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WO2024184291A1 - Procédé de traitement cosmétique comprenant l'application d'une composition comprenant au moins une silicone vinylique, au moins une silicone mercapto et au moins une substance grasse liquide - Google Patents

Procédé de traitement cosmétique comprenant l'application d'une composition comprenant au moins une silicone vinylique, au moins une silicone mercapto et au moins une substance grasse liquide Download PDF

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Publication number
WO2024184291A1
WO2024184291A1 PCT/EP2024/055541 EP2024055541W WO2024184291A1 WO 2024184291 A1 WO2024184291 A1 WO 2024184291A1 EP 2024055541 W EP2024055541 W EP 2024055541W WO 2024184291 A1 WO2024184291 A1 WO 2024184291A1
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Prior art keywords
silicones
composition
weight
silicone
vinyl
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Inventor
Andrew Greaves
Chloe THIEULET
Constance Magne
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LOreal SA
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LOreal SA
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    • 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
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus 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
    • A61K8/30—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
    • A61K8/84—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
    • A61K8/899—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
    • 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
    • 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
    • A61K2800/81—Preparation or application process involves irradiation

Definitions

  • Cosmetic treatment process comprising the application of a composition comprising at least one vinyl silicone, at least one mercapto silicone and at least one liquid fatty substance
  • the present invention relates to a process for the cosmetic treatment of keratin fibres, in particular the hair.
  • Hair is generally damaged and embrittled by the action of external atmospheric agents such as light and bad weather, and also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving and/or relaxing.
  • Hair is thus damaged by these various factors and may over time become dry, coarse, brittle or dull, notably in fragile areas, and more particularly at the ends.
  • compositions intended to condition the hair are intended to condition the hair appropriately, giving it satisfactory cosmetic properties, especially in terms of smoothness, sheen, softness, suppleness, lightness, a natural feel and good disentangling properties.
  • the purpose of these compositions is thus to protect, repair, and transform the hair cosmetically.
  • These hair care compositions intended to be applied regularly to the hair, may be, for example, conditioning shampoos, hair conditioners, masks or sera, and may be in the form of gels, hair lotions or care creams that are more or less thick.
  • the present invention relates in particular to a process for the cosmetic treatment of keratin fibres, in particular human keratin fibres such as the hair, comprising the application to the keratin fibres of one or more non-acrylate silicones comprising one or more vinyl groups, of one or more silicones comprising one or more mercapto groups, and of one or more liquid fatty substances, using one or more compositions containing them, - the heating of the keratin fibres to a temperature ranging from 40°C to 210°C, followed by the photochemical treatment of the keratin fibres in the presence of one or more photoinitiators.
  • the process makes it possible to condition keratin fibres satisfactorily, especially improving the disentangling and the soft feel, and doing so in a long-lasting manner.
  • the process according to the invention makes it possible to give keratin fibres satisfactory and shampoo-resistant cosmetic properties.
  • the process of the invention makes it possible to afford improved disentangling and an improved soft feel, even after five shampoo washes, relative to a composition comprising the combination of an acrylate-functionalized silicone and a silicone functionalized with one or more mercapto groups.
  • the keratin fibres may be protected, repaired and transformed cosmetically in a long-lasting manner.
  • keratin fibres denotes human keratin fibres and more particularly the hair.
  • non-acrylate silicone denotes silicones which do not comprise an acrylate or methacrylate function.
  • Non-acrylate silicones comprising at least one vinyl group may be denoted by the term vinyl silicones.
  • sicone is intended to denote, in accordance with what is generally accepted, any organosilicon polymer or oligomer of linear or cyclic, branched or crosslinked structure, of variable molecular weight, which can be obtained by polymerization and/or polycondensation of suitably functionalized silanes, and formed essentially from a repetition of main units in which the silicon atoms are linked together via oxygen atoms (siloxane bond -Si-O-Si-), optionally substituted hydrocarbon-based radicals being directly linked via a carbon atom to said silicon atoms.
