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WO2018235890A1 - Procédé de remodelage de cheveux - Google Patents

Procédé de remodelage de cheveux Download PDF

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Publication number
WO2018235890A1
WO2018235890A1 PCT/JP2018/023578 JP2018023578W WO2018235890A1 WO 2018235890 A1 WO2018235890 A1 WO 2018235890A1 JP 2018023578 W JP2018023578 W JP 2018023578W WO 2018235890 A1 WO2018235890 A1 WO 2018235890A1
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WIPO (PCT)
Prior art keywords
hair
agent
component
mass
group
Prior art date
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PCT/JP2018/023578
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English (en)
Japanese (ja)
Inventor
琢哉 日比野
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Kao Corp
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Kao Corp
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Classifications

    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00—Processes of waving, straightening or curling hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • 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
    • A61K8/34—Alcohols
    • 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
    • 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 method of treating hair which can deform the hair semipermanently or permanently.
  • Patent Document 1 JP-A-2016-108319
  • Patent Document 2 JP-A-2016-108320
  • Patent Document 3 JP-A-2016-108321
  • the present invention comprises a single composition containing components (A), (B) and (C), or a composition containing components (A) and (C) and components (B) and (C).
  • a hair deformation treatment method comprising the step of applying to the hair a hair deformation treatment agent comprising a plurality of compositions comprising the following composition, wherein the component (B) of the composition constituting the hair deformation treatment agent
  • the present invention provides a method for treating hair distortion, wherein all or part of component (B) is present in a non-dissolved state in a composition containing (A): one or more compounds selected from glyoxylic acid, glyoxylic acid hydrate, glyoxylate, and glyoxylamide (B): having an electron donating group at at least one position of the meta position, ortho Phenolic compounds in which at least one position of position and para position is a hydrogen atom (however, the electron donating group at meta position may form a benzene ring which a hydroxyl group may substitute with
  • Patent Documents 1 to 3 have no description on the shape imparting effect by processing conditions or the influence on the hardness.
  • the present invention relates to a method for treating hair deformation that can effectively and semi-permanently deform the hair without damaging or improving the hair's stiffness, or with less damage to the hair.
  • the present inventors in hair deformation treatment using glyoxylic acid and phenol compounds, a composition containing phenol compounds in a state of not dissolving in a solvent, for example, a composition containing phenol compounds in a slurry state
  • a composition containing phenol compounds in a slurry state By using the hair deformation treatment agent as a component, it has been found that deformation treatment is possible without impairing or improving the hardness of the hair, and the present invention has been completed.
  • the hair deformation treatment method of the present invention is highly safe for the human body, and can improve the shape of the hair semipermanently or permanently without damaging or improving hair damage and stiffness, and this hair deformation can be a shampoo. It does not collapse even if washed with etc.
  • the hair can be freely repeated semipermanently to permanent deformation only by applying heat, without the need to infiltrate the hair with the hair treatment agent again.
  • hair which has been arbitrarily and repeatedly deformed by heat is also high in hair-shape resistance to hair-washing and does not lose its shape due to shampoo, water or the like.
  • “semi-permanent to permanent hair deformation” means that the hair-resistance is extremely excellent and the shape of the hair does not change even after repeated shampooing. Specifically, when the deformed hair is washed with shampoo, thoroughly washed away with water, and naturally dried, it means that the shape of the hair is maintained before and after shampooing. It should be noted that maintaining the shape of the hair means that, for example, in the case of wave-shaped hair, the number of waves does not substantially change before and after shampooing, and in the case of straight-shaped hair, waves and crimped hair are substantially generated by shampoo. It says that it does not occur.
  • hair deformation refers to deformation that does not occur due to cleavage and recombination of S—S bond of protein in the hair, and it is possible to transform straight hair into curls and the like. It includes deforming the hair to which deformation such as curling has been applied, natural crimped hair and the like into a straight hair shape.
  • the hair deformation treatment agent used in the present invention may be either a one-part hair deformation treatment agent composed of a single composition or a multi-agent hair deformation treatment agent composed of a plurality of compositions such as a two-component method.
  • the form of is also included.
  • the multi-agent type hair deformation treatment agent is a single application type in which the first agent and the second agent are mixed and applied to the hair, a sequential application type in which the agent is applied sequentially to the hair by the first agent, the second agent, etc. are categorized.
  • the total composition of the hair deformation treatment agent refers to the composition of a single composition constituting the one-part hair deformation treatment agent in the case of a one-part hair deformation treatment agent, a single application type
  • hair is applied to all the components constituting the multi-component hair deformation treating agent in an amount ratio such that the ratio of each component is within the range intended by the present invention It refers to the composition of the mixture that has been previously mixed.
  • all the compositions constituting the multi-component hair deformation treatment agent were intended for the ratio of each component in the present invention.
  • the composition of the mixture in the case of virtually mixing at an amount ratio such that it falls within the range is referred to as "the total composition of the hair deformation treatment agent".
  • Component (A) includes, in addition to glyoxylic acid, hydrates of glyoxylic acid, salts of glyoxylic acid, and glyoxyamide.
  • Glyoxylic acid hydrate includes glyoxylic acid monohydrate.
  • Examples of glyoxylic acid salts include glyoxylic acid alkali metal salts and glyoxylic acid alkaline earth metal salts, and examples of the alkali metal salts include lithium salts, sodium salts, potassium salts and the like, and examples of the alkaline earth metal salts And magnesium salts, calcium salts and the like.
  • Examples of glyoxyl amides include N-glyoxyloylcarbocysteine, N-glyoxyloylkeratin amino acid and the like.
  • the content of the component (A) in the hair deformation treatment agent used in the present invention makes the change of the hair shape after treatment more remarkable, and makes the hair resistance of the hair shape more excellent, and the hair shape by heating
  • Component (B) is a phenolic compound having an electron donating group at at least one position, preferably at two positions in the meta position, and at least one position in the ortho position and the para position with a hydrogen atom.
  • the electron donating group at the meta position of the phenol compound may form a benzene ring together with the adjacent carbon atom, and the benzene ring may be further substituted with a hydroxyl group.
  • the molecular weight of the component (B) is preferably 100 or more, more preferably 110 or more, and preferably 1000 or less, more preferably 700 or less, and still more preferably 500 or less.
  • the following components (B1), (B2), and (B3) are mentioned, for example.
  • Component (B1) is a resorcin represented by the following formula.
  • the component (B2) is a compound represented by the following general formula (1).
  • R 1 represents a hydrogen atom or a methyl group
  • a 1 and A 2 which may be the same or different, each represents a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms, or an aralkyl having 7 to 12 carbon atoms which may have a substituent Group or arylalkenyl group, linear or branched alkoxy group or alkenyloxy group having 1 to 6 carbon atoms, halogen atom or -CO-R 2 (R 2 is linear or branched alkyl having 1 to 12 carbon atoms Group or alkenyl group, an aralkyl group having 7 to 12 carbon atoms which may have a substituent, an arylalkenyl group, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent; B represents a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms, an a
  • a 1 , A 2 , B and E are hydrogen atoms, and the remaining groups do not contain a sulfo group.
  • D is a hydrogen atom or a methyl group
  • the substituent when the aralkyl group, the aryl alkenyl group or the aromatic hydrocarbon group has a substituent, examples of the substituent include a hydroxyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, or an alkenyl group Groups, and alkoxy groups having 1 to 12 carbon atoms.
  • carbon number of an aralkyl group, an aryl alkenyl group, and an aromatic hydrocarbon group points out the total carbon number containing the number of carbon atoms of a substituent.
  • the linear or branched alkyl or alkenyl group having 1 to 6 carbon atoms as R 3 and E is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec- Examples include butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1-methylpentyl, n-hexyl, isohexyl, vinyl, allyl, butenyl and hexenyl groups.
  • Examples of the linear or branched alkoxy or alkenyloxy group having 1 to 6 carbon atoms as A 1 , A 2 and E include groups in which an oxygen atom is bonded to the above-mentioned alkyl or alkenyl group having 1 to 6 carbons.
  • Examples of the linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms as A 1 , A 2 , R 2 and B include, in addition to the aforementioned alkyl and alkenyl groups having 1 to 6 carbons, n-heptyl Group, 2,4-dimethylpentyl group, 1-n-propylbutyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, 1-methylnonyl group, n-decyl group, 3, 7-dimethyl group Examples include octyl group, 2-isopropyl-5-methylhexyl group, n-undecyl group, n-dodecyl group, decenyl group and the like.
  • Examples of the linear or branched alkoxy group or alkenyloxy group having 1 to 12 carbon atoms in D include groups in which an oxygen atom is bonded to the above-mentioned alkyl or alkenyl group having 1 to 12 carbon atoms.
  • aralkyl or aryl alkenyl group having 7 to 12 carbon atoms for A 1 , A 2 , R 2 or B, benzyl, hydroxybenzyl, dihydroxybenzyl, phenylethyl, phenyl Ethenyl group, hydroxyphenylethyl group, dihydroxyphenylethyl group, hydroxyphenylethenyl group, dihydroxyphenylethenyl group, phenylpropyl group, phenylpropenyl group, phenylbutyl group, phenylbutenyl group, phenylpentyl group, phenylpentenyl group , Phenylhexyl group, phenylhexenyl group and the like.
  • the aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent in R 2 includes phenyl group, hydroxyphenyl group, dihydroxyphenyl group, trihydroxyphenyl group, naphthyl group, hydroxynaphthyl group, dihydroxynaphthyl group And the like.
