WO2017159656A1 - Composition cosmétique - Google Patents

Composition cosmétique Download PDF

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Publication number
WO2017159656A1
WO2017159656A1 PCT/JP2017/010126 JP2017010126W WO2017159656A1 WO 2017159656 A1 WO2017159656 A1 WO 2017159656A1 JP 2017010126 W JP2017010126 W JP 2017010126W WO 2017159656 A1 WO2017159656 A1 WO 2017159656A1
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Prior art keywords
group
carbon atoms
compound
formula
salt
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PCT/JP2017/010126
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English (en)
Japanese (ja)
Inventor
シュヴェンドゥ ビスワス
貴謙 杉本
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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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
    • A61K8/40—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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to a composition containing an acylamino acid polyhydric alcohol ester compound and a hardly soluble substance, and a cosmetic containing the composition.
  • insoluble active ingredients are blended in cosmetics in order to impart various functions.
  • a poorly soluble ultraviolet absorber that absorbs ultraviolet rays is blended (Patent Document 1)
  • inorganic powder that efficiently scatters ultraviolet rays is blended. (Patent Document 2).
  • a base having high solubilizing ability and dispersibility and excellent in feeling of use and safety is required.
  • a base capable of improving the dispersibility of the powder is required.
  • oil agents with high solubilizing ability of poorly soluble molecules and high dispersibility of inorganic powders include oil agents such as isopropyl myristate (IPM) and lauroyl sarcosine isopropyl (SL-205) (Patent Documents 3 and 4), suncare cosmetics.
  • IPM isopropyl myristate
  • SL-205 lauroyl sarcosine isopropyl
  • suncare cosmetics A widely used alkyl benzoate (C 12 -C 15 ) and the like are known.
  • these oil agents having high solubilizing ability and dispersibility simultaneously have a strong squeaky feeling, and there remain problems in use.
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 26 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms
  • n is an integer of 1 to 5
  • X is a hydrocarbon group having 3 or more carbon atoms
  • a and b are each independently an integer of 1 or more.
  • a composition comprising at least one compound selected from the group consisting of a compound represented by the formula: and a salt thereof, or a salt thereof, and (B) a hardly soluble substance.
  • R 1 is an alkyl group having 4 to 26 carbon atoms.
  • R 1 is an alkyl group having 7 to 17 carbon atoms.
  • R 2 is an alkyl group having 1 to 6 carbon atoms.
  • R 5 is a methyl group.
  • n is 1 or 2.
  • X is a hydrocarbon group having 3 to 9 carbon atoms.
  • (B) is a substance having a solubility of 1% by weight or less in water at 25 ° C.
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 26 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms
  • n is an integer of 1 to 5
  • X is a hydrocarbon group having 3 or more carbon atoms
  • a and b are each independently an integer of 1 or more.
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 26 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms
  • n is an integer of 1 to 5
  • X is a hydrocarbon group having 3 or more carbon atoms
  • a and b are each independently an integer of 1 or more.
  • a method for solubilizing a hardly soluble substance comprising causing a hardly soluble substance to coexist with at least one compound selected from the group consisting of a compound represented by the formula:
  • a hardly soluble substance can be solubilized, it can be applied to various cosmetics. According to the present invention, it is possible to alleviate the squeaky feeling of cosmetics containing hardly soluble substances and the like, and therefore it is possible to provide cosmetics with a good feeling of use. According to the present invention, it is possible to provide a cosmetic having ultraviolet blocking ability in a wide range (UV-A and UV-B region).
  • FIG. 1 is a graph showing the results of measuring transmittance at wavelengths between 280 nm and 600 nm when the compositions of Examples 3-1 and 3-2 and Comparative Examples 3-1 and 3-2 are added to inorganic pigments. It is.
  • the vertical axis represents the transmittance (% T), and the horizontal axis represents the wavelength ( ⁇ ).
  • composition of the present invention comprises: (A) Formula (1-1):
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 26 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms
  • n is an integer of 1 to 5
  • X is a hydrocarbon group having 3 or more carbon atoms
  • a and b are each independently an integer of 1 or more.
  • each symbol has the same meaning as defined above.
  • It contains at least one compound selected from the group consisting of a compound represented by the above and a salt thereof, or a salt thereof, and (B) a poorly soluble substance.
  • alkyl group having 4 to 26 carbon atoms means straight or branched chain having 4 to 26 carbon atoms.
  • alkyl group having 7 to 17 carbon atoms means a linear or branched alkyl group having 7 to 17 carbon atoms, and includes, for example, a heptyl group, an isoheptyl group, a neoheptyl group, an octyl group, Examples include isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and the like.
  • the “alkyl group having 1 to 6 carbon atoms” means a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, Examples thereof include a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.
