WO2021229025A1 - Dérivés de dibenzylidène alditol, composition les comprenant et leur utilisation en cosmétique - Google Patents

Dérivés de dibenzylidène alditol, composition les comprenant et leur utilisation en cosmétique Download PDF

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WO2021229025A1
WO2021229025A1 PCT/EP2021/062766 EP2021062766W WO2021229025A1 WO 2021229025 A1 WO2021229025 A1 WO 2021229025A1 EP 2021062766 W EP2021062766 W EP 2021062766W WO 2021229025 A1 WO2021229025 A1 WO 2021229025A1
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oil
thio
formula
chosen
compounds
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English (en)
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Eric PHALEMPIN
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L'oreal
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Definitions

  • a subject matter of the present invention is a composition comprising at least one specific dibenzylidene alditol derivative of formula (I), a cosmetic treatment process comprising said derivative, novel dibenzylidene alditol derivatives, their process of preparation and their use in cosmetics, in particular for thickening lipophilic media, such as oils, and more particularly in "cosmetic sticks", such as lipsticks.
  • Cosmetic compositions are generally thickened in order to make possible easy application.
  • the formulator has available numerous possibilities for thickening and gelling both hydrophilic media and lipophilic media, such as oils.
  • a person skilled in the art generally uses crystallizable compounds which are essentially waxes, such as polyethylene waxes, candelilla waxes, carnauba waxes or beeswaxes, and also pasty compounds, predominantly lanolins.
  • a mixture consisting of 50-70% of oils and of pasty compounds can be brought to the level of consistency making it possible to manufacture a disintegratable "stick" by addition of 12-20% of waxes.
  • the sticks thus obtained have the disadvantages of being dull and brittle.
  • Dibenzylidene alditol derivatives are known in the literature, for example as gelling agents for hydrocarbons or for polar media (Xylitol Based Phase Selective Organogelators for Potential Oil Spillage Recovery, RSC Adv., 2017, 7, p. 37175, WO 2018/002947, and JP63304079).
  • these dibenzylidene alditols are not known as gelling agents for cosmetic oily media.
  • sorbitol dibenzylidene esters As thickeners for lipophilic media but their use generally requires a high temperature (approximately 120°C), which is not always compatible with the formulated media to be thickened, in particular for reasons of instability or of degradation of certain ingredients (EP 2 542556 A1).
  • the thickened medium may lack uniformity of thickness, such as, for example, a liquid part and/or the presence of a solid, or also result in opaque thickened media, which can be a handicap in certain applications.
  • R 1 to R' 5 which are identical or different, represent a hydrogen atom, a halogen atom, such as fluorine, chlorine or bromine; or a group chosen from: i) linear or branched (Ci-Ce)alkyl, ii) -0-R a , iii) -C(X)-0-Rbor-0-C(X)-Rb, iv) - NRcR d and v) -C(X)-NR c R d or -N(R c )-C(X)-R d , with R a representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, an aryl(Ci-C4)alkyl group, such as benzyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl; R representing a hydrogen atom or a (Ci-C4)alkyl group; R c
  • R represents a radical chosen from i) -Xi; ii) -C(X)-Xi; iii) -C(X)-0-Xi; iv) -C(X)-N(Rc)-Xi; with X as defined above; preferably, X represents an oxygen atom; and Xi representing a) a (C 4 -C 8 )cycloalkyl group, such as cyclohexyl; or b) a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 6 to 24 carbon atoms, said chain being:
  • heteroatoms or divalent radicals chosen from: O, S, N(R C ), C(O) or their combinations, such as -O-C(O)-, - C(0)-0-, -C(0)-N(Rc)- or -N(R c )-C(0)-; and/or
  • halogen atoms and/or groups which are identical or different, chosen from: -0-R a , -C(0)-0-R b ,
  • R a and R b represent a (Ci-C4)alkyl group, such as methyl.
  • Another subject-matter of the invention is a cosmetic treatment process employing one or more compounds of formula (I) as defined above.
  • Another subject-matter of the invention is the compounds of formula (I) as defined above.
  • Another subject-matter of the invention is a process for the preparation of compounds of formula (I) as defined above.
  • composition preferably a cosmetic composition, comprising one or more compounds of formula (I) as defined above.
  • fatty substance is understood to mean an organic compound which is insoluble in water at ordinary temperature (25 °C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, and preferably of less than 1%, more preferentially still of less than 0.1%); in addition, fatty substances are soluble in organic solvents under the same temperature and pressure conditions, such as, for example, in halogenated solvents, such as chloroform or dichloromethane, lower alcohols, such as ethanol, or aromatic solvents, such as benzene or toluene.
  • halogenated solvents such as chloroform or dichloromethane
  • lower alcohols such as ethanol
  • aromatic solvents such as benzene or toluene.
  • organic or inorganic acid salt' is understood more particularly to mean the salts chosen from a salt derived i) from hydrochloric acid HCI, ii) from hydrobromic acid HBr, iii) from sulfuric acid H2SO4, iv) from alkylsulfonic acids: Alk-S(0) 2 0H, such as from methylsulfonic acid and from ethylsulfonic acid; v) from arylsulfonic acids: Ar- S(0) 2 0H, such as from benzenesulfonic acid and from toluenesulfonic acid; vi) from citric acid; vii) from succinic acid; viii) from tartaric acid; ix) from lactic acid; x) from alkoxysulfinic acids: Alk-0-S(0)0H, such as from methoxysulfinic acid and from ethoxysulfinic acid; xi) from aryloxysulfinic acids, such
  • salts of organic or inorganic bases is understood to mean salts of alkaline bases or agents as defined below, such as alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, aqueous ammonia, amines or alkanolamines.
