WO2023112671A1 - Cosmetic colorant and cosmetic using same - Google Patents

Cosmetic colorant and cosmetic using same Download PDF

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Publication number
WO2023112671A1
WO2023112671A1 PCT/JP2022/044100 JP2022044100W WO2023112671A1 WO 2023112671 A1 WO2023112671 A1 WO 2023112671A1 JP 2022044100 W JP2022044100 W JP 2022044100W WO 2023112671 A1 WO2023112671 A1 WO 2023112671A1
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Prior art keywords
group
cosmetic
carbon atoms
formula
derivative represented
Prior art date
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PCT/JP2022/044100
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French (fr)
Japanese (ja)
Inventor
博子 中田
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株式会社 資生堂
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Priority to JP2023567666A priority Critical patent/JPWO2023112671A1/ja
Priority to CN202280075560.6A priority patent/CN118251205A/en
Publication of WO2023112671A1 publication Critical patent/WO2023112671A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • the present invention relates to a cosmetic coloring material that produces bright fluorescent color and has transparency (clear feeling), and cosmetics using the same. More specifically, the present invention relates to a cosmetic coloring material obtained by combining a dye having a specific structure and a predetermined material, and a cosmetic containing the same.
  • Lip cosmetics such as lipsticks and glosses that color the lips, and makeup cosmetics such as cheeks (blushers) and eye shadows are cosmetics that exert such an important cosmetic effect as to completely change the impression of the user's appearance. Color is one of the key factors in choosing a product. BACKGROUND ART In recent years, there has been a demand for makeup cosmetics that give vivid and transparent (clear) impressions.
  • Coloring materials blended in cosmetics include organic synthetic pigments (also called tar pigments) and inorganic pigments, and organic synthetic pigments are classified into dyes and organic pigments. Among them, dyes are often used as raw materials for coloring materials exhibiting fluorescent coloration. Attempts have been made to obtain excellent fluorescent color development by combining specific materials with specific dyes.
  • One of such dyes is a dye having a fluorescein skeleton.
  • Red No. 218, Orange No. 201 and the like are generally known as dyes having a fluorescein skeleton.
  • coloring materials in which inorganic materials such as hydroxyapatite and calcium carbonate are combined with dyes, and specific polyglycerol fatty acid esters are combined Patent Documents 1 and 2).
  • Patent Documents 1 and 2 the properties of the resulting colorant vary greatly depending on the materials combined with the dye.
  • such a coloring material is used as a coloring material for cosmetics, it is required that the properties required for the cosmetic are satisfied and at the same time, the fluorescent color development excellent as the cosmetic is exhibited.
  • the cosmetic coloring material according to the present invention has been studied from such a point of view, and one of its purposes is to realize a color and brightness different from those of conventional coloring materials as a cosmetic coloring material, To provide cosmetics that meet the needs of users by increasing variations as materials. Another object is to develop a coloring material that is less subject to such restrictions, since the solubility of the coloring material in water, oil, etc. changes depending on the material combined with the dye, which may limit the application of the coloring material. to provide.
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • n1 is an integer from 1 to 3
  • R 2 is an alkylene chain having 1 to 5 carbon atoms
  • n2 is an integer from 1 to 3
  • a cosmetic coloring material comprising a compound selected from the group consisting of: [2] The coloring material according to [1], wherein the component (A) is oil-soluble. [3] The colorant of [1] or [2], wherein component (A) is selected from the group consisting of fluorescein, carboxylated fluorescein, halogenated fluorescein, and salts thereof. [4] Component (B) is a compound selected from the group consisting of hydroxyethylimidazolidinone, 1-piperidinepropionic acid, glycylglycine, and PEG/poly-1,2-butanediol-52/32 dimethyl ether The colorant according to any one of [1] to [3].
  • a cosmetic comprising one or more compounds selected from the group consisting of [6]
  • the cosmetic according to [5] wherein the content of component (A) is 0.0001 to 5.0% by mass based on the total mass of the cosmetic.
  • the cosmetic according to any one of [5] to [7] which is an oily cosmetic.
  • the cosmetic according to any one of [5] to [7] which is an aqueous cosmetic, an oil-in-water cosmetic, or a water-in-oil cosmetic in which the coloring material is blended.
  • the cosmetic according to any one of [5] to [9] which is substantially free of powder.
  • the cosmetic coloring material according to the present invention can provide vivid color development, particularly fluorescent color development and transparency (clear feeling), and cosmetics using it can provide novel cosmetic effects. It is a thing.
  • This coloring material can be combined with a wide range of base materials for cosmetics, and can provide a higher degree of freedom in designing cosmetics.
  • the cosmetic coloring material according to the present invention is It contains (A) a dye having a fluorescein skeleton and (B) a specific material, and exhibits vivid color development, particularly fluorescence color development. Each of these components is described below.
  • the (A) component blended in the cosmetic colorant according to the present invention is a dye having a fluorescein skeleton.
  • Component (A) is not particularly limited as long as it is a dye having a fluorescein skeleton, but is preferably selected from the group consisting of fluorescein, carboxylated fluorescein, halogenated fluorescein, and salts thereof, since it exhibits particularly excellent color development. . More specific examples include tetrachlorotetrabromofluorescein (Red No. 218), tetrabromofluorescein (Red No. 223), dibromofluorescein (Orange No.
  • halogenated fluoresceins such as tetrachlorotetrabromofluorescein (Red No. 218), tetrabromofluorescein (Red No. 223), and dibromofluorescein (Orange No. 201) are particularly preferred.
  • Coloring materials containing these halogenated fluoresceins and derivatives thereof have high oil solubility and are suitable for use in oily cosmetics. In addition, it can be easily blended into the oil phase of a water-in-oil type cosmetic or an oil-in-water type cosmetic.
  • fluorescein, carboxylated fluorescein, and salts thereof tend to exhibit strong fluorescent coloration even when combined with an aqueous solvent, they can also be used in aqueous cosmetics. In addition, it can be easily blended into the aqueous phase of a water-in-oil type cosmetic or an oil-in-water type cosmetic.
  • (A) component can also combine two or more types of dyes as needed. New colors can be achieved by combining dyes.
  • (B) Component The (B) component blended in the cosmetic colorant according to the present invention, when combined with the (A) component, achieves characteristic coloration, particularly fluorescent coloration.
  • This component (B) is that it has an amide group, an amino group, a quaternary ammonium structure, a lactam ring structure, a polyoxyalkylene structure, etc., but if it has them, it does not necessarily produce an effect. do not have.
  • excellent fluorescent color development can be achieved by using at least one of the following (B1) to (B4) as the component (B).
  • the component (B1) that can be used in the coloring material according to the present invention is represented by formula (b1).
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • X is —CH 2 — or —N(R 2 )—
  • R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • n1 is an integer from 1 to 3
  • the above hydrocarbon group is not particularly limited, and may be, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cycloalkylalkyl group, a haloalkyl group, an alkoxyalkyl group, or an alkoxycarbonylalkyl group, preferably is an alkyl group.
  • R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms
  • X is —CH 2 — or —NH— and n1 is 1.
  • cyclic carboxamide derivative represented by formula (b1) include the following.
  • the most preferred component (B1) is 1-(2-hydroxyethyl)-2-imidazolidinone.
  • (B2) Cyclic Amino Group-Containing Carboxylic Acid Derivative or Its Salt
  • the component (B2) that can be used in the coloring material according to the present invention is represented by formula (b2).
  • R 2 is an alkylene chain having 1 to 5 carbon atoms
  • n2 is an integer from 1 to 3
  • R 2 is methylene, ethylene, or propylene, n2 is 2;
  • the most preferred (B2) component is piperidine propionic acid.
  • (B3) a glycylglycine derivative or a salt thereof
  • the (B3) component that can be used in the coloring material according to the present invention is represented by the formula (b3).
  • R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms
  • a preferred form is (b3) in which R 3 is hydrogen, methyl, or ethyl.
  • the most preferred (B3) component is glycylglycine where R3 is hydrogen.
  • (B4) an alkylene oxide derivative
  • the (B4) component that can be used in the coloring material according to the present invention is represented by the formula (b4).
  • R 4 O—[BO) l (EO) m (BO) n ]—R 4 (b4)
  • R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms
  • BO is an oxybutylene group
  • EO is an oxyethylene group
  • m and n are the average added moles of BO and EO, respectively; 1 ⁇ m ⁇ 70, 1 ⁇ l + n ⁇ 70,
  • the ratio of EO to the total number of BO and EO is 20-80% by mass.
  • this alkylene oxide derivative has a block-type polymer main chain in which EO, which is an oxyethylene group, and BO, which is an oxybutylene group, form blocks.
  • R4 is preferably hydrogen, a methyl group, or an ethyl group.
  • BO can have a linear or branched structure. Specifically, BO can have a structure derived from an alkyldiol having 4 carbon atoms. Specifically, derived from 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,3-propanediol, 1-dimethyl-1,2-ethanediol takes an oxyalkylene structure.
  • m is preferably 5 to 150.
  • the most preferred (B4) component is PEG/poly-1,2-butanediol-52/32 dimethyl ether.
  • the component (B) may be a salt of the compounds represented by the formulas (b1) to (b4) other than those described above.
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, magnesium salts, ammonium salts and the like.
  • organic salts include acetates, lactates, maleates, fumarates, tartrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, amino acid salts and the like.
  • the component (B) can be blended either alone or in combination of two or more.
  • the cosmetic colorant according to the present invention contains a combination of the above-described components (A) and (B). These generally exhibit fluorescent coloration when they come into contact with each other in solution or dispersion. Therefore, the cosmetic coloring material is generally in the form of a solution or a dispersion liquid, but may be in the form of a powder mixture containing no solvent or dispersion medium. Further, when it is blended in cosmetics, it may be blended in the form of a solution or dispersion with other ingredients of the cosmetic, or it may be blended in the form of a powder mixture. ) components may be blended separately.
  • the solvent or dispersion medium used when the cosmetic coloring material according to the present invention takes the form of a solution or dispersion can be arbitrarily selected from those used for cosmetics.
  • water or an organic solvent, especially an oily component generally used in cosmetics is preferably used.
  • the oily component includes liquid oil, solid oil and semi-solid oil. These are classified according to their hardness, and when the hardness at 25° C. is 0.1 to 10 N, they are classified as semi-solid oils. This hardness can be measured with a rheometer manufactured by Rheotec, with a pressure-sensitive axis of 5 ⁇ , a penetration speed of 2 cm/min, and a penetration of 3 mm.
