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

Abstract

The present invention provides a composition comprising the reaction product of: a) itaconic anhydride; and b) an amino compound comprising at least one free amino group, wherein the amino compound is selected from the group consisting of amino acids, peptides and hydrolyzed proteins; wherein the composition comprises an itaconic acid modified amino compound wherein the itaconic acid modified amino compound is the reaction product of a) and b), and wherein the amount of itaconic anhydride used in the reaction is calculated to react with 10 mol% to 100 mol% of free amino groups of the amino compound. The invention further provides personal care formulations, hair care formulations, skin care formulations comprising the compositions, methods of treating hair or skin and uses of the compositions.

Description

Field of the Invention

[0002] The present invention relates to compositions, personal care formulations (such as shampoos or conditioners) comprising the compositions, methods of treating hair or skin with the compositions, and uses of the compositions to provide benefits to hair or skin.

[0003] background

[0004] The need for personal care formulations, in particular hair care or skin care products, is well known. Such products may be used to cleanse or condition human skin or human hair, or to address various problems encountered by human hair after treatments such as bleaching or coloring, or due to exposure to negative environmental factors such as heat and pollution. Some hair care formulations are also intended to improve the qualities of the hair such as strength, shine or ease of brushing / combing.

[0005] Silicon-containing compositions may have adverse environmental properties or be undesirable for use in personal care formulations.

[0006] There is a continuing need to develop improved personal care formulations, particularly hair care or skin care formulations, and suitable ingredients for use in such formulations. SUMMARY OF THE INVENTION

[0007] The present invention is based in part on the surprising recognition that the reaction products of itaconic anhydride with amino acid-containing compounds, in particular hydrolyzed proteins, can prepare compositions according to the present invention that are beneficial for personal care formulations, in particular for the care and / or conditioning of hair and / or skin. For example, the compositions according to the present invention can be used as hair benefit agents in conditioners or shampoos. The benefits provided by the compositions of the present invention can be selected from hair strengthening, cleaning, conditioning, smoothing, repairing, shine, vitality, softness, anti-frizz, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improved movement, volume and styling.

[0008] Thus, viewed from a first aspect, the invention provides a composition comprising the reaction product of:

[0009] a) itaconic anhydride; and

[0010] b) an amino compound comprising at least one free amino group, wherein the amino compound is selected from the group consisting of amino acids, peptides and hydrolyzed proteins;

[0011] wherein the composition comprises an itaconic acid-modified amino compound, wherein the itaconic acid-modified amino compound is the reaction product of a) and b), and wherein 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, preferably calculated by formaldehyde titration as described herein.

[0012] The composition of the present invention may have the advantage of not comprising any reactants obtained from petrochemical sources. Itaconic anhydride may be obtained from renewable sources. Itaconic anhydride may be obtained from citric acid. Itaconic anhydride may be obtained from biological sources, preferably from microbial sources.

[0013] Viewed from a second aspect, the present invention provides a personal care formulation comprising the composition of the first aspect.

[0014] Viewed from a third aspect, the present invention provides a personal care formulation comprising the reaction product of itaconic anhydride and hydrolyzed protein, wherein the personal care formulation comprises from 0.1 to 10 wt % of the reaction product of itaconic anhydride and hydrolyzed protein, based on the total weight of the formulation, and wherein the personal care formulation is suitable for topical application.

[0015] Viewed from a fourth aspect, the present invention provides a hair care formulation comprising a composition according to the first aspect and additional hair care ingredients.

[0016] Viewed from a fifth aspect, the invention provides a skin care formulation comprising a composition according to the first aspect and a further skin care ingredient.

[0017] Viewed from a sixth aspect, the invention provides a method of treating hair or skin comprising the step of applying to the hair or skin a composition according to the first aspect.

[0018] 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, wherein the composition provides a benefit to the hair, and wherein the benefit is selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improving hair direction, hair volume and styling.

[0019] Viewed from an eighth aspect, the present invention provides the use of a composition according to the first aspect of the invention for treating the hair or skin to provide a benefit to the hair or skin.

[0020] Viewed from a ninth aspect, the present invention provides the use of a composition according to the first aspect for treating hair to provide a benefit to the hair selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improved hair direction, hair volume and styling.

[0021] All features described herein may be combined with any of the above aspects in any combination. DETAILED DESCRIPTION OF THE INVENTION

[0023] It is to be understood that any amount or upper or lower range limits used herein may be independently combined.

[0024] It should be understood that when describing the number of carbon atoms in a substituent group (e.g., "C1 to C6"), this number refers to the total number of carbon atoms present in the substituent group, including any carbon atoms present in any branching groups. In addition, when describing the number of carbon atoms in, for example, a fatty acid, this refers to the total number of carbon atoms, including the carbon atoms at the carboxylic acid and any carbon atoms present in any branching groups.

[0025] The term "residue" as used herein is the portion of a reactant molecule that remains in a reaction product compound after a reaction has occurred.

[0026] Many chemicals that can be used to prepare the compositions of the present invention are obtained from natural sources. Such chemicals, due to their natural sources, generally include mixtures of chemical substances. Due to the presence of such mixtures, the various parameters defined herein may be average values ​​and may be non-integer values.

