WO2019086505A2 - Composition comprenant des thiolactones comprenant une fonction carbonate et procédé de traitement de matières kératiniques l'utilisant - Google Patents

Composition comprenant des thiolactones comprenant une fonction carbonate et procédé de traitement de matières kératiniques l'utilisant Download PDF

Info

Publication number
WO2019086505A2
WO2019086505A2 PCT/EP2018/079798 EP2018079798W WO2019086505A2 WO 2019086505 A2 WO2019086505 A2 WO 2019086505A2 EP 2018079798 W EP2018079798 W EP 2018079798W WO 2019086505 A2 WO2019086505 A2 WO 2019086505A2
Authority
WO
WIPO (PCT)
Prior art keywords
compound
acid
formula
preferentially
group
Prior art date
Application number
PCT/EP2018/079798
Other languages
English (en)
Other versions
WO2019086505A3 (fr
Inventor
Christian Blaise
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 WO2019086505A2 publication Critical patent/WO2019086505A2/fr
Publication of WO2019086505A3 publication Critical patent/WO2019086505A3/fr

Links

Classifications

    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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

Definitions

  • the present invention relates to i) a process for treating keratin materials, in particular human keratin fibres, comprising the application of a composition comprising at least one particular thiolactone comprising a carbonate function, in particular for shaping keratin fibres and/or straightening/relaxing, ii) a composition comprising the particular thiolactone(s) comprising a carbonate function, iii) and novel thiolactones comprising a carbonate function, iv) a process for preparing the novel thiolactones comprising carbonate function, and v) the use of said thiolactones comprising a carbonate function in cosmetics.
  • compositions which make it possible to introduce a temporary change to their head of hair, while targeting good shape-retention of the effect produced.
  • Heat treatments are generally used to modify the shape of the head of hair in a long-lasting manner. These treatments allow a visual modification of the appearance of the hairstyle, combining a decrease in the degree of frizziness, a modification of the overall volume of the head of hair, a decrease in little curls, a gain in manageability, a straighter visual appearance, a substantial gain in sheen, and a resistance to humidity in order to maintain the hairstyle throughout the day.
  • this type of treatment has the advantage of facilitating the daily maintenance of the head of hair, with the use of fewer care products, in particular rinse- out care products such as hair conditioners or masks, or leave-in care products such as sera, care creams or balms, or taming mousses. Drying of the hair is facilitated, with a much shortened blow-drying time and a decrease in the daily use of flat irons, in terms both of time and intensity. This thus makes it possible to limit the risks of damaging the hair through combined factors of mechanical and thermal stress.
  • a first technique is based on the use of compositions based on thiol-based reducing agents. These techniques require strict adherence to the application conditions recommended by the suppliers, in particular in terms of amount and leave-in time. In addition, they may be contraindicated on hair that is too sensitized and may not be compatible with same-day application of other treatments, such as dyeing or bleaching operations. Moreover, they have an unpleasant smell.
  • Another technique is based on the use of compositions based on formol (or formaldehyde) and derivatives thereof.
  • Patent application WO 201 1/104 282 thus proposed a novel process for semi-permanently straightening the hair, which consists in applying an a-keto acid solution to the hairfor 15 to 120 minutes, then drying and, finally, straightening the head of hair with an iron at a temperature of about 200°C.
  • the a-keto acid employed is preferably glyoxylic acid.
  • glyoxylic acid may not be well tolerated, and its volatility, amplified by the use of heat from the iron, can also pose a problem.
  • compositions of the prior art may adversely affect the hair and/or adversely affect its colour.
  • Treatments using a composition comprising a base combined with a heat treatment have also been proposed for straightening the hair. Such treatments make it possible to obtain good relaxing of curls, but can lead to impairment of the hair fibre.
  • Document EP 1837010 especially describes a straightening/relaxing process using a composition comprising sodium hydroxide and a heat treatment.
  • Document WO 2007/144707 describes a straightening/relaxing process using a composition comprising a non-hydroxylated base such as monoethanolamine or ethylenediamine, combined with a heat treatment.
  • Document WO 2009/1 17344 also describes a straightening/relaxing process using a composition comprising a non- hydroxylated base and a protein-denaturing agent, combined with a heat treatment.
  • compositions comprising weak acids at alkaline pH, combined with a heat treatment.
  • Document WO 2010/049434 describes, for example, a straightening/relaxing process in which a composition comprising a dicarboxylic acid, such as maleic acid, and a heat treatment are applied.
  • composition comprising at least one thiolactone comprising a carbonate function, chosen from the compounds of formula (I) below:
  • X represents an oxygen or sulfur atom, preferably an oxygen atom
  • Y represents an oxygen or sulfur atom or an NR group with R representing a hydrogen atom or a (Ci-Ce)alkyl group, preferably Y represents an oxygen atom;
  • Ri , R2, R3 and R 4 which may be identical or different, represent a hydrogen atom or an optionally substituted (Ci-Ce)alkyl group, such as methyl, ethyl or hydroxyethyl, preferably Ri , R2, R3 and R 4 are identical, particularly Ri , R2, R3 and R 4 represent a hydrogen atom;
