COMPOSITION SUITABLE FOR KERATINOUS FIBERS

A composition using glyoxylic acid derivatives and quaternary esters provides durable keratin fiber remodeling without reducing agents, addressing the limitations of conventional methods by enhancing shape retention and reducing damage and odor.

FR3158229B3Active Publication Date: 2026-02-13LOREAL SA
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Patent Information

Application Number
FR2024000240
Authority / Receiving Office
FR · FR
Patent Type
Utility models
Current Assignee / Owner
Filing Date
2024-01-11
Publication Date
2026-02-13
Estimated Expiration
2034-01-11

AI Technical Summary

Technical Problem

Conventional permanent straightening methods for keratin fibers using reducing and oxidizing agents are time-consuming, damaging, and produce bad odors, while existing methods without these agents provide only short-lasting results.

Method used

A composition for keratin fibers comprising glyoxylic acid derivatives, keto acids, and quaternary esters, applied at temperatures above 50°C, which provides durable remodeling effects without ammonia or thiol compounds.

Benefits of technology

The composition achieves long-lasting straightening or curling effects with reduced fiber damage and odor, maintaining shape after shampooing, and is easier to use with shorter processing times.

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Abstract

COMPOSITION SUITABLE FOR KERATINOUS FIBERS The present invention relates principally to a composition for keratinous fibers such as hair, comprising: (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; (b) at least one compound, other than (a), selected from the group consisting of keto acids, their salts, and mixtures thereof; and (c) at least one quater ester. The present invention can improve the smoothing of keratinous fibers such as hair based on heating the keratinous fibers with glyoxylic acid or one of its derivatives, providing more durable remodeling effects. Figure for abstract: none
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Description

Title of the invention: COMPOSITION SUITABLE FOR KERATINOUS FIBERS technical field

[0001] The present invention relates primarily to a composition suitable for remodeling, preferably smoothing, keratinous fibers such as hair. PRIORITY OF THE TECHNOLOGY

[0002] Straightening keratin fibers, such as hair, by heating them with a flat iron is a popular method for making unruly keratin fibers easier to style and for making them less voluminous and more attractive. Such a straightening process using a heated iron is convenient for quick styling, but the hairstyle only lasts a short time, for example, until the next shampoo. A more permanent straightening method is required by many consumers.

[0003] Furthermore, conventional permanent straightening processes using a reducing agent and an alkaline agent, as well as an oxidizing agent, with heating, can offer keratin fibers a durable hairstyle, but they have several disadvantages such as a long treatment time, damage to keratin fibers and a bad smell.

[0004] WO 2014 / 131469 discloses a process for smoothing keratinous fibers by heating with an iron, without the aid of reducing and oxidizing agents, in which glyoxylic acid is used to smooth the keratinous fibers.

[0005] US-A-2023 / 742 discloses a semi-permanent hair smoothing composition including 15% to 20% by weight of glyoxylic acid and 0.1% to 5% by weight of levulinic acid. Cetrimonium chloride is also included in the compositions disclosed in its Examples section. DISCLOSURE OF THE INVENTION

[0006] There remains a need to improve the remodeling of keratinous fibers based on treatment of keratinous fibers with glyoxylic acid or one of its derivatives.

[0007] An objective of the present invention is to provide a composition that is useful for remodeling keratinous fibers such as hair, based on a treatment of the keratinous fibers with glyoxylic acid or one of its derivatives, which can provide the keratinous fibers with more durable remodeling effects.

[0008] The above objective of the present invention can be achieved by a composition for keratinous fibers, such as hair, comprising: a. at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; b. at least one compound, different from (a) compound, selected from the group consisting of keto acids, their salts, and mixtures thereof; and c. at least one quater ester.

[0009] The quantity of the (a) compound(s) in the composition according to the present invention may be less than 15% by weight, preferably less than 14% by weight, and more preferably less than 13% by weight, relative to the total weight of the composition.

[0010] The (b) compound can be chosen from levulinic acid, one of its salts and one of its mixtures.

[0011] The quantity of (b) compound(s) in the composition according to the present invention may be 10% by weight or less, preferably 8% by weight or less, and more preferably 6% by weight or less, relative to the total weight of the composition.

[0012] The (c) quat ester may be selected from the group consisting of distea-roylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate and one of their mixtures.

[0013] The quantity of the (c) quat ester(s) in the composition according to the present invention can be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0014] The composition according to the present invention may further comprise (d) water.

[0015] The composition according to the present invention may further comprise (e) at an oil.

[0016] The composition according to the present invention may further comprise (f) at least one fatty alcohol.

[0017] The pH of the composition according to the present invention may be 7 or less, preferably 6 or less, and more preferably 5 or less.

[0018] The composition according to the present invention may not comprise any ammonia or thiol compound, or may comprise less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of ammonia or thiol compound, relative to the total weight of the composition.

[0019] The composition according to the present invention may not include any reducing agent or oxidizing agent, or may include less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of a reducing agent or an oxidizing agent, relative to the total weight of the composition.

[0020] The composition according to the present invention can be intended for remodeling, preferably for smoothing, keratinous fibers such as hair.

[0021] The present invention also relates to a remodeling process, preferably a smoothing process, of keratinous fibers such as hair, comprising the following steps: i. application of the composition according to the present invention on keratinous fibers; ii. Optional rinsing of keratinous fibers with or without drying of the keratinous fibers after rinsing; and iii. remodeling, preferably smoothing, of keratinous fibers, preferably at a temperature above 50 °C, more preferably above 100 °C, and even more preferably above 150 °C.

[0022] The present invention also relates to a device for remodeling, preferably smoothing, keratinous fibers such as hair, comprising:

[0023] at least one device selected from the group consisting of an iron, a curling iron, a comb, a dryer and one of their combinations, preferably at least one heated iron, heated curling iron, heated comb or heated dryer which is capable of supplying the keratin fibers with a temperature above 50 °C, preferably above 100 °C, and more preferably above 150 °C; and

[0024] the composition according to the present invention. Best embodiment of the invention

[0025] After diligent research, the inventors discovered that it is possible to propose a composition which is useful for remodeling keratinous fibers such as hair, based on a treatment of the keratinous fibers with glyoxylic acid or one of its derivatives, and which can provide the keratinous fibers with more durable remodeling effects.

[0026] Thus, the present invention relates primarily to a composition for keratinous fibers, such as hair, comprising: a. at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; b. at least one compound, different from (a) compound, selected from the group consisting of keto acids, their salts, and mixtures thereof; and c. at least one quater ester.

[0027] The present invention can improve the remodeling of keratinous fibers such as hair, based on a treatment of the keratinous fibers with glyoxylic acid or one of its derivatives, providing more durable remodeling effects.

[0028] The remodeling of keratinous fibers, such as hair, here encompasses the straightening or curling of keratinous fibers.

[0029] The present invention can provide keratinous fibers such as hair with more durable remodeling effects. In particular, the present invention can further maintain the straight or curly shape of keratinous fibers, or can prevent or reduce the loss of the straight or curly shape of keratinous fibers over time.

[0030] For example, if keratin fibers are originally wavy, the present invention can offer better prevention against a return of keratin fibers to their original wavy shape, after straightening of the keratin fibers, in particular after shampooing.

[0031] The present invention can also provide keratin fibers with sufficient immediate remodeling effects. For example, keratin fibers treated with the present invention to be smoothed may exhibit less volume or less frizz due to the reduction of the keratin fiber curls. The remodeling effects offered by the present invention can last a long time, for example, even after shampooing the keratin fibers. Thus, the present invention can also provide a keratin fiber shape with good shampoo resistance.

