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WO2019121631A1 - Procédé de traitement de fibres de kératine par l'utilisation d'un colorant direct de fluorescéine halochromique, d'un révélateur alcalin, puis d'un effaceur acide - Google Patents

Procédé de traitement de fibres de kératine par l'utilisation d'un colorant direct de fluorescéine halochromique, d'un révélateur alcalin, puis d'un effaceur acide Download PDF

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Publication number
WO2019121631A1
WO2019121631A1 PCT/EP2018/085417 EP2018085417W WO2019121631A1 WO 2019121631 A1 WO2019121631 A1 WO 2019121631A1 EP 2018085417 W EP2018085417 W EP 2018085417W WO 2019121631 A1 WO2019121631 A1 WO 2019121631A1
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Prior art keywords
composition
hydrogen atom
alkyl
formula
alkali metal
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PCT/EP2018/085417
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English (en)
Inventor
Maxime POURRET
Frédéric Simonet
Arnaud Bonnamy
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L'oreal
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Publication of WO2019121631A1 publication Critical patent/WO2019121631A1/fr

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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
    • A61K8/4973—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
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D19/00—Devices for washing the hair or the scalp; Similar devices for colouring the hair
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D19/00—Devices for washing the hair or the scalp; Similar devices for colouring the hair
    • A45D19/0041—Processes for treating the hair of the scalp
    • A45D19/0066—Coloring or bleaching
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a process for treating keratin fibers, especially human keratin fibers such as the hair, using i) at least one fluorescein direct dye of formula (I) or (G) as defined below, then ii) an alkaline revealer, and then iii) an eraser at acidic pH.
  • a subject of the invention is also a composition comprising at least one fluorescein direct dye of formula (I) or (G) as defined below and at least one thickener and/or at least one hydrotropic solvent, and a multi compartment kit comprising i), ii) and iii) in three separate compartments.
  • oxidation dye precursors which are generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds such as diaminopyrazole derivatives.
  • oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds via a process of oxidative condensation.
  • couplers or color modifiers the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta diphenols and certain heterocyclic compounds such as indole compounds.
  • the "permanent" coloring obtained by means of these oxidation dyes should moreover satisfy a certain number of requirements. Thus, it should have no toxicological drawbacks, it should allow shades to be obtained in the desired intensity, and it should show good resistance to external agents such as light, bad weather, washing, permanent waving treatments, perspiration and rubbing.
  • the dyes should also allow gray hair to be covered and, finally, they should be as unselective as possible, i.e. they should produce the smallest possible differences in color along the same keratin fiber, which in general is differently sensitized (i.e. damaged) between its end and its root. It is also known practice to dye keratin fibers, and in particular human keratin fibers such as the hair, with dye compositions containing direct dyes. These dyes are colored and coloring molecules that have affinity for keratin fibers, They are applied to the keratin fibers for a time necessary to obtain the desired coloring, and are then rinsed out.
  • the conventional dyes that are used are, in particular, dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, cationic azo, xanthene, acridine, azine, triarylmethane type, or natural dyes.
  • the colorings obtained are temporary or semi-permanent, since the nature of the interactions that bind the direct dyes to the keratin fiber and their desorption from the surface and/or the core of the fiber are responsible for their weak dyeing power and their poor persistence with respect to washing, inclement weather or perspiration.
  • These direct dyes are also generally light-sensitive due to the low resistance of the chromophore to photochemical attack, and lead to fading of the coloring of the hair over time.
  • the prior art processes do not describe successive steps of “switch on - switch off - switch on - switch off' dyeing.
  • the dyes are not always sufficiently persistent, and/or there is a decrease in the color properties of the color revealed in terms of color build-up, intensity, chromaticity, persistence especially with respect to successive shampoo washing, and/or selectivity of the color between the root and the end.
  • these dyes are not always switchable for " switch off- switch on” or "switch on - switch off’ changes.
  • Another problem encountered is that of rapid and sharp revealing or erasure of the color without any residual color remaining after the“switch off' color erasure step.
  • the aim of the invention is to provide keratin fiber colorings with intense colors, and a good color build-up which can switch as a function of the pH ideally close to neutrality, even after several cycles, with a rapid and sharp effect of the " switch off - switch on " or " switch on - switch off " color change, with structured effects (geometrical, graphic, etc. effect), without any color transfer from one lock to another (e.g. possibility on a braid comprising three dyes of different colors of there being no color diffusion from one lock to another even after several pH revealing cycles), and which can allow revealing or erasure of the color without running, and avoid denaturing of the keratin fibers.
  • Another aim is to be able to obtain coloring in fundamental colors that can be erased or change color sharply, visibly and rapidly.
  • composition (A) comprising one or more fluorescein compounds of formula (I) or (G), and also mineral or organic base salts thereof, optical, geometrical and tautomeric isomers thereof, and also solvates thereof such as hydrates:
  • R" represents a hydrogen atom, a halogen atom such as chlorine or bromine, or a group chosen from i) (C1 -C6)alkyl which is optionally substituted, in particular with one or more halogen atoms such as bromine, ii) optionally substituted (C1 -C6)alkoxy, iii) Ra-C(X)-, iv) Ra-C(X)-X-, v) Ra-X-C(X)-, and vi) iso(thio)cyanate with Ra representing a hydrogen atom, a heterocyclic group such as N-succinimide or a (C1 -C4)alkyl group optionally substituted with one or more halogen atoms such as bromine or iodine, or with one or more carboxyl groups; preferably, R" represents a hydrogen atom or a halogen atom such as chlorine or bromine;
  • R'" represents i) a hydrogen atom, ii) a halogen atom such as chlorine, bromine or iodine or a group chosen from iii) (C1 -C6)alkyl which is optionally substituted, especially with one or more groups from among: a) hydroxyl, b) (di)(C1 -C4)(alkyl)amino, c) (di)carboxy(C1 -C4)alkylamino, iv) (C1 -C6)alkoxy and v) hydroxyl; preferably i) a hydrogen atom, ii) a halogen atom such as chlorine, bromine or iodine or a group chosen from iii) (C1 -C6)alkyl which is optionally substituted, especially with one or more groups from among: a) hydroxyl, b) (di)(C1 -C4)(alkyl)amino, c) (d
  • X represents a heteroatom such as O, S or NR’ with R' representing a hydrogen atom or a (C1 -C6)alkyl group, preferably O;
  • M represents a hydrogen atom, an alkali metal or alkaline-earth metal, an ammonium group or a (C1 -C6)alkyl(thio)carbonyl group, in particular (C1 - C4)alkylcarbonyl such as acyl;
  • M’ represents a hydrogen atom, an alkali metal, an alkaline-earth metal or an ammonium group, preferably hydrogen or an alkali metal such as sodium ; and then:
  • composition (A) comprises one or more compounds of formula (I)
  • the application of composition (A) is followed ii) by a revealing (" switch on”) step which consists in applying to said fibers a composition (B) at basic pH; followed iii) by a step of switching off or erasing the color (" switch off') which consists in applying to said fibers a composition (C) at acidic pH; and
  • composition (A) comprises one or more compounds of formula (G)
  • the application of composition (A) is followed iii) by a step of switching off the color which consists in applying to said fibers a composition (C) at acidic pH, followed ii) by a revealing step which consists in applying to said fibers a composition (B) at basic pH;
  • steps ii) and iii) may be repeated several times.
  • composition (A-i) comprising a) one or more fluorescein compounds of formulae (I) and/or (G) as defined previously and optionally b) one or more thickeners, in particular polymeric thickeners, and/or one or more hydrotropic solvents, in particular aromatic hydrotropic solvents.