[0027] The term "hydrolyzed protein" is used herein to refer to a protein that has been hydrolyzed. Hydrolyzed protein can include protein fragments, polypeptides, peptides, amino acids and / or peptones. Hydrolyzed protein can be produced by acid hydrolysis, alkaline hydrolysis and / or enzymatic hydrolysis of a protein (preferably a naturally occurring protein or a protein from a renewable source). Enzymatic hydrolysis is preferred. Without being bound by theory, when compared with acid hydrolysis or alkaline hydrolysis, the advantage of enzymatic hydrolysis is that enzymatic hydrolysis is more selective to the site on the hydrolyzed protein, so when compared with acid hydrolysis or alkaline hydrolysis, an improved amino compound for the preparation of the composition of the present invention is produced. Typically, acid hydrolysis can produce the smallest fragment by weight average molecular weight, alkaline hydrolysis can produce the largest fragment, and enzymatic hydrolysis can produce a medium-sized fragment between acid hydrolysis and alkaline hydrolysis. The size of the fragment in the hydrolyzed protein is directly proportional to the number of amino acid residues in the fragment, because the fragment is from the long amino acid chain that constitutes the unhydrolyzed protein. Acid hydrolysis may be disadvantageous due to the need for high temperature and / or high pressure. Alkaline hydrolysis can be disadvantageous due to the need to use harsh or hazardous chemicals.

[0028] The amino compound used to prepare the composition of the present invention may be a chemically unmodified hydrolyzed protein. The term "chemically unmodified hydrolyzed protein" refers to a protein that has not been further chemically modified (or reacted) besides being hydrolyzed.

[0029] The amino compound used to prepare the composition of the present invention may be a partially hydrolyzed protein. The term "partially hydrolyzed protein" refers to a protein that has not been completely hydrolyzed, ie, has not been hydrolyzed to the extent that only a single amino acid remains in the amino compound.

[0030] As used herein, the term "personal care formulation" refers to a consumer product for the treatment, cleaning, care or conditioning of an individual. The aforementioned consumer product may include, but is not limited to, chemicals, compositions, products or combinations thereof that are used or applied in connection with or in the treatment, cleaning, cleansing, care or conditioning of an individual (particularly including the skin, hair and oral cavity), such as personal washing, hair care and styling, skin care formulations, cosmetics, hygiene products, oral care and deodorants.

[0031] Compositions of the present invention

[0032] The composition of the present invention comprises the reaction product of:

[0033] a) itaconic anhydride; and

[0034] b) an amino compound comprising at least one free amino group, wherein said compound is selected from the group consisting of amino acids, peptides and hydrolyzed proteins;

[0035] wherein the composition comprises an itaconic acid modified amino compound, wherein the itaconic acid modified amino compound is the reaction product of a) and b), and wherein 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 formaldehyde titration as described herein.

[0036] Preferably, the composition also comprises water. The composition may comprise at least 10% by weight of water, preferably at least 20% by weight of water, more preferably at least 30% by weight of water, particularly 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 comprise up to 90% by weight of water, preferably up to 80% by weight of water, based on the total weight of the composition.

[0037] The composition may also include itaconic acid. Itaconic acid may be formed by a small amount of side reaction of itaconic anhydride with water. This side reaction may reduce the amount of itaconic anhydride that actually reacts with the free amino groups of the amino compound by a small amount when compared to the theoretical amount calculated by formaldehyde titration as described herein. It is therefore preferred to minimize the side reaction of itaconic anhydride with water by selecting suitable reaction conditions. Preferably, the amount of itaconic anhydride added to react with the amino compound is the calculated theoretical amount to react with a specified mole % of amino groups in the amino compound. Preferably, the theoretical amount is calculated by formaldehyde titration.

[0038] Itaconic anhydride can be obtained from renewable sources. Preferably, itaconic anhydride is not obtained from petrochemical sources. Itaconic anhydride can be obtained from citric acid. Itaconic anhydride can be obtained from a biological source, preferably from a microbial source. Preferably, itaconic anhydride is substantially pure itaconic anhydride, such as at least 85 wt % itaconic anhydride, preferably at least 90 wt % itaconic anhydride, more preferably at least 95 wt % itaconic anhydride.

[0039] 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 because animal sources may be undesirable for consumers. Preferably, the composition does not contain components of animal origin. Preferably, the composition does not contain components of petrochemical origin. According to ASTM D6866, preferably, the carbon-containing portion of the composition is at least 80% biobased, more preferably at least 90%, particularly at least 95%, desirably at least 99%, especially 100% biobased based on the total weight of the carbon-containing portion of the composition. Preferably, the composition is suitable for vegan consumers.

[0040] Preferably, the amino compound comprises hydrolyzed protein, more preferably consists essentially of hydrolyzed protein, more preferably, the amino compound is 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 can be used. The enzyme is preferably not of animal origin. Preferably, the enzyme is from a microbial source. (Multiple) enzymes can include carbohydrases and / or proteases. Preferably, the enzyme includes a protease. The hydrolysis can be carried out to the extent required to achieve the desired weight average molecular weight of the hydrolyzed protein. The extent of hydrolysis can be changed by changing the temperature, the acid / alkali / enzyme used and the time used. The resulting hydrolyzed protein can be filtered and / or treated to remove undesirable materials. For example, if acid hydrolysis is used, the hydrolyzed protein can be treated to remove any chloride ions present.

[0041] The hydrolyzed protein can be obtained from a natural source. The hydrolyzed protein can be obtained from a renewable source. Preferably, the hydrolyzed protein is obtained from a plant source. The plant source can be selected from potato, wheat, cottonseed, pea, chickpea and soybean, preferably selected from potato, wheat, pea and chickpea, more preferably selected from potato 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 may be advantageous because wheat protein may be undesirable for some consumers.

