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WO2024122393A1 - Composition pour le défrisage amélioré de fibres de kératine - Google Patents

Composition pour le défrisage amélioré de fibres de kératine Download PDF

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Publication number
WO2024122393A1
WO2024122393A1 PCT/JP2023/042435 JP2023042435W WO2024122393A1 WO 2024122393 A1 WO2024122393 A1 WO 2024122393A1 JP 2023042435 W JP2023042435 W JP 2023042435W WO 2024122393 A1 WO2024122393 A1 WO 2024122393A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
weight
keratin fibers
acid
glyoxylic acid
Prior art date
Application number
PCT/JP2023/042435
Other languages
English (en)
Inventor
Tomotaka Michitsuji
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2022197248A external-priority patent/JP2024082988A/ja
Priority claimed from FR2300409A external-priority patent/FR3144917A1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2024122393A1 publication Critical patent/WO2024122393A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the present invention relates to a composition, in particular a cosmetic composition, for straightening keratin fibers such as hair,
  • Straightening keratin fibers such as hair by heating the keratin fibers with an iron is popular for making unruly keratin fibers manageable and making keratin fibers have less volume and look more desirable.
  • Such a straightening method using a heating iron is convenient for quick styling, but the style lasts only short period of time, e.g., until the next shampooing.
  • a long-lasting straightening method is required for many consumers.
  • WO 2014/131469 discloses a composition for straightening keratin fibers by heating with an iron, without using reducing and oxidizing agents, wherein the composition includes glyoxylic acid.
  • An objective of the present invention is to provide an improved composition for straightening keratin fibers such as hair, based on heating the keratin fibers with glyoxylic acid or a derivative thereof, which can prevent or reduce color fading of the keratin fibers and/or can provide the keratin fibers with longer-lasting straightening effects.
  • composition for straightening keratin fibers, such as hair, with heating comprising:
  • the pH of the composition according to the present invention may be 7 or less, preferably 6 or less, and more preferably 5 or less.
  • the amount of the (a) compound(s) in the composition according to the present invention may be from 0.1% to 50% by weight, preferably from 0.5% to 40% by weight, and more preferably from 1% to 30% by weight, relative to the total weight of the composition.
  • the metal of the (b) organic acid metal salt may be selected from magnesium, calcium, and zinc.
  • the organic acid of the (b) organic acid metal salt may be selected from a-hydroxy acids, preferably selected from the group consisting of glycolic acid, lactic acid, malic acid, citric acid, tartaric acid, mandelic acid, and gluconic acid.
  • the (b) organic acid metal salt may be magnesium, calcium or zinc gluconate.
  • the amount of the (b) organic acid metal salt(s) in the composition according to the present invention may be from 0.1% to 15% by weight, preferably from 0.2% to 10% by weight, and more preferably from 0.3% to 5% by weight, relative to the total weight of the composition.
  • the amount of the (c) water in the composition according to the present invention may be from 20% to 99% by weight, preferably from 30% to 95% by weight, and more preferably from 40% to 90% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (d) at least one betaine compound, preferably selected from the group consisting of trimethylglycine, carnitine, and L-proline betaine or stachydrine, and mixtures thereof.
  • betaine compound preferably selected from the group consisting of trimethylglycine, carnitine, and L-proline betaine or stachydrine, and mixtures thereof.
  • the amount of the (d) betaine compound(s) in the composition according to the present invention may be from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may not comprise any ammonia or a thiol compound, or may comprise less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of ammonia or a thiol compound, relative to the total weight of the composition.
  • composition according to the present invention may not comprise any reducing agent or oxidizing agent, or may comprise less than 1% by weight, preferably less than 0.5% by weight, and more preferably less than 0.1% by weight of a reducing agent or an oxidizing agent, relative to the total weight of the composition.
