WO2022230090A1 - Composition de coloration capillaire - Google Patents

Composition de coloration capillaire Download PDF

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Publication number
WO2022230090A1
WO2022230090A1 PCT/JP2021/016911 JP2021016911W WO2022230090A1 WO 2022230090 A1 WO2022230090 A1 WO 2022230090A1 JP 2021016911 W JP2021016911 W JP 2021016911W WO 2022230090 A1 WO2022230090 A1 WO 2022230090A1
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Prior art keywords
hair
oxidation
oxidation dye
dye
agent
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PCT/JP2021/016911
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English (en)
Japanese (ja)
Inventor
知彦 遠藤
栄里 伊藤
成人 加藤
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ホーユー株式会社
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Application filed by ホーユー株式会社 filed Critical ホーユー株式会社
Priority to PCT/JP2021/016911 priority Critical patent/WO2022230090A1/fr
Priority to JP2022072615A priority patent/JP2023165419A/ja
Publication of WO2022230090A1 publication Critical patent/WO2022230090A1/fr

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    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to a hair dye composition containing 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof.
  • an oxidative hair dye comprising a first agent containing an alkaline agent and an oxidation dye and a second agent containing an oxidizing agent such as hydrogen peroxide is known.
  • the alkaline agent promotes the action of the oxidizing agent contained in the second agent, and also swells the hair to improve the penetration of the dye into the hair.
  • the oxidizing agent decomposes the melanin pigment in the hair and forms an oxidation dye polymer inside the hair. After the alkaline agent is removed, the hair cuticle is closed and the oxidation dye polymer is enclosed inside the hair.
  • the oxidative hair dye composition disclosed in Patent Document 1 contains a dye intermediate such as toluene-2,5-diamine as the main component of the dye.
  • the oxidative hair dye composition using p-phenylenediamine or the like is excellent in hair dyeing power, there is a problem that it is inferior in ease of washing and removal from the skin.
  • the present invention contains 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof as a dye, and a specific oxidation dye, thereby facilitating washing and removal from the skin while maintaining hair dyeing power (hereinafter referred to as , “skin cleansing property”) can be improved.
  • the hair dye composition of one embodiment of the present invention includes (A) 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof as an oxidation dye, and (B) an oxidation dye (1) an oxidation dye that does not have a benzene ring, (2) an oxidation dye that does not have an amine group, (3) has a benzene ring and a heterocyclic ring, and whether the benzene ring and the heterocyclic ring are directly bonded , an oxidation dye attached through one covalent bond or attached through two or three consecutive covalent bonds; (4) a benzene ring and an amine group, wherein all amine groups are (5) an oxidation dye that is a secondary or tertiary amine and is substituted with a carbon chain having 2 or more carbon atoms, (5) a benzene ring and a primary amine group, where all primary amine groups having functional groups attached to the carbons flanking the carbon
  • the (B) oxidation dye satisfies any two or more of the requirements of (1), (2), and (3) to (6). may include any one or more of
  • the oxidation dye (B) is 4-chlororesorcinol, 2,7-naphthalenediol, 3-amino-2,4-dichlorophenol, 2-methylresorcinol, 2,4,5, 6-tetraaminopyrimidine, 2-amino-4-hydroxyethylaminoanisole, hydroxyethyl-3,4-methylenedioxaniline, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3, 5-pyridinediamine, 2-amino-3-hydroxypyridine, 2,5,6-triamino-4-pyrimidinol, 1-hydroxyethyl-4,5-diaminopyrazole, resorcinol, 1,5-naphthalenediol, 1-naphthol , 2-methyl-5-hydroxyethylaminophenol, 5,6-dihydroxyindoline, 5,6-dihydroxyindole, and salts thereof.
  • the (B) oxidation dye may contain at least 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof.
  • the hair dye composition may have a pH of 10.5 or less at the time of use.
  • the hair dye composition may further contain (D) a polymerization accelerator.
  • a hair dye composition according to another aspect of the present invention does not contain an oxidizing agent, and (A) 6-methoxy-2-methylamino-3-aminopyridine as an oxidation dye or As salts and (B) oxidation dyes, (1) oxidation dyes having no benzene ring, (2) oxidation dyes having no amine group, (3) having a benzene ring and a heterocyclic ring, and the benzene ring and (4) a benzene ring and an amine group to which the heterocyclic ring is directly attached, attached via one covalent bond, or attached via two or three consecutive covalent bonds; all amine groups are secondary or tertiary amines and are substituted with carbon chains having 2 or more carbon atoms; (5) having a benzene ring and a primary amine group; 2, for the primary amine group of 2 (6) an oxidation dye having a functional group having two or more continuous covalent bonds; It is characterized
  • the oxidation dye (B) is 2,7-naphthalenediol, 3-amino-2,4-dichlorophenol, 2-methylresorcinol, and 2,4,5,6-tetraaminopyrimidine. , isatin, 1,5-naphthalenediol, 5,6-dihydroxyindoline, 5,6-dihydroxyindole, 5-amino-6-chloro-o-cresol, and salts thereof.
  • the (B) oxidation dye may be any one or more of 5,6-dihydroxyindoline, 5,6-dihydroxyindole, and salts thereof.
  • the (C) oxidation dye further optionally has a benzene ring and an amine group, and the positional relationship between the amine groups or the positional relationship between the amine group and the hydroxyl group includes an ortho position or a para position.
  • the oxidation dye excluding the (B) oxidation dye
  • the mass ratio (A/C) of the content of the (A) oxidation dye to the total content of the (C) oxidation dye is 1 or more good.
  • the mass ratio of the content of the alkali agent to the content of the oxidation dye (A) may be 0.1 or more.
  • any one or more of A, B, and C means “A only, B only, C only, A and B, A and C, B and C, or A and B and C.” means
  • the hair dye composition of the present embodiment is a multi-component hair dye composition, for example, a two-component hair dye composition such as a first component containing an oxidation dye or the like and a second component containing an oxidizing agent or the like. configured as The components of the two-agent type hair dye composition are exemplified below.
