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WO2015011258A1 - Process for treating the hair with at least one silicone polymer functionalized with at least one alkoxysilane unit and at least one particular alkoxysilane - Google Patents

Process for treating the hair with at least one silicone polymer functionalized with at least one alkoxysilane unit and at least one particular alkoxysilane Download PDF

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Publication number
WO2015011258A1
WO2015011258A1 PCT/EP2014/066017 EP2014066017W WO2015011258A1 WO 2015011258 A1 WO2015011258 A1 WO 2015011258A1 EP 2014066017 W EP2014066017 W EP 2014066017W WO 2015011258 A1 WO2015011258 A1 WO 2015011258A1
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WO
WIPO (PCT)
Prior art keywords
weight
formula
process according
composition
hair
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PCT/EP2014/066017
Other languages
French (fr)
Inventor
Grégory Plos
Anne Bouchara
Patrice Lerda
Nicolas Daubresse
Original Assignee
L'oreal
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Filing date
Publication date
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Publication of WO2015011258A1 publication Critical patent/WO2015011258A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers
    • 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
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups

Definitions

  • the invention relates to a process for treating the hair, in particular for shaping the hair.
  • hair shaping products Two major categories of hair shaping products are generally used: styling products and perming products.
  • Styling products allow non-permanent shaping of the hair. They are used on wet or dry hair before shaping by hand or using a brush or a comb. They are in the form of gels, foams, waxes, pastes, lacquers or sprays. After they have been applied to the hair and after drying, these products harden substantially. This is reflected by an unnatural, embodied, dry feel required for the hold and volume of the hairstyle. Moreover, they do not show good resistance to moisture, and a head of hair loses its shape when exposed to a humid atmosphere, all the more so in a hot and humid atmosphere. Thus, firstly, the general shape of the hairstyle is rapidly lost and, secondly, the hair becomes frizzy, more particularly for hair that is naturally frizzy.
  • silicones or silicone derivatives, in particular amino silicones and amino silicones bearing silanol functions that are capable of reacting together to form new bonds.
  • Silicones give a natural, soft, non- greasy and non-set feel. They may also be partially water-resistant, which makes it possible to conserve the soft, natural feel. However, they cannot afford shaping of the head of hair or combat the appearance of frizziness, unless a very large amount of product is applied, which gives a greasy feel. As they only sparingly compensate for the dry feel when they are combined with other types of styling product such as fixing polymers, the combination of these two techniques remains relatively unsatisfactory.
  • Perming products allow long-lasting shaping of a head of hair.
  • the technique used for permanently reshaping the hair consists, in a first stage, in opening the -S-S- disulfide bonds of keratin (cystine) by applying to the hair, which has been placed under tension beforehand (with curlers and other tensioning means), a reducing composition (reduction step) and then, preferably after having rinsed the head of hair thus treated, in reconstituting the said disulfide bonds in a second stage by applying to the hair, which is still under tension, an oxidizing composition (oxidation step, also known as the fixing step) so as to finally give the hair the desired shape.
  • a chemical treatment such as that above is long-lasting over time and especially withstands the action of washing with water or with shampoos.
  • the object of the present invention is, precisely, to satisfy these needs.
  • the invention relates to a hair treatment process using:
  • the present invention also relates to the use of one or more polymers containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups and of one or more alkoxysilanes of formula (II) and/or of hydrolysis products thereof and/or oligomers thereof as defined previously, for treating the hair, and in particular for shaping the hair.
  • the process of the invention uses one or more polymers a) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
  • the polymer(s) a) containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups are of formula (I) below:
  • - Z 2 represents a group -CH 2 -NR 3 R 4 ;
  • - Z 3 represents a group OR 5 or R 6 ;
  • R 3 which may be identical or different, represent a hydrogen atom or a group R 7 ;
  • R-i, R 5 , R 6 and R 7 which may be identical or different, represent a Ci-C 6 alkyl group and R 4 represents a Ci-C 6 alkyl group or a C 5 -C 6 cycloalkyl group;
  • R 3 and R 4 possibly forming, with the nitrogen atom that bears them, a 5- to 8- membered heterocycle comprising from 1 to 3 heteroatoms,
  • R a and R b which may be identical or different, represent a Ci-C 2 alkyl group, and n represents an integer greater than 1 .
  • the Ci-C 6 alkyl groups are methyl or ethyl groups.
  • Ri is an ethyl group.
  • R 4 represents a C 5 -C 6 cycloalkyl group, it preferably represents a C 6 cycloalkyl group such as cyclohexyl.
  • n ranges from 1 to 10 000, preferably from 5 to 1000 and even more preferably from 8 to 400.
  • Z 2 represents a group -CH 2 -NR 3 R 4
  • R 4 represents an alkyl group, preferably a cyclohexyl
  • R 3 represents a hydrogen atom
  • R 5 represents an ethyl group.
  • R 3 and R 4 form, with the nitrogen that bears them, a cyclic group, preferably morpholino, and R 5 represents an ethyl group.
  • SiR a R b -[OSiR a R b ]n- is a unit derived from a linear silicone with a weight-average molecular mass (Mw) ranging from 200 to 40 000 and more preferentially from 400 to 25 000.
  • Mw weight-average molecular mass
  • polymers used in the process according to the invention mention will be made of: olymers of formula (la)
  • the polymers of formula (la) may be obtained by reacting a silicone bearing hydroxyl end groups with triethoxycyclohexylaminomethylsilane especially according to the techniques described in document WO 2005/108 495.
  • polymer (laa), corresponding to formula (la), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol. olymers of formula (lb)
  • the polymers of formula (lb) may be obtained by reacting a silicone bearing hydroxyl end groups with diethoxycyclohexylaminomethylmethylsilane especially according to the techniques described in document WO 2005/108 495.
  • polymer (Iba), corresponding to formula (lb), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
  • the polymers of formula (Ic) may be obtained by reacting a silicone bearing hydroxyl end groups with tnethoxymorpholinomethylsilane especially according to the techniques described in document WO 2009/019 165.
  • polymer (lea), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
  • polymer (leb), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass of 10 600 g/mol.
  • polymer (Ice), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass of 14 600 g/mol.
  • polymer (led), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 21 100 g/mol.
  • polymer (Ice), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 550 g/mol.
  • polymer (lef) corresponding to formula
  • polymer (leg), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 1200 g/mol.
