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WO2024141527A1 - Procédé de traitement de matières kératiniques à l'aide d'au moins un composé alcoxysilane portant des fonctions acétoacétate et au moins un agent de réticulation - Google Patents

Procédé de traitement de matières kératiniques à l'aide d'au moins un composé alcoxysilane portant des fonctions acétoacétate et au moins un agent de réticulation Download PDF

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Publication number
WO2024141527A1
WO2024141527A1 PCT/EP2023/087795 EP2023087795W WO2024141527A1 WO 2024141527 A1 WO2024141527 A1 WO 2024141527A1 EP 2023087795 W EP2023087795 W EP 2023087795W WO 2024141527 A1 WO2024141527 A1 WO 2024141527A1
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composition
formula
group
optionally
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PCT/EP2023/087795
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English (en)
Inventor
Laurent SABATIE
Boris STEVANT
Xavier FROGNEUX-PLE
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L'oreal
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Publication of WO2024141527A1 publication Critical patent/WO2024141527A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • 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
    • 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
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • Cosmetic products conventionally require the use of one or more film-forming polymers in order to obtain a quality deposit of these products on keratin materials and in particular to satisfy the expectations detailed below.
  • dispersions of polymer particles of nanometric size are used in makeup products such as mascaras, eyeliners, eyeshadows or lipsticks, and in hair application products, and more particularly in their organic and notably oily phases, as film-forming agent.
  • patent EP 1 392 222 it is also known practice from patent EP 1 392 222 to use a cosmetic composition for caring for and/or treating keratin materials, comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds, and from patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds and a surfactant or a hair-conditioning agent.
  • a cosmetic composition for caring for and/or treating keratin materials comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds
  • patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds and a surfactant or a hair-conditioning agent.
  • compositions and processes for forming deposits on keratin substrates having good staying power over time, using compounds bearing acetoacetate functions and functionalized active agents in order to be covalently bonded to the keratin materials are also known from WO 2014/099108.
  • Japanese document JP2003326843 describes inks for inkjet printing comprising polymers with amino groups and coupling agents of silane type.
  • keratin materials is intended to denote notably the lips, skin, nails and keratin fibres, in particular the eyelashes, eyebrows and the hair, preferably the lips and/or the hair.
  • cosmetic active agent means an organic or organosilicon compound or a mineral compound which can be incorporated into a cosmetic composition to give an effect on keratin materials, whether this effect is immediate or provided by repeated applications.
  • composition means that said composition contains an amount of less than 5% by weight of water, preferentially less than 3% by weight of water, better still less than 1% by weight of water, relative to the total weight of the composition in question; even more preferentially, the composition under consideration is free of water.
  • the process for treating keratin materials according to the invention using the ingredients i), ii), optionally iii) and optionally iv), is a process for caring for the skin.
  • composition termed “C2”, comprising i) at least one compound of formula (I), as defined previously and hereinbelow, ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow;
  • the process for treating keratin materials according to the invention uses a composition, termed “C2”, comprising i) at least one compound of formula (I), as defined previously and hereinbelow, ii) at least one crosslinking agent, in particular as defined hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously, preferably, said composition “C2” comprising iii) water.
  • the treatment process according to the invention comprises a single step of applying composition “C2” or composition “C3” to said keratin materials.
  • one-gesture application mode means the direct application to the target keratin materials of a single composition in accordance with the invention, namely composition “C2” or “C3”.
  • composition “C2” or “C3” After application of composition “C2” or “C3”, a persistent, non-tacky deposit is advantageously obtained.
  • the deposit obtained is also resistant to food oils, water, sebum and friction.
  • two-gesture application mode means the successive application, to the target keratin material, of two different compositions, for example “Cl” and “C4”, or “C2” and “C4”, or “C3” and “C4”, preferably “Cl” and then “C4”, “C2” and then “C4”, or “C3” and then “C4”.
  • the process of the invention is performed in three gestures.
  • three-gesture application mode means the sequential application of three different compositions “Cl” to “C5”. According to this application mode, for example, according to one embodiment, successive application is performed on the keratin materials, a) of a composition “Cl”, then P) of a composition “C4”, then y) of a composition “C5”, preferably “Cl” then “C4” or, respectively, “C5” or “C5” or, respectively, “C4”.
