EP4724032A1

EP4724032A1 - Composition and process for treating keratin fibres using at least one particular pyrimidine derivative and at least one unsaturated fatty acid

Info

Publication number: EP4724032A1
Application number: EP24732433.8A
Authority: EP
Inventors: Andrew Greaves
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2023-06-09
Filing date: 2024-06-06
Publication date: 2026-04-15
Also published as: WO2024251908A1; FR3149504A1

Abstract

The present invention relates to a composition comprising at least one unsaturated fatty acid and at least one particular pyrimidine derivative and also to a process for treating keratin fibres using this composition.

Description

COMPOSITION AND PROCESS FOR TREATING KERATIN FIBRES USING AT LEAST ONE PARTICULAR PYRIMIDINE DERIVATIVE AND AT LEAST ONE UNSATURATED FATTY ACID

TECHNICAL FIELD OF THE INVENTION

BACKGROUND OF THE INVENTION

The hair can be damaged and embrittled by external atmospheric agents such as pollution and bad weather, and also by mechanical or chemical treatments, or certain routines, such as brushing, combing, dyeing, bleaching, permanent-waving, relaxing and repeated washing. The hair may end up deformed and damaged and may in the long run become dry, coarse, brittle, dull, split and/or limp.

To overcome this, it is common practice to resort to hair compositions intended for conditioning the hair by giving it satisfactory cosmetic properties, notably smoothness, sheen, a soft feel, suppleness, lightness, good disentangling properties leading to easy combing, and good manageability of the hair which is thus easier to style and holds its shape. However, the conditioning effect obtained with these hair care products fades rapidly over time, does not always show satisfactory persistence with respect to shampoo washing and does not prevent irreversible deformation of the hair due to elongation of the fibres, for example during combing or disentangling, nor does it repair or prevent hair breakage.

It is known practice to use pyrimidine derivatives such as thiamine (vitamin B1) or a salt thereof in hair compositions intended for conditioning the hair so as to preserve or even improve the quality of the hair. However, the storage in solution of these derivatives, in particular when they are used in hair care products formulated at acidic pH, generates an odour that is unpleasant for the consumer and therefore limits their use, in particular at high concentration.

Thus, there is a real need to develop a hair composition characterized by good storage stability with respect to odour, which comprises at least one particular pyrimidine derivative, making it possible to prevent irreversible deformation of the hair, notably of damaged and/or sensitized hair, due to elongation of the fibres, for example during combing or disentangling, and to repair or prevent breakage of the hair, notably of damaged and/or sensitized hair.

The applicant has discovered, surprisingly, that all or some of these objectives can be achieved by means of the composition according to the present invention.

SUMMARY OF THE INVENTION

According to a first aspect, a subject of the present invention is a composition comprising:
i) one or more pyrimidine derivatives chosen from the compounds of formula (I) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:
T xAn^- (I)
in which formula (I):
▪ T represents a compound chosen from the compounds of formula (II) below:

(II)
in which formula (II):
▪ R¹ represents a (C₁-C₄)alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: hydroxyl (-OH), phenyl (-C₆H₅) or -C(O)OM in which M represents a hydrogen atom, an alkali metal or alkaline-earth metal, or a negative charge;
▪ R² represents a hydrogen atom or a (C₁-C₄)alkyl group;
▪ R³ represents a hydrogen atom or a (C₁-C₄)alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: a hydroxyl (-OH), -C(O)OM in which M is as defined above, chloride, fluoride, -CHO, -ONO₂, -OSO₃H, -OPO₃H₂ and/or optionally interrupted with one or more groups or heteroatoms, which may be identical or different, chosen from O, S, N, -C(O)- or -S(O)-;
▪ R⁴ represents a hydrogen atom or a (C₁-C₄)alkyl group optionally substituted with a hydroxyl group (-OH);
▪ x represents a stoichiometric coefficient greater than or equal to zero, chosen so as to ensure the electrical neutrality of the compound of formula (I);
▪ An^- represents an inorganic or organic anion chosen from Cl^-, Br^-, I^-, F^-, OH^-, NO₂ ^-, NO₃ ^-, PO₄ ^3-, SO₄ ^2-, H₂PO₄ ^-, H₃P₂O₇ ^-, R-SO₂-O^-, R-O-SO₃ ^-, anions derived from amino acids, preferably of L configuration, more preferentially L-prolinate, L-glutamate or L-aspartate;
▪ R represents a (C₁-C₄)alkyl group;
ii) one or more fatty acids chosen from unsaturated fatty acids, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof;
in which:
- the composition comprises a total content of compounds T, isomers thereof and mixtures thereof, of greater than or equal to 2% by weight relative to the total weight of the composition; and
- the molar ratio of total amount of fatty acids ii)/total amount of compounds T present in the composition is greater than 0.5; and
- the pH of the composition is between 3.5 and 6.5.

