Composition and process of treatment of keratin fibers using at least one particular pyridine derivative and at least one unsaturated fatty acid.

Abstract

The present invention relates to a composition comprising at least one particular pyridine derivative and at least one unsaturated fatty acid, as well as a process for treating keratin fibers using this composition.

Description

Title of the invention: Composition and process for treating keratin fibers using at least one particular pyridine derivative and at least one unsaturated fatty acid. Technical field of the invention

[0001] The present invention relates to a composition comprising at least one particular pyridine derivative and at least one unsaturated fatty acid, as well as a process for treating keratin fibers using this composition. Context of the invention

[0002] External atmospheric agents such as pollution and inclement weather, as well as mechanical or chemical treatments, or certain routines such as brushing, combing, dyeing, bleaching, perming, straightening, and repeated washing, can damage and weaken hair. Hair can become deformed and damaged and, over time, become dry, rough, brittle, dull, split, and / or limp.

[0003] To remedy this, it is common to use hair care products designed to condition the hair by providing satisfactory cosmetic properties, including smoothing, shine, softness, suppleness, lightness, and good detangling properties, resulting in easier combing and better manageability. The hair is thus easier to style and retains its shape. However, the conditioning effect obtained with these hair care products diminishes rapidly over time, does not always remain effective after shampooing, and does not prevent irreversible hair deformation due to fiber elongation, for example, during combing or detangling, nor does it repair or prevent hair breakage.

[0004] It is known that pyridine derivatives such as pyridoxine or one of its salts can be used in hair care compositions intended to condition hair in order to maintain or even improve hair quality. However, these derivatives can cause yellowing or browning of the hair care compositions containing them during storage. For this reason, the use of these derivatives in hair care compositions has been relatively limited to date, notably preventing their use at high concentrations.

[0005] Thus, there is a real need to develop a hair composition characterized by good color stability during storage which includes at least one specific pyridine derivative to prevent irreversible deformation of hair, particularly damaged and / or sensitized hair, due to the elongation of fibers, for example during combing or detangling, and to repair or prevent breakage of hair, especially damaged and / or sensitized hair.

[0006] The applicant has surprisingly discovered that all or part of these objectives can be achieved by the composition according to the present invention. Summary of the invention

[0007] According to a first aspect, the present invention relates to a composition comprising: (i) one or more pyridine derivatives selected from the following compounds of formula (I), their salts, their isomers, their solvates such as hydrates and mixtures thereof: Formula (I) in which: ■ R1 represents a (Ci-C4)alkyl group possibly substituted by one or more groups, identical or different, chosen from: hydroxyl (-OH) or amino (-NH2); ■ R2 represents: - a (Ci-C4)alkyl group optionally substituted by one or more identical or different groups selected from hydroxyl (-OH) or amino (-NH2) and / or optionally interrupted by one or more oxygen, sulfur, or nitrogen atoms, preferably oxygen; or - a group (-CHO); ■ R3 represents: - a (CrC4)alkyl group possibly substituted by one or more groups, identical or different, chosen from hydroxyl (-OH) or amino (-NH2) or phosphate (-OP(O)(OH)2) and / or possibly interrupted by one or more groups or heteroatoms, identical or different, chosen from O, S, N, -C(O)- and their combinations such as -SC(O)-, preferably chosen from O, or -SC(O)-; ii) one or more fatty acids selected from unsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures; in which: - the composition comprises a total content of compounds of formula (I), their isomers and mixtures thereof exceeding 0.9% by weight relative to the total weight of the composition; and - the molar ratio of total quantity of pyridine derivatives i) / total quantity of fatty acids ii) present in the composition is less than or equal to 1.15.

[0008] According to a second aspect, the present invention relates to a process for treating keratin fibers comprising i) the application to the keratin fibers of a composition as defined above.

[0009] According to a third aspect, the present invention relates to the use of a composition as defined above to prevent irreversible deformation of keratin fibers during combing and / or detangling.

[0010] According to a fourth aspect, the present invention relates to the use of a composition as defined above to repair and / or prevent the breakage of keratin fibers.

[0011] According to a fifth aspect, the present invention relates to the use of one or more fatty acids ii) as defined above to stabilize a composition comprising one or more pyridine derivatives i) as defined above. Detailed description of the invention

[0012] For the purposes of the present invention, and unless otherwise indicated:

[0013] ■ By "keratin fibers" we mean fibers of human or animal origin such as such as hair, body hair, eyelashes, eyebrows, wool, angora, cashmere, or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferably hair.

