HAIR TREATMENTS

FIELD OF THE INVENTION

[0001] The present invention relates to various compositions and methods for treating or preventing damage to hair, especially in over-processed or chemically treated hair.

BACKGROUND OF THE INVENTION

[0002] Human hair is frequently subjected to chemical processes that damage the structural integrity of the hair fiber. Hair is formed from layers of keratin protein which are polymeric, as well as the natural pigments that provide the inherent natural hair color. Due to various beauty and fashion trends, as well as the desire to avoid grey hair, consumers frequently subject their hair to harsh chemical processes such as application of chemicals that are highly reactive and initiate the breaking of intramolecular bonds within keratin, or the destruction of melanin, or both. Popular beauty treatments that involve chemical hair processes including oxidation hair lightening and oxidative hair coloring, during which oxidizing agents such as peroxides, persulfates, and oxidizing enzymes are applied to the hair. Other popular beauty treatments that involve chemical processes are permanent waves and hair relaxers and straighteners, which involve the application of reducing agents such as formaldehyde, lye, and thiol reducing agents such as thioglycolates. These beauty treatments are referred to interchangeably as chemical processes or chemical treatments.

[0003] Because hair constantly grows, new hair growth must be treated to match previously treated hair. Therefore, chemical treatments are often performed several times year, year after year. Hair that repeatedly undergoes chemical treatments is referred to as over processed or damaged hair.

[0004] Hair damage occurs in a number of ways. The oxidizing and reducing agents react with and damage the cuticle which is the exterior layer of dead cells and proteins protecting the cortex of keratin in the hair fiber. The degraded cuticle results in more penetration of oxidizing or reducing chemicals. The damaged cuticle also results in daily assault from environmental UV light, ozone, and moisture all of which further compromise the structural integrity of the hair fiber. Chemical processes also degrade melanin, creating voids in the hair fiber where moisture can diffuse into. Hair fibers, once damaged and with more voids, permit greater diffusion of materials into and out of the hair. Chemical treatment agents penetrate further into the cortex where they react with keratin protein fibrils. Intramolecular keratin bonds are broken, and the keratin proteins degrade into low molecular weight keratin peptide fragments, which are more water soluble. With repeated hair washing the peptide fragments are washed away creating even more porous hair. Over-processed hair becomes increasingly porous with less keratin content compared to virgin untreated hair, has weakened intramolecular bonds, is mechanically compromised, and easily breaks.

[0005] Standard treatment for ameliorating the condition of over-processed hair is to apply topical hair conditioners to the hair on a regular basis. Hair conditioners are products that use hydrophobic fluids, oils, and cationic surfactants to coat the exterior of hair fibers to improve the surface and visual characteristics of the hair.

[0006] Other solutions to treat over-processed hair have been suggested. For example, U.S. Patent No. 3,472,243 describes applying to damaged hair vinyl monomers, along with oxidizing agents to polymerize the monomer inside the hair fiber. Also, U.S. Patent No. 3,634,022 describes applying olefinically unsaturated polymerizable monomers and an effective amount of a peroxide initiator to hair to yield improved hair setting and hair conditioning benefits.

[0007] However, these solutions suffer from several disadvantages. One disadvantage of these compositions and methods is that the in situ polymerization of vinyl monomers produces only polyvinyl polymers, such as polyacrylates. Polyvinyl polymers are stiff fixatives commonly used in coatings and hair sprays. Hair treated with such compositions are stiff and lack the natural bounce and flow of virgin human hair. Furthermore, polyvinyl polymers have only a carbon-carbon backbone, unlike natural keratin with consists of many amide bonds. The existence of polyvinyl polymers inside of hair creates different attractive and repulsive forces compared to the native proteins of hair. Thus, when hair dyes are applied, the hair may not retain the dye in the same manner as natural keratin fibrils.

[0008] Thus, there remains a need for compositions and methods to repair the hair fiber from the inside, to fill voids within fibers, to reduce the porosity of the hair fiber, and increase the hydrophobicity and strength of fibers within the internal hair cortex. By strengthening the internal cortex, hair can withstand repeated chemical oxidation and reduction treatments and maintain structural integrity of the hair fibers.

