate or mesylate and ethylsulfonate; iv) an arylsulfonate: Ar-S(0)20 such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) an alkyl sulfate: Alk-0-S(0)0 such as methyl sulfate or ethyl sulfate
  • addition salts of the compounds of formulae (I) and (II) according to the invention are in particular chosen from addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, methanesulfonates, phosphates and acetates, and the addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
  • an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, methanesulfonates, phosphates and acetates
  • a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
  • the solvates of the compounds of formulae (I) and (II) according to the invention more particularly represent the hydrates of said compounds and/or the combination of said compounds with a linear or branched Ci to C4 alcohol such as methanol, ethanol, isopropanol or n-propanol.
  • a linear or branched Ci to C4 alcohol such as methanol, ethanol, isopropanol or n-propanol.
  • the solvates are hydrates.
  • the invention uses a composition comprising one or more compounds of formula (I) for stripping the artificial colour from human keratin fibres such as the hair.
  • R represents in formula (I):
  • R1 represents in formula (I):
  • R10 and R1 1 which may be identical or different, represent a C1 -C3 alkyl radical
  • Rd corresponding to a linear C1-C4 and preferably C1 alkyl radical, an ammonium radical NTRaRbRc in which R a , Rb and R c denote, independently of one another, a C1-C3 and preferably C1 alkyl radical, a saturated or unsaturated, optionally aromatic, 5- or 6-membered heterocycle, chosen from:
  • R a corresponds to a C1-C3 and preferably C1 alkyl radical
  • heterocycle being optionally substituted with an amino radical - NR10R11 in which R10 and Rn are as defined above, or with an ammonium radical N + R a RbRc in which R a , Rb and Rc are as defined above.
  • the cationic heterocycle is chosen from:
  • the cationic heterocycle is aromatic and especially corresponds to: in which Rd corresponds to a linear C1-C4 and preferably C1 alkyl radical.
  • the heterocycle is chosen from:
  • the heterocycle is aromatic and is chosen from:
  • the R2, R3, R4, R5, R6, R7, Re and R9 groups preferably represent, independently of one another, a hydrogen atom, or a linear C1-C4 alkyl radical, optionally substituted with a C1-C4 alkoxy group.
  • An- and X represent, independently of one another, an anion chosen from halides, in particular chloride and bromide; (Ci-C6)alkylsulfonates chosen from methylsulfonate or mesylate and ethylsulfonate; arylsulfonates chosen from benzenesulfonate and toluenesulfonate or tosylate; tartrate; citrate; lactate;
  • An- is an anion chosen from halides, in particular chloride and bromide, and para-toluenesulfonate.
  • An- is more particularly an anion chosen from halides, in particular chloride and bromide, and X
  • the compounds of formula (I) or (II) are chosen from the following compounds:
  • the compounds of formula (I) are chosen from the compounds (1 ) to (37), better still from the compounds (1 ) to (3) and (10) to (37), and even better still from the compounds (1 ), (1 1 ) and (12) and also mixtures thereof.
  • the compound(s) (I) and (II) and/or the addition salt(s) thereof and/or the solvate(s) thereof is (are) used in a proportion ranging from 0.1 % to 100% by weight, more preferentially from 1 % to 50% by weight, better still from 2% to 20% by weight, even better still from 5% to 15% by weight, relative to the total weight of the composition.
  • the pH of the composition used in the invention ranges generally from 1 to 7, preferably from 1 to 6, better from 2 to 5 and better still from 2 to 4.
  • the method according to the invention may also use one or more chemical oxidizing agents.
  • chemical oxidizing agents used conventionally, mention may be made of hydrogen peroxide, compounds that can produce hydrogen peroxide by hydrolysis, such as urea peroxide or persalts such as perborates, percarbonates and persulfates, hydrogen peroxide being particularly preferred.
  • the chemical oxidizing agent(s) is (are) used in a proportion ranging from 2% to 20% by weight, even better still from 7% to 12% by weight, relative to the total weight of the composition.
  • the method uses one or more chemical oxidizing agents, preferably hydrogen peroxide.
  • the method preferably uses a composition C) comprising one or more compounds of formula (I) or of formula (II) and/or the addition salts thereof and/or the solvates thereof, and one or more chemical oxidizing agents, preferably hydrogen peroxide.
  • the composition C) can be obtained by mixing, at the time of use (extemporaneous mixing), a composition C1 ) comprising one or more compounds of formula (I) or of formula (II) and/or the addition salts thereof and/or the solvates thereof, and a composition C2) comprising one or more chemical oxidizing agents, preferably hydrogen peroxide.
  • the term“ready-to-use composition” is used to refer to the composition applied to the keratin fibres, such as the hair.
  • the ready-to-use composition can result from the mixing of the compositions C1 ) and C2) as previously described, and corresponding to the composition C).
