WO2025129285A1 - Compositions and methods for improving penetration of active agents for keratin fibers - Google Patents

Compositions and methods for improving penetration of active agents for keratin fibers Download PDF

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Publication number
WO2025129285A1
WO2025129285A1 PCT/BR2023/050474 BR2023050474W WO2025129285A1 WO 2025129285 A1 WO2025129285 A1 WO 2025129285A1 BR 2023050474 W BR2023050474 W BR 2023050474W WO 2025129285 A1 WO2025129285 A1 WO 2025129285A1
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Prior art keywords
chosen
betaine
composition
acid
salts
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PCT/BR2023/050474
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French (fr)
Inventor
Pedro Henrique CARVALHO
João Paulo Duarte GUIMARAES
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LOreal SA
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LOreal SA
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Priority to PCT/BR2023/050474 priority Critical patent/WO2025129285A1/en
Priority to FR2404732A priority patent/FR3157127B3/en
Publication of WO2025129285A1 publication Critical patent/WO2025129285A1/en
Anticipated expiration legal-status Critical
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362Polycarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/002Preparations for repairing the hair, e.g. hair cure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners

Definitions

  • the present disclosure relates to compositions and methods for improving penetration of agents for treating keratin fibers, for example agents for repairing damaged hair fibers, providing strength to hair fibers, and/or reducing elasticity of hair fibers.
  • compositions and processes to change or enhance the appearance of their hair, e.g., by changing the color, style, and/or shape of the hair, and/or by imparting various properties to hair, such as shine and conditioning.
  • many compositions and processes for changing the appearance of the hair such as compositions and processes for permanently altering the color or shape of the hair, involve harsh chemical treatments.
  • repeated styling can lead to damaged hair, for example due to repeated use of heat and styling tools. All of these processes can break bonds within the hair fibers, which if not reformed results in damaged hair.
  • hair lightening and dyeing compositions and processes generally require the presence of a strong alkalizing agent such as ammonia, as well as additional compounds such as oxidizing agents.
  • a strong alkalizing agent such as ammonia
  • additional compounds such as oxidizing agents.
  • these components must first break down the natural components in the hair fibers.
  • hair straightening, relaxing, and permanent waving compositions also involve harsh chemicals to change the shape of the hair by breaking the disulfide bonds in the hair fibers.
  • consumers desire hair that is strong, does not break easily, is able to be stretched or manipulated while retaining the ability to return to its original state without breakage (i.e., has decreased elasticity), and that feels soft and healthy to the touch and also appears shiny and healthy.
  • compositions that satisfactorily address these issues has proven to be challenging.
  • some compositions that attempt to address the problem simply coat the hair with compounds that can improve the feel and appearance of the hair; however, this approach is only temporary and superficial. Instead of preventing or repairing hair damage, this approach simply masks the damage until the hair is next rinsed or washed.
  • Other compositions attempt to address the damage within the hair fiber, but to date have not been satisfactory. This is believed to be, in part, due to ineffective penetration of active agents into the hair fibers, for example hair that has been subject to application of treatment compositions, resulting in a build-up of such compositions on the surface of the hair fiber.
  • compositions comprising one or more of these components, in combination with active agents, exhibit surprisingly reduced signs of damage including greater strength and/or decreased elasticity, in particular hair that has been damaged by harsh chemical treatments such as bleaching, dyeing, permanent waving, straightening, relaxing, etc.
  • the present disclosure relates to compositions and methods for improving penetration of active agents into keratin fibers, for example active agents for preventing, minimizing, or repairing hair damage such as damage caused by harsh chemical compositions and processes.
  • the disclosure relates to compositions for treating keratin fibers, such as hair, the compositions comprising at least one penetration-enhancing solvent and at least one active agent.
  • the penetration-enhancing solvent(s) may be chosen from polyols
  • the active agent(s) may be chosen from amino acids, osmolytes, and/or carboxylic acids.
  • compositions comprise (a) at least one penetration-enhancing solvent chosen from diols and/or triols, (b) at least one amino acid and/or salt thereof, (c) at least one osmolyte, and (d) at least one carboxylic acid and/or salt thereof.
  • compositions comprise (a) at least one penetration-enhancing solvent chosen from polyols such as, for example, C2-C8 diols and/or C2-C8 triols, for example glycols, (b) at least one amino acid chosen from compounds of formula (I) and/or salts thereof, (c) at least one osmolyte chosen from carbohydrates, polyamines, and/or compounds of formula (II), and (d) at least one carboxylic acid and/or salt thereof.
  • polyols such as, for example, C2-C8 diols and/or C2-C8 triols, for example glycols
  • amino acid chosen from compounds of formula (I) and/or salts thereof for example glycols
  • osmolyte chosen from carbohydrates, polyamines, and/or compounds of formula (II)
  • carboxylic acid and/or salt thereof at least one carboxylic acid and/or salt thereof.
  • compositions comprise (a) at least one penetration-enhancing solvent chosen from C2-C8 diols and/or C2-C8 triols, for example glycols, (b) at least one basic amino acid and/or a salt thereof, (c) at least one osmolyte chosen from carbohydrate sugars, polyamines, and/or betaines, preferably at least one betaine chosen from compounds of formula (II), and (d) at least one carboxylic acid and/or salt thereof.
  • penetration-enhancing solvent chosen from C2-C8 diols and/or C2-C8 triols, for example glycols
  • at least one basic amino acid and/or a salt thereof for example glycols
  • at least one osmolyte chosen from carbohydrate sugars, polyamines, and/or betaines, preferably at least one betaine chosen from compounds of formula (II)
  • betaines preferably at least one betaine chosen from compounds of formula (II)
  • compositions comprise (a) at least one penetration-enhancing solvent chosen from glycols, for example propylene glycol and/or dipropylene glycol, (b) arginine and/or a salt thereof, (c) at least one compound of formula (II), and (d) at least one carboxylic acid and/or salt thereof.
  • the pH of the compositions is generally less than 7, such as less than about 6, for example ranging from about 2 to about 5, or from about 3 to about 4.
  • the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition.
  • the penetration-enhancing solvents comprise at least one polyol.
  • the penetration-enhancing solvents may comprise, consist essentially of, or consist of C2-C16 diols and/or C2-C16 triols, for example C2- C8 diols and/or C2-C8 triols.
  • the penetration-enhancing solvents may comprise, consist essentially of, or consist of glycols, for example propylene glycol and/or dipropylene glycol.
  • compositions comprise at least one amino acid chosen from basic amino acids, for example arginine, histidine, lysine, salts thereof, or combinations thereof.
  • the total amount of basic amino acids and salts thereof ranges from about 0.1% to about 15%, preferably from about 1 % to about 12%, more preferably from about 2% to about 10%, more preferably still from about 3% to about 7%, and most preferably from about 4% to about 6% by weight, relative to the total weight of the composition.
  • compositions comprise at least one amino acid chosen from acidic or neutral amino acids and salts thereof, for example serine.
  • the total amount of acidic and/or neutral amino acids and salts thereof ranges from about 0.01 % to about 5%, preferably from about 0.05% to about 4%, more preferably from about 0.1 % to about 3%, and most preferably from about 0.25% to about 2.5% by weight, relative to the total weight of the composition.
  • the compositions comprise a mixture of basic, acidic, and/or neutral amino acids, for example the compositions may comprise arginine and serine.
  • the total amount of amino acids and salts thereof present in the composition ranges from about 0.1 % to about 15%, preferably from about 1 % to about 12%, more preferably from about 2% to about 10%, more preferably still from about 3% to about 7%, and most preferably from about 4% to about 6% by weight, relative to the total weight of the composition.
  • compositions according to the disclosure comprise one or more amino acids chosen from glycine, proline, methionine, serine, arginine, lysine, histidine, salts of any of the foregoing (in particular alkali metal, alkaline earth metal, or zinc salts), and combinations of two or more thereof.
  • the compositions comprise at least one osmolyte chosen from carbohydrate sugars, methylsulfonium compounds, polyamines, and/or amino acid derivatives such as betaines, preferably chosen from compounds of formula (II).
  • the total amount of osmolytes present in the composition ranges from about 0.01 % to about 10%, preferably from about 1 % to about 5%, more preferably from about 1 .25% to about 4%, more preferably still from about 1 .5% to about 3%, and most preferably from about 2% to about 2.5% by weight, relative to the total weight of the composition.
  • the composition has a weight ratio of the total amount of amino acids to the total amount of osmolytes that is equal to or greater than about 0.5, such as greater than about 1 , preferably ranging from about 1.25 to about 3.5, more preferably from about 1.5 to about 3, more preferably still from about 1.75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
  • the compositions comprise at least one carboxylic acid chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, maleic acid, lactic acid, salts thereof, or combinations of two or more thereof, and preferably citric acid, lactic acid, salts thereof, or combinations of two or more thereof.
  • the total amount of carboxylic acids and salts thereof may range from about 0.5% to about 20%, preferably from about 1% to about 15%, more preferably from about 2% to about 12%, more preferably still from about 3% to about 10%, and most preferably from about 4% to about 7% by weight, relative to the total weight of the composition.
  • the composition has a weight ratio of the total amount of amino acids and salts thereof to the total amount of carboxylic acids and salts thereof of greater than about 0.5, such as greater than about 0.7, preferably ranging from about 0.75 to about 2, and more preferably from about 0.8 to about 1 .5.
  • compositions may further comprise water and/or at least one nonaqueous solvent in addition to the penetration-enhancing solvent(s).
  • the compositions comprise water and at least one additional non-aqueous solvent.
  • the compositions may optionally also include at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations of two or more thereof.
  • the compositions comprise (a) at least one penetration-enhancing solvent chosen from glycols, for example propylene glycol, dipropylene glycol, or mixtures thereof, (b) at least one basic amino acid, for example arginine and/or salts thereof, (c) from about 1 % to about 5% of glycine betaine, (d) at least one carboxylic acid, for example citric acid and/or salts thereof, (e) water, and (f) optionally serine, wherein the total amount of penetration-enhancing solvents ranges from about 8% to about 40%, wherein the total amount of basic amino acids ranges from about 1 % to about 10%, and wherein all amounts are by weight, relative to the total weight of the composition.
  • a penetration-enhancing solvent chosen from glycols, for example propylene glycol, dipropylene glycol, or mixtures thereof
  • at least one basic amino acid for example arginine and/or salts thereof
  • glycine betaine from about 1 % to about 5%
  • the pH of the compositions is generally less than 7, for example ranging from about 2 to about 5, or from about 3 to about 4.
  • the compositions have a weight ratio of the total amount of basic amino acids to glycine betaine of greater than 1 , preferably from about 1 .25 to about 3.5, more preferably from about 1 .5 to about 3, more preferably still from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
  • the compositions have a weight ratio of the total amount of basic amino acids to the total amount of carboxylic acids of greater than about 0.75, preferably ranging from about 0.75 to about 2, more preferably from about 0.8 to about 1.5.
  • the compositions may comprise at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations thereof.
  • the amount of serine can range from about 0.01 % to about 2%, preferably from about 0.05% to about 1 .5%, more preferably from about 0.05% to about 1 %, and most preferably from about 0.05% to about 0.5% by weight, relative to the total weight of the composition.
  • compositions may have a weight ratio of the total amount of basic amino acids to serine of greater than about 2, preferably ranging from about 2 to about 15, more preferably from about 4 to about 14, more preferably still from about 6 to about 13, and most preferably from about 8 to about 12, and/or a weight ratio of glycine betaine to serine of greater than about 2, preferably ranging from about 2 to about 10, more preferably from about 3 to about 8, more preferably still from about 3.5 to about 7, and most preferably from about 4 to about 6.
  • compositions comprise (a) at least one penetration-enhancing solvent, (b) at least one amino carboxylic acid or a salt thereof, preferably chosen from arginine and/or a salt thereof, (c) at least one betaine derivative, preferably chosen from glycine betaine, (d) at least one carboxylic acid, preferably chosen from citric acid, lactic acid, and/or salts thereof, and (e) water.
  • the composition may comprise (a) at least one penetration-enhancing solvent chosen from propylene glycol, dipropylene glycol, or mixtures thereof, (b) from about 4% to about 6% of arginine, (c) from about 1 .5% to about 3.5% of glycine betaine, (d) at least one carboxylic acid, (e) water, and (f) optionally serine, wherein the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30%, and wherein all amounts are by weight, relative to the total weight of the composition.
  • penetration-enhancing solvent chosen from propylene glycol, dipropylene glycol, or mixtures thereof
  • the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably
  • the pH of the compositions is generally less than 7, for example ranging from about 2 to about 5, or from about 3 to about 4.
  • the compositions have a weight ratio of the amount of arginine to glycine betaine of greater or equal to about 5, such as greater than 1 , preferably from about 1 .25 to about 3.5, more preferably from about 1 .5 to about 3, more preferably still from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
  • the compositions have a weight ratio of the amount of arginine to the total amount of carboxylic acids of greater than or equal to about 0.5 or greater than about 0.7, preferably ranging from about 0.75 to about 2, more preferably from about 0.8 to about 1 .5.
  • the compositions may comprise at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations thereof.
  • the amount of serine can range from about 0.01 % to about 2%, preferably from about 0.05% to about 1.5%, more preferably from about 0.05% to about 1%, and most preferably from about 0.05% to about 0.5% by weight, relative to the total weight of the composition.
  • compositions may have a weight ratio of the amount of arginine to serine of greater than about 2, preferably ranging from about 2 to about 15, more preferably from about 4 to about 14, more preferably still from about 6 to about 13, and most preferably from about 8 to about 12, and/or a weight ratio of glycine betaine to serine of greater than about 2, preferably ranging from about 2 to about 10, more preferably from about 3 to about 8, more preferably still from about 3.5 to about 7, and most preferably from about 4 to about 6.
  • the disclosure also relates to methods of treating keratin fibers, preferably hair, comprising applying a composition according to the disclosure to the keratin fibers.
  • the methods may, for example, be methods of reducing, preventing, and/or repairing damage, and/or may be methods of improving the overall general health and appearance of the hair.
  • the disclosure further relates to methods of enhancing penetration of at least one active agent into keratin fibers, the methods comprising including at least one penetration-enhancing solvent in a composition comprising the active agent(s), wherein the at least one penetration-enhancing solvent is chosen from polyols, preferably diols and/or triols, for example propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, or mixtures of two or more thereof, and the at least one active agent is chosen from amino acids, osmolytes, carboxylic acids, or combinations of two or more thereof.
  • the at least one penetration-enhancing solvent is chosen from polyols, preferably diols and/or triols, for example propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether
  • FIGS. 1A-1 B are graphs showing the elasticity of hair fibers of swatches S1 -S8 after one treatment (1A) and five treatments (1 B).
  • FIGS. 2A-2B are graphs showing the elasticity of hair fibers of swatches S9-S16 after one treatment (2A) and five treatments (2B).
  • FIG. 3 is a graph showing the elasticity of hair fibers of swatches S17- S21 after five treatments.
  • FIGS. 4A-4B are graphs showing the break stress of hair fibers treated with compositions according to the disclosure and comparative compositions.
  • FIGS. 5A-5B show the structures of certain exemplary osmolytes that can be included in compositions according to the disclosure.
  • compositions and methods for improving penetration of active agents for treating keratin fibers, such as hair for example active agents for repairing damaged keratin fibers, providing strength to keratin fibers, and/or reducing elasticity of keratin fibers.
  • the compositions comprise at least one penetration-enhancing solvent and at least one active agent.
  • the methods comprise enhancing penetration of active agents into keratin fibers as well as treating keratin fibers, e.g., hair, with the compositions.
  • compositions according to the present disclosure comprise at least one penetration-enhancing solvent and at least one active agent.
  • compositions according to the disclosure comprise at least one penetration-enhancing solvent chosen from polyols. These solvents have been surprisingly discovered to be particularly effective at improving penetration of active agents into the hair fibers, even in the presence of build-up of treatment or styling products on the surface of the hair fibers.
  • the polyols can be chosen from diols and triols. In other embodiments, the polyols can be chosen from C2-C16 polyols, such as C2- C12 polyols, C2-C8 polyols, or C3-C8 polyols. In various embodiments, the polyols that can be used are linear or branched, saturated or unsaturated, and substituted or unsubstituted polyols.
  • one or more polyols can be chosen from C2-C16, C2-C12, C2-C8, or C3-C8 diols, or C2-C16, C2-C12, C2-C8, or C3-C8 triols, any of which may be linear or branched, saturated or unsaturated, and substituted or unsubstituted.
  • polyols such as isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl, and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol may be chosen.
  • the polyols are chosen from propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, 1 ,2,6- hexanetriol, 1 ,2,4-butanetriol, trimethylolpropane, 2-butene-1 ,4-diol, 2-ethyl-1 ,3- hexanediol, 2-methyl-2,4-pentanediol, caprylyl glycol, 1 ,2-hexanediol, 1 ,2-pentanediol, 2-ethyl-2-methyl-1 ,3-propanediol, 3,3-dimethyl-1 ,2-butanediol, 2,2-diethyl- 1 ,3- propanediol, 2-methyl-2-propyl-1 ,3-propanedii
  • the polyols are chosen from glycols such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, 1 ,3-propanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, caprylyl glycol, glycerin, diglycerin, and combinations of two or more thereof.
  • glycols such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, 1 ,3-propanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, caprylyl glycol, glycerin, diglycerin, and combinations of two or more thereof.
  • the penetration-enhancing solvent comprises at least one polyol chosen from propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, glycerin, or combinations of two or more thereof.
  • the penetration-enhancing solvent comprises, consists essentially of, or consists of one or more C2-C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols.
  • the penetration-enhancing solvent comprises, consists essentially of, or consists of one or more glycols, for example propylene glycol and/or dipropylene glycol, and in particularly preferred embodiments, the penetrationenhancing solvent comprises, consists essentially of, or consists of dipropylene glycol.
  • the total amount of penetration-enhancing solvents may vary, and in various embodiments may range from about 2% to about 65%, such as, for example, from about 4% to about 60%, from about 6% to about 55%, from about 8% to about 50%, from about 9% to about 45%, from about 10% to about 40%, from about 12% to about 38%, or from about 15% to about 35% by weight, relative to the total weight of the composition.
  • the total amount of penetration enhancing solvents may range from about 2% to about 20%, such as, for example, from about 4% to about 16%, from about 6% to about 14%, from about 8% to about 12%, or from about 9% to about 1 1% by weight, relative to the total weight of the composition.
  • the total amount of penetration enhancing solvents may range from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition.
  • the compositions comprise at least about 5%, such as at least about 8%, or at least about 10% of penetration-enhancing solvent(s).
  • the total amount of penetrationenhancing solvents may range from about 5% to about 50%, such as from about 8% to about 45%, from about 8% to about 40%, from about 8% to about 35%, from about 8% to about 30%, from about 8% to about 25%, from about 10% to about 45%, from about 10% to about 40%, from about 10% to about 35%, from about 10% to about 30%, from about 10% to about 25%, from about 12% to about 45%, from about 12% to about 40%, from about 12% to about 35%, from about 12% to about 30%, from about 12% to about 25%, from about 15% to about 45%, from about 15% to about 40%, from about 15% to about 35%, from about 15% to about 30%, from about 15% to about 25%, from about 18% to about 45%, from about 18% to about 40%, from about 18% to about 35%, from about 18% to about 30%, or from about 18% to about 25% by weight, relative to the total weight of the composition.
  • the total amount of penetration-enhancing solvents may range from about 5% to about 15%, such as from about 5% to about 14%, about 5% to about 13%, about 5% to about 12%, about 5% to about 11 %, about 5% to about 10%, about 6% to about 15%, about 6% to about 14%, about 6% to about 13%, about 6% to about 12%, about 6% to about 1 1 %, about 6% to about 10%, about 7% to about 15%, about 7% to about 14%, about 7% to about 13%, about 7% to about 12%, about 7% to about 1 1 %, about 7% to about 10%, about 8% to about 15%, about 8% to about 14%, about 8% to about 13%, about 8% to about 12%, about 8% to about 1 1 %, about 8% to about 10%, about 9% to about 15%, about 9% to about 14%, about 9% to about 13%, about 9% to about 12%, about 9% to about 1 1 %, or about 8% to about 10%
  • the penetration-enhancing solvent comprises propylene glycol, dipropylene glycol, glycerin, or a mixture of two or more thereof, and the total amount of penetration-enhancing solvents ranges from about 5% to about 40%, preferably from about 8% to about 35% or about 10% to about 30%, or ranges from about 2% to about 20%, such as from about 4% to about 18%, from about 5% to about 15%, or from about 7% to about 14% by weight, relative to the total weight of the composition.
  • the penetration-enhancing solvent consists of or consists essentially of propylene glycol, dipropylene glycol, glycerin, or a mixture of two or more thereof, and the total amount of penetrationenhancing solvents ranges from about 5% to about 40%, preferably from about 8% to about 35% or about 10% to about 30%, or ranges from about 2% to about 20%, such as from about 4% to about 18%, from about 5% to about 15%, or from about 7% to about 14% by weight, or is about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 1 1 %, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21 %, about 22%, about 23%, about 24%, or about 25% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • the penetration-enhancing solvent comprises, consists essentially of, or consists of C2-C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols, and the total amount of penetrationenhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition.
  • the penetration-enhancing solvent comprises, consists essentially of, or consists of C2- C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols, and the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition.
  • compositions according to the disclosure comprise at least one active agent.
  • Active agents that can be used include amino acids, osmolytes, carboxylic acids, and combinations of two or more thereof.
  • the compositions comprise at least one osmolyte, at least one amino acid, and at least one carboxylic acid.
  • compositions according to the disclosure comprise at least one amino acid.
  • compositions according to the disclosure can comprise one, two, or three amino acids.
  • Amino acids that can be chosen include those that are basic, acidic, or neutral at neutral pH. In preferred embodiments, compositions include at least one basic amino acid.
  • amino acid includes amino carboxylic acids and salts thereof as well as amino sulfonic acids and salts thereof.
  • Amino carboxylic acids that may be chosen include, for example, alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, and combinations of two or more thereof.
  • amino sulfonic acids include aminomethane sulfonic acid, 2-aminoethane sulfonic acid (taurine), aminopropane sulfonic acid, aminobutane sulfonic acid, aminohexane sulfonic acid, aminoisopropyl sulfonic acid, aminododecyl sulfonic acid, aminobenzene sulfonic acid, aminotoluene sulfonic acid, sulfanilic acid, chlorosu Ifani lie acid, diamino benzene sulfonic acid, amino phenol sulfonic acid, amino propyl benzene sulfonic acid, amino hexyl benzene sulfonic acid, and combinations of two or more thereof.
  • Salts of amino acids are also included in the term “amino acid,” whether or not so stated.
  • salts that may be chosen include salts with organic or mineral bases, for example the salts of alkali metals, such as the lithium, sodium, or potassium salts; the salts of alkaline earth metals, such as the magnesium or calcium salts, and the zinc salts.
  • amino acids can be in either the D-, L-, or DL- configuration.
  • it is advantageous to choose amino acids in the L- configuration for example L-proline, L-methionine, L-serine, L-arginine, L-lysine, or combinations of two or more thereof.
  • R forms, together with the nitrogen atom, a saturated heterocycle comprising 5 ring members, this ring not being substituted.
  • the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of arginine and/or salts thereof. In other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of histidine and/or salts thereof. In still other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of lysine and/or salts thereof. In still further embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of basic amino acids and/or salts thereof.