  • the halogen atom of A 1, A 2 a fluorine atom, a chlorine atom, a bromine atom.
  • Specific examples of the compound represented by the general formula (1) include resorcine derivatives represented by the following general formula (1-1), benzophenone derivatives represented by the general formula (1-2), and Naphthol derivatives represented by 1-3-a) or (1-3-b) can be mentioned.
  • R 1 , A 1 , A 2 , B and E have the same meaning as described above, and D 1 represents a hydroxyl group or a methoxy group.
  • R 1 represents the same meaning as described above, D 2 represents a hydroxyl group or an alkoxy group having 1 to 12 carbon atoms, and G represents a hydroxyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, or an alkenyl group Group or an alkoxy group having 1 to 6 carbon atoms, n is an integer of 0 to 2; ]
  • the following compounds (1-1-1) to (1-1-3) are preferable.
  • a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an alkenyl group is preferable, and a hydrogen atom is more preferable.
  • B is preferably a hydrogen atom, an alkyl or alkenyl group having 1 to 4 carbon atoms, an arylalkenyl group having 7 to 10 carbon atoms which may have a substituent, a hydroxyl group, and a hydrogen atom or a substituent More preferable is an arylalkenyl group having 7 to 10 carbon atoms and a hydroxyl group.
  • E a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an alkenyl group is preferable, and a hydrogen atom is more preferable.
  • Examples of the compound corresponding to (1-1-1) include 1,3-dimethoxybenzene, 3,5-dimethoxyphenol, 2,6-dimethoxyphenol, 5- (hydroxyphenylethenyl) -1,3- Dimethoxybenzene (common name: pterostilbene) etc. are mentioned.
  • a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms, and an aralkyl or aryl alkenyl group having 7 to 12 carbon atoms which may have a substituent are preferable.
  • a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or an arylalkenyl group having 7 to 10 carbon atoms which may have a substituent is preferable.
  • B represents a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms, an aralkyl or aryl alkenyl group having 7 to 12 carbon atoms which may have a substituent, -OR 3
  • R 3 is preferably a hydrogen atom, or a linear or branched alkyl or alkenyl group having 1 to 6 carbon atoms, and may have a hydrogen atom, an alkyl or alkenyl group having 1 to 4 carbons, or a substituent
  • Preferred is a C7-10 arylalkenyl group, a hydroxyl group is more preferable, and a hydrogen atom, a C7-10 arylalkenyl group which may have a substituent, and a hydroxyl group are more preferable.
  • E is preferably a hydrogen atom, a hydroxyl group, a linear or branched alkyl or alkenyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy or alkenyloxy group having 1 to 4 carbon atoms, and a hydrogen atom or a hydroxyl group Is preferred.
  • Examples of the compound corresponding to (1-1-2) include 3-methoxyphenol, 5-methoxyresorcinol, 3-methoxybenzene-1,2-diol, 4-butyl-3-methoxyphenol, 3-methoxy- 4- (1-phenylethyl) phenol, 5- (4-hydroxyphenylethenyl) -1-hydroxy-3-methoxybenzene (conventional name: Pinostilbene), etc. may be mentioned.
  • resorcin derivatives represented by the general formula (1-1-3) include those represented by the following general formula (i) or (ii).
  • a 1 , A 2 and B are as defined above, and E 1 is a hydroxyl group, a linear or branched alkyl group having 1 to 6 carbon atoms or alkenyl group, or a linear group having 1 to 6 carbon atoms] Or a branched alkoxy group or alkenyloxy group.
  • a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms is preferable, and a hydrogen atom is more preferable.
  • B a hydrogen atom, an aralkyl group having 7 to 12 carbon atoms which may have a substituent, or an arylalkenyl group, -OR 3 (R 3 is a hydrogen atom or a linear or branched chain having 1 to 4 carbon atoms Preferred is an alkyl group or an alkenyl group).
  • a hydroxyl group a linear or branched alkyl or alkenyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy or alkenyloxy group having 1 to 4 carbon atoms is preferable.
  • 2-alkylresorcins such as 2-methylresorcin, 2-ethylresorcin, 2-propylresorcin, etc .
  • Pyrogallol 2-alkoxyresorcins such as 2-methoxyresorcin
  • Gallic acid esters such as gallic acid, methyl gallate, ethyl gallate, propyl gallate, butyl gallate and the like
  • 5- (phenylethenyl) 2-isopropylresorcin etc. may be mentioned.
  • a resorcin derivative represented by the general formula (ii) a resorcin derivative further represented by the general formula (ii-1) or (ii-2) is preferable.
  • resorcin derivatives represented by the general formula (ii-1) include 4-methylresorcin, 4-ethylresorcin, 4-propylresorcin, 4-isopropylresorcin, 4-butylresorcin (conventional name: Rucinol), 4-isobutyl resorcinol, 4-sec-butyl resorcinol, 4-tert-butyl resorcinol, 4-pentyl resorcinol, 4-isopentyl resorcinol, 4-sec-pentyl resorcinol, 4-tert-pentyl resorcinol, 4-neopentyl resorcinol, 4-Hexyl resorcinol, 4-isohexyl resorcinol, 4-heptyl resorcinol, 4-octyl resorcinol, 4- (2-ethylhexyl) res
  • 4-alkyl resorcins 4-alkenyl resorcins such as 4-vinyl resorcinol, 4-allyl resorcinol, 4-butenyl resorcinol, 4-hexenyl resorcinol, 4-decenyl resorcinol; 4-benzyl resorcinol, 4- (1-phenylethyl) resorcinol (conventional name: Simwhite 377), 4-furanylethyl resorcinol, 4-tetrahydropyranyl resorcinol, 4- (2-phenylethyl) resorcinol , 4-aralkyl resorcins such as 4- (3-phenylpropyl) resorcin; 4-hydroxy such as 4- (4-hydroxybenzyl) resorcinol, 4- (2,4-dihydroxybenzyl) resorcinol, 4- (4-hydroxyphenylethyl) resor
  • the condensation product of the component (A) and the component (B) formed in the hair makes the change of the hair shape after treatment more remarkable, and makes the hair shape resistance to hair washing more excellent.
  • 4-alkylresorcinol, 4-aralkylresorcinol from the viewpoint of making the change in shape during semipermanent re-deformation of the hair shape due to heating more remarkable, and making the hair-shape hair resistance after re-deformation even better. It is preferable to use one or more selected from 4-halogenated resorcins, and more preferable to use one or more selected from 4-hexylresorcin, rucinol, shim white, and 4-chlororesorcin.
  • a 1 and A 2 are as defined above, and B 1 is a linear or branched alkyl or alkenyl group having 1 to 12 carbon atoms, or a substituent having 7 to 12 carbon atoms] And an aralkyl group or an arylalkenyl group, -OR 3 or -COOR 3 (R 3 is a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 6 carbon atoms).
  • a resorcin derivative represented by the general formula (ii-2) As the resorcin derivative represented by the general formula (ii-2), a resorcin derivative further represented by the general formula (ii-2-a) or (ii-2-b) is preferable.
  • resorcin derivatives represented by the general formula (ii-2-a) include 5-methylresorcin, 5-ethylresorcin, 5-propylresorcin, 5-isopropylresorcin, 5-butylresorcin, 5-isobutylresorcin, 5- sec-butyl resorcinol, 5-tert-butyl resorcinol, 5-pentyl-resorcinol (conventional name: Olivetol), 5-isopentyl resorcinol, 5-neopentyl resorcinol, 5-hexyl resorcinol, 5-isohexyl resorcinol, 5-heptyl resorcin, 5-octyl resorcinol, 5- (2-ethylhexyl) resorcinol, 5-nonyl resorcinol, 5-decyl resorcinol,
  • a 1 and A 2 a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 4 carbon atoms, or an alkoxy or alkenyloxy group having 1 to 4 carbon atoms is preferable.
  • resorcin derivatives represented by the general formula (ii-2-b) 2-methylbenzene-1,3,5-triol, 2-ethylbenzene-1,3,5-triol, 2-propylbenzene-1, 3,5-triol, 2-butylbenzene-1,3,5-triol, 2-hexylbenzene-1,3,5-triol, 2-octylbenzene-1,3,5-triol, 2-dodecylbenzene 2-alkylbenzene-1,3,5-triols such as 1,3,5-triol; 2-aralkyl such as 2-benzylbenzene-1,3,5-triol, 2- (phenylethyl) benzene-1,3,5-triol, 2- (phenylpropyl) benzene-1,3,5-triol 1,3,5-triol; 2-acetylbenzene-1,3,5-triol, 2-propanoylbenzene-1,3,5-triol, 2-butanoyl
  • benzophenone derivatives represented by the general formula (1-2) include 4-benzoylresorcin (conventional name: benzophenone-1 (benzophenone-1)), 4- (hydroxybenzoyl) resorcin, 4- (dihydroxybenzoyl) resorcin, 4- (2,4-Dihydroxybenzoyl) resorcinol (conventional name: benzophenone-2 (benzophenone-2)), 4- (methylbenzoyl) resorcinol, 4- (ethylbenzoyl) resorcinol, 4- (dimethylbenzoyl) resorcinol, 4 -(Diethylbenzoyl) resorcinol, 4-naphthoylresorcinol, 2-hydroxy-4-methoxybenzophenone (conventional name: benzophenone-3 (benzophenone-3), 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (conventional use
  • R 1 is a hydrogen atom or It is preferably an alkyl group having 1 to 4 carbon atoms or alkenyl, more preferably a hydrogen atom.
