WO2022065433A1 - 毛髪用化粧料 - Google Patents

毛髪用化粧料 Download PDF

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Publication number
WO2022065433A1
WO2022065433A1 PCT/JP2021/035086 JP2021035086W WO2022065433A1 WO 2022065433 A1 WO2022065433 A1 WO 2022065433A1 JP 2021035086 W JP2021035086 W JP 2021035086W WO 2022065433 A1 WO2022065433 A1 WO 2022065433A1
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Prior art keywords
hair
membered ring
groups
group
carbon atoms
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English (en)
French (fr)
Japanese (ja)
Inventor
瑞希 坂田
克也 三浦
芽育 堀
鷹行 井本
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Nissan Chemical Corp
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Nissan Chemical Corp
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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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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 cosmetic that colors hair, and more particularly to a hair cosmetic that suppresses bleaching by containing at least one lipid peptide-type compound.
  • the coloring component leaks out by washing the hair, that is, the hair is decolorized or faded. There is also concern that housing will be contaminated.
  • hair has three structures: a central part called medura (hair medulla), a cortex (fur quality) in the middle part surrounding the medura, and an outermost cuticle (hair cuticle). If the component that colors the hair can stay in the cuticle located on the outermost side, it is expected that the decolorization will be suppressed and that the coloring component will not flow out even after repeated washing of the hair.
  • medura hair medulla
  • cortex cortex
  • outermost cuticle hair cuticle
  • Patent Gazette 1 Various hair cosmetics for cuticles have been reported, but hair intended to restore cuticles of hair damaged by chlorine in pools and tap water and prevent the hair from becoming dry and stiff.
  • the protective cosmetics (Patent Gazette 1) and the water-dispersed biocellulose fine fiber network dispersion have only been found to have the effect of not damaging the cuticle on the surface of the keratin structure (Patent Gazette 2). No technique has been reported to retain the colored components.
  • a hair cosmetic containing at least one lipid peptide-type compound consisting of a low-molecular-weight lipid peptide or a pharmaceutically usable salt thereof forms a film on the hair surface and forms a film on the hair surface. It has been found to retain water (Patent Document 3).
  • the above-mentioned techniques related to cuticles are all techniques for suppressing damage to the cuticle or recovering the damaged cuticle, and are not intended for the components used for coloring the hair to stay in the cuticle. Therefore, there has been a strong demand for hair cosmetics capable of suppressing fading of hair by retaining the hair in the cuticle layer.
  • An object of the present invention is to provide a hair cosmetic that can color hair more easily and is less likely to cause outflow of coloring components after washing, that is, bleaching and fading of hair.
  • the present inventor has added at least one lipid peptide-type compound to a component that colors hair (hereinafter, also referred to as a coloring component), whereby the coloring component becomes a lipid.
  • a coloring component a component that colors hair
  • the present invention has been completed by finding that it stays in the cuticle layer of hair together with the peptide and suppresses decolorization when the hair is washed.
  • the present invention contains, as a first aspect, at least one lipid peptide-type compound consisting of a small molecule lipid peptide or a pharmaceutically usable salt thereof, and a dye or pigment as a component for coloring hair. It is a hair cosmetic characterized by.
  • the lipid peptide type compound is a compound in which a peptide portion having a repeating binding structure of amino acids is bonded to a lipid portion composed of an aliphatic group having 9 to 23 carbon atoms. 1 is the hair cosmetic according to the viewpoint.
  • the lipid peptide type compound comprises at least one of the compounds represented by the following formulas (1) to (3) or pharmaceutically usable salts thereof.
  • R 1 represents an aliphatic group having 9 to 23 carbon atoms
  • R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms.
  • R 3 represents-(CH 2 ) n -X group, n represents a number of 1 to 4, X represents an amino group, a guanidino group, -CONH 2 groups, or 1 to 3 nitrogen atoms.
  • R 4 represents an aliphatic group having 9 to 23 carbon atoms
  • R 5 to R 7 each independently have a hydrogen atom and a branched chain having 1 or 2 carbon atoms.
  • X represents amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms 1 to 3.
