WO2016142635A1 - Method for the cosmetic treatment of thick hair with a pyridine dicarboxylic acid compound - Google Patents

Method for the cosmetic treatment of thick hair with a pyridine dicarboxylic acid compound Download PDF

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Publication number
WO2016142635A1
WO2016142635A1 PCT/FR2016/050557 FR2016050557W WO2016142635A1 WO 2016142635 A1 WO2016142635 A1 WO 2016142635A1 FR 2016050557 W FR2016050557 W FR 2016050557W WO 2016142635 A1 WO2016142635 A1 WO 2016142635A1
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Prior art keywords
hair
iron
compound
thick
formula
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PCT/FR2016/050557
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French (fr)
Inventor
Nawel Baghdadli
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L'oreal
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Priority to CN201680015294.2A priority Critical patent/CN107427435A/en
Publication of WO2016142635A1 publication Critical patent/WO2016142635A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/002Preparations for repairing the hair, e.g. hair cure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the invention relates to a method for the cosmetic treatment of thick hair, in particular Asian hair, using one or more pyridine dicarboxylic acid compounds.
  • the hair can be damaged or weakened by the action of chemical treatments such as dyes, discolorations, perms, straightening, repeated washing.
  • chemical treatments such as dyes, discolorations, perms, straightening, repeated washing.
  • the hair becomes sensitized, is thus damaged by these different treatments and can eventually become dry, rough, brittle, dull, forked or soft.
  • compositions for conditioning the hair in a suitable manner by providing satisfactory cosmetic properties.
  • These hair care compositions may be, for example, conditioning shampoos, after shampoos, masks, serums.
  • the conditioning effect obtained generally fades during successive shampoos and has an unsatisfactory shampoo remanence. This is especially true for thick hair.
  • the subject of the present invention is a method for the cosmetic treatment of thick hair comprising the application to said hair of a cosmetic composition comprising one or more pyridine dicarboxylic acid compounds as defined below.
  • the hair treated with the method according to the invention remains disciplined because it does not show the presence of frizz.
  • the hair is aligned, smooth; in addition, they have a better surface quality, are more resistant, break less easily, seem less fragile.
  • the treated hair is also brighter.
  • the process according to the invention has the advantage of conferring good shampoo remanence on these properties of fiber quality, reinforcement and resistance.
  • the treated hair is reinforced, protected or even repaired, sustainable environment.
  • the process according to the invention makes it possible in particular to improve the quality of the hair, to protect it, to strengthen it, to make it more resistant, less brittle, and even to repair it when it is damaged.
  • Patent Application FR2838336 discloses the use of pyridine dicarboxylic acid compounds for the anti-hair loss treatment. However, the use of this family of compounds for the purpose of conditioning, protecting, strengthening, thick hair was neither described nor suggested in this document.
  • thick hair hair having an individual diameter of at least 90 microns, preferably at least 100 microns; in particular between 90 and 120 microns, or even between 100 and 120 microns.
  • the thick hair is especially Asian hair.
  • the invention consists of a method of cosmetic treatment of Asian hair, comprising the application to said hair of a cosmetic composition comprising one or more pyridine dicarboxylic acid compounds as defined above. after.
  • Said pyridine-2,4-dicarboxylic acid compound used according to the invention is chosen from the compounds of formula (I) below:
  • R1 and R2 are independently of each other OH, OR ', -NH 2 , -NHR', -NR'R ", with R 'and R" representing, independently of one another, a linear or branched, saturated or unsaturated C 1 -C 18 alkyl, optionally substituted by at least one group chosen from OH, C 1 -C 6 alkoxy, C 1 -C 6 acyloxy, amino, (C 1 -C 6) alkyloxycarbonyl, or alkyl (C1-C6) amino, or C6-C10 aryl, as well as their salts.
  • R 1 and R 2 represent, independently of one another, OH, OR ', with R' representing a linear or branched, saturated C 1 -C 12 alkyl, optionally optionally substituted with at least one OH, (C 1 -C 4) alkoxy, (C 1 -C 4) acyloxy, (C 1 -C 4) alkyloxycarbonyl, or (C 1 -C 4) alkylamino, or phenyl.
  • R1 and R2 represent, independently of each other, OH, OR ', and R' represents a linear or branched, saturated C1-C6 alkyl, optionally substituted by at least one OH, alkoxy group or (C1-C4), (C1-C4) acyloxy, (C1-C4) alkyloxycarbonyl, or (C1-C4) alkylamino, or phenyl, or a salt of one of these compounds.
  • the following pyridine-2,4-dicarboxylic acid derivatives are preferred in the context of the present invention:
  • Salts of the compounds of formula (I) are, according to the invention, the organic or inorganic salts of a compound of formula (I), these salts being physiologically acceptable.
  • mineral salts mention may be made of sodium or potassium salts as well as the salts of zinc (Zn 2+ ), calcium (Ca 2+ ), copper (Cu 2+ ), iron (Fe 2+ ), strontium (Sr 2+ ), magnesium (Mg 2+ ), manganese (Mn 2+ ); hydroxides, carbonates and halides, especially chlorides.
  • organic salts mention may be made of the triethanolamine, monoethanolamine, diethanolamine, hexadecylamine, N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine and tris-hydroxymethylaminomethane salts.
  • the compounds of formula (I) are known as such; they are particularly described, as well as their manufacture, in patent EP1352629.
  • the compound (s) of formula (I) are present in the cosmetic composition used according to the invention in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition, preferably ranging from 0.5 to 8% by weight, preferably ranging from 0.5 to 6% by weight.
  • the cosmetic composition used according to the invention contains in particular a cosmetically acceptable medium, that is to say compatible with human keratin materials such as the skin (body, face, eye contour, scalp), the hair, eyelashes, eyebrows, hair, nails, lips.