  • hydrocarbon-based radicals that are the most common are alkyl radicals, especially of Ci-Cio, and in particular methyl, fluoroalkyl radicals, the alkyl part of which is of Ci-Cio, and aryl radicals and in particular phenyl.
  • the non-acrylate silicone(s) comprising at least one vinyl group comprises a polysiloxane portion comprising one or more non-(meth)acrylate reactive vinyl groups.
  • the portion constituted of a non-silicone organic chain comprising one or more reactive vinyl groups is grafted onto the main chain of the polymer constituted by the polysiloxane portion.
  • the vinyl-functionalized silicone(s) is (are) chosen from vinyl silicone homopolymers and vinyl silicone copolymers.
  • the non-acrylate silicone(s) is (are) chosen from copolymers comprising, in their structure, at least one siloxane unit comprising a vinyl function and at least one dimethylsiloxane and/or diphenylsiloxane and/or methylphenylsiloxane unit.
  • the vinyl silicone polymer(s) has (have) the formula (I), (II) or (IT) below: in which:
  • Ra which may be identical or different, denote a saturated or unsaturated, linear or branched, optionally cyclic hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P,
  • Ra preferably denotes a Ci-Cioo, preferably C1-C12, divalent alkylene group, better still a propylene group,
  • Rb which may be identical or different, denote a group chosen from an alkyl group containing 1 to 6 carbon atoms, an alkoxy group containing 1 to 6 carbon atoms and/or a phenyl group.
  • Rb which may be identical or different, preferably denote a methyl group or a methoxy group, preferably methyl t ranges from 0 to 140, preferably from 10 to 120, u ranges from 1 to 140, preferably from 10 to 120, v ranges from 1 to 140, preferably from 1 to 20,
  • X represents a vinyl group.
  • R' a corresponding to a Ci- C20, preferably C1-C5, alkylene group
  • R' represents a C1-C10 alkylene group.
  • X and X are identical.
  • the vinyl-functionalized silicone(s) not comprising an acrylate group are chosen from dimethyl/diphenylsiloxane copolymers comprising a vinyl group at each end, in particular that sold under the trade name PDV 0325 by Gelest, and the vinylphenylsiloxane/phenylmethylsiloxane copolymers terminated at each end by a vinylphenylmethylsiloxane group, in particular that sold under the trade name PVV 3522 by Gelest.
  • the vinyl silicone(s) may be present in the composition according to the invention in a content preferably ranging from 0.1% to 30% by weight, better still from 0.5% to 20% by weight, even better still from 1% to 10% by weight, most preferentially from 1% to 5% by weight relative to the total weight of the composition containing them.
  • composition of use in the invention comprises (ii) one or more silicones chosen from silicones functionalized with one or more mercapto groups.
  • a mercapto or thiol group is an -SH group. The two terms will be used interchangeably.
  • the silicones containing thiol groups of the invention may be silicones with one or more thiol end groups and/or one or more pendent thiol groups borne by atoms not located at the end of the silicone chain.
  • the thiol groups may be borne by carbon or silicon atoms. They are preferably borne by carbon atoms. Even more preferably, they are borne by a carbon atom belonging to an alkyl chain, preferably comprising preferably 2 or 3 carbon atoms, said alkyl chains being borne by siloxane groups and in particular alkyl siloxane, notably methylsiloxane.
  • the thiol silicones of the invention may have, in their structure, siloxane groups not substituted with thiol groups or with groups bearing thiol functions.
  • the silicones containing thiol groups of the invention may have alkyl ends, in particular methyl or hydroxyl ends.
  • the silicone(s) functionalized with one or more mercapto groups according to the invention may be chosen from the compounds having the following formulae: in which:
  • Ri denotes a saturated or unsaturated, linear or branched, optionally cyclic hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P,
  • Ri preferably denotes a Ci-Cioo alkylene group, better still a C1-C12 group, preferentially a propylene group,
  • R2 which may be identical or different, denote an alkyl group containing 1 to 6 carbon atoms or an alkoxy group containing 1 to 6 carbon atoms.