  • alkyl radical' it is saturated, linear or branched, C-i-Cs, preferably C 1 -C6, more preferentially C 1 -C 4 , hydrocarbon radical, such as methyl or ethyl;
  • an "alkoxy radicaf' is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C16, preferentially C-i-Cs, hydrocarbon radical;-
  • the expression "at least one” is equivalent to "one or more”;
  • R 1 to R' 5 which are identical or different, represent a hydrogen atom, a halogen atom, such as fluorine, chlorine or bromine; or a group chosen from: i) linear or branched (Ci-C6)alkyl, ii) -0-R a , iii) -C(0)-0-R b or -0-C(0)-R b , iv) -NR c R d and v) - C(0)-NR c RdOr -N(R c )-C(0)-R , with:
  • - R a representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, an aryl(Ci-C4)alkyl group, such as benzyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl;
  • R c and R d which are identical or different, representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl;
  • two adjacent Ri to R' 5 radicals can also form, together with the carbon atoms which carry them, an unsaturated (Cs-Cs) ring, such as benzo;
  • R represent a radical chosen from i) -Xi; ii) -C(0)-Xi; iii) -C(0)-0-Xi; iv) -C(O)- N(Rc)-Xi; with Xi representing a) a (C4-C8)cycloalkyl group, such as cyclohexyl; or b) a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 6 to 24 carbon atoms (particularly from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atom), said chain being:
  • heteroatoms or divalent radicals chosen from: O, S, N(Rc), C(O) or their combinations, such as -O-C(O)-, -C(0)-0-, -C(0)-N(R c )- or -N(Rc)-C(0)-, and/or
  • halogen atoms or groups which are identical or different, chosen from: -0-R a , -C(0)-0-R b , -NR c R d and (C4-C8)cycloalkyl with R a and R b as defined above; preferably, R a and R b represent a (Ci-C4)alkyl group, such as methyl.
  • the compounds of formula (I) of the invention are of formula (la), and also their organic or inorganic acid or base salts, and their solvates, such as hydrates:
  • the compounds of formula (I) or (la) of the invention are such that R 1 is identical to R' 1 , R 2 is identical to R' 2 , R 3 is identical to R' 3 , R 4 is identical to R' 4 and R 5 is identical to R' 5 .
  • the compounds of formula (I) or (la) are such that the R 1 to R' 5 radicals, which are identical or different, represent i) a hydrogen atom or ii) a (Ci-Ce)alkyl group; iii) an -0-R a group or iv) a -C(0)-0-R b group with R a and R as defined above; preferably, R a represents a hydrogen atom, a (Ci-C 4 )alkyl group or a benzyl group; and R b represents a hydrogen atom or a (Ci-C 4 )alkyl group.
  • the compounds of formula (I) or (la) are such that R is as defined above and Xi preferably represents a) a (C 4 -C 8 )cycloalkyl radical, b) a saturated or unsaturated and linear or branched C 10 -C 24 hydrocarbon chain, said chain optionally being interrupted by one or more heteroatoms or divalent radicals chosen from -0-, -N(R C )-, -C(O)- and their combinations, such as -O-C(O)-, -C(0)-0-, -C(0)-N(R c )- or -N(R C )- C(O)-, and/or said chain optionally being substituted by one or more identical or different radicals chosen from the -0-R a or -C(0)-0-R b radicals with R a representing a (Ci-C 4 )alkyl group and R b representing a (Ci-C 4 )al
  • the compounds of formula (I) or (la) of the invention are such that R 1 to R' 5 , which are identical or different, represent a hydrogen atom or a group chosen from (Ci-Ce)alkyl or -0-R a with R a representing a hydrogen atom or (Ci-C 4 )alkyl group, preferably R 1 to R' 5 represent a hydrogen atom.
  • R b represents a hydrogen atom or a (Ci-C 4 )alkyl group; more preferentially, R b represents a (Ci-C 4 )alkyl group.
  • the compounds of formula (I) or (la) of the invention are such that R c and R d , which are identical or different, represent a (Ci-C 4 )alkyl group.
  • the compounds of formula (I) or (la) of the invention are such that R is as defined above, preferably represents X-i.
  • the compounds of formula (I) or (la) of the invention are such that R represents a -C(0)-Xi radical with Xi preferably representing a saturated or unsaturated and linear or branched C10-C24 hydrocarbon chain, preferably a linear or branched C10-C24 hydrocarbon chain.
  • the compounds of formula (I) or (la) of the invention are such that Xi represents a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms, said chain optionally being interrupted by one or more heteroatoms or divalent radicals chosen from -0-, -N(R C )-, -C(O)- and their combinations, such as -O-C(O)-, - C(0)-0-, -C(0)-N(Rc)- or -N(R c )-C(0)-, and/or said chain optionally being substituted by one or more identical or different radicals chosen from -0-R a or - C(0)-0-R b radicals with R a representing a (Ci-C4)alkyl group and R b representing a (Ci-C4)alkyl group.
  • the compounds of formula (I) or (la) of the invention are such that Xi represents a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.
  • the compounds of formula (I) or (la) are such that R 1 to R' 5 are identical. More particularly, the compounds of formula (I) or (la) of the invention are such that R 1 to R 5 and R' 1 to R' 5 represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group. More preferentially still, the compounds of formula (I) or (la) of the invention are such that R 1 to R' 5 represent a hydrogen atom.
  • the compounds of formula (I) or (la) are such that R 1 to R' 5 represent a hydrogen atom and R represents a -C(0)-Xi radical with Xi denoting a hydrocarbon chain as defined above and in particular with Xi denoting a linear or branched C10-C24 hydrocarbon chain.
  • the compounds of formula (I) of the invention are chosen from those of following formula (1-1), and also its optical or geometrical isomers, and its solvates, such as hydrates:
  • the compounds of formula (I), (1-1) or (la) of the invention are chosen from those of following formula (I'a), and also its geometrical isomers, and solvates, such as hydrates:
  • the compounds of formula (I), (1-1), (la) or (I'a) of the invention are such that Xi is as defined above, and preferentially Xi represents a linear or branched, preferably linear, hydrocarbon chain comprising from 1 to 3 unsaturations, in particular 1 insaturation, and comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.
  • the compounds of formula (I), (1-1), (la) or (I'a) of the invention are such that Xi represents a saturated, linear or branched, hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.
  • Xi represents a -(ChhVCH- R1R2 chain with Ri and R2, which are identical or different, representing a hydrogen atom or a (Ci-Ce)alkyl group, such as methyl, and p representing an integer of inclusively between 9 and 21, preferably between 11 and 19, more particularly between 13 and 17, such as 14 or 15.
  • (la) or (I'a) of the invention are such that Xi represents an unsaturated, linear or branched (preferably linear), hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.
  • Xi represents an unsaturated, linear or branched (preferably linear), hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.