  • the present invention also relates to a process for straightening keratin fibers, such as hair, comprising the steps of:
  • composition comprises:
  • the present invention also relates to a kit for straightening keratin fibers such as hair, comprising: at least one heater, preferably a heating iron, which is capable of providing the keratin fibers with a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C; and at least one composition comprising
  • the present invention also relates to a use of (b) at least one organic acid metal salt in a composition for straightening keratin fibers such as hair, with heating, comprising:
  • the present invention mainly relates to a composition, preferably a cosmetic composition, for straightening keratin fibers such as hair, with heating, comprising:
  • the present invention can improve a composition for straightening keratin fibers such as hair, based on heating the keratin fibers with glyoxylic acid or a derivative thereof, by providing the keratin fibers with less color fading effects and/or longer-lasting straightening effects.
  • the present invention can prevent or reduce the color fading of keratin fibers.
  • the color of keratin fibers before and after being treated with the present invention can be maintained or does not substantially change.
  • the color of dyed keratin fibers would not substantially change before and after being treated with the present invention.
  • the present invention can provide keratin fibers such as hair with longer-lasting straightening effects.
  • the present invention can lengthen or prolong the straightening effects for keratin fibers provided by using a composition including only glyoxylic acid or a derivative thereof.
  • the present invention can further maintain the straight shape of keratin fibers, or can prevent or reduce loss of the straight shape of keratin fibers over time.
  • the present invention can provide better prevention for the keratin fibers returning to the original wavy shape, after straightening the keratin fibers, in particular after shampooing.
  • the use of at least one organic acid metal salt can prevent or reduce color change of keratin fibers by straightening and/or can lengthen or prolong the straightening effects for the keratin fibers provided by glyoxylic acid or a derivative thereof.
  • the use of at least one organic acid metal salt can prevent or reduce color fading of dyed keratin fibers and/or can further maintain the straight shape of the keratin fibers provided by glyoxylic acid or a derivative thereof, or can prevent or reduce waving of the keratin fibers.
  • the present invention can also provide keratin fibers with sufficient immediate straightening effects.
  • the keratin fibers treated with the present invention can have less volume or less frizz due to the reduction of curls of the keratin fibers.
  • the straightening effects provided by the present invention can last a long time, for example, even after shampooing the keratin fibers.
  • the present invention can also provide the shape of keratin fibers with good resistance to shampooing.
  • the present invention can provide keratin fibers with less damage as compared to conventional straightening processes, because the present invention does not need to use any reducing/oxidizing agents. Therefore, it can be easy to comb the keratin fibers treated by the present invention. Thus, the keratin fibers treated with the present invention can be easy to manage. Also, the keratin fibers treated by the present invention can be stronger than those treated by conventional straightening processes.
  • the present invention can use no or very little ammonia or a thiol compound, and therefore, odor during the use of the present invention can be reduced as compared to the conventional processes which require the use of ammonia or a thiol compound. Also, the present invention can have good usability, for example, short processing time.
  • composition according to the present invention for straightening keratin fibers such as hair, with heating, comprises:
  • the above composition be a cosmetic composition, more preferably a cosmetic composition for straightening keratin fibers, and even more preferably a cosmetic composition for one-step straightening keratin fibers. It is particularly preferable that the keratin fibers be hair.
  • composition according to the present invention includes (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof.
  • a single type of (a) compound may be used, but two or more different types of (a) compounds may be used in combination.
  • the (a) compound is selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof.
  • the (a) compound is selected from glyoxylic acid and derivatives thereof.
  • glyoxylic acid solvates mention may be made of, for example, glyoxylic acid hydrates such as glyoxylic acid monohydrate.
  • glyoxylic acid salts mention may be made of, for example, alkaline metal salts or alkaline earth metal salts of glyoxylic acid such as sodium or potassium glyoxylate, and magnesium or calcium glyoxylate.
  • glyoxylic acid esters mention may be made of, for example, alkyl esters of glyoxylic acid such as methyl glyoxylate and ethyl glyoxylate.