  • polymer (lch), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 1700 g/mol.
  • the polymers of formula (Id) may be obtained by reacting a silicone bearing hydroxyl end groups with diethoxymorpholinomethylmethylsilane especially according to the techniques described in document WO 2009/019 165.
  • the polymer of formula (Ida), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
  • the polymer of formula (Idb), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 10 600 g/mol.
  • the polymer of formula (Idc), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 14 600 g/mol.
  • the polymer of formula (Idd), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 21 100 g/mol.
  • aminomethyl-silyl functional groups in the composition containing them generally ranges from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
  • the process according to the invention uses one or more alkoxysilanes of formula (II) below and/or the hydrolysis products thereof and/or oligomers thereof:
  • R', R" and R' which may be identical or different, represent a C1-C3 alkyl group
  • R"" represents a Ci-C 2 o alkyl group optionally substituted with a hydroxyl, amino or alkylamino group.
  • alkoxysilane hydrolysis products means silanes whose alkoxy groups may be partially or totally replaced with one or more hydroxyl groups.
  • oligomer means the polymerization products of the compounds of formula (II) comprising from 2 to 10 silicon atoms.
  • the alkoxysilane compound(s) of formula (II) are chosen from at least the monomers MTES (methyltriethoxysilane) and APTES (3-aminopropyltriethoxysilane), hydrolysis products thereof, oligomers thereof, and mixtures thereof, and even more preferably chosen from the monomer APTES (3- aminopropyltriethoxysilane), hydrolysis product thereof, oligomer thereof, and mixtures thereof.
  • the alkoxysilane(s) of formula (II) and/or the hydrolysis products thereof and/or oligomers thereof may represent from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
  • the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and the alkoxysilane(s) of formula (II) are present in two different compositions.
  • the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and the alkoxysilane(s) of formula (II) are present in a single composition.
  • the process according to the invention may also use one or more catalysts for catalysing the hydrolysis-condensation reactions of the alkoxysilane functions of the polymer containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
  • the catalyst may be chosen from acids and bases.
  • the acid may be chosen from mineral acids and organic acids.
  • the acid may be chosen in particular from lactic acid, acetic acid, citric acid, tartaric acid, hydrochloric acid, sulfuric acid and phosphoric acid, preferably hydrochloric acid.
  • the base may be chosen from mineral bases and organic bases.
  • the base may be chosen from ammonia and sodium hydroxide.
  • the catalyst may be present in the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, or it may be mixed at the time of use with the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, or alternatively may be applied sequentially to the hair before or after the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)- silyl functional groups.
  • the catalyst may be present in a composition comprising the alkoxysilane of formula (II) when it is separate from the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
  • the catalyst(s) may represent from 0.0001 % to 10% by weight, preferably from 0.001 % to 5% by weight and more particularly from 0.01 % to 2% by weight relative to the total weight of the composition containing them.
  • composition(s) used in the process according to the invention may be aqueous or anhydrous. If the composition(s) are aqueous, they preferably comprise less than 5% water, better still less than 3% water and even better still less than 2% water by weight relative to the total weight of the composition.
  • composition(s) used in the process according to the invention may comprise one or more organic solvents, preferably chosen from alcohols, alkanes, esters and silicones, and mixtures thereof.
  • the alcohols are linear or branched Ci-C 6 monoalcohols or polyols.
  • the esters may be natural or synthetic.
  • the esters may be chosen especially from plant oils and esters of fatty acids or of fatty alcohols, such as isopropyl myristate.
  • the alkanes may be chosen especially from linear or branched C 6 -Ci 5 alkanes and liquid paraffins.
  • the silicones may be chosen especially from cyclic silicones comprising from 4 to 6 silicon atoms and linear polydimethylsiloxanes.
  • the organic solvent is chosen from ethanol, propanol, isopropanol, glycerol, undecane, tridecane, isododecane, isopropyl myristate, ethyl adipate, ethyl acetate, linear low-molecular-weight silicones or cyclic silicones such as cyclopentasiloxane, and also mixtures thereof.
  • the solvent is chosen from ethanol, isopropanol and glycerol, and even more preferably is isopropanol.
  • the organic solvents that may be used in the compositions used in the process of the invention are liquids which preferably have a viscosity at 25°C and at atmospheric pressure of less than or equal to 100 cSt.
  • the organic solvent(s) may represent from 10% to 99.8%, preferably from 30% to 98% by weight and better still from 35% to 95% by weight relative to the total weight of the composition containing them.
  • the composition used in the process of the invention comprises one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, APTES (3-aminopropyltriethoxysilane) and/or hydrolysis product thereof and/or oligomer thereof and isopropanol.
  • APTES 3-aminopropyltriethoxysilane
  • composition(s) may be in the form of a solution, a dispersion or an emulsion.
  • the polymer containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups may be emulsified as an oil-in-water or water-in-oil emulsion or as a multiple emulsion.
  • composition(s) used in the process according to the invention may also contain one or more additives chosen from conditioning agents, nonionic, anionic and amphoteric surfactants, vitamins and provitamins including panthenol, water-soluble and liposoluble sunscreens, fillers and solid particles, for instance mineral and organic, coloured or uncoloured pigments, nacreous agents and opacifiers, glitter flakes, mineral fillers, dyes, sequestrants, plasticizers, solubilizers, acidifying agents, basifying agents, mineral and organic thickeners, antioxidants, antifoams, moisturizers, emollients, hydroxy acids, penetrants, fragrances and preserving agents.
  • additives chosen from conditioning agents, nonionic, anionic and amphoteric surfactants, vitamins and provitamins including panthenol, water-soluble and liposoluble sunscreens, fillers and solid particles, for instance mineral and organic, coloured or uncoloured pigments, nacreous agents and opacifiers, glitter flakes
  • composition(s) used in the process of the invention may be in the form of a foam, a gel, a serum, a cream, a paste, a wax, a liquid lotion or a lacquer.
  • composition(s) may be packaged in a pump-dispenser bottle or in an aerosol device.
  • the liquid phase/propellant weight ratio of the pressurized composition(s) is preferably between 50 and 0.05, and in particular between 50 and 1 .
  • any liquefiable gas that is usually used in aerosol devices will be used as propellant gas.
  • propellant gas Use will be made especially of dimethyl ether, C3-C5 alkanes, chlorinated and/or fluorinated, halogenated or non-halogenated, and volatile, hydrocarbons usually used in aerosol devices.
