Compositions, personal care formulations, methods and uses for treating or preventing damage to hair

Abstract

The present invention provides a composition comprising a reaction product of a) itaconic anhydride and b) an amino compound containing at least one free amino group selected from the group consisting of amino acids, peptides, and hydrolyzed proteins, wherein the composition contains an itaconic acid-modified amino compound which is the reaction product of a) and b), and the amount of itaconic anhydride used in the reaction is calculated to react with 10 mol% to 100 mol% of the free amino groups of the amino compound. The present invention further provides a personal care formulation, a hair care formulation, a skin care formulation, a method for treating hair or skin, and use of the present composition containing the composition.

Description

Technical Field

[0001] The present invention relates to a composition, a personal care formulation comprising a composition such as a shampoo or a hair conditioner, a method of treating hair or skin with the composition, and the use of the composition for benefiting hair or skin.

Background Art

[0002] The need for personal care formulations, particularly hair care or skin care products, is well known. Such products can be used to wash or condition human skin or human hair, or to address various problems that human hair encounters, such as after treatments like bleaching or coloring, or due to exposure to negative environmental factors such as heat and pollution. Some hair care formulations can improve the quality of hair, such as strength, shine, and ease of brushing / combing.

[0003] Silicon-containing compositions may have an unfavorable environmental profile or may not be desirable for use in personal care formulations.

Summary of the Invention

Problems to be Solved by the Invention

[0004] There is a continuing need for improved personal care formulations, particularly hair care or skin care formulations, and for the development of suitable ingredients for such formulations.

Means for Solving the Problems

[0005] The present invention is based in part on the surprising recognition that reaction products of itaconic anhydride with amino acid-containing compounds, particularly hydrolyzed proteins, can be used to produce compositions according to the invention that are beneficial for personal care formulations, particularly for the care and / or conditioning of hair and / or skin. For example, the compositions according to the invention can be used as hair benefit agents in hair conditioners or shampoos. The benefits provided by the compositions of the invention can be selected from hair strengthening, cleansing, conditioning, detangling, repair, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume and styling.

[0006] Accordingly, viewed from a first aspect, the present invention provides a) itaconic anhydride and b) an amino compound containing at least one free amino group selected from the group consisting of amino acids, peptides and hydrolyzed proteins A composition comprising a reaction product thereof, the composition comprising an itaconic-modified amino compound which is the reaction product of a) and b), and the amount of itaconic anhydride used in the reaction being calculated to react with 10 mol% to 100 mol% of the free amino groups of the amino compound, preferably calculated by the formol titration described herein.

[0007] The compositions of the present invention can be advantageous by not containing reactants obtained from petrochemical sources. Itaconic anhydride can be obtained from renewable sources. Itaconic anhydride can be obtained from citric acid. Itaconic anhydride can be obtained from biological sources, preferably microbiological sources.

[0008] Viewed from a second aspect, the present invention provides a personal care formulation comprising the composition of the first aspect.

[0009] Viewed from a third aspect, the present invention provides a personal care formulation comprising a reaction product of itaconic anhydride and a hydrolyzed protein, the personal care formulation comprising from 0.1% to 10% by weight of the reaction product of itaconic anhydride and a hydrolyzed protein, based on the total weight of the formulation, and being suitable for topical application.

[0010] Viewed from a fourth aspect, the present invention provides a hair care formulation comprising the composition according to the first aspect and a further hair care component.

[0011] Viewed from a fifth aspect, the present invention provides a skin care formulation comprising the composition according to the first aspect and a further skin care component.

[0012] Viewed from a sixth aspect, the present invention provides a method of treating hair or skin comprising the step of applying a composition according to the first aspect to the hair or skin.

[0013] Viewed from a seventh aspect, the present invention provides a method of treating hair comprising the step of applying to the hair a composition according to the first aspect that provides to the hair a benefit selected from hair strengthening, cleansing, conditioning, detangling, repairing, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume and styling.

[0014] Viewed from an eighth aspect, the present invention provides the use of a composition according to the first aspect of the present invention for treating hair or skin to provide a benefit to the hair or skin.

[0015] Viewed from a ninth aspect, the present invention provides the use of a composition according to the first aspect for treating hair to provide to the hair a benefit selected from hair strengthening, cleansing, conditioning, detangling, repairing, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume and styling.

[0016] All of the features described in this specification may be combined in any combination with any of the above aspects.

Embodiments for Carrying Out the Invention

[0017] It will be understood that the upper or lower limits of amounts or ranges used in this specification may be combined independently.

[0018] When describing the number of carbon atoms in a substituent (for example, "C1 - C6"), it will be understood that the number refers to the total number of carbon atoms present in the substituent, including those present in branched groups. Further, for example, when describing the number of carbon atoms in a fatty acid, this refers to the total number of carbon atoms including those of the carboxylic acid and those present in branched groups.

[0019] As used in this specification, the term "residue" is the portion of a reactant molecule that remains in the reaction product compound after the reaction has occurred.

[0020] Many of the chemical substances that may be used to produce the compositions of the present invention are obtained from natural sources. Such chemical substances typically contain mixtures of chemical species due to their natural origin. Due to the presence of such mixtures, the various parameters defined in this specification may be average values and may be non - integer.

[0021] As used herein, the term "hydrolyzed protein" means a protein that has been hydrolyzed. Hydrolyzed proteins can include protein fragments, polypeptides, peptides, amino acids, and / or peptones. Hydrolyzed proteins can be produced by acid hydrolysis, alkaline hydrolysis, and / or enzymatic hydrolysis of a protein, preferably a protein of natural origin or a protein from a renewable source. Enzymatic hydrolysis is preferred. Without being bound by theory, the advantage of enzymatic hydrolysis compared to acid or alkaline hydrolysis is that enzymatic hydrolysis is more selective at the sites on the protein being hydrolyzed, and thus, improved amino compounds for use in the production of the compositions of the present invention result when compared to acid or alkaline hydrolysis. Generally, acid hydrolysis produces the smallest fragments in terms of weight average molecular weight, alkaline hydrolysis produces the largest fragments, and enzymatic hydrolysis produces fragments of intermediate size between acid hydrolysis and alkaline hydrolysis. The size of the hydrolyzed protein fragments is proportional to the number of amino acid residues in the fragment since the fragment is derived from the long-chain amino acid chains that make up the non-hydrolyzed protein. Acid hydrolysis can be disadvantageous because high temperatures and / or high pressures are required. Alkaline hydrolysis can be disadvantageous because it requires the use of irritating or dangerous chemicals.

