WO2013117843A1 - Cosmetic composition comprising a multifunctional compound, compound and cosmetic treatment method - Google Patents
Cosmetic composition comprising a multifunctional compound, compound and cosmetic treatment method Download PDFInfo
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- WO2013117843A1 WO2013117843A1 PCT/FR2013/050214 FR2013050214W WO2013117843A1 WO 2013117843 A1 WO2013117843 A1 WO 2013117843A1 FR 2013050214 W FR2013050214 W FR 2013050214W WO 2013117843 A1 WO2013117843 A1 WO 2013117843A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
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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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- 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
- A61Q5/002—Preparations for repairing the hair, e.g. hair cure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/42—Y being a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Definitions
- Cosmetic composition comprising a multifunctional compound, compound and cosmetic treatment method
- the present invention relates to a cosmetic composition, in particular a hair composition, capable of being used to bring about a permanent change to keratin materials, and a treatment method using said composition.
- a cosmetic composition in particular a hair composition
- a treatment method using said composition In the hair field, consumers want to have compositions to make a temporary change to their hair, and aiming for a good performance of the effect achieved.
- the change persists shampoos for at least 15 days, or more depending on the nature of the change.
- One of the known treatments for modifying the texture of the hair consists of the combination of heat and a composition comprising formalin. This treatment is especially effective to give a better appearance to damaged hair, and / or to treat long hair and curly hair.
- formalin is associated with its ability to crosslink proteins by reaction on its nucleophilic sites.
- the heat used can be that of iron (flat tongs or curling iron), whose temperature can reach in general 200 ° C, or even more.
- glyoxylic acid may give rise to some important limitations; in particular, its pH of action is acid, in particular of the order of 4, or even lower, which may not always be well tolerated, especially when the scalp is sensitive and / or irritated.
- cosmetic formulations with acidic pH can alter the hair and / or alter the color.
- the treatment sought is particularly intended to provide repair artificially colored hair. It is therefore preferred to avoid the use of assets that can provide a reinforcing effect but contribute to altering the hair and / or their artificial color.
- the composition according to the invention will not cause a change in the color of the hair, and will not cause hair breakage problem.
- the composition will not alter the integrity of the fiber, especially its cuticle. It will further improve the mechanical properties of the hair, such as moisture resistance and shine, and reduce the effects of frizz.
- an object of the present invention is a cosmetic composition
- a cosmetic composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) as defined below.
- compositions according to the invention makes it possible to obtain a solution for strengthening and / or repairing the hair, in a manner that is durable and compatible with any type of prior or future hair treatment.
- the principle of the invention consists in using molecules carrying on the one hand at least one first function of glyoxylic acid or derivative type or equivalent, and on the other hand at least one second function, identical or different from said first function. , able to react with the hair.
- This second function is preferably an electrophilic function. It may be an aldehyde function, optionally in the form of an acetal or hemiacetal that may belong to glyoxylic acid or its derivatives, in particular its hydrate or its protected forms, for example ethyldiethoxyacetate or methyldimethoxyacetate, giving respectively, by acid catalysis, the ethyl ester and the methyl ester of glyoxylic acid.
- This function can also be a ketone function, or a sulfur function capable of reacting with the sulphured functions of the hair, with or without pretreatment; in particular, it may be a thiol, thiosulfate or disulfide function, for example.
- the composition When applied to the skin or the nails, the composition may make it possible to obtain a surface sclerotization effect, in particular an antiperspirant effect, a reinforcing effect and / or a repair effect; or a grafting effect.
- a surface sclerotization effect in particular an antiperspirant effect, a reinforcing effect and / or a repair effect; or a grafting effect.
- the expression “at least one" is equivalent to the expression “one or more”.
- composition according to the invention therefore comprises at least one compound of formula (I), alone or as a mixture:
- x is an integer from 1 to 4;
- Z represents a group chosen from the following groups:
- R1 representing a hydrogen atom or a C1-C10 alkyl group
- R2 and R3 independently of one another, representing a hydrogen atom or a radical derived from a mono- or polyalcohol containing 1 at 30 carbon atoms
- y is an integer ranging from 1 to 4.
- Z or A denotes Z or A is an entity capable of reacting with the sulfur functional groups of keratin materials, in particular the hair, with or without pretreatment, said entity being or comprising at least one group chosen from the following groups: mercapto (SH); (C1-C10) alkylsulfinyl (RS (O) -) and in particular methylsulfinyl; alkoxy (C1-C10) -sulfinyl (RO-S (O) -) and in particular methoxysulfinyl; aryl (C 6 -C 30) -thio and in particular phenylthio; C1 -C10 alkyl-dithio and in particular methyldithio; thiopseudourea (-SC (NH) NH2) or thiopseudouronium; thiocyanate; thiosulfate; aldehyde.
- x is 1.
- Z represents a group chosen from:
- R1 H or C1-C4 alkyl.
- Z represents:
- w is 1.
- L represents a - (CH 2 ) n- chain or a - (CH 2 ) n -S- (CH 2 ) n "- chain with n being an integer from 1 to 4, and n 'and n ", identical or different, being integers ranging from 1 to 10.
- y is 1.
- A represents an entity capable of reacting with the sulphured functions of the hair, without pretreatment.
- A is chosen from one of the following groups:
- A represents a group chosen from:
- the compounds of formula (I) are in particular chosen from the following compounds, alone or as a mixture:
- R2 identical or different, preferably identical, representing an ethyl group, or the two R2 groups taken together form a ring, the two oxygen atoms then being connected by a divalent group (CH 2 ) 2 or (CH 2 ) 3-
- the compounds of formula (I) may also be in the form of salts, hydrates, acetals or hemiacetals, for example resulting from the interaction of the aldehyde function with water or a C 1 -C 6 alcohol, for example, especially ethanol.
- Acetals can be cyclic or acyclic.
- the compound of formula (I) or the mixture of said compounds is preferably present in the cosmetic composition at a concentration of between 0.01% and 50% by weight, in particular 0.1% to 20% by weight, preferably 1% by weight. 15%, relative to the total weight of the composition.
- the cosmetic composition also comprises a cosmetically acceptable medium, that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the nails.
- a cosmetically acceptable medium that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the nails.
- compositions according to the invention can be in any of the galenical forms conventionally used, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension or oily; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid strength, of the O / W, W / O or multiple type; a suspension or emulsion of soft consistency of cream (O / W) or (W / O) type; an aqueous or anhydrous gel, or any other cosmetic form.
- compositions can be packaged in pump bottles or in aerosol containers, in order to ensure application of the composition under vaporized form (lacquer) or in the form of foam.
- Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of hair.
- the composition preferably comprises at least one propellant.
- the composition according to the invention may be aqueous or anhydrous. It is preferably aqueous and then comprises water at a concentration preferably of between 5 and 98% by weight, in particular 20 and 95% by weight, more preferably 50 and 90% by weight, relative to the total weight of the composition.
- the composition may also comprise one or more organic solvents, in particular water-soluble solvents, such as C 1 -C 7 alcohols; mention may especially be made of C 1 -C 7 aliphatic or aromatic monoalcohols, polyols and C3-C7 polyol ethers, which can therefore be used alone or as a mixture with water.
- the composition comprises a mixture of water / ethanol, water / isopropanol or water / benzyl alcohol.
- composition according to the invention may further comprise at least one usual cosmetic ingredient, especially chosen from propellants; the oils; solid fatty substances and especially C8-C40 esters, C8-C40 acids; C8-C40 alcohols; nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, zwitterionic surfactants; solar filters; moisturizing agents; antidandruff agents; antioxidants; chelating agents; reducing agents; oxidation bases, couplers, oxidizing agents, direct dyes; defixing agents such as thiols and alkali hydroxides; pearlescent and opacifying agents; plasticizing or coalescing agents; hydroxy acids; pigments; the charges; silicones and in particular polydimethylsiloxanes (PDMS); thickeners, polymeric or not; gelling agents; emulsifiers; polymers in particular conditioning or styling; the perfumes; alkalizing or acidifying agents; silanes; crosslinking agents such as polyphenols,
- the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which can be understood, in general, for each ingredient, between 0.01 to 80% by weight.