[0014] ■ By "abhed keratin fibers", we mean dry, rough keratin fibers, brittle, split and / or soft.

[0015] ■ By "sensitized keratin fibers", we mean bleached keratin fibers, artificially colored, straightened and / or permed.

[0016] ■ By "fatty acid", we mean a carboxylic acid, linear or branched, saturated or unsaturated, comprising 8 to 30 carbon atoms.

[0017] ■ By "unsaturated fatty acid" is meant a fatty acid comprising in its structure a or several ethylenic unsaturations, preferably one or two ethylenic unsaturations.

[0018] ■ by "alkyl group" is meant a saturated, linear or branched hydrocarbon radical, comprising from 1 to 30 carbon atoms, preferably from 1 to 26 carbon atoms, more preferably from 1 to 22 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl, n-decyl, n-undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl or eicosyl.

[0019] ■ By "(Cx-Cy) alkyl group" is meant an alkyl group comprising from x to y atoms of carbon.

[0020] ■ by "alkenyl group" is meant a hydrocarbon radical, linear or branched, comprising one or more ethylenic unsaturations, preferably one or two ethylenic unsaturations, conjugated or not, and from 2 to 40 carbon atoms, preferably from 2 to 26 carbon atoms, more preferably from 2 to 24 carbon atoms, for example ethylenyl, n-propylenyl, iso-propylenyl, butylenyl, n-pentylenyl, n-hexylenyl, n-decylenyl, n-dodecylenyl, tetradecylenyl, hexadecylenyl or eicosylenyl.

[0021] ■ by "(Cx-Cy)alkenyl group" we mean an alkenyl group comprising from x to y carbon atoms.

[0022] ■ by "salt" is meant an addition salt with an organic acid or base or Mineral. Addition salts with an acid are chosen from among those with organic or mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, citric acid, succinic acid, tartaric acid, lactic acid, tosylic acid, benzenesulfonic acid, phosphoric acid, or acetic acid. Addition salts with a base are chosen from among those with organic or mineral bases such as alkali metal hydroxides, alkaline earth metal hydroxides, ammonia, amines, or alkanolamines.

[0023] ■ by "isomer" we mean an optical, geometric or tautomeric isomer.

[0024] The expressions "at least one" and "one or more" are synonymous and may can be used interchangeably. Composition

[0025] According to a first aspect, the present invention relates to a composition as defined above.

[0026] The applicant has found, surprisingly, that the composition according to the present invention makes it possible to prevent irreversible deformation of hair, in particular of damaged and / or sensitized hair, due to the elongation of the fibers, for example during combing or detangling, and to repair or prevent breakage of hair, in particular of damaged and / or sensitized hair, while being stable and not undergoing any change in color over time, in particular during storage. Pyridine derivatives

[0027] The composition comprises i) one or more pyridine derivatives selected from compounds of formula (I) as defined above, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0028] Preferably, the pyridine derivative(s) i) are chosen from the following compounds 1 to 10, their salts, their isomers, their solvates such as hydrates and mixtures thereof: Compound 1 Ht HX ÜK J Pyridoxine HP 0 Compound 2 - r ■f^ -qX \ :ÙH : Pyridoxfce phosphate HO Ch Compound 3 X Pyridoxaf “'SF' Compound 4 HJ HP -v HX^ OH Pyndoxamine Compound 5 n Pyridoxam phosphate H ÇH.; Compound 6 HQ^ 4-Deoxypyridoxine Compound 7 HO » 1 1 Pyridoxine 5-thbacetate Compound 8 CH, , .GH, G '' 5-(Hydroxymethyl)-4-(methoxymethyl)-2-methylpyridine-3-ethanol Compound 9 HQ 2,5-D-methyl3-hydropyridinemethanol Compound 10 HP « 1 XI 3-Hydroxy-2,4,5-trihydromethylpyridine

[0029] More preferably, the pyridine derivative(s) i) are chosen from compound 1, its salts, its solvates such as hydrates and mixtures thereof.

[0030] Even more preferably, the pyridine derivative(s) i) are chosen from pyridoxine, pyridoxine hydrochloride and mixtures thereof.

[0031] The composition comprises a total content of compounds of formula (I), their isomers and their mixtures of more than 0.9% by weight, preferably from 1.1% to 10% by weight, more preferably from 1.5% to 9% by weight, even more preferably from 2% to 7% by weight relative to the total weight of the composition.

