Methods of treating materials, compositions for use in the methods, and related uses thereof

Abstract

The present invention relates to methods, compositions, and related uses thereof. A method of treating a material, the method comprising contacting the material with a composition comprising an aldehyde substituted with a hydroxyl group.

Description

[0001] This application is a divisional application of parent application number 201780025081.2. The parent application was filed on April 21, 2017; the invention is entitled "Method, Composition and Related Uses Thereof". Technical Field

[0002] This invention relates to methods for treating materials, compositions for such methods, and related uses. Specifically, this invention relates to methods for treating keratinous materials (especially hair) to provide benefits to the materials. Background Technology

[0003] For many people, the appearance, condition, and cleanliness of their hair are of paramount importance. Consequently, numerous hair care products are available, offering a wide range of benefits and containing a multitude of different ingredients. However, popular hairstyles constantly evolve with fashion trends, and technological advancements in hair styling tools mean a continuous need for different and improved hair care compositions. Furthermore, as we gain a greater understanding of the toxicity of certain chemicals and their environmental impact, it is increasingly necessary to consider these factors when developing cosmetic products.

[0004] For example, formaldehyde was a previously used ingredient in cosmetic hair care compositions. However, formaldehyde is a suspected carcinogen, and therefore its use in cosmetic compositions is now strictly regulated and highly undesirable.

[0005] The appearance, condition, and cleanliness of textiles and fabrics are also quite important, as the stresses encountered in the environments in which they are used can have a detrimental effect on them. Summary of the Invention

[0006] One object of the present invention is to provide means for providing at least one property of reinforcing materials.

[0007] According to a first aspect of the invention, a method for processing a material is provided, the method comprising contacting the material with a composition comprising an aldehyde substituted with a hydroxyl group.

[0008] This invention relates to a method of processing materials. In some embodiments, the material may be a textile material. In such embodiments, the textile material suitably comprises wool, preferably comprising wool as its main component.

[0009] In a preferred embodiment, the material is keratin. More preferably, the material comprises keratin fibers. The preferred material is hair. The hair can be human hair or animal hair. In a particularly preferred embodiment, the method of the present invention is a method for treating human hair. Most preferably, it is a method for treating human hair growing on the head.

[0010] However, it should be understood that the method of the present invention can also be used to treat hair that is not growing on the head, such as wigs or animal hair, such as wool.

[0011] The method of the present invention involves contacting a material (preferably hair) with a composition comprising an aldehyde that has been substituted with a hydroxyl group.

[0012] According to a second aspect of the invention, a composition comprising a hydroxyl-substituted aldehyde is provided.

[0013] In a preferred embodiment, the method of the first aspect of the invention includes contacting a material with the composition of the second aspect. Therefore, the preferred features of the second aspect are equally applied to the first aspect.

[0014] Preferred features of the first and second aspects of the invention will now be described. Where appropriate, any feature may be applied to any other aspect.

[0015] The composition of the second aspect of the present invention comprises an aldehyde that has been substituted with a hydroxyl group.

[0016] It may contain any suitable aldehyde that has been substituted with a hydroxyl group.

[0017] The suitable aldehydes used in this article have at least 2 carbon atoms. Preferably, they have at least 3 carbon atoms.

[0018] Suitable aldehydes used herein may have up to 36 carbon atoms, preferably up to 30 carbon atoms, more preferably up to 24 carbon atoms, and most preferably up to 20 carbon atoms, for example up to 18 carbon atoms or up to 16 carbon atoms.

[0019] Some preferred aldehydes used in this article have 3 to 20 carbon atoms, for example 3 to 16 carbon atoms.

[0020] Some preferred aldehydes used in this article have 3 to 12 carbon atoms, for example 3 to 11 carbon atoms.

[0021] Some of the particularly preferred aldehydes used in this article have 3 to 9 carbon atoms, more preferably 3 to 8 carbon atoms.

[0022] Some other preferred aldehydes used in this article have 8 to 16 carbon atoms, for example 10 to 14 carbon atoms.

[0023] Aldehydes may contain one or more hydroxyl substituents.

[0024] Aldehydes suitably contain one, two, or three hydroxyl substituents, preferably one or two substituents.

[0025] In some preferred embodiments, the aldehyde is not a sugar.

[0026] The preferred aldehyde contains a hydroxyl substituent.

[0027] Aldehydes preferably have hydroxyl substituents at the 2, 3 or 4 positions.

[0028] In some implementations, the aldehyde may have hydroxyl substituents at positions 2 and 3 or 2 and 4.

[0029] Aldehydes may suitably have hydroxyl substituents at the 2- and / or 3-positions.

[0030] Aldehydes may suitably have hydroxyl substituents at the 2 or 3 position.

[0031] In a particularly preferred embodiment, the aldehyde has a hydroxyl substituent at the 2-position. Therefore, the aldehyde is suitably an α-hydroxy aldehyde or a 2-hydroxy aldehyde.

[0032] Aldehydes have a hydroxyl substituent. They may have one or more other substituents.

[0033] Suitable alternative substituents may be selected from other hydroxyl substituents, other aldehyde groups, ketone groups, carboxyl groups, acyl groups, halogen groups, alkoxy groups, alkyl groups, nitro groups, amino groups, thiooxy groups, mercapto groups, amide groups, ester groups, nitrile groups, or isonitrile groups.

[0034] Preferred halogen substituents are chlorine, fluorine, and bromine.

[0035] Preferred alkoxy substituents are methoxy, ethoxy, propoxy, and butoxy, including their isomers.

[0036] The preferred alkyl substituents are C1 to C8 alkyl, more preferably C1 to C6 alkyl, including its isomers.

[0037] In some embodiments, the hydroxyaldehyde may include additional aldehyde functional groups. These additional aldehyde groups may suitably be α-substituted.

[0038] In a preferred embodiment, the aldehyde comprises a hydrocarbon chain. This is suitably a chain having a carbon skeleton. However, compounds in which the carbon skeleton is interrupted by one or more heteroatoms are also within the scope of the invention. For example, the carbon skeleton may be interrupted by one or more oxygen, sulfur, or nitrogen molecules; therefore, the aldehyde may comprise an ether, thioether, amine, or disulfide moiety.

[0039] Aldehydes can be predominantly aliphatic or predominantly aromatic. Aliphatic aldehydes are preferred. However, they may contain one or more double bonds and / or one or more cyclic groups. They can be linear or branched.