  • the ready-to-use composition used in the method of the invention preferably comprises the compound(s) of formula (I) or (II) and/or the addition salts thereof and/or the solvates thereof in a total content ranging from 0.1 % to 100% by weight, more preferentially from 1 % to 50% by weight, better still from 2% to 20% by weight, even better still from 5% to 15% by weight, relative to the total weight of the ready-to-use composition.
  • the ready-to-use composition may also comprise one or more fatty substances, which are preferably liquid(s) (or oil(s)).
  • fatty substance is intended to mean 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 have in their structure at least one
  • hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, ethanol, benzene, liquid petroleum jelly or
  • o ⁇ G is intended to mean a "fatty substance” that is liquid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013x10 5 Pa).
  • non-silicone oil is intended to mean an oil not containing any silicon atoms (Si) and the term “silicone oil” is intended to mean an oil containing at least one silicon atom.
  • the fatty substances are chosen from C6-C16 hydrocarbons, non-silicone (hydrocarbon-based) oils comprising more than 16 carbon atoms, of plant, animal, mineral or synthetic origin, triglycerides of plant or synthetic origin, fluoro oils, fatty alcohols, non-salified fatty acids, esters of fatty acid and/or of fatty alcohol other than triglycerides, non-silicone waxes other than solid fatty alcohols and than solid synthetic esters, and silicones, and mixtures thereof.
  • C6-C16 hydrocarbons non-silicone (hydrocarbon-based) oils comprising more than 16 carbon atoms, of plant, animal, mineral or synthetic origin, triglycerides of plant or synthetic origin, fluoro oils, fatty alcohols, non-salified fatty acids, esters of fatty acid and/or of fatty alcohol other than triglycerides, non-silicone waxes other than solid fatty alcohols and than solid synthetic esters, and silicones
  • 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.
  • C6-C16 hydrocarbons mention may in particular be made of C6-C16 alkanes, the latter being linear, branched, or optionally cyclic.
  • Examples that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
  • the hydrocarbon-based oils comprising more than 16 carbon atoms may be linear or branched. They may be chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam®, squalane, squalene, and mixtures thereof.
  • hydrocarbon-based oils of plant origin mention may be made of the refined plant perhydrosqualene sold under the name Fitoderm by the company Cognis; the plant squalane sold, for example, under the name Squalive by the company Biosynthis.
  • a hydrocarbon-based oil of animal origin that may be mentioned is
  • the triglycerides of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, more particularly from those present in plant oils, for instance sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, jojoba oil, shea butter oil or synthetic caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, and mixtures thereof.
  • the fluoro oils may be chosen from 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 alternatively 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.
  • the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 8 to 30 carbon atoms. Examples that may be mentioned include cetyl alcohol, stearyl alcohol and a mixture thereof (cetylstearyl alcohol),
  • octyldodecanol 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol, linolenyl alcohol, ricinoleyl alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof.
  • the fatty acids that may be used in the context of the invention are more particularly chosen from saturated or unsaturated carboxylic acids containing from 6 to 30 carbon atoms and in particular from 9 to 30 carbon atoms. They are advantageously chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid. These fatty acids are, in the composition of the invention, not salified with organic or mineral bases, so as not to give rise to soaps.
  • esters of fatty acids and/or of fatty alcohols other than the triglycerides mentioned above and plant waxes mention may be made in particular of esters of saturated or unsaturated, linear C1-C26 or branched C3-C26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear Ci-C26 or branched C3-C26 aliphatic monoalcohols or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
  • octyldodecyl behenate isocetyl behenate; cetyl lactate; C12-C15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate;
  • isocetyl isostearate isocetyl laurate; isocetyl stearate; isodecyl octanoate;
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1 -C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • diisopropyl adipate di-n-propyl adipate; dioctyl adipate; diisostearyl adipate;
  • dioctyl maleate dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate;
  • pentaerythrityl monoricinoleate pentaerythrityl tetraisononanoate
  • pentaerythrityl tetrapelargonate pentaerythrityl tetraisostearate
  • pentaerythrityl tetraoctanoate propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate;
  • triisopropyl citrate triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate; and polyethylene glycol distearates, and mixtures thereof.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2- hexyldecyl laurate, isononyl isononanoate or cetyl octanoate, and mixtures thereof.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobut
  • composition may also comprise, as fatty ester, sugar esters and diesters of C6-C30 and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C6-C30 and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C6-C30 and preferably C12-C22 fatty acids.