  • the composition applied first for example “Cl”
  • the base coat is conventionally referred to as the “base coat”
  • the composition(s) superposed thereon are generally referred to as the “top coat”.
  • compositions “Cl” to “C5” After application of the various compositions “Cl” to “C5”, a persistent, non-tacky deposit is advantageously obtained.
  • the deposit obtained is also resistant to food oils, water and shampoo washing.
  • the keratin materials are dried after application of compositions “Cl” to “C5”, in particular after application of each different composition.
  • the drying step can be implemented with a drying device such as a helmet, a hair dryer or a climazon.
  • the drying temperature is comprised between 40 °C and 110 °C, preferably between 50 °C and 90°C.
  • a step of shaping the keratin fibers can be implemented with a hair straightener (“fer a lisser”), a straightening or curling iron or a steam iron, preferably a hair straightener or a steam iron.
  • the step of shaping the keratin fibres is carried out at a temperature ranging from 120 °C to 230 °C, notably from 150 °C to 210 °C, even more preferentially from 160 °C to 210 °C, better from 180 °C to 210 °C.
  • the iron can be applied to the keratin fibers in successive separate touches of a few seconds, or by progressive movement or sliding along the hair.
  • the application of the iron is done in continuous movement from the root to the tip of the hair, in one or more passes.
  • the present invention relates to a cosmetic treatment process for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the successive application of at least:
  • composition termed “Cl”, comprising i) at least one compound of formula (I), as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; and then
  • compositions “C4” comprising ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; at least one of the compositions “Cl” and/or “C4” containing at least one dyestuff, in particular as defined previously and hereinbelow, preferably at least one pigment, and more preferentially composition “Cl” comprises at least one pigment.
  • the present invention relates to a cosmetic treatment process for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the successive application of at least:
  • compositions “C2” or “C3” contain at least iv) one dyestuff, in particular as defined hereinbelow, and/or composition “C4” contains at least one dyestuff, in particular as defined hereinbelow; preferably composition “C2” or “C3” comprises at least one pigment.
  • the compound(s) of formula (I) according to the invention are such that R b and R c , which may be identical or different, represent a hydrogen atom and R d represents a linear or branched (Ci-C4)alkyl group, preferably R d represents a methyl group.
  • the compound(s) of formula (I) according to the invention are such that ALK represents a saturated or unsaturated, linear or branched, acyclic, divalent hydrocarbon-based group, comprising from 1 to 6 carbon atoms, preferably a (Ci-C4)alkylene group, more preferentially propylene.
  • the compound(s) of formula (I) or (I’) are such that X represents -O-. According to another preferred embodiment, the compound(s) of formula (I) or (I’) are such that X represents a group -N(R a )- with R a as defined previously, preferably X represents a group -N(H)-.
  • the compound(s) of formula (I) or (I’) are such that R 1 represents a (Ci-C4)alkyl group, preferably a (Ci-C2)alkyl group.
  • the compound(s) of formula (I) or (I’) are such that R 1 represents a methyl group.
  • the compound(s) of formula (I) or (I’) are such that R 1 represents an ethyl group.
  • the compound(s) of formula (I) or (I’) are such that R 1 represents a hydrogen atom.
  • the compound(s) of formula (I) or (I’) are such that R 2 represents a (Ci-C2)alkyl group.
  • the compound(s) of formula (I) or (I’) are such that R 2 represents a methyl group.
  • the compound(s) of formula (I) or (I’) can be obtained according to methods known to those skilled in the art.
  • the compound(s) of formula (I) or (I’) may be synthesized according to the routes described in JP2005314325, JP2016069290, WO2014027766, US20190315778, or in the publication “Photoactive Diazoketo-Functionalized Self- Assembled Monolayer for Biomolecular Patterning”, Langmuir (2009), 25(16), 8888-8893.
  • the compound(s) of formula (I) are used in a medium containing at least one water-soluble solvent.
  • a composition used in the treatment process according to the invention preferably comprises one or more water- soluble solvents, more preferentially ethanol, in a content ranging from 5% to 90%, better still from 10% to 85% by weight, preferably from 25% to 80% by weight, relative to the total weight of said composition.
