Process for treating keratin fibres using one or more particular peptides or a composition comprising same
Applying peptides with specific sequences at a pH of 3.5 to 6.5 addresses the limitations of existing hair care products by improving fiber quality, reducing breakage, and preventing deformation in damaged hair, offering sustainable conditioning.
Patent Information
- Application Number
- PCT/EP2025/064147
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-05-24
- Filing Date
- 2025-05-22
- Publication Date
- 2025-11-27
AI Technical Summary
Existing hair care products fail to provide long-lasting conditioning effects and do not prevent irreversible deformation or breakage of keratin fibers, especially in damaged and sensitized hair, while also lacking environmental sustainability.
A process involving the application of peptides with specific sequences, particularly those with a C-terminal end of lysine or arginine, and their salts or solvates, at a pH between 3.5 and 6.5, to treat keratin fibers, enhancing properties like softness, manageability, and preventing breakage.
The process improves the quality of keratin fibers by reducing breakage, enhancing softness and smoothness, and preventing irreversible deformation during combing and disentangling, while being environmentally friendly.
Abstract
Description
PROCESS FOR TREATING KERATIN FIBRES USING ONE OR MORE PARTICULAR PEPTIDES OR A COMPOSITION COMPRISING SAMETECHNICAL FIELD OF THE INVENTION
[0001] The present invention relates to a process for treating keratin fibres using one or more particular peptides or a composition comprising same.BACKGROUND OF THE INVENTION
[0002] 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.
[0003] 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.
[0004] These hair care compositions, which are intended to be applied regularly to the hair, can be, for example, conditioners, masks or serums, and can be provided in the form of gels, hair lotions and care creams which are more or less thick.
[0005] However, the conditioning effect conferred by such hair care products generally fades rapidly over time, does not always show satisfactory persistence with respect to shampoo washing and does not make it possible to prevent irreversible deformation of the hair due to elongation of the fibres, for example during combing or disentangling, nor to repair or prevent hair breakage.
[0006] Moreover, the formulation of environmentally friendly cosmetic products, i.e. products the design and development of which take account of environmental issues, is becoming a major concern for contributing towards meeting global challenges. It thus proves essential to propose more sustainable compositions, thereby making it possible to respond to these environmental issues by reducing in particular the use of compounds of petrochemical origin.
[0007] There is thus a real need to develop a hair treatment process that makes it possible to overcome these drawbacks and which is capable in particular of preserving or even improving the quality of the fibre, especially the softness, the disentangling, the smooth feel, the manageability and / or the sheen and / or to prevent the irreversible deformation of the hair due to elongation of the fibres, for example during combing or disentangling, in particular of damaged and / or sensitized hair, and / or to repair or prevent hair breakage, especially of damaged and / or sensitized hair.
[0008] The applicant has discovered, surprisingly, that all or some of these objectives can be achieved by the process according to the present invention.SUMMARY OF THE INVENTION
[0009] According to a first aspect, the present invention provides a process for treating keratin fibres comprising a) the application, to the keratin fibres, of one or more compounds P or of a composition (C) comprising same, the compound(s) P being chosen from peptides having a sequence consisting of 3 to 6 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0010] According to a second aspect, the present invention provides a composition (C) as defined above, wherein the pH of the composition (C) is between 3.5 and 6.5, preferably between 3.5 and 5.5, more preferentially between 4 and 5, more preferentially still between 4.25 and 4.75; most preferentially, the pH of the composition (C) is 4.
[0011] According to a third aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for caring for keratin fibres, preferably for giving keratin fibres a soft and / or smooth feel and / or sheen, more preferentially for giving them a soft and / or smooth feel.
[0012] According to a fourth aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for preventing the irreversible deformation of keratin fibres during combing and / or disentangling.
[0013] According to a fifth aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for repairing and / or preventing breakage of keratin fibres.
[0014] DETAILED DESCRIPTION OF THE INVENTION
[0015] For the purposes of the present invention and unless otherwise indicated:
[0016] ▪ the term "keratin fibres" is understood to mean 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.
[0017] ▪ the term "damaged keratin fibres" is understood to mean keratin fibres that are dry, rough, brittle, split and / or limp.