  • sugar esters are intended to mean oxygen-bearing hydrocarbon-based compounds bearing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the esters of sugars and of fatty acids may especially be chosen from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6-C30, preferably C12-C22, fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from mono-, di-, tri- and tetraesters, polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and
  • arachidonates or mixtures thereof such as, in particular, oleopalmitate,
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleate or dioleate, stearate, behenate,
  • esters or mixtures of esters of sugar and of fatty acid examples include:
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% d iester-triester-polyester;
  • the non-silicone wax(es) other than solid fatty alcohols and solid synthetic esters are chosen especially from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by the company Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that may be used according to the invention are especially marine waxes, such as the wax sold by the company Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
  • the fatty substance(s) do not comprise any C2-C3 oxyalkylene units. Preferably, they do not contain any glycerol units. More particularly, the fatty substances are other than fatty acids.
  • the fatty substances are chosen from compounds that are liquid or pasty at ambient temperature and at atmospheric pressure.
  • the fatty substance is a compound that is liquid at a temperature of 25°C and at atmospheric pressure, or oil.
  • the fatty substances are not silicone-based.
  • the fatty substances are preferably chosen from C6-C16 hydrocarbons, hydrocarbon-based oils comprising more than 16 carbon atoms, of plant, animal, mineral or synthetic origin, triglycerides of plant or synthetic origin, fatty alcohols, fatty acid and/or fatty alcohol esters, or mixtures thereof.
  • the fatty substance is chosen from linear or branched hydrocarbon- based oils, of mineral or synthetic origin, comprising more than 16 carbon atoms, or mixtures thereof, for instance liquid petroleum jelly.
  • the ready-to-use composition used in the method of the invention comprises one or more fatty substances, which are preferably liquid
  • the total content thereof preferably ranges from 1 % to 90% by weight, more preferentially from 10% to 80% by weight, better still from 20% to 70%, even more
  • the ready-to-use composition may also comprise one or more surfactants, preferably one or more non-ionic surfactants.
  • the non-ionic surfactants preferably one or more non-ionic surfactants.
  • surfactant(s) are chosen from oxyalkylenated (OA), preferably oxyethylenated, non-ionic surfactants.
  • the ready-to-use composition comprises at least one oxyalkylenated (OA) non-ionic surfactant comprising a number of OA units ranging from 1 to 9 and at least one oxyalkylenated (OA) non-ionic surfactant comprising at least 10 OA units.
  • OA oxyalkylenated
  • oxyalkylenated non-ionic surfactant(s) comprising a number of OA units ranging from 1 to 9 to the amount of oxyalkylenated non-ionic surfactant(s) comprising at least 10 OA units is greater than 1 , preferably greater than or equal to 1.2, better still greater than or equal to 1.5 and even better still greater than or equal to 2.
  • the oxyalkylenated non-ionic surfactants according to the invention are chosen from oxyethylenated non-ionic surfactants.
  • the ready-to-use composition according to the invention comprises at least one oxyethylenated (OE) non-ionic surfactant comprising a number of OE units ranging from 1 to 9 and at least one oxyethylenated (OE) non-ionic surfactant comprising at least 10 OE units.
  • OE oxyethylenated
  • the weight ratio, in the ready-to-use composition of the invention, of the amount of oxyethylenated non-ionic surfactant(s) comprising a number of OE units ranging from 1 to 9 to the amount of oxyethylenated non-ionic surfactant(s) comprising at least 10 OE units is greater than 1 , preferably greater than or equal to 1.2, better still greater than or equal to 1.5 and even better still greater than or equal to 2.
  • This weight ratio may range, for example, from 1.2 to 15, better still from 1.5 to 10 and even better still from 2 to 5.
  • oxyethylenated non-ionic surfactants comprising a number of OE units ranging from 1 to 9 and the oxyethylenated (OE) non-ionic surfactants comprising at least 10 OE units can be chosen from the following categories: •oxyethylenated (C8-C24)alkylphenols,
  • the oxyethylenated non-ionic surfactant comprising at least 10 OE units and the oxyethylenated non-ionic surfactant comprising from 1 to 9 OE units are chosen from oxyethylenated, saturated or unsaturated, linear or branched, preferably linear, C8-C30, preferably C12-C22 and better still C14-C20, fatty alcohols, for instance cetyl alcohol, oleyl alcohol, oleocetyl alcohol, behenyl alcohol, cetearyl alcohol and stearyl alcohol, and mixtures thereof, and more preferably stearyl alcohol.
  • oxyethylenated non-ionic surfactant comprising from 1 to 9 OE units, of oxyethylenated non-ionic surfactants comprising from 2 to 8 and preferably from 2 to 4 OE units, for instance the products of addition of ethylene oxide and stearyl alcohol such as stearyl alcohol 2 OE (CTFA name: Steareth-2).