[0040] In some particularly preferred embodiments, the aldehyde has formula (I): (I) Where R is hydrogen or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms.

[0041] R can be hydrogen or an optionally substituted alkyl, alkenyl or aryl group having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms.

[0042] R is preferably hydrogen or an optionally substituted alkyl or alkenyl group having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, suitably 1 to 10 carbon atoms.

[0043] In some embodiments, R is an optionally substituted alkyl or alkenyl group having 1 to 7 carbon atoms, preferably 1 to 6 carbon atoms.

[0044] In some embodiments, R is an optionally substituted alkyl or alkenyl group having 8 to 14 carbon atoms, preferably 8 to 12 carbon atoms.

[0045] R may be substituted by one or more substituents selected from ketone, hydroxyl, halogen, carboxyl, acyl, nitro, amino, mercapto, alkoxy, thiooxy, ester, nitrile, isonitrile, or amide. The carbon skeleton may be interrupted by one or more heteroatoms, such as one or more oxygen, nitrogen, or sulfur atoms.

[0046] In some preferred embodiments, R is an unsubstituted alkyl group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms.

[0047] In a preferred embodiment, R is an unsubstituted alkyl group having 4 to 16 carbon atoms, preferably 8 to 12 carbon atoms.

[0048] R can be selected from hydroxymethylene, methyl, butyl, hexyl, octyl, decyl, and dodecyl. These groups can be straight-chain or branched. They are preferably straight-chain.

[0049] R is suitably selected from hydroxymethylene, methyl, n-butyl and n-hexyl.

[0050] R can be selected from methyl, n-butyl, n-hexyl, n-octyl, n-decyl, and n-dodecyl.

[0051] R is preferably selected from methyl, n-butyl and n-hexyl.

[0052] The optimal choice R is selected from n-butyl and n-hexyl.

[0053] In some preferred embodiments, the aldehyde is an aliphatic aldehyde with a hydroxyl group substituted.

[0054] Suitable hydroxyl-substituted aldehydes used in this article include 2-hydroxydecaldehyde, 2-hydroxydodecaldehyde, 2-hydroxytetradecaldehyde, 2-hydroxyhexanal, 2-hydroxyoctanaldehyde, 2-hydroxypropanaldehyde, glyceraldehyde, 6-hydroxyhexanal, 3-hydroxypropanaldehyde, 4-hydroxybut-2-enal, 2-hydroxybutanaldehyde, 3-hydroxybutanaldehyde, and 4-hydroxybutanaldehyde.

[0055] Suitable hydroxyl-substituted aldehydes used in this article include 2-hydroxydecaldehyde, 2-hydroxydodecaldehyde, 2-hydroxytetradecaldehyde, 2-hydroxyhexanal, 2-hydroxyoctanaldehyde, 2-hydroxypropanaldehyde, 6-hydroxyhexanal, 3-hydroxypropanaldehyde, 4-hydroxybut-2-enal, 2-hydroxybutanaldehyde, 3-hydroxybutanaldehyde, and 4-hydroxybutanaldehyde.

[0056] Preferred hydroxyl-substituted aldehydes used in this article include 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, glyceraldehyde, 6-hydroxyhexanal, 3-hydroxypropanal, 4-hydroxybut-2-enal, 2-hydroxybutanal, 3-hydroxybutanal, and 4-hydroxybutanal.

[0057] Preferred hydroxyl-substituted aldehydes used in this article include 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, 6-hydroxyhexanal, 3-hydroxypropanal, 4-hydroxybut-2-enal, 2-hydroxybutanal, 3-hydroxybutanal, and 4-hydroxybutanal.

[0058] More preferred hydroxyl-substituted aldehydes used in this article include 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, and glyceraldehyde.

[0059] The most preferred hydroxyl-substituted aldehydes used in this article are 2-hydroxyhexanal, 2-hydroxyoctanal, and 2-hydroxypropanal.

[0060] More preferred hydroxyl-substituted aldehydes used in this article include 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, and glyceraldehyde.

[0061] The most preferred hydroxyl-substituted aldehydes used in this article are 2-hydroxyhexanal, 2-hydroxyoctanal, and 2-hydroxypropanal.

[0062] The composition suitably contains at least 0.1% by weight of a hydroxyl-substituted aldehyde, suitably at least 0.5% by weight, preferably at least 1% by weight, for example at least 1.5% by weight.

[0063] The composition may contain up to 50% by weight of a hydroxyl-substituted aldehyde, preferably up to 30% by weight, suitably up to 20% by weight, preferably up to 10% by weight, more preferably up to 5% by weight, such as up to 4% by weight, up to 3% by weight or up to 2.75% by weight.

[0064] In some embodiments, the composition comprises 0.1 to 10% by weight of a hydroxyaldehyde, preferably 0.5 to 5% by weight, suitably 0.5 to 3% by weight.

[0065] In some alternative embodiments, the composition may contain a much higher concentration of hydroxyaldehyde, such as 20 to 100% by weight, preferably 50 to 100% by weight, such as 70 to 100% by weight or 90 to 100% by weight.

[0066] The composition of the second aspect may comprise a mixture of two or more hydroxyl-substituted aldehydes. In such embodiments, the above amounts refer to the total amount of all such compounds present in the composition.

[0067] In some embodiments, the composition of the second aspect comprises a mixture of two or more hydroxyl-substituted aldehydes.

[0068] In some embodiments, the composition of the second aspect comprises 2-hydroxyoctanal and one or more other hydroxylated aldehydes.

[0069] In some embodiments, the composition of the second aspect comprises glyceraldehyde and one or more other hydroxyl-substituted aldehydes.

[0070] In some embodiments, the composition of the second aspect comprises 2-hydroxyoctanal and glyceraldehyde. It may optionally comprise one or more other hydroxylated aldehydes.

[0071] In some embodiments, the composition contains less than 0.1% by weight of glyceraldehyde, suitably less than 0.01% by weight. The composition is suitably glyceraldehyde-free.

[0072] In some embodiments, the composition of the third aspect comprises a first hydroxyl-substituted aldehyde having fewer than 10 carbon atoms and a second hydroxyl-substituted aldehyde having 10 or more carbon atoms. It may optionally comprise one or more additional hydroxyl-substituted aldehydes. For example, the composition of the third aspect may comprise a first hydroxyl-substituted aldehyde having 3 to 9 carbon atoms, preferably 3 to 8 carbon atoms, and a second hydroxyl-substituted aldehyde having 10 to 18 carbon atoms, preferably 10 to 16 carbon atoms, more preferably 10 to 14 carbon atoms. It may optionally comprise one or more additional hydroxyl-substituted aldehydes.