  • Liquids such as olive oil, avocado oil, camellia oil, macadamia nut oil, evening primrose oil, jojoba oil, rapeseed oil, egg yolk oil, sesame oil, castor oil, safflower oil, cottonseed oil, soybean oil, teaseed oil, rice bran oil, or germ oil Fats and oils; Hydrocarbon oils such as squalane, isododecane, hydrogenated polyisobutene, hydrogenated polydecene, or liquid paraffin; Pentaerythrityl tetraethylhexanoate, di(phytosteryl/octyldodecyl) lauroyl glutamate, triisostearin, glyceryl diisostearate, triethylhexanoin, dimer dilinoleic acid (phytosteryl/behenyl), dimer dilinoleic acid (phytosteryl/isostearyl/cet
  • Solid or semi-solid oils include solid oils, waxes, hydrocarbons, higher alcohols and fatty acids.
  • Solid oils such as Japanese wax, cocoa butter, or hydrogenated castor oil
  • Waxes such as carnauba wax, beeswax, candelilla wax, rice bran wax, or jojoba wax:
  • Hydrocarbon waxes and semi-solid oils such as polyethylene wax, paraffin wax, ceresin, ozokerite, microcrystalline wax, or petrolatum;
  • Higher alcohols such as behenyl alcohol, cetanol, or batyl alcohol; Dipentaerythrityl hexahydroxystearate, macadamia nut fatty acid phytosteryl, tetra (behenate/benzoate/ethylhexanoate) pentaerythrityl, dimer dilinoleate (phytosteryl/behenyl), or macadamia nut oil polyglyceryl-6 ester subbehenate semi-solid
  • the cosmetic coloring material according to the present invention exhibits fluorescent coloration due to interaction between the components (A) and (B)
  • the compounding ratio of the components (A) and (B) must be within a specific range. is preferred.
  • the ratio of the content of component (B) to the content of component (A) is preferably 0.002 to 120,000, more preferably 0.05 to 2,500. is more preferable.
  • the form of the formulation is not particularly limited. That is, the cosmetic according to the present invention can take any form such as an oily cosmetic, an aqueous cosmetic, an oil-in-water emulsified cosmetic, or a water-in-oil emulsified cosmetic. Moreover, the cosmetic according to the present invention may be a liquid cosmetic or a solid cosmetic. Depending on the solubility of the cosmetic coloring material, it can be blended in the cosmetic oil phase or in the aqueous phase. However, since the cosmetic colorant according to the present invention is generally highly oil-soluble, it is preferably blended with oily solid cosmetics and oily liquid cosmetics.
  • emulsified cosmetics it is preferable to blend the cosmetic coloring material according to the present invention in the oil phase.
  • the cosmetic according to the present invention exhibits excellent fluorescent color development in any form, oil-based cosmetics or aqueous cosmetics tend to achieve better transparency than emulsified cosmetics, and are therefore preferable.
  • the cosmetic according to the present invention can give a unique and vivid impression due to fluorescence coloration, it is preferably a makeup cosmetic, particularly lipstick, lip gloss, eye shadow, or mascara. It is preferably a makeup cosmetic.
  • the cosmetic according to the present invention contains various components to be described later.
  • the content of component (A) should be 0.0001 based on the total weight of the cosmetic. is preferably from 0.001 to 1.0% by mass, preferably from 0.001 to 1.0% by mass, and preferably from 0.01 to 15% by mass, It is more preferably 0.05 to 13% by mass.
  • the cosmetic according to the present invention can contain various ingredients that can be generally used in cosmetics, depending on the form of the formulation.
  • oily components oily thickeners, ultraviolet absorbers, moisturizing agents, film-forming agents, water-soluble polymers, water-soluble agents, oil-soluble agents, sequestering agents, antioxidants, water, perfumes, and cosmetics according to the present invention.
  • a coloring material or the like different from the coloring material can be appropriately blended as needed.
  • oil-based component those listed in the section on the cosmetic colorant can be used.
  • Oily thickeners include dextrin palmitate, dextrin stearate, dextrin palmitate stearate, dextrin isostearate, (palmitate/2-ethylhexanoate) dextrin, silica silylate, disteardimonium hectorite, dimethylalkyl ammonium hectorite, distearyldimethylammonium chloride-treated aluminum magnesium silicate, and the like.
  • UV absorbers include benzoic acid UV absorbers such as para-aminobenzoic acid, anthranilic acid UV absorbers such as methyl anthramylate, salicylic acid UV absorbers such as octyl salicylate and phenyl salicylate, isopropyl paramethoxycinnamate, Octyl paramethoxycinnamate (ethylhexyl methoxycinnamate), cinnamic acid UV absorbers such as glyceryl mono-2-ethylhexanoate di-paramethoxycinnamate, 2,4-dihydroxybenzophenone, 2-hydroxy-4 -Methoxybenzophenone, benzophenone UV absorbers such as 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, urocanic acid, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 4-tert-butyl -4'-Methoxybenzoylmethane and the like
  • Moisturizers include 1,3-butylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, hexanediol, glycerin, diglycerin, xylitol, maltitol, maltose, and D-mannite.
  • Coating agents include pullulan tri(trimethylsiloxy)silylpropylcarbamate, polymethylsilsesquioxane, polypropylsilsesquioxane, trimethylsiloxysilicate, (acrylates/dimethicone) copolymer, (ethylene/propylene) copolymer, isostearic acid.
  • Silicone resins such as dextrin, fluorine-modified silicone and acrylic silicone, latexes of polyvinyl alcohol, polyvinylpyrrolidone, polyvinyl acetate and polyvinyl acetate, dextrin, cellulose derivatives such as alkyl cellulose and nitrocellulose, and the like.
  • Water-soluble polymers include plant-based polymers such as gum arabic, carrageenan, pectin, agar, quince seed (quince), starch, algae colloid (brown algae extract), microbial-based polymers such as dextran and pullulan, collagen, and casein. , animal polymers such as gelatin, starch polymers such as carboxymethyl starch and methylhydroxypropyl starch, alginic acid polymers such as sodium alginate, vinyl polymers such as carboxyvinyl polymer (CARBOPOL, etc.), polyoxyethylene acrylic polymers such as polyoxyethylene-polyoxypropylene copolymers, sodium polyacrylate, polyacrylamide, and polymethyl methacrylate; molecules and the like.
  • plant-based polymers such as gum arabic, carrageenan, pectin, agar, quince seed (quince), starch, algae colloid (brown algae extract), microbial-based polymers such as dextran and pullulan, collagen, and casein.
  • Water-soluble drugs include inosit, pyridoxine hydrochloride, benzyl nicotinate, nicotinamide, dl- ⁇ -tocopherol nicotinate, magnesium ascorbate phosphate, ascorbate 2-glucoside, vitamin D2 (ergocasiferol), dl- ⁇ - Vitamins such as tocopherol 2-L ascorbic acid phosphate potassium salt, pantothenic acid, biotin, anti-inflammatory agents such as allantoin and glycyrrhetinic acid, whitening agents such as arbutin, astringents such as zinc oxide and tannic acid, sulfur, Examples include lysozyme chloride, pyridoxine hydrochloride, ⁇ -oryzanol and the like.
  • Oil-soluble drugs include vitamin A, retinol, retinol palmitate, dl- ⁇ -tocopherol, dl- ⁇ -tocopherol acetate, azulene, glucosylhesperidin, and stearyl glycyrrhetinate.
  • Sequestering agents include sodium edetate, sodium metaphosphate, phosphoric acid, and the like.
  • Antioxidants include ascorbic acid, ⁇ -tocopherol, dibutylhydroxytoluene, and butylhydroxyanisole.
  • dispersants examples include surfactants for stably dispersing oily ingredients and powder ingredients in cosmetics.
  • the surfactant can be arbitrarily selected from cationic, anionic, nonionic, amphoteric surfactants, etc. according to the purpose.
  • the cosmetic according to the present invention contains a coloring material obtained by combining the components (A) and (B), but may contain other coloring materials, such as dyes, in order to adjust the coloring.
  • powdered ingredients are sometimes added to common cosmetics.
  • powders include inorganic powders, organic powders, copolymer resin powders, inorganic pigments and organic pigments.
  • these powders can also be blended as needed, but the powders may impair the vividness and transparency of the fluorescent coloration of the cosmetic of the present invention. Therefore, when the cosmetic according to the present invention contains a powder component, it is preferable that the blending ratio of the powder component is 5% by mass or less based on the total mass of the cosmetic, and it is particularly preferred that the powder component is not included at all. preferable.
  • non-colored powders other than pigments have a strong tendency to impair the fluorescent color development of the cosmetic composition according to the present invention, so the blending ratio thereof is preferably small. Therefore, when a powder component is blended into the cosmetic according to the present invention, the blending ratio of the non-colored powder is preferably 5% by mass or less based on the total mass of the powder component.
  • the non-colored powder is a colorless or white powder, such as polyamide powder, hydroxyapatite, and calcium carbonate.
  • Examples 101-107, Comparative Examples 101-105 An oily solid cosmetic was prepared by blending the components shown in Table 1 below.
  • a panel of 10 persons evaluated the "appearance color development", “transparency”, “applied color”, and “staining" of the cosmetics of each example according to the following criteria.
  • D 5 or less judged to be effective.
  • Examples 201 to 205, Comparative Example 201 Aqueous cosmetics were prepared by blending the components shown in Table 2 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
  • Examples 301-304, Comparative Examples 301-303 An oily cosmetic was prepared by blending the components shown in Table 3 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
  • Example 401 An oily cosmetic was prepared by blending the components shown in Table 4 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
  • Examples 501-503, Comparative Example 501 An oil-in-water cosmetic was prepared by blending the components shown in Table 5 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
  • Examples 601-603 A water-in-oil type cosmetic was prepared by blending the components shown in Table 6 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.

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Abstract

The present invention provides a cosmetic colorant and a cosmetic with which it is possible to impart a vivid fluorescent color and a transparency effect. The cosmetic colorant according to the present invention contains (A) a dye having a fluorescein skeleton, and (B) a cyclic carboxamide derivative, a cyclic amino group-containing carboxylic acid derivative, a glycylglycine derivative, an alkylene oxide derivative, or a salt of these derivatives. The present invention also pertains to a cosmetic containing the cosmetic colorant.

Description

化粧用色材およびそれを用いた化粧料Cosmetic coloring materials and cosmetics using the same
　本発明は、鮮やかな蛍光発色をするとともに透明感（クリア感）のある化粧用色材、およびそれを用いた化粧料に関するものである。さらに詳しくは、特定構造を有する染料と、所定材料とを組み合わせた化粧用色材及びそれを含有する化粧料に関するものである。 The present invention relates to a cosmetic coloring material that produces bright fluorescent color and has transparency (clear feeling), and cosmetics using the same. More specifically, the present invention relates to a cosmetic coloring material obtained by combining a dye having a specific structure and a predetermined material, and a cosmetic containing the same.
