Compositions and methods for the treatment of keratinous fibers

Abstract

COMPOSITIONS AND METHODS FOR THE TREATMENT OF KERATINOUS FIBERS. The disclosure relates to compositions comprising (a) at least one carboxylic acid or a salt thereof; (b) at least one cyclodextrin or a derivative thereof; and (c) at least one solvent. The compositions may be used to provide lasting curl definition and / or control of frizz and / or volume of hair, even in high humidity. The disclosure also relates to methods of manufacturing and using the compositions. Figure for abstract: 1

Description

Title of the invention: COMPOSITIONS AND METHODS FOR THE TREATMENT OF KERATINOUS FIBERS technical field

[0001] This disclosure relates to compositions and methods for treating keratin fibers, such as curly or wavy hair. The compositions improve curl definition and / or control frizz and / or hair volume. The disclosure also relates to methods of manufacturing and using the compositions. CONTEXT

[0002] Consumers with curly or wavy hair are often dissatisfied with its appearance. For example, curly hair may appear frizzy, with poor curl definition. While there are products designed to reduce frizz and / or improve curl definition, these products have drawbacks such as making hair feel greasy, weighing it down, or being ineffective, particularly in humid climates. Therefore, there is a demand for new and improved products that can enhance the visual appearance of curls, for example, by improving curl definition and / or reducing volume and / or frizz.

[0003] It has now been surprisingly discovered that compositions comprising at least one carboxylic acid and at least one cyclodextrin are capable of improving the appearance of curly or wavy hair, for example by enhancing curl definition and hold, and / or by controlling frizz. These benefits have been shown to persist even under conditions of high humidity. SUMMARY

[0004] This disclosure relates to compositions for treating keratinous fibers, such as curly or wavy hair, by improving curl definition and / or frizz control, and / or reducing the visual volume of hair, as well as methods of using the compositions.

[0005] In one embodiment, the disclosure relates to compositions comprising (a) at least one carboxylic acid or a salt thereof, (b) at least one cyclodextrin or a derivative thereof; and (c) at least one solvent. In various embodiments, the compositions have a molar ratio of (a):(b) ranging from approximately 0.5:1 to approximately 25:3, such as approximately 4:1 to approximately 15:1 or approximately 6:1 to approximately 10:1.

[0006] In various embodiments, (a) at least one carboxylic acid or a salt thereof may be selected from monocarboxylic acids, dicarboxylic acids

[0007]

[0008]

[0009]

[0010]

[0011] Boxylic acids, tricarboxylic acids, their salts, or mixtures thereof, such as citric acid, lactic acid, malic acid, maleic acid, tartaric acid, glycolic acid, their salts, or mixtures thereof. In additional embodiments, a polycarboxylic acid having more than three carboxyl groups, such as phytic acid, may be used, alone or in combination with one or more monocarboxylic acids, dicarboxylic acids, tricarboxylic acids, their salts, or mixtures thereof. (a) At least one carboxylic acid or a salt thereof may, in various embodiments, be present in an amount ranging from about 0.01% to about 20% by weight, relative to the weight of the composition, such as, for example, about 0.1% to about 10% or about 0.5% to about 8%. In various embodiments, (b) at least one cyclodextrin or a derivative thereof may be selected from compounds of formula: where R is selected from H, CH3, or a hydroxypropyl group, and n ranges from 6 to 8. For example, at least one cyclodextrin or a derivative thereof may be selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl-α-cyclodextrin, methyl-β-cyclodextrin, methyl-γ-cyclodextrin, or mixtures thereof. (b) At least one cyclodextrin or a derivative thereof may, in various embodiments, be present in an amount ranging from about 0.01% to about 20% by weight, relative to the weight of the composition, such as, for example, about 0.1% to about 10% or about 0.4% to about 6%. The disclosure also relates to methods of using the compositions, for example, methods of treating hair by applying the compositions disclosed to the hair. These methods may impart to the hair one or more of the following improvements: curl definition, volume control, and / or frizz control, which, in various embodiments, may last for one or more hours, even in high humidity. The disclosure further relates to methods of manufacturing the compositions, in which, by choosing specific weight or molar ratios of the components, compositions providing particular degrees of curl definition and / or volume control and / or frizz control can be obtained. BRIEF DESCRIPTION OF THE FIGURES

[0012] The accompanying drawings, which are incorporated herein and form part of this descriptive memorandum, illustrate exemplary embodiments of the disclosure and, together with the general description given above and the description provided herein, serve to explain the characteristics of the disclosure.

[0013] [Fig.1] Fig.1 is a graph showing the definition of curls conferred on hair by compositions Cl at C4 and IA at T0 and T24H.

[0014] [Fig. 2] Figures 2A to 2E are images of hair strands treated with compositions Cl to C4 and IA taken at T0, T0Combing and T24H.

[0015] [Fig. 3] Figures 3A and 3B are graphs showing the effective frizz (3A) and the effective frizz surface (3B) of hair treated with compositions Cl to C4 and IA at T0, T1H and T24H.

[0016] [Fig. 4] Figures 4A to 4E are images of hair strands treated with compositions Cl to C4 and IA taken at T0, T0.5H, T1H, T2H and T24H.

[0017] [Fig. 5] Figures 5A and 5B are graphs showing the effective frizz (5A) and the effective frizz area (5B) of hair treated with compositions Cl and 2A, 2B toTO, T1Het T24H.

[0018] [Fig. 6] Figures 6A to 6C are images of hair strands treated with compositions Cl and 2A, 2B taken at T0 and T24H.

[0019] [Fig. 7] Figures 7A and 7B are images of hair strands treated with compositions Cl and 2C, 2D taken at T0 and T1H.

[0020] [Fig. 8] Figures 8A and 8B are images of hair strands treated with compositions 2E and 2G taken at T0 and T1H.

[0021] [Fig. 9] Figures 9A and 9B are images of hair strands treated with compositions 3A and 3D taken at T0 and T1H, with a comparative strand treated with composition Cl at T1H.

[0022] [Fig. 10] Figures 10A to 10C are graphs showing the frizz (10A), curl definition (10B) and curliness (10C) of hair treated with compositions Cl and 4A to 4F to T4H.

[0023] [Fig. 11] Figures 1 IA and 1 IB are graphs showing the frizz (1 IA) and the frizz zone (1 IB) of hair treated with compositions Cl and 4A to 4F to T4H.

[0024] [Fig. 12] Figures 12A to 12G are images of hair strands treated with compositions Cl and 4A to 4F to T4H.

[0025] It is understood that the preceding and following descriptions are merely illustrative and explanatory, and are not intended to be restrictive of any claimed subject matter. DETAILED DESCRIPTION

[0026] The disclosure relates to compositions for hair styling, such as improving the appearance of curly hair, which in various embodiments can provide one or more of the following characteristics: curl definition, curl retention and / or frizz control, as well as methods of manufacturing and using the compositions. I. Compositions

[0027] In various embodiments, the compositions according to the disclosure include (a) at least one carboxylic acid; (b) at least one cyclodextrin; and (c) at least one solvent. Carboxylic acid

[0028] The compositions according to the disclosure comprise at least one carboxylic acid, including its salts. The carboxylic acids that may be used include, in various embodiments, monocarboxylic acids (one carboxylic group) or polycarboxylic acids (two or more carboxylic groups). Preferably, the carboxylic acids are non-polymer carboxylic acids. The carboxylic acids may be selected, in some embodiments, from those having a molecular weight less than about 900 g / mol, such as less than about 700 g / mol, less than about 500 g / mol, less than about 300 g / mol, or less than about 200 g / mol.