  • the cosmetically acceptable medium of the composition used in the process according to the invention is advantageously an aqueous medium.
  • organic solvent there may be mentioned for example C 2 -C 4 alcohols such as ethanol and isopropanol; polyols, especially those having from 2 to 6 carbon atoms such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether; and their mixtures.
  • the cosmetic composition comprises from 50 to 99.5% by weight of water relative to the weight of the composition.
  • the cosmetic composition used according to the invention may also comprise one or more usual cosmetic additives, chosen in particular from nonionic, anionic, cationic and amphoteric surfactants, vitamins and provitamines including panthenol, sunscreens, fillers, substances and the like.
  • the cosmetic composition used according to the invention may be in any of the galenical forms conventionally used for capillary application and especially in the form of an aqueous solution, aqueous-alcoholic solution, oil-in-water (O / W) emulsion or water-in solution.
  • the cosmetic composition is in the form of an aqueous or aqueous-alcoholic solution or gel.
  • the method according to the invention may comprise a step of heating the thick hair at a temperature of at least 100 ° C, preferably ranging from 100 to 250 ° C.
  • the step of heating the keratinous fibers is carried out at a temperature ranging from 150 to 220 ° C., preferably ranging from 160 to 220 ° C., preferably ranging from 160 to 200 ° C., in particular ranging from 170 to 190 ° C.
  • the heating step is carried out, when it is present, after the step of applying the cosmetic composition comprising the compound (s) (I) to the keratinous fibers.
  • the heating step can help to give a good shaping of the hair. It can also make it possible to optimize the effects of the process, in particular to optimize the remanence of the cosmetic properties after one or more shampoos.
  • This heating step is advantageously carried out by means of an iron.
  • iron is meant, in the sense of the present invention, a device for heating the keratinous fibers contacting said fibers and the heating device.
  • the end of the iron coming into contact with the keratin fibers generally has two flat surfaces. These two surfaces can be metallic or ceramic. In particular, these two surfaces can be smooth or notched or curved.
  • the heating step may be carried out by means of a straightening iron, a frizz iron ser, a cranberry iron or a steam iron.
  • the heating step is performed by means of a smoothing iron.
  • the iron can be applied by successive separate keys of a few seconds, or by progressive displacement or sliding along wicks of keratinous fibers, especially hair.
  • the application of the iron, in particular the iron to be smoothed, in the process according to the invention is done in continuous movement from the root to the tip of the hair, in one or more passages, in particular in two to twenty minutes. passages.
  • the duration of each passage of the iron can go from 2 seconds to 1 minute.
  • the heating step is carried out for a duration ranging from 2 seconds to 30 minutes, preferably from 2 seconds to 20 minutes, better from 2 seconds to 10 minutes, better from 3 seconds to 5 minutes, and even better from 5 seconds to 2 minutes.
  • the method according to the invention may also comprise an additional step of drying the keratin fibers after the application of the composition comprising the pyridine dicarboxylic acid compound (s); when the process comprises a step of heating the keratinous fibers carried out at a temperature of at least 100 ° C., the drying step is preferably carried out before this heating step.
  • the drying step can be performed by means of a hairdryer, a helmet or by free drying.
  • the drying step is advantageously carried out at a temperature ranging from 20 to 70 ° C.
  • the keratin fibers may be optionally rinsed with water or washed with a shampoo.
  • the keratinous fibers are then optionally dried by means of a hairdryer or a helmet or in the open air.
  • the treatment method according to the invention can be carried out on sensitized thick hair, such as thick, bleached, artificially colored, relaxed or permed hair.
  • the method according to the invention can be implemented on dry or wet hair.
  • the cosmetic composition used according to the invention is advantageously applied to the thick hair in an amount ranging from 0.1 to 10 grams, preferably from 0.2 to 5 grams of composition per gram of thick hair.
  • the composition After application to the thick hair of the cosmetic composition comprising the pyridine dicarboxylic acid compound (s), and before carrying out the step of heating the hair, it is possible to leave the composition applied for a duration ranging from 1 to 60 minutes preferably from 2 to 50 minutes, preferably from 5 to 45 minutes.
  • the exposure time can be carried out at a temperature ranging from 15 to 45 ° C, preferably at room temperature (25 ° C).
  • the treatment method according to the invention can be implemented during and / or after an additional cosmetic treatment process of thick hair, in particular durable shaping (permanent, straightening) or coloring.
  • the treatment method is implemented in post-treatment of a fading process, artificial coloring, straightening and / or a permanent process for repairing the hair.
  • the method according to the invention can be implemented during a cosmetic treatment process in order to repair the hair.
  • the treatment method according to the invention is implemented on thick hair, especially sensitized hair such as bleached, colored, stripped or permed.
  • the treatment method according to the invention can also be implemented on Asian hair, especially sensitized hair such as bleached, colored, relaxed or permed.
  • the treatment method can be used during and / or after a cosmetic treatment process for thick hair, in particular:

Abstract

The invention relates to a method for the cosmetic treatment of thick hair, especially Asian hair, comprising the application of a cosmetic composition comprising a pyridine dicarboxylic acid compound.

Description

L'invention concerne un procédé de traitement cosmétique des cheveux épais, en particulier des cheveux asiatiques, mettant en œuvre un ou plusieurs composés d'acide pyridine dicarboxylique. Les cheveux peuvent être abîmés ou fragilisés par l'action de traitements chimiques tels que les teintures, les décolorations, les permanentes, les défrisages, les lavages répétés. Les cheveux deviennent sensibilisés, se retrouvent ainsi endommagés par ces différents traitements et peuvent à la longue devenirs secs, rêches, cassants, ternes, fourchus ou mous.  The invention relates to a method for the cosmetic treatment of thick hair, in particular Asian hair, using one or more pyridine dicarboxylic acid compounds. The hair can be damaged or weakened by the action of chemical treatments such as dyes, discolorations, perms, straightening, repeated washing. The hair becomes sensitized, is thus damaged by these different treatments and can eventually become dry, rough, brittle, dull, forked or soft.