[0042] Preferably, the amino compound comprises oligomers of amino acids, which may also be referred to as oligopeptides. These oligomers may be hydrolyzed protein fragments. The amino compound may comprise oligomers having an average size of 2 to 20 amino acids (also referred to as residues), preferably oligomers of 2 to 15 amino acids, more preferably oligomers of 2 to 10 amino acids. Preferably, the average size is a weight average size. The amino acids in the oligomer may be identical or different amino acids. The amino acids in the oligomer preferably include at least one glutamic acid residue or histidine residue, more preferably include at least one glutamic acid residue. The amino compound may not be a single amino acid. Preferably, the amino compound is not composed of a single amino acid. Alternatively, the amino compound may include glutamic acid or histidine as a single amino acid, preferably glutamic acid.

[0043] 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 up to 20,000 Da, preferably up to 10,000 Da, preferably up to 8,000 Da, preferably up to 5,000 Da, preferably up to 3000 Da, preferably up to 1500 Da, preferably up to 1000 Da. The molecular weight can be measured by size exclusion chromatography, preferably size exclusion HPLC (SE-HPLC) as described in the test method below. Preferably, the amino compound has a weight average molecular weight in the range of 100 Da to 5000 Da, preferably a weight average molecular weight in the range of 100 Da to 3000 Da, preferably a weight average molecular weight in the range of 100 to 1500 Da.

[0044] Preferably, the composition of the present invention is substantially free of quaternary ammonium compounds. The term "substantially free" is used to mean that the composition comprises preferably less than 10 wt %, more preferably less than 5 wt %, more preferably less than 2 wt % and most preferably less than 1 wt % based on the total weight of the composition. Preferably, the composition does not contain quaternary ammonium compounds.

[0045] Preferably, the composition of the present invention is substantially free of silicone compounds. The term "substantially free" is used to mean that the composition comprises preferably less than 10 wt%, more preferably less than 5 wt%, more preferably less than 2 wt% and most preferably less than 1 wt%, based on the total weight of the composition. Preferably, the composition does not contain silicone compounds. Preferably, the composition does not contain organosilanes, organosilicones or silicone compounds.

[0046] The composition can also include one or more preservatives. The composition can include at least 0.1% by weight preservative based on the gross weight of the composition, preferably at least 0.2% by weight, more preferably at least 0.4% by weight, particularly at least 0.6% by weight. The composition can include at most 10% by weight preservative based on the gross weight of the composition, preferably at most 5% by weight, more preferably at most 3% by weight, particularly at most 2% by weight. The preservative can include phenoxyethanol, benzoate or sorbate, more preferably, the preservative is selected from benzoate and sorbate, more preferably, the preservative includes sodium benzoate and / or potassium sorbate. Alternatively, the composition may not include a preservative.

[0047] The composition may be a liquid at room temperature (25°C). The composition may be a solution or dispersion of the itaconic acid-modified amino compound in a solvent, preferably a solution, and preferably, the solvent comprises water.

[0048] Alternatively, the composition may not contain water, or may contain residual water after drying to a solid or powder form. Spray drying may be used to dry the composition. The composition may be a solid or a powder.

[0049] The ratio of reactants

[0050] The reactants of the composition of the present invention include:

[0051] a) itaconic anhydride; and

[0052] b) an amino compound comprising at least one free amino group, wherein said compound is selected from the group consisting of amino acids, peptides and hydrolyzed proteins;

[0053] The composition comprises an itaconic acid modified amino compound, wherein the itaconic acid modified amino compound is the reaction product of a) and b), and wherein 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 performed by formaldehyde titration as described herein.

[0054] The ratio of reactants can surprisingly affect the properties of the composition of the present invention. In the itaconic acid modified amino compound, 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 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 itaconic anhydride. 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 carried out by formaldehyde titration as described herein.

[0055] Personal care preparations

[0056] Preferably, the composition of the invention is suitable for use in a personal care formulation.Viewed from a second aspect, the invention provides a personal care formulation comprising a composition of the invention. Preferably, the personal care formulation is for topical application to the skin or hair.

[0057] The personal care formulation may be selected from moisturizers, body butters, gel creams, high fragrance content products, balms, conditioners, hair relaxer formulations, shampoos, hair styling products, leave-in hair care products, anhydrous products, antiperspirant and deodorant products, cleansers, two-in-one foaming emulsions, emulsifier-free products, mild formulations, scrub formulations (e.g., scrub formulations containing solid beads), water-in-silicone formulations, pigment-containing products, sprayable emulsions (e.g., hair detanglers), makeup, bath products, make-up removers, eye make-up removers, and wipes. Preferably, the personal care formulation is selected from conditioners, hair relaxer formulations, shampoos, hair styling products, leave-in hair care products, and sprayable emulsions (e.g., hair detanglers).

[0058] Preferably, the composition of the present invention is present in a personal care formulation in 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 a personal care formulation in 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.

[0059] Preferably, the personal care formulation comprises the reaction product of itaconic anhydride and hydrolyzed protein, wherein the personal care formulation comprises 0.01 to 10 wt %, preferably 0.1 to 10 wt % of the reaction product of itaconic anhydride and hydrolyzed protein, based on the total weight of the formulation, and wherein the personal care formulation is suitable for topical application.