  • the “alkenyl group having 4 to 26 carbon atoms” means a linear or branched alkenyl group having 4 to 26 carbon atoms, specifically, a 1-butenyl group, a 2-butenyl group.
  • 3-butenyl group pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group , Icosenyl group, henecocenyl group, dococenyl group and the like.
  • alkenyl group having 4 to 16 carbon atoms means a linear or branched alkenyl group having 4 to 16 carbon atoms, specifically, a 1-butenyl group, a 2-butenyl group.
  • Examples include 3-butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group and the like.
  • alkenyl group having 2 to 6 carbon atoms means a linear or branched alkenyl group having 2 to 6 carbon atoms, and specifically includes an ethenyl group, a 1-propenyl group, 2 -Propenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, pentenyl group, hexenyl group and the like can be mentioned.
  • the “hydrocarbon group having 3 or more carbon atoms” means a divalent or more straight chain or branched hydrocarbon group having 3 or more carbon atoms (preferably a divalent or more hydrocarbon group having 3 or more carbon atoms. Linear or branched saturated hydrocarbon group), specifically, the following formula
  • hydrocarbon group having 4 or more carbon atoms refers to a divalent or more straight chain or branched hydrocarbon group having 4 or more carbon atoms (preferably a divalent or more hydrocarbon group having 4 or more carbon atoms).
  • Linear or branched saturated hydrocarbon group specifically, the following formula
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 26 carbon atoms.
  • R 1 is preferably an alkyl group having 4 to 26 carbon atoms, more preferably an alkyl group having 7 to 17 carbon atoms, still more preferably a linear alkyl group having 7 to 17 carbon atoms, particularly preferably. Is an undecyl group.
  • R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
  • R 2 is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group.
  • n is an integer of 1 to 5. n is preferably 1 or 2, more preferably 1.
  • X is a hydrocarbon group having 3 or more carbon atoms.
  • X is preferably a hydrocarbon group having 3 to 9 carbon atoms, more preferably a hydrocarbon group having 4 to 6 carbon atoms, and more preferably a hydrocarbon group having 4 or 5 carbon atoms.
  • a and b are each independently an integer of 1 or more. a and b are preferably each independently an integer of 1 to 3, and a + b is an integer of 2 to 5, more preferably a and b are both 1.
  • R 1 is an alkyl group having 4 to 26 carbon atoms or an alkenyl group having 4 to 16 carbon atoms
  • X is A compound which is a hydrocarbon group having 4 or more carbon atoms is preferred.
  • Preferred examples of the compound represented by formula (1-1) or formula (1-2) include the following compounds.
  • R 1 is an alkyl group having 4 to 26 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms
  • n is 1 or 2
  • X is a hydrocarbon group having 3 to 9 carbon atoms
  • R 1 is an alkyl group having 7 to 17 carbon atoms
  • R 2 is an alkyl group having 1 to 6 carbon atoms
  • n is 1 or 2
  • X is a hydrocarbon group having 4 to 9 carbon atoms
  • R 1 is an undecyl group
  • R 2 is a methyl group
  • n is 1
  • X is a hydrocarbon group having 4 or 5 carbon atoms
  • Examples of the salt of the compound (1-1) and the compound (1-2) in the present invention include alkali metal salts such as lithium salt, sodium salt and potassium salt; alkaline earth metal salts such as calcium salt and magnesium salt; ammonium salt ; Methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, tris (hydroxymethyl) methylamine, dicyclohexylamine, N, N'-dibenzylethylenediamine, guanidine, pyridine, picoline, choline, cinchonine And salts with organic amine bases such as meglumine.
  • alkali metal salts such as lithium salt, sodium salt and potassium salt
  • alkaline earth metal salts such as calcium salt and magnesium salt
  • ammonium salt ; Methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, tri
  • the method for producing the compounds (1-1) and (1-2) in the present invention is not particularly limited, and can be produced by combining known methods. Specifically, it can be synthesized by the following method, but is not limited thereto.
  • N-acyl-N-alkylamino acid (i) and alcohol (ii) are present in the presence of an acid catalyst such as paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, hydrogen fluoride and the like.
  • an acid catalyst such as paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, hydrogen fluoride and the like.
  • it can be obtained by condensation in the absence.
  • each symbol has the same meaning as described above.
  • 0.1 to 1 equivalent, preferably 0.5 to 0.55 equivalent of alcohol (ii) is used with respect to N-acyl-N-alkylamino acid (i).
  • the alcohol (ii) is preferably 0.2 to 5 equivalents, preferably the N-acyl-N-alkylamino acid (i). 0.7 to 2 equivalents are used.
  • the ratio of compound (1-1) and compound (1-2) in the final product obtained was changed.
  • the reaction