According to a second aspect, a subject of the present invention is a process for treating keratin fibres, comprising a) the application to the keratin fibres of a composition as defined previously.

According to a third aspect, a subject of the present invention is the use of a composition as defined previously for preventing irreversible deformation of keratin fibres during combing and/or disentangling.

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

According to a fifth aspect, a subject of the present invention is the use of one or more fatty acids ii) as defined previously for stabilizing a composition comprising one or more pyrimidine derivatives i) as defined previously.

DETAILED DESCRIPTION OF THE INVENTION

For the purposes of the present invention and unless otherwise indicated:

▪ the term “keratin fibres” means fibres of human or animal origin, such as head hair, bodily hairs, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibres are preferably human keratin fibres, more preferentially the head hair.

▪ the term “damaged keratin fibres” means keratin fibres that are dry, rough, brittle, split and/or soft.

▪ the term “sensitized keratin fibres” means keratin fibres that have been bleached, artificially coloured, relaxed and/or permed.

▪ the term “fatty acid” means a linear or branched, saturated or unsaturated carboxylic acid comprising from 8 to 30 carbon atoms.

▪ the term “unsaturated fatty acid” means a fatty acid comprising one or more ethylenic unsaturations in its structure, preferably one or two ethylenic unsaturations.

▪ the term “alkyl group” is understood to mean 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.

▪ the term “(C_x-C_y)alkyl group” means an alkyl group comprising from x to y carbon atoms.

▪ the term “alkenyl group” means a linear or branched hydrocarbon-based radical comprising one or more ethylenic unsaturations, preferably one or two ethylenic unsaturations, these being conjugated or non-conjugated, and from 2 to 4 carbon atoms, preferably from 2 to 26 carbon atoms, more preferentially 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.

▪ the term “(C_x-C_y)alkenyl group” means an alkenyl group comprising from x to y carbon atoms.

▪ the term “salt” means an addition salt with an organic or mineral acid or base. The addition salts with an acid are notably chosen from addition salts with organic or mineral acids such as hydrochloric acid, hydrobromic acid, hydriodic acid, nitric acid, sulfuric acid, citric acid, succinic acid, tartaric acid, lactic acid, tosylic acid, benzenesulfonic acid, phosphoric acid or acetic acid. The addition salts with a base are notably chosen from the addition salts with organic or mineral bases such as alkali metal hydroxides, alkaline-earth metal hydroxides, ammonia, amines or alkanolamines.

▪ the term “isomer” means an optical, geometrical or tautomeric isomer.

▪ the term “thiamine” means the compound of formula:

▪ the term “greater than” means strictly greater than.

The terms “at least one” and “one or more” are synonymous and may be used interchangeably.

The expressions “between... and...”, “comprises from ... to...”, “formed from ... to...” and “ranging from... to...” should be understood as being inclusive of the limits, unless otherwise specified.

Composition

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

The applicant has found, surprisingly, that the composition according to the present invention makes it possible to prevent irreversible deformation of the hair, notably of damaged and/or sensitized hair, due to elongation of the fibres, for example during combing and/or disentangling, and to repair and/or prevent breakage of the hair, notably of damaged and/or sensitized hair, while at the same time being stable and not undergoing any change in odour over time, notably during storage.

Pyrimidine derivatives

The composition comprises i) one or more pyrimidine derivatives chosen from the compounds of formula (I) as defined previously, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

In formula (I), x is a stoichiometric coefficient greater than or equal to zero, chosen so as to ensure the electrical neutrality of the compound of formula (I). By way of example, x may be equal to zero, thereby meaning that the anion An^- is absent and that the compound T represents an internal salt.

Preferably, the pyrimidine derivative(s) i) are chosen from thiamine salts, isomers thereof, solvates thereof such as hydrates, and mixtures thereof.

More preferably, the pyrimidine derivative(s) i) are chosen from thiamine chloride, thiamine nitrate, thiamine chloride hydrochloride, and mixtures thereof.

Even more preferentially, the pyrimidine derivative i) chosen is thiamine chloride hydrochloride.

The composition comprises a total content of compounds T, isomers thereof and mixtures thereof, of greater than or equal to 2% by weight, preferably ranging from 2% to 10% by weight, more preferentially ranging from 2.5% to 10% by weight, even more preferentially ranging from 3% to 8% by weight, most preferably ranging from 3% to 7%, relative to the total weight of the composition.