BRIEF SUMMARY OF THE INVENTION

[0009] Various aspects of the present invention are directed to compositions for treating hair (e.g., damaged hair, over-processed hair, and/or chemically treated hair). In various embodiments, the compositions comprise (a) itaconic acid or a salt, ester, and/or anhydride thereof and (b) a basic amino acid and/or an amino alcohol. For example, the composition can comprise (a) itaconic acid and/or a salt, ester, or anhydride thereof, (b) arginine and/or lysine, and (c) a solvent comprising water, wherein the composition has a concentration of itaconic acid or salt, ester and/or anhydride thereof that is from about 1 wt.% to about 10 wt.% and a concentration of arginine and/or lysine that is from about 0.5 wt.% to about 10 wt.%.

[0010] Further aspects of the present invention are directed to kits for treating hair. In various embodiments, the kits comprise a first monomer component comprising itaconic acid and/or a salt, ester, or anhydride thereof; a second monomer component comprising the basic amino acid and/or amino alcohol; and a hair chemical component comprising an oxidizing agent or precursor thereof.

[0011] Other aspects of the present invention are directed to methods of treating hair fibers. In some embodiments, the methods comprise contacting the hair fibers with a composition comprising itaconic acid or a salt, ester, and/or anhydride thereof and a basic amino acid and/or amino alcohol and then exposing the hair fibers to an oxidizing agent. In further embodiments, the methods comprise contacting the hair fibers with a composition comprising itaconic acid or a salt, ester and/or anhydride thereof and a basic amino acid and/or amino alcohol and an oxidizing agent.

[0012] Still further aspects are directed to processes for preparing various compositions as described herein. In various embodiments, the processes comprise combining (a) itaconic acid and/or a salt, ester, or anhydride thereof and (b) a basic amino acid and/or amino alcohol.

[0013] Other objects and features will be in part apparent and in part pointed out hereinafter.

DETAILED DESCRIPTION OF THE INVENTION

[0014] In general, the present invention is directed to compositions and methods for treating hair and methods of producing these compositions. In particular, various aspects relate to compositions and methods for treating or preventing damage to hair, especially in over processed or chemically treated hair. Applicants have surprisingly discovered that co-polymers of vinyl monomers (e.g., itaconic acid) and an amino acid and/or amino alcohol can be produced in situ (e.g., on the hair fibers) upon application of an oxidizing agent to initiate polymerization. These compositions and methods can provide for improved ability to repair, strengthen and retain dye in the hair. Accordingly, various compositions provided herein comprise (a) itaconic acid or a salt, ester, and/or anhydride thereof and (b) a basic amino acid and/or an amino alcohol. Various methods for treating hair fibers comprise contacting the hair fibers with (a) itaconic acid or a salt, ester, and/or anhydride thereof, (b) a basic amino acid and/or amino alcohol, (c) an oxidizing agent, or any mixture comprising two or more of these ingredients. Additional embodiments are described herein.

Compositions

[0015] As noted, various aspects of the present invention are directed to compositions for treating hair or hair fibers. In various embodiments, the compositions comprise at least two different water-soluble monomers. For instance, the first monomer can be an olefinic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and the second monomer(s) can comprise an amino acid and/or amino alcohol. Accordingly, in some embodiments, the composition comprises (a) itaconic acid and/or a salt, ester, or anhydride thereof and (b) a basic amino acid and/or an amino alcohol.

[0016] In various embodiments, the composition has a concentration of the olefinic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) that is about 0.1 wt.% or greater, about 1 wt.% or greater, about 2 wt.% or greater, about 5 wt.% or greater, about 10 wt.% or greater, or about 20 wt.% or greater. For example, in some embodiments, the composition can have a concentration of olefinic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) that is from about 0.1 wt.% to about 20 wt.%, from about 0.1 wt.% to about 10 wt.%, from about 0.1 wt.% to about 7.5 wt.%, from about 0.1 wt.% to about 5 wt.%, from about 0.1 wt.% to about 2.5 wt.%, from about 1 wt.% to about 20 wt.%, from about 1 wt.% to about 10 wt.%, from about 1 wt.% to about 7.5 wt.%, from about 1 wt.% to about 5 wt.%, or from about 1 wt.% to about 2.5 wt.%.