　唇を彩る口紅やグロス等の口唇化粧料、チーク（頬紅）あるいはアイシャドーといったメーキャップ化粧料は、その使用者の外観の印象を一変させる程の重要な化粧効果を発揮する化粧料であり、その色は製品を選択する上で鍵となる要素の一つである。近年、彩りが鮮やかで透明な（クリアな）印象のメーキャップ化粧料が求められており、例えば輝度の高い蛍光発色を呈する口紅等が注目されている。 Lip cosmetics such as lipsticks and glosses that color the lips, and makeup cosmetics such as cheeks (blushers) and eye shadows are cosmetics that exert such an important cosmetic effect as to completely change the impression of the user's appearance. Color is one of the key factors in choosing a product. BACKGROUND ART In recent years, there has been a demand for makeup cosmetics that give vivid and transparent (clear) impressions.
　メーキャップ化粧料には各種基材と色材（着色剤）とが配合されるが、口唇や肌に適用した際の発色を担うのは色材である。化粧料に配合される色材には、有機合成色素（タール色素とも呼ばれる）と無機顔料とが含まれ、有機合成色素は、染料と有機顔料とに分類される。このうち、蛍光発色を呈する色材の原料としては染料が多く用いられる。そして、特定の染料に対して、特定の材料を組み合わせることによって、優れた蛍光発色を得る試みがなされている。 Various base materials and coloring materials (coloring agents) are blended in makeup cosmetics, but it is the coloring materials that are responsible for the color development when applied to the lips and skin. Coloring materials blended in cosmetics include organic synthetic pigments (also called tar pigments) and inorganic pigments, and organic synthetic pigments are classified into dyes and organic pigments. Among them, dyes are often used as raw materials for coloring materials exhibiting fluorescent coloration. Attempts have been made to obtain excellent fluorescent color development by combining specific materials with specific dyes.
　そのような染料の一つとして、フルオロセイン骨格を有する染料が挙げられる。フルオロセイン骨格を有する染料として、赤色２１８号、橙２０１号などが一般的に知られている。そして、それらの染料に各種の材料を組み合わせて蛍光発色を実現することが検討されている。例えば、染料にヒドロキシアパタイトや炭酸カルシウムなどの無機材料を組み合わせたり、特定のポリグリセリン脂肪酸エステルを組み合わせたりした色材が検討されている（特許文献１および２）。しかしながら、染料に対して組み合わせる材料によって、得られる色材の特性は大きく変化する。このような色材を化粧用色材として用いる場合には、化粧料において要求される特性を満たすと同時に、化粧料として優れた蛍光発色を呈することが求められる。 One of such dyes is a dye having a fluorescein skeleton. Red No. 218, Orange No. 201 and the like are generally known as dyes having a fluorescein skeleton. In addition, it is being studied to combine various materials with these dyes to achieve fluorescent coloring. For example, coloring materials in which inorganic materials such as hydroxyapatite and calcium carbonate are combined with dyes, and specific polyglycerol fatty acid esters are combined (Patent Documents 1 and 2). However, the properties of the resulting colorant vary greatly depending on the materials combined with the dye. When such a coloring material is used as a coloring material for cosmetics, it is required that the properties required for the cosmetic are satisfied and at the same time, the fluorescent color development excellent as the cosmetic is exhibited.
特開２０１６－１３８０９５公報Japanese Patent Application Laid-Open No. 2016-138095 特開２０２１－０９８６７３公報Japanese Patent Application Laid-Open No. 2021-098673
　本発明による化粧用色材は、このような観点から検討されたものであり、ひとつの目的は、化粧用色材として、従来の色材とは異なる色彩や輝度を実現して、化粧用色材としてのバリエーションを増やし、使用者のニーズに合った化粧料を提供することである。また他の目的は、染料に組み合わせる材料によって、水や油などに対する色材の溶解性が変化するので、色材の用途が限定されることがあるが、そのような制限を受けにくい色材を提供することである。 The cosmetic coloring material according to the present invention has been studied from such a point of view, and one of its purposes is to realize a color and brightness different from those of conventional coloring materials as a cosmetic coloring material, To provide cosmetics that meet the needs of users by increasing variations as materials. Another object is to develop a coloring material that is less subject to such restrictions, since the solubility of the coloring material in water, oil, etc. changes depending on the material combined with the dye, which may limit the application of the coloring material. to provide.
　本発明によれば、以下の発明が提供される。
［１］　（Ａ）フルオレセイン骨格を持つ染料、および
　（Ｂ）下記（Ｂ１）～（Ｂ４）からなる群から選択される化合物：
（Ｂ１）式（ｂ１）で表される環状カルボキサミド誘導体またはその塩
Figure JPOXMLDOC01-appb-C000007
 （式中、
　Ｒ１は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、
　Ｘは、－ＣＨ２－または－Ｎ（Ｒ２）－であり、ここで、Ｒ２は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、かつ
　ｎ１は、１～３の整数である）、
　（Ｂ２）式（ｂ２）で表される環状アミノ基含有カルボン酸誘導体またはその塩、
Figure JPOXMLDOC01-appb-C000008
 （式中、
　Ｒ２は、炭素数１～５のアルキレン鎖であり、
　ｎ２は１～３の整数である）、
　（Ｂ３）式（ｂ３）で表されるグリシルグリシン誘導体またはその塩、
Figure JPOXMLDOC01-appb-C000009
 （式中、
　Ｒ３は、水素、炭素数１～６のアルキル基、炭素数６～１０のアリール基、炭素数２～７のアシル基、または炭素数７～１１のアロイル基である）
　（Ｂ４）式（ｂ４）で表されるアルキレンオキシド誘導体、
　Ｒ４Ｏ－［（ＢＯ）ｌ（ＥＯ）ｍ（ＢＯ）ｎ］－Ｒ４　（ｂ４）
（式中、
　Ｒ４は、それぞれ独立に、水素、または炭素数１～４の炭化水素基であり、　ＢＯはオキシブチレン基、ＥＯはオキシエチレン基であり、
　ｌ、ｍおよびｎは、それぞれＢＯおよびＥＯの平均付加モル数であり、
１≦ｍ≦７０、
１≦ｌ＋ｎ≦７０であり、
ＢＯとＥＯの合計数に対するＥＯの割合は２０～８０質量％である。）からなる群から選択される化合物
を含んでなる、化粧料用色材。
［２］　（Ａ）成分が、油溶性である、［１］に記載の色材。
［３］　（Ａ）成分が、フルオレセイン、カルボキシル化フルオレセイン、ハロゲン化フルオレセイン、およびそれらの塩からなる群から選択される、［１］または［２］に記載の色材。
［４］　（Ｂ）成分が、ヒドロキシエチルイミダゾリジノン、１－ピペリジンプロピオン酸、グリシルグリシン、およびＰＥＧ／ポリ－１，２－ブタンジオール－５２／３２ジメチルエーテルからなる群から選択される化合物である、［１］～［３］いずれかに記載の色材。
［５］　（Ａ）フルオレセイン骨格を持つ染料、および
　（Ｂ）下記（Ｂ１）～（Ｂ４）からなる群から選択される化合物：
（Ｂ１）式（ｂ１）で表される環状カルボキサミド誘導体またはその塩
Figure JPOXMLDOC01-appb-C000010
 （式中、
　Ｒ１は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、
　Ｘは、－ＣＨ２－または－Ｎ（Ｒ２）－であり、ここで、Ｒ２は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、かつ
　ｎ１は、１～３の整数である）、
　（Ｂ２）式（ｂ２）で表される環状アミノ基含有カルボン酸誘導体またはその塩、
Figure JPOXMLDOC01-appb-C000011
 （式中、
　Ｒ２は、炭素数１～５のアルキレン鎖であり、
　ｎ２は１～３の整数である）、
　（Ｂ３）式（ｂ３）で表されるグリシルグリシン誘導体またはその塩、
Figure JPOXMLDOC01-appb-C000012
 （式中、
　Ｒ３は、水素、炭素数１～６のアルキル基、炭素数６～１０のアリール基、炭素数２～７のアシル基、または炭素数７～１１のアロイル基である）
　（Ｂ４）式（ｂ４）で表されるアルキレンオキシド誘導体、
Ｒ４Ｏ－［（ＢＯ）ｌ（ＥＯ）ｍ（ＢＯ）ｎ］－Ｒ４　（ｂ４）
（式中、
　Ｒ４は、それぞれ独立に、水素、または炭素数１～４の炭化水素基であり、　ＢＯはオキシブチレン基、ＥＯはオキシエチレン基であり、
　ｌ、ｍおよびｎは、それぞれＢＯおよびＥＯの平均付加モル数であり、
１≦ｍ≦７０、
１≦ｌ＋ｎ≦７０であり、
ＢＯとＥＯの合計数に対するＥＯの割合は２０～８０質量％である。）
からなる群から選択される化合物
を１種または２種以上含んでなる、化粧料。　
［６］　前記化粧料の総質量を基準とした、（Ａ）成分の含有率が、０．０００１～５．０質量％である、［５］に記載の化粧料。
［７］　前記化粧料の総質量を基準とした、（Ｂ）成分の含有率が、０．０１～１５質量％である、［５］または［６］に記載の化粧料。
［８］　油性化粧料である、［５］～［７］のいずれかに記載の化粧料。
［９］　前記色材が配合された、水性化粧料、水中油型化粧料または油中水型化粧料である、［５］～［７］のいずれか１項に記載の化粧料。
［１０］　粉末を実質的に含まない、［５］～［９］のいずれかに記載の化粧料。 According to the present invention, the following inventions are provided.
[1] (A) a dye having a fluorescein skeleton, and (B) a compound selected from the group consisting of the following (B1) to (B4):
(B1) a cyclic carboxamide derivative represented by formula (b1) or a salt thereof
Figure JPOXMLDOC01-appb-C000007
 (In the formula,
R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n1 is an integer from 1 to 3),
(B2) a cyclic amino group-containing carboxylic acid derivative represented by formula (b2) or a salt thereof;
Figure JPOXMLDOC01-appb-C000008
 (In the formula,
R 2 is an alkylene chain having 1 to 5 carbon atoms,
n2 is an integer from 1 to 3),
(B3) a glycylglycine derivative represented by formula (b3) or a salt thereof;
Figure JPOXMLDOC01-appb-C000009
 (In the formula,
R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms)
(B4) an alkylene oxide derivative represented by formula (b4),
R 4 O—[(BO) l (EO) m (BO) n ]—R 4 (b4)
(In the formula,
R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, BO is an oxybutylene group, EO is an oxyethylene group,
l, m and n are the average added moles of BO and EO, respectively;
1≦m≦70,
1 ≤ l + n ≤ 70,
The ratio of EO to the total number of BO and EO is 20-80% by mass. ), a cosmetic coloring material comprising a compound selected from the group consisting of:
[2] The coloring material according to [1], wherein the component (A) is oil-soluble.