  • Carbon dioxide, nitrous oxide, nitrogen or compressed air, or mixtures thereof, may also be used as propellant.
  • the compound(s) constituting the propellant gas used are chosen from non-halogenated C 3 -C 5 alkanes, such as propane, n-butane and isobutane, halogenated, and in particular chlorinated and/or fluorinated, C 3 -C 5 alkanes, such as 1 ,1 -difluoroethane, and mixtures thereof.
  • non-halogenated C 3 -C 5 alkanes such as propane, n-butane and isobutane
  • halogenated and in particular chlorinated and/or fluorinated
  • C 3 -C 5 alkanes such as 1 ,1 -difluoroethane, and mixtures thereof.
  • the alkane(s) of the propellant gas are non-halogenated.
  • the propellant gas is dimethyl ether or a mixture of propane, n-butane and isobutane.
  • the composition introduced into the aerosol device may, for example, be in the form of a lotion, or dispersions or emulsions which, after dispensing from the aerosol device, form foams to be applied to keratin materials.
  • foams are preferably sufficiently stable not to rapidly liquefy and preferably must also rapidly disappear, either spontaneously or during the massaging which serves to make the composition penetrate into keratin materials and/or to distribute the composition over keratin materials and more particularly the head of hair and/or the hair.
  • composition(s) may also contain at least one cationic, nonionic, anionic or amphoteric surfactant.
  • the propellant gas is present in the composition(s) used in the process according to the invention in proportions preferably ranging from 1 % to 99% by weight, more preferentially from 1 .5% to 50% by weight and better still from 2% to 30% by weight relative to the total weight of the composition containing it.
  • the aerosol device used for packaging the composition(s) used in the process of the invention may be made up of two compartments, consisting of an outer aerosol can comprising an inner bag hermetically sealed to a valve.
  • the composition is introduced into the inner bag and a compressed gas is introduced between the bag and the can at a pressure sufficient to make the product come out in the form of a spray through a nozzle orifice.
  • a compressed gas is sold, for example, under the name EP Spray by the company EP-Spray System SA.
  • the said compressed gas is preferably used at a pressure of between 1 and 12 bar and even better still between 9 and 1 1 bar.
  • composition(s) are applied to dry or wet hair.
  • the heating tool may be a straightening iron, a curling iron, a crimping iron, a waving iron, a hood or a hairdryer.
  • the hair treatment process may consist in applying to the hair a composition comprising compounds a) and b) as defined previously, or in sequentially applying two compositions comprising, respectively, for one at least one compound a) and for the other at least one compound b) and optionally in simultaneously or sequentially applying one or more catalysts chosen from organic or mineral basic compounds, especially ammonia or sodium hydroxide, organic or mineral acids, especially hydrochloric acid, oleic acid or lactic acid, and mixtures thereof.
  • the application may be performed in a single stage.
  • a composition containing both one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), and one or more alkoxysilanes of formula (II), preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition, and optionally one or more catalysts as defined previously, will be applied.
  • the composition applied to the hair may result from the mixing of a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), a solvent, and less than 5% by weight of water relative to the total weight of the composition, and of a composition comprising one or more catalysts as defined previously, one or more alkoxysilanes of formula (II) being present in one or other of the two compositions.
  • the application may be performed in two or three stages: in a step (A), the composition comprising one or more catalysts as defined previously is applied, in a step (B), the composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups preferably of formula (I), preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition is applied, one or more alkoxysilanes of formula (II) being present in at least one of the two compositions or in a third composition applied in a step (C).
  • a step (A) the composition comprising one or more catalysts as defined previously is applied
  • a step (B) the composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups preferably of formula (I), preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition is applied, one or more alkoxys
  • step (A) may be performed, followed by step (B), or alternatively step (B) may be performed, followed by step (A), with or without intermediate drying.
  • step (A) is performed, followed by step (B).
  • step (C) will preferably be performed before step (B).
  • intermediate drying is preferably performed before step (B).
  • the process according to the invention may be performed using one or more compositions packaged in a device containing several compartments comprising either:
  • a first compartment containing a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and one or more alkoxysilanes of formula (II) and/or hydrolysis products thereof, and/or oligomers thereof as defined previously, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition; and
  • a first compartment containing a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition;
  • a second compartment comprising one or more alkoxysilanes of formula (II), and/or hydrolysis products thereof, and/or oligomers thereof as defined previously, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition,
  • one or more catalysts possibly being present in one or other of the compositions contained in the first and second compartment, or in a composition contained in a third compartment.
  • the device may be intended for a one-stage or a two-stage application.
  • compositions of the first and second compartments may be dispensed simultaneously at the time of application.
  • the present invention relates to the use of one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I) as defined previously, and of one or more alkoxysilanes of formula (II) and/or of hydrolysis products thereof and/or oligomers thereof, for treating the hair, and in particular for shaping the hair.
  • the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups preferably of formula (I) and the alkoxysilane(s) of formula (II) and/or the hydrolysis products thereof and/or the oligomers thereof are present in a single composition, preferably comprising at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition.
  • a single composition preferably comprising at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition.
  • compositions may be prepared for performing the process of the invention, the contents being expressed on a weight basis relative to the total weight of the composition.
  • compositions 3, 13, 20 and 23 were prepared.
  • compositions according to Examples 1 to 25 may be applied to locks of straight chestnut-brown Caucasian hair, with a bath ratio of 0.5.
  • the lock may then be rolled upon a curling iron for 30 seconds.
  • the locks may be suspended vertically over a paper and their relaxation evaluated over time by marking the end of the lock on the paper.
  • the locks may be placed in a chamber at controlled humidity (70%) for 24 hours.
  • the application may also be performed in one stage on short hair to obtain, after drying, a good styling effect. 3) Application as an aerosol
  • composition according to Examples 26 to 29 may be applied to medium- length hair, to obtain good fixing, a soft, non-tacky cosmetic feel after drying, which is easy to remove by brushing and does not leave any residues.

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  • Silicon Polymers (AREA)

Abstract

The invention relates to a hair treatment process using: a) one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups; b) one or more alkoxysilanes of formula (II) below and/or the hydrolysis products thereof and/or oligomers thereof: (ii) in which formula (II) k is 0 or 1, R', R" and R"", which may be identical or different, represent a C1-C3 alkyl group, R"" represents a C1-C20 alkyl group optionally substituted with a hydroxyl, amino or alkylamino group, compounds a) and b) being able to be applied using one or more compositions.