- the oils may preferably be present in a proportion of 0.01 to 80% by weight, especially 0.02 to 40% by weight, or even 0.5 to 20% by weight, relative to the total weight of the composition. They can be carbonaceous. Mention may in particular be made of vegetable, animal or mineral oils, hydrogenated or not, linear or branched, saturated or unsaturated hydrocarbon, cyclic or aliphatic synthetic oils, such as, for example, polyalpha-olefins, in particular bind polydecenes and polyisobutenes; liquid fatty alcohols such as isostearyl alcohol, octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleic alcohol; liquid esters such as isopropyl myristate or isopropyl palmitate. Mention may also be made of silicone oils, volatile or not, organomodified or otherwise, water-soluble or not
- the composition may also comprise one or more solid fatty substances, and in particular one or more fatty alcohols, fatty esters and / or fatty acids, different from the above oils, having 8 to 40 carbon atoms; these solid fatty substances may preferentially be present in a proportion of 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition. Mention may in particular be made of C12-C32, especially C12-C26, linear chain fatty alcohols, and in particular cetyl alcohol, stearyl alcohol and cetylstearyl alcohol.
- Mention may also be made of C16-C40 linear or branched chain fatty acids, and in particular 18-methyl eicosanoic acid, coconut oil acids or hydrogenated coconut oil acids; stearic acid, lauric acid, palmitic acid and oleic acid, behenic acid, and mixtures thereof.
- the fatty acids are unsalified.
- Mention may also be made of linear chain fatty esters containing in total between 8 and 40 carbon atoms, such as myristyl, cetyl or stearyl myristates, palmitates and stearates, alone or as a mixture.
- compositions of the present invention will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention.
- the pH of the composition may be acidic, neutral or alkaline.
- the composition contains no or little glyoxylic acid, especially less than 10% by weight relative to the weight of compound (s) of formula (I).
- the cosmetic composition according to the invention can be in the form of a product for the care, cleaning and / or makeup of the skin of the body or the face, the lips, the eyebrows, the eyelashes, the nails and the skin.
- hair a sunscreen or self-tanning product, a personal care product, a hair product, especially care, cleaning, styling, shaping, hair dyeing. It finds particularly a particularly interesting application in the hair field, including the maintenance of the hairstyle or the shaping of the hair, or the care, the cosmetic treatment or the cleaning of the hair.
- the hair compositions are preferably shampoos, conditioners, styling or care gels, lotions or care creams, conditioners, masks, serums, styling lotions, blow-dry lotions, fixing and styling compositions such as lacquers or spray; restructuring lotion for hair; anti-hair loss lotion or gel, anti-parasitic shampoo, anti-dandruff lotion or shampoo, anti-seborrhoeic shampoo.
- the lotions may be packaged in various forms, in particular in vaporizers, pump-bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam.
- composition according to the invention finds an interesting application for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments; the compounds according to the invention can in particular be used after the treatment, after a step of coloring, bleaching or straightening the hair.
- composition according to the invention may also be derived from the mixture, for example at the time of use, of at least one composition comprising at least one compound of formula (I), alone or as a mixture, said composition preferably being anhydrous ; with at least one second composition preferably comprising water and optionally other ingredients, in particular at least one agent increasing the reactivity of the compound (I).
- compositions to be used at the time of use for example by mixing at the time of use of several, including two compositions, one of which comprises the compound of formula (I), alone or in admixture, and is preferably anhydrous.
- two compositions one of which comprises the compound of formula (I), alone or in admixture, and is preferably anhydrous.
- a first composition comprising the compound of formula (I), alone or as a mixture, for example in the form of a powder
- second composition comprising water and optionally other ingredients, in particular at least one agent increasing the reactivity of the compound (I).
- first composition comprising the compound of formula (I), alone or as a mixture, in solution or dispersion in an anhydrous solvent, for example ethanol, propylene glycol, glycerol or a PDMS, with a second composition including water and possibly other ingredients.
- anhydrous solvent for example ethanol, propylene glycol, glycerol or a PDMS
- the subject of the invention is also a process for the cosmetic treatment, in particular of make-up, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, lips, nails , hair and / or eyelashes, comprising the application on said materials of a cosmetic composition comprising at least one compound according to the invention.
- it is a cosmetic treatment method for the condition
- the shaping, strengthening and / or repairing of the hair in particular to provide or improve the disentangling, the smoothing, the combability, the maneuverability, the softness of the hair.
- it may be a cosmetic treatment method for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments.
- the method may also comprise at least one rinsing step and / or a heat treatment step.
- the application of the composition may optionally be followed by a rinsing step and / or a heat treatment step, for example at a temperature of between 150 ° C. and 250 ° C.
- It may in particular be a heat treatment step including with an iron, curling or smoothing, at a temperature between 150 ° C and 250 ° C.
- compositions with or without temperature, preferably with temperature, for example by using a flat gripper or a curling iron capable of raising the temperature to a value of between 150 ° C. and 250 ° C.
- the treatment method may also comprise an additional treatment step intended to increase the reactivity of the keratin.
- a step may be carried out prior to the step of applying the composition comprising the compound (s) of formula (I).
- the subject of the invention is also the compounds of formula ( ⁇ ) new: (Z) x- (L) w- (A) y ( ⁇ )
- x is an integer from 1 to 4.
- Z represents a group chosen from the following groups:
- R1 representing a hydrogen atom or a C1-C10 alkyl group
- R2 and R3 independently of one another, representing a hydrogen atom or a radical derived from a mono- or polyalcohol containing 1 at 30 carbon atoms
- Z or A denotes Z or A is an entity capable of reacting with the sulfur functional groups of keratin materials, in particular the hair, with or without pretreatment, said entity being or comprising at least one group chosen from the following groups: mercapto (SH); (C1-C10) alkylsulfinyl (RS (O) -) and in particular methylsulfinyl; alkoxy (C1-C10) -sulfinyl (RO-S (O) -) and in particular methoxysulfinyl; aryl (C 6 -C 30) -thio and in particular phenylthio; C1 -C10 alkyl-dithio and in particular methyldithio; thiopseudourea (-SC (NH) NH2) or thiopseudouronium; thiocyanate; thiosulfate.
- SH mercapto
- RS (O) -) alkylsulfiny
- the 3 formulas are applied to strands of damaged hair, with and without reducing pretreatment.
- the reducing treatment consists in applying for 15 minutes a formula based on thioglycolic acid Dulcia Vital 1, then rinsing.
- the locks After application and a 10-minute exposure, the locks are treated with an iron set at 180 ° C. Three passes are made at a speed of about 2 cm / s. Then, rinse and wash the hair.
- the hair treated with the formulas 2 and 3 are superior in transformation of the hair, compared to the hair treated with the formula 1.
- Formula 4 is applied to locks of natural hair having undergone a prior reduction treatment (treatment described in Example 1). It is heated for 10 minutes with the helmet taking the precaution of wrapping the hair with a plastic film.
- the locks After application and a 10-minute exposure, the locks are treated with an iron set at 180 ° C. Three passes are made at a speed of about 2 cm / s. Then, rinse and wash the hair.
- Hair treated with Formula 4 is more processed than Formula 1 treated in that it gives a glossy feel and a thicker appearance.
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Description
Composition cosmétique comprenant un composé multifonctionnel, composé et procédé de traitement cosmétique Cosmetic composition comprising a multifunctional compound, compound and cosmetic treatment method
La présente invention concerne une composition cosmétique, notamment capillaire, susceptible d'être employée pour apporter un changement rémanent aux matières kératiniques, et un procédé de traitement employant ladite composition. Dans le domaine capillaire, les consommateurs souhaitent disposer de compositions permettant d'apporter un changement temporaire à leur chevelure, et ce en visant une bonne tenue de l'effet réalisé. En général, on désire que le changement persiste aux shampooings pendant au minimum 15 jours, voire plus selon la nature dudit changement. The present invention relates to a cosmetic composition, in particular a hair composition, capable of being used to bring about a permanent change to keratin materials, and a treatment method using said composition. In the hair field, consumers want to have compositions to make a temporary change to their hair, and aiming for a good performance of the effect achieved. In general, it is desired that the change persists shampoos for at least 15 days, or more depending on the nature of the change.