[0017] Further, in various embodiments, the composition has a concentration of the basic amino acid and/or amino alcohol that is about 0.5 wt.% or greater, about 1 wt.% or greater, about 2 wt.% or greater, about 5 wt.% or greater, about 10 wt.% or greater, or about 20 wt.% or greater. For example, in certain embodiments, the composition has a concentration of the basic amino acid and/or amino alcohol that is from about 0.5 wt.% to about 20 wt.%, from about 0.5 wt.% to about 15 wt.%, from about 0.5 wt.% to about 10 wt.%, from about 0.5 wt.% to about 7.5 wt.%, from about 1 wt.% to about 20 wt.%, from about 1 wt.% to about 15 wt.%, from about 1 wt.% to about 10 wt.%, from about 1 wt.% to about 7.5 wt.%, from about 5 wt.% to about 20 wt.%, from about 5 wt.% to about 15 wt.%, from about 5 wt.% to about 10 wt.%, or from about 5 wt.% to about 7.5 wt.%. [0018] In some embodiments, the weight of basic amino acid and/or an amino alcohol in the composition is greater than the weight of the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof). For example, the weight ratio of the basic amino acid and/or amino alcohol to the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) can be about 1.5:1 or greater, about 2:1 or greater, about 3 : 1 or greater, about 4:1 or greater, about 5: 1 or greater, about 10: 1 or greater, or about 20: 1 or greater. In these and other embodiments, the weight ratio of the basic amino acid and/or amino alcohol to the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) is from about 1 : 1 to about 50:1, from about 1:1 to about 25:1, from about 1:1 to about 10:1, from about 1:1 to about 5:1, from about 1: 1 to about 3:1, from about 3: 1 to about 50:1, from about 3: 1 to about 25:1, from about 3 : 1 to about 10 : 1 , or from about 3 : 1 to about 5:1.

[0019] In further embodiments, the weight of the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) in the composition is greater than the weight of the basic amino acid and/or an amino alcohol. For example, the weight ratio of the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) to the basic amino acid and/or amino alcohol is about 1.5 : 1 or greater, about 2: 1 or greater, about 3 : 1 or greater, about 4: 1 or greater, about 5: 1 or greater, about 10: 1 or greater, or about 20: 1 or greater. In these and other embodiments, the weight ratio of olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) to the basic amino acid and/or amino alcohol is from about 1 : 1 to about 50:1, from about 1:1 to about 25:1, from about 1:1 to about 10:1, from about 1:1 to about 5:1, from about 1: 1 to about 3:1, from about 3: 1 to about 50:1, from about 3: 1 to about 25:1, from about 3 : 1 to about 10 : 1 , or from about 3 : 1 to about 5:1.

[0020] As noted, in various embodiments, the composition can comprise itaconic acid and/or a salt, ester, or anhydride thereof (e.g., the olefmic monomer comprises or consists of itaconic acid and/or a salt, ester, or anhydride thereof). In some embodiments, the composition comprises itaconic acid or salt thereof. In various embodiments, the composition comprises itaconic acid.

[0021] As noted, the composition comprises a basic amino acid and/or an amino alcohol. In various embodiments, the composition comprises the basic amino acid. In some embodiments, the basic amino acid comprises arginine, lysine, and/or histidine. In certain embodiments, the basic amino acid comprises arginine and/or lysine. In various embodiments, the basic amino acid comprises, consists essentially of (e.g., the basic amino acid is 95 wt.% or more, or even 99 wt.% or more arginine), or consists of arginine. In some embodiments, the basic amino acid comprises, consists essentially of (e.g., the basic amino acid is 95 wt.% or more, or even 99 wt.% or more arginine), or consists of lysine.

[0022] In various embodiments, the composition comprises the amino alcohol. In some embodiments, the amino alcohol comprises at least one alcohol selected from the group consisting of triethanolamine, diethanolamine, monoethanolamine, 2-amino-2 -methyl- 1- propanyl, and combinations thereof. In certain embodiments, the composition comprises a combination of the basic amino acid and amino alcohol.