[0018] ▪ the term "sensitized keratin fibres" is understood to mean keratin fibres that have been bleached, artificially coloured, relaxed and / or permanent-waved.
[0019] ▪ the term "heterocyclic group" is understood to mean a fused or nonfused, saturated or unsaturated, aromatic or non-aromatic, mono- or polycyclic group comprising from 3 to 10 carbon atoms and at least one of the ring members of which is a heteroatom chosen from a nitrogen, oxygen or sulfur atom.
[0020] ▪ the term "alkyl group" is understood to mean a saturated, linear or branched hydrocarbon radical comprising from 1 to 30 carbon atoms, preferentially from 1 to 26 carbon atoms, more preferentially 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.
[0021] ▪ the term "(Cx-Cy)alkyl group" is understood to mean an alkyl group comprising from x to y carbon atoms.
[0022] ▪ the term "salt" is understood to mean an addition salt with an organic or mineral acid or base. The addition salts with an acid are chosen in particular from addition salts with organic or mineral acids such as hydrochloric acid, hydrobromic acid, hydroiodic 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 chosen in particular from the addition salts with organic or mineral bases such as alkali metal hydroxides, alkaline-earth metal hydroxides, ammonia, amines or alkanolamines.
[0023] ▪ the term "isomer" is understood to mean an optical, geometrical or tautomeric isomer.
[0024] The expressions "at least one" and "one or more" are synonymous and may be used interchangeably.
[0025] 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.Process for treating keratin fibres
[0026] According to a first aspect, the present invention provides a process for treating keratin fibres as defined above.
[0027] The applicant has found, surprisingly, that the process according to the present invention makes it possible to preserve or even improve the quality of the keratin fibres, in particular of damaged and / or sensitized keratin fibres, so as to repair them and / or reduce the breakage thereof and also to improve the softness, the disentangling, the smooth feel, the manageability and / or the sheen thereof.Compounds P
[0028] The compound(s) P are chosen from peptides having a sequence consisting of 3 to 6 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0029] The compound(s) P may be chosen from peptides having a sequence consisting of 3 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0030] The compound(s) P may be chosen from peptides having a sequence consisting of 4 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0031] The compound(s) P may be chosen from peptides having a sequence consisting of 5 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0032] The compound(s) P may be chosen from peptides having a sequence consisting of 6 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0033] Preferably, the compound(s) P are chosen from peptides having a sequence consisting of 3 or 4 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0034] According to a first embodiment, the compound(s) P are chosen from peptides having a sequence consisting of 3 to 6 amino acids, preferably of 3 or 4 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0035] According to a second embodiment, the compound(s) P are chosen from peptides having a sequence consisting of 3 to 6 amino acids, preferably of 3 or 4 amino acids, and the sequence comprises lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof. According to this second embodiment, the C-terminal end of the peptides may not be chosen from lysine or arginine.
[0036] According to a third embodiment, the compound(s) Pare chosen from peptides having a sequence consisting of 3 to 6 amino acids, preferably of 3 or 4 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.
[0037] The compound(s) P are non-acylated.
[0038] Preferably, the compound(s) P are chosen from the compounds of formula (I):AA1-AA2-(AAi)n-AA3(I)in which formula (I):- AA1, AA2, AA3and AAi, which may be identical or different, denote an amino acid;- n denotes an integer equal to 0, 1, 2 or 3, preferably n is equal to 0 or 1;- when n is equal to 2 or 3, the amino acids AAiare identical or different;it being understood that:- at least one of the amino acids AA1, AA2, AA3or AAiis chosen from lysine or arginine; and- if AA3denotes lysine or arginine then AA1, AA2and AAidenote any amino acid; and- if AA3is other than lysine and arginine, then at least two adjacent amino acids are chosen from lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine.
[0039] Preferably, the amino acids AA1, AA2, AA3and AAiare independently chosen from arginine, lysine, glycine, proline, alanine, valine, leucine, threonine, beta-alanine, isoleucine, phenylalanine, asparagine or methionine, preferably from arginine, lysine, glycine, proline, alanine, valine, leucine or threonine.