[0060] The present invention can provide a personal care formulation comprising the composition of the present invention and a personal care ingredient. The personal care ingredient can be selected from a cleanser, a hair conditioner, a hair styling agent, an antidandruff agent, a hair growth promoter, a fragrance, a pigment, a moisturizer, a film former, a hair dye, a cosmetic, a thickener, an emulsifier, a humectant, an emollient, an antibacterial agent, a deodorant active agent, 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, an adhesive, an enzyme, an enzyme inhibitor, an enzyme activator, a coenzyme, a plant extract, a ceramide, a buffer, a filler, a chelating agent, a cosmetic biocide, an external analgesic, a substantivity increasing agent, a sunscreen, a pH adjusting agent, a reducing agent, a sequestrant, a skin bleaching and / or lightening agent, a skin conditioner, a skin soothing and / or healing agent, a skin treatment agent, a vitamin or a preservative.

[0061] Preferably, the personal care ingredients are selected from cleansers, hair conditioners, skin conditioners, hair styling agents, anti-dandruff agents, hair growth promoters, fragrances, pigments, moisturizers, film formers, humectants, alpha-hydroxy acids, hair dyes, cosmetics, thickeners, antibacterial agents, deodorants, and surfactants.

[0062] Many other personal care ingredients can be used in the personal care formulations according to the present invention. These ingredients can be oil-soluble, water-soluble or insoluble. Examples of such ingredients include:

[0063] (i) a preservative, preferably a preservative approved for cosmetic use, in particular a preservative as listed in Annex 5 of the EU Cosmetics Regulation. The preservative preferably comprises sodium benzoate, potassium sorbate or phenoxyethanol. The preservative may comprise parabens (alkyl esters of 4-hydroxybenzoic acid), substituted urea or hydantoin derivatives, such as those commercially sold under the trade names Germaben II, Nipaguard BPX and Nipaguard DMDMH. The preservative may be used in a concentration ranging from 0.5% to 2% by weight based on the total weight of the formulation;

[0064] (ii) fragrance, when used typically in a concentration ranging from 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 formulation;

[0065] (iii) wetting agents or solvents, such as alcohols, polyols (such as glycerol and polyethylene glycol), usually used in a concentration ranging from 1% to 10% by weight based on the total weight of the formulation;

[0066] (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;

[0067] (v) vitamins and their precursors, including: (a) vitamin A, such as retinyl palmitate and other retinoic acid 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 tocopheryl acetate, (e) vitamin F, such as polyunsaturated fatty acid esters, such as gamma-linolenic acid;

[0068] (vi) skin care agents, such as ceramides, as natural materials or functional mimics of natural ceramides;

[0069] (vii) natural phospholipids, such as lecithin;

[0070] (viii) a preparation containing vesicles;

[0071] (ix) plant extracts having beneficial skin care properties;

[0072] (x) Skin lightening agents such as kojic acid, arbutin and similar materials;

[0073] (xi) Skin repair compound actives such as allantoin and similar series;

[0074] (xii) caffeine and similar compounds;

[0075] (xiii) cooling additives such as menthol or camphor;

[0076] (xiv) Insect repellents, such as N,N-diethyl-3-methylbenzamide (DEET) and citrus or eucalyptus oils;

[0077] (xv) essential oils; and

[0078] (xvi) Pigments, including finely divided pigments, especially oxides and silicates, for example iron oxide (especially coated iron oxide) and / or titanium dioxide, and ceramic materials, such as boron nitride, or other solid components, such as those used in makeup and cosmetics, to provide a suspoemulsion, usually in an amount ranging from 1% to 15% by weight, but usually at least 5% by weight, and especially about 10% by weight, based on the total weight of the formulation.

[0079] Personal care formulations can include spices or materials that impart fragrance to provide a pleasant aroma. In one aspect, spices are provided by natural sources, such as, but not limited to, alfalfa, almonds, amber, angelica root, fennel, apple, apricot, banana, basil, laurel, bay, benzoin, bergamot, bitter orange, black pepper, rosewood (redwood), melaleuca, cardamom, carrot seed, cypress, cinnamon, lemongrass, citrus, sage, cloves, cocoa, coconut, coffee, coriander, cranberry, cypress, elemi, eucalyptus globulus, thyme ... The fragrance is selected from mint, pineapple, raspberry, Roman chamomile, rose, rosemary, sandalwood, spearmint, spruce, strawberry, tea, thyme, vanilla, vetiver, violet, yarrow, ylang-ylang, etc. Preferably, the fragrance is selected from mint or vanilla.

[0080] Preferably, the personal care formulation is a skin care formulation. The present invention may provide a skin care formulation comprising a composition of the present invention and a skin care ingredient. Preferably, the skin care ingredient is as described herein. Preferably, the skin care formulation is for topical application to the skin.

[0081] Preferably, the composition of the present invention is present in a skin care formulation in 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 a skin care formulation in 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.

[0082] Preferably, the personal care formulation is a hair care formulation.The present invention may provide a hair care formulation comprising a composition of the present invention and hair care ingredients.Preferably, the hair care formulation is for topical application to the hair.

[0083] Hair care ingredients can be selected from shine enhancers, moisturizers, herbal additives, hair strengtheners, vitamin additives, colorants, hair thickeners; fixatives and styling agents; UV absorbers; silicone oils; essential oils and fragrances; thickeners or viscosity enhancers; detergents; stabilizers; emollients; chelating agents; multivalent sequestrants; preservatives; disinfectants; antioxidants / free radical scavengers; antistatic agents; conditioning agents; detangling ingredients; emulsifiers or dispersants.

[0084] Preferably, the hair care preparations are hair cleansing, conditioning, detangling, color protection or styling preparations, particularly preferably hair cleansing or conditioning preparations.

[0085] Preferably, the composition of the present invention is present in a hair care formulation in 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 a hair care formulation in 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.