  • the oxyethylenated non-ionic surfactants comprising at least 10 OE units used in the invention may in particular contain a number of oxyethylene groups, ranging from 10 to 50, preferably from 15 to 30 and better still from 15 to 25, for instance the products of addition of ethylene oxide and stearyl alcohol such as stearyl alcohol 20 OE (CTFA name: Steareth-20).
  • the content of oxyalkylenated, preferably oxyethylenated, non-ionic surfactant(s) comprising from 1 to 9 oxyalkylene units, preferably oxyethylene units, in the ready-to-use composition according to the invention may range from 0.5% to 15% by weight, preferably from 1 % to 10% by weight and better still from 2% to 6% by weight relative to the total weight of the composition.
  • the content of oxyalkylenated, preferably oxyethylenated, non-ionic surfactants comprising at least 10 oxyalkylene groups, preferably oxyethylene groups, in the ready-to-use composition according to the invention may range from 0.1 % to
  • the total amount of oxyalkylenated, preferably oxyethylenated, non-ionic surfactants in the ready-to-use composition may range from 1 % to 25% by weight, preferably from 2% to 15% by weight and better still from 3% to 7% by weight relative to the total weight of the composition.
  • the ready-to-use composition used in the method of the invention generally comprises water.
  • the water content can range from 10% to 95% by weight, preferably from 20% to 70%, better still from 20% to 50% by weight, relative to the ready-to-use composition.
  • composition comprising one or more compounds of formulae (I) and (II) and/or the addition salts thereof and/or the solvates thereof may comprise one or more additional ingredients chosen from ionic liquids, organic solvents, anionic surfactants, cationic surfactants or non-ionic surfactants, other than those listed above, and amphoteric surfactants, cationic, anionic, non-ionic or amphoteric polymers or mixtures thereof, antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers or nacreous agents, antioxidants, hydroxy acids, fragrances, preservatives, pigments and ceramides.
  • additional ingredients chosen from ionic liquids, organic solvents,
  • Another subject of the invention is a method for stripping the artificial colour from human keratin fibres, such as the hair, which comprises the steps consisting:
  • Another subject of the invention is a method implementing:
  • a step of dyeing human keratin fibres such as the hair using a dye composition comprising one or more dyes chosen from oxidation dyes and/or direct dyes,
  • a step of stripping the artificial colour from said fibres using a composition comprising one or more compounds of formulae (I) and (II) and/or the addition salts thereof and/or the solvates thereof as previously described, preferably in the presence of one or more chemical oxidizing agents, preferably hydrogen peroxide.
  • the method preferably uses a composition C) as defined above.
  • a subject of the invention is the use of a composition comprising one or more compounds of formula (I) or of formula (II) and/or the addition salts thereof and/or the solvates thereof as previously described, for stripping the artificial colour from human keratin fibres such as the hair.
  • the following oxidizing composition A was prepared from the following ingredients in the following proportions indicated as % by weight of product relative to the total weight of the composition in Table 1 :
  • a 1 g lock of natural hair containing 90% grey hairs was dyed beforehand with a Movida chestnut brown dye under the following conditions: 5 g of dye mixture, obtained by mixing the dye support and the oxidizing agent that are sold by L’Oreal, in the proportions 1 + 2, were applied to the lock for a leave-on time of 15 minutes.
  • the lock was then rinsed, washed with a shampoo, and then dried.
  • the following oxidizing composition B was prepared from the following ingredients in the following proportions indicated as % by weight of product relative to the total weight of the composition in Table 2:
  • the three parameters denote, respectively, the colour intensity (L*), the green/red colour axis (a*) and the blue/yellow colour axis (b*).
  • L* colour intensity
  • a* green/red colour axis
  • b* blue/yellow colour axis
  • Lo*, ao* and bo* represent the values measured on the locks of hair dyed with Movida dye.
  • the method using compound 12 according to the invention results in a higher AEab* value, and thus in better stripping compared with the comparative method on previously dyed locks. Moreover, the treatment carried out with compound 12 on natural locks results in a lower DE’ value, and thus in less degradation of the melanin pigments of the hair compared with the comparative treatment.
  • a lock was dyed with a Movida chestnut brown dye in the same way as that indicated in Example 1 , with the exception that the leave-on time was 10 minutes.
  • the lock was then rinsed, then shampooed and dried.
  • the method using compound 1 or 11 according to the invention results in a higher AEab* value, and thus in better stripping compared with the comparative method, on previously dyed locks.
  • the treatment carried out with compound 1 or 11 on natural locks results in a lower DE’ value, and thus in less degradation of the melanin pigments of the hair compared with the comparative treatment.