  • a solubilizing agent such as water
  • the numerical value of mass % indicating the content of the component is the numerical value in the dosage form including them.
  • the first part of the hair dye composition may further preferably contain an alkali agent, (D) a polymerization accelerator, etc., in addition to the oxidation dye as described above.
  • ((A) oxidation dyes are classified into couplers and dye intermediates, and are usually colored by polymerization of dye intermediates or by polymerization of dye intermediates and couplers.
  • (A) 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof is contained as an essential dye.
  • Specific examples of salts include hydrochloride, sulfate, hydrobromide and the like.
  • these (A) oxidation dyes one kind of (A) oxidation dye may be used alone, or two kinds of (A) oxidation dyes may be used in combination.
  • 6-methoxy-2-methylamino-3-aminopyridine dihydrochloride (HC Blue7) is preferred from the viewpoint of excellent dye stability.
  • the lower limit of the content of the oxidation dye (A) in the mixture of the first agent and the second agent, that is, the hair dye composition applied to the hair at the time of hair dyeing treatment, is appropriately set, but preferably It is 0.1% by mass or more, more preferably 0.2% by mass or more, and still more preferably 0.3% by mass or more.
  • the upper limit of the content of the (A) oxidation dye in the mixture is appropriately set, but from the viewpoint of the solubility of the (A) oxidation dye, it is preferably 2% by mass or less, more preferably 1.4% by mass. Below, more preferably 1% by mass or less. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the hair dye composition of the present embodiment contains the following (B) oxidation dye as an oxidation dye.
  • (B) oxidation dyes one kind of (B) oxidation dye may be used alone, or two or more kinds of (B) oxidation dyes may be used in combination.
  • (B) oxidation dye does not include (A) oxidation dye.
  • the oxidation dye is selected from the specific examples shown below that satisfy one or more of the following conditions (1) to (6).
  • an oxidation dye that satisfies any one or more of (1) and (2) and any two or more of (3) to (6).
  • (1) and (2) or hydroxyethyl-3,4-methylenedioxaniline (HYDROXYETHYL-3,4-METHYLENEDIOXYANILINE), 3-amino-2,4-dichlorophenol (3-AMINO-2,4-DICHLOROPHENOL), 2-amino-4-hydroxyethylaminoanisole (2-AMINO-4-HYDROXYETHYLAMINOANISOLE), 2-methyl-5-hydroxyethylaminophenol (2-METHYL-5-HYDROXYETHYLAMINOPHENOL ) are more preferred.
  • oxidation dye (1) examples include 2,6-dihydroxy-4-methyl-pyridine, 2,4,5,6-tetra Aminopyrimidine (2,4,5,6-TETRAAMINOPYRIMIDINE), 2,6-dihydroxy-3,4-dimethylpyridine (2,6-DIHYDROXY-3,4-DIMETHYLPYRIDINE), 2,6-dimethoxy-3,5- Pyridinediamine (2,6-DIMETHOXY-3,5-PYRIDINEDIAMINE), 2,6-bis-(2-hydroxyethyl)-3,5-pyridinamine (2,6-BIS-(2-HYDROXYETHYL)-3, 5-PYRIDINEDIAMINE), 5-amino-2,6-dimethoxy-3-hydroxypyridine (5-AMINO-2,6-DIMETHOXY-3-HYDROXYPYRIDINE), 4,5-diamino-1-methylpyrazole (4,5- DIAMINO-1-MET
  • oxidation dyes include 5-Hydroxy-1,4-benzodioxane, 3,4-methylenedioxyphenol (3,4 -METHYLENEDIOXYPHENOL), 2-Bromo-4,5-methylene-dioxy-phenol, 1,7-NAPHTHALENEDIOL, pyrocatechol ( PYROCATECHOL), RESORCINOL, 4-CHLORORESORCINOL, PYROGALLOL, 1-NAPHTHOL, 1,5-NAPHTHALENEDIOL, 2,7- 2,7-NAPHTHALENEDIOL, HYDROQUINONE, 1-Methyl-2,4,5-trihydroxy-benzene, 1,2,4 - 1,2,4-TRIHYDROXYBENZENE, 2-METHYLRESORCINOL, 2,3-NAPHTHALENEDIOLE, THYMOL, 2,3-dihydroxy-1 , 2,3-Dihydroxy-1,4-naphthoquinone
  • (3) above oxidation dyes include 3,4-methylenedioxyaniline (3,4-METHYLENEDIOXYANILINE), 4,5-diamino-1-((4-chlorophenyl)methyl)-1H - Pyrazole (4,5-DIAMINO-1-((4-CHLOROPHENYL)METHYL)-1H-PYRAZOLE), 5-Hydroxy-1,4-benzodioxane, 3,4 - 3,4-METHYLENEDIOXYPHENOL, 2-Bromo-4,5-methylene-dioxy-phenol, HYDROXYBENZOMORPHOLINE, 4 - 4-HYDROXYINDOLE, 5,6-DIHYDROXYINDOLE, 6-HYDROXYINDOLE, 5,6-DIHYDROXYINDOLINE, phenylmethylpyrazolone (PHENYL METHYL PYRAZOLONE), HYDROXYETH
  • (4) of oxidation dyes include hydroxybenzomorpholine, 4-hydroxyindole, 5,6-dihydroxyindole, 6-hydroxy indole (6-HYDROXYINDOLE), 5,6-dihydroxyindoline (5,6-DIHYDROXYINDOLINE), 2-methyl-5-hydroxyethylaminophenol (2-METHYL-5-HYDROXYETHYLAMINOPHENOL), 3-ethylamino-p-cresol ( 3-ETHYLAMINO-p-CRESOL), N,N-diethyl-m-aminophenol (N,N-DIETHYL-m-AMINOPHENOL), 2,6-hydroxyethylaminotoluene (2,6-HYDROXYETHYLAMINOTOLUENE), 5-( 2-hydroxyethyl)-amino-4-methoxy-2-methylphenol (5-(2-Hydroxyethyl)-amino-4-methoxy-2-methyl
  • oxidation dye (5) examples include 3-amino-2,4-dichlorophenol (3-AMINO-2,4-DICHLOROPHENOL), 2-amino-4-hydroxyethylaminoanisole (2 -AMINO-4-HYDROXYETHYLAMINOANISOLE), 4,6-bis-(2-hydroxyethoxy)-m-phenylenediamine (4,6-BIS(2-HYDROXYETHOXY)-m-PHENYLENEDIAMINE), 2,4-dimethoxy-1, 3-diamino-benzene (2,4-Dimethoxy-1,3-diamino-benzene), N-cyclopentyl-m-aminophenol (N-CYCLOPENTYL-m-AMINOPHENOL), 5-amino-4-methoxy-2-methyl - Phenol (5-Amino-4-methoxy-2-methyl-phenol), including salts thereof.