  • the total amount of amino acids may range from about 0.1 % to about 15%, such as about 0.1 % to about 12%, about 0.1% to about 10%, about 0.1 % to about 9%, about 0.1 % to about 8%, about 0.1 % to about 7%, about 0.1 % to about 6%, about 0.1 % to about 5.5%, about 0.1 % to about 5%, about 0.1 % to about 4.5%, about 0.1% to about 4%, about 0.1 % to about 3.5%, about 0.1 % to about 3%, about 0.1 % to about 2.5%, about 0.1 % to about 2%, about 0.1 % to about 1 .5%, about 0.1% to about 1%, about 0.5% to about 15%, about 0.5% to about 12%, about 0.5% to about 10%, about 0.5% to about 9%, about 0.5% to about 8%, about 0.5% to about 7%, about 0.5% to about 6%, about 0.5% to about 5.5%, about 0.5% to about 5%, about 0.5% to about 5%, about
  • the total amount of amino acids ranges from about 2.5% to about 7.5%, about 3% to about 7%, about 3.5% to about 6.5%, about 3.75% to about 6.25%, about 4% to about 6%, about 4.25% to about 5.75%, about 4.5% to about 5.5%, about 4.75% to about 5.25%, or about 4.8% to about 5.2% by weight, relative to the total weight of the composition.
  • the total amount of amino acids may be about 4.5%, about 4.6%, about 4.7%, about 4.8%, about 4.9%, about 5.0%, about 5.1 %, about 5.2%, about 5.3%, about 5.4%, or about 5.5% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • the compositions comprise a total amount of basic amino acids in any of the foregoing ranges and amounts.
  • the compositions comprise arginine and/or a salt thereof.
  • arginine is present in the composition in an amount greater than the combined amounts of the other amino acid(s) present, for example arginine comprises greater than about 50%, such as greater than about 60%, greater than about 70%, greater than about 80%, greater than about 90%, greater than about 95%, greater than about 98%, or greater than about 99% of all amino acids present in the composition.
  • arginine is the only the basic amino acid in the composition.
  • the composition comprises arginine in an amount ranging from about 1 % to about 10%, such as from about 2.5% to about 7.5%, preferably from about 3% to about 7%, more preferably from about 3.5% to about 6.5%, more preferably from about 3.75% to about 6.25%, more preferably from about 4% to about 6%, more preferably from about 4.25% to about 5.75%, more preferably still from about 4.5% to about 5.5%, yet more preferably from about 4.75% to about 5.25%, and most preferably from about 4.8% to about 5.2%, or may be present in an amount of about 4.5%, about 4.6%, about 4.7%, about 4.8%, about 4.9%, about 5.0%, about 5.1 %, about 5.2%, about 5.3%, about 5.4%, or about 5.5% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • compositions according to the disclosure comprise serine and/or a salt thereof.
  • the amount of serine may range from about 0.01% to about 2%, such as from about 0.01 % to about 1 .5%, about 0.01 % to about 1 %, about 0.01 % to about 0.5%, about 0.01% to about 0.4%, about 0.01 % to about 0.3%, about 0.01% to about 0.2%, about 0.01 % to about 0.1 %, about 0.05% to about 2%, about 0.05% to about 1.5%, about 0.05% to about 1 %, about 0.05% to about 0.5%, about 0.05% to about 0.4%, about 0.05% to about 0.3%, about 0.05% to about 0.2%, about 0.05% to about 0.1 %, about 0.1 % to about 2%, about 0.1 % to about 1 .5%, about 0.1 % to about 1 %, or about 0.1 % to about 0.5% by weight, relative to the total weight of the composition.
  • the compositions may comprise serine in an amount ranging from about 0.05% to about 1 .5%, preferably from about 0.1 % to about 1 %, more preferably from about 0.25% to about 0.75%, and most preferably from about 0.4% to about 0.6%, such as about 0.1 %, about 0.25%, about 0.5%, about 0.75%, or about 1% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • the composition may be advantageous to choose at least one basic amino acid and at least one additional amino acid chosen from acidic and/or neutral amino acids.
  • the composition may have a weight ratio of the total amount of basic amino acids to the total amount of serine ranging from about 2 to about 15, such as from about 4 to about 14, from about 6 to about 13, from about 8 to about 12, or from about 9 to about 11 .
  • the weight ratio of the total amount of basic amino acids to serine may be about 8, about 9, about 10, about 1 1 , or about 12.
  • the composition comprises serine and has a weight ratio of the total amount of basic amino acids to serine ranging from about 2 to about 15, preferably from about 8 to about 12, more preferably from about 9 to about 1 1 , or is about 8, about 9, about 10, about 1 1 , or about 12, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • compositions comprise serine and arginine, and have a weight ratio of arginine to serine ranging from about 2 to about 15, preferably from about 8 to about 12, more preferably from about 9 to about 1 1 , or is about 8, about 9, about 10, about 1 1 , or about 12, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • Osmolytes are molecules, typically of lower molecular weight, used by cells to maintain cell volume, regulate osmotic pressure, and maintain cellular homeostasis, for example in response to environmental stressors.
  • Organic osmolytes include amino carboxylic acids, amino sulfonic acids, salts thereof, and derivatives thereof, carbohydrates such sugars and sugar alcohols (polyols), polyamines, betaines, methylsulfonium compounds (e.g., dimethylsulfonopropionate), and urea.
  • “osmolytes” includes derivatives of amino carboxylic acids, derivatives of amino sulfonic acids, and salts of the derivatives (referred to herein collectively as “amino acid derivatives”), but does not include amino carboxylic acids, amino sulfonic acids, or salts thereof which are described above, and does not include polyols.
  • compositions according to the disclosure comprise one or more osmolytes, preferably one or more organic osmolytes. In some embodiments, the compositions comprise more than one osmolyte. Without intending to be bound by theory, it is believed that the use of osmolytes as active agents in compositions according to the disclosure permits treated hair to maintain moisture equilibrium, thus reducing potential damage to the hair, or restores moisture equilibrium to already- damaged hair, thereby allowing the treated hair to recover strength and/or reduced elasticity associated with healthy hair.
  • compositions according to the disclosure comprise one or more osmolytes chosen from carbohydrate sugars, polyamines, amino acid derivatives such as betaines, and more preferably are chosen from compounds of formula (II) or salts thereof:
  • R1 , R2, and R3 are independently chosen from C1 -C4 alkyl groups, preferably C1 -C2 alkyl groups, more preferably methyl;
  • A is N or S; m and n are independently 0 or 1 ;
  • Useful and non-limiting polyamine compounds may comprise primary and/or secondary and/or tertiary and/or quaternary amine functional groups.
  • polyamines that can be chosen include diamines, triamines, tetramines, pentamines, and polymeric polyamines or polyimines, such as, for example, hexamethylenediamine, diethylenetetramine, diethylenetriamine, polyethyleneimine (PEI), polyvinyl amine, polyether amine, polylysine, ethylene diamine, 1 ,3- diaminopropane, cadaverine, spermidine, spermine, putrescine, tetraethylmethylenediamine, triethylenetetramine, or combinations of two or more thereof.
  • useful polyamines are chosen from putrescine, spermidine, and/or spermine.
  • betaines include glycine betaine, valine betaine, alanine betaine, proline betaine, hydroxyproline betaine, etc. Salts of betaines can also be used and are expressly included in the term “betaine” unless expressly stated otherwise.
  • betaines are chosen from those corresponding to formula (II).
  • Exemplary useful compounds of formula (II) include the compounds shown in FIGS. 5A-5B. As shown in FIG. 5A, in some embodiments the compounds of formula (II) are in zwitterionic form, and as shown in FIG. 5B, in some embodiments the compounds of formula (II) have a corresponding counterion, X’.
  • the counterion is not limited, and can be any suitable counterion, for example a chloride ion, bromide ion, iodide ion, sulfate anion, sulfonate anion, methyl sulfate anion, phosphate anion, nitrate anion, etc.
  • a “compound of formula (II)” expressly includes both the ionic form of the compound as well as salt forms, whether or not so stated.
  • exemplary useful compounds of formula (II) include betaine and betaine derivatives (referred to herein as “betaines”), for example valine betaine, glutamic acid betaine, glutamine betaine, trimethyl lysine, glycine betaine (trimethyl glycine), histidine betaine, N-methyl histidine betaine, alanine betaine, beta-alanine betaine, choline sulfate, pipecolic acid betaine, proline betaine, hydroxyproline betaine, tyrosine betaine, phenylalanine betaine, tryptophan betaine, leucine betaine, isoleucine betaine, and/or dimethylsulfoniopropionate.
  • the osmolyte is glycine betaine (trimethyl glycine), alone or in combination with one or more additional osmolytes, for example one or more additional compounds of formula (II).
  • compositions according to the disclosure comprise at least one compound of formula (II).
  • compositions according to the disclosure comprise one or more compounds of formula (II) that is a zwitterionic amino acid derivative bearing a quaternary ammonium group and comprising in total from 1 to 12 carbon atoms, such as from 2 to 10 carbon atoms, or from 3 to 8 carbon atoms.
  • compositions according to the disclosure comprise at least one compound of formula (II) wherein X is a divalent alkyl group, linear or branched, preferably saturated, having from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 2 carbon atoms (not substituted), such as methylene or ethylene.
  • X is a divalent alkyl group, linear or branched, preferably saturated, having from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 2 carbon atoms (not substituted), such as methylene or ethylene.
  • the composition comprises at least one osmolyte, and the osmolyte comprises, consists essentially of, or consists of one or more of the compounds shown in FIGS. 5A-5B.
  • compositions according to the disclosure comprise trimethyl glycine (referred to interchangeably as glycine betaine), optionally in combination with at least one additional osmolyte, and in particularly preferred embodiments the osmolyte in the composition comprises, consists essentially of, or consists of glycine betaine optionally with at least one additional compound of formula (II).
  • carbohydrate sugars that can be used include C3-C6 monosaccharides, for example pentoses and/or derivatives thereof, or hexoses and/or derivatives thereof.
  • the sugars may optionally be chosen from chosen from xylose, arabinose, ribose, 2-deoxy-ribose, ribulose, deoxy-ribulose, arabinose, xylulose, allose, altrose, glucose (including dextrose), glucosamine, mannose, gulose, idose, galactose, talose, sorbose, psicose, fructose, tagatose, or combinations of two or more thereof.
  • the sugars are chosen from disaccharides, for example sucrose (also saccharose), maltose, lactose, cellobiose, trehalose, dextran, or from polysaccharides, for example maltotriose, starch, dextrins, cellulose, glycogen, or combinations of two or more thereof.
  • the sugars are preferably chosen from trehalose, glucose, sucrose, fructose, fructans, or combinations of two or more thereof.
  • the total amount of osmolytes present in the composition may range from about 0.01 % to about 15%, such as, for example, from about 0.1 % to about 10%, from about 0.1 % to about 9%, from about 0.1 % to about 8%, from about 0.1 % to about 7%, from about 0.1 % to about 6%, from about 0.1 % to about 5%, from about 0.1 % to about 4%, from about 0.1 % to about 3%, from about 0.1 % to about 2%, from about 0.1 % to about 1 %, from about 0.5% to about 10%, from about 0.5% to about 9%, from about 0.5% to about 8%, from about 0.5% to about 7%, from about 0.5% to about 6%, from about 0.5% to about 5%, from about 0.5% to about 4%, from about 0.5% to about 3%, from about 0.5% to about 2%, from about 0.5% to about 1 %, from about 1 % to about 10%, from about 0.1 % to about 9%, from about
  • the total amount of osmolytes present in the composition may be about 2.0%, about 2.1 %, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • compositions comprise at least one betaine, and the total amount of betaines ranges from about 0.5% to about 5%, for example from about 1% to about 5%, preferably from about 1 .25% to about 4%, more preferably from about 1 .5% to about 3.5%, more preferably from about 2% to about 3% or from about 2% to about 2.5%, more preferably still from about 2.25% to about 2.75%, and most preferably from about 2.3% to about 2.6%, or may be about 2.0%, about 2.1%, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • the composition comprises glycine betaine in an amount ranging from about 0.5% to about 5%, for example about 1 % to about 5%, preferably from about 1 .25% to about 4%, more preferably from about 1 .5% to about 3.5%, more preferably from about 2% to about 3% or from about 2% to about 2.5%, more preferably still from about 2.25% to about 2.75%, and most preferably from about 2.3% to about 2.6%, or the glycine betaine may be present in an amount of about 2.0%, about 2.1 %, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • amounts of amino acids and osmolytes may be chosen to provide a weight ratio of the total amount of amino acid(s) and salts thereof in the composition to the total amount of osmolytes in the composition that is greater than about 0.1 , for example greater than about 0.2, greater than about 0.5, greater than about 1 , greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2.
  • the weight ratio of the total amount of amino acid(s) and salts thereof to the total amount of osmolytes may range from about 0.1 to about 10, such as from about 0.2 to about 8, from about 0.5 to about 6, from about 1 to about 5, from about 1 .2 to about 4, or from about 1 .5 to about 3.5. In other embodiments, the weight ratio of the total amount of amino acid(s) and salts thereof to the total amount of osmolytes may range from greater than 1 to about 4, such as from about 1 .25 to about 3.5, from about 1 .5 to about 3, from about 1 .75 to about 2.5, from about 1 .75 to about 2.25, or from about 1 .8 to about 2.2.
  • the weight ratio of the total amount of amino acid(s) in the composition to the total amount of osmolytes in the composition may be about 1.1 , about 1 .2, about 1 .3, about 1 .4, about 1 .5, about 1 .6, about 1 .7, about 1 .8, about 1 .9, about 2, about 2.1 , about 2.2, about 2.3, about 2.4, or about 2.5, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • compositions comprise a total amount of amino acids chosen from compounds of formula (I) and a total amount of osmolytes chosen from compounds of formula (II) such that a weight ratio of compounds of formula (l):compounds of formula (II) is greater than about 0.5, greater than about 0.75, or greater than about 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2.
  • the weight ratio of compounds of formula (I): compounds of formula (II) in the composition may range from about 0.5 to about 6, for example from about 1 to about 4, from about 1 .25 to about 3.5, from about 1 .5 to about 3, from about 1 .75 to about 2.5, from about 1 .75 to about 2.25, or from about 1.8 to about 2.2.
  • the weight ratio of compounds of formula (l):compounds of formula (II) in the composition may be about 0.5, about 0.6, about 0.7, about 0.8, about 0.9, about 1 , about 1.1 , about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, about 1.9, about 2, about 2.1 , about 2.2, about 2.3, about 2.4, or about 2.5, including all ranges and subranges using any of the foregoing as upper and lower limits.
  • the composition comprises arginine and glycine betaine and has a weight ratio of arginine to glycine betaine of greater than 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2, for example ranging from greater than 1 to about 4, preferably from about 1 .5 to about 3, more preferably from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
  • the composition comprises arginine, serine, and glycine betaine and has a weight ratio of the total amount of [arginine + serine] to glycine betaine of greater than 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1.75, or greater than about 2, for example ranging from greater than 1 to about 4, preferably from about 1 .5 to about 3, more preferably from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
  • compositions according to the disclosure include at least one carboxylic acid.
  • useful carboxylic acids include organic compounds that include, for example, one (mono-), two (di-), three (tri-), or more acid functional groups and at least one carbon atom.
  • Carboxylic acids that can be used may optionally have a molecular weight of less than about 500 g/mol, less than about 400 g/mol, less than about 300 g/mol, or less than about 200 g/mol. In preferred embodiments, the carboxylic acids have a molecular weight of less than about 300 g/mol, or less than about 200 g/mol.
  • carboxylic acids comprise from 2 to 20 carbon atoms, such as from 2 to 18 carbon atoms, from 3 to 16 carbon atoms, or from 3 to 14 carbon atoms.
  • the compositions comprise one or more hydroxylated (poly)carboxylic acids comprising from 2 to 10 carbon atoms, such as from 2 to 8 carbon atoms, or from 3 to 6 carbon atoms, and may be saturated or unsaturated, and linear or branched, and/or a salt thereof. These (poly)acids are different from the compounds of amino acids type described above.
  • Useful (poly)acids comprise at least one -COOH group (in acid or salified form); they can thus comprise a single -COOH group (monoacid) or can comprise more than one, for example two - COOH groups (in acid or salified form), or two or three -COOH groups (in acid or salified form) (polyacids).
  • Useful (poly)acids also comprise at least one -OH group, such as from one to three or from two to three -OH groups, for example one, two, or three -OH groups.
  • the (poly)acids comprise in total from 2 to 8 or from 3 to 6 carbon atoms, and from two to three -OH groups, and their hydrocarbon chain is saturated or unsaturated, linear or branched, and preferably saturated and linear.
  • the hydroxylated (poly)carboxylic acids and/or their salts comprise in total from 3 to 6 carbon atoms, from one to three -OH groups, and from two to three -COOH groups (in acid or salified form).
  • the term “(poly)acid” includes both monoacids and polyacids.
  • Non-limiting examples of mono-carboxylic acids that can be chosen include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, lactic acid, salts thereof, or combinations of two or more thereof.
  • the carboxylic acid may comprise, consist essentially of, or consist of lactic acid and/or a salt thereof.
  • Non-limiting examples of di-carboxylic acids that can be chosen include oxalic acid, malonic acid, malic acid, glutaric acid, citraconic acid, succinic acid, adipic acid, tartaric acid, fumaric acid, maleic acid, salts thereof, or combinations of two or more thereof.
  • the compositions may include oxalic acid, malonic acid, malic acid, maleic acid, salts thereof, or combinations of two or more thereof.
  • Non-limiting examples of tricarboxylic acids include citric acid, isocitric acid, aconitic acid, propane-1 ,2,3-tricarboxylic acid, salts thereof, or combinations of two or more thereof.
  • the carboxylic acid may comprise, consist essentially of, or consist of citric acid and/or a salt thereof.
  • the carboxylic acid(s) may be chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, maleic acid, lactic acid, salts thereof, or combinations of two or more thereof.
  • the carboxylic acids are chosen from a-hydroxy acids and their salts, and in particular from lactic acid, glycolic acid, tartaric acid, or citric acid, and their salts, in particular alkali metal or alkaline earth metal salts.
  • citric acid, lactic acid, and/or tartaric acid and/or their salts in particular alkali metal or alkaline earth metal salts, such as sodium citrate and/or sodium tartrate; and preferably citric acid and/or its salts, in particular alkali metal or alkaline earth metal salts, such as sodium citrate.
  • the total amount of carboxylic acid(s) may range from about 0.5% to about 20% by weight, relative to the total weight of the composition.
  • the total amount of carboxylic acids ranges from about 1 % to about 15%, such as about about 1 % to about 12%, about 1 % to about 10%, about 1 % to about 9%, about 1 % to about 8%, about 1 % to about 7%, about 1 % to about 6%, about 1 % to about 5.5%, about 1 % to about 5%, about 1 % to about 4.5%, about 1 % to about 4%, about 1 % to about 3.5%, about 1 % to about 3%, about 1 % to about 2.5%, about 1 % to about 2%, about 1 % to about 1 .5%, about 1 .5% to about 15%, about 1 .5% to about 12%, about 1 .5% to about 10%, about 1 .5% to about 9%, about 1 .5% to about 8%, about 1 .5% to about 7%
  • the total amount of carboxylic acid(s) ranges from about 0.5% to about 20%, such as from about 2% to about 15%, from about 4% to about 10%, about 4.5% to about 8%, about 5% to about 7%, about 5.5% to about 6.5%, about 5.7% to about 6.3%, or about 5.8% to about 6.2% by weight, relative to the total weight of the composition.
  • the composition comprises at least one carboxylic acid chosen from citric acid, lactic acid, tartaric acid, salts thereof, or combinations thereof, and has a total amount of carboxylic acids and salts ranging from about 0.5% to about 20%, such as from about 2% to about 15%, from about 4% to about 10%, preferably from about 4.5% to about 8%, more preferably from about 5% to about 7%, more preferably from about 5.5% to about 6.5%, more preferably still from about 5.7% to about 6.3%, and most preferably from about 5.8% to about 6.2% by weight, relative to the total weight of the composition.
  • carboxylic acid chosen from citric acid, lactic acid, tartaric acid, salts thereof, or combinations thereof
  • has a total amount of carboxylic acids and salts ranging from about 0.5% to about 20%, such as from about 2% to about 15%, from about 4% to about 10%, preferably from about 4.5% to about 8%, more preferably from about 5% to about 7%, more preferably from about 5.5% to about 6.5%, more
  • the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids of greater than about 0.75.
  • the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids of greater than about 0.8, such as greater than about 0.9, greater than about 1 , greater than about 1.1 , greater than about 1.2, greater than about 1.3, greater than about 1.4, or greater than about 1.5.
  • the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids ranging from about 0.75 to about 2, such as from about 0.8 to about 1.5, from about 0.8 to about 1 .35, or from about 0.8 to about 1 .2.
  • the composition comprises arginine and at least one carboxylic acid chosen from citric acid, lactic acid, tartaric acid, salts thereof, or combinations thereof, and has a weight ratio of the total amount of amino acids and salts thereof to the total amount of carboxylic acids and salts thereof ranging from about 0.75 to about 2, preferably from about 0.8 to about 1 .5, more preferably from about 0.8 to about 1 .35, and most preferably from about 0.8 to about 1 .2.
  • Additional Solvents Compositions according to the disclosure optionally comprise at least one solvent in addition to the penetration-enhancing solvents discussed above.
  • additional solvents may be chosen from water, non-aqueous solvents other than the penetration-enhancing solvents discussed above, or a combination thereof.
  • the additional solvent includes water.
  • the composition comprises from about 50% to about 98% of water, by weight, relative to the total weight of the composition.
  • the composition comprises water in an amount ranging from about 50% to about 95% water by weight, such as from about 50% to about 90%, about 55% to about 90%, about 60% to about 90%, or about 60% to about 80% by weight, relative to the total weight of the composition.
  • the additional solvent may include at least one non-aqueous solvent other than the penetration-enhancing solvents discussed above.
  • additional non-aqueous solvents include, for example, organic solvents, fatty alcohols, fatty ethers, fatty esters, vegetable oils, mineral oils, liposomes, laminar lipid materials, or combinations of two or more thereof.
  • the total amount of additional non-aqueous solvents in the composition may range from about 0.001% to about 10%, such as from about 0.01 % to about 10%, from about 0.1 % to about 10%, or from about 0.1 % to about 5% by weight, relative to the total weight of the composition.
  • the additional solvent comprises water and at least one additional non-aqueous solvent, wherein the total amount of nonaqueous solvents ranges from about 0.01 % to about 8%, preferably from about 0.05% to about 5%, more preferably from about 0.1 % to about 3% by weight, relative to the total weight of the composition.
  • compositions according to the disclosure may optionally comprise at least one surfactant.
  • the compositions may comprise one or more cationic surfactants and/or amphoteric surfactants, and in some embodiments the compositions may comprise mixtures of surfactants having the same or different ionicities.
  • compositions may optionally include one or more anionic surfactants and/or nonionic surfactants
  • the compositions are free or substantially free of anionic surfactants and/or nonionic surfactants.
  • the compositions comprise less than about 3%, such as less than about 2.5%, less than about 2%, less than about 1 .75%, less than about 1.5%, less than about 1.25%, less than about 1%, less than about 0.75%, less than about 0.5%, less than about 0.25%, less than about 0.2%, less than about 0.1 %, less than about 0.05%, less than about 0.01 %, or less than about 0.001 % of anionic surfactants and/or nonionic surfactants.
  • the compositions comprise at least one cationic surfactant.
  • cationic surfactant means a surfactant that is positively charged when it is contained in the composition(s) according to the disclosure. This surfactant may bear one or more positive permanent charges or may contain one or more functions that are cationizable in the composition according to the disclosure.