[0032] In embodiments according to the invention in which one or more pyridine derivatives (i) are in the form of a salt or a solvate of a compound of formula (I), the term "total content of compounds of formula (1)" means not the salt or solvate content but the content of compounds of formula (I). By way of example, when the composition according to the invention comprises only pyridoxine hydrochloride, the total content of compounds of formula (I) is, not the content of pyridoxine hydrochloride, but the content of pyridoxine. Fatty acids

[0033] The composition comprises ii) one or more fatty acids selected from unsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures;

[0034] According to a preferred embodiment, the fatty acid(s) ii) are selected from the following compounds of formula (II), their salts, their isomers, their solvates such as hydrates and mixtures thereof: UH (II) Formula (II) in which R represents a (C8-C40)alkenyl group optionally substituted by one or more hydroxyl groups (-OH), preferably a (C10-C30)alkenyl group optionally substituted by one or more hydroxyl groups (-OH), more preferably a (C12-C24)alkenyl group optionally substituted by one or more hydroxyl groups (-OH).

[0035] According to a particular embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (II) as defined above, their salts, their isomers, their solvates such as hydrates and their mixtures, formula (II) in which R represents an unsubstituted (C8-C40)alkenyl group, preferably an unsubstituted (Cio-C3o)alkenyl group, more preferably an unsubstituted (C[2-C24)alkenyl group.

[0036] According to another particular embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (II) as defined above, their salts, their isomers, their solvates such as hydrates and their mixtures, formula (II) in which R represents a (C8-C40)alkenyl group substituted by one or more hydroxyl groups (-OH), preferably a (Ci0-C30)alkenyl group substituted by one or more hydroxyl groups (-OH), more preferably a (Ci2-C24)alkenyl group substituted by one or more hydroxyl groups (-OH).

[0037] According to another particular embodiment, the fatty acid(s) ii) are selected from the compounds of formula (II) as defined above, their salts, their isomers, their solvates such as hydrates and mixtures thereof, formula (II) in which R represents a (C8-C40)alkenyl group substituted by a hydroxyl group (-OH), preferably a (C10-C30)alkenyl group substituted by a hydroxyl group (-OH), more preferably a (Ci2-C24)alkenyl group substituted by a hydroxyl group (-OH).

[0038] According to a particular embodiment, the fatty acid(s) ii) are selected from monounsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures, preferably from myristoleic acid, palmitoleic acid, vaccenic acid, paullinic acid, oleic acid, elaidic acid, gadoleic acid, gondolic acid, erucic acid, nervonic acid, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0039] According to a particular embodiment, the fatty acid(s) ii) are selected from polyunsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures, preferably from linoleic acid, linole-laidic acid, eicosadienoic acid, docosadienoic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, α-cosapentaenoic acid, docosahexaenoic acid, ruminic acid, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0040] According to a particular embodiment, the fatty acid(s) ii) are selected from hydroxylated monounsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures, preferably from 10-Hydroxy-cis-12-octadecenoic acid, 10-Hydroxy-trans-1-octadecenoic acid, 12-Hydroxy-cis-9-octadecenoic acid, 13-Hydroxy-cis-9-octadecenoic acid, ricinoleic acid, isoricinoleic acid, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0041] According to a particular embodiment, the fatty acid(s) ii) are chosen from hydroxylated polyunsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures, preferably from densipolic acid, auricolic acid, dimorphecolic acid, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0042] According to a more preferred embodiment, the fatty acid(s) ii) are selected from myristoleic acid, palmitoleic acid, vaccenic acid, paullinic acid, oleic acid, elaidic acid, gondoic acid, erucic acid, nervonic acid, linoleic acid, linolelaidic acid, eicosadienoic acid, docosadienoic acid, their salts, their isomers, their solvates such as hydrates and mixtures thereof.

[0043] According to an even more preferred embodiment, the fatty acid(s) ii) are chosen from oleic acid, its salts, its solvates such as hydrates and their mixtures, preferably oleic acid.

[0044] The fatty acid(s) ii) are present in the composition in a total content preferably ranging from 1.7% to 13% by weight, more preferably ranging from 1.9% to 9% in weight, even more preferably ranging from 2% to 6.5% by weight relative to the total weight of the composition.

[0045] The molar ratio of total quantity of pyridine derivatives i) / total quantity of fatty acids ii) present in the composition is less than or equal to 1.15, preferably from 0.3 to 1.15, more preferably from 0.5 to 1.10.