[0029] In some embodiments, at least one carboxylic acid may be chosen from monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, en-tanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, lactic acid, or their salts.

[0030] In additional embodiments, at least one carboxylic acid may be selected from dicarboxylic acids such as oxalic acid, malonic acid, malic acid, glutaric acid, citraconic acid, succinic acid, adipic acid, tartaric acid, fumaric acid, maleic acid, sebacic acid, azelaic acid, dodecanedioic acid, phthalic acid, isophthalic acid, terephthalic acid, 2,6-naphthalene dicarboxylic acid, or their salts.

[0031] In further additional embodiments, at least one carboxylic acid may be chosen from tricarboxylic acids such as citric acid, isocitric acid, aconitric acid, propane-1,2,3-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid, or their salts.

[0032] In further embodiments, at least one car- acid Boxyl acid can be chosen from polycarboxylic acids that have more than three carboxylic groups, such as phytic acid.

[0033] In various embodiments, the compositions comprise a mixture of two or more carboxylic acids or their salts. For example, the compositions may comprise a mixture of two or more monocarboxylic acids or their salts, or may comprise a mixture of two or more polycarboxylic acids or their salts, such as two or more dicarboxylic acids, two or more tricarboxylic acids, or a mixture of one or more dicarboxylic acids and one or more tricarboxylic acids. Mixtures of one or more monocarboxylic acids or their salts with one or more polycarboxylic acids or their salts are also envisaged. In additional embodiments, the composition comprises only one carboxylic acid or one of its salts.

[0034] In some embodiments, at least one carboxylic acid is chosen from citric acid, lactic acid, malic acid, maleic acid, tartaric acid, glycolic acid, phytic acid, their salts, or a mixture of two or more of the preceding.

[0035] In various embodiments, at least one carboxylic acid or a salt thereof may be present in the compositions in an amount of about 0.01% to about 20% by weight, as well as about 0.1% to about 18%, about 0.5% to about 15% or about 1% to about 13% by weight, relative to the total weight of the composition. By way of non-limiting example, at least one carboxylic acid or a salt thereof is present in the composition in a total amount ranging from approximately 0.5% to approximately 15%, by weight, for example, from approximately 0.5% to approximately 12%, from approximately 0.5% to approximately 10%, from approximately 0.5% to approximately 9%, from approximately 0.5% to approximately 8%, from approximately 0.5% to approximately 7%, from approximately 0.5% to approximately 6%, from approximately 0.5% to approximately 5%, from approximately 0.5% to approximately 4%, from approximately 0.5% to approximately 3%, from approximately 1% to approximately 15%, from approximately 1% to approximately 12%, from approximately 1% to approximately 10%, from approximately 1% to approximately 9%, from approximately 1% to approximately 8%,from about 1% to about 7%, from about 1% to about 6%, from about 1% to about 5%, from about 1% to about 4%, from about 1% to about 3%, from about 2% to about 15%, from about 2% to about 12%, from about 2% to about 10%, from about 2% to about 9%, from about 2% to about 8%, from about 2% to about 7%, from about 2% to about 6%, or from about 2% to about 5%, by weight, relative to the total weight of the composition, including all ranges and subranges thereof. In some embodiments, at least one carboxylic acid or a salt thereof is present in an amount ranging from about 0.5% to about 13%, preferably from about 0.5% to about 10%, and more preferably from about 0.5% to about 8% by weight, relative to the total weight of the composition.

[0036] In one embodiment, the at least one carboxylic acid comprises or consists of citric acid, lactic acid, malic acid, maleic acid, tartaric acid, glycolic acid, phytic acid, their salts, or a mixture thereof, and is present in an amount ranging from about 0.1% to about 10%, such as 0.3% to about 9%, or about 0.5% to about 8% by weight, relative to the total weight of the composition, including all ranges and sub-ranges thereof. Cyclodextrin

[0037] The compositions according to the disclosure comprise at least one cyclodextrin, which includes its derivatives. Cyclodextrins are a family of cyclic oligosaccharides consisting of a macrocyclic ring of glucose subunits linked by α-1,4 glycosidic bonds.

[0038] Cyclodextrins that can be used include those of the formula:

[0039] in which:

[0040] R is chosen from H, CH3, or a hydroxypropyl group, and n is from 6 to 8.

[0041] For example, in embodiments where R = H, the cyclodextrin may be α-cyclodextrin (n = 6), β-cyclodextrin (n = 7), or γ-cyclodextrin (n = 8). By way of example, α-cyclodextrin sold by WACKER under the name CAVAMAX W6 PHARMA, β-cyclodextrin sold by WACKER under the name CAVAMAX W7 PHARMA, or γ-cyclodextrin sold by WACKER under the name CAVAMAX W8 PHARMA may be used.

[0042] In other embodiments where R = CH3, the cyclodextrin may be a methyl-cyclodextrin, such as methyl-α-cyclodextrin (n = 6), methyl-β-cyclodextrin (n = 7), or methyl-γ-cyclodextrin (n = 8). For example, methyl-β-cyclodextrin sold by WACKER under the name CAVASOL W7 may be chosen.

[0043] In various embodiments, the at least one cyclodextrin may comprise a mixture of cyclodextrins and / or their derivatives. For example, the at least one cyclodextrin may be a mixture of α-cyclodextrin, β-cyclodextrin, and / or γ-cyclodextrin. In another embodiment, the at least one cyclodextrin comprises β-cyclodextrin. In yet another embodiment, the cyclodextrin is solely β-cyclodextrin, and no other cyclodextrin or any of the Its derivatives are not present in the composition.

[0044] At least one cyclodextrin may be present in the compositions in an amount of about 0.01% to about 20% by weight, as well as about 0.1% to about 18%, about 0.5% to about 15%, or about 1% to about 13% by weight, relative to the total weight of the composition. By way of non-limiting example, at least one cyclodextrin is present in the composition with a total amount ranging from about 0.5% to about 15%, by weight, for example, from about 0.5% to about 12%, from about 0.5% to about 10%, from about 0.5% to about 9%, from about 0.5% to about 8%, from about 0.5% to about 7%, from about 0.5% to about 6%, from about 0.5% to about 5%, from about 0.5% to about 3%, from about 1% to about 15%, from about 1% to about 12%, from about 1% to about 10%, from about 1% to about 9%, from about 1% to about 8%, from about 1% to about 7%, from about 1% to about 6%, from about 1% to about 5%, from about 1% to about 4%, from about 1% to about 3%, from about 2% to about 15%, from about 2% to about 12%, from about 2% to about 10%, from about 2% to about 9%, from about 2% to about 8%, from about 2% to about 7%, from about 2% to about 6%, or from about 2% to about 5% by weight, relative to the total weight of the composition, including all ranges and subranges thereof. In some embodiments, at least one cyclodextrin is present in an amount ranging from about 1% to about 13%, preferably from about 1% to about 7%, and more preferably from about 1% to about 5% by weight, relative to the total weight of the composition.

[0045] In one embodiment, at least one cyclodextrin comprises or consists of β-cyclodextrin, and is present in an amount ranging from approximately 0.1% to approximately 10%, such as 0.2% to approximately 8%, approximately 0.3% to approximately 7%, or approximately 0.4% to approximately 6% by weight, relative to the total weight of the composition, including all its ranges and sub-ranges. Solvent

[0046] The compositions according to the disclosure comprise at least one solvent. In various embodiments, the solvent comprises, consists essentially of, or consists of water. In a preferred embodiment, the solvent consists essentially of water, and the total amount of water ranges from approximately 50% to 99.9%, based on the total weight of the composition.