Landscapes

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

Abstract

La présente invention concerne un procédé de décapage de la couleur artificielle des fibres de kératine telles que les cheveux avec des sels de dihydroxyisoquinolinium, ainsi que l'utilisation de sels de dihydroxyisoquinolinium pour décaper la couleur artificielle de fibres de kératine humaines telles que les cheveux.
PCT/EP2019/067493 2018-06-29 2019-06-28 Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de dihydroxyisoquinolinium WO2020002690A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1855963A FR3083101B1 (fr) 2018-06-29 2018-06-29 Procede de decapage de la couleur artificielle des fibres keratiniques avec des sels de dihydroxyisoquinolinium
FR1855963 2018-06-29

Publications (1)

Publication Number Publication Date
WO2020002690A1 true WO2020002690A1 (fr) 2020-01-02

Family

ID=65031320

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/067493 WO2020002690A1 (fr) 2018-06-29 2019-06-28 Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de dihydroxyisoquinolinium

Country Status (2)

Country Link
FR (1) FR3083101B1 (fr)
WO (1) WO2020002690A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007047688A1 (de) * 2007-10-04 2009-04-09 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen 3,4-Dihydroisochinoliniumderivaten und Wasserstoffperoxid
WO2017109183A1 (fr) * 2015-12-23 2017-06-29 L'oreal Utilisation de sels de dihydroisoquinolinium pour traiter des matières kératiniques, compositions et procédés de mise en œuvre
WO2017109184A1 (fr) * 2015-12-23 2017-06-29 L'oreal Utilisation de dérivés doubles de dihydroisoquinolinium pour traiter des matières kératiniques, compositions et procédés de mise en œuvre
FR3046167A1 (fr) * 2015-12-23 2017-06-30 Oreal Utilisation de sels de dihydroisoquinolinium non substitue pour le traitement des matieres keratiniques, compositions et procedes de mise en oeuvre

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007047688A1 (de) * 2007-10-04 2009-04-09 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen 3,4-Dihydroisochinoliniumderivaten und Wasserstoffperoxid
WO2017109183A1 (fr) * 2015-12-23 2017-06-29 L'oreal Utilisation de sels de dihydroisoquinolinium pour traiter des matières kératiniques, compositions et procédés de mise en œuvre
WO2017109184A1 (fr) * 2015-12-23 2017-06-29 L'oreal Utilisation de dérivés doubles de dihydroisoquinolinium pour traiter des matières kératiniques, compositions et procédés de mise en œuvre
FR3046167A1 (fr) * 2015-12-23 2017-06-30 Oreal Utilisation de sels de dihydroisoquinolinium non substitue pour le traitement des matieres keratiniques, compositions et procedes de mise en oeuvre