[0046] According to a preferred embodiment, the composition according to the present invention comprises: (i) one or more pyridine derivatives selected from pyridoxine, its salts, its solvates such as hydrates and mixtures thereof, preferably selected from pyridoxine, pyridoxine hydrochloride and mixtures thereof; ii) one or more fatty acids selected from oleic acid, its salts, its solvates such as hydrates, and mixtures thereof, preferably oleic acid, it being understood that: - the composition comprises a total pyridoxine content of more than 0.9% by weight relative to the total weight of the composition; and - the molar ratio of total quantity of pyridine derivatives i) / total quantity of fatty acids ii) present in the composition is less than or equal to 1.15. Other characteristics of the composition

[0047] The composition is a cosmetic composition, i.e. which comprises a cosmetically acceptable medium, that is to say a medium compatible with human keratin fibers.

[0048] The composition may include a solvent selected from water, ethanol, isopropanol, glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether and mixtures thereof.

[0049] The composition may include a solvent selected from water, C2-C4 alcohols, polyols, polyol ethers and mixtures thereof.

[0050] Preferably, the composition comprises a solvent selected from water, ethanol, isopropanol, propylene glycol and mixtures thereof.

[0051] More preferably, the composition comprises a solvent selected from water, ethanol, propylene glycol and mixtures thereof.

[0052] The composition may further comprise at least one cosmetic ingredient selected from non-ionic, anionic, cationic and amphoteric surfactants, vitamins and pro-vitamins other than vitamin B6 including panthenol, fillers, colorants, pearlescent agents, opacifying agents, sequestering agents, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickening agents smoothing agents, oils, antifoaming agents, moisturizing agents, emollients, penetration enhancers, perfumes, preservatives and mixtures thereof.

[0053] These common cosmetic ingredients may be present in the composition in typical quantities, easily determinable by those skilled in the art, and which may range, for each ingredient, from 0.01% to 20% by weight relative to the total weight of the composition. Those skilled in the art shall ensure that the ingredients included in the composition, as well as their quantities, are chosen in such a way that they do not impair the properties of the composition.

[0054] The composition may be in all the galenic forms conventionally used for hair application. By way of non-limitation, the composition may be in the form of a lotion, cream, mousse, gel, spray or hairspray.

[0055] The composition can be used in rinsed or non-rinsed application.

[0056] The composition may be in the form of a shampoo, a mask, of a conditioning formula or pre-shampoo treatment. The formula may also be in the form of a component to be added or mixed before application to a shampoo, mask, or conditioning formula.

[0057] The composition may be packaged in a pump bottle or an aerosol container to ensure application of the composition in spray form (lacquer) or as a foam. In these cases, the composition preferably includes at least one propellant.

[0058] The pH of the composition is preferably from 3 to 10, more preferably from 3 to 7, even more preferably from 3.5 to 5. Preferably, the pH of the composition is equal to 4. The pH can be adjusted using an organic or mineral acid or an organic or mineral base commonly used in cosmetics.

[0059] According to a preferred embodiment, the composition comprises a total content of coloring agents of less than 0.1% by weight, preferably less than 0.01% by weight, more preferably less than 0.001% by weight relative to the total weight of the composition, even more preferably, the composition is free of coloring agents.

[0060] By "coloring agent" is meant an oxidation dye, a direct dye or a pigment.

[0061] The term "oxidation dye" refers to an oxidation dye precursor selected from oxidation bases and couplers. Oxidation bases and couplers are compounds that are slightly colored or colorless and which, through a condensation reaction in the presence of an oxidizing agent, give a colored species.

[0062] The term "direct colorant" means a natural and / or synthetic colorant, including in the form of extract(s), other than oxidation colorants. These are colored compounds. which will diffuse superficially on the fiber. They can be ionic or non-ionic, i.e. anionic, cationic, neutral or non-ionic. Keratin fiber processing method

[0063] According to a second aspect, the present invention relates to a process for treating keratin fibers comprising i) the application to the keratin fibers of a composition as defined above.

[0064] The composition can be applied to dry or wet keratin fibers, preferably to wet keratin fibers.

[0065] Preferably, the keratin fibers are damaged and / or sensitized keratin fibers, in particular damaged and / or sensitized hair.

[0066] The bath ratio of the composition applied to the keratin fibers can range from 0.1 to 10. As an example, the bath ratio can be 0.4. By bath ratio, we mean the ratio between the total weight of the applied composition and the total weight of keratin fibers to be treated.

[0067] The process may include at least one additional step successive to step i) chosen from the following steps ii) to iv): ii) a step of applying the composition to the keratin fibers, preferably lasting at least 10 seconds, said application step possibly being carried out under an airtight film such as a papillote or plastic film; iii) a rinsing and / or washing step of the keratin fibers; iv) a step of drying the keratin fibers in ambient air or using a heating device.