[0047] The compositions according to the disclosure may include a cosmetically acceptable solvent other than water, for example in combination with water. By way of non-limiting example, the solvent other than water may be selected from monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol and phenylethyl alcohol, or glycols or ethers of Glycols such as, for example, monomethyl, monoethyl, and monobutyl ethers of ethylene glycol, propylene glycol, or their ethers such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol, as well as alkyl ethers of diethylene glycol, for example, monoethyl ether or monobutyl ether of diethylene glycol. Other suitable examples include ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propanediol, and glycerin. Mixtures of the above components may also be chosen, including mixtures of the above components with water.

[0048] The solvent may be present in the composition in an amount ranging from about 50% to about 99.9% by weight, relative to the total weight of the composition, including all intermediate ranges and sub-ranges.For example, the total amount of solvent can range from approximately 70% to approximately 99%, from approximately 75% to approximately 99%, from approximately 80% to 99%, from approximately 85% to 99%, from approximately 90% to approximately 99%, from approximately 95% to approximately 99%, from approximately 97% to approximately 99%, from approximately 70% to approximately 98%, from approximately 75% to approximately 98%, from approximately 80% to approximately 98%, from approximately 85% to approximately 98%, from approximately 90% to approximately 98%, from approximately 95% to approximately 98%, from approximately 70% to approximately 95%, from approximately 70% to approximately 95%, from approximately 80% to approximately 95%, from approximately 85% to 95%, from approximately 90% to approximately 95%, from approximately 70% to approximately 99%, from approximately 70% to approximately 99%, from approximately 70% to approximately 99%, from approximately 70% to approximately 99%, from approximately 70% to approximately 99%, from approximately 70% to approximately 99%, from approximately 75 ... at approximately 90%, from approximately 75% to approximately 90%, from approximately 80% to 90%, or from approximately 85% to 90% by weight, relative to the total weight of the composition, including all ranges and sub-ranges thereof. Additional components

[0049] The compositions according to the disclosure may optionally include any additional or auxiliary components suitable for use in these compositions. These components may include, but are not limited to, thickening agents, conditioning agents, tints / pigments, moisturizing agents, fillers, structuring agents, gloss enhancers, antioxidants, perfumes, buffers, dispersants, plant extracts, preservatives, opacifiers, sunscreens, vitamins, pH adjusting agents, and antistatic agents.

[0050] Optional additional or auxiliary components may be present in an amount of up to about 15%, such as about 0.01% to about 15%, about 0.01% to about 10% by weight, about 0.01% to about 5% by weight, or about 0.01% to about 1% by weight, relative to the total weight of the composition.

[0051] In various embodiments, the compositions may have a pH less than or equal to about 7. For example, the pH of the compositions may range from about 2 to about 6, such as from about 3 to about 5, from about 3.5 to about 5, from about 3 to about 4.5, from about 3.5 to about 4.5, or from about 3 to about 4, including all intermediate ranges and sub-ranges.

[0052] The compositions according to the disclosure are typically in the form of a liquid, cream, or lotion, but are not limited to this. In some embodiments, the compositions are a non-aerosol product that can be dispensed from a bottle, tube, or spray bottle. When the compositions are formulated as aerosol products, they may further comprise at least one propellant. II. Methods A. Methods for manufacturing the compositions

[0053] The disclosure also relates to methods of manufacturing the compositions described herein. In certain embodiments, it may be particularly advantageous to choose specific molar or weight ratios of carboxylic acid(s), cyclodextrin(s), and / or solvent(s) (e.g., water). For example, by choosing specific molar or weight ratios of these components, it is possible to tailor the compositions to provide varying degrees of curl definition and / or frizz control.