[0023] In various embodiments, the compositions described herein can have a pH of about 7 or less, about 6.5 or less, about 6 or less, about 5.5 or less, about 5 or less, about 4.5 or less, about 4 or less, or about 3 or less. In some embodiments, the compositions described herein can have a pH of from about 3 to about 7, from about 3 to about 6, from about 3 to about 5, from about 3 to about 4, from about 4 to about 7, from about 4 to about 6, or from about 4 to about 5.

[0024] In various embodiments, the compositions described herein further comprise a solvent. For example, the solvent can comprise an aqueous solvent (e.g., the solvent can comprise, consist essentially of (e.g., water is 95 wt.% or more, or even 99 wt.% or more of the solvent), or consist of water). When prepared as a solution, the total amount of monomers in solution can be about 10 wt.% or less or from about 1 wt.% to about 10 wt.%. For example, when the solvent is water, the total concentration of (a) itaconic acid and/or a salt, ester, or anhydride thereof and (b) basic amino acid, and/or amino alcohol can be less than about 10 wt.% or from about 1 wt.% to about 10 wt.%.

[0025] As noted, it has been discovered that the two or more monomers as described herein (e.g., itaconic acid and the amino acid and/or amino alcohol) can advantageously polymerize in situ to form flexible but strong polymers that can strengthen hair fibers and ameliorate hair damage due to chemical treatments. In various embodiments, an oxidizing agent is used to induce polymerization in the hair fibers. Accordingly, in some embodiments, the compositions described herein further comprise an oxidizing agent or precursor thereof. In certain embodiments, the oxidizing agent comprises a conventional chemical used in hair treatment formulations to change the color of the hair fibers.

[0026] In various embodiments, the oxidizing agent can comprise at least one chemical selected from the group consisting of hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts (e.g., persulfates, perborates, peracids and precursors thereof as well as percarbonates of alkali metals or alkaline earth metals) and combinations thereof. In some embodiments, the oxidizing agent comprises at least one chemical selected from the group consisting of hydrogen peroxide, persulfates, and combinations thereof. In various embodiments, the oxidizing agent is provided as a conventional or commercial hair treatment composition (e.g., a dyeing composition, bleaching paste, or other chemical treatment).

[0027] The compositions can be formulated in various suitable forms including, for example, low to moderate viscosity liquids, lotions, milks, mousses, sprays, gels, creams, shampoos, conditioners, and the like. In various embodiments, the compositions described herein are formulated as a hair conditioner or shampoo. Various compositions described herein can be applied to hair fibers prior to exposure of the hair fibers to the oxidizing agent.

[0028] The compositions described herein may further comprise one or more additives (e.g., cosmetically acceptable ingredients). Examples of cosmetically acceptable ingredients are those listed in the International Cosmetic Ingredient Dictionary and Handbook and those listed in the United States Pharmacopeia. Cosmetically acceptable ingredients include, but are not limited to preservatives, antioxidants, chelating agents, sunscreen agents, vitamins, dyes, hair coloring agents, proteins, amino acids, natural extracts such as plant extracts, humectants, fragrances, perfumes, oils, emollients, lubricants, butters, penetrants, thickeners, viscosity modifiers, polymers, resins, hair fixatives, film formers, surfactants, detergents, emulsifiers, opacifying agents, volatiles, propellants, liquid vehicles, carriers, salts, pH adjusting agents (e.g., citric acid), neutralizing agents, buffers, hair conditioning agents, anti-static agents, anti-frizz agents, anti-dandruff agents, absorbents, and combinations thereof.