[0086] The formulation may be in the form of an aqueous "leave-on" or aqueous "rinse-off" end-use product. For such formulations, a diluent solution may be used. Preferably, a buffered solution is used, wherein the pH of the solution is adjusted to be slightly acidic, with a pH in the range of 4 to 6. In the case of a rinse-off formulation, instructions are provided to rinse off the diluted formulation after application. Such instructions may also require that the product be left on the hair for a period of time, such as 1 to 30 minutes, depending on the level of treatment desired. For a leave-on formulation, the rinse-off step is omitted.

[0087] In the case where the formulation is a shampoo or conditioner for making hair straighter, the shampoo or conditioner may be in the form of a dispersion, emulsion or solution. A preferred system is one that forms liquid crystals. The liquid crystals are preferably lyotropic (i.e. both concentration and temperature dependent), more preferably lamellar phase liquid crystals, and in particular L-alpha phase (pure) liquid crystals.

[0088] Hair care formulations can contain many different types of hair care ingredients such as;

[0089] (i) Cationic hair conditioning agents, for example ethoxylated phosphate fatty quaternary ammonium salts, such as those marketed by Croda as Arlasilk TM Those marketed as; fatty amidoamines, such as those marketed as Incromine by Croda TM Those marketed as; fatty quaternary ammonium salts, such as those marketed by Croda as Incroquat TM 、Crodazosoft TM , Rejuvasoft TM or VibraRiche TM Those sold as styrofoam are typically used at concentrations ranging from 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 those marketed by Croda as Crodacel TM and MiruStyle TMQuaternized cellulose, quaternized protein (such as Croda as Croquat TM , Crosilkquat TM 、Kerestore TM and Hydrotriticum TM those that are sold).

[0090] (ii) Fatty alcohols, such as stearyl alcohol, cetearyl alcohol, cetyl alcohol, oleyl alcohol, are generally used in a concentration range of 2 wt % to 5 wt % based on the total weight of the formulation.

[0091] (iii) wetting agents or solvents, such as alcohols and polyols (e.g., glycerol and polyethylene glycol), usually used in a concentration ranging from 1% to 10% by weight based on the total weight of the formulation;

[0092] (iv) reconstructors, such as hydrolyzed proteins (e.g. wheat protein), which are used to penetrate the hair and strengthen the hair structure through polymer cross-linking;

[0093] (v) polishing or detangling materials that bind to the hair and reflect light, for example silicones, such as dimethicone, phenyl trimethicone, dimethiconol and / or trimethylsilylamodimethicone, typically in a concentration ranging from 0.2% to 10% by weight based on the total weight of the formulation;

[0094] (vi) acidity regulators, such as citric acid, lactic acid, which typically maintain the pH of the conditioner at about 4 to 6;

[0095] (vii) heat protectants, usually heat absorbing polymers, which protect the hair from overheating (for example caused by a hair dryer or curling iron or hot curling rollers), such as those marketed by Croda as Mirustyle TM Those sold as MFP (quaternized starch); and

[0096] (viii) UV protectants, for protecting the hair or formulation components from UV radiation degradation, such as Crodasorb, marketed by Croda TM Those sold by UV-HPP.

[0097] Shampoo preparations

[0098] A preferred personal care formulation according to the invention is a shampoo comprising from 0.1 to 20% by weight of a composition according to the invention, based on the total weight of the formulation, and further comprising:

[0099] a) at least one surfactant selected from the group consisting of:

[0100] i) anionic surfactants in a total amount of 0.1 to 30 wt. %, preferably 0.5 to 20 wt. %, more preferably 1 to 15 wt. %, more preferably 3 to 10 wt. %, more preferably 5 to 7 wt. %, based on the total weight of the preparation, wherein the at least one anionic surfactant is selected from the group consisting of 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 selected from these anionic surfactants;

[0101] ii) a nonionic surfactant selected from the group consisting of alkanolamides, sugar-based surfactants and ethoxylated surfactants; and

[0102] iii) zwitterionic surfactants, in a total amount of 0.1 to 15 wt%, preferably 0.2 to 10 wt%, more preferably 0.5 to 8 wt%, more preferably 1 to 5 wt%, more preferably 2 to 4 wt%, based on the total weight of the formulation, wherein the zwitterionic surfactant is selected from amphoacetates / amphodiacetates, amine oxides, sulfobetaines and betaines, more preferably, the zwitterionic surfactant comprises cocamidopropyl betaine.

[0103] b) at least one additional hair care ingredient as described herein; and

[0104] c) Water.

[0105] Hair conditioner preparations

[0106] A preferred personal care formulation according to the invention is a rinse-off conditioner comprising from 0.1 to 20 wt. % of a composition according to the invention, based on the total weight of the formulation, and further comprising:

[0107] a) at least one surfactant selected from the group consisting of:

[0108] i) cationic surfactants, in a total amount of 0.01 to 8 wt.%, preferably 0.1 to 6 wt.%, more preferably 0.5 to 5 wt.%, more preferably 1.0 to 4 wt.%, more preferably 1.5 to 3.5 wt.%, relative to the total weight of the formulation, wherein preferably the cationic surfactants are selected from quaternary ammonium compounds having at least one C8-C24 alkyl residue, esterquats having at least one C8-C24 acyl residue and amidoamines,

[0109] ii) a nonionic surfactant selected from the group consisting of alkanolamides, sugar-based surfactants and ethoxylated surfactants;

[0110] b) optionally at least one linear saturated 1-alkanol having 12 to 30 carbon atoms, in a total amount of 0.2 to 10% by weight, particularly preferably 0.5 to 7% by weight, relative to the total weight of the preparation, including at least one linear saturated 1-alkanol selected from the group consisting of lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol and behenyl alcohol, and mixtures selected from these 1-alkanols, and

[0111] c) optionally at least one oil in a total amount of 0.01 to 10% by weight, preferably 0.1 to 3% by weight, particularly preferably 0.5 to 1% by weight, relative to the total weight of the preparation; and

[0112] d) Water.