[0054] Therefore, it may be useful to prepare a premix of carboxylic acid(s), cyclodextrin(s), and solvent(s), which can then be diluted to the desired concentration with additional solvent(s) and other additives before the composition is applied to the hair. By way of example, the premix can be prepared with a weight ratio of carboxylic acid(s):cyclodextrin(s):solvent(s) ranging from approximately 0.3:1:0.2 to approximately 5:1:0.3. For example, the weight ratio could be approximately 2:3:1, approximately 1:1:3, approximately 5:3:1, approximately 8:3:1, or approximately 10:3:1. The premix can have a molar ratio of carboxylic acid(s):cyclodextrin(s):solvent(s) ranging from about 0.5:1:5 to about 25:3:90.For example, the molar ratio can be approximately 1:1:10, approximately 2:1:10, approximately 3:1:10, approximately 4:1:10, approximately 5:1:10, approximately 6:1:10, approximately 7:1:10, approximately 8:1:10, approximately 9:1:10, approximately 10:1:10, approximately 11:1:10, approximately 12:1:10, approximately 13:1:10, approximately 14:1:10, approximately 15:1:10, approximately 16:1:10, approximately 17:1:10, approximately 18:1:10, approximately 19:1:10, approximately 20:1:10, and approximately 1:1:15, approximately 2:1:15, approximately 3:1:15, approximately 4:1:15, approximately 5:1:15, approximately 6:1:15, approximately 7:1:15, approximately 8:1:15, approximately 9:1:15, approximately 10:1:15, approximately 11:1:15, approximately 12:1:15, approximately 13:1:15, approximately 14:1:15, approximately 15:1:15, approximately 16:1:15, approximately 17:1:15, approximately 18:1:15, approximately 19:1:15, approximately 20:1:15, approximately 1:1:20, approximately 2:1:20, . approximately 3:1:20, approximately 4:1:20, approximately 5:1:20, approximately 6:1:20, approximately 7:1:20, approximately 8:1:20, approximately 9:1:20, approximately 10:1:20, approximately 11:1:20, approximately 12:1:20, approximately 13:1:20, approximately 14:1:20, approximately 15:1:20, approximately 16:1:20, approximately 17:1:20, approximately 18:1:20, approximately 19:1:20, approximately 20:1:20, approximately 1:1:25, approximately 2:1:25, approximately 3:1:25, approximately 4:1:25, approximately 5:1:25, approximately 6:1:25, approximately 7:1:25, approximately 8:1:25, approximately 9:1:25, approximately 10:1:25, approximately 11:1:25, approximately 12:1:25, approximately 13:1:25, approximately 14:1:25, approximately 15:1:25, approximately 16:1:25, approximately 17:1:25, approximately 18:1:25, approximately 19:1:25, approximately 20:1:25, approximately 1:1:30, approximately 2:1:30, approximately 3:1:30, approximately 4:1:30, approximately 5:1:30, approximately 6:1:30, approximately 7:1:30, approximately 8:1:30, approximately 9:1:30, approximately 10:1:30, approximately 11:1:30, approximately 12:1:30, approximately 13:1:30, approximately 14:1:30, approximately 15:1:30, approximately 16:1:30,from approximately 17:01:30, from approximately 18:01:30, from approximately 19:01:30, from approximately 20:01:30, from approximately 1:01:35, from approximately 2:01:35, from approximately 3:01:35, from approximately 4:01:35, from approximately 5:01:35, from approximately 6:01:35, from approximately 7:01:35, from approximately 8:01:35, from approximately 9:01:35, from approximately 10:01:35, from approximately 11:01:35, from approximately 12:01:35, from approximately 13:01:35, from approximately 14:01:35, from approximately 15:01:35, from approximately 16:01:35, from approximately 17:01:35, from approximately 18:01:35, approximately 19:01:35, approximately 20:01:35, approximately 1:01:40, approximately 2:01:40, approximately 3:01:40, approximately 4:01:40, approximately 5:01:40, approximately 6:01:40, approximately 7:01:40, approximately 8:01:40, approximately 9:01:40, approximately 10:01:40, approximately 11:01:40, approximately 12:01:40, approximately 13:01:40, approximately 14:01:40, approximately 15:01:40, approximately 16:01:40, approximately 17:01:40, approximately 18:01:40, approximately 19:1:40, approximately 20:1:40, approximately 1:1:45, approximately 2:1:45, approximately 3:1:45, approximately 4:1:45, approximately 5:1:45, approximately 6:1:45, approximately 7:1:45, approximately 8:1:45, approximately 9:1:45, approximately 10:1:45,from approximately 11:01:45, from approximately 12:01:45, from approximately 13:01:45, from approximately 14:01:45, from approximately 15:01:45, from approximately 16:01:45, from approximately 17:01:45, from approximately 18:01:45, from approximately 19:01:45, from approximately 20:01:45, from approximately 1:01:50, from approximately 2:01:50, from approximately 3:01:50, from approximately 4:01:50, from approximately 5:01:50, from approximately 6:01:50, from approximately 7:01:50, from approximately 8:01:50, from approximately 9:01:50, from approximately 10:01:50, from approximately 11:01:50, from approximately 12:01:50, approximately 13:01:50, approximately 14:01:50, approximately 15:01:50, approximately 16:01:50, approximately 17:01:50, approximately 18:01:50, approximately 19:01:50, approximately 20:01:50, approximately 1:02:10, approximately 2:02:10, approximately 3:02:10, approximately 4:02:10, approximately 5:02:10, approximately 6:02:10, approximately 7:02:10, approximately 8:02:10, approximately 9:02:10, approximately 10:02:10, approximately 11:02:10, approximately 12:02:10, approximately 13:2:10, approximately 14:2:10, approximately 15:2:10, approximately 16:2:10, approximately 17:2:10, approximately 18:2:10, approximately 19:2:10, approximately 20:2:10, approximately 1:2:15, approximately 2:2:15, approximately 3:2:15,approximately 4:2:15, approximately 5:2:15, approximately 6:2:15, approximately 7:2:15, approximately 8:2:15, approximately 9:2:15, approximately 10:2:15, approximately 11:2:15, approximately 12:2:15, approximately 13:2:15, , from approximately 14:02:15, from approximately 15:02:15, from approximately 16:02:15, from approximately 17:02:15, from approximately 18:02:15, from approximately 19:02:15, from approximately 20:02:15, from approximately 1:02:20, from approximately 2:02:20, from approximately 3:02:20, from approximately 4:02:20, from approximately 5:02:20, from approximately 6:02:20, from approximately 7:02:20, from approximately 8:02:20, from approximately 9:02:20, from approximately 10:02:20, from approximately 11:02:20, from approximately 12:02:20, from approximately 13:02:20, from approximately 14:02:20, from approximately 15:02:20, approximately 16:02:20, approximately 17:02:20, approximately 18:02:20, approximately 19:02:20, approximately 20:02:20, approximately 1:02:25, approximately 2:02:25, approximately 3:02:25, approximately 4:02:25, approximately 5:02:25, approximately 6:02:25, approximately 7:02:25, approximately 8:02:25, approximately 9:02:25, approximately 10:02:25, approximately 11:02:25, approximately 12:02:25, approximately 13:02:25, approximately 14:02:25, approximately 15:02:25, approximately 16:02:25, approximately 17:02:25, approximately 18:02:25, approximately 19:02:25, approximately 20:02:25, approximately 1:02:30, approximately 2:02:30, approximately 3:02:30, approximately 4:02:30, approximately 5:02:30, approximately 6:02:30, approximately 7:02:30from approximately 8:02:30, from approximately 9:02:30, from approximately 10:02:30, from approximately 11:02:30, from approximately 12:02:30, from approximately 13:02:30, from approximately 14:02:30, from approximately 15:02:30, from approximately 16:02:30, from approximately 17:02:30, from approximately 18:02:30, from approximately 19:02:30, from approximately 20:02:30, from approximately 1:02:35, from approximately 2:02:35, from approximately 3:02:35, from approximately 4:02:35, from approximately 5:02:35, from approximately 6:02:35, from approximately 7:02:35, from approximately 8:02:35, from approximately 9:02:35, approximately 10:02:35, approximately 11:02:35, approximately 12:02:35, approximately 13:02:35, approximately 14:02:35, approximately 15:02:35, approximately 16:02:35, approximately 17:02:35, approximately 18:02:35, approximately 19:02:35, approximately 20:02:35, approximately 1:02:40, approximately 2:02:40, approximately 3:02:40, approximately 4:02:40, approximately 5:02:40, approximately 6:02:40, approximately 7:02:40, approximately 8:02:40, approximately 9:02:40, approximately 10:02:40, approximately 11:02:40, approximately 12:02:40, approximately 13:02:40, approximately 14:02:40, approximately 15:02:40, approximately 16:02:40, approximately 17:02:40, approximately 18:02:40, approximately 19:02:40, approximately 20:02:40,approximately 1:02:45, approximately 2:02:45, approximately 3:02:45, approximately 4:02:45, approximately 5:02:45, approximately 6:02:45, approximately 7:02:45, approximately 8:02:45, approximately 9:02:45, approximately 10:02:45, approximately 11:02:45, approximately 12:02:45, approximately 13:02:45, approximately 14:02:45, approximately 15:02:45, approximately 16:02:45, approximately 17:02:45, approximately 18:02:45, approximately 19:02:45, approximately 20:02:45, approximately 1:02:50, approximately 2:2:50, approximately 3:2:50, approximately 4:2:50, approximately 5:2:50, approximately 6:2:50, approximately 7:2:50, approximately 8:2:50, approximately 9:2:50, approximately 10:2:50, approximately 11:2:50, approximately 12:2:50, approximately 13:2:50, approximately 14:2:50, approximately 15:2:50, approximately 16:2:50, approximately 17:2:50, approximately 18:2:50, approximately 19:2:50, or approximately 20:2:50, including all beaches and sub-beaches thereof.

[0055] In one embodiment, the premix comprises at least one carboxylic acid selected from citric acid, at least one cyclodextrin selected from B-cyclodextrin, and water in a weight ratio ranging from approximately 0.3:1:0.3 to approximately 5:1:0.3, and a molar ratio ranging from approximately 2:1:10 to approximately 30:1:10, such that approximately 6:1:10.

[0056] Once the specific carboxylic acid(s), cyclodextrin(s), and solvent(s), as well as their desired ratio, have been selected, the premix can be prepared by any conventional method. By way of example only, the premix can be prepared by simply mixing the components in the selected ratio, preferably with heating. For example, the mixture can be mixed at a temperature of approximately 40 °C to approximately 100 °C, such as from approximately 50 °C to approximately 95 °C.