Description

PROCESS FOR TREATING THE HAIR WITH AT LEAST ONE SILICONE POLYMER FUNCTIONALIZED WITH AT LEAST ONE ALKOXYSILANE UNIT AND AT LEAST
ONE PARTICULAR ALKOXYSILANE
The invention relates to a process for treating the hair, in particular for shaping the hair.
Two major categories of hair shaping products are generally used: styling products and perming products.
Styling products allow non-permanent shaping of the hair. They are used on wet or dry hair before shaping by hand or using a brush or a comb. They are in the form of gels, foams, waxes, pastes, lacquers or sprays. After they have been applied to the hair and after drying, these products harden substantially. This is reflected by an unnatural, embodied, dry feel required for the hold and volume of the hairstyle. Moreover, they do not show good resistance to moisture, and a head of hair loses its shape when exposed to a humid atmosphere, all the more so in a hot and humid atmosphere. Thus, firstly, the general shape of the hairstyle is rapidly lost and, secondly, the hair becomes frizzy, more particularly for hair that is naturally frizzy.
To improve the feel, it is known practice to use silicones, or silicone derivatives, in particular amino silicones and amino silicones bearing silanol functions that are capable of reacting together to form new bonds. Silicones give a natural, soft, non- greasy and non-set feel. They may also be partially water-resistant, which makes it possible to conserve the soft, natural feel. However, they cannot afford shaping of the head of hair or combat the appearance of frizziness, unless a very large amount of product is applied, which gives a greasy feel. As they only sparingly compensate for the dry feel when they are combined with other types of styling product such as fixing polymers, the combination of these two techniques remains relatively unsatisfactory.
Moreover, these styling products are removed on shampooing. They therefore need to be applied daily.
Perming products allow long-lasting shaping of a head of hair.
Generally, the technique used for permanently reshaping the hair consists, in a first stage, in opening the -S-S- disulfide bonds of keratin (cystine) by applying to the hair, which has been placed under tension beforehand (with curlers and other tensioning means), a reducing composition (reduction step) and then, preferably after having rinsed the head of hair thus treated, in reconstituting the said disulfide bonds in a second stage by applying to the hair, which is still under tension, an oxidizing composition (oxidation step, also known as the fixing step) so as to finally give the hair the desired shape. The new shape given to the hair by a chemical treatment such as that above is long-lasting over time and especially withstands the action of washing with water or with shampoos.
However, such a technique is not entirely satisfactory. Specifically, this technique is very effective for modifying the shape of the hair, but is very degrading to hair fibres.
These two systems do not afford sufficient cosmeticity and/or durability of the effect obtained.
Document WO 201 1/080 034 describes compositions comprising a macromolecule with an alkoxysilyl function and a trialkoxysilane, for treating the hair, especially for temporarily reshaping keratin fibres, which show good resistance to washing. However, the cosmetic properties given to the hair are not entirely satisfactory.
Consequently, there is still a need for a hair treatment process for giving the hair the desired shape in a long-lasting manner, while at the same time having very good cosmetic properties, especially in terms of softness, sheen and absence of a tacky feel.
The object of the present invention is, precisely, to satisfy these needs.
According to one of its aspects, the invention relates to a hair treatment process using:
a) one or more polymers containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups;
b) one or more alkoxysilanes of formula (II) below and/or the hydrolysis products thereof and/or oligomers thereof:
Figure imgf000003_0001
in which formula (II) k is 0 or 1 , R', R" and R"\ which may be identical or different, represent a C1-C3 alkyl group, R"" represents a Ci-C2o alkyl group optionally substituted with a hydroxyl, amino or alkylamino group, compounds a) and b) being able to be implemented using one or more compositions. The present invention also relates to the use of one or more polymers containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups and of one or more alkoxysilanes of formula (II) and/or of hydrolysis products thereof and/or oligomers thereof as defined previously, for treating the hair, and in particular for shaping the hair. The process of the invention uses one or more polymers a) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
Preferably, the polymer(s) a) containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups are of formula (I) below:
Figure imgf000004_0001
in which:
- Z2 represents a group -CH2-NR3R4;
- Z3 represents a group OR5 or R6;
- R3, which may be identical or different, represent a hydrogen atom or a group R7;
- R-i, R5, R6 and R7, which may be identical or different, represent a Ci-C6 alkyl group and R4 represents a Ci-C6 alkyl group or a C5-C6 cycloalkyl group;
R3 and R4 possibly forming, with the nitrogen atom that bears them, a 5- to 8- membered heterocycle comprising from 1 to 3 heteroatoms,
- Ra and Rb, which may be identical or different, represent a Ci-C2 alkyl group, and n represents an integer greater than 1 .
Preferably, the Ci-C6 alkyl groups are methyl or ethyl groups.
Preferably, Ri is an ethyl group.
When R4 represents a C5-C6 cycloalkyl group, it preferably represents a C6 cycloalkyl group such as cyclohexyl.
Preferably, n ranges from 1 to 10 000, preferably from 5 to 1000 and even more preferably from 8 to 400.
According to a particular embodiment of the invention, Z2 represents a group -CH2-NR3R4, R4 represents an alkyl group, preferably a cyclohexyl, R3 represents a hydrogen atom and R5 represents an ethyl group.
According to another particular embodiment of the invention, R3 and R4 form, with the nitrogen that bears them, a cyclic group, preferably morpholino, and R5 represents an ethyl group.
Preferably, in formula (I), SiRaRb-[OSiRaRb]n- is a unit derived from a linear silicone with a weight-average molecular mass (Mw) ranging from 200 to 40 000 and more preferentially from 400 to 25 000. As examples of polymers used in the process according to the invention, mention will be made of: olymers of formula (la)
Figure imgf000005_0001
(la)
The polymers of formula (la) may be obtained by reacting a silicone bearing hydroxyl end groups with triethoxycyclohexylaminomethylsilane especially according to the techniques described in document WO 2005/108 495.
According to a particular example, polymer (laa), corresponding to formula (la), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol. olymers of formula (lb)
Figure imgf000005_0002
(lb)
The polymers of formula (lb) may be obtained by reacting a silicone bearing hydroxyl end groups with diethoxycyclohexylaminomethylmethylsilane especially according to the techniques described in document WO 2005/108 495.