[0113] Methods of treating hair or skin

[0114] Viewed from a further aspect the invention provides a method of treating the hair or skin comprising the step of applying to the hair or skin a composition according to the invention.

[0115] Preferably, the composition provides a benefit to the hair or skin, and wherein the benefit is selected from cleansing and conditioning.

[0116] Preferably, the composition comprises any of the features described herein in relation to the composition of the invention.

[0117] The method may comprise rinsing the composition from the hair or skin using water. Alternatively, the method may comprise leaving the composition on the hair or skin.

[0118] Viewed from another aspect, the present invention provides a method of treating hair comprising the step of applying to the hair a composition according to the present invention, wherein the composition provides a benefit to the hair, and wherein the benefit is selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improving hair direction, hair volume and styling.

[0119] Preferably the composition is part of a shampoo or conditioner formulation, preferably comprising any of the features described herein.

[0120] Preferably, the composition comprises any of the features described herein in relation to the composition of the invention.

[0121] Use of a composition for treating hair or skin

[0122] Viewed from a further aspect the invention provides the use of a composition according to the invention for treating the hair or skin to provide a benefit to the hair or skin selected from cleansing and conditioning.

[0123] Viewed from a further aspect the invention provides the use of a composition according to the invention for treating hair to provide a benefit to the hair selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improved hair direction, volume and styling.

[0124] Preferably, the composition is part of a shampoo or conditioner formulation, preferably comprising any of the features described herein.

[0125] Preferably, the composition comprises any of the features described herein in relation to the composition of the invention. Example

[0126] The present invention is illustrated by the following non-limiting examples. Unless otherwise stated, all parts and percentages are given by weight.

[0127] It should be understood that unless otherwise stated herein, or unless otherwise stated in the referenced test methods and procedures, all tests and physical properties listed are determined at atmospheric pressure and ambient temperature (i.e., approximately 23°C).

[0128] Test Method

[0129] The following test methods were used in this specification:

[0130] (i) Formaldehyde titration, a titration method for determining the degree of substitution of amino groups, described by Cobbett, WG, Gibbs, JA and Leach, AA (1964). J. Appl. Chem. (London), 14, 296-302.

[0131] (ii) pH was measured at room temperature (25°C) using a Fisher Scientific Accumet AE150 pH meter. Based on the initial pH reading, the pH of the formulation was adjusted to a range of 4.0-5.0 using 10 wt% sodium hydroxide solution (if the pH was higher) or 10 wt% citric acid solution (if the pH was lower). The pH was measured immediately after preparation of the formulation and 24 hours after preparation of the formulation.

[0132] (iii) The active substance content (in % by weight) in the sample is calculated by measuring the total non-volatile content and the ash content. The total non-volatile content measurement is performed on a sample of known weight by oven drying at 105°C for 17-19 hours to remove the moisture and any other volatile components present. After cooling in a desiccator, the residual weight is used to calculate the total non-volatile content (in % by weight) of the sample. For the ash content, a sample of known weight is carefully heated to a temperature of 575–600°C using increasing temperature steps in the presence of air and maintained at temperature for 16–18 hours (or longer if necessary). After cooling in a desiccator, the residual weight is used to calculate the ash content (in % by weight) of the sample. The active substance content (in % by weight) in the sample is then calculated by subtracting the weight % of ash from the weight % of the total non-volatile content.

[0133] (iv) Weight average molecular weight was determined by size exclusion high performance liquid chromatography (SE-HPLC). The HPLC equipment and settings used are provided in Table 1.

[0134] Table 1: HPLC equipment and settings

[0135] (v) Single hair fiber tensile test data were measured in a controlled environment room using a tensile testing machine (MTT690) equipped with an automatic loading system (model ALS1500) and a fiber size analysis system (model FDAS770) from Diastron Ltd. (Andover, Hants, UK). First, 50 random single fibers from each bundle of hair treated with each sample were prepared for testing with an AAS 1600 (automatic assembly system) from Diastron Ltd. Each hair fiber sample had a length specification of 30 mm. The prepared hair fiber sample was then loaded onto a rotating sample tray and pre-balanced for at least 1 hour at 50% relative humidity (RH) and room temperature (~25°C) before the experiment was performed. After pre-balancing, each fiber sample was moved from the sample tray to FDAS770 using ALS1500. FDAS770 uses a laser micrometer to measure the size (cross-sectional area, in square micrometers) of the fiber sample by scanning 5 sections along the fiber length. The fiber sample is then moved back to the sample tray, where a pneumatic rod pulls one end of the fiber sample taut, while a pneumatic jaw equipped with a 2 kg (20 N) load cell grabs the other end of the fiber sample and slowly stretches the hair fiber sample at a stretching rate of 20 mm / min until the fiber reaches the breaking point. At the breaking point, a stress-strain curve is generated for each fiber sample. Data for breaking stress (gmf / square micron) is generated, which is defined as the stress at which the hair fiber will break. Example 1

[0136] The amino compounds used to prepare the compositions of the present invention can be prepared by any of the following methods A to D.