  • R 8 represents an aliphatic group having 9 to 23 carbon atoms
  • R 9 to R 12 can independently have a hydrogen atom and a branched chain having 1 or 2 carbon atoms, respectively. 1 to 4 alkyl groups, or-(CH 2 ) n -X groups, n represents numbers 1 to 4, X represents amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms 1 to 3.
  • the present invention is the hair cosmetic according to any one of the first aspect to the third aspect, wherein the component that colors the hair is a dye as a fourth aspect.
  • the present invention comprises, as a fifth aspect, a step of blending a component that colors hair with at least one lipid peptide type compound consisting of a small molecule lipid peptide or a pharmaceutically usable salt thereof. It is a preparation method.
  • the present invention is a compound in which the lipid peptide type compound is a compound in which a peptide portion having a repeating binding structure of amino acids is bonded to a lipid portion composed of an aliphatic group having 9 to 23 carbon atoms.
  • 5 is the method for preparing a hair cosmetic according to the viewpoint.
  • the lipid peptide type compound comprises at least one of the compounds represented by the following formulas (1) to (3) or pharmaceutically usable salts thereof. The method for preparing a hair cosmetic according to the sixth aspect, which is characteristic.
  • R 1 represents an aliphatic group having 9 to 23 carbon atoms
  • R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms.
  • R 3 represents-(CH 2 ) n -X group, n represents a number of 1 to 4, X represents an amino group, a guanidino group, -CONH 2 groups, or 1 to 3 nitrogen atoms.
  • R 4 represents an aliphatic group having 9 to 23 carbon atoms
  • R 5 to R 7 each independently have a hydrogen atom and a branched chain having 1 or 2 carbon atoms.
  • X represents amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms 1 to 3.
  • R 8 represents an aliphatic group having 9 to 23 carbon atoms
  • R 9 to R 12 can independently have a hydrogen atom and a branched chain having 1 or 2 carbon atoms, respectively. 1 to 4 alkyl groups, or-(CH 2 ) n -X groups, n represents numbers 1 to 4, X represents amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms 1 to 3.
  • the present invention is a method for suppressing decolorization from hair by using the hair cosmetic according to any one of the first aspect to the fourth aspect as the eighth aspect.
  • the present invention by containing at least one lipid peptide type compound, it is possible to provide a hair cosmetic in which the component that colors the hair does not easily flow out from the hair. That is, the component that colors the hair stays in the cuticle, so that the bleaching of the hair can be suppressed.
  • FIG. 1 is an atomic force microscope (AFM) image of a hair sample 11 to which the hair cosmetic of Example 1 was applied and a hair sample 21 to which purified water of Comparative Example 1 was applied.
  • FIG. 2 is a graph showing the permeation amount of Lawson in the hair sample 12, the hair sample 22, the hair sample 13, and the hair sample 23.
  • FIG. 3 is a graph showing the amount of indigo extracted in the hair sample 14, the hair sample 24, the hair sample 15, and the hair sample 25.
  • the present invention relates to a cosmetic for hair, which comprises at least one lipid peptide type compound consisting of a small molecule lipid peptide or a pharmaceutically usable salt thereof and a component for coloring the hair.
  • the above-mentioned lipid peptide type compound is preferably a compound in which a peptide portion having a repeating binding structure of an amino acid is bonded to a lipid moiety composed of an aliphatic group having 9 to 23 carbon atoms.
  • lipid peptide type compound the compound represented by the following formulas (1) to (3) (lipid peptide) or a pharmaceutically usable salt thereof (hydrophilic moiety and hydrophilicity). It is more preferably composed of at least one of the low molecular weight compounds having a peptide portion as a moiety.
  • R 1 represents an aliphatic group having 9 to 23 carbon atoms
  • R 1 is a linear aliphatic group having 11 to 23 carbon atoms which can have 0 to 2 unsaturated bonds. Is preferable.
  • Specific examples of the lipid moiety (acyl group) composed of R1 and an adjacent carbonyl group include a lauroyl group, a dodecylcarbonyl group, a myristyl group, a tetradecylcarbonyl group, a palmitoyl group, a margalloyl group, an oleoyl group, and an eridoyl group.
  • Linole oil group Linole oil group, stearoyl group, buxenoyl group, octadecylcarbonyl group, arachidoyl group, eicosylcarbonyl group, behenoyl group, ercanoyle group, dococilcarbonyl group, lignosail group, nervonoyl group and the like, and are particularly preferable.