According to a particular example, polymer (Iba), corresponding to formula (lb), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
- polymers of formula (lc)
Figure imgf000006_0001
The polymers of formula (Ic) may be obtained by reacting a silicone bearing hydroxyl end groups with tnethoxymorpholinomethylsilane especially according to the techniques described in document WO 2009/019 165.
According to a particular example, polymer (lea), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
According to another particular example, polymer (leb), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass of 10 600 g/mol.
According to another particular example, polymer (Ice), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass of 14 600 g/mol.
According to another particular example, polymer (led), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 21 100 g/mol.
According to another particular example, polymer (Ice), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 550 g/mol.
According to another particular example, polymer (lef), corresponding to formula
(Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 1000 g/mol.
According to another particular example, polymer (leg), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 1200 g/mol.
According to another particular example, polymer (lch), corresponding to formula (Ic), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 1700 g/mol.
- polymers of formula (Id)
Figure imgf000007_0001
The polymers of formula (Id) may be obtained by reacting a silicone bearing hydroxyl end groups with diethoxymorpholinomethylmethylsilane especially according to the techniques described in document WO 2009/019 165.
According to a particular example, the polymer of formula (Ida), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 4750 g/mol.
According to another particular example, the polymer of formula (Idb), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 10 600 g/mol.
According to another particular example, the polymer of formula (Idc), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 14 600 g/mol.
According to another particular example, the polymer of formula (Idd), corresponding to formula (Id), is obtained according to the operating scheme presented above, starting with a silicone with a weight-average molecular mass Mw of 21 100 g/mol.
The content of the polymer(s) a) containing silicone units and bearing alkoxy-
(aminomethyl)-silyl functional groups, preferably of formula (I), in the composition containing them generally ranges from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
As indicated previously, the process according to the invention uses one or more alkoxysilanes of formula (II) below and/or the hydrolysis products thereof and/or oligomers thereof:
Figure imgf000008_0001
in which formula (II) k is 0 or 1 , R', R" and R'", which may be identical or different, represent a C1-C3 alkyl group, R"" represents a Ci-C2o alkyl group optionally substituted with a hydroxyl, amino or alkylamino group.
The term "alkoxysilane hydrolysis products" means silanes whose alkoxy groups may be partially or totally replaced with one or more hydroxyl groups.
The term "oligomer" means the polymerization products of the compounds of formula (II) comprising from 2 to 10 silicon atoms.
According to a preferred embodiment, the alkoxysilane compound(s) of formula (II) are chosen from at least the monomers MTES (methyltriethoxysilane) and APTES (3-aminopropyltriethoxysilane), hydrolysis products thereof, oligomers thereof, and mixtures thereof, and even more preferably chosen from the monomer APTES (3- aminopropyltriethoxysilane), hydrolysis product thereof, oligomer thereof, and mixtures thereof.
The alkoxysilane(s) of formula (II) and/or the hydrolysis products thereof and/or oligomers thereof may represent from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
According to one embodiment, the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and the alkoxysilane(s) of formula (II) are present in two different compositions.
According to a preferred embodiment, the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and the alkoxysilane(s) of formula (II) are present in a single composition.
The process according to the invention may also use one or more catalysts for catalysing the hydrolysis-condensation reactions of the alkoxysilane functions of the polymer containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
The catalyst may be chosen from acids and bases.
The acid may be chosen from mineral acids and organic acids. The acid may be chosen in particular from lactic acid, acetic acid, citric acid, tartaric acid, hydrochloric acid, sulfuric acid and phosphoric acid, preferably hydrochloric acid.
The base may be chosen from mineral bases and organic bases.
The base may be chosen from ammonia and sodium hydroxide.
The catalyst may be present in the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, or it may be mixed at the time of use with the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, or alternatively may be applied sequentially to the hair before or after the composition comprising the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)- silyl functional groups.
As a variant, the catalyst may be present in a composition comprising the alkoxysilane of formula (II) when it is separate from the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups.
The catalyst(s) may represent from 0.0001 % to 10% by weight, preferably from 0.001 % to 5% by weight and more particularly from 0.01 % to 2% by weight relative to the total weight of the composition containing them.
The composition(s) used in the process according to the invention may be aqueous or anhydrous. If the composition(s) are aqueous, they preferably comprise less than 5% water, better still less than 3% water and even better still less than 2% water by weight relative to the total weight of the composition.
The composition(s) used in the process according to the invention may comprise one or more organic solvents, preferably chosen from alcohols, alkanes, esters and silicones, and mixtures thereof.
The alcohols are linear or branched Ci-C6 monoalcohols or polyols.
The esters may be natural or synthetic.
The esters may be chosen especially from plant oils and esters of fatty acids or of fatty alcohols, such as isopropyl myristate.
The alkanes may be chosen especially from linear or branched C6-Ci5 alkanes and liquid paraffins.
The silicones may be chosen especially from cyclic silicones comprising from 4 to 6 silicon atoms and linear polydimethylsiloxanes.
Preferably, the organic solvent is chosen from ethanol, propanol, isopropanol, glycerol, undecane, tridecane, isododecane, isopropyl myristate, ethyl adipate, ethyl acetate, linear low-molecular-weight silicones or cyclic silicones such as cyclopentasiloxane, and also mixtures thereof. According to a preferred embodiment, the solvent is chosen from ethanol, isopropanol and glycerol, and even more preferably is isopropanol.
The organic solvents that may be used in the compositions used in the process of the invention are liquids which preferably have a viscosity at 25°C and at atmospheric pressure of less than or equal to 100 cSt.
When they are present, the organic solvent(s) may represent from 10% to 99.8%, preferably from 30% to 98% by weight and better still from 35% to 95% by weight relative to the total weight of the composition containing them.
According to a preferred embodiment, the composition used in the process of the invention comprises one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, APTES (3-aminopropyltriethoxysilane) and/or hydrolysis product thereof and/or oligomer thereof and isopropanol.
The composition(s) may be in the form of a solution, a dispersion or an emulsion. The polymer containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups may be emulsified as an oil-in-water or water-in-oil emulsion or as a multiple emulsion.
The composition(s) used in the process according to the invention may also contain one or more additives chosen from conditioning agents, nonionic, anionic and amphoteric surfactants, vitamins and provitamins including panthenol, water-soluble and liposoluble sunscreens, fillers and solid particles, for instance mineral and organic, coloured or uncoloured pigments, nacreous agents and opacifiers, glitter flakes, mineral fillers, dyes, sequestrants, plasticizers, solubilizers, acidifying agents, basifying agents, mineral and organic thickeners, antioxidants, antifoams, moisturizers, emollients, hydroxy acids, penetrants, fragrances and preserving agents.