[0057] Once the premix has been prepared, it can then be diluted with an additional solvent and other additives to the desired concentration of the final composition as disclosed. The additional solvent may be the same as the premix solvent, may be different from the premix solvent, or may be a combination of the premix solvent with one or more solvents other than the premix solvent. In various embodiments, the compositions as disclosed may contain a premix:additional solvent ratio ranging from approximately 1:99 to approximately 50:50.For example, compositions according to the disclosure may contain a premix:additional solvent ratio ranging from about 2:98 to about 40:60, or from about 3:97 to about 35:65, such as about 2.5:97.5, about 5:95, about 7.5:92.5, about 10:90, about 12.5:87.5, about 15:85, about 17.5:81.5, about 20:80, about 25:75, or about 30:70, including all ranges and subranges thereof. In preferred embodiments, the premix:additional solvent ratio ranges from about 5:95 to about 15:85.

[0058] Thus, in various embodiments, the compositions according to the disclosure may have carboxylic acid(s):cyclodextrin(s) weight ratios ranging from about 1:3 to about 6:1, for example about 1:3, about 1:2.5, about 1:2, about 1:1.5, about 1:1, about 1.5:1, about 2:1, about 2.5:1, about 3:1, about 3.5:1, about 4:1, about 4.5:1, about 5:1, about 5.5:1, or about 6:1, including all ranges and sub-ranges thereof.

[0059] The compositions may have carboxylic acid(s):cyclodextrin(s) molar ratios ranging from about 0.5:1 to about 25:3, for example about 4:1 to about 15:1, about 5:1 to about 12:1, or about 6:1 to about 10:1, such as, for example, about 1:1, about 2:1, about 3:1, about 4:1, about 5:1, about 6:1, about 7:1, about 8:1, about 9:1, about 10:1, about 11:1, about 12:1, about 13:1, about 14:1, about 15:1, about 16:1, about 17:1, about 18:1, about 19:1, about 20:1, about 3:2, about 5:2, about 7:2, approximately 9:2, approximately 11:2, approximately 13:2, approximately 15:2, approximately 17:2, approximately 19:2, approximately 1:3, approximately 2:3, approximately 4:3, approximately 5:1, approximately 7:3, approximately 8:3, approximately 10:3, approximately 11:3, approximately 13:3, approximately 14:3, approximately 16:3, approximately 17:3, approximately 19:3, or approximately 20:3, including all beaches and sub-beaches thereof. B. Hair Treatment Methods

[0060] The disclosure also relates to methods for improving the appearance of curly hair through the use of the compositions described herein, for example by improving curl definition and / or reducing hair volume and / or frizz. The methods generally involve applying any one of the compositions as disclosed to the hair.

[0061] The compositions disclosed herein may be useful in a variety of contexts, whether for chemically treated or untreated hair, and / or for natural or artificial curls. The degree of curl or curl type of the hair may vary and is not limited. For example, the curls of hair treated with the compositions disclosed herein may range from slightly wavy to very kinky and curly, and may have different textures and colors.

[0062] Typically, the methods according to the disclosure may include applying an effective amount of a composition disclosed herein to curly hair, whether the hair is dry, wet, damp, or slightly wet when the composition is applied. As used herein, the term "effective amount" refers to a quantity sufficient to provide a desired effect to the hair, taking into account the degree of curl, length, volume, and texture of the hair. Generally, from about 0.1 gram to about 5 grams of product are applied per gram of hair, depending on the specific formulation of the product, the hair length, hair volume, and the type of hairstyle.

[0063] The composition applied to the hair can be evenly distributed by combing it with the fingers or a tool such as a comb or other. If desired, after applying the compositions disclosed herein, the hair can be styled or shaped, for example, scrunched, twisted, or otherwise, which can help define curls. The hair can then be air-dried or dried with a hairdryer, for example, a hooded dryer. The composition can remain on the hair as a leave-in product for any period of time, for example, about 10, 20, or 30 minutes or longer, such as a few hours or a few days, or until the next time the hair is washed or rinsed.

[0064] In some embodiments, a composition disclosed herein is used alone on the hair, without the use of other hair treatment compositions. In other embodiments, the compositions may be applied to the hair before, during, or after the application of another hair treatment or styling composition, such as a styling gel, hairspray, etc. Thus, a composition disclosed herein may be applied to the hair and layered over another composition that is also applied to the hair.

[0065] In various embodiments, the hair treatment methods using the compositions disclosed provide the hair with various lasting benefits described above, without a greasy feel or flaking, compared to hair not treated with a composition disclosed. The term "lasting," as used here, means that the curl-defining, volume-reducing, and / or frizz-control effects and other benefits imparted to the hair can remain for a desired period of time, such as at least one or a few hours, a few days, or until the hair is rinsed or washed.

[0066] After describing in detail the numerous embodiments of the present invention, it will be evident that modifications and variations are possible without departing from the scope of the disclosure defined in the appended claims. Furthermore, it should be noted that all the examples in this disclosure, while illustrating numerous embodiments of the disclosure, are provided by way of non-limiting examples and should therefore not be considered as limiting the various aspects thus illustrated. It should be understood that all definitions given herein are provided solely for the purposes of this disclosure.

[0067] As used herein, the terms "comprising," "having," and "including" (or "comprise," "have," and "include") are used in their broad and non-limiting sense. The expression "consisting essentially of" restricts the scope of a claim to the specified materials or steps and to those that do not materially affect the fundamental and novel characteristics of the compositions.

[0068] The expression "one or more" means "at least one" and therefore includes individual components as well as mixtures / combinations. Similarly, the expression "a salt of it" also refers to "salts of it." Thus, when the disclosure refers to "an element selected from the group consisting of A, B, C, D, E, F, a salt of these, or mixtures of these," it indicates that one or more of A, B, C, D, and F may be included, one or more of a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included, or a mixture of any two of A, B, C, D, E, F, a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included.

[0069] As used herein, the expressions "and mixtures thereof", "and a mixture of these", "and their combinations", "and a combination of these", "or their mixtures", "or a mixture of these", "or their combinations", and "or a combination of these" are used interchangeably to indicate that the list of components immediately preceding the expression, such as "A, B, C, D, or mixtures thereof", means that the component(s) may be chosen from A, B, C, D, A+B, A+B+C, A+D, A+C+D, etc., without limitation of their variations. Thus, the components may be used individually or in any combination of these.

[0070] For the purposes of this disclosure, it should be noted that, to provide a more concise description, some of the quantitative expressions given herein are not qualified by the term "approximately." It is understood that, whether the term "approximately" is used explicitly or implicitly, each quantity given herein is intended to refer to the actual value given, and it is also intended to refer to the approximation of that given value that would be reasonably deduced on the basis of ordinary competence in the art, including approximations due to the experimental and / or measurement conditions of that given value. All ranges and quantities given herein are intended to include subranges and quantities using any disclosed point as an endpoint. Thus, a range of "1% to 10%, such as 2% to 8%, such as 3% to 5%" is intended to encompass ranges of "1% to 8%", "1% to 5%", "2% to 10%", and so on.Similarly, a given range of "approximately 1% to 10%" is understood to have the term "approximately" modifying both the 1% and 10% endpoints. The term "approximately" is used here to indicate a difference of up to + / - 10% from the stated number, such as + / - 9%, + / - 8%, + / - 7%, + / - 6%, + / - 5%, + / - 4%, + / - 3%, + / - 2%, or + / - 1%. Likewise, all endpoints of the ranges are understood to be disclosed individually; for example, a range of 1:2 to 2:1 is understood to disclose a ratio of both 1:2 and 2:1.

[0071] The term “active substance”, as used here with respect to the percentage quantity of an ingredient or raw material, refers to 100% activity of the ingredient or raw material.