Fatty acids

The composition comprises ii) one or more fatty acids chosen from unsaturated fatty acids, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:

According to a preferred embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (III) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:
(III)
in which formula (III) R represents a (C₈-C₄₀)alkenyl group optionally substituted with one or more hydroxyl groups (-OH), preferably a (C₁₀-C₃₀)alkenyl group optionally substituted with one or more hydroxyl groups (-OH), more preferentially a (C₁₂-C₂₄)alkenyl group optionally substituted with one or more hydroxyl groups (-OH).

According to one particular embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (III) as defined previously, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof, in which formula (III) R represents an unsubstituted (C₈-C₄₀)alkenyl group, preferably an unsubstituted (C₁₀-C₃₀)alkenyl group, more preferentially an unsubstituted (C₁₂-C₂₄)alkenyl group.

According to another particular embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (III) as defined previously, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof, in which formula (III) R represents a (C₈-C₄₀)alkenyl group substituted with one or more hydroxyl groups (-OH), preferably a (C₁₀-C₃₀)alkenyl group substituted with one or more hydroxyl groups (-OH), more preferentially a (C₁₂-C₂₄)alkenyl group substituted with one or more hydroxyl groups (-OH).

According to another particular embodiment, the fatty acid(s) ii) are chosen from the compounds of formula (III) as defined previously, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof, in which formula (III) R represents a (C₈-C₄₀)alkenyl group substituted with a hydroxyl group (-OH), preferably a (C₁₀-C₃₀)alkenyl group substituted with a hydroxyl group (-OH), more preferentially a (C₁₂-C₂₄)alkenyl group substituted with a hydroxyl group (-OH).

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

According to a particular embodiment, the fatty acid(s) ii) are chosen from polyunsaturated fatty acids, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof, preferably 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, ruminic acid, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

According to a particular embodiment, the fatty acid(s) ii) are chosen from hydroxylated monounsaturated fatty acids, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof, preferably 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, isoricinoleic acid, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

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

According to a more preferred embodiment, the fatty acid(s) ii) are chosen 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, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

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

The fatty acid(s) ii) are present in the composition in a total content preferably ranging from 2% to 15% by weight, more preferentially ranging from 2% to 10% by weight, relative to the total weight of the composition.

The molar ratio of total amount of fatty acids ii)/total amount of compounds T present in the composition is greater than 0.5, preferably greater than or equal to 1, more preferentially ranging from 1 to 2.

According to a preferred embodiment, the composition according to the present invention comprises:
i) one or more pyrimidine derivatives chosen from thiamine salts, isomers thereof, solvates thereof such as hydrates, and mixtures thereof, preferably chosen from thiamine chloride, thiamine nitrate, thiamine chloride hydrochloride and mixtures thereof, more preferentially thiamine chloride hydrochloride;
ii) one or more fatty acids chosen from oleic acid, salts thereof, solvates thereof such as hydrates, and mixtures thereof, preferably oleic acid;
it being understood that:
- the composition comprises a total content of compounds T, isomers thereof and mixtures thereof, of greater than or equal to 2% by weight relative to the total weight of the composition; and
- the molar ratio of total amount of fatty acids ii)/total amount of compounds T present in the composition is greater than 0.5; and
- the pH of the composition is between 3.5 and 6.5.

Other characteristics of the composition

The composition is a cosmetic composition, i.e. a composition which comprises a cosmetically acceptable medium, i.e. a medium that is compatible with human keratin fibres.

The composition may comprise a solvent chosen from 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.

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

Preferably, the composition comprises a solvent chosen from water, ethanol, isopropanol, propylene glycol, and mixtures thereof.

More preferentially, the composition comprises a solvent chosen from water, ethanol, propylene glycol, and mixtures thereof.

The composition may also comprise at least one cosmetic ingredient chosen from non-ionic, anionic, cationic and amphoteric surfactants, vitamins and provitamins other than vitamin B1, including panthenol, fillers, dyestuffs, nacreous agents, opacifiers, sequestrants, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antifoams, moisturizers, emollients, penetrants, fragrances, preserving agents, and mixtures thereof.

These usual cosmetic ingredients may be present in the composition in usual amounts, which may readily be determined by a person 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. A person skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the composition.

The composition may be in any presentation form conventionally used for a haircare application. In a non-limiting manner, the composition may be in the form of a lotion, a cream, a mousse, a gel, a spray or a lacquer.

The composition may be used in a rinse-off or leave-on application.

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

The composition may be packaged in a pump bottle or in an aerosol container, so as to apply the composition in vaporized (lacquer) or foam form. In these cases, the composition preferably comprises at least one propellant.