  • the treatment process according to the invention as described previously comprises the application to keratin materials of (i) at least one or more compounds of formula (I), and (ii) at least one crosslinking agent.
  • crosslinking agent also termed “R” denotes a compound that is capable of establishing with at least one acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention: at least one covalent bond, at least one donor-acceptor (dative) bond, and/or at least one coordination bond, and thus of crosslinking this or these compound(s).
  • crosslinking agent and “crosslinker” are equivalent.
  • crosslinking agent(s) R that are suitable for use in the invention may be chosen from compounds bearing amine, thiol, and/or acrylate functions.
  • a crosslinking agent R may also denote a metal alkoxide.
  • the metal alkoxide compounds are defined below.
  • non-polymeric compound means a compound which is not directly obtained via a monomer polymerization reaction.
  • (Poly)amine compounds that may be mentioned in particular include N-methyl-1,3- diaminopropane, N-propyl- 1,3 -diaminopropane, N-isopropyl- 1,3 -diaminopropane, N- cyclohexyl-l,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2- aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3- aminopropyl)amine, N-(3-aminopropyl)-l,4-diaminobutane, N,N- dimethyldipropylenetriamine, 1 ,2-bis(3-aminopropylamino)ethane, N,N’ -bis(3- aminopropyl)
  • the (poly)amine compounds are monoamine compounds, i.e. they contain only one primary and/or secondary amine group, preferably a primary amine group (NH2).
  • RT is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-Ce hydrocarbon-based chain substituted with a group chosen from primary amine groups NH2 or secondary amine groups -N(H)R with R representing a C1-C4 alkyl, an aryl or a benzyl substituted with an amino group or with a C1-C4 aminoalkyl group; RT may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R being linked to the silicon atom directly via a carbon atom,
  • a heteroatom O, S, NH
  • CO carbonyl group
  • the (poly)amine compounds are diamine compounds, i.e. they contain two primary and/or secondary amine groups, preferably primary amine groups (NH2).
  • formula (VII) is such that R a represents a hydroxyl or (Ci- C4)alkyl group, such as methyl, ALK 1 represents a (Cs-C6)alkylene group substituted with an NH group; preferably, ALK 1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight- average molecular mass of the compound of formula (VI) ranges from 5000 g.mol 1 to 500000 g.mol 1 .
  • the (poly)amine compounds are chosen from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group, such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.
  • - q denotes an integer greater than or equal to 2; preferably, q is between 2 and 10 inclusive and preferably between 2 and 5;
  • the (poly)thiol compound(s) are chosen from thiolated alkoxysiloxanes, such as those of formula (VIII’) below: R’i-Si(OR’2)z(R’ 3 )x (VIII’) in which formula (VIII’):
  • - 1 is an integer between 1 and 4, preferably 2;
  • - R 4 and R’ 4 which may be identical or different, represent a hydrogen atom or a (Ci-C6)alkyl group, such as methyl; - L 1 represents a divalent, saturated, linear or branched C1-C20 hydrocarbon-based radical.
  • the thiolated alkoxysiloxanes are chosen from those of formula (IX’) below: (R’ 1 O)(R’ 2 )(R’ 3 )Si-CH(R 4 )-CH(R 5 )-(L 2 ) q -SH (IX’) in which formula (IX’):
  • - X represents an oxygen or sulfur atom, preferably a sulfur atom
  • - R’ 1 denotes a (Ci-C6)alkyl radical
  • R 4 represents a hydrogen atom or a C1-C4 alkyl group, in particular methyl
  • - L 2 represents a linear or branched, saturated C1-C20 divalent hydrocarbon-based group, optionally interrupted with a heteroatom such as -N(H)-, and/or optionally substituted with one or more hydroxyl, thiol or amino groups.
  • the thiolated alkoxysilane(s) are chosen from 4-(trimethoxy silyl)- 1 -butanol, 3- (trimethoxy silyl)- 1 -propanol, 3-(triethoxysilyl)-l-propanol, 11 -(trimethoxy silyl)- 1- undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)ethanethiol, 3- (triethoxy silyl)- 1 -propanethiol, 2-(trimethoxysilyl)ethanethiol, 3 -(trimethoxy silyl)- 1- propanethiol and 3-(dimethoxymethylsilyl)-l-propanethiol.