[0072] All quantities indicated here are relative to the quantity of active material, unless otherwise stated.

[0073] All percentages, parts and ratios indicated herein are based on the total weight of the compositions in this disclosure, unless otherwise stated.

[0074] As used herein, the expressions "application of a composition to keratinous materials" and "application of a composition to hair," and variations thereof, are intended to mean bringing keratinous materials, including hair and skin, into contact with at least one of the compositions in the disclosure, in any manner. This may also mean bringing keratinous materials into contact in an effective quantity.

[0075] Unless otherwise indicated, all percentages stated here are by weight, relative to the weight of the total composition.

[0076] As used herein, the term "curly hair" refers to any hair including a curl. The curl may be natural or artificial, that is, formed by chemical or physical treatment of the hair. The degree of curl of the hair may vary and is not limited.

[0077] As used herein, hair with enhanced or reinforced curl definition may have curls with a shape that has a pure curl appearance rather than being curly, curls that appear more individualized, curls that are more closed in appearance, and / or curls that have an enhanced visual appearance of hair color and / or highlights.

[0078] A "no-rinse" composition or product means a composition such as a hair treatment composition that is not rinsed and / or removed by washing with water or an acceptable solvent after the composition has been applied to the keratinous fiber, such as hair; instead, the composition may remain on the keratinous fibers for a desired period of time, such as 1 hour, 2 hours, 3 hours, 4 hours, up to 8 hours, overnight, or for as long as necessary, until the next washing or rinsing of the keratinous fibers.

[0079] The terms “substantially free” or “essentially free” as used herein mean that the specific material may be used in a manufacturing process in small quantities that do not materially affect the fundamental and novel characteristics of the compositions as disclosed. The terms may also mean that the specific material is not used in a manufacturing process but may still be present in a raw material that is included in the composition.

[0080] As used herein, the term "salts" referred to throughout the disclosure may include salts having a counterion such as an alkali metal, alkaline earth metal, or ammonium counterion. This list of counterions is not, however, exhaustive.

[0081] It should be understood that, with regard to the carboxylic acid salts described herein, it is intended to encompass the use of a salt of a carboxylic acid as an ingredient added to a composition according to the disclosure, or the salt of the carboxylic acid which is formed when the carboxylic acid is used as an ingredient in a composition according to the disclosure.

[0082] As used herein, the term "substantially free" or "essentially free" means that the specific material may be present in small amounts that do not materially affect the fundamental and novel characteristics of the compositions as disclosed. For example, there may be less than 2% by weight of a specific material added to a composition, based on the total weight of the compositions (provided that an amount of less than 2% by weight does not materially affect the fundamental and novel characteristics of the compositions as disclosed). Similarly, the compositions may include less than 2%, less than 1.5%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, or less than 0.01%. or none of the specified materials. Furthermore, all components positively stated in this disclosure may be negatively excluded from the claims; for example, a claimed composition may be "free," "essentially free," or "substantially free" of one or more components positively stated in this disclosure. The terms "substantially free" or "essentially free" as used herein may also mean that the specific material is not added to the composition but may still be present in a raw material included in the composition.

[0083] As used herein, the term "treat" (and its grammatical variations) refers to the application of the compositions of this disclosure to the surface of keratinous materials, such as hair.

[0084] Unless expressly stated otherwise, no method described herein is intended to be interpreted as requiring that its steps be performed in a specific order. Consequently, where a method claim does not expressly mention an order to be followed for its steps, or where it is not specifically stated in the claims or descriptions that the steps must be limited to a specific order, no particular order is to be inferred. EXAMPLES

[0085] The following examples are intended to be non-limiting and explanatory in nature only. In the examples, quantities are expressed as a percentage by weight (% by weight) of active substances, relative to the total weight of the composition, unless otherwise indicated.

[0086] Methods for analyzing the definition of curls and / or the control of frizz

[0087] The hair treated in the examples below was assessed visually, and / or were analyzed by RUMBA (Bossa Nova Technologies, LLC) and / or with photographic images to determine hair volume and surface area.

[0088] The RUMBA system, used to evaluate curl definition, is a polarization imaging system that takes successive images of a hair sample illuminated by an infrared LED and under several polarization states, using a rotating polarizer. The images provide a modulated intensity on each pixel, which is caused by the birefringence of the hair fiber and contains the angular signature that can be extracted with the system's software to construct an orientation image of the sample.

[0089] The orientation data can be mapped onto a 2D image to visualize the entire sample. From this orientation data, it is It is possible to define a coefficient related to hair straightness: the straighter the hair fibers in the strand, the closer the orientation distribution will be to a single angular value. The standard deviation of such a distribution is therefore inversely proportional to the perceived straightness.

[0090] The same procedure is used for alignment, the alignment of a strand of hair being defined as the fact that the hair fibers are "locally straight". Thus, a straightness coefficient is defined at a small scale of the 2D orientation map, which makes it possible to obtain a straightness coefficient on each pixel of the image. AI Example - Compositions

[0091] A premix according to the disclosure was prepared as shown in Table 1.

[0092] [Table 1] COMPONENT QUANTITY (g) CITRIC ACID 1.15 B-CYCLODEXTRIN 1.32 WATER 0.18

[0093] Table 1: Premix

[0094] The components of Table 1 were mixed at a temperature of about 85 °C for a period of about 2 to 3 hours, to prepare a premix as disclosed.

[0095] An inventive composition containing 5% of the premix of Table 1 was prepared by diluting it with additional water (premix:additional water = 5:95), and four comparative compositions were prepared as shown in Table 2. The admixture of composition C4 was prepared by mixing 100 mL of a 4.4% citric acid solution in water with 100 mL of a 4.2% B-cyclodextrin solution in water.

[0096] [Tables2] Inventive Component Comparative IA Cl C2 C3 C4 premix 5 - - - - CITRIC ACID - - 2.2 - - B-CYCLODEXTRIN E - - - 2.1 - ADMINISTERING - - - - 4.3 WATER QS to 100 QS to 100 QS to 100 QS to 100 QS to 100 Table 2: Compositions

[0097] Each of the IA and Cl compositions at C4 was adjusted to a pH of about 4 with a 0.1 M sodium hydroxide solution.

[0098] Example IB - Demonstration of the effects on hair

[0099] To demonstrate the beneficial effects of the compositions as disclosed on curly hair, approximately 0.4 grams of each of compositions IA and Cl to C4 was applied to three separate strands of curly hair (Caucasian type). The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were then left to dry overnight in a room with a relative humidity of 20%. After drying overnight, the strands were evaluated.

[0100] Using the RUMBA system, the treated hair was first analyzed after overnight drying (T0), then after combing (T0combing), and finally after 24 hours of exposure to 80% relative humidity (T24H). Based on the RUMBA analysis, as shown in [Fig. 1], the strands treated with composition C1 resulted in hair with less curl definition, followed by compositions C2, C4, and C3, respectively, while composition IA, according to the disclosure, had the most defined curls, both at T0 and T24H. Table 3 below summarizes the results of this analysis.

[0101] [Tables3] T0 T24H Cl 7.3 12.5 C2 9.2 13.7 C3 10.4 21.3 C4 9.8 19.1 IA 12.0 22.8 Table 3: Average alignment coefficient (l / °)

[0102] Fig. 1 is a graphical representation of the data in Table 3, the bars at each point representing the standard deviation.