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Kosmetik und Hygiene", 30 June 2004, WILEY-VCH, Weinheim, ISBN: 978-3-527-30996-2, article WILFRIED UMBACH: "9.5 Haarfarbänderungsmittel - 9.5.1.3 Anwendung", pages: 299, XP055563746 *

Also Published As

Publication number Publication date
FR3083101A1 (fr) 2020-01-03
FR3083101B1 (fr) 2022-07-15

Similar Documents

Publication Publication Date Title
US7879113B2 (en) Composition comprising at least one fatty substance and at least one silicate, dyeing or lightening process using it and devices or kits therefor
KR101781964B1 (ko) 지방 물질 및 격리제를 포함하는 2-부분 케라틴 섬유 염색 및/또는 표백제
EP2926802B1 (fr) Compositions de coloration capillaire, kits, procédé et leur utilisation
US20100180389A1 (en) Composition comprising at least one fatty substance and at least one surfactant comprising ethylene oxide, dyeing or lightening process using it and devices therefor
FR2940104A1 (fr) Procede de traitement des cheveux mettant en oeuvre une emulsion directe comprenant un agent oxydant et une composition contenant un agent alcalin
FR2954121A1 (fr) Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties, comprenant un corps gras particulier et une reductone.
BRPI0817147B1 (pt) Processo de coloração e/ou de clareamento das fibras queratínicas humanas, composição e dispositivo com múltiplos compartimentos
WO2014174114A2 (fr) Procédé de coloration de cheveux utilisant du henné puis de l'indigo et une huile et/ou un beurre
BRPI0911109B1 (pt) processo de coloração ou de clareamento das matérias queratínicas humanas e dispositivo com múltiplos compartimentos
EP3346970A1 (fr) Composition pour modifier la couleur de fibres de kératine
WO2011076646A2 (fr) Agent de coloration et/ou de blanchiment de fibres kératiniques, comprenant une émulsion inverse comprenant un agent oxydant
WO2014131870A1 (fr) Procédé de teinture et/ou de décoloration de fibres de kératine au moyen d'une composition oxydante sous forme de nanoémulsion huile dans eau
WO2013083702A1 (fr) Composition à base de poudre de henné rouge et de beurre(s), et procédé de teinture de cheveux à l'aide de ladite composition
WO2020002690A1 (fr) Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de dihydroxyisoquinolinium
WO2016097126A1 (fr) Composition de coloration ou d'éclaircissement de fibres kératiniques, sous la forme d'une micro-émulsion à base d'huile(s) particulière(s), de solvants hydrotropiques et de tensioactif(s)
WO2014174116A2 (fr) Composition basée sur une poudre de henné ou d'indigo ayant une prédispersion d'huile, et procédé de coloration de cheveux utilisant cette composition
FR2971158A1 (fr) Procede d'eclaircissement ou de coloration en presence de (bi)carbonate d'ammonium et d'une base minerale, dispositif
WO2020002685A1 (fr) Procédé de décapage de la couleur artificielle des fibres de kératine avec des sels de pyridinium
WO2011131676A2 (fr) Procédé de coloration ou d'éclaircissement et émulsion inverse pour le traitement des cheveux comprenant un solvant particulier
WO2016097124A1 (fr) Composition pour la coloration ou l'éclaircissement de fibres de kératine, sous la forme d'une microémulsion à base d'huile(s) et de tensioactif(s)
JP7104954B2 (ja) 酸化染毛剤組成物
WO2014131872A2 (fr) Composition cosmétique se présentant sous la forme d'une nanoémulsion huile dans l'eau pour la coloration directe de fibres kératiniques
EP2914347A2 (fr) Composition riche en huile et son utilisation dans un procédé de coloration directe éclaircissant ou non éclaircissant
JP7134454B2 (ja) 毛髪脱色・脱染剤組成物又は染毛剤組成物
JP7044236B2 (ja) 毛髪変形用還元性組成物

Legal Events

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

Ref document number: 19733087

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19733087

Country of ref document: EP

Kind code of ref document: A1