[0137] Method A

[0138] Potato protein concentrate is added to hydrochloric acid solution and mixed until fully dispersed. The resulting dispersion is heated to reflux conditions. The dispersion is heated until the weight average molecular weight of the protein (measured by SE-HPLC as described in the test method) stops decreasing, typically in the range of 200-500 Da. After hydrolysis is complete, the pH of the solution is increased by adding sodium hydroxide. The protein hydrolysate is purified by filtering and treating with activated carbon. After purification, more sodium hydroxide is added to make the solution alkaline, and the solution is concentrated to the desired active substance content (within the range of 20 to 30% by weight active substance content) by evaporation or ultrafiltration, wherein ultrafiltration has the benefit of desalination. The resulting product will be referred to as amino compound A.

[0139] Method B

[0140] Potato protein concentrate is added to the hydrochloric acid solution and mixed until fully dispersed. The resulting dispersion is heated to reflux conditions. The dispersion is heated until the weight average molecular weight of the protein stops decreasing, typically in the range of 200-500 Da. The acidic protein hydrolysate is then recovered by filtration. The pH of the solution is then increased by passing the solution through an ion exchange resin to remove chloride ions. The protein hydrolysate is purified by treating with activated carbon. After purification, more sodium hydroxide is added to make the solution alkaline, and the solution is concentrated to the desired active substance content (within the range of 20 to 30% by weight active substance content). The resulting product will be referred to as amide B.

[0141] Method C

[0142] Potato protein concentrate is added to the water and mixed until fully dispersed. The resulting dispersion is heated to the desired temperature, then sodium hydroxide solution is used to regulate pH. By stirring under the desired temperature and pH range, enzyme (carbohydrase and protease) catalysis of the hydrolysis of potato protein is used to achieve the usual weight average molecular weight of about 400 to 700 Da. After the hydrolysis, the pH of the hydrolysis mixture is reduced to acidity by adding hydrochloric acid solution, and the enzyme is denatured by heating. Purify the protein hydrolysate by filtering and treating with activated carbon. Then sodium hydroxide is used to adjust the hydrolyzed protein solution of the gained dilution to alkaline pH, and then concentrated into the desired active substance content (within the range of 20 to 30% by weight active substance content). Products therefrom will be referred to as amide C.

[0143] Method D

[0144] Potato protein concentrate is added to the water and mixed until fully dispersed. The gained dispersion is heated to the desired temperature, then sodium hydroxide solution is used to regulate pH. By stirring under the desired temperature and pH range, enzyme (carbohydrase and protease) catalysis of the hydrolysis of potato protein is used to realize the common weight average molecular weight of about 700 to 950 Da. After the hydrolysis, the pH of the hydrolysis mixture is reduced to acidity by adding hydrochloric acid solution, and the enzyme is denatured by heating. Purify the protein hydrolysate by filtering and treating with activated carbon. Then sodium hydroxide is used that the hydrolyzed protein solution of the gained dilution is adjusted to alkaline pH, and then concentrated into the desired active substance content (within 20 to 30% by weight active substance content range). Products therefrom will be referred to as amide D. Example 2

[0145] The composition of the present invention is prepared by reacting amino compound A, B, C or D with itaconic anhydride in a suitable container according to the following method:

[0146] 1. Place the amino compound into a container.

[0147] 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 to avoid or reduce the production of itaconic acid.

[0148] 3. Add a calculated amount of itaconic anhydride (calculated by formaldehyde titration, a technique described by Cobbett, WG, Gibbs, JA and Leach, AA (1964). J. Appl. Chem. (London), 14, 296-302). This calculation is based on the reaction proceeding to completion, but some itaconic anhydride may react with water to form itaconic acid and prevent complete reaction of itaconic anhydride with the amino compound. An example of the required calculated amount of itaconic anhydride in grams is, for example, 200 (exemplary weight of amino compound in g) x 55 (exemplary result of formaldehyde titration) x 0.02 (molar concentration of NaOH used in formaldehyde titration) x 112 (molecular weight of itaconic anhydride) x 0.75 (75 mole % of free amino groups required for the reaction) / 1000 (unit conversion).

[0149] 4. During the addition of itaconic anhydride and initiation of the reaction, maintain a temperature of 15-45°C, preferably 20-35°C, and a pH of 9.5-11.0, preferably 10.0-10.5.

[0150] 5. The reaction conditions are maintained for another 1-4 hours (preferably 1-2 hours).

[0151] 6. Acidify with a mineral acid such as hydrochloric acid to pH 3.5-5.5 (preferably 4.0-5.0).

[0152] 7. Preserved by adding preservatives.

[0153] 8. Cool and adjust pH to pH 3.5-5.5 (preferably 4.0-5.0).

[0154] 9. Filter.

[0155] The samples in Table 2 below were prepared using the methods from Examples 1 and 2, with the exception of Sample 1, which had no itaconic acid modification and therefore used only Example 1. All samples were adjusted to between pH 3.5-5.

[0156] Table 2: Prepared samples Example 3

[0157] The hair samples were conditioned and tensile tested using the following procedure:

[0158] a) Bleach European brown, undamaged hair to the desired level of damage using a commercial bleaching system (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach)

[0159] b) Divide a single hair strand into multiple smaller strands to undergo different treatments and compare

[0160] c) Soak each tress in a solution containing 1% (w / w) active substance for 30 minutes.

[0161] d) For control, soak a small hair tress in DI water for 30 minutes

[0162] e) Use a hair dryer to dry each small section of hair using a low heat, high power setting

[0163] 50 fibers were taken from each tress and the Hair Tensile Test data was measured as described above in the Test Methods section.