The pH of the composition is between 3.5 and 6.5, preferably between 3.5 and 5.5, more preferentially between 4 and 5, even more preferentially between 4.25 and 4.75. Preferably, the pH of the composition is equal to 4. The pH may be adjusted using an organic or mineral acid or an organic or mineral base usually used in cosmetics.

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

The term “colouring agent” means an oxidation dye, a direct dye or a pigment.

The term “oxidation dye” means an oxidation dye precursor chosen from oxidation bases and couplers. Oxidation bases and couplers are colourless or sparingly coloured compounds, which, via a condensation reaction in the presence of an oxidizing agent, give a coloured species.

The term “direct dye” means a natural and/or synthetic dye, including in the form of an extract or extracts, other than oxidation dyes. These are coloured compounds that will spread superficially on the fibre. They may be ionic or non-ionic, i.e. anionic, cationic, neutral or non-ionic.

Process for treating keratin fibres

The composition may be applied to dry or wet keratin fibres, preferably wet keratin fibres.

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

The bath ratio of the composition applied to the keratin fibres may range from 0.01 to 10. By way of example, the bath ratio may be 0.2. The term “bath ratio” means the ratio between the total weight of the composition applied and the total weight of keratin fibres to be treated.

The process may comprise at least one additional step following step a), chosen from steps b) to d) below:
b) a step of applying the composition to the keratin fibres, preferably for a period of at least 10 seconds, said application step optionally being performed under an airtight film of wrapper or plastic film type;
c) a step of rinsing and/or washing the keratin fibres;
d) a step of drying the keratin fibres in ambient air or using a heating device.

Preferably, the process comprises the additional steps b) and d) as described previously and performed in that order.

The step of applying the composition may last from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.

The washing step may be performed, for example, using a shampoo.

The temperature of the heating device may range from 45°C to 230°C, preferably from 45°C to 100°C, more preferentially from 50°C to 80°C. A hairdryer, a heating hood, an iron or a heating brush may be used, for example, as heating device.

The drying step d) may also be a combination of drying with air or with a heating device at a temperature ranging from 50°C to 80°C, such as a hairdryer or a heating hood, possibly followed by an ironing step, preferably with a straightening iron.

Steps a) to c) or steps a) to d) may be repeated as many times as required and each cycle of steps a) to c) or a) to d) 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.

In the case where the process does not comprise a step c) of rinsing and/or washing the keratin fibres, the composition may, for example, comprise a solvent mixture such as a water/ethanol mixture which comprises at least 10%, preferably at least 20% and more preferentially at least 30% by weight of ethanol. The use of such a mixture can notably facilitate the evaporation of the composition.

Uses

According to a fifth aspect, a subject of the present invention is the use of one or more fatty acids ii) as defined above, for stabilizing a composition, preferably for stabilizing the odour of a composition comprising one or more pyrimidine derivatives i) as defined above, the composition comprising a total content of compounds T, isomers thereof and mixtures thereof preferably of greater than 1.90% by weight, more preferentially greater than or equal to 2% by weight, even more preferentially ranging from 2% to 10% by weight, most preferentially ranging from 3% to 8% by weight, and better still ranging from 3% to 7% by weight relative to the total weight of the composition.

Examples

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

a. Preparation of the formulations

The following compositions A₁ to A₃₀ and B₁ to B₃ were prepared. The pH of the water/ethanol mixture was adjusted to pH=4 or 6.3 with sodium hydroxide. These compositions were evaluated as regards their stability and/or resistance to breakage and/or to irreversible deformation.