  • the thiolated alkoxysilane(s) are chosen from 2- (triethoxysilyl)ethanethiol (18236-15-2) and 3 -(triethoxy silyl)- 1 -propanethiol (14814-09-6).
  • the (poly)thiol compound(s) are chosen from polymeric (poly)thiol compounds.
  • Examples that may be mentioned include the polymers described in the following articles: Polymers containing groups of biological activity, C.G. Overberger et al., Polytechnic Institute of Brooklyn, http://pac.iupac.org/publications/pac/pdf/1962/pdf/0402x0521.pdf; EP 1 247 515 A2; US 3 676 440; and EP 1 572 778.
  • polymeric (poly)thiol compounds of the invention are preferably organic and/or silicone compounds, more preferentially of formula (X):
  • - POLY denotes a polymer-based radical, preferably carbon-based or silicone-based; POLY being optionally interrupted with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof such as -O-, -O-C(X)-, -N(R)-C(X)-, -Si(R c )(Rd)-O- with R representing a hydrogen atom or a (C i -CoJal kyl group such as methyl; and/or POLY being optionally substituted with one or more halogen atoms, or a group chosen from R a (Rb)N- and -(X’) a -C(X)-(X”)b-R a ; X, X’ and X”, which may be identical or different, represent an oxygen or sulfur atom or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; R a
  • the methods for preparing the polymeric (poly)thiol compounds used according to the invention are known to those skilled in the art; several methods are reported hereinbelow in a non-limiting manner.
  • the polymeric (poly)thiol compounds used according to the invention may be obtained by polymerization or polycondensation of monomer units bearing thiol or protected thiol functions, optionally as a copolymerization or co-polycondensation of monomer units free of thiol or protected thiol functions.
  • the polymeric (poly)thiol compounds used according to the invention are polymers which are soluble in cosmetic media, particularly in aqueous or aqueous -alcoholic media. They are more preferentially obtained from amino polymers and the ammonium salts thereof or from poly hydroxylated polymers.
  • the thiolated polymers used according to the invention are polymers that are soluble in lipophilic media.
  • the polythiol compound is a polymeric compound of formula (X) in which q denotes an integer greater than or equal to 2, and POLY denotes a carbon-based and/or silicon-based, preferably silicon-based, polymeric radical, POLY also possibly containing one or more heteroatoms chosen from O, N or S, and/or one or more functions chosen from (thio)ester, (thio)ketone, (thio)amide, (thio)urea and (thio)carbamate functions, and/or possibly being substituted with one or more linear or branched (Ci-Cio)alkyl or linear or branched (Ci-Cio)alkoxy groups, it being understood that when POLY is substituted, the thiol functions may be borne by the substituent(s).
  • formula (X) in which q denotes an integer greater than or equal to 2
  • POLY denotes a carbon-based and/or silicon-based, preferably silicon-based, polymeric radical
  • POLY also possibly
  • the weight-average molecular weight of the polythiol polymer compounds is generally between 500 and 400 000 g.moT 1 , preferably between 500 and 150000 g.moT 1 .