[0073] In some embodiments, the composition of the third aspect comprises one or more hydroxy-substituted aldehydes selected from 2-hydroxydecaldehyde, 2-hydroxydodecaldehyde, and 2-hydroxytetradecaldehyde, and one or more additional hydroxy-substituted aldehydes selected from 2-hydroxyhexanal, 2-hydroxyoctanaldehyde, 2-hydroxypropanaldehyde, glyceraldehyde, 6-hydroxyhexanal, 3-hydroxypropanaldehyde, 4-hydroxybut-2-enal, 2-hydroxybutanaldehyde, 3-hydroxybutanaldehyde, and 4-hydroxybutanaldehyde.

[0074] In some embodiments, the composition of the third aspect comprises one or more hydroxy-substituted aldehydes selected from 2-hydroxydecaldehyde, 2-hydroxydodecanaldehyde, and 2-hydroxytetradecanaldehyde, and one or more additional hydroxy-substituted aldehydes selected from 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanaldehyde, 6-hydroxyhexanal, 3-hydroxypropanaldehyde, 4-hydroxybut-2-enal, 2-hydroxybutanaldehyde, 3-hydroxybutanaldehyde, and 4-hydroxybutanaldehyde.

[0075] In some embodiments, the composition of the third aspect may comprise one or more hydroxy-substituted aldehydes selected from 2-hydroxydecaldehyde, 2-hydroxydodecaldehyde and 2-hydroxytetradecaldehyde, and one or more additional hydroxy-substituted aldehydes selected from 2-hydroxyhexanal, 2-hydroxyoctanaldehyde, 2-hydroxypropanaldehyde and glyceraldehyde.

[0076] In some embodiments, the composition of the third aspect may comprise one or more hydroxy-substituted aldehydes selected from 2-hydroxydecaldehyde, 2-hydroxydodecaldehyde and 2-hydroxytetradecaldehyde, and one or more additional hydroxy-substituted aldehydes selected from 2-hydroxyhexanal, 2-hydroxyoctanaldehyde and 2-hydroxypropanaldehyde.

[0077] The compositions of the present invention can be provided in any suitable form. They can be in the form of gels, pastes, creams, or waxes. They can be in the form of liquid compositions. These compositions can be in the form of solutions, dispersions, or emulsions. They can be provided as solid compositions, for example, as powders or as strips. In some embodiments, concentrated compositions to be diluted prior to use can be provided. In some embodiments, the composition of the second aspect can be part of a precursor composition to be mixed with one or more additional components prior to contact with a material.

[0078] The form and properties of the composition in the second aspect will depend on its intended use.

[0079] In some embodiments, the composition is a laundry detergent composition. In such embodiments, the composition suitably comprises one or more optional self-washing agents, surfactants, chelating agents, bleaching agents, optical brighteners, enzymes, fragrances, and other such ingredients commonly found in laundry detergent compositions. The composition can be a hand-wash laundry detergent composition or an automatic laundry detergent composition.

[0080] In a particularly preferred embodiment, the composition is a hair care composition.

[0081] The method of the first aspect of the invention preferably provides benefits to the material being treated. The method suitably enhances at least one property of the material treated according to the method.

[0082] In a preferred embodiment, the method is a hair treatment method that provides beneficial effects on hair. It suitably enhances at least one property of the hair. The method of the first aspect suitably includes contacting the hair with the composition of the second aspect.

[0083] The composition of the second aspect of the invention is preferably a hair-beneficial composition. It suitably enhances at least one property of the hair.

[0084] In some embodiments, the compositions and methods of the present invention may provide temporary alterations to the properties of hair, for example, by providing increased shine or luster, or improved softness or combability.

[0085] Temporary changes in hair properties may be due to the composition coating the hair surface but forming weak interactions, making the composition easy to wash or brush off.

[0086] In some preferred embodiments, the compositions and methods of the present invention can provide longer-lasting benefits to hair, such as wash resistance.

[0087] The long-lasting benefits to hair can be achieved through the interaction of hydroxyl aldehyde molecules with hair. Not wishing to be limited by theory, it is believed that aldehydes react with amino groups in the keratin fibers of hair to form Schiff bases. These Schiff bases can then react with other amino groups in the hair to form covalent cross-links, thereby permanently imparting specific hair benefits, and / or form hydrophobic bonds between alkyl or aryl groups, which are part of the hydroxyl-substituted aldehyde compound that binds the Schiff base to the amino groups in the hair, to permanently impart specific hair benefits. This mechanism can be applied to all the benefits covered by this invention, such as curling, straightening, hair strengthening, hair protein retention, binding of additional proteins to hair, heat durability, chemical resistance, UV stability, shine, softness, and combability. To provide these benefits, it should be understood that hydroxyl-substituted aldehyde compounds will act by fully or partially penetrating the hair core (cortex) and reacting with amino groups partially or throughout the hair fiber, and / or reacting with amino groups on or near the hair surface. In the latter case, the alkyl / aryl groups of the hydroxyl-substituted aldehyde compound will covalently bind to the surface of the hair fiber to provide benefits such as shine / luster, protection, softness, and combability.

[0088] The compositions and methods of the present invention can be used for permanent curling or straightening of hair.

[0089] The compositions and methods of the present invention can improve hair strength.

[0090] The compositions and methods of the present invention can prevent or inhibit the loss of proteins from hair, and / or they can be used to bind additional proteins to hair.

[0091] The compositions and methods of the present invention can provide damage protection for hair. For example, the compositions and methods of the present invention can protect against heat or sunlight damage.

[0092] In some embodiments, the compositions and methods of the present invention can provide chemical resistance, for example, protection against chlorine and other compounds found in swimming pools.

[0093] The compositions and methods of the present invention can suitably enhance at least one hair property selected from shine, gloss, softness, combability, strength, straightness, curliness, heat durability and UV stability.