[0040] The amino acids AA1, AA2, AA3and AAimay be in the form of an optical isomer of L, D or DL configuration, preferably of L configuration.
[0041] More preferably, the amino acids AA1, AA2, AA3and AAiare chosen from L-arginine, L-lysine, glycine, L-proline, L-alanine, L-valine, L-leucine, L-threonine, beta-alanine, L-isoleucine, L-phenylalanine, L-asparagine or L-methionine, preferably from L-arginine, L-lysine, glycine, L-proline, L-alanine, L-valine, L-leucine or L-threonine.
[0042] According to a preferred embodiment, the compound(s) Pare chosen from Leucine-Alanine-Lysine (LAK), Valine-Proline-Lysine (VPK), Glycine-Lysine-Arginine (GKR), Arginine-Proline-Arginine (RPR), Threonine-Lysine-Proline-Arginine (TKPR), Alanine-Lysine-Lysine (AKK), Valine-Lysine-Lysine (VKK), Arginine-Arginine-Arginine (RRR), Arginine-Lysine-Arginine-Arginine (RKRR), Arginine-Arginine-Lysine-Lysine-Proline (RRKKP), Lysine-Lysine-Lysine (KKK), Arginine-Glycine-Lysine (RGK), salts thereof, solvates thereof such as the hydrates, and mixtures thereof, preferably from Leucine-Alanine-Lysine (LAK), Valine-Proline-Lysine (VPK), Glycine-Lysine-Arginine (GKR), Arginine-Proline-Arginine (RPR), Threonine-Lysine-Proline-Arginine (TKPR), Alanine-Lysine-Lysine (AKK), Valine-Lysine-Lysine (VKK), Arginine-Arginine-Arginine (RRR), Arginine-Lysine-Arginine-Arginine (RKRR), Arginine-Arginine-Lysine-Lysine-Proline (RRKKP), salts thereof, solvates thereof such as the hydrates, and mixtures thereof.
[0043] According to a more preferred embodiment, the compound(s) Pare chosen from L-leucine-L-alanine-L-lysine (LAK), L-valine-L-proline-L-lysine (VPK), glycine-L-lysine-L-arginine (GKR), L-arginine-L-proline-L-arginine (RPR), L-threonine-L-lysine-L-proline-L-arginine (TKPR), L-alanine-L-lysine-L-lysine (AKK), L-valine-L-lysine-L-lysine (VKK), L-arginine-L-arginine-L-arginine (RRR), L-arginine-L-lysine-L-arginine-L-arginine (RKRR), L-arginine-L-arginine-L-lysine-L-lysine-L-proline (RRKKP), L-lysine-L-lysine-L-lysine (KKK), L-arginine-Glycine-L-lysine (RGK), salts thereof, solvates thereof such as the hydrates, and mixtures thereof, preferably from L-leucine-L-alanine-L-lysine (LAK), L-valine-L-proline-L-lysine (VPK), glycine-L-lysine-L-arginine (GKR), L-arginine-L-proline-L-arginine (RPR), L-threonine-L-lysine-L-proline-L-arginine (TKPR), L-alanine-L-lysine-L-lysine (AKK), L-valine-L-lysine-L-lysine (VKK), L-arginine-L-arginine-L-arginine (RRR), L-arginine-L-lysine-L-arginine-L-arginine (RKRR), L-arginine-L-arginine-L-lysine-L-lysine-L-proline (RRKKP), salts thereof, solvates thereof such as the hydrates, and mixtures thereof.
[0044] Preferably, the compound(s) P are other than the peptides chosen from Arginine-Arginine-Arginine (RRR), Lysine-Lysine-Lysine (KKK), salts thereof, solvates thereof such as the hydrates, and mixtures thereof.
[0045] The chemical synthesis of the peptides may be carried out in solution or on a solid phase. The process consists in forming, in a directed and selective manner, an amide bond between an N-protected amino acid and an amino acid bearing a free amino group and a protected carboxyl group. In solid-phase synthesis, the carboxyl-protecting group is bonded to a polymeric support. After formation of the bond, the group protecting the amino function of the peptide is removed, and the following N-protected amino acid is coupled.Composition (C)
[0046] According to one embodiment, the compound(s) P are included in a composition (C).