Pour remédier à ces inconvénients, il est usuel d'avoir recours à des soins capillaires qui mettent en œuvre des compositions destinées à conditionner les cheveux de manière convenable en leur apportant des propriétés cosmétiques satisfaisantes. Ces compositions de soins capillaires peuvent être, par exemple, des shampooings conditionneurs, des après shampooings, des masques, des sérums. Toutefois, l'effet conditionneur obtenu s'estompe généralement au cours des shampoings successifs et présente une rémanence au shampooing peu satisfaisante. Ceci est tout particulièrement vrai pour les cheveux épais. To overcome these disadvantages, it is customary to use hair care that implement compositions for conditioning the hair in a suitable manner by providing satisfactory cosmetic properties. These hair care compositions may be, for example, conditioning shampoos, after shampoos, masks, serums. However, the conditioning effect obtained generally fades during successive shampoos and has an unsatisfactory shampoo remanence. This is especially true for thick hair.
Il existe donc un besoin de disposer d'un procédé de traitement cosmétique des cheveux, notamment des cheveux épais, en particulier des cheveux épais sensibilisés, capable de les conditionner durablement, en particulier pour leur conférer une bonne discipline et une bonne brillance, l'effet conditionneur étant avantageusement rémanent après un ou plusieurs shampoings effectués sur les cheveux traités. There is therefore a need for a method for the cosmetic treatment of hair, in particular thick hair, in particular thick, sensitized hair, capable of conditioning them durably, in particular to give them good discipline and good gloss. conditioning effect being advantageously remanent after one or more shampoos performed on the treated hair.
La demanderesse a découvert que l'application d'un composé d'acide pyridine dicarboxylique tel que défini ci-après, sur des cheveux épais, permet d'obtenir de bonnes propriétés cosmétiques de discipline et de qualité des cheveux et de brillance, avec un effet durable dans le temps, notamment après un ou plusieurs shampooings. The applicant has discovered that the application of a pyridine dicarboxylic acid compound as defined below, on thick hair, makes it possible to obtain good cosmetic properties of discipline and quality of hair and shine, with a lasting effect over time, especially after one or more shampoos.
Ainsi, la présente invention a pour objet un procédé de traitement cosmétique des cheveux épais comprenant l'application sur lesdits cheveux d'une composition cosmétique comprenant un ou plusieurs composés d'acide pyridine dicarboxylique tels que définis ci-après. Thus, the subject of the present invention is a method for the cosmetic treatment of thick hair comprising the application to said hair of a cosmetic composition comprising one or more pyridine dicarboxylic acid compounds as defined below.
En particulier, les cheveux traités avec le procédé selon l'invention restent disciplinés car on ne constate pas la présence de frisottis. Ainsi les cheveux sont alignés, lisses ; en outre, ils présentent une meilleur qualité de surface, sont plus résistants, se cassent moins facilement, semblent moins fragiles. Par ailleurs, les cheveux traités sont également plus brillants. In particular, the hair treated with the method according to the invention remains disciplined because it does not show the presence of frizz. Thus the hair is aligned, smooth; in addition, they have a better surface quality, are more resistant, break less easily, seem less fragile. In addition, the treated hair is also brighter.
Le procédé selon l'invention présente l'avantage de conférer une bonne rémanence au shampoing de ces propriétés de qualité de la fibre, renforcement, résistance. Ainsi, les cheveux traités sont renforcés, protégés, voire réparés, de ma- nière durable. The process according to the invention has the advantage of conferring good shampoo remanence on these properties of fiber quality, reinforcement and resistance. Thus, the treated hair is reinforced, protected or even repaired, sustainable environment.
Ainsi, le procédé selon l'invention permet notamment d'améliorer la qualité des cheveux, de les protéger, de les renforcer, de les rendre plus résistants, moins cassants, voire de les réparer lorsqu'ils sont abîmés.  Thus, the process according to the invention makes it possible in particular to improve the quality of the hair, to protect it, to strengthen it, to make it more resistant, less brittle, and even to repair it when it is damaged.
On connaît de la demande de brevet FR2838336 l'utilisation de composés d'acide pyridine dicarboxylique pour le traitement antichute des cheveux. Toutefois, l'utilisation de cette famille de composés dans le but de conditionner, protéger, renforcer, les cheveux épais n'était ni décrite, ni suggérée dans ce document. Patent Application FR2838336 discloses the use of pyridine dicarboxylic acid compounds for the anti-hair loss treatment. However, the use of this family of compounds for the purpose of conditioning, protecting, strengthening, thick hair was neither described nor suggested in this document.
Par cheveux épais, on entend des cheveux ayant un diamètre individuel d'au moins 90 microns, de préférence d'au moins 100 microns; en particulier compris entre 90 et 120 microns, voire entre 100 et 120 microns. By thick hair is meant hair having an individual diameter of at least 90 microns, preferably at least 100 microns; in particular between 90 and 120 microns, or even between 100 and 120 microns.
De préférence, les cheveux épais sont tout particulièrement des cheveux asiatiques.  Preferably, the thick hair is especially Asian hair.
Ainsi, dans un mode de réalisation particulier, l'invention consiste en un procédé de traitement cosmétique des cheveux asiatiques, comprenant l'application sur lesdits cheveux d'une composition cosmétique comprenant un ou plusieurs composés d'acide pyridine dicarboxylique tels que définis ci-après.  Thus, in a particular embodiment, the invention consists of a method of cosmetic treatment of Asian hair, comprising the application to said hair of a cosmetic composition comprising one or more pyridine dicarboxylic acid compounds as defined above. after.