  • Non-limiting examples of useful cationic surfactants include brassicamidopropyl dimethylamine, behenalkonium chloride, benzethonium chloride, cetylpyridinium chloride, behentrimonium chloride, lauralkonium chloride, cetalkonium chloride, cetrimonium bromide, cetrimonium chloride, cethylamine hydrofluoride, chlorallylmethenamine chloride (Quaternium-15), distearyldimonium chloride (Quaternium-5), dodecyl dimethyl ethylbenzyl ammonium chloride (Quaternium-14), Quaternium-22, Quaternium-26, Quaternium-18 hectorite, dimethylaminoethylchloride hydrochloride, cysteine hydrochloride, diethanolammonium POE (10) oletyl ether phosphate, diethanolammonium POE (3)oleyl ether phosphate, tallow alkonium chloride, dimethyl
  • the compositions comprise at least one cationic surfactant chosen from brassicamidopropyl dimethylamine, behentrimonium chloride, cetrimonium chloride, stearamidopropyl dimethylamine, or combinations of two or more thereof.
  • the total amount of cationic surfactants may range up to about 10%, such as up to about 9%, up to about 8%, up to about 7%, up to about 6%, up to about 5%, up to about 4%, up to about 3.5%, up to about 3%, up to about 2.5%, up to about 2%, up to about 1 .5%, up to about 1 %, or up to about 0.5% by weight, relative to the total weight of the composition.
  • the total amount of cationic surfactants may range from about 0.001 % to about 10%, from about 0.01 % to about 8%, from about 0.1 % to about 6%, or from about 0.5% to about 4% by weight, relative to the total weight of the composition.
  • the compositions comprise at least one cationic surfactant, and have a total amount of cationic surfactants ranging from about 0.25% to about 8%, preferably from about 0.5% to about 7%, more preferably from about 0.75% to about 6%, and most preferably from about 1 % to about 5% by weight, relative to the total weight of the composition.
  • compositions comprise at least one amphoteric surfactant.
  • amphoteric surfactants include derivatives of aliphatic secondary and tertiary amines where the aliphatic radical can be straight or branched chain and one of the aliphatic substituents contains from about
  • amphoteric surfactants include sodium cocaminopropionate, sodium cocaminodipropionate, sodium cocoamphoacetate, sodium cocoamphohydroxypropylsulfonate, sodium cocoamphopropionate, sodium cornamphopropionate, sodium lauraminopropionate, sodium lauroamphoacetate, sodium lauroamphohydroxypropylsulfonate, sodium lauroamphopropionate, sodium cornamphopropionate, sodium lauriminodipropionate, ammonium cocaminopropionate, ammonium cocaminodipropionate, ammonium cocoamphoacetate, ammonium cocoamphohydroxypropylsulfonate, ammonium cocoamphopropionate, ammonium cornamphopropionate, ammonium lauraminopropionate, ammonium cocaminodipropionate, ammonium cocoamphoacetate, ammonium cocoamphohydroxypropylsulfonate, ammonium cocoamphopropionat
  • Betaine surfactants may also be used.
  • coco dimethyl carboxymethyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alphacarboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, cetyl dimethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine, stearyl bis-(2- hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma-carboxypropyl betaine, lauryl bis-(2-hydroxypropyl) alpha-carboxyethyl betaine, coco dimethyl sulfopropyl betaine, stearyl dimethyl sulfopropyl betaine, lauryl dimethyl sulfoethyl betaine, lauryl bis-(2-hydroxyethyl) sulfopropyl betaine, oleyl betaine, or cocamidopropyl betaine may be chosen.
  • the total amount of amphoteric surfactants may range up to about 10%, such as up to about 9%, up to about 8%, up to about 7%, up to about 6%, up to about 5%, up to about 4%, up to about 3.5%, up to about 3%, up to about 2.5%, up to about 2%, up to about 1.5%, up to about 1 %, or up to about 0.5% by weight, relative to the total weight of the composition.
  • the total amount of amphoteric surfactants may range from about 0.001 % to about 6%, from about 0.01 % to about 4%, from about 0.1 % to about 3%, or from about 0.5% to about 2% by weight, relative to the total weight of the composition.
  • the compositions are free or substantially free of amphoteric surfactants.
  • compositions according to the disclosure may include at least one fatty compound.
  • the at least one fatty compound may be chosen from lower alkanes, fatty alcohols, fatty acids, esters of fatty acids, esters of fatty alcohols, oils such as mineral, vegetable, animal, silicone and non-silicone oils, silicone and non-silicone waxes, or combinations of any two or more thereof.
  • compositions according to the disclosure include at least one fatty compound chosen from volatile and non-volatile silicone oils, which may optionally be amino functionalized.
  • fatty compound chosen from volatile and non-volatile silicone oils, which may optionally be amino functionalized.
  • silicone oils that can be used include dimethicone, amodimethicone, cyclomethicone, polysilicone-1 1 , phenyl trimethicone, trimethylsilylamodimethicone, and stearoxytrimethylsilane.
  • the composition may comprise at least one silicone chosen from amodimethicone, PEG-7 Dimethicone, PEG- 8 Dimethicone, PEG-9 Dimethicone, PEG-10 Dimethicone, PEG-12 Dimethicone, PEG-14 Dimethicone, PEG-17 Dimethicone, PEG/PPG-3/10 Dimethicone, PEG/PPG-4/12 Dimethicone, PEG/PPG- 17/18 Dimethicone, cetyl PEG/PPG-10/1 dimethicone, Dimethicone PEG-8 Benzoate, Dimethicone PEG-7 Phosphate, Dimethicone PEG-8 Phosphate, Dimethicone PEG- 10 Phosphate, or a mixture of two or more thereof.
  • the compositions comprise a silicone oil component that comprises, consists essentially of, or consists of dimethicone, amodimethicone, or a mixture thereof.
  • the silicone oil may be chosen from polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, which groups each contain from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyl-diphenyl)trisiloxanes, or (2-phenylethyl) trimethylsiloxysilicates.
  • PDMSs polydimethylsiloxanes
  • phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyl-diphen
  • compositions according to the disclosure include at least one fatty compound chosen from fatty alcohols.
  • fatty alcohol refers to any alcohol with a carbon chain of C5 or greater, such as, for example, C8 or greater, C10 or greater, or C12 or greater, such as from 6 to 30 carbon atoms or from 8 to 30 carbon atoms.
  • the fatty alcohols may be alkoxylated or non- alkoxylated, saturated or unsaturated, and linear or branched.
  • fatty alcohols may be chosen from arachidyl alcohol, behenyl alcohol, caprylic alcohol, cetearyl alcohol, cetyl alcohol, coconut alcohol, decyl alcohol, hydrogenated tallow alcohol, jojoba alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol, palm alcohol, palm kernel alcohol, stearyl alcohol, tallow alcohol, tridecyl alcohol, or combinations of two or more thereof.
  • the compositions comprise a fatty alcohol component that comprises, consists essentially of, or consists of cetyl alcohol, stearyl alcohol, cetearyl alcohol, or mixtures thereof.
  • Useful and non-limiting fatty acids may be straight or branched chain acids and/or may be saturated or unsaturated.
  • Non-limiting examples of fatty acids include diacids, triacids, and other multiple acids as well as salts of these fatty acids.
  • the fatty acid may optionally include or be chosen from lauric acid, palmitic acid, stearic acid, behenic acid, arichidonic acid, oleic acid, isostearic acid, sebacic acid, or combinations thereof.
  • fatty acid esters or fatty alcohol esters may be chosen.
  • esters of saturated or unsaturated, linear or branched C1 -C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched C1 - C26 aliphatic mono- or polyalcohols, the total carbon number of the esters more particularly being greater than or equal to 10 may be used.
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1 -C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C26 di-, tri-, tetra-, or pentahydroxy alcohols may also be used.
  • compositions according to the disclosure comprise at least one wax.
  • waxes that can be used include beeswax, hydrogenated alkyl olive esters, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax, rice wax, rice bran wax, montan wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, palm kernel glycerides/hydrogenated palm glycerides, palm butter, sumac wax, citrus aurantium dulcis (orange) peel wax, theobroma grandiflorum seed butter, helianthus annuus (sunflower) seed wax, siliconyl candellila wax, Chinese wax, cetyl palmitate, lanolin, shellac, spermaceti, cetyl esters, hydrogenated castor wax; triglyceride esters such as tribehenin (glyceryl tribehenate); synthetic waxes such as those of the hydro
  • the composition comprises one or more fatty compounds chosen from oils of animal, vegetable, or mineral origin (e.g. lanolin, squalene, fish oil, perhydrosqualene, mink oil, turtle oil, soybean oil, grape seed oil, sesame oil, maize oil, rapeseed oil, sunflower oil, cottonseed oil, avocado oil, olive oil, castor seed oil, jojoba seed oil, peanut oil, sweet almond oil, palm oil, cucumber oil, hazelnut oil, apricot kernel oil, wheat germ oil, calophyllum oil, macadamia oil, coconut oil, cereal germ oil, candlenut oil, thistle oil, candelilla oil, safflower oil, or shea butter), linear or branched hydrocarbons (e.g.
  • oils of animal, vegetable, or mineral origin e.g. lanolin, squalene, fish oil, perhydrosqualene, mink oil, turtle oil, soybean oil, grape seed oil, sesame oil, maize oil,
  • polybutene hydrogenated polyisobutene, polyisoprene, polydecenes such as hydrogenated polydecene, or also linear, branched and/or cyclic alkanes which are optionally volatile, such as, for example, isohexadecane, isododecane, isodecane, or isohexadecane), mono- and/or polyesters of fatty acids and/or of fatty alcohols (e.g.
  • Nonlimiting examples of fatty acids that may be used include optionally branched and/or unsaturated fatty acids such as myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, isostearic acid, or mixtures of two or more thereof.
  • the total amount of fatty compounds in the composition may range from about 0.1 % to about 20%, such as from about 1 % to about 20%, from about 2% to about 15%, from about 3% to about 12%, or from about 5% to about 10% by weight, relative to the total weight of the composition.
  • the compositions comprise at least one fatty compound chosen from silicone oils, fatty alcohols, waxes, or combinations thereof, where the total amount of fatty compounds in the composition ranges from about 1% to about 20%, preferably from about 2% to about 15%, more preferably from about 3% to about 12%, and most preferably from about 5% to about 10% by weight, relative to the total weight of the composition.
  • compositions according to the disclosure optionally comprise at least one thickening agent.
  • useful thickening agents include, but are not limited to, semisynthetic polymers, such as semisynthetic cellulose derivatives, synthetic polymers, such as carbomers, poloxamers, and acrylates/beheneth-25 methacrylate copolymer, acrylates copolymer, polyethyleneimines (e.g., PEI-10), naturally occurring polymers, such as acacia, tragacanth, alginates (e.g., sodium alginate), carrageenan, vegetable gums, such as xanthan gum, guar gum, petroleum jelly, waxes, particulate associate colloids, such as bentonite, colloidal silicon dioxide, and microcrystalline cellulose, celluloses such as hydroxyethylcellulose and hydroxypropylcellulose, and guars such as hydroxypropyl guar.
  • semisynthetic polymers such as semisynthetic cellulose derivatives
  • the thickening agent may be chosen from associative thickening polymers such as anionic associative polymers, amphoteric associative polymers, cationic associative polymers, or nonionic associative polymers.
  • associative thickening polymers such as anionic associative polymers, amphoteric associative polymers, cationic associative polymers, or nonionic associative polymers.
  • a non-limiting example of an amphoteric associative polymer is acrylates/beheneth-25 methacrylate copolymer, and non-limiting examples of anionic associative polymers include acrylates copolymer and acrylates crosspolymer-4.
  • the total amount of thickening agents may range from about 0.01 % to about 8%, such as from about 0.05% to about 5%, from about 0.1 % to about 4%, from about 0.2% to about 3%, or from about 0.3% to about 2% by weight, relative to the total weight of the composition.
  • compositions according to the disclosure may optionally include one or more auxiliary components.
  • auxiliary components include preservatives, fragrances, pH adjusters, salts, antioxidants, vitamins, vitamin derivatives, ceramides, botanical extracts, proteins, protein hydrolysates, protein isolates, hydrotropes, pearlescent agents, buffers, sequestering agents, and the like.
  • the total amount of auxiliary components typically ranges from about 0.01 % to about 10% based on the total weight of the composition.
  • the individual amounts of each component or the total amount of components may range from about 0.1 % to about 10%, about 0.1 % to about 8%, about 0.1 % to about 5%, about 0.1 % to about 4%, about 0.1 % to about 3%, about 0.1 % to about 2%, about 1 % to about 10%, about 1 % to about 8%, about 1% to about 5%, about 1 % to about 4%, about 1 % to about 3%, or about 1 % to about 2% by weight, based on the total weight of the composition.
  • compositions according to the disclosure typically have a pH of less than or equal to 7, such as less than or equal to about 6, less than or equal to about 5, less than or equal to about 4.5, or less than or equal to about 4.
  • the compositions may have a pH ranging from about 1 to about 7, such as from about 2 to about 6, from about 2.5 to about 5.5, from about 2.5 to about 5, from about 2.5 to about 4.5, or from about 3 to about 4.
  • the pH of the composition may be, for example, about 3, about 3.25, about 3.5, about 3.75, or about 4, including all ranges and subranges thereof.
  • compositions may be in any suitable form.
  • the compositions may be a liquid, a gel, a gel cream, a high-, medium- or low-density cream, a serum, a lotion, etc.
  • the disclosure further relates to methods of improving penetration of active agents into keratin fibers, e.g. hair.
  • the methods comprise including at least one penetration-enhancing solvent as described herein in a composition comprising at least one active agent.
  • the active agents may, in various embodiments, comprise at least one amino acid, at least one osmolyte, and/or at least one carboxylic acid, as described herein.
  • the active agent comprises, consists essentially of, or consists of at least one amino acid and/or a salt thereof and at least one osmolyte.
  • the active agent comprises, consists essentially of, or consists of at least one basic amino acid, glycine betaine, and at least one carboxylic acid.
  • the active agent comprises, consists essentially of, or consists of arginine and/or a salt thereof, glycine betaine, and citric acid and/or a salt thereof.
  • the disclosure further relates to methods of treating keratin fibers, in order to provide enhanced penetration of active agents into the hair, using compositions according to the disclosure.
  • the methods are able to provide surprisingly greater benefits to the hair due to the greater ability of the active agents to penetrate into the hair fibers.
  • the methods comprise applying a composition according to the disclosure onto the hair, optionally leaving the composition on the hair for a period of time (“processing time,” “resting period,” or “leave-in period”), and optionally rinsing the composition from the hair.
  • various treatments using compositions according to the disclosure may also include a step of heating the hair to which the composition has been applied, for example during the leave-in period while the composition is on the hair.
  • a blow dryer, hood dryer, etc. may be used.
  • the leave-in period may last for a period of time deemed appropriate to allow the active agents to provide benefits to the keratin fibers, such as about 30 seconds, about 1 minute, about 2 minutes, about 5 minutes, about 10 minutes, about 15 minutes, about 20 minutes, about 30 minutes, about 45 minutes, about 1 hour, about 2 hours, etc., or may range from a period of time using any of the foregoing as upper and lower limits.
  • the leave-in period may range from about 30 seconds to about 60 minutes, from about 30 seconds to about 45 minutes, from about 30 seconds to about 30 minutes, from about 30 seconds to about
  • 20 minutes from about 30 seconds to about 15 minutes, from about 30 seconds to about 10 minutes, from about 30 seconds to about 5 minutes, from about 1 minute to about 60 minutes, from about 1 minute to about 45 minutes, from about 1 minute to about 30 minutes, from about 1 minute to about 20 minutes, from about 1 minute to about 15 minutes, from about 1 minute to about 10 minutes, from about 1 minute to about 5 minutes, from about 2 minutes to about 60 minutes, from about 2 minutes to about 45 minutes, from about 2 minutes to about 30 minutes, from about 2 minutes to about 20 minutes, from about 2 minutes to about 15 minutes, from about 2 minutes to about 10 minutes, from about 2 minutes to about 5 minutes, etc.
  • hair treated with compositions and methods according to the disclosure has less damage than hair not treated according to the disclosure, which is achieved by successful penetration of the active agents into the hair fibers.
  • the reduction in damage is particularly notable in hair that has been damaged due to harsh chemical treatments such as bleaching, dyeing, permanent waving, straightening, relaxing, etc., as well as due to repeated styling such as with heat or styling tools.
  • the hair repaired using compositions and methods according to the disclosure may have lower elasticity and/or greater tensile strength than hair similarly damaged but not treated according to the disclosure.
  • a salt thereof also relates to “salts thereof.”
  • the disclosure refers to “an element selected from the group consisting of A, B, C, D, E, F, a salt thereof, or mixtures thereof,” it indicates that that one or more of A, B, C, D, and F may be included, one or more of a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, or a salt of F may be included, or a mixture of any two of A, B, C, D, E, F, a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included.
  • amino acids and/or salts thereof means “amino acids and salts thereof” as well as “amino acids or salts thereof,” and expressly covers instances of either.
  • salts may include salts having a counterion such as an alkali metal, alkaline earth metal, or ammonium counterion. This list of counterions, however, is non-limiting. Salts also include a dissociated form of a compound, e.g., in an aqueous solution.
  • the phrases “and mixtures thereof,” “and mixtures of two or more thereof,” “and a mixture thereof,” “and combinations thereof,” “and a combination thereof,” and combinations of two or more thereof,” “and a combination of two or more thereof,” “or mixtures thereof,” “or combinations thereof,” “or combinations of two or more thereof,” “or a combination thereof,” and the like are used interchangeably to denote that the listing of components immediately preceding the phrase, such as “A, B, C, D, or mixtures thereof” signify that the component(s) may be chosen from A, from B, from C, from D, from A+B, from A+B+C, from A+D, from A+C+D, etc., without limitation on the variations thereof. Thus, the components may be used individually or in any combination thereof.
  • ком ⁇ онент As used herein, if a component is described as being present “in an amount up to” a certain amount, it is intended that such component is, in fact, present in the composition, i.e. is present in an amount greater than 0%. All amounts given herein are relative to the amount of active material, unless otherwise indicated.
  • ranges provided are meant to include every specific range within, and combination of sub ranges between, the given ranges.
  • a range from 1 -5 includes specifically 1 , 2, 3, 4 and 5, as well as sub ranges such as 2-5, 3-5, 2-3, 2-4, 1 -4, etc.
  • applying a composition onto hair and variations thereof are intended to mean contacting the hair with at least one of the compositions of the disclosure, in any manner. It may also mean contacting the hair in an effective amount.
  • treating hair refers to the application of the compositions of the present disclosure onto the surface of hair.
  • treating hair also refers to contacting hair with the compositions of the present disclosure.
  • a "rinse-off" product refers to a composition such as a hair treatment composition that is removed from the hair after a processing time, e.g. is rinsed and/or washed with water. At least a portion, and typically most, of the composition is removed from the hair.
  • the terms “improving penetration,” “improved penetration,” “enhancing penetration,” “enhanced penetration,” or the like, of active agents means any increase in the amount of active agents present in the hair fiber.
  • the increase in amount of active agents present in the hair fiber can be determined for example by measuring the denaturation temperature of the hair using Differential Scanning Calorimetry (crimpled, closed pan), where an increase in the denaturation temperature signifies an increase in the amount of actives present.
  • an increase or improvement in penetration in active agents also results in healthier, stronger, less damaged hair which may be determined by various methods, such as, for example, break stress testing, elasticity, etc.
  • the term “substantially free” or “essentially free” as used herein means that there is less than about 5% by weight of a specific material added to a composition, based on the total weight of the composition.
  • the compositions may include less than about 4%, less than about 3%, less than about 2%, less than about 1 .5%, less than about 1 %, less than about 0.5%, less than about 0.1 %, less than about 0.01%, less than about 0.001 %, or less than about 0.0001% of the specified material.
  • any component described herein for use in the hair treatment compositions can be present in the compositions in amounts less than about 5%, less than about 4%, less than about 3%, less than about 2%, less than about 1 %, less than about 0.5%, less than about 0.1 %, less than about 0.01 %, less than about 0.001 %, or less than about 0.0001 %, and the composition will be considered “substantially free” of such material.
  • a composition that is “free” of a component is understood to contain none of the specified component.
  • a composition that is “free” of waxes may not have wax included as an intended component but may nevertheless contain a pigment that is coated with a wax, as such wax would be considered a minor component of the pigment material and would not be expected to provide benefits to the composition that would be expected by including a wax per se as an intended component.
  • compositions 1 A-1 F according to the disclosure were prepared as shown in Table 1 .
  • the pH of each of compositions 1 A-1 F was about 3.5.
  • compositions contained a synergistic combination of active agents
  • a penetration-enhancing solvent propylene glycol or dipropylene glycol
  • compositions according to the disclosure were evaluated.
  • swatches (S1 -S8) of virgin Caucasian hair were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes.
  • the swatches were rinsed and then seven of the swatches (S1 -S7) were subjected to the following treatment routines (swatch S8 did not have any treatment after the bleaching composition was rinsed from the hair).
  • Swatch S1 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated every day for five days.
  • Swatches S2-S7 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • one of compositions 1 A-1 F (Table 2A) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated every day for five days.
  • the integrity of the hair fibers of each of swatches S1 -S8 was studied after the first and fifth days. Elasticity was evaluated to determine whether the hair fibers stretched, and if so, whether they returned to their original state (lower elasticity, i.e. healthy), whether the fibers stretched easily and remained stretched (higher elasticity, i.e. damaged), or whether the hair fibers broke upon testing.
  • the evaluation was performed by stretching a standardized amount of wet hair fibers, with two experts independently evaluating each swatch.
  • the experts were trained to stretch the area of the swatch being evaluated by uniformly applying manual pulling force using the hands/fingers.
  • the behavior of the swatch was classified by each expert according to a 6-level scale as follows, with the result reported for each swatch as the average of the two:
  • Swatch S9 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair. The treatment was repeated a second time. This treatment protocol was repeated every day for five days.
  • Swatches S10-S15 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • one of compositions 1 A-1 F (Table 2B) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair. This treatment protocol was repeated every day for five days.
  • Examples 2A-2B therefore demonstrate that compositions according to the disclosure surprisingly enhance penetration of the active agents into the damaged hair fibers, allowing the active agents to repair the damage. Surprisingly, Example 2B demonstrates that this benefit is observed even in hair that has substantial build-up of hair products coated on the hair fibers.
  • compositions 2A-2E according to the disclosure were prepared as shown in Table 3.
  • compositions contained a synergistic combination of active agents
  • Example 4 Evaluation of Damage Repair In order to evaluate the ability of compositions according to the disclosure to enhance penetration of the active agents into damaged hair fibers to minimize, prevent, or repair damage to hair, the following studies were conducted.
  • a comparative product, C1 had the following listing of ingredients on the package: Water (Aqua/Eau), Bis-Aminopropyl Diglycol Dimaleate, Propylene Glycol, Cetearyl Alcohol, Behentrimonium Methosulfate, Cetyl Alcohol, Phenoxyethanol, Glycerin, Hydroxyethyl Ethylcellulose, Stearamidopropyl Dimethylamine , Quaternium- 91 , Sodium Benzoate, Cetrimonium Methosulfate, Cetrimonium Chloride, Fragrance (Parfum), Tetrasodium EDTA, Polyquaternium-37, Benzyl Benzoate, Etidronic Acid, Ascorbic Acid, Phytantriol, Tocopheryl Acetate, Aloe Barbadensis Leaf Juice, Panthenol, Simmondsia Chinensis (Jojoba) Seed Oil, Citric Acid, Potassium Sorbate.
  • composition C1 which is described as a “pre-shampoo hair treatment that reduces breakage and split ends for visibly healthier hair,” is advertised as part of a system that asserts it can “relink broken disulfide bonds damaged by chemical services, heat, and styling.”
  • the instructions for composition C1 are to use the product prior to using the shampoo (“C1 -S”) and conditioner (“C1 -C”) that form part of this system, both of which include bis-aminopropyl diglycol dimaleate as the stated active agent.