  • the polythiol compounds are chosen from polyorganosiloxanes including thiol groups on end chains, such as those of formula (XI) below:
  • R a and R b which may be identical or different, preferably identical, represent a group from among: (Ci-C4)alkyl such as methyl, (Ci-C4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Ci-C4)alkoxy such as benzoxy, preferably (Ci-C4)alkyl such as methyl;
  • n represents an integer greater than or equal to 1 and more particularly the value of n is such that the weight- average molecular weight of the silicone ranges from 500 to 55 000 g.moT 1 ; in particular, n is an integer ranging from 1 to 100, preferably ranging from 5 to 50 and preferentially ranging from 10 to 30, and
  • L 4 and L 5 which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated, optionally cyclic hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, and in particular represent a covalent bond or a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene, (Ci-C6)alkylenoxy(Ci- C6)alkylene, (Ci-C6)alkylenoxy(Ci-C6)alkylenoxy or oxy(Ci-C6)alkylenoxy(Ci-C6)alkylene group, preferably a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci- Ce) alky lenoxy (C i -Ce) alkylene group, preferably
  • the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferentially polythiol poly dimethylsiloxanes, notably chosen from those of formula (XII): HS-L 4 -Si(CH3)2-O-[Si(CH3)2-O] n -Si(CH3) 2 -L 5 -SH (XII) in which formula (XII):
  • L 4 and L 5 are as defined previously in formula (IX), in particular L 4 and L 5 represent a (Ci- C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci-C6)alkylenoxy(Ci-C6)alkylene group, more preferentially a divalent group chosen from -R2-, -O-R2-, -R2-O- and -R2- O-R2-, preferably -R2-O-R2-, with R2 representing a linear or branched, preferably linear, (C2-C6)alkylene group, such as ethylene or n-propylene, preferably n-propylene; and
  • polythiol compounds of formula (XII) mention may be made of mercaptosiloxanes or thiolated siloxanes in which the thiol functions are at the chain ends, sold by the company Shin-Etsu under the reference X-22-167B, and mercaptosiloxane in which the mercapto functions are pendent, sold by the company Shin-Etsu under the reference KF-2001, or polydimethylsiloxanes in which the thiol functions are at the chain ends, via thio-n-propyl, 80-120 groups, sold by the company Gelest under the name DMS-SM 21.
  • the polythiol compounds are chosen polyorganosiloxanes including thiol groups on side chains, such as those of formula (XIII): R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALKi-SH)-O]ii-Si(R b )(R d )-R a (XIII) in which formula (XIII):
  • R a and R b are as defined in formula (XI) and R d is as defined for R a and R b , preferably R a , R b and R d , which are identical, represent a (Ci-C6)alkyl group, such as methyl;
  • R d may also represent a (Ci-C6)alkyl group substituted with a (Ci -Chalky lamino or amino or thiol group, preferably (Ci-C4)alkyl such as methyl;
  • the (poly)thiol compounds are chosen from hyperbranched polymers comprising at least one thiol group and dendrimers bearing at least one thiol group, such as thiolated PAMAM dendrimers.
  • the (poly)thiol compounds used according to the invention are chosen from polydiallylsiloxanes, notably polydimethylsiloxanes, including at least two thiol groups such as those of formula (XIII).
  • the crosslinking agent is a (poly)acrylate compound.
  • n which may be identical or different, represent an integer greater than 2 and more particularly the values of m and n are such that the weight- average molecular weight of said polyorganosiloxane is between 1000 and 55 000 g.mol 1 .
  • - Y is as defined previously, and is preferably an oxygen atom.
  • the (poly)acrylate compound is combined in its implementation with an amine catalyst as described, for example, in Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019).
  • the amine catalyst(s) are chosen from piperidine, DMAP (dimethylaminopyridine), DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), more preferentially chosen from DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8- diazabicy clo [5.4.0] unde
  • the (poly)acrylate compounds are chosen from those of formula (XIV), notably trimethylolpropane triacrylate, and those of formula (XV), notably copolymers of dimethylsiloxanes and of acryloxypropylmethylsiloxanes.
  • the organometallic compound(s) are chosen from the alkoxides of formula (XIVa), in which M represents an atom chosen from transition metals, such as zirconium or titanium, metals of the lanthanide family, posttransition metals, such as aluminium or tin, metalloids, such as boron, and alkaline-earth metals, such as magnesium, preferably M represents a titanium atom; n represents the valency of the atom represented by M, notably 1, 2, 3 or 4, in particular 4; Ri represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t-butyl group.
  • M represents an atom chosen from transition metals, such as zirconium or titanium, metals of the lanthanide family, posttransition metals, such as aluminium or tin, metalloids, such as boron, and alkaline-earth metals, such
  • said (poly)thiol compounds B) are chosen from a) poly dialkylsiloxanes bearing thiol functions, and b) alkoxysilanes bearing thiol functions, and in particular are chosen from a) poly dialkylsiloxanes bearing thiol functions, preferentially poly dimethylsiloxanes comprising thiol groups on the side chain (such as mercaptopropyl), notably those of formula (XIII).