[0103] Figures 2A to 2E show images of hair strands treated with comparative compositions Cl to C4 and the inventive composition IA, obtained with the RUMBA analyzer. Each figure shows the front and back image of each of the three strands treated with each composition, at T0, T0 combing, and T24H. Figures 2A to 2E visually confirm what is shown in Table 3 and in [Fig. 1], namely that the hair treated with composition IA according to the disclosure showed better curl definition and better frizz control than the hair treated with comparative compositions Cl to C4, which is particularly noticeable after the hair was subjected to high humidity for 24 hours (T24H).

[0104] The treated hair strands were also analyzed under controlled environmental conditions (temperature and humidity), in which photographic images of the strands were obtained at specified times and evaluated for changes in hair volume and surface area over time, in order to assess frizz. The treated hair was first analyzed after overnight drying (T0), then after 0.5 hours (T0.5H), 1 hour (T1H), 2 hours (T2H), and 24 hours (T24H) of exposure to 80% relative humidity conditions, in order to measure frizz and frizz surface area of ​​each strand. As can be seen in Figures 3A and 3B, strands treated with composition Cl gave hair with less frizz control, followed by compositions C2, C3 and C4 respectively, while composition IA according to disclosure provided superior frizz control.

[0105] Figures 4A to 4E show images of the hair strands that were treated with the comparative compositions Cl to C4 and the inventive composition IA. Each figure shows the three strands treated with each composition, at T0, T0.5H, T1H, T2H, and T24H. Figures 4A to 4E visually confirm that the treated hair with composition IA according to the disclosure demonstrated better frizz control than hair treated with comparative compositions Cl to C4, which is particularly noticeable after the hair has been subjected to high humidity for 24 hours (T24H).

[0106] Example 2A - Demonstration of the advantage over a range of molar ratios

[0107] To demonstrate the improved frizz control of hair treated with compositions according to the disclosure over a range of molar ratios of carboxylic acid:cyclodextrin, two compositions were prepared according to the disclosure, containing molar ratios of 6:1 (composition 2A) and 10:1 (composition 2B) citric acid:B-cyclodextrin in water, following the same procedure as in Example IA, and compared to composition Cl of Example IA.

[0108] Approximately 0.4 grams of each of compositions 2A, 2B, and Cl was applied to three separate strands of curly (Caucasian) hair. The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were left to air dry overnight. After drying overnight, the strands were evaluated.

[0109] The treated hair strands were also analyzed under controlled environmental conditions (temperature and humidity), in which photographic images of the strands were obtained at specified times and evaluated for changes in hair volume and surface area over time, in order to assess frizz. The treated hair was first analyzed after overnight drying (T0), then after 1 hour (T1H) and 24 hours (T24H) of exposure to 80% relative humidity, in order to measure frizz and frizz surface area of ​​each strand. As can be seen in Figures 5A and 5B, the strands treated with composition Cl resulted in hair with less frizz control, while compositions 2A and 2B, as disclosed, provided frizz control to the treated hair, with hair treated with composition 2B demonstrating the greatest degree of frizz control.

[0110] Figures 6A to 6C show images of hair strands that were treated with the comparative composition Cl and the inventive compositions 2A and 2B. Each figure shows the three strands treated with each composition, at T0 and T24H. Figures 6A to 6C visually confirm that the hair treated with compositions 2A and 2B according to the disclosure demonstrated better frizz control than the hair treated with the comparative composition Cl, both at T0 and T24H. [YES] Example 2B - Demonstration of the advantage over a range of molar ratios

[0112] To demonstrate the improvement in curl definition and frizz control hair treated with compositions according to the disclosure within a range of Molar ratios: Two premixes were prepared according to the disclosure, following the procedure in Example IA, to prepare premixes with molar ratios of 6:1:10 (premix 2C) and 3:1:10 (premix 2D) citric acid:B-cyclodextrin:water, following the same procedure as in Example IA. Premixes 2C and 2D were then mixed with water in a ratio of 5:95 premix:water to prepare compositions 2C and 2D, which were compared to the Cl composition of Example IA.

[0113] Approximately 0.4 grams of each of compositions 2C, 2D, and Cl was applied to two separate strands of curly (Caucasian) hair. The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were left to air dry overnight.

[0114] After drying overnight, the strands were visually assessed (T0), then subjected to 80% relative humidity conditions and visually assessed again after 1 hour (T1H), as shown in Figures 7A and 7B. As can be seen in the figures, after one hour of high humidity, the hair strands treated with compositions 2C and 2D exhibit significantly better curl definition and frizz control than the strands treated with composition CL

[0115] Example 2C - Demonstration of the advantage over a range of molar ratios

[0116] To demonstrate the improvement in curl definition and frizz control For hair treated with the compositions as disclosed, within a range of molar ratios, four premixes were prepared according to the disclosure, following the procedure in Example IA, to prepare premixes with molar ratios of 2:1:10 (premix 2E), 6:1:10 (premix 2F), 15:1:10 (premix 2G), and 20:1:10 (premix 2H). The citric acid:B-cyclodextrin:water premixes were prepared following the same procedure as in Example IA. The premixes were then mixed with water at a ratio of 5:95 premix:water to prepare compositions 2E through 2H.

[0117] Approximately 0.15 gram (A) or 0.4 gram (B) of each of compositions 2E to 2H was applied to two separate strands of curly (Caucasian) hair. The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were left to air dry overnight.

[0118] After drying overnight, the strands were visually assessed (T0), then subjected to 80% relative humidity and visually assessed again after 1 hour (T1H), as shown in Figures 8A and 8B. As can be seen in the figures, after one hour of high humidity, the hair strands show that curl definition, frizz control, or both, are maintained over a range of molar ratios.

[0119] Example 3 - Demonstration of the advantage over a range of concentrations

[0120] To demonstrate the improvement in curl definition and frizz control of hair treated with compositions as disclosed in a range of premix concentrations in the final composition, four compositions were prepared. A premix having a molar concentration of 6:1:10 citric acid:B-cyclodextrin:water was prepared as in Example IA, and was then mixed with additional water at premix:water ratios of 2.5:97.5 (composition 3A), 5:95 (composition 3B), 15:85 (composition 3C), and 30:70 (composition 3D).

[0121] Approximately 0.15 gram (A) or 0.4 gram (B) of each of compositions 3A to 3D was applied to two separate strands of curly (Caucasian) hair. The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were left to air dry overnight.

[0122] After drying overnight, the strands were visually assessed (T0), then subjected to 80% relative humidity and visually assessed again after 1 hour (T1H), as shown in Figures 9A and 9B. The strands after 1 hour were compared to a strand treated with composition Cl from Example IA. As can be seen in the figures, after one hour in high humidity, the hair strands treated with compositions 3A to 3D, at both concentrations of the applied composition, show that curl definition, frizz control, or both, are maintained over a range of premix concentrations in the final composition.

[0123] Example 4A - Compositions with a range of carboxylic acids

[0124] To demonstrate that the benefits of improved curl definition and / or frizz control are imparted to curly hair by using other carboxylic acids according to the disclosure, six compositions were prepared with the following amounts of acid, B-cyclodextrin and water.

[0125] [Tables4] Composition Acid (%) B-cyclodextrin (%) Water (%) 4A Lactic acid* 1.5 1.5 q.s. to 100 4B Malic acid 1.4 1.5 q.s. to 100 4C Maleic acid 1.1 1.1 q.s. to 100 4D Tartaric acid 0.8 1.5 q.s. to 100 4E Glycolic acid 1.5 1.5 q.s. to 100 4F Phytic acid** 1.2 1.1 q.s. to 100

[0126] * Added as an active ingredient at 90% in water

[0127] **added as an active ingredient at 50% in water

[0128] Each of the compositions 4A to 4F was adjusted to a pH of about 3.5 to 4.0 with a 0.1 M sodium hydroxide solution.