  • R2 preferably denotes a methyl group or a methoxy group, more particularly a methyl group, n ranges from 0 to 140, preferably from 20 to 120, ni ranges from 1 to 140, 1 to 20, m ranges from 1 to 140, preferably from 20 to 120.
  • the mercapto-functionalized silicone(s) used in the present invention is or are chosen from the silicones of formula (III).
  • the silicone functionalized with one or more mercapto groups is one of formula (IV) in which the mercapto functions are pendent.
  • the group R in formula IV is a C3H6 alkylene group and the group R2 is a methyl radical.
  • the silicone(s) functionalized with one or more mercapto groups according to the invention may be chosen from mercapto(Ci-Cio)alkyl(Ci- Ce)alkylsiloxane homopolymers. Mention may be made of (meratopropyl)methylsiloxane homopolymers such as the product provided under the trade name SMS 992 by Gelest Incorporated.
  • mercapto-functionalized silicones used in the present invention mention may be made of mercaptopoly siloxane in which the mercapto functions are located at chain ends, sold by Shin-Etsu under the reference X-22-167B, and mercaptopolysiloxane, in which the mercapto functions are pendent, sold by Shin- Etsu under the reference KF-2001.
  • the silicone(s) functionalized with a mercapto group may be present in the composition containing them in a content which may preferably range from 0.1% to 30% by weight, better still from 0.5% to 20% by weight, even better still from 1% to 10% by weight, preferentially from 1% to 5% by weight of silicones containing thiol groups, relative to the total weight of the composition.
  • the functionalized silicone(s) may be introduced into the composition(s) either in pure form or in the presence of one or more silicone-based or hydrocarbonbased solvents, or in the form of a latex.
  • the mercapto silicones/vinyl silicones weight ratio ranges from 0.2 to 5, particularly from 0.5 to 1.5, more particularly from 0.8 to 1.2 and better still close to 1, even better still equal to 1.
  • the process of the invention uses one or more liquid fatty substances.
  • fatty substance means an organic compound that is insoluble in water at 25°C and at atmospheric pressure (1.013> ⁇ 10 5 Pa) (solubility of less than 5% by weight, preferably less than 1% by weight and even more preferentially less than 0.1% by weight). They bear in their structure at least one hydrocarbon-based chain including at least 6 carbon atoms and/or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or decamethylcyclopentasiloxane.
  • the fatty substances that may be used in the present invention are neither (poly)oxyalkylenated nor (poly)glycerolated.
  • Nonsilicone fatty substance means a fatty substance not containing any Si- O bonds
  • sicone fatty substance means a fatty substance containing at least one Si-0 bond
  • the fatty substances of use according to the invention are liquid fatty substances (or oils).
  • a liquid fatty substance is understood to be a fatty substance having a melting point of less than or equal to 25°C at atmospheric pressure (1.013x l0 5 Pa).
  • the melting point corresponds to the temperature of the most endothermic peak observed on thermal analysis (differential scanning calorimetry or DSC) as described in the Standard ISO 11357-3; 1999.
  • the melting point may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name MDSC 2920 by TA Instruments.
  • DSC differential scanning calorimeter
  • all the melting points are determined at atmospheric pressure (1.013* 10 5 Pa).
  • liquid fatty substance(s) according to the invention may be chosen from Ce to Ci6 liquid hydrocarbons, liquid hydrocarbons comprising more than 16 carbon atoms, nonsilicone oils of animal origin, oils of triglyceride type of plant or synthetic origin, fluoro oils, liquid fatty alcohols, liquid fatty acid and/or fatty alcohol esters other than triglycerides, and silicone oils, and mixtures thereof.