  • glyoxylic acid amides mention may be made of, for example, N-glyoxyloylcarbocysteine and N- glyoxyloyl keratin amino acids.
  • glyoxylic acid it is preferable to use glyoxylic acid as the (a) compound.
  • the amount of the (a) compound(s) in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be 50% by weight or less, preferably 40% by weight or less, and more preferably 30% by weight or less, relative to the total weight of the composition.
  • the amount of the (a) compound(s) in the composition according to the present invention may be from 0.1% to 50% by weight, preferably from 0.5% to 40% by weight, and more preferably from 1% to 30% by weight, relative to the total weight of the composition.
  • composition according to the present invention includes (b) at least one organic acid metal salt. Two or more such salts may be used in combination. Thus, a single type of such a salt or a combination of different types of such salts may be used.
  • organic acid metal salts are used, it is possible that the types of organic acid are different and/or the types of metal are different.
  • the metal of the (b) organic acid metal salt may be selected from alkaline metals, in particular sodium and potassium.
  • the metal of the (b) organic acid metal salt may be selected from alkaline earth metals, in particular magnesium and calcium.
  • the metal of the (b) organic acid metal salt may be selected from transition metals and the group 12 elements in the periodic table such as zinc.
  • the organic acid of the (b) organic acid metal salt may be selected from a-hydroxy acids.
  • a-hydroxy acids may be represented by the following formula (I): wherein
  • R1 H, -OH, -NH2, -CH2COOH or a linear or branched C1-4 alkyl
  • the a-hydroxy acids may be selected from the following: glycolic acid, oxalic acid, lactic acid, 1 -hydroxy- 1 -cyclopropanecarboxylic acid, 2-hydroxy-3- butenoic acid, 2-hydroxyisobutyric acid, 2-hydroxy-n-butyric acid, isoserine, glyceric acid, 2- hydroxy- 3 -methylbutyric acid, 2-hydroxy-2-methylbutyric acid, 2-hydroxyvaleric acid, 4- amino-2-hydroxybutyric acid, 1 -hydroxycyclohexanecarboxylic acid, dihydroxyfumaric acid, citramalic acid, tartaric acid, citric acid, 2-hydroxy-4-(methylthio)butyric acid, mandelic acid, 2 -hydroxy-3 -methylvaleric acid, glyoxylurea, [3-imidazolelactic acid, 2 -trifluoromethyl -2- hydroxypropionic acid, hexahydromandelic acid, 2-hydroxyoctanoic
  • the a-hydroxy acid be selected from the group consisting of glycolic acid, oxalic acid, L-lactic acid, DL-lactic acid, D-lactic acid, malic acid, tartaric acid, DL- glyceric acid, arabic acid, gluconic acid, hydroxytartronic acid, lactamide, N- methyllactamide, N-ethyllactamide, and N-2 -hydroxy ethyllactamide.
  • a-hydroxy acid be selected from the group consisting of gluconic acid, glycolic acid, lactic acid, malic acid, citric acid, tartaric acid, and mandelic acid.
  • the (b) organic acid metal salt be magnesium gluconate, calcium gluconate or zinc gluconate.
  • the amount of the (b) organic acid metal salt(s) in the composition according to the present invention is 0.1% by weight or more, preferably 0.2% by weight or more, and more preferably 0.3% by weight or more, relative to the total weight of the composition.
  • the amount of the (b) organic acid metal salt(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) organic acid metal salt(s) in the composition according to the present invention may be from 0.1% to 15% by weight, preferably from 0.2% to 10% by weight, and more preferably from more than 0.3% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention includes (c) water.
  • composition according to the present invention is not anhydrous.
  • the amount of the (c) water in the composition according to the present invention is 20% by weight or more, preferably 30% by weight or more, and more preferably 40% by weight or more relative to the total weight of the composition.
  • the amount of the (c) water in the composition according to the present invention may be 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less relative to the total weight of the composition.