[0094] Preferably, the present invention provides one or more benefits selected from increased and / or permanent / semi-permanent gloss or shine, improved and / or permanent / semi-permanent combability, improved and / or permanent / semi-permanent strength, increased and / or permanent / semi-permanent softness, reduced protein loss, improved heat durability, increased chemical resistance, permanent / semi-permanent curl and / or permanent / semi-permanent straightness.

[0095] The composition suitably comprises one or more diluents or carriers. Preferred diluents and carriers are cosmetically permitted compounds, suitable examples of which should be known to those skilled in the art. Examples of suitable carriers include organic solvents, such as hydrocarbon solvents (e.g., isododecane), alcohols (e.g., ethanol, propanol, and butanol), propylene carbonate, benzyl alcohol, aliphatic or aromatic esters (e.g., vegetable oils, isopropyl myristate, C12-15 alkyl benzoates), perfluorocarbon solvents, and silicone oils.

[0096] In some embodiments, the composition is an aqueous composition. Water is suitably the primary solvent present in the composition. In some embodiments, water provides at least 50% by weight, preferably at least 60% by weight, more preferably at least 70% by weight, suitably at least 80% by weight, such as at least 90% by weight or at least 95% by weight of all solvents present in the composition. In some embodiments, one or more additional water-miscible solvents may be present. Examples of suitable water-miscible solvents include monohydric and polyhydric alcohols, such as ethanol, glycerol, and isopropanol.

[0097] In some embodiments, the compositions of the present invention are not aqueous, and the primary diluent or carrier is a lipophilic substance. In such embodiments, the compositions may contain one or more higher fatty alcohols, mineral oils, and / or vegetable oils as primary solvents.

[0098] In some embodiments, the composition is substantially aqueous, but the aldehyde is dispersed in a lipophilic phase in which it is soluble.

[0099] In some embodiments, the composition may consist essentially of one or more hydroxyl-substituted aldehydes and one or more diluents or carriers. In preferred embodiments, the composition comprises one or more additional components. Suitable components are those generally used in personal care compositions and are known to those skilled in the art.

[0100] As detailed above, the compositions of the present invention may comprise different components depending on their intended use. In some embodiments, the composition may be used immediately after hair dyeing. Alternatively, the composition may be used once or multiple times as a hair treatment composition. In some embodiments, it may be provided as a composition to prevent color loss. Alternatively, the composition may be in the form of a shampoo, conditioner, or hair styling product, such as a paste, wax, mousse, gel, or spray, or any other form of hair treatment that may be used to provide general hair care benefits. Compositions that perform multiple functions, such as combined shampoo and conditioner compositions, are also within the scope of the present invention.

[0101] The composition suitably comprises one or more components selected from surfactants (including anionic, amphoteric, nonionic, and cationic surfactants), conditioning agents (including quaternary ammonium compounds, cationic polymers, silicones, synthetic or natural oils or resins, etc.), fatty alcohols, electrolytes or other rheology modifiers, emulsifiers / pearlizers, scalp benefits, fragrances, dyes, UV filters, penetration enhancers (e.g., propylene carbonate, benzyl alcohol, etc.), preservatives, antioxidants, emulsifiers, pH adjusters and buffers, and shaping polymers (e.g., polyvinylpyrrolidone, etc.).

[0102] In some embodiments, the composition contains a pH adjuster.

[0103] Suitable pH adjusters used in this article may include lactic acid, sodium hydroxide, sodium phosphate and their salts, and buffers.

[0104] The pH of the composition will depend on its intended use. However, in a preferred embodiment, the composition has a pH between 3 and 9, preferably between 3.5 and 8, more preferably between 4 and 7, and most preferably between 4 and 6.

[0105] In some preferred embodiments, the composition is a hair care composition. Suitable hair care compositions include shampoo compositions, conditioning compositions, hair styling compositions, and compositions for permanent curling, loosening, or permanent straightening, or hair coloring.

[0106] Suitable additional ingredients to be used in hair care compositions and their amounts should be known to those skilled in the art. The relative ratios of the components of these compositions and their formulation are within the capabilities of those skilled in the art.

[0107] The composition is suitably a substantially aqueous composition, and suitably contains at least 50% by weight water, preferably at least 60% by weight, more preferably at least 70% by weight.

[0108] The composition suitably comprises one or more surfactants. For example, the composition may comprise 0.1 to 60% by weight of surfactant, preferably 1 to 30% by weight, and suitably 5 to 25% by weight.

[0109] The composition suitably comprises one or more anionic surfactants. For example, the composition may comprise 0.1 to 60% by weight of anionic surfactant, preferably 1 to 30% by weight, and suitably 5 to 25% by weight.

[0110] In some embodiments, the composition may contain a quaternary ammonium salt in an amount suitable for 0.1 to 20% by weight, preferably 0.1 to 10% by weight.

[0111] In some embodiments, the composition further comprises a succinimide ester. Suitable compounds of this type are described in FR2937543.

[0112] Therefore, the present invention can provide hair care compositions comprising hydroxyl-substituted aldehydes and succinimide esters.

[0113] In such embodiments, the aldehyde is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, and the succinimide ester is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight.

[0114] Succinimide esters are preferably compounds of formula (I): (I) Where R is an optionally substituted hydrocarbon group having 5 to 36 carbon atoms; and R 1 It is hydrogen or a solubilizing group.

[0115] Preferably, R is an optionally substituted alkyl, alkenyl, or aryl group having 5 to 20 carbon atoms. More preferably, R is selected from phenyl and CH3(CH2). n , where n is between 4 and 10.

[0116] R 1 Suitable for use is a hydrogen or sulfonate moiety, preferably hydrogen.

[0117] In some embodiments, the composition further comprises a chelating agent. Preferred chelating agents are polycarboxylic acid-derived chelating agents.

[0118] Therefore, the present invention can provide hair care compositions comprising hydroxyl-substituted aldehydes and polycarboxylic acid-derived chelating agents.

[0119] In such embodiments, the aldehyde is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, and the chelating agent is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight.

[0120] The chelating agent is suitably selected from glutamic acid, N,N-diacetic acid (GLDA), diethylenetriaminepentaacetic acid (DTPA), iminodisuccinic acid (IDS), ethylenediaminetetraacetic acid (EDTA), ethylenediaminedisuccinic acid (EDDS), hydroxyethylethylenediaminetriacetic acid (HEDTA), citric acid, and mixtures thereof.

[0121] In some preferred embodiments, the chelating agent is selected from DTPA, GLDA, IDS, and mixtures thereof. In some particularly preferred embodiments, the chelating agent is selected from DTPA, GLDA, and mixtures thereof.