  • the fatty alcohols, esters and acids more particularly contain at least one saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 40 and better still from 8 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • Ce-Ci6 liquid hydrocarbons the latter may be linear, branched, or optionally cyclic, and are preferably chosen from alkanes. Examples that may be mentioned include hexane, cyclohexane, undecane, dodecane, isododecane, tridecane, isohexadecane and isodecane, and mixtures thereof.
  • the liquid hydrocarbons comprising more than 16 carbon atoms may be linear or branched, and of mineral or synthetic origin, and are preferably chosen from liquid paraffins or liquid petroleum jelly, polydecenes, hydrogenated polyisobutenes such as Parleam®, and mixtures thereof.
  • hydrocarbon oils or non-silicone oils of animal origin
  • the triglyceride oils of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides including from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by Stearinerie Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel, jojoba oil and shea butter oil, and mixtures thereof.
  • liquid fatty acid triglycerides including from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean
  • fluoro oils they may be chosen from perfluoromethylcyclopentane and perfluoro-l,3-dimethylcyclohexane, sold under the names Flutec® PCI and Flutec® PC3 by BNFL Fluorochemicals; perfluoro- 1,2- dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by 3M, or bromoperfluorooctyl sold under the name Foralkyl® by Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethylperfluoromorpholine sold under the name PF 5052® by 3M.
  • the liquid fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols, preferably unsaturated or branched alcohols, including from 6 to 40 carbon atoms and preferably from 8 to 30 carbon atoms. These fatty alcohols are neither oxyalkylenated nor glycerolated. Examples that may be mentioned include octyl dodecanol, 2- butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, isostearyl alcohol, oleyl alcohol, linolenyl alcohol, ricinoleyl alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof. Preferably, oleyl alcohol will be used.
  • liquid esters of fatty acids and/or of fatty alcohols other than the triglycerides mentioned above mention may be made notably of esters of saturated or unsaturated, linear Ci to C26 or branched C3 to C26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear Ci to C26 or branched C3 to C26 aliphatic monoalcohols or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
  • esters of monoalcohols Preferably, for the esters of monoalcohols, at least one from among the alcohol and the acid is branched.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; isostearyl octanoate; isocetyl octanoate; octyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methyl acetyl ricinoleate; octyl isononanoate; 2-ethylhexyl isononanoate; octyldodecy
  • ethyl palmitate and isopropyl palmitate alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate, and mixtures thereof.
  • Esters of C4 to C22 dicarboxylic or tricarboxylic acids and of Ci to C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2 to C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • the process of the invention can be carried out with, as fatty ester, sugar esters and diesters of Ce to C30, preferably C12 to C22, fatty acids.
  • sugar esters and diesters of Ce to C30, preferably C12 to C22, fatty acids.
  • sugar esters and diesters of Ce to C30, preferably C12 to C22, fatty acids.
  • sugar esters and diesters of Ce to C30, preferably C12 to C22, fatty acids.
  • suitable sugars include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, particularly alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen notably from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated Ce to C30 and preferably C12 to C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the esters may also be chosen from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates, arachidonates or mixtures thereof notably such as the mixed oleo-palmitate, oleo-stearate and palmito- stearate esters.
  • monoesters and diesters and notably sucrose, glucose or methylglucose mono- or di-oleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates, and mixtures thereof.
  • the silicone oils that may be used in the composition according to the present invention may be volatile or non-volatile, cyclic, linear or branched silicone oils, which are unmodified or modified with organic groups, and preferably have a viscosity from 5> ⁇ 10’ 6 to 2.5 m 2 /s at 25°C, and preferably MO’ 5 to 1 m 2 /s.
  • the silicone oils are chosen from polydialkylsiloxanes, particularly polydimethylsiloxanes (PDMS), and liquid polyorganosiloxanes comprising at least one aryl group.
  • PDMS polydimethylsiloxanes
  • liquid polyorganosiloxanes comprising at least one aryl group.
  • silicone oils may also be organomodified.