  • the amount of (c) water in the composition according to the present invention may be from 20% to 99% by weight, preferably from 30% to 95% by weight, and more preferably from 40% to 90% by weight relative to the total weight of the composition.
  • composition according to the present invention may further include (d) at least one betaine compound.
  • a single type of specific betaine compound may be used, or two or more different types of betaine compounds may be used in combination.
  • betaine compound here means an amphoteric compound having a positively charged cationic moiety and a negatively charged anionic moiety, wherein no hydrogen atom is bound to a positively charged atom in the positively charged cationic moiety and the positively charged cationic moiety may not be adjacent to the negatively charged anionic moiety.
  • the (d) betaine compound here is not a surfactant, which comprises at least one hydrophilic part and at least one hydrophobic part.
  • the positively charged cationic moiety in the (d) betaine compound includes, but is not limited to, a quaternary ammonium cation, a phosphonium cation, and a sulfonium cation.
  • the (d) betaine compound includes a quaternary ammonium cation as the positively charged cationic moiety.
  • the negatively charged anionic moiety in the (d) betaine compound includes, but is not limited to, a carboxylate anion.
  • the (d) betaine compound may be selected from the group consisting of trimethylglycine, carnitine, L-proline betaine or stachydrine, and mixtures thereof and preferably be trimethylglycine.
  • the amount of the (d) betaine compound(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1 % by weight or more relative to the total weight of the composition. It may be even more preferable that the amount of the (d) betaine compound(s) in the composition according to the present invention be 0.2% by weight or more relative to the total weight of the composition.
  • the amount of the (d) betaine compound(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less relative to the total weight of the composition, It may be even more preferable that the amount of the (d) betaine compound(s) in the composition according to the present invention be 3% by weight or less relative to the total weight of the composition.
  • the amount of the (d) betaine compound(s) in the composition according to the present invention may range from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight relative to the total weight of the composition. It may be even more preferable that the amount of the (d) betaine compound(s) in the composition according to the present invention be from 0.2% to 3% by weight relative to the total weight of the composition.
  • composition according to the present invention may have a pH of 7 or less, preferably 6 or less, and more preferably 5 or less, which is measured at 25°C.
  • composition according to the present invention may have a pH of 3 or more, which is measured at 25°C.
  • composition according to the present invention may have a pH of from 3 to 7, preferably from 3 to 6, and more preferably from 3 to 5, which is measured at 25°C.
  • the composition for straightening keratin fibers may include at least one alkaline agent. Two or more alkaline agents may be used in combination. Thus, a single type of alkaline agent or a combination of different types of alkaline agents may be used.
  • the alkaline agent is different from the (d) betaine compound.
  • composition according to the present invention include alkaline agent(s), if the (a) compound can function to reduce the pH of the composition.
  • the alkaline agent may be an inorganic alkaline agent. It is preferable that the alkaline agent be non-volatile. It is preferable that the inorganic alkaline agent be selected from the group consisting of alkaline metal hydroxides; alkaline earth metal hydroxides; and alkaline metal phosphates and monohydrogen phosphates such as sodium phosphate or sodium monohydrogen phosphate.
  • inorganic alkaline metal hydroxides mention may be made of sodium hydroxide, lithium hydroxide and potassium hydroxide.
  • alkaline earth metal hydroxides mention may be made of calcium hydroxide and magnesium hydroxide.
  • sodium hydroxide and potassium hydroxide are preferable.
  • the alkaline agent may be an organic alkaline agent. It is preferable that the organic alkaline agent be selected from the group consisting of monoamines and diamines.
  • alkanolamines such as mono-, di- and tri-ethanolamine, comprising 1 to 3 hydroxyalkyl(Ci-C4) groups.
  • alkanolamines may be selected from monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N,N-dimethyl ethanolamine, 2-amino-2-methyl- 1 -propanol, triisopropanolamine, 2-amino-2-methy 1-1, 3 -propanediol, 3 -amino- 1,2- propanediol, 3-dimethylamino-l,2-propanediol, and tris(hydroxymethylamino)methane.