[0122] In some embodiments, the composition further comprises an amine salt of a carboxylic acid. Preferred compounds of this type are amine salts of carboxylic acids having 4 to 10 carbon atoms.

[0123] Therefore, the present invention can provide hair care compositions comprising amine salts of hydroxyl-substituted aldehydes and carboxylic acids.

[0124] In such embodiments, the aldehyde is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, and the amine salt is suitably present in an amount of 0.1 to 50% by weight, preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight.

[0125] Carboxylic acids suitably have 4 to 10 carbon atoms, preferably 6 to 8 carbon atoms.

[0126] Preferred salts are secondary or tertiary alkylamines and / or alkanolamines or substituted alkylene diamines. Triethanolamine and diethanolamine are particularly preferred.

[0127] The optimal salt is a triethanolamine or diethanolamine salt of hexanoic acid or octanoic acid.

[0128] In some embodiments, the composition further comprises an amine salt of a carboxylic acid and a polycarboxylic acid-derived chelating agent.

[0129] In some embodiments, the composition further comprises an amine salt of a carboxylic acid and a succinimide ester.

[0130] In some embodiments, the composition further comprises succinimide ester and a polycarboxylic acid-derived chelating agent.

[0131] In some embodiments, the composition further comprises an amine salt of a carboxylic acid, a succinimide ester, and a polycarboxylic acid-derived chelating agent.

[0132] In some embodiments, the composition may further comprise a crosslinking agent comprising two or more reactive moieties and a linker. Compounds of this type are described, for example, in US2015 / 034117 and US2015 / 0034119.

[0133] In some embodiments, the reactive moiety is an activated carboxylic acid or sulfonic acid derivative, and the linker is a polyamino compound that can form a salt or covalent bond with the reactive moiety.

[0134] In some embodiments, the reactive moiety is a maleic acid derivative, and the linking group has two or more amino groups linked by alkylene or oxyalkylene chains. The crosslinking agent can be a maleimide or a maleic acid amine salt.

[0135] In some embodiments, the reactive portion is a maleate ion, and the linking group includes a quaternary ammonium ion linked by an alkylene or oxyalkylene chain.

[0136] Some preferred crosslinking agents have the following structures: A crosslinking agent comprising two or more reactive moieties and a linker may be present in an amount of 0.1 to 30% by weight, preferably 0.1 to 10% by weight, suitably 0.5 to 5% by weight.

[0137] In some embodiments, the composition of the second aspect of the present invention is a shampoo composition.

[0138] The suitable shampoo compositions of the present invention typically comprise 0.5 to 60% by weight of one or more anionic surfactants, preferably 1 to 50% by weight, more preferably 5 to 30% by weight, such as 8 to 20% by weight or 8 to 12% by weight; optionally 0.1 to 30% by weight of an amphoteric surfactant, preferably 1 to 15% by weight, such as 2 to 12% by weight; and optionally 0.1 to 40% by weight of a nonionic surfactant, preferably 0.5 to 30% by weight, such as 1 to 15% by weight or 2 to 12% by weight.

[0139] The shampoo composition of the present invention may contain one or more ingredients selected from the following: anionic surfactants (e.g., sodium lauryl ether sulfate, sodium lauroyl methyl hydroxyethyl sulfonate, sodium cocoyl methyl hydroxyethyl sulfonate, sodium α-olefin sulfonate, sodium lauryl sulfoacetate, sodium monoalkyl phosphate, sodium dialkyl phosphate, and sodium methyl cocoyl taurate), amphoteric surfactants (e.g., cocamidopropyl betaine, sodium lauroyl amphoteric acetate, cocamidopropyl hydroxysulfonate betaine, and disodium cocoyl diacetate), foam promoters (e.g., cocoyl diethanolamine, cocoyl monoethanolamine, cocoyl monoisopropanolamine lauryl ether-3), fatty alkyl alcohols (e.g., cetyl alcohol, stearyl alcohol, and behenyl alcohol), nonionic surfactants (e.g., alkyl polyglucosides and alkyl ether ethoxylates), and cationic polymers (e.g., guar gum hydroxypropyl trimethylammonium chloride, polyquaternium-10). Silicones (e.g., polydimethylsiloxanes such as dimethylpolysiloxane and polydimethylsiloxane alcohol), rheology modifiers (e.g., carbomer, PEG-150 distearate, and xanthan gum), synthetic or natural oils or resins (e.g., mineral oils or vegetable oils), anti-dandruff agents (e.g., piroctone ketone ethanolamine, zinc pyrithione, and salicylic acid), styling agents (e.g., polyisobutylene and polyvinylpyrrolidone / vinyl acetate copolymers), moisturizers (e.g., panthenol and glycerin), non-polymer conditioning agents (e.g., quaternary ammonium compounds such as behenyltrimethylammonium chloride and stearyl dimethylbenzylammonium chloride), emulsifiers / pearlizers (e.g., styrene / acrylate copolymers and ethylene glycol distearate), scalp benefits, fragrances, colorants, hair dyes, sunscreens, UV filters, preservatives, penetration enhancers (e.g., propylene carbonate, benzyl alcohol, etc.), and diluents and carriers as defined herein.

[0140] Some preferred shampoo compositions of the present invention comprise 0.5 to 60% by weight of one or more anionic surfactants (e.g., sodium lauryl ether sulfate, sodium lauroyl methyl hydroxyethyl sulfonate, sodium cocoyl hydroxyethyl sulfonate, sodium α-olefin sulfonate, sodium lauryl sulfoacetate, sodium monoalkyl phosphate, and sodium dialkyl phosphate); and 0 to 30% by weight of amphoteric surfactants (e.g., cocamidopropyl betaine, sodium lauroyl amphoteric acetate, and cocamidopropyl hydroxysulfonate betaine).

[0141] In some embodiments, the composition of the second aspect of the present invention is a conditioning composition.

[0142] Suitable conditioning compositions of the present invention may typically comprise 0.1 to 20% by weight of one or more cationic surfactants, preferably 0.5 to 8% by weight, more preferably 1 to 4% by weight; and 0.1 to 20% by weight of one or more fatty alkanols, preferably 0.5 to 8% by weight, more preferably 1 to 4% by weight; and optionally 0.1 to 20% by weight of one or more nonionic surfactants, preferably 0.5 to 8% by weight, more preferably 1 to 4% by weight; and optionally 0.1 to 20% by weight of one or more cationic polymers, preferably 0.5 to 8% by weight, more preferably 1 to 4% by weight.