  • organomodified silicone oils that may be used in accordance with the invention are preferably liquid silicones as defined previously that comprise in their structure one or more organofunctional groups attached via a hydrocarbon-based group, chosen, for example, from amine groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or nonvolatile.
  • silicone oils are more particularly chosen from those with a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane, particularly sold under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, and Silbione® 70045 V5 by Rhodia, and mixtures thereof.
  • linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity of less than or equal to 5* 10' 6 m 2 /s at 25°C.
  • An example is decamethyltetrasiloxane notably sold under the name SH 200 by Toray Silicone. Silicones falling within this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, pages 27-32, Todd & Byers Volatile Silicone Fluids for Cosmetics.
  • Volatile polydialkylsiloxanes are preferably used as silicone liquid fatty substances.
  • liquid fatty substance(s) are chosen from:
  • liquid fatty substance(s) are chosen from isoparaffins and volatile silicones.
  • isoparaffin is understood to mean a branched alkane comprising at least 7 carbon atoms.
  • the isoparaffins may be chosen from isooctane, isodecane, isododecane and isohexadecane.
  • the isoparaffins of the invention may also be chosen from mixtures of compounds and in particular from products having the following references from the Handbook of Cosmetic Ingredients (INCI names): C7-8 Isoparaffin, C8-9 Isoparaffin, C9-11 Isoparaffin, C9-12 Isoparaffin, C9-13 Isoparaffin, C9-14 Isoparaffin, C9-16 Isoparaffin, C10-11 Isoparaffin, C10- 12 Isoparaffin, Cl 0-13 Isoparaffin, Cl 1-12 Isoparaffin, Cl 1-13 Isoparaffin, Cl 1-14 Isoparaffin, Cl 2- 14 Isoparaffin, Cl 2- 15 Isoparaffin, Cl 2-20 Isoparaffin, Cl 3-14 Isoparaffin, C13-16 Isoparaffin, C14-16 Isoparaffin, C15-19 Isoparaffin, C18-24 Isoparaffin, Cl 8-50 Isoparaffin, Cl 8-70 Isoparaffin, C20-40 Is
  • the isoparaffins of the invention comprise from 7 to 19 carbon atoms, better still from 7 to 16 carbon atoms and even better still from 10 to 16 carbon atoms.
  • the isoparaffin is isododecane.
  • the vapour pressure of the volatile silicones of the invention at ambient temperature and at atmospheric pressure ranges from 2.66 Pa to 40 000 Pa, better still from 13 Pa to 12 000 Pa.
  • the kinematic viscosity of the volatile silicones of the invention is less than or equal to 5* 10' 6 m 2 /s (5 cSt) at 25°C and at atmospheric pressure.
  • the volatile silicones of the invention are preferably linear and even more preferentially comprise from 2 to 9 silicon atoms.
  • the total content of one or more liquid fatty substances preferably ranges from 0.1% to 99.5% by weight, better still from 10% to 99% by weight, even better still from 25% to 98% by weight, most preferentially from 50% to 98%, and even more preferentially from 75% to 98%, by weight relative to the total weight of the composition containing them.
  • the useful composition may comprise water and/or organic solvents other than the liquid fatty substances.
  • compositions are preferably anhydrous, that is to say comprising less than 5% water at ambient temperature (20 to 25°C) and at atmospheric pressure (1.013x l0 5 Pa).
  • Organic solvents that may be mentioned include alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, or polyols or polyol ethers, for instance glycerol, ethylene glycol monomethyl, monoethyl or monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether, butylene glycol, dipropylene glycol, and also diethylene glycol alkyl ethers, for instance diethylene glycol monoethyl ether or monobutyl ether.
  • alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol
  • polyols or polyol ethers for instance glycerol, ethylene glycol monomethyl, monoethyl or monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether, butylene glyco
  • compositions may also contain one or more conditioning agents other than the above compounds, such as silicones other than vinyl silicones and thiol silicones, mineral or plant oils, plant waxes, solid fatty substances, cationic or amphoteric surfactants and cationic or amphoteric polymers.