  • the diamines may be described in the structure (B) below: wherein W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C 1 -C 4 alkyl radical, and R a , Rb, R c and Rd independently denote a hydrogen atom, an alkyl radical or a C 1 -C 4 hydroxyalkyl radical, which may be exemplified by 1,3 -propanediamine and derivatives thereof.
  • W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C 1 -C 4 alkyl radical
  • R a , Rb, R c and Rd independently denote a hydrogen atom, an alkyl radical or a C 1 -C 4 hydroxyalkyl radical, which may be exemplified by 1,3 -propanediamine and derivatives thereof.
  • the amount of the alkaline agent(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0,05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the alkaline agent(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the alkaline agent(s) may be used in a total amount of from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • composition for straightening keratin fibers may include at least one acid which is different from the (a) compound or (d) betaine compound. Two or more acids may be used in combination, Thus, a single type of acid or a combination of different types of acids may be used.
  • the acid may be used to adjust the pH of the composition according to the present invention.
  • composition according to the present invention include acid(s), if the (a) compound can function to increase the pH of the composition.
  • HC1 hydrochloric acid
  • the amount of the acid(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the acid(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the acid(s) may be used in a total amount of from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may also comprise at least one other optional ingredient, chosen in particular from: oils, preferably polar oils, and more preferably ester oils, in the form of a liquid at 25°C under atmospheric pressure; solid fatty substances and in particular C 8 -C 40 esters, C 8 -C 40 acids, and C 8 -C 40 alcohols, at 25°C under atmospheric pressure; thickeners; sunscreens; moisturizers; antidandruff agents; antioxidants; chelating agents; nacreous agents and opacifiers; plasticizers or coalescers; fillers; emulsifiers; polymers, in particular conditioning polymers, such as cationic polymers; fragrances; silanes; crosslinking agents; surfactants including anionic, cationic, amphoteric and nonionic surfactants .
  • the composition can, of course, comprise several cosmetic ingredients appearing in the above list.
  • composition according to the present invention may include one or several cosmetically acceptable organic solvents, which may be alcohols: in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol and caprylyl glycol; other polyols such as glycerol; and ethers such as ethylene glycol monomethyl, monoethyl, and monobutyl ethers, propylene glycol monomethyl, monoethyl, and monobutyl ethers, and butylene glycol monomethyl, monoethyl, and monobutyl ethers.
  • alcohols in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol and caprylyl glycol; other polyols such as glycerol; and
  • the above optional ingredient(s) can be present in normal amounts which can be easily determined by those skilled in the art and which can be, for each ingredient, between 0.01% and 80% by weight. Those skilled in the art will take care to choose the ingredients included in the composition, and also the amounts thereof, such that they do not harm the properties of the compositions used for the present invention.
  • the composition according to the present invention be free of ammonia or a thiol compound.
  • free of ammonia or a thiol compound means that the composition according to the present invention does not include a substantial amount of ammonia or a thiol compound.
  • the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of ammonia or a thiol compound, in particular no ammonia or thiol compound.
  • the thiol compound here means a compound which has at least one thiol (-SH) group.
  • the thiol compound may be a reducing agent.
  • the thiol reducing agent may be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol monothioglycolate; thiolactic acid and derivatives thereof, in particular esters thereof such as glycerol monothiolactate; 3 -mercaptopropionic acid and derivatives thereof, in particular esters thereof such as glycerol 3 -mercaptopropionate and ethyleneglycol 3 -mercaptopropionate; cysteamine and derivatives thereof, in particular C 1 -C 4 acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine; monothioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alky
  • salts mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amine salts; alkaline metal salts; and, alkaline earth metal salts.
  • primary-, secondary- or tertiary-amine for example, monoethanolamine, diisopropanolamine or triethanolamine, respectively, may be mentioned.