  • A represents an oxygen atom or an amino group -N(R 5 )- with R 5 representing a hydrogen atom or an optionally substituted (Ci-Ce)alkyl group, such as methyl or hydroxyethyl; preferably, R5 represents a hydrogen atom;
  • B represents a linear or branched, saturated or unsaturated, preferably saturated, divalent hydrocarbon-based chain comprising from 1 to 18 carbon atoms, which is in particular C1-C12, linear or branched, optionally substituted, optionally cyclic and/or interrupted with one or more non-contiguous atoms or groups chosen from i) oxygen atoms, ii) sulfur atoms, iii) -N(R 5 )-, iv) -N + (R6)(R7)-, Q " with R 5 as defined previously and R6 and R7, which may be identical or different, denoting a (hydroxy)(C1 -C4)alkyl group such as methyl, ethyl or hydroxyethyl and Q " representing an anionic counterion, such as halide (CI " or Br).
  • Another subject of the invention is a process for treating keratin materials, in particular keratin fibres, especially human keratin fibres such as the hair, for shaping keratin fibres and/or straightening/relaxing said materials, using at least one compound of formula (I) as defined previously.
  • Another subject of the invention is the compounds of formula (I) as defined previously.
  • Another subject of the invention is a process for preparing the compounds of formula (I) as defined previously.
  • Another subject of the invention is the cosmetic use of the compounds of formula (I) as defined previously, in particular for treating keratin materials, in particular keratin fibres, in particular human keratin fibres such as the hair, preferably for shaping keratin fibres and/or straightening/relaxing said fibres.
  • the compounds of formula (I) of the invention make it possible in particular to obtain good relaxing of curls, that is long-lasting in particular with respect to shampooing operations, while at the same time limiting damage to the hair.
  • the compounds of formula (I) as defined previously have in particular the advantage of conferring good persistence, after shampooing, of good cosmetic properties of conditioning said keratin fibres, in particular human keratin fibres such as the hair.
  • said keratin fibres treated are conditioned in a long-lasting manner.
  • organic or mineral acid salt is intended to mean cosmetically acceptable addition salts of a cationic or cationizable group of the compound of formula (I) with an organic or mineral acid salt, more particularly the salts chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(0)20H such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(0)20H such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-0-S(0)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi
  • organic or mineral base salt is intended to mean cosmetically acceptable addition salts of an anionic or anionizable group of formula (I) with an organic or mineral alkaline agent salt, more particularly the salts chosen from an ammonia derivative salt, alkali metal carbonates or bicarbonates, such as sodium or potassium carbonates and sodium or potassium bicarbonates, alkali metal or alkaline-earth metal hydroxides, preferably sodium or potassium hydroxide, or mixtures thereof;
  • anionic counterion is intended to mean and an anion or an anionic salt of an organic or mineral acid counterbalancing the cationic charge of the compound of formula (I) when it contains same; more particularly, the anionic counterion is chosen from i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, among which are C1-C6 alkylsulfonates: Alk-S(0)20 " such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S(0)20 " such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-0-S(0)0 " such as methyl sulfate and ethyl
  • alkyl is intended to mean a linear or branched radical containing from 1 to 6 carbon atoms, in particular from 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl, preferably methyl;
  • (hydroxy) alkyl' is intended to mean a hydroxyalkyl radical or an alkyl radical, with "alkyl' as defined previously;
  • alkoxy is intended to mean an alkyl oxy group with "alkyl' as defined previously;
  • alkyl, hydrocarbon-based chain or alkylene groups is intended to mean that said groups can be substituted with one or more groups, which may be identical or different, chosen from i) hydroxyl, ii) halogen, iii) (Ci-C4)alkoxy, iv) hydroxy(C2-C4)alkoxy; v) (di)(hydroxy(Ci- C4)alkyl)amino, vi) R a -Z a -C(Zb)-Z c -, and vii) R a -Z a -S(0)t-Z c - with Z a and Zb, which may be identical or different, representing an oxygen or sulfur atom or a group NR a ', Zc representing a bond, an oxygen or sulfur atom or a group NR a ; R a representing a hydrogen atom or a (Ci-C4)alkyl group and R a ' representing a hydrogen atom
  • an "aryP' radical represents a monocyclic or polycyclic fused or non-fused carbon- based group, comprising from 6 to 22 carbon atoms, at least one ring of which is aromatic; in particular, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl, preferably phenyl;
  • a heteroaryl radicai' represents a 5- to 22-membered, monocyclic or polycyclic, fused or non-fused group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen and sulfur atoms, at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl,
  • addition salts that may be used in the context of the invention are especially chosen from salts of addition with a cosmetically acceptable base such as the basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, aqueous ammonia, amines or alkanolamines;
  • a cosmetically acceptable base such as the basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, aqueous ammonia, amines or alkanolamines;