[0032] The present invention can cause less damage to keratin fibers compared to conventional permanent remodeling processes, because the present invention does not require the use of reducing / oxidizing agents. Consequently, it can be easy to comb the keratin fibers treated by the present invention. Thus, keratin fibers treated with the present invention can be easy to style. Also, keratin fibers treated by the present invention can be more resistant than those treated by conventional permanent remodeling technologies.

[0033] Furthermore, the present invention can use little or no ammonia or thiol compound, and consequently, the odor during the use of the present invention can be reduced compared to conventional processes that require the use of ammonia or a thiol compound. In addition, the present invention may offer ease of use, for example, a short processing time.

[0034] We will describe the present invention in detail below. [Composition]

[0035] The composition according to the present invention comprises:

[0036] (a) at least one compound selected from the group consisting of glyoxylic acid, the glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof;

[0037] (b) at least one compound, different from (a) compound, chosen from the group consisting in ketoacids, their salts, and their mixtures; and

[0038] (c) at least one quater ester.

[0039] Preferably, the composition according to the present invention should be a cosmetic composition, more preferably a cosmetic composition for remodeling keratin fibers, and even more preferably a cosmetic composition for remodeling keratin fibers in a single step. It is particularly preferable that the keratin fibers be hair.

[0040] (Glyoxylic acid and its derivatives)

[0041] The composition according to the present invention comprises (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides and mixtures thereof.

[0042] Only one type of (a) compound may be used, or two or more different types of (a) compounds may be used in combination.

[0043] Compound (a) is selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof. In other words, compound (a) is selected from glyoxylic acid and its derivatives.

[0044] Examples of glyoxylic acid solvates include, for instance, glyoxylic acid hydrates such as glyoxylic acid monohydrate.

[0045] Examples of glyoxylic acid salts include alkali metal salts or alkaline earth metal salts of glyoxylic acid such as sodium or potassium glyoxylate, and magnesium or calcium glyoxylate.

[0046] Examples of glyoxylic acid esters include alkyl esters of glyoxylic acid such as methyl glyoxylate and ethyl glyoxylate.

[0047] Examples of glyoxylic acid amides include N-glyoxyloylcarbocysteine ​​and N-glyoxyloyl keratin amino acids.

[0048] It is preferable to use glyoxylic acid as (a) compound.

[0049] The quantity of (a) compound(s) in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.

[0050] The quantity of the (a) compound(s) in the composition according to the present invention may be less than 15% by weight, preferably less than 14% by weight, and more preferably less than 13% by weight, relative to the total weight of the composition.

[0051] Thus, the quantity of the (a) compound(s) in the composition according to the present invention can be from 0.1% to less than 15% by weight, preferably from 0.5% to less than 14% by weight, and more preferably from 1% to less than 13% by weight, relative to the total weight of the composition.

[0052] In one embodiment, the quantity of the (a) compound(s) in the composition according to the present invention may be 12% by weight or less, preferably 11% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.

[0053] Thus, in this embodiment, the quantity of the (a) compound(s) in the composition according to the present invention can be from 0.1% to 12% by weight, preferably from 0.5% to 11% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.

[0054] (Ketoacid)

[0055] The composition according to the present invention comprises (b) at least one compound, different from (a) compound, selected from ketoacids, their salts, and mixtures thereof. Two or more (b) compounds may be used in combination. Thus, a single type of (b) compound or a combination of different types of (b) compounds may be used.

[0056] Ketoacids can be chosen from α-ketoacids, γ-ketoacids, γ-ketoacids and mixtures thereof.

[0057] α-Aketo acids can be compounds represented by the general formula (I):

[0058] R1-C(=O)-COOH (I)

[0059] in which

[0060] R1 designates a linear or branched Ci-C6 alkyl group, optionally substituted by OH, COOH or a halogen atom such as a chlorine or bromine atom.

[0061] Examples of α-keto acids include pyruvic acid.

[0062] The [3-keto acids can be represented by the general formula (II):

[0063] R2-C(=O)-R3-COOH (II)

[0064] in which • R2 denotes a linear or branched Ci-C6 alkyl group, optionally substituted by OH, COOH, or a halogen atom such as a chlorine or bromine atom; and • R3 designates a methylene group, optionally substituted by a halogen atom such as a chlorine or bromine atom.

[0065] Examples of [3-ketoacids include acetoacetic acid.

[0066] γ-ketoacids can be represented by the general formula (III):

[0067] R2-C(=O)-R4-COOH (III)

[0068] in which • R2 designates a linear or branched Ci-C6 alkyl group, optionally substituted by OH, COOH or a halogen atom such as a chlorine atom or bromine; and • R4 designates an ethylene group, optionally substituted by a halogen atom such as a chlorine or bromine atom.

[0069] Examples of γ-ketoacids include levulinic acid.

[0070] Ketoacid salts can be alkali metal salts or alkaline earth metal salts of ketoacid such as sodium or potassium salts of ketoacid, and magnesium or calcium salts of ketoacid.

[0071] It is preferable to use, as the (b) compound(s), γ-keto acid, and more preferably, levulinic acid and / or one of its salts such as sodium levulinate.

[0072] The quantity of (b) compound(s) in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.

[0073] The quantity of (b) compound(s) in the composition according to the present invention may be 10% by weight or less, preferably 8% by weight or less, and more preferably 6% by weight or less, relative to the total weight of the composition.

[0074] Thus, the quantity of the (b) compound(s) in the composition according to the present invention can be from 0.1% to 10% by weight, preferably from 0.5% to 8% by weight, and more preferably from 1% to 6% by weight, relative to the total weight of the composition.

[0075] In one embodiment, the quantity of the (b) compound(s) in the composition according to the present invention may be 5% by weight or less, preferably 4% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.

[0076] Thus, the quantity of the (b) compound(s) in the composition according to the present invention can be from 0.1% to 5% by weight, preferably from 0.5% to 4% by weight, and more preferably from 1% to 3% by weight, relative to the total weight of the composition.

[0077] In another embodiment, the (b) compound(s) may be present in a smaller quantity than the (a) compound(s) in the composition according to the present invention. For example, the weight ratio between the quantity of the (a) compound(s) and the (b) compound(s) included in the composition according to the present invention may range from 1:1 to 15:1, preferably from 1:1 to 10:1, and more preferably from 1:1 to 4:1.

[0078] (Ester Quat)

[0079] The composition according to the present invention comprises (c) at least one quater ester. Two or more quaternary esters may be used in combination. Thus, a single type of quaternary ester or a combination of different types of quaternary esters may be used.

[0080] The term "quaternary ester" here refers to a chemical compound comprising both at least one quaternary nitrogen atom and at least one ester bond in its cationic portion. Preferably, this refers to a class of surfactant quaternary ammonium compounds having the general formula R*R2R3R4N+A, in which at least one, preferably two, of the groups, preferably hydrocarbon groups, R1 to R4 have 6 or more carbon atoms, preferably 8 or more carbon atoms, and more preferably 10 or more carbon atoms, and at least one ester bond such as -C(=O)-O- and -OC(=O)-, and A denotes any anionic counterion.

[0081] Preferably, the (c) quat ester is selected from among quat diesters that have a quaternary nitrogen atom and two groups, preferably two hydrocarbon groups, in which each of the groups has 6 or more carbon atoms, preferably 8 or more carbon atoms, and more preferably 10 or more carbon atoms, and at least one ester bond, preferably one ester bond, as mentioned above. It is more preferable that, in the quat diesters, the oxygen atom of the ester bond is linked to the quaternary nitrogen atom via a C1-3 alkyl group such as an ethyl group.