  • a 1 and A 2 is a hydrogen atom, a hydroxyl group, preferably has a straight-chain or branched alkyl or alkoxy group having 1 to 4 carbon atoms of 1 to 4 carbon atoms, those which are hydrogen atom or a hydroxyl group More preferable.
  • D is a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
  • E is a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
  • Such compounds include 1-naphthol, 2-naphthol, 3-methylnaphthalen-1-ol, naphthalene-1,4-diol, naphthalene-1,5-diol, naphthalene-1,8-diol and the like.
  • the benzophenone derivatives represented by (1-2) and the naphthol derivatives represented by the general formula (1-3-a) or (1-3-b) are preferable.
  • 2-methylresorcin, 4-chlororesorcin, 4-alkylresorcin, 4-aralkylresorcin, 4-acylated resorcin, 5-alkylresorcin, 5-aralkylresorcin, 5-hydroxyarylalkenylresorcin, 2,4,6 Preference is given to trihydroxyphenylaralkyl ketones, gallic acid and gallic acid esters.
  • 4-butyl resorcinol (conventional name: Rucinol), 4-hexyl resorcinol, 4- (1-phenylethyl) resorcinol (conventional name: Simwhite 377 (Symwhite 377)), 4-furanyl ethyl resorcinol, 4 -Tetrahydropyranyl resorcinol, 5- (hydroxyphenylethenyl) resorcinol (conventional name: resveratrol), 3-hydroxyphenyl-1- (benzene-2,4,6-triol) propan-1-one (Conventional name: Phloretin), 4- (2,4-Dihydroxybenzoyl) resorcinol (conventional name: benzophenone-2 (benzophenone-2)), 5- (hydroxyphenylethenyl) -1,3-dimethoxybenzene ( Common name: Pterostilbene, 1-naphthol is preferred, 2-methylresorcinol, 2-
  • the condensation product of the component (A) and the component (B) to be formed in the hair makes the change of the hair shape after treatment more remarkable, and From the viewpoint of improving the damage repairability of hair damaged by the treatment (repairing the damaged hair by chemical treatment such as relaxor, permanent, hair color, hair bleach etc), the general formula (1-1 M-Dimethoxybenzene derivative represented by formula (1), resorcinol derivative represented by formula (1-1-3), benzophenone derivative represented by formula (1-2), formula (1-3) One or two or more selected from naphthol derivatives represented by a) or (1-3-b) are preferable.
  • resorcinol 5-alkylresorcin, 5-aralkylresorcinol, gallic acid and gallic acid ester.
  • the molecular weight of the compound represented by the general formula (1) is preferably 120 or more, and from the viewpoint of improving the penetration into the hair, it is preferably 1000 or less, more preferably 500 or less, still more preferably 300 or less.
  • the component (B3) is a compound represented by the following general formula (2).
  • R 4 represents a hydrogen atom or a methyl group
  • X represents a hydrogen atom, a hydroxyl group or a methoxy group
  • Y represents a hydrogen atom, an oxygen atom, a hydroxyl group or a methoxy group
  • Z represents a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms
  • R x is a hydrogen atom, an oxygen atom, a hydroxyl group, a methoxy group, or an aromatic hydrocarbon group which may be substituted by up to 3 hydroxyl groups or methoxy groups and may form a condensed ring with 1,3-dioxolane
  • R y is a hydrogen atom, a hydroxyl group, a methoxy group, or an aromatic hydrocarbon group which may be substituted by up to 3 hydroxyl groups or methoxy groups and may form a condensed ring with 1,3-dioxolane
  • R y is a
  • R x or Y represents only double bond when an oxygen atom, a single bond in other cases.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x or R y is an o, p-dihydroxy aromatic hydrocarbon group, In other cases it is a hydrogen atom.
  • the linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms as Z is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, A tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, 1-methylpentyl group, vinyl group, allyl group, butenyl group and the like can be mentioned.
  • aromatic hydrocarbon group in R x or R y a phenyl group, a naphthyl group and the like can be mentioned.
  • aromatic hydrocarbon group in which a condensed ring with 1,3-dioxolane is formed include 1,3-benzodioxol-5-yl group.
  • Examples of the arylcarbonyloxy group in R y include benzoyloxy group and the like, and examples of the aralkylcarbonyloxy group include benzyl carbonyloxy group, phenylethyl carbonyloxy group, phenylpropyl carbonyloxy group, phenylbutyl carbonyloxy group and the like.
  • Specific examples of the compound represented by the general formula (2) include the following (2-1) to (2-5).
  • R 4 and X have the same meaning as described above, Y 1 represents a hydrogen atom, a hydroxyl group or a methoxy group, R x1 represents an aromatic hydrocarbon group which may be substituted by up to three hydroxyl groups or methoxy groups and may form a condensed ring with 1,3-dioxolane; R y1 is a hydrogen atom, a hydroxyl group, a methoxy group, an aromatic hydrocarbon group which may be substituted by up to 3 hydroxyl groups or methoxy groups and may form a condensed ring with 1,3-dioxolane, or a hydroxyl group or This represents an arylcarbonyloxy group or an aralkylcarbonyloxy group which may be substituted by up to three methoxy groups.
  • Y 1 represents a hydrogen atom, a hydroxyl group or a methoxy group
  • R x1 represents an aromatic hydrocarbon group which may be substituted by up to three hydroxyl groups or methoxy
  • R 4 , X, Z and R x1 have the same meaning as described above, and R y2 represents a hydrogen atom, a hydroxyl group or a methoxy group.
  • R y2 represents a hydrogen atom, a hydroxyl group or a methoxy group.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 , X, Z, R x1 and R y2 have the same meaning as described above.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 , X, Z and a broken line have the same meaning as described above, Y 2 represents a hydrogen atom or an oxygen atom, R x2 represents a hydrogen atom, a hydroxyl group or a methoxy group, R y3 represents an aromatic hydrocarbon group which may have up to three hydroxyl groups or methoxy groups or may form a condensed ring with 1,3-dioxolane.
  • the broken line and the solid line adjacent to Y 2 is, Y 2 represents only double bond when an oxygen atom, a single bond in other cases.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R y3 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 , X and R x1 have the same meaning as described above, and R y11 may be substituted with up to three hydroxyl groups, methoxy groups, or hydroxyl groups or methoxy groups, and condensation with 1,3-dioxolane
  • R 4 and X in the formula have the same meaning as described above, and R x1 has up to 3 hydroxyl groups or methoxy groups A compound which represents an aromatic hydrocarbon group which may be substituted, and R y1 represents a hydrogen atom, a hydroxyl group, a methoxy group, or an arylcarbonyloxy group or an aralkylcarbonyloxy group which may be substituted by up to 3 hydroxyl groups or methoxy groups. .
  • Examples of compounds corresponding to (2-1-A) include catechin (Catechin), epicatechin (Epicatechin), epigallocatechin (Epigallocatechin), mesiadanol (Meciadanol), afzelechin (Afzelechin), epiafzelechin (Epiafzelechin), catechin gallate Catechin gallate), epicatechin gallate (Epicatechin gallate), epigallocatechin gallate (Epigallocatechin gallate), filoflavan (Phylloflavan), fisetinidol (Fisetinidol), guiburutinidol (Guibourtinidol), robinetinidol (Robinetinidol) and the like.
  • R 4 , X and R x1 have the same meaning as described above, and Y 11 represents a hydroxyl group or a methoxy group.
  • R 4 and X in the formula have the same meaning as described above, Y 11 represents a hydroxyl group, and R x1 represents a hydroxyl group or methoxy Compounds are preferred which exhibit aromatic hydrocarbon radicals which may be substituted up to three.
  • Examples of the compound corresponding to (2-1-B) include apiphorol (Apiforol), luteoforol (Luteoforol) and the like.
  • R 4 and X in the formula have the same meaning as described above, Y 11 represents a hydroxyl group or a methoxy group, and R Compounds in which x1 is an hydroxyl group or an aromatic hydrocarbon group which may have up to 3 methoxy groups substituted, and R y1 is a hydroxyl group or a methoxy group are preferable.
  • Examples of the compound corresponding to (2-1-C) include leucocyanidin (Lucococyanidin), leuco delphinidin (Leucodelphinidin), leucopelargonidin (Leucopelargonidin), leucopeonidin (Leucopeponidin), leucophysetinidin (Leucofisetinidin) and the like.
  • R 4 , X, Z and R x1 have the same meaning as described above.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 and X in the formula are as defined above, Z is a hydrogen atom, and R x1 is a hydroxyl group or three methoxy groups.
  • Compounds which exhibit an aromatic hydrocarbon group which may be substituted are preferred.
  • Examples of the compound corresponding to (2-2-A) include eriodictyol (Eriodictyol), naringenin (Naringenin), pinocembulin (Pinocembrin), hesperetin (Hesperetin), homoeriodiocthiol (Homoeriodictyol), isochrapnetin (Isosakuranetin), and stelvin. (Sterubin), sakura netin (Sakuranetin), alpinetine (Alpinetin), butin (Butin) and the like.
  • R 4 , X, Z and R x1 have the same meaning as described above, and R y21 represents a hydroxyl group or a methoxy group.
  • R y21 represents a hydroxyl group or a methoxy group.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 and X in the formula are as defined above, Z is a hydrogen atom, and R x1 is a hydroxyl group or three methoxy groups.
  • the compound which shows the aromatic hydrocarbon group which may be substituted, and R y1 shows a hydroxyl group or a methoxy group is preferable.