[0143] The conditioning compositions of the present invention comprise wash-out and leave-in conditioning agents (including 'hair masks') and hair shine or appearance enhancement products, anti-frizz treatment serums and other treatments designed to be applied to hair immediately after coloring or at any subsequent time, and hair growth solutions. These compositions may contain one or more additional ingredients selected from the following: cationic surfactants (including mono- and dialiphatic alkyl tertiary amines and quaternary ammonium compounds (e.g., mono- and dialiphatic alkyl quaternary ammonium compounds, such as hexadecyltrimethylammonium chloride, stearyltrimethylammonium chloride, and behenyltrimethylammonium chloride)), fatty alkanols (e.g., cetyl alcohol, stearyl alcohol, and behenyl alcohol), nonionic surfactants (e.g., alkyl polyglucosides and alkyl ether ethoxylates, such as cetearyl alcohol polyether-20), cationic polymers (e.g., guar gum hydroxypropyltrimethylammonium chloride)... Ammonium chloride, polyquaternium-10), silicones (e.g., polydimethylsiloxanes such as dimethylpolysiloxane and polydimethylsiloxane alcohol), rheology modifiers (e.g., hydroxyethyl cellulose and polyquaternium-37), humectants (e.g., panthenol and glycerin), non-polymer conditioning agents (e.g., quaternary ammonium compounds such as behenyltrimethylammonium chloride and stearyldimethylbenzylammonium chloride), scalp benefits, fragrances, colorants, hair dyes, sunscreens, UV filters, preservatives, penetration enhancers (e.g., propylene carbonate, benzyl alcohol, etc.), and diluents and carriers as defined herein.

[0144] Some preferred conditioning compositions of the present invention comprise 0.1 to 20% by weight of a cationic surfactant (e.g., mono- and di-aliphatic alkyl quaternary ammonium compounds, mono- and di-aliphatic alkyl tertiary amines), 0.1% to 20% by weight of aliphatic alkanols and 0.1% to 20% by weight of a nonionic surfactant (e.g., cetearyl alcohol polyether-20).

[0145] In some embodiments, the composition of the second aspect of the present invention is a hair styling composition.

[0146] Suitable hair styling compositions of the present invention may typically comprise 0.1 to 40% by weight of one or more hair styling polymers, preferably 0.1 to 30% by weight, more preferably 0.5 to 10% by weight.

[0147] The hair styling compositions of the present invention (including gels, mousses with and without propellants, hair sprays with and without propellants, hair conditioners, hair waxes, hair creams, shine oils, and compositions designed for use in conjunction with heat styling appliances such as hair dryers, curling irons, straighteners, and heat packs (e.g., for use in hair salons)) may contain one or more additional ingredients selected from the following: hair styling polymers (e.g., polyvinylpyrrolidone, polyvinylpyrrolidone / vinyl acetate copolymer, octylacrylamide / acrylate / butylaminoethyl methacrylate copolymer, methyl vinyl ether / maleic anhydride copolymer, and polyethylene wax), rheology modifiers (e.g., carbomer, acrylate copolymers, hydroxyethyl cellulose, xanthan gum, and polyquaternium-37), aminomethylpropanol, fatty alkanols (e.g., cetyl alcohol, stearyl alcohol, and behenyl alcohol), ethanol, propanol, isopropanol, petrolatum, mineral oil, ceresin, beeswax, carnauba wax, silicone ( Examples of surfactants include polydimethylsiloxanes such as dimethylpolysiloxane and polydimethylsiloxane alcohol, polyethylene glycol, anionic surfactants (e.g., sodium lauryl ether sulfate and sodium lauroyl methyl hydroxyethyl sulfonate), amphoteric surfactants (e.g., cocamidopropyl betaine and disodium cocoamphodiacetate), nonionic surfactants (e.g., alkyl polyglucosides and alkyl ether ethoxylates), cationic polymers (e.g., guar hydroxypropyl trimethylammonium chloride, polyquaternium-10), silicones (e.g., polydimethylsiloxanes such as dimethylpolysiloxane and polydimethylsiloxane alcohol), humectants (e.g., panthenol and glycerin), nonpolymer conditioning agents (e.g., quaternary ammonium compounds such as behenyltrimethylammonium chloride and stearyl dimethyl benzyl ammonium chloride), scalp benefits, fragrances, colorants, hair dyes, sunscreens, UV filters, preservatives, penetration enhancers (e.g., propylene carbonate, benzyl alcohol, etc.), and diluents and carriers as defined herein.

[0148] Some preferred hair styling compositions of the present invention comprise 0.1 to 40% by weight of one or more hair styling polymers / resins (e.g., polyvinylpyrrolidone, polyvinylpyrrolidone / vinyl acetate copolymer, octylacrylamide / acrylate / butylaminoethyl methacrylate copolymer, methyl vinyl ether / maleic anhydride copolymer, and polyethylene wax).

[0149] Those skilled in the art will understand that hair can be given one or more properties such as hair conditioning, shine, and hair styling from a single product containing suitable ingredients. Therefore, compositions having such beneficial effects on hair are also covered in this invention.

[0150] In some embodiments, the composition of the second aspect is a permanent hair curling composition.

[0151] Suitable permanent hair curling compositions of the present invention typically contain 0.1 to 20% by weight of one or more reducing agents, preferably 0.5 to 15% by weight, more preferably 3 to 12% by weight.

[0152] Some preferred permanent hair curl compositions of the present invention comprise 0.5 to 15% by weight of one or more reducing agents (e.g., thioglycolic acid, ammonium thioglycolate, thiohydroxylactic acid, cysteine, cysteine, glyceryl monothioglycolate, sodium sulfite / sodium bisulfite); and an amount of alkalizing agent (e.g., ammonia, monoethanolamine) sufficient to adjust the pH of the reducing component to between pH 8 and 13. The permanent hair curl compositions are typically supplied in a package containing a second composition comprising 0.5 to 10% by weight of one or more oxidizing agents (e.g., hydrogen peroxide, sodium bromate, sodium percarbonate, and sodium perborate), applied after the reducing agent composition has been applied, allowing for treatment and then washing off.

