Compositions and methods for treating keratin fibres with at least one specific pyridine derivative and at least one unsaturated fatty acid

The color instability of the hair care composition during storage is solved by compositions of specific pyridine derivatives and unsaturated fatty acids, and prevents irreversible deformation of the hair and repairs breakage during combing or untangling.

CN120359015APending Publication Date: 2025-07-22LOREAL SA
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Patent Information

Application Number
CN202380085664.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2022-12-14
Filing Date
2023-12-12
Publication Date
2025-07-22

AI Technical Summary

Technical Problem

Existing hair care compositions are prone to yellowing or browning during storage and are not effective in preventing irreversible deformation and breakage of hair during combing or untangling.

Method used

Using a composition containing a specific pyridine derivative and an unsaturated fatty acid, the molar ratio of the pyridine derivative to the fatty acid is less than or equal to 1.15, and the content of the pyridine derivative in the composition is greater than 0.9%, for treating keratin fibers to prevent irreversible deformation and repairing fracture.

Benefits of technology

Color stability of the composition is achieved while preventing irreversible deformation and repair of the hair during combing or untangling or preventing hair breakage.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention relates to a composition comprising at least one specific pyridine derivative and at least one unsaturated fatty acid, and also to a method for treating keratin fibres using said composition.
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Description

Technical field

[0001] The present invention relates to a composition comprising at least one specific pyridine derivative and at least one unsaturated fatty acid, and also to a method for treating keratin fibers using said composition. Background art

[0002] Hair can be damaged and become brittle due to external atmospheric factors such as pollution and bad weather, and also due to mechanical or chemical treatments or certain daily actions such as brushing, combing, dyeing, bleaching, permanent waving, relaxing and repeated washing. Hair can ultimately become deformed and damaged, and can become dry, rough, brittle, dull, split and / or fine and limp over a long period of time.

[0003] To overcome this problem, it is common practice to use hair care compositions aimed at conditioning hair by giving it satisfactory cosmetic properties, especially smoothness, gloss, softness, suppleness, lightness, good detangling properties, making the hair easy to comb and manage, so that the hair is easier to style and maintain its shape. However, the conditioning effect obtained with these hair care compositions fades rapidly over time, does not always show satisfactory persistence to shampooing, and does not prevent irreversible deformation of the hair due to fiber elongation, for example during combing or detangling, nor does it repair or prevent hair breakage.

[0004] It is known practice to use pyridine derivatives such as pyridoxine or its salts in hair care compositions intended for conditioning hair in order to maintain or even improve the quality of the hair. However, these derivatives can cause yellowing or browning of the hair care compositions containing them during their storage. For this reason, the use of these derivatives in hair care compositions has so far been relatively limited, especially to prevent their use at high concentrations.

[0005] Therefore, there is a real need to develop a hair care composition characterized by good color stability during storage, which comprises at least one specific pyridine derivative, such that it is possible to prevent irreversible deformation of the hair, especially damaged and / or sensitized hair, due to fiber elongation (for example during combing or detangling), and to repair or prevent breakage of the hair, especially damaged and / or sensitized hair.

[0006] The Applicant has surprisingly found that all or some of these objectives can be achieved by the composition according to the invention. Summary of the invention

[0007] According to a first aspect, the subject of the present invention is a composition comprising:

[0008] i) A pyridine derivative of one or more compounds selected from the following formula (I), its salts, its isomers, its solvates such as hydrates, and mixtures thereof:

[0009]

[0010] In formula (I):

[0011] ■R 1 represents a (C1-C4) alkyl group optionally substituted by one or more identical or different groups selected from the following: hydroxyl (-OH) or amino (-NH2);

[0012] ■R 2 represents:

[0013] -(C1-C4) alkyl group, which is optionally substituted by one or more identical or different groups selected from hydroxyl (-OH) or amino (-NH2) and / or optionally inserted with one or more oxygen, sulfur or nitrogen atoms, preferably oxygen; or

[0014] - group (-CHO);

[0015] ■R 3 represents:

[0016] -(C1-C4) alkyl group, which is optionally substituted by one or more identical or different groups selected from hydroxyl (-OH) or amino (-NH2) or phosphate (-OP(O)(OH)2) and / or optionally inserted with one or more identical or different groups selected from O, S, N, -C(O)- and its combinations such as -SC(O)-, preferably selected from O or -SC(O)- or heteroatoms;

[0017] ii) One or more fatty acids selected from unsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof;

[0018] wherein:

[0019] - The composition contains a total content of the compound of formula (I), its isomers and their mixtures greater than 0.9% by weight relative to the total weight of the composition; and

[0020] - The molar ratio of the total amount of the pyridine derivative i) present in the composition to the total amount of the fatty acid ii) is less than or equal to 1.15.

[0021] According to a second aspect, the subject of the present invention is a method for treating keratin fibers, the method comprising i) applying to the keratin fibers a composition as previously defined.

[0022] According to a third aspect, the subject of the invention is the use of a composition as defined previously for preventing irreversible deformation of keratin fibers during combing and / or detangling.

[0023] According to a fourth aspect, the subject of the invention is the use of a composition as defined previously for repairing and / or preventing breakage of keratin fibers.

[0024] According to a fifth aspect, the subject of the invention is the use of one or more fatty acids ii) as defined previously for stabilizing a composition comprising one or more pyridine derivatives i) as defined previously. Detailed Description

[0025] For the purposes of the present invention and unless otherwise indicated:

[0026] ■ The term "keratin fiber" means a fiber of human or animal origin, such as hair, body hair, eyelashes, eyebrows, wool, mohair, cashmere or fur. According to the invention, the keratin fiber is preferably a human keratin fiber, more preferably hair.

[0027] ■ The term "damaged keratin fiber" means a dry, rough, brittle, split and / or soft keratin fiber.

[0028] ■ The term "sensitized keratin fiber" means a keratin fiber that has been bleached, artificially colored, relaxed and / or permed.

[0029] ■ The term "fatty acid" means a straight-chain or branched-chain, saturated or unsaturated carboxylic acid containing from 8 to 30 carbon atoms.

[0030] ■ The term "unsaturated fatty acid" means a fatty acid that contains one or more ethylenic unsaturations, preferably one or two ethylenic unsaturations, in its structure.

[0031] ■ The term "alkyl" means a saturated straight-chain or branched-chain hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 1 to 26 carbon atoms, more preferably from 1 to 22 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl, n-decyl, n-undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl or eicosyl.

[0032] ■ The term "(C x -C y ) alkyl" means an alkyl containing from x to y carbon atoms.

[0033] The term "alkenyl" means a straight-chain or branched hydrocarbon-based group containing one or more ethylenic unsaturations, preferably one or two ethylenic unsaturations and from 2 to 40 carbon atoms, preferably from 2 to 26 carbon atoms, more preferably from 2 to 24 carbon atoms, such as vinyl, n-propenyl, isopropenyl, butenyl, n-pentenyl, n-hexenyl, n-decenyl, n-dodecenyl, tetradecenyl, hexadecenyl or eicosenyl.

[0034] ■ The term "(C x -C y ) alkenyl" means an alkenyl group containing from x to y carbon atoms.

[0035] ■ The term "salt" means an addition salt with an organic or inorganic acid or base. Addition salts with acids are especially selected from addition salts with organic or inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, citric acid, succinic acid, tartaric acid, lactic acid, toluenesulfonic acid, benzenesulfonic acid, phosphoric acid or acetic acid. Addition salts with bases are especially selected from addition salts with organic or inorganic bases such as alkali metal hydroxides, alkaline earth metal hydroxides, ammonia, amines or alkanolamines.

[0036] ■ The term "isomer" means an optical, geometric or tautomeric isomer.

[0037] The terms "at least one / species" and "one / species or more / more species" are synonymous and can be used interchangeably.

[0038] Composition

[0039] According to a first aspect, the subject of the present invention is a composition as previously defined.