[0129] Example 4B - Demonstration of the benefits for hair with a range of carboxylic acids

[0130] To demonstrate the improvement in curl definition and frizz control of hair treated with the compositions disclosed over a range of carboxylic acids, three separate strands of curly (Caucasian type) hair were washed with a standard shampoo, rinsed, and the excess water was removed by hand. Then, approximately 0.4 grams of each of compositions 4A to 4F or Cl from Example IA was applied to each of the three hair strands.

[0131] The compositions were massaged into the hair to ensure even distribution, and the treated hair was scrunched five times by hand. The strands were then left to dry overnight in a room with a relative humidity of 20%. After drying overnight, the strands were evaluated.

[0132] Using the RUMBA system, images of the treated hair were obtained after overnight drying (T0), and then again after 4 hours of exposure to 80% relative humidity (T4H). According to the analysis performed by the RUMBA system, as can be seen in Figures 10A to 10C, the strands treated with composition Cl exhibited less frizz control and less curl definition, while each of compositions 4A to 4F provided better frizz control and / or better curl definition.

[0133] The treated hair strands were also analyzed under conditions in Controlled environmental conditions (temperature and humidity) were used, in which photographic images of the hair strands were obtained at specified times and evaluated for changes in hair volume and surface over time to assess frizz. The treated hair was analyzed after 4 hours (T4H) of exposure to 80% relative humidity. As shown in Figures 11A and 11B, the strands treated with composition Cl resulted in hair with less frizz control, while compositions 4A through 4F, as disclosed, provided frizz control for the treated hair, even for compositions with a higher water content.

[0134] Figures 12A to 12G show images of hair strands that were treated with the comparative composition Cl and the inventive compositions 4A to 4F to T4H. Figures 12A to 12G visually confirm that the hair treated with compositions 4A to 4F according to the disclosure demonstrated better frizz control than the hair treated with the comparative composition CL

[0135] The above examples demonstrate that the compositions according to the disclosure provide better curl definition and / or better frizz control to hair, which lasts over time even after exposure to high humidity, over a range of different molar ratios, concentrations and components.

[0136] It will be obvious to those skilled in the art that various modifications and variations can be made to the compositions and methods according to the disclosure without departing from the spirit or scope of the disclosure. Thus, it is intended that the disclosure will cover such modifications and variations and their equivalents.

Claims

Demands

1. A composition for treating keratinous fibers, comprising: (a) at least one carboxylic acid or a salt thereof; (b) at least one cyclodextrin or a derivative thereof selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl derivatives of α-cyclodextrin, β-cyclodextrin or γ-cyclodextrin, hydroxypropyl derivatives of α-cyclodextrin, β-cyclodextrin or γ-cyclodextrin, or mixtures thereof; and (c) at least one solvent; wherein the composition has a molar ratio of (a):(b) from 5:1 to 12:1, and wherein the composition has a pH less than or equal to 7.

2. Composition according to claim 1, wherein the molar ratio of (a):(b) ranges from 6:1 to 10:1, preferably 6:1, 7:1, 8:1, 9:1, 10:1, 11:2, 13:2, 15:2, 17:2, 19:2, 16:3, 17:3, 19:3, or 20:3, and wherein at least one carboxylic acid or a salt thereof is selected from monocarboxylic acids, dicarboxylic acids, tricarboxylic acids, their salts, or mixtures thereof.

3. Composition according to claim 1 or claim 2, wherein at least one carboxylic acid or a salt thereof is selected from citric acid, lactic acid, malic acid, maleic acid, tartaric acid, glycolic acid, phytic acid, their salts, or mixtures thereof, and wherein at least one carboxylic acid or a salt thereof is present in an amount from 0.01% to 20%, preferably from 0.1% to 18%, from 0.5% to 15%, or from 1% to 13% by weight, relative to the total weight of the composition.

4. Composition according to any one of claims 1 to 3, wherein at least one cyclodextrin or a derivative thereof is selected from those of formula: | >OR / 1 RO^*****T^ k 1 °--. n in which: R is selected from H, CH3, or a hydroxypropyl group, and n ranges from 6 to 8.

5. Composition according to any one of claims 1 to 4, wherein at least one cyclodextrin or a derivative thereof is present in an amount from 0.01% to 20%, preferably from 0.1% to 18%, from 0.5% to 15%, or from 1% to 13% by weight, relative to the total weight of the composition.

6. A composition according to any one of claims 1 to 5, wherein the solvent is present in the composition in an amount from 50% to 99.9%, preferably from 70% to 99%, from 75% to 99%, from 80% to 99%, from 85% to 99%, from 90% to 99%, from 95% to 99%, from 97% to 99%, from 70% to 98%, from 75% to 98%, from 80% to 98%, from 85% to 98%, from 90% to 98%, from 95% to 98%, from 70% to 95%, from 75% to 95%, from 80% to 95%, from 85% to 95%, from 90% to 95%, from 70% to 90%, from 75% to 90%, 80% to 90%, or 85% to 90% by weight, relative to the total weight of the composition, and wherein the solvent comprises water and optionally at least one additional solvent selected from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propanediol, glycerin, ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, phenylethyl alcohol,glycols or glycol ethers such as monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol, butylene glycol, hexylene glycol or dipropylene glycol, alkyl ethers of diethylene glycol such as monoethyl ether or monobutyl ether of diethylene glycol, or mixtures thereof.

7. A composition according to any one of claims 1 to 6, comprising: (a) 0.1% to 10% of at least one carboxylic acid, wherein the at least one carboxylic acid is selected from citric acid, lactic acid, malic acid, maleic acid, tartaric acid, glycolic acid, phytic acid, their salts, or mixtures thereof; (b) 0.1% to 10% of at least one cyclodextrin, wherein the at least one cyclodextrin is selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl derivatives thereof, hydroxypropyl derivatives thereof, or mixtures thereof; and (c) 50% to 99.9% by weight of water and optionally at least one additional solvent; in which the composition has a molar ratio of (a):(b) ranging from 5:1 at 12:1; wherein the composition has a pH ranging from 2 to 6, preferably from 3 to 5, from 3.5 to 5, from 3 to 4.5, from 3.5 to 4.5, or from 3 to 4; and wherein all quantities are by weight, relative to the total weight of the composition.

8. Composition according to any one of claims 1 to 7, further comprising at least one additional component selected from thickening agents, conditioning agents, tints, pigments, moisturizing agents, fillers, structuring agents, glossing agents, antioxidants, perfumes, buffers, dispersants, plant extracts, preservatives, opacifiers, sunscreens, vitamins, pH adjusting agents, antistatic agents, or mixtures thereof, and wherein the at least one additional component is present in an amount of up to 15%, preferably from 0.01% to 15%, from 0.01% to 10%, from 0.01% to 5%, or from 0.01% to 1% by weight, relative to the total weight of the composition.

9. A hair treatment method comprising improving the definition of hair curls and / or providing frizz control to hair and / or providing volume control to hair, comprising applying to hair a composition according to any one of claims 1 to 8.

10. A method for improving the definition of hair curls and / or providing frizz control to hair and / or providing volume control to hair, comprising applying to the hair a composition according to any one of claims 1 to 8.

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