[0068] Preferably, the process includes the additional steps ii) and iv) as described above and carried out in that order.

[0069] More preferably, the process comprises all the additional steps ii), iii) and iv) as described above and carried out in that order.

[0070] The composition setting step can last from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.

[0071] The washing step can, for example, be carried out using shampoo.

[0072] The temperature of the heating device can range from 45°C to 230°C, preferably from 45°C to 100°C, more preferably from 50°C to 80°C. A hair dryer, a heated helmet, an iron, or a heated brush can be used as a heating device, for example.

[0073] Step iv) of drying can also be a combination of air drying or drying with a heating device at a temperature ranging from 50°C to 80°C such as a hair dryer or a heated helmet, possibly followed by a step of passing through the iron, preferably a straightening iron.

[0074] Steps i) to iii) or steps i) to iv) may be repeated as many times as necessary Each cycle of steps i) to iii) or i) to iv) may be spaced from the next by a few minutes to a few days or weeks. Different hair treatments of the invention may be performed between different application cycles, before or after.

[0075] In the case where the process does not include step iii) of rinsing and / or washing the keratin fibers, the composition may, for example, include a solvent mixture such as a water / ethanol mixture comprising at least 10%, preferably at least 20%, and more preferably at least 30% by weight of ethanol. The use of such a mixture makes it possible, in particular, to facilitate the evaporation of the composition. Uses

[0076] According to a third aspect, the present invention relates to the use of a composition as defined above to prevent irreversible deformation of keratin fibers during combing and detangling.

[0077] Preferably, the keratin fibers are damaged and / or sensitized keratin fibers, in particular damaged and / or sensitized hair.

[0078] According to a fourth aspect, the present invention relates to the use of a composition as defined above to repair and / or prevent the breakage of keratin fibers.

[0079] Preferably, the keratin fibers are damaged and / or sensitized keratin fibers, in particular damaged and / or sensitized hair.

[0080] According to a fifth aspect, the present invention relates to the use of one or more unsaturated fatty acids as defined above to stabilize a composition, preferably to stabilize the color of a composition comprising one or more pyridine derivatives as defined above. Examples

[0081] The following examples provide a better understanding of the invention without, however, being limiting in nature.

[0082] a. Preparation of formulas

[0083] Two types of compositions, Ax and By, were prepared in which the amount of Pyridoxine HCl varies from 1% to 5% by weight and the amount of oleic acid varies from 0% to 8% by weight. Some of these compositions were evaluated with regard to their stability and / or resistance to breakage and / or irreversible deformation.

[0084] [Tables 1] Composition Ax Ingredients % by mass Cetearyl Alcohol 7 Myristyle stearate and myristyle palmitate mixture 2 Behentrimonium Chloride 3.75 Amodimethicone (And) Trideceth-6 (And) Cetrimonium Chloride 8.5 Pyridoxine HCl 1 to 5 Oleic Acid 0 to 8 Preservatives 0.43 NaOH 5N Qsp pH 4.0 Water Qsp 100

[0085] [Tables2] Composition by Ingredients % mass Ethanol 30 1,2-Propylene glycol 20 Pyridoxine HCl 1 to 5 Oleic acid 0 to 8 NaOH 5N Qsp pH 4.0 Water Qsp 100

[0086] b. Stability study of compositions

[0087] Some of the Ax and Byont compositions were placed in vials and then in an oven at 66°C for one week to study the evolution of color during storage. The intensity of the color change of the compositions (yellowing / browning) after storage was evaluated using the following scale: 0 = no difference, 1 = slight, 2 = intense, 3 = very intense. Only formulas with a score of 0 are considered colorfast.

[0088] c. Study of breakage and irreversible deformation of hair

[0089] Some of the Ax and Byon compositions were applied according to the application protocol described below and evaluated with regard to their integrity, namely their resistance to the breakage and irreversible deformation according to the test protocol described below. Application protocol

[0090] Strands of Caucasian hair, damaged by two successive bleachings, weighing 2.7g and measuring 27cm in length, are washed with DOP shampoo, then squeezed dry between the fingers (2 passes). The damp strands are then laid on a flat surface and the Axou By compositions are applied to said strands with a bath ratio of 0.4 (i.e., 0.4g of composition per 1g of hair).

[0091] The hair is then massaged with the fingers using circular motions along each strand (5 times), and the strands are left for 5 minutes. The strands are then rinsed under tap water for 10 seconds, squeezed dry, and then dried at 60°C (10 min / g of hair). These steps are repeated for a total of 5 applications.