[0022] The amino compounds used in the production of the compositions of the present invention may be chemically unmodified hydrolyzed proteins. The term "chemically unmodified hydrolyzed protein" means a protein that has not undergone further chemical modification (or reaction) other than hydrolysis.

[0023] The amino compounds used in the production of the compositions of the present invention may be partially hydrolyzed proteins. The term "partially hydrolyzed protein" means a protein that has not been completely hydrolyzed, i.e., not hydrolyzed to the extent that only individual amino acids remain in the amino compound.

[0024] As used herein, the term "personal care formulation" means a consumer product for the treatment, cleansing, care or conditioning of humans. Said products include, but are not limited to, chemical substances, compositions, products, or combinations thereof related to or having use or application in the treatment, cleansing, cleansing, care or conditioning of humans (especially including the skin, hair and mouth), such as personal detergents, hair care and styling agents, skin care formulations, cosmetics, hygiene products, oral care agents and deodorant agents.

[0025] The composition of the present invention The composition of the present invention is a) Itaconic anhydride and b) an amino compound containing at least one free amino group selected from the group consisting of amino acids, peptides and hydrolyzed proteins and comprises a reaction product thereof, the composition comprises an itaconic acid-modified amino compound which is the reaction product of a) and b), and the amount of itaconic anhydride used is calculated to react with 10 mol% to 100 mol% of the free amino groups of the amino compound. Preferably, the amount of itaconic anhydride required is calculated by the formal titration described herein.

[0026] Preferably, the composition further contains water. The composition may contain at least 10% by weight of water, preferably at least 20% by weight of water, more preferably at least 30% by weight of water, especially at least 40% by weight of water, desirably at least 50% by weight of water, especially at least 60% by weight of water, based on the total weight of the composition. The composition may contain up to 90% by weight of water, preferably up to 80% by weight of water, based on the total weight of the composition.

[0027] The composition may further contain itaconic acid. Itaconic acid may be formed by a minor side reaction of itaconic anhydride with water. This side reaction may slightly reduce the amount of itaconic anhydride that actually reacts with the free amino groups of the amino compound when compared to the theoretical amount calculated by the formal titration described herein. Therefore, it may be preferable to minimize the side reaction of itaconic anhydride with water by selecting appropriate reaction conditions. Preferably, the amount of itaconic anhydride added to react with the amino compound is the theoretical amount calculated to react with a specific molar % of the amino groups in the amino compound. Preferably, the theoretical amount is calculated by formal titration.

[0028] Itaconic anhydride may be obtained from a renewable source. Preferably, itaconic anhydride is not obtained from a petrochemical source. Itaconic anhydride may be obtained from citric acid. Itaconic anhydride may be obtained from a biological source, preferably a microbiological source. Preferably, itaconic anhydride is substantially pure itaconic anhydride, for example at least 85 wt% itaconic anhydride, preferably at least 90 wt% itaconic anhydride, more preferably at least 95 wt% itaconic anhydride.

[0029] Preferably, the amino compound is obtained from a renewable source. Preferably, the amino compound is not obtained from an animal protein source. This is advantageous since animal sources may not be desirable for consumers. Preferably, the composition does not contain animal-derived components. Preferably, the composition does not contain petrochemical-derived components. Preferably, the carbon-containing portion of the composition is at least 80% bio-based, more preferably at least 90%, particularly at least 95%, desirably at least 99%, particularly 100% bio-based according to ASTM D6866, based on the total weight of the carbon-containing portion of the composition. Preferably, the composition is suitable for vegan consumers.

[0030] Preferably, the amino compound comprises a hydrolyzed protein, more preferably consists essentially of a hydrolyzed protein, and even more preferably is a hydrolyzed protein. The hydrolyzed protein can be produced by acid, alkali or enzymatic hydrolysis, preferably acid or enzymatic hydrolysis. Enzymatic hydrolysis is particularly preferred. One or more enzymes may be used. The enzyme is preferably not of animal origin. Preferably, the enzyme is of microbial origin. The enzyme may comprise a carbohydrase and / or a protease. Preferably, the enzyme comprises a protease. The hydrolysis can be carried out to the extent necessary to achieve the desired weight average molecular weight of the hydrolyzed protein. The degree of hydrolysis can be varied by changing the temperature, the acid / alkali / enzyme used, and the elapsed time. The resulting hydrolyzed protein may be filtered and / or processed to remove unwanted substances. For example, when acid hydrolysis is used, the hydrolyzed protein can be treated to remove any chloride ions present.

[0031] The hydrolyzed protein can be obtained from natural sources. The hydrolyzed protein can be obtained from renewable sources. Preferably, the hydrolyzed protein is obtained from vegetable sources. The vegetable sources can be selected from potatoes, wheat, cottonseed, pea, chickpea and soybean, preferably selected from potatoes, wheat, pea and chickpea, and even more preferably selected from potatoes and chickpea. Preferably, the amino compound is a hydrolyzed vegetable protein, preferably a hydrolyzed potato protein. The composition may not contain hydrolyzed wheat protein or protein obtained from a wheat source. This can be advantageous as wheat protein may not be preferred for certain consumers.