[0029] For example, surfactants include various anionic, cationic, nonionic, and amphoteric surfactants. Anionic surfactants include, but are not limited to, those containing carboxylate, sulfonate and sulfate ions. Examples of anionic surfactants include sodium, potassium, ammonium of long chain alkyl sulfonates and alkyl aryl sulfonates. Cationic surfactants include, but are not limited to, quaternary ammonium compounds such as benzalkonium chloride, benzethonium chloride, cetrimonium bromide, stearyl dimethylbenzyl ammonium chloride, polyoxyethylene and coconut amine. Examples of nonionic surfactants include ethylene glycol monostearate, propylene glycol myristate, glyceryl monostearate, glyceryl stearate, polyglyceryl-4-oleate, sorbitan acylate, sucrose acylate, PEG-150 laurate, PEG-400 monolaurate, polyoxyethylene monolaurate, polysorbates, polyoxyethylene octylphenylether, PEG- 1000 cetyl ether, polyoxyethylene tridecyl ether, polypropylene glycol butyl ether, Poloxamer® 401, stearoyl monoisopropanolamide, and polyoxyethylene hydrogenated tallow amide. Examples of amphoteric surfactants include sodium N-dodecyl-b- alanine, sodium N-lauiyl-P-iminodipropionate, myristoamphoacetate, lauiyl betaine and lauryl sulfobetaine. Emollients include, for example, silicone compounds, polyols (e.g., propanediol), and triglycerides

[0030] Emulsifiers include, but are not limited to, copolymers of an unsaturated ester and styrene sulfonate monomer, cetearyl alcohol, glyceryl ester, polyoxyethylene glycol ether of cetearyl alcohol, stearic acid, polysorbate-20, ceteareth-20, lecithin, glycol stearate, polysorbate- 60, polysorbate-80, and combinations thereof.

[0031] Preservatives include, but are not limited to, glycerin containing compounds, benzyl alcohol, parabens, sodium benzoate, ethylenediamine-tetraacetic acid (EDTA), potassium sorbate, and so on. Antioxidants include, for example, tocopheryls, BHT, ascorbic acid, camellia sinensis leaf extract, ascorbyl palmitate, magnesium ascorbyl phosphate, carotenoids, resveratrol, triethyl citrate, arbutin, kojic acid, tetrahexydecyl ascorbate, superoxide dismutase, zinc, sodium metabisulfite, lycopene, ubiquinone, and combinations thereof.

[0032] Conditioning agents include, for example, silicone-based agents, panthenol, hydrolyzed wheat and/or soy protein, amino acids, rice bran wax, meadowfoam seed oil, mango seed oil, grape seed oil, jojoba seed oil, sweet almond oil, hydroxyethyl behenamidopropyl dimonium chloride, aloe leaf extract, aloe barbadensis leaf juice, phytantriol, panthenol, retinyl palmitate, behentrimonium methosulfate, cyclopentasiloxane, quatemium-91, stearamidopropyl dimethylamine, and combinations thereof.

[0033] Viscosity modifying agents include, for example, viscous liquids, such as polyethylene glycol, semisynthetic polymers, cellulose derivatives, synthetic polymers, naturally occurring polymers, bentonite, colloidal silicon dioxide, and microcrystalline cellulose, and salts, such as sodium chloride, and combinations thereof.

[0034] Opacifying agents include, but are not limited to, glycol distearate and ethoxylated fatty alcohols.

[0035] In some embodiments, the compositions described herein comprise at least one of a viscosity modifier (e.g., xanthan gum or equivalent), a preservative (e.g., phenoxyethanol), an emollient (e.g., propanediol), a conditioning agent (e.g., stearamidopropyl dimethylamine, behentrimomium methosulfate, and/or sunflower oil), or an emulsifier (e.g., cetearyl alcohol). In certain embodiments, the composition comprises itaconic acid, arginine, cetearyl alcohol, behentrimonium methosulfate, stearamidopropyl dimethylamine, sunflower oil, xanthan gum, propanediol, and phenoxyethanol. Kits

[0036] Various aspects of the present invention also include kits for treating hair. In various embodiments, a kit for treating hair comprises: a first monomer component comprising an olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof); a second monomer component comprising the basic amino acid and/or amino alcohol; and a hair chemical component comprising an oxidizing agent or precursor thereof. The amount of the oxidizing agent in the hair chemical component is sufficient to effectively polymerize the first and second monomer components to provide the intended protective/repairing effects.