  • conditioning agents such as silicones other than vinyl silicones and thiol silicones, mineral or plant oils, plant waxes, solid fatty substances, cationic or amphoteric surfactants and cationic or amphoteric polymers.
  • amino silicones may be envisaged in particular.
  • the cosmetic compositions may also contain one or more other compounds chosen from non-ionic or anionic surfactants, silicones other than thiol silicones and than non-acrylate vinyl silicones, reducing agents and in particular thiols other than thiol silicones, oxidizing agents and in particular hydrogen peroxide or persalts such as persulfates, colouring agents such as pigments, direct dyes or oxidation dyes, conditioning polymers, non-durable shaping agents such as styling polymers, which are preferably anionic or non-ionic, thickening agents, fillers, alkaline agents or acids, photoinitiators, and mixtures thereof
  • the composition also comprises one or more amino silicones.
  • composition used according to the invention may be, independently of others, in the form of a lotion, a gel, a mousse, a cream or a paste.
  • the compositions have a dynamic viscosity of less than 500 cps at ambient temperature (20 to 25°C) and at atmospheric pressure (1.013> ⁇ 10 5 Pa).
  • the process according to the invention comprises a step of applying to said fibres a composition comprising one or more vinyl silicones, and one or more mercapto silicones and one or more liquid fatty substances.
  • the process according to the invention comprises (a) a step of applying to said fibres a composition comprising one or more non-acrylate vinyl silicones and (b) a step of applying to said fibres a composition comprising one or more mercapto silicones, at least one of the two compositions comprising one or more liquid fatty substances.
  • step (a) may be performed before step (b) or vice versa.
  • the leave-on time of the composition or of each of the compositions defined above may be between 30 seconds and 1 hour, preferably from 1 to 30 minutes and better still from 2 to 15 minutes.
  • the treatment process according to the invention may be left on or rinsed off.
  • the keratin fibres may be heated in the course of the process according to the invention at least to a temperature ranging from 40°C to 210°C.
  • the keratin fibres are heated after the application of the vinyl silicone(s) and the mercapto silicone(s).
  • the process according to the invention comprises:
  • step (c) at least one step of heating the keratin fibres to a temperature ranging from 40°C to 210°C performed after steps (a) and (b).
  • the process according to the invention may comprise two steps of heating the keratin fibres.
  • the process comprises a step of heating the keratin fibres to a temperature ranging from 40°C to 80°C and a step of heating the keratin fibres to a temperature ranging from 100°C to 210°C, preferably from 120 to 180°C, by means of a heat source.
  • this operation may be performed using a hairstyling hood, a hairdryer, a round or flat iron, an infrared ray dispenser or other heating appliances.
  • the heat source ranging from 100°C to 210°C is a smoothing iron.
  • the process according to the invention may comprise a step of photochemical treatment of the keratin fibres in replacement for or in addition to the heating step as described previously.
  • the photochemical treatment step is carried out in the presence of one or more photoinitiators in an amount preferentially ranging from 1% to 20% by weight relative to the non-acrylate vinyl silicone.
  • composition(s) of use in the invention comprise one or more photoinitiators.
  • the photoinitiator(s) are chosen from the following compounds:
  • photoinitiator of dyes known as "photosensitizing dyes” such as ethyl eosin, eosin Y, fluorescein, rose bengal, methylene blue, erythrosin, phloxime, thionine, riboflavin, and methylene green.
  • photoinitiators are chosen from:
  • the preferred photoinitiator is the compound ethyl (2, 4, 6- trimethylbenzoyl) phenyl phosphinate (TPO-L).
  • the photoinitiator(s) is (are) preferably present in the composition in an amount ranging from 0.001% to 20% by weight, relative to the total weight of the composition, preferably ranging from 0.01% to 10% by weight, preferentially ranging from 0.05% to 5% by weight, even better still ranging from 0.1% to 3% by weight.