  • Examples thereof include a lauroyl group, a myritoyl group, a palmitoyl group, a carbonyl group, a stearoyl group, an oleoyl group, an elelideyl group and a behenoyle group.
  • R 2 contained in the peptide portion represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms.
  • the alkyl group having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms is a branched chain having 1 to 4 carbon atoms in the main chain and 1 or 2 carbon atoms.
  • alkyl group that can have, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group or a tert-butyl group. And so on.
  • R 2 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which can have a branched chain having 1 carbon atom, and more preferably a hydrogen atom.
  • An alkyl group having 1 to 3 carbon atoms capable of having a branched chain having 1 carbon atom is an alkyl group having 1 to 3 carbon atoms in the main chain and capable of having a branched chain having 1 carbon atom. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an i-butyl group or a sec-butyl group, and a methyl group, an i-propyl group, etc. are preferable. It is an i-butyl group or a sec-butyl group.
  • R 3 represents a ⁇ (CH 2 ) n—X group.
  • n represents a number of 1 to 4
  • X is a 5-membered ring or a 5-membered ring capable of having 1 to 3 amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms. It represents a 6-membered ring or a fused heterocycle composed of a 5-membered ring and a 6-membered ring.
  • X is preferably an amino group, a guanidino group, a carbamoyl group (-CONH 2 group), a pyrrole group, an imidazole group, a pyrazole group or an indole group, and more. It is preferably an imidazole group. Further, in the above- (CH 2 ) n-X group, n is preferably 1 or 2, and more preferably 1.
  • the- (CH 2 ) n- group is preferably an aminomethyl group, a 2-aminoethyl group, a 3-aminopropyl group, a 4-aminobutyl group, a carbamoylmethyl group, a 2-carbamoylethyl group, or a 3-carbamoyl group.
  • 2-Carbamoylethyl group, 3-guanidinobutyl group, 4-imidazole methyl group or 3-indolemethyl group more preferably 4-imidazole methyl group.
  • a particularly suitable lipid peptide as a lipid peptide type compound is a compound formed from the following lipid part and peptide part (amino acid assembly part).
  • amino acids include alanine (Ala), asparagine (Asn), glutamine (Gln), glycine (Gly), histidine (His), isolocin (Ile), leucine (Leu), and lysine (Leu). Lys), tryptophan (Trp), valine (Val).
  • Lauroyl-Gly-His Lauroyl-Gly-Gln, Lauroyl-Gly-Asn, Lauroyl-Gly-Trp, Lauroyl-Gly-Lys, Lauroyl-Ala-His, Lauroyl-Ala-Gln, Lauroyl-Ala-Asn, Lauroyl- Ala-Trp, Lauroyl-Ala-Lys; Miritoil-Gly-His, Miritoil-Gly-Gln, Miritoil-Gly-Asn, Miritoil-Gly-Trp, Miritoil-Gly-Lys, Miritoil-Ala-His, Miritoil-Ala- Gln, Millitoyl-Ala-Asn, Millistyl-Ala-Trp, Millistyl-Ala-Lys; Palmitoyl-Gly-His, Palmitoyl-Gly-Gln, Palmito
  • lauroyl-Gly-His lauroyl-Ala-His
  • myristoyl-Gly-His myristoyl-Ala-His
  • palmitoyl-Gly-His palmitoyl-Ala-His
  • stearoyl-Gly-His stearoyl-Ala.
  • -His is mentioned.
  • R 4 represents an aliphatic group having 9 to 23 carbon atoms, and a preferable specific example thereof is the same group as defined by R 1 described above.
  • R5 to R7 are independently hydrogen atoms, or alkyl groups having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms, or-(. CH 2 ) represents an n—X group, and at least one or more of R5 to R7 represents a ⁇ (CH 2 ) n—X group.
  • n represents a number from 1 to 4
  • X is a 5- or 6-membered ring capable of having 1 to 3 amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms, or 5-membered rings and 6-membered rings.
  • preferred specific examples of R5 to R7 include the same groups as those defined in R2 and R3 described above.