[0037] Features relating to the compositions described herein can apply to any of the components of the kits. For example, the oxidizing agent can comprise at least one chemical selected from the group consisting of hydrogen peroxide, urea peroxide, alkali metal bromates, ferricyanides, peroxygenated salts, persulfates, and combinations thereof. Also, the components of the kit can include additives as described herein.

[0038] In some embodiments, the first monomer component and the second monomer component are present as a premixed composition. In certain embodiments, the premixed composition is a composition as described herein.

[0039] In other embodiments, the first monomer component and the second monomer component are separate compositions (e.g., in separate packaging or containers within the kit).

[0040] In various embodiments the kit contains more than one container (or more than one compartment in a given container) to avoid mixing of the oxidizing agent or precursor thereof with the monomer components before use.

[0041] The kit may further include a developer bottle, gloves, shampoo, and/or conditioner. Instructions for use of the kit can also be included.

Method of Use

[0042] Further aspects of the present invention are directed to methods for treating hair fibers. In general, the methods comprise contacting hair fibers with a composition as described herein. As detailed below, the compositions described herein that comprise (a) the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and (b) the amino acid and/or amino alcohol may be applied to hair fibers before, simultaneously with, and/or after application of an oxidizing agent. When the compositions are applied simultaneously with the oxidizing agent, they may be applied as a single formulation (e.g., comprising itaconic acid, an amino acid and/or amino alcohol, and the oxidizing agent). [0043] In various embodiments, the methods comprise contacting hair fibers with a composition comprising (a) the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and (b) the amino acid and/or amino alcohol as described herein and exposing the hair fibers treated with the composition to an oxidizing agent (e.g., contacting the hair fibers to an oxidizing agent). In some embodiments, the methods comprise contacting hair fibers with a hair treatment composition comprising (a) the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and (b) the amino acid and/or amino alcohol, and (c) an oxidizing agent (e.g., a premixed composition of (a), (b), and (c)).

[0044] It is believed that the monomers in the compositions described herein can react in the presence of the oxidizing agent to form a co-polymer. Ideally, this reaction can occur within or inside a hair fiber. For example, within a hair fiber, keratin polymers can act as a molecular sieve, forming a catalytic environment where many possible reaction structures are possible. For example, when a basic amino acid such as arginine is used, the arginine can be oxidized by the oxidizer to form hydroxyl -arginine. In turn, hydroxyl -arginine can condense with the carboxylic acid groups of the olefmic monomer (e.g., itaconic acid) to form ester and amide bonds. Therefore, the copolymers formed in the hair may include, but are not limited to, polyesters, polyamides, polyester-amides, and copolymers of the esters and amides with oligomeric polyolefin. The polymerization reaction may produce a variety of copolymer structures.

[0045] In various embodiments, the hair fibers are contacted with compositions comprising the monomers (e.g., itaconic acid and amino acid and/or amino alcohol) before exposing the hair to an oxidizing agent.

[0046] As noted herein, in various embodiments, the oxidizing agent can comprise hydrogen peroxide, urea peroxide, a persulfate, alkali metal bromates or ferricyanides, peroxygenated salts (e.g., persulfates, perborates, peracids, and precursors thereof and percarbonates of alkali metals or of alkaline-earth metals). In some embodiments, the oxidizing agent is provided in a hair treatment formulation comprising a dye, a bleaching composition, or other oxidizing hair treatment components.

[0047] In other embodiments, the oxidizing agent can be UV light (e.g., sunlight). For example, in various embodiments, the methods can comprise contacting the hair fibers with a composition comprising itaconic acid or a salt, ester and/or anhydride thereof and a basic amino acid and/or amino alcohol, as described above, and then exposing the hair fibers to UV light. In other embodiments, the hair fibers might be pre-treated with the composition comprising itaconic acid or a salt, ester and/or anhydride thereof and a basic amino acid and/or amino alcohol prior to a hair treatment procedure (e.g., bleaching, dyeing, relaxing). Any of the compositions described above can be used in these methods.

[0048] In various embodiments, the compositions are aqueous compositions and may be applied to the hair by any means suitable (e.g., spraying, dripping, drenching, etc.). In some embodiments, the monomers are incorporated into a hair conditioning product and applied to the hair before, during and/or following exposure to the oxidizing agent.