Needless to say, a person skilled in the art will take care to select the optional additional compounds and/or the amount thereof such that the advantageous properties of the compositions used in the process according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
The composition(s) used in the process of the invention may be in the form of a foam, a gel, a serum, a cream, a paste, a wax, a liquid lotion or a lacquer.
The composition(s) may be packaged in a pump-dispenser bottle or in an aerosol device.
When they are packaged in an aerosol-type device, the liquid phase/propellant weight ratio of the pressurized composition(s) is preferably between 50 and 0.05, and in particular between 50 and 1 .
For the aerosol formulations, any liquefiable gas that is usually used in aerosol devices will be used as propellant gas. Use will be made especially of dimethyl ether, C3-C5 alkanes, chlorinated and/or fluorinated, halogenated or non-halogenated, and volatile, hydrocarbons usually used in aerosol devices. Carbon dioxide, nitrous oxide, nitrogen or compressed air, or mixtures thereof, may also be used as propellant.
Preferably, the compound(s) constituting the propellant gas used are chosen from non-halogenated C3-C5 alkanes, such as propane, n-butane and isobutane, halogenated, and in particular chlorinated and/or fluorinated, C3-C5 alkanes, such as 1 ,1 -difluoroethane, and mixtures thereof.
According to a particularly preferred embodiment, the alkane(s) of the propellant gas are non-halogenated. Even more preferentially, the propellant gas is dimethyl ether or a mixture of propane, n-butane and isobutane.
In the case of aerosol foams, the composition introduced into the aerosol device may, for example, be in the form of a lotion, or dispersions or emulsions which, after dispensing from the aerosol device, form foams to be applied to keratin materials.
These foams are preferably sufficiently stable not to rapidly liquefy and preferably must also rapidly disappear, either spontaneously or during the massaging which serves to make the composition penetrate into keratin materials and/or to distribute the composition over keratin materials and more particularly the head of hair and/or the hair.
In the case of aerosol foams, the composition(s) may also contain at least one cationic, nonionic, anionic or amphoteric surfactant.
The propellant gas is present in the composition(s) used in the process according to the invention in proportions preferably ranging from 1 % to 99% by weight, more preferentially from 1 .5% to 50% by weight and better still from 2% to 30% by weight relative to the total weight of the composition containing it.
The aerosol device used for packaging the composition(s) used in the process of the invention may be made up of two compartments, consisting of an outer aerosol can comprising an inner bag hermetically sealed to a valve. The composition is introduced into the inner bag and a compressed gas is introduced between the bag and the can at a pressure sufficient to make the product come out in the form of a spray through a nozzle orifice. Such a device is sold, for example, under the name EP Spray by the company EP-Spray System SA. The said compressed gas is preferably used at a pressure of between 1 and 12 bar and even better still between 9 and 1 1 bar.
The composition(s) are applied to dry or wet hair.
Depending on the desired type of hairstyle, it is applied in combination with a heating tool or at room temperature.
The heating tool may be a straightening iron, a curling iron, a crimping iron, a waving iron, a hood or a hairdryer. The hair treatment process may consist in applying to the hair a composition comprising compounds a) and b) as defined previously, or in sequentially applying two compositions comprising, respectively, for one at least one compound a) and for the other at least one compound b) and optionally in simultaneously or sequentially applying one or more catalysts chosen from organic or mineral basic compounds, especially ammonia or sodium hydroxide, organic or mineral acids, especially hydrochloric acid, oleic acid or lactic acid, and mixtures thereof.
According to a particular embodiment, the application may be performed in a single stage. In this case, a composition containing both one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), and one or more alkoxysilanes of formula (II), preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition, and optionally one or more catalysts as defined previously, will be applied.
In this one-stage embodiment, the composition applied to the hair may result from the mixing of a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), a solvent, and less than 5% by weight of water relative to the total weight of the composition, and of a composition comprising one or more catalysts as defined previously, one or more alkoxysilanes of formula (II) being present in one or other of the two compositions.
According to another embodiment, the application may be performed in two or three stages: in a step (A), the composition comprising one or more catalysts as defined previously is applied, in a step (B), the composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups preferably of formula (I), preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition is applied, one or more alkoxysilanes of formula (II) being present in at least one of the two compositions or in a third composition applied in a step (C).
In the embodiment with two steps (A) and (B), step (A) may be performed, followed by step (B), or alternatively step (B) may be performed, followed by step (A), with or without intermediate drying. Preferably, step (A) is performed, followed by step (B). In the embodiment with three steps (A), (B) and (C), step (C) will preferably be performed before step (B).
In these particular embodiments, intermediate drying is preferably performed before step (B). The process according to the invention may be performed using one or more compositions packaged in a device containing several compartments comprising either:
- a first compartment containing a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups and one or more alkoxysilanes of formula (II) and/or hydrolysis products thereof, and/or oligomers thereof as defined previously, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition; and
- a second compartment containing a composition comprising one or more catalysts,
or:
- a first compartment containing a composition comprising one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition;
- a second compartment comprising one or more alkoxysilanes of formula (II), and/or hydrolysis products thereof, and/or oligomers thereof as defined previously, preferably at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition,
one or more catalysts possibly being present in one or other of the compositions contained in the first and second compartment, or in a composition contained in a third compartment.
The device may be intended for a one-stage or a two-stage application.
In the case of a one-stage application, the compositions of the first and second compartments may be dispensed simultaneously at the time of application.
Finally, the present invention relates to the use of one or more polymers containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I) as defined previously, and of one or more alkoxysilanes of formula (II) and/or of hydrolysis products thereof and/or oligomers thereof, for treating the hair, and in particular for shaping the hair.
Preferably, in the said use, the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups preferably of formula (I) and the alkoxysilane(s) of formula (II) and/or the hydrolysis products thereof and/or the oligomers thereof are present in a single composition, preferably comprising at least one organic solvent, and preferably less than 5% by weight of water relative to the total weight of the composition. The invention is illustrated in greater detail in the examples that follow, which are given as non-limiting illustrations of the invention.
Examples
The following compositions may be prepared for performing the process of the invention, the contents being expressed on a weight basis relative to the total weight of the composition.