  • 3-amino-2,4-dichlorophenol (3-
  • (6) above oxidation dyes include HYDROXYBENZOMORPHOLINE, 4-HYDROXYINDOLE, 5,6-dihydroxyindole (5,6-DIHYDROXYINDOLE), 6-hydroxy indole (6-HYDROXYINDOLE), 5,6-dihydroxyindoline (5,6-DIHYDROXYINDOLINE), 2-methyl-5-hydroxyethylaminophenol (2-METHYL-5-HYDROXYETHYLAMINOPHENOL), 3-ethylamino-p-cresol ( 3-ETHYLAMINO-p-CRESOL), N,N-diethyl-m-aminophenol (N,N-DIETHYL-m-AMINOPHENOL), 2,6-hydroxyethylaminotoluene (2,6-HYDROXYETHYLAMINOTOLUENE), 5-( 2-hydroxyethyl)-amino-4-methoxy-2-methylphenol (5-
  • salts include hydrochlorides, sulfates, hydrobromides, and the like.
  • the oxidation dye is at least one selected from these specific examples.
  • 4-chlororesorcinol 2,7-naphthalenediol, 3-amino-2,4-dichlorophenol, 2-methylresorcinol, 2,4,5,6-tetraaminopyrimidine, 2- amino-4-hydroxyethylaminoanisole, hydroxyethyl-3,4-methylenedioxaniline, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3,5-pyridinediamine, 2-amino -3-hydroxypyridine, 2,5,6-triamino-4-pyrimidinol, 1-hydroxyethyl-4,5-diaminopyrazole, resorcinol, 1,5-naphthalenediol, 1-naphthol, 2-methyl-5-hydroxy It is preferably one or more of ethylaminophenol, 5,6-dihydroxyindoline, 5,6-dihydroxyindole, and salts thereof.
  • the (B) oxidation dye preferably contains (B-1) an oxidation dye having a heterocyclic structure from the viewpoint of further improving the hair dyeing power.
  • (B-1) oxidation dyes having a heterocyclic structure include 1-hydroxyethyl-4,5-diaminopyrazole, 2,4,5,6-tetraaminopyrimidine, and hydroxyethyl-3,4-methylene. dioxaniline, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3,5-pyridinediamine, 5,6-dihydroxyindoline, 5,6-dihydroxyindole, salts thereof, and the like; be done.
  • the (B) oxidation dye preferably contains 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof from the viewpoint of excellent hair dyeing power and hot water fading suppressing effect.
  • 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof has high saturation and exhibits a warm color such as bright red, so it is possible to obtain a color tone with low saturation and reduced redness. difficult. Even in such a case, redness can be suppressed and a purple tone with low saturation can be expressed by combining with (A) the oxidation dye 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof.
  • (B) 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof and 2,4,5,6-tetraaminopyrimidine, 2,7-naphthalenediol, or a salt thereof are used in combination as oxidation dyes. is preferred. With such a configuration, redness can be suppressed and yellowness can be expressed. By expressing yellowness, it is possible to express natural familiarity when blond hair, bleached hair, or gray hair is dyed.
  • the lower limit of the content of (B) the oxidation dye in the mixture is appropriately set, but is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and still more preferably 1% by mass or more. .
  • the upper limit of the content of (B) the oxidation dye in the mixture is set as appropriate, but is preferably 6% by mass or less, more preferably 5% by mass or less, and even more preferably 4% by mass or less.
  • the content of the oxidation dye is 6% by mass or less, the skin cleansing property can be further improved, and the stability of the formulation is also improved.
  • the oxidation dye (B) is 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof, redness is suppressed. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the lower limit of the sum of the content of (A) the oxidation dye and the content of the (B) oxidation dye in the mixture is appropriately set, but is preferably 0.5% by mass or more, more preferably 1% by mass or more. , more preferably 1.5% by mass or more.
  • the mass is 0.5% by mass or more, particularly the hair dyeing power and the effect of suppressing hot water fading can be further improved.
  • the upper limit of the sum of the content of (A) the oxidation dye and the content of the (B) oxidation dye in the mixture is set appropriately, but is preferably 7.5% by mass or less, more preferably 5.5% by mass. % or less, more preferably 4.8 mass % or less.
  • the mass is 7.5% by mass or less, the skin cleansing property can be particularly improved, and the stability of the formulation is further improved.
  • the oxidation dye (B) is 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof, redness is suppressed. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the lower limit of the mass ratio (B/A) of the content of the (B) oxidation dye to the content of the (A) oxidation dye in the mixture is appropriately set, but is preferably 0.2 or more, more preferably 1 or more, more preferably 2 or more.
  • the mass ratio is 0.2 or more, discoloration with hot water can be particularly suppressed, and the hair dyeing power can be further improved.