[0040] The Applicant has surprisingly found that the composition according to the invention makes it possible to prevent irreversible deformation of the hair, in particular damaged and / or sensitized hair, due to elongation of the fibres (for example during combing or detangling), and to repair or prevent breakage of the hair, in particular damaged and / or sensitized hair, while being stable and not undergoing any colour change over time, in particular during storage.

[0041] Pyridine derivative

[0042] The composition comprises i) one or more pyridine derivatives selected from compounds of formula (I) as previously defined, their salts, their isomers, their solvates such as hydrates and their mixtures.

[0043] Preferably, the pyridine derivative i) is selected from the following compounds 1 to 10, their salts, their isomers, their solvates such as hydrates and their mixtures:

[0044]

[0045]

[0046] More preferably, the pyridine derivative (i) is selected from Compound 1, its salts, its solvates such as hydrates, and mixtures thereof.

[0047] Even more preferably, the pyridine derivative (i) is selected from pyridoxine, pyridoxine hydrochloride, and mixtures thereof.

[0048] The composition comprises a total content of the compound of formula (I), its isomers, and mixtures thereof that is greater than 0.9% by weight, preferably in the range of 1.1% to 10% by weight, more preferably in the range of 1.5% to 9% by weight, and even more preferably in the range of 2% to 7% by weight, based on the total weight of the composition.

[0049] In embodiments where one or more of the pyridine derivatives (i) are in the form of salts or solvates of the compound of formula (I) according to the present invention, the term "total content of the compound of formula (I)" does not refer to the salt or solvate content, but rather to the content of the compound of formula (I). For example, when the composition according to the present invention contains only pyridoxine hydrochloride, the total content of the compound of formula (I) is not the pyridoxine hydrochloride content, but rather the pyridoxine content.

[0050] Fatty acid

[0051] The composition comprises (ii) one or more fatty acids selected from unsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof:

[0052] According to a preferred embodiment, the fatty acid (ii) is selected from compounds of the following formula (II), their salts, their isomers, their solvates such as hydrates, and mixtures thereof:

[0053]

[0054] In formula (II), R represents an (C8-C 40 ) alkenyl group optionally substituted with one or more hydroxyl groups (-OH), preferably an (C 10 -C 30 ) alkenyl group optionally substituted with one or more hydroxyl groups (-OH), more preferably an (C 12 -C 24 ) alkenyl group optionally substituted with one or more hydroxyl groups (-OH).

[0055] According to a specific embodiment, the fatty acid (ii) is selected from compounds of formula (II) as previously defined, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, in which formula (II), R represents an unsubstituted (C8-C 40 ) alkenyl group, preferably an unsubstituted (C 10 -C30 ) alkenyl, more preferably unsubstituted (C 12 -C 24 ) alkenyl.

[0056] According to another specific embodiment, fatty acid ii) is selected from compounds of formula (II) as defined previously, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, wherein in formula (II), R represents (C8-C) substituted by one or more hydroxyl groups (-OH) 40 ) alkenyl, preferably (C 10 -C 30 ) alkenyl substituted by one or more hydroxyl groups (-OH), more preferably (C 12 -C 24 ) alkenyl substituted by one or more hydroxyl groups (-OH).

[0057] According to another specific embodiment, fatty acid ii) is selected from compounds of formula (II) as defined previously, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, wherein in formula (II), R represents (C8-C) substituted by a hydroxyl group (-OH) 40 ) alkenyl, preferably (C 10 -C 30 ) alkenyl substituted by a hydroxyl group (-OH), more preferably (C 12 -C 24 ) alkenyl substituted by a hydroxyl group (-OH).

[0058] According to a specific embodiment, fatty acid ii) is selected from monounsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, preferably selected from myristoleic acid, palmitoleic acid, vaccenic acid, gadoleic acid, oleic acid, elaidic acid, gondoic acid, cetoleic acid, erucic acid, nervonic acid, their salts, their isomers, their solvates such as hydrates, and mixtures thereof.