[0049] In various embodiments, the monomers (e.g., itaconic acid and the basic amino acid and/or amino alcohol) can be added to a water phase of a hair conditioner emulsion. The hair conditioning emulsion may further comprise one or more additives as described above.

[0050] As noted, in various embodiments, the methods comprise contacting hair fibers with a hair treatment composition comprising (a) the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and (b) the amino acid and/or amino alcohol, and (c) an oxidizing agent (e.g., a premixed composition of (a), (b), and (c)). In some embodiments, these methods further comprise combining the oxidizing agent with the composition comprising (a) the olefmic monomer (e.g., itaconic acid and/or a salt, ester, or anhydride thereof) and (b) the amino acid and/or amino alcohol to form the hair treatment composition. For example, an oxidizing agent (e.g., hydrogen peroxide, persulfate or equivalent) can be combined with a composition comprising the itaconic acid and an amino acid and/or amino alcohol as described above to form the hair treatment composition. These hair treatment compositions can be applied to the hair within a relatively short period after forming the compositions. For example, the hair treatment compositions can be applied to the hair fibers within about 2 hours, within about 1 hour, within about 30 minutes, within about 20 minutes, within about 10 minutes, or within about 5 minutes of forming the hair treatment composition.

[0051] In various embodiments described herein, the methods of treating hair can further comprise exposing the hair fibers to UV light.

[0052] The compositions and methods described herein can have beneficial and restorative properties for hair fibers. Accordingly, in various embodiments, the methods of treating hair fibers described herein can comprise protecting or mitigating damage induced by the oxidizing agent. In some embodiments, the methods of treating hair fibers can comprise repairing damage to the hair fibers. In various embodiments, the methods of treating hair fibers can comprise increasing hydrophobicity, decreasing porosity, and/or increasing dye retention of the hair fibers. In certain embodiments, the methods of treating hair fibers can also comprise chemically treating the hair fibers. For example, the methods of treating can comprise bleaching, dyeing or relaxing the hair fibers.

[0053] In various embodiments, the methods comprise combining a composition as described herein with a bleaching compound to form a bleaching composition and contacting the hair fibers with the bleaching composition. In some embodiments, the methods comprise combining a composition as described herein with an oxidative hair dye to form a dyeing composition and contacting the hair fibers with the dyeing composition. In certain embodiments, the methods comprise combining a composition as described herein with a hair relaxing agent to form a hair relaxing composition and contacting the hair fibers with the hair relaxing composition.

[0054] In certain embodiments, the methods described herein can comprise contacting the hair fibers with itaconic acid and arginine.

Processes of Preparing the Compositions

[0055] Still further aspects are directed to processes for preparing various compositions described herein. In various embodiments, the processes comprise combining (a) itaconic acid and/or a salt, ester, or anhydride thereof and (b) a basic amino acid and/or amino alcohol. The processes can further comprise combining one or more other ingredients as described herein with the a) itaconic acid and/or a salt, ester, or anhydride thereof, (b) a basic amino acid and/or amino alcohol, or any mixture thereof.

[0056] All percentages are by weight of the total composition unless specifically stated otherwise. When more than one composition is used during a treatment, the total weight to be considered is the total weight of all the compositions applied on hair simultaneously (i.e. the weight found “on head”) unless otherwise specified. All ratios are weight ratios unless specifically stated otherwise.

[0057] As used herein the terms “hair” and “hair fibers” to be treated may be “living” (i.e., on a living body) or may be “non-living” (i.e., in a wig, hairpiece or other aggregation of non-living keratinous fibers). Mammalian hair, particularly human hair is preferred. However wool, fur and other keratin containing fibers are suitable substrates for the compositions according to the present invention.

[0058] Having described the invention in detail, it will be apparent that modifications and variations are possible without departing from the scope of the invention defined in the appended claims. EXAMPLES

[0059] The following non-limiting examples are provided to further illustrate the present invention.

Example 1: Treating over-processed bleached hair.