Figure imgf000014_0001
Figure imgf000014_0002
Examples 20 21 22 23 24 25
Polymer (laa) 5 Polymer (Iba) 5
Polymer (lea) 5 5
Polymer (Ida) 5
Polymer (Idb) 5
Aminopropyltriethoxysilane 1 1 1 1 1
Methyltriethoxysilane 1
Isododecane 94 94 94 94
Undecane/tridecane 94 94
Examples in the form of an aerosol system
Figure imgf000015_0001
Compositions 3, 13, 20 and 23 were prepared.
Various application modes are envisaged:
1 ) One-stage application with a heating tool:
The compositions according to Examples 1 to 25 may be applied to locks of straight chestnut-brown Caucasian hair, with a bath ratio of 0.5.
The lock may then be rolled upon a curling iron for 30 seconds.
To evaluate the hold over time, the locks may be suspended vertically over a paper and their relaxation evaluated over time by marking the end of the lock on the paper.
To evaluate the resistance to moisture, the locks may be placed in a chamber at controlled humidity (70%) for 24 hours.
2) Application of styling product without heating
The application may also be performed in one stage on short hair to obtain, after drying, a good styling effect. 3) Application as an aerosol
The composition according to Examples 26 to 29 may be applied to medium- length hair, to obtain good fixing, a soft, non-tacky cosmetic feel after drying, which is easy to remove by brushing and does not leave any residues.

Claims

1. Hair treatment process using:
a) one or more polymers containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups;
b) one or more alkoxysilanes of formula (II) below and/or the hydrolysis products thereof and/or oligomers thereo
Figure imgf000017_0001
in which formula (II) k is 0 or 1 , R', R" and R"\ which may be identical or different, represent a C1-C3 alkyl group, R"" represents a Ci-C2o alkyl group optionally substituted with a hydroxyl, amino or alkylamino group, compounds a) and b) being able to be implemented using one or more compositions.
2. Process according to Claim 1 , in which the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups are chosen from the compounds of formula (I) below:
-R, R1 \
O R„ O
-Si— O-Si- -Si- -O— Si— Z2
I
R. R.
(I)
in which formula (I):
- Z2 represents a group -CH2-NR3R4;
- Z3 represents a group OR5 or R6;
- R3, which may be identical or different, represent a hydrogen atom or a group R7;
- R-i, R5, R6 and R7, which may be identical or different, represent a Ci-C6 alkyl group and R4 represents a Ci-C6 alkyl group or a C5-C6 cycloalkyl group;
R3 and R4 possibly forming, with the nitrogen atom that bears them, a 5- to 8- membered heterocycle comprising from 1 to 3 heteroatoms, - Ra and Rb, which may be identical or different, represent a Ci-C2 alkyl group, and n represents an integer greater than 1 .
3. Process according to Claim 2, in which the CrC6 alkyl groups are methyl or ethyl groups.
4. Process according to either of Claims 2 and 3, in which R4 represents a C6 cycloalkyi group such as cyclohexyl.
5. Process according to any one of Claims 2 to 4, in which n ranges from 1 to 10 000, preferably from 5 to 1000 and even more preferably from 8 to 400.
6. Process according to any one of Claims 2 to 5, in which SiRaRb-[OSiRaRb]n- of formula (I) is a unit derived from a linear silicone with a weight-average molecular mass (Mw) ranging from 200 to 40 000 and more preferentially from 400 to 25 000.
7. Process according to any one of the preceding claims, in which the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), represent from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
8. Process according to any one of the preceding claims, in which the compound(s) b) are chosen from the monomers MTES (methyltriethoxysilane) and APTES (3- aminopropyltriethoxysilane), hydrolysis products thereof, oligomers thereof, and mixtures thereof and preferably is chosen from the monomer APTES (3- aminopropyltriethoxysilane), hydrolysis product thereof, oligomer thereof, and mixtures thereof.
9. Process according to any one of the preceding claims, in which the compound(s) b) represent from 0.1 % to 40% by weight, preferably from 0.5% to 30% by weight and more particularly from 1 % to 10% by weight relative to the total weight of the composition in which they are used.
10. Process according to any one of the preceding claims, in which the compound(s) a) and b) are implemented using a single composition.
1 1 . Process according to any one of the preceding claims, in which the composition(s) comprise at least one organic solvent, preferably chosen from alcohols, alkanes, esters and silicones, and mixtures thereof, preferentially chosen from ethanol, propanol, isopropanol, glycerol, undecane, tridecane, isododecane, isopropyl myristate, ethyl adipate, ethyl acetate, linear low-molecular-weight silicones or cyclic silicones such as cyclopentasiloxane, and also mixtures thereof, and more preferably from ethanol, isopropanol and glycerol, and mixtures thereof, and even more preferably is isopropanol.
12. Process according to the preceding claim, characterized in that the organic solvent(s) represent from 10% to 99.8%, preferably from 30% to 98% by weight and better still from 35% to 95% by weight relative to the total weight of the composition in which they are used.
13. Process according to any one of the preceding claims, characterized in that the compositions comprising compounds a) and b) comprise less than 5% by weight of water, preferably less than 3% by weight of water and more preferably less than 2% by weight of water relative to the total weight of the composition.
14. Process according to any one of the preceding claims, using one or more catalysts, the catalyst(s) preferably being chosen from organic or mineral basic compounds, especially ammonia or sodium hydroxide, organic or mineral acids, especially hydrochloric acid, oleic acid or lactic acid, and mixtures thereof.
15. Process according to Claim 14, characterized in that the catalyst(s) are present in a content ranging from 0.0001 % to 10% by weight, preferably from 0.001 % to 5% by weight and better still from 0.01 % to 2% by weight relative to the total weight of the composition containing them.
16. Process according to the preceding claims, which also comprises a step of heating the hair using a heating tool chosen from a straightening iron, a curling iron, a crimping iron, a waving iron, a hood and a hairdryer.
17. Use of one or more polymers containing silicone units and bearing alkoxy- (aminomethyl)-silyl functional groups, preferably of formula (I) according to Claim 2, and of one or more alkoxysilanes of formula (II) and/or of hydrolysis products thereof and/or oligomers thereof according to Claim 1 or 8, for treating the hair, and in particular for shaping the hair.