Ledit composé d'acide pyridine-2,4-dicarboxylique utilisé selon l'invention est choisi parmi les composés de formule (I) suivante : Said pyridine-2,4-dicarboxylic acid compound used according to the invention is chosen from the compounds of formula (I) below:
Figure imgf000003_0001
dans laquelle R1 et R2 représentent indépendamment l'un de l'autre OH, OR', - NH2, -NHR', -NR'R", avec R' et R" représentant, indépendamment l'un de l'autre, un alkyle en C1 -C18, linéaire ou ramifié, saturé ou insaturé, éventuellement substitué par au moins un groupe choisi parmi OH, alcoxy en C1 -C6, acyloxy en C1 -C6, amino, alkyl(C1 -C6)oxycarbonyl, ou alkyl(C1 -C6)amino, ou aryle en C6-C10, ainsi que leurs sels.
Figure imgf000003_0001
wherein R1 and R2 are independently of each other OH, OR ', -NH 2 , -NHR', -NR'R ", with R 'and R" representing, independently of one another, a linear or branched, saturated or unsaturated C 1 -C 18 alkyl, optionally substituted by at least one group chosen from OH, C 1 -C 6 alkoxy, C 1 -C 6 acyloxy, amino, (C 1 -C 6) alkyloxycarbonyl, or alkyl (C1-C6) amino, or C6-C10 aryl, as well as their salts.
Plus particulièrement, R1 et R2 représentent, indépendamment l'un de l'autre, OH, OR', avec R' représentant un alkyle en C1 -C12, linéaire ou ramifié, saturé, éven- tuellement substitué par au moins un groupe OH, alcoxy en (C1 -C4), acyloxy en (C1 -C4), alkyl(C1 -C4)oxycarbonyl, ou alkyl(C1 -C4)amino, ou phényle. More particularly, R 1 and R 2 represent, independently of one another, OH, OR ', with R' representing a linear or branched, saturated C 1 -C 12 alkyl, optionally optionally substituted with at least one OH, (C 1 -C 4) alkoxy, (C 1 -C 4) acyloxy, (C 1 -C 4) alkyloxycarbonyl, or (C 1 -C 4) alkylamino, or phenyl.
De façon particulièrement préférée, R1 et R2 représentent indépendamment l'un de l'autre OH, OR', et R' représente un alkyle en C1 -C6, linéaire ou ramifié, saturé, éventuellement substitué par au moins un groupe OH, alcoxy en (C1 -C4), acyloxy en (C1 -C4), alkyl(C1 -C4)oxycarbonyl, ou alkyl(C1 -C4)amino, ou phényle, ou un sel de l'un de ces composés. Les dérivés d'acide pyridine-2,4-dicarboxylique suivants sont préférés dans le cadre de la présente invention : In a particularly preferred manner, R1 and R2 represent, independently of each other, OH, OR ', and R' represents a linear or branched, saturated C1-C6 alkyl, optionally substituted by at least one OH, alkoxy group or (C1-C4), (C1-C4) acyloxy, (C1-C4) alkyloxycarbonyl, or (C1-C4) alkylamino, or phenyl, or a salt of one of these compounds. The following pyridine-2,4-dicarboxylic acid derivatives are preferred in the context of the present invention:
- l'acide pyridine-2,4-dicarboxylique (composé 2) ou un de ses sels, notamment sel disodique (composé 1 )  pyridine-2,4-dicarboxylic acid (compound 2) or a salt thereof, in particular disodium salt (compound 1)
- l'ester diméthylique de l'aide pyridine-2,4-dicarboxylique (composé 3)  dimethyl ester of pyridine-2,4-dicarboxylic acid (compound 3)
- l'ester diéthylique de l'acide pyridine-2,4-dicarboxylique (composé 4)  the diethyl ester of pyridine-2,4-dicarboxylic acid (compound 4)
- l'ester 2-éthylique d'acide pyridine 2,4-dicarboxylique (composé 8)  pyridine 2,4-dicarboxylic acid 2-ethyl ester (compound 8)
- l'ester 4-éthylique d'acide pyridine 2,4-dicarboxylique (composé 10)  pyridine 2,4-dicarboxylic acid 4-ethyl ester (compound 10)
- l'ester diisopropylique d'acide pyridine-2,4-dicarboxylique (composé 6)  pyridine-2,4-dicarboxylic acid diisopropyl ester (compound 6)
- le di-n-propylamide d'acide pyridine-2,4-dicarboxylique  pyridine-2,4-dicarboxylic acid di-n-propylamide
- l'ester 2-isopropylique d'acide 2-4-pyridine dicarboxylique (composé7)  2-4-pyridine dicarboxylic acid 2-isopropyl ester (compound 7)
- l'ester de glycolate de méthyle d'acide pyridine-2,4-dicarboxylique  pyridine-2,4-dicarboxylic acid methyl glycol ester
Figure imgf000004_0001
Composé 3
Figure imgf000004_0001
Compound 3
Composé 4Compound 4
Composé 5 Compound 5
Composé 6  Compound 6 
Figure imgf000006_0001
Figure imgf000006_0001
Figure imgf000007_0001
Figure imgf000007_0001
Par sels des composés de formule (I), on entend selon l'invention les sels organiques ou minéraux d'un composé de formule (I), ces sels étant physiologique- ment acceptables. Comme sels minéraux, on peut citer les sels de sodium ou de potassium ainsi que les sels de zinc (Zn2+), de calcium (Ca2+), de cuivre (Cu2+), de fer (Fe2+), de strontium (Sr2+), de magnésium (Mg2+), de manganèse (Mn2+); les hydroxydes, les carbonates et les halogénures, notamment les chlorures. Comme sels organiques, on peut citer les sels de triéthanolamine, mono-éthanolamine, diéthanolamine, hexadécylamine, N,N,N',N'-tétrakis-(hydroxy-propyl-2)éthylène diamine et tris-hydroxyméthyl aminométhane. Salts of the compounds of formula (I) are, according to the invention, the organic or inorganic salts of a compound of formula (I), these salts being physiologically acceptable. As mineral salts, mention may be made of sodium or potassium salts as well as the salts of zinc (Zn 2+ ), calcium (Ca 2+ ), copper (Cu 2+ ), iron (Fe 2+ ), strontium (Sr 2+ ), magnesium (Mg 2+ ), manganese (Mn 2+ ); hydroxides, carbonates and halides, especially chlorides. As organic salts, mention may be made of the triethanolamine, monoethanolamine, diethanolamine, hexadecylamine, N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine and tris-hydroxymethylaminomethane salts.