[0082] In one embodiment of the present invention, the (c) quat ester can be represented by the following general formula (1):

[0083] RW-O-CH2CH2-N+(R3)2-CH2CH2-O-OCR2 A (1)

[0084] in which • each of R'CO and OCR2 independently designates a linear or branched acyl group, saturated or unsaturated, preferably saturated, having 10 to 28 carbon atoms, preferably 12 to 24 carbon atoms, and more preferably 14 to 20 carbon atoms, • R3 independently designates an alkyl group at C,4 such as a methyl group, or a hydroxyalkyl group at C1_4 such as a hydroxyethyl group (-CH2CH2OH), and • A is a counterion.

[0085] In a preferred embodiment, the radicals R1 and R2 in formula (1) are each independently linear alkyl groups having 9 to 27 carbon atoms, preferably 11 to 23 carbon atoms, and more preferably 13 to 19 carbon atoms.

[0086] In formula (1), the counterion A- can be chosen from chloride, bromide, methosulfate MeSO4 (where Me is methyl, CH3), tosylate, phosphate, sulfate, hydrogen sulfate, lactate and citrate, more preferably from chloride and methosulfate MeSO4. The counterion A- can in particular be chloride.

[0087] In a more preferred embodiment, in formula (1) above, R'CO and OCR2 can be derived from • (a) octadecanoic acid: this yields, for example, distea-roylethyl dimonium chloride, • (1b) eicosanoic acid: this gives, for example, dieosanoic chloride soylethyl dimonium • Docosanoic acid: this yields, for example, didoco-soylethyl dimonium chloride, • (Id) tetracosanoic acid: this yields, for example, ditetra-cosoylethyl dimonium chloride, • (the) oleic acid: this yields, for example, dio-oleoylethyl hydroxyethylmonium methosulfate, • (If) the fatty acid in C20-22: this gives, for example, dibehen-noylethyl dimonium chloride, • (1g) the C18 22 fatty acid: this gives, for example, stea- chloride roylethyl behenoylethyl dimonium or distearoylethyl dimonium chloride or distearoylethyl hydroxyethylmonium methosulfate, and • (Ih) the fatty acid in C16-22: this gives, for example, dipalmitoylethyl dimonium chloride or dipalmitoylethyl hydroxyethylmonium methosulfate.

[0088] Preferably, the (c) quat ester is selected from the group consisting of distearoylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate, dibehenoylethyl dimonium chloride, dipalmitoylethyl dimonium chloride and one of their mixtures.

[0089] In particular, it is preferable that the (c) quat ester be selected from the group consisting of distearoylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate, and mixtures thereof. Varisoft EQ 65 MB, marketed by Evonik, may be used as distearoylethyl dimonium chloride. Varisoft EQ 90, marketed by Evonik, may be used as dioleoylethyl hydroxyethylmonium methosulfate.

[0090] The quantity of the (c) quat ester(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0091] The quantity of the (c) quat ester(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.

[0092] Thus, the quantity of the (c) quat ester(s) in the composition according to the present invention can be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0093] (Water)

[0094] The composition according to the present invention may include (d) water.

[0095] Thus, if the composition according to the present invention comprises (d) water, the composition according to the present invention is not anhydrous.

[0096] The quantity of (d) water in the composition according to the present invention may be 20% by weight or more, preferably 30% by weight or more, and more preferably 40% by weight or more, relative to the total weight of the composition.

[0097] Furthermore, the quantity of (d) water in the composition according to the present invention may be 95% by weight or less, preferably 90% by weight or less, and more preferably 85% by weight or less, relative to the total weight of the composition.

[0098] The quantity of (d) water in the composition according to the present invention can be from 20% to 95% by weight, preferably from 30% to 90% by weight, and more preferably from 40% to 85% by weight, relative to the total weight of the composition.

[0099] (Oil)

[0100] The composition according to the present invention may comprise (e) at least one oil. Two or more oils may be used in combination. Thus, a single type of oil or a combination of different types of oils may be used.

[0101] Here, "oil" means a fatty compound or oily substance that is in the form of a liquid, paste, or solid at room temperature (25 °C) under atmospheric pressure (760 mmHg). Oils commonly used in cosmetics can be used alone or in combination. These oils can be volatile or non-volatile.

[0102] The (e) oil may be a non-polar oil such as a hydrocarbon oil, a silicone oil or the like; a polar oil such as a vegetable or animal oil and an ester oil or an ether oil; or a mixture thereof.

[0103] The (e) oil may be chosen from the group consisting of oils of vegetable or animal origin, synthetic oils, silicone oils and hydrocarbon oils.

[0104] Examples of oils of vegetable origin include, for example, linseed oil, camellia oil, macadamia nut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, jojoba esters, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil, and mixtures thereof.

[0105] Examples of synthetic oils include alkane oils such as isododecane and isohexadecane, ester oils, ether oils and artificial triglycerides.

[0106] The ester oils are preferably liquid esters of saturated or unsaturated, linear or branched, Ci-C26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched, Ci-C26 aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.

[0107] Preferably, for monoalcohol esters, at least one of the alcohol and acid from which the esters of the present invention are derived is branched.

[0108] Among the monoesters of monoacids and monoalcohols, ethyl palmitate, ethylhexyl palmitate, isopropyl palmitate, dicaprylyl carbonate, alkyl myristates such as isopropyl myristate or ethyl myristate, cetyl palmitate, isocetyl stearate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate may be mentioned.

[0109] Esters of dicarboxylic or tricarboxylic acids in C4-C22 and of alcohols in Ci-C22, and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of non-sugar dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols in C4-C26, can also be used.

[0110] Examples include: diethyl sebacate; isopropyl lauroyl sarcosinate; diisopropyl sebacate; bis(2-ethylhexyl) sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; bis(2-ethylhexyl) adipate; diisostearyl adipate; bis(2-ethylhexyl) maleate; triisopropyl citrate; trii-socetyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; neopentyl glycol diheptanoate; diethylene glycol dii-sononanoate.

[0111] As ester oils, esters and sugar diesters of C6-C30 fatty acids, and preferably C12-C22, may be used. It should be noted that the term "sugar" refers to oxygen-bearing hydrocarbon compounds containing several alcohol functional groups, with or without aldehyde or ketone functional groups, and comprising at least four carbon atoms. These sugars may be monosaccharides, oligosaccharides, or polysaccharides.

[0112] Examples of suitable sugars that may be cited include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose and their derivatives, including alkyl derivatives, such as methyl derivatives, for example methylglucose.

[0113] Sugar esters of fatty acids may be selected in particular from the group comprising the esters or mixtures of esters of sugars described above and of fatty acids in C6-C30, and preferably in linear or branched C12-C22, saturated or unsaturated. If they are unsaturated, these compounds can have one to three conjugated or non-conjugated carbon-carbon double bonds.

[0114] The esters according to this variant can also be chosen from monoesters, diesters, triesters, tetraesters, polyesters and their mixtures.

[0115] These esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, in particular, mixed esters of oleopalmitate, oleostearate and palmitostearate, as well as pentaerythrityl tetraethyl hexanoate.

[0116] More particularly, monoesters and diesters are used, and in particular monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates of sucrose, glucose or methylglucose.

[0117] An example that can be cited is the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.

[0118] By way of examples of preferred ester oils, the following may be cited, for example: diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyle propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanoate, 2-ethylhexyl caprylate / caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicaprylyl carbonate, isopropyl lauroyl sarcosinate, isononyl isononanoate, ethylhexyl palmitate, isohexyl laurate, hexyl laurate, stearate isocetyl, isopropyl isostearate, isopropyl myristate, isodecyl oleate, glyceryl tri(2-ethylhexanoate), pentaerythrityl tetra(2-ethylhexanoate), 2-ethylhexyl succinate, diethyl sebacate, and mixtures thereof.