Composition	Mass % thiamine Cl HCl (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine Cl HCl molar ratio	Water	Ethanol	pH
A₁ (Invention)	8.43 (6.63)	7.05	1.00	41.57	42.95	4
A₂ (Invention)	5.62 (4.42)	4.7	1.00	44.38	45.3	4
A₃ (Invention)	4.21 (3.31)	3.53	1.00	45.79	46.47	4
A₄ (Invention)	2.81 (2.21)	2.35	1.00	47.19	47.65	4
A₅ (Invention)	5.62 (4.42)	9.4	2.00	44.38	40.6	4
A₆ (Invention)	3.37 (2.65)	5.64	2.00	46.63	44.36	4
A₇ (Comparative)	1.53 (1.20)	2.56	2.00	48.47	47.44	4
A₈ (Comparative)	16.85 (13.26)	0	0.00	83.15	0	4
A₉ (Comparative)	8.43 (6.63)	0	0.00	91.57	0	4
A₁₀ (Comparative)	5.62 (4.42)	0	0.00	94.38	0	4
A₁₁ (Comparative)	3.37 (2.65)	0	0.00	96.63	0	4
A₁₂ (Comparative)	0	14.1	N/A	0	85.9	4
A₁₃ (Comparative)	0	7.05	N/A	0	92.95	4
A₁₄ (Comparative)	0	4.7	N/A	0	95.3	4
A₁₅ (Comparative)	0	2.82	N/A	0	97.18	4
A₁₆ (Invention)	8.43 (6.63)	14.1	2.00	41.57	35.9	4
A₁₇ (Invention)	4.21 (3.31)	7.05	2.00	45.79	42.95	4
A₁₈ (Invention)	2.81 (2.21)	4.7	2.00	47.19	45.3	4
A₁₉ (Comparative)	1.69 (1.33)	2.82	1.99	48.31	47.18	4
A₂₀ (Invention)	6.74 (5.30)	8.46	1.50	43.26	41.54	4
A₂₁ (Invention)	3.74 (2.94)	4.7	1.50	46.26	45.3	4
A₂₂ (Invention)	2.59 (2.04)	3.25	1.50	47.41	46.75	4
A₂₃ (Invention)	7.66 (6.03)	7.69	1.20	42.34	42.31	4
A₂₄ (Invention)	4.01 (3.15)	4.03	1.20	45.99	45.97	4
A₂₅ (Invention)	2.72 (2.14)	2.73	1.20	47.28	47.27	4
A₂₆ (Comparative)	1.65 (1.30)	1.66	1.20	48.35	48.34	4
A₂₇ (Comparative)	16.85 (13.26)	0	0.00	83.15	0	6.3
A₂₈ (Invention)	5.62 (4.42)	9.4	2.00	44.38	40.6	6.3
A₂₉ (Comparative)	2.41 (1.90)	2	0.99	47.59	48	4
A₃₀ (Comparative)	2.41 (1.90)	1	0.50	47.59	49	4

Composition	Mass % thiamine nitrate (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine nitrate molar ratio	Water	Ethanol	pH
B₁ (Invention)	3 (2.43)	3	1.16	47	47	4
B₂ (Invention)	3 (2.43)	4	1.55	47	46	4
B₃ (Invention)	3 (2.43)	5	1.93	47	45	4

b. Study of the stability of the compositions

Each of the compositions A₁ to A₃₀ and B₁ to B₃ were placed in two separate flasks sealed with Parafilm to prevent vapour leaks. One of the two flasks was placed in an oven at 66°C for 1 week to study the storage stability at elevated temperatures. The other flask was left at ambient temperature (22°C). After one week, the flasks are left to stand for 2 h so that the flasks at 66°C return to ambient temperature. Then, each bottle, one after the other, is opened for 5 seconds and an olfactory evaluation is made. The intensity of the change in odour of the formulations, after storage, is evaluated using the scale: 0 = no odour, 1 = very weak odour, 2 = weak odour, 3 = noticeable odour, 4 = intense and unpleasant odour, 5 = very intense and very unpleasant odour.

Only the formulations with a score of 0 to 2 inclusive are judged to be stable.

c. Study of breakage and irreversible deformation of the hair

The compositions A₁ to A₃₀ and B₁ to B₃ were applied according to the application protocol described below and evaluated with regard to their integrity, namely their resistance to breakage and to irreversible deformation according to the test protocol described below.

Application protocol

Damaged locks of hair (type 1 cf. De la Mettrie R, et al. Shape variability and classification of human hair: A worldwide approach. Human Biology. 2007; 79: 265-281) are washed with DOP shampoo, then wrung between the fingers (2 passes). The wet locks are then placed on a flat surface and then the compositions A₁ to A₃₀ and B₁ to B₃, freshly prepared, are applied separately to said locks with a bath ratio of 0.2 (namely 0.2 g of composition per 1 g of hair).

The locks are then massaged with the fingers, making circular movements throughout each lock (5 times), then the locks are left to dry in an incubator at 60°C (10 min/g of hair). These shampooing and formulation application and drying steps are repeated to have 6 applications in total.

A damaged and untreated lock of hair is used as a reference.

Test protocol

The test consists in pulling on the damp hair to see if it breaks, deforms irreversibly or becomes deformed and then returns to its original shape and length. The test is commonly used by hairdressers to evaluate the integrity of their clients’ hair. The test consists in taking a lock of hair, soaking it in water for 30 seconds and then taking and holding three hair fibres between the index finger and thumb of both hands (each hand takes one end of the fibres). The fibres are then put under slight tension by moving the fingers and thumbs of each hand apart so that there are 3 centimetres of fibre between the hands, and then pulling so that the fibres are deformed by a further 1 cm. A ruler is used to ensure that the stretching distances are respected. The fibres are held for 3 seconds and then the tension is gently released. The fibres are placed horizontally on absorbent paper for 5 minutes to allow them to dry, and are then evaluated.