[0032] Preferably, the amino compound includes oligomers of amino acids, which are also known as oligopeptides. These oligomers can be hydrolyzed protein fragments. The amino compound can include oligomers of amino acids with an average size of 2 to 20 amino acids (also known as residues), preferably 2 to 15 amino acids, more preferably 2 to 10 amino acids. Preferably, the average size is the weight-average size. The amino acids in the oligomer may be the same amino acid or different amino acids. The amino acids in the oligomer preferably include at least one glutamic acid residue or histidine residue, more preferably at least one glutamic acid residue. The amino compound may not be an individual amino acid. Preferably, the amino compound does not consist of individual amino acids. Alternatively, the amino compound may include glutamic acid or histidine, preferably glutamic acid, as an individual amino acid.

[0033] The weight-average molecular weight (Mw) of the amino compound can be at least 100 Daltons (Da), preferably at least 200 Da, preferably at least 300 Da. The weight-average molecular weight of the amino compound can be at most 20,000 Da, preferably at most 10,000 Da, preferably at most 8,000 Da, preferably at most 5,000 Da, preferably at most 3,000 Da, preferably at most 1,500 Da, preferably at most 1,000 Da. The molecular weight can be measured by size-exclusion chromatography, preferably by size-exclusion HPLC (SE-HPLC) as described in the following test method. Preferably, the amino compound has a weight-average molecular weight in the range of 100 Da to 5,000 Da, preferably 100 Da to 3,000 Da, preferably 100 to 1,500 Da.

[0034] Preferably, the composition of the present invention is substantially free of quaternary ammonium compounds. The use of the term "substantially free of" means that the composition contains, based on the total weight of the composition, preferably less than 10% by weight, more preferably less than 5% by weight, still more preferably less than 2% by weight, and most preferably less than 1% by weight. Preferably, the composition does not contain a quaternary ammonium compound.

[0035] Preferably, the composition of the present invention is substantially free of silicone compounds. The composition may be solid or powder. The use of the term "substantially free of" means that the composition contains, based on the total weight of the composition, preferably less than 10% by weight, more preferably less than 5% by weight, still more preferably less than 2% by weight, and most preferably less than 1% by weight. Preferably, the composition does not contain a silicone compound. Preferably, the composition does not contain an organosilane, an organosilicon, or a silicone compound.

[0036] The composition may further contain one or more preservatives. The composition may contain, based on the total weight of the composition, at least 0.1% by weight, preferably at least 0.2% by weight, more preferably at least 0.4% by weight, and particularly at least 0.6% by weight of a preservative. The composition may contain, based on the total weight of the composition, a maximum of 10% by weight, preferably a maximum of 5% by weight, more preferably a maximum of 3% by weight, and particularly a maximum of 2% by weight of a preservative. The preservative may include phenoxyethanol, benzoate, or sorbate, and more preferably, the preservative is selected from benzoate and sorbate, and more preferably, the preservative contains sodium benzoate and / or potassium sorbate. Alternatively, the composition may not contain a preservative.

[0037] The composition may be liquid at room temperature (25°C). The composition may be a solution or dispersion of an itaconic acid-modified amino compound in a solvent, preferably a solution, and preferably, the solvent contains water.

[0038] Alternatively, the composition may not contain water, or may contain residual water after being dried to a solid or powder form. Spray drying may be used to dry the composition. The composition may be a solid or a powder.

[0039] Ratio of reactants The reactants for the composition of the present invention are a) Itaconic anhydride and b) an amino compound containing at least one free amino group selected from the group consisting of amino acids, peptides and hydrolyzed proteins and.

[0040] The composition contains an itaconic acid-modified amino compound which is the reaction product of a) and b), and the amount of itaconic anhydride used is calculated to react with 10 mol% to 100 mol% of the free amino groups of the amino compound. Preferably, the calculation is by the formol titration described herein.

[0041] Surprisingly, the ratio of the reactants can affect the properties of the composition of the present invention. At least 10 mol%, more preferably at least 15 mol%, more preferably at least 20 mol%, more preferably at least 40 mol%, more preferably at least 60 mol%, more preferably at least 70 mol% of the free amino groups in the amino compound can react with the itaconic anhydride in the itaconic acid-modified amino compound. Up to 99 mol%, preferably up to 98 mol%, more preferably up to 95 mol% of the free amino groups in the amino compound can react with the itaconic anhydride in the itaconic acid-modified amino compound. Preferably, the amount of itaconic anhydride used is calculated to react with 40 mol% to 100 mol% of the free amino groups in the amino compound. More preferably, the amount of itaconic anhydride used is calculated to react with 60 mol% to 99 mol% of the free amino groups in the amino compound. Preferably, the calculation is by the formol titration described herein.

[0042] Personal care formulations Preferably, the composition of the present invention is suitable for use in personal care formulations. From a second aspect, the present invention provides a personal care formulation comprising the composition of the present invention. Preferably, the personal care formulation is for topical application to the skin or hair.

[0043] The personal care formulation can be selected from a moisturizer, a body butter, a gel cream, a high-concentration fragrance-containing product, a fragrance cream, a hair conditioner, a hair relaxer formulation, a hair shampoo, a hair styling product, a leave-on hair product, a water-free product, an antiperspirant and deodorant product, a cleanser, a 2-in-1 foaming emulsion, an emulsifier-free product, a mild formulation, a scrub formulation, such as a solid bead-containing formulation, an aqueous silicone formulation, a pigment-containing product, a sprayable emulsion such as a hair detangler, a color cosmetic, a shower product, a makeup remover, an eye makeup remover, and a wipe. Preferably, the personal care formulation is selected from a hair conditioner, a hair relaxer formulation, a hair shampoo, a hair styling product, a leave-on hair product, and a sprayable emulsion such as a hair detangler.

[0044] Preferably, the composition of the present invention is present in the personal care formulation at a concentration of at least 0.01% w / w, preferably at least 0.1% w / w, more preferably at least 0.5% w / w, and most preferably at least 0.8% w / w, based on the total weight of the formulation. Preferably, the composition of the present invention is present in the personal care formulation at a concentration of at most 20% w / w, preferably at most 15% w / w, more preferably at most 10% w / w, and most preferably at most 8% w / w, based on the total weight of the formulation.