  • the process according to the invention comprises a step (ii) of light irradiation of the keratin fibres, consisting in exposing the keratin fibres to light radi ati on/ photochemi cal treatment.
  • This step (ii) of light irradiation of the keratin fibres is carried out after the step (i) of applying the composition as described above.
  • step (ii) of light irradiation/photochemical treatment of the keratin fibres consists in exposing the keratin fibres to artificial light radiation. More preferentially, step (ii) of light irradiation of the keratin fibres consists in exposing the keratin fibres to artificial light radiation, the wavelength of which is between 250 and 750 nm, even more preferentially between 280 and 700 nm, better still between 300 and 600 nm, and even better still between 350 and 500 nm.
  • the UV-visible radiation has a wavelength of 385 nm, 405 nm or 455 nm ( ⁇ 10 nanometers).
  • step (ii) of light irradiation of the keratin fibres consists in exposing the keratin fibres to artificial light radiation, the irradiance of which is within the range extending from 0.1 to 50 W/cm 2 of keratin fibres, more preferentially from 0.5 to 30 W/cm 2 , even more preferentially from 1 to 10 W/cm 2 .
  • the irradiation/photochemical treatment step of the process according to the invention is carried out using one or more light sources, preferably one or more light-emitting sources.
  • the UV-visible radiation is emitted by one or more light-emitting sources made up of one or more light-emitting elements such as lightemitting diodes (LEDs) or organic light-emitting diodes (OLEDs).
  • LEDs lightemitting diodes
  • OLEDs organic light-emitting diodes
  • the light-emitting source can be chosen from light-emitting diodes (LEDs) or organic light-emitting diodes (OLEDs).
  • LEDs light-emitting diodes
  • OLEDs organic light-emitting diodes
  • the irradiation step is carried out by means of one or more light-emitting sources, thereby making it possible to efficiently reduce the treatment time of the process.
  • the irradiation source used in the process according to the invention is carried by a clamp such as described in French patent application No. 1903781 which can be moved along a lock of hair.
  • the UV-visible radiation may be continuous or may be pulsed at a pulse frequency ranging from 0.001 to 1000 Hz and preferably ranging from 0.01 to 100 Hz.
  • the irradiation source may be moved along a lock of hair one or more consecutive times.
  • the irradiation step is carried out immediately after the application of the composition to the keratin fibres.
  • the term "immediately after” is understood to mean less than 5 minutes after the end of the application of the composition.
  • the duration of exposure of the keratin fibres to light radiation is greater than or equal to 1 second, more preferentially between 1 second and 45 minutes, even more preferentially between 2 seconds and 30 minutes, even better still between 5 seconds and 15 minutes.
  • the invention also relates to a multi-compartment device comprising a first compartment containing a composition comprising one or more vinyl silicones and a second compartment containing a composition comprising one or more silicones comprising one or more mercapto groups, at least one of the two compositions comprising one or more liquid fatty substances.
  • compositions were prepared:
  • compositions A, B and C described in the table above are applied to locks of sensitized SA20 hair (weight 2.7 g, length 27 cm) according to the following protocol:
  • a shampoo is applied to each of the locks, at a rate of 1 g per 2.8 g of locks, and the locks are then massaged for a time of 10 seconds.
  • the shampoo is left on for a time of 3 minutes, before rinsing with water at a temperature of 37°C, 10 passes being performed.
  • the lock is then dried.
  • This protocol is repeated five times and a second sensory evaluation of the disentangling is performed (measurement T5).
  • composition A according to the invention led to a persistence, with respect to shampoo washing, of the disentangling and smooth feel properties after 5 shampoo washes.
  • the IR spectra show the presence of silicones on the locks treated with composition A after 5 shampoo washes, whereas there are no longer any for the locks treated with compositions B and C.