Des traitements existent déjà pour modifier la couleur ou la forme des cheveux ainsi que, dans une certaine mesure, la texture des cheveux. L'un des traitements connus pour modifier la texture des cheveux consiste en l'association de chaleur et d'une composition comprenant du formol. Ce traitement est spécialement efficace pour conférer un meilleur aspect aux cheveux abîmés, et/ou pour traiter les cheveux longs et les cheveux bouclés. Treatments already exist to change the color or shape of the hair and, to a certain extent, the texture of the hair. One of the known treatments for modifying the texture of the hair consists of the combination of heat and a composition comprising formalin. This treatment is especially effective to give a better appearance to damaged hair, and / or to treat long hair and curly hair.
On associe l'action du formol à sa capacité de réticuler les protéines par réaction sur ses sites nucléophiles. La chaleur utilisée peut être celle du fer (pince plate ou fer à friser), dont la température peut atteindre en général 200°C, voire plus. The action of formalin is associated with its ability to crosslink proteins by reaction on its nucleophilic sites. The heat used can be that of iron (flat tongs or curling iron), whose temperature can reach in general 200 ° C, or even more.
Toutefois, on cherche de plus en plus à éviter l'emploi de telles substances, qui peuvent se révéler agressives pour les matières kératiniques en général, le cheveu en particulier. However, it is increasingly sought to avoid the use of such substances, which can be aggressive for keratin materials in general, the hair in particular.
Il a ainsi été proposé, par la demande WO201 1/104282, un nouveau procédé pour lisser de manière semi-permanente les cheveux, consistant à appliquer une solu- tion d'alphacétoacide sur le cheveu pendant 15 à 120 minutes, puis à sécher et enfin à lisser au fer, à une température d'environ 200°C, la chevelure. L'alphacé- toacide employé est de préférence l'acide glyoxylique. It has thus been proposed by the application WO201 1/104282, a new method for semi-permanently smoothing the hair, consisting in applying a solution of alphaketoacid on the hair for 15 to 120 minutes, then drying and finally to smooth iron, at a temperature of about 200 ° C, the hair. The alpha-endoacid used is preferably glyoxylic acid.
Toutefois, on a constaté que l'utilisation de l'acide glyoxylique pouvait engendrer quelques limitations importantes; en particulier, son pH d'action est acide, notamment de l'ordre de 4, voire inférieur, ce qui peut ne pas toujours être bien toléré, en particulier quand le cuir chevelu est sensible et/ou irrité. However, it has been found that the use of glyoxylic acid may give rise to some important limitations; in particular, its pH of action is acid, in particular of the order of 4, or even lower, which may not always be well tolerated, especially when the scalp is sensitive and / or irritated.
Il n'est pas non plus souhaitable de l'employer à de fortes concentrations, de par son caractère acide intrinsèque. Nor is it desirable to use it in high concentrations because of its intrinsic acidity.
Sa volatilité, amplifiée par l'utilisation de chaleur (fer), peut également poser problème. Its volatility, amplified by the use of heat (iron), can also be a problem.
Par ailleurs, les formulations cosmétiques à pH acide peuvent altérer les cheveux et/ou en altérer la couleur. Or, le traitement recherché est tout particulièrement destiné à apporter une réparation aux cheveux colorés artificiellement. On préfère donc éviter l'emploi d'actifs susceptibles d'apporter un effet de renforcement mais contribuant à altérer les cheveux et/ou leur couleur artificielle. In addition, cosmetic formulations with acidic pH can alter the hair and / or alter the color. However, the treatment sought is particularly intended to provide repair artificially colored hair. It is therefore preferred to avoid the use of assets that can provide a reinforcing effect but contribute to altering the hair and / or their artificial color.
Or, la demanderesse a maintenant découvert, de façon inattendue et surprenante, que certains composés bien particuliers permettaient d'apporter les propriétés recherchées aux matières kératiniques. Now, the plaintiff has now discovered, unexpectedly and surprisingly, that certain particular compounds allowed to bring the desired properties to the keratin materials.
En particulier, la composition selon l'invention ne va pas engendrer de changement de la couleur des cheveux, et ne va pas provoquer de problème de casse du cheveu. La composition n'altérera pas l'intégrité de la fibre, notamment sa cuticule. Elle va en outre améliorer les propriétés mécaniques des cheveux, telles que la tenue à l'humidité et la brillance, et réduire les effets de frisottis. In particular, the composition according to the invention will not cause a change in the color of the hair, and will not cause hair breakage problem. The composition will not alter the integrity of the fiber, especially its cuticle. It will further improve the mechanical properties of the hair, such as moisture resistance and shine, and reduce the effects of frizz.
Ainsi, un objet de la présente invention est une composition cosmétique compre- nant, dans un milieu cosmétiquement acceptable, au moins un composé de formule (I) tel que défini ci-après. Thus, an object of the present invention is a cosmetic composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) as defined below.
On a constaté que l'utilisation des compositions selon l'invention permet d'obtenir une solution pour le renforcement et/ou la réparation des cheveux, de façon du- rable et compatible avec tout type de traitement capillaire préalable ou à venir. It has been found that the use of the compositions according to the invention makes it possible to obtain a solution for strengthening and / or repairing the hair, in a manner that is durable and compatible with any type of prior or future hair treatment.
Le principe de l'invention consiste à utiliser des molécules portant d'une part au moins une première fonction de type acide glyoxylique ou dérivés ou équivalent, et d'autre part au moins une seconde fonction, identique ou différente de ladite pre- mière fonction, apte à réagir avec les cheveux. Cette seconde fonction est de préférence une fonction électrophile. Il peut s'agir d'une fonction aldéhyde, éventuellement sous forme d'acétal ou d'hémiacétal qui peut appartenir à l'acide glyoxylique ou à ses dérivés, en particulier son hydrate ou ses formes protégées, par exemple l'éthyldiéthoxyacétate ou le méthyldiméthoxyacétate, donnant respecti- vement, par catalyse acide par exemple, l'ester éthylique et l'ester méthylique de l'acide glyoxylique. Cette fonction peut aussi être une fonction cétone, ou encore une fonction soufrée apte à réagir avec les fonctions soufrées du cheveu, avec ou sans prétraitement; en particulier, elle peut être une fonction thiol, thiosulfate ou disulfure, par exemple. The principle of the invention consists in using molecules carrying on the one hand at least one first function of glyoxylic acid or derivative type or equivalent, and on the other hand at least one second function, identical or different from said first function. , able to react with the hair. This second function is preferably an electrophilic function. It may be an aldehyde function, optionally in the form of an acetal or hemiacetal that may belong to glyoxylic acid or its derivatives, in particular its hydrate or its protected forms, for example ethyldiethoxyacetate or methyldimethoxyacetate, giving respectively, by acid catalysis, the ethyl ester and the methyl ester of glyoxylic acid. This function can also be a ketone function, or a sulfur function capable of reacting with the sulphured functions of the hair, with or without pretreatment; in particular, it may be a thiol, thiosulfate or disulfide function, for example.
Lorsqu'elle est appliquée sur la peau ou les ongles, la composition peut permettre d'obtenir un effet de sclérotisation de surface, notamment un effet antitranspirant, un effet de renforcement et/ou de réparation; ou encore un effet de greffage. Dans la présente description, l'expression "au moins un" est équivalente à l'expression "un ou plusieurs". When applied to the skin or the nails, the composition may make it possible to obtain a surface sclerotization effect, in particular an antiperspirant effect, a reinforcing effect and / or a repair effect; or a grafting effect. In the present description, the expression "at least one" is equivalent to the expression "one or more".