  • thiol reducing agent examples include, but are not limited to, sugar N-mercapto alkyl amides such as N-(mercapto-2-ethyl)gluconamide, P-mercaptopropionic acid and derivatives thereof; thiomalic acid; pantheteine; N-(mercaptoalkyl)co-hydroxyalkyl amides such as those described in European Patent Application No. 0 354 835 and N-mono- or N,N- dialkylmercapto 4-butyramides such as those described in European Patent Application No. 0 368 763; aminomercaptoalkyl amides such as those described in European Patent Application No.
  • alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (2/3) hydroxy-2 propyl thioglycolate; and the hydroxy-2 methyl- 1 ethyl thioglycolate-based mixture (67/33) described in French Patent Application No. 2 679 448.
  • composition according to the present invention may comprise a reducing agent; however, it is preferable that the composition according to the present invention comprises a reduced amount of a reducing agent or an oxidizing agent, preferably free of a reducing agent or an oxidizing agent.
  • the term “free of a reducing agent or an oxidizing agent” means that the composition according to the present invention does not include a substantial amount of a reducing agent or an oxidizing agent.
  • the composition according to the present invention includes 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less of a reducing agent or an oxidizing agent, in particular no reducing agent or no oxidizing agent.
  • the reducing agent may be a thiol reducing agent or a non-thiol reducing agent.
  • the thiol reducing agent is as described above.
  • the non-thiol reducing agent here means a reducing agent with no thiol group.
  • the non- thiol reducing agent may be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides.
  • the non-thiol reducing agent may be selected from ammonium sulfites and bisulfites as well as metal sulfites and bisulfites, more preferably alkali metal or alkali earth metal sulfites and bisulfites, and more preferably sodium sulfites and bisulfites.
  • the oxidizing agent may be chosen from hydrogen peroxide, alkali metal bromates, ferricyanides peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis.
  • the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates and persalts such as perborates and persulphates
  • compositions according to the present invention may be in any form suitable for topical application, and in particular in the form of an aqueous, alcoholic or aqueous-alcoholic, or oily solution or suspension; a solution or a dispersion of a lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of O/W, W/O or multiple type (if the composition according to the present invention includes at least one oil); a suspension or emulsion of a soft consistency of cream (O/W) or (W/O) type; an aqueous gel, or any other cosmetic form.
  • compositions according to the present invention may be in any galenical forms.
  • the compositions according to the present invention may be in the form of any treatment for hair in general, such as a cream, a lotion, a gel, and the like.
  • the present invention also relates to a process for straightening keratin fibers, preferably hair, comprising the steps of:
  • composition comprises:
  • the process according to the present invention is for the purpose of straightening keratin fibers, such as hair, preferably straightening for a long period of time, and more preferably straightening even after shampooing several times.
  • the process according to the present invention can be a semi-permanent straightening process.
  • the keratin fibers be cleaned before the step (i).
  • This cleaning step may be performed by, for example, shampooing the keratin fibers, followed by rinsing off the keratin fibers. After rinsing off, the keratin fibers may be dried. It is preferable that the keratin fibers are wet just before the step (i).
  • step (i) the composition, which is described above, is applied to keratin fibers such as hair.
  • the application of the composition may be performed by any means, such as a brush and a comb.
  • the bath ratio of the applied composition to the keratin fibers may range from 0.1 to 10, more particularly from 0.5 to 5, and preferably between 0.8 and 2.
  • the term "bath ratio" is intended to mean the weight ratio between the total weight of the applied composition and the total weight of the keratin fibers.
  • the keratin fibers be left as they are for a certain amount of time; typically from 1 minute to 1 hour, preferably from 2 to 30 minutes, and more preferably from 3 to 10 minutes, if necessary, in order to let the composition penetrate into the keratin fibers.
  • the process according to the present invention may comprise an optional step (ii) of rinsing off the keratin fibers with or without drying the keratin fibers after being rinsed off.