[0119] Examples of artificial triglycerides include, for example, capryl caprylyl glycerides, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate / caprylate) and glyceryl tri(caprate / caprylate / linolenate).

[0120] Examples of silicone oils include, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenopolysiloxane and the like; cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.

[0121] Preferably, silicone oils are selected from liquid polydialkylsiloxanes, in particular liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group.

[0122] These silicone oils can also be organo-modified. The organo-modified silicones that can be used according to the present invention are silicone oils as defined above and comprise in their structure one or several organofunctional groups attached via a hydrocarbon-based group.

[0123] Organopolysiloxanes are defined in more detail in Chemistry and Technology of Silicones (1968) by Walter Noll, Academy Press. They can be volatile or non-volatile.

[0124] When volatile, silicones are particularly chosen from those having a boiling point between 60 °C and 260 °C, and even more particularly from: i. Cyclic polydialkylsiloxanes comprising 3 to 7, and preferably 4 to 5, silicon atoms. Examples include octamethylcyclotetrasiloxane, sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia; decamethylcyclopentasiloxane, sold under the name Volatile Silicone® 7158 by Union Carbide and Silbione® 70045 V5 by Rhodia; and dodecamethylcyclopentasiloxane, sold under the name Silsoft 1217 by Momentive Performance Materials, and mixtures thereof. Also included are cyclocopolymers of the dimethylsiloxane / methylal-kylsiloxane type, such as Silicone Volatile® FZ 3109, sold by Union Carbide, with the formula:

[0125] We can also mention mixtures of cyclic polydialkylsiloxanes with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetramethylsilylpentaerythritol (50 / 50) and the mixture of octamethylcyclotetrasiloxane and oxy-l,r-bis(2,2,2',2',3,3'-hexatrimethylsilyloxy)neopentane; i. Linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity less than or equal to 5 x 10⁶ m² / s at 25 °C. An example is decamethyltetrasiloxane, sold in particular under the name SH 200 by Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 1976, pp. 27–32, Todd & Byers, Volatile Silicone Fluids for Cosmetics. The viscosity of silicones is measured at 25 °C according to ASTM 445 Annex C.

[0126] Non-volatile polydialkylsiloxanes can also be used. These non-volatile silicones are more particularly chosen from among the polydialkylsiloxanes, among which the main examples are polydimethylsiloxanes containing trimethylsilyl terminal groups.

[0127] Among these polydialkylsiloxanes, the following commercial products may be cited, without limitation: • Silbione® oils from the 47 and 70 047 ranges or Mirasil® oils sold by Rhodia, for example oil 70 047 V 500 000; • the oils from the Mirasil® range sold by the company Rhodia; oils from the 200 series by Dow Corning, such as DC200 with a viscosity of 60,000 mm2 / s; Viscasil® oils from General Electric and certain oils from the SF range (SF 96, SF 18) from General Electric.

[0128] We can also mention polydimethylsiloxanes containing dimethylsilanol terminal groups known as dimethiconol (CTFA), such as the oils in the 48 range from the Rhodia company.

[0129] Silicones containing aryl groups include polydiarylsiloxanes, in particular polydiphenylsiloxanes and polyalkylarylsiloxanes. Examples that may be cited include products sold under the following names: Rhodia's Silbione® oils from the 70 641 range; the oils from the Rhodorsil® 70 633 and 763 ranges from Rhodia; Dow Corning 556 Cosmetic Grade Fluid; silicones from Bayer's PK range, such as product PK20; certain oils from General Electric's SF range, such as SF 1023, SF 1154, SF 1250 and SF 1265.

[0130] Organomodified liquid silicones may, in particular, contain polyethyleneoxy and / or polypropyleneoxy groups. Examples include KF-6017 silicone offered by Shin-Etsu, and Silwet® L722 and L77 oils from Union Carbide.

[0131] Hydrocarbon oils may be selected from: lower C6-Ci6 alkanes, linear or branched, optionally cyclic. Examples that can be cited include hexane, undecane, dodecane, tridecane, and isoparaffins, for example isohexadecane, isododecane, and isodecane; and linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffins, liquid petroleum jelly, hydrogenated polydecenes and polyisobutenes such as Parleam® and squalane.

[0132] Preferred examples of hydrocarbon oils include, for example, linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, Vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosane and decene / butene copolymers; and mixtures thereof.

[0133] It is preferable that the (e) oil be chosen from among polar oils, more preferably ester oils, and even more preferably monoester oils.

[0134] The quantity of the oil(s) in the composition according to the present invention may be 1% by weight or more, preferably 3% by weight or more, and more preferably 5% by weight or more, relative to the total weight of the composition.

[0135] Furthermore, the quantity of the oil(s) in the composition according to the present invention may be 40% by weight or less, preferably 30% by weight or less, and more preferably 20% by weight or less, relative to the total weight of the composition.

[0136] The quantity of the oil(s) in the composition according to the present invention can be from 1% to 40% by weight, preferably from 3% to 30% by weight, and more preferably from 5% to 20% by weight, relative to the total weight of the composition.

[0137] (Fatty alcohol)

[0138] The composition according to the present invention may comprise (f) at least one fatty alcohol. Only one type of fatty alcohol may be used, or two or more different types of fatty alcohols may be used in combination.

[0139] The term "fatty" here means the inclusion of a relatively large number of carbon atoms. Thus, alcohols with 6 or more carbon atoms, preferably 8 or more, and more preferably 10 or more, are included within the scope of fatty alcohols. Fatty alcohols can be saturated or unsaturated. Fatty alcohols can be linear or branched. Two or more fatty alcohols can be used in combination.

[0140] The (f) fatty alcohol may have the structure R-OH in which R is selected from saturated and unsaturated, linear and branched radicals containing from 8 to 40 carbon atoms, for example from 8 to 30 carbon atoms. In at least one embodiment, R is selected from Ci2-C24 alkyl and Ci2-C24 alkenyl groups. R may or may not be substituted by at least one hydroxyl group.

[0141] Non-limiting examples of (f) fatty alcohols that may be cited include lauric alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, arachidonylic alcohol, erucyl alcohol, cetearyl alcohol and any mixture thereof.

[0142] Examples of suitable fatty alcohols include, but are not limited to, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol and mixtures thereof.

[0143] Fatty alcohol can represent a mixture of fatty alcohols, which means that several species of fatty alcohol can coexist, in mixture form, in a commercial product.

[0144] According to at least one embodiment, the fatty alcohol used in the composition according to the present invention is chosen from a mixture of cetyl alcohol and stearyl alcohol (cetearyl alcohol).

[0145] It is preferable that the (f) fatty alcohol be chosen from the group consisting of cetyl alcohol, cetearyl alcohol and stearyl alcohol.

[0146] The quantity of the fatty alcohol(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.

[0147] Furthermore, the quantity of the (f) fatty alcohol(s) in the composition according to the present invention may be 20% by weight or less, preferably 5% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.

[0148] The quantity of the (f) fatty alcohol(s) in the composition according to the present invention can range from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.

[0149] (Non-ionic surfactant)

[0150] The composition according to the present invention may comprise (g) at least one nonionic surfactant. Only one type of nonionic surfactant may be used, or two or more different types of nonionic surfactants may be used in combination.