La composition selon l'invention comprend donc au moins un composé de formule (I), seul ou en mélange: The composition according to the invention therefore comprises at least one compound of formula (I), alone or as a mixture:
(Z)x-(L)w-(A)y (I) dans laquelle : (Z) x- (L) w- (A) y (I) wherein:
- x est un entier allant de 1 à 4; - Z représente un groupement choisi parmi les groupements suivants : x is an integer from 1 to 4; Z represents a group chosen from the following groups:
avec R1 représentant un atome d'hydrogène ou un groupe alkyl en C1 -C10, avec R2 et R3, indépendamment l'un de l'autre, représentant un atome d'hydrogène ou un radical issu d'un mono- ou polyalcool comportant 1 à 30 atomes de carbone, with R1 representing a hydrogen atom or a C1-C10 alkyl group, with R2 and R3, independently of one another, representing a hydrogen atom or a radical derived from a mono- or polyalcohol containing 1 at 30 carbon atoms,
- w représente 0 ou 1 ; - w represents 0 or 1;
- L, qui est un linker (agent de liaison), représente une chaîne hydrocarbonée en C1 -C100, saturée ou insaturée, pouvant éventuellement être interrompue et/ou terminée par un ou plusieurs groupements choisis parmi les atomes d'oxygène ou de soufre, les groupes CO, NH, NR2 (R = alkyl en C1 -C10), SO2, SO3, ainsi que les groupes mono- ou polycycliques, saturés ou insaturés, comportant éventuel- lement un ou plusieurs hétéroatomes comme les atomes d'azote, d'oxygène ou de soufre, ladite chaîne hydrocarbonée et/ou ledit cycle pouvant être substitué par un ou plusieurs groupements choisis parmi les groupes amino; mono- ou dialkyl C1 - C10 amino; mono- ou dihydroxyalkyle C1 -C10 amino; cyano, hydroxy, nitro, halogène, alcoxy en C1 -C10, carboxy, sulfo, alkyle en C1 -C10, sulfonamido, carboxa- mido, alcoxy C1 -C10 carbonyle, acyle C2-C10; perfluoro; L, which is a linker (linking agent), represents a saturated or unsaturated C 1 -C 100 hydrocarbon-based chain which may optionally be interrupted and / or terminated by one or more groups chosen from oxygen or sulfur atoms, CO, NH, NR 2 (R = C 1 -C 10 alkyl), SO 2, SO 3, as well as saturated or unsaturated mono- or polycyclic groups, optionally containing one or more heteroatoms such as nitrogen atoms, oxygen or sulfur, said hydrocarbon chain and / or said ring may be substituted by one or more groups selected from amino groups; mono- or dialkyl C1-C10 amino; C1-C10 amino or dihydroxyalkyl amino; cyano, hydroxy, nitro, halogen, C1-C10 alkoxy, carboxy, sulpho, C1-C10 alkyl, sulphonamido, carboxamido, C1-C10 alkoxycarbonyl, C2-C10 acyl; perfluoroalkyl;
- y est un entier allant de 1 à 4; y is an integer ranging from 1 to 4;
- A désigne Z ou bien A est une entité apte à réagir avec les fonctions soufrées des matières kératiniques, notamment du cheveu, avec ou sans prétraitement, ladite entité étant ou comprenant au moins un groupe choisi parmi les groupes suivants: mercapto (SH); alkyl(C1 -C10)-sulfinyl (R-S(O)-) et en particulier méthyl- sulfinyl; alkoxy(C1 -C10)-sulfinyl (RO-S(O)-) et en particulier méthoxysulfinyl; aryl(C6-C30)-thio et en particulier phénylthio; alkyl(C1 -C10)-dithio et en particulier méthyldithio; thiopseudourée (-S-C(NH)NH2) ou thiopseudouronium; thiocyanate; thiosulfate; aldéhyde. De préférence, x est égal à 1 . - A denotes Z or A is an entity capable of reacting with the sulfur functional groups of keratin materials, in particular the hair, with or without pretreatment, said entity being or comprising at least one group chosen from the following groups: mercapto (SH); (C1-C10) alkylsulfinyl (RS (O) -) and in particular methylsulfinyl; alkoxy (C1-C10) -sulfinyl (RO-S (O) -) and in particular methoxysulfinyl; aryl (C 6 -C 30) -thio and in particular phenylthio; C1 -C10 alkyl-dithio and in particular methyldithio; thiopseudourea (-SC (NH) NH2) or thiopseudouronium; thiocyanate; thiosulfate; aldehyde. Preferably, x is 1.
De préférence, Z représente un groupement choisi parmi : Preferably, Z represents a group chosen from:
Avec R1 = H ou alkyl en C1 -C4. With R1 = H or C1-C4 alkyl.
Préférentiellement, Z représente : Preferably, Z represents:
De préférence, w est égal à 1 . Preferably, w is 1.
De préférence, L représente une chaîne -(CH2)n- ou une chaîne -(CH2)n'-S-S- (CH2)n"- avec n étant un entier allant de 1 à 4; et n' et n", identiques ou différents, étant des entiers allant de 1 à 10. Preferably, L represents a - (CH 2 ) n- chain or a - (CH 2 ) n -S- (CH 2 ) n "- chain with n being an integer from 1 to 4, and n 'and n ", identical or different, being integers ranging from 1 to 10.
Préférentiellement, L représente une chaîne -(CH2)n- avec n=2 ou bien une chaîne -(CH2)n'-S-S-(CH2)n"- avec n'=n"=2. Preferably, L represents a - (CH 2 ) n- chain with n = 2 or a - (CH 2 ) n -S- (CH 2 ) n "- chain with n '= n" = 2.
De préférence, y est égal à 1 . Preferably, y is 1.
De préférence, A représente une entité apte à réagir avec les fonctions soufrées du cheveu, sans prétraitement. Preferably, A represents an entity capable of reacting with the sulphured functions of the hair, without pretreatment.
Préférentiellement, A est choisi parmi l'un des groupes suivants : Preferably, A is chosen from one of the following groups:
ainsi que les groupes suivants : mercapto (SH); alkyl(C1 -C10)-sulfinyl et en parti- culier méthylsulfinyl; thiopseudourée; thiopseudouronium; aldéhyde. as well as the following groups: mercapto (SH); (C1-C10) -sulfinyl and in particular methylsulfinyl; thiopseudourea; thiopseudouronium; aldehyde.
Et encore mieux, A représente un groupe choisi parmi : And even better, A represents a group chosen from:
X- étant un contre-ion cosmétiquement acceptable X- being a cosmetically acceptable counterion
Les composés de formule (I) sont en particulier choisis parmi les composés suivants, seuls ou en mélange : The compounds of formula (I) are in particular chosen from the following compounds, alone or as a mixture:
R2, identique ou différent, de préférence identique, représentant un groupe éthyle, ou bien les deux groupes R2 pris ensemble forment un cycle, les deux atomes d'oxygène étant alors reliés par un groupe divalent (CH2)2 ou (CH2)3- R2, identical or different, preferably identical, representing an ethyl group, or the two R2 groups taken together form a ring, the two oxygen atoms then being connected by a divalent group (CH 2 ) 2 or (CH 2 ) 3-
Les composés de formule (I) peuvent également être sous forme de sels, hydrates, acétals ou hémiacétals, par exemple résultant de l'interaction de la fonction aldéhyde avec de l'eau ou un alcool en C1 -C6 par exemple, notamment l'éthanol. Les acétals peuvent être cycliques ou acycliques. The compounds of formula (I) may also be in the form of salts, hydrates, acetals or hemiacetals, for example resulting from the interaction of the aldehyde function with water or a C 1 -C 6 alcohol, for example, especially ethanol. Acetals can be cyclic or acyclic.