[0092] A damaged and untreated strand of hair is used as a reference. Test protocol

[0093] The test consists of pulling on wet hair to see if the hair breaks, becomes irreversibly deformed, or deforms and then returns to its original shape and length. The test is commonly used by hairdressers to assess the integrity of their clients' hair. The test involves taking a strand of hair, soaking it in water for 30 seconds, and then taking and holding three hair fibers between the index finger and thumb of each hand (each hand holds one end of the fibers). The fibers are then placed under slight tension by moving the fingers and thumbs of each hand apart so that there are 3 centimeters of fibers between the hands, and then pulling so that the fibers deform an additional 1 cm. A ruler is used to ensure that the stretching distances are correctly maintained. The fibers are held for 3 seconds, and then the tension is gently released.The fibers are placed horizontally on absorbent paper for 5 minutes to dry and then evaluated.

[0094] The test is repeated 5 times, for a total of 15 fibers.

[0095] The hair integrity performance is classified according to the following rules: • If the sum of irreversibly broken and deformed fibers is equal to or greater than 10, the hair has very poor integrity. • If the sum of irreversibly broken and deformed fibers is between 6 and 9 inclusive, the hair has poor integrity. • If the sum of irreversibly broken and deformed fibers is between 2 and 5 inclusive, the hair has good integrity. • If the sum of irreversibly broken and deformed fibers is 1 or less, the hair has very good integrity.

[0096] d. Results of stability measurements:

[0097] The results of the stability measurements for each of the compositions tested are summarized in the table below.

[0098] [Tables3] Compositions Composition Type % mass Pyridoxine HCl (% mass Pyridoxine) % mass Oleic acid Molar ratio Pyridoxine HCl / Oleic acid Intensity of color change Ai Bi Comparative 1(0.8) 0 N / A 1 A2 b2 Comparative 2(1.6) 0 N / A 2 A3 b3 Comparative 3(2.5) 0 N / A 2 A4 b4 Comparative 4(3.3) 0 N / A 3 A5 b5 Comparative 5(4.1) 0 N / A 3 Ae b6 Comparative 1(0.8) 1 1.37 1 A7 b7 Comparative 1(0.8) 2 0.69 0 As Bs Comparative 1(0.8) 3 0.46 0 A9 b9 Comparative 1(0.8) 4 0.34 0 A10 B10 Comparative 1(0.8) 5 0.27 0 An Bu Comparative 1(0.8) 6 0.23 0 A12 B12 Comparative 1(0.8) 7 0.20 0 Ab B13 Comparative 1(0.8) 8 0.17 0 A14 B14 Comparative 2(1.6) 1 2.75 2 A15 B15 Comparative 2(1.6) 2 1.37 1 A16 B16 Invention 2(1.6) 3 0.92 0 A17 Bp Invention 2(1.6) 4 0.69 0 Aïs Bis Invention 2(1.6) 5 0.55 0 A19 B19 Invention 2(1.6) 6 0.46 0 A20 B 20 Invention 2(1.6) 7 0.39 0 A21 B21 Invention 2(1.6) 8 0.34 0 A22 B 22 Comparative 3(2.5) 1 4.12 2 A23 B 23 Comparative 3(2.5) 2 2.06 2 A24 B24 Comparative 3(2.5) 3 1,37 1 A25 B25 Invention 3(2,5) 4 1,03 0 , A 26 B 26 Invention 3(2.5) 5 0.82 0 A27 B27 Invention 3(2.5) 6 0.69 0 A28 B 28 Invention 3(2.5) 7 0.59 0 A29 B 29 Invention 3(2.5) 8 0.52 0 A10 B 30 Comparative 4(3.3) 1 5.49 3 A31 B31 Comparative 4(3.3) 2 2.75 3 A32 B 32 Comparative 4(3.3) 3 1.83 2 A33 B 33 Comparative 4(3.3) 4 1.37 1 A34 B 34 Invention 4(3.3) 5 1.10 0 A35 B 35 Comparative 5(4.1) 1 6.87 3 A36 B 36 Comparison 5(4.1) 2 3.43 3 A37 B37 Comparison 5(4.1) 3 2.29 3 A38 B38 Comparison 5(4.1) 4 1.72 2 A39 B 39 Comparison 5(4.1) 5 1.37 1 A40 B 40 Invention 5(4.1) 6 1.14 0 A41 B41 Comparison 1(0.8) 1.1 1.25 1 A42 B42 Comparison 1(0.8) 1.25 1.10 0 A43 B43 Comparison 1(0.8) 1.5 0.92 0 A44 B 44 Comparison 1(0.8) 1.75 0.78 0 A45 B45 Comparison 2(1.6) 2.1 1.31 1 A46 B46 Comparative 2(1.6) 2.25 1.22 1 A47 B47 Invention 2(1.6) 2.5 1.10 0 A48 B 48 Invention 2(1.6) 2.75 1.00 0 A49 B49 Comparative 3(2.5) 3.1 1.33 1 A50 B 50 Comparative 3(2.5) 3.25 1.27 1 A51 B51 Comparative 3(2.5) 3.5 1.18 1 A52 B52 Invention 3(2.5) 3.75 1,10 0 A53 B 53 Comparison 4(3,3) 4.1 1.34 1 A54 B 54 Comparison 4(3,3) 4.25 1.29 1 A55 B55 Comparison 4(3,3) 4.5 1.22 1 A56 B 56 Comparison 4(3,3) 4.75 1.16 1 , A57 B 57 Comparison 5(4,1) 5.1 1.35 1 A58 B58 Comparison 5(4,1) 5.25 1.31 1 A59 B 59 Comparison 5(4,1) 5.5 1.25 1 Aeo B 60 Comparison 5(4,1) 5.75 1.19 1