  • heterocycloalkyl is intended to mean a monocyclic or bicyclic, preferably monocyclic, fused or non-fused group which is saturated or contains one or more ethylenic unsaturations, which is non-aromatic, comprising from 5 to 10 ring members, comprising in at least one ring a heteroatom such as nitrogen, possibly containing from 1 to 3 additional non-adjacent heteroatoms chosen from nitrogen, oxygen and sulfur atoms, this heterocycle possibly being substituted with one or more radicals, which may be identical or different, chosen from alkyl, hydroxyalkyl and alkoxy radicals; preferentially, according to the present invention, the term "heterocycloalkyl' denotes a saturated or unsaturated, preferably saturated, 5- to 8-membered heterocycle, and more preferentially it is chosen from piperidyl, pyrrolidinyl, piperazinyl and morpholinyl;
  • cycloalkyi is intended to mean a monocyclic or bicyclic, preferably monocyclic, fused or non-fused hydrocarbon-based group which is saturated or contains one or more ethylenic unsaturations, which is non-aromatic, comprising from 5 to 10 ring members, this cycloalkyi possibly being substituted with one or more radicals, which may be identical or different, chosen from alkyl, hydroxyalkyl and alkoxy radicals, preferentially, according to the present invention, the cycloalkyi is saturated and comprises from 5 to 8 ring members, and more preferentially is chosen from cyclopentyl and cyclohexyl;
  • cycloalkylene is intended to mean a cycloalkyi group as defined previously, which is divalent;
  • heterocycloalkylene is intended to mean a heterocycloalkyl group as defined previously, which is divalent;
  • cyclic is intended to mean that the hydrocarbon-based chain can represent or comprise one or more mono or polycyclic divalent group(s) comprising from 5 to 18 ring members, it being possible for said chain to optionally be interrupted with one or more non-contiguous heteroatoms, which may be identical or different, chosen from oxygen, nitrogen or sulfur, and/or that at least one of the ring members of the mono or polycyclic divalent group(s) can denote a heteroatom chosen from oxygen, nitrogen or sulfur; in particular, the term "cyclic” represents a cycloalkylene or heterocycloalkylene group, preferably a cycloalkylene group as defined previously, and more preferentially is chosen from cyclopentylene and cyclohexylene;
  • ary or heteroaryr radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from: an optionally substituted C1-C6 alkyl radical;
  • a 5- or 6-membered heterocycloalkyl radical a 5- or 6-membered heteroaryl radical, optionally substituted with a (Ci- C 4 )alkyl radical, preferentially methyl;
  • Ci- C3 alkyl radicals an amino group optionally substituted with one or two optionally substituted Ci- C3 alkyl radicals, said alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom,
  • an acylamino radical (-NR-C(O)-R') in which the R radical is a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the R' radical is a C1-C2 alkyl radical;
  • R radicals which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • an alkylsulfonylamino radical (R'-S(0)2-N(R)-) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' represents a C1-C4 alkyl radical or a phenyl radical; an aminosulfonyl radical ((R)2N-S(0)2-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • a polyhaloalkyl group preferentially trifluoromethyl
  • Thiolactones comprising a carbonate function of formula (I) are such that A represents an amino group -N(R 5 )- with R 5 representing a hydrogen atom or a (Ci-C 4 )alkyl group, more preferentially A represents a group -N(H)-.
  • the thiolactone(s) comprising a carbonate function of formula (I) are such that A represents an oxygen atom.
  • the thiolactone(s) comprising a carbonate function of formula (I) are such that p represents 1.
  • the thiolactone(s) comprising a carbonate function of formula (I) of the invention are such that B represents a linear or branched hydrocarbon-based C1-C12 divalent chain optionally interrupted with one or more oxygen atoms, or with one or more groups -N(R 5 )- with R 5 representing a hydrogen atom or a (Ci-C4)alkyl group such as methyl, said hydrocarbon-based chain preferably being optionally interrupted with 1 to 5 oxygen atoms, such as 2, 3 or 4 non-contiguous oxygen atoms. More preferentially, B represents a linear, uninterrupted hydrocarbon-based C1-C6 divalent chain, such as methylene, ethylene, propylene or butylene.
  • the thiolactone(s) comprising a carbonate function of formula (I) of the invention are such that B represents a divalent group chosen from:
  • q' is inclusively between 0 and 6, preferably between 0 and 4, more preferentially between 0 and 2;
  • q is inclusively between 0 and 9, preferably between 0 and 6, more preferentially between 0 and 3;
  • r and t which may be identical or different, are inclusively between 0 and 18, preferably between 0 and 12, more preferentially between 0 and 6;
  • r + 2q + t is an integer inclusively between 1 and 18, preferably between 1 and 12, more preferentially between 1 and 6;
  • r + 3q' + t is an integer inclusively between 1 and 18, preferably between 1 and 12, more preferentially between 1 and 6.
  • the thiolactone(s) comprising a carbonate function of formula (I) of the invention are such that B represents a divalent group chosen from: and -(CH 2 )u-N + (R6)(R7)-(CH 2 ) ⁇ , Q " with u and v, which may be identical or different, representing an integer inclusively between 0 and 18, preferentially between 0 and 12, more preferentially between 0 and 6, and such that u+v is inclusively between 1 and 18, preferentially between 1 and 12 and more preferentially between 1 and 6, with Q " , R 5 , R6 and R7 being as defined previously.
  • the thiolactone(s) comprising a carbonate function of formula (I) of the invention are such that B represents a -(CH2)w- divalent group, with w representing an integer inclusively between 1 and 18, particularly between 1 and 12, more particularly between 1 and 6, preferentially between 1 and 4, such as 1 or 4.
  • B represents an optionally substituted monocyclic (C4-C7)cycloalkylene group, such as cyclohexylene.
  • B represents a (hetero)arylene group such as phenylene, which is optionally substituted.