[0059] According to a specific embodiment, fatty acid ii) is selected from polyunsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, preferably selected from linoleic acid, linolelaidic acid, eicosadienoic acid, docosadienoic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, rumenic acid, their salts, their isomers, their solvates such as hydrates, and mixtures thereof.

[0060] According to a specific embodiment, the fatty acid ii) is selected from hydroxylated monounsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, preferably selected from 10-hydroxy-cis-12-octadecenoic acid, 10-hydroxy-trans-11-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, 13-hydroxy-cis-9-octadecenoic acid, ricinoleic acid, isolinoleic acid, their salts, their isomers, their solvates such as hydrates, and mixtures thereof.

[0061] According to a specific embodiment, the fatty acid ii) is selected from hydroxylated polyunsaturated fatty acids, their salts, their isomers, their solvates such as hydrates, and mixtures thereof, preferably selected from hydroxylated octadecadienoic acid (densipolic acid), hydroxylated octadecatrienoic acid (auricolic acid), octadecadienoic acid, their salts, their isomers, their solvates such as hydrates, and mixtures thereof.

[0062] According to a more preferred embodiment, the fatty acid ii) is selected from myristoleic acid, palmitoleic acid, petroselinic acid, gadoleic acid, oleic acid, elaidic acid, cetoleic acid, erucic acid, nervonic acid, linoleic acid, elaidolinoleic acid, eicosadienoic acid, docosadienoic acid, their salts, their isomers, their solvates such as hydrates, and mixtures thereof.

[0063] According to an even more preferred embodiment, the fatty acid ii) is selected from oleic acid, its salts, its solvates such as hydrates, and mixtures thereof, preferably oleic acid.

[0064] The fatty acid ii) is present in the composition in a total content preferably in the range of 1.7% to 13% by weight, more preferably in the range of 1.9% to 9% by weight, and even more preferably in the range of 2% to 6.5% by weight, based on the total weight of the composition.

[0065] The molar ratio of the total amount of the pyridine derivative i) present in the composition to the total amount of the fatty acid ii) is less than or equal to 1.15, preferably in the range of 0.3 to 1.15, and more preferably in the range of 0.5 to 1.10.

[0066] According to a preferred embodiment, the composition according to the invention comprises:

[0067] 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;

[0068] ii) one or more fatty acids selected from oleic acid, its salts, its solvates such as hydrates, and mixtures thereof, preferably oleic acid;

[0069] It should be understood that:

[0070] - The composition comprises a total pyridoxine content of more than 0.9% by weight relative to the total weight of the composition; and

[0071] - The molar ratio of the total amount of the pyridine derivative (i) present in the composition to the total amount of the fatty acid (ii) is less than or equal to 1.15.

[0072] Other characteristics of the composition

[0073] The composition is a cosmetic composition, i.e. a composition comprising a cosmetically acceptable medium, i.e. a medium compatible with human keratin fibres.

[0074] The composition may comprise a solvent selected from the group consisting of water, ethanol, isopropanol, glycerol, 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.

[0075] The composition may comprise a solvent selected from water, C2-C4 alcohols, polyols, polyol ethers and mixtures thereof.

[0076] Preferably, the composition comprises a solvent selected from water, ethanol, isopropanol, propylene glycol and mixtures thereof.

[0077] More preferably, the composition comprises a solvent selected from water, ethanol, propylene glycol and mixtures thereof.

[0078] The composition may further comprise at least one cosmetic ingredient selected from the group consisting of nonionic, anionic, cationic and amphoteric surfactants, vitamins and provitamins other than vitamin B6 (including panthenol), fillers, dyes, pearlescent agents, opacifiers, chelating agents, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, defoamers, humectants, emollients, penetrants, fragrances, preservatives and mixtures thereof.

[0079] These conventional cosmetic ingredients may be present in the composition in amounts that can be readily determined by a person skilled in the art, and for each ingredient, the amount thereof may range from 0.01% to 20% by weight relative to the total weight of the composition. A person skilled in the art will carefully select the ingredients included in the composition and also their amounts such that they do not impair the properties of the composition.