  • the upper limit of the mass ratio (B/A) of the content of the (B) oxidation dye to the content of the (A) oxidation dye in the mixture is appropriately set, but is preferably 9 or less, more preferably 6 or less. , and more preferably 3 or less. When the mass ratio is 9 or less, particularly the skin cleansing property can be further improved. Also, when the oxidation dye (B) is 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof, redness is suppressed. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the hair dye composition of the present embodiment optionally has a benzene ring and an amine group as (C) the oxidation dye, and the positional relationship between the amine groups or the positional relationship between the amine group and the hydroxyl group is in the ortho or para position. It may contain an oxidation dye containing (excluding the (B) oxidation dye). As for these (C) oxidation dyes, one kind of (C) oxidation dye may be used alone, or two or more kinds of (C) oxidation dyes may be used in combination.
  • oxidation dyes include 1,2-Diamino-benzene, TOLUENE-2,5-DIAMINE, and p-phenylenediamine.
  • p-PHENYLENEDIAMINE 2-CHLORO-p-PHENYLENEDIAMINE, N-PHENYL-p-PHENYLENEDIAMINE, o-aminophenol (o-AMINOPHENOL) ), p-aminophenol (p-AMINOPHENOL), p-methylaminophenol (p-METHYLAMINOPHENOL), 3,4-diaminobenzoic acid (3,4-DIAMINOBENZOIC ACID), 2-methoxy-p-phenylenediamine (2- METHOXY-p-PHENYLENEDIAMINE), N,N-diethyl-p-phenylenediamine (N,N-DIETHYL-p-PHENYLENEDIAMINE), N-methoxyethyl-p-phenyl
  • the content of (C) the oxidation dye in the mixture is appropriately set, but is preferably 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.3% by mass or less. When it is 1% by mass or less, the skin cleansing property is particularly improved, and the stability of the formulation is also improved. In addition, (C) the oxidation dye, when not blended in the mixture, further improves the skin cleansing properties in particular.
  • the lower limit of the mass ratio (A/C) of the content of (A) oxidation dye to the content of (C) oxidation dye in the mixture is set as appropriate, but is preferably 1 or more, more preferably 1.5. or more, more preferably 2 or more. When the mass ratio is 1 or more, the skin cleanability can be improved.
  • the lower limit of the total mass ratio ((A+B)/C) of the total content of (A) oxidation dye and (B) oxidation dye to the content of (C) oxidation dye in the mixture is set as appropriate, but is preferred. is 2 or more, more preferably 3 or more, and still more preferably 4 or more. When the mass ratio is 2 or more, the skin cleansing property can be further improved.
  • the first agent may contain a reducing agent if necessary.
  • a reducing agent improves the stability of the dye.
  • the stability of the dye is maintained even during storage such as set aside, and the hair dyeing effect immediately after opening can be maintained.
  • reducing agents include ascorbic acids, thioglycolic acids, cysteines, mercapto compounds, sulfites, hydrogensulfites and thiosulfates.
  • Ascorbic acids include, for example, ascorbic acid, erythorbic acid, salts thereof, derivatives thereof, and the like.
  • Specific examples of salts include sodium salts, potassium salts, calcium salts, ammonium salts, monoethanolamine salts, diethanolamine salts and the like.
  • Specific examples of derivatives include disodium ascorbate sulfate, disodium erythorbate sulfate, magnesium ascorbate phosphate, ascorbyl palmitate, ascorbyl stearate, ascorbyl dipalmitate, ascorbyl tetra-2-hexyldecanoate, and myristine.
  • Ascorbyl Acid Ascorbyl Laurate, Ascorbyl Acetate, Ascorbyl Propionate, Ascorbyl Tartrate, Ascorbyl Citrate, Ascorbyl Succinate, Ascorbyl Benzoate, Potassium (Ascorbyl/Tocopheryl) Phosphate, Ethyl Ascorbyl, Allantoin Ascorbate, Chitosan Ascorbate, Ascorbyl Acid methylsilanol, tetradecylhexyl ascorbyl, aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl glucoside, ascorbyl methylsilanol pectinate and the like.
  • thioglycolic acids include thioglycolic acid, thioglycolic acid salts, esters of thioglycolic acid, and the like.
  • cysteines include cysteine, cysteine hydrochloride, N-acetyl-L-cysteine and the like.
  • mercapto compounds include thioglycerol, thiolactic acid, thiomalic acid, cysteamine, and the like.
  • sulfites include sulfurous acid, ammonium sulfite, sodium sulfite, and the like.
  • hydrogen sulfite include ammonium hydrogen sulfite, sodium hydrogen sulfite, and the like.
  • thiosulfates include thiosulfate and sodium thiosulfate.
  • ascorbic acid, ammonium sulfite and sodium sulfite are preferred.
  • These reducing agents may be used singly or in combination of two or more reducing agents.
  • the lower limit of the content of the reducing agent in the mixture is appropriately set, but is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and still more preferably 0.1% by mass or more.
  • the content of the reducing agent is 0.01% by mass or more, the stability of the dye can be further improved.
  • the upper limit of the content of the reducing agent in the mixture is appropriately set, but is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less.
  • the content of the reducing agent is 10% by mass or less, the hair dyeing power can be further improved. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the first agent may preferably contain an alkaline agent.
  • the alkaline agent functions to improve the hair dyeing power by promoting the action of the oxidizing agent contained in the second agent.
  • One kind of alkali agent may be used alone, or two or more kinds of alkali agents may be used in combination.
  • alkaline agents include ammonia, alkanolamines, silicates, carbonates, hydrogencarbonates, carbamates, metasilicates, phosphates, organic amines, basic amino acids, and the like.
  • Specific examples of alkanolamine include monoethanolamine and triethanolamine.
  • Specific examples of silicates include sodium silicate, potassium silicate, and calcium silicate.
  • carbonates include sodium carbonate, ammonium carbonate, magnesium carbonate and the like.