[0153] In some embodiments, the composition of the second aspect of the present invention is a hair relaxation composition.

[0154] The hair relaxation composition of the present invention may contain one or more components selected from sodium hydroxide, lithium hydroxide, potassium hydroxide, calcium hydroxide, and guanidine carbonate. These components are suitably present in an amount of 0.5 to 5% by weight.

[0155] Other types of permanent hair straightening compositions may contain one or more ingredients selected from formaldehyde, glyoxylic acid, glutaraldehyde, and glyoxylcarboxycysteine. These components are suitably present in an amount of 0.1 to 10% by weight.

[0156] The aforementioned permanent curly, loose, and permanent straight hair compositions may further comprise one or more additional ingredients selected from the following: anionic surfactants (e.g., sodium lauryl ether sulfate and sodium lauroyl methyl hydroxyethyl sulfonate), amphoteric surfactants (e.g., cocamidopropyl betaine and disodium cocoamphodiacetate), quaternary ammonium compounds (e.g., hexadecyltrimethylammonium chloride, stearyltrimethylammonium chloride, and behenyltrimethylammonium chloride), fatty alkanols (e.g., cetyl alcohol, stearyl alcohol, and behenyl alcohol), and nonionic surfactants (e.g., alkyl polyglucosides and alkyl ether ethoxylates). The following are permitted substances: hydroxypropyltrimethylammonium chloride (HCC), cationic polymers (e.g., guar gum hydroxypropyltrimethylammonium chloride, polyquaternium-10), silicones (e.g., polydimethylsiloxanes such as dimethylpolysiloxane and polydimethylsiloxane alcohol), emulsifiers (e.g., styrene-acrylate copolymers), rheology modifiers (e.g., hydroxyethyl cellulose and xanthan gum), humectants (e.g., panthenol and glycerin), non-polymer conditioning agents (e.g., quaternary ammonium compounds such as behenyltrimethylammonium chloride and stearyldimethylbenzylammonium chloride), fragrances, sunscreens, UV filters, colorants, and diluents and carriers as defined herein.

[0157] In some embodiments, the composition of the second aspect of the present invention is a hair coloring composition.

[0158] The hair coloring composition may contain a dye compound, and / or may contain a dye precursor compound that, when mixed with an oxidizing composition, generates an active dye in situ in the hair.

[0159] The oxidative hair coloring compositions of the present invention may contain one or more intermediates, such as p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, p-toluenediamine, p-aminophenol-phenylmethylpyrazolone, m-phenylenediamine, resorcinol, 1-naphthol, 1-hydroxyethyl-4,5-diaminopyrazole, and m-aminophenol. Depending on the desired shade, these intermediates may be present in any combination and ratio at a total intermediate concentration of 0.01% to 15%. Such compositions typically further contain one or more alkalizing agents, such as ammonia, ammonium hydroxide, sodium hydroxide, and monoethanolamine. The chromogenic compositions for oxidative dyeing contain oxidizing agents, such as hydrogen peroxide, sodium bromate, sodium percarbonate, or sodium perborate. These are typically present in amounts from 0.1% to 30% by weight.

[0160] The direct dye coloring compositions of the present invention may contain one or more direct dyes, such as those from the categories of nitrophenylenediamine (e.g., 4-nitro-o-phenylenediamine), nitroaminophenol (e.g., 2-amino-4-nitrophenol), and aminoanthraquinone (e.g., Disperse Red 11). These are typically present in amounts from 0.1% to 20% by weight, depending on the desired lightness or darkness.

[0161] In some preferred embodiments, the compositions of the present invention are not hair coloring compositions. Preferred compositions contain less than 0.1% by weight, preferably less than 0.01% by weight, of a dye compound and / or a dye precursor compound. Preferred compositions do not contain dye compounds and / or dye precursor compounds. Compounds that provide color to the composition, such as pigments and pearlescent agents, may be present, but suitably the composition does not contain any compounds that can be used to color hair.

[0162] In the first aspect of the method, the material is contacted with a composition comprising an aldehyde substituted with a hydroxyl group.

[0163] The material, preferably hair, can be wet or dry when in contact with the composition.

[0164] The composition is suitably applied to a material and spread across the surface of the material. In a preferred embodiment where the material is hair, the composition can be applied into the hair as a shampoo and / or combed through the hair.

[0165] The composition of the present invention can remain on the material or can be removed from the material. It can be suitably washed with warm water.

[0166] In some embodiments, the composition may be brought into contact with the material, spread extensively, and then removed immediately.

[0167] The composition can be suitably removed from the material by washing, preferably by water.

[0168] In some embodiments, the composition can be washed from the material by washing with a cleaning agent composition.

[0169] In some embodiments, the composition can be mechanically removed from the material, for example, by brushing.

[0170] In some embodiments, the composition can be retained on the material during the normal cycle and removed only when the material is washed.

[0171] In some embodiments where the material is hair, the composition can be applied to the hair in the manner of a shampoo, spread and rubbed into the hair, and then rinsed with water.

[0172] In some embodiments where the material is hair, the composition can be applied to the hair as a conditioner, spread throughout the hair (optionally using combing), left on the hair for a short time, and then washed off the hair with water.

[0173] In some embodiments where the material is hair, the composition can be applied to and retained on the hair in a styling manner. The composition can be sprayed, rubbed, combed, or otherwise spread through the hair in a manner known to those skilled in the art.

[0174] In embodiments where the composition is retained on hair, it is suitably retained on the hair until the next step of washing the hair, although some of the composition may be brushed or wiped off during normal activity.

[0175] In the method of the present invention, the composition is suitably brought into contact with the material (preferably hair) at ambient temperature. In some embodiments, the composition may be brought into contact with the material at a temperature greater than ambient temperature.

[0176] In some embodiments, the composition may be brought into contact with hair, and then the hair carrying the composition may be heated and / or manipulated and / or dried. Thus, the hair may be dried with a hair dryer or straightened after the composition is applied.

[0177] The first method of the present invention may include heating the hair. This heating step may include commonly used heating techniques, such as blow-drying, or using pliers, a straightener, or a cover.

[0178] The present invention may include contacting the material with a composition comprising a hydroxyl-substituted aldehyde once or more.

[0179] This invention can be used frequently, for example, each time hair (or another material) is washed. Alternatively, this invention can be used less frequently but periodically, for example, weekly or monthly.