[0080] The composition may be in any presentation form conventionally used for hair care applications. By way of non-limiting example, the composition may be in the form of a lotion, cream, mousse, gel, spray or hairspray.

[0081] The composition may be used by rinse-off or leave-on application.

[0082] The composition may be in the form of a shampoo, a hair mask, a conditioning composition or a pre-shampoo. The composition may also be in the form of a composition that is added to or mixed with a shampoo, a hair mask or a conditioning composition before application.

[0083] The composition may be packaged in a pump bottle or an aerosol container for applying the composition in a vaporized (hairspray) or foamed form. In these cases, the composition preferably comprises at least one propellant.

[0084] The pH of the composition is preferably from 3 to 10, more preferably from 3 to 7 and even more preferably from 3.5 to 5. Preferably, the pH of the composition is equal to 4. The pH can be adjusted using organic or inorganic acids or organic or inorganic bases commonly used in cosmetics.

[0085] According to a preferred embodiment, the composition comprises a total content of colorants 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 colorants.

[0086] The term "colorant" means an oxidation dye, a direct dye or a pigment.

[0087] The term "oxidation dye" means an oxidation dye precursor selected from oxidation developing bases and couplers. Oxidation developing bases and couplers are colorless or slightly colored compounds which form colored substances via a condensation reaction in the presence of an oxidizing agent.

[0088] The term "direct dye" means natural and / or synthetic dyes other than oxidation dyes, including in the form of one or more extracts. These are colored compounds which will spread on the surface onto the fibers. They can be ionic or non-ionic, i.e. anionic, cationic, neutral or non-ionic.

[0089] Method for treating keratin fibers

[0090] According to a second aspect, the subject matter of the present invention is a method for treating keratin fibers, the method comprising i) applying to the keratin fibers a composition as previously defined.

[0091] The composition may be applied to dry or wet keratin fibers, preferably wet keratin fibers.

[0092] Preferably, the keratin fibers are damaged and / or sensitized keratin fibers, in particular damaged and / or sensitized hair.

[0093] The bath ratio range of the composition applied to the keratin fibers can be from 0.1 to 10. For example, the bath ratio can be 0.4. The term "bath ratio" means the ratio between the total weight of the applied composition and the total weight of the keratin fibers to be treated.

[0094] The method can include at least one additional step selected from the following steps ii) to iv) after step i):

[0095] ii) The step of applying the composition to the keratin fibers, preferably for a period of at least 10 seconds, and the application step can optionally be carried out under an airtight film of the wrapper or plastic film type;

[0096] iii) The step of rinsing and / or washing the keratin fibers;

[0097] iv) The step of drying the keratin fibers in ambient air or using a heating device.

[0098] Preferably, the method includes additional steps ii) and iv) as described previously and in that order.

[0099] More preferably, the method can include all additional steps ii), iii) and iv) as described previously and in that order.

[0100] The step of applying the composition can last from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.

[0101] The washing step can be carried out using a shampoo, for example.

[0102] 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 heating cap, hair straighteners or a heated brush can be used as the heating device, for example.

[0103] The drying step iv) can also be a combination of drying with air or with a heating device (such as a hair dryer or a heating cap) with a temperature range of 50°C to 80°C, and possibly then a straightening step (preferably with a hair straightener).

[0104] Steps i) to iii) or steps i) to iv) can be repeated as many times as needed, and each cycle of steps i) to iii) or i) to iv) can be spaced from the next cycle by several minutes to several days or weeks. Different hair treatments of the present invention can be carried out between different application cycles, before or after.

[0105] In the case where step iii) of rinsing and / or washing the keratin fibres is not included in the method, the composition may for example comprise a solvent mixture such as a water / ethanol mixture, the 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 may in particular promote the evaporation of the composition.

[0106] Use

[0107] According to a third aspect, the subject of the invention is the use of a composition as defined previously for preventing irreversible deformation of keratin fibres during combing and detangling.

[0108] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.

[0109] According to a fourth aspect, the subject of the invention is the use of a composition as defined previously for repairing and / or preventing breakage of keratin fibres.