  • the compounds of formula (I) of the invention are chosen from the following compounds (1) to (3):
  • the compounds of formula (I) of the invention are chosen from the following compounds (1a) to (3a):
  • this (thio)esterification stage can be carried out by the chemical route, for example by reaction with a (thio)acid Xi-C(X)-OH in acid catalysis, or also by a trans(thio)esterification reaction with a (thio)ester, such as X-i- C(X)-0-R3, with R3 representing a (Ci-C 4 )alkyl group, such as methyl, preferably in acid catalysis, or also by reaction of (C) with a (thio)acid halide Xi-C(X)-Hal with Xi as defined above and Hal representing a halogen atom, such as chlorine or iodine, preferably chloride: Xi-C(0)-Cl, or by any other (thio)esterification method, such as, for example, those described in Advanced Organic Chemistry, 6 th Ed.,
  • This (thio)esterification reaction can in particular be carried out by the biocatalytic route with a supported or unsupported lipase in a solvent, preferably a polar aprotic solvent, such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran or methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification of (C) to give (G) is carried out with a supported lipase, which makes possible the recycling of the enzyme on conclusion of the reaction; or
  • Route B to the synthesis of a (thio)carbonate in order to result in the compounds (I") of the invention; this stage can be carried out by the chemical route, for example by the reaction with an activator composed of a (Ci-Ce)alkyl 1 ,3-dicarbonyl derivative in the presence of magnesium perchlorate, or with a 4,5-dichloro-6-oxopyridazin- 1(6/-/)-carboxylate derivative in the presence of a base, such as potassium tert- butoxide, or, for example, by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see in particular pp. 10, 16, 19 and 58).
  • a base such as potassium tert- butoxide
  • Route C to the synthesis of a (thio)carbamate or (thio)urethane in order to result in the compounds (G") of the invention; this stage can be carried out by the chemical route, for example by the reaction with a C1-C6 alkyl iso(thio)cyanate, obtained by the treatment of an aliphatic alcohol with a phosphine, such as triphenylphosphine/2,3- dichloro-5,6-dicyanobenzoquinone/Bu 4 NOCN, or, for example, by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see in particular pp. 8, 10, 16 and 17).
  • a phosphine such as triphenylphosphine/2,3- dichloro-5,6-dicyanobenzoquinone/Bu 4 NOCN
  • Route D to the synthesis of an ether oxide in order to result in the compounds (I"") of the invention; this stage can be carried out by the chemical route, for example by the reaction with a halide X-i-Hal, for example the alkyl iodide Xi I, in the presence of a strong base, such as a reducing metal (Li, Na, K) or a sodium or potassium hydride, or also by reaction of (C) with an alcohol, of XiOH type, in the presence of an acid, preferably an inorganic acid, such as sulfuric acid, with removal of water, or by reaction of (C) with an organomagnesium compound of R-MgHal type, followed by condensation with a halide Xi-Hal as defined above, or by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see, in particular pp. 8 and 10).
  • a strong base such as a reducing metal (Li, Na, K) or a
  • alditols (A) denote in particular xylitol or ribitol.
  • Another subject-matter of the invention is a process for the preparation of the compounds of formula (I) for which R 1 is different from R' 1 , and/or R 2 is different from R' 2 , and/or R 3 is different from R' 3 , and/or R 4 is different from R' 4 and/or R 5 is different from R' 5 comprising a first stage 1 ) in which the alditol (A) as defined above is reacted with a molar equivalent of aldehyde (B) as defined above in a solvent, preferably a polar protic solvent, such as water, in the presence of a catalyst chosen in particular from organic or inorganic acids, such as hydrochloric acid or para-toluenesulfonic acid, and preferably the medium is heated to a temperature of inclusively between 30°C and 80°C, in particular of inclusively between 40°C and 70°C, for a period of time preferentially of between 30 minutes and 2 days; after cooling the medium down to ambient temperature (25
  • this (thio)esterification stage can be carried out by the chemical route, for example by reaction with a (thio)acid Xi-C(X)-OH in acid catalysis, or also by a trans(thio)esterification reaction with a (thio)ester, such as X-i- C(X)-0-R3, with R3 representing a (Ci-C 4 )alkyl group, such as methyl, preferably in acid catalysis, or also by reaction of (Cb) with a (thio)acid halide Xi-C(X)-Hal with Xi as defined above and Hal representing a halogen atom, such as chlorine or iodine, preferably chloride: Xi-C(0)-Cl, or by any (thio)esterification method as mentioned above;
  • This (thio)esterification reaction is in particular carried out by the biocatalytic route with a supported or unsupported lipase in a solvent, preferably a polar aprotic solvent, such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran or methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification of (Cb) to give (I'b) is carried out with a supported lipase, which makes possible the recycling of the enzyme on conclusion of the reaction; or
  • Route B' to the synthesis of a (thio)carbonate in order to result in the compounds (l"b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with an activator composed of a (Ci-Ce)alkyl 1 ,3-dicarbonyl derivative in the presence of magnesium perchlorate, or with a 4,5-dichloro-6- oxopyridazin-1(6/-/)-carboxylate derivative in the presence of a base, such as potassium tert- butoxide, or, for example, by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see in particular pp. 10, 16, 19 and 58).
  • a base such as potassium tert- butoxide
  • Route C to the synthesis of a (thio)carbamate or (thio)urethane in order to result in the compounds (l'"b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with a C 1 -C 6 alkyl iso(thio)cyanate, obtained by the treatment of an aliphatic alcohol with a phosphine, such as triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu 4 NOCN, or, for example, by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see in particular pp. 8, 10, 16 and 17).
  • a phosphine such as triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu 4 NOCN
  • Route D' to the synthesis of an ether oxide in order to result in the compounds (l""b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with a halide Xi-Hal, for example the alkyl iodide Xi I, in the presence of a strong base, such as a reducing metal (Li, Na, K) or a sodium or potassium hydride, or also by reaction of (Cb) with an alcohol, of X 1 OH type, in the presence of an acid, preferably an inorganic acid, such as sulfuric acid, or by reaction of (Cb) with an organomagnesium compound of R-MgHal type, followed by condensation with a halide Xi-Hal as defined above, or by any method described in Advanced Organic Chemistry, 6 th Ed., Jerry March, from Wiley Interscience (see, in particular pp. 8 and 10). [Chem. 11]
  • Another subject-matter of the invention is a composition
  • a composition comprising one or more compounds of formula (I), (1-1), (la), (I'a), (1), (2), (3), (1a), (2a) or (3a) as defined above, and also their organic or inorganic acid or base salts, their optical or geometrical isomers, and their solvates, such as hydrates.