Les composés de formule (I) sont connus en tant que tels; ils sont notamment décrits, ainsi que leur fabrication, dans le brevet EP1352629. De préférence, le ou les composés de formule (I) sont présents dans la composition cosmétique utilisée selon l'invention en une teneur allant de 0,1 à 10% en poids, par rapport au poids total de la composition, de préférence allant de 0,5 à 8% en poids, préférentiellement allant de 0,5 à 6% en poids. La composition cosmétique utilisée selon l'invention contient notamment un milieu cosmétiquement acceptable, c'est-à-dire compatible avec les matières kérati- niques humaines telles que la peau (corps, visage, contour des yeux, cuir chevelu), les cheveux, les cils, les sourcils, les poils, les ongles, les lèvres. Le milieu cosmétiquement acceptable de la composition mise en œuvre dans le procédé selon l'invention est avantageusement un milieu aqueux. Il peut par exemple être constitué par de l'eau ou par un mélange d'eau et d'au moins un solvant organique cosmétiquement acceptable. A titre de solvant organique, on peut par exemple citer les alcools en C2-C4 tels que l'éthanol et l'isopropanol ; les po- lyols, notamment ceux ayant de 2 à 6 atomes de carbones comme la glycérine, le propylène glycol, le butylène glycol, le pentylène glycol, l'hexylène glycol, le dipro- pylène glycol, le diéthylène glycol; les éthers de polyols comme le 2- butoxyéthanol, le monométhyléther de propylèneglycol, le monoéthyléther et le monométhyléther du diéthylèneglycol; et leurs mélanges. The compounds of formula (I) are known as such; they are particularly described, as well as their manufacture, in patent EP1352629. Preferably, the compound (s) of formula (I) are present in the cosmetic composition used according to the invention in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition, preferably ranging from 0.5 to 8% by weight, preferably ranging from 0.5 to 6% by weight. The cosmetic composition used according to the invention contains in particular a cosmetically acceptable medium, that is to say compatible with human keratin materials such as the skin (body, face, eye contour, scalp), the hair, eyelashes, eyebrows, hair, nails, lips. The cosmetically acceptable medium of the composition used in the process according to the invention is advantageously an aqueous medium. It may for example consist of water or a mixture of water and at least one cosmetically acceptable organic solvent. As organic solvent, there may be mentioned for example C 2 -C 4 alcohols such as ethanol and isopropanol; polyols, especially those having from 2 to 6 carbon atoms such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether; and their mixtures.
De préférence, la composition cosmétique comprend de 50 à 99,5% en poids d'eau par rapport au poids de la composition. Preferably, the cosmetic composition comprises from 50 to 99.5% by weight of water relative to the weight of the composition.
La composition cosmétique utilisée selon l'invention peut en outre comprendre un ou plusieurs additifs cosmétiques usuels, notamment choisis parmi les tensioactifs non ioniques, anioniques, cationiques et amphotères, les vitamines et provitamines dont le panthénol, les filtres solaires, les charges, les matières colorantes, les agents nacrants, les agents opacifiants, les agents séquestrants, les polymères notamment filmogènes, les agents conditionneurs, les agents plastifiants, les agents épaississants, les huiles, les agents antioxydants, les agents anti- mousse, les agents hydratants, les agents émollients, les agents de pénétration, les parfums et les agents conservateurs. The cosmetic composition used according to the invention may also comprise one or more usual cosmetic additives, chosen in particular from nonionic, anionic, cationic and amphoteric surfactants, vitamins and provitamines including panthenol, sunscreens, fillers, substances and the like. colorants, pearlescent agents, opacifying agents, sequestering agents, polymers especially film-forming agents, conditioning agents, plasticizers, thickeners, oils, antioxidants, anti-foaming agents, moisturizing agents, agents emollients, penetrating agents, perfumes and preservatives.
La composition cosmétique utilisée selon l'invention peut se présenter sous toutes les formes galéniques classiquement utilisées pour une application capillaire et notamment sous forme de solution aqueuse, solution hydroalcoolique, d'émulsion huile-dans-eau (H/E) ou eau-dans-huile (E/H) ou multiple (triple : E/H/E ou H/E/H), de gel aqueux, de gel hydroalcoolique. The cosmetic composition used according to the invention may be in any of the galenical forms conventionally used for capillary application and especially in the form of an aqueous solution, aqueous-alcoholic solution, oil-in-water (O / W) emulsion or water-in solution. oil (W / O) or multiple (triple: W / O / W or O / W / H), aqueous gel, hydroalcoholic gel.
De préférence, la composition cosmétique est sous forme de solution ou de gel aqueux ou hydroalcoolique.  Preferably, the cosmetic composition is in the form of an aqueous or aqueous-alcoholic solution or gel.