[3] The colorant of [1] or [2], wherein component (A) is selected from the group consisting of fluorescein, carboxylated fluorescein, halogenated fluorescein, and salts thereof.
[4] Component (B) is a compound selected from the group consisting of hydroxyethylimidazolidinone, 1-piperidinepropionic acid, glycylglycine, and PEG/poly-1,2-butanediol-52/32 dimethyl ether The colorant according to any one of [1] to [3].
[5] (A) a dye having a fluorescein skeleton, and (B) a compound selected from the group consisting of the following (B1) to (B4):
(B1) a cyclic carboxamide derivative represented by formula (b1) or a salt thereof
Figure JPOXMLDOC01-appb-C000010
 (In the formula,
R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n1 is an integer from 1 to 3),
(B2) a cyclic amino group-containing carboxylic acid derivative represented by formula (b2) or a salt thereof;
Figure JPOXMLDOC01-appb-C000011
 (In the formula,
R 2 is an alkylene chain having 1 to 5 carbon atoms,
n2 is an integer from 1 to 3),
(B3) a glycylglycine derivative represented by formula (b3) or a salt thereof;
Figure JPOXMLDOC01-appb-C000012
 (In the formula,
R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms)
(B4) an alkylene oxide derivative represented by formula (b4),
R 4 O—[(BO) l (EO) m (BO) n ]—R 4 (b4)
(In the formula,
R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, BO is an oxybutylene group, EO is an oxyethylene group,
l, m and n are the average added moles of BO and EO, respectively;
1≦m≦70,
1 ≤ l + n ≤ 70,
The ratio of EO to the total number of BO and EO is 20-80% by mass. )
A cosmetic comprising one or more compounds selected from the group consisting of
[6] The cosmetic according to [5], wherein the content of component (A) is 0.0001 to 5.0% by mass based on the total mass of the cosmetic.
[7] The cosmetic according to [5] or [6], wherein the content of component (B) is 0.01 to 15% by mass based on the total mass of the cosmetic.
[8] The cosmetic according to any one of [5] to [7], which is an oily cosmetic.
[9] The cosmetic according to any one of [5] to [7], which is an aqueous cosmetic, an oil-in-water cosmetic, or a water-in-oil cosmetic in which the coloring material is blended.
[10] The cosmetic according to any one of [5] to [9], which is substantially free of powder.
　本発明による化粧用色材は、鮮やかな発色、特に蛍光発色と透明感（クリア感）とを与えることができるものであり、それを用いた化粧料は、新規は化粧効果を与えることができるものである。そして、この色材は、広範な化粧料基材と組み合わせることができるものであり、化粧料の設計により高い自由度を与えることができる。 The cosmetic coloring material according to the present invention can provide vivid color development, particularly fluorescent color development and transparency (clear feeling), and cosmetics using it can provide novel cosmetic effects. It is a thing. This coloring material can be combined with a wide range of base materials for cosmetics, and can provide a higher degree of freedom in designing cosmetics.
発明の具体的説明Specific description of the invention
［化粧用色材］
　本発明による化粧用色材は、
　（Ａ）フルオレセイン骨格を持つ染料、および（Ｂ）特定の材料を含み、鮮やかな発色、特に蛍光発色を呈するのである。これらの各成分について説明すると以下のとおりである。 [Colorants for cosmetics]
The cosmetic coloring material according to the present invention is
It contains (A) a dye having a fluorescein skeleton and (B) a specific material, and exhibits vivid color development, particularly fluorescence color development. Each of these components is described below.
（Ａ）成分
　本発明による化粧用色材に配合される（Ａ）成分は、フルオレセイン骨格を持つ染料である。（Ａ）成分は、フルオレセイン骨格を有する染料であれば特に限定されないが、フルオレセイン、カルボキシル化フルオレセイン、ハロゲン化フルオレセイン、およびそれらの塩からなる群から選択されるものが特に優れた発色を呈するので好ましい。さらに具体的には、テトラクロロテトラブロモフルオレセイン（赤色２１８号）、テトラブロモフルオレセイン（赤色２２３号）、ジブロモフルオレセイン（橙色２０１号）、フルオロセイン、５－カルボキシフルオロセインなどが挙げられる。これらのフルオロセイン骨格を有する染料は、それ自体が蛍光発色を呈するものであるが、後述する（Ｂ）成分と組み合わせることで、化合物自体が呈する発色とは異なった、鮮やかな蛍光発色が実現できる。 (A) Component The (A) component blended in the cosmetic colorant according to the present invention is a dye having a fluorescein skeleton. Component (A) is not particularly limited as long as it is a dye having a fluorescein skeleton, but is preferably selected from the group consisting of fluorescein, carboxylated fluorescein, halogenated fluorescein, and salts thereof, since it exhibits particularly excellent color development. . More specific examples include tetrachlorotetrabromofluorescein (Red No. 218), tetrabromofluorescein (Red No. 223), dibromofluorescein (Orange No. 201), fluorescein, and 5-carboxyfluoroscein. These dyes having a fluorescein skeleton themselves exhibit fluorescent coloration, but when combined with the component (B) described later, vivid fluorescent coloration different from the coloration exhibited by the compound itself can be realized. .
　これらのうち、テトラクロロテトラブロモフルオレセイン（赤色２１８号）、テトラブロモフルオレセイン（赤色２２３号）、ジブロモフルオレセイン（橙色２０１号）などのハロゲン化フルオロセインは特に好ましい。これらのハロゲン化フルオロセインおよびその誘導体を含む色材は、油溶性が高く、油性化粧料に用いるのに適している。また、油中水型化粧料や水中油型化粧料の油相に配合することも容易である。 Of these, halogenated fluoresceins such as tetrachlorotetrabromofluorescein (Red No. 218), tetrabromofluorescein (Red No. 223), and dibromofluorescein (Orange No. 201) are particularly preferred. Coloring materials containing these halogenated fluoresceins and derivatives thereof have high oil solubility and are suitable for use in oily cosmetics. In addition, it can be easily blended into the oil phase of a water-in-oil type cosmetic or an oil-in-water type cosmetic.
　また、フルオレセイン、カルボキシル化フルオレセイン、およびそれらの塩は水性溶媒と組み合わせた場合でも、強い蛍光発色を呈する傾向にあるので、水性化粧料に用いることもできる。また、油中水型化粧料や水中油型化粧料の水相に配合することも容易である。 In addition, since fluorescein, carboxylated fluorescein, and salts thereof tend to exhibit strong fluorescent coloration even when combined with an aqueous solvent, they can also be used in aqueous cosmetics. In addition, it can be easily blended into the aqueous phase of a water-in-oil type cosmetic or an oil-in-water type cosmetic.
　（Ａ）成分は、必要に応じて２種類以上の染料を組み合わせることもできる。染料を組み合わせることで、新たな色彩を実現することもできる。 (A) component can also combine two or more types of dyes as needed. New colors can be achieved by combining dyes.
（Ｂ）成分
　本発明により化粧用色材に配合される（Ｂ）成分は、（Ａ）成分と組み合わせることで、特徴的な発色、特に蛍光発色を実現するものである。この（Ｂ）成分は、アミド基、アミノ基、４級アンモニウム構造、ラクタム環構造、ポリオキシアルキレン構造などを有することをひとつの特徴とするが、それらを有すれば必ず効果が発現するものではない。一方、本発明者らの検討によれば、以下の（Ｂ１）～（Ｂ４）の少なくともひとつを（Ｂ）成分として用いることで、優れた蛍光発色を実現できることがわかった。 (B) Component The (B) component blended in the cosmetic colorant according to the present invention, when combined with the (A) component, achieves characteristic coloration, particularly fluorescent coloration. One of the characteristics of this component (B) is that it has an amide group, an amino group, a quaternary ammonium structure, a lactam ring structure, a polyoxyalkylene structure, etc., but if it has them, it does not necessarily produce an effect. do not have. On the other hand, according to the studies of the present inventors, it was found that excellent fluorescent color development can be achieved by using at least one of the following (B1) to (B4) as the component (B).
（Ｂ１）環状カルボキサミド誘導体またはその塩
　本発明による色材に用いることができる（Ｂ１）成分は、式（ｂ１）で表されるものである。
Figure JPOXMLDOC01-appb-C000013
 （式中、
　Ｒ１は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、
　Ｘは、－ＣＨ２－または－Ｎ（Ｒ２）－であり、ここで、Ｒ２は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、かつ
　ｎ１は、１～３の整数である）、 (B1) Cyclic carboxamide derivative or its salt The component (B1) that can be used in the coloring material according to the present invention is represented by formula (b1).
Figure JPOXMLDOC01-appb-C000013
 (In the formula,
R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n1 is an integer from 1 to 3),
　上記の炭化水素基は、特に限定されず、例えば、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、シクロアルキルアルキル基、ハロアルキル基、アルコキシアルキル基、アルコキシカルボニルアルキル基であってよく、好ましくはアルキル基である。 The above hydrocarbon group is not particularly limited, and may be, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cycloalkylalkyl group, a haloalkyl group, an alkoxyalkyl group, or an alkoxycarbonylalkyl group, preferably is an alkyl group.
　好ましい形態は、（ｂ１）において、
　Ｒ１が、炭素数１～３のヒドロキシアルキル基であり、
　Ｘが、－ＣＨ２－または－ＮＨ－であり、かつ
　ｎ１が、１である。 A preferred form is, in (b1),
R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms,
X is —CH 2 — or —NH— and n1 is 1.
　式（ｂ１）で表される環状カルボキサミド誘導体の具体例としては、例えば、以下が挙げられる。
Figure JPOXMLDOC01-appb-C000014
 　最も好ましい（Ｂ１）成分は、１－（２－ヒドロキシエチル）－２－イミダゾリジノンである。 Specific examples of the cyclic carboxamide derivative represented by formula (b1) include the following.
Figure JPOXMLDOC01-appb-C000014
 The most preferred component (B1) is 1-(2-hydroxyethyl)-2-imidazolidinone.
　（Ｂ２）環状アミノ基含有カルボン酸誘導体またはその塩
　本発明による色材に用いることができる（Ｂ２）成分は、式（ｂ２）で表されるものである。
Figure JPOXMLDOC01-appb-C000015
 （式中、
　Ｒ２は、炭素数１～５のアルキレン鎖であり、
　ｎ２は１～３の整数である） (B2) Cyclic Amino Group-Containing Carboxylic Acid Derivative or Its Salt The component (B2) that can be used in the coloring material according to the present invention is represented by formula (b2).