  • Examples of the compound corresponding to (2-2-B) include aromadendrin (Aromadendrin), taxifolin (Taxifolin), dihydro kaempferide and the like.
  • R 4 , X, Z and R x1 have the same meaning as described above.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 and X in the formula have the same meaning as described above, Z represents a hydrogen atom, and R x1 represents three hydroxyl groups or methoxy groups. Compounds which exhibit an aromatic hydrocarbon group which may be substituted are preferred.
  • Examples of compounds corresponding to (2-3-A) include luteolin (Luteolin), apigenin (Apigenin), chrysin (Chrysin), noraltocarpetin (Norartocarpetin), tricetin (Tricetin), diosmetin (diosmetin), and acetetine (Acacetin) , Chrysoeriol, Genkwanin, Techtochrysin, Tricin, 4 ', 7-Dihydroxyflavone (4', 7-Dihydroxyflavone), Pratol (Pratol) and the like.
  • R 4 , X, Z, R x1 and R y 21 have the same meaning as described above.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R x1 is an o, p-dihydroxy aromatic hydrocarbon group, otherwise Are hydrogen atoms.
  • R 4 and X in the formula are as defined above, Z is a hydrogen atom, and R x1 is up to 3 hydroxyl groups or methoxy groups.
  • the compound which shows the aromatic hydrocarbon group which may be substituted, and R y1 shows a hydroxyl group or a methoxy group is preferable.
  • Examples of compounds corresponding to (2-3-B) include quercetin (Quercetin), myricetin (Myricetin), morin (Morin), kaempferol (Kaempferol), galangin (Galangin), kaemperide (Kaempferide), tamarixetin (Tamarixetin), and laricitrin.
  • R 4 , X, Z and R y3 have the same meaning as described above.
  • Z is a linear or branched alkyl or alkenyl group having 1 to 5 carbon atoms only when R y3 is an o, p-dihydroxy aromatic hydrocarbon group, and in the other cases Are hydrogen atoms.
  • R 4 and X in the formula have the same meaning as described above, and Z is a hydrogen atom or a linear or branched chain having 1 to 5 carbon atoms.
  • Z is a hydrogen atom or a linear or branched chain having 1 to 5 carbon atoms.
  • the compound which shows an aromatic hydrocarbon group which shows an alkyl group or an alkenyl group and which R ⁇ y3 may substitute with a hydroxyl group or a methoxy group to 3 or may form a condensed ring with 1, 3- dioxolane is preferable.
  • R 4 and X in the formula have the same meaning as described above, and R y 3 may be substituted with up to 3 hydroxyl groups or methoxy groups 1
  • the compound which shows the aromatic hydrocarbon group which may form a condensed ring with 2, 3- dioxolane is preferable.
  • Examples of the compound corresponding to (2-4-B) include equol (Equol) and the like.
  • R 4 and R x2 in the formula may have the same meaning as described above, and R y3 may be substituted with up to 3 hydroxyl groups or methoxy groups.
  • Compounds which exhibit an aromatic hydrocarbon group which may form a condensed ring with 1,3-dioxolane are preferred.
  • Examples of the compound corresponding to (2-4-C) include Haginin D, Haginin E, 2-Methoxyjudaicin and the like.
  • umbelliferone (Umbelliferone) etc. are mentioned.
  • flavan-3-ol flavan-3-ol represented by the general formula (2-1-A)
  • an isoflavan represented by the general formula (2-4-B) a coumarin represented by the general formula (2-5)
  • Coumarins are preferred, and more specifically, catechin (Catechin), epicatechin (Epicatechin), epigallocatechin (Epigallocatechin), catechin gallate (Catechin gallate), epicatechin gallate (Epicatechin gallate), epigallocatechin gallate (Epicatechin gallate) Epigallocatechin gallate), Quercetin (Quercetin), Morin (Morin), Hesperetin (Hespere
  • catechin epigallocatechin, epigallocatechin gallate, morin, naringenin and equol are preferable.
  • mixtures containing the above-mentioned compounds, such as green tea extract, can also be used.
  • molecular weight 150 or more is preferable. Further, from the viewpoint of improving the penetration into the hair, the molecular weight is preferably 1000 or less, more preferably 700 or less, and still more preferably 500 or less.
  • the condensation product of the component (A) and the component (B) which are formed in the hair makes the change of the hair shape after treatment more remarkable and the hair resistance to hair shape is further excellent
  • the formula (ii-1) is used from the viewpoint of making the shape change during semipermanent re-deformation of the hair shape due to heating more remarkable, and making the hair shape after the re-deformation even more excellent in the hair-washing resistance.
  • the component (B) can be used alone or in combination of two or more kinds, and two or more types of (B1) to (B3) can be used in combination.
  • (B2) or (B3) is preferable in that the hair shape can be deformed more firmly by the constitution of the present invention.
  • component (B) examples include 4- (1-phenylethyl) resorcinol, 4-hexyl resorcinol, 4-butyl resorcinol, morin, resorcinol, 4-chlororesorcinol, 4-furanylethyl resorcinol, 2- More preferred is at least one selected from methylresorcinol and 4-tetrahydropyranyl resorcin, and more preferred is at least one selected from 4- (1-phenylethyl) resorcin, 4-hexylresorcin and morin.
  • all or part of the component (B) is not contained in the composition containing the component (B) among the compositions constituting the hair deformation treatment agent from the viewpoint of not impairing the hardness of the hair after treatment. It must be present in solution.
  • that the component (B) is in a non-dissolved state means that the component (B) is not dissolved in the solvent (mainly water of the component (C)) in the composition, even at a temperature above the melting point. Even when the component (B) is heated and melted to be in a liquid state, it may be in a state not dissolved in the solvent of the composition.
  • component (B) exists in a non-dissolved state in the composition can be confirmed by observing the presence or absence of the component (B) in a separated state using a microscope at 20 ° C. it can.
  • a method of making component (B) into a non-dissolving state in the composition containing component (B) for example, the component of increasing the content of component (B) in the composition containing component (B) The content of the lower alcohol in the composition containing (B) may be reduced.
  • the mass of the component (B) in the non-dissolving state in the composition containing the component (B) of the composition constituting the hair deformation treatment agent ([component (B) non-dissolving ]) and the component (B) in the solution is preferably 1/99 from the viewpoint of not impairing the hardness of the hair after treatment. Or more, more preferably 10/90 or more, and still more preferably 50/50 or more.
  • the content of the component (B) in the following description refers to the total amount of the component (B) contained in a dissolved state and the component (B) contained in a non-dissolved state in the entire composition of the hair deformation treatment agent I assume.
  • the total content of the component (B) as a whole in the hair deformation treatment agent used in the present invention makes the change of the hair shape after treatment more remarkable, makes the hair resistance of the hair shape more excellent, and heating From the viewpoint of making the change of shape during semi-permanent re-deformation of the hair shape more remarkable and to make the hair-resistance of the hair shape after re-deformation even more excellent, based on the entire composition of the hair deformation treatment agent, It is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, still more preferably 1.0% by mass or more, still more preferably 1.5% by mass or more, still more preferably 5% by mass or more, further preferably 10% by mass or more In addition to the above-mentioned viewpoints, from the viewpoint of formulation compoundability and economy, it is preferably 90% by mass or less, more preferably 60% by mass or less, still more preferably 40% by mass or less, still more preferably 30% by mass or less, more preferably Is 25 The amount%, more preferably not more than
  • the molar ratio (B) / (A) of the components (A) and (B) applied to the hair by the hair deformation treating agent used in the present invention is the composition of the components (A) and (B) formed in the hair.
  • the condensation product makes the change of the hair shape after treatment more remarkable, makes the hair shape more resistant to hair washing, and makes the change of the shape during semi-permanent re-deformation of the hair shape due to heating more remarkable.
  • the hair deformation treatment agent used in the present invention is preferably 0.001 or more, more preferably 0.1 or more, still more preferably 0.2 or more, still more preferably, from the viewpoint of making the hair resistance of the hair shape after re-transformation even more excellent.
  • the Mashiku is 1.6 or less.
  • the hair deformation treatment agent used in the present invention has (C) water as a medium.
  • both the first agent and the second agent use water as a medium.
  • the hair deformation treating agent of the present invention can also contain a lower alcohol having 1 to 3 carbon atoms, such as methanol and ethanol, but the component (B) has high solubility in the lower alcohol, so the component (B) It is also preferable to reduce the content of the lower alcohol in the composition containing the compound as a method for undissolving part or all of the component (B) in the hair deforming treatment agent.
  • a lower alcohol having 1 to 3 carbon atoms such as methanol and ethanol
  • the component (B) has high solubility in the lower alcohol, so the component (B) It is also preferable to reduce the content of the lower alcohol in the composition containing the compound as a method for undissolving part or all of the component (B) in the hair deforming treatment agent.
  • the content of the lower alcohol in the composition containing the component (B) is preferably 13% by mass from the viewpoint of making part or all of the component (B) insoluble in the composition containing the component (B) Or less, more preferably 10% by mass or less, still more preferably 7% by mass or less, still more preferably 5% by mass or less, still more preferably 3% by mass or less, still more preferably 1% by mass or less, still more preferably 0.5% by mass or less It is.
  • the hair deformation treatment agent used in the present invention may be in any form of one-component type, multi-component type such as two-component type, but the permeability of component (A) and component (B) into the hair From the viewpoint of improving the effect of the present invention and enhancing the effect of the present invention, it is more preferable to use a sequentially applied multi-component system, and more preferably a two-component system, containing component (A) and component (B) in different agents.