Le procédé selon l'invention peut comprendre une étape de chauffage des cheveux épais à une température d'au moins 100°C, de préférence allant de 100 à 250°C. De préférence, l'étape de chauffage des fibres kératiniques est réalisée à une température allant de 150 à 220°C, de préférence allant de 160 à 220°C, pré- férentiellement allant de 160 à 200°C, notamment allant de 170 à 190°C. The method according to the invention may comprise a step of heating the thick hair at a temperature of at least 100 ° C, preferably ranging from 100 to 250 ° C. Preferably, the step of heating the keratinous fibers is carried out at a temperature ranging from 150 to 220 ° C., preferably ranging from 160 to 220 ° C., preferably ranging from 160 to 200 ° C., in particular ranging from 170 to 190 ° C.
On effectue l'étape de chauffage, lorsqu'elle est présente, après l'étape d'application de la composition cosmétique comprenant le ou les composés (I) sur les fibres kératiniques. L'étape de chauffage peut aider à conférer une bonne mise en forme des cheveux. Elle peut également permettre d'optimiser les effets du procédé, notamment d'optimiser la rémanence des propriétés cosmétiques après un ou plusieurs shampooings. Cette étape de chauffage est avantageusement réalisée au moyen d'un fer.  The heating step is carried out, when it is present, after the step of applying the cosmetic composition comprising the compound (s) (I) to the keratinous fibers. The heating step can help to give a good shaping of the hair. It can also make it possible to optimize the effects of the process, in particular to optimize the remanence of the cosmetic properties after one or more shampoos. This heating step is advantageously carried out by means of an iron.
Par « fer », on entend, au sens de la présente invention, un dispositif de chauffage des fibres kératiniques mettant en contact lesdites fibres et le dispositif de chauffage.  By "iron" is meant, in the sense of the present invention, a device for heating the keratinous fibers contacting said fibers and the heating device.
L'extrémité du fer venant en contact avec les fibres kératiniques présente généra- lement deux surfaces planes. Ces deux surfaces peuvent être métalliques ou en céramique. En particulier, ces deux surfaces peuvent être lisses ou crantées ou courbes.  The end of the iron coming into contact with the keratin fibers generally has two flat surfaces. These two surfaces can be metallic or ceramic. In particular, these two surfaces can be smooth or notched or curved.
L'étape de chauffage peut être effectuée au moyen d'un fer à lisser, d'un fer à fri- ser, d'un fer à cranter ou d'un fer vapeur. De préférence, l'étape de chauffage est effectuée au moyen d'un fer à lisser. The heating step may be carried out by means of a straightening iron, a frizz iron ser, a cranberry iron or a steam iron. Preferably, the heating step is performed by means of a smoothing iron.
A titre d'exemple de fers utilisables dans le procédé de lissage selon l'invention, on peut citer tous types de fers plats, et en particulier ceux décrits dans les bre- vets US5957140 et US5046516.  By way of example of irons that can be used in the smoothing process according to the invention, mention may be made of all types of flat bars, and in particular those described in patents US5957140 and US5046516.
L'application du fer peut être effectuée par touches séparées successives de quelques secondes, ou par déplacement ou glissement progressif le long des mèches de fibres kératiniques, notamment de cheveux.  The iron can be applied by successive separate keys of a few seconds, or by progressive displacement or sliding along wicks of keratinous fibers, especially hair.
De préférence, l'application du fer, notamment du fer à lisser, dans le procédé se- Ion l'invention se fait en mouvement continu de la racine à la pointe du cheveu, en un ou plusieurs passages, en particulier en deux à vingt passages. La durée de chaque passage du fer peut aller de 2 secondes à 1 minute.  Preferably, the application of the iron, in particular the iron to be smoothed, in the process according to the invention is done in continuous movement from the root to the tip of the hair, in one or more passages, in particular in two to twenty minutes. passages. The duration of each passage of the iron can go from 2 seconds to 1 minute.
De préférence, l'étape de chauffage est effectuée pendant une durée pouvant aller de 2 secondes à 30 minutes, préférentiellement de 2 secondes à 20 minutes, mieux de 2 secondes à 10 minutes, mieux de 3 secondes à 5 minutes, et encore mieux de 5 secondes à 2 minutes. Preferably, the heating step is carried out for a duration ranging from 2 seconds to 30 minutes, preferably from 2 seconds to 20 minutes, better from 2 seconds to 10 minutes, better from 3 seconds to 5 minutes, and even better from 5 seconds to 2 minutes.
Le procédé selon l'invention peut également comprendre une étape supplémen- taire de séchage des fibres kératiniques après l'application de la composition comprenant le ou les composés d'acide pyridine dicarboxylique ; lorsque le procédé comprend une étape de chauffage des fibres kératiniques effectuée à une température d'au moins 100°C, l'étape de séchage est de préférence effectuée avant cette étape de chauffage. L'étape de séchage peut être réalisée au moyen d'un sèche-cheveux, d'un casque ou encore par séchage libre. L'étape de séchage est avantageusement effectuée à une température allant de 20 à 70°C. The method according to the invention may also comprise an additional step of drying the keratin fibers after the application of the composition comprising the pyridine dicarboxylic acid compound (s); when the process comprises a step of heating the keratinous fibers carried out at a temperature of at least 100 ° C., the drying step is preferably carried out before this heating step. The drying step can be performed by means of a hairdryer, a helmet or by free drying. The drying step is advantageously carried out at a temperature ranging from 20 to 70 ° C.
Après l'étape de chauffage, les fibres kératiniques peuvent être éventuellement rincées à l'eau ou lavées avec un shampooing. Les fibres kératiniques sont en- suite éventuellement séchées au moyen d'un sèche-cheveux ou d'un casque ou à l'air libre. After the heating step, the keratin fibers may be optionally rinsed with water or washed with a shampoo. The keratinous fibers are then optionally dried by means of a hairdryer or a helmet or in the open air.