[0047] The composition (C) preferably comprises a total content of compounds P ranging from 0.005% to 25% by weight, more preferentially ranging from 0.01% to 20% by weight, more preferentially still ranging from 0.05% to 10% by weight, most preferentially ranging from 0.1% to 2% by weight, relative to the total weight of the composition (C).
[0048] The composition (C) 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.
[0049] Preferably, the composition (C) comprises water. The composition (C) may comprise, in addition to water, at least one water-miscible solvent, preferably chosen from 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.
[0050] The composition (C) may comprise, in addition to water, a solvent chosen from C2-C4alcohols, polyols, polyol ethers, and mixtures thereof.
[0051] Preferably, the composition (C) comprises water and optionally a solvent chosen from ethanol, isopropanol, propylene glycol and mixtures thereof.
[0052] The composition (C) preferably comprises from 30% to 99.995% by weight of water, more preferentially from 50% to 99.995% by weight of water.
[0053] The composition (C) may additionally comprise at least one cosmetic ingredient chosen from nonionic, anionic, cationic and amphoteric surfactants, fillers, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antifoams, moisturizers, emollients, penetrants, fragrances, preserving agents, and mixtures thereof.
[0054] These usual cosmetic ingredients may be present in the composition (C) 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 (C). A person skilled in the art will take care to choose the ingredients included in the composition (C), and also the amounts thereof, so that they do not harm the properties of the composition (C).
[0055] The composition (C) may be in any presentation form conventionally used for hair application. In a nonlimiting manner, the composition (C) may be in the form of a lotion, a cream, a mousse, a gel, a spray or a lacquer.
[0056] The composition (C) may be used in a rinse-off or leave-on application.
[0057] The composition (C) may be in the form of a shampoo, a mask, a conditioning composition or a pre-shampoo. The composition (C) 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.
[0058] The composition (C) may be packaged in a pump bottle or in an aerosol container, so as to apply the composition (C) in vaporized (lacquer) or mousse form. In these cases, the composition (C) preferably comprises at least one propellant.
[0059] The pH of composition (C) is preferably between 3.5 and 6.5, more preferentially between 3.5 and 5.5, more preferentially still between 4 and 5, most preferentially still between 4.25 and 4.75. Preferably, the pH of the composition (C) 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.
[0060] The composition (C) may be applied to dry or wet keratin fibres, preferably wet keratin fibres.
[0061] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.
[0062] 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 0.4. The term "bath ratio" is understood to mean the ratio between the total weight of the composition applied and the total weight of keratin fibres to be treated.
[0063] The process may comprise at least one additional step a') of washing the keratin fibres prior to or simultaneously with step a), preferably prior to step a) and / or at least one additional step successive to step a) and chosen from the following steps b) to d):b) a step of applying the composition (C) to the keratin fibres, preferably for a duration of at least 10 seconds, said application step optionally being performed under an airtight film of curl-paper 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.
[0064] Preferably, the process comprises step a') as described above and also the additional steps b), c) and d) as described above and performed in that order.
[0065] The step of applying the composition may have a duration ranging from 10 seconds to 60 minutes, preferably ranging from 30 seconds to 30 minutes, more preferentially ranging from 30 seconds to 15 minutes.
[0066] The washing step a') or c) may be performed, for example, using a shampoo.
[0067] 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.
[0068] 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.
[0069] Steps a') and a) to c) or steps a') and 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. Hair treatments different from the invention may be performed between different application cycles, before or after.
[0070] 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 in particular facilitate the evaporation of the composition.Uses
[0071] According to a third aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for caring for keratin fibres, preferably for giving keratin fibres a soft and / or smooth feel and / or sheen, more preferentially for giving them a soft and / or smooth feel.
[0072] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.
[0073] According to a fourth aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for preventing the irreversible deformation of keratin fibres during combing and / or disentangling.
[0074] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.