  • the amount of the compound(s) of formula (I), (1-1), (la), (I'a), (1), (2), (3), (1a), (2a) or (3a) of the invention present in the composition depends, of course, on the texture desired for said composition, which can range from a fluid gel to a stick, and/or on the properties desired. [0040] Preferably, the amount of compounds of formula (I), (1-1), (la), (I'a), (1), (2),
  • (1a), (2a) or (3a) is less than or equal to 15%, more preferentially less than or equal to 10% by weight and in particular less than or equal to 8% by weight, with respect to the total weight of the cosmetic composition; it can be between 0.005% and 15% by weight, preferably between 0.01% and 13% by weight, in particular between 0.1% and 10% by weight, indeed even between 0.2% and 9% by weight and better still between 0.5% and 8% by weight, with respect to the total weight of the cosmetic composition.
  • composition of the invention denotes in particular a cosmetic composition.
  • Cosmetic composition is understood to mean a physiologically acceptable composition.
  • hysiologically acceptable composition is understood to mean a composition compatible with the keratin materials of human beings, such as the skin, in particular of the body and of the face, lips, the scalp, the hair, the eyelashes, the eyebrows and the nails.
  • the composition of the invention additionally comprises ii) one or more liquid fatty substances.
  • the fatty substances of the invention are chosen from hydrocarbons, fatty alcohols, fatty esters, silicones and fatty ethers, or their mixtures. More particularly, the fatty substances of the invention are not (poly)oxyalkylenated.
  • liquid fatty substances is understood to mean fatty substances which are liquid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 5 Pa).
  • the liquid fatty substances of the invention exhibit in particular a viscosity of less than or equal to 2 Pa.s, more particularly of less than or equal to 1 Pa.s and more particularly still of less than or equal to 0.1 Pa.s, more preferentially of less than or equal to 0.09 Pa.s at a temperature of 25°C and at a shear rate of 1 s 1 .
  • [0049] exhibit in a viscosity of between 0.001 Pa.s and 2 Pa.s, more particularly of inclusively between 0.01 and 1 Pa.s and more particularly still of inclusively between 0.014 and 0.1 Pa.s, more preferentially of inclusively between 0.015 and 0.09 Pa s, at a temperature of 25°C and at a shear rate of 1 s -1 .
  • liquid hydrocarbon is understood to mean a hydrocarbon composed solely of carbon and hydrogen atoms which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 5 Pa).
  • liquid hydrocarbons are chosen from:
  • hydrocarbons of mineral, animal or synthetic origin of more than 16 carbon atoms such as liquid paraffins, liquid petrolatum, polydecenes, hydrogenated polyisobutene, such as Parleam®, or squalane.
  • liquid hydrocarbon(s) are chosen from liquid paraffins and liquid petrolatum.
  • liquid fatty alcohof' Is understood to mean a non-glycerolated and non-oxyalkylenated fatty alcohol which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 5 Pa).
  • the liquid fatty alcohols of the invention comprise 8 to 30 carbon atoms, more preferentially C10-C22, more preferentially still C14-C20 and better still C16-C18 liquid fatty alcohols.
  • liquid fatty alcohols of the invention can be saturated or unsaturated.
  • the liquid saturated fatty alcohols are preferably branched. They can optionally comprise, in their structure, at least one aromatic or non-aromatic ring. Preferably, they are acyclic.
  • liquid saturated fatty alcohols of the invention are chosen from octyldodecanol, isostearyl alcohol or 2-hexyldecanol.
  • the fatty substance(s) are chosen from liquid unsaturated fatty alcohols. These liquid unsaturated fatty alcohols exhibit, in their structure, at least one double or triple bond.
  • the fatty alcohols of the invention have, in their structure, one or more double bonds. When several double bonds are present, they are preferably 2 or 3 in number and they can be conjugated or non-conjugated.
  • These unsaturated fatty alcohols can be linear or branched.
  • liquid unsaturated fatty alcohols of the invention are chosen from oleyl alcohol, linoleyl alcohol, linolenyl alcohol or undecylenyl alcohol.
  • Oleyl alcohol is very particularly preferred.
  • liquid fatty ester is understood to mean an ester resulting from a fatty acid and/or from a fatty alcohol which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg, i.e. 1.013 x 10 5 Pa).
  • the esters are preferably liquid esters of saturated or unsaturated and linear or branched C1-C26 aliphatic mono- or polyacids and of saturated or unsaturated and linear or branched C1-C26 aliphatic mono- or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • one at least of the alcohol or of the acid from which the esters of the invention result is branched.
  • alkyl myristates such as isopropyl myristate or ethyl myristate
  • isocetyl stearate 2-ethylhexyl isononanoate
  • isodecyl neopentanoate isostearyl neopentanoate
  • Use may also be made of esters of C4-C22 di- or tricarboxylic acids and of Ci- C22 alcohols and esters of mono-, di- or tricarboxylic acids and of non-sugar di-, tri-, tetra- or pentahydroxy C4-C26 alcohols.
  • composition can also comprise, as liquid fatty ester, sugar esters and diesters of C6-C30, preferably C12-C22, fatty acids.
  • sugar esters and diesters of C6-C30, preferably C12-C22, fatty acids.
  • sucrose is understood to mean oxygen-carrying hydrocarbon compounds which have several alcohol functional groups, with or without an aldehyde or ketone functional group, and which comprise at least 4 carbon atoms.
  • sugars can be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars for example, of sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose, and their derivatives, in particular alkylated derivatives, such as methylated derivatives, for example methylglucose.
  • the esters of sugars and of fatty acids can in particular be chosen from the group consisting of the esters and mixtures of esters of sugars described above and of saturated or unsaturated and linear or branched C6-C30, preferably C12- C22, fatty acids. If they are unsaturated, these compounds can comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this alternative form can also be chosen from mono-, di-, tri- and tetraesters, polyesters and their mixtures.
  • esters can, for example, be oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates or arachidonates, or their mixtures, such as, in particular, mixed oleate/palmitate, oleate/stearate and palmitate/stearate esters.
  • oils of vegetable origin or synthetic triglycerides which can be used in the composition of the invention as liquid fatty esters, for example, of:
  • triglyceride oils of vegetable or synthetic origin such as liquid triglycerides of fatty acids comprising from 6 to 30 carbon atoms, such as triglycerides of heptanoic or octanoic acids, or also, for example, sunflower oil, maize oil, soybean oil, pumpkin oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, such as those sold by Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel, jojoba oil or shea butter oil.
  • liquid triglycerides of fatty acids comprising from 6 to 30 carbon atoms such as triglycerides of heptanoic or octanoic acids, or also, for example, sunflower oil, maize oil, soybean oil, pumpkin oil, grapeseed oil
  • liquid fatty esters resulting from monoalcohols will be used as esters according to the invention.