  • Another subject of the invention is a multi-compartment kit which comprises, i) in a first compartment: the fluorescein compounds of formula (I) or (G) as defined previously, ii) in a second compartment: a composition (B) at basic pH; and iii) in a third compartment: a composition (C) at acidic pH. i)
  • the keratin fiber treatment process of the invention involves in the first step a step of applying a composition (A) comprising one or more compounds of formula (I) or (G) as defined previously, or a step of applying (A-i) as defined previously.
  • the triarylmethane or sulfonophthalein compounds of formula (I) or (G) are dyes which have a color change zone at a pH inclusively between 4.5 and 8.
  • alkyl radical means a linear or branched, saturated hydrocarbon-based radical comprising from 1 to 6 carbon atoms, preferably comprising between 1 and 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl.
  • alkoxy radical is a radical alk-O- with the alkyl radical being as defined previously.
  • a carboxyl radical represents a carboxylic acid group -C(0)-0H.
  • X is as defined previously, preferably represents an oxygen atom; and M is as defined previously, preferably an alkali metal or a hydrogen atom, preferentially an alkali metal such as sodium;
  • X is as defined previously, preferably represents an oxygen atom
  • M is as defined previously, preferably an alkali metal or a hydrogen atom, preferentially an alkali metal such as sodium;
  • M’ is as defined previously, in particular represents a hydrogen atom or an alkali metal such as sodium;
  • halogen atom such as bromine
  • Hal represents a halogen atom such as chlorine
  • X is as defined previously, preferably represents an oxygen atom
  • M is as defined previously, preferably an alkali metal such as sodium or a hydrogen atom, preferentially an alkali metal such as sodium;
  • Hal represents a halogen atom such as chlorine
  • X is as defined previously, preferably represents an oxygen atom
  • M is as defined previously, preferably an alkali metal such as sodium or a hydrogen atom, preferentially an alkali metal such as sodium; and
  • M is as defined previously, in particular represents a hydrogen atom or an alkali metal such as sodium;
  • M is as defined previously, preferably a (Ci-C 4 )alkylcarbonyl group such as acyl ; ’
  • M is as defined previously, preferably a (Ci-C 4 )alkylcarbonyl group such as acyl;
  • M’ is as defined previously, in particular represents a hydrogen atom or an alkali metal such as sodium;
  • (Ci-C 4 )alkylcarbonyl group such as methylcarbonyl; preferably hydrogen; and M’ is as defined previously, in particular represents a hydrogen atom or an alkali metal such as sodium, preferably hydrogen;
  • Ra represents a hydrogen atom or a (Ci-C 4 )alkyl group
  • Rb represents a (Ci-C 4 )alkyl group optionally substituted with one or more halogen atoms such as bromine or iodine;
  • X is as defined previously, preferably represents an oxygen atom
  • p represents an integer between 1 and 5 inclusive; preferably, p is equal to 1 ; in particular, Rb is in position 3 or 4 of the phenyl group; and
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium, preferably hydrogen;
  • Rb represents (Ci-C 4 )alkyl optionally substituted with one or more halogen atoms such as bromine or iodine;
  • X is as defined previously, preferably represents an oxygen atom;
  • p represents an integer between 1 and 5 inclusive; preferably, p is equal to 1 ; in particular, Rb is in position 3 or 4 of the phenyl group;
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium, preferably hydrogen;
  • M is as defined previously, in particular represents a hydrogen atom or an alkali metal such as sodium, preferably hydrogen;
  • X is as defined previously, preferably represents an oxygen atom; and M is as defined previously, preferably an alkali metal or a hydrogen atom, preferentially an alkali metal such as sodium;
  • X is as defined previously, preferably represents an oxygen atom
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium;
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium;
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium;
  • alkali metal such as sodium
  • M is as defined previously, preferably a hydrogen atom or an alkali metal such as sodium;
  • the compounds of formulae (la) to (I’h) mention may be made of the compounds of formulae (la) to (I’h), and also the alkali metal or alkaline-earth metal salts thereof.
  • the compound(s) of formula (I) or (G) represent a compound of formula (la), (I'a), (lc), (I'c), (Id), (I'd), (le) or (le').
  • the compound(s) of formula (I) or (G) represent a compound of formula (1), (V), (2), (2’), (4), (4’), (5) and (5’); (6) and (6’), preferentially (4), (4’), (5) or (5'), more preferentially (5) or (5').
  • the compounds chosen from the compounds of formulae (I) and (G) as defined previously preferentially represent from 0.001 % to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of composition (A).
  • composition (A-i) comprises one or more compounds of formulae (I) and/or (G) as defined previously in an amount of between 0.001 % to 10% by weight, preferably between 0.005% to 5% by weight relative to the total weight of composition (A-i).
  • the organic or mineral base addition salts of the compounds of formula (I) in which the sulfonate ring is closed and the dyes corresponding to the compounds of formula (G) in which the sulfonate ring is open are especially chosen from the base addition salts chosen from the alkaline agents as defined below, in particular chosen from sodium hydroxide, potassium hydroxide, ammonia and alkanolamines.
  • Compositions (A) and (Ai) as defined previously may also comprise one or more direct dyes other than the compounds of formulae (I) and/or (G) as defined previously, which may be chosen especially from nitrobenzene dyes, azo direct dyes, methine direct dyes and natural dyes. These direct dyes may be of nonionic, anionic or cationic nature.
  • compositions (A) and (A-i) as defined previously also comprise one or more halochromic additional dyes other than the fluoresceins of formula (I) or (G) as defined previously.
  • the halochromic additional dye(s) other than fluoresceins are chosen from the triarylmethane compounds of formulae (II) and (IG), and also the mineral or organic base salts thereof, the optical, geometrical and tautomeric isomers thereof, and also the solvates thereof such as hydrates:
  • - R represents a hydrogen atom, a halogen atom such as chlorine or bromine, or a group chosen from (Ci-C6)alkyl and (Ci-C6)alkoxy;
  • - R’ represent a hydrogen atom or (Ci-C6)alkyl or a benzyl group
  • - R represents a hydrogen atom or a (Ci-C6)alkyl or (Ci-C6)alkoxy group
  • - R represents a hydrogen atom, a halogen atom such as chlorine or bromine, or a group chosen from hydroxyl, (Ci-C 4 )alkyl, (Ci-C6)alkoxy and carboxyl;
  • - X represents a heteroatom such as O, S and NR', preferably O; and M represents a hydrogen atom, an alkali metal, an alkaline-earth metal or ammonium.
  • the compound(s) of formula (II) or (IG) represent a compound of formula (lla), (ll'a), (Mb) and (ll'b), (lie), (ll'c), (lie) or (N'e).
  • the compound(s) of formula (II) or (IG) represent a compound of formula (II) or (IG) chosen from:
  • the compounds of formula (II) or (IG) represent a compound of formula 1, V, 2, 2 3, 3’, 5, and 5’.
  • composition (A) or (Ai) comprises one or more additional dyes, preferably chosen from those of formulae (II) and/or (IG) as defined previously in an amount of between 0.001 % to 10% by weight, preferably between 0.005% to 5% by weight relative to the total weight of composition (Ai).
  • Compositions (A) or (Ai) may also comprise one or more oxidation dyes chosen from the oxidation bases and couplers conventionally used in oxidation dyeing.