[0075] According to a fifth aspect, the present invention provides for the use of one or more compounds P as defined above or of a composition (C) as defined above, for repairing and / or preventing breakage of keratin fibres.
[0076] Preferably, the keratin fibres are damaged and / or sensitized keratin fibres, in particular damaged and / or sensitized hair.Examples
[0077] The examples that follow will allow the invention to be understood more clearly, without, however, being limiting in nature.Example 1
[0078] a.Preparation of the compositions
[0079] The following compositions C1 to C11 were prepared from the ingredients mentioned in the table below.
[0080] CompositionPeptide – Mass1N NaOH or 1N HClDistilled waterC1(Invention)LAK – 0.25 gqs pH 4qs 10 gC2(Invention)VPK – 0.50 gqs pH 4qs 10 gC3(Invention)GKR – 1.0 gqs pH 4qs 10 gC4(Invention)RPR – 0.50 gqs pH 4qs 10 gC5(Invention)TKPR – 2.0 gqs pH 4qs 10 gC6(Invention)VKK – 1.0 gqs pH 4qs 10 gC7(Invention)AKK – 0.48 gqs pH 4qs 10 gC8(Invention)RRR – 0.51 gqs pH 4qs 10 gC9(Invention)RKRR – 0.45 gqs pH 4qs 10 gC10(Invention)RRKKP – 0.40 gqs pH 4qs 10 gC11(Comparative – Placebo)-qs pH 4qs 10 g
[0081] b.Evaluation of the breakage and irreversible deformation of the hair
[0082] The compositions C1 to C11 were applied to locks of hair according to the application protocol described below and the locks were evaluated with regard to their integrity, namely their resistance to breakage and to irreversible deformation according to the test protocol described below.Application protocol
[0083] Locks of dark brown hair (type II, cf. de La Mettrie R, et al. Shape variability and classification of human hair: A worldwide approach. Human Biology. 2007; 79: 265–281) are bleached by two successive bleaching operations and then washed with DOP shampoo and finally squeezed out between the fingers (2 passes). The wet locks are placed on a flat surface and then the compositions C1 to C11 are applied separately to the locks with a bath ratio of 0.4 (i.e. 0.4 g of composition per 1 g of hair). The locks are then gently massaged with the fingers using circular movements throughout each lock (twice), and the locks are then left to rest for 5 minutes. The locks are then rinsed with tap water for 10 seconds, squeezed dry and then dried in an oven at 60°C (10 min / g of hair). These steps of shampooing, formulation application, rinsing and then drying are repeated in order to have 5 applications in total.Test protocol
[0084] 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 stretched 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.
[0085] The test is carried out in parallel on 5 sets of 3 fibres, i.e. a total of 15 fibres.
[0086] The hair integrity performance is graded according to the following rules:
[0087] ▪ If the sum of the broken and irreversibly deformed fibres is greater than or equal to 10, the hair has very poor integrity.
[0088] ▪ If the sum of the broken and irreversibly deformed fibres is between 6 and 9 inclusive, the hair has a poor integrity.
[0089] ▪ If the sum of the broken and irreversibly deformed fibres is between 2 and 5 inclusive, the hair has a good integrity.
[0090] ▪ If the sum of the broken and irreversibly deformed fibres is 1 or less, the hair has a very good integrity.Results of the integrity measurements
[0091] The results of the integrity measurements for each of the compositions C1 to C11 tested are summarized in the table below.
[0092] CompositionNumber of broken fibresNumber of irreversibly deformed fibresComments on the integrityC1(Invention)12GoodC2(Invention)02GoodC3(Invention)02GoodC4(Invention)03GoodC5(Invention)02GoodC6(Invention)02GoodC7(Invention)04GoodC8(Invention)03GoodC9(Invention)02GoodC10(Invention)01Very goodC11(Comparative – Placebo)36Poor
[0093] The results show that the compositions according to the present invention make it possible to prevent irreversible deformation of the hair and hair breakage.Example 2
[0094] a.Preparation of the compositions
[0095] The following compositions C12 to C16 were prepared from the ingredients mentioned in the table below.