  • Isopropyl myristate or isopropyl palmitate are preferred.
  • liquid fatty ethers are chosen from liquid dialkyl ethers, such as dicaprylyl ether.
  • compositions of the invention contain ii) one or more fatty substances which are liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 5 Pa). These liquid fatty substances can thus be of natural or synthetic origin.
  • the liquid fatty substance(s) ii) of the invention are chosen from a) linear or branched hydrocarbons of more than 16 carbon atoms, such as liquid paraffins, liquid petrolatum, polydecenes or hydrogenated polyisobutylene, such as squalane, preferably squalane, b) liquid saturated or unsaturated and linear or branched fatty alcohols, such as octyldodecanol, and c) vegetable oils, such as olive oil, wheat germ oil, maize oil, sunflower oil, shea oil, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, red kuri squash oil, sesame oil, pumpkin oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, saf
  • the compound(s) of formula (I), (1-1), (la) or (l'a) of the invention make it possible to structure ii) the cosmetic liquid fatty substances normally employed, and in particular the liquid fatty substances as defined above.
  • the liquid fatty substance(s) ii) used in the composition according to the present invention can be present in the composition in an amount varying from 1 % to 99% by weight, preferably in an amount varying from 5% to 99% by weight and more preferentially still in an amount varying from 10% to 99% by weight, with respect to the total weight of the composition.
  • the compounds of formula (I), (1-1 ), (la) or (I'a) according to the invention can also find an application in the field of the industry of paints, varnishes and adhesives, as structuring or thickening, indeed even gelling, agent.
  • Said medium can comprise one or more additional ingredients, distinct from the compounds of formula (I), (1-1), (la) or (I'a) as defined above.
  • composition of the invention can comprise one or more organic solvents.
  • organic solvent is understood to mean an organic substance capable of dissolving another substance without chemically modifying it.
  • C2-C6 alkanols such as ethanol and isopropanol
  • the composition additionally comprises one or more polyols chosen in particular from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerol.
  • composition of the invention can comprise additional compounds, such as cosmetic active principles, such as humectant agents, moisturizing agents, anti-ageing active principles, sunscreens, vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, surfactants, antioxidants, cosmetic active principles, propellants, ceramides, additional film-film agents, polymers or their mixtures.
  • cosmetic active principles such as humectant agents, moisturizing agents, anti-ageing active principles, sunscreens, vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, surfactants, antioxidants, cosmetic active principles, propellants, ceramides, additional film-film agents, polymers or their mixtures.
  • composition according to the invention can in particular be provided in the form:
  • a make-up product in particular for the skin of the face, the body or the lips or the eyelashes, such as a lipstick, concealer, foundation, product for concealing imperfections or stick;
  • a body hygiene composition such as a shower gel or a shampoo, preferably in stick form;
  • a solid composition such as a soap or a cleansing bar, preferably in stick form
  • compositions for caring for or cleaning the skin preferably in stick form.
  • the composition additionally comprises one or more colouring agents chosen in particular from pigments and dyes, preferably direct dyes.
  • the composition comprises one or more colouring agents chosen from pulverulent colourants, such as pigments, fillers, pearlescent agents and glitter, and/or fat-soluble or water-soluble dyes.
  • the composition comprises one or more colouring agents chosen from pigments, direct dyes and their mixtures.
  • the composition according to the invention comprises one or more pigments.
  • igment is understood to mean any pigment, of synthetic or natural origin, which gives colour to keratin materials.
  • solubility of the pigments in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight and preferably less than 0.01%.
  • the pigments which can be used are chosen in particular from the organic and/or inorganic pigments known in the art, in particular those which are described in the Kirk-Othmer Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry. Mention may in particular be made, as pigments, of organic and inorganic pigments, such as those defined and described in Ullmann’s Encyclopedia of Industrial Chemistry, "Pigments, Organic", 2005, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20371 et ibid., "Pigments, Inorganic, 1. General", 2009, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20_243.pub3.
  • These pigments can be provided in the pigment powder or paste form. They can be coated or uncoated.
  • the pigments can, for example, be chosen from inorganic pigments, organic pigments, lakes, special effect pigments, such as pearlescent agents or glitter, and their mixtures.
  • the pigment can be an inorganic pigment.
  • inorganic pigment is understood to mean any pigment which satisfies the definition of Ullmann’s Encyclopedia in the chapter "Pigments, Inorganic”. Mention may be made, among the inorganic pigments of use in the present invention, of iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.
  • the pigment can be an organic pigment.
  • organic pigment is understood to mean any pigment which satisfies the definition of Ullmann’s Encyclopedia in the chapter “Pigments, Organic”.
  • the organic pigment can in particular be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane or quinophthalone compounds.
  • the white or coloured organic pigments can be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Colour Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Colour Index under the references Cl 11680, 11710, 15985,
  • pigment pastes of organic pigments such as the products sold by Hoechst under the name: - Cosmenyl Yellow IOG: Pigment Yellow 3 (Cl 11710);
  • the pigments in accordance with the invention can also be in the form of composite pigments, such as are described in Patent EP 1 184426.
  • These composite pigments can be composed in particular of particles comprising:
  • the term "lake” is understood to mean dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium. Mention may be made, among the organic dyes, of cochineal carmine.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.
  • Mention may be made, among the dyes, of cochineal carmine. Mention may also be made of the dyes known under the following names: D & C Red 21 (Cl 45380), D & C Orange 5 (Cl 45370), D & C Red 27 (Cl 45410), D & C Orange 10 (Cl 45425), D & C Red 3 (Cl 45430), D & C Red 4 (Cl 15510), D & C Red 33 (Cl 17200), D & C Yellow 5 (Cl 19140), D & C Yellow 6 (Cl 15985), D & C Green (Cl 61570), D & C Yellow 10 (Cl 77002), D & C Green 3 (Cl 42053) or D & C Blue 1 (Cl 42090).
  • the pigment(s) can also be special effect pigments.
  • special effect pigments is understood to mean pigments which create in a general way a coloured appearance (characterized by a certain shade, a certain vividness and a certain brightness) which is non-uniform and which changes as a function of the conditions of observation (light, temperature, angles of observation, and the like). They thereby contrast with coloured pigments, which provide a conventional uniform opaque, semi-transparent or transparent shade.