  • the oxidation dyes in composition (A) or (Ai) particularly represent from 0.001 % to 20% and preferably from 0.01 % to 10% by weight relative to the total weight of composition (A) or (Ai).
  • the process according to the invention involves, after the step of applying composition (A) or (A1 ) as defined previously, a revealing step using a revelation or revealing composition (B).
  • the revealing composition (B) is at basic pH, i.e. it is an aqueous composition with a pH of greater than 7, preferably between 7.5 and 12.5, particularly between 8.5 and 12, more particularly between 9 and 1 1 .5.
  • the revealing composition (B) contains one or more alkaline agents, which may be any agent for increasing the pH of the composition in which it is present.
  • the alkaline agent(s) are chosen from Bronsted-Lowry bases and Lewis bases.
  • They may be mineral or organic.
  • alkaline agent(s) are chosen from:
  • alkanolamines in particular mono-, di- or tri-(Ci-C6)alkanolamines such as mono-, di- and triethanolamines, isopropanolamine, 2-amino-2- methyl-1 -propanol (AMP), 2-amino-2-methyl-1 ,3-propanediol (AMPD) and 2-amino-1 ,3-propanediol, and also derivatives thereof,
  • alkali metal or alkaline-earth metal silicates or metasilicates such as sodium metasilicates
  • carbonates and bicarbonates particularly of a primary amine, secondary amine or tertiary amine, or of an alkali metal or alkaline-earth metal, or of ammonium, and
  • W represents a divalent C1-C6 alkylene radical optionally substituted with a hydroxyl group or a C-i-Ce alkyl radical, Rx,
  • R y , Rz and Rt which may be identical or different, represent a hydrogen atom or a C-i-Ce alkyl, C-i-Ce hydroxyalkyl or C-i-Ce aminoalkyl group.
  • Examples of such compounds of formula (III) that may be mentioned include 1 ,3-diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • the mineral or organic hydroxides are preferably chosen from hydroxides of an alkali metal, hydroxides of an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide, hydroxides of a transition metal, such as hydroxides of metals from Groups III, IV, V and VI of the Periodic Table of the Elements, hydroxides of lanthanides or actinides, quaternary ammonium hydroxides and guanidinium hydroxide.
  • the hydroxide may be formed in situ, for instance guanidine hydroxide, by reacting calcium hydroxide and guanidine carbonate.
  • the preferred alkaline agents are chosen from ammonia, carbonates or bicarbonates such as ammonium or sodium carbonate, ammonium or sodium bicarbonate, basic amino acids such as arginine, alkanolamines such as monoethanolamine (MEA), 2-amino-2-methyl-1 -propanol (AMP), 2-amino-2- methyl-1 ,3-propanediol (AMPD) and 2-amino-1 ,3-propanediol, preferably alkanolamines such as MEA.
  • MEA monoethanolamine
  • AMP 2-amino-2-methyl-1 -propanol
  • AMPD 2-amino-2- methyl-1 ,3-propanediol
  • 2-amino-1 ,3-propanediol preferably alkanolamines such as MEA.
  • the alkaline agent(s) as defined previously may represent, for example, from 0.1 % to 20% by weight, and preferably from 1 % to 15% by weight, relative to the total weight of composition (B).
  • the process of the invention involves a switching-off step using an acidic composition (C).
  • Composition (C) is at acidic pH, i.e. it is an aqueous composition with a pH of less than 7, preferably less than 6 and ranging down to 0.5 inclusive, particularly at a pH inclusively between 1 and 5, preferably between 1 .3 and 3.
  • the switching-off composition (C) comprises one or more organic or mineral acids preferably chosen from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H2S0 4 , iv) phosphoric or orthophosphoric acid H3P0 4 , v) (Ci-C6)alkylsulfonic acids: Alk-S(0)20H, such as methanesulfonic acid and ethanesulfonic acid; vi) arylsulfonic acids: Ar-S(0)20H such as benzenesulfonic acid and toluenesulfonic acid; vii) carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid or succinic acid, viii) sulfonic acids; ix) (C-i- C6)alkoxysulfinic acids: Alk-0-S(0)0H such as methoxysulfinic acid and ethoxysulfini
  • carboxylic acid means a compound comprising at least one carboxylic acid -C(0)-0H group, preferably of formula (I) as defined previously, preferably comprising between 1 and 4 carboxylic acid groups, such as 1 or 2; chosen from: i) (Ci-C6)alkyl-[C(0)-0H] n and ii) het-[C(0)-0H] n , with n an integer between 1 and 4 inclusive, preferably between 1 and 2, het representing a heterocylic group, such as pyrrolidone, it being possible for the alkyl or het group to be optionally substituted with one or more groups chosen from OH, and (di)(Ci- C 4 )(alkyl)amino.
  • formula (I) as defined previously, preferably comprising between 1 and 4 carboxylic acid groups, such as 1 or 2; chosen from: i) (Ci-C6)alkyl-[C(0)-0H] n and ii) het
  • the acids used in the switching-off composition (C) of the invention are chosen from orthophosphoric acid, and carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, more particularly chosen from orthophosphoric acid and carboxylic acid such as acetic acid.
  • compositions (A), (A-i), (B) and (C) of the invention are in a cosmetic medium, i.e. a medium that is suitable for dyeing keratin fibers, especially human keratin fibers such as the hair, also known as a dyeing support, which generally comprises water or at least one organic solvent or a mixture of water and of at least one organic solvent.
  • a cosmetic medium i.e. a medium that is suitable for dyeing keratin fibers, especially human keratin fibers such as the hair
  • a dyeing support which generally comprises water or at least one organic solvent or a mixture of water and of at least one organic solvent.
  • compositions (A), (A-i), (B) or (C) comprises one or more liquid organic compounds with a Hansen solubility parameter dH of greater than 0 and less than 16 MPa 1/2 .
  • composition (A) or (A-i) comprising the compound(s) of formula (I) and/or (G) also comprises one or more liquid organic compounds with a Hansen solubility parameter dH of greater than 0 and less than 16 MPa 1/2 .
  • such a liquid organic compound is also known as a hydrotropic compound.
  • hydrotropic compound means a compound that is capable of increasing the solubility of hydrophobic compounds in aqueous phases.
  • Said liquid compounds more preferentially have a Hansen solubility parameter dH of between 5 and 15.8 MPa 1/2 , even more preferentially between 8 and 15.8 MPa 1/2 and better still between 8 and 15 MPa 1/2 .
  • This value of the solubility parameter 5H is related to the formation of hydrogen bonds. It may be recalled that there are three major types of interaction in organic compounds: non-polar interactions, permanent dipole-dipole interactions and interactions of hydrogen bonding type, the latter forming the subject of the parameter defining the hydrotropic compound present in the composition used in accordance with the invention.
  • solubility parameter 5H is usually given for a temperature of 25 °C and at atmospheric pressure (760 mmHg, i.e. 1 .013 x 10 5 Pa).
  • liquid organic compounds with a Hansen solubility parameter value 5H of greater than 0 and less than 16 MPa 1/2 are nonionic compounds.
  • said liquid organic compound(s) with a Hansen solubility parameter value 5H of greater than 0 and less than 16 MPa 1/2 are chosen from alcohol ethers, aliphatic esters, aliphatic ethers, aromatic ethers, alkanols bearing aryl substituents, lactones and sulfones, and mixtures thereof.