[0096] CompositionPeptide – Mass (mg) – Concentration1N NaOH or 1N HClDistilled waterC12(Invention)LAK – 30 mg (0.01 M)qs pH 4qs 10 gC13(Invention)VPK – 34 mg (0.01 M)qs pH 4qs 10 gC14(Invention)TKPR – 58 mg (0.01 M)qs pH 4qs 10 gC15(Invention)AKK – 35 mg (0.01 M)qs pH 4qs 10 gC16(Comparative – Placebo)-qs pH 4qs 10 g
[0097] b.Evaluation of the hydrophobicity of the hair
[0098] The compositions C12 to C16 were applied to locks of hair according to the application protocol described below and the locks were evaluated with regard to their hydrophobicity according to the test protocol described below.Application protocol
[0099] Locks of dark brown hair (type II, 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 Elseve Dream Long shampoo (0.2 g of shampoo / g of hair). The locks are gently massaged with the fingers using circular movements throughout the lock (twice) for a total of about 15 seconds, rinsed under tap water for 60 seconds and then squeezed out between the fingers (2 passes throughout the lock). The wet locks are placed on a flat surface and then the compositions C12 to C16 are applied separately to the locks with a bath ratio of 0.2 (i.e. 0.2 g of composition per 1 g of hair). The locks are then gently massaged with the fingers using circular movements throughout each lock (twice), and then treated with Elseve Dream Long conditioner (0.1 g of conditioner / g of hair). The locks are gently massaged with the fingers using circular movements throughout the lock (twice) for a total of about 15 seconds, rinsed under tap water for 15 seconds, squeezed out between the fingers (2 passes throughout the lock), combed and then dried in an oven at 60°C (10 min / g of hair).Test protocol
[0100] The surface of natural hair is hydrophobic, due to the presence of natural lipids, the most widespread of which is 18-methyleicosanoic acid. These surface lipids are grafted to the epicuticle by a thioester bond, providing the natural hair with lubrication that facilitates the disentangling and styling thereof. In damaged hair, environmental conditions (e.g. exposure to UV) or exposure to cosmetic treatments (e.g. bleaching) can cleave these thioester bonds, which leads to a loss of surface lipids, replaced by sulfonic acid functions. This makes the surface of the hair more hydrophilic and compromises its natural lubrication (Popescu and Höcker, Chem. Soc. Rev., 2007, 36, 1282-1291). Consequently, a highly desirable property of the hair is the hydrophobicity of its surface.
[0101] After the cosmetic treatments described in the application protocol, the hair is collected into locks of 1.5 g by weighing with a precision balance (Perkin-Elmer). The lock is cut into smaller locks of 3.5 cm length using razor blades. A plastic cable tie is attached to the middle of each small lock to prevent the fibres from slipping.
[0102] The 3.5 cm small lock is fixed in the specimen holder of a Zwickiline Z2.5 mechanical testing machine (Zwick, Germany) equipped with a 100 Newton (N) measuring cell. The small lock is immersed at a constant rate of 100 mm / min in a beaker filled with MilliQ® water. The water is changed between each measurement after carefully cleaning the beaker. The force required to fully penetrate the lock into the water is recorded and represented in the form of a force / displacement curve. As it enters the water, the small lock resists immersion, causing an increase in the force exerted by the testing machine to ensure a constant displacement. The area under this curve makes it possible to determine the total energy of immersion. Subtracting from this the value measured for a cable tie alone results in a value for the energy of immersion which is correlated with the water contact angle at the surface of the hair measured by the method of Willhelmy (Neumann and Good, Techniques of Measuring Contact Angles, in Surface and colloids science, Vol. 11: experimental methods, 1979, Springer US, pp 31-91). The impact of hair treatments on the hydrophobicity properties is determined by comparing the energy of immersion for reference small locks with the energy of immersion for small locks treated with the compositions according to the invention. The higher the energy of immersion, the more hydrophobic the surface of the hair.Results of the hydrophobicity measurements
[0103] The results of the hydrophobicity measurements for each of the compositions C12 to C16 tested are summarized in the table below.