  • crosslinking agent(s) is(are) chosen from:
  • chitosans such as poly(D-glucosamine)
  • R a and R b which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, or an aryl(Ci-C4)alkoxy group, in particular benzoxy, preferably a (Ci-C4)alkyl group, more preferentially methyl,
  • n and m which may be identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the weight-average molecular weight of said polyorganosiloxane is between 1000 and 55 000 g.mol 1 ;
  • the cosmetic active agent(s) iv) is(are) chosen from: a) dyestuffs (or colouring agents), in particular chosen from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof.
  • the term “pigment” means any compound that is capable of imparting colour to keratin materials. These compounds have a solubility in water at 25 °C and at atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.
  • a pigment that is suitable for use in the invention may be chosen from organic pigments.
  • special effect pigments those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.
  • the direct dyes are chosen from the compounds of formulae (E) and (F) below: [Chem 3]
  • the direct dyes are chosen from anionic direct dyes.
  • the dyestuffs may be present in concentrations ranging from 0.01% to 30% by weight, preferably from 0.02% to 20% by weight and more particularly from 0.05% to 15% by weight relative to the total weight of the composition containing them.
  • At least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises one or more care active agents, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition considered.
  • the care active agent may be at least one hydrophilic active agent and/or one lipophilic active agent, and preferably a hydrophilic care active agent.
  • the care active agent(s) may in particular be present, in the composition containing same, in a content ranging from 0.01% to 30% by weight, relative to the weight of the composition, and preferably from 0.02% to 25% by weight.
  • lipophilic UV-screening agent means any cosmetic or dermatological screening agent that can be fully dissolved in molecular form in a liquid fatty phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
  • insoluble UV-screening agent means any cosmetic or dermatological screening agent which is not defined either as a lipophilic UV-screening agent or as a hydrophilic UV- screening agent, and which is in the form of particles in aqueous phase or liquid fatty phase.
  • the UV-screening agents of the composition according to the invention may afford UVA and/or UVB photoprotection.
  • compositions which are preferably cosmetic compositions, may comprise at least one organic and/or mineral UV-screening agent (for screening out the UV radiation of sunlight).
  • the UV-screening agent(s) may be mineral UV-screening agents, which are generally pigments.
  • the pigments may or may not be coated.
  • the mineral UV-screening agents may be chosen from coated or uncoated pigments, and in particular from coated titanium oxide pigments, silicone-treated titanium oxides, uncoated titanium oxide pigments, uncoated zinc oxide pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and mixtures thereof.
  • compositions “Cl” to “C5” are free of mineral UV- screening agents.
  • the amount of the mineral UV-screening agent(s) present in compositions “Cl”, “C2”, “C3”, “C4” or “C5” according to the invention may range from 0.01% to 20% by weight relative to the total weight of the composition containing same. It ranges, for example, from 1% to 15% by weight, relative to the total weight of the composition.
  • compositions comprise a combination of UV- screening agents as described in patent FR 2 977 490, patent application WO 2013/004777 or patent application US 2014/0134120.
  • the process for treating keratin materials notably keratin fibres, and compositions “Cl”, “C2”, “C3”, “C4” or “C5” use or comprise one or more dyestuffs chosen from pigments, direct dyes and mixtures thereof, preferably pigments; more preferentially, the pigment(s) of the invention are chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7. substances
  • the process of the invention uses v) one or more fatty substances, in particular one or more oils, preferably volatile oils.
  • compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process of the invention contains a fatty phase.
  • compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process of the invention comprises one or more fatty substances, in particular one or more oils, preferably volatile oils.
  • oils refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).