  • Said liquid organic compound(s) with a Hansen solubility parameter value 5H of greater than 0 and less than 16 MPa 1/2 may be chosen from: • alcohol ethers, in particular Ci-C 4 ethers of C5-C30 alcohols, which are preferably saturated, linear or branched, optionally interrupted with one or more non-adjacent ether functions;
  • aromatic ethers in particular of Ce-C-io, of a C-i-Ce alkyl optionally bearing a hydroxyl group;
  • alkanols bearing an aryl substituent preferably for which the aryl part is Ce-C-io, advantageously Ce, and the alkyl part of the alkanol is Ci-C 4 , this alkyl part possibly ending or being interrupted with a heteroatom, advantageously oxygen or a hydroxyl group, preferably such as benzyl alcohol;
  • R' represents a hydrogen, a linear or branched C-i-Cs alkyl or a linear or branched Ci-C 4 hydroxyalkyl and n has the value 1 , 2 or 3, and preferably R' represents a hydrogen, a linear or branched C-i-Ce alkyl or a linear or branched C1-C2 hydroxyalkyl;
  • sulfones especially cyclic sulfones, in particular sulfolanes, preferably substituted with one or more (Ci-C 4 )alkyl groups such as 3-methyl sulfolane.
  • said liquid organic compound(s) according to the invention are chosen from dipropylene glycol monomethyl ether acetate, dipropylene glycol methyl ether, dipropylene glycol mono-n-butyl ether (the INCI name of which is PPG-2 Butyl Ether), tripropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, 3- phenyl-1 -propanol, 2-phenyl-1 -propanol, benzyl alcohol, benzyloxyethanol and phenoxyethanol, and mixtures of these compounds.
  • the liquid organic compound with a Hansen solubility parameter 5H of greater than 0 and less than 16 MPa 1/2 is preferably chosen from i) alcohol ethers, ii) aliphatic esters, iii) aromatic ethers, iv) alkanols bearing aryl substituents, preferably for which the aryl part is Ce-C-io, advantageously Ce, and the alkyl part of the alkanol is Ci-C 4 , this alkyl part possibly being terminated or interrupted with a heteroatom, advantageously oxygen, or a hydroxyl group, preferably such as benzyl alcohol and phenoxyethanol, v) 5- to 7-membered cyclic sulfones optionally substituted with one or more (Ci-C 4 )alkyl groups such as 3-methyl sulfolane, and mixtures thereof.
  • the liquid organic compound(s) with a Hansen solubility parameter value 5H of greater than 0 and less than 16 MPa 1/2 are chosen from aromatic alcohols, and mixtures thereof; even more preferentially chosen from alkanols bearing aryl substituents and even more preferentially benzyl alcohol and/or phenoxyethanol.
  • benzyl alcohol is present in an amount of between 1 % and 10%, such as 5% by weight relative to the total weight of composition (A), (A-i), (B) or (C), more particularly composition (A) or (A-i); and phenoxyethanol is present in an amount of between 0.5% and 3%, such as 1 % by weight relative to the total weight of composition (A), (A-i), (B) or (C), more particularly composition (A) or (A-i).
  • the liquid organic compound(s) with a Hansen solubility parameter value dH of greater than 0 and less than 16 MPa 1/2 is (are) chosen from 5- to 7-membered cyclic sulfones optionally substituted with one or more (Ci-C 4 ) alkyl groups, such as 3-methyl sulfolane.
  • the liquid organic compound(s) with a Hansen solubility parameter value 5H of greater than 0 and less than 16 MPa 1/2 preferably represent a total content ranging from 0.05% to 35% by weight, preferably from 1 % to 20% by weight, better still from 2% to 10% by weight, in particular between 5% and 7%, such as 6% by weight relative to the total weight of composition (A), (A-i), (B) or (C), more particularly composition (A) or (A-i).
  • the non-hydrotrooic organic solvents preferably represent a total content ranging from 0.05% to 35% by weight, preferably from 1 % to 20% by weight, better still from 2% to 10% by weight, in particular between 5% and 7%, such as 6% by weight relative to the total weight of composition (A), (A-i), (B) or (C), more particularly composition (A) or (A-i).
  • composition (A) or (A-i) comprising the compound(s) of formula (I) or (G) comprises one or more additional organic solvents (other than the liquid organic compound(s) with a Hansen solubility parameter 5H of greater than 0 and less than or equal to 16 MPa 1/2 ).
  • Additional organic solvents include Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers.
  • Additional organic solvents that may more particularly be mentioned include C2-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers.
  • At least one of the compositions of the process according to the invention preferably comprises one or more Ci-C 4 lower alkanols, such as ethanol or isopropanol, more preferably one or more C2-C 4 lower alkanols, such as ethanol or isopropanol.
  • composition (A) or (A-i) comprising the compound(s) of formula (I) or (G) preferably comprises one or more Ci-C 4 lower alkanols, such as ethanol or isopropanol, more preferably one or more C2-C 4 lower alkanols, such as ethanol or isopropanol.
  • compositions of the process according to the invention comprises ethanol.
  • the additional organic solvents may be present in a total content preferably between 1 % and 40% by weight and even more preferentially between 5% and 30% by weight approximately relative to the total weight of the composition which contains them, in particular relative to the total weight of composition (A) or (A-i). vi)
  • the thickeners may be present in a total content preferably between 1 % and 40% by weight and even more preferentially between 5% and 30% by weight approximately relative to the total weight of the composition which contains them, in particular relative to the total weight of composition (A) or (A-i).
  • compositions (A), (A-i), (B) or (C) also comprises one or more thickeners, preferably polymeric thickeners. More particularly, composition (A) or (A-i) also comprises one or more thickeners preferably chosen from associative or non- associative cationic, nonionic, anionic or zwitterionic organic polymers, of natural or synthetic origin.
  • Thickening polymers that may be mentioned include non-associative thickening polymers bearing sugar units.
  • the term“sugar unit means a unit derived from a carbohydrate of formula C n (H20) n -i or (CFfeO which may be optionally modified by substitution and/or by oxidation and/or by dehydration.
  • sugar units of the thickening polymers of the invention are preferably derived from the following sugars:
  • Thickening polymers of the invention include native gums such as:
  • ⁇ gum arabic branched polymer of galactose, arabinose, rhamnose and glucuronic acid
  • ⁇ ghatti gum polymer derived from arabinose, galactose, mannose, xylose and glucuronic acid
  • ⁇ karaya gum (polymer derived from galacturonic acid, galactose, rhamnose and glucuronic acid);
  • gum tragacanth (or tragacanth) (polymer of galacturonic acid, galactose, fucose, xylose and arabinose);
  • gums derived from algae including:
  • ⁇ agar (polymer derived from galactose and anhydrogalactose);
  • ⁇ alginates polymers of mannuronic acid and of glucuronic acid
  • gums derived from seeds or tubers including:
  • ⁇ guar gum (polymer of mannose and galactose);
  • locust bean gum polymer of mannose and galactose
  • ⁇ fenugreek gum polymer of mannose and galactose
  • ⁇ tamarind gum polymer of galactose, xylose and glucose
  • ⁇ konjac gum polymer of glucose and mannose
  • microbial gums including:
  • ⁇ xanthan gum polymer of glucose, mannose acetate, mannose/pyruvic acid and glucuronic acid
  • ⁇ gellan gum polymer of partially acylated glucose, rhamnose and glucuronic acid
  • e) plant extracts including:
  • These polymers can be physically or chemically modified.
  • physical treatment mention may in particular be made of the temperature.
  • these chemical or physical treatments are applied to guar gums, locust bean gums, starches and celluloses.
  • nonionic guar gums that may be used according to the invention may be modified with C-i-Ce (poly)hydroxyalkyl groups.