Figure JPOXMLDOC01-appb-C000015
 (In the formula,
R 2 is an alkylene chain having 1 to 5 carbon atoms,
n2 is an integer from 1 to 3)
　好ましい形態は、（ｂ２）において、
　Ｒ２が、メチレン、エチレン、またはプロピレン、であり、
　ｎ２が、２である。 A preferred form is, in (b2),
R 2 is methylene, ethylene, or propylene,
n2 is 2;
　最も好ましい（Ｂ２）成分は、ピペリジンプロピオン酸である。 The most preferred (B2) component is piperidine propionic acid.
　（Ｂ３）グリシルグリシン誘導体またはその塩、
　本発明による色材に用いることができる（Ｂ３）成分は、式（ｂ３）で表されるものである。
Figure JPOXMLDOC01-appb-C000016
 （式中、
　Ｒ３は、水素、炭素数１～６のアルキル基、炭素数６～１０のアリール基、炭素数２～７のアシル基、または炭素数７～１１のアロイル基である） (B3) a glycylglycine derivative or a salt thereof,
The (B3) component that can be used in the coloring material according to the present invention is represented by the formula (b3).
Figure JPOXMLDOC01-appb-C000016
 (In the formula,
R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms)
　好ましい形態は、（ｂ３）において、Ｒ３が、水素、メチル、またはエチルである。最も好ましい（Ｂ３）成分は、Ｒ３が水素であるグリシルグリシンである。 A preferred form is (b3) in which R 3 is hydrogen, methyl, or ethyl. The most preferred (B3) component is glycylglycine where R3 is hydrogen.
　（Ｂ４）アルキレンオキシド誘導体、
　本発明による色材に用いることができる（Ｂ４）成分は、式（ｂ４）で表されるものである。
　Ｒ４Ｏ－［ＢＯ）ｌ（ＥＯ）ｍ（ＢＯ）ｎ］－Ｒ４　（ｂ４）
（式中、
　Ｒ４は、それぞれ独立に、水素、または炭素数１～４の炭化水素基であり、　ＢＯはオキシブチレン基、ＥＯはオキシエチレン基であり、
　ｌ、ｍおよびｎは、それぞれＢＯおよびＥＯの平均付加モル数であり、
１≦ｍ≦７０、
１≦ｌ＋ｎ≦７０であり、
ＢＯとＥＯの合計数に対するＥＯの割合は２０～８０質量％である。）　  (B4) an alkylene oxide derivative,
The (B4) component that can be used in the coloring material according to the present invention is represented by the formula (b4).
R 4 O—[BO) l (EO) m (BO) n ]—R 4 (b4)
(In the formula,
R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, BO is an oxybutylene group, EO is an oxyethylene group,
l, m and n are the average added moles of BO and EO, respectively;
1≦m≦70,
1 ≤ l + n ≤ 70,
The ratio of EO to the total number of BO and EO is 20-80% by mass. )
　このアルキレンオキシド誘導体は、一つの態様では、オキシエチレン基であるＥＯと、オキシブチレン基であるＢＯとがブロックを構成しているブロック型ポリマー主鎖を有するものである。 In one aspect, this alkylene oxide derivative has a block-type polymer main chain in which EO, which is an oxyethylene group, and BO, which is an oxybutylene group, form blocks.
　Ｒ４は、水素、メチル基、またはエチル基であることが好ましい。 R4 is preferably hydrogen, a methyl group, or an ethyl group.
　ＢＯは、直鎖状または分岐鎖状の構造をとりうる。具体的には、ＢＯは炭素数４のアルキルジオールに由来する構造をとりえる。具体的には、１，２－ブタンジオール、１，３－ブタンジオール、１，４－ブタンジオール、２－メチル－１，３－プロパンジオール、１－ジメチル－１，２－エタンジオールなどに由来するオキシアルキレン構造を取る。 BO can have a linear or branched structure. Specifically, BO can have a structure derived from an alkyldiol having 4 carbon atoms. Specifically, derived from 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,3-propanediol, 1-dimethyl-1,2-ethanediol takes an oxyalkylene structure.
　なお、ｍは、５～１５０であることが好ましい。 It should be noted that m is preferably 5 to 150.
　最も好ましい（Ｂ４）成分は、ＰＥＧ／ポリ－１，２－ブタンジオール－５２／３２ジメチルエーテルである。 The most preferred (B4) component is PEG/poly-1,2-butanediol-52/32 dimethyl ether.
　（Ｂ）成分は、上記した以外の、式（ｂ１）～（ｂ４）で表される化合物の塩であってもよい。塩の種類は、薬理学的に許容される塩であれば特に限定されず、無機塩であっても有機塩であってもよい。無機塩としては、例えば、塩酸塩、硫酸塩、リン酸塩、臭化水素酸塩、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩、マグネシウム塩、アンモニウム塩等が挙げられる。有機塩としては、例えば、酢酸塩、乳酸塩、マレイン酸塩、フマル酸塩、酒石酸塩、メタンスルホン酸塩、ｐ－トルエンスルホン酸塩、トリエタノールアミン塩、アミノ酸塩等が挙げられる。 The component (B) may be a salt of the compounds represented by the formulas (b1) to (b4) other than those described above. The type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt. Examples of inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, magnesium salts, ammonium salts and the like. Examples of organic salts include acetates, lactates, maleates, fumarates, tartrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, amino acid salts and the like.
　（Ｂ）成分は、１種または２種以上を配合することができる。 The component (B) can be blended either alone or in combination of two or more.
　本発明による化粧用色材は、上記した（Ａ）成分と（Ｂ）成分との組み合わせを含むものである。これらは一般に溶液中または分散液中で相互に接触することで蛍光発色を呈する。このため、化粧用色材としては溶液または分散液の形態を取るのが一般的であるが、溶媒又は分散媒を含まない粉末混合物の形態であってもよい。また、化粧料に配合される場合も、化粧料の他の成分に溶液または分散液の形状で配合されても、粉末混合物の形状で配合されてもよく、また、（Ａ）成分と（Ｂ）成分とを個別に配合してもよい。 The cosmetic colorant according to the present invention contains a combination of the above-described components (A) and (B). These generally exhibit fluorescent coloration when they come into contact with each other in solution or dispersion. Therefore, the cosmetic coloring material is generally in the form of a solution or a dispersion liquid, but may be in the form of a powder mixture containing no solvent or dispersion medium. Further, when it is blended in cosmetics, it may be blended in the form of a solution or dispersion with other ingredients of the cosmetic, or it may be blended in the form of a powder mixture. ) components may be blended separately.
　本発明による化粧料色材が溶液または分散液の形態を取る場合に用いられる溶媒または分散媒は、化粧用に用いられるものから任意に選択することができる。一般的には水または有機溶媒、特に化粧料に一般的に用いられる油性成分が好ましく用いられる。 The solvent or dispersion medium used when the cosmetic coloring material according to the present invention takes the form of a solution or dispersion can be arbitrarily selected from those used for cosmetics. In general, water or an organic solvent, especially an oily component generally used in cosmetics is preferably used.
　油性成分としては、液状油分、固形油分または半固形油分が挙げられる。これらは、その硬度によって分類され、２５℃における硬度が０．１～１０Ｎであるときに半固形油分とされ、それ未満の硬度であると液状油分、それを超えると固形油分と分類できる。この硬度は、レオテック社製レオメーターで、感圧軸５φ、針入速度２ｃｍ／ｍｉｎ、針入度３ｍｍで測定することができる。 The oily component includes liquid oil, solid oil and semi-solid oil. These are classified according to their hardness, and when the hardness at 25° C. is 0.1 to 10 N, they are classified as semi-solid oils. This hardness can be measured with a rheometer manufactured by Rheotec, with a pressure-sensitive axis of 5φ, a penetration speed of 2 cm/min, and a penetration of 3 mm.
　液状油分としては、
　オリーブ油、アボカド油、ツバキ油、マカデミアナッツ油、月見草油、ホホバ油、ナタネ油、卵黄油、ゴマ油、ヒマシ油、サフラワー油、綿実油、大豆油、茶実油、コメヌカ油、または胚芽油等の液体油脂類；
　スクワラン、イソドデカン、水添ポリイソブテン、水添ポリデセン、または流動パラフィン等の炭化水素油；
　テトラエチルヘキサン酸ペンタエリスリチル、ラウロイルグルタミン酸ジ（フィトステリル／オクチルドデシル）、トリイソステアリン、ジイソステアリン酸グリセリル、トリエチルヘキサノイン、ダイマージリノール酸（フィトステリル／ベヘニル）、ダイマージリノール酸（フィトステリル／イソステアリル／セチル／ステアリル／ベヘニル）、パルミチン酸イソプロピル、トリイソステアリン、パルミチン酸エチルヘキシル、ミリスチン酸ミリスチル、ミリスチン酸イソプロピル、ジピバリン酸トリプロピレングリコール、セバシン酸ジイソプロピル、ネオペンタン酸イソデシル、イソステアリン酸イソセチル、２－エチルヘキサン酸セチル、２－ヘプチルウンデシルパルミテート、アジピン酸ジイソブチル、セバシン酸２－ヘキシルデシル、イソプロピルミリステート、２－オクチルドデシルオレエート、リンゴ酸ジイソステアリル、ジ－２－エチルヘキサン酸エチレングリコール、トリ－２－ヘプチルウンデカン酸グリセライド、グリセリルジイソステアレート、グリセリルトリイソステアレート、トリオクタン酸グリセリン、トリイソパルミチン酸グリセリン、トリ－２－エチルヘキサン酸トリメチロールプロパン、またはテトラ－２－エチルヘキサン酸ペンタエリスリトール等のエステル油類；
　ジメチルポリシロキサン、またはメチルフェニルポリシロキサン（ジフェニルシロキシフェニルトリメチコン）等の鎖状シリコーン油；
　オクタメチルシクロテトラシロキサン、またはデカメチルシクロペンタシロキサン等の環状シリコーン油；
　高級アルコール、脂肪酸、トリグリセリン、ならびに
　フッ素変性油
等が挙げられる。 As liquid oil,
Liquids such as olive oil, avocado oil, camellia oil, macadamia nut oil, evening primrose oil, jojoba oil, rapeseed oil, egg yolk oil, sesame oil, castor oil, safflower oil, cottonseed oil, soybean oil, teaseed oil, rice bran oil, or germ oil Fats and oils;
Hydrocarbon oils such as squalane, isododecane, hydrogenated polyisobutene, hydrogenated polydecene, or liquid paraffin;
Pentaerythrityl tetraethylhexanoate, di(phytosteryl/octyldodecyl) lauroyl glutamate, triisostearin, glyceryl diisostearate, triethylhexanoin, dimer dilinoleic acid (phytosteryl/behenyl), dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/ stearyl/behenyl), isopropyl palmitate, triisostearin, ethylhexyl palmitate, myristyl myristate, isopropyl myristate, tripropylene glycol dipivalate, diisopropyl sebacate, isodecyl neopentanoate, isocetyl isostearate, cetyl 2-ethylhexanoate, 2 -heptyl undecyl palmitate, diisobutyl adipate, 2-hexyldecyl sebacate, isopropyl myristate, 2-octyldodecyl oleate, diisostearyl malate, ethylene glycol di-2-ethylhexanoate, tri-2-heptyl Esters such as glyceryl undecanoate, glyceryl diisostearate, glyceryl triisostearate, glyceryl trioctanoate, glyceryl triisopalmitate, trimethylolpropane tri-2-ethylhexanoate, or pentaerythritol tetra-2-ethylhexanoate oils;
Chain silicone oils such as dimethylpolysiloxane or methylphenylpolysiloxane (diphenylsiloxyphenyltrimethicone);
Cyclic silicone oils such as octamethylcyclotetrasiloxane or decamethylcyclopentasiloxane;
Examples include higher alcohols, fatty acids, triglycerin, and fluorine-denatured oils.