  • the thiolactones comprising a carbonate function of the invention are chosen from the compounds of formulae ( ⁇ ) to (III') below:
  • Ri , R2, R3 and R 4 which may be identical or different, are as defined previously, and preferably represent a hydrogen atom;
  • a and B are as defined previously, and preferably A represents O or NH and/or B represents a (Ci-Ce)alkylene group, in particular a linear (Ci-C4)alkylene group.
  • the thiolactone(s) comprising a carbonate function are chosen from the compounds of formulae ( ⁇ ) and ( ⁇ ), preferably in- More particularly, the thiolactone(s) comprising a carbonate function are chosen from the compounds of formulae (I'a) and (I'b),
  • formulae (I'a) and (I'b) B is as defined previously, in particular linear (Ci- C4)alkylene, such as methylene, ethylene, propylene or butylene; and R5 is as defined previously, and preferably represents a hydrogen atom.
  • thiolactones comprising a carbonate function of the invention are chosen from the compounds 1 to 6 below:
  • the compounds of formula (I) are chosen from the compounds 1_, 2, 3 or 4 defined above, and also the organic or mineral acid or base salts thereof, the optical isomers thereof, and the solvates thereof such as hydrates, and more particularly the compound V
  • Another subject of the invention is the process for preparing the thiolactones comprising a carbonate function of formula (I) according to the following synthesis scheme 1 , 2, or 3.
  • a strong base preferably an organolithium base, such as lithium diisopropylamide
  • one molar equivalent of the compound (b) reacts with one equivalent of compound (c), preferably in a halogenated solvent, such as in dichloromethane, at low temperature (0°C) so as to give the compound (la) according to the invention (step ii));
  • the alpha-ethylenic bis(thio)acid reagent (f) with at least one molar equivalent of a reagent CH3-C (Y)-SH, preferably in a non-protic solvent such as dichloromethane, or THF, and in particular at a temperature of between 30°C and 100°C, preferably between 40°C and 80°C, so as to give the compound (g) (step v); followed by an acidification step, preferably with a mineral acid such as hydrochloric acid (6 N), in particular at a temperature between 50°C and 1 10°C, preferably between 60°C and 90°C, so as to give the thiolactone (h) (step vi)); the latter being able to react according to step ii) under the same conditions according to scheme 1 , so as to give the compounds (lb) according to the invention for which, in formula (I), a is 1 .
  • a is 1 .
  • step viii the solvent is evaporated off, and then a thiol or alcohol compound R' a -YH, preferably ethanol, is added, so as to give the di(thio)ester compound (I)
  • R a , R' a and R b which may be identical or different, representing a (Ci-Ce)alkyl group such as methyl, Hal and Hal', which may be identical or different, represent a halogen atom such as chlorine or bromine, preferably chlorine.
  • composition of the invention comprises one or more compound(s) of formulae
  • the composition comprises one or more compound(s) of formulae (I) or (l') to ( ⁇ ) or 1_ to 6, or even in particular 1. to 4 as defined previously, in an amount inclusively between 0.01 % and 50% by weight relative to the total weight of the composition, in particular between 0.1 % and 30%, more particularly between 1 % and 20%, preferentially between 2% and 15%, more preferentially between 5% and 15%, such as 10%, by weight relative to the total weight of the composition.
  • the pH of the composition used in the process of the invention is greater than or equal to 1 and less than or equal to 7.
  • the pH of the composition ranges from 2 to 6 and more preferably from 3 to 5.5.
  • the composition(s) of the invention are in particular cosmetic compositions, i.e. compositions which contain a physiologically acceptable medium, that is to say a medium that is compatible with human keratin materials such as the skin (of the body, face, around the eyes or the scalp), the hair, the eyelashes, the eyebrows, bodily hair, the nails or the lips.
  • the physiologically acceptable medium of the composition(s) used in the process according to the invention is advantageously an aqueous medium. It may be constituted, for example, of water or of a mixture of water and of at least one cosmetically acceptable organic solvent.
  • organic solvents include C2-C4 lower alcohols, such as ethanol and isopropanol; polyols, especially those containing from 2 to 6 carbon atoms, for instance glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; polyol ethers, for instance 2-butoxyethanol, propylene glycol monomethyl ether and diethylene glycol monomethyl ether or monoethyl ether; and mixtures thereof.
  • the cosmetic compositions of the invention are preferably aqueous and then comprise water at a concentration ranging from 10% to 99.5%, better still from 30% to 95% and even better still from 50% to 95% by weight relative to the total weight of the composition.
  • composition used according to the invention may also contain one or more cosmetic additives chosen from non-ionic, anionic, cationic and amphoteric surfactants, vitamins and provitamins, including panthenol, sunscreens, fillers, colorants, nacreous agents, opacifiers, sequestrants, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antioxidants, antifoams, moisturizers, emollients, penetrants, fragrances and preservatives; preferably one or more non-ionic, anionic, cationic or amphoteric surfactants, cationic, anionic or neutral polymers, or associative polymers.
  • cosmetic additives chosen from non-ionic, anionic, cationic and amphoteric surfactants, vitamins and provitamins, including panthenol, sunscreens, fillers, colorants, nacreous agents, opacifiers, sequestrant
  • the usual cosmetic ingredients may be present in usual amounts, which can be readily determined by those skilled in the art and which may be, for each ingredient, between 0.01 % and 80% by weight. Those skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the compositions of the present invention.