Le procédé de traitement selon l'invention peut être mis en œuvre sur des cheveux épais sensibilisés, tels que des cheveux épais décolorés, colorés artificielle- ment, défrisés ou permanentés. The treatment method according to the invention can be carried out on sensitized thick hair, such as thick, bleached, artificially colored, relaxed or permed hair.
Le procédé selon l'invention peut être mis en œuvre sur des cheveux secs ou humides.  The method according to the invention can be implemented on dry or wet hair.
La composition cosmétique utilisée selon l'invention est avantageusement appli- quée sur les cheveux épais en une quantité allant de 0,1 à 10 grammes, de préférence de 0,2 à 5 grammes de composition par gramme de cheveux épais. The cosmetic composition used according to the invention is advantageously applied to the thick hair in an amount ranging from 0.1 to 10 grams, preferably from 0.2 to 5 grams of composition per gram of thick hair.
Après application de la composition cosmétique sur les cheveux épais, ces derniers peuvent être essorés pour retirer l'excès de composition ou bien lavés à l'eau ou avec un shampooing. After application of the cosmetic composition to the thick hair, these can be dewatered to remove the excess of composition or washed at water or with a shampoo.
Après application sur les cheveux épais de la composition cosmétique comprenant le ou les composés d'acide pyridine dicarboxylique, et avant d'effectuer l'étape de chauffage des cheveux, on peut laisser poser la composition appliquée pendant une durée allant de 1 à 60 minutes, de préférence allant de 2 à 50 minutes, préfé- rentiellement allant de 5 à 45 minutes. Le temps de pose peut être effectué à une température allant de 15 à 45°C, de préférence à la température ambiante (25°C). Le procédé de traitement selon l'invention peut être mis en œuvre pendant et/ou après un procédé de traitement cosmétique additionnel des cheveux épais, notamment de mise en forme durable (permanente, défrisage) ou de coloration. After application to the thick hair of the cosmetic composition comprising the pyridine dicarboxylic acid compound (s), and before carrying out the step of heating the hair, it is possible to leave the composition applied for a duration ranging from 1 to 60 minutes preferably from 2 to 50 minutes, preferably from 5 to 45 minutes. The exposure time can be carried out at a temperature ranging from 15 to 45 ° C, preferably at room temperature (25 ° C). The treatment method according to the invention can be implemented during and / or after an additional cosmetic treatment process of thick hair, in particular durable shaping (permanent, straightening) or coloring.
En particulier, le procédé de traitement est mis en œuvre en post-traitement d'un procédé de décoloration, de coloration artificielle, de défrisage et/ou d'un procédé de permanente afin de réparer les cheveux. In particular, the treatment method is implemented in post-treatment of a fading process, artificial coloring, straightening and / or a permanent process for repairing the hair.
Le procédé selon l'invention peut être mis en œuvre pendant un procédé de traitement cosmétique afin de réparer les cheveux.  The method according to the invention can be implemented during a cosmetic treatment process in order to repair the hair.
Le procédé de traitement selon l'invention est mis en œuvre sur des cheveux épais, notamment sensibilisés tels que des cheveux décolorés, colorés, défrisés ou permanentés.  The treatment method according to the invention is implemented on thick hair, especially sensitized hair such as bleached, colored, stripped or permed.
Le procédé de traitement selon l'invention peut également être mis en œuvre sur des cheveux asiatiques, notamment sensibilisés tels que des cheveux décolorés, colorés, défrisés ou permanentés. En variante, le procédé de traitement peut être mis en œuvre pendant et/ou après un procédé de traitement cosmétique des cheveux épais, en particulier :  The treatment method according to the invention can also be implemented on Asian hair, especially sensitized hair such as bleached, colored, relaxed or permed. As a variant, the treatment method can be used during and / or after a cosmetic treatment process for thick hair, in particular:
- pendant et/ou après un procédé de coloration ou un procédé de permanente ou un procédé de défrisage des cheveux, et  during and / or after a dyeing process or a permanent method or a process for straightening the hair, and
- après un procédé de décoloration des cheveux.  - after a process of hair bleaching.

Claims

REVENDICATIONS
1 . Procédé de traitement cosmétique des cheveux épais comprenant une étape d'application sur lesdits cheveux d'une composition cosmétique comprenant un ou plusieurs composés d'acide pyridine dicarboxylique de formule (I) suivante: 1. A method of cosmetic treatment of thick hair comprising a step of applying to said hair a cosmetic composition comprising one or more pyridine dicarboxylic acid compounds of formula (I) below:
Figure imgf000011_0001
dans laquelle R1 et R2 représentent indépendamment l'un de l'autre OH, OR', - NH2, -NHR', -NR'R", avec R' et R" représentant, indépendamment l'un de l'autre, un alkyle en C1 -C18, linéaire ou ramifié, saturé ou insaturé, éventuellement substitué par au moins un groupe choisi parmi OH, alcoxy en C1 -C6, acyloxy en C1 -C6, amino, alkyl(C1 -C6)oxycarbonyl, ou alkyl(C1 -C6)amino, ou aryle en C6-C10, ainsi que leurs sels.
Figure imgf000011_0001
wherein R1 and R2 are independently of each other OH, OR ', -NH 2 , -NHR', -NR'R ", with R 'and R" representing, independently of one another, a linear or branched, saturated or unsaturated C 1 -C 18 alkyl, optionally substituted by at least one group chosen from OH, C 1 -C 6 alkoxy, C 1 -C 6 acyloxy, amino, (C 1 -C 6) alkyloxycarbonyl, or alkyl (C1-C6) amino, or C6-C10 aryl, as well as their salts.