　固形油分または半固形油分としては、固体油脂、ロウ類、炭化水素、高級アルコール、脂肪酸が挙げられる。例えば、
　モクロウ、カカオ脂、または硬化ヒマシ油等の固体油脂；
　カルナウバロウ、ミツロウ、キャンデリラロウ、コメヌカロウ、またはホホバ（ｊｏｊｏｂａ）ロウ等のロウ類：
　ポリエチレンワックス、パラフィンワックス、セレシン、オゾケライト、マイクロクリスタリンワックス、またはワセリン等の炭化水素系ワックスおよび半固形油分；
　ベヘニルアルコール、セタノール、またはバチルアルコール等の高級アルコール；
　ヘキサヒドロキシステアリン酸ジペンタエリスリチル、マカダミアナッツ脂肪酸フィトステリル、テトラ（ベヘン酸／安息香酸／エチルヘキサン酸）ペンタエリスリチル、ダイマージリノール酸（フィトステリル／ベヘニル）、またはマカダミアナッツ油ポリグリセリルー６エステルズベヘネート等の半固形のエステル油類；
　シリコンワックス、
ならびに
　ショ糖脂肪酸エステル
等が挙げられる。 Solid or semi-solid oils include solid oils, waxes, hydrocarbons, higher alcohols and fatty acids. for example,
Solid oils such as Japanese wax, cocoa butter, or hydrogenated castor oil;
Waxes such as carnauba wax, beeswax, candelilla wax, rice bran wax, or jojoba wax:
Hydrocarbon waxes and semi-solid oils such as polyethylene wax, paraffin wax, ceresin, ozokerite, microcrystalline wax, or petrolatum;
Higher alcohols such as behenyl alcohol, cetanol, or batyl alcohol;
Dipentaerythrityl hexahydroxystearate, macadamia nut fatty acid phytosteryl, tetra (behenate/benzoate/ethylhexanoate) pentaerythrityl, dimer dilinoleate (phytosteryl/behenyl), or macadamia nut oil polyglyceryl-6 ester subbehenate semi-solid ester oils;
silicone wax,
and sucrose fatty acid esters.
　本発明による化粧料色材は、（Ａ）成分と（Ｂ）成分との相互作用によって蛍光発色を呈するので、（Ａ）成分と（Ｂ）成分との配合比が特定の範囲内にあることが好ましい。具体的には、（Ａ）成分の含有量を基準とした、（Ｂ）成分の含有量の比が、０．００２～１２０，０００であることが好ましく、０．０５～２，５００であることがより好ましい。 Since the cosmetic coloring material according to the present invention exhibits fluorescent coloration due to interaction between the components (A) and (B), the compounding ratio of the components (A) and (B) must be within a specific range. is preferred. Specifically, the ratio of the content of component (B) to the content of component (A) is preferably 0.002 to 120,000, more preferably 0.05 to 2,500. is more preferable.
［化粧料］
　本発明による化粧料は、上記した、本発明による化粧用色材を含むものであれば、その製剤の形態は時に限定されない。すなわち、本発明による化粧料は、油性化粧料、水性化粧料、水中油型乳化化粧料、油中水型乳化化粧料など、任意の形態を取ることができる。また、本発明による化粧料は液状化粧料であっても、固形化粧料であってもよい。そして、化粧用色材の溶解性に応じて、それらの化粧用の油相に配合することも、水相に配合することもできる。しかしながら、本発明による化粧用色材は一般に油溶性が高いので、それを油性固形化粧料、油性液状化粧料に配合することが好ましい。また、乳化化粧料においては、油相に本発明による化粧用色材を配合することが好ましい。また、本発明による化粧料はいずれの形態であっても優れた蛍光発色を呈するが、油性化粧料または水性化粧料は、乳化化粧料よりも優れた透明性を実現できる傾向にあるので好ましい。また、乳化化粧料においては、外相、すなわち油中水型乳化化粧料においては油相に、水中油型乳化化粧料においては水相に、本発明による化粧用色材を配合することが好ましい。 [Cosmetics]
As long as the cosmetic according to the present invention contains the above-described cosmetic coloring material according to the present invention, the form of the formulation is not particularly limited. That is, the cosmetic according to the present invention can take any form such as an oily cosmetic, an aqueous cosmetic, an oil-in-water emulsified cosmetic, or a water-in-oil emulsified cosmetic. Moreover, the cosmetic according to the present invention may be a liquid cosmetic or a solid cosmetic. Depending on the solubility of the cosmetic coloring material, it can be blended in the cosmetic oil phase or in the aqueous phase. However, since the cosmetic colorant according to the present invention is generally highly oil-soluble, it is preferably blended with oily solid cosmetics and oily liquid cosmetics. Further, in emulsified cosmetics, it is preferable to blend the cosmetic coloring material according to the present invention in the oil phase. In addition, although the cosmetic according to the present invention exhibits excellent fluorescent color development in any form, oil-based cosmetics or aqueous cosmetics tend to achieve better transparency than emulsified cosmetics, and are therefore preferable. In emulsified cosmetics, it is preferable to blend the cosmetic coloring material according to the present invention into the external phase, ie, the oil phase of water-in-oil emulsified cosmetics and the aqueous phase of oil-in-water emulsified cosmetics.
　また、本発明による化粧料は、蛍光発色によって独特で鮮やかな印象を与えることができるものであるので、メーキャップ化粧料であることが好ましく、特に口紅、リップグロス、アイシャドー、またはマスカラなどのポイントメーキャップ化粧料であることが好ましい。 In addition, since the cosmetic according to the present invention can give a unique and vivid impression due to fluorescence coloration, it is preferably a makeup cosmetic, particularly lipstick, lip gloss, eye shadow, or mascara. It is preferably a makeup cosmetic.
　本発明による化粧料は、後述する各種の成分を含むものであるが、化粧料として十分は蛍光発色を呈するために、化粧料の総質量を基準として、（Ａ）成分の含有率が、０．０００１～５．０質量％であることが好ましく、０．００１～１．０質量％であることがより好ましく、（Ｂ）成分の含有率が、０．０１～１５質量％であることが好ましく、０．０５～１３質量％であることがより好ましい。 The cosmetic according to the present invention contains various components to be described later. In order to sufficiently exhibit fluorescence as a cosmetic, the content of component (A) should be 0.0001 based on the total weight of the cosmetic. is preferably from 0.001 to 1.0% by mass, preferably from 0.001 to 1.0% by mass, and preferably from 0.01 to 15% by mass, It is more preferably 0.05 to 13% by mass.
　本発明による化粧料は、その製剤の形態に応じて、一般的に化粧料に用いることができる各種の成分を含むことができる。例えば油性成分、油性増粘剤、紫外線吸収剤、保湿剤、被膜剤、水溶性高分子、水溶性薬剤、油溶性薬剤、金属イオン封鎖剤、酸化防止剤、水、香料、本発明による化粧用色材とは異なる色材等を必要に応じて適宜配合することができる。 The cosmetic according to the present invention can contain various ingredients that can be generally used in cosmetics, depending on the form of the formulation. For example, oily components, oily thickeners, ultraviolet absorbers, moisturizing agents, film-forming agents, water-soluble polymers, water-soluble agents, oil-soluble agents, sequestering agents, antioxidants, water, perfumes, and cosmetics according to the present invention. A coloring material or the like different from the coloring material can be appropriately blended as needed.
　油性成分としては、上記した化粧用色材の項で挙げたものを用いることができる。 As the oil-based component, those listed in the section on the cosmetic colorant can be used.
　油性増粘剤としては、パルミチン酸デキストリン、ステアリン酸デキストリン、パルミチン酸ステアリン酸デキストリン、イソステアリン酸デキストリン、（パルミチン酸／２－エチルヘキサン酸）デキストリン、シリル化シリカ、ジステアルジモニウムヘクトライト、ジメチルアルキルアンモニウムヘクトライト、塩化ジステアリルジメチルアンモニウム処理ケイ酸アルミニウムマグネシウム等が挙げられる。 Oily thickeners include dextrin palmitate, dextrin stearate, dextrin palmitate stearate, dextrin isostearate, (palmitate/2-ethylhexanoate) dextrin, silica silylate, disteardimonium hectorite, dimethylalkyl ammonium hectorite, distearyldimethylammonium chloride-treated aluminum magnesium silicate, and the like.
　紫外線吸収剤としては、パラアミノ安息香酸等の安息香酸系紫外線吸収剤、アントラミル酸メチル等のアントラニル酸系紫外線吸収剤、サリチル酸オクチル、サリチル酸フェニル等のサリチル酸系紫外線吸収剤、パラメトキシケイ皮酸イソプロピル、パラメトキシケイ皮酸オクチル（メトキシケイ皮酸エチルヘキシル）、ジパラメトキシケイ皮酸モノ－２－エチルヘキサン酸グリセリル等のケイ皮酸系紫外線吸収剤、２，４－ジヒドロキシベンゾフェノン、２－ヒドロキシ－４－メトキシベンゾフェノン、２－ヒドロキシ－４－メトキシベンゾフェノン－５－スルホン酸等のベンゾフェノン系紫外線吸収剤、ウロカニン酸、２－（２‘－ヒドロキシ－５’－メチルフェニル）ベンゾトリアゾール、４－ｔｅｒｔ－ブチル－４'－メトキシベンゾイルメタン等が挙げられる。 UV absorbers include benzoic acid UV absorbers such as para-aminobenzoic acid, anthranilic acid UV absorbers such as methyl anthramylate, salicylic acid UV absorbers such as octyl salicylate and phenyl salicylate, isopropyl paramethoxycinnamate, Octyl paramethoxycinnamate (ethylhexyl methoxycinnamate), cinnamic acid UV absorbers such as glyceryl mono-2-ethylhexanoate di-paramethoxycinnamate, 2,4-dihydroxybenzophenone, 2-hydroxy-4 -Methoxybenzophenone, benzophenone UV absorbers such as 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, urocanic acid, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 4-tert-butyl -4'-Methoxybenzoylmethane and the like.