[0104] CompositionEnergy of immersion (mJ)C12(Invention)0.0175C13(Invention)0.0160C14(Invention)0.0190C15(Invention)0.0159C16(Comparative)0.0105
[0105] The results show that the compositions according to the present invention make it possible to improve the hydrophobicity of the fibre. The hair thus treated is easier to style and disentangle.
[0106] c.Evaluation of the smooth feel by the friction test on dry hair
[0107] The compositions C12 to C16 were applied to locks of hair according to the application protocol described in paragraph b. above.Test protocol
[0108] The surface of natural hair is perceived as smooth, i.e. with a low coefficient of friction, whereas the surface of damaged hair is perceived as rough, i.e. with a high coefficient of friction.
[0109] Hair treatments that damage the hair, such as dyeing and bleaching, are known to increase the hair’s coefficient of friction.
[0110] Consequently, the lower the coefficient of friction of the hair, the better the sensation of repaired hair and the ease with which the head of hair can be combed and disentangled under dry conditions.
[0111] In this test, a small lock 3.5 cm in length as prepared in paragraph b. above is fixed in the specimen holder of a Zwickiline Z2.5 mechanical testing machine (Zwick, Germany) equipped with a 100 Newton (N) measuring cell. A normal force of 0.5 N is applied to the small locks using forceps covered with disposable plastic foam. The foam is replaced after each measurement. The testing machine applies a movement at a constant rate of 100 mm / min to extract the small lock from the forceps. During removal, the force required to extract the lock of hair is measured as a function of the displacement. The force / displacement curve obtained is characterized by a plateau at the end of the stroke, and the average force at the plateau is recorded. The impact of the hair treatments on the friction properties is determined by comparing the average force at the plateau for reference small locks with the average force at the plateau for treated small locks.
[0112] For measurements in the dry state (dry friction force), the hair is conditioned at 25°C and 45% relative humidity.Results of the measurements of the smooth feel
[0113] The results of the measurements of the smooth feel for each of the compositions C12 to C16 tested are summarized in the table below.
[0114] CompositionFriction force (N)C12(Invention)0.330C13(Invention)0.305C14(Invention)0.347C15(Invention)0.345C16(Comparative)0.375
[0115] Lower friction forces are observed on dry hair for the hair treated by the process according to the present invention, compared to the untreated hair. The surface of the hair is smoother. The treated hair is softer and easier to comb and to disentangle, compared to the untreated hair.Example 3
[0116] a.Preparation of the compositions
[0117] The following compositions C17 to C19 were prepared from the ingredients mentioned in the table below.
[0118] CompositionPeptide – Mass1N NaOH or 1N HClDistilled waterC17(Invention)RGK – 1.25 gqs pH 6qs 10 gC18(Invention)KKK – 0.50 gqs pH 6qs 10 gC19(Comparative – Placebo)-qs pH 6qs 10 g
[0119] b.Evaluation of the breakage and irreversible deformation of the hair
[0120] The compositions C17 to C19 were applied to locks of hair according to the application protocol described in Example 1 and the locks were evaluated with regard to their integrity, namely their resistance to breakage and to irreversible deformation according to the test protocol described in Example 1.Results of the integrity measurements
[0121] The results of the integrity measurements for each of the compositions C17 to C19 tested are summarized in the table below.