[0099] The results show that the compositions according to the present invention are stable.

[0100] e. Result of integrity measures

[0101] The results of the integrity measurements for each of the compositions tested are summarized in the table below.

[0102] [Tables4] Composition Type of composition % by mass Pyridoxine HCl (% by mass Pyridoxine) % by mass Oleic acid Molar ratio Pyridoxine HCl / Oleic acid Number of broken fibers Number of irreversibly deformed fibers Damaged and untreated hair - - - - 1 7 B42 Comparative 1(0.8) 1.25 1.10 1 6 Bei Comparative 2.25(1.9) 0 N / A 0 8 Bô2 Comparative 0(0) 2.25 0 0 7 B47 Invention 2(1.6) 2.5 1.10 0 2 Bô3 Comparative 4.5(3.7) 0 N / A 0 6 B 64 Comparative 0(0) 4.5 0 0 6 B52 Invention 3(2.5) 3.75 1.10 0 3 Bô5 Comparison 6.75(5.6) 0 N / A 0 6 B 66 Comparison 0(0) 6.75 0 0 7 B34 Invention 4(3.3) 5 1.10 0 2 Be7 Comparison 9(7.4) 0 N / A 0 6 B68 Comparison 0(0) 9 0 0 7 B40 Invention 5(4.1) 6 1.14 0 0 B 69 Comparison 11(9) 0 N / A 0 7 B70 Comparison 0(0) 11 0 0 6

[0103] The results show that the compositions according to the present invention make it possible to prevent irreversible hair deformation and hair breakage.

Claims

1. Demands Composition includes: (i) one or more pyridine derivatives selected from the following compounds of formula (I), their salts, their isomers, their solvates such as hydrates and mixtures thereof: Formula (I) in which: ■ R1 represents a (Ci-C4)alkyl group possibly substituted by one or more groups, identical or different, chosen from: hydroxyl (-OH) or amino (-NH2); ■ R2 represents: - a (Ci-C4)alkyl group possibly substituted by one or more groups, identical or different, chosen from hydroxyl (-OH) or amino (-NH2) and / or possibly interrupted by one or more atoms of oxygen, sulfur or nitrogen, preferably oxygen; or - a (-CHO) group; ■ R3 represents: - a (CrC4)alkyl group possibly substituted by one or more groups, identical or different, chosen from hydroxyl (-OH) or amino (-NH2) or phosphate (-OP(O)(OH)2) and / or possibly interrupted by one or more groups or heteroatoms, identical or different, chosen from O, S, N, -C(O)- and their combinations such as —SC(O)-, preferably chosen from O, or -SC(O)-; ii) one or more fatty acids selected from unsaturated fatty acids, their salts, their isomers, their solvates such as hydrates and their mixtures; in which: - the composition comprises a total content of compounds of formula (I), their isomers and mixtures thereof exceeding 0.9% by weight relative to the total weight of the composition; and - the molar ratio of the total quantity of pyridine derivatives i) to the total quantity of fatty acids ii) present in the composition is less than or