  • a suitable lipid peptide is a compound formed from the following lipid part and peptide part (amino acid assembly part). Lauroyl-Gly-Gly-His, Millistyl-Gly-Gly-His, Millistyl-Gly-Gly-Gln, Millistyl-Gly-Gly-Asn, Millistyl-Gly-Gly-Trp, Millistyl-Gly-Gly-Lys, Millist Gly-Ala-His, Miritoil-Gly-Ala-Gln, Miritoil-Gly-Ala-Asn, Miritoil-Gly-Ala-Trp, Miritoil-Gly-Ala-Lys, Miritoil-Ala-Gly-His, Miritoil-Ala- Gly-Gln, Millistyl-Ala-Gly-Asn, Millistyl-Ala-Gly-His, Miritoil-A
  • the most preferable ones are lauroyl-Gly-Gly-His, Millistyl-Gly-Gly-His, Palmitoyl-Gly-Gly-His, Palmitoyl-Gly-His-Gly, Palmitoyl-His-Gly-Gly, and stearoyl.
  • -Gly-Gly-His can be mentioned.
  • R 8 represents an aliphatic group having 9 to 23 carbon atoms, and a preferable specific example thereof is the same group as defined by R 1 described above.
  • R 9 to R 12 are independently hydrogen atoms, or alkyl groups having 1 to 4 carbon atoms which can have a branched chain having 1 or 2 carbon atoms, or-(. CH 2 ) represents an n—X group, and at least one or more of R 9 to R 12 represents a ⁇ (CH 2 ) n—X group.
  • n represents a number from 1 to 4
  • X is a 5- or 6-membered ring capable of having 1 to 3 amino groups, guanidino groups, -CONH 2 groups, or nitrogen atoms, or 5-membered rings and 6-membered rings.
  • preferred specific examples of R 9 to R 12 include the same groups as those defined in R 2 and R 3 described above.
  • suitable lipid peptide type compounds include lauroyl-Gly-Gly-Gly-His, myristyl-Gly-Gly-Gly-His, and palmitoyl-Gly-Gly-Gly-His. , Palmitoyl-Gly-Gly-His-Gly, Palmitoyl-Gly-His-Gly-Gly, Palmitoyl-His-Gly-Gly-Gly, Stearoyl-Gly-Gly-Gly-Gly-His and the like.
  • the content of the lipid peptide type compound is, for example, 0.01 to 30% by mass, preferably 0.02 to 10% by mass, and more preferably 0.03 with respect to the total mass of the hair cosmetic. Up to 5% by mass.
  • the lipid peptide type compound at least one of the compounds represented by the above formulas (1) to (3) (lipid peptide) or pharmaceutically usable salts thereof may be used. More preferably, these compounds can be used alone or in combination of two or more.
  • the hair cosmetic of the present invention may contain water, alcohol, polyhydric alcohol or a mixed solution thereof in addition to at least one of the above lipid peptide type compounds.
  • Examples of the above water include purified water, purified water, hard water, soft water, natural water, deep ocean water, electrolytic alkaline ionized water, electrolytically acidic ionized water, ionized water, and cluster water.
  • the alcohol is a monohydric alcohol, and is, for example, an alcohol having 1 to 6 carbon atoms dissolved in water at an arbitrary ratio, specifically, methanol, ethanol, 2-propanol, i-butanol, etc., and higher grade alcohols. Alcohols, specifically oleyl alcohol, phenyl alcohol and the like can be mentioned.
  • the polyvalent alcohol is a dihydric or higher alcohol, and is, for example, propylene glycol, 1,3-butanediol, 2-ethyl-1,3-hexanediol, glycerin, isopentyldiol, ethylhexanediol, or erythrulose.
  • Examples thereof include xylene glycol, pentylene glycol, methylpropanediol, mentandiol, laurylglycol and polypropylene glycol.
  • the content thereof when the polyhydric alcohol is contained, the content thereof may be, for example, 1% by mass to 60% by mass, preferably 1% by mass to 30% by mass, based on the total mass of the hair cosmetic. can. In the present invention, when the polyhydric alcohol is contained, the polyhydric alcohol may be used alone or in combination of two or more.
  • “Ingredients that color hair] examples of the component that colors hair include dyes, dyes, colorants, pigments, and the like, but dyes are preferable.
  • the dyes are brown 201, black 401, purple 201, purple 401, blue 1, blue 2, blue 201, blue 202, blue 203, blue 204, blue 205, and blue 403.