  • compositions used in the process according to the invention may be in any formulation form conventionally used, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic, or oily, solution or suspension; a solution or a dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O/W, W/O or multiple type; a suspension or emulsion of soft consistency of cream (O/W) or (W/O) type; an aqueous or anhydrous gel, or any other cosmetic form.
  • compositions may be packaged in pump-action bottles or in aerosol containers, so as to apply the composition in vaporized (lacquer) form or in the form of a mousse.
  • Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for treating the hair.
  • the composition preferably comprises at least one propellant. pH of the composition(s):
  • the composition comprising the thiolactone(s) comprising a carbonate function of formula (I), or ( ⁇ ) to ( ⁇ ) or 1_ to 6, in particular 1 to 4, as defined previously is aqueous and has an acid pH.
  • the pH is adjusted so that the pH is greater than or equal to 1 and less than 7, in particular greater than or equal to 2 and less than 6, more particularly inclusively between 2.5 and 5.8, preferably between 3 and
  • the pH values may be adjusted with an organic or mineral acid, or with an alkaline agent chosen from mineral or organic or hybrid alkaline agents or mixtures thereof.
  • organic acid is intended to mean an acid, i.e. a compound that is capable of releasing a cation or proton H + or H30 + , in aqueous medium, which comprises at least one optionally unsaturated, linear or branched C1-C20 hydrocarbon-based chain, a (hetero)cycloalkyl or (hetero)aryl group and at least one acidic chemical function chosen in particularfrom carboxyl C(0)OH, sulfuric SO3H, SO2H, and phosphoric PO3H2,
  • the acids used are chosen from hydrochloric acid HCI, hydrobromic acid HBr, sulfuric acid H2SO4, alkylsulfonic acids: (Ci-C6)Alk-S(0)20H such as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar-S(0)20H such as benzenesulfonic acid and toluenesulfonic acid; (Ci-C6)alkoxysulfinic acids: Alk- 0-S(0)OH such as methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; phosphoric acid H3PO4; triflic acid CF3SO3H and tetrafluoroboric acid HBF4, and carboxylic acid(s) of formula (D) below:
  • A represents a saturated or unsaturated, cyclic or non-cyclic, and aromatic or non- aromatic hydrocarbon-based group, which is monovalent when t is 0 or polyvalent when t is greater than or equal to 1 , comprising from 1 to 50 carbon atoms, which is optionally interrupted with one or more heteroatoms and/or optionally substituted, especially with one or more hydroxyl groups; preferably, A represents a monovalent (Ci-Ce)alkyl group or a polyvalent (Ci-Ce)alkylene group optionally substituted with one or more hydroxyl groups.
  • carboxylic acids of formula (II) as defined above, and preferably the acid(s) used, is (are) an alpha-hydroxy acid such as lactic acid, glycolic acid, tartaric acid or citric acid.
  • the mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, alkali metal and alkaline-earth metal hydroxides, preferably sodium or potassium hydroxide, or mixtures thereof.
  • the alkaline agent(s) are organic amines, i.e. they contain at least one substituted or unsubstituted amino group.
  • the organic alkaline agent(s) are more preferentially chosen from organic amines with a pKb at 25°C of less than 12, preferably of less than 10 and even more advantageously of less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (E) below:
  • ⁇ W is a divalent C1-C6 alkylene radical optionally substituted with a hydroxyl group or a C-I-C6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as oxygen or NR U ;
  • R x , R y , R z , R' and R u which may be identical or different, represent a hydrogen atom or a C1-C6 alkyl, C1-C6 hydroxyalkyl or C1-C6 aminoalkyl radical.
  • the alkanolamine is ethanolamine (or monoethanolamine).
  • the composition comprises, as alkaline agent, one or more alkanolamines (preferably ethanolamine) and aqueous ammonia.
  • the alkanolamine(s) are present in a predominant amount relative to the aqueous ammonia.
  • one subject of the present invention is a process for treating keratin materials, in particular keratin fibres, especially human keratin fibres such as the hair, comprising:
  • the process is a process for treating keratin materials, especially human keratin fibres such as the hair, comprising: a) the application to said keratin materials of a composition containing at least one thiolactone comprising a carbonate function chosen from those of formula (I) and of formulae ( ⁇ ) to (III") and to 6, in particular 1_ to 4, as defined previously, and also the organic or mineral acid or base salt forms thereof, the optical isomers thereof, and the solvates thereof such as hydrates,
  • step of straightening/relaxing said keratin materials by means of a straightening iron at a temperature of at least 100°C or a step of shaping the keratin fibres.
  • the process is a process for treating keratin materials, especially human keratin fibres such as the hair, comprising:
  • a straightening iron at a temperature of at least 100°C or a step of shaping the keratin fibres.
  • the straightening iron is used at a temperature of at least 100°C, preferably at a temperature between, limits included, 100°C and 300°C, preferably between 120°C and 280°C, more preferably between 150°C and 250°C, and better still between 200 and 250°C.
  • composition of the invention may be applied to dry or wet keratin materials, preferably to dry or wet hair, preferably to dry hair.
  • the bath ratio of the applied composition may range from 0.1 to 20, more particularly from 0.2 to 15 and preferably between 0.5 and 13, even more preferentially from 1 to 12.