  • swatches (S17-S21 ) of virgin Caucasian hair were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes.
  • the swatches were rinsed and then four of the swatches (S17-S20) were subjected to the following treatment routines (swatch S21 did not have any treatment after the bleaching composition was rinsed from the hair).
  • Swatch S17 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
  • Swatches S18 and S19 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • one of compositions 2D (S18) or 2B (S19) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
  • composition C1 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated.
  • Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
  • FIG. 4A shows the break stress (MPa) for a control swatch (CTL), which was the same hair but unbleached, swatch S17, which was bleached but without subsequent treatment, and swatches S18 and S19, treated with compositions 2D and 2B respectively, and S20, treated with the comparative compositions.
  • CTL control swatch
  • the break stress of the control swatch (CTL) was more than twice that of swatch S17, demonstrating the significant damage caused by the bleaching process.
  • the break stress of the treated swatches was increased compared to swatch S17.
  • the swatches were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • Swatch S22 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a mask composition was applied to the hair and allowed to remain on the hair, after which the hair was rinsed.
  • a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • Swatch S23 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • composition 2C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • composition C1 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated.
  • Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • the swatches were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • Swatches S27 and S28 were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • One of either composition 2B (S28) or 2D (S27) was applied to the hair and allowed to remain on the hair, after which the hair was rinsed.
  • a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • composition C1 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated.
  • Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed.
  • conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed.
  • a leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
  • FIG. 4B shows the break stress (MPa) for a control swatch (CTL), which was the same hair but unbleached, swatch S26, which was bleached but without subsequent treatment, swatches S27 and S28, treated with compositions 2D and 2B respectively, and S29, treated with the comparative compositions.
  • CTL control swatch
  • Examples 4A-4C thus demonstrate that compositions according to the disclosure have surprisingly enhanced penetration of the active agents into the damaged hair fibers, allowing the active agents to repair the damage. Surprisingly, Example 4B demonstrates that this benefit is even observed in hair that has substantial build-up of hair products coated on the hair fibers. The damage repair achieved with compositions according to the disclosure is also surprisingly greater than that achieved with a commercial product that asserts to do the same.
  • Example 5 Penetration Enhancing Compositions
  • compositions 3A-3D according to the disclosure were prepared as shown in Table 4.
  • Compositions 3A-3D are expected to similarly provide improved penetration of the active agents contained therein to hair, in order to more effectively introduce components into the hair fiber that can minimize, prevent, and/or repair damage.
  • compositions according to the disclosure can be prepared and are likewise expected to similarly improve penetration of active agents into the hair in order to minimize, prevent, or repair damage to hair.
  • compositions and methods according to the disclosure surprisingly and unexpectedly enhance penetration of active agents in order to minimize, prevent, or repair damage to hair.

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Abstract

The disclosure relates to compositions and methods for improving penetration of active agents into keratin fibers. The compositions comprise at least one penetration-enhancing solvent and at least one active agent for treating hair. The methods comprise enhancing penetration of active agents into keratin fibers as well as treating keratin fibers with the compositions.

Description

COMPOSITIONS AND METHODS FOR IMPROVING PENETRATION OF ACTIVE AGENTS FOR KERATIN FIBERS
TECHNICAL FIELD
The present disclosure relates to compositions and methods for improving penetration of agents for treating keratin fibers, for example agents for repairing damaged hair fibers, providing strength to hair fibers, and/or reducing elasticity of hair fibers.
BACKGROUND
Consumers use cosmetic compositions and processes to change or enhance the appearance of their hair, e.g., by changing the color, style, and/or shape of the hair, and/or by imparting various properties to hair, such as shine and conditioning. However, many compositions and processes for changing the appearance of the hair, such as compositions and processes for permanently altering the color or shape of the hair, involve harsh chemical treatments. Additionally, repeated styling can lead to damaged hair, for example due to repeated use of heat and styling tools. All of these processes can break bonds within the hair fibers, which if not reformed results in damaged hair.
For example, hair lightening and dyeing compositions and processes generally require the presence of a strong alkalizing agent such as ammonia, as well as additional compounds such as oxidizing agents. In order to alter the color of the hair, these components must first break down the natural components in the hair fibers. Similarly, hair straightening, relaxing, and permanent waving compositions also involve harsh chemicals to change the shape of the hair by breaking the disulfide bonds in the hair fibers.
It is known that, while such processes effectively alter the color and shape of the hair, the chemical agents used inherently result in damage to the hair and negatively impact the strength, elasticity, and porosity of the hair fibers. For example, hair that has been bleached, dyed, relaxed, straightened, waved, repeatedly styled, etc., is often dry, frizzy, and generally unhealthy in feel and appearance. Additionally, the damaged hair is brittle and/or has increased elasticity, which result in greater incidence of hair breakage. As such, consumers seek compositions and processes for preventing or minimizing such damage and/or for repairing hair that has been damaged by these treatments and processes. In particular, consumers desire hair that is strong, does not break easily, is able to be stretched or manipulated while retaining the ability to return to its original state without breakage (i.e., has decreased elasticity), and that feels soft and healthy to the touch and also appears shiny and healthy.
However, formulating compositions that satisfactorily address these issues has proven to be challenging. For example, some compositions that attempt to address the problem simply coat the hair with compounds that can improve the feel and appearance of the hair; however, this approach is only temporary and superficial. Instead of preventing or repairing hair damage, this approach simply masks the damage until the hair is next rinsed or washed. Other compositions attempt to address the damage within the hair fiber, but to date have not been satisfactory. This is believed to be, in part, due to ineffective penetration of active agents into the hair fibers, for example hair that has been subject to application of treatment compositions, resulting in a build-up of such compositions on the surface of the hair fiber.
The present inventors have now discovered that certain components are surprisingly effective at improving penetration of active agents into the keratin fibers, e.g., hair. Surprisingly, this effect was observed even in hair that had a substantial build-up of product coated on the hair. Hair treated with compositions comprising one or more of these components, in combination with active agents, exhibit surprisingly reduced signs of damage including greater strength and/or decreased elasticity, in particular hair that has been damaged by harsh chemical treatments such as bleaching, dyeing, permanent waving, straightening, relaxing, etc.
SUMMARY
The present disclosure relates to compositions and methods for improving penetration of active agents into keratin fibers, for example active agents for preventing, minimizing, or repairing hair damage such as damage caused by harsh chemical compositions and processes.
In various embodiments, the disclosure relates to compositions for treating keratin fibers, such as hair, the compositions comprising at least one penetration-enhancing solvent and at least one active agent. In various embodiments, the penetration-enhancing solvent(s) may be chosen from polyols, and the active agent(s) may be chosen from amino acids, osmolytes, and/or carboxylic acids.
In some embodiments, the compositions comprise (a) at least one penetration-enhancing solvent chosen from diols and/or triols, (b) at least one amino acid and/or salt thereof, (c) at least one osmolyte, and (d) at least one carboxylic acid and/or salt thereof. In other embodiments, the compositions comprise (a) at least one penetration-enhancing solvent chosen from polyols such as, for example, C2-C8 diols and/or C2-C8 triols, for example glycols, (b) at least one amino acid chosen from compounds of formula (I) and/or salts thereof, (c) at least one osmolyte chosen from carbohydrates, polyamines, and/or compounds of formula (II), and (d) at least one carboxylic acid and/or salt thereof. In further embodiments, the compositions comprise (a) at least one penetration-enhancing solvent chosen from C2-C8 diols and/or C2-C8 triols, for example glycols, (b) at least one basic amino acid and/or a salt thereof, (c) at least one osmolyte chosen from carbohydrate sugars, polyamines, and/or betaines, preferably at least one betaine chosen from compounds of formula (II), and (d) at least one carboxylic acid and/or salt thereof. In still further embodiments, the compositions comprise (a) at least one penetration-enhancing solvent chosen from glycols, for example propylene glycol and/or dipropylene glycol, (b) arginine and/or a salt thereof, (c) at least one compound of formula (II), and (d) at least one carboxylic acid and/or salt thereof. The pH of the compositions is generally less than 7, such as less than about 6, for example ranging from about 2 to about 5, or from about 3 to about 4.
In various embodiments, the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition. The penetration-enhancing solvents comprise at least one polyol. In some embodiments, the penetration-enhancing solvents may comprise, consist essentially of, or consist of C2-C16 diols and/or C2-C16 triols, for example C2- C8 diols and/or C2-C8 triols. In some embodiments, the penetration-enhancing solvents may comprise, consist essentially of, or consist of glycols, for example propylene glycol and/or dipropylene glycol.
In some embodiments the compositions comprise at least one amino acid chosen from basic amino acids, for example arginine, histidine, lysine, salts thereof, or combinations thereof. In various embodiments, the total amount of basic amino acids and salts thereof ranges from about 0.1% to about 15%, preferably from about 1 % to about 12%, more preferably from about 2% to about 10%, more preferably still from about 3% to about 7%, and most preferably from about 4% to about 6% by weight, relative to the total weight of the composition. In further embodiments the compositions comprise at least one amino acid chosen from acidic or neutral amino acids and salts thereof, for example serine. In various embodiments, the total amount of acidic and/or neutral amino acids and salts thereof ranges from about 0.01 % to about 5%, preferably from about 0.05% to about 4%, more preferably from about 0.1 % to about 3%, and most preferably from about 0.25% to about 2.5% by weight, relative to the total weight of the composition. In still further embodiments, the compositions comprise a mixture of basic, acidic, and/or neutral amino acids, for example the compositions may comprise arginine and serine. In various embodiments, the total amount of amino acids and salts thereof present in the composition ranges from about 0.1 % to about 15%, preferably from about 1 % to about 12%, more preferably from about 2% to about 10%, more preferably still from about 3% to about 7%, and most preferably from about 4% to about 6% by weight, relative to the total weight of the composition.
In some preferred embodiments, compositions according to the disclosure comprise one or more amino acids chosen from glycine, proline, methionine, serine, arginine, lysine, histidine, salts of any of the foregoing (in particular alkali metal, alkaline earth metal, or zinc salts), and combinations of two or more thereof.
In various embodiments, the compositions comprise at least one osmolyte chosen from carbohydrate sugars, methylsulfonium compounds, polyamines, and/or amino acid derivatives such as betaines, preferably chosen from compounds of formula (II). In various embodiments, the total amount of osmolytes present in the composition ranges from about 0.01 % to about 10%, preferably from about 1 % to about 5%, more preferably from about 1 .25% to about 4%, more preferably still from about 1 .5% to about 3%, and most preferably from about 2% to about 2.5% by weight, relative to the total weight of the composition. In various embodiments, the composition has a weight ratio of the total amount of amino acids to the total amount of osmolytes that is equal to or greater than about 0.5, such as greater than about 1 , preferably ranging from about 1.25 to about 3.5, more preferably from about 1.5 to about 3, more preferably still from about 1.75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
In various embodiments, the compositions comprise at least one carboxylic acid chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, maleic acid, lactic acid, salts thereof, or combinations of two or more thereof, and preferably citric acid, lactic acid, salts thereof, or combinations of two or more thereof. In various embodiments, the total amount of carboxylic acids and salts thereof may range from about 0.5% to about 20%, preferably from about 1% to about 15%, more preferably from about 2% to about 12%, more preferably still from about 3% to about 10%, and most preferably from about 4% to about 7% by weight, relative to the total weight of the composition. In various embodiments, the composition has a weight ratio of the total amount of amino acids and salts thereof to the total amount of carboxylic acids and salts thereof of greater than about 0.5, such as greater than about 0.7, preferably ranging from about 0.75 to about 2, and more preferably from about 0.8 to about 1 .5.
The composition may further comprise water and/or at least one nonaqueous solvent in addition to the penetration-enhancing solvent(s). Optionally, the compositions comprise water and at least one additional non-aqueous solvent. The compositions may optionally also include at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations of two or more thereof.
In certain embodiments, the compositions comprise (a) at least one penetration-enhancing solvent chosen from glycols, for example propylene glycol, dipropylene glycol, or mixtures thereof, (b) at least one basic amino acid, for example arginine and/or salts thereof, (c) from about 1 % to about 5% of glycine betaine, (d) at least one carboxylic acid, for example citric acid and/or salts thereof, (e) water, and (f) optionally serine, wherein the total amount of penetration-enhancing solvents ranges from about 8% to about 40%, wherein the total amount of basic amino acids ranges from about 1 % to about 10%, and wherein all amounts are by weight, relative to the total weight of the composition. The pH of the compositions is generally less than 7, for example ranging from about 2 to about 5, or from about 3 to about 4. In various embodiments, the compositions have a weight ratio of the total amount of basic amino acids to glycine betaine of greater than 1 , preferably from about 1 .25 to about 3.5, more preferably from about 1 .5 to about 3, more preferably still from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25. In some embodiments, the compositions have a weight ratio of the total amount of basic amino acids to the total amount of carboxylic acids of greater than about 0.75, preferably ranging from about 0.75 to about 2, more preferably from about 0.8 to about 1.5. Optionally, the compositions may comprise at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations thereof. In embodiments where the composition comprises serine, the amount of serine can range from about 0.01 % to about 2%, preferably from about 0.05% to about 1 .5%, more preferably from about 0.05% to about 1 %, and most preferably from about 0.05% to about 0.5% by weight, relative to the total weight of the composition. Further, the compositions may have a weight ratio of the total amount of basic amino acids to serine of greater than about 2, preferably ranging from about 2 to about 15, more preferably from about 4 to about 14, more preferably still from about 6 to about 13, and most preferably from about 8 to about 12, and/or a weight ratio of glycine betaine to serine of greater than about 2, preferably ranging from about 2 to about 10, more preferably from about 3 to about 8, more preferably still from about 3.5 to about 7, and most preferably from about 4 to about 6.
In preferred embodiments, the compositions comprise (a) at least one penetration-enhancing solvent, (b) at least one amino carboxylic acid or a salt thereof, preferably chosen from arginine and/or a salt thereof, (c) at least one betaine derivative, preferably chosen from glycine betaine, (d) at least one carboxylic acid, preferably chosen from citric acid, lactic acid, and/or salts thereof, and (e) water. For example, the composition may comprise (a) at least one penetration-enhancing solvent chosen from propylene glycol, dipropylene glycol, or mixtures thereof, (b) from about 4% to about 6% of arginine, (c) from about 1 .5% to about 3.5% of glycine betaine, (d) at least one carboxylic acid, (e) water, and (f) optionally serine, wherein the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30%, and wherein all amounts are by weight, relative to the total weight of the composition. The pH of the compositions is generally less than 7, for example ranging from about 2 to about 5, or from about 3 to about 4. In various embodiments, the compositions have a weight ratio of the amount of arginine to glycine betaine of greater or equal to about 5, such as greater than 1 , preferably from about 1 .25 to about 3.5, more preferably from about 1 .5 to about 3, more preferably still from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25. In some embodiments, the compositions have a weight ratio of the amount of arginine to the total amount of carboxylic acids of greater than or equal to about 0.5 or greater than about 0.7, preferably ranging from about 0.75 to about 2, more preferably from about 0.8 to about 1 .5. Optionally, the compositions may comprise at least one additional component chosen from fatty compounds, surfactants, thickening agents, or combinations thereof. In embodiments where the composition comprises serine, the amount of serine can range from about 0.01 % to about 2%, preferably from about 0.05% to about 1.5%, more preferably from about 0.05% to about 1%, and most preferably from about 0.05% to about 0.5% by weight, relative to the total weight of the composition. Further, the compositions may have a weight ratio of the amount of arginine to serine of greater than about 2, preferably ranging from about 2 to about 15, more preferably from about 4 to about 14, more preferably still from about 6 to about 13, and most preferably from about 8 to about 12, and/or a weight ratio of glycine betaine to serine of greater than about 2, preferably ranging from about 2 to about 10, more preferably from about 3 to about 8, more preferably still from about 3.5 to about 7, and most preferably from about 4 to about 6.
The disclosure also relates to methods of treating keratin fibers, preferably hair, comprising applying a composition according to the disclosure to the keratin fibers. The methods may, for example, be methods of reducing, preventing, and/or repairing damage, and/or may be methods of improving the overall general health and appearance of the hair.
The disclosure further relates to methods of enhancing penetration of at least one active agent into keratin fibers, the methods comprising including at least one penetration-enhancing solvent in a composition comprising the active agent(s), wherein the at least one penetration-enhancing solvent is chosen from polyols, preferably diols and/or triols, for example propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, or mixtures of two or more thereof, and the at least one active agent is chosen from amino acids, osmolytes, carboxylic acids, or combinations of two or more thereof.
BRIEF DESCRIPTION OF THE FIGURES
FIGS. 1A-1 B are graphs showing the elasticity of hair fibers of swatches S1 -S8 after one treatment (1A) and five treatments (1 B).
FIGS. 2A-2B are graphs showing the elasticity of hair fibers of swatches S9-S16 after one treatment (2A) and five treatments (2B).
FIG. 3 is a graph showing the elasticity of hair fibers of swatches S17- S21 after five treatments.
FIGS. 4A-4B are graphs showing the break stress of hair fibers treated with compositions according to the disclosure and comparative compositions. FIGS. 5A-5B show the structures of certain exemplary osmolytes that can be included in compositions according to the disclosure.
DETAILED DESCRIPTION
The disclosure relates to compositions and methods for improving penetration of active agents for treating keratin fibers, such as hair, for example active agents for repairing damaged keratin fibers, providing strength to keratin fibers, and/or reducing elasticity of keratin fibers. The compositions comprise at least one penetration-enhancing solvent and at least one active agent. The methods comprise enhancing penetration of active agents into keratin fibers as well as treating keratin fibers, e.g., hair, with the compositions.
I. COMPOSITIONS
The compositions according to the present disclosure comprise at least one penetration-enhancing solvent and at least one active agent.
Penetration-Enhancing Solvents
Compositions according to the disclosure comprise at least one penetration-enhancing solvent chosen from polyols. These solvents have been surprisingly discovered to be particularly effective at improving penetration of active agents into the hair fibers, even in the presence of build-up of treatment or styling products on the surface of the hair fibers.
In various embodiments, the polyols can be chosen from diols and triols. In other embodiments, the polyols can be chosen from C2-C16 polyols, such as C2- C12 polyols, C2-C8 polyols, or C3-C8 polyols. In various embodiments, the polyols that can be used are linear or branched, saturated or unsaturated, and substituted or unsubstituted polyols. Thus, in various embodiments, one or more polyols can be chosen from C2-C16, C2-C12, C2-C8, or C3-C8 diols, or C2-C16, C2-C12, C2-C8, or C3-C8 triols, any of which may be linear or branched, saturated or unsaturated, and substituted or unsubstituted.
By way of non-limiting example, polyols such as isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl, and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol may be chosen. In some embodiments, the polyols are chosen from propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, 1 ,2,6- hexanetriol, 1 ,2,4-butanetriol, trimethylolpropane, 2-butene-1 ,4-diol, 2-ethyl-1 ,3- hexanediol, 2-methyl-2,4-pentanediol, caprylyl glycol, 1 ,2-hexanediol, 1 ,2-pentanediol, 2-ethyl-2-methyl-1 ,3-propanediol, 3,3-dimethyl-1 ,2-butanediol, 2,2-diethyl- 1 ,3- propanediol, 2-methyl-2-propyl-1 ,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 2,5- dimethyl-2,5-hexanediol, 5-hexene-1 ,2-diol, 2-ethyl-1 ,3-hexanediol, 4-methyl-1 ,2- pentanediol, or combinations of two or more thereof. In some preferred embodiments, the polyols are chosen from glycols such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, 1 ,3-propanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, caprylyl glycol, glycerin, diglycerin, and combinations of two or more thereof. In a particularly preferred embodiment, the penetration-enhancing solvent comprises at least one polyol chosen from propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, glycerin, or combinations of two or more thereof. In at least certain preferred embodiments, the penetration-enhancing solvent comprises, consists essentially of, or consists of one or more C2-C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols. In other preferred embodiments, the penetration-enhancing solvent comprises, consists essentially of, or consists of one or more glycols, for example propylene glycol and/or dipropylene glycol, and in particularly preferred embodiments, the penetrationenhancing solvent comprises, consists essentially of, or consists of dipropylene glycol.
The total amount of penetration-enhancing solvents may vary, and in various embodiments may range from about 2% to about 65%, such as, for example, from about 4% to about 60%, from about 6% to about 55%, from about 8% to about 50%, from about 9% to about 45%, from about 10% to about 40%, from about 12% to about 38%, or from about 15% to about 35% by weight, relative to the total weight of the composition. In other embodiments, the total amount of penetration enhancing solvents may range from about 2% to about 20%, such as, for example, from about 4% to about 16%, from about 6% to about 14%, from about 8% to about 12%, or from about 9% to about 1 1% by weight, relative to the total weight of the composition. In still other embodiments, the total amount of penetration enhancing solvents may range from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition. In at least some embodiments, the compositions comprise at least about 5%, such as at least about 8%, or at least about 10% of penetration-enhancing solvent(s).
For example, in some embodiments, the total amount of penetrationenhancing solvents may range from about 5% to about 50%, such as from about 8% to about 45%, from about 8% to about 40%, from about 8% to about 35%, from about 8% to about 30%, from about 8% to about 25%, from about 10% to about 45%, from about 10% to about 40%, from about 10% to about 35%, from about 10% to about 30%, from about 10% to about 25%, from about 12% to about 45%, from about 12% to about 40%, from about 12% to about 35%, from about 12% to about 30%, from about 12% to about 25%, from about 15% to about 45%, from about 15% to about 40%, from about 15% to about 35%, from about 15% to about 30%, from about 15% to about 25%, from about 18% to about 45%, from about 18% to about 40%, from about 18% to about 35%, from about 18% to about 30%, or from about 18% to about 25% by weight, relative to the total weight of the composition.
In other embodiments, the total amount of penetration-enhancing solvents may range from about 5% to about 15%, such as from about 5% to about 14%, about 5% to about 13%, about 5% to about 12%, about 5% to about 11 %, about 5% to about 10%, about 6% to about 15%, about 6% to about 14%, about 6% to about 13%, about 6% to about 12%, about 6% to about 1 1 %, about 6% to about 10%, about 7% to about 15%, about 7% to about 14%, about 7% to about 13%, about 7% to about 12%, about 7% to about 1 1 %, about 7% to about 10%, about 8% to about 15%, about 8% to about 14%, about 8% to about 13%, about 8% to about 12%, about 8% to about 1 1 %, about 8% to about 10%, about 9% to about 15%, about 9% to about 14%, about 9% to about 13%, about 9% to about 12%, about 9% to about 1 1 %, or about 9% to about 10%, or is about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 1 1 %, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21 %, about 22%, about 23%, about 24%, or about 25% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In at least some embodiments, the penetration-enhancing solvent comprises propylene glycol, dipropylene glycol, glycerin, or a mixture of two or more thereof, and the total amount of penetration-enhancing solvents ranges from about 5% to about 40%, preferably from about 8% to about 35% or about 10% to about 30%, or ranges from about 2% to about 20%, such as from about 4% to about 18%, from about 5% to about 15%, or from about 7% to about 14% by weight, relative to the total weight of the composition. In another preferred embodiment, the penetration-enhancing solvent consists of or consists essentially of propylene glycol, dipropylene glycol, glycerin, or a mixture of two or more thereof, and the total amount of penetrationenhancing solvents ranges from about 5% to about 40%, preferably from about 8% to about 35% or about 10% to about 30%, or ranges from about 2% to about 20%, such as from about 4% to about 18%, from about 5% to about 15%, or from about 7% to about 14% by weight, or is about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 1 1 %, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21 %, about 22%, about 23%, about 24%, or about 25% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In a further preferred embodiment, the penetration-enhancing solvent comprises, consists essentially of, or consists of C2-C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols, and the total amount of penetrationenhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition. In a still further preferred embodiment, the penetration-enhancing solvent comprises, consists essentially of, or consists of C2- C16 diols and/or C2-C16 triols, for example C2-C8 diols and/or C2-C8 triols, and the total amount of penetration-enhancing solvents ranges from about 2% to about 50%, preferably from about 5% to about 45%, more preferably from about 7% to about 40%, more preferably still from about 8% to about 35%, and most preferably from about 8% to about 30% by weight, relative to the total weight of the composition.