  • C-i-Ce (poly)hydroxyalkyl groups mention may be made, by way of example, of hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
  • guar gums are well known from the prior art and may be prepared, for example, by reacting corresponding alkene oxides, for instance propylene oxides, with the guar gum so as to obtain a guar gum modified with hydroxypropyl groups.
  • the degree of hydroxyalkylation preferably varies from 0.4 to 1 .2 and corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functional groups present on the guar gum.
  • nonionic guar gums optionally modified with hydroxyalkyl groups are sold, for example, under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120 by the company Rhodia Chimie.
  • the botanical origin of the starch molecules used in the present invention may be cereals or else tubers.
  • the starches are chosen, for example, from corn starch, rice starch, cassava starch, barley starch, potato starch, wheat starch, sorghum starch and pea starch.
  • the starches may be chemically or physically modified, in particular by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidation, heat treatments.
  • Distarch phosphates or compounds rich in distarch phosphate will preferentially be used, for instance the product sold under the references Prejel VA-70-T AGGL (gelatinized hydroxypropyl cassava distarch phosphate), Prejel TK1 (gelatinized cassava distarch phosphate) and Prejel 200 (gelatinized acetyl cassava distarch phosphate) by the company Avebe, or Structure Zea from National Starch (gelatinized corn distarch phosphate).
  • amphoteric starches may also be used, these amphoteric starches comprising one or more anionic groups and one or more cationic groups.
  • the anionic and cationic groups may be bonded to the same reactive site of the starch molecule or to different reactive sites; they are preferably bonded to the same reactive site.
  • the anionic groups may be of carboxylic, phosphate or sulfate type, preferably carboxylic.
  • the cationic groups may be of primary, secondary, tertiary or quaternary amine type.
  • the starch molecules may be derived from any plant source of starch, in particular such as corn, potato, oat, rice, tapioca, sorghum, barley or wheat. It is also possible to use the hydrolyzates of the starches mentioned above.
  • the starch is preferably derived from potato.
  • the non-associative thickening polymers of the invention may be cellulose- based polymers not including a C10-C30 fatty chain in their structure.
  • cellulose-based polymer means any polysaccharide compound having in its structure sequences of glucose residues linked together via b-1 ,4 bonds; in addition to unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.
  • the cellulose-based polymers of the invention may be chosen from unsubstituted celluloses, including those in a microcrystalline form, and cellulose ethers.
  • cellulose ethers cellulose esters and cellulose ester ethers are distinguished.
  • cellulose esters are mineral esters of cellulose (cellulose nitrates, sulfates, phosphates, etc.), organic cellulose esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates and acetatetrimellitates, etc.), and mixed organic/mineral esters of cellulose, such as cellulose acetatebutyrate sulfates and cellulose acetatepropionate sulfates.
  • cellulose ester ethers mention may be made of hydroxypropylmethylcellulose phthalates and ethylcellulose sulfates.
  • nonionic cellulose ethers without a C10-C30 fatty chain i.e. which are " non-associative"
  • anionic cellulose ethers without a fatty chain mention may be made of (poly)carboxy(Ci-C 4 )alkylcelluloses and salts thereof.
  • carboxymethylcelluloses for example Blanose 7M from the company Aqualon
  • carboxymethylhydroxyethylcelluloses for example Blanose 7M from the company Aqualon
  • cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described in particular in patent US 4 131 576, such as (poly)hydroxy(Ci-C 4 )alkyl celluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted in particular with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
  • the commercial products corresponding to this definition are more particularly the products sold under the names Celquat® L 200 and Celquat® H 100 by the company National Starch.
  • non-associative thickening polymers not bearing sugar units that may be used, mention may be made of crosslinked acrylic acid or methacrylic acid homopolymers or copolymers, crosslinked 2-acrylamido-2- methylpropanesulfonic acid homopolymers and crosslinked acrylamide copolymers thereof, ammonium acrylate homopolymers, or copolymers of ammonium acrylate and of acrylamide, alone or as mixtures thereof.
  • a first family of non-associative thickening polymers that is suitable for use is represented by crosslinked acrylic acid homopolymers.
  • homopolymers of this type mention may be made of those crosslinked with an allyl alcohol ether of the sugar series, for instance, the products sold under the names Carbopol 980, 981 , 954, 2984 and 5984 by the company Noveon or the products sold under the names Synthalen M and Synthalen K by the company 3 VSA.
  • the non-associative thickening polymers may also be crosslinked (meth)acrylic acid copolymers, such as the polymer sold under the name Aqua SF1 by the company Noveon.
  • the non-associative thickening polymers may be chosen from crosslinked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and the crosslinked acrylamide copolymers thereof.
  • composition may similarly comprise, as non-associative thickening polymers, ammonium acrylate homopolymers or copolymers of ammonium acrylate and of acrylamide.
  • ammonium acrylate homopolymers that may be mentioned is the product sold under the name Microsap PAS 5193 by the company Hoechst.
  • copolymers of ammonium acrylate and of acrylamide that may be mentioned is the product sold under the name Bozepol C Wunsch or the product PAS 5193 sold by the company Hoechst.
  • aqueous-phase thickening polymers mention may also be made of the non-cellulose-based associative polymers that are well known to those skilled in the art and in particular of nonionic, anionic, cationic or amphoteric nature.
  • associative polymers are polymers that are capable, in an aqueous medium, of reversibly associating with each other or with other molecules.
  • Their chemical structure more particularly comprises at least one hydrophilic region and at least one hydrophobic region.
  • hydrophobic group means a radical or polymer with a saturated or unsaturated, linear or branched hydrocarbon-based chain, comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms and more preferentially from 18 to 30 carbon atoms.
  • the hydrocarbon-based group is derived from a monofunctional compound.
  • the hydrophobic group may be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol or decyl alcohol. It may also denote a hydrocarbon-based polymer, for instance polybutadiene.
  • anionic associative polymers those that are particularly preferred according to the invention are polymers formed from 20% to 60% by weight of acrylic acid and/or of methacrylic acid, from 5% to 60% by weight of lower alkyl (meth)acrylates, from 2% to 50% by weight of fatty-chain allyl ether, and from 0 to 1 % by weight of a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol di methacrylate or methylenebisacrylamide.
  • a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol di methacrylate or methylenebisacrylamide.
  • crosslinked terpolymers of methacrylic acid, of ethyl acrylate and of polyethylene glycol (10 EO) stearyl alcohol ether (Steareth-10), in particular those sold by the company Ciba under the names Salcare SC 80® and Salcare SC 90®, which are aqueous 30% emulsions of a crosslinked terpolymer of methacrylic acid, of ethyl acrylate and of steareth-10 allyl ether (40/50/10);
  • Alkyl esters of unsaturated carboxylic acids that are useful in the invention comprise, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate and dodecyl acrylate, and the corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate and dodecyl methacrylate.
  • Anionic polymers of this type are described and prepared, for example, according to patents US 3 915 921 and US 4 509 949.
  • anionic associative polymers of this type use will more particularly be made of those constituted of 95% to 60% by weight of acrylic acid (hydrophilic unit), 4% to 40% by weight of C10-C30 alkyl acrylate (hydrophobic unit) and 0% to 6% by weight of crosslinking polymerizable monomer, or else of those constituted of 98% to 96% by weight of acrylic acid (hydrophilic unit), 1 % to 4% by weight of C10-C30 alkyl acrylate (hydrophobic unit) and 0.1 % to 0.6% by weight of crosslinking polymerizable monomer such as those described above.