[0045] Preferably, the personal care formulation comprises a reaction product of itaconic anhydride and a hydrolyzed protein, and the personal care formulation comprises 0.01 to 10% by weight, preferably 0.1 to 10% by weight, of the reaction product of itaconic anhydride and a hydrolyzed protein, based on the total weight of the formulation, and the personal care formulation is suitable for topical application.

[0046] The present invention can provide a personal care formulation comprising a composition of the present invention and a personal care ingredient. The personal care ingredient may be selected from a detergent, a hair conditioning agent, a hair styling agent, an anti-dandruff agent, a hair growth promoter, a fragrance, a pigment, a humectant, a film-forming agent, a hair color, a makeup agent, a thickening agent, an emulsifying agent, a wetting agent, an emollient, a preservative, a deodorizing activator, a dermatologically acceptable carrier, a surfactant, an abrasive, an absorbent, a fragrance, a colorant, an essential oil, an astringent, an anti-acne agent, an anti-caking agent, an antifoaming agent, an antioxidant, a binder, an enzyme, an enzyme inhibitor, an enzyme activator, a coenzyme, a plant extract, a ceramide, a buffer, a bulking agent, a chelating agent, a biocide for cosmetics, a topical analgesic, a substantial additive, an opacifying agent, a pH adjuster, a reducing agent, a blocker, a skin bleaching agent and / or a whitening agent, a skin conditioning agent, a skin soother and / or a healing agent, a skin treatment agent, a vitamin agent or a preservative.

[0047] Preferably, the personal care ingredient is selected from a detergent, a hair conditioning agent, a skin conditioning agent, a hair styling agent, an anti-dandruff agent, a hair growth promoter, a fragrance, a pigment, a humectant, a film-forming agent, a wetting agent, an α-hydroxy acid, a hair color, a makeup agent, a thickening agent, a preservative, a deodorant agent, a surfactant.

[0048] Many other personal care ingredients can be used in the personal care formulation according to the present invention. These ingredients may be oil-soluble, water-soluble or insoluble. Examples of such ingredients include the following: (i) Preservatives, preferably those approved for use as cosmetics, especially those listed in Annex V of the European Union Cosmetics Regulation. The preservative preferably contains sodium benzoate, potassium sorbate or phenoxyethanol. The preservative may include parabens (alkyl esters of 4-hydroxybenzoic acid), substituted ureas or hydantoin derivatives, for example those commercially available under the trade names Germaben II, Nipaguard BPX and Nipaguard DMDMH. The preservative may be used at a concentration in the range of 0.5% to 2% by weight based on the total weight of the formulation; (ii) Perfumes, typically used at concentrations in the range of 0.1% to 10% by weight, more typically up to about 5% by weight, and especially up to about 2% by weight, based on the total weight of the composition; (iii) Humectants or solvents, such as alcohols, polyols such as glycerol, and polyethylene glycols, typically used at concentrations in the range of 1% to 10% by weight based on the total weight of the composition; (iv) Alpha-hydroxy acids, such as glycolic acid, citric acid, lactic acid, malic acid, tartaric acid and their esters; self-tanning agents, such as dihydroxyacetone; (v) Vitamins and their precursors, including: (a) vitamin A, such as retinyl palmitate and other tretinoin precursor molecules, (b) vitamin B, such as panthenol and its derivatives, (c) vitamin C, such as ascorbic acid and its derivatives, (d) vitamin E, such as tocopherol acetate, (e) vitamin F, such as polyunsaturated fatty acid esters such as gamma-linolenic acid ester; (vi) Skin care agents such as ceramides, as functional mimics of natural materials or natural ceramides; (vii) Natural phospholipids, such as lecithin; (viii) Vesicle-containing compositions; (ix) Plant extracts having advantageous skin care properties; (x) Skin lightening agents such as kojic acid, arbutin and similar substances; (xi) Skin repair compound actives such as allantoin and similar series; (xii) Caffeine and similar compounds; (xiii) Cooling additives such as menthol or camphor; (xiv) Insect repellents such as N,N-diethyl-3-methylbenzamide (DEET) and citrus or eucalyptus oils; (xv) Essential oils; and (xvi) Typically, for providing a suspoemulsion, it is used in an amount in the range of 1% to 15% by weight, usually at least 5% by weight, particularly about 10% by weight, based on the total weight of the formulation. It includes fine pigments, particularly oxides and silicates such as iron oxides, particularly coated iron oxides, and / or titanium dioxide, and ceramic materials such as boron nitride, or pigments containing other solid components such as those used in makeup and cosmetics.

[0049] Personal care formulations may contain a fragrance or a scent-providing substance to provide a pleasant smell. In one aspect, the fragrance is provided from natural sources such as, but not limited to, alfalfa, almond, amber, angelica root, anise, apple, apricot, banana, basil, bay, bay laurel, benzoin, bergamot, bitter orange, black pepper, boadroze (rosewood), cajeput, cardamom, carrot seed, cedarwood, cinnamon, citronella, citrus, clary sage, clove, cocoa, coconut, coffee, coriander, cranberry, cypress, elemi, eucalyptus globulus, eucalyptus, fennel, frankincense, galbanum, geranium, german chamomile, ginger, grapefruit, helichrysum, hyssop, jasmine, juniper berry, lavender, lemon, lemongrass, lily, linden blossom, mango, marjoram, melissa, mint, myrrh, myrtle, neroli, niaouli, nutmeg, orange, oregano, palm, parsley, patchouli, peach, peppermint, petitgrain, pine, pineapple, raspberry, roman chamomile, rose, rosemary, sandalwood, spearmint, spruce, strawberry, tea, thyme, vanilla, vetiver, violet, yarrow, iran, etc. Preferably, the fragrance is selected from mint or vanilla.