  • the term "bath ratio" is intended to mean the ratio between the total weight of the applied composition and the total weight of keratin materials to be treated.
  • the process of the invention may comprise other intermediate steps aimed at improving the straightening of the keratin fibres.
  • the step of applying the composition may be followed by a leave-on time.
  • the leave-on time namely the time of contact of the composition on the hair, is preferably at least 5 minutes, preferably between 10 and 60 minutes and preferably between 15 and 45 minutes.
  • the hair can then optionally be drained, preferably drained, either with the fingers or with a towel.
  • a drying step a2) is carried out before the straightening step using a straightening iron.
  • the straightening with the straightening iron is performed in several passes over the dry hair, in general 3 to 10 passes.
  • the process is a process for treating keratin materials, especially human keratin fibres such as the hair, comprising:
  • a1 a leave-on time of at least 5 minutes, preferably between 10 and 60 minutes, preferably between 15 and 45 minutes.
  • the process of the invention comprising the steps of applying the composition according to the invention to the hair, then of straightening with an iron, is performed one or more times, optionally separated by one or more cosmetic treatments, preferably a shampooing operation, until the desired shape or shape intensity is obtained.
  • a subject of the invention is also the cosmetic use of one or more thiolactones comprising a carbonate function chosen from those of formulae (I), ( ⁇ ) to ( ⁇ ), and 1 to 6, in particular 1_ to 4, as defined previously, in particular for treating keratin fibres, in particular human keratin fibres such as the hair, preferably for shaping keratin fibres and/or straightening/relaxing said fibres.
  • the reaction medium is then left at ambient temperature for 8 h and then concentrated under reduced pressure.
  • the residue thus obtained is taken up with heptane in order to crystallize the expected compound.
  • the precipitate obtained is then filtered on a sinter funnel and dried under vacuum in the presence of P2O5 to constant weight.
  • the expected compound is thus obtained in the form of white powder, the spectroscopic analyses of which are in accordance with the expected product.
  • the first step is identical to the 1 st step of Example 1.
  • the second step is identical to the 2nd step of Example 1.
  • the first step is identical to the 1 st step of Example 1.
  • the second step is identical to the 2nd step of Example 1.
  • 3rd step Synthesis of 4-(2-oxo-1 ,3-dioxolan-4-yl)butyl 5-oxotetrahydrothiophene-3- carboxylate
  • reaction mixture is maintained at the reflux for 5 h after the addition of the bromine, then is left to return to ambient temperature, before being concentrated to dryness under reduced pressure so as to give a slightly coloured oil.
  • This oil is then added, dropwise, to 500 ml of ethanol while maintaining the temperature at 10°C by means of an ice bath, then the medium is concentrated to dryness under reduced pressure, before being purified by vacuum distillation. A colourless oil is obtained, the spectroscopic analyses of which are in accordance with the expected product.
  • the mixture is then filtered, the precipitate formed is separated from the filtrate and the filtrate is evaporated under reduced pressure.
  • the oil obtained is then dissolved in 300 ml of dichloromethane and then the organic phase is washed with 200 ml of sodium hydrogen carbonate solution, 2000 ml of 2 N hydrochloric acid and 200 ml of a saturated solution of ammonium chloride.
  • the organic phase is subsequently dried and then evaporated under reduced pressure. A yellow oil is obtained, the spectroscopic analyses of which are in accordance with the expected product.
  • reaction medium is then brought to ambient temperature for 3 h, and then 50 ml of a 0.25 M ammonium chloride solution are added thereto.
  • the organic phase is recovered and then washed with 3 times 50 ml of water, dried over sodium sulfate, filtered, then the solvent is evaporated off under reduced pressure.
  • the product obtained is purified by silica column chromatography with 95/5 v/v dichloromethane/methanol as eluent. A whitish- grey solid is obtained, the spectroscopic analyses of which are in accordance with the expected product.
  • Step 1 Application of cleansing shampoo (so as to obtain clean hair):
  • Step 2 Application of the test product of the invention:
  • the locks are then shampooed according to the following protocol, which may be repeated according to the desired number of shampooing operations:
  • a lock of natural Caucasian wavy hair of length not treated with the compounds of the invention (that is to say a look undergoing only steps 1 and 3 of the protocol) is compared with a lock of Caucasian wavy hair of length treated with the compounds of the invention (steps 1 , 2 and 3) by performing 10 successive shampooing operations in step 3.
  • the straightening effect is visualized by measuring the length of each lock after treatment.
  • the composition containing the compound of the invention (compound of Example 1 ) applied in step 2 is a 70 water/30 ethanol aqueous alcoholic composition containing 10% of compound of Example 1 .
  • the pH of this composition is 4.7.
  • Step 1 Application of cleansing shampoo (so as to obtain clean hair):
  • Step 2 Application of the compound according to the invention and of the comparative combination A + B: 1 Weigh out 0.59 g of compound A (0.0046 mol) and 0.48 grams of compound B (0.0046 mol) then add 10 ml of water. Idem for compound 1 of the invention, weigh out 1 g of compound 1 (0.0046 mol) and dissolve it in 10 ml of water.
  • the locks are then shampooed according to the following protocol, which may be repeated according to the number of shampooing operations performed:

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)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne i) un procédé de traitement de matières kératiniques, en particulier de fibres kératiniques humaines, comprenant l'application d'une composition comprenant au moins une thiolactone comprenant une fonction carbonate de formule (I), en particulier pour la mise en forme de fibres kératiniques et/ou le lissage/défrisage, ii) une composition comprenant la ou les thiolactones comprenant une fonction carbonate de formule (I), iii) de nouvelles thiolactones comprenant une fonction carbonate de formule (I), iv) un procédé de préparation des nouvelles thiolactones comprenant une fonction carbonate de formule (I), et v) l'utilisation desdites thiolactones comprenant une fonction carbonate dans des produits cosmétiques, (I) dans laquelle formule (I) R1, R2, R3, R4, X, Y, A, B, a et b sont tels que définis dans la description.
PCT/EP2018/079798 2017-11-03 2018-10-31 Composition comprenant des thiolactones comprenant une fonction carbonate et procédé de traitement de matières kératiniques l'utilisant WO2019086505A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1760354A FR3073143B1 (fr) 2017-11-03 2017-11-03 Composition comprenant des thiolactones a fonction carbonate et procede de traitement des matieres keratiniques la mettant en œuvre
FR1760354 2017-11-03

Publications (2)

Publication Number Publication Date
WO2019086505A2 true WO2019086505A2 (fr) 2019-05-09
WO2019086505A3 WO2019086505A3 (fr) 2019-08-15

Family

ID=61224013

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/079798 WO2019086505A2 (fr) 2017-11-03 2018-10-31 Composition comprenant des thiolactones comprenant une fonction carbonate et procédé de traitement de matières kératiniques l'utilisant

Country Status (2)

Country Link
FR (1) FR3073143B1 (fr)
WO (1) WO2019086505A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111909374A (zh) * 2020-07-23 2020-11-10 河北工业大学 一种具有自修复性能的锂电池粘结剂的制备方法及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1837010A2 (fr) 2006-03-17 2007-09-26 L'Oréal Processus de relaxation ou de défrisage des cheveux
WO2007144707A2 (fr) 2006-06-09 2007-12-21 Nokia Corporation Découverte locale de services de réseaux mobiles
WO2009117344A2 (fr) 2008-03-19 2009-09-24 L'oreal Utilisation d'une composition et procédé impliquant l'utilisation d'une base non-hydroxyde et d'un dénaturant de protéine du type thermique pour relaxer ou raidir les cheveux
WO2010049434A2 (fr) 2008-10-29 2010-05-06 L'oreal Traitement pour lisser ou défriser les cheveux au moyen d'acides dicarboxyliques faibles avec de la chaleur
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1519281A (fr) * 1966-04-18 1968-03-29 Unilever Nv Traitement modifiant la forme des cheveux
DE602006013314D1 (de) * 2005-05-12 2010-05-12 Showa Denko Kk Dauerhafte haarverformung und gleichzeitige haarfärbung
ATE467440T1 (de) * 2007-01-16 2010-05-15 Unilever Nv Haarstärkungszusammensetzung

