WO2021101946A1 - Traitements capillaires - Google Patents

Traitements capillaires Download PDF

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Publication number
WO2021101946A1
WO2021101946A1 PCT/US2020/060981 US2020060981W WO2021101946A1 WO 2021101946 A1 WO2021101946 A1 WO 2021101946A1 US 2020060981 W US2020060981 W US 2020060981W WO 2021101946 A1 WO2021101946 A1 WO 2021101946A1
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WO
WIPO (PCT)
Prior art keywords
composition
hair
salt
ester
anhydride
Prior art date
Application number
PCT/US2020/060981
Other languages
English (en)
Inventor
Daniel Winn
Lorraine LAMPE
Original Assignee
Actera Ingredients, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Actera Ingredients, Inc. filed Critical Actera Ingredients, Inc.
Publication of WO2021101946A1 publication Critical patent/WO2021101946A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81—Preparation or application process involves irradiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • the present invention relates to various compositions and methods for treating or preventing damage to hair, especially in over-processed or chemically treated hair.
  • 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.
  • 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.
  • 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.
  • hair can withstand repeated chemical oxidation and reduction treatments and maintain structural integrity of the hair fibers.
  • compositions for treating hair e.g., damaged hair, over-processed hair, and/or chemically treated hair.
  • 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.
  • 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.%.
  • kits for treating hair 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.
  • 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.
  • 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.
  • Still further aspects are directed to processes for preparing various compositions as described herein.
  • 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 present invention is directed to compositions and methods for treating hair and methods of producing these compositions.
  • various aspects relate to compositions and methods for treating or preventing damage to hair, especially in over processed or chemically treated hair.
  • co-polymers of vinyl monomers e.g., itaconic acid
  • 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.
  • 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 for treating hair or hair fibers comprise at least two different water-soluble monomers.
  • 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.
  • 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.
  • 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.
  • the olefinic monomer e.g., itaconic acid and/or a salt, ester, or anhydride thereof
  • 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.%.
  • olefinic monomer e.g., itaconic acid and/or a salt, ester, or an
  • 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.
  • 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.%.
  • 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).
  • the weight ratio of the basic amino acid and/or amino alcohol to the olefmic monomer 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.
  • the weight ratio of the basic amino acid and/or amino alcohol to the olefmic monomer 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • the composition comprises itaconic acid or salt thereof.
  • the composition comprises itaconic acid.
  • the composition comprises a basic amino acid and/or an amino alcohol.
  • the composition comprises the basic amino acid.
  • the basic amino acid comprises arginine, lysine, and/or histidine.
  • the basic amino acid comprises arginine and/or lysine.
  • 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.
  • 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.
  • the composition comprises the amino alcohol.
  • 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.
  • the composition comprises a combination of the basic amino acid and amino alcohol.
  • 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.
  • the compositions described herein further comprise a solvent.
  • 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).
  • the total amount of monomers in solution can be about 10 wt.% or less or from about 1 wt.% to about 10 wt.%.
  • 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.%.
  • the two or more monomers as described herein can advantageously polymerize in situ to form flexible but strong polymers that can strengthen hair fibers and ameliorate hair damage due to chemical treatments.
  • an oxidizing agent is used to induce polymerization in the hair fibers.
  • the compositions described herein further comprise an oxidizing agent or precursor thereof.
  • the oxidizing agent comprises a conventional chemical used in hair treatment formulations to change the color of the hair fibers.
  • 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.
  • the oxidizing agent comprises at least one chemical selected from the group consisting of hydrogen peroxide, persulfates, and combinations thereof.
  • the oxidizing agent is provided as a conventional or commercial hair treatment composition (e.g., a dyeing composition, bleaching paste, or other chemical treatment).
  • 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.
  • 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.
  • compositions described herein may further comprise one or more additives (e.g., cosmetically acceptable ingredients).
  • 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
  • surfactants include various anionic, cationic, nonionic, and amphoteric surfactants.
  • Anionic surfactants include, but are not limited to, those containing carboxylate, sulfonate and sulfate ions.
  • 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.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • Opacifying agents include, but are not limited to, glycol distearate and ethoxylated fatty alcohols.
  • 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).
  • 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
  • an emulsifier e.g., cetearyl alcohol
  • the composition comprises itaconic acid, arginine, cetearyl alcohol, behentrimonium methosulfate, stearamidopropyl dimethylamine, sunflower oil, xanthan gum, propanediol, and phenoxyethanol. Kits
  • kits 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.
  • 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.
  • the components of the kit can include additives as described herein.
  • the first monomer component and the second monomer component are present as a premixed composition.
  • the premixed composition is a composition as described herein.
  • the first monomer component and the second monomer component are separate compositions (e.g., in separate packaging or containers within the kit).
  • 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.
  • the kit may further include a developer bottle, gloves, shampoo, and/or conditioner. Instructions for use of the kit can also be included.
  • 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.
  • the compositions 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).
  • 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).
  • 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).
  • 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)).
  • 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)).
  • the monomers in the compositions described herein can react in the presence of the oxidizing agent to form a co-polymer.
  • this reaction can occur within or inside a hair fiber.
  • keratin polymers can act as a molecular sieve, forming a catalytic environment where many possible reaction structures are possible.
  • a basic amino acid such as arginine
  • the arginine can be oxidized by the oxidizer to form hydroxyl -arginine.
  • hydroxyl -arginine can condense with the carboxylic acid groups of the olefmic monomer (e.g., itaconic acid) to form ester and amide bonds.
  • 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.
  • 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.
  • the monomers e.g., itaconic acid and amino acid and/or amino alcohol
  • 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).
  • the oxidizing agent is provided in a hair treatment formulation comprising a dye, a bleaching composition, or other oxidizing hair treatment components.
  • the oxidizing agent can be UV light (e.g., sunlight).
  • 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.
  • 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.
  • the compositions are aqueous compositions and may be applied to the hair by any means suitable (e.g., spraying, dripping, drenching, etc.).
  • the monomers are incorporated into a hair conditioning product and applied to the hair before, during and/or following exposure to the oxidizing agent.
  • the monomers e.g., itaconic acid and the basic amino acid and/or amino alcohol
  • the hair conditioning emulsion may further comprise one or more additives as described above.
  • 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)).
  • 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.
  • an oxidizing agent e.g., hydrogen peroxide, persulfate or equivalent
  • 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.
  • 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.
  • the methods of treating hair can further comprise exposing the hair fibers to UV light.
  • 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.
  • 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.
  • the methods described herein can comprise contacting the hair fibers with itaconic acid and arginine.
  • Still further aspects are directed to processes for preparing various compositions described herein.
  • 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.
  • 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.
  • wool, fur and other keratin containing fibers are suitable substrates for the compositions according to the present invention.
  • Example 1 Treating over-processed bleached hair.
  • 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.
  • 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.
  • 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.
  • Example 2 Increased hydrophobicity and faster drying.
  • 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.
  • Example 4 Inventive composition applied to hair and exposed to UV light.
  • 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.