[0050] Preferably, the personal care formulation is a skin care formulation. The present invention can provide a skin care formulation comprising the composition of the present invention and a skin care component. Preferably, the skin care component is as described herein. Preferably, the skin care formulation is for topical application to the skin.

[0051] Preferably, the composition of the present invention is present in the skin care formulation at a concentration of at least 0.01% w / w, preferably at least 0.1% w / w, more preferably at least 0.5% w / w, and most preferably at least 0.8% w / w, based on the total weight of the formulation. Preferably, the composition of the present invention is present in the skin care formulation at a concentration of up to 20% w / w, preferably up to 15% w / w, more preferably up to 10% w / w, and most preferably up to 8% w / w, based on the total weight of the formulation.

[0052] Preferably, the personal care formulation is a hair care formulation. The present invention can provide a hair care formulation comprising the composition of the present invention and a hair care component. Preferably, the hair care formulation is for topical application to the hair.

[0053] The hair care component can be selected from a gloss enhancer, a humectant, a herb additive, a hair strengthening agent, a vitamin additive, a colorant, a hair thickener; a setting agent and a styling agent; an ultraviolet absorber; a silicone oil; an essential oil and a fragrance; a thickener or a viscosity increasing agent; a detergent; a stabilizer; an emollient; a chelating agent; a blocking agent; a preservative; a bactericide; an antioxidant / radical scavenger; an antistatic agent; a conditioning agent; a detangling component; an emulsifier or a dispersant.

[0054] Preferably, the hair care formulation is a hair cleansing, conditioning, detangling, color protection or styling formulation, and particularly preferably, a hair cleansing or conditioning formulation.

[0055] Preferably, the composition of the present invention is present in the hair care formulation at a concentration of at least 0.01% w / w, preferably at least 0.1% w / w, more preferably at least 0.5% w / w, and most preferably at least 0.8% w / w, based on the total weight of the formulation. Preferably, the composition of the present invention is present in the hair care formulation at a concentration of up to 20% w / w, preferably up to 15% w / w, more preferably up to 10% w / w, and most preferably up to 8% w / w, based on the total weight of the formulation.

[0056] The formulation may be in the form of an aqueous "leave-on" or aqueous "rinse-off" end-use product. For such formulations, a diluted solution may be used. Preferably, a buffered solution with a pH adjusted to weakly acidic in the range of 4 to 6 is used. In the case of a rinse-off formulation, there is an instruction to rinse off the diluted formulation after application. Depending on the required level of treatment, such an instruction may require leaving the product on the hair for a certain period of time, such as 1 minute to 30 minutes. In the case of a leave-on formulation, the rinsing step is omitted.

[0057] If the formulation is a hair shampoo or conditioner having the function of straightening hair, the shampoo or conditioner may be in the form of a dispersion, emulsion or solution. One of the preferred systems is one that forms a liquid crystal. The liquid crystal is preferably a lyotropic liquid crystal (i.e., dependent on both concentration and temperature), more preferably a lamellar phase liquid crystal, and particularly an L-α phase (neat) liquid crystal.

[0058] The hair care formulation can contain many different types of hair care ingredients such as the following; (i) Cationic hair conditioning agents, such as ethoxylated phosphate fats quats, e.g., those sold as Arlasilk™ by Croda; fatty amidoamines, e.g., those sold as Incromine™ by Croda; fatty quats, e.g., those sold as Incroquat™, Crodazosoft™, Rejuvasoft™ or VibraRiche™ by Croda, typically used at a concentration in the range of 1% to 5% by weight based on the total weight of the formulation. These are typically combined with polymeric hair conditioning cationic materials such as quaternized celluloses sold as Crodacel™ and MiruStyle™ by Croda, quaternized proteins such as those sold as Croquat™, Crosilkquat™, Kerestore™ and Hydrotriticum™ by Croda. (ii) Fatty alcohols, such as stearyl, cetearyl, cetyl, oleyl alcohol, typically used at a concentration in the range of 2% to 5% by weight based on the total weight of the formulation. (iii) Humectants or solvents, such as alcohols and polyols, e.g., glycerol, and polyethylene glycol, typically used at a concentration in the range of 1% to 10% by weight based on the total weight of the formulation when used. (iv) Reconstructing agents, such as hydrolyzed proteins, e.g., wheat gluten, which have the function of penetrating into the hair and strengthening the hair structure by polymer cross-linking. (v) Gloss or detangling agents that bind to the hair and reflect light, e.g., silicones, such as dimethicone, phenyltrimethicone, dimethiconol and / or trimethylsilylamodimethicone, typically at a concentration in the range of 0.2% to 10% by weight based on the total weight of the formulation. (vi) pH adjusters, such as citric acid, lactic acid, which generally maintain the pH of the conditioner at about 4 - 6. (vii) Thermal protectors that protect hair from excessive heat by broad dryers or curling irons or hot rollers, usually heat-absorbing polymers, such as those sold by Croda as Mirustyle™ MFP (cationized starch); and (viii) UV protectants for protecting hair or formulation components from degradation by UV light, such as those sold by Croda as Crodasorb™ UV-HPP.

[0059] Shampoo formulations Preferred personal care formulations according to the present invention contain from 0.1 to 20% by weight of the composition of the present invention, based on the total weight of the formulation, and further a) i) Anionic surfactants in an amount of from 0.1 to 30% by weight, preferably from 0.5 to 20% by weight, more preferably from 1 to 15% by weight, more preferably from 3 to 10% by weight, more preferably from 5 to 7% by weight, based on the total weight of the formulation, wherein at least one anionic surfactant is selected from alkyl sulfates, sulfonates, and phosphates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 C atoms in the alkyl group and 2 to 6 ethylene oxide groups in the molecule, acyl isethionates having 8 to 24 C atoms in the acyl group, and acylated amino acids and protein fatty acid condensates having 8 to 24 C atoms in the acyl group, and mixtures of these anionic surfactants; ii) Nonionic surfactants selected from alkanolamides, sugar-based surfactants and ethoxylated surfactants; and iii) Zwitterionic surfactants in an amount of from 0.1 to 15% by weight, preferably from 0.2 to 10% by weight, more preferably from 0.5 to 8% by weight, more preferably from 1 to 5% by weight, still more preferably from 2 to 4% by weight, based on the total weight of the formulation, selected from amphoacetates / amphodiacetates, amine oxides, sultaines and betaines, more preferably containing cocamidopropyl betaine at least one surfactant selected from; b) at least one additional hair care ingredient as described herein; c) water and is a shampoo containing.