  • the first agent initially applied to the hair contains the components (B) and (C)
  • the second agent applied to the hair after the application of the first agent It is preferable to contain (A) and (C).
  • the content of the component (B) in the first agent is preferably 0.2% by mass or more, from the viewpoint of making part or all of the component (B) insoluble in the first agent. More preferably 0.5% by mass or more, still more preferably 1.0% by mass or more, still more preferably 1.5% by mass or more, still more preferably 5% by mass or more, and still more preferably 10% by mass or more. And 90% by mass or less, more preferably 60% by mass or less, still more preferably 40% by mass or less, still more preferably 30% by mass or less, still more preferably 25% by mass or less, from the viewpoint of formulation compoundability and economy. More preferably, it is 23% by mass or less.
  • the content of the component (A) in the second agent is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 2.5% by mass or more, in terms of glyoxylic acid Is 3% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less, still more preferably 15% by mass or less, still more preferably 12% by mass or less .
  • the mixing ratio is not particularly limited, but it is preferable that the composition after the combination be the hair deformation treatment agent of the present invention. Therefore, in the case of the multi-component type, the content of each component is the content in the composition after the combination unless otherwise specified.
  • the pH of the hair modification treatment agent of the present invention is preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, still more preferably 2 or less, in the case of one-component type, from the viewpoint of permeability into hair.
  • it is preferably 1 or more, more preferably 1.2 or more, and still more preferably 1.5 or more.
  • the agent containing the component (A), that is, the second agent is preferably in the above range, and the pH after mixing all the agents is more preferably in the above range.
  • the pH of the hair treatment agent refers to a value obtained by measuring as it is with a pH meter at room temperature (25 ° C.) without diluting the hair deformation agent.
  • a pH adjuster may be appropriately used.
  • a pH adjuster ammonia or a salt thereof as an alkaline agent; alkanolamine or a salt thereof such as monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol; 1,3-propanediamine etc.
  • inorganic acids such as hydrochloric acid and phosphoric acid, hydrochlorides such as monoethanolamine hydrochloride and the like; phosphates such as monopotassium dihydrogen phosphate and disodium dihydrogen phosphate monobasic, components such as lactic acid and malic acid Organic acids other than (A) can be used.
  • the hair deformation treatment agent used in the present invention preferably contains a cationic surfactant from the viewpoint of improving the feel of the hair after hair treatment and further improving the effects of the present invention.
  • the cationic surfactant is preferably a mono long-chain alkyl quaternary ammonium salt having one alkyl group having 8 to 24 carbon atoms and three alkyl groups having 1 to 4 carbon atoms.
  • the at least one mono long chain alkyl quaternary ammonium surfactant is selected from compounds represented by the following general formula.
  • R 4 is a saturated or unsaturated linear or branched alkyl group having 8 to 22 carbon atoms, R 8 -CO-NH- (CH 2 ) m -or R 8 -CO-O- (CH 2 ) m- (R 8 represents a saturated or unsaturated linear or branched alkyl chain having 7 to 21 carbon atoms, m represents an integer of 1 to 4), R 5 , R 6 and R 7 independently represents an alkyl group having 1 to 4 carbon atoms or a hydroxylalkyl group having 1 to 4 carbon atoms, and X - represents a chloride ion, a bromide ion, a methosulfate ion or an ethosulfate ion. ]
  • Suitable cationic surfactants include, for example, long chain quaternary ammonium compounds such as cetyl trimethyl ammonium chloride, myristyl trimethyl ammonium chloride, behentrimonium chloride, cetyl trimethyl ammonium bromide, stearamidopropyltrimonium chloride, etc. These can be used alone or as a mixture of these.
  • the content of the cationic surfactant in the hair deformation treatment agent used in the present invention is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and preferably 10% by mass or less, more preferably 5 It is less than mass%.
  • the cationic surfactant may be contained in the first agent, may be contained in the second agent, and is contained in both the first agent and the second agent It may be
  • the hair deformation treatment agent used in the present invention preferably contains silicone from the viewpoint of improving the feel of the hair after hair treatment and improving the cohesion.
  • silicone dimethylpolysiloxane and amino-modified silicone are preferred.
  • any cyclic or non-cyclic dimethylpolysiloxane polymer may be used.
  • SH200 series BY22-019, BY22-020, BY11-026, B22-029, BY22-034, BY22 -050A, BY22-055, BY22-060, BY22-083, FZ-4188 (all from Toray Dow Corning), KF-9088, KM-900 series, MK-15H, MK-88 (all from Shin-Etsu Chemical Co., Ltd.) Company).
  • any silicone having an amino group or an ammonium group can be used.
  • a preferred amino-modified silicone for example, a compound represented by the following formula can be used.
  • R ′ represents a hydrogen atom, a hydroxyl group or R X
  • R X represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms
  • J represents R X , R ′ ′-(NHCH 2 CH 2 ) a NH 2 , OR X or a hydroxyl group
  • R ′ ′ represents a divalent hydrocarbon group having 1 to 8 carbon atoms
  • a represents a number of 0 to 3
  • b and c represent the number average 10 or more and less than 20000, preferably 20 or more and less than 3000, more preferably 30 or more and less than 1000, and still more preferably 40 or more and less than 800.
  • amino-modified silicones include amino-modified silicones such as SF8452C, SS3551 (all from Toray Dow Corning), KF-8004, KF-867S, and KF-8015 (all from Shin-Etsu Chemical Co., Ltd.)
  • Amodimethicone emulsions such as silicone oil, SM8704C, SM8904, BY22-079, FZ-4671, and FZ4672 (all of which are manufactured by Toray Dow Corning) can be mentioned.
  • the content of silicone in the hair deformation treatment agent used in the present invention is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and preferably 20% by mass or less. More preferably, it is 10% by mass or less, still more preferably 5% by mass or less.
  • silicone may be contained in the first agent, may be contained in the second agent, or may be contained in both the first agent and the second agent. .
  • the hair deformation processing agent used by this invention contains a cationic polymer from a viewpoint of improving the feel of the hair after hair processing.
  • the cationic polymer refers to a polymer having a cationic group or a group which can be ionized into a cationic group, and also includes an amphoteric polymer which becomes cationic as a whole. That is, an aqueous solution containing an amino group or an ammonium group in the side chain of the polymer chain or containing a diallyl quaternary ammonium salt as a constitutional unit, such as cationic cellulose derivatives, cationic starch, cationic guar gum derivatives, diallyl quaternary Polymers or copolymers of ammonium salts, quaternized polyvinyl pyrrolidone derivatives and the like can be mentioned.
  • diallyl quaternary ammonium salt is preferred from the viewpoint of the softness, smoothness and finger-passing ability in rinsing and shampooing, ease of putting together in dry state and moisturizing ability, and the stability of the agent.
  • a polymer containing as a constituent unit, a quaternized polyvinyl pyrrolidone derivative and a cationized cellulose derivative are preferable, and a polymer or copolymer of a diallyl quaternary ammonium salt and a cationized cellulose derivative are more preferable.
  • diallyl quaternary ammonium salt polymers or copolymers include dimethyldiallylammonium chloride polymer (polyquaternium-6, eg, Mercote 100; Lubrizol Advanced Materials), dimethyldiallylammonium chloride / Acrylic acid copolymer (Polyquaternium-22, eg, Mercoat 280, 295; Lubrisol Advanced Materials, Inc.), dimethyldiallylammonium chloride / acrylamide copolymer (Polyquaternium-7, eg, Mercot 550; Lubrisol Advanced, Materials Inc.).
  • suitable quaternized polyvinyl pyrrolidone derivatives include polymers obtained by polymerizing vinyl pyrrolidone copolymer and dimethylaminoethyl methacrylate (polyquaternium 11 such as Gafcut 734, Gaffcut 755, Gaffcut 755N (all, Ashland)) Can be mentioned.
  • suitable cationized cellulose include polymers in which hydroxycellulose is loaded with glycidyltrimethylammonium chloride (Polyquaternium 10, for example, Leogard G, GP (above, Lion Corporation), Polymer JR-125, JR-400, JR-30M, LR-400, LR-30M (above, Ammer Co., Ltd.) and hydroxyethyl cellulose dimethyldiallyl ammonium chloride (Polyquaternium-4, for example, Cell coat H-100, L-200 (above, Akzo Nobel) Etc.).
  • Polyquaternium 10 polymers in which hydroxycellulose is loaded with glycidyltrimethylammonium chloride
  • Polyquaternium 10 for example, Leogard G, GP (above, Lion Corporation)
  • Polymer JR-125, JR-400, JR-30M, LR-400, LR-30M above, Ammer Co., Ltd.
  • the content of the cationic polymer in the hair deformation treatment agent used in the present invention is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, still more preferably 0.05% by mass or more, and preferably 20% by mass
  • the following content is more preferably 10% by mass or less.
  • the cationic polymer may be contained in the first agent, may be contained in the second agent, and is contained in both the first agent and the second agent. It is also good.
  • the hair deformation treatment agent used in the present invention may contain an antioxidant in an amount usually contained.
  • an antioxidant what is generally used in the field
  • the hair deformation treatment agent used in the present invention can appropriately contain, in addition to the above components, components that are usually blended in hair cosmetics. However, it is preferable that the hair deformation treatment agent used in the present invention does not substantially contain a precursor blended in an oxidative hair dye that dyes the hair by the oxidation reaction of the precursor and the coupler. That is, the hair deformation treating agent used in the present invention has at least one amino group, another amino group or hydroxyl group at the ortho position or para position of one amino group, and has a closed shell quinoid structure when oxidized. It does not contain substantially the aromatic compound which it has.