  • Red No. 225 Red No. 226, Red No. 227, Red No. 228, Red No. 230-1, Red No. 230-2, Red 231, Red 232, Red 3, Red 401, Red 404, Red 405, Red 501, Red 502, Red 503, Red 504, Red 505, Red 506, Orange 201 No., Orange No. 203, Orange No. 204, Orange No. 205, Orange No. 206, Orange No. 207, Orange No. 401, Orange No. 402, Orange No. 403, Yellow No. 201, Yellow No. 202-1, Yellow No. 202-2, Yellow 203, Yellow 204, Yellow 205, Yellow 4, Yellow 401, Yellow 402, Yellow 403-1, Yellow 404, Yellow 405, Yellow 406, Yellow 407, Yellow 5, etc.
  • Riboflavin natural dyes / dyes such as rutin; p-phenylenediamine, toluene-2,5-diamine, o-, m-, or p-aminophenol, m-phenylenediamine, 5-amino-2-methylphenol, Oxidation dye intermediates and couplers such as resorcin, 1-naphthol, 2,6-diaminopyridine and salts thereof; automatic oxidation dyes such as indolin; dihydroxyacetones are preferred.
  • Pigments include inorganic white pigments such as titanium dioxide and zinc oxide; inorganic red pigments such as red iron oxide (Bengala) and iron titanate; inorganic brown pigments such as ⁇ -iron oxide; yellow iron oxide, ocher and the like.
  • Inorganic yellow pigments Inorganic black pigments such as black iron oxide and low-order titanium oxide; Inorganic purple pigments such as mango violet and cobalt violet; Inorganic green pigments such as chromium oxide, chromium hydroxide and cobalt titanate; Ultramarine blue , Navy blue and other inorganic blue pigments; titanium oxide coated mica, titanium oxide coated bismuth chloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, pearl pigments such as fish scale foil; talc, sericite, mica, Constitution pigments such as kaolin, calcium carbonate, magnesium carbonate, anhydrous silicic acid, barium sulfate, aluminum hydroxide; metal powder pigments such as aluminum powder, copper powder and gold; surface-treated inorganic and metal powder pigments; zirconium, barium or aluminum lake Organic pigments such as; surface-treated organic pigments and the like are preferable.
  • the cosmetic of the present invention can generally contain cosmetic additives, additives for non-pharmaceutical products, additives that can be used as pharmaceutical additives, and the like, if necessary, and for example, oil-based bases and moisturizers.
  • the hair cosmetic of the present invention can be produced, for example, by mixing and stirring at least one lipid peptide-type compound, water and, if desired, other components while heating, and then allowing to allow to cool.
  • Example 1 Preparation of hair treatment liquid
  • the hair treatment liquid of Example 1 was prepared according to Table 1 below.
  • the B phase was heated and stirred to 75 ° C. in a 200 mL beaker (manufactured by HARIO Co., Ltd.).
  • Phase A heated to 75 ° C. was added to phase B, and the mixture was heated and stirred for 5 minutes. Then, stirring and cooling were performed until the temperature reached 40 ° C. In the above steps, all the stirring was performed at 200 rpm.
  • Pal-GH is an abbreviation for Palmitoyl-Gly-His.
  • EX Hybrid (manufactured by Mandom Corporation) is applied to 50 black human hairs (BS-BA, manufactured by Bulux Co., Ltd.) and left at room temperature for 1 hour to decolorize the hair. rice field. Then, the hair was washed with distilled water and dried for 30 minutes in a constant temperature dryer (OF-300B, manufactured by AS ONE Co., Ltd.) set at 60 ° C. The above operation was repeated a total of three times.
  • BS-BA black human hairs
  • OF-300B manufactured by AS ONE Co., Ltd.
  • the hair was immersed in 1 L of an aqueous solution prepared by dissolving 1% by mass of sodium dodecyl sulfate (manufactured by Wako Pure Chemical Industries, Ltd.) in distilled water, and washed with distilled water.
  • Bleached hair was prepared by removing excess water with Kay Dry (manufactured by Nippon Paper Crecia Co., Ltd.) and then drying at room temperature overnight.