  • the keratin fibers is rinsed off in order to remove the composition from the keratin fibers.
  • the step of rinsing may be performed with water. It is preferable that the keratin fibers be dried after being rinsed off.
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair dryer.
  • the keratin fibers can be treated by the step (iii) after the step (i), without being rinsed off.
  • the keratin fibers which are preferably dry, are subjected to straightening at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C, with a heater, preferably a heating iron,
  • This temperature may be less than 250°C, preferably less than 240°C, and more preferably less than 230°C.
  • this temperature may be more than 50°C and less than 250°C, preferably more than 100°C and less than 240°C, and more preferably more than 150°C and less than 230°C.
  • the heating iron any conventional heating iron can be used.
  • the heating iron can have at least one plate, preferably two plates, which can be heated by, for example, electric heating.
  • the heated plate(s) can be applied onto the keratin fibers and moved along with the direction of the keratin fibers to straighten them.
  • the heating iron has two plates, and that keratin fibers are sandwiched between the two plates of the heating iron, in which at least one of the plates can be heated, and then the two plates are moved along with the direction of the keratin fibers to straighten them.
  • the heating iron in particular a part thereof contacting with keratin fibers, such as a heating plate or heating plates, has a temperature of more than 50°C and less than 250°C, more preferably more than 100°C and less than 240°C, and even more preferably more than 150°C and less than 230°C.
  • the step (iii) can be performed by one or more strokes of moving the heating iron along with the direction of keratin fibers.
  • the step (iii) can be controlled by not only the temperature of the heating iron but also the number of strokes of the heating iron.
  • the heating time may depend on the temperature of the heating iron but also the number of strokes of the heating iron. It may be, for example, from 1 second to 10 minutes, and preferably from a few seconds to 5 minutes.
  • the present invention also relates to a kit for straightening keratin fibers such as hair, comprising: at least one heater which is capable of providing the keratin fibers with a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C; and at least one composition comprising
  • the heater in the kit is not limited as long as it can heat keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C.
  • This temperature may be less than 250°C, preferably less than 240°C, and more preferably less than 230°C.
  • this temperature may be more than 50°C and less than 250°C, preferably more than 100°C and less than 240°C, and more preferably more than 150°C and less than 230°C.
  • the heater be a heating iron as explained in the above [Process],
  • the above composition may further comprise (d) at least one betaine compound.
  • the (d) betaine compound may be selected from the group consisting of trimethylglycine, carnitine, and L-proline betaine or stachydrine, and mixtures thereof.
  • the present invention also relates to a use of (b) at least one organic acid metal salt in a composition for straightening keratin fibers such as hair, with heating, comprising:
  • the heating is not limited as long as it can heat keratin fibers at a temperature of more than 50°C, preferably more than 100°C, and more preferably more than 150°C.
  • This temperature may be less than 250°C, preferably less than 240°C, and more preferably less than 230°C.
  • this temperature may be more than 50°C and less than 250°C, preferably more than 100°C and less than 240°C, and more preferably more than 150°C and less than 230°C.
  • (b) at least one organic acid metal salt(s) can prevent or reduce the color change of keratin fibers, in particular dyed keratin fibers, due to the straightening by a composition comprising the (a) compound.
  • (b) at least one organic acid metal salt(s) can lengthen or prolong the straightening effects for keratin fibers provided by the (a) compound.
  • the above composition may further comprise (d) at least one betaine compound.
  • the (d) betaine compound may be selected from the group consisting of trimethylglycine, carnitine, and L-proline betaine or stachydrine, and mixtures thereof.
  • compositions according to Examples 1-9 and Comparative Examples 1-5 were prepared by mixing the ingredients shown in Tables 1 and 2.
  • the numerical values for the amounts of the ingredients are all based on “% by weight” as raw materials.
  • the hair swatch was wetted by running lukewarm water for 5 seconds with running a finger through it.