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Abstract

L'invention concerne diverses compositions et méthodes pour traiter ou prévenir des dommages causés aux cheveux, en particulier sur des cheveux sur-traités ou traités chimiquement.
PCT/US2020/060981 2019-11-18 2020-11-18 Traitements capillaires WO2021101946A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024002818A1 (fr) * 2022-06-28 2024-01-04 Croda International Plc Composition, formulations de soins personnels, procédé et utilisation pour traiter ou prévenir des dommages aux cheveux

Citations (7)

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Publication number Priority date Publication date Assignee Title
WO2000071658A1 (fr) * 1999-05-26 2000-11-30 The Procter & Gamble Company Compositions detergents comprenant des renforçateurs de savonnage polymeres offrant une plus grande douceur et une meilleure sensation au contact de la peau
US7531008B2 (en) * 2005-11-30 2009-05-12 L'oreal S.A. Use of at least one cationic cyanin derivative for dyeing the hair, composition containing it, process for treating keratin fibers using the composition, and device therefor
US8668745B2 (en) * 2010-12-17 2014-03-11 Henkel Ag & Co. Kgaa Brightening agent comprising acylpyridinium compounds and defined alkalizing agents
US20150313816A1 (en) * 2012-11-09 2015-11-05 L'oreal Composition comprising a dicarbonyl compound and an acid, the process for straightening keratin fibres using this composition
WO2017197931A1 (fr) * 2016-05-19 2017-11-23 知识产权全资产有限公司 Ingrédient et procédé pour le renforcement des cheveux
US20170340553A1 (en) * 2016-05-31 2017-11-30 Henkel Ag & Co. Kgaa Paste-like bleaching agent and method for gentle oxidative hair lightening
US20180369099A1 (en) * 2015-12-08 2018-12-27 Clariant International Ltd. Oligoester Ammonium Salts And Their Use In Compositions For Conditioning Hair

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071658A1 (fr) * 1999-05-26 2000-11-30 The Procter & Gamble Company Compositions detergents comprenant des renforçateurs de savonnage polymeres offrant une plus grande douceur et une meilleure sensation au contact de la peau
US7531008B2 (en) * 2005-11-30 2009-05-12 L'oreal S.A. Use of at least one cationic cyanin derivative for dyeing the hair, composition containing it, process for treating keratin fibers using the composition, and device therefor
US8668745B2 (en) * 2010-12-17 2014-03-11 Henkel Ag & Co. Kgaa Brightening agent comprising acylpyridinium compounds and defined alkalizing agents
US20150313816A1 (en) * 2012-11-09 2015-11-05 L'oreal Composition comprising a dicarbonyl compound and an acid, the process for straightening keratin fibres using this composition
US20180369099A1 (en) * 2015-12-08 2018-12-27 Clariant International Ltd. Oligoester Ammonium Salts And Their Use In Compositions For Conditioning Hair
WO2017197931A1 (fr) * 2016-05-19 2017-11-23 知识产权全资产有限公司 Ingrédient et procédé pour le renforcement des cheveux
US20170340553A1 (en) * 2016-05-31 2017-11-30 Henkel Ag & Co. Kgaa Paste-like bleaching agent and method for gentle oxidative hair lightening

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024002818A1 (fr) * 2022-06-28 2024-01-04 Croda International Plc Composition, formulations de soins personnels, procédé et utilisation pour traiter ou prévenir des dommages aux cheveux

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