  • the compound of component (B) is a compound similar in structure to resorcinol representative of couplers used for oxidative hair dye, but the present invention polymerizes component (A) and component (B) in the hair It is characterized in that it makes it possible to freely deform the shape of the hair by subsequent heating, which is a technology completely different from the use of resorcinol in an oxidative hair dye.
  • the hair deformation treating agent used in the present invention does not substantially contain boric acid or silicic acid.
  • the hair deformation treatment agent used in the present invention does not substantially contain a hair reducing agent.
  • the present invention is characterized in that it enables deformation of the hair without breaking the S-S bond of protein in the hair, and the hair is cut by cutting the S-S bond in the hair using a reducing agent.
  • the hair reducing agent includes, for example, thiol glycols such as thioglycolic acid, dithioglycolic acid, cysteine, acetylcysteine, butyrolactone thiol, hydrogen sulfite and salts thereof.
  • the phrase "does not substantially contain” means that the content of the target compound in the hair deformation treatment agent is preferably less than 0.1% by mass, more preferably less than 0.01% by mass, and further It preferably means that the hair deformation treatment agent does not contain the target compound.
  • the hair deformation treatment agent used in the present invention is highly safe for the human body, and less damage to hair, so it can be suitably used particularly for human hair.
  • the hair deformation treatment method of the present invention preferably includes the following steps (i) and (ii). (i) applying and permeating the hair deformation treatment agent of the present invention to the hair (ii) shaping the hair impregnated with the hair deformation treatment agent while heating
  • the hair deforming agent may be applied to dry hair or to wet hair, but in order to swell the hair and promote the penetration of the hair treating agent into the hair. Before the step (i), it is preferable to wet the hair with water.
  • the amount of the hair deformation treatment agent to be applied to the hair in step (i) is preferably 0.05 or more, more preferably 0.1 or more, still more preferably, in bath ratio (mass of hair deformation treatment agent / weight of hair) to the weight of hair Is preferably at least 0.25, more preferably at least 0.5, and preferably at most 5, more preferably at most 3, and further preferably at most 2.
  • the above-described bath ratio is preferable for each of the first agent and the second agent from the viewpoint of improving the coatability.
  • the hair to be treated may be all or part of the hair.
  • the hair deformation treating agent can be applied to the hair by any method.
  • the hair deformation treatment agent is a multi-agent type
  • the hair is added to the hair. It may be applied, or after one of the first and second agents is applied to the hair, the other may be applied over the application portion.
  • the other agent is applied over and over.
  • the standing time in that case is preferably 1 minute or more, more preferably 3 minutes or more, still more preferably 5 minutes or more, in order to allow the hair deformation treatment agent to penetrate and diffuse into the hair, and preferably 1 hour or less More preferably, it is 30 minutes or less, More preferably, it is 20 minutes or less.
  • heating may be performed from the viewpoint of promoting the penetration of the hair deformation treatment agent. In the case of heating, heating at 40 to 90 ° C. is preferred.
  • the order of application may be arbitrary, but from the viewpoint of promoting the penetration of the hair deformation treatment agent and enhancing the effect, after applying the first agent to the hair, the second agent is applied to the hair It is more preferable to apply.
  • the step of rinsing the first agent before applying the second agent when the first agent and the second agent are applied one on another, after the first agent is applied and allowed to stand, the step of rinsing the first agent before applying the second agent ( Hereinafter, it may include an intermediate rinse step). It is preferable not to include the intermediate rinse step from the viewpoint of shortening the treatment time.
  • the molecular weight of the component (B) contained in the first agent is preferably 100 to 180, and more preferably 100 to 140, from the viewpoint of further enhancing the hair deforming effect.
  • the molecular weight of the component (B) contained in the first agent is preferably 140 to 1000, from the viewpoint of further enhancing the hair deforming effect and improving the feel after deformation. It is more preferable that it is -1000.
  • the application amount of the first agent and the second agent is not particularly determined.
  • the molar ratio (B) / (A) of the amount of component (B) in the first agent applied to hair to the amount of component (A) in the second agent applied to hair is preferably 0.1 or more, more preferably Is 0.3 or more, more preferably 0.5 or more, still more preferably 0.7 or more, preferably 5 or less, more preferably 2.5 or less, still more preferably 2 or less, still more preferably 1.5 or less, more preferably 1.2 or less Apply as.
  • the application amount to the hair of the component (B) calculated from the content of the component (B) in the first agent and the application amount of the first agent on the hair, and in the second agent may be in the above-mentioned range in molar ratio.
  • a step of leaving the hair on which the hair deformation treating agent has been applied may be inserted.
  • the standing time in that case is preferably 1 minute or more, more preferably 3 minutes or more, still more preferably 5 minutes or more, in order to allow the hair deformation treatment agent to penetrate and diffuse into the hair, and preferably 1 hour or less More preferably, it is 30 minutes or less, More preferably, it is 20 minutes or less.
  • the hair in the step of leaving, from the viewpoint of promoting the penetration of the hair deformation treatment agent, the hair may be heated. In the case of heating, heating at 40 to 90 ° C. is preferred. This heating is preferable in that the lower oligomers can be polymerized in the hair before the step (ii), so that the step (ii) can be more advantageously advanced.
  • the hair may or may not be rinsed, but the components of the hair deforming treatment agent are sufficiently retained in the hair and the hair has a semipermanent shape. From the viewpoint of further strengthening the effect of applying the hair shape and applying the heat and re-performing the hair shape semi-permanently, it is preferable not to rinse.
  • the heating temperature in the step (ii) increases the interaction between the components (A) and (B) and the proteins in the hair, and promotes the condensation reaction between the components (A) and (B) in the hair.
  • the temperature is preferably 50.degree. C. or more, more preferably 60.degree. C. or more, still more preferably 80.degree. C. or more.
  • It is 250 degrees C or less, More preferably, it is 240 degrees C or less, More preferably, it is 230 degrees C or less.
  • a heating method a method using a hair iron, an electric heating rod, a hot curler or the like can be mentioned.
  • the heating time in step (ii) is appropriately selected depending on the heating device and heating temperature used, but from the viewpoint of causing the hair deformation treating agent to penetrate and diffuse into the hair and causing sufficient polymerization, preferably 1 second or more. Seconds or more, more preferably 1 minute or more, further preferably 5 minutes or more, further preferably 15 minutes or more, further preferably 30 minutes or more, and for hair damage suppression, preferably 2 hours or less, more preferably It is 1 hour or less, more preferably 45 minutes or less.
  • the shaping in step (ii) includes both straight and curled shaping.
  • Methods for shaping the hair into a straight shape include a method in which the hair is pulled with a tool such as a hand, a comb or a brush while blowing with a dryer, a method in which heating is performed using a hair iron, etc. From the above, the method of using a hair iron is preferable. To straighten the shape of the hair while heating it with a hair iron, hold the hair with a flat iron and then slide it from the root to the end of the hair with a tool such as a hand, a comb or a brush. According to the method etc. which both are pinched and held as it is with a flat iron while pulling, and the combination of the both.
  • Step (ii) is preferably performed in an environment where evaporation of water is suppressed.
  • a specific means for suppressing the evaporation of water a method of covering the hair to which the hair deformation treating agent is applied with a film-like material made of a material that does not transmit water vapor, a cap, etc. And the like.
  • the hair may be rinsed or not rinsed, but rinsing is preferred from the viewpoint of preventing a reduction in hair feel due to excess polymer.
  • components (A) and (B) penetrate into the hair and cause interaction with proteins in the hair.
  • a thermoplastic condensation product of component (A) and component (B) is formed in the hair.
  • the hair shape can be easily deformed by heating the hair, and once it is applied, the hair is repeatedly semipermanently to permanent, just by applying heat without applying the hair deformation treatment again.
  • the hair deformation imparted by the method of the present invention does not break even when washed with a shampoo or the like.
  • thermoforming processing method After the hair is deformed by the method comprising step (i) or step (ii), heat can be applied to re-permanently re-shape the hair into another shape.
  • a temperature preferably 30 ° C. or more, more preferably 40 ° C. or more, and 230 ° C. or less, more preferably 220 ° C. or less, still more preferably 210 ° C. or less.
  • a hair deformation treatment agent nor a hair treatment agent containing a reducing agent such as a so-called permanent agent or a known hair deformation treatment agent such as an alkaline relaxer be applied.
  • the temperature reached at the time of heating the hair changes the hair shape semipermanently or permanently regardless of the type of hair iron used, the material of the heating unit, the set temperature, and the operation method of the hair iron From the viewpoint, it is preferably 80 ° C. or higher, more preferably 120 ° C. or higher, still more preferably 150 ° C., and from the viewpoint of achieving both prevention of hair damage and semipermanent or permanent deformation of the hair shape, Is 230 ° C. or less, more preferably 220 ° C. or less, still more preferably 210 ° C. or less.
  • the heating temperature of hair can be measured, for example, using a radiation thermometer (model number ST653) manufactured by SENTRY.
  • the hair When re-shaping straight hair that has been straightened to curl, the hair may be wound around a rod, curler, etc. and held while heating, or the hair may be straightened.
  • the method of winding and holding on an iron etc. is mentioned.
  • the temperature reached upon heating of the hair is preferably 30 ° C. or more, more preferably 40 ° C. or more, from the viewpoint of deforming the hair shape semipermanently to permanent.