Active Agents
Compositions according to the disclosure comprise at least one active agent. Active agents that can be used include amino acids, osmolytes, carboxylic acids, and combinations of two or more thereof. In preferred embodiments, the compositions comprise at least one osmolyte, at least one amino acid, and at least one carboxylic acid.
Amino Acids Optionally, compositions according to the disclosure comprise at least one amino acid. Optionally, in various embodiments, compositions according to the disclosure can comprise one, two, or three amino acids. Amino acids that can be chosen include those that are basic, acidic, or neutral at neutral pH. In preferred embodiments, compositions include at least one basic amino acid.
As used herein, the term “amino acid” includes amino carboxylic acids and salts thereof as well as amino sulfonic acids and salts thereof. As used herein, amino acids are understood to refer to organic compounds containing a carboxylic acid group ( — COOH) (amino carboxylic acids) and/or sulfonic acid group ( — S(=O)2-OH) (amino sulfonic acids) and an amino group ( — NH2) which may be primary or secondary, or may be intra-cyclic, along with a side chain (R group) specific to each amino acid.
Amino carboxylic acids that may be chosen include, for example, alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, and combinations of two or more thereof. Exemplary amino sulfonic acids include aminomethane sulfonic acid, 2-aminoethane sulfonic acid (taurine), aminopropane sulfonic acid, aminobutane sulfonic acid, aminohexane sulfonic acid, aminoisopropyl sulfonic acid, aminododecyl sulfonic acid, aminobenzene sulfonic acid, aminotoluene sulfonic acid, sulfanilic acid, chlorosu Ifani lie acid, diamino benzene sulfonic acid, amino phenol sulfonic acid, amino propyl benzene sulfonic acid, amino hexyl benzene sulfonic acid, and combinations of two or more thereof.
Salts of amino acids are also included in the term “amino acid,” whether or not so stated. By way of non-limiting example, salts that may be chosen include salts with organic or mineral bases, for example the salts of alkali metals, such as the lithium, sodium, or potassium salts; the salts of alkaline earth metals, such as the magnesium or calcium salts, and the zinc salts.
Furthermore, amino acids can be in either the D-, L-, or DL- configuration. In some preferred embodiments, it is advantageous to choose amino acids in the L- configuration, for example L-proline, L-methionine, L-serine, L-arginine, L-lysine, or combinations of two or more thereof. In some embodiments it is particularly advantageous to choose one or more amino carboxylic acids. Thus, in various embodiments, the compositions according to the disclosure comprise one or more amino acids of formula (I):
Figure imgf000014_0001
wherein: p is an integer equal to 1 or 2, and when p = 1 , R forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, preferably 5 ring members, it being possible for this ring to be substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl; or when p = 2, R represents a hydrogen atom or a saturated, linear, or branched (C1 -C12)alkyl group, preferably a (C1 -C4)alkyl group, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, -CONH2, -NH-C(NH)-NH2, or an imidazole ring.
In some embodiments when p = 1 , R forms, together with the nitrogen atom, a saturated heterocycle comprising 5 ring members, this ring not being substituted.
In some embodiments when p = 2, R represents a hydrogen atom or a saturated, linear, or branched (C1 -C4)alkyl group, optionally substituted by one or more groups chosen from hydroxyl (-OH), amino (-NH2), -CONH2, -NH-C(NH)-NH2, or an imidazole ring. In some embodiments p is preferably 2.
In some embodiments, the compositions comprise one or more amino acids chosen from glycine, proline, methionine, serine, arginine, lysine, histidine, salts of any of the foregoing (in particular alkali metal, alkaline earth metal, or zinc salts), or combinations of two or more thereof. In at least certain embodiments, the amino acid compounds in the composition consist essentially of or consist of amino acids chosen from glycine, proline, methionine, serine, arginine, lysine, histidine, salts of any of the foregoing (in particular alkali metal, alkaline earth metal, or zinc salts), or combinations of two or more thereof. In some embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of glycine and/or salts thereof. In other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of arginine and/or salts thereof. In other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of proline and/or salts thereof. In still other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of methionine and/or salts thereof. In other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of serine and/or salts thereof. In still other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of arginine and/or salts thereof. In other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of histidine and/or salts thereof. In still other embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of lysine and/or salts thereof. In still further embodiments, the amino acid(s) useful in the compositions may comprise, consist essentially of, or consist of basic amino acids and/or salts thereof.
In various embodiments, the total amount of amino acids may range from about 0.1 % to about 15%, such as about 0.1 % to about 12%, about 0.1% to about 10%, about 0.1 % to about 9%, about 0.1 % to about 8%, about 0.1 % to about 7%, about 0.1 % to about 6%, about 0.1 % to about 5.5%, about 0.1 % to about 5%, about 0.1 % to about 4.5%, about 0.1% to about 4%, about 0.1 % to about 3.5%, about 0.1 % to about 3%, about 0.1 % to about 2.5%, about 0.1 % to about 2%, about 0.1 % to about 1 .5%, about 0.1% to about 1%, about 0.5% to about 15%, about 0.5% to about 12%, about 0.5% to about 10%, about 0.5% to about 9%, about 0.5% to about 8%, about 0.5% to about 7%, about 0.5% to about 6%, about 0.5% to about 5.5%, about 0.5% to about 5%, about 0.5% to about 4.5%, about 0.5% to about 4%, about 0.5% to about 3.5%, about 0.5% to about 3%, about 0.5% to about 2.5%, about 0.5% to about 2%, about 0.5% to about 1.5%, about 0.5% to about 1%, about 1 % to about 15%, about 1 % to about 12%, about 1 % to about 10%, about 1 % to about 9%, about 1 % to about 8%, about 1 % to about 7%, about 1 % to about 6%, about 1 % to about 5.5%, about 1 % to about 5%, about 1 % to about 4.5%, about 1 % to about 4%, about 1 % to about 3.5%, about 1 % to about 3%, about 1 % to about 2.5%, about 1 % to about 2%, about 1 % to about 1 .5%, about 1 .5% to about 15%, about 1 .5% to about 12%, about 1 .5% to about 10%, about 1 .5% to about 9%, about 1 .5% to about 8%, about 1 .5% to about 7%, about 1 .5% to about 6%, about 1 .5% to about 5.5%, about 1 .5% to about 5%, about 1 .5% to about 4.5%, about 1 .5% to about 4%, about 1 .5% to about 3.5%, about 1 .5% to about 3%, about 1 .5% to about 2.5%, about 1 .5% to about 2%, about 2% to about 15%, about 2% to about 12%, about 2% to about 10%, about 2% to about 9%, about 2% to about 8%, about 2% to about 7%, about 2% to about 6%, about 2% to about 5.5%, about 2% to about 5%, about 2% to about 4.5%, about 2% to about 4%, about 2% to about 3.5%, about 2% to about 3%, about 2% to about 2.5%, about 2.5% to about 15%, about 2.5% to about 12%, about 2.5% to about 10%, about 2.5% to about 9%, about 2.5% to about 8%, about 2.5% to about 7%, about 2.5% to about 6%, about 2.5% to about 5.5%, about 2.5% to about 5%, about 2.5% to about 4.5%, about 2.5% to about 4%, about 2.5% to about 3.5%, about 2.5% to about 3%, about 3% to about 15%, about 3% to about 12%, about 3% to about 10%, about 3% to about 9%, about 3% to about 8%, about 3% to about 7%, about 3% to about 6%, about 3% to about 5.5%, about 3% to about 5%, about 3% to about 4.5%, about 3% to about 4%, about 3% to about 3.5%, about 3.5% to about 15%, about 3.5% to about 12%, about 3.5% to about 10%, about 3.5% to about 9%, about 3.5% to about 8%, about 3.5% to about 7%, about 3.5% to about 6%, about 3.5% to about 5.5%, about 3.5% to about 5%, about 3.5% to about 4.5%, about 3.5% to about 4%, about 4% to about 15%, about 4% to about 12%, about 4% to about 10%, about 4% to about 9%, about 4% to about 8%, about 4% to about 7%, about 4% to about 6%, about 4% to about 5.5%, about 4% to about 5%, about 4% to about 4.5%, about 4.5% to about 15%, about 4.5% to about 12%, about 4.5% to about 10%, about 4.5% to about 9%, about 4.5% to about 8%, about 4.5% to about 7%, about 4.5% to about 6%, about 4.5% to about 5.5%, or about 4.5% to about 5% by weight, relative to the total weight of the composition. In preferred embodiments, the total amount of amino acids ranges from about 2.5% to about 7.5%, about 3% to about 7%, about 3.5% to about 6.5%, about 3.75% to about 6.25%, about 4% to about 6%, about 4.25% to about 5.75%, about 4.5% to about 5.5%, about 4.75% to about 5.25%, or about 4.8% to about 5.2% by weight, relative to the total weight of the composition. For example, the total amount of amino acids may be about 4.5%, about 4.6%, about 4.7%, about 4.8%, about 4.9%, about 5.0%, about 5.1 %, about 5.2%, about 5.3%, about 5.4%, or about 5.5% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits. In some preferred embodiments, the compositions comprise a total amount of basic amino acids in any of the foregoing ranges and amounts.
In one preferred embodiment, the compositions comprise arginine and/or a salt thereof. In another preferred embodiment, where more than one amino acid is present, arginine is present in the composition in an amount greater than the combined amounts of the other amino acid(s) present, for example arginine comprises greater than about 50%, such as greater than about 60%, greater than about 70%, greater than about 80%, greater than about 90%, greater than about 95%, greater than about 98%, or greater than about 99% of all amino acids present in the composition. In a further preferred embodiment, arginine is the only the basic amino acid in the composition.
In various preferred embodiments, the composition comprises arginine in an amount ranging from about 1 % to about 10%, such as from about 2.5% to about 7.5%, preferably from about 3% to about 7%, more preferably from about 3.5% to about 6.5%, more preferably from about 3.75% to about 6.25%, more preferably from about 4% to about 6%, more preferably from about 4.25% to about 5.75%, more preferably still from about 4.5% to about 5.5%, yet more preferably from about 4.75% to about 5.25%, and most preferably from about 4.8% to about 5.2%, or may be present in an amount of about 4.5%, about 4.6%, about 4.7%, about 4.8%, about 4.9%, about 5.0%, about 5.1 %, about 5.2%, about 5.3%, about 5.4%, or about 5.5% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In another preferred embodiment, compositions according to the disclosure comprise serine and/or a salt thereof. If present, the amount of serine may range from about 0.01% to about 2%, such as from about 0.01 % to about 1 .5%, about 0.01 % to about 1 %, about 0.01 % to about 0.5%, about 0.01% to about 0.4%, about 0.01 % to about 0.3%, about 0.01% to about 0.2%, about 0.01 % to about 0.1 %, about 0.05% to about 2%, about 0.05% to about 1.5%, about 0.05% to about 1 %, about 0.05% to about 0.5%, about 0.05% to about 0.4%, about 0.05% to about 0.3%, about 0.05% to about 0.2%, about 0.05% to about 0.1 %, about 0.1 % to about 2%, about 0.1 % to about 1 .5%, about 0.1 % to about 1 %, or about 0.1 % to about 0.5% by weight, relative to the total weight of the composition. For example, in some preferred embodiments, the compositions may comprise serine in an amount ranging from about 0.05% to about 1 .5%, preferably from about 0.1 % to about 1 %, more preferably from about 0.25% to about 0.75%, and most preferably from about 0.4% to about 0.6%, such as about 0.1 %, about 0.25%, about 0.5%, about 0.75%, or about 1% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In some embodiments, it may be advantageous to choose at least one basic amino acid and at least one additional amino acid chosen from acidic and/or neutral amino acids. For example, in preferred embodiments it may be advantageous to include at least one basic amino acid and serine in compositions according to the disclosure, and to choose total amounts of basic amino acids and serine such that the composition has a weight ratio of the total amount of basic amino acids to the total amount of serine that is greater than about 2, such as greater than about 3, greater than about 4, greater than about 5, or greater than about 6. For example, the composition may have a weight ratio of the total amount of basic amino acids to the total amount of serine ranging from about 2 to about 15, such as from about 4 to about 14, from about 6 to about 13, from about 8 to about 12, or from about 9 to about 11 . In further examples, the weight ratio of the total amount of basic amino acids to serine may be about 8, about 9, about 10, about 1 1 , or about 12. In some preferred embodiments, the composition comprises serine and has a weight ratio of the total amount of basic amino acids to serine ranging from about 2 to about 15, preferably from about 8 to about 12, more preferably from about 9 to about 1 1 , or is about 8, about 9, about 10, about 1 1 , or about 12, including all ranges and subranges using any of the foregoing as upper and lower limits.
In still further preferred embodiments, the compositions comprise serine and arginine, and have a weight ratio of arginine to serine ranging from about 2 to about 15, preferably from about 8 to about 12, more preferably from about 9 to about 1 1 , or is about 8, about 9, about 10, about 1 1 , or about 12, including all ranges and subranges using any of the foregoing as upper and lower limits.
Osmolytes
Osmolytes are molecules, typically of lower molecular weight, used by cells to maintain cell volume, regulate osmotic pressure, and maintain cellular homeostasis, for example in response to environmental stressors. Organic osmolytes include amino carboxylic acids, amino sulfonic acids, salts thereof, and derivatives thereof, carbohydrates such sugars and sugar alcohols (polyols), polyamines, betaines, methylsulfonium compounds (e.g., dimethylsulfonopropionate), and urea. For purposes of this disclosure, “osmolytes” includes derivatives of amino carboxylic acids, derivatives of amino sulfonic acids, and salts of the derivatives (referred to herein collectively as “amino acid derivatives”), but does not include amino carboxylic acids, amino sulfonic acids, or salts thereof which are described above, and does not include polyols.
Optionally, compositions according to the disclosure comprise one or more osmolytes, preferably one or more organic osmolytes. In some embodiments, the compositions comprise more than one osmolyte. Without intending to be bound by theory, it is believed that the use of osmolytes as active agents in compositions according to the disclosure permits treated hair to maintain moisture equilibrium, thus reducing potential damage to the hair, or restores moisture equilibrium to already- damaged hair, thereby allowing the treated hair to recover strength and/or reduced elasticity associated with healthy hair.
In preferred embodiments, compositions according to the disclosure comprise one or more osmolytes chosen from carbohydrate sugars, polyamines, amino acid derivatives such as betaines, and more preferably are chosen from compounds of formula (II) or salts thereof:
(R1 )(R2)(R3)m-A+-CR4R5-(X)n-Y-
(H) wherein:
R1 , R2, and R3 are independently chosen from C1 -C4 alkyl groups, preferably C1 -C2 alkyl groups, more preferably methyl;
A is N or S; m and n are independently 0 or 1 ;
X is a divalent alkyl group (= an alkylene group), linear or branched, saturated or unsaturated, having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, optionally substituted by one or more groups chosen from hydroxyl (- OH) or amino (-NH2); and
Y’ is -COO- or -OSO3-; with the provisos that: o when A is S, then m = 0 and R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains), (C1 -C10) hydrocarbon chain, preferably (C1 -C6), more preferably (C1 -C4); optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or -C(NH)- and/or optionally substituted by one or more groups chosen from hydroxyl (-OH), amino (-NH2), -SH, -COOH, or -CONH2; o when A is N and m = 0, R4 represents a hydrogen atom or a saturated, linear or branched (C1 -C8)alkyl, preferably (C1 -C4)alkyl, group; and R5 forms, with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, preferably 5 to 6 ring members, it being possible for this ring to be substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl ; and o when A is N and m = 1 , then R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains) (C1 -C10) hydrocarbon chain, preferably (C1 -C6), more preferably (C1 -C4); optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or -C(NH)- and/or optionally substituted by one or more groups chosen from hydroxyl (-OH), amino (-NH2), -SH, -COOH, or -CONH2.
Useful and non-limiting polyamine compounds may comprise primary and/or secondary and/or tertiary and/or quaternary amine functional groups. By way of example, polyamines that can be chosen include diamines, triamines, tetramines, pentamines, and polymeric polyamines or polyimines, such as, for example, hexamethylenediamine, diethylenetetramine, diethylenetriamine, polyethyleneimine (PEI), polyvinyl amine, polyether amine, polylysine, ethylene diamine, 1 ,3- diaminopropane, cadaverine, spermidine, spermine, putrescine, tetraethylmethylenediamine, triethylenetetramine, or combinations of two or more thereof. In some embodiments, useful polyamines are chosen from putrescine, spermidine, and/or spermine.
Useful and nonlimiting examples of betaines include glycine betaine, valine betaine, alanine betaine, proline betaine, hydroxyproline betaine, etc. Salts of betaines can also be used and are expressly included in the term “betaine” unless expressly stated otherwise. In particularly preferred embodiments, betaines are chosen from those corresponding to formula (II). Exemplary useful compounds of formula (II) include the compounds shown in FIGS. 5A-5B. As shown in FIG. 5A, in some embodiments the compounds of formula (II) are in zwitterionic form, and as shown in FIG. 5B, in some embodiments the compounds of formula (II) have a corresponding counterion, X’. The counterion is not limited, and can be any suitable counterion, for example a chloride ion, bromide ion, iodide ion, sulfate anion, sulfonate anion, methyl sulfate anion, phosphate anion, nitrate anion, etc. Thus, as used herein a “compound of formula (II)” expressly includes both the ionic form of the compound as well as salt forms, whether or not so stated.
As shown in FIGS. 5A-5B, exemplary useful compounds of formula (II) include betaine and betaine derivatives (referred to herein as “betaines”), for example valine betaine, glutamic acid betaine, glutamine betaine, trimethyl lysine, glycine betaine (trimethyl glycine), histidine betaine, N-methyl histidine betaine, alanine betaine, beta-alanine betaine, choline sulfate, pipecolic acid betaine, proline betaine, hydroxyproline betaine, tyrosine betaine, phenylalanine betaine, tryptophan betaine, leucine betaine, isoleucine betaine, and/or dimethylsulfoniopropionate. In a preferred embodiment, the osmolyte is glycine betaine (trimethyl glycine), alone or in combination with one or more additional osmolytes, for example one or more additional compounds of formula (II).
In some preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II). In additional preferred embodiments, compositions according to the disclosure comprise one or more compounds of formula (II) that is a zwitterionic amino acid derivative bearing a quaternary ammonium group and comprising in total from 1 to 12 carbon atoms, such as from 2 to 10 carbon atoms, or from 3 to 8 carbon atoms.
In some preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II) wherein R1 = R2 = methyl; A is N; and/or Y is COO-. In some other preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II) wherein R3 is methyl. In other preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II) wherein X is a divalent alkyl group, linear or branched, preferably saturated, having from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, optionally substituted by one group chosen from hydroxyl or amino. In still other preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II) wherein X is a divalent alkyl group, linear or branched, preferably saturated, having from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 2 carbon atoms (not substituted), such as methylene or ethylene. In other preferred embodiments, compositions according to the disclosure comprise at least one compound of formula (II) wherein R4 and R5, which may be the same or different, are chosen from a hydrogen atom, a saturated, linear or branched (C1 -C10) alkyl group, preferably (C1 -C6)alkyl, more preferably (C1 -C4) alkyl; a phenyl group; a benzyl group; an alkyl group substituted by a cyclic group (saturated or not, mono or bi-cyclic); a cyclic group (saturated or not, mono or bi-cyclic) substituted by an alkyl group; all these groups being optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or -C(NH)- and/or optionally substituted by one or more groups chosen from hydroxyl (-OH), amino (-NH2), -SH, -COOH, -CONH2; more preferably where R4 is hydrogen and/or where R5 is a hydrogen atom or a saturated, linear or branched (C1 -C6)alkyl, more preferably (C1 -C4) alkyl; optionally substituted by one group chosen from hydroxyl (-OH), amino (-NH2), -COOH, or -CONH2. In some preferred embodiments, when A is N and m = 0, R5 forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, preferably 5 to 6 ring members, optionally substituted by one hydroxy group. In further preferred embodiments, R1 = R2 = methyl, A is N, Y is COO-, and X (if present) is a divalent alkyl group that may be linear or branched, saturated or unsaturated, having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 2 carbon atoms.
In one preferred embodiment, the composition comprises at least one compound of formula (II) wherein R1 = R2 = R3 = methyl; A is N; Y is COO-; X is a divalent alkyl group, linear or branched, preferably saturated, having from 1 to 4 carbon atoms, optionally substituted by one group chosen from hydroxyl or amino, more preferably 1 to 2 carbon atoms (not substituted), such as methylene or ethylene; R4 is hydrogen; and R5 forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, preferably 5 to 6 ring members, optionally substituted by one hydroxy group.
In preferred embodiments, the composition comprises at least one osmolyte, and the osmolyte comprises, consists essentially of, or consists of one or more of the compounds shown in FIGS. 5A-5B. In more preferred embodiments, compositions according to the disclosure comprise trimethyl glycine (referred to interchangeably as glycine betaine), optionally in combination with at least one additional osmolyte, and in particularly preferred embodiments the osmolyte in the composition comprises, consists essentially of, or consists of glycine betaine optionally with at least one additional compound of formula (II). Useful and non-limiting examples of carbohydrate sugars that can be used include C3-C6 monosaccharides, for example pentoses and/or derivatives thereof, or hexoses and/or derivatives thereof. For example, the sugars may optionally be chosen from chosen from xylose, arabinose, ribose, 2-deoxy-ribose, ribulose, deoxy-ribulose, arabinose, xylulose, allose, altrose, glucose (including dextrose), glucosamine, mannose, gulose, idose, galactose, talose, sorbose, psicose, fructose, tagatose, or combinations of two or more thereof. In at least some embodiments, the sugars are chosen from disaccharides, for example sucrose (also saccharose), maltose, lactose, cellobiose, trehalose, dextran, or from polysaccharides, for example maltotriose, starch, dextrins, cellulose, glycogen, or combinations of two or more thereof. In some embodiments, the sugars are preferably chosen from trehalose, glucose, sucrose, fructose, fructans, or combinations of two or more thereof.