[0110] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.

[0111] According to a fifth aspect, the subject of the invention is the use of one or more unsaturated fatty acids ii) as defined previously for stabilizing the composition, preferably for stabilizing the colour of a composition comprising one or more pyridine derivatives as defined previously.

[0112] Examples

[0113] The following examples provide a better understanding of the invention, which is however not restrictive in nature.

[0114] a. Preparation of the formulation

[0115] Two types of compositions A x and B y were prepared, in which the amount of pyridoxine hydrochloride ranged from 1% to 5% by weight and the amount of oleic acid ranged from 0% to 8% by weight. Some of these compositions were evaluated for their stability and / or anti-breakage and / or anti-irreversible deformation properties.

[0116] [Table 1]

[0117]

[0118] [Table 2]

[0119]

[0120] b. Study on the stability of the composition

[0121] Place some of Composition A x and B y in a flask and then place it in an oven at 66 °C for one week to study the change in color during storage. The intensity of the color change (yellowing / browning) of the composition after storage was evaluated using the following scale: 0 = no difference, 1 = slight, 2 = strong, 3 = very strong. Only the formulations scored 0 were judged to be color stable.

[0122] c. Study on hair breakage and irreversible deformation

[0123] Administer some of Composition A x and B y according to the administration protocol described below and evaluate it for its integrity (i.e., its resistance to fracture and irreversible deformation) according to the test protocol described below.

[0124] Application protocol

[0125] Wash a 2.7 g and 27 cm long Caucasian hair lock damaged by two consecutive bleaching operations with DOP shampoo and then squeeze it dry (twice) between the fingers. Then place the wet hair lock on a flat surface and apply Composition A x or B y to the hair lock at a bath ratio of 0.4 (i.e., 0.4 g composition / 1 g hair).

[0126] Then massage the hair with the fingers, using a circular motion (five times) on each hair lock, and then let the hair lock stand for 5 minutes. Then rinse the hair lock with tap water for 10 seconds, squeeze it dry, and then dry it at 60 °C (10 min / g hair). Repeat these different steps for a total of five applications.

[0127] Use damaged and untreated hair locks as a reference.

[0128] Test protocol

[0129] The test includes pulling wet hair to see if it breaks, deforms irreversibly or becomes deformed and then returns to its original shape and length. Hairdressers typically use this test to evaluate the integrity of their customers' hair. The test includes taking a lock of hair, soaking it in water for 30 seconds, and then taking three hair fibers and pinching them between the index finger and thumb of both hands (holding one end of the fiber in each hand). The fibers are then placed under slight tension by separating the fingers and thumb of each hand so that there is 3 cm of fiber between the hands, and then pulling to deform the fiber by another 1 cm. A ruler is used to ensure that the stretching distance is adhered to. The fiber is held for 3 seconds and then the tension is gently released. The fiber is placed horizontally on absorbent paper for 5 minutes to dry it, and then evaluated.

[0130] Repeat the test five times, for a total of 15 fibers.

[0131] The hair integrity performance is graded according to the following rules:

[0132] · If the sum of the broken and irreversibly deformed fibers is greater than or equal to 10, the hair has very poor integrity.

[0133] · If the sum of the broken and irreversibly deformed fibers is 6 to 9 (including the end values), the hair has poor integrity.

[0134] · If the sum of the broken and irreversibly deformed fibers is 2 to 5 (including the end values), the hair has good integrity.

[0135] · If the sum of the broken and irreversibly deformed fibers is 1 or less, the hair has very good integrity.

[0136] d. Results of stability measurements:

[0137] The results of the stability measurements for each composition tested are summarized in the table below.

[0138] [Table 3]

[0139]

[0140]

[0141]

[0142] The results show that the compositions according to the invention are stable.

[0143] e. Results of integrity measurements

[0144] The results of the integrity measurements for each composition tested are summarized in the table below.

[0145] [Table 4]

[0146]

[0147]

[0148] The results show that the compositions according to the invention make it possible to prevent irreversible deformation of the hair and hair breakage.