  • it is 180 ° C. or less, more preferably 120 ° C. or less, still more preferably 100 ° C. or less, still more preferably 80 ° C. or less, still more preferably 60 ° C. or less from the viewpoint of achieving both prevention and semipermanent or permanent deformation of hair shape. It is less than ° C.
  • heating when heating, it may be a method of heating while the hair is dry, or a method of heating after it is wetted with water, but the shape of the hair is deformed semipermanently to permanently. From the point of view of heating, a method of heating after wetting with water is preferred.
  • the heating time of the hair when re-shaping the hair is appropriately selected depending on the heating tool and heating temperature used, but from the viewpoint of deforming the hair shape semi-permanently to permanently, preferably 1 second or more, more preferably 5 Seconds, preferably 1 minute or more, more preferably 5 minutes or more, further preferably 15 minutes or more, further preferably 30 minutes or more, and for hair damage suppression, preferably 2 hours or less, more preferably It is 1 hour or less, more preferably 45 minutes or less.
  • Pattern 1 When the hair deformation treating agent is one-part type 1) Optionally wet the hair with water. 2) A hair deformation treatment containing the following components (A), (B) and (C) is applied to the hair and allowed to penetrate.
  • the hair on which the hair deforming treatment agent has been applied is allowed to stand for 1 minute or more and 1 hour or less. At this time, heating may optionally be performed at 40 to 90.degree. 4) Shape the hair while heating at 50-250 ° C. 5) optionally rinse
  • Pattern 2 In the case of a two-component type with a single application of the hair deformation treatment agent 1) Optionally wet the hair with water. 2) Apply the hair deformation treatment agent, which is a mixture of the first agent containing the following components (B) and (C), and the second agent containing the components (A) and (C), to the hair and make it penetrate .
  • the hair on which the hair deforming treatment agent has been applied is allowed to stand for 1 minute or more and 1 hour or less. At this time, heating may optionally be performed at 40 to 90.degree. 4) Shape the hair while heating at 50-250 ° C. 5) optionally rinse the hair. 6) Optionally reshape the hair while heating at 40-230 ° C.
  • Pattern 3 In the case of a two-component type in which the hair deformation treatment agent is applied sequentially 1) Optionally, wet water. 2) The first agent containing the following components (B) and (C) is applied to the hair and allowed to penetrate.
  • a second agent containing the following components (A) and (C) is applied one on top of the first agent-coated portion of the hair and allowed to penetrate.
  • the hair is maintained for 1 minute to 1 hour Leave below. At this time, heating may optionally be performed at 40 to 90.degree.
  • 9) Optionally reshape the hair while heating at 40-230 ° C.
  • the first containing 4- (1-phenylethyl) resorcinol (sim white) as the component (B) Agent and a second agent comprising a second agent containing glyoxylic acid as component (A), using a two-component hair deformation treatment agent, an intermediate rinse step between the application of the first agent and the application of the second agent
  • the hair deformation treatment method to be performed is preferable.
  • a hair deformation treatment method comprising the following steps (i-1), (i-2), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 50/50, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1 and leaving at 40 to 90 ° C.
  • ⁇ Specific embodiment 2> From the viewpoint of shortening the treatment time, as shown below, it contains a first agent containing 4- (1-phenylethyl) resorcinol (sim white) as component (B), and glyoxylic acid as component (A). It is preferable to use a sequentially applied two-component hair deformation treatment agent comprising a second agent, and a hair deformation treatment method in which an intermediate rinse step is not performed between the application of the first agent and the application of the second agent.
  • a sequentially applied two-component hair deformation treatment agent comprising a second agent, and a hair deformation treatment method in which an intermediate rinse step is not performed between the application of the first agent and the application of the second agent.
  • a hair deformation treatment method comprising the following steps (i-1), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 20/80, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1 and leaving at 40 to 90 ° C.
  • ⁇ Specific embodiment 3> From the viewpoint of shortening the treatment time, as shown below, it contains a first agent containing glyoxylic acid as component (A), and 4- (1-phenylethyl) resorcinol (sim white) as component (B) It is preferable to use a sequentially applied two-component hair deformation treatment agent comprising a second agent, and a hair deformation treatment method in which an intermediate rinse step is not performed between the application of the first agent and the application of the second agent.
  • a hair deformation treatment method comprising the following steps (i-1), (i-3) and (ii).
  • (i-1) The first agent containing the components (A) and (C) and having a pH of 1 to 4 in a hair ratio (weight of first agent / weight of hair) 0.1 / 1 to 5 / Apply at 1 and stand at 40 to 90 ° C.
  • the hair deformation processing method containing the following process (i) and (ii).
  • the mass of the component (B) in the undissolved state ([component (B) undissolved ]) containing the components (A) to (C) and the mass of the component (B) in the dissolved state ([component (B) ) dissolved]) and the mass ratio of [component (B) insoluble] / [component (B) dissolved] is 100 / 0-50 / 50
  • the hair deformation treatment agent has a pH of 1-4
  • ⁇ Specific embodiment 5> From the viewpoint of improving the feel after hair deformation treatment, as shown below, it comprises a first agent containing 4-hexylresorcinol as component (B) and a second agent containing glyoxylic acid as component (A)
  • a hair deformation treatment method in which an intermediate rinse step is performed between the application of the first agent and the application of the second agent using a two-component hair deformation treatment agent of a sequential application type.
  • a hair deformation treatment method comprising the following steps (i-1), (i-2), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 50/50, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1, and leaving at 40 to 90 ° C.
  • the hair treatment method of the present invention is a technology that enables freely changing the hair according to a completely different principle from the perming treatment using a reducing agent and the relaxor treatment using a strongly alkaline hair treatment agent.
  • the step of applying a hair treatment agent containing a reducing agent or a strongly alkaline hair treatment agent to the hair is not included. Therefore, the hair treatment method of the present invention can be said to be advantageous as compared with the above-mentioned conventional hair deforming method, that the hair can be deformed without damaging the hair and without damaging the stiffness.
  • a single composition containing components (A), (B) and (C), or a composition containing components (A) and (C) and a composition containing components (B) and (C) A method for treating hair deformation, comprising the step of applying to the hair a hair deforming treatment agent comprising a plurality of compositions comprising: a composition comprising component (B) of the composition constituting the hair deformation treating agent A method for treating hair deformation, wherein all or part of the component (B) is present in a non-dissolved state.
  • the mass ratio [component (B) not dissolved ] / [component (B) dissolved ] is preferably 1/99 or more, more preferably 10/90 or more, still more preferably 50/50 or more, ⁇ 1>
  • the molar ratio (B) / (A) of the content of component (B) to the content of component (A) in the total composition of the hair deformation treatment agent is preferably 0.001 or more, more preferably 0.1 or more, still more preferably 0.2 Or more, more preferably 0.25 or more, still more preferably 0.30 or more, still more preferably 0.4 or more, preferably 10 or less, more preferably 5 or less, still more preferably 2.5 or less, still more preferably 2.3 or less, more preferably
  • the hair deformation treatment method according to ⁇ 1> or ⁇ 2> which is 2.1 or less, more preferably 1.9 or less, further preferably 1.7 or less, further preferably 1.6 or less.
  • the content of the component (A) in the total composition of the hair deformation treatment agent is, in terms of glyoxylic acid, preferably 1.0% by mass or more, more preferably 2.0% by mass or more, still more preferably 2.5% by mass or more, still more preferably 3.0. % By mass, preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less, still more preferably 15% by mass or less, still more preferably 12% by mass or less.
  • the hair deformation treatment method according to any one of 1> to ⁇ 3>.
  • the content of the component (B) in the total composition of the hair deformation treating agent is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, still more preferably 1.0% by mass or more, still more preferably 1.5% by mass or more
  • the content is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 90% by mass or less, more preferably 60% by mass or less, still more preferably 40% by mass or less, still more preferably 30% by mass or less.
  • the content of the lower alcohol in the composition containing the component (B) is preferably 13% by mass or less, more preferably 10% by mass or less, still more preferably 7% by mass or less, still more preferably 5% by mass or less, more preferably
  • ⁇ 7> The hair deformation treatment method according to any one of ⁇ 1> to ⁇ 6>, wherein the component (A) is preferably glyoxylic acid.
  • Component (B) is preferably resorcin, 2-methylresorcin, 4-butylresorcin (conventional name: Rucinol), 4-hexylresorcin, 4- (1-phenylethyl) resorcin (conventional name: Sim White 377) (Symwhite 377)), 4-chlororesorcinol, 5- (hydroxyphenylethenyl) resorcinol (conventional name: resveratrol), 5- (hydroxyphenylethenyl) -1,3-dimethoxybenzene (conventional name: Pterostilbene (Pterostilbene), 3-hydroxyphenyl-1- (benzene-2,4,6-triol) propan-1-one (conventional name: Phloretin, 4- (2,4-dihydroxybenzoyl) resorcinol (Conventional name: benzophenone-2 (benzophenone-2)), 1-naphthol, catechin (Cate
  • Component (B) is preferably 4- (1-phenylethyl) resorcinol, 4-hexyl resorcinol, 4-butyl resorcinol, morin, resorcinol, 4-chlororesorcinol, 4-furanylethyl resorcinol, 2-methyl resorcinol and 4 At least one member selected from -tetrahydropyranyl resorcins, more preferably one or more members selected from 4- (1-phenylethyl) resorcin, 4-hexylresorcin and morin, ⁇ 1> to ⁇ 8>
  • the hair deformation treatment method according to any one of the above.