[0060] Hair conditioner formulation A preferred personal care formulation according to the present invention contains 0.1 to 20% by weight of the composition of the present invention, based on the total weight of the formulation, and further, a) i) a cationic surfactant in an amount of 0.01 to 8% by weight, preferably 0.1 to 6% by weight, more preferably 0.5 to 5% by weight, more preferably 1.0 to 4% by weight, more preferably 1.5 to 3.5% by weight, based on the total weight of the formulation, preferably a quaternary ammonium compound having at least one C8 - C24 alkyl residue, an esterquat having at least one C8 - C24 acyl residue, and an amidoamine, a cationic surfactant selected from ii) a nonionic surfactant selected from alkanolamides, sugar - based surfactants, and ethoxylated surfactants at least one surfactant selected from; b) optionally, at least one linear saturated 1 - alkanol having 12 to 30 carbon atoms in an amount of 0.2 to 10% by weight, particularly preferably 0.5 to 7% by weight, based on the total weight of the formulation, selected from lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, and behenyl alcohol, and at least one linear saturated 1 - alkanol selected from mixtures of these 1 - alkanols; c) optionally, at least one oil in an amount of 0.01 to 10% by weight, preferably 0.1 to 3% by weight, particularly preferably 0.5 to 1% by weight, based on the total weight of the formulation; d) water and is a rinse - off hair conditioner containing.

[0061] Method for treating hair or skin Viewed from another aspect, the present invention provides a method for treating hair or skin, comprising the step of applying a composition according to the present invention to the hair or skin.

[0062] Preferably, the composition provides a benefit selected from cleaning and conditioning the hair or skin.

[0063] Preferably, the composition comprises any of the features described herein with respect to the composition of the present invention.

[0064] The method may include rinsing the composition from the hair or skin with water. Alternatively, the method may include leaving the composition on the hair or skin.

[0065] Viewed from another aspect, the present invention provides a method for treating hair, comprising the step of applying to the hair a composition according to the present invention that provides a benefit selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume, and styling.

[0066] Preferably, the composition is part of a hair shampoo or conditioner formulation and preferably comprises any of the features described herein.

[0067] Preferably, the composition comprises any of the features described herein with respect to the composition of the present invention.

[0068] Use of a composition for treating hair or skin Viewed from another aspect, the present invention provides the use of a composition according to the present invention for treating hair or skin to provide a benefit selected from cleaning and conditioning the hair or skin.

[0069] Viewed from another aspect, the present invention provides the use of a composition according to the present invention for treating hair to provide the hair with benefits selected from hair strengthening, cleansing, conditioning, detangling, repairing, gloss, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume and styling.

[0070] Preferably, the composition is part of a hair shampoo or conditioner formulation, preferably comprising any of the features described herein.

[0071] Preferably, the composition comprises any of the features described herein with respect to the composition of the present invention.

Examples

[0072] The present invention will be described by the following non-limiting examples. All parts and percentages are given by weight unless otherwise specified.

[0073] It is understood that all the tests and physical properties described were determined at atmospheric pressure and ambient temperature (i.e., about 23 °C) unless otherwise specified herein or in the referenced test methods and procedures.

[0074] Test Methods In this specification, the following test methods were used.

[0075] (i) The formal titration method is a titration method for determining the degree of substitution of amino groups described by Cobbett, W.G., Gibbs, J.A. and Leach, A.A. (1964). J. Appl. Chem. (London), 14, 296 - 302.

[0076] (ii) The pH was measured at room temperature (25 °C) using a Fisher Scientific Accumet AE150 pH Meter. Depending on the initial pH measurement value, the pH of the formulation was adjusted to the range of 4.0 - 5.0 using a 10 wt% aqueous sodium hydroxide solution (when the pH was high) or a 10 wt% aqueous citric acid solution (when the pH was low). The pH was measured immediately after formulation preparation and after 24 hours.

[0077] (iii) The active substance content (wt%) in the sample was calculated from the measurements of the total non-volatile content and the ash content. The total non-volatile content was measured by oven-drying a sample of known weight at 105 °C for 17 - 19 hours to remove the existing moisture and other volatile components. After cooling in a desiccator, the residual weight was used to calculate the total non-volatile content (wt%) of the sample. For the ash content, a sample of known weight was carefully heated in the presence of air to a temperature of 575 - 600 °C using a stepwise temperature increase and held at that temperature for 16 - 18 hours (or longer if necessary). After cooling in a desiccator, the residual weight was used to calculate the ash content (wt%) of the sample. Next, the active substance content (wt%) in the sample was calculated by subtracting the weight% of the ash content from the weight% of the total non-volatile content.

[0078] (iv) The weight-average molecular weight was measured by size exclusion high performance liquid chromatography (SE-HPLC). The HPLC apparatus and settings used are shown in Table 1.