[0151] Nonionic surfactants are well-known compounds in themselves (see, for example, in this regard, "Handbook of Surfactants" by M.R. Porter, Blackie & Son, publishers (Glasgow and London), 1991, pages 116-178). Thus, they may, for example, be chosen from alcohols, alpha-diols, alkylphenols, and fatty acid esters, these compounds being ethoxylated, propoxylated, or glycerolated and having at least one fatty chain comprising, for example, 8 to 30 carbon atoms, knowing that the number of ethylene oxide or propylene oxide groups may range from 2 to 50, and that the number of glycerol groups may range from 1 to 30. Maltose derivatives may also be mentioned.Other examples include, but are not limited to, copolymers of ethylene oxide and / or propylene oxide; condensates of ethylene oxide and / or propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, 2 to 30 mol of ethylene oxide; polyglycerol fatty amides comprising, for example, 1.5 to 5 glycerol groups, such as 1.5 to 4; ethoxylated fatty acid esters of sorbitan comprising 2 to 30 mol of ethylene oxide; ethoxylated oils of vegetable origin; fatty acid esters of sucrose; fatty acid esters of polyethylene glycol; mono- or diesters of polyethoxylated fatty acids of (C6-C24)alkyl polyglycosides of glycerol; N-(C6-C24)alkylglucamine derivatives, amine oxides such as (C10-C14)alkylamine oxides or N-(Cio-Ci4)acylaminopropylmorpholine oxides; silicone surfactants; and mixtures thereof.

[0152] Non-ionic surfactants may preferably be chosen from monooxyalkylated, polyoxyalkylated, monoglycerolated or poly- non-ionic surfactants glycerolated. The oxyalkylene motifs are more particularly oxyethylene or oxypropylene motifs, or one of their combinations, and are preferably oxyethylene motifs.

[0153] Examples of monooxyalkylated or polyoxyalkylated nonionic surfactants that may be cited include:

[0154] monooxyalkylated or polyoxyalkylated (C8-C24)alkylphenols,

[0155] saturated or unsaturated, linear or branched, monooxyalkylated or polyoxyalkylated C8-C30 alcohols,

[0156] saturated or unsaturated, linear or branched, monooxyalkylated or polyoxyalkylated C8-C30 amides,

[0157] polyoxyethylenated esters of saturated or unsaturated, linear or branched C8-C30 acids, and of monoalkylene glycol or polyalkylene glycols,

[0158] monooxyalkylated or polyoxyalkylated esters of saturated or unsaturated, linear or branched C8-C30 acids, and of sorbitol,

[0159] saturated or unsaturated vegetable oils, monooxyalkylated or polyoxyalkylated, and

[0160] ethylene oxide and / or propylene oxide condensates, among others, alone or in mixture.

[0161] Surfactants preferably contain a number of moles of ethylene oxide and / or propylene oxide between 1 and 100, preferably between 1 and 50, and more preferably between 1 and 20.

[0162] According to one embodiment of the present invention, the non-ionic monooxyalkylated surfactants can be selected from monooxyethylated fatty alcohol (ethylene glycol fatty alcohol ether), monooxyethylated fatty ester (ethylene glycol fatty acid ester), and mixtures thereof.

[0163] Examples of monooxyalkylated fatty esters that may be cited include glycol distearate.

[0164] According to one embodiment of the present invention, the non-ionic polyoxyalkylated surfactants can be selected from polyoxyethylenated fatty alcohol (polyethylene glycol fatty alcohol ether), polyoxyethylenated fatty ester (polyethylene glycol fatty acid ester), and mixtures thereof.

[0165] Examples of polyoxyethylenated fatty alcohols (or C8-C30 alcohols) that may be cited include ethylene oxide adducts with lauryl alcohol, in particular those containing 2 to 20 oxyethylene units and more particularly those containing 2 to 10 oxyethylene units (CTFA names Laureth-2 to Laureth-20); ethylene oxide adducts with behenyl alcohol, in particular those containing 2 to 20 oxyethylene units (CTFA names Beheneth-2 to Beheneth-20); ethylene oxide adducts with cetearyl alcohol (a mixture of cetyl alcohol and stearyl alcohol), including those containing 2 to 20 oxyethylene motifs (CTFA names Ceteareth-2 to Ceteareth-20); ethylene oxide adducts with cetyl alcohol, including those containing 2 to 20 oxyethylene motifs (CTFA names Ceteth-2 to Ceteth-20); ethylene oxide adducts with stearyl alcohol, including those containing 2 to 20 oxyethylene motifs (CTFA names Steareth-2 to Steareth-20); ethylene oxide adducts with isostearyl alcohol, including those containing 2 to 20 oxyethylene motifs (CTFA names Isosteareth-2 to Isosteareth-20) and mixtures thereof.

[0166] Examples of unsaturated polyoxyethylenated fatty alcohols (or C8-C30 alcohols) that may be cited include ethylene oxide adducts with oleyl alcohol, in particular those containing 2 to 20 oxyethylene motifs and more particularly those containing 2 to 10 oxyethylene motifs (CTFA names Oleth-2 to Oleth-20); and mixtures thereof.

[0167] It is preferable that the (g) non-ionic surfactant be chosen from monooxyalkylated, polyoxyalkylated non-ionic surfactants, more preferably polyoxyalkylated non-ionic surfactants, and even more preferably polyoxyethylated fatty alcohols.

[0168] The quantity of the (g) non-ionic surfactant(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.

[0169] Furthermore, the quantity of the (g) non-ionic surfactant(s) in the composition according to the present invention may be 20% by weight or less, preferably 5% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.

[0170] The quantity of the (g) non-ionic surfactant(s) in the composition according to the present invention can range from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.

[0171] (pH)

[0172] The composition according to the present invention may have a pH of 7 or less, preferably of 6 or less, and more preferably of 5 or less, which is measured at 25 °C.

[0173] The composition according to the present invention may have a pH of 2.8 or more, which is measured at 25 °C.

[0174] The composition according to the present invention may have a pH of 2.8 to 7, preferably of 3.0 to 6, and more preferably of 3.2 to 5, which is measured at 25 °C.

[0175] (Alkaline agent)

[0176] The composition according to the present invention may comprise at least one agent alkaline. Two or more alkaline agents can be used in combination. Thus, a single type of alkaline agent or a combination of different types of alkaline agents can be used.

[0177] It is preferable that the composition according to the present invention include one or more alkaline agent(s), if the (a) compound or the (b) compound can be used to reduce the pH of the composition.

[0178] The alkali agent may be an inorganic alkali agent. Preferably, the alkali agent should be non-volatile. Preferably, the inorganic alkali agent should be chosen from the group consisting of alkali metal hydroxides; alkaline earth metal hydroxides; and alkali metal phosphates and monohydrogen phosphates such as sodium phosphate or sodium monohydrogen phosphate.

[0179] Examples of inorganic alkali metal hydroxides include sodium hydroxide, lithium hydroxide, and potassium hydroxide. Examples of alkaline earth metal hydroxides include calcium hydroxide and magnesium hydroxide. Sodium hydroxide and potassium hydroxide are preferable as inorganic alkali metals.

[0180] The alkali agent may be an organic alkali agent. Preferably, the organic alkali agent should be chosen from the group consisting of monoamines and diamines.

[0181] Examples of monoamines include alkanolamines such as mono-, di-, and triethanolamine, comprising 1 to 3 hydroxyalkyl groups (C1-C4). In particular, alkanolamines may be selected from monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N,N-dimethylethanolamine, 2-amino-2-methyl-1-propanol, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino-1,2-propanediol, and tris(hydroxymethylamino)methane.

[0182] Diamines can be described by the structure (B) below: FC R. <B) N. / NW-N / X Rs Rd

[0183] in which W denotes an alkylene such as propylene optionally substituted by a C1-C4 hydroxyl or alkyl radical, and Ra, Rb, Rc and Rd independently denote a hydrogen atom, an alkyl radical or a C1-C4 hydroxyalkyl radical, an example of which may be 1,3-propanediamine and its derivatives.