Claims

1. A composition, the composition comprising: i) one or more pyridine derivatives selected from compounds of formula (I) below, their salts, their isomers, their solvates such as hydrates and mixtures thereof: In formula (I): ■R 1 represents a (C1-C4) alkyl group optionally substituted by one or more identical or different groups selected from the following: hydroxy (-OH) or amino (-NH2); ■R 2 Indicates: -(C1-C4)alkyl, which is optionally substituted by one or more identical or different groups selected from hydroxy (-OH) or amino (-NH2) and / or optionally interrupted by one or more oxygen, sulfur or nitrogen atoms, preferably oxygen; or -the group (-CHO); ■R 3 Indicates: -(C1-C4)alkyl, which is optionally substituted by one or more identical or different groups selected from hydroxy (-OH) or amino (-NH2) or phosphate (-OP(O)(OH)2) and / or optionally interrupted by one or more identical or different groups or heteroatoms selected from O, S, N, -C(O)- and combinations thereof such as -SC(O)-, preferably selected 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 mixtures thereof; wherein: -the composition comprises a total content of the compounds of formula (I), their isomers and mixtures thereof greater than 0.9% by weight relative to the total weight of the composition; and -the molar ratio of the total amount of the pyridine derivatives i) present in the composition to the total amount of the fatty acids ii) is less than or equal to 1.

15.

2. The composition according to claim 1, wherein The pyridine derivatives i) are selected from the following compounds 1 to 10, their salts, their isomers, their solvates such as hydrates and mixtures thereof: Preferably selected from compound 1, its salts, its isomers, its solvates such as hydrates and mixtures thereof, more preferably selected from pyridoxine, pyridoxine hydrochloride and mixtures thereof.

3. The composition according to any one of the preceding claims, wherein, The composition comprises a total content of the compounds of formula (I), their isomers and mixtures thereof in the range of 1.1% to 10% by weight, preferably in the range of 1.5% to 9% by weight, more preferably in the range of 2% to 7% by weight relative to the total weight of the composition.

4. The composition according to any one of the preceding claims, wherein, The fatty acids ii) are selected from compounds of formula (II) below, their salts, their isomers, their solvates such as hydrates and mixtures thereof: In formula (II), R represents an alkenyl group of (C8-C 40 ), optionally substituted by one or more hydroxyl groups (-OH), preferably an alkenyl group of (C 10 -C 30 ), more preferably an alkenyl group of (C 12 -C 24 ), optionally substituted by one or more hydroxyl groups (-OH).

5. The composition according to any one of the preceding claims, wherein, The fatty acids ii) are selected from myristoleic acid, palmitoleic acid, petroselinic acid, icosenoic acid, oleic acid, elaidic acid and cetoleic 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.

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

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

10.

8. The composition according to any one of the preceding claims, wherein, The pH of the composition is 3 to 10, preferably 3 to 7, more preferably 3.5 to 5, and even more preferably the pH of the composition is 4.

9. The 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 selected from water, ethanol, isopropanol, propylene glycol and mixtures thereof, more preferably selected from water, ethanol, propylene glycol and mixtures thereof.

10. A method for treating keratin fibers, the method comprising i) applying to the keratin fibers a composition as defined in any one of the preceding claims.

11. The method according to the preceding claim, the method comprising at least one additional step selected from steps ii) to iv) below after step i): ii) applying the composition to the keratin fibers, preferably for a period of at least 10 seconds, the applying step optionally being carried out under an airtight film of the wrapper or plastic film type; iii) rinsing and / or washing the keratin fibers; iv) drying the keratin fibers in ambient air or using a heating device.

12. Use of a composition as defined in any one of claims 1 to 9 for preventing 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. The 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 for stabilizing the composition, preferably for stabilizing 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 the compound of formula (I), its isomers and mixtures thereof which is greater than 0.9% by weight, preferably in the range of 1.1% to 10% by weight, more preferably in the range of 1.5% to 9% by weight, even more preferably in the range of 2% to 7% by weight relative to the total weight of the composition.