In various embodiments, the total amount of osmolytes present in the composition may range from about 0.01 % to about 15%, such as, for example, from about 0.1 % to about 10%, from about 0.1 % to about 9%, from about 0.1 % to about 8%, from about 0.1 % to about 7%, from about 0.1 % to about 6%, from about 0.1 % to about 5%, from about 0.1 % to about 4%, from about 0.1 % to about 3%, from about 0.1 % to about 2%, from about 0.1 % to about 1 %, from about 0.5% to about 10%, from about 0.5% to about 9%, from about 0.5% to about 8%, from about 0.5% to about 7%, from about 0.5% to about 6%, from about 0.5% to about 5%, from about 0.5% to about 4%, from about 0.5% to about 3%, from about 0.5% to about 2%, from about 0.5% to about 1 %, from about 1 % to about 10%, from about 1 % to about 9%, from about 1 % to about 8%, from about 1 % to about 7%, from about 1% to about 6%, from about 1 % to about 5%, from about 1 % to about 4%, from about 1% to about 3%, from about 1 % to about 2%, from about 1 .5% to about 10%, from about 1 .5% to about 9%, from about 1 .5% to about 8%, from about 1 .5% to about 7%, from about 1 .5% to about 6%, from about 1 .5% to about 5%, from about 1 .5% to about 4%, from about 1 .5% to about 3%, from about 1 .5% to about 2%, from about 2% to about 10%, from about 2% to about 9%, from about 2% to about 8%, from about 2% to about 7%, from about 2% to about 6%, from about 2% to about 5%, from about 2% to about 4%, from about 2% to about 3%, from about 2.25% to about 10%, from about 2.25% to about 9%, from about 2.25% to about 8%, from about 2.25% to about 7%, from about 2.25% to about 6%, from about 2.25% to about 5%, from about 2.25% to about 4%, from about 2.25% to about 3%, from about 2.5% to about 10%, from about 2.5% to about 9%, from about 2.5% to about 8%, from about 2.5% to about 7%, from about 2.5% to about 6%, from about 2.5% to about 5%, from about 2.5% to about 4%, from about 2.5% to about 3% by weight, relative to the total weight of the composition. For example, the total amount of osmolytes present in the composition may be about 2.0%, about 2.1 %, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In preferred embodiments the compositions comprise at least one betaine, and the total amount of betaines ranges from about 0.5% to about 5%, for example from about 1% to about 5%, preferably from about 1 .25% to about 4%, more preferably from about 1 .5% to about 3.5%, more preferably from about 2% to about 3% or from about 2% to about 2.5%, more preferably still from about 2.25% to about 2.75%, and most preferably from about 2.3% to about 2.6%, or may be about 2.0%, about 2.1%, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
In a particularly preferred embodiment, the composition comprises glycine betaine in an amount ranging from about 0.5% to about 5%, for example about 1 % to about 5%, preferably from about 1 .25% to about 4%, more preferably from about 1 .5% to about 3.5%, more preferably from about 2% to about 3% or from about 2% to about 2.5%, more preferably still from about 2.25% to about 2.75%, and most preferably from about 2.3% to about 2.6%, or the glycine betaine may be present in an amount of about 2.0%, about 2.1 %, about 2.2%, about 2.3%, about 2.4%, about 2.5%, about 2.6%, about 2.7%, about 2.8%, about 2.9%, or about 3.0% by weight, relative to the total weight of the composition, including all ranges and subranges using any of the foregoing as upper and lower limits.
It may be advantageous, in some embodiments, to choose amounts of amino acids and osmolytes to provide a weight ratio of the total amount of amino acid(s) and salts thereof in the composition to the total amount of osmolytes in the composition that is greater than about 0.1 , for example greater than about 0.2, greater than about 0.5, greater than about 1 , greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2. In various embodiments, the weight ratio of the total amount of amino acid(s) and salts thereof to the total amount of osmolytes may range from about 0.1 to about 10, such as from about 0.2 to about 8, from about 0.5 to about 6, from about 1 to about 5, from about 1 .2 to about 4, or from about 1 .5 to about 3.5. In other embodiments, the weight ratio of the total amount of amino acid(s) and salts thereof to the total amount of osmolytes may range from greater than 1 to about 4, such as from about 1 .25 to about 3.5, from about 1 .5 to about 3, from about 1 .75 to about 2.5, from about 1 .75 to about 2.25, or from about 1 .8 to about 2.2. For example, the weight ratio of the total amount of amino acid(s) in the composition to the total amount of osmolytes in the composition may be about 1.1 , about 1 .2, about 1 .3, about 1 .4, about 1 .5, about 1 .6, about 1 .7, about 1 .8, about 1 .9, about 2, about 2.1 , about 2.2, about 2.3, about 2.4, or about 2.5, including all ranges and subranges using any of the foregoing as upper and lower limits.
In some embodiments, the compositions comprise a total amount of amino acids chosen from compounds of formula (I) and a total amount of osmolytes chosen from compounds of formula (II) such that a weight ratio of compounds of formula (l):compounds of formula (II) is greater than about 0.5, greater than about 0.75, or greater than about 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2. In some embodiments, the weight ratio of compounds of formula (I): compounds of formula (II) in the composition may range from about 0.5 to about 6, for example from about 1 to about 4, from about 1 .25 to about 3.5, from about 1 .5 to about 3, from about 1 .75 to about 2.5, from about 1 .75 to about 2.25, or from about 1.8 to about 2.2. For example, the weight ratio of compounds of formula (l):compounds of formula (II) in the composition may be about 0.5, about 0.6, about 0.7, about 0.8, about 0.9, about 1 , about 1.1 , about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, about 1.9, about 2, about 2.1 , about 2.2, about 2.3, about 2.4, or about 2.5, including all ranges and subranges using any of the foregoing as upper and lower limits.
In a particularly preferred embodiment, the composition comprises arginine and glycine betaine and has a weight ratio of arginine to glycine betaine of greater than 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1 .75, or greater than about 2, for example ranging from greater than 1 to about 4, preferably from about 1 .5 to about 3, more preferably from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25. In another particularly preferred embodiment, the composition comprises arginine, serine, and glycine betaine and has a weight ratio of the total amount of [arginine + serine] to glycine betaine of greater than 1 , for example greater than about 1 .25, greater than about 1 .5, greater than about 1.75, or greater than about 2, for example ranging from greater than 1 to about 4, preferably from about 1 .5 to about 3, more preferably from about 1 .75 to about 2.5, and most preferably from about 1 .75 to about 2.25.
Carboxylic Acids
Optionally, compositions according to the disclosure include at least one carboxylic acid. According to various embodiments of the disclosure, useful carboxylic acids include organic compounds that include, for example, one (mono-), two (di-), three (tri-), or more acid functional groups and at least one carbon atom.
Carboxylic acids that can be used may optionally have a molecular weight of less than about 500 g/mol, less than about 400 g/mol, less than about 300 g/mol, or less than about 200 g/mol. In preferred embodiments, the carboxylic acids have a molecular weight of less than about 300 g/mol, or less than about 200 g/mol.
Salts of carboxylic acids can also be used and are expressly included in the term “carboxylic acid” unless expressly stated otherwise. The salts include salts with organic or mineral bases, for example the salts of alkali metals, such as the lithium, sodium, or potassium salts; the salts of alkaline earth metals, such as the magnesium or calcium salts, and the zinc salts. The alkali metal or alkaline earth metal salts are preferred in some embodiments, and in particular the sodium salts.
In preferred embodiments, carboxylic acids comprise from 2 to 20 carbon atoms, such as from 2 to 18 carbon atoms, from 3 to 16 carbon atoms, or from 3 to 14 carbon atoms. In some preferred embodiments, the compositions comprise one or more hydroxylated (poly)carboxylic acids comprising from 2 to 10 carbon atoms, such as from 2 to 8 carbon atoms, or from 3 to 6 carbon atoms, and may be saturated or unsaturated, and linear or branched, and/or a salt thereof. These (poly)acids are different from the compounds of amino acids type described above. Useful (poly)acids comprise at least one -COOH group (in acid or salified form); they can thus comprise a single -COOH group (monoacid) or can comprise more than one, for example two - COOH groups (in acid or salified form), or two or three -COOH groups (in acid or salified form) (polyacids). Useful (poly)acids also comprise at least one -OH group, such as from one to three or from two to three -OH groups, for example one, two, or three -OH groups. Preferably, the (poly)acids comprise in total from 2 to 8 or from 3 to 6 carbon atoms, and from two to three -OH groups, and their hydrocarbon chain is saturated or unsaturated, linear or branched, and preferably saturated and linear. In some preferred embodiments, the hydroxylated (poly)carboxylic acids and/or their salts comprise in total from 3 to 6 carbon atoms, from one to three -OH groups, and from two to three -COOH groups (in acid or salified form). Unless stated otherwise, as used herein the term “(poly)acid” includes both monoacids and polyacids.
Non-limiting examples of mono-carboxylic acids that can be chosen include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, lactic acid, salts thereof, or combinations of two or more thereof. In some embodiments, the carboxylic acid may comprise, consist essentially of, or consist of lactic acid and/or a salt thereof.
Non-limiting examples of di-carboxylic acids that can be chosen include oxalic acid, malonic acid, malic acid, glutaric acid, citraconic acid, succinic acid, adipic acid, tartaric acid, fumaric acid, maleic acid, salts thereof, or combinations of two or more thereof. In some embodiments, the compositions may include oxalic acid, malonic acid, malic acid, maleic acid, salts thereof, or combinations of two or more thereof.
Non-limiting examples of tricarboxylic acids include citric acid, isocitric acid, aconitic acid, propane-1 ,2,3-tricarboxylic acid, salts thereof, or combinations of two or more thereof. In some embodiments, the carboxylic acid may comprise, consist essentially of, or consist of citric acid and/or a salt thereof.
In some embodiments, the carboxylic acid(s) may be chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, maleic acid, lactic acid, salts thereof, or combinations of two or more thereof. In particularly preferred embodiments, the carboxylic acids are chosen from a-hydroxy acids and their salts, and in particular from lactic acid, glycolic acid, tartaric acid, or citric acid, and their salts, in particular alkali metal or alkaline earth metal salts. It may in some embodiments be particularly advantageous to choose citric acid, lactic acid, and/or tartaric acid and/or their salts, in particular alkali metal or alkaline earth metal salts, such as sodium citrate and/or sodium tartrate; and preferably citric acid and/or its salts, in particular alkali metal or alkaline earth metal salts, such as sodium citrate.
The total amount of carboxylic acid(s) may range from about 0.5% to about 20% by weight, relative to the total weight of the composition. For example, in some embodiments, the total amount of carboxylic acids ranges from about 1 % to about 15%, such as about about 1 % to about 12%, about 1 % to about 10%, about 1 % to about 9%, about 1 % to about 8%, about 1 % to about 7%, about 1 % to about 6%, about 1 % to about 5.5%, about 1 % to about 5%, about 1 % to about 4.5%, about 1 % to about 4%, about 1 % to about 3.5%, about 1 % to about 3%, about 1 % to about 2.5%, about 1 % to about 2%, about 1 % to about 1 .5%, about 1 .5% to about 15%, about 1 .5% to about 12%, about 1 .5% to about 10%, about 1 .5% to about 9%, about 1 .5% to about 8%, about 1 .5% to about 7%, about 1 .5% to about 6%, about 1 .5% to about 5.5%, about 1 .5% to about 5%, about 1 .5% to about 4.5%, about 1 .5% to about 4%, about 1 .5% to about 3.5%, about 1 .5% to about 3%, about 1 .5% to about 2.5%, about 1 .5% to about 2%, about 2% to about 15%, about 2% to about 12%, about 2% to about 10%, about 2% to about 9%, about 2% to about 8%, about 2% to about 7%, about 2% to about 6%, about 2% to about 5.5%, about 2% to about 5%, about 2% to about 4.5%, about 2% to about 4%, about 2% to about 3.5%, about 2% to about 3%, about 2% to about 2.5%, about 2.5% to about 15%, about 2.5% to about 12%, about 2.5% to about 10%, about 2.5% to about 9%, about 2.5% to about 8%, about 2.5% to about 7%, about 2.5% to about 6%, about 2.5% to about 5.5%, about 2.5% to about 5%, about 2.5% to about 4.5%, about 2.5% to about 4%, about 2.5% to about 3.5%, about 2.5% to about 3%, about 3% to about 15%, about 3% to about 12%, about 3% to about 10%, about 3% to about 9%, about 3% to about 8%, about 3% to about 7%, about 3% to about 6%, about 3% to about 5.5%, about 3% to about 5%, about 3% to about 4.5%, about 3% to about 4%, about 3% to about 3.5%, about 3.5% to about 15%, about 3.5% to about 12%, about 3.5% to about 10%, about 3.5% to about 9%, about 3.5% to about 8%, about 3.5% to about 7%, about 3.5% to about 6%, about 3.5% to about 5.5%, about 3.5% to about 5%, about 3.5% to about 4.5%, about 3.5% to about 4%, about 4% to about 15%, about 4% to about 12%, about 4% to about 10%, about 4% to about 9%, about 4% to about 8%, about 4% to about 7%, about 4% to about 6%, about 4% to about 5.5%, about 4% to about 5%, about 4% to about 4.5%, about 4.5% to about 15%, about 4.5% to about 12%, about 4.5% to about 10%, about 4.5% to about 9%, about 4.5% to about 8%, about 4.5% to about 7%, about 4.5% to about 6%, about 4.5% to about 5.5%, about 4.5% to about 5%, about 5% to about 15%, about 5% to about 12%, about 5% to about 10%, about 5% to about 9%, about 5% to about 8%, about 5% to about 7%, about 5% to about 6.5%, about 5% to about 6%, about 5% to about 5.5%, about 5.5% to about 15%, about 5.5% to about 12%, about 5.5% to about 10%, about 5.5% to about 9%, about 5.5% to about 8%, about 5.5% to about 7%, about 5.5% to about 6.5%, about 5.5% to about 6%, about 6% to about 15%, about 6% to about 12%, about 6% to about 10%, about 6% to about 9%, about 6% to about 8%, about 6% to about 7%, or about 6% to about 6.5% by weight, relative to the total weight of the composition.
In preferred embodiments, the total amount of carboxylic acid(s) ranges from about 0.5% to about 20%, such as from about 2% to about 15%, from about 4% to about 10%, about 4.5% to about 8%, about 5% to about 7%, about 5.5% to about 6.5%, about 5.7% to about 6.3%, or about 5.8% to about 6.2% by weight, relative to the total weight of the composition. For example, in some preferred embodiments, the composition comprises at least one carboxylic acid chosen from citric acid, lactic acid, tartaric acid, salts thereof, or combinations thereof, and has a total amount of carboxylic acids and salts ranging from about 0.5% to about 20%, such as from about 2% to about 15%, from about 4% to about 10%, preferably from about 4.5% to about 8%, more preferably from about 5% to about 7%, more preferably from about 5.5% to about 6.5%, more preferably still from about 5.7% to about 6.3%, and most preferably from about 5.8% to about 6.2% by weight, relative to the total weight of the composition.
It may be advantageous in some embodiments to choose amounts of amino acids and carboxylic acids such that the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids of greater than about 0.75. For example, in various embodiments, the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids of greater than about 0.8, such as greater than about 0.9, greater than about 1 , greater than about 1.1 , greater than about 1.2, greater than about 1.3, greater than about 1.4, or greater than about 1.5. In some embodiments, the composition has a weight ratio of the total amount of amino acids to the total amount of carboxylic acids ranging from about 0.75 to about 2, such as from about 0.8 to about 1.5, from about 0.8 to about 1 .35, or from about 0.8 to about 1 .2. In some preferred embodiments, the composition comprises arginine and at least one carboxylic acid chosen from citric acid, lactic acid, tartaric acid, salts thereof, or combinations thereof, and has a weight ratio of the total amount of amino acids and salts thereof to the total amount of carboxylic acids and salts thereof ranging from about 0.75 to about 2, preferably from about 0.8 to about 1 .5, more preferably from about 0.8 to about 1 .35, and most preferably from about 0.8 to about 1 .2.
Additional Solvents Compositions according to the disclosure optionally comprise at least one solvent in addition to the penetration-enhancing solvents discussed above. In various embodiments, additional solvents may be chosen from water, non-aqueous solvents other than the penetration-enhancing solvents discussed above, or a combination thereof.
In some embodiments, the additional solvent includes water. In certain embodiments, the composition comprises from about 50% to about 98% of water, by weight, relative to the total weight of the composition. In certain embodiments, the composition comprises water in an amount ranging from about 50% to about 95% water by weight, such as from about 50% to about 90%, about 55% to about 90%, about 60% to about 90%, or about 60% to about 80% by weight, relative to the total weight of the composition.
In further embodiments, the additional solvent may include at least one non-aqueous solvent other than the penetration-enhancing solvents discussed above. Exemplary and non-limiting additional non-aqueous solvents that can be used include, for example, organic solvents, fatty alcohols, fatty ethers, fatty esters, vegetable oils, mineral oils, liposomes, laminar lipid materials, or combinations of two or more thereof.
If present, the total amount of additional non-aqueous solvents in the composition may range from about 0.001% to about 10%, such as from about 0.01 % to about 10%, from about 0.1 % to about 10%, or from about 0.1 % to about 5% by weight, relative to the total weight of the composition.
In some preferred embodiments, the additional solvent comprises water and at least one additional non-aqueous solvent, wherein the total amount of nonaqueous solvents ranges from about 0.01 % to about 8%, preferably from about 0.05% to about 5%, more preferably from about 0.1 % to about 3% by weight, relative to the total weight of the composition.
Surfactants
Compositions according to the disclosure may optionally comprise at least one surfactant. For example, the compositions may comprise one or more cationic surfactants and/or amphoteric surfactants, and in some embodiments the compositions may comprise mixtures of surfactants having the same or different ionicities.
Although the compositions may optionally include one or more anionic surfactants and/or nonionic surfactants, in at least some embodiments, the compositions are free or substantially free of anionic surfactants and/or nonionic surfactants. For example, in some embodiments the compositions comprise less than about 3%, such as less than about 2.5%, less than about 2%, less than about 1 .75%, less than about 1.5%, less than about 1.25%, less than about 1%, less than about 0.75%, less than about 0.5%, less than about 0.25%, less than about 0.2%, less than about 0.1 %, less than about 0.05%, less than about 0.01 %, or less than about 0.001 % of anionic surfactants and/or nonionic surfactants.
In at least some embodiments, the compositions comprise at least one cationic surfactant. The term “cationic surfactant” means a surfactant that is positively charged when it is contained in the composition(s) according to the disclosure. This surfactant may bear one or more positive permanent charges or may contain one or more functions that are cationizable in the composition according to the disclosure. Non-limiting examples of useful cationic surfactants include brassicamidopropyl dimethylamine, behenalkonium chloride, benzethonium chloride, cetylpyridinium chloride, behentrimonium chloride, lauralkonium chloride, cetalkonium chloride, cetrimonium bromide, cetrimonium chloride, cethylamine hydrofluoride, chlorallylmethenamine chloride (Quaternium-15), distearyldimonium chloride (Quaternium-5), dodecyl dimethyl ethylbenzyl ammonium chloride (Quaternium-14), Quaternium-22, Quaternium-26, Quaternium-18 hectorite, dimethylaminoethylchloride hydrochloride, cysteine hydrochloride, diethanolammonium POE (10) oletyl ether phosphate, diethanolammonium POE (3)oleyl ether phosphate, tallow alkonium chloride, dimethyl dioctadecylammoniumbentonite, stearalkonium chloride, domiphen bromide, denatonium benzoate, myristalkonium chloride, laurtrimonium chloride, ethylenediamine dihydrochloride, guanidine hydrochloride, pyridoxine HCI, iofetamine hydrochloride, meglumine hydrochloride, methylbenzethonium chloride, myrtrimonium bromide, oleyltrimonium chloride, polyquaternium-1 , procainehydrochloride, cocobetaine, stearalkonium bentonite, stearalkoniumhectonite, stearyl trihydroxyethyl propylenediamine dihydrofluoride, tallowtrimonium chloride, hexadecyltrimethyl ammonium bromide, stearamidopropyl dimethylamine, or combinations thereof. In preferred embodiments, the compositions comprise at least one cationic surfactant chosen from brassicamidopropyl dimethylamine, behentrimonium chloride, cetrimonium chloride, stearamidopropyl dimethylamine, or combinations of two or more thereof. If present, the total amount of cationic surfactants may range up to about 10%, such as up to about 9%, up to about 8%, up to about 7%, up to about 6%, up to about 5%, up to about 4%, up to about 3.5%, up to about 3%, up to about 2.5%, up to about 2%, up to about 1 .5%, up to about 1 %, or up to about 0.5% by weight, relative to the total weight of the composition. For example, the total amount of cationic surfactants may range from about 0.001 % to about 10%, from about 0.01 % to about 8%, from about 0.1 % to about 6%, or from about 0.5% to about 4% by weight, relative to the total weight of the composition. In at least some preferred embodiments, the compositions comprise at least one cationic surfactant, and have a total amount of cationic surfactants ranging from about 0.25% to about 8%, preferably from about 0.5% to about 7%, more preferably from about 0.75% to about 6%, and most preferably from about 1 % to about 5% by weight, relative to the total weight of the composition.
In at least some embodiments, the compositions comprise at least one amphoteric surfactant. Non-limiting examples of useful amphoteric surfactants include derivatives of aliphatic secondary and tertiary amines where the aliphatic radical can be straight or branched chain and one of the aliphatic substituents contains from about
8 to about 18 carbon atoms and one contains an anionic group such as carboxy, sulfonate, sulfate, phosphate, or phosphonate. Exemplary amphoteric surfactants include sodium cocaminopropionate, sodium cocaminodipropionate, sodium cocoamphoacetate, sodium cocoamphohydroxypropylsulfonate, sodium cocoamphopropionate, sodium cornamphopropionate, sodium lauraminopropionate, sodium lauroamphoacetate, sodium lauroamphohydroxypropylsulfonate, sodium lauroamphopropionate, sodium cornamphopropionate, sodium lauriminodipropionate, ammonium cocaminopropionate, ammonium cocaminodipropionate, ammonium cocoamphoacetate, ammonium cocoamphohydroxypropylsulfonate, ammonium cocoamphopropionate, ammonium cornamphopropionate, ammonium lauraminopropionate, ammonium lauroamphoacetate, ammonium lauroamphohydroxypropylsulfonate, ammonium lauroamphopropionate, ammonium cornamphopropionate, ammonium lauriminodipropionate, triethanonlamine cocaminopropionate, triethanonlamine cocaminodipropionate, triethanonlamine cocoamphoacetate, triethanonlamine cocoamphohydroxypropylsulfonate, triethanonlamine cocoamphopropionate, triethanonlamine cornamphopropionate, triethanonlamine lauraminopropionate, triethanonlamine lauroamphoacetate, triethanonlamine lauroamphohydroxypropylsulfonate, triethanonlamine lauroamphopropionate, triethanonlamine cornamphopropionate, triethanonlamine lauriminodipropionate, cocoamphodipropionic acid, disodium caproamphodiacetate, disodium caproamphoadipropionate, disodium capryloamphodiacetate, disodium capryloamphodipriopionate, disodium cocoamphocarboxyethylhydroxypropylsulfonate, disodium cocoamphodiacetate, disodium cocoamphodipropionate, disodium dicarboxyethylcocopropylenediamine, disodium laureth-5 carboxyamphodiacetate, disodium lauriminodipropionate, disodium lauroamphodiacetate, disodium lauroamphodipropionate, disodium oleoamphodipropionate, disodium PPG-2-isodecethyl-7 carboxyamphodiacetate, lauraminopropionic acid, lauroamphodipropionic acid, lauryl aminopropylglycine, and lauryl diethylenediaminoglycine.
Betaine surfactants may also be used. For example, coco dimethyl carboxymethyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alphacarboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, cetyl dimethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine, stearyl bis-(2- hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma-carboxypropyl betaine, lauryl bis-(2-hydroxypropyl) alpha-carboxyethyl betaine, coco dimethyl sulfopropyl betaine, stearyl dimethyl sulfopropyl betaine, lauryl dimethyl sulfoethyl betaine, lauryl bis-(2-hydroxyethyl) sulfopropyl betaine, oleyl betaine, or cocamidopropyl betaine may be chosen.
If present, the total amount of amphoteric surfactants may range up to about 10%, such as up to about 9%, up to about 8%, up to about 7%, up to about 6%, up to about 5%, up to about 4%, up to about 3.5%, up to about 3%, up to about 2.5%, up to about 2%, up to about 1.5%, up to about 1 %, or up to about 0.5% by weight, relative to the total weight of the composition. For example, the total amount of amphoteric surfactants may range from about 0.001 % to about 6%, from about 0.01 % to about 4%, from about 0.1 % to about 3%, or from about 0.5% to about 2% by weight, relative to the total weight of the composition. In at least some embodiments, the compositions are free or substantially free of amphoteric surfactants.