　保湿剤としては、１，３－ブチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、ヘキシレングリコール、ヘキサンジオール、グリセリン、ジグリセリン、キシリトール、マルチトール、マルトース、Ｄ－マンニット等が挙げられる。 Moisturizers include 1,3-butylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, hexanediol, glycerin, diglycerin, xylitol, maltitol, maltose, and D-mannite.
　被膜剤としては、トリ（トリメチルシロキシ）シリルプロピルカルバミド酸プルラン、ポリメチルシルセスキオキサン、ポリプロピルシルセスキオキサン、トリメチルシロキシケイ酸、（アクリレーツ／ジメチコン）コポリマー、（エチレン／プロピレン）コポリマー、イソステアリン酸デキストリン、フッ素変成シリコーン、アクリルシリコーン等のシリコーン系樹脂やポリビニルアルコール、ポリビニルピロリドン、ポリ酢酸ビニル、ポリ酢酸アルキルのラテックス類、デキストリン、アルキルセルロースやニトロセルロース等のセルロース誘導体等が挙げられる。 Coating agents include pullulan tri(trimethylsiloxy)silylpropylcarbamate, polymethylsilsesquioxane, polypropylsilsesquioxane, trimethylsiloxysilicate, (acrylates/dimethicone) copolymer, (ethylene/propylene) copolymer, isostearic acid. Silicone resins such as dextrin, fluorine-modified silicone and acrylic silicone, latexes of polyvinyl alcohol, polyvinylpyrrolidone, polyvinyl acetate and polyvinyl acetate, dextrin, cellulose derivatives such as alkyl cellulose and nitrocellulose, and the like.
　水溶性高分子としては、アラビアゴム、カラギーナン、ペクチン、カンテン、クインスシード（マルメロ）、デンプン、アルゲコロイド（褐藻エキス）等の植物系高分子、デキストラン、プルラン等の微生物系高分子、コラーゲン、カゼイン、ゼラチン等の動物系高分子、カルボキシメチルデンプン、メチルヒドロキシプロピルデンプン等のデンプン系高分子、アルギン酸ナトリウム等のアルギン酸系高分子、カルボキシビニルポリマー（ＣＡＲＢＯＰＯＬなど）等のビニル系高分子、ポリオキシエチレン系高分子、ポリオキシエチレンポリオキシプロピレン共重合体系高分子、ポリアクリル酸ナトリウム、ポリアクリルアミド、ポリメタクリル酸メチル等のアクリル系高分子、ベントナイト、ケイ酸アルミニウムマグネシウム、ラポナイト等の無機系水溶性高分子等が挙げられる。 Water-soluble polymers include plant-based polymers such as gum arabic, carrageenan, pectin, agar, quince seed (quince), starch, algae colloid (brown algae extract), microbial-based polymers such as dextran and pullulan, collagen, and casein. , animal polymers such as gelatin, starch polymers such as carboxymethyl starch and methylhydroxypropyl starch, alginic acid polymers such as sodium alginate, vinyl polymers such as carboxyvinyl polymer (CARBOPOL, etc.), polyoxyethylene acrylic polymers such as polyoxyethylene-polyoxypropylene copolymers, sodium polyacrylate, polyacrylamide, and polymethyl methacrylate; molecules and the like.
　水溶性薬剤としては、イノシット、塩酸ピリドキシン、ニコチン酸ベンジル、ニコチン酸アミド、ニコチン酸ｄｌ－α－トコフェロール、アスコルビン酸リン酸マグネシウム、アスコルビン酸２－グルコシド、ビタミンＤ２（エルゴカシフェロール）、ｄｌ－α－トコフェロール２－Ｌアスコルビン酸リン酸ジエステルカリウム塩、パントテン酸、ビオチン等のビタミン類、アラントイン、グリチルレチン酸等の抗炎症剤、アルブチン等の美白剤、酸化亜鉛、タンニン酸等の収斂剤、イオウ、塩化リゾチーム、塩酸ピリドキシン、γ－オリザノール等が挙げられる。 Water-soluble drugs include inosit, pyridoxine hydrochloride, benzyl nicotinate, nicotinamide, dl-α-tocopherol nicotinate, magnesium ascorbate phosphate, ascorbate 2-glucoside, vitamin D2 (ergocasiferol), dl-α - Vitamins such as tocopherol 2-L ascorbic acid phosphate potassium salt, pantothenic acid, biotin, anti-inflammatory agents such as allantoin and glycyrrhetinic acid, whitening agents such as arbutin, astringents such as zinc oxide and tannic acid, sulfur, Examples include lysozyme chloride, pyridoxine hydrochloride, γ-oryzanol and the like.
　油溶性薬剤としては、ビタミンＡ、レチノール、パルミチン酸レチノール、ｄｌ－α－トコフェロール、酢酸ｄｌ－α－トコフェロール、アズレン、グルコシルヘスペリジン、およびグリチルレチン酸ステアリル等が挙げられる。 Oil-soluble drugs include vitamin A, retinol, retinol palmitate, dl-α-tocopherol, dl-α-tocopherol acetate, azulene, glucosylhesperidin, and stearyl glycyrrhetinate.
　金属イオン封鎖剤としては、エデト酸ナトリウム塩、メタリン酸ナトリウム、リン酸等が挙げられる。 Sequestering agents include sodium edetate, sodium metaphosphate, phosphoric acid, and the like.
　酸化防止剤としては、アスコルビン酸、α－トコフェロール、ジブチルヒドロキシトルエン、ブチルヒドロキシアニソール等が挙げられる。 Antioxidants include ascorbic acid, α-tocopherol, dibutylhydroxytoluene, and butylhydroxyanisole.
　分散剤としては、油性成分や粉末成分などを化粧料中に安定に分散させるための界面活性剤などが挙げられる。界面活性剤としてはカチオン性、アニオン性、非イオン性、両性などの界面活性剤から目的に応じて任意に選択することができる。 Examples of dispersants include surfactants for stably dispersing oily ingredients and powder ingredients in cosmetics. The surfactant can be arbitrarily selected from cationic, anionic, nonionic, amphoteric surfactants, etc. according to the purpose.
　本発明による化粧料は、（Ａ）成分と（Ｂ）成分との組み合わせによる色材を含むが、発色の色彩などを調製するために、その他の色材、例えば染料などを含むことができる。 The cosmetic according to the present invention contains a coloring material obtained by combining the components (A) and (B), but may contain other coloring materials, such as dyes, in order to adjust the coloring.
　また、一般的な化粧料には、粉末成分が配合されることがある。このような粉末として、無機粉末、有機粉末、共重合体樹脂粉末、無機顔料、有機顔料などが挙げられる。本発明においても、必要に応じてこれらの粉末を配合することができるが、粉末は本発明による化粧料の蛍光発色の鮮やかさや透明性を損なうことがある。このため、本発明による化粧料は、粉末成分を含む場合には、化粧料の総質量を基準として、粉末成分の配合率が、５質量％以下であることが好ましく、全く含まないことが特に好ましい。また、粉末成分のうち、顔料以外の非着色粉末は本発明による化粧料の蛍光発色を損なう傾向が強いので、その配合率は少ないことが好ましい。このため、本発明による化粧料に粉末成分を配合する場合には、粉末成分の総質量を基準として、非着色粉末の配合率が５質量％以下であることが好ましい。 ここで、非着色粉末とは、無色または白色の粉末であり、例えばポリアミド粉末、ヒドロキシアパタイト、炭酸カルシウムである。 In addition, powdered ingredients are sometimes added to common cosmetics. Examples of such powders include inorganic powders, organic powders, copolymer resin powders, inorganic pigments and organic pigments. In the present invention, these powders can also be blended as needed, but the powders may impair the vividness and transparency of the fluorescent coloration of the cosmetic of the present invention. Therefore, when the cosmetic according to the present invention contains a powder component, it is preferable that the blending ratio of the powder component is 5% by mass or less based on the total mass of the cosmetic, and it is particularly preferred that the powder component is not included at all. preferable. Among the powder components, non-colored powders other than pigments have a strong tendency to impair the fluorescent color development of the cosmetic composition according to the present invention, so the blending ratio thereof is preferably small. Therefore, when a powder component is blended into the cosmetic according to the present invention, the blending ratio of the non-colored powder is preferably 5% by mass or less based on the total mass of the powder component. Here, the non-colored powder is a colorless or white powder, such as polyamide powder, hydroxyapatite, and calcium carbonate.
　以下、実施例を挙げて本発明をさらに詳しく説明するが、本発明はこれらの実施例により限定されるものではない。配合量については特に断りのない限り質量％を示す。 The present invention will be described in more detail below with reference to examples, but the present invention is not limited by these examples. Unless otherwise specified, the compounding amount is shown in mass %.
実施例１０１～１０７、比較例１０１～１０５
　下記の表１に示された成分を配合して、油性固形化粧料を調製した。各例の化粧料について、１０人のパネラーが「外観発色」、「透明感」、「塗布色」、および「染めつき」について判定を行い、以下の基準で評価した。
Ａ：　９人以上が効果があると判定した。
Ｂ：　７～８人が効果があると評判定した。
Ｃ：　６人が評価があると判定した。
Ｄ：　５人以下が効果があると判定した。 Examples 101-107, Comparative Examples 101-105
An oily solid cosmetic was prepared by blending the components shown in Table 1 below. A panel of 10 persons evaluated the "appearance color development", "transparency", "applied color", and "staining" of the cosmetics of each example according to the following criteria.
A: Nine or more people determined that it was effective.
B: 7 to 8 people rated it as effective.
C: It was judged that 6 persons had evaluation.
D: 5 or less judged to be effective.