  • pearlescent pigments such as titanium oxide-coated mica covered with an iron oxide, mica covered with an iron oxide, mica covered with bismuth oxychloride, titanium oxide-coated mica covered with chromium oxide, titanium oxide-coated mica covered with an organic dye, in particular of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride. They can also be mica particles, at the surface of which are superimposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • the pearlescent agents can more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or glint.
  • pearlescent agents which can be employed in the context of the present invention, of gold-coloured pearlescent agents sold in particular by Engelhard under the names Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze pearlescent agents sold in particular by Merck under the names Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona), by Eckart under the name Prestige Bronze and by Engelhard under the name Super Bronze (Cloisonne); orange pearlescent agents sold in particular by Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by Merck under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); brown-coloured pearlescent agents sold in particular by Engelhard under the names Nu-Antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); pearlescent agents with a copper
  • multilayer pigments based on synthetic substrates such as alumina, silica, sodium calcium borosilicate or calcium aluminium borosilicate, and aluminium, can be envisaged.
  • pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Flelicones HC from Wacker) or interference holographic glitter (Geometric Pigments or Spectra f/x from Spectratek).
  • Special effect pigments also comprise fluorescent pigments, whether these are substances which are fluorescent in daylight or which produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, for example sold by Quantum Dots Corporation.
  • the variety of the pigments which can be used in the present invention makes it possible to obtain a rich palette of colours and also specific optical effects, such as metallic effects or interference effects.
  • the size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.
  • the pigments can be dispersed in the product by virtue of a dispersing agent.
  • dispersing agent is understood to mean a compound which makes it possible to protect the dispersed particles from their agglomeration or flocculation.
  • This dispersing agent can be a surfactant, an oligomer, a polymer or a mixture of several of them, carrying one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can become attached physically or chemically to the surface of the pigments.
  • These dispersing agents additionally exhibit at least one functional group compatible with or soluble in the continuous medium. Said agent can be charged: it can be anionic, cationic, zwitterionic or neutral.
  • the dispersing agents used are chosen from esters of 12-hydroxystearic acid, more particularly, and of Ce to C20 fatty acid and of polyol, for instance glycerol or diglycerol, such as poly( 12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name of Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name), sold under the reference Dehymyls PGPH by Henkel, or also polyhydroxystearic acid, such as the product sold under the reference Arlacel P100 by Uniqema, and their mixtures.
  • esters of 12-hydroxystearic acid more particularly, and of Ce to C20 fatty acid and of polyol, for instance glycerol or diglycerol, such as poly( 12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name of Solsper
  • compositions of the invention Mention may be made, as other dispersing agents which can be used in the compositions of the invention, of quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17000, sold by Avecia, and polydimethylsiloxane/oxypropylene mixtures, such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C.
  • quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17000, sold by Avecia
  • polydimethylsiloxane/oxypropylene mixtures such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C.
  • the pigments used in the cosmetic composition according to the invention can be surface-treated with an organic agent.
  • the pigments surface-treated beforehand of use in the context of the invention are pigments which have been completely or partially subjected to a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature with an organic agent, such as those which are described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention.
  • organic agents can, for example, be chosen from amino acids; waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polysaccharides, for example chitosan, cellulose and its derivatives; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; proteins; alkanolamines; silicone compounds, for example silicones, polydimethylsiloxanes, alkoxysilanes, alkylsilanes or siloxysilicates; organofluorine compounds, for example perfluor
  • the surface-treated pigments of use in the cosmetic composition according to the invention may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.
  • the surface-treated pigments of use in the context of the present invention can be prepared according to surface-treatment techniques well known to a person skilled in the art or found as such commercially.
  • the surface-treated pigments are covered with an organic layer.
  • the organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.
  • the surface treatment can thus be carried out, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is described in particular in Patent US 4578266.
  • the agent for the surface treatment can represent from 0.1% to 50% by weight of the total weight of the surface-treated pigments, preferably from 0.5% to 30% by weight and more preferentially still from 1% to 10% by weight.
  • the surface treatments of the pigments are chosen from the following treatments:
  • PEG-silicone treatment such as the AQ surface treatment sold by LCW;
  • a chitosan treatment such as the CTS surface treatment sold by LCW;
  • dimethicone/trimethylsiloxysilicate treatment such as the Covasil 4.05 surface treatment sold by LCW;
  • a lauroyl lysine dimethicone treatment such as the LL/SI surface treatment sold by LCW;
  • a magnesium myristate treatment such as the MM surface treatment sold by LCW;
  • an aluminium dimyristate treatment such as the Ml surface treatment sold by Miyoshi;
  • an isostearyl sebacate treatment such as the HS surface treatment sold by Miyoshi;
  • a dimethicone/disodium stearoyl glutamate treatment such as the SA/NAI surface treatment sold by Miyoshi;
  • an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment such as the FSA surface treatment sold by Daito;
  • a polymethylhydrosiloxane/perfluoroalkyl phosphate treatment such as the FS01 surface treatment sold by Daito;
  • a lauroyl lysine/aluminium tristearate treatment such as the LL-StAI surface treatment sold by Daito;
  • an octyltriethylsilane treatment such as the OTS surface treatment sold by Daito;
  • an octyltriethylsilane/perfluoroalkyl phosphate treatment such as the FOTS surface treatment sold by Daito;
  • an acrylate/dimethicone copolymer treatment such as the ASC surface treatment sold by Daito;
  • an isopropyl titanium triisostearate treatment such as the ITT surface treatment sold by Daito;
  • microcrystalline cellulose and carboxymethyl cellulose treatment such as the AC surface treatment sold by Daito;
  • an acrylate copolymer treatment such as the APD surface treatment sold by Daito; - a perfluoroalkyl phosphate/isopropyl titanium triisostearate treatment, such as the PF + ITT surface treatment sold by Daito.
  • composition in accordance with the present invention can furthermore comprise one or more pigments which are not surface-treated.
  • the pigment(s) are inorganic pigments.
  • the pigment(s) are chosen from pearlescent agents.
  • the dispersing agent is present with organic pigments in the composition of the invention in particulate form of submicronic size.
  • micronization method is understood to mean pigments, the particle size of which has been micronized by a micronization method and the mean particle size of which is less than a micrometre (m ⁇ p), in particular between 0.1 and 0.9 mhp and preferably between 0.2 and 0.6 mGh.
  • the dispersing agent and the pigment(s) are present in a (dispersing agentpigment) amount of between 0.5: 1 and 2: 1 , particularly between 0.75: 1 and 1.5: 1 or better still between 0.8: 1 and 1.2: 1.