  • the hair treated with the purified water of Comparative Example 1 was designated as a hair sample 21, and the hair treated with the hair treatment liquid of Example 1 was designated as a hair sample 11, and analyzed using AFM-IR (nano-IR2 manufactured by Anasys Instruments).
  • An AFM image of 10 ⁇ 15 ⁇ m was obtained by AFM-IR, and then imaging was performed in the same measurement range at a wavelength specific to Pal-GH in the hair cosmetic [1].
  • the wavelength of imaging was 1390 cm-1.
  • the results are shown in FIG.
  • the hair sample 21 has a low absorption strength in the cuticle layer, but the hair sample 11 has a constant strength in the entire hair, so that it is possible that Pal-GH has penetrated into the cuticle layer of the hair sample 11. It could be confirmed.
  • the dyed hair was rubbed and washed with a commercially available shampoo (TSUBAKI Premium Repair Shampoo Co., Ltd., manufactured by Shiseido Co., Ltd.) 10 times at a time, and the process of washing with running water until the bubbles disappeared was carried out 20 times. Then, the hair of the hair sample 12 and the hair sample 22 was prepared by drying for 1 hour with a constant temperature dryer (OF-300B, manufactured by AS ONE Co., Ltd.) set at 60 ° C.
  • OF-300B manufactured by AS ONE Co., Ltd.
  • the hair of the hair sample 23 and the hair sample 13 was prepared by drying for 1 hour with a constant temperature dryer (OF-300B, manufactured by AS ONE Co., Ltd.) set at 60 ° C.
  • a constant temperature dryer OF-300B, manufactured by AS ONE Co., Ltd.
  • Example 4 Preparation of Indigo Dye
  • the indigo dyes of Comparative Example 4 and Example 4 were prepared according to Table 4 below.
  • the B phase was heated and stirred to 75 ° C. in a 200 mL beaker (manufactured by HARIO Co., Ltd.).
  • Phase A heated to 75 ° C. was added to phase B, and the mixture was heated and stirred for 5 minutes. Then, stirring and cooling were performed until the temperature reached 40 ° C. In the above steps, all the stirring was performed at 200 rpm.
  • the hair of the hair sample 24 and the hair sample 14 was prepared by drying for 1 hour with a constant temperature dryer (OF-300B, manufactured by AS ONE Co., Ltd.) set at 60 ° C.
  • OF-300B manufactured by AS ONE Co., Ltd.
  • the indigo extracted from the hair was quantified by performing a filtration treatment using a Milex-FG filter 0.20 ⁇ m and measuring by high performance liquid chromatography (manufactured by HPLC Agilent). The test was carried out three times for each sample, and the average value thereof was calculated.
  • the quantitative conditions for HPLC are as follows.
  • Comparative Example 5 Example 5; Preparation of shampoo
  • the shampoos of Comparative Example 5 and Example 5 were prepared according to Table 5 below.
  • Phase B was heated and stirred to 75 ° C. in a 200 mL beaker (manufactured by HARIO, Inc.).
  • Phase A heated to 75 ° C. was added to phase B, and the mixture was heated and stirred for 5 minutes. Then, stirring and cooling were performed until the temperature reached 40 ° C. In the above steps, all the stirring was performed at 200 rpm.
  • the hair of the hair sample 25 and the hair sample 15 was prepared by drying for 1 hour with a constant temperature dryer (OF-300B, manufactured by AS ONE Co., Ltd.) set at 60 ° C.
  • OF-300B manufactured by AS ONE Co., Ltd.
  • Extraction of indigo in dyed hair Cut the hair of hair sample 25 and hair sample 15 to 0.5 cm, weigh 1.2 g and put it in a 50 mL sample tube, and use acetonitrile (manufactured by Genuine Chemical Co., Ltd.). ) 24 mL was added and ultrasonically treated for 1 hour to extract indigo in the hair.
  • the Indigo extracted from the hair was quantified by performing a filtration treatment using a Milex-FG filter 0.20 ⁇ m and measuring by high performance liquid chromatography (manufactured by HPLC Agilent). The test was carried out three times for each sample, and the average value thereof was calculated.
  • the quantitative conditions for HPLC are as follows.

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PCT/JP2021/035086 2020-09-28 2021-09-24 毛髪用化粧料 Ceased WO2022065433A1 (ja)

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