[0184] The quantity of the alkali agent(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0185] Furthermore, the quantity of the alkali agent(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.

[0186] Thus, the quantity of the alkali agent(s) in the composition according to the present invention can be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0187] (Acid)

[0188] The composition according to the present invention may comprise at least one acid that is different from (a) compound or (b) compound. Two or more acids may be used in combination. Thus, a single type of acid or a combination of different types of acids may be used.

[0189] The acid can be used to correct the pH of the composition according to the present invention.

[0190] As an acid, we can cite all inorganic or organic acids that are commonly used in cosmetic products, such as citric acid, lactic acid, sulfuric acid, phosphoric acid or hydrochloric acid (HCl).

[0191] The quantity of the acid or acids in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0192] Furthermore, the quantity of the acid or acids in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.

[0193] Thus, the quantity of the acid or acids in the composition according to the present invention can be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0194] (Other optional ingredients)

[0195] The composition according to the present invention may also include at least one other optional ingredient, selected in particular from: anionic and amphoteric surfactants; thickeners; sunscreens; moisturizers; anti-dandruff agents; antioxidants; antibacterial agents such as benzoic acid; preservatives such as phenoxyethanol; chelating agents; pearlescent and opacifying agents; plasticizers or coalescers; fillers; emulsifiers; Polymers, particularly conditioning polymers such as cationic polymers; and perfumes. The composition may, of course, include several cosmetic ingredients from the list above.

[0196] The composition according to the present invention may include one or more cosmetically acceptable organic solvents, which may be alcohols: in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol and caprylyl glycol; other polyols such as glycerol; and ethers such as monomethyl, monoethyl and monobutyl ethers of ethylene glycol, monomethyl, monoethyl and monobutyl ethers of propylene glycol and monomethyl, monoethyl and monobutyl ethers of butylene glycol.

[0197] Depending on their nature and the purpose of the composition, the above optional ingredient(s) may be present in normal quantities that can be easily determined by those skilled in the art and that may be, for each ingredient, between 0.01% and 80% by weight. Those skilled in the art shall take care to choose the ingredients included in the composition, as well as their quantities, so that they do not impair the properties of the compositions used for the present invention.

[0198] (Ammonia and thiol compound)

[0199] Preferably, the composition according to the present invention should be free of ammonia or thiol compounds. The expression "free of ammonia or thiol compounds" means that the composition according to the present invention does not include a substantial amount of ammonia or thiol compounds. Preferably, the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of ammonia or thiol compounds, in particular no ammonia or thiol compounds.

[0200] Due to the very small amount or absence of ammonia and / or thiol compound, the bad odor during the use of the composition according to the present invention can be reduced or prevented.

[0201] The compound thiol here refers to a compound which has at least one thiol group (-SH).

[0202] The thiol compound can be a reducing agent. The thiol reducing agent can be selected from the group consisting of thioglycolic acid and its derivatives, in particular its esters such as glycerol or glycol monothioglycolate; thiolactic acid and its derivatives, in particular its esters such as glycerol monothiolactate; 3-mercaptopropionic acid and its derivatives, in particular its esters such as glycerol 3-mercaptopropionate and ethylene glycol 3-mercaptopropionate; cysteamine and its derivatives, in particular its C1-C4 acyl derivatives such as N- acetylcysteamine and N-propionylcysteamine; mono-thioglycerol and its derivatives, in particular its esters; cysteine ​​and its derivatives, in particular its esters such as N-acetylcysteine, N-alcanoylcysteine ​​and cysteine ​​alkyl esters; thioglycerin and its derivatives, in particular its s-alkyl derivatives; and its salts.

[0203] Examples of the above-mentioned salts include ammonium salts; primary, secondary, or tertiary amine salts; alkali metal salts; and alkaline earth metal salts. Examples of primary, secondary, or tertiary amines include monoethanolamine, diisopropanolamine, and triethanolamine, respectively.

[0204] Other examples of thiol reducing agents include, but are not limited to, sugar N-mercapto alkyl amides such as N-(mercapto-2-ethyl)gluconamide, [3-mercaptopropionic acid and its derivatives; thiomalic acid; panthetin; N-(mercaptoalkyl)co-hydroxyalkyl amides such as those described in European Patent Application No. 0 354 835 and N-mono- or N,N-dialkylmercapto 4-butyramides such as those described in European Patent Application No. 0 368 763; aminomer-captoalkyl amides such as those described in European Patent Application No. 0 432 000 and alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; 2-hydroxypropyl thioglycolate (2 / 3) and the mixture based on 2-hydroxymethyl-1-ethyl thioglycolate (67 / 33) described in French patent application no. 2,679,448.

[0205] (Reducing agent and oxidizing agent)

[0206] The composition according to the present invention may include a reducing agent; however, it is preferable that the composition according to the present invention include a reduced amount of reducing agent or oxidizing agent, and preferably be free of reducing agent or oxidizing agent.

[0207] The expression "free of reducing agent or oxidizing agent" means that the composition according to the present invention does not include a substantial amount of reducing agent or oxidizing agent. Preferably, the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of a reducing agent or an oxidizing agent, in particular no reducing agent or no oxidizing agent.

[0208] The reducing agent may be a thiol reducing agent or a non-thiol reducing agent. The thiol reducing agent is as described above.

[0209] The non-thiol reducing agent herein means a reducing agent without a thiol group. The non-thiol reducing agent may be selected from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones, and hydrides. The non-thiol reducing agent may be selected from ammonium sulfites and bisulfites, as well as metal sulfites and bisulfites, more preferably from metal sulfites and bisulfites. alkaline or alkaline-earth metal and more preferably among sodium sulfites and bisulfites.

[0210] The oxidizing agent may be selected from hydrogen peroxide, alkali metal bromates, ferricyanides, peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis. For example, the oxidizing agent may be selected from an aqueous solution of hydrogen peroxide, urea peroxide, alkali metal bromates, and persalts such as perborates and persulfates.

[0211] (Form)

[0212] The compositions used for the present invention may be in any form suitable for topical application, and in particular in the form of an aqueous, alcoholic or alcoholic-aqueous or oily solution or suspension; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O / W, W / O or multiple type (if the composition according to the present invention includes at least one oil); a soft consistency suspension or emulsion of the cream (O / W) or (W / O) type; an aqueous gel or any other cosmetic form.

[0213] The compositions used for the present invention may be in any pharmaceutical form. For example, the compositions used for the present invention may be in the form of any hair treatment in general, such as a cream, lotion, gel, or similar product.

[0214] The composition according to the present invention can be used for the treatment, preferably the remodeling and more preferably the smoothing of keratinous fibers such as hair. [Process]

[0215] The present invention also relates to a remodeling process, preferably a smoothing process, of keratinous fibers such as hair, comprising the following steps: i. Application of the composition according to the present invention to keratinous fibers: ii. Optional rinsing of the keratinous fibers, with or without drying of the keratinous fibers after rinsing; and iii. remodeling, preferably smoothing of keratinous fibers, preferably at a temperature above 50 °C, more preferably above 100 °C, and even more preferably above 150 °C.

[0216] Details of the composition used in the process according to the present invention are explained in the section entitled [Composition] above.

[0217] The process according to the present invention is intended for remodeling, preferably smoothing, keratinous fibers, such as hair, more preferably to smoothing over a long period and, even more preferably, smoothing even after several shampoos. In this sense, the process according to the present invention can be a semi-permanent remodeling, preferably smoothing, process.

[0218] It is preferable to clean the keratin fibers before step (i). This cleaning step can be carried out, for example, by shampooing the keratin fibers and then rinsing them. After rinsing, the keratin fibers can be dried. It is preferable for the keratin fibers to be wetted just before step (i).