  • those most particularly preferred according to the present invention are the products sold by the company Goodrich under the trade names Pemulen TR1 ®, Pemulen TR2® and Carbopol 1382®, and even more preferentially Pemulen TR1 ®, and the product sold by the company SEPPIC under the name Coatex SX®.
  • maleic anhydride/C3o-C38 a-olefin/alkyl maleate terpolymers such as the product (maleic anhydride/C3o-C38 a-olefin/isopropyl maleate copolymers) sold under the name Performa V 1608® by the company Newphase Technologies.
  • a nonionic monourethane which is the product of reaction of a monohydric surfactant with a monoethylenically unsaturated monoisocyanate
  • Example 3 such as those described in patent application EP-A-0 173 109 and more particularly the terpolymer described in Example 3, namely a methacrylic acid/methyl acrylate/behenyl alcohol dimethyl -meta- isopropenylbenzylisocyanate ethoxylated (40 EO) terpolymer, as an aqueous 25% dispersion.
  • a methacrylic acid/methyl acrylate/behenyl alcohol dimethyl -meta- isopropenylbenzylisocyanate ethoxylated (40 EO) terpolymer as an aqueous 25% dispersion.
  • these compounds also comprise as monomer an ester of an a,b- monoethylenically unsaturated carboxylic acid and of a Ci-C 4 alcohol.
  • Aculyn 22® sold by the company Rohm & Haas, which is a methacrylic acid/ethyl acrylate/oxyalkylenated stearyl methacrylate terpolymer;
  • amphiphilic polymers including at least one ethylenically unsaturated monomer bearing a sulfonic group, in free or partially or totally neutralized form and comprising at least one hydrophobic part. These polymers may be crosslinked or non-crosslinked. They are preferably crosslinked.
  • the ethylenically unsaturated monomers bearing a sulfonic group are in particular chosen from vinylsulfonic acid, styrenesulfonic acid, (meth)acrylamido(Ci-C22)alkylsulfonic acids, A/-(Ci-
  • C22)alkyl(meth)acrylamido(Ci-C22)alkylsulfonic acids such as undecylacrylamidomethanesulfonic acid, and also partially or totally neutralized forms thereof.
  • (Meth)acrylamido(C-i-C22)alkylsulfonic acids for instance acrylamidomethanesulfonic acid, acrylamidoethanesulfonic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, methacrylamido-2-methylpropanesulfonic acid, 2-acrylamido-n-butanesulfonic acid, 2-acrylamido-2,4,4-trimethylpentanesulfonic acid, 2- methacrylamidododecylsulfonic acid or 2-acrylamido-2,6-dimethyl-3- heptanesulfonic acid, and also partially or totally neutralized forms thereof, will more preferentially be used.
  • APMS 2-Acrylamido-2-methylpropanesulfonic acid
  • the polymers of this family may be chosen especially from random amphiphilic AMPS polymers modified by reaction with a C6-C22 n- monoalkylamine or di-n-alkylamine, and such as those described in patent application WO 00/31 154 (forming an integral part of the content of the description). These polymers may also contain other ethylenically unsaturated hydrophilic monomers chosen, for example, from (meth)acrylic acids, b- substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid and maleic acid, or mixtures of these compounds.
  • the preferred polymers of this family are chosen from amphiphilic copolymers of AMPS and of at least one ethylenically unsaturated hydrophobic monomer.
  • copolymers may also contain one or more ethylenically unsaturated monomers not including a fatty chain, such as (meth)acrylic acids, b-substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid and maleic acid, or mixtures of these compounds.
  • ethylenically unsaturated monomers not including a fatty chain such as (meth)acrylic acids, b-substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid and maleic acid, or mixtures of these compounds.
  • terpolymers including from 10 mol% to 90 mol% of acrylamide units, from 0.1 mol% to 10 mol% of AMPS units and from 5 mol% to 80 mol% of n- (C6-Ci8)alkylacrylamide units, such as those described in patent US-5 089 578.
  • copolymers of totally neutralized AMPS and of dodecyl methacrylate and also crosslinked and non-crosslinked copolymers of AMPS and of n-dodecylmethacrylamide, such as those described in the Morishima articles mentioned above.
  • cationic associative polymers mention may be made of:
  • Polyacrylate- 1 Crosspolymer is the product of polymerization of a monomer mixture comprising:
  • - (Ill) quaternized (poly)hydroxyethylcelluloses modified with groups including at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups including at least 8 carbon atoms, or mixtures thereof.
  • the alkyl radicals borne by the above quaternized celluloses or hydroxyethylcelluloses preferably include from 8 to 30 carbon atoms.
  • the aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups.
  • Examples of quaternized alkylhydroxyethylcelluloses containing C8-C30 fatty chains that may be indicated include the products Quatrisoft LM 200®, Quatrisoft LM-X 529-18-A®, Quatrisoft LM-X 529-18-B® (C12 alkyl) and Quatrisoft LM-X 529-8® (Cis alkyl) sold by the company Aqualon, and the products Crodacel QM®, Crodacel QL® (C12 alkyl) and Crodacel QS® (C18 alkyl) sold by the company Croda and the product Softcat SL 100® sold by the company Aqualon.
  • vinylpyrrolidone/dimethylaminopropylmethacrylamide/dodecyldimethylmethacryl -amidopropylammonium tosylate terpolymers vinylpyrrolidone/dimethylaminopropylmethacrylamide/cocoyldimethylmethacryl- amidopropylammonium tosylate terpolymers, vinylpyrrolidone/dimethylaminopropylmethacrylamide/lauryldimethylmethacryla- midopropylammonium tosylate or chloride terpolymers are used in particular.
  • amphoteric associative polymers are preferably chosen from those including at least one noncyclic cationic unit. Even more particularly, those prepared from or comprising 1 to 20 mol%, preferably 1.5 to 15 mol% and even more particularly 1.5 to 6 mol% of fatty-chain monomer relative to the total number of moles of monomers are preferred.
  • Amphoteric associative polymers according to the invention are described and prepared, for example, in patent application WO 98/44012.
  • amphoteric associative polymers the ones that are preferred are acrylic acid/(meth)acrylamidopropyltrimethylammonium chloride/stearyl methacrylate terpolymers.
  • the associative polymers of nonionic type that may be used according to the invention are preferably chosen from:
  • polyurethane polyethers including in their chain both hydrophilic blocks usually of polyoxyethylenated nature and hydrophobic blocks, which may be aliphatic sequences alone and/or cycloaliphatic and/or aromatic sequences;
  • celluloses or derivatives thereof modified with groups including at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups or mixtures thereof wherein the alkyl groups are of Cs, and in particular:
  • nonionic alkylhydroxyethylcelluloses such as the products Natrosol Plus Grade 330 CS and Polysurf 67 (Cie alkyl) sold by the company Aqualon;
  • nonionic nonoxynylhydroxyethylcelluloses such as the product Amercell HM-1500 sold by the company Amerchol;
  • nonionic alkylcelluloses such as the product Bermocoll EHM 100 sold by the company Berol Nobel;
  • associative guar derivatives for instance hydroxypropyl guars modified with a fatty chain, such as the product Esaflor HM 22 (modified with a C22 alkyl chain) sold by the company Lamberti; the product Miracare XC 95-3 (modified with a Ci 4 alkyl chain) and the product RE 205-146 (modified with a C20 alkyl chain) sold by Rhodia Chimie.