Les composés selon l'invention peuvent en particulier être préparés selon les procédés illustrés ci-après, qui pourront aisément être adaptés par l'homme du métier sur la base de ses connaissances générales. Préparation du composé (a) The compounds according to the invention can in particular be prepared according to the processes illustrated below, which can easily be adapted by those skilled in the art on the basis of his general knowledge. Preparation of the compound (a)
DCI = Dicyclohexylcarbodiimide DCI = Dicyclohexylcarbodiimide
HOBT = hydroxybenzotriazole HOBT = hydroxybenzotriazole
Préparation du composé (b) Preparation of compound (b)
Préparation du composé (d) Preparation of the compound (d)
1) DCI, HOBT 1) DCI, HOBT
Préparation du composé (e) Preparation of the compound (e)
Le composé de formule (I) ou le mélange desdits composés, est de préférence présent dans la composition cosmétique à une concentration comprise entre 0,01 % et 50% en poids, notamment 0,1 à 20% en poids, préférentiellement 1 % à 15%, par rapport au poids total de la composition. The compound of formula (I) or the mixture of said compounds is preferably present in the cosmetic composition at a concentration of between 0.01% and 50% by weight, in particular 0.1% to 20% by weight, preferably 1% by weight. 15%, relative to the total weight of the composition.
La composition cosmétique comprend par ailleurs un milieu cosmétiquement acceptable, c'est-à-dire un milieu compatible avec les matières kératiniques, notamment la peau du visage ou du corps, les lèvres, les cheveux, les cils, les sourcils et les ongles. The cosmetic composition also comprises a cosmetically acceptable medium, that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the nails.
Les compositions selon l'invention peuvent se présenter sous toutes les formes galéniques classiquement utilisées, et notamment sous forme d'une solution ou suspension aqueuse, alcoolique ou hydroalcoolique, ou huileuse; d'une solution ou d'une dispersion du type lotion ou sérum; d'une émulsion, notamment de con- sistance liquide ou semi-liquide, du type H/E, E/H ou multiple; d'une suspension ou émulsion de consistance molle de type crème (H/E) ou (E/H); d'un gel aqueux ou anhydre, ou de toute autre forme cosmétique. The compositions according to the invention can be in any of the galenical forms conventionally used, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension or oily; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid strength, of the O / W, W / O or multiple type; a suspension or emulsion of soft consistency of cream (O / W) or (W / O) type; an aqueous or anhydrous gel, or any other cosmetic form.
Ces compositions peuvent être conditionnées dans des flacons pompes ou dans des récipients aérosols, afin d'assurer une application de la composition sous forme vaporisée (laque) ou sous forme de mousse. De telles formes de conditionnement sont indiquées, par exemple, lorsqu'on souhaite obtenir un spray ou une mousse, pour le traitement des cheveux. Dans ces cas, la composition comprend de préférence au moins un agent propulseur. These compositions can be packaged in pump bottles or in aerosol containers, in order to ensure application of the composition under vaporized form (lacquer) or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of hair. In these cases, the composition preferably comprises at least one propellant.
La composition selon l'invention peut être aqueuse ou anhydre. Elle est de préférence aqueuse et comprend alors de l'eau à une concentration de préférence comprise entre 5 et 98% en poids, notamment 20 et 95% en poids, mieux 50 et 90% en poids, par rapport au poids total de la composition The composition according to the invention may be aqueous or anhydrous. It is preferably aqueous and then comprises water at a concentration preferably of between 5 and 98% by weight, in particular 20 and 95% by weight, more preferably 50 and 90% by weight, relative to the total weight of the composition.
La composition peut également comprendre un ou plusieurs solvants organiques, notamment hydrosolubles, tels que les alcools en C1 -C7; on peut notamment citer les monoalcools aliphatiques ou aromatiques en C1 -C7, les polyols et les éthers de polyols en C3-C7, qui peuvent donc être employés seuls ou en mélange avec de l'eau. Avantageusement, la composition comprend un mélange eau/éthanol, eau/isopropanol ou eau/alcool benzylique. The composition may also comprise one or more organic solvents, in particular water-soluble solvents, such as C 1 -C 7 alcohols; mention may especially be made of C 1 -C 7 aliphatic or aromatic monoalcohols, polyols and C3-C7 polyol ethers, which can therefore be used alone or as a mixture with water. Advantageously, the composition comprises a mixture of water / ethanol, water / isopropanol or water / benzyl alcohol.
La composition selon l'invention peut en outre comprendre au moins un ingrédient cosmétique usuel, notamment choisi parmi les propulseurs; les huiles; les corps gras solides et notamment les esters en C8-C40, les acides en C8-C40; les al- cools en C8-C40; les tensioactifs non ioniques, les tensioactifs cationiques, les tensioactifs anioniques, les tensioactifs amphotères, les tensioactifs zwittério- niques; les filtres solaires; les agents hydratants; les agents antipelliculaires; les agents antioxydants; les agents chélatants; les agents réducteurs; les bases d'oxydation, les coupleurs, les agents oxydants, les colorants directs; les agents défrisants tels que les thiols et les hydroxydes alcalins; les agents nacrants et opacifiants; les agents plastifiants ou de coalescence; les hydroxyacides; les pigments; les charges; les silicones et en particulier les polydiméthylsiloxanes (PDMS); les épaississants, polymériques ou non; les gélifiants; les émulsionnants; les polymères notamment conditionneurs ou coiffants; les parfums; les agents d'alcalinisation ou d'acidification; les silanes; les agents de réticulation tels que les polyphénols, les aldéhydes, la DHA. La composition peut bien évidemment comprendre plusieurs ingrédients cosmétiques figurant dans la liste ci-dessus. The composition according to the invention may further comprise at least one usual cosmetic ingredient, especially chosen from propellants; the oils; solid fatty substances and especially C8-C40 esters, C8-C40 acids; C8-C40 alcohols; nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, zwitterionic surfactants; solar filters; moisturizing agents; antidandruff agents; antioxidants; chelating agents; reducing agents; oxidation bases, couplers, oxidizing agents, direct dyes; defixing agents such as thiols and alkali hydroxides; pearlescent and opacifying agents; plasticizing or coalescing agents; hydroxy acids; pigments; the charges; silicones and in particular polydimethylsiloxanes (PDMS); thickeners, polymeric or not; gelling agents; emulsifiers; polymers in particular conditioning or styling; the perfumes; alkalizing or acidifying agents; silanes; crosslinking agents such as polyphenols, aldehydes, DHA. The composition may of course include several cosmetic ingredients listed above.
Selon leur nature et la destination de la composition, les ingrédients cosmétiques usuels peuvent être présents en des quantités usuelles, aisément déterminables par l'homme du métier, et qui peuvent être comprises, de manière générale, pour chaque ingrédient, entre 0,01 à 80% en poids. Depending on their nature and the purpose of the composition, the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which can be understood, in general, for each ingredient, between 0.01 to 80% by weight.
Les huiles peuvent être préférentiellement présentes à raison de 0,01 à 80% en poids, notamment 0,02 à 40% en poids, voire 0,5 à 20% en poids, par rapport au poids total de la composition. Elles peuvent être carbonées. On peut notamment citer les huiles végétales, animales ou minérales, hydrogénées ou non, les huiles synthétiques hydrocarbonées, cycliques ou aliphatiques, linéaires ou ramifiées, saturées ou insaturées, telles que par exemple les polyalpha-oléfines, en particu- lier les polydécènes et polyisobutènes; les alcools gras liquides tels que l'alcool isostéarylique, l'octyldodécanol, le 2-butyloctanol, le 2-hexyldécanol, le 2- undécylpentadécanol, l'alcool oléique ou l'alcool linoléique; les esters liquides comme le myristate d'isopropyle ou le palmitate d'isopropyle. On peut aussi citer les huiles de silicone, volatiles ou non, organo-modifiées ou non, hydrosolubles ou non; les huiles fluorées ou perfluorées; ainsi que leurs mélanges. The oils may preferably be present in a proportion of 0.01 to 80% by weight, especially 0.02 to 40% by weight, or even 0.5 to 20% by weight, relative to the total weight of the composition. They can be carbonaceous. Mention may in particular be made of vegetable, animal or mineral oils, hydrogenated or not, linear or branched, saturated or unsaturated hydrocarbon, cyclic or aliphatic synthetic oils, such as, for example, polyalpha-olefins, in particular bind polydecenes and polyisobutenes; liquid fatty alcohols such as isostearyl alcohol, octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleic alcohol; liquid esters such as isopropyl myristate or isopropyl palmitate. Mention may also be made of silicone oils, volatile or not, organomodified or otherwise, water-soluble or not; fluorinated or perfluorinated oils; as well as their mixtures.