The test is repeated five times, for a total of 15 fibres.

The hair integrity performance is graded according to the following rules:
● If the sum of the broken and irreversibly deformed fibres is greater than or equal to 10, the hair has very poor integrity.
● If the sum of the broken and irreversibly deformed fibres is between 6 and 9 inclusive, the individual hair has a poor integrity.
● If the sum of the broken and irreversibly deformed fibres is between 2 and 5 inclusive, the individual hair has a good integrity.
● If the sum of the broken and irreversibly deformed fibres is 1 or less, the individual hair has a very good integrity.

d. Results of the stability measurements:

The results of the stability measurements for each of the compositions tested are summarized in the tables below.

Composition	Mass % thiamine Cl HCl (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine Cl HCl molar ratio	pH	Intensity of change in odour
Composition	Mass % thiamine Cl HCl (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine Cl HCl molar ratio	pH	After one week at ambient temperature	After one week at 66°C
A₁ (Invention)	8.43 (6.63)	7.05	1.00	4	2	2
A₂ (Invention)	5.62 (4.42)	4.7	1.00	4	2	2
A₃ (Invention)	4.21 (3.31)	3.53	1.00	4	1	2
A₄ (Invention)	2.81 (2.21)	2.35	1.00	4	0	1
A₅ (Invention)	5.62 (4.42)	9.4	2.00	4	0	2
A₆ (Invention)	3.37 (2.65)	5.64	2.00	4	0	2
A₇ (Comparative)	1.53 (1.20)	2.56	2.00	4	0	0
A₈ (Comparative)	16.85 (13.26)	0	0.00	4	0	4
A₉ (Comparative)	8.43 (6.63)	0	0.00	4	0	4
A₁₀ (Comparative)	5.62 (4.42)	0	0.00	4	0	4
A₁₁ (Comparative)	3.37 (2.65)	0	0.00	4	0	3
A₁₂ (Comparative)	0	14.1	N/A	4	0	0
A₁₃ (Comparative)	0	7.05	N/A	4	0	0
A₁₄ (Comparative)	0	4.7	N/A	4	0	0
A₁₅ (Comparative)	0	2.82	N/A	4	0	0
A₁₆ (Invention)	8.43 (6.63)	14.1	2.00	4	0	2
A₁₇ (Invention)	4.21 (3.31)	7.05	2.00	4	0	0
A₁₈ (Invention)	2.81 (2.21)	4.7	2.00	4	0	0
A₁₉ (Comparative)	1.69 (1.33)	2.82	1.99	4	0	0
A₂₀ (Invention)	6.74 (5.30)	8.46	1.50	4	1	2
A₂₁ (Invention)	3.74 (2.94)	4.7	1.50	4	0	0
A₂₂ (Invention)	2.59 (2.04)	3.25	1.50	4	0	0
A₂₃ (Invention)	7.66 (6.03)	7.69	1.20	4	0	0
A₂₄ (Invention)	4.01 (3.15)	4.03	1.20	4	0	0
A₂₅ (Invention)	2.72 (2.14)	2.73	1.20	4	0	0
A₂₆ (Comparative)	1.65 (1.30)	1.66	1.20	4	0	0
A₂₇ (Comparative)	16.85 (13.26)	0	0.00	6.3	0	0
A₂₈ (Invention)	5.62 (4.42)	9.4	2.00	6.3	0	2
A₂₉ (Comparative)	2.41 (1.90)	2	0.99	4	0	2
A₃₀ (Comparative)	2.41 (1.90)	1	0.50	4	0	3

Composition	Mass % thiamine nitrate (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine nitrate molar ratio	pH	Intensity of change in odour
Composition	Mass % thiamine nitrate (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine nitrate molar ratio	pH	After one week at ambient temperature	After one week at 66°C
B₁ (Invention)	3 (2.43)	3	1.16	4	0	1
B₂ (Invention)	3 (2.43)	4	1.55	4	0	0
B₃ (Invention)	3 (2.43)	5	1.93	4	0	0

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

e. Results of the integrity measurements

The results of the integrity measurements for each of the compositions A₁ to A₃₀ and B₁ to B₃ tested are summarised in the tables below.