  • hydrogencarbonate include sodium hydrogencarbonate and ammonium hydrogencarbonate.
  • carbamates include ammonium carbamate and the like.
  • metasilicates include sodium metasilicate and potassium metasilicate.
  • phosphate include triammonium phosphate and diammonium hydrogen phosphate.
  • organic amines include 2-amino-2-methyl-1-propanol (AMP), 2-amino-2-methyl-1,3-propanediol, and guanidine.
  • basic amino acids include arginine and lysine. Among these, ammonia, monoethanolamine, and carbonate are preferred.
  • the lower limit of the content of the alkaline agent in the mixture is set appropriately, but the amount that lowers the pH of the mixture is preferably 7 or more, more preferably 7.5 or more, and still more preferably 8. or more, particularly preferably 8.5 or more, most preferably 9 or more.
  • the upper limit of the content of the alkaline agent is appropriately set, it is contained in such an amount that the upper limit of the pH of the mixture is preferably 12 or less.
  • the pH is preferably 10.5 or less, more preferably 10 or less, and 9.5 or less. is more preferred.
  • the pH is preferably 10.5 or less, and in gray hair dyeing, the pH is preferably 9.8 or less.
  • the pH When the pH is 10.5 or less, the lightness is high and a bright color tone can be expressed, and a hair color for black hair such as bleach or fashion color can be expressed, and a bright color can be expressed for gray hair.
  • the pH when the pH is 9.8 or less, the lightness is low and a dark color tone can be expressed, so that it can be mainly applied to hair color for gray hair.
  • the content of the alkaline agent in the mixture described in this specification indicates the content of the pure alkaline agent excluding the solvent in the raw material reagent.
  • the lower limit of the content of the alkaline agent in the mixture is appropriately set, but is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and still more preferably 0.5% by mass or more.
  • the upper limit of the content of the alkaline agent in the mixture is appropriately set, but is preferably 7% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the lower limit of the mass ratio of the content of the alkaline agent to the content of the oxidation dye (A) in the mixture (alkali agent/A) is appropriately set, but is preferably 0.1 or more, more preferably 0.5. or more, more preferably 1 or more. When the mass ratio is 0.1 or more, the hair dyeing power and the skin cleansing property can be further improved.
  • the upper limit of the mass ratio (alkaline agent/A) is appropriately set, but is preferably 15 or less, more preferably 10 or less, and even more preferably 6 or less. When the mass ratio is 15 or less, the hair dyeing power and the skin cleansing property can be further improved. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the lower limit of the mass ratio of the content of the alkaline agent to the total content of (A) the oxidation dye and (B) the oxidation dye is set as appropriate, but is preferably 0.05 or more, more preferably It is 0.1 or more, more preferably 0.4 or more.
  • the upper limit of the mass ratio is appropriately set, but is preferably 4 or less, more preferably 3 or less, and still more preferably 2 or less.
  • the mass ratio is 4 or less, the hair dyeing power can be further improved. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the first agent may further contain (D) a polymerization accelerator.
  • a polymerization accelerator improves hair dyeing power and skin cleansing properties. Moreover, redness can be further suppressed.
  • Polymerization accelerators include, for example, iodine compounds, transition metals such as iron compounds and copper compounds, and the like. Examples of iodine compounds include iodine (I), iodides with counter ions released in the solubilizer, and compounds that release iodine during use.
  • iodides include alkali metal salts of iodides such as potassium iodide, sodium iodide and lithium iodide, ammonium iodide, hydrogen iodide, cesium iodide and silver iodide.
  • a natural material containing iodine for example, an extract containing iodide such as iodinated garlic extract may be applied.
  • iron compounds include ferric chloride, ferric oxide, sodium iron chlorophyllin, and the like.
  • copper compounds include copper sulfate, sodium copper chlorophyllin, and the like.
  • potassium iodide is preferred from the viewpoint of being excellent in the effect of improving the hair dyeing power.
  • One (D) component may be used alone, or two or more (D) components may be used in combination.
  • the lower limit of the content of component (D) in the mixture is set as appropriate, but is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.02% by mass or more, Particularly preferably, it is 0.05% by mass or more.
  • the content of the component is 0.001% by mass or more, the hair dyeing power can be further improved.
  • the upper limit of the content of component (D) in the mixture is set as appropriate, but is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less.
  • the content of the component (D) is 5% by mass or less, the skin washing property can be further improved, and the hair dyeing power is further improved. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the hair dye composition may optionally contain components other than those mentioned above, such as oily components, surfactants, polyhydric alcohols, solubilizers, water-soluble polymers, pH adjusters other than those mentioned above, preservatives, stabilizing agents, agents, plant extracts, crude drug extracts, vitamins, fragrances, antioxidants, chelating agents, ultraviolet absorbers, and the like.
  • oils and fats examples include oils and fats, waxes, higher alcohols, hydrocarbons, higher fatty acids, alkylglyceryl ethers, esters, and silicones. Fats and oils may be animal oils or vegetable oils. One type of oily component may be used alone, or two or more types of oily components may be used in combination.
  • polyhydric alcohols examples include glycol and glycerin.
  • a single polyhydric alcohol may be used alone, or two or more polyhydric alcohols may be used in combination.
  • Surfactants include anionic surfactants, cationic surfactants, amphoteric surfactants, and nonionic surfactants.
  • a single surfactant may be used alone, or two or more surfactants may be used in combination.
  • a solubilizer is added, for example, when the dosage form is liquid.
  • solubilizers used include, for example, water and organic solvents (solvents).
  • solvents solvents
  • a single solubilizer may be used alone, or two or more solubilizers may be used in combination.
  • water is preferably applied because of its excellent ability to dissolve other components in the first agent.
  • the lower limit of water content in the mixture is set appropriately, but is preferably 40% by mass or more, more preferably 50% by mass or more.