  • the hair deformation treatment method according to any one of ⁇ 1> to ⁇ 9>, including the following steps (i) and (ii). (i) applying a one-part hair deformation treating agent containing components (A), (B) and (C) to hair and infiltrating the hair (ii) forming the hair impregnated with the hair deformation treating agent while heating Step to attach
  • the hair deformation treatment method according to any one of ⁇ 1> to ⁇ 9>, including the following steps (i) and (ii).
  • a first agent and a second agent of a multi-agent hair deformation treating agent comprising a first agent containing the components (B) and (C) and a second agent containing the components (A) and (C)
  • the step of applying to hair and infiltrating ii) the step of heating the hair infiltrated with the hair deformation treatment agent while heating
  • the hair deformation treatment method according to any one of ⁇ 1> to ⁇ 9>, including the following steps (i) and (ii). (i) applying to a hair a first agent of a multi-agent hair distortion treating agent comprising a first agent containing the components (B) and (C) and a second agent containing the components (A) and (C) Infiltrating and infiltrating and infiltrating the second agent onto the first agent-applied portion of the hair, and (ii) shaping while heating the hair infiltrated with the hair deformation treating agent
  • a hair deformation treatment method comprising the following steps (i-1), (i-2), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 50/50, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1 and leaving at 40 to 90 ° C.
  • a hair deformation treatment method comprising the following steps (i-1), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 50/50, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1 and leaving at 40 to 90 ° C.
  • a hair deformation treatment method comprising the following steps (i-1), (i-3) and (ii).
  • (i-1) The first agent containing the components (A) and (C) and having a pH of 1 to 4 in a hair ratio (weight of first agent / weight of hair) 0.1 / 1 to 5 / Apply at 1 and stand at 40 to 90 ° C.
  • the hair deformation processing method containing the following process (i) and (ii).
  • the mass of the component (B) in the undissolved state ([component (B) undissolved ]) containing the components (A) to (C) and the mass of the component (B) in the dissolved state ([component (B) ) dissolved]) and the mass ratio of [component (B) insoluble] / [component (B) dissolved] is 100/0 ⁇ 50/50
  • hair deformation treatment agent has a pH of 1-4
  • a hair deformation treatment method comprising the following steps (i-1), (i-2), (i-3) and (ii).
  • (i-1) The mass of the component (B) in an undissolved state ([component (B) undissolved ]) containing the components (B) and (C) and the mass of the component (B) in a dissolved state ([component (B) Dissolution ] mass ratio to [component (B) non-dissolution ] / [component (B) dissolution ] is 100/0 to 50/50, and pH is 1.5 to 8; Applying a bath ratio (mass of first agent / mass of hair) 0.1 / 1 to 5/1, and leaving at 40 to 90 ° C.
  • Examples 1 to 6 and Comparative Examples 1 to 3 The two-component hair deformation treatment agents of Examples 1 to 6 and Comparative Examples 1 and 2 shown in Tables 1 and 2 were prepared, subjected to the following hair treatments, and the shape-imparting effects and the hardness of the treated hairs were evaluated. . In addition, also when the hair deformation process is performed using the commercially available perm agent (Kao Professional Salon Service, Topform TG) as Comparative Example 3, it shows. These results are shown together in Tables 1 and 2.
  • ⁇ Semipermanent curl shape giving process> 1.
  • a straight bundle of 0.5 g length and 25 cm length of Caucasian straight hair (untreated hair) was wet with tap water at 30 ° C. for 30 seconds.
  • the hair bundle was applied with 1 g of the first agent, covered with a wrap and sealed, and heated in an oven set at 90 ° C. for 1 hour.
  • the tress was removed from the oven and allowed to return to room temperature (25 ° C.). 4.
  • the hair tress is rinsed for 30 seconds in running water at 30 ° C in tap water, foamed for 60 seconds in a shampoo for evaluation, rinsed for 30 seconds in running water at 30 ° C in tap water, and then the wet hair tress is wound around a plastic rod of 14 mm in diameter , Fixed with a clip. 5. 1 g of the second agent was applied to the hair bundle wound around the rod, the entire rod was covered with a wrap and sealed, and heated in an oven set at 90 ° C. for 1 hour. 6. The tress was removed from the oven and allowed to return to room temperature. 7. The tress was removed from the rod, rinsed in running tap water at 30 ° C. for 30 seconds, and frothed with the evaluation shampoo for 60 seconds. 8.
  • the root of the hair bundle was gently pulled out from the water and lightly shaken to cut off the water .
  • the sample was hung in a laboratory for 2 hours, allowed to stand, dried, passed through a comb, then hung and photographed from the side. Based on the photograph, the radius of curvature of the strongest curled portion of the hair bundle was determined, and the curl diameter was determined by doubling this radius.
  • a composition containing the component (B) in the case of a single composition containing the components (A), (B) and (C), the hair deformation treating agent is the single composition, the component (A) And the composition containing the components (B) and (C), and the composition containing the components (B) and (C) when it is composed of a plurality of compositions containing the composition containing the components (B) and (C)
  • a formulation having the same composition as the substance was prepared, and the mass ratio [component (B) non-dissolution ] / [component (B) dissolution ] was determined by the following “method ⁇ ” or “method ⁇ ”.
  • Method ⁇ The composition containing the component (B) is centrifuged (apparatus: Tomy MX-301, 6000 rpm, 20 minutes), and the mass of the dissolved component (B) is the measured absorbance value (apparatus: JASCO made) Calculated from V-560). Thereafter, the mass ratio of the component (B) in the undissolved state to the component (B) in the dissolved state in the composition containing the component (B) based on the following formula [component (B) not dissolved ] / [component ( B) Dissolution was calculated.
  • Curl diameter is 1 or more and 2 or less times of used rod (diameter 14 mm)
  • Curl diameter is 2 or more and less than 3 times of used rod (diameter 14 mm)
  • Curl diameter is used rod ((14 mm) 3 times or more and less than 4 times of diameter 14 mm)
  • the curled diameter is 4 times or more and less than 50 times of the used rod (diameter 14 mm)
  • Straight hair remains, no change in shape before treatment
  • Example 7 After the hair treatment of Example 1, the set was ironed at 150 ° C. to straighten the hair. The treated hair was clean and straight.
  • Example 8 A one-part hair deformation treatment agent of Example 8 shown in Table 3 was prepared, the following hair treatment was carried out, and the shape-imparting effect and hardness of the hair treated in the same manner as described above were evaluated. The results are shown in Table 3 together.
  • ⁇ Semipermanent curl shape giving process> 1.
  • a wet bundle of 0.5 cm long, 25 cm long, of caussian straight hair (untreated hair) was wet with tap water at 30 ° C. for 30 seconds, and then the wet hair bundle was wound around a plastic rod having a diameter of 14 mm and fixed with a clip.
  • 1 g of one-part hair deformation treatment agent was applied to the hair bundle wound around the rod, the whole of the rod was covered with a wrap and sealed, and heated in an oven set at 90 ° C. for 1 hour.
  • the tress was removed from the oven and allowed to return to room temperature (25 ° C.). 4.
  • the tress was removed from the rod, rinsed in running tap water at 30 ° C.
  • Example 9 In step 4 of ⁇ semipermanent curl forming process> of Example 1, the hair bundle is made of plastic having a diameter of 14 mm without performing “rinse with running water” to “foaming with a shampoo for evaluation” to “rinse with running water”. The hair bundle was treated in the same manner except that it was wound around a rod and fixed with a clip, and evaluation was made in the same manner. As a result, the effect of semipermanent curl shape formation was “B”, and the hardness of hair was “A”.
  • Example 10 In the process 2 of ⁇ semipermanent curl forming process> of Example 1, the same amount of the second agent is used instead of the first agent, and the same amount of the first agent is used instead of the second agent in the step 5,
  • step 4 without performing “rinse with running water” to “foaming with a shampoo for evaluation” to “rinse with running water”, the hair bundle is wound around a plastic rod having a diameter of 14 mm and fixed similarly with a clip. The tufts were treated and evaluated in the same manner. As a result, the effect of semipermanent curl shape formation was "C”, and the hardness of hair was "B".

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Abstract

La présente invention concerne un procédé de remodelage des cheveux qui comprend une étape consistant à appliquer un agent de remodelage des cheveux, ledit agent de remodelage des cheveux comprenant soit une composition unique contenant des composants (A) à (C), soit une pluralité de compositions comprenant une composition contenant des composants (A) et (C) et une composition contenant des composants (B) et (C), aux cheveux, où, dans les compositions contenant le composant (B) constituant l'agent de remodelage des cheveux, une partie ou la totalité du composant (B) existe dans un état non dissous. (A) : l'acide glyoxylique, etc. (B) : un composé de phénol comportant un groupe électrodonneur au niveau d'un ou plusieurs sites en position méta et un atome d'hydrogène en position ortho et/ou para. (C) : de l'eau.
PCT/JP2018/023578 2017-06-22 2018-06-21 Procédé de remodelage de cheveux Ceased WO2018235890A1 (fr)

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EP4021379B1 (fr) * 2019-08-29 2025-06-18 Kao Corporation Composition, procédé et kit de lissage et de bouclage de fibres kératiniques semi-permanent

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JP2016108319A (ja) * 2014-12-05 2016-06-20 花王株式会社 毛髪変形処理剤
JP2016108321A (ja) * 2014-12-05 2016-06-20 花王株式会社 毛髪変形処理剤
WO2017167596A1 (fr) * 2016-03-29 2017-10-05 Kao Germany Gmbh Procédé de traitement capillaire
JP2017218397A (ja) * 2016-06-03 2017-12-14 花王株式会社 毛髪処理方法

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