[0219] In step (i), the composition according to the present invention, which is explained above, is applied to keratinous fibers such as hair. The application of the composition according to the present invention can be carried out by any means, such as a brush or a comb.

[0220] The bath ratio between the composition applied according to the present invention and the keratinous fibers can range from 0.1 to 10, more particularly from 0.5 to 5, and is preferably between 0.3 and 2. The expression "bath ratio" is intended to designate the weight ratio between the total weight of the composition applied and the total weight of the keratinous fibers.

[0221] It may be possible, after the application of the composition according to the present invention, to leave the keratinous fibers as they are for a certain period of time; typically from 1 minute to 1 hour, preferably from 2 to 30 minutes, and more preferably from 3 to 10 minutes, if necessary, in order to allow the composition to penetrate the keratinous fibers.

[0222] After step (i), the process according to the present invention may include the optional step (ii) of rinsing the keratinous fibers with or without drying the keratinous fibers after rinsing.

[0223] Thus, if step (ii) is present, the keratin fibers are rinsed to remove the composition according to the present invention from the keratin fibers. The rinsing step can be carried out with water. It is preferable that the keratin fibers be dried after rinsing. Drying of the keratin fibers can be carried out with a conventional drying method such as a hairdryer.

[0224] Furthermore, if step (ii) is not present, the keratinous fibers can be treated by step (iii) after step (i) without rinsing.

[0225] In step (iii), the keratinous fibers, which are preferably dry, are subjected to remodeling, preferably smoothing, preferably at a temperature above 50 °C, more preferably above 100 °C, and even more preferably above 150 °C, with at least one device selected from the group consisting of an iron, a comb, a heated dryer, and one of their combinations, preferably with a combination of a comb and a heated dryer. This temperature may be in less than 250 °C, preferably less than 240 °C, and more preferably less than 230 °C. Thus, this temperature can be greater than 50 °C and less than 250 °C, preferably greater than 100 °C and less than 240 °C, and more preferably greater than 150 °C and less than 230 °C.

[0226] Reshaping can be carried out by supplying the keratin fibers with any mechanical force such as mechanical tension. Mechanical tension can be applied to the keratin fibers by any reshaping means to deform the keratin fibers into a predetermined shape. For example, mechanical power can be supplied by at least one reshaping means selected from the group consisting of at least one iron, at least one curler, at least one comb, and one combination thereof. Any conventional iron, curler, or comb can be used as a reshaping means. A dryer that can blow gas such as air can also be used as a reshaping means.

[0227] The reshaping means may include at least one heating element. Thus, the reshaping means may be at least one heated iron and / or at least one heated curling iron and / or at least one heated comb and / or at least one heated dryer that can blow hot gas such as hot air. It may be preferable to use at least one heated iron and / or at least one heated curling iron.

[0228] As a heating iron, any conventional heating iron can be used. The heating iron may have at least one plate, preferably two plates, which can be heated, for example, by electric heating. The heated plate(s) can be applied to the keratin fibers and moved in the direction of the keratin fibers to smooth them.

[0229] It is preferable that the heating iron has two plates, and that the keratin fibers are sandwiched between the two plates of the heating iron, in which at least one of the plates can be heated, and then the two plates are moved in the direction of the keratin fibers to smooth them.

[0230] It is preferable that the heating iron, in particular a part thereof in contact with keratinous fibers, such as a heating plate or heating plates, has a temperature above 50 °C and below 250 °C, more preferably above 100 °C and below 240 °C, and even more preferably above 150 °C and below 230 °C.

[0231] Step (iii) can be carried out by one or more passes of the heating iron in the direction of the keratin fibers. Step (iii) can be controlled not only by the temperature of the heating iron but also by the number of passes of the heating iron.

[0232] The heating time can depend on the temperature of the heating iron, but also on the number of times the heating iron is passed over the surface. It can be, for example, from 1 second to 10 minutes, and preferably from a few seconds to 5 minutes.

[0233] As a heating roller, any conventional heating roller can be used. If the keratin fibers are wrapped around a heating roller, this wrapping can be carried out along the entire length of the keratin fibers or, for example, over half the length of the keratin fibers. Depending, for example, on the desired hairstyle and the number of curls, the wrapping can be done with thicker or thinner sections of hair.

[0234] It is preferable that the heating element, in particular a part thereof in contact with keratinous fibers, such as a heating plate or heating plates, has a temperature above 50 °C and below 250 °C, more preferably above 100 °C and below 240 °C, and even more preferably above 150 °C and below 230 °C.

[0235] Step (iii) can be carried out by holding the keratin fibers on a heated spool so that a mechanical tension is applied to the keratin fibers. Step (iii) can be controlled not only by the temperature of the heated spool but also by the strength of the mechanical tension.

[0236] The heating time can depend on the temperature of the heating element but also on the strength of the mechanical tension. It can be, for example, from 1 second to 10 minutes, and preferably from a few seconds to 5 minutes.

[0237] If necessary, prior to step (ii), mechanical tension may be applied to the keratinous fibers as explained above. [Necessary]

[0238] The present invention also relates to a device for remodeling, preferably smoothing, keratinous fibers such as hair, comprising:

[0239] at least one device selected from the group consisting of an iron, a curling iron, a comb, a dryer and one of their combinations, preferably at least one heated iron, heated curling iron, heated comb or heated dryer which is capable of supplying the keratin fibers with a temperature above 50 °C, preferably above 100 °C, and more preferably above 150 °C; and

[0240] the composition according to the present invention.

[0241] Any conventional iron or simmer, including any conventional heated iron or heated simmer, can be used as above iron or simmer in the necessary according to the present invention.

[0242] The heating element in the device is not limited as long as it can heat the keratin fibers to a temperature above 50 °C, preferably above 100 °C, and more preferably above 150 °C. This temperature may be below 250 °C, preferably below 240 °C, and more preferably below 230 °C. Thus, this temperature may be above 50 °C and below 250 °C, preferably above 100 °C and below 240 °C, and more preferably- significantly above 150 °C and below 230 °C.

[0243] The straightening iron or curling iron, as well as the composition, in the necessary according to the present invention can be used as explained in the section entitled [Process] above.

[0244] Details of the composition used in the device according to the present invention are explained in the section entitled [Composition] above. [Use]

[0245] The present invention may relate to the use of (c) at least one quat ester in a composition for remodeling, preferably smoothing, keratinous fibers such as hair, preferably with heating, comprising: a. at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; and b. at least one compound, other than (a) compound, selected from the group consisting of keto acids, their salts, and mixtures thereof.

[0246] in order to prolong the remodeling effects for keratin fibers treated by the composition, in particular in order to further maintain the smoothed shape of keratin fibers, or to prevent or reduce waviness of keratin fibers.

[0247] Heating is not limited as long as it can heat the keratin fibers to a temperature above 50 °C, preferably above 100 °C, and more preferably above 150 °C. This temperature may be below 250 °C, preferably below 240 °C, and more preferably below 230 °C. Thus, this temperature may be above 50 °C and below 250 °C, preferably above 100 °C and below 240 °C, and more preferably above 150 °C and below 230 °C.

[0248] The above composition may further comprise (d) water and / or (e) at least one oil and / or (f) at least one fatty alcohol and / or (g) at least one non-ionic surfactant.

[0249] The above explanations concerning (a) compound, (b) compound and (c) quat ester, as well as (d) water, (e) oil, (f) fatty alcohol and (g) nonionic surfactant, may be applied to those in the above composition used for use according to the present invention.