18. Use according to Claim 17, in which the polymer(s) containing silicone units and bearing alkoxy-(aminomethyl)-silyl functional groups, preferably of formula (I), and the alkoxysilane(s) of formula (II) and/or the hydrolysis products thereof and/or the oligomers thereof are present in the same composition.
PCT/EP2014/066017 2013-07-26 2014-07-25 Process for treating the hair with at least one silicone polymer functionalized with at least one alkoxysilane unit and at least one particular alkoxysilane WO2015011258A1 (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016120322A1 (en) * 2015-01-29 2016-08-04 L'oreal Composition comprising a silicone functionalized with at least one alkoxysilane unit and a nonionic or anionic fixing polymer
FR3045287A1 (en) * 2015-12-22 2017-06-23 Oreal AEROSOL DEVICE BASED ON AT LEAST TWO SPECIFIC ALCOXYSILANES, ONE AT LEAST COMPRISING A C1-6 ALKYL CHAIN
WO2018065070A1 (en) * 2016-10-07 2018-04-12 Wacker Chemie Ag Secondary aminosiloxanes and method for production thereof
US10463600B2 (en) 2015-01-29 2019-11-05 L'oreal Aerosol composition comprising a silicone functionalized with at least one alkoxysilane unit and an amphoteric and/or cationic fixing polymer
US10524999B2 (en) 2015-12-14 2020-01-07 L'oreal Composition comprising a combination of particular alkoxysilanes and a fatty substance
US10722450B2 (en) 2015-01-29 2020-07-28 L'oreal Process for treating the hair with at least one silicone functionalized with at least one alkoxysilane unit, and steam
WO2021002163A1 (en) * 2019-07-02 2021-01-07 信越化学工業株式会社 Organopolysiloxane compound, composition comprising said compound, and method for preparing same
US11395794B2 (en) 2015-12-14 2022-07-26 L'oreal Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3044920B1 (en) * 2015-12-14 2019-08-09 L'oreal COMPOSITION COMPRISING AN ASSOCIATION OF PARTICULAR ALCOXYSILANES AND A FATTY BODY

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007037197A1 (en) * 2007-08-07 2009-02-12 Wacker Chemie Ag Crosslinkable compositions based on organosilicon compounds
FR2950531A1 (en) * 2009-09-29 2011-04-01 Oreal Cosmetic treatment of keratin fibers, such as human keratin fibers, preferably hair, comprises applying, on the fibers, composition comprising alkoxysilane and composition comprising silicones functionalized by one or more mercapto groups
FR2966356A1 (en) * 2010-10-26 2012-04-27 Oreal Cosmetic composition, useful for the cosmetic treatment of hair and as shampoo to facilitate disentangling of the hair, comprises alkoxysilane compounds having one or more fatty chain and other alkoxysilanes
WO2013068967A2 (en) * 2011-11-09 2013-05-16 L'oreal Cosmetic composition comprising an alpha-alkoxysilane obtained from an acrylate
WO2013079258A2 (en) * 2011-11-29 2013-06-06 Henkel Ag & Co. Kgaa Pretreatment agents for keratin fibers comprising 4-morpholino-methyl-substituted silicone(s)

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007037197A1 (en) * 2007-08-07 2009-02-12 Wacker Chemie Ag Crosslinkable compositions based on organosilicon compounds
FR2950531A1 (en) * 2009-09-29 2011-04-01 Oreal Cosmetic treatment of keratin fibers, such as human keratin fibers, preferably hair, comprises applying, on the fibers, composition comprising alkoxysilane and composition comprising silicones functionalized by one or more mercapto groups
FR2966356A1 (en) * 2010-10-26 2012-04-27 Oreal Cosmetic composition, useful for the cosmetic treatment of hair and as shampoo to facilitate disentangling of the hair, comprises alkoxysilane compounds having one or more fatty chain and other alkoxysilanes
WO2013068967A2 (en) * 2011-11-09 2013-05-16 L'oreal Cosmetic composition comprising an alpha-alkoxysilane obtained from an acrylate
WO2013079258A2 (en) * 2011-11-29 2013-06-06 Henkel Ag & Co. Kgaa Pretreatment agents for keratin fibers comprising 4-morpholino-methyl-substituted silicone(s)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"One step ahead-Organofunctionalsilanes", INTERNET CITATION, 21 March 2006 (2006-03-21), XP002471879, Retrieved from the Internet <URL:http://web.archive.org/web/20060321065158/http://www.wacker.com/internet/webcache/de_DE/_Downloads/GENIOSIL_Brosch_en.pdf> [retrieved on 20080306] *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016120322A1 (en) * 2015-01-29 2016-08-04 L'oreal Composition comprising a silicone functionalized with at least one alkoxysilane unit and a nonionic or anionic fixing polymer
US10463600B2 (en) 2015-01-29 2019-11-05 L'oreal Aerosol composition comprising a silicone functionalized with at least one alkoxysilane unit and an amphoteric and/or cationic fixing polymer
US10603268B2 (en) 2015-01-29 2020-03-31 L'oreal Composition comprising a silicone functionalized with at least one alkoxysilane unit and a nonionic or anionic fixing polymer
US10722450B2 (en) 2015-01-29 2020-07-28 L'oreal Process for treating the hair with at least one silicone functionalized with at least one alkoxysilane unit, and steam
US10524999B2 (en) 2015-12-14 2020-01-07 L'oreal Composition comprising a combination of particular alkoxysilanes and a fatty substance
EP3389604B1 (en) 2015-12-14 2020-04-08 L'Oréal Composition comprising a combination of particular alkoxysilanes and a fatty substance
US11395794B2 (en) 2015-12-14 2022-07-26 L'oreal Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes
FR3045287A1 (en) * 2015-12-22 2017-06-23 Oreal AEROSOL DEVICE BASED ON AT LEAST TWO SPECIFIC ALCOXYSILANES, ONE AT LEAST COMPRISING A C1-6 ALKYL CHAIN
WO2018065070A1 (en) * 2016-10-07 2018-04-12 Wacker Chemie Ag Secondary aminosiloxanes and method for production thereof
WO2021002163A1 (en) * 2019-07-02 2021-01-07 信越化学工業株式会社 Organopolysiloxane compound, composition comprising said compound, and method for preparing same
JPWO2021002163A1 (en) * 2019-07-02 2021-01-07
JP7279790B2 (en) 2019-07-02 2023-05-23 信越化学工業株式会社 Organopolysiloxane compound, composition containing the compound and method for producing the same

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