2. equal to 1.15; and - the pH of composition is from 3 to 10. Composition according to claim 1 wherein the pyridine derivative(s) i) are selected from the following compounds 1 to 10, their salts, their isomers, their solvates such as hydrates and mixtures thereof: Compound 1 w U s Pyridoxine Compound 2 "'h 0 Pyridcxme phosphate Compound 3 Oh ho Is J .XX PyEidûxaî Compound 4 CiCC Pyndoxamine Compound 5 0 XAX f "x" Pyndoxanàne phosphate Compound 6 CH:. ÜH KO 1, .XI 4-Deoxy py ndoxihe Compound 7 ..... Xx J XX Pyridoxine 5-ihioacetate Compound 8 <7 6 \__ / I........_ \ / 5-(Hydroxymethyl)-4-(methoxymethyl()-2-methylpyrrhim-3-oi Compound 9 HX' 2,5-Dimethyl i-3-hydroxy-4-pyridinemethanot Compound 10 '''yX OH 3-Hydroxy-2,4.5-trihydroxymethylpyridin^

3.

4. preferably chosen from compound 1, its salts, its isomers, its solvates such as hydrates and mixtures thereof, more preferably chosen from pyridoxine, pyridoxine hydrochloride and mixtures thereof. A composition according to any one of the preceding claims, wherein the pyridine derivative(s) (i) are present in the composition in a total content of from 1.1% to 10% by weight, preferably from 1.5% to 9% by weight, more preferably from 2% to 7% by weight relative to the total weight of the composition. A composition according to any one of the preceding claims, wherein the fatty acid(s) (ii) are selected from the following compounds of formula (II), their salts, isomers, and solvates such as hydrates and their mixtures: Formula (II) in which R represents a (C8-C40)alkenyl group optionally substituted by one or more hydroxyl groups (-OH), preferably a (Cio-C3O)alkenyl group optionally substituted by one or more hydroxyl groups (-OH), more preferably a (Ci2-C24)alkenyl group optionally substituted by one or more hydroxyl groups (-OH).

5. Composition according to any one of the preceding claims, wherein the fatty acid(s) ii) are selected from myritoleic acid, palmitoleic acid, vaccenic acid, paullinic acid, oleic acid, elaidic acid, gondoic acid, erucic acid, nervonic acid, linoleic acid, linolelaidic acid, ei-cosadienoic acid, docosadienoic acid, their salts, isomers, solvates such as hydrates and mixtures thereof.

6. Composition according to any one of the preceding claims, wherein the fatty acid(s) ii) are present in the composition in a total content of 1.7% to 13% by weight, preferably of 1.9% to 9% by weight, more preferably of 2% to 6.5% by weight relative to the total weight of the composition.

7. Composition according to any one of the preceding claims, wherein the molar ratio of total quantity of pyridine derivatives (i) / total quantity of fatty acids (ii) present in the composition is from 0.3 to 1.15, more preferably from 0.5 to 1.

10.

8. Composition according to any one of the preceding claims, wherein the composition pH is from 3 to 7, preferably from 3.5 to 5, more preferably the composition pH is 4.

9. Composition according to any one of the preceding claims, wherein the composition comprises a solvent selected from water, C2-C4 alcohols, polyols, polyol ethers and mixtures thereof, preferably from water, ethanol, isopropanol, propylene glycol and mixtures thereof, more preferably from water, ethanol, propylene glycol and mixtures thereof.

10. A process for treating keratin fibers comprising i) the application on keratin fibers of a composition as defined in any one of the preceding claims.

11. A method according to the preceding claim comprising at least one additional step successive to step i) selected from the following steps ii) to iv): ii) a step of applying the composition to the keratin fibers, preferably of a duration of at least 10 seconds, said application step being optionally carried out under an airtight film such as a foil packet or plastic film; iii) a step of rinsing and / or washing the keratin fibers; iv) a step of drying the keratin fibers in ambient air or with the aid of a heating device.

12. Use of a composition as defined in any one of claims 1 to 9 to prevent irreversible deformation of keratin fibers during combing and / or detangling.

13. Use of a composition as defined in any one of claims 1 to 9 for repairing and / or preventing breakage of keratin fibers.

14. Use according to claim 12 or 13, wherein the keratin fibers are damaged and / or sensitized keratin fibers.

15. Use of one or more fatty acids ii) as defined in any one of claims 1, 4 or 5 to stabilize a composition, preferably to stabilize the color of a composition comprising one or more pyridine derivatives i) as defined in claim 1 or 2.

16. Use according to the preceding claim, wherein the composition comprises a total content of compounds of formula (I), their isomers and mixtures of more than 0.9% by weight, preferably from 1.1% to 10% by weight, more preferably from 1.5% to 9% by weight, even more preferably from 2% to 7% by weight relative to the total weight of the composition.