[0079] [Table 1]

[0080] (v) Tensile test data for single hair fibers were measured in a controlled environmental chamber using a tensile testing machine (MTT690) from Diastron Ltd. (Andover, Hants, UK) equipped with an automatic load system (model ALS1500) and a fiber dimension analysis system (model FDAS770). Fifty single fibers were randomly selected from each hair tress processed for each sample and first prepared for testing with the AAS1600 (Auto-Assembly System) from Diastron Ltd. The length of each hair fiber sample was 30 mm. Next, the prepared hair fiber samples were placed on a rotary sample tray and pre-equilibrated at a relative humidity (RH) of 50% and room temperature (about 25 °C) for at least 1 hour before the experiment. After pre-equilibration, the ALS1500 was used to transfer each fiber sample from the sample tray to the FDAS770. In the FDAS770, a laser micrometer was used to measure the dimensions (cross-sectional area in square microns) of the fiber sample by scanning 5 slices along the length of the fiber. The fiber sample was then returned to the sample tray, and a pneumatically actuated rod held one end of the tensioned fiber sample while a jaw equipped with a pneumatically actuated 2 kg (20 N) load cell grasped the other end of the fiber sample, and the fiber sample was slowly stretched at an elongation rate of 20 mm / min until the fiber reached the breaking point. At the breaking point, each fiber sample created a stress-strain curve. Data on the breaking stress (gmf / square micron) were created and defined as the stress at which the hair fiber breaks.

[0081] Example 1 The amino compounds used to produce the compositions of the present invention can be produced by any of the following methods A - D.

[0082] Method A Potato protein concentrate was added to a hydrochloric acid solution and mixed until well dispersed. The resulting dispersion was heated to reflux conditions. The dispersion was heated until the weight-average molecular weight of the protein (measured by SE-HPLC described in the test method) no longer decreased in the range of usually 200 - 500 Da. When the hydrolysis was complete, sodium hydroxide was added to raise the pH of the solution. The protein hydrolyzate was purified by filtration and activated carbon treatment. After purification, further sodium hydroxide was added to make the solution basic, and concentrated to the desired active substance content (in the range of 20 - 30% by weight of the active substance content) by evaporation or ultrafiltration which has the advantage of salt removal. The resulting product is called amino compound A.

[0083] Method B Potato protein concentrate was added to a hydrochloric acid solution and mixed until well dispersed. The resulting dispersion was heated to reflux conditions. The dispersion was heated until the weight-average molecular weight of the protein no longer decreased in the range of usually 200 - 500 Da. Then, the acidic protein hydrolyzate was recovered by filtration. Next, the solution was passed through an ion exchange resin to remove chloride ions and the pH of the solution was raised. The protein hydrolyzate was purified by activated carbon treatment. After purification, further sodium hydroxide was added to make the solution basic and concentrated to the desired active substance content (in the range of 20 - 30% by weight of the active substance content). The resulting product is called amino compound B.

[0084] Method C Potato protein concentrate was added to water and mixed until well dispersed. The resulting dispersion was heated to the desired temperature, and then the pH was adjusted using a sodium hydroxide solution. Hydrolysis of the potato protein was catalyzed by using enzymes (carbohydrase and protease) and stirring within the desired temperature and pH ranges to achieve a typical weight average molecular weight of about 400 - 700 Da. After hydrolysis, a hydrochloric acid solution was added to lower the pH of the hydrolysis mixture to acidic, and heated to denature the enzymes. The protein hydrolysate was purified by filtration and activated carbon treatment. Then, using sodium hydroxide, the resulting diluted hydrolyzed protein solution was adjusted to a basic pH and concentrated to the desired active substance content (in the range of 20 - 30% by weight of the active substance content). The resulting product is called amino compound C.

[0085] Method D Potato protein concentrate was added to water and mixed until well dispersed. The resulting dispersion was heated to the desired temperature, and then the pH was adjusted using a sodium hydroxide solution. Hydrolysis of the potato protein was catalyzed by using enzymes (carbohydrase and protease) and stirring within the desired temperature and pH ranges to achieve a typical weight average molecular weight of about 700 - 950 Da. After hydrolysis, a hydrochloric acid solution was added to lower the pH of the hydrolysis mixture to acidic, and heated to denature the enzymes. The protein hydrolysate was purified by filtration and activated carbon treatment. Then, using sodium hydroxide, the resulting diluted hydrolyzed protein solution was adjusted to a basic pH and concentrated to the desired active substance content (in the range of 20 - 30% by weight of the active substance content). The resulting product is called amino compound D.

[0086] Example 2 According to the following method, amino compound A, B, C or D is reacted with itaconic anhydride in a suitable container to produce the composition of the present invention: 1. Charge the amino compound into the container. 2. Adjust the pH to 9.5 - 11.0 (preferably 10.0 - 10.5) with sodium hydroxide. A high pH is preferred to promote the reaction of itaconic anhydride with the amino compound rather than with water in order to avoid or reduce the formation of itaconic acid. 3. Add the calculated amount of itaconic anhydride (calculated by formol titration, a technique described in Cobbett, W.G., Gibbs, J.A. and Leach, A.A. (1964). J. Appl. Chem. (London), 14, 296 - 302). This calculation is based on the reaction proceeding to completion, but a portion of the itaconic anhydride may react with water to form itaconic acid, which may prevent the complete reaction between itaconic anhydride and the amino compound. An example of the calculated amount of itaconic anhydride required in grams is, for example, 200 (exemplary weight (g) of the amino compound) × 55 (exemplary result of formol titration) × 0.02 (molar concentration of NaOH used in formol titration) × 112 (molecular weight of itaconic anhydride) × 0.75 (75 mol% of free amino groups required for the reaction) / 1000 (unit conversion). 4. Maintain the temperature at 15 - 45°C, preferably 20 - 35°C, and the pH at 9.5 - 11.0, preferably 10.0 - 10.5, between the addition of itaconic anhydride and the start of the reaction. 5. Maintain the reaction conditions for an additional 1 - 4 hours (preferably 1 - 2 hours). 6. Acidify to pH 3.5 - 5.5 (preferably 4.0 - 5.0) with a mineral acid such as hydrochloric acid. 7. Add a preservative and store. 8. Cool and adjust the pH to 3.5 - 5.5 (preferably 4.0 - 5.0). 9. Filter.

[0087] The samples in Table 2 below were prepared using the methods of Example 1 and Example 2, but Sample 1 had no itaconic modification and only Example 1 was used. All samples were adjusted to pH 3.5 - 5.