  • composition A according to the invention led to a persistence, with respect to shampoo washing, of the disentangling and smooth feel properties after 10 shampoo washes, contrary to the comparative compositions not containing the two silicones.
  • compositions A and B described in the table above are applied to locks of sensitized and bleached SA20 hair according to the following protocol:
  • compositions with a bath ratio of: 0.05 g of formula per gram of hair
  • composition A according to the invention led to a persistence, with respect to shampoo washing, of the disentangling and smooth feel properties after 5 shampoo washes, contrary to the comparative composition containing a vinyl acrylate silicone.
  • composition A according to the invention (non-avrylate vinyl silicone) led to a persistence, with respect to shampoo washing, of the disentangling and smooth feel properties after 10 shampoo washes, contrary to the comparative composition containing a vinyl acrylate silicone.
  • composition A according to the invention led to a persistence, with respect to shampoo washing, of the disentangling and smooth feel properties after 10 shampoo washes.

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Abstract

La présente invention concerne un procédé de traitement de fibres kératiniques, comprenant : l'application sur les fibres kératiniques d'une ou plusieurs silicones non acrylate comprenant un ou plusieurs groupes vinyle, d'une ou plusieurs silicones comprenant un ou plusieurs groupes mercapto, et d'une ou plusieurs substances grasses liquides, à l'aide d'une ou de plusieurs compositions les contenant, le chauffage des fibres kératiniques à une température allant de 40°C à 210°C, suivi du traitement photochimique des fibres kératiniques en présence d'un ou plusieurs photo-initiateurs.
PCT/EP2024/055541 2023-03-03 2024-03-04 Procédé de traitement cosmétique comprenant l'application d'une composition comprenant au moins une silicone vinylique, au moins une silicone mercapto et au moins une substance grasse liquide Pending WO2024184291A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2301992A FR3146278A1 (fr) 2023-03-03 2023-03-03 Composition comprenant au moins une silicone vinylique, au moins une silicone mercapto et au moins un corps gras liquide
FRFR2301992 2023-03-03

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WO2024184291A1 true WO2024184291A1 (fr) 2024-09-12

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FR (1) FR3146278A1 (fr)
WO (1) WO2024184291A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0141380A2 (fr) * 1983-10-26 1985-05-15 Dow Corning Corporation Composition de silicone durcissant rapidement sous radiation ultra-violette
US20160032102A1 (en) * 2014-08-01 2016-02-04 Abirami Srikanth Thermally stable, high refractive index curable silicone compositions
WO2018185339A1 (fr) * 2017-04-07 2018-10-11 L'oreal Procédé de coloration des cheveux comprenant au moins un pigment, au moins un polymère à fonction acrylate et au moins un silicone fonctionnalisé choisi parmi les silicones fonctionnalisées avec au moins un groupe mercapto ou thiol
WO2021158327A1 (fr) * 2020-02-04 2021-08-12 Dow Silicones Corporation Gel d'amortissement à base de silicone haute fréquence

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0141380A2 (fr) * 1983-10-26 1985-05-15 Dow Corning Corporation Composition de silicone durcissant rapidement sous radiation ultra-violette
US20160032102A1 (en) * 2014-08-01 2016-02-04 Abirami Srikanth Thermally stable, high refractive index curable silicone compositions
WO2018185339A1 (fr) * 2017-04-07 2018-10-11 L'oreal Procédé de coloration des cheveux comprenant au moins un pigment, au moins un polymère à fonction acrylate et au moins un silicone fonctionnalisé choisi parmi les silicones fonctionnalisées avec au moins un groupe mercapto ou thiol
WO2021158327A1 (fr) * 2020-02-04 2021-08-12 Dow Silicones Corporation Gel d'amortissement à base de silicone haute fréquence

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Cosmetics and Toiletries", vol. 91, TODD & BYERS, pages: 27 - 32
WALTER NOLL'S: "Chemistry and Technology of Silicones", 1968, ACADEMIC PRESS

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