  • the water-soluble polymer gives the hair dye composition moderate viscosity. Therefore, the hair dye composition may contain a water-soluble polymer within a range that does not impair the effects of the present invention.
  • water-soluble polymers include natural polymers, semi-synthetic polymers, synthetic polymers, and inorganic polymers. One water-soluble polymer may be used alone, or two or more water-soluble polymers may be used in combination.
  • a pH adjuster may be contained to adjust the pH of the hair dye composition (mixture).
  • the pH adjuster is appropriately selected from known components other than the components listed in each item above.
  • Examples of pH adjusters include inorganic acids, organic acids, salts thereof, hydroxides of alkali metals or alkaline earth metals, and the like.
  • Specific examples of pH adjusters include hydrochloric acid and sodium hydroxide.
  • one type of other component may be used alone, or two or more types of other components may be used in combination.
  • the dosage form of the first agent is not particularly limited, and specific examples include liquid forms such as aqueous solutions and milky lotions, gel forms, foam forms, cream forms, and solid forms at 25°C.
  • a dispersant may be blended. It can also be an aerosol, a non-aerosol, etc. In the case of a non-aerosol, it can further take various forms such as a squeeze foamer type and a pump foamer type.
  • a known propellant and foaming agent can be applied. Specific examples of the propellant or foaming agent include liquefied petroleum gas (LPG), dimethyl ether (DME), nitrogen gas, carbon dioxide gas, and the like.
  • the second agent can also contain the above-described solubilizer and the like.
  • the oxidizing agent further improves the bleaching properties of melanin contained in hair. Therefore, an inorganic oxidant is applied.
  • the oxidizing agent include hydrogen peroxide, urea peroxide, melamine peroxide, sodium percarbonate, potassium percarbonate, sodium perborate, potassium perborate, ammonium persulfate, potassium persulfate, sodium persulfate, Sodium peroxide, potassium peroxide, magnesium peroxide, barium peroxide, calcium peroxide, strontium peroxide, sulfate hydrogen peroxide adduct, phosphate hydrogen peroxide adduct, pyrophosphate hydrogen peroxide adducts and the like.
  • hydrogen peroxide and percarbonate are preferred, and hydrogen peroxide is more preferred.
  • a single oxidizing agent may be used alone, or two or more oxidizing agents may be used in combination.
  • the lower limit of the content of the oxidizing agent in the second agent is appropriately set, but is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, and still more preferably 2.0% by mass or more. be. When the content of the oxidizing agent is 0.1% by mass or more, the decolorization of melanin can be further improved.
  • the upper limit of the content of the oxidizing agent in the second agent is appropriately set, but is preferably 15.0% by mass or less, more preferably 9.0% by mass or less, and still more preferably 6.0% by mass. It is below. When the content of the oxidizing agent is 15.0% by mass or less, hair damage and the like can be further suppressed. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the second agent When hydrogen peroxide is added as an oxidizing agent to the second agent, the second agent preferably contains a stabilizing agent such as sodium stannate, ethylene glycol phenyl ether (phenoxyethanol ), hydroxyethanediphosphonic acid and salts thereof.
  • a stabilizing agent such as sodium stannate, ethylene glycol phenyl ether (phenoxyethanol ), hydroxyethanediphosphonic acid and salts thereof.
  • hydroxyethanediphosphonates include tetrasodium hydroxyethanediphosphonate and disodium hydroxyethanediphosphonate.
  • the second agent may contain each component that is generally contained in a hair dye composition and does not inhibit the action of each component described above.
  • the ingredients contained in the first agent described above may be contained as appropriate within a range that does not impair the effects of the present invention.
  • the dosage form of the second agent is not particularly limited, and specific examples thereof include liquid forms such as aqueous solutions and milky lotions, gel forms, foam forms, cream forms, and solid forms at 25°C. It can also be an aerosol, a non-aerosol, etc. In the case of a non-aerosol, it can further take various forms such as a squeeze foamer type and a pump foamer type. Moreover, in the case of aerosol, a known propellant and foaming agent can be applied. Moreover, in the case of a solid dosage form, a dispersant may be blended.
  • the mixing ratio of the first agent and the second agent of the two-agent hair dye composition is appropriately set in consideration of the concentration, mixability, application method, etc. of each component in the mixture.
  • the lower limit of the mass of the first agent is preferably 0.1 or more, more preferably 0.5 or more.
  • the upper limit of the mass of the first agent is preferably 10 or less, more preferably 2 or less. Ranges with any combination of the above upper and lower limits are also envisioned.
  • the dosage form of the mixture is not particularly limited as long as it can be applied to hair, and specific examples include liquid forms such as aqueous solutions and milky lotions, gel forms, foam forms, and cream forms at 25°C. .
  • a cream or paste form is preferred from the viewpoints of improving ease of brushing, spreadability and adhesion to the hair, and excellent application operability.
  • the hair dye composition may be further foamed or misted. In the case of forming the foam as described above, even if it is formed by self-foaming by mixing the hair dye composition in a mixing container and a mixing device, the hair dye composition is filled in a shaking container and shaken.
  • a known foaming device such as a non-aerosol foamer or an aerosol foamer may be used.
  • the hair dye composition As a means for applying the hair dye composition to the hair, it may be applied to the hair using an applicator such as a comb, brush, brush, or applicator. Alternatively, the hair dye composition may be applied to the hair with gloved hands.
  • an applicator such as a comb, brush, brush, or applicator.
  • the hair dye composition may be applied to the hair with gloved hands.
  • the hair dye composition of the present embodiment contains (A) 6-methoxy-2-methylamino-3-aminopyridine or a salt thereof and (B) a predetermined oxidation dye. Therefore, it is possible to improve the skin cleansing property while maintaining the hair dyeing power. In addition, when a reducing agent is further contained, the stability of the dye can be improved.