  • the polyurethane polyethers include at least two hydrocarbon- based lipophilic chains containing from 6 to 30 carbon atoms, separated by a hydrophilic block, the hydrocarbon-based chains possibly being side chains or chains at the end of the hydrophilic block.
  • the polymer may include a hydrocarbon-based chain at one end or at both ends of a hydrophilic block.
  • the polyurethane polyethers may be multiblock, in particular in triblock form.
  • the hydrophobic blocks may be at each end of the chain (for example: triblock copolymer bearing a hydrophilic central block) or distributed both at the ends and in the chain (for example, multiblock copolymer).
  • These same polymers may also be graft polymers or star polymers.
  • the nonionic fatty-chain polyurethane polyethers may be triblock copolymers, the hydrophilic block of which is a polyoxyethylene chain including from 50 to 1000 oxyethylene groups.
  • the nonionic polyurethane polyethers include a urethane bond between the hydrophilic blocks, hence the origin of the name.
  • nonionic fatty-chain polyurethane polyethers include those in which the hydrophilic blocks are linked to the lipophilic blocks via other chemical bonds.
  • nonionic fatty-chain polyurethane polyethers that may be used in the invention, it is also possible to use Rheolate 205® containing a urea function, sold by the company Rheox, or Rheolate® 208, 204 or 212, and also Acrysol RM 184®.
  • the product DW 1206B® from Rohm & Haas containing a C20 alkyl chain and a urethane bond, sold at a solids content of 20% in water, may also be used.
  • Use may also be made of solutions or dispersions of these polymers, especially in water or in aqueous-alcoholic medium.
  • examples of such polymers that may be mentioned are Rheolate® 255, Rheolate® 278 and Rheolate® 244 sold by the company Rheox.
  • Use may also be made of the products DW 1206F and DW 1206J sold by the company Rohm & Haas.
  • polyurethane polyethers that may be used according to the invention are in particular those described in the article by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sci., 271 , 380-389 (1993).
  • a polyurethane polyether that may be obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate.
  • Aculyn 46® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of stearyl alcohol and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 15% by weight in a matrix of maltodextrin (4%) and water (81 %);
  • Aculyn 44® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of decyl alcohol and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 35% by weight in a mixture of propylene glycol (39%) and water (26%)].
  • the polymers in the cosmetic compositions in accordance with the present invention advantageously have in solution or in dispersion, at 1 % active material in water, a viscosity, measured using a Rheomat RM 180 rheometer at 25 °C, of greater than 0.1 ps and even more advantageously greater than 0.2 cp, at a shear rate of 200 s 1 .
  • the thickener(s) are chosen from polysaccharides, in particular cellulose polymers, and more particularly hydroxy(Ci- 4 )alkylcelluloses such as hydroxyethylcelluloses (HEC), hydroxypropylmethylcelluloses (HPMC), xanthan gums, guar gums and polyvinylpyrrolidones (PVP).
  • polysaccharides in particular cellulose polymers, and more particularly hydroxy(Ci- 4 )alkylcelluloses such as hydroxyethylcelluloses (HEC), hydroxypropylmethylcelluloses (HPMC), xanthan gums, guar gums and polyvinylpyrrolidones (PVP).
  • HEC hydroxyethylcelluloses
  • HPMC hydroxypropylmethylcelluloses
  • PVP polyvinylpyrrolidones
  • the organic thickening polymer(s) are chosen from cellulose polymers, and more particularly hydroxy(Ci-C 4 )alkylcelluloses such as hydroxyethylcelluloses (HEC) and hydroxypropylmethylcelluloses (HPMC).
  • cellulose polymers and more particularly hydroxy(Ci-C 4 )alkylcelluloses such as hydroxyethylcelluloses (HEC) and hydroxypropylmethylcelluloses (HPMC).
  • the organic thickening polymer(s) represent a total content ranging from 0.01 % to 10% by weight and preferably from 0.1 % to 5% by weight relative to the total weight of composition (A), (A-i), (B) or (C) and preferably (A) or (A-i).
  • compositions (A), (A-i), (B) or (C) of the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof other than the thickening polymers described previously, antioxidants, penetrants, sequestrants, fragrances, dispersants, cations, film forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair
  • adjuvants conventionally used in compositions for dyeing the hair such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof other than the thickening polymers described
  • the above adjuvants generally represent an amount for each of them of between 0.01 % and 20% by weight relative to the weight of composition (A), (A-i), (B) or (C).
  • the pH of composition (A), (A-i), (B) or (C) may be adjusted to the desired value by means of alkaline agents as defined previously in ii) or by using acids as defined previously in iii), or alternatively by means of standard buffer systems.
  • compositions according to the invention may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibers, and especially human hair.
  • the process of the invention makes it possible especially to obtain colors that change or colouration of which the color disappears and then reappears (switch off - switch on), or appears and disappears (switch on - switch off) within a pH zone that does not impair the keratin fibers and without any substantial loss of color, especially in terms of color intensity or color build-up.
  • the process of the invention makes it possible especially to obtain changing colors or whose color disappears and then reappears (switch off - switch on), or appears and disappears (switch on - switch off) within a pH zone that does not impair the keratin fibers and without any substantial loss of color, especially in terms of color intensity or color build-up.
  • the process of the invention makes it possible to obtain keratin fiber colorings with intense colors, and a good color build-up which can switch as a function of the pH, even after several cycles, with a rapid and sharp effect of the " switch off - switch on” color change, with structured effects (geometrical, graphic, etc. effect), without any color transfer from one lock to another (e.g. possibility on a braid comprising three dyes of different colors of there being no color diffusion from one lock to another even after several pH revealing cycles), and which can avoid denaturing of the keratin fibers.
  • the coloring is erased or switched off when the keratin fibers have regained a color close or even identical to their original color especially on dark keratin fibers.
  • the coloring is modified when the coloring obtained is different from that obtained during the preceding step.
  • the coloring is reformed when the coloring obtained on the keratin fibers is identical to that which was obtained during a preceding step and which was subsequently modified.
  • the coloring obtained depends on the compound(s) of formula (I) or (G) that are applied to the keratin fibers. When all of these compounds have their sulfonate ring open like the compounds (G), the coloring is intense and chromatic.
  • the coloring is then modified in intensity and/or chromaticity depending on whether the keratin fibers are treated with one or more compounds of formula (I), the sulfonate ring of which is closed, or one or more compounds of formula (G), the sulfonate ring of which is open, and depending on their relative pH sensitivity.
  • the process of the invention is performed on light-colored keratin fibers in particular with a tone depth (European scale) of between 8 and 10.
  • tone depth is the unit known to hairstyling professionals, and published in the book “Science des.s capillaires [Science of hair treatment]” by Charles Zviak 1988, published by Masson, pages 215 and 278; the tone depths range, according to the European scale, from 1 (black) to 10 (very light blond), one unit corresponding to one tone, the higher the figure, the lighter the shade;
  • the process is performed on dark keratin fibers, in particular chestnut-brown fibers with a tone depth (European scale) of less than or equal to 6, preferably less than or equal to 4.
  • the process is characterized in that the following steps are performed: i) a step of applying a composition (A) or (A-i), comprising one or more fluorescein compounds of formula (I) as defined previously, preferably at the acidic pH for which the compound is weakly colored or even colorless;
  • a revealing step which consists in applying to said fibers a composition (B) at basic pH;
  • a switching-off step which consists in applying to said fibers a composition (C) at acidic pH;
  • steps ii) and iii) may be repeated several times.