[0164] The results were compared to a DI water control. The average results are provided in Table 3 below.

[0165] Table 3: Test results of hair treated with no washing

[0166] *Indicates significant improvement compared with the control (Student t test, 95% confidence interval)

[0167] Table 3 shows the increase in breaking stress of hair treated with amino compound B. A further improvement was seen with itaconic acid-modified amino compound A. Hair treated with itaconic acid-modified amino compound A had significantly higher breaking stress compared to the control. Example 4

[0168] The hair samples were conditioned and tensile tested using the following procedure:

[0169] a) Bleach European brown, undamaged hair to the desired level of damage using a commercial bleaching system (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach)

[0170] b) Divide a single hair strand into multiple smaller strands to undergo different treatments and compare

[0171] c) Soak each tress in a solution containing 1% (w / w) active substance for 30 minutes.

[0172] d) For control, soak a small hair tress in DI water for 30 minutes

[0173] e) After 30 minutes, rinse your hair under warm water for 30 seconds

[0174] f) Use a hair dryer to dry each small section of hair using a low heat, high power setting

[0175] 50 fibers were taken from each tress and the Hair Tensile Test data was measured as described above in the Test Methods section.

[0176] The results were compared to a DI water control. The average results are provided in Table 4 below.

[0177] Table 4: Rinse-treated hair test results

[0178] * Indicates significant improvement compared with the control (Student t test, 95% confidence interval)

[0179] Although the hair tresses in Table 4 were rinsed, the results were consistent between Tables 3 and 4. Amino compound B showed improvement compared to the control. Itaconic acid-modified amino compound A showed further improvement, significantly different from the control. Example 5

[0180] The hair samples were conditioned and tensile tested using the following procedure:

[0181] a) Bleach European brown, undamaged hair to the desired level of damage using a commercial bleaching system (Clynol Viton Cream Peroxide 12% and Clynol Viton Blue Powder Bleach)

[0182] b) Divide a single hair strand into multiple smaller strands to undergo different treatments and compare

[0183] c) Soak each tress in a solution containing 1% (w / w) active substance for 30 minutes.

[0184] d) For control, soak a small hair tress in DI water for 30 minutes

[0185] e) Use a hair dryer to dry each small section of hair using a low heat, high power setting

[0186] 50 fibers were taken from each tress and the hair tensile test data was measured as described in the Test Methods section above. Each test (except Sample 7) was repeated with a tress from the same original tress to provide 2 x 50 fibers for each treatment, for a total of 100 fibers.

[0187] The results were compared to a DI water control. The average results are provided in Table 5 below.

[0188] Table 5: Hair test results from different modification levels

[0189] * Indicates significant improvement compared with the control (Student t test, 95% confidence interval)

[0190] # indicates a test of 50 fibers

[0191] Table 5 shows the increase in breaking stress when treating hair with itaconic acid modified hydrolyzed potato protein. The 75% and 90% itaconic acid modified hydrolyzed potato protein showed significant improvement compared to the control.

[0192] It will be appreciated that the invention is not limited to the details of the above embodiments, which have been described by way of example only. Many variations are possible.

Claims

1. A composition comprising the reaction product of: a) itaconic anhydride; and b) an amino compound comprising at least one free amino group, wherein the amino compound is selected from the group consisting of amino acids, peptides and hydrolyzed proteins; wherein the composition comprises an itaconic acid-modified amino compound, wherein the itaconic acid-modified amino compound is the reaction product of a) and b), and wherein 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. A composition according to any one of the preceding claims, further comprising a preservative, preferably selected from benzoates and sorbates.

5. The composition according to any one of the preceding claims, wherein the amino compound is a hydrolyzed protein, preferably a hydrolyzed vegetable protein, preferably a hydrolyzed potato protein.

6. A composition according to any one of the preceding claims, wherein the amino compound is not a single amino acid.

7. A composition according to any one of the preceding claims, wherein the amino compound has a weight average molecular weight in the range of 100 Da to 5000 Da, preferably in the range of 100 Da to 3000 Da, more preferably in the range of 100 to 1500 Da, the weight average molecular weight preferably being measured by size exclusion chromatography.

8. A composition according to any one of the preceding claims which does not comprise organosilane, organosilicon or siloxane compounds.

9. A composition according to any preceding claim which does not contain a quaternary ammonium compound.

10. A personal care formulation comprising a composition according to any one of the preceding claims.

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

12. A hair care formulation comprising a composition according to any one of claims 1 to 9 and additional hair care ingredients.

13. A skin care formulation comprising a composition according to any one of claims 1 to 9 and an additional skin care ingredient.

14. A method of treating hair or skin comprising the step of applying to the hair or skin a composition according to any one of claims 1 to 9.

15. The method of claim 14, wherein the composition provides a benefit to the hair or skin, and wherein the benefit is selected from the group consisting of cleansing and conditioning.

16. A method of treating hair, said method comprising the step of applying to said hair a composition according to any one of claims 1 to 9, wherein said composition provides a benefit to said hair, and wherein said benefit is selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improved hair direction, volume and styling.

17. Use of a composition according to any one of claims 1 to 9 for treating hair or skin to provide a benefit selected from cleansing and conditioning to the hair or skin.

18. Use of a composition according to any one of claims 1 to 9 for treating hair to provide a benefit to the hair selected from hair strengthening, cleaning, conditioning, detangling, repairing, shine, vitality, softness, frizz prevention, cuticle smoothing, elasticity, moisture control, curl retention, heat protection, improved hair direction, volume and styling.

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