  • (B) 1-hydroxyethyl-4,5-diaminopyrazole or a salt thereof and 2,4,5,6-tetraaminopyrimidine, 2,7-naphthalenediol, or a salt thereof are used in combination as oxidation dyes. In this case, redness can be suppressed and yellowness can be expressed.
  • the content of (C) oxidation dye is specified within a predetermined range. Therefore, it is possible to substantially eliminate or reduce the content of dye intermediates such as p-phenylenediamine and toluene-2,5-diamine. Therefore, it may be used even in subjects who are allergic to certain dyes, for example.
  • the hair dye composition of the present embodiment can be bleached to remove the color, the recoloring property is improved.
  • the hair dye composition of the above embodiment can be used as a dye other than the oxidation dye described above, within a range that does not impede the effects of the present invention, for example, "Standards for Quasi-drug Ingredients" (published in June 2006, Yakuji Nippo company) may be included as appropriate.
  • the above embodiment is configured as a multi-component hair dye composition consisting of (A) a first agent containing an oxidation dye and the like, and a second agent containing an oxidizing agent and the like.
  • the hair dye composition is not limited to a two-agent type, and may be composed of a three-agent or more agent type by forming a part of each component contained in the first agent and the second agent as a separate agent.
  • the first agent of a two-agent type is divided into two, one containing a dye and an optional alkaline agent, and the other having a composition other than that, to form a three-agent hair dye composition.
  • it has better formulation stability.
  • a dye, an alkali agent, and an oxidizing agent may be separately blended.
  • a dye, an alkali agent, and an oxidizing agent may be combined to the extent that the effect of the present invention is achieved.
  • the dye and the oxidizing agent may be stored in the same agent.
  • powdered agents are used, they are dissolved in the solvents mentioned above at the time of use.
  • the hair dye composition is composed of three or more formulations or a composition containing powdered agents, it is still included in the present invention as long as the effect of the present invention is exhibited.
  • the hair dye composition of the second embodiment differs from the hair dye composition of the first embodiment in that it does not contain an oxidizing agent.
  • the following description will focus on differences from the hair dye composition of the first embodiment.
  • the hair dye composition of the second embodiment is configured as a one-component hair dye composition containing (A) the oxidation dye and (B) the oxidation dye and the like.
  • This one-part type hair dye composition may contain, in addition to the oxidation dyes described above, preferably an alkaline agent, (D) a polymerization accelerator, and the like. Further optionally, the above (C) oxidation dye may be included.
  • the oxidation dye (B) is 2,7-naphthalenediol, 3-amino-2,4-dichlorophenol, 2-methylresorcinol, 2,4,5,6-tetraaminopyrimidine, isatin , 1,5-naphthalenediol, 5,6-dihydroxyindoline, 5,6-dihydroxyindole, 5-amino-6-chloro-o-cresol, and salts thereof. is preferred. Thereby, better hair dyeing power can be obtained without using an oxidizing agent.
  • These (B) oxidation dyes may be used alone or in combination of two or more.
  • 5,6-dihydroxyindole, 5,6-dihydroxyindole, and salts thereof are preferred from the viewpoint of being superior in hair dyeing power, long-term use accumulation property, suppression of discoloration in hot water, and suppression of redness.
  • the hair dye composition of the second embodiment may, if necessary, further contain components other than the components described above, for example, components contained in the hair dye composition described in the section of the first embodiment.
  • the second embodiment can appropriately adopt the modifications described in the first embodiment as long as they are not technically inconsistent.
  • the content and content ratio of each component in the mixture of the first embodiment are the content and content ratio in one agent when the hair dye composition of the second embodiment is configured as one dosage form. shall be shown.
  • the second embodiment can be implemented with the following changes.
  • the second embodiment and the following modified examples can be combined with each other within a technically consistent range.
  • the dosage form of the hair dye composition of the second embodiment is not particularly limited.
  • the dosage form of the hair dye composition is a foam
  • the effect of suppressing hair dyeing spots can be further improved compared to a cream dosage form.
  • the hair dye composition has a cream-like formulation
  • the hair dyeing power can be further improved compared to a foam-like formulation.
  • the second embodiment is configured as a one-component hair dye composition containing (A) an oxidation dye and the like.
  • the hair dye composition is not limited to a one-agent type, and may be composed of a two-part type or more by forming a part of each component contained as a separate agent.
  • a two-agent hair dye composition may be constructed by dividing the agent into two, one containing the optional alkaline agent and the other having other compositions. In this case, it has better formulation stability. Examples Next, the embodiment will be described more specifically with reference to examples and comparative examples. It should be noted that the present invention is not limited to the configurations described in Examples.
  • ⁇ Test Example 1 Two-component hair dye composition> As a hair dye composition, a cream-like first agent containing each component shown in Tables 1 to 3 and an emulsion-like second agent of formulation 1 containing each component shown in Table 4 were prepared. Hydrochloric acid and sodium hydroxide were used as pH adjusters. The numerical value in the column of each component in each table indicates the content of the component in that column, and the unit is % by mass. The notations A to D in the "Component" column in each table indicate compounds corresponding to the respective components described in the claims of the present application.
  • the mass ratio of the content of (A) oxidation dye to the content of (C) oxidation dye is shown in the "A component/C component" column in the table.
  • alkaline agent when mixed 1:1
  • the mass ratio of the content of (B) oxidation dye to the content of (A) oxidation dye is shown in the "B component/A component" column in the table.
  • salt-type dyes using acids in the table below use 6-methoxy-2-methylamino-3-aminopyridine as a starting material.
  • 2 mol of hydrochloric acid produced per 1 mol of hydrochloride is neutralized by adding NaOH as an alkaline agent or pH adjuster. That is, among the agents listed in the table, salt-form dyes using acid, for example, 6-methoxy-2-methylamino-3-aminopyridine dihydrochloride, 6-methoxy-2-methylamino-3 - Contained as a free form of aminopyridine.