  • the process is characterized in that the following steps are performed:
  • composition (A) or (A-i) comprising one or more compounds chosen from: (1), (2), (3), (4), (5) and (6), more particularly (1), (2), (4), (5) and (6),
  • a switching-off step which consists in applying to said fibers a composition (C) at acidic pH;
  • steps ii) and iii) may be repeated several times.
  • the process is characterized in that the following steps are performed:
  • composition (A) or (A-i) comprising one or more fluorescein compounds of formula (G) as defined previously;
  • a switching-off step which consists in applying to said fibers a composition (C) at acidic pH;
  • the process is characterized in that the following steps are performed:
  • composition (A) or (A-i) comprising one or more compounds chosen from: (1’), (2’), (3’), (4’), (5’) and (6’), more particularly (1’), (2’), (4’), (5’) and (6’);
  • a switching-off step which consists in applying to said fibers a composition (C) at acidic pH;
  • steps ii) and iii) may be repeated several times.
  • composition (A) or (A-i) of the process according to the invention may optionally be followed by rinsing, preferably with rinsing.
  • composition (B) of the process of the invention may also optionally be followed by rinsing, preferably without rinsing.
  • composition (C) of the process of the invention may also optionally be followed by rinsing, preferably with rinsing.
  • composition (A) or (A-i) of the process according to the invention is followed by drying, preferably after rinsing.
  • composition (B) of the process of the invention may also optionally be followed by drying.
  • composition (C) of the process of the invention may also optionally be followed by drying.
  • the drying step may be performed either in the air (natural drying) or with any heating device such as a hairdryer or heating lamps or a heating hood, optionally in combination with straightening with a brush (blow drying), takes place before the straightening step using a straightening iron.
  • any heating device such as a hairdryer or heating lamps or a heating hood, optionally in combination with straightening with a brush (blow drying), takes place before the straightening step using a straightening iron.
  • composition (A) or (A-i) of the invention may be applied to dry or wet keratin fibers, preferably to dry or wet hair, preferably to dry hair.
  • the bath ratio of composition (A) or (A-i) applied may range from 0.1 to 20, more particularly from 0.2 to 15, preferably between 0.5 and 13, even more preferentially from 1 to 12.
  • bath ratio means the ratio between the total weight of the applied composition and the total weight of keratin materials to be treated.
  • the leave-on time of composition (A) or (Ai) of the invention is preferably between 3 and 120 minutes, preferably between 5 and 60 minutes and even more preferentially between 10 and 40 minutes, such as 30 minutes.
  • the application temperature is generally set at between room temperature and 80 °C, preferably between 25 and 55 °C and more particularly between 28 and 40 °C.
  • Another subject of the invention is a multi-compartment device or kit which comprises, i) in a first compartment: the fluorescein compounds of formula (I) or (G) as defined previously and optionally one or more halochromic additional dyes other than the fluoresceins of formula (I) or (G) as defined previously, ii) in a second compartment: a composition (B) at basic pH ; and iii) in a third compartment: a composition (C) at acidic pH.
  • the multi-compartment kit of the invention comprises, i) in a first compartment: a composition (A) or (A-i) as defined previously, ii) in a second compartment: a composition (B) at basic pH; and iii) in a third compartment: a composition (C) at acidic pH.
  • compositions were prepared; the amounts are given in g per 100 g of composition.
  • compositions (A'), (A") and (A’”) according to the invention are applied to locks according to the same protocol, namely:
  • the "switch" treatment is applied.
  • composition (B') is applied to each lock by spraying.
  • composition (C) is applied to each lock by spraying.
  • compositions according to the invention (A’a), (A”a) and (A”’a).
  • L*, a * and b * represent the values measured on locks of hair after treatment and Lo*, ao* and bo* represent the values measured on locks of hair before treatment.
  • DE* the higher the value of DE*, the greater the color build up.
  • L*ON, a * oN and b * oN represent the values measured on locks of hair after treatment with composition (A'), (A") or (A’”) on the one hand, and (A’a), (A”a) and (A”’a) on the other hand, and then application of the revealing composition (B’) and L*OFF, 3*OFF and b*oFF represent the values measured on locks of hair after treatment with composition (A'), (A") or (A’”) on the one hand, and (A’a), (A”a) and (A’”a) on the other hand, then application of the revealing composition (B') and then application of the erasing composition (C).
  • the process according to the invention allows successive appearance(s)/disappearance(s) of color within a few seconds, generally on applying the revealing composition, without the need to use a hairdryer. Numerous ON/OFF cycles may be performed in sequence, and very good persistence of the order of 5 to 8 shampoo washes was observed. Moreover, the integrity and feel of the hair are respected.
  • Example 2
  • compositions were prepared:
  • compositions (A-i) and (P) are applied to locks (1.5g of composition /g of hair) according to the same protocol, namely:
  • the "switch" treatment is applied.
  • composition (B-i) is applied to each lock by spraying.
  • composition (C-i) is applied to each lock by spraying.
  • the color of the locks was evaluated in the CIE L * a * b * system, using a Konica- Minolta 3600d colorimeter (illuminant D65, angle 10°).
  • composition (B-i) The variation in coloring between the locks of hair treated and revealed (switched on) with composition (B-i) and erased (switched off) with composition (C-i) is defined by AE*ON-OFF as in example 1 .

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

Abstract

La présente invention concerne un procédé de traitement de fibres de kératine, en particulier de fibres de kératine humaines telles que les cheveux, utilisant i) au moins un colorant direct de fluorescéine de formule (I) ou (I') tel que défini dans la description, ii) un révélateur alcalin, iii) un effaceur à pH acide. L'invention a également pour objet une composition comprenant au moins un colorant direct de fluorescéine de formule (I) ou (I') tel que défini dans la description et au moins un épaississant et/ou au moins un solvant hydrotropique, et un kit à plusieurs compartiments comprenant i), ii) et iii) dans trois compartiments séparés. La présente invention permet en particulier d'obtenir une coloration de fibres kératiniques avec des teintes intenses et persistantes qui peuvent être modifiées, effacées et reformées plusieurs fois sans perte de couleur.
PCT/EP2018/085417 2017-12-21 2018-12-18 Procédé de traitement de fibres de kératine par l'utilisation d'un colorant direct de fluorescéine halochromique, d'un révélateur alcalin, puis d'un effaceur acide WO2019121631A1 (fr)

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FR1762789 2017-12-21
FR1762789A FR3075611B1 (fr) 2017-12-21 2017-12-21 Procede de traitement des fibres keratiniques mettant en œuvre un colorant direct fluoresceine halochrome, un revelateur alcalin puis un effaceur acide

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CN116375612A (zh) * 2023-04-06 2023-07-04 吉林医药学院 一种3,4,5,6-四卤酚磺酞碱金属盐及其制备方法和应用
CN116375613A (zh) * 2023-04-06 2023-07-04 吉林医药学院 一种四溴酚蓝碱金属盐及其制备方法和应用
CN116444402A (zh) * 2023-04-06 2023-07-18 吉林百纯化学科技有限公司 一种didntb碱金属盐及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116375612A (zh) * 2023-04-06 2023-07-04 吉林医药学院 一种3,4,5,6-四卤酚磺酞碱金属盐及其制备方法和应用
CN116375613A (zh) * 2023-04-06 2023-07-04 吉林医药学院 一种四溴酚蓝碱金属盐及其制备方法和应用
CN116444402A (zh) * 2023-04-06 2023-07-18 吉林百纯化学科技有限公司 一种didntb碱金属盐及其制备方法和应用

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