Fatty Compounds
Optionally, compositions according to the disclosure may include at least one fatty compound. In certain embodiments, the at least one fatty compound may be chosen from lower alkanes, fatty alcohols, fatty acids, esters of fatty acids, esters of fatty alcohols, oils such as mineral, vegetable, animal, silicone and non-silicone oils, silicone and non-silicone waxes, or combinations of any two or more thereof.
In some embodiments, compositions according to the disclosure include at least one fatty compound chosen from volatile and non-volatile silicone oils, which may optionally be amino functionalized. Non-limiting examples of silicone oils that can be used include dimethicone, amodimethicone, cyclomethicone, polysilicone-1 1 , phenyl trimethicone, trimethylsilylamodimethicone, and stearoxytrimethylsilane. For example, the composition may comprise at least one silicone chosen from amodimethicone, PEG-7 Dimethicone, PEG- 8 Dimethicone, PEG-9 Dimethicone, PEG-10 Dimethicone, PEG-12 Dimethicone, PEG-14 Dimethicone, PEG-17 Dimethicone, PEG/PPG-3/10 Dimethicone, PEG/PPG-4/12 Dimethicone, PEG/PPG- 17/18 Dimethicone, cetyl PEG/PPG-10/1 dimethicone, Dimethicone PEG-8 Benzoate, Dimethicone PEG-7 Phosphate, Dimethicone PEG-8 Phosphate, Dimethicone PEG- 10 Phosphate, or a mixture of two or more thereof. In some preferred embodiments, the compositions comprise a silicone oil component that comprises, consists essentially of, or consists of dimethicone, amodimethicone, or a mixture thereof.
As further examples, the silicone oil may be chosen from polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, which groups each contain from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyl-diphenyl)trisiloxanes, or (2-phenylethyl) trimethylsiloxysilicates.
In some embodiments, compositions according to the disclosure include at least one fatty compound chosen from fatty alcohols. In certain embodiments, “fatty alcohol” refers to any alcohol with a carbon chain of C5 or greater, such as, for example, C8 or greater, C10 or greater, or C12 or greater, such as from 6 to 30 carbon atoms or from 8 to 30 carbon atoms. The fatty alcohols may be alkoxylated or non- alkoxylated, saturated or unsaturated, and linear or branched.
By way of example, fatty alcohols may be chosen from arachidyl alcohol, behenyl alcohol, caprylic alcohol, cetearyl alcohol, cetyl alcohol, coconut alcohol, decyl alcohol, hydrogenated tallow alcohol, jojoba alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol, palm alcohol, palm kernel alcohol, stearyl alcohol, tallow alcohol, tridecyl alcohol, or combinations of two or more thereof. In some preferred embodiments, the compositions comprise a fatty alcohol component that comprises, consists essentially of, or consists of cetyl alcohol, stearyl alcohol, cetearyl alcohol, or mixtures thereof.
Useful and non-limiting fatty acids may be straight or branched chain acids and/or may be saturated or unsaturated. Non-limiting examples of fatty acids include diacids, triacids, and other multiple acids as well as salts of these fatty acids. For example, the fatty acid may optionally include or be chosen from lauric acid, palmitic acid, stearic acid, behenic acid, arichidonic acid, oleic acid, isostearic acid, sebacic acid, or combinations thereof.
In some embodiments, fatty acid esters or fatty alcohol esters may be chosen. For example, esters of saturated or unsaturated, linear or branched C1 -C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched C1 - C26 aliphatic mono- or polyalcohols, the total carbon number of the esters more particularly being greater than or equal to 10 may be used. In other embodiments, esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1 -C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C26 di-, tri-, tetra-, or pentahydroxy alcohols may also be used. As non-limiting examples, isostearyl lactate, lauryl lactate, linoleyl lactate, oleyl lactate, (iso)stearyl octanoate, isocetyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, isocetyl isostearate, isocetyl laurate, isocetyl stearate, isodecyl octanoate, isodecyl oleate, isononyl isononanoate, isostearyl palmitate, methyl acetyl ricinoleate, myristyl stearate, octyl isononanoate, 2-ethylhexyl isononanoate, octyl palmitate, octyl pelargonate, octyl stearate, octyldodecyl erucate, oleyl erucate, ethyl and isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, 2-octyldodecyl, myristyl or stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, diethyl sebacate, diisopropyl sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate, diisostearyl adipate, dioctyl maleate, glyceryl undecylenate, octyldodecyl stearoyl stearate, pentaerythrityl monoricinoleate, pentaerythrityl tetraisononanoate, pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate, pentaerythrityl tetraoctanoate, propylene glycol dicaprylate, propylene glycol dicaprate, tridecyl erucate, triisopropyl citrate, triisostearyl citrate, glyceryl trilactate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate, and/or polyethylene glycol distearates may be chosen. In a preferred embodiment, the composition comprises at least one fatty acid ester and/or fatty alcohol ester, for example pentaerythrityl tetraisostearate.
In some embodiments, compositions according to the disclosure comprise at least one wax. Non-limiting examples of waxes that can be used include beeswax, hydrogenated alkyl olive esters, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax, rice wax, rice bran wax, montan wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, palm kernel glycerides/hydrogenated palm glycerides, palm butter, sumac wax, citrus aurantium dulcis (orange) peel wax, theobroma grandiflorum seed butter, helianthus annuus (sunflower) seed wax, siliconyl candellila wax, Chinese wax, cetyl palmitate, lanolin, shellac, spermaceti, cetyl esters, hydrogenated castor wax; triglyceride esters such as tribehenin (glyceryl tribehenate); synthetic waxes such as those of the hydrocarbon type and polyethylene waxes obtained from the polymerization or copolymerization of ethylene, polypropylene waxes, or mixtures of two or more of any of these waxes. In some preferred embodiments, the compositions comprise a wax component that comprises, consists essentially of, or consists of cetyl esters.
In some embodiments, the composition comprises one or more fatty compounds chosen from oils of animal, vegetable, or mineral origin (e.g. lanolin, squalene, fish oil, perhydrosqualene, mink oil, turtle oil, soybean oil, grape seed oil, sesame oil, maize oil, rapeseed oil, sunflower oil, cottonseed oil, avocado oil, olive oil, castor seed oil, jojoba seed oil, peanut oil, sweet almond oil, palm oil, cucumber oil, hazelnut oil, apricot kernel oil, wheat germ oil, calophyllum oil, macadamia oil, coconut oil, cereal germ oil, candlenut oil, thistle oil, candelilla oil, safflower oil, or shea butter), linear or branched hydrocarbons (e.g. polybutene, hydrogenated polyisobutene, polyisoprene, polydecenes such as hydrogenated polydecene, or also linear, branched and/or cyclic alkanes which are optionally volatile, such as, for example, isohexadecane, isododecane, isodecane, or isohexadecane), mono- and/or polyesters of fatty acids and/or of fatty alcohols (e.g. mono- and polyesters of hydroxy acids and of fatty alcohols, esters of benzoic acid and of fatty alcohols, polyesters of polyols, dipentaerythrityl C5-C9 esters, trimethylolpropane polyesters, propylene glycol polyesters, or polyesters of hydrogenated castor oil), perfluorinated and/or organofluorinated oils, fluorosilicone oils, or mixtures of two or more thereof. Nonlimiting examples of fatty acids that may be used include optionally branched and/or unsaturated fatty acids such as myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, isostearic acid, or mixtures of two or more thereof.
If present, the total amount of fatty compounds in the composition may range from about 0.1 % to about 20%, such as from about 1 % to about 20%, from about 2% to about 15%, from about 3% to about 12%, or from about 5% to about 10% by weight, relative to the total weight of the composition. In some preferred embodiments, the compositions comprise at least one fatty compound chosen from silicone oils, fatty alcohols, waxes, or combinations thereof, where the total amount of fatty compounds in the composition ranges from about 1% to about 20%, preferably from about 2% to about 15%, more preferably from about 3% to about 12%, and most preferably from about 5% to about 10% by weight, relative to the total weight of the composition.
Thickening Agents
Compositions according to the disclosure optionally comprise at least one thickening agent. Useful thickening agents include, but are not limited to, semisynthetic polymers, such as semisynthetic cellulose derivatives, synthetic polymers, such as carbomers, poloxamers, and acrylates/beheneth-25 methacrylate copolymer, acrylates copolymer, polyethyleneimines (e.g., PEI-10), naturally occurring polymers, such as acacia, tragacanth, alginates (e.g., sodium alginate), carrageenan, vegetable gums, such as xanthan gum, guar gum, petroleum jelly, waxes, particulate associate colloids, such as bentonite, colloidal silicon dioxide, and microcrystalline cellulose, celluloses such as hydroxyethylcellulose and hydroxypropylcellulose, and guars such as hydroxypropyl guar.
In some embodiments, the thickening agent may be chosen from associative thickening polymers such as anionic associative polymers, amphoteric associative polymers, cationic associative polymers, or nonionic associative polymers. A non-limiting example of an amphoteric associative polymer is acrylates/beheneth-25 methacrylate copolymer, and non-limiting examples of anionic associative polymers include acrylates copolymer and acrylates crosspolymer-4.
If present, the total amount of thickening agents may range from about 0.01 % to about 8%, such as from about 0.05% to about 5%, from about 0.1 % to about 4%, from about 0.2% to about 3%, or from about 0.3% to about 2% by weight, relative to the total weight of the composition.
Auxiliary Components Compositions according to the disclosure may optionally include one or more auxiliary components. Non-limiting examples include preservatives, fragrances, pH adjusters, salts, antioxidants, vitamins, vitamin derivatives, ceramides, botanical extracts, proteins, protein hydrolysates, protein isolates, hydrotropes, pearlescent agents, buffers, sequestering agents, and the like.
The total amount of auxiliary components, if present, typically ranges from about 0.01 % to about 10% based on the total weight of the composition. For example, in some embodiments the individual amounts of each component or the total amount of components may range from about 0.1 % to about 10%, about 0.1 % to about 8%, about 0.1 % to about 5%, about 0.1 % to about 4%, about 0.1 % to about 3%, about 0.1 % to about 2%, about 1 % to about 10%, about 1 % to about 8%, about 1% to about 5%, about 1 % to about 4%, about 1 % to about 3%, or about 1 % to about 2% by weight, based on the total weight of the composition.
Compositions according to the disclosure typically have a pH of less than or equal to 7, such as less than or equal to about 6, less than or equal to about 5, less than or equal to about 4.5, or less than or equal to about 4. For example, the compositions may have a pH ranging from about 1 to about 7, such as from about 2 to about 6, from about 2.5 to about 5.5, from about 2.5 to about 5, from about 2.5 to about 4.5, or from about 3 to about 4. In some embodiments, the pH of the composition may be, for example, about 3, about 3.25, about 3.5, about 3.75, or about 4, including all ranges and subranges thereof.
The compositions may be in any suitable form. For example, the compositions may be a liquid, a gel, a gel cream, a high-, medium- or low-density cream, a serum, a lotion, etc.
II. METHODS
The disclosure further relates to methods of improving penetration of active agents into keratin fibers, e.g. hair. The methods comprise including at least one penetration-enhancing solvent as described herein in a composition comprising at least one active agent. The active agents may, in various embodiments, comprise at least one amino acid, at least one osmolyte, and/or at least one carboxylic acid, as described herein. For example, in some preferred embodiments, the active agent comprises, consists essentially of, or consists of at least one amino acid and/or a salt thereof and at least one osmolyte. In other preferred embodiments, the active agent comprises, consists essentially of, or consists of at least one basic amino acid, glycine betaine, and at least one carboxylic acid. In further preferred embodiments, the active agent comprises, consists essentially of, or consists of arginine and/or a salt thereof, glycine betaine, and citric acid and/or a salt thereof.
The disclosure further relates to methods of treating keratin fibers, in order to provide enhanced penetration of active agents into the hair, using compositions according to the disclosure. The methods are able to provide surprisingly greater benefits to the hair due to the greater ability of the active agents to penetrate into the hair fibers. The methods comprise applying a composition according to the disclosure onto the hair, optionally leaving the composition on the hair for a period of time (“processing time,” “resting period,” or “leave-in period”), and optionally rinsing the composition from the hair. Although not required, various treatments using compositions according to the disclosure may also include a step of heating the hair to which the composition has been applied, for example during the leave-in period while the composition is on the hair. For example, a blow dryer, hood dryer, etc., may be used.
The leave-in period may last for a period of time deemed appropriate to allow the active agents to provide benefits to the keratin fibers, such as about 30 seconds, about 1 minute, about 2 minutes, about 5 minutes, about 10 minutes, about 15 minutes, about 20 minutes, about 30 minutes, about 45 minutes, about 1 hour, about 2 hours, etc., or may range from a period of time using any of the foregoing as upper and lower limits. By way of non-limiting example, the leave-in period may range from about 30 seconds to about 60 minutes, from about 30 seconds to about 45 minutes, from about 30 seconds to about 30 minutes, from about 30 seconds to about
20 minutes, from about 30 seconds to about 15 minutes, from about 30 seconds to about 10 minutes, from about 30 seconds to about 5 minutes, from about 1 minute to about 60 minutes, from about 1 minute to about 45 minutes, from about 1 minute to about 30 minutes, from about 1 minute to about 20 minutes, from about 1 minute to about 15 minutes, from about 1 minute to about 10 minutes, from about 1 minute to about 5 minutes, from about 2 minutes to about 60 minutes, from about 2 minutes to about 45 minutes, from about 2 minutes to about 30 minutes, from about 2 minutes to about 20 minutes, from about 2 minutes to about 15 minutes, from about 2 minutes to about 10 minutes, from about 2 minutes to about 5 minutes, etc.
Surprisingly, hair treated with compositions and methods according to the disclosure has less damage than hair not treated according to the disclosure, which is achieved by successful penetration of the active agents into the hair fibers. The reduction in damage is particularly notable in hair that has been damaged due to harsh chemical treatments such as bleaching, dyeing, permanent waving, straightening, relaxing, etc., as well as due to repeated styling such as with heat or styling tools. The hair repaired using compositions and methods according to the disclosure may have lower elasticity and/or greater tensile strength than hair similarly damaged but not treated according to the disclosure.
Having described the many embodiments of the present invention in detail, it will be apparent that modifications and variations are possible without departing from the scope of the disclosure defined in the appended claims. Furthermore, it should be appreciated that all examples in the present disclosure, while illustrating many embodiments of the disclosure, are provided as non-limiting examples and are, therefore, not to be taken as limiting the various aspects so illustrated. It is to be understood that all definitions herein are provided for the present disclosure only.
In this application, the use of the singular includes the plural unless specifically stated otherwise. The singular forms “a,” “an,” “the,” and “at least one” are understood to encompass the plural as well as the singular unless the context clearly dictates otherwise. The expression “one or more” means “at least one” and thus includes individual components as well as mixtures/combinations. Likewise, the term “a salt thereof” also relates to “salts thereof.” Thus, where the disclosure refers to “an element selected from the group consisting of A, B, C, D, E, F, a salt thereof, or mixtures thereof,” it indicates that that one or more of A, B, C, D, and F may be included, one or more of a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, or a salt of F may be included, or a mixture of any two of A, B, C, D, E, F, a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included.
The term “and/or” should be understood to include both the conjunctive and the disjunctive. For example, “amino acids and/or salts thereof’ means “amino acids and salts thereof” as well as “amino acids or salts thereof,” and expressly covers instances of either.
As used herein, the term “salts” referred to throughout the disclosure may include salts having a counterion such as an alkali metal, alkaline earth metal, or ammonium counterion. This list of counterions, however, is non-limiting. Salts also include a dissociated form of a compound, e.g., in an aqueous solution. As used herein, the phrases “and mixtures thereof,” “and mixtures of two or more thereof,” “and a mixture thereof,” “and combinations thereof,” “and a combination thereof,” and combinations of two or more thereof,” “and a combination of two or more thereof,” “or mixtures thereof,” “or a mixture thereof,” “or combinations thereof,” “or combinations of two or more thereof,” “or a combination thereof,” and the like are used interchangeably to denote that the listing of components immediately preceding the phrase, such as “A, B, C, D, or mixtures thereof” signify that the component(s) may be chosen from A, from B, from C, from D, from A+B, from A+B+C, from A+D, from A+C+D, etc., without limitation on the variations thereof. Thus, the components may be used individually or in any combination thereof.
For purposes of the present disclosure, it should be noted that to provide a more concise description, some of the quantitative expressions given herein are not qualified with the term “about.” It is understood that whether the term “about” is used explicitly or not, every quantity given herein is meant to refer to the actual given value, and it is also meant to refer to the approximation to such given value that would reasonably be inferred based on the ordinary skill in the art, including approximations due to the experimental and/or measurement conditions for such given value, unless otherwise stated.
All ranges and amounts given herein are intended to include sub-ranges and amounts using any disclosed point as an end point, and all endpoints are intended to be included unless expressly stated otherwise. Thus, a range of “1 % to 10%, such as 2% to 8%, such as 3% to 5%,” is intended to encompass ranges of “1 % to 8%,” “1 % to 5%,” “2% to 10%,” and so on. All numbers, amounts, ranges, etc., are intended to be modified by the term “about,” whether or not expressly stated, unless expressly stated otherwise. Similarly, a range given of “about 1 % to 10%” is intended to have the term “about” modifying both the 1 % and the 10% endpoints. The term “about” is used herein to indicate a difference of up to +/- 10% from the stated number, such as +/- 9%, +/- 8%, +/- 7%, +/- 6%, +/- 5%, +/- 4%, +/- 3%, +/- 2%, or +/- 1 %. Unless expressly stated otherwise, “about” means +/- 5%. Likewise, all endpoints of ranges are understood to be individually disclosed, such that, for example, a range of 1 :2 to 2:1 is understood to disclose a ratio of both 1 :2 and 2:1 .
As used herein, if a component is described as being present “in an amount up to” a certain amount, it is intended that such component is, in fact, present in the composition, i.e. is present in an amount greater than 0%. All amounts given herein are relative to the amount of active material, unless otherwise indicated.
All percentages, parts and ratios herein are based upon the total weight of the compositions of the present disclosure, unless otherwise indicated.
As used herein, all ranges provided are meant to include every specific range within, and combination of sub ranges between, the given ranges. Thus, a range from 1 -5, includes specifically 1 , 2, 3, 4 and 5, as well as sub ranges such as 2-5, 3-5, 2-3, 2-4, 1 -4, etc.
As used herein, the phrase “applying a composition onto hair” and variations thereof are intended to mean contacting the hair with at least one of the compositions of the disclosure, in any manner. It may also mean contacting the hair in an effective amount.
The term “treating hair” (and its grammatical variations) as used herein refers to the application of the compositions of the present disclosure onto the surface of hair. The term “treating hair” (and its grammatical variations) as used herein also refers to contacting hair with the compositions of the present disclosure.
A "rinse-off" product refers to a composition such as a hair treatment composition that is removed from the hair after a processing time, e.g. is rinsed and/or washed with water. At least a portion, and typically most, of the composition is removed from the hair.
As used herein, the terms “improving penetration,” “improved penetration,” “enhancing penetration,” “enhanced penetration,” or the like, of active agents means any increase in the amount of active agents present in the hair fiber. The increase in amount of active agents present in the hair fiber can be determined for example by measuring the denaturation temperature of the hair using Differential Scanning Calorimetry (crimpled, closed pan), where an increase in the denaturation temperature signifies an increase in the amount of actives present. However, as described herein, an increase or improvement in penetration in active agents also results in healthier, stronger, less damaged hair which may be determined by various methods, such as, for example, break stress testing, elasticity, etc.
Unless otherwise defined for any specific embodiment, the term “substantially free” or “essentially free” as used herein means that there is less than about 5% by weight of a specific material added to a composition, based on the total weight of the composition. For example, the compositions may include less than about 4%, less than about 3%, less than about 2%, less than about 1 .5%, less than about 1 %, less than about 0.5%, less than about 0.1 %, less than about 0.01%, less than about 0.001 %, or less than about 0.0001% of the specified material. As such, it is contemplated that any component described herein for use in the hair treatment compositions can be present in the compositions in amounts less than about 5%, less than about 4%, less than about 3%, less than about 2%, less than about 1 %, less than about 0.5%, less than about 0.1 %, less than about 0.01 %, less than about 0.001 %, or less than about 0.0001 %, and the composition will be considered “substantially free” of such material. A composition that is “free” of a component is understood to contain none of the specified component. However, it is understood that the terms “free” and “substantially free” refer to the amount of a component added to the composition, without including an amount of the component present in the composition as a minor component in a raw material. For example, a composition that is “free” of waxes may not have wax included as an intended component but may nevertheless contain a pigment that is coated with a wax, as such wax would be considered a minor component of the pigment material and would not be expected to provide benefits to the composition that would be expected by including a wax per se as an intended component.
Unless otherwise expressly stated, it is in no way intended that any method set forth herein be construed as requiring that its steps be performed in a specific order. Accordingly, where a method claim does not expressly recite an order to be followed by its steps or it is not specifically stated in the claims or descriptions that the steps are to be limited to a specific order, it not intended that any particular order be inferred.
The examples that follow serve to illustrate embodiments of the present disclosure without, however, being limiting in nature. It will be apparent to those skilled in the art that various modifications and variations can be made in the compositions and methods of the invention without departing from the spirit or scope of the invention. Thus, it is intended that the present disclosure covers the modifications and variations that come within the scope of the appended claims and their equivalents.
EXAMPLES
The following Examples are intended to be non-limiting and explanatory in nature only. In the Examples, amounts are expressed in percentage by weight (wt%) of active materials, relative to the total weight of the composition, unless otherwise indicated.
Example 1 - Compositions
Compositions 1 A-1 F according to the disclosure were prepared as shown in Table 1 . The pH of each of compositions 1 A-1 F was about 3.5.
TABLE 1
Figure imgf000044_0001
The compositions contained a synergistic combination of active agents
(carboxylic acids (citric and/or lactic acid), osmolytes (glycine betaine), and amino acids (arginine and/or serine)), with a penetration-enhancing solvent (propylene glycol or dipropylene glycol).
Example 2 - Evaluation of Damage Repair
In order to evaluate the ability of compositions according to the disclosure to enhance penetration of the active agents into hair fibers to minimize, prevent, or repair damage to hair, the following studies were conducted.
Example 2A - Ultra Bleached Hair
Eight swatches (S1 -S8) of virgin Caucasian hair were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes. The swatches were rinsed and then seven of the swatches (S1 -S7) were subjected to the following treatment routines (swatch S8 did not have any treatment after the bleaching composition was rinsed from the hair).
Swatch S1 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated every day for five days.
Swatches S2-S7 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, one of compositions 1 A-1 F (Table 2A) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated every day for five days.
TABLE 2A
Figure imgf000045_0001
The integrity of the hair fibers of each of swatches S1 -S8 was studied after the first and fifth days. Elasticity was evaluated to determine whether the hair fibers stretched, and if so, whether they returned to their original state (lower elasticity, i.e. healthy), whether the fibers stretched easily and remained stretched (higher elasticity, i.e. damaged), or whether the hair fibers broke upon testing.
The evaluation was performed by stretching a standardized amount of wet hair fibers, with two experts independently evaluating each swatch. The experts were trained to stretch the area of the swatch being evaluated by uniformly applying manual pulling force using the hands/fingers. The behavior of the swatch was classified by each expert according to a 6-level scale as follows, with the result reported for each swatch as the average of the two:
0 = Natural, healthy hair (no damage);
1 = Low elasticity (when stretched, hair fibers present slight elasticity, returning to the initial state after the test);
2 = Moderate elasticity (when stretched, hair fibers present elasticity, returning to the initial state after the test); 3 = High elasticity (when stretched, hair fibers present elasticity and some of the hair fibers do not return to the initial state after the test);
4 = Very high elasticity (when stretched, hair fibers present elasticity and most of the hair fibers do not return to the initial state after the test); and
5 = Immediate break (when stretched, hair fibers present high elasticity and break during the test).