  • the first agent and the second agent were mixed at a mass ratio of 1:1 to prepare a mixture of the hair dye composition of each example.
  • 2 g of the resulting mixture was applied to 1 g of a white hair bundle sample for evaluation (manufactured by Beaulux Co., Ltd.) having a length of 10 cm (hereinafter simply referred to as hair bundle) using a brush.
  • hair bundle a white hair bundle sample for evaluation
  • the mixture attached to the hair bundle was washed away with water, and the hair bundle was shampooed (Bigen Treatment Shampoo manufactured by Hoyu Co., Ltd.) twice and rinsed (Bigen Treatment Shampoo manufactured by Hoyu Co., Ltd.). rinse) was applied once.
  • the hair tresses were dried with warm air to obtain dyed hair tresses of each example.
  • the hair tresses of each example were evaluated for hair dyeing power, skin cleanability, suppression of hot water fading, and redness suppression, if necessary, according to the methods described below.
  • An average value of 5.6 points or more is “Very excellent: 6”
  • an average value of 4.6 points or more and less than 5.6 points is “Excellent: 5”
  • 3.6 points or more and less than 4.6 points is “Good : 4”
  • 2.6 points or more and less than 3.6 points are “Fair: 3”
  • 1.6 points or more and less than 2.6 points are “Slightly poor: 2”
  • less than 1.6 points are “Poor: 1 ” as the evaluation result.
  • the results are shown in the "hair dyeing power" column of each table.
  • An average score of 5.6 or more is “not feeling redness: 6”
  • an average score of 4.6 or more and less than 5.6 is “not much redness: 5”
  • 3.6 or more and 4.6 Less than a point is “weak redness: 4”
  • 2.6 points or more and less than 3.6 points is “feeling a little redness: 3”
  • 1.6 points or more and less than 2.6 points is “feeling redness: 2”
  • the hair tresses of each example subjected to the fading treatment were arranged side by side for comparison, and visually evaluated by 20 expert panelists.
  • the evaluation criteria were as follows: hair bundles evaluated by 17 or more panelists as having little color fading due to fading treatment and excellent hair color retention were evaluated as 6 points; 4 points for hair bundles of 8 to 10 persons, 3 points for hair bundles for 5 to 7 persons, 2 points for hair bundles for 4 or less persons, and 1 point for hair bundles of 4 or less persons.
  • the results are shown in the column "Suppression of hot water fading" in each table.
  • Example 1-4 the first agent of Example 1-4 and the first agent of Example 1-4 excluding ascorbic acid were prepared and stored at room temperature for one month.
  • the hair dyeing power was evaluated in the same manner as in Examples 1-4 above. As a result, it was confirmed that the hair dyeing power was inferior to that of the first agent of Example 1-4 when using the first agent without ascorbic acid.
  • the content of the alkaline agent in one agent is shown in the "Alkaline agent" column in the table.
  • the total amount of (A) oxidation dye content and (B) oxidation dye content in one agent is shown in the "A component + B component" column in the table.
  • the hair bundle sample coated with the hair dye composition was left in a constant temperature bath at 30° C. for 10 minutes, and then washed with water. After that, the washed hair bundle sample was dried with warm air to obtain a hair bundle sample for evaluation after being dyed once.
  • a hair bundle sample for evaluation after three times of hair dyeing was prepared by repeating these series of steps three times. At that time, from the second time onwards, before applying the hair dye composition, the hair bundle samples were washed with "Bigen Treatment Shampoo" (manufactured by Hoyu Co., Ltd.) and towel-dried.
  • the average score is calculated for the scoring results of the five panelists, and the average score is 4.6 or more as “excellent: 5”, 3.6 points or more and less than 4.6 points as “good: 4”, 2.6 points or more
  • a score of less than 3.6 was rated as "acceptable: 3”
  • a score of 1.6 or more and less than 2.6 was rated as "slightly unsatisfactory: 2”
  • a score of less than 1.6 was rated as "defective: 1".
  • the results are shown in the "continuous use accumulation" column of each table.
  • Example 2-1 As shown in Table 5, it was confirmed that even the hair dye composition containing no oxidizing agent had excellent hair dyeing power. Especially in Example 2-1, the hair dyeing power was evaluated as 6, and the hair was dyed beautifully without dyeing spots.

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Abstract

L'invention concerne une composition de coloration capillaire qui présente une meilleure rinçabilité du cuir chevelu tout en maintenant la résistance de la coloration des cheveux. La composition de coloration capillaire selon la présente invention comprend : (A) de la 6-méthoxy-2-méthylamino-3-aminopyridine ou similaire, en tant que colorant d'oxydation ; et (B) un colorant d'oxydation qui satisfait à une condition prescrite, par exemple typiquement un colorant d'oxydation qui ne contient pas de cycle benzène.
PCT/JP2021/016911 2021-04-28 2021-04-28 Composition de coloration capillaire WO2022230090A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001526196A (ja) * 1997-12-19 2001-12-18 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン 酸化染料用の新規第一中間体組み合わせ
JP2002508351A (ja) * 1997-12-17 2002-03-19 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン 新規ｐ−アミノフェノール誘導体およびその使用
JP2017178907A (ja) * 2016-03-31 2017-10-05 ホーユー株式会社 酸化染毛剤組成物
JP2019064952A (ja) * 2017-09-29 2019-04-25 ホーユー株式会社 酸化染毛剤組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002508351A (ja) * 1997-12-17 2002-03-19 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン 新規ｐ−アミノフェノール誘導体およびその使用
JP2001526196A (ja) * 1997-12-19 2001-12-18 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン 酸化染料用の新規第一中間体組み合わせ
JP2017178907A (ja) * 2016-03-31 2017-10-05 ホーユー株式会社 酸化染毛剤組成物
JP2019064952A (ja) * 2017-09-29 2019-04-25 ホーユー株式会社 酸化染毛剤組成物

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