  • the dispersing agent is suitable for dispersing the pigments and is compatible with a formulation curable by condensation.
  • compatible is understood to mean, for example, that said dispersing agent is miscible in the oily phase of the composition or of the dispersion containing the pigment(s), and it does not delay or reduce the curing.
  • the dispersing agent is preferably cationic.
  • the dispersing agent(s) can thus have a silicone backbone, such as silicone polyether and dispersing agents of aminosilicone type. Mention may be made, among the suitable dispersing agents, of:
  • - aminosilicones i.e. silicones comprising one or more amino groups, such as those sold under the names and references: Byk LPX 21879, by Byk, GP-4, GP- 6, GP-344, GP-851 , GP-965, GP-967 and GP-988-1 , sold by Genesee Polymers,
  • Tego® RC 902 Tego® RC 922, Tego® RC 1041 and Tego® RC 1043, sold by Evonik
  • PDMS polydimethylsiloxane
  • carboxyl groups such as X- 22162 and X-22370, sold by Shin-Etsu
  • epoxy silicones such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682 and GP-695, sold by Genesee Polymers, orTego® RC 1401, Tego® RC 1403 and Tego® RC 1412, sold by Evonik.
  • the dispersing agent(s) are of aminosilicone type and are positively charged.
  • dispersing agents having chemical groups which are capable of reacting with the reactants of the oily phase and thus are capable of improving the 3D network formed from the aminosilicones.
  • dispersing agents of epoxy silicone pigments can react chemically with the aminosilicone prepolymer amino group(s) to increase the cohesion of the aminosilicone film comprising the pigment(s).
  • the pigment(s) iii) of the invention are chosen from carbon black, iron oxides, in particular red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and purple triarylmethane pigments, such as Blue 1 Lake, azo pigments, in particular red azo pigments, such as D&C Red 7, or an alkali metal salt of Lithol Red, such as the calcium salt of Lithol Red B.
  • the amount of pigments varies from 0.5% up to 40% and preferably from 1 % to 20%, with respect to the weight of the composition and dispersion comprising them.
  • composition can comprise one or more direct dye(s).
  • direct dye is understood to mean natural and/or synthetic dyes, other than oxidation dyes. These are dyes which will diffuse superficially over keratin materials, in particular keratin fibres.
  • They can be ionic or non-ionic, in particular cationic, anionic or non-ionic.
  • Suitable direct dyes comprise azo direct dyes; (poly)methine dyes, such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
  • the dye(s), in particular pulverulent dye(s), are present in the composition in a content of from 0.01% to 50% by weight, with respect to the weight of the composition, preferably from 0.1% to 40% by weight, indeed even from 1% to 30% by weight.
  • the pigments can be white or coloured, inorganic and/or organic, and interference or non-interference pigments. Mention may be made, among the inorganic pigments, of titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also iron oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Mention may be made, among the organic pigments, of carbon black, pigments of D & C type, and lakes based on cochineal carmine and on barium, strontium, calcium or aluminium.
  • the pearlescent pigments can be chosen from white pearlescent pigments, such as mica covered with titanium or with bismuth oxychloride, coloured pearlescent pigments, such as titanium oxide-coated mica with iron oxides, titanium oxide- coated mica with in particular ferric blue or chromium oxide or titanium oxide- coated mica with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride.
  • fillers should be understood as meaning colourless or white, mineral or synthetic and lamellar or non-lamellar particles which are intended to give body or stiffness to the composition, and/or softness, mattness and uniformity to the make-up.
  • the fillers can be inorganic or organic of any shape: platelet, spherical or oblong.
  • organic carboxylic acids having from 8 to 22 carbon
  • the fat-soluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, b- carotene, soybean oil, Sudan brown, DC Yellow 11 , DC Violet 2, DC Orange 5 or quinoline yellow. They can represent from 0.01 % to 20% of the weight of the composition and better still from 0.1% to 6%.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue and can represent from 0.01 % to 6% of the total weight of the composition.
  • the composition comprises i) one or more compounds of formula (I) as defined above, ii) one or more liquid fatty substances as defined above and iii) one or more pigments as defined above.
  • the composition according to the invention can be provided in the form of a suspension, a dispersion, in particular of oil in water, by virtue of vesicles; an oil- in-water, water-in-oil or multiple emulsion; a gel or a foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a two-phase or multi phase lotion; a loose, compact or cast powder; an anhydrous paste.
  • This composition can have the appearance of a lotion, a cream, a pomade, a soft paste, an ointment, a foam, a cast or moulded solid, in particular in stick or dish form, or a compacted solid.
  • the cosmetic composition according to the invention can be provided in the form of a product for caring for and/or making up the skin of the body or face, the lips, the nails, the eyelashes, the eyebrows and/or the hair, an antisun or self tanning product, or a hair product for caring for, treating, cleaning, conditioning, shaping, making up or colouring the hair.
  • a make-up composition in particular a product for the complexion, such as a foundation, a face powder or an eyeshadow; a product for the lips, such as a lipstick, a lip gloss or a lip care product; a concealer product; a blusher, a mascara or an eyeliner; a product for making up the eyebrows, a lip or eye pencil; a product for the nails, such as a nail varnish or a nail care product; a product for making up the body; a product for making up the hair (hair mascara).
  • a product for the complexion such as a foundation, a face powder or an eyeshadow
  • a product for the lips such as a lipstick, a lip gloss or a lip care product
  • a concealer product such as a lipstick, a lip gloss or a lip care product
  • a mascara or an eyeliner a product for making up the eyebrows, a lip or eye pencil
  • a product for the nails such as a nail varnish or a nail care product
  • compositions for the protection, cleaning, hygiene or care of the skin of the face, the neck, the hands or the body in particular an anti-wrinkle composition; a moisturizing or treating composition; an antisun or artificial tanning (self-tanning) composition; a deodorant or antiperspirant composition.
  • a hair care product in particular for colouring, form retention of the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, lotions for hairsetting, blow-drying lotions, or fixing and styling compositions, such as lacquers or sprays.
  • the cosmetic composition according to the invention is provided in the form of a product for making up the body, lips, eyelashes, hair or nails, optionally having non-therapeutic care and/or treatment properties.
  • Another subject-matter of the invention is a process for the cosmetic treatment of keratin materials, such as the skin of the body or face, the lips, the nails, the hair, the eyebrows and/or the eyelashes, comprising the application, to said materials, of a composition, in particular a cosmetic composition, as defined above.