[0060] Over-processed hair was created by subjecting virgin human black hair tresses to repeated bleaching with a conventional salon bleaching system: a 40 volume developer (hydrogen peroxide) and a persulfate oxidizing powder manufactured by L'Oreal. The bleaching treatment was applied following the manufacturer’s instructions and was repeated four times, each time for two hours, until all natural black melanin pigment was oxidized to a blond color and the hair fibers were noticeably damaged. The over-processed hair tresses were subjected to a final hair bleaching process per the manufacturer’s instructions.

[0061] For Tress 1, a 10 ml of aqueous test composition was added to the bleaching paste immediately prior to application on the hair. The aqueous test composition contained 6.5 wt.% itaconic acid and 2.0 wt.% arginine.

[0062] For Tress 2, the final bleaching was performed without any hair repair solution.

[0063] For Tress 3, a comparative hair repair solution, which contains maleic acid, was added to the bleaching paste immediately prior to application on the hair.

[0064] After the final bleaching and drying of the hair tresses, an expert hair technician combed each tress 10 times. The technician’s evaluation is reported in Table 1. Tress 1 with the test composition was smooth and shiny, with all fibers aligning with each other with little breakage. Tress 2, with no repair solution, exhibited frizz with many hairs having lost their natural curl. Tress 2 was also significantly more damaged. Combing Tress 2 resulted in significant breakage. Tress 3, which used the comparative hair repair solution, had less natural curl and noticeably more breakage than Tress 1 with the test composition.

Table 1. Example 2: Increased hydrophobicity and faster drying.

[0065] Tress 1 and Tress 2 obtained from Example 1 were wetted with equal quantities of distilled water and immediately hung to air dry. After 1 hour, the tresses were weighed to determine the amount of water remaining in the fibers. Tress 1, which had previously been treated with the test composition, had 50% of its water remaining in it. Tress 2, which had not been treated with any hair repair solution, had 62% of its water remaining in it. This example demonstrates that the test composition made the hair of Tress 1 less porous and more hydrophobic, which resulted in faster hair drying.

Example 3: Retention of hair dye after oxidative hair dyeing.

[0066] Hair tresses were dyed using a conventional oxidative hair dye in the shade of red following the manufacturer’s instructions. With Tress 1, 10 ml of the test composition was added to the hair dying paste. With Tress 2, no hair repair solution was added to the dying pastes. After the hair was dyed and left to air dry, both hair tresses were washed by hand with equal amounts of a consumer shampoo product. The foam from each tress washing was retained. The foam samples were photographed, and analyzed by colorimetric software (Image Analysis Summarizer vO.76). The colorimetry results using the L*a*b system of the International Commission on Illumination are reported in Table 2.

[0067] In this system, larger L values indicate a lighter color intensity, whereas larger a values indicate a greater red color, and larger b values indicate a greater yellow color. The reported results are the median value of all pixels in the photos of the foam. Tress 1, which was treated with the test composition, had greater color fastness and less washout of color by shampoo. Washout foam from Tress 2, which was not treated with the test composition, was significantly darker (lower L value) and was more red and yellow (larger a and b values) indicating quantitatively that more red dye was being washed out by the shampoo.

Table 2.

Example 4: Inventive composition applied to hair and exposed to UV light.

[0068] Three women, whose history of hair treatments including decades of chemical treatments such as bleaching, dying, and relaxing, and reported to have damaged hair, applied the composition of Table 3 to their hair, and left the composition on for a minimum of 3 hours. The composition of Table 3 is a hair conditioning emulsion that contains the inventive combination of itaconic acid and arginine. The three subjects exposed their hair to direct daylight for some or all the period of testing. All three subjects reported significant improvement in hair quality, less frizz, and easier ability to comb their hair.

Table 3.

[0069] When introducing elements of the present invention or the preferred embodiments(s) thereof, the articles "a", "an", "the" and "said" are intended to mean that there are one or more of the elements. The terms "comprising", "including" and "having" are intended to be inclusive and mean that there may be additional elements other than the listed elements.

[0070] In view of the above, it will be seen that the several objects of the invention are achieved and other advantageous results attained.

[0071] As various changes could be made in the above compositions, methods, and processes without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.