Composition	Mass % thiamine Cl HCl (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine Cl HCl molar ratio	pH	Number of broken fibres	Number of irreversibly deformed fibres
A₁ (Invention)	8.43 (6.63)	7.05	1.00	4	0	1
A₂ (Invention)	5.62 (4.42)	4.7	1.00	4	0	1
A₃ (Invention)	4.21 (3.31)	3.53	1.00	4	0	3
A₄ (Invention)	2.81 (2.21)	2.35	1.00	4	0	4
A₅ (Invention)	5.62 (4.42)	9.4	2.00	4	0	0
A₆ (Invention)	3.37 (2.65)	5.64	2.00	4	0	1
A₇ (Comparative)	1.53 (1.20)	2.56	2.00	4	0	6
A₈ (Comparative)	16.85 (13.26)	0	0.00	4	0	5
A₉ (Comparative)	8.43 (6.63)	0	0.00	4	0	5
A₁₀ (Comparative)	5.62 (4.42)	0	0.00	4	0	5
A₁₁ (Comparative)	3.37 (2.65)	0	0.00	4	1	6
A₁₂ (Comparative)	0	14.1	N/A	4	0	6
A₁₃ (Comparative)	0	7.05	N/A	4	0	6
A₁₄ (Comparative)	0	4.7	N/A	4	0	6
A₁₅ (Comparative)	0	2.82	N/A	4	0	7
A₁₆ (Invention)	8.43 (6.63)	14.1	2.00	4	0	1
A₁₇ (Invention)	4.21 (3.31)	7.05	2.00	4	0	1
A₁₈ (Invention)	2.81 (2.21)	4.7	2.00	4	0	3
A₁₉ (Comparative)	1.69 (1.33)	2.82	1.99	4	0	7
A₂₀ (Invention)	6.74 (5.30)	8.46	1.50	4	0	2
A₂₁ (Invention)	3.74 (2.94)	4.7	1.50	4	0	4
A₂₂ (Invention)	2.59 (2.04)	3.25	1.50	4	0	5
A₂₃ (Invention)	7.66 (6.03)	7.69	1.20	4	0	1
A₂₄ (Invention)	4.01 (3.15)	4.03	1.20	4	0	2
A₂₅ (Invention)	2.72 (2.14)	2.73	1.20	4	0	4
A₂₆ (Comparative)	1.65 (1.30)	1.66	1.20	4	0	7
A₂₇ (Comparative)	16.85 (13.26)	0	0.00	6.3	0	6
A₂₈ (Invention)	5.62 (4.42)	9.4	2.00	6.3	0	2
A₂₉ (Comparative)	2.41 (1.90)	2	0.99	4	0	6
A₃₀ (Comparative)	2.41 (1.90)	1	0.50	4	1	6

Composition	Mass % thiamine nitrate (mass % thiamine)	Mass % oleic acid	Oleic acid/thiamine nitrate molar ratio	pH	Number of broken fibres	Number of irreversibly deformed fibres
B₁ (Invention)	3 (2.43)	3	1.16	4	0	3
B₂ (Invention)	3 (2.43)	4	1.55	4	0	2
B₃ (Invention)	3 (2.43)	5	1.93	4	0	2

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

Claims

Composition comprising:
i) one or more pyrimidine derivatives chosen from the compounds of formula (I) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:
T xAn^- (I)
in which formula (I):
▪ T represents a compound chosen from the compounds of formula (II) below:

(II)
in which formula (II):
▪ R¹ represents a (C₁-C₄)alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: hydroxyl (-OH), phenyl (-C₆H₅) or -C(O)OM in which M represents a hydrogen atom, an alkali metal or alkaline-earth metal, or a negative charge;
▪ R² represents a hydrogen atom or a (C₁-C₄)alkyl group;
▪ R³ represents a hydrogen atom or a (C₁-C₄)alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: a hydroxyl (-OH), -C(O)OM in which M is as defined above, chloride, fluoride, -CHO, -ONO₂, -OSO₃H, -OPO₃H₂ and/or optionally interrupted with one or more groups or heteroatoms, which may be identical or different, chosen from O, S, N, -C(O)- or -S(O)-;
▪ R⁴ represents a hydrogen atom or a (C₁-C₄)alkyl group optionally substituted with a hydroxyl group (-OH);
▪ x represents a stoichiometric coefficient greater than or equal to zero, chosen so as to ensure the electrical neutrality of the compound of formula (I);
▪ An^- represents an inorganic or organic anion chosen from Cl^-, Br^-, I^-, F^-, OH^-, NO₂ ^-, NO₃ ^-, PO₄ ^3-, SO₄ ^2-, H₂PO₄ ^-, H₃P₂O₇ ^-, R-SO₂-O^-, R-O-SO₃ ^-, anions derived from amino acids, preferably of L configuration, more preferentially L-prolinate, L-glutamate or L-aspartate;
▪ R represents a (C₁-C₄)alkyl group;
ii) one or more fatty acids chosen from unsaturated fatty acids, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof;
in which:
- the composition comprises a total content of compounds T, isomers thereof and mixtures thereof, of greater than or equal to 2% by weight relative to the total weight of the composition; and
- the molar ratio of total amount of fatty acids ii)/total amount of compounds T present in the composition is greater than 0.5; and
- the pH of the composition is between 3.5 and 6.5.
Composition according to Claim 1, in which the pyrimidine derivative(s) i) are chosen from thiamine salts, isomers thereof, solvates thereof such as hydrates, and mixtures thereof; preferably, the pyrimidine derivative(s) i) are chosen from thiamine chloride, thiamine nitrate, thiamine chloride hydrochloride and mixtures thereof; more preferentially, the pyrimidine derivative i) chosen is thiamine chloride hydrochloride.
Composition according to either one of the preceding claims, in which the compound(s) T, isomers thereof and mixtures thereof are present in the composition in a total content ranging from 2% to 10% by weight, more preferentially ranging from 2.5% to 10% by weight, even more preferentially ranging from 3% to 8% by weight, most preferentially ranging from 3% to 7% relative to the total weight of the composition.
Composition according to any one of the preceding claims, in which the fatty acid(s) ii) are chosen from the compounds of formula (III) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:
(III)
in which formula (III) R represents a (C₈-C₄₀)alkenyl group optionally substituted with one or more hydroxyl groups (-OH), preferably a (C₁₀-C₃₀)alkenyl group optionally substituted with one or more hydroxyl groups (-OH), more preferentially a (C₁₂-C₂₄)alkenyl group optionally substituted with one or more hydroxyl groups (-OH).
Composition according to any one of the preceding claims, in which the fatty acid(s) ii) are chosen 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, salts thereof, isomers thereof, solvates thereof such as hydrates, and mixtures thereof; preferably, the fatty acid(s) ii) are chosen from oleic acid, salts thereof, solvates thereof such as hydrates, and mixtures thereof; more preferentially the fatty acid ii) is oleic acid.
Composition according to any one of the preceding claims, in which the fatty acid(s) ii) are present in the composition in a total content ranging from 2% to 15% by weight, preferably ranging from 2% to 10% by weight, relative to the total weight of the composition.
Composition according to any one of the preceding claims, in which the molar ratio of total amount of fatty acids ii)/total amount of compounds T present in the composition is greater than or equal to 1, preferably ranging from 1 to 2.
Composition according to any one of the preceding claims, in which the composition comprises a solvent chosen from water, C₂-C₄ alcohols, polyols, polyol ethers and mixtures thereof, preferably from water, ethanol, isopropanol, propylene glycol and mixtures thereof, more preferentially from water, ethanol, propylene glycol and mixtures thereof.
Composition according to any one of the preceding claims, in which the pH of the composition is between 3.5 and 5.5, preferably between 4 and 5, more preferentially between 4.25 and 4.75; even more preferentially, the pH of the composition is 4.
Process for treating keratin fibres, comprising a) the application to the keratin fibres of a composition as defined in any one of the preceding claims.
Process according to the preceding claim, comprising at least one additional step following step a), chosen from steps b) to d) below:
b) a step of applying the composition to the keratin fibres, preferably for a period of at least 10 seconds, said application step optionally being performed under an airtight film of wrapper or plastic film type;
c) a step of rinsing and/or washing the keratin fibres;
d) a step of drying the keratin fibres in ambient air or using a heating device.
Use of a composition as defined in any one of Claims 1 to 9, for preventing the irreversible deformation of keratin fibres during combing and/or disentangling.
Use of a composition as defined in any one of Claims 1 to 9, for repairing and/or preventing the breakage of keratin fibres.
Use according to Claim 12 or 13, in which the keratin fibres are damaged and/or sensitized keratin fibres.
Use of one or more fatty acids ii) as defined in any one of Claims 1, 4 or 5, for stabilizing a composition, preferably for stabilizing the odour of a composition comprising one or more pyrimidine derivatives i) as defined Claim 1 or 2, the composition comprising a total content of compounds T, isomers thereof and mixtures thereof preferably of greater than 1.90% by weight, more preferentially greater than or equal to 2% by weight, even more preferentially ranging from 2% to 10% by weight, most preferentially ranging from 3% to 8% by weight, and better still ranging from 3% to 7% by weight relative to the total weight of the composition.