[0088]

Table 2

[0089] Example 3 The following procedure was used to process hair samples and conduct tensile tests: a) Using commercially available bleaching systems (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach), bleach undamaged European brown hair to the desired damage level. b) Divide a single hair tress into multiple mini-tresses and subject them to different treatments for comparison. c) Immerse each mini-tress in a solution containing 1% (w / w) active substance for 30 minutes. d) As a control, immerse the mini-tresses in DI water for 30 minutes. e) Use a hair dryer to dry each mini-tress at a low temperature and high power setting.

[0090] Tensile test data for the hair was collected by taking 50 fibers from each mini-tress and measuring them as described in the items of the above test method.

[0091] The results were compared to the DI water control. The average results are shown in Table 3 below.

[0092]

Table 3

[0093] Table 3 shows an increase in the breaking stress of the hair treated with amino compound B. Further improvement is seen with itaconic acid-modified amino compound A. The hair treated with itaconic acid-modified amino compound A showed a significantly higher breaking stress compared to the control.

[0094] Example 4 The following procedure was used to process hair samples and conduct tensile tests: a) Use commercially available bleaching systems (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach) to bleach undamaged European brown hair to the desired damage level. b) Divide a single hair tress into multiple mini-tresses and subject them to different treatments for comparison. c) Immerse each mini-tress in a solution containing 1% (w / w) active substance for 30 minutes. d) As a control, immerse the mini-tresses in DI water for 30 minutes. e) After 30 minutes, rinse the tresses in warm water for 30 seconds. f) Use a hair dryer to dry each mini-tress on a low heat, high power setting.

[0095] Tensile test data for the hair was obtained by collecting 50 fibers from each mini-tress and measuring them as described in the items of the above test method.

[0096] The results were compared with the DI water control. The average results are shown in Table 4 below.

[0097]

Table 4

[0098] In Table 4, despite rinsing the tresses, the results are consistent between Tables 3 and 4. Amino compound B showed improvement compared to the control. Itaconic acid-modified amino compound A showed further improvement with a significant difference compared to the control.

[0099] Example 5 The following procedure was used to process hair samples and conduct tensile tests: a) Use commercially available bleaching systems (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach) to bleach undamaged European brown hair to the desired damage level. b) Divide a single hair tress into multiple mini-tresses, apply different treatments, and compare them. c) Immerse each mini-tress in a solution containing 1% (w / w) active substance for 30 minutes. d) As a control, immerse the mini-tresses in DI water for 30 minutes. e) Use a hair dryer to dry each mini-tress with a low heat and high power setting.

[0100] The tensile test data of the hair was obtained by collecting 50 fibers from each mini-tress and measuring them as described in the items of the above test method. (Except for sample 7) Each test was repeated using mini-tresses taken from the same original hair, and a total of 100 fibers, 2×50 for each treatment, were obtained.

[0101] The results were compared with the DI water control. The average results are shown in Table 5 below.

[0102]

Table 5

[0103] Table 5 shows the increase in breaking stress when the hair is treated with itaconic acid-modified hydrolyzed potato protein. 75% and 90% itaconic acid-modified hydrolyzed potato protein showed significant improvement compared to the control.

[0104] It should be understood that the present invention is not limited to the details of the above-described embodiments which are presented by way of example only. Many modifications are possible.

Claims

1. a) Itaconic acid anhydride and b) an amino compound containing at least one free amino group selected from the group consisting of amino acids, peptides, and hydrolyzed proteins A composition comprising the reaction product of, The composition comprises an itacone-modified amino compound which is a reaction product of a) and b), and the amount of itaconic anhydride used in the reaction is calculated to react with 10 mol% to 100 mol% of the free amino groups of the amino compound.

2. The composition according to claim 1, further comprising water.

3. The composition according to claim 1 or 2, further comprising itaconic acid.

4. The composition according to claim 1 or 2, further comprising a preservative preferably selected from benzoates and sorbates.

5. The composition according to claim 1 or 2, wherein the amino compound is a hydrolyzable protein, preferably a hydrolyzable plant protein, preferably a hydrolyzable potato protein.

6. The composition according to claim 1 or 2, wherein the amino compound is not individual amino acids.

7. The composition according to claim 1 or 2, wherein the amino compound preferably has a weight-average molecular weight in the range of 100 Da to 5000 Da, more preferably 100 Da to 3000 Da, and more preferably 100 Da to 1500 Da, as measured by size exclusion chromatography.

8. The composition according to claim 1 or 2, which does not contain organosilane, organosilicon, or silicone compounds.

9. The composition according to claim 1 or 2, which does not contain a quaternary ammonium compound.

10. A personal care formulation comprising the composition according to claim 1 or 2.

11. A personal care formulation comprising a reaction product of itaconic acid anhydride and hydrolyzed protein, wherein the formulation contains 0.1 to 10% by weight of the reaction product of itaconic acid anhydride and hydrolyzed protein based on the total weight of the formulation, and is suitable for topical application.

12. A hair care formulation comprising the composition according to claim 1 or 2 and further hair care ingredients.

13. A skincare formulation comprising the composition according to claim 1 or 2 and further skincare ingredients.

14. A method for treating hair or skin, comprising the step of applying the composition according to claim 1 or 2 to the hair or skin.

15. The method according to claim 14, wherein the composition provides the hair or skin with a benefit selected from cleansing and conditioning.

16. A method for treating hair, comprising the step of applying a composition according to claim 1 or 2 to the hair, which provides the hair with a benefit selected from hair strengthening, cleansing, conditioning, detangling, repair, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume, and styling.

17. Use of the composition according to claim 1 or 2 for treating the hair or skin to provide the benefits selected from cleansing and conditioning.

18. Use of the composition according to claim 1 or 2 for treating the hair to provide the hair with benefits selected from hair strengthening, cleansing, conditioning, detangling, repair, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, humidity control, curl retention, heat protection, improved movement, volume, and styling.