[0250] According to a preferred embodiment, the composition according to the present invention comprises:

[0251] from 0.1% to less than 15% by weight, relative to the total weight of the composition, of (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides and mixtures thereof;

[0252] from 0.1% to 10% by weight, relative to the total weight of the composition, of (b) at least one compound selected from the group consisting of levulinic acid, one of its salts and one of its mixtures; and

[0253] from 0.01% to 15% by weight, relative to the total weight of the composition, of (c) at least one quat ester selected from the group consisting of distearoylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate, and a mixture thereof.

[0254] According to a preferred embodiment, the composition according to the present invention comprises:

[0255] from 1% to less than 13% by weight, relative to the total weight of the composition, of (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides and mixtures thereof;

[0256] from 1% to 6% by weight, relative to the total weight of the composition, of (b) at least one compound selected from the group consisting of keto acids, their salts and mixtures thereof; and

[0257] from 0.1% to 5% by weight, relative to the total weight of the composition, of (c) at least one quat ester selected from the group consisting of distearoylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate, and a mixture thereof. EXAMPLES

[0258] We will describe the present invention in more detail by means of examples. However, these examples should not be interpreted as limiting the scope of the present invention. Example 1 and Comparative Examples 1 to 3 [Preparation]

[0259] Each of the compositions according to Example 1 and Comparative Examples 1 to 3 was prepared by mixing the ingredients shown in Table 1. The numerical values ​​for the quantities of the ingredients are all based on the "% by weight" as raw materials.

[0260] [Tables 1] Ex. 1 Ex. Comp. 1 Ex. Comp. 2 Ex. Comp. 3 Cetearyl alcohol 5 5 5 5 Isopropyl myristate 10 10 10 10 Glyoxylic acid (50% wt. MA) (1) 20 20 20 20 Levulinic acid (60% wt. MA) (2) 5 5 5 5 Distearoylethyl dimonium chloride (65% wt. MA) (3) 1 - - - Cetrimonium chloride (25% wt. MA) (4) - - 2.6 - Steareth-20 - - - 1.5 pH adjuster qs pH 3 qs pH 3 qs pH 3 qs pH 3 Water qsp 100 qsp 100 qsp 100 qsp 100 Smoothing effects (TO / Tlsh) 5 / 4 5 / 2 5 / 3 5 / 4 Surface (TO / Tlsh) 813 / 1159 765 / 1484 898 / 1334 892 / 1419

[0261] MA: Active ingredient

[0262] (1) sold by WEYLCHEM under the name GLYOXO-HIGH PURE 50 (containing 50% active ingredient).

[0263] (2) sold by the company DR STRAETMANS (EVONIK) under the name DERMOSOFT 700 B (containing 60% active ingredient).

[0264] (3) sold by EVONIK GOLDSCHMIDT under the name VARISOFT EQ 65 MB (containing 65% active ingredient)

[0265] (4) sold by BASF under the name DEHYQUART A OR (containing 25% of active ingredient) [Evaluations]

[0266] Each of the above compositions was used to smooth a strand of hair, and then the strand of hair was evaluated, in accordance with the following protocols.

[0267] 1) A lock of natural black Chinese hair, slightly wavy, of a length A 27 cm strand of hair was washed with an SLES shampoo composition shown in Table 2 below. The hair strand was rinsed thoroughly with water. faucet.

[0268] [Tables2] % by weight Hexylene glycol 1 Sodium chloride 1 Water qs 100 Cocobetaine 9 Sodium laureth sulfate (70% by weight) 15 Preservatives 0.7 Polyquaternium-10 0.3

[0269] 2) Each of the compositions according to Example 1 and Comparative Examples 1 to 3 has was applied in an amount of 1 g to the wet strand of hair.

[0270] 3) The hair strand was left for 10 minutes at room temperature (25 °C).

[0271] 4) The lock of hair was rinsed thoroughly with tap water.

[0272] 5) The strand of hair was dried with a hairdryer (Nobby NB3100, TESCOM DENKI Co., Ltd, Japan) for about 90 seconds until dry.

[0273] 6) The hair strand was straightened in 3 passes with a straightening iron (ADST Premium DS2, Hakko Limited, Japan) at 180°C, 4 seconds / pass.

[0274] 7) The level of smoothness of the hair strand was assessed visually immediately after step 6 (for the smoothing effect at T0) according to the following criteria.

[0275] 5: Very good

[0276] 4: Good

[0277] 3: Passable

[0278] 2: Bad

[0279] 1: Very bad

[0280] The results are shown to the left of “ / ” on the “Smoothing Effects (TO / Tlsh)” line of Table 1.

[0281] 8) A photograph of the lock of hair was taken just after step 6, and the surface (expressed by the number of pixels) of the hair strand was determined using free software in the public domain, Image J. The results are shown to the left of " / " on the "Surface (TO / Tlsh)" line of Table 1.

[0282] 9) The hair strand was washed again with the shampoo composition SLS shown in Table 2, thoroughly rinsed with tap water and dried with hair dryer (for about 90 seconds until dry).

[0283] 10) The level of smoothness and the surface area of ​​the hair strand were evaluated at new as above (Tlsh). The results are shown to the right of " / " on the "Smoothing effects (TO / Tlsh)" and "Surface (TO / Tlsh)" lines of Table 1.

[0284] The evaluation results in Table 1 show that the use of a quat ester with a combination of glyoxylic acid and levulinic acid helps to maintain the smooth shape of the hair or reduce the increase in hair volume, which reflects the straightening or waving of the hair, more than the use of the combination of glyoxylic acid and levulinic acid alone (Comparative Example 1), the combination of glyoxylic acid, levulinic acid and a cationic surfactant that is not a quat ester (Comparative Example 2) or the combination of glyoxylic acid, levulinic acid and a nonionic surfactant (Comparative Example 3).

Claims

Demands

1. Composition for keratinous fibers, such as hair, comprising: (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; (b) at least one compound, other than (a) compound, selected from the group consisting of keto acids, their salts, and mixtures thereof; and (c) at least one quaternary ester.

2. Composition according to claim 1, wherein compound (b) is selected from levulinic acid, one of its salts and one of their mixtures.

3. Composition according to any one of claims 1 to 2, wherein the (c) quaternary ester is selected from the group consisting of distearoylethyl dimonium chloride, dioleoylethyl hydroxyethylmonium methosulfate, and a mixture thereof.

4. Composition according to any one of claims 1 to 3, wherein the composition further comprises (d) water.

5. Composition according to any one of claims 1 to 4, wherein the composition further comprises (e) at least one oil.

6. Composition according to any one of claims 1 to 5, wherein the composition further comprises (f) at least one fatty alcohol.

7. Composition according to any one of claims 1 to 6, wherein the pH of the composition is 7 or less, preferably 6 or less, and more preferably 5 or less.

8. Use of a composition according to any one of claims 1 to 7, for remodeling, preferably smoothing, keratinous fibers, such as hair.

9. A remodeling, preferably smoothing, process for keratinous fibers, such as hair, comprising the steps of: (i) applying the composition according to any one of claims 1 to 8 to the keratinous fibers; (ii) optionally rinsing the keratinous fibers with or without drying the keratinous fibers after rinsing; and (iii) remodeling, preferably smoothing, the keratinous fibers, preferably at a temperature above 50 °C, more preferably above 100 °C, and even more preferably above 150 °C.

10. Remodeling device, preferably for straightening, of keratinous fibers such as hair, comprising: at least one device selected from the group consisting of an iron, a curling iron, a comb, a dryer and one of their combinations, preferably at least one heated iron, heated curling iron, heated comb or heated dryer which is capable of supplying the keratinous fibers with a temperature above 50 °C, preferably above 100 °C, and more preferably above 150 °C; and the composition according to any one of claims 1 to 8.