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000018
実施例２０１～２０５，比較例２０１
　下記の表２に示された成分を配合して、水性化粧料を調製した。各例の化粧料について、実施例１０１と同じ基準によって評価を行った。 Examples 201 to 205, Comparative Example 201
Aqueous cosmetics were prepared by blending the components shown in Table 2 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000019
実施例３０１～３０４，比較例３０１～３０３
　下記の表３に示された成分を配合して、油性化粧料を調製した。各例の化粧料について、実施例１０１と同じ基準によって評価を行った。 Examples 301-304, Comparative Examples 301-303
An oily cosmetic was prepared by blending the components shown in Table 3 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000020
実施例４０１
　下記の表４に示された成分を配合して、油性化粧料を調製した。各例の化粧料について、実施例１０１と同じ基準によって評価を行った。 Example 401
An oily cosmetic was prepared by blending the components shown in Table 4 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000021
実施例５０１～５０３，比較例５０１
　下記の表５に示された成分を配合して、水中油型化粧料を調製した。各例の化粧料について、実施例１０１と同じ基準によって評価を行った。 Examples 501-503, Comparative Example 501
An oil-in-water cosmetic was prepared by blending the components shown in Table 5 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000022
実施例６０１～６０３
　下記の表６に示された成分を配合して、油中水型化粧料を調製した。各例の化粧料について、実施例１０１と同じ基準によって評価を行った。 Examples 601-603
A water-in-oil type cosmetic was prepared by blending the components shown in Table 6 below. The cosmetics of each example were evaluated according to the same criteria as in Example 101.
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023

Claims (9)

  1. 　（Ａ）フルオレセイン骨格を持つ染料、および
    　（Ｂ）下記（Ｂ１）～（Ｂ４）からなる群から選択される化合物：
    （Ｂ１）式（ｂ１）で表される環状カルボキサミド誘導体またはその塩
    Figure JPOXMLDOC01-appb-C000001
     （式中、
    　Ｒ１は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、
    　Ｘは、－ＣＨ２－または－Ｎ（Ｒ２）－であり、ここで、Ｒ２は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、かつ
    　ｎ１は、１～３の整数である）、
    　（Ｂ２）式（ｂ２）で表される環状アミノ基含有カルボン酸誘導体またはその塩、
    Figure JPOXMLDOC01-appb-C000002
     （式中、
    　Ｒ２は、炭素数１～５のアルキレン鎖であり、
    　ｎ２は１～３の整数である）、
    　（Ｂ３）式（ｂ３）で表されるグリシルグリシン誘導体またはその塩、
    Figure JPOXMLDOC01-appb-C000003
     （式中、
    　Ｒ３は、水素、炭素数１～６のアルキル基、炭素数６～１０のアリール基、炭素数２～７のアシル基、または炭素数７～１１のアロイル基である）
    　（Ｂ４）式（ｂ４）で表されるアルキレンオキシド誘導体、
    Ｒ４Ｏ－［（ＢＯ）ｌ（ＥＯ）ｍ（ＢＯ）ｎ］－Ｒ４　（ｂ４）
    （式中、
    　Ｒ４は、それぞれ独立に、水素、または炭素数１～４の炭化水素基であり、　ＢＯはオキシブチレン基、ＥＯはオキシエチレン基であり、
    　ｌ、ｍおよびｎは、それぞれＢＯおよびＥＯの平均付加モル数であり、
    １≦ｍ≦７０、
    １≦ｌ＋ｎ≦７０であり、
    ＢＯとＥＯの合計数に対するＥＯの割合は２０～８０質量％である。）
    からなる群から選択される化合物
    を１種または２種以上含んでなる、化粧料用色材。     (A) a dye having a fluorescein skeleton, and (B) a compound selected from the group consisting of (B1) to (B4) below:
    (B1) a cyclic carboxamide derivative represented by formula (b1) or a salt thereof
    Figure JPOXMLDOC01-appb-C000001
     (In the formula,
    R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
    X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n1 is an integer from 1 to 3),
    (B2) a cyclic amino group-containing carboxylic acid derivative represented by formula (b2) or a salt thereof;
    Figure JPOXMLDOC01-appb-C000002
     (In the formula,
    R 2 is an alkylene chain having 1 to 5 carbon atoms,
    n2 is an integer from 1 to 3),
    (B3) a glycylglycine derivative represented by formula (b3) or a salt thereof;
    Figure JPOXMLDOC01-appb-C000003
     (In the formula,
    R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms)
    (B4) an alkylene oxide derivative represented by formula (b4),
    R 4 O—[(BO) l (EO) m (BO) n ]—R 4 (b4)
    (In the formula,
    R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, BO is an oxybutylene group, EO is an oxyethylene group,
    l, m and n are the average added moles of BO and EO, respectively;
    1≦m≦70,
    1 ≤ l + n ≤ 70,
    The ratio of EO to the total number of BO and EO is 20-80% by mass. )
    A coloring material for cosmetics, comprising one or more compounds selected from the group consisting of:
  2. 　（Ａ）成分が、油溶性である、請求項１に記載の色材。 The coloring material according to claim 1, wherein the component (A) is oil-soluble.
  3. 　（Ａ）成分が、フルオレセイン、カルボキシル化フルオレセイン、ハロゲン化フルオレセイン、およびそれらの塩からなる群から選択される、請求項１または２に記載の色材。 The coloring material according to claim 1 or 2, wherein the component (A) is selected from the group consisting of fluorescein, carboxylated fluorescein, halogenated fluorescein, and salts thereof.
  4. 　（Ｂ）成分が、ヒドロキシエチルイミダゾリジノン、１－ピペリジンプロピオン酸、グリシルグリシン、およびＰＥＧ／ポリ－１，２－ブタンジオール－５２／３２ジメチルエーテルからなる群から選択される化合物である、請求項１または２に記載の色材。 Component (B) is a compound selected from the group consisting of hydroxyethylimidazolidinone, 1-piperidinepropionic acid, glycylglycine, and PEG/poly-1,2-butanediol-52/32 dimethyl ether. 3. The coloring material according to Item 1 or 2.
  5. 　（Ａ）フルオレセイン骨格を持つ染料、および
    　（Ｂ）下記（Ｂ１）～（Ｂ４）からなる群から選択される化合物：
    （Ｂ１）式（ｂ１）で表される環状カルボキサミド誘導体またはその塩
    Figure JPOXMLDOC01-appb-C000004
     （式中、
    　Ｒ１は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、
    　Ｘは、－ＣＨ２－または－Ｎ（Ｒ２）－であり、ここで、Ｒ２は、水酸基で置換されていてもよい炭素数１～６の炭化水素基、または水素原子であり、かつ
    　ｎ１は、１～３の整数である）、
    　（Ｂ２）式（ｂ２）で表される環状アミノ基含有カルボン酸誘導体またはその塩、
    Figure JPOXMLDOC01-appb-C000005
     （式中、
    　Ｒ２は、炭素数１～５のアルキレン鎖であり、
    　ｎ２は１～３の整数である）、
    　（Ｂ３）式（ｂ３）で表されるグリシルグリシン誘導体またはその塩、
    Figure JPOXMLDOC01-appb-C000006
     （式中、
    　Ｒ３は、水素、炭素数１～６のアルキル基、炭素数６～１０のアリール基、炭素数２～７のアシル基、または炭素数７～１１のアロイル基である）
    　（Ｂ４）式（ｂ４）で表されるアルキレンオキシド誘導体、
    Ｒ４Ｏ－［（ＢＯ）ｌ（ＥＯ）ｍ（ＢＯ）ｎ］－Ｒ４　（ｂ４）
    （式中、
    　Ｒ４は、それぞれ独立に、水素、または炭素数１～４の炭化水素基であり、　ＢＯはオキシブチレン基、ＥＯはオキシエチレン基であり、
    　ｌ、ｍおよびｎは、それぞれＢＯおよびＥＯの平均付加モル数であり、
    １≦ｍ≦７０、
    １≦ｌ＋ｎ≦７０であり、
    ＢＯとＥＯの合計数に対するＥＯの割合は２０～８０質量％である。）
    からなる群から選択される化合物
    を１種または２種以上含んでなる、化粧料。     (A) a dye having a fluorescein skeleton, and (B) a compound selected from the group consisting of (B1) to (B4) below:
    (B1) a cyclic carboxamide derivative represented by formula (b1) or a salt thereof
    Figure JPOXMLDOC01-appb-C000004
     (In the formula,
    R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
    X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n1 is an integer from 1 to 3),
    (B2) a cyclic amino group-containing carboxylic acid derivative represented by formula (b2) or a salt thereof;
    Figure JPOXMLDOC01-appb-C000005
     (In the formula,
    R 2 is an alkylene chain having 1 to 5 carbon atoms,
    n2 is an integer from 1 to 3),
    (B3) a glycylglycine derivative represented by formula (b3) or a salt thereof;
    Figure JPOXMLDOC01-appb-C000006
     (In the formula,
    R 3 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an acyl group having 2 to 7 carbon atoms, or an aroyl group having 7 to 11 carbon atoms)
    (B4) an alkylene oxide derivative represented by formula (b4),
    R 4 O—[(BO) l (EO) m (BO) n ]—R 4 (b4)
    (In the formula,
    R 4 is each independently hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, BO is an oxybutylene group, EO is an oxyethylene group,
    l, m and n are the average added moles of BO and EO, respectively;
    1≦m≦70,
    1 ≤ l + n ≤ 70,
    The ratio of EO to the total number of BO and EO is 20-80% by mass. )
    A cosmetic comprising one or more compounds selected from the group consisting of
  6. 　前記化粧料の総質量を基準とした、（Ａ）成分の含有率が、０．０００１～５．０質量％である、請求項５に記載の化粧料。 The cosmetic according to claim 5, wherein the content of component (A) is 0.0001 to 5.0% by mass based on the total mass of the cosmetic.
  7. 　前記化粧料の総質量を基準とした、（Ｂ）成分の含有率が、０．０１～１５質量％である、請求項５または６に記載の化粧料。 The cosmetic according to claim 5 or 6, wherein the content of component (B) is 0.01 to 15% by mass based on the total mass of the cosmetic.
  8. 　油性化粧料である、請求項５または６に記載の化粧料。 The cosmetic according to claim 5 or 6, which is an oily cosmetic.
  9. 　粉末を実質的に含まない、水性化粧料、水中油型化粧料または油中水型化粧料である、請求項５または６に記載の化粧料。 The cosmetic according to claim 5 or 6, which is an aqueous cosmetic, an oil-in-water cosmetic, or a water-in-oil cosmetic, which does not substantially contain powder.
PCT/JP2022/044100 2021-12-13 2022-11-30 Cosmetic colorant and cosmetic using same WO2023112671A1 (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020032243A1 (en) * 2018-08-10 2020-02-13 株式会社 資生堂 Emulsion cosmetic
WO2020204191A1 (en) * 2019-04-05 2020-10-08 株式会社 資生堂 Cosmetic containing ultraviolet wavelength conversion substance and medicinal agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020032243A1 (en) * 2018-08-10 2020-02-13 株式会社 資生堂 Emulsion cosmetic
WO2020204191A1 (en) * 2019-04-05 2020-10-08 株式会社 資生堂 Cosmetic containing ultraviolet wavelength conversion substance and medicinal agent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD 27 July 2018 (2018-07-27), COPARCOS: "Long Wear Lipcolour", XP093072088, retrieved from MINTEL Database accession no. 5852211 *

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