La composition peut aussi comprendre un ou plusieurs corps gras solides, et en particulier un ou plusieurs alcools gras, esters gras et/ou acides gras, différents des huiles ci-dessus, ayant 8 à 40 atomes de carbone; ces corps gras solides peuvent préférentiellement être présents à raison de 0,01 à 50% en poids, notamment 0,1 à 20% en poids par rapport au poids total de la composition. On peut notamment citer les alcools gras à chaînes linéaires en C12-C32, notamment en C12-C26, et en particulier l'alcool cétylique, l'alcool stéarylique, l'alcool cétylstéa- rylique. On peut citer également les acides gras à chaînes linéaires ou ramifiées en C16-C40, et notamment l'acide méthyl-18 eicosanoïque, les acides d'huile de coprah ou d'huile de coprah hydrogénée; l'acide stéarique, l'acide laurique, l'acide palmitique et l'acide oléique, l'acide béhénique, et leurs mélanges. De préférence, les acides gras sont non salifiés. On peut encore citer les esters gras à chaînes linéaires, comportant au total entre 8 et 40 atomes de carbone, tels que les myris- tates, palmitates et stéarates de myristyle, de cétyle, de stéaryle, seuls ou en mélange. The composition may also comprise one or more solid fatty substances, and in particular one or more fatty alcohols, fatty esters and / or fatty acids, different from the above oils, having 8 to 40 carbon atoms; these solid fatty substances may preferentially be present in a proportion of 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition. Mention may in particular be made of C12-C32, especially C12-C26, linear chain fatty alcohols, and in particular cetyl alcohol, stearyl alcohol and cetylstearyl alcohol. Mention may also be made of C16-C40 linear or branched chain fatty acids, and in particular 18-methyl eicosanoic acid, coconut oil acids or hydrogenated coconut oil acids; stearic acid, lauric acid, palmitic acid and oleic acid, behenic acid, and mixtures thereof. Preferably, the fatty acids are unsalified. Mention may also be made of linear chain fatty esters containing in total between 8 and 40 carbon atoms, such as myristyl, cetyl or stearyl myristates, palmitates and stearates, alone or as a mixture.
L'homme de métier veillera à choisir les ingrédients entrant dans la composition, ainsi que leurs quantités, de manière à ce qu'ils ne nuisent pas aux propriétés des compositions de la présente invention. Those skilled in the art will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention.
Le pH de la composition peut être acide, neutre ou alcalin. The pH of the composition may be acidic, neutral or alkaline.
Selon une variante de l'invention, la composition ne contient pas ou peu d'acide glyoxylique, notamment moins de 10% en poids par rapport au poids de compo- sé(s) de formule (I). According to a variant of the invention, the composition contains no or little glyoxylic acid, especially less than 10% by weight relative to the weight of compound (s) of formula (I).
La composition cosmétique selon l'invention peut se présenter sous la forme d'un produit de soin, de nettoyage et/ou de maquillage de la peau du corps ou du vi- sage, des lèvres, des sourcils, des cils, des ongles et des cheveux, d'un produit solaire ou autobronzant, d'un produit d'hygiène corporelle, d'un produit capillaire, notamment de soin, de nettoyage, de coiffage, de mise en forme, de coloration des cheveux. Elle trouve notamment une application particulièrement intéressante dans le domaine capillaire, notamment pour le maintien de la coiffure ou la mise en forme des cheveux, ou encore le soin, le traitement cosmétique ou le nettoyage des cheveux. Les compositions capillaires sont de préférence des shampooings, des après-shampooings, des gels de coiffage ou de soin, des lotions ou crèmes de soin, des conditionneurs, des masques, des sérums, des lotions de mise en plis, des lotions pour le brushing, des compositions de fixation et de coiffage telles que les laques ou spray; de lotion restructurante pour cheveux; de lotion ou gel anti- chute, de shampoing antiparasitaire, de lotion ou shampoing antipelliculaire, de shampoing traitant antiséborrhéique. Les lotions peuvent être conditionnées sous diverses formes, notamment dans des vaporisateurs, des flacons-pompe ou dans des récipients aérosol afin d'assurer une application de la composition sous forme vaporisée ou sous forme de mousse. The cosmetic composition according to the invention can be in the form of a product for the care, cleaning and / or makeup of the skin of the body or the face, the lips, the eyebrows, the eyelashes, the nails and the skin. hair, a sunscreen or self-tanning product, a personal care product, a hair product, especially care, cleaning, styling, shaping, hair dyeing. It finds particularly a particularly interesting application in the hair field, including the maintenance of the hairstyle or the shaping of the hair, or the care, the cosmetic treatment or the cleaning of the hair. The hair compositions are preferably shampoos, conditioners, styling or care gels, lotions or care creams, conditioners, masks, serums, styling lotions, blow-dry lotions, fixing and styling compositions such as lacquers or spray; restructuring lotion for hair; anti-hair loss lotion or gel, anti-parasitic shampoo, anti-dandruff lotion or shampoo, anti-seborrhoeic shampoo. The lotions may be packaged in various forms, in particular in vaporizers, pump-bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam.
De manière encore plus particulière, la composition selon l'invention trouve une application intéressante pour le soin et le traitement cosmétique, notamment la protection, des cheveux, en particulier des cheveux affaiblis et/ou abîmés, par exemple par des traitements chimiques ou mécaniques; on peut notamment util i- ser les composés selon l'invention en post-traitement, après une étape de coloration, de décoloration ou de défrisage des cheveux. Even more particularly, the composition according to the invention finds an interesting application for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments; the compounds according to the invention can in particular be used after the treatment, after a step of coloring, bleaching or straightening the hair.
La composition selon l'invention peut également être issue du mélange, par exemple au moment de l'emploi, d'au moins une composition comprenant au moins un composé de formule (I), seul ou en mélange, ladite composition étant de préférence anhydre; avec au moins une deuxième composition comprenant de préférence de l'eau et éventuellement d'autres ingrédients, notamment au moins un agent augmentant la réactivité du composé (I). The composition according to the invention may also be derived from the mixture, for example at the time of use, of at least one composition comprising at least one compound of formula (I), alone or as a mixture, said composition preferably being anhydrous ; with at least one second composition preferably comprising water and optionally other ingredients, in particular at least one agent increasing the reactivity of the compound (I).
En effet, il est possible de préparer la composition à utiliser au moment de l'emploi, par exemple par mélange au moment de l'emploi de plusieurs, notamment deux, compositions dont l'une comprend le composé de formule (I), seul ou en mélange, et est de préférence anhydre. Par exemple, on peut mélanger une première composition comprenant le composé de formule (I), seul ou en mélange, par exemple sous forme de poudre, avec une deuxième composition comprenant de l'eau et éventuellement d'autres ingrédients, notamment au moins un agent augmentant la réactivité du composé (I). On peut également mélanger une première composition comprenant le composé de formule (I), seul ou en mélange, en solution ou dispersion dans un solvant anhydre, par exemple l'éthanol, le propylène glycol, la glycérine, un PDMS, avec une deuxième composition comprenant de l'eau et éventuel- lement d'autres ingrédients. Indeed, it is possible to prepare the composition to be used at the time of use, for example by mixing at the time of use of several, including two compositions, one of which comprises the compound of formula (I), alone or in admixture, and is preferably anhydrous. For example, it is possible to mix a first composition comprising the compound of formula (I), alone or as a mixture, for example in the form of a powder, with a second composition comprising water and optionally other ingredients, in particular at least one agent increasing the reactivity of the compound (I). It is also possible to mix a first composition comprising the compound of formula (I), alone or as a mixture, in solution or dispersion in an anhydrous solvent, for example ethanol, propylene glycol, glycerol or a PDMS, with a second composition including water and possibly other ingredients.