  • the hair swatch (lg) was washed by 6 strokes of the finger through with 0.4g of a shampoo including 10.5% of sodium laureth sulfate, and rinsed off for 10 seconds with running a finger through it.
  • the hair swatch was dried by the hair dryer until the hair swatch was dried completely.
  • L*a*b* lightness / green-red I blue-yellow
  • the frizz control performance for the hair swatch provided by each composition was evaluated by visual observation in accordance with the following criteria. When the hair has less frizz or less flyaway hairs, it has a higher score.
  • compositions according to Examples 1-9 including: (a) at least one compound selected from the group consisting of glyoxylic acid, glyoxylic acid solvates, glyoxylic acid salts, glyoxylic acid esters, glyoxylic acid amides, and mixtures thereof; (b) at least one organic acid metal salt; and (c) water, were able to reduce color fading of dyed keratin fibers by the straightening process, and were able to reduce loss of the straight shape of the straightened keratin fibers even after shampooing several times.
  • compositions according to Comparative Examples 1-3 did not include the ingredient (a), and therefore, they could not maintain straightening effects even after 1 shampooing.
  • compositions according to Comparative Examples 4 and 5 did not include the ingredient (b), and therefore, they could not provide long-lasting straightening effects.

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Abstract

La présente invention concerne une composition pour le défrisage de fibres de kératine, telles que les cheveux, avec chauffage, comprenant : (a) au moins un composé choisi dans le groupe constitué par l'acide glyoxylique, les solvates d'acide glyoxylique, les sels d'acide glyoxylique, les esters d'acide glyoxylique, les amides d'acide glyoxylique et leurs mélanges ; (b) au moins un sel métallique d'acide organique ; et (c) de l'eau. La présente invention peut améliorer une composition pour le défrisage de fibres de kératine telles que les cheveux sur la base du chauffage des fibres de kératine avec de l'acide glyoxylique ou un dérivé de celui-ci, en conférant aux fibres de kératine moins d'effets de décoloration et/ou des effets de défrisage plus durables.
PCT/JP2023/042435 2022-12-09 2023-11-21 Composition pour le défrisage amélioré de fibres de kératine WO2024122393A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2022-197248 2022-12-09
JP2022197248A JP2024082988A (ja) 2022-12-09 2022-12-09 ケラチン繊維の改善された直毛化のための組成物
FR2300409A FR3144917A1 (fr) 2023-01-16 2023-01-16 Composition pour lissage amélioré des fibres kératineuses
FR2300409 2023-01-16

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EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0432000A1 (fr) 1989-11-20 1991-06-12 L'oreal Composition rÀ©ductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
EP0514282A1 (fr) 1991-05-17 1992-11-19 L'oreal Nouveaux alkylamino mercaptoalkylamides ou l'un de leurs sels cosmétiquement acceptables, et leur utilisation en tant qu'agents réducteurs, dans un procédé de déformation permanente des cheveux
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Publication number Priority date Publication date Assignee Title
EP0354835A1 (fr) 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)oméga-hydroxyalkylamides et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
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FR2679448A1 (fr) 1991-07-23 1993-01-29 Oreal Melange azetrope de thioglycolate d'hydroxy-2 propyle et de thioglycolate d'hydroxy-2 methyl-1 ethyle, son procede d'obtention et son utilisation dans un procede de deformation permanente des cheveux.
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US20170165160A1 (en) * 2014-08-29 2017-06-15 Henkel Ag & Co. Kgaa Method of increasing the wash resistance of artificially colored hair
US20160058683A1 (en) * 2014-08-31 2016-03-03 Cosphatech LLC Hair-Straightening Compositions and Methods
US20170281524A1 (en) * 2016-03-28 2017-10-05 Sweet Distribuidora, Importaco E Exportacao De Cosmeticos Ltda Cosmetic haircare product for the straightening of hair in shampoo format
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