[0180] It has been unexpectedly discovered that the method of the present invention can be significantly beneficial to hair. This benefit can be temporary, permanent, or semi-permanent.

[0181] The methods and compositions of the present invention can benefit hair by improving shine.

[0182] The methods and compositions of the present invention can benefit hair by improving its strength.

[0183] The methods and compositions of the present invention can benefit hair by improving heat protection.

[0184] The methods and compositions of the present invention can provide permanent curl or straightening of hair under mild conditions.

[0185] The methods and compositions of the present invention can benefit hair by improving manageability and / or combability.

[0186] According to a third aspect of the invention, there is a use for enhancing at least one hair property with hydroxyl-substituted aldehydes. Preferred features of the third aspect are as defined with respect to the first and second aspects.

[0187] A particularly preferred compound used in this invention is 2-hydroxyoctanal.

[0188] According to a fourth aspect of the invention, a compound of the following formula is provided. According to the fifth aspect, a method for preparing the compound of the fourth aspect is provided.

[0189] The compounds of the fifth aspect can be prepared by any suitable method. Such methods are known to those skilled in the art. A suitable method is described in Example 1.

[0190] According to a seventh aspect of the invention, a composition comprising the compound of the sixth aspect is provided.

[0191] The preferred composition is a hair care composition, with preferred characteristics as defined with respect to the second aspect.

[0192] The invention will now be further defined with reference to the following non-limiting embodiments. Detailed Implementation

[0193] Example 1 The hydroxyl-substituted aldehyde compounds used in this invention are prepared using the following method.

[0194] These are generated from the corresponding 1,2-diol compounds via the selective oxidation of α-alcohols. The copper catalyst is weighed in a high-temperature oil in a three-necked flask. The flask is then assembled with a side arm, a receiving flask, and a water-cooled condenser. The reaction is heated to the correct temperature under a nitrogen stream and / or vacuum using stirring.

[0195] The desired alcohol is added continuously at a constant rate. The product is collected by distillation from the reaction mixture. Vacuum or nitrogen is applied to ensure rapid distillation of the aldehyde, minimizing the chance of further oxidation. Extraction conditions depend on the aldehyde being prepared. Yields are generally greater than 75%.

[0196] Example 2 The following is an evaluation of the permanent / semi-permanent hair conditioning effects of the compositions of the present invention.

[0197] method 1. A 15.2cm / 3g bleached straight hair bundle was pre-washed with a standard commercially available non-conditioning shampoo and blow-dried. The 'total combing work' of each bundle was determined using a Dia-Stron® MTT175 miniature tensile tester equipped with combing accessories.

[0198] 2. Apply 2 ml of an aqueous solution containing 1% w / w 2-hydroxydodecanoal and 1% w / w SLES to the hair strands, comb through, and let stand for 5 minutes.

[0199] 3. Use a Tormaline® ceramic soldering iron to press the hair strand flat, slowly passing it over the hair strand 5 times.

[0200] 4. Wash the hair strands thoroughly to remove unbound material from the hair.

[0201] 5. Comb and blow-dry the hair.

[0202] 6. The 'total combing power' of each treated hair strand was measured again using a Dia-Stron® MTT175 miniature tensile tester equipped with combing accessories.

[0203] result After treating the hair strands according to the present invention, the 'total combing effort' is reduced by 36.5% compared to the initial value before treatment. + 3.5% (average of two parallel measurements of hair strands). This indicates the effect of permanent / semi-permanent hair conditioning. It is believed to be due to the reaction of hair with 2-hydroxydodecanealdehyde.

[0204] Example 3 The permanent / semi-permanent hair straightening effect of the compositions of the present invention is evaluated as follows.

[0205] method 1. A 15.2cm / 3g bleached straight hair bundle was pre-washed with a standard commercially available non-conditioning shampoo, combed, hung vertically, and allowed to air dry under ambient conditions for 6 hours, and then its initial length was measured.

[0206] 2. For 'treated' hair strands, apply 2 ml of an aqueous solution containing 2% w / w 2-hydroxyoctanal and 1% w / w SLES to the hair strands, comb through, and let stand for 5 minutes.

[0207] 3. For the control hair strand, apply 2 ml of aqueous solution containing 1% w / w SLES to the hair strand, comb through it, and let it stand for 5 minutes.

[0208] 4. Use a Tormaline® ceramic soldering iron to press the hair strand flat, slowly passing it over the hair strand 5 times.

[0209] 5. Wash the hair strands thoroughly to remove unbound material from the hair.

[0210] 6. Comb the hair straight, hang it vertically, and let it air dry for 6 hours under ambient conditions.

[0211] 7. Measure the final length of the hair bundle.

[0212] 8. Calculate the straightness using the following equation: in: L0 = Total straightened length of the hair bundle L1 = Initial untreated tight curl length of the hair strand L2 = The final length of the hair strand after straightening, washing, and air drying.

[0213] result After treating the hair strand according to the present invention, compared with the control hair strand 21.2 ( + Comparing 9.5% (the average of three parallel hair bundles), the straightening degree was 79.2%. + 5.9% (average of three parallel measurements). This indicates a permanent / semi-permanent straightening effect. This is believed to be due to the reaction of the hair with 2-hydroxyoctanal.

Claims

1. A method of treating a material, the method comprising contacting the material with a composition comprising an aldehyde substituted with a hydroxyl group.

2. The method of claim 1, wherein the material is keratin.

3. The method of claim 1 or 2, wherein the material is human hair or animal hair, preferably human hair.

4. The method of claim 3, wherein the material is growing human hair or animal hair, preferably growing human hair.

5. A hair care composition comprising a hydroxyl-substituted aldehyde.

6. The hair care composition of claim 5, wherein the composition comprises two or more hydroxyl-substituted aldehydes.

7. The method or composition of any of the preceding claims, wherein the aldehyde is an α-hydroxy aldehyde.

8. The method or composition of any of the preceding claims, wherein the aldehyde is selected from 2-hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal or glyceraldehyde.

9. The method or composition of any of the preceding claims, wherein the aldehyde is selected from 2-hydroxypropanal, 2-hydroxyhexanal, or 2-hydroxyoctanal.

10. The method or composition of any of the preceding claims, wherein the composition comprises a first hydroxyl-substituted aldehyde having less than 10 carbon atoms and a second hydroxyl-substituted aldehyde having 10 or more carbon atoms.

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