  • it is a process for making up the skin, lips, eyelashes, nails, eyebrows, hair and/or lips, more preferentially a process for treating the lips, more preferentially still for making up the lips.
  • the composition occurs in the form of a stick preferably comprising an amount of less than 7% by weight of water, preferably of less than 5% by weight of water, more preferentially still of less than 3% by weight of water, better still of less than 1% by weight of water, with respect to the total weight of the composition; more preferentially still, the composition is anhydrous or devoid of water.
  • the compounds according to the invention can also find an application in the field of the industry of paints, varnishes and adhesives, as structuring or thickening, indeed even gelling, agent, preferably in the cosmetics industry.
  • the solution is separated from the molecular sieve and from the enzyme by centrifugation (5000 revolutions per minute, 10 minutes).
  • the solution is concentrated to dryness on a rotary evaporator under reduced pressure.
  • the crude product is purified on an ion-exchange resin IRA67 (2 g w/w) in dichloromethane (10V) for 1 hour.
  • the mixture is filtered and the solution is concentrated on a rotary evaporator under reduced pressure to result in a white solid having a melting point of 105°C.
  • Example 2 Synthesis of the monostearate of formula (I) with R representing -C(0)-(CH 2 )i6-CH 3 and R 1 , R' 1 , R 2 , R' 2 , R 3 , R' 3 , R 4 , R' 4 , R 5 and R' 5 representing a hydrogen atom: [Chem. 14]
  • Example 3 Synthesis of the monoisostearate of formula (I) with R representing -C(0)-(CH 2 )i 3 -C(H)(CH 3 ) 2 and R 1 , R 2 , R 3 , R 4 and R 5 representing a hydrogen atom: [Chem. 15]
  • the solution is separated from the molecular sieve and from the enzyme by centrifugation (5000 revolutions per minute, 10 minutes).
  • the solution is concentrated to dryness on a rotary evaporator under reduced pressure.
  • the crude product is purified on an ion-exchange resin IRA67 (2 g w/w) in dichloromethane (10V) for 1 hour.
  • the mixture is filtered and the solution is concentrated on a rotary evaporator under reduced pressure in order to obtain a white solid corresponding to the expected product.
  • the comparatives are according to Examples 1 , 2 and 3 starting from sorbitol:
  • Example 5 dibenzylidene-d-sorbitol monostearate
  • Example 6 dibenzylidene-d-sorbitol monoisostearate
  • Example 7 (outside the invention): Synthesis of the monoisostearate of formula (I) with R representing -C(0)-(CH 2 ) 4 -CH3 and R 1 , R 2 , R 3 , R 4 and R 5 representing a hydrogen atom.
  • the gelling process is as follows: the product to be evaluated is weighed in order to obtain a concentration of 2% w/V (i.e. 20 mg in 1 ml of oil). The oil is added at ambient temperature. The mixture is stirred magnetically and heated at 60°C for one hour in a 20 ml flask (Screw Vials 24 mm Clear Glass 27.5 x 57 mm). The flask is subsequently allowed to cool to ambient temperature without specific action for at least 2 hours. The gelling was evaluated by visual observation of the magnetic bar present in the gel when the flask is inverted.
  • Example 3 10 mg of Example 3 (2% w/V) are mixed with 0.1 g of DC Red 7 (5% w/V) and 2 ml of squalane in a 10 ml flask. This mixture is heated at 60°C for one hour under magnetic stirring. The solution is added to a 2.5 ml precut syringe. The syringe is left standing at ambient temperature for 2 hours, in order to result in the Stick 2, and then pressed in order to carry out the evaluation.
  • Sticks 3 and 4 were prepared in the same way as Stick 2 except that the DC Red 7 was replaced by the same amount by weight of iron oxide (Stick 3) and of Red 7 Lake (Stick 4) (see appended Fig. 3 and Fig. 4).

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Abstract

La présente invention concerne une composition comprenant au moins un dérivé de dibenzylidène alditol spécifique de formule (I), un procédé de traitement cosmétique comprenant ledit dérivé, de nouveaux dérivés de dibenzylidène alditol, leur procédé de préparation et leur utilisation en cosmétique, en particulier dans des " bâtons cosmétiques ", tels que des rouges à lèvres. Formule (I), dans laquelle : R, R1 à R'5 sont tels que définis dans la description.
PCT/EP2021/062766 2020-05-13 2021-05-12 Dérivés de dibenzylidène alditol, composition les comprenant et leur utilisation en cosmétique WO2021229025A1 (fr)

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FR2004722A FR3110163B1 (fr) 2020-05-13 2020-05-13 Derives de dibenzylidene alditol, composition les comprenant, et leur utilisation en cosmetique
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
JPS63297384A (ja) * 1987-05-28 1988-12-05 Kao Corp ジベンジリデン化多価アルコ−ルエ−テル誘導体
JPS63304079A (ja) 1987-06-03 1988-12-12 Kao Corp 非水系ゲル化剤及びこれを含有するゲル化粧料
FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
WO2011107403A1 (fr) * 2010-03-02 2011-09-09 L'oreal Composés de type ester de dibenzylidène-sorbitol, procédé de préparation, utilisation, compositions comprenant ceux-ci et procédé de traitement cosmétique
WO2018002947A1 (fr) 2016-06-30 2018-01-04 Hindustan Petroleum Corporation Ltd. Gélifiants à base de sucre c5 pour déversements de pétrole

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
JPS63297384A (ja) * 1987-05-28 1988-12-05 Kao Corp ジベンジリデン化多価アルコ−ルエ−テル誘導体
JPS63304079A (ja) 1987-06-03 1988-12-12 Kao Corp 非水系ゲル化剤及びこれを含有するゲル化粧料
FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
WO2011107403A1 (fr) * 2010-03-02 2011-09-09 L'oreal Composés de type ester de dibenzylidène-sorbitol, procédé de préparation, utilisation, compositions comprenant ceux-ci et procédé de traitement cosmétique
EP2542556A1 (fr) 2010-03-02 2013-01-09 L'Oréal Composés de type ester de dibenzylidène-sorbitol, procédé de préparation, utilisation, compositions comprenant ceux-ci et procédé de traitement cosmétique
WO2018002947A1 (fr) 2016-06-30 2018-01-04 Hindustan Petroleum Corporation Ltd. Gélifiants à base de sucre c5 pour déversements de pétrole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
COSMETICS AND TOILETRIES, vol. 105, February 1990 (1990-02-01), pages 53 - 64

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