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1837010A2 (fr) 2006-03-17 2007-09-26 L'Oréal Processus de relaxation ou de défrisage des cheveux
WO2007144707A2 (fr) 2006-06-09 2007-12-21 Nokia Corporation Découverte locale de services de réseaux mobiles
WO2009117344A2 (fr) 2008-03-19 2009-09-24 L'oreal Utilisation d'une composition et procédé impliquant l'utilisation d'une base non-hydroxyde et d'un dénaturant de protéine du type thermique pour relaxer ou raidir les cheveux
WO2010049434A2 (fr) 2008-10-29 2010-05-06 L'oreal Traitement pour lisser ou défriser les cheveux au moyen d'acides dicarboxyliques faibles avec de la chaleur
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111909374A (zh) * 2020-07-23 2020-11-10 河北工业大学 一种具有自修复性能的锂电池粘结剂的制备方法及其应用
CN111909374B (zh) * 2020-07-23 2022-03-29 河北工业大学 一种具有自修复性能的锂电池粘结剂的制备方法及其应用

Also Published As

Publication number Publication date
FR3073143B1 (fr) 2019-10-11
FR3073143A1 (fr) 2019-05-10
WO2019086505A3 (fr) 2019-08-15

Similar Documents

Publication Publication Date Title
JP6764792B2 (ja) ケラチン処理調合物及び方法
US6240929B1 (en) Heterocyclic quaternary polyammonium silicon polymers and their use in cosmetic compositions
EP1143916A2 (fr) Compositions topiques comprenant des thiols fonctionnels proteges
JP2004315820A (ja) チオール官能基を含むＮ−α−及びＮ−ε−リジン及びオルニチン誘導体、並びにその美容的使用
WO2013117771A2 (fr) Procédé de traitement cosmétique et composition comprenant un dérivé d'acide glyoxylique
US20220409508A1 (en) Process for curl-relaxing and/or straightening keratin fibres, using reducing agents and polar organic solvents, and straightening kit
JP2011525475A (ja) カチオン性界面活性剤化合物を含む化粧品組成物、新規化合物、コンディショナーとしての使用、並びに美容処理方法
US20020012639A1 (en) Topical compositions comprising protected functional thiols
FR2978038A1 (fr) Procede de coloration des fibres keratiniques precede d'un traitement a base de liquide ionique
WO2019086505A2 (fr) Composition comprenant des thiolactones comprenant une fonction carbonate et procédé de traitement de matières kératiniques l'utilisant
WO2018115091A1 (fr) Composition comprenant des bisthiolactones et procédé de traitement de matières kératiniques l'utilisant
WO2011154457A1 (fr) Composition comprenant au moins une 2-pyrrolidone fonctionnalisée en position 4 avec un acide carboxylique ou un amide, utile pour le traitement après-shampooing de matériau kératinique
US20140366905A1 (en) Process for treating keratin fibers
WO2017103038A2 (fr) Composition de coloration de fibres kératiniques comprenant un colorant direct styryle ou naphylamide portant une fonction hydroxyalkyle, procédé de coloration et colorant
WO2017081125A1 (fr) Procédé de traitement de fibres de kératine avec une composition comprenant un agent de réticulation et un fer à vapeur
US20210007957A1 (en) Process for curl-relaxing and/or straightening keratin fibres, using a thiol-based reducing agent and a dicarboxylic acid derivative, and straightening kit
ES2824276T3 (es) Procedimiento para tratar fibras queratínicas con un polímero de alcoxisilano que soporta un grupo nucleófilo y un (tio)éster activado
US20190328640A1 (en) Process for Relaxing Curls and/or Straightening Keratin Fibres, Using a Composition Low in Reducing Agents and Straightening Kit
WO2018115258A1 (fr) Procédé de traitement de matières kératiniques par l'utilisation d'une composition comprenant un composé de type thiolactone et d'une composition comprenant un agent alcalin et/ou un dérivé aminé d'alkoxysilane
EP3558250A1 (fr) Composition comprenant un composé de type thiolactone et un solvant particulier et procédé de traitement de matières kératiniques avec la composition
WO2018115093A1 (fr) Composition acide comprenant des thiolactones et procédé de traitement de matières kératiniques mettant en œuvre ladite composition
EP3374030A1 (fr) Procédé de traitement de fibres de kératine au moyen d'un composé de disulfure cationique
US10993899B2 (en) Composition for dyeing keratin fibres, comprising a styryl or naphthylamide direct dye bearing an aminoalkyl function, dyeing process and dye
WO2018115394A1 (fr) Procédé de défrisage et/ou de lissage de fibres kératiniques faisant appel à des agents réducteurs et à des composés disulfures cationiques, et kit de lissage
JPH04112813A (ja) 毛髪処理剤組成物

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18865374

Country of ref document: EP

Kind code of ref document: A2