L'invention a également pour objet un procédé de traitement cosmétique, notamment de maquillage, de soin, de nettoyage, de coloration, de mise en forme, des matières kératiniques, notamment de la peau du corps ou du visage, des lèvres, des ongles, des cheveux et/ou des cils, comprenant l'application sur lesdites matières d'une composition cosmétique comprenant au moins un composé selon l'invention. The subject of the invention is also a process for the cosmetic treatment, in particular of make-up, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, lips, nails , hair and / or eyelashes, comprising the application on said materials of a cosmetic composition comprising at least one compound according to the invention.
De préférence, il s'agit d'un procédé de traitement cosmétique pour le condition- nement, la mise en forme, le renforcement et/ou la réparation des cheveux, en particulier pour apporter ou améliorer le démêlage, le lissage, la peignabilité, la maniabilité, la douceur de la chevelure. Preferably, it is a cosmetic treatment method for the condition The shaping, strengthening and / or repairing of the hair, in particular to provide or improve the disentangling, the smoothing, the combability, the maneuverability, the softness of the hair.
Tout particulièrement, il peut s'agir d'un procédé de traitement cosmétique pour le soin et le traitement cosmétique, notamment la protection, des cheveux, en particulier des cheveux affaiblis et/ou abîmés, par exemple par des traitements chimiques ou mécaniques. In particular, it may be a cosmetic treatment method for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments.
Le procédé peut également comprendre au moins une étape de rinçage et/ou une étape de traitement thermique. Ainsi, l'application de la composition peut être éventuellement suivie d'une étape de rinçage et/ou d'une étape de traitement thermique, par exemple à une température comprise entre 150°C et 250°C. The method may also comprise at least one rinsing step and / or a heat treatment step. Thus, the application of the composition may optionally be followed by a rinsing step and / or a heat treatment step, for example at a temperature of between 150 ° C. and 250 ° C.
Il peut notamment s'agir d'une étape de traitement thermique notamment avec un fer, à friser ou à lisser, à une température comprise entre 150°C et 250°C. It may in particular be a heat treatment step including with an iron, curling or smoothing, at a temperature between 150 ° C and 250 ° C.
On peut notamment utiliser la composition avec ou sans température, de préférence avec température, par exemple en utilisant une pince plate ou un fer à friser apte à monter la température à une valeur comprise entre 150°C et 250°C. In particular, it is possible to use the composition with or without temperature, preferably with temperature, for example by using a flat gripper or a curling iron capable of raising the temperature to a value of between 150 ° C. and 250 ° C.
Il est à notre que le procédé de traitement peut également comprendre une étape additionnelle de traitement destiné à augmenter la réactivité de la kératine. En particulier, une telle étape peut être effectuée préalablement à l'étape d'application de la composition comprenant le ou les composé(s) de formule (I). It is our view that the treatment method may also comprise an additional treatment step intended to increase the reactivity of the keratin. In particular, such a step may be carried out prior to the step of applying the composition comprising the compound (s) of formula (I).
Il peut s'agir d'une étape additionnelle destinée à modifier l'ionisation des protéines, ou bien une étape de traitement réducteur destiné à faire apparaître des fonctions thiols ou thiosulfates (traitement par des sulfites, des thiols, des phos- phines, des hydrures, par exemple). It may be an additional step intended to modify the ionization of the proteins, or a reducing treatment step intended to reveal thiol or thiosulphate functions (treatment with sulphites, thiols, phosphines, hydrides, for example).
L'invention a également pour objet les composés de formule (Γ) nouveaux : (Z)x-(L)w-(A)y (Γ) The subject of the invention is also the compounds of formula (Γ) new: (Z) x- (L) w- (A) y (Γ)
dans laquelle : in which :
- x est un entier allant de 1 à 4; x is an integer from 1 to 4;
- Z représente un groupement choisi parmi les groupements suivants : Z represents a group chosen from the following groups:
avec R1 représentant un atome d'hydrogène ou un groupe alkyl en C1 -C10, avec R2 et R3, indépendamment l'un de l'autre, représentant un atome d'hydrogène ou un radical issu d'un mono- ou polyalcool comportant 1 à 30 atomes de carbone, with R1 representing a hydrogen atom or a C1-C10 alkyl group, with R2 and R3, independently of one another, representing a hydrogen atom or a radical derived from a mono- or polyalcohol containing 1 at 30 carbon atoms,
- w représente 0 ou 1 ; - w represents 0 or 1;
- L, qui est un linker (agent de liaison), représente une chaîne hydrocarbonée en C1 -C100, saturée ou insaturée, pouvant éventuellement être interrompue et/ou terminée par un ou plusieurs groupements choisis parmi les atomes d'oxygène ou de soufre, les groupes CO, NH, NR2 (R = alkyl en C1 -C10), SO2, SO3, ainsi que les groupes mono- ou polycycliques, saturés ou insaturés, comportant éventuellement un ou plusieurs hétéroatomes comme les atomes d'azote, d'oxygène ou de soufre, ladite chaîne hydrocarbonée et/ou ledit cycle pouvant être substitué par un ou plusieurs groupements choisis parmi les groupes amino; mono- ou dialkyl C1 - C10 amino; mono- ou dihydroxyalkyle C1 -C10 amino; cyano, hydroxy, nitro, halogène, alcoxy en C1 -C10, carboxy, sulfo, alkyle en C1 -C10, sulfonamido, carboxa- mido, alcoxy C1 -C10 carbonyle, acyle C2-C10; perfluoro; - y est un entier allant de 1 à 4; L, which is a linker (linking agent), represents a saturated or unsaturated C 1 -C 100 hydrocarbon-based chain which may optionally be interrupted and / or terminated by one or more groups chosen from oxygen or sulfur atoms, the groups CO, NH, NR2 (R = C1 -C10 alkyl), SO2, SO3, as well as mono- or polycyclic groups, saturated or unsaturated, optionally containing one or more heteroatoms such as nitrogen, oxygen atoms; or sulfur, said hydrocarbon chain and / or said ring may be substituted by one or more groups selected from amino groups; mono- or dialkyl C1-C10 amino; C1-C10 amino or dihydroxyalkyl amino; cyano, hydroxy, nitro, halogen, C1-C10 alkoxy, carboxy, sulpho, C1-C10 alkyl, sulphonamido, carboxamido, C1-C10 alkoxycarbonyl, C2-C10 acyl; perfluoroalkyl; y is an integer ranging from 1 to 4;
- A désigne Z ou bien A est une entité apte à réagir avec les fonctions soufrées des matières kératiniques, notamment du cheveu, avec ou sans prétraitement, ladite entité étant ou comprenant au moins un groupe choisi parmi les groupes suivants: mercapto (SH); alkyl(C1 -C10)-sulfinyl (R-S(O)-) et en particulier méthyl- sulfinyl; alkoxy(C1 -C10)-sulfinyl (RO-S(O)-) et en particulier méthoxysulfinyl; aryl(C6-C30)-thio et en particulier phénylthio; alkyl(C1 -C10)-dithio et en particulier méthyldithio; thiopseudourée (-S-C(NH)NH2) ou thiopseudouronium; thiocyanate; thiosulfate. L'invention est illustrée plus en détail dans l'exemple de réalisation suivant. Exemple 1 - A denotes Z or A is an entity capable of reacting with the sulfur functional groups of keratin materials, in particular the hair, with or without pretreatment, said entity being or comprising at least one group chosen from the following groups: mercapto (SH); (C1-C10) alkylsulfinyl (RS (O) -) and in particular methylsulfinyl; alkoxy (C1-C10) -sulfinyl (RO-S (O) -) and in particular methoxysulfinyl; aryl (C 6 -C 30) -thio and in particular phenylthio; C1 -C10 alkyl-dithio and in particular methyldithio; thiopseudourea (-SC (NH) NH2) or thiopseudouronium; thiocyanate; thiosulfate. The invention is illustrated in more detail in the following embodiment. Example 1
On prépare les compositions suivantes : Formule 1 (comparative) The following compositions are prepared: Formula 1 (comparative)
Acide glyoxylique (Merck) 1 mol% Glyoxylic acid (Merck) 1 mol%
Glycérol 30 g Glycerol 30 g
Ammoniaque 20% qs pH 7 Ammonia 20% qs pH 7
Eau qsp 100 g Water qs 100 g
Formule 2 (invention) Formula 2 (invention)
Composé (a) 1 mol% Compound (a) 1 mol%
Glycérol 30 g Glycerol 30 g
Eau qsp 100 g Water qs 100 g
Formule 3 (invention) Formula 3 (invention)
Composé (b) 1 mol% Compound (b) 1 mol%
Glycérol 30 g Glycerol 30 g
Eau qsp 100 g Water qs 100 g
Composés : Compounds
On applique les 3 formules sur des mèches de cheveux abîmés, avec et sans pré- traitement réducteur. Le traitement réducteur consiste à appliquer pendant 15 minutes une formule à base d'acide thioglycolique Dulcia Vital 1 , puis à rincer. The 3 formulas are applied to strands of damaged hair, with and without reducing pretreatment. The reducing treatment consists in applying for 15 minutes a formula based on thioglycolic acid Dulcia Vital 1, then rinsing.