2. Procédé selon la revendication 1 , dans lequel R1 et R2 représentent indépendamment l'un de l'autre OH, OR' avec R' représentant un alkyle en C1 -C12, linéaire ou ramifié, saturé, éventuellement substitué par au moins un groupe OH, alcoxy en (C1 -C4), acyloxy en (C1 -C4), alkyl(C1 -C4)oxycarbonyl, ou alkyl(C1 - C4)amino, ou phényle. 2. Process according to claim 1, in which R1 and R2 represent, independently of one another, OH, OR 'with R' representing a linear or branched, saturated C1-C12 alkyl, optionally substituted by at least one group OH, (C 1 -C 4) alkoxy, (C 1 -C 4) acyloxy, (C 1 -C 4) alkyloxycarbonyl, or (C 1 -C 4) alkylamino, or phenyl.
3. Procédé selon l'une des revendications précédentes, dans lequel R1 et R2 représentent indépendamment l'un de l'autre OH, OR', et R' représente un alkyle en C1 -C6, linéaire ou ramifié, saturé, éventuellement substitué par au moins un groupe OH, alcoxy en (C1 -C4), acyloxy en (C1 -C4), alkyl(C1 -C4)oxycarbonyl, ou alkyl(C1 -C4)amino, ou phényle, ou un sel de l'un de ces composés. 3. Method according to one of the preceding claims, wherein R1 and R2 independently represent one of the other OH, OR ', and R' represents a linear or branched, saturated, C1-C6 alkyl, optionally substituted by at least one OH, (C 1 -C 4) alkoxy, (C 1 -C 4) acyloxy, (C 1 -C 4) alkyloxycarbonyl, or (C 1 -C 4) alkylamino, or phenyl, or a salt of one of these compounds.
4. Procédé selon l'une des revendications précédentes, dans lequel le ou les composés de formule (I) sont choisis parmi :
Figure imgf000012_0001
Figure imgf000013_0001
4. Method according to one of the preceding claims, wherein the compound or compounds of formula (I) are chosen from:
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000014_0001
5. Procédé selon l'une quelconque des revendications précédentes, dans lequel le ou les composés de formule (I) sont présents dans la composition en une teneur allant de 0,1 à 10% en poids, par rapport au poids total de la composition, de pré- férence allant de 0,5 à 8% en poids, préférentiellement allant de 0,5 à 6% en poids. 5. Process according to any one of the preceding claims, in which the compound or compounds of formula (I) are present in the composition in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition. preferably 0.5 to 8% by weight, preferably 0.5 to 6% by weight.
6. Procédé selon l'une quelconque des revendications précédentes, comprenant en outre une étape de chauffage des cheveux épais à une température d'au moins 100°C, de préférence allant de 100 à 250°C, mieux à une température allant de 150 à 220°C, de préférence allant de 160 à 220°C, préférentiellement allant de 160 à 200°C, notamment allant de 170 à 190°C. The method of any of the preceding claims, further comprising a step of heating the thick hair to a temperature of at least 100 ° C, preferably from 100 to 250 ° C, more preferably at a temperature of 150 at 220 ° C, preferably ranging from 160 to 220 ° C, preferably ranging from 160 to 200 ° C, in particular ranging from 170 to 190 ° C.
7. Procédé selon la revendication 6, dans lequel l'étape de chauffage est effectuée après l'étape d'application de la composition cosmétique comprenant le ou les composés de formule (I). 7. The method of claim 6, wherein the heating step is performed after the step of applying the cosmetic composition comprising the compound (s) of formula (I).
8. Procédé selon l'une des revendications 6 à 7, dans lequel l'étape de chauffage est effectuée au moyen d'un fer, notamment d'un fer à lisser, d'un fer à friser, d'un fer à cranter ou d'un fer vapeur. 8. Method according to one of claims 6 to 7, wherein the heating step is performed by means of an iron, including a hair straightener, a curling iron, a cranberry iron or a steam iron.
9. Procédé selon l'une des revendications 6 à 8, dans lequel l'étape de chauffage est effectuée par l'application d'un fer, notamment d'un fer à lisser, faite en mouvement continu de la racine à la pointe des cheveux, en un ou plusieurs passages. 9. Method according to one of claims 6 to 8, wherein the heating step is performed by the application of an iron, including a smoothing iron, made in continuous movement from the root to the tip of the hair, in one or more passages.
10. Procédé selon l'une des revendications précédentes, comprenant en outre une étape supplémentaire de séchage des cheveux épais effectuée après l'application de la composition cosmétique comprenant le ou les composés de formule (I). 10. Method according to one of the preceding claims, further comprising an additional step of drying the thick hair performed after the application of the cosmetic composition comprising the compound (s) of formula (I).
1 1 . Procédé selon l'une des revendications précédentes, dans lequel les cheveux épais ont un diamètre individuel d'au moins 90 microns, de préférence d'au moins 100 microns; en particulier compris entre 90 et 120 microns, voire entre 100 et 120 microns. 1 1. Method according to one of the preceding claims, wherein the thick hair has an individual diameter of at least 90 microns, preferably at least 100 microns; in particular between 90 and 120 microns, or even between 100 and 120 microns.
12. Procédé selon l'une des revendications précédentes, pour améliorer la qualité des cheveux, les protéger, les renforcer, les rendre plus résistants, moins cas- sants, et/ou les réparer notamment lorsqu'ils sont abîmés. 12. Method according to one of the preceding claims, to improve the quality of the hair, protect, strengthen, make them more resistant, less stressful, and / or repair them especially when they are damaged.
13. Procédé selon l'une des revendications précédentes, dans lequel les cheveux épais sont des cheveux asiatiques. 13. Method according to one of the preceding claims, wherein the thick hair is Asian hair.
14. Procédé selon l'une des revendications précédentes, dans lequel les cheveux épais sont des cheveux sensibilisés. 14. Method according to one of the preceding claims, wherein the thick hair is sensitized hair.
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CN107427435A (en) 2017-12-01
FR3033497B1 (en) 2018-05-18

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