  • hydrocarbon-based oil means an oil formed essentially from, or even constituted of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • the oil(s) v) is(are) chosen from volatile oils, in particular:
  • oils containing from 8 to 16 carbon atoms in particular branched Cs-Ci6 alkanes, in particular isoalkanes, more particularly isoalkanes (also known as isoparaffins), preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C11-C16 alkanes, alone or as mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C12) and n-tetradecane (C14), the undecanetridecane mixture, mixtures of n-undecane (C11) and n-tridecane mixture, mixture
  • esters containing from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;
  • RT-O-C(O)-O-R’2 in which RT and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen more preferentially from dibutyl carbonate or dipentyl carbonate;
  • Ri and R2 independently of each other, denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;
  • silicone oils in particular comprising from 2 to 7 silicon atoms, and optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; more preferentially, the volatile oil(s) v) are chosen from Cs-C
  • compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process according to the invention comprises one or more non-volatile oils, preferably chosen from:
  • non-volatile silicone oils in particular chosen from non-volatile silicones having the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyl trimethicone, diphenylsiloxy phenyl trimethicone; and also mixtures thereof;
  • the non-volatile carbonate oils may be chosen from the carbonates of formula Rs-O- C(O)-O-R9, with Rs and R9, which may be identical or different, representing a linear or branched C4 to C12 and preferentially Cf> to C10 alkyl chain;
  • the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dioctyl carbonate;
  • Branched alkyl groups that may be mentioned include a 1,1 -dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2 -heptylundecyl group, a 2-octyldodecyl group, a 1,3- dimethylbutyl group, a l-(l-methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5-trimethylhex
  • the non-volatile oil(s) are chosen from hydrogenated or non-hydrogenated polyisobutenes, preferably hydrogenated, in particular the non-volatile compounds of the Parleam® range; mixtures of C15-C19 alkanes, and from linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(0)-0 represents a carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, as defined previously, in particular isononyl isononanoate.
  • the process of the invention uses one or more hydrocarbon-based oils containing from 8 to 16 carbon atoms, and notably branched Cs-Ci6 alkanes, in particular isoalkanes, preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, alone or as mixtures, and more preferentially isododecane.
  • hydrocarbon-based oils containing from 8 to 16 carbon atoms, and notably branched Cs-Ci6 alkanes, in particular isoalkanes, preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, alone or as mixtures, and more preferentially isododecane.
  • the process for treating keratin materials according to the invention uses water, and the composition(s) “Cl” to “C5” used in the process of the invention comprise water.
  • compositions “Cl”, “C2”, “C3”, “C4” and/or “C5”, preferably “Cl”, “C2” and/or “C3”, are aqueous-alcoholic.
  • they comprise an ethanol/water mixture, in particular in a volume ratio of between 1/99 and 99/1, more particularly between 10/90 and 90/10, even more particularly between 20/80 and 80/20, preferably 40/60 and 60/40, such as 50/50.
  • compositions “Cl”, “C2”, “C3”, “C4” or “C5” may be in anhydrous, water-in-oil emulsion or oil-in-water emulsion form.
  • a composition “Cl”, “C2”, “C3”, “C4” or “C5” may be in the form of a makeup product, in particular a coloured makeup product, for the skin, in particular a foundation, optionally having care properties, a blusher, a face powder, an eyeshadow, a concealer, an eyeliner; a lip makeup product such as a lipstick, optionally having care properties, a lip gloss or lip pencils; a makeup product for the integuments such as the nails or eyelashes, in particular in the form of a cake mascara, or for the eyebrows and the hair, or a product for the temporary tattooing of bodily skin.
  • the present invention is also directed towards a multicompartment kit or device, notably a cosmetic kit or device, comprising:
  • the locks of hair are left at room temperature for 18 hours at 80% relative humidity.
  • the hair is dyed uniformly and intensely.
  • compositions D makes it possible to significantly improve the colour persistence compared to the application of a “base coat” only (composition E) or of a “top coat” only (compositions F).
  • the deposits are then evaluated according to the protocols of resistance to olive oil, to sebum and to water, and of resistance to adhesive tape, of the formulations on Bioskin.

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Abstract

La présente invention concerne un procédé de traitement de matières kératiniques, comprenant l'application sur lesdites matières kératiniques, en une ou plusieurs étapes successives, d'au moins i) un ou plusieurs composés de formule (I), ainsi que leurs isomères optiques ou géométriques et/ou leurs solvates, tels que des hydrates, ou une composition les contenant dans laquelle formule (I) X, R1, R2, Rb, Rc, Rd, ALK, m et n sont tels que définis dans la description, ii) au moins un agent de réticulation, iii) éventuellement de l'eau.
PCT/EP2023/087795 2022-12-27 2023-12-26 Procédé de traitement de matières kératiniques à l'aide d'au moins un composé alcoxysilane portant des fonctions acétoacétate et au moins un agent de réticulation WO2024141527A1 (fr)

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DE19755649A1 (de) 1997-12-15 1999-06-17 Basf Ag Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen
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