Après application et une pose de 10 minutes, on traite les mèches avec un fer réglé à 180°C. On réalise 3 passages à la vitesse de 2 cm/s environ. Puis, on rince et on lave les cheveux. After application and a 10-minute exposure, the locks are treated with an iron set at 180 ° C. Three passes are made at a speed of about 2 cm / s. Then, rinse and wash the hair.
Sans traitement réducteur préalable, les cheveux traités par les formules 2 et 3 sont supérieurs en transformation du cheveu, comparés aux cheveux traités par la formule 1 . Without prior reducing treatment, the hair treated with the formulas 2 and 3 are superior in transformation of the hair, compared to the hair treated with the formula 1.
Avec traitement réducteur préalable, les cheveux traités par les formules 2 et 3, sont très supérieurs aux cheveux traités par la formule 1 . With prior reduction treatment, the hair treated with formulas 2 and 3, are much higher than the hair treated with formula 1.
Exemple 2 Example 2
On prépare la composition suivante : The following composition is prepared:
Formule 4 (invention) 0,5 mol% Formula 4 (invention) 0.5 mol%
30 g 30 g
qsp 100 g qsp 100 g
X étant un contre-ion X being a counter-ion
cosmétiquement acceptable cosmetically acceptable
On applique la formule 4 sur des mèches de cheveux naturels ayant subi un traitement réducteur préalable (traitement décrit à l'exemple 1 ). On chauffe pendant 10 minutes au casque en prenant la précaution d'envelopper les cheveux avec un film plastique. Formula 4 is applied to locks of natural hair having undergone a prior reduction treatment (treatment described in Example 1). It is heated for 10 minutes with the helmet taking the precaution of wrapping the hair with a plastic film.
Après application et une pose de 10 minutes, on traite les mèches avec un fer réglé à 180°C. On réalise 3 passages à la vitesse de 2 cm/s environ. Puis, on rince et on lave les cheveux. After application and a 10-minute exposure, the locks are treated with an iron set at 180 ° C. Three passes are made at a speed of about 2 cm / s. Then, rinse and wash the hair.
Pour comparaison, on réalise un traitement identique avec la formule 1 comparative, décrite à l'exemple 1 . For comparison, an identical treatment is carried out with the comparative formula 1, described in Example 1.
Les cheveux traités par la formule 4 sont plus transformés que ceux traités par la formule 1 , en ce sens qu'ils donnent un toucher brillant et un aspect plus épais. Hair treated with Formula 4 is more processed than Formula 1 treated in that it gives a glossy feel and a thicker appearance.
Claims
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1251210A FR2986795B1 (en) | 2012-02-09 | 2012-02-09 | COSMETIC COMPOSITION COMPRISING A MULTIFUNCTIONAL COMPOUND, COMPOUND AND COSMETIC PROCESSING METHOD |
| FR1251210 | 2012-02-09 | ||
| US201261640176P | 2012-04-30 | 2012-04-30 | |
| US61/640,176 | 2012-04-30 |
Publications (1)
| Publication Number | Publication Date |
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| WO2013117843A1 true WO2013117843A1 (en) | 2013-08-15 |
Family
ID=45992462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR2013/050214 Ceased WO2013117843A1 (en) | 2012-02-09 | 2013-02-01 | Cosmetic composition comprising a multifunctional compound, compound and cosmetic treatment method |
Country Status (2)
| Country | Link |
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| FR (1) | FR2986795B1 (en) |
| WO (1) | WO2013117843A1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015094760A1 (en) * | 2013-12-19 | 2015-06-25 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US10434051B2 (en) | 2014-12-19 | 2019-10-08 | The Procter And Gamble Company | Shaping keratin fibers using arabinose and ethylene carbonate |
| US10568826B2 (en) | 2014-12-19 | 2020-02-25 | The Procter And Gamble Company | Shaping keratin fibres using a pretreatment and a protein crosslinking composition |
| US10729630B2 (en) | 2013-12-19 | 2020-08-04 | The Procter & Gamble Company | Shaping keratin fibres using an active agent comprising at least two functional groups selected from: —C(OH)- and —C(=O)OH |
| US10912726B2 (en) | 2013-12-19 | 2021-02-09 | The Procter And Gamble Company | Shaping keratin fibres using a reducing composition and a fixing composition |
| US10945931B2 (en) | 2015-06-18 | 2021-03-16 | The Procter And Gamble Company | Shaping keratin fibres using dialdehyde compounds |
| US11096879B2 (en) | 2013-12-19 | 2021-08-24 | The Procter And Gamble Plaza | Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O- |
| US11103434B2 (en) | 2013-12-19 | 2021-08-31 | The Procter And Gamble Company | Shaping keratin fibres using carbonate ester |
| US11110046B2 (en) | 2013-12-19 | 2021-09-07 | The Procter And Gamble Company | Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid |
| US11129784B2 (en) | 2013-12-19 | 2021-09-28 | The Procter And Gamble Company | Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof |
| US11154480B2 (en) | 2013-12-19 | 2021-10-26 | The Procter And Gamble Company | Shaping keratin fibres using a sugar |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11103434B2 (en) | 2013-12-19 | 2021-08-31 | The Procter And Gamble Company | Shaping keratin fibres using carbonate ester |
| JP2016540005A (en) * | 2013-12-19 | 2016-12-22 | ザ プロクター アンド ギャンブル カンパニー | Molding of keratin fiber using carbonate ester |
| US10064799B2 (en) | 2013-12-19 | 2018-09-04 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US10729630B2 (en) | 2013-12-19 | 2020-08-04 | The Procter & Gamble Company | Shaping keratin fibres using an active agent comprising at least two functional groups selected from: —C(OH)- and —C(=O)OH |
| US10912726B2 (en) | 2013-12-19 | 2021-02-09 | The Procter And Gamble Company | Shaping keratin fibres using a reducing composition and a fixing composition |
| US11096879B2 (en) | 2013-12-19 | 2021-08-24 | The Procter And Gamble Plaza | Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O- |
| WO2015094760A1 (en) * | 2013-12-19 | 2015-06-25 | The Procter & Gamble Company | Shaping keratin fibres using carbonate ester |
| US11110046B2 (en) | 2013-12-19 | 2021-09-07 | The Procter And Gamble Company | Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid |
| US11129784B2 (en) | 2013-12-19 | 2021-09-28 | The Procter And Gamble Company | Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof |
| US11154480B2 (en) | 2013-12-19 | 2021-10-26 | The Procter And Gamble Company | Shaping keratin fibres using a sugar |
| US10434051B2 (en) | 2014-12-19 | 2019-10-08 | The Procter And Gamble Company | Shaping keratin fibers using arabinose and ethylene carbonate |
| US10568826B2 (en) | 2014-12-19 | 2020-02-25 | The Procter And Gamble Company | Shaping keratin fibres using a pretreatment and a protein crosslinking composition |
| US10945931B2 (en) | 2015-06-18 | 2021-03-16 | The Procter And Gamble Company | Shaping keratin fibres using dialdehyde compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2986795B1 (en) | 2015-08-21 |
| FR2986795A1 (en) | 2013-08-16 |
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