The results showed that the hair fibers of swatches S2-S7, treated with one of compositions 1 A-1 F, surprisingly had lower elasticity than the fibers of swatches S1 or S8 after both day 1 (FIG. 1 A) and day 5 (FIG. 1 B). In other words, the hair of swatches S1 and S8 was damaged by the harsh bleaching process, leading to increased elasticity, whereas the damage to swatches S2-S7 had been repaired by treatment with one of compositions 1 A-1 F.
Example 2B - Straightened and Ultra Bleached Hair
Eight swatches (S9-S16) of Caucasian hair that had been previously straightened using formaldehyde were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes. The swatches were rinsed and then seven of the swatches (S9-S15) were subjected to the following treatment routines.
Swatch S9 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair. The treatment was repeated a second time. This treatment protocol was repeated every day for five days.
Swatches S10-S15 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, one of compositions 1 A-1 F (Table 2B) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair. This treatment protocol was repeated every day for five days.
TABLE 2B
Figure imgf000047_0001
The integrity of the hair fibers of each of swatches S9-S16 was studied in the same manner as described in Example 2A. The results showed that the hair fibers of swatches S10-S15, treated with one of compositions 1 A-1 F, surprisingly had lower elasticity than the fibers of swatches S9 and S16 after both day 1 (FIG. 2A) and day 5 (FIG. 2B).
Examples 2A-2B therefore demonstrate that compositions according to the disclosure surprisingly enhance penetration of the active agents into the damaged hair fibers, allowing the active agents to repair the damage. Surprisingly, Example 2B demonstrates that this benefit is observed even in hair that has substantial build-up of hair products coated on the hair fibers.
Example 3 - Compositions
Compositions 2A-2E according to the disclosure were prepared as shown in Table 3.
TABLE 3
Figure imgf000047_0002
Figure imgf000048_0001
The compositions contained a synergistic combination of active agents
(carboxylic acids (citric acid), osmolytes (glycine betaine), and amino acids (arginine)), with a penetration-enhancing solvent (dipropylene glycol).
Example 4 - Evaluation of Damage Repair In order to evaluate the ability of compositions according to the disclosure to enhance penetration of the active agents into damaged hair fibers to minimize, prevent, or repair damage to hair, the following studies were conducted.
A comparative product, C1 , had the following listing of ingredients on the package: Water (Aqua/Eau), Bis-Aminopropyl Diglycol Dimaleate, Propylene Glycol, Cetearyl Alcohol, Behentrimonium Methosulfate, Cetyl Alcohol, Phenoxyethanol, Glycerin, Hydroxyethyl Ethylcellulose, Stearamidopropyl Dimethylamine , Quaternium- 91 , Sodium Benzoate, Cetrimonium Methosulfate, Cetrimonium Chloride, Fragrance (Parfum), Tetrasodium EDTA, Polyquaternium-37, Benzyl Benzoate, Etidronic Acid, Ascorbic Acid, Phytantriol, Tocopheryl Acetate, Aloe Barbadensis Leaf Juice, Panthenol, Simmondsia Chinensis (Jojoba) Seed Oil, Citric Acid, Potassium Sorbate. Composition C1 , which is described as a “pre-shampoo hair treatment that reduces breakage and split ends for visibly healthier hair,” is advertised as part of a system that asserts it can “relink broken disulfide bonds damaged by chemical services, heat, and styling.” The instructions for composition C1 are to use the product prior to using the shampoo (“C1 -S”) and conditioner (“C1 -C”) that form part of this system, both of which include bis-aminopropyl diglycol dimaleate as the stated active agent.
Example 4A - Ultra Bleached Hair: Elasticity and Strength
Five swatches (S17-S21 ) of virgin Caucasian hair were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes. The swatches were rinsed and then four of the swatches (S17-S20) were subjected to the following treatment routines (swatch S21 did not have any treatment after the bleaching composition was rinsed from the hair).
Swatch S17 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
Swatches S18 and S19 were each cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, one of compositions 2D (S18) or 2B (S19) was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
Swatch S20 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated. Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. This treatment protocol was repeated four more times.
Once all five treatments of swatches S17-S20 were completed, the integrity of the hair fibers of each of swatches S17-S21 was studied in the same manner as described in Example 2A. The results showed that the hair fibers of swatches S18 and S19, treated with compositions 2D and 2B respectively, had lower elasticity than the fibers of swatches S17 and S20-S21 (FIG. 3).
Next, the strength was evaluated using a fiber tensile testing instrument from Dia-Stron known as an MTT (Miniature Tensile Tester). The results showed that the hair of swatches S18 and S19, treated with compositions 2D and 2B respectively, was surprisingly stronger than the hair of swatches S17 or S20, meaning that more force was required to break the individual hair fibers of swatches S18-S19. FIG. 4A shows the break stress (MPa) for a control swatch (CTL), which was the same hair but unbleached, swatch S17, which was bleached but without subsequent treatment, and swatches S18 and S19, treated with compositions 2D and 2B respectively, and S20, treated with the comparative compositions. As FIG. 4A shows, the break stress of the control swatch (CTL) was more than twice that of swatch S17, demonstrating the significant damage caused by the bleaching process. After five (5) treatments with either composition 2D (swatch S18), 2B (swatch S19), or the comparative compositions (S20), the break stress of the treated swatches was increased compared to swatch S17. Surprisingly, the increase in break stress for swatches S18-S19 was considered to be statistically significant compared to that of swatch S20, meaning that compositions 2D and 2B repaired the hair to a greater degree than the comparative compositions.
Example 4B - Straightened and Ultra Bleached Hair: Elasticity
Four swatches (S22-S25) of Caucasian hair that had been previously straightened using formaldehyde were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes. The swatches were rinsed and for a treatment period of five weeks, all four swatches were subjected to the following routine twice a week. First, the swatches were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
Three of the swatches (S22-S24) were subjected to the following additional treatment routines one time each week for the 5-week period.
Swatch S22 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. A mask composition was applied to the hair and allowed to remain on the hair, after which the hair was rinsed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
Swatch S23 was cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, composition 2C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, a commercially available conditioner composition was applied and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
Swatch S24 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated. Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
After the five-week treatment period, the elasticity and strength of the hair fibers of each of swatches S22-S25 were studied in the same manner as described in Example 2A. The results showed that the hair fibers of swatch S23, treated with composition 2C, had lower elasticity than the fibers of any of swatches S22 or S24- S25.
Example 4C - Straightened and Ultra Bleached Hair: Strength
Four swatches (S26-S29) of Caucasian hair that had been previously straightened using formaldehyde were bleached with a composition prepared by mixing a commercial bleach powder with a commercial oxidizing composition (40V hydrogen peroxide) at a mixing ratio of 1 :1.5 (bleach powderoxidizing composition) and processed at a temperature of about 55°C for about 45 minutes. The swatches were rinsed and for a treatment period of five weeks, all four swatches were subjected to the following routine.
First, the swatches were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
Three of the swatches (S27-S29) were subjected to the following additional treatment routines one time each week for the 5-week period.
Swatches S27 and S28 were cleansed with a commercially available shampoo by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. One of either composition 2B (S28) or 2D (S27) was applied to the hair and allowed to remain on the hair, after which the hair was rinsed. Immediately, a commercially available conditioner composition was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
Swatch S29 was treated with composition C1 by applying the composition to the swatch and distributing it to ensure the hair was fully coated. Composition C1 was allowed to remain on the hair for a resting period of about five minutes, and then the swatch was thoroughly rinsed. Immediately, the swatch was cleansed with shampoo C1 -S by wetting the swatch, applying the shampoo to the swatch, lathering the shampoo, allowing it to rest on the swatch for a period of about one minute, then rinsing the swatch until all shampoo was removed. Immediately, conditioner C1 -C was applied to the swatch and distributed to ensure the hair was fully coated, allowed to remain for a resting period of about five minutes, and then the swatch was thoroughly rinsed. A leave-on conditioning product and a leave-on flat iron serum were applied to the hair.
MTT testing was performed in the same manner as described in Example 4A. The results showed that the hair of swatches S27 and S28, treated with compositions 2D and 2B respectively, was surprisingly stronger than the hair of swatches S26 or S29, meaning that more force was required to break the individual hair fibers of swatches S27-S28. FIG. 4B shows the break stress (MPa) for a control swatch (CTL), which was the same hair but unbleached, swatch S26, which was bleached but without subsequent treatment, swatches S27 and S28, treated with compositions 2D and 2B respectively, and S29, treated with the comparative compositions. As FIG. 4B shows, the break stress of the control swatch (CTL) was approximately three times that of swatch S26, showing the significant damage caused by the bleaching process. After five (5) treatments with either composition 2B (swatch S28), 2D (swatch S27), the break stress of the treated swatches was increased compared to swatch S26, and the improvement was considered to be statistically significant. FIG. 4B shows, however, that the break stress of the swatch treated with the comparative composition (S29) had no improvement in break stress.
Examples 4A-4C thus demonstrate that compositions according to the disclosure have surprisingly enhanced penetration of the active agents into the damaged hair fibers, allowing the active agents to repair the damage. Surprisingly, Example 4B demonstrates that this benefit is even observed in hair that has substantial build-up of hair products coated on the hair fibers. The damage repair achieved with compositions according to the disclosure is also surprisingly greater than that achieved with a commercial product that asserts to do the same. Example 5 - Penetration Enhancing Compositions
Compositions 3A-3D according to the disclosure were prepared as shown in Table 4.
TABLE 4
Figure imgf000054_0001
Compositions 3A-3D are expected to similarly provide improved penetration of the active agents contained therein to hair, in order to more effectively introduce components into the hair fiber that can minimize, prevent, and/or repair damage.
Example 6 - Additional Compositions
The following compositions according to the disclosure can be prepared and are likewise expected to similarly improve penetration of active agents into the hair in order to minimize, prevent, or repair damage to hair. TABLE 5
Figure imgf000055_0001
The above examples demonstrate that the compositions and methods according to the disclosure surprisingly and unexpectedly enhance penetration of active agents in order to minimize, prevent, or repair damage to hair.

Claims

1 . A method for improving penetration of active agents into hair, the method comprising applying to the hair a composition comprising: a) at least one penetration-enhancing solvent chosen from polyols; b) at least one active agent chosen from osmolytes; c) optionally, at least one additional active agent chosen from:
(i) at least one compound chosen from amino acids or salts thereof; or
(ii) at least one compound chosen from carboxylic acids or salts thereof; and d) water wherein the total amount of polyols is at least about 2% by weight, relative to the total weight of the composition, wherein the total amount of osmolytes is at least about 0.5% by weight, relative to the total weight of the composition, and wherein the pH of the composition is less than 7.
2. The method of claim 1 , wherein the total amount of polyols in the composition ranges from about 2% to about 65%, preferably from about 5% to about 50%, more preferably from about 5% to about 35%, and most preferably from about 7% to about 25% by weight, relative to the total weight of the composition.
3. The method of claim 1 or claim 2, wherein the polyols are chosen from C2-C16 diols, C2-C16 triols, or combinations or two or more thereof, preferably from C2-C8 diols, C2-C8 triols, or combinations or two or more thereof.
4. The method of any one of claims 1 to 3, wherein the polyols are chosen from propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, glycerin, or combinations of two or more thereof.
5. The method of any one of claims 1 to 4, wherein the composition comprises at least one osmolyte chosen from carbohydrate sugars, polyamines, betaines, or combinations of two or more thereof, preferably comprising at least one betaine chosen from compounds of formula (II) or salts thereof:
(R1 )(R2)(R3)m-A+-CR4R5-(X)n-Y-
(H) wherein: R1 , R2, and R3 are independently chosen from C1 -C4 alkyl groups;
A is N or S; m and n are independently 0 or 1 ;
X is a divalent C1 -C6 alkyl group, linear or branched, saturated or unsaturated, optionally substituted by one or more groups chosen from hydroxyl (-OH) or amino (-NH2); and
Y’ is -COO- or -OSO3-; with the provisos that: o when A is S, then m = 0 and R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains), (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, or -CONH2; o when A is N and m = 0, R4 represents a hydrogen atom or a saturated, linear, or branched (C1 -C8)alkyl, and R5 forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, optionally substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl; and o when A is N and m = 1 , then R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains) (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, or -CONH2.
6. The method of any one of claims 1 to 5, wherein the composition comprises at least one osmolyte chosen from carbohydrate sugars, preferably from C3-C6 monosaccharides, more preferably from pentoses, hexoses, derivatives thereof, or combinations of two or more thereof.
7. The method of any one of claims 1 to 6, wherein the composition comprises at least one osmolyte chosen from polyamines, preferably chosen from diamines, triamines, tetramines, pentamines, or combinations of two or more thereof.
8. The method of any one of claims 1 to 7, wherein the composition comprises at least one osmolyte chosen from compounds of formula (II) or salts thereof, preferably chosen from zwitterionic amino acid derivatives bearing a quaternary ammonium group and comprising from 1 to 12 carbon atoms, preferably from 2 to 10 carbon atoms, more preferably from 3 to 8 carbon atoms.
9. The method of any one of claims 1 to 8, wherein the composition comprises at least one osmolyte chosen from compounds of formula (II) chosen from valine betaine, glutamic acid betaine, glutamine betaine, trimethyl lysine, glycine betaine, histidine betaine, N-methyl histidine betaine, alanine betaine, beta-alanine betaine, choline sulfate, pipecolic acid betaine, proline betaine, hydroxyproline betaine, tyrosine betaine, phenylalanine betaine, tryptophan betaine, leucine betaine, isoleucine betaine, salts thereof, or combinations of two or more thereof, preferably comprising glycine betaine.
10. The method of any one of claims 1 to 9, wherein the composition comprises at least one compound of formula (II), wherein:
R1 and R2 are methyl;
A is N; and/or
Y is COO-.
1 1 . The method of any one of claims 1 to 10, wherein the total amount of osmolytes ranges from about 0.5% to about 10%, preferably from about 1% to about 8%, more preferably from about 1 % to about 5%, and most preferably from about 1 .5% to about 3.5% by weight, relative to the total weight of the composition.
12. The method of any one of claims 1 to 1 1 , wherein the composition comprises at least one active agent chosen from amino acids or salts thereof, preferably chosen from amino acids of formula (I) or salts thereof:
Figure imgf000058_0001
wherein: p is an integer equal to 1 or 2, and when p = 1 , R forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, preferably 5 ring members, optionally substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl; or when p = 2, R represents a hydrogen atom or a saturated, linear, or branched (C1 -C12)alkyl group, preferably a (C1 -C4)alkyl group, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, -CONH2, -NH-C(NH)-NH2, or an imidazole ring.
13. The method of any one of claims 1 to 12, wherein the composition comprises at least one amino acid chosen from arginine, glycine, proline, methionine, serine, lysine, histidine, salts thereof, or combinations of two or more thereof.
14. The method of any one of claims 1 to 13, wherein the composition comprises at least one active agent chosen from amino acids or salts thereof, and the total amount of amino acids and salts thereof ranges from about 2% to about 15%, preferably from about 2.5% to about 12%, more preferably from about 3% to about 10%, and most preferably from about 3.5% to about 8% by weight, relative to the total weight of the composition.
15. The method of any one of claims 1 to 14, wherein the composition comprises at least one active agent chosen from carboxylic acids or salts thereof, preferably chosen from monocarboxylic acids, dicarboxylic acids, tricarboxylic acids, salts thereof, or combinations of two or more thereof.
16. The method of any one of claims 1 to 15, wherein the composition comprises at least one active agent chosen from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, lactic acid, oxalic acid, malonic acid, malic acid, glutaric acid, citraconic acid, succinic acid, adipic acid, tartaric acid, fumaric acid, maleic acid, citric acid, isocitric acid, aconitic acid, propane-1 ,2,3-tricarboxylic acid, salts thereof, or combinations of two or more thereof.
17. The method of any one of claims 1 to 16, wherein the composition comprises at least one active agent chosen from carboxylic acids or salts thereof, and the total amount of carboxylic acids and salts thereof ranges from about 3% to about 15%, preferably from about 3% to about 12%, more preferably from about 3.5% to about 10%, and most preferably from about 4% to about 8% by weight, relative to the total weight of the composition.
18. The method of any one of claims 1 to 17, wherein the composition further comprises at least one additional component chosen from water, fatty compounds, surfactants, thickening agents, or combinations of two or more thereof.
19. The method of any one of claims 1 to 18, wherein the composition comprises: a) at least one C2-C8 polyol; b) at least one compound of formula (II) or salt thereof; and c) at least basic amino acid or salt thereof.
20. The method of any one of claims 1 to 19, wherein the composition comprises: a) at least one glycol; b) glycine betaine; c) at least one compound chosen from arginine or salts thereof and at least one compound chosen from citric acid, lactic acid, or salts thereof.
21 . A method for improving penetration of active agents into hair, the method comprising applying to the hair a composition comprising: a) at least one penetration-enhancing solvent chosen from polyols, wherein the polyols include at least one glycol; b) at least one osmolyte chosen from compounds of formula (II) or salts thereof:
(R1 )(R2)(R3)m-A+-CR4R5-(X)n-Y-
(H) wherein:
R1 , R2, and R3 are independently chosen from C1 -C4 alkyl groups;
A is N or S; m and n are independently 0 or 1 ;
X is a divalent C1 -C6 alkyl group, linear or branched, saturated or unsaturated, optionally substituted by one or more groups chosen from hydroxyl (-OH) or amino (-NH2); and
Y’ is -COO- or -OSO3-; with the provisos that: o when A is S, then m = 0 and R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains), (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, or -CONH2; o when A is N and m = 0, R4 represents a hydrogen atom or a saturated, linear, or branched (C1 -C8)alkyl, and R5 forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, optionally substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl ; and o when A is N and m = 1 , then R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains) (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, or -CONH2; c) at least one compound chosen from amino acids or salts thereof; and d) at least one compound chosen from carboxylic acids or salts thereof, wherein the total amount of polyols ranges from about 2% to about 65% by weight, relative to the total weight of the composition, wherein the total amount of amino acids and salts thereof ranges from about 2% to about 15% by weight, relative to the total weight of the composition, and wherein the total amount of carboxylic acids and salts thereof ranges from about 2% to about 15% by weight, relative to the total weight of the composition.
22. The method of claim 21 , wherein the polyols comprise at least one compound chosen from propylene glycol, dipropylene glycol, tripropylene glycol, propanediol, propylene carbonate, PPG-3 methyl ether, dimethyl isosorbide, hexylene glycol, ethanol, glycerin, or combinations of two or more thereof.
23. The method of claim 21 or claim 22, wherein the total amount of polyols ranges from about 2% to about 65%, preferably from about 5% to about 50%, more preferably from about 5% to about 35%, and most preferably from about 7% to about 25% by weight, relative to the total weight of the composition.
24. The method of any one of claims 21 to 23, wherein the compounds of formula (II) are chosen from valine betaine, glutamic acid betaine, glutamine betaine, trimethyl lysine, glycine betaine, histidine betaine, N-methyl histidine betaine, alanine betaine, beta-alanine betaine, choline sulfate, pipecolic acid betaine, proline betaine, hydroxyproline betaine, tyrosine betaine, phenylalanine betaine, tryptophan betaine, leucine betaine, isoleucine betaine, or combinations of two or more thereof, preferably comprising glycine betaine.
25. The method of any one of claims 21 to 24, wherein the total amount of osmolytes ranges from about 0.5% to about 10%, preferably from about 1 % to about 8%, more preferably from about 1 % to about 5%, and most preferably from about 1 .5% to about 3.5% by weight, relative to the total weight of the composition.
26. The method of any one of claims 21 to 25, wherein the composition comprises: a) at least one penetration-enhancing solvent chosen from propylene glycol, dipropylene glycol, glycerin, or a combination of two or more thereof; b) glycine betaine or a salt thereof; and c) at least one basic amino acid or salt thereof.
27. A composition for treating keratin fibers, comprising: a) (R1 )(R2)(R3)m-A+- at least one penetration-enhancing solvent chosen from polyols, wherein the polyols include at least one glycol; b) at least one osmolyte chosen from compounds of formula (II) or salts thereof:
CR4R5-(X)n-Y-
(H) wherein:
R1 , R2, and R3 are independently chosen from C1 -C4 alkyl groups;
A is N or S; m and n are independently 0 or 1 ;
X is a divalent C1 -C6 alkyl group, linear or branched, saturated or unsaturated, optionally substituted by one or more groups chosen from hydroxyl (-OH) or amino (-NH2); and
Y’ is -COO- or -OSO3-; with the provisos that: o when A is S, then m = 0 and R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains), (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or - C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (- OH), amino (-NH2), -SH, -COOH, or -CONH2; o when A is N and m = 0, R4 represents a hydrogen atom or a saturated, linear, or branched (C1 -C8)alkyl, and R5 forms, together with the nitrogen atom, a saturated heterocycle comprising from 5 to 8 ring members, optionally substituted by one or more groups chosen from hydroxyl or (C1 -C4)alkyl ; and o when A is N and m = 1 , then R4 and R5 are independently chosen from a hydrogen atom or a saturated, unsaturated, linear, branched and/or cyclic (including aromatic and polycyclic chains) (C1 -C10) hydrocarbon chain, optionally interrupted by one or more heteroatoms or groups chosen from -S-, -N=, -NH-, or -C(NH)-, and/or optionally substituted by one or more groups chosen from hydroxyl (-OH), amino (-NH2), -SH, -COOH, or -CONH2; c) at least one compound chosen from basic amino acids or salts thereof; and d) at least one compound chosen from carboxylic acids or salts thereof, wherein the total amount of polyols ranges from about 5% to about 35% by weight, relative to the total weight of the composition, wherein the total amount of amino acids and salts thereof ranges from about 3% to about 10% by weight, relative to the total weight of the composition, and wherein the total amount of carboxylic acids and salts thereof ranges from about 3% to about 10% by weight, relative to the total weight of the composition, and wherein the pH of the composition ranges from about 2 to about 5.
28. The composition of claim 27, comprising at least one penetrationenhancing solvent chosen from propylene glycol, dipropylene glycol, glycerin, or a combination of two or more thereof.
29. The composition of claim 27 or 28, wherein the compounds of formula (II) are chosen from valine betaine, glutamic acid betaine, glutamine betaine, trimethyl lysine, glycine betaine, histidine betaine, N-methyl histidine betaine, alanine betaine, beta-alanine betaine, choline sulfate, pipecolic acid betaine, proline betaine, hydroxyproline betaine, tyrosine betaine, phenylalanine betaine, tryptophan betaine, leucine betaine, isoleucine betaine, salts thereof, or combinations of two or more thereof, preferably comprising glycine betaine.
30. The composition of any one of claims 27 to 29, wherein the total amount of osmolytes ranges from about 0.5% to about 10%, preferably from about 1 % to about 8%, more preferably from about 1 % to about 5%, and most preferably from about 1 .5% to about 3.5% by weight, relative to the total weight of the composition.
31 . The composition of any one of claims 27 to 30, comprising at least one compound of formula (II) or salt thereof, wherein:
R1 and R2 are methyl;
A is N; and/or
Y is COO-.
32. The composition of any one of claims 27 to 31 , comprising: a) propylene glycol, dipropylene glycol, glycerin, or a combination of two or more thereof; b) glycine betaine; and c) arginine or salt thereof.
33. The composition of any one of claims 27 to 32, further comprising serine in an amount ranging from about 0.01 % to about 2% by weight, relative to the total weight of the composition.
34. The composition of any one of claims 27 to 33, further comprising at least one additional component chosen from fatty compounds, surfactants, thickening agents, non-aqueous solvents other than glycols, or combinations of two or more thereof.
PCT/BR2023/050474 2023-12-20 2023-12-20 Compositions and methods for improving penetration of active agents for keratin fibers Pending WO2025129285A1 (en)

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