[0122] CompositionNumber of broken fibresNumber of irreversibly deformed fibresComments on the integrityC17(Invention)02GoodC18(Invention)13GoodC19(Comparative – Placebo)37Very bad
[0123] 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
Process for treating keratin fibres comprising a) the application, to the keratin fibres, of one or more compounds P or of a composition (C) comprising same, the compound(s) P being chosen from peptides having a sequence consisting of 3 to 6 amino acids, the C-terminal end of the peptides being chosen from lysine or arginine and / or the sequence of the peptides comprising lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine, salts of these peptides, solvates thereof such as the hydrates, and mixtures thereof.Process for treating keratin fibres according to the preceding claim, wherein the compound(s) P are chosen from the compounds of formula (I):AA1-AA2-(AAi)n-AA3(I)in which formula (I):- AA1, AA2, AA3and AAi, which may be identical or different, denote an amino acid;- n denotes an integer equal to 0, 1, 2 or 3, preferably n is equal to 0 or 1;- when n is equal to 2 or 3, the amino acids AAiare identical or different;it being understood that:- at least one of the amino acids AA1, AA2, AA3or AAiis chosen from lysine or arginine; and- if AA3denotes lysine or arginine then AA1, AA2and AAidenote any amino acid; and- if AA3is other than lysine and arginine, then at least two adjacent amino acids are chosen from lysine-lysine or arginine-arginine or lysine-arginine or arginine-lysine.Process according to the preceding claim, wherein the amino acids AA1, AA2, AA3and AAiare independently chosen from arginine, lysine, glycine, proline, alanine, valine, leucine, threonine, beta-alanine, isoleucine, phenylalanine, asparagine or methionine, preferably from arginine, lysine, glycine, proline, alanine, valine, leucine or threonine.Process according to any one of the preceding claims, wherein the compound(s) Pare chosen from Leucine-Alanine-Lysine (LAK), Valine-Proline-Lysine (VPK), Glycine-Lysine-Arginine (GKR), Arginine-Proline-Arginine (RPR), Threonine-Lysine-Proline-Arginine (TKPR), Alanine-Lysine-Lysine (AKK), Valine-Lysine-Lysine (VKK), Arginine-Arginine-Arginine (RRR), Arginine-Lysine-Arginine-Arginine (RKRR), Arginine-Arginine-Lysine-Lysine-Proline (RRKKP), Lysine-Lysine-Lysine (KKK), Arginine-Glycine-Lysine (RGK), salts thereof, solvates thereof such as the hydrates, and mixtures thereof.Process according to any one of the preceding claims, wherein the compound(s) P are other than the peptides chosen from Arginine-Arginine-Arginine (RRR), Lysine-Lysine-Lysine (KKK), salts thereof, solvates thereof such as the hydrates, and mixtures thereof.Process according to any one of the preceding claims, wherein the composition (C) comprises a total content of compounds P ranging from 0.005% to 25% by weight, preferably ranging from 0.01% to 20% by weight, more preferentially ranging from 0.05% to 10% by weight, more preferentially still ranging from 0.1% to 2% by weight, relative to the total weight of the composition (C).Process according to any one of the preceding claims, wherein the composition (C) comprises water, preferably from 30% to 99.995% by weight of water, preferably from 50% to 99.995% by weight of water.Process according to any one of the preceding claims, wherein the pH of the composition (C) is between 3.5 and 6.5, preferably between 3.5 and 5.5, more preferentially between 4 and 5, more preferentially still between 4.25 and 4.75; most preferentially, the pH of the composition (C) is 4.Process according to any one of the preceding claims, further comprising at least one additional step a') of washing the keratin fibres prior to or simultaneously with step a), preferably prior to step a) and / or at least one additional step successive to step a) and chosen from the following steps b) to d):b) a step of applying the composition (C) to the keratin fibres, preferably for a duration of at least 10 seconds, said application step optionally being performed under an airtight film of curl-paper 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.Composition (C) as defined in any one of Claims 1 to 7, wherein the pH of the composition (C) is between 3.5 and 6.5, preferably between 3.5 and 5.5, more preferentially between 4 and 5, more preferentially still between 4.25 and 4.75; most preferentially, the pH of the composition (C) is 4.Use of one or more compounds P as defined in any one of Claims 1 to 5 or of a composition (C) as defined in any one of Claims 1 to 8, for caring for keratin fibres, preferably for giving keratin fibres a soft and / or smooth feel and / or sheen, more preferentially for giving them a soft and / or smooth feel.Use of one or more compounds P as defined in any one of Claims 1 to 5 or of a composition (C) as defined in any one of Claims 1 to 8, for preventing the irreversible deformation of keratin fibres during combing and / or disentangling.Use of one or more compounds P as defined in any one of Claims 1 to 5 or of a composition (C) as defined in any one of Claims 1 to 8, for repairing and / or preventing breakage of keratin fibres.Use according any one of Claims 11 to 13, wherein the keratin fibres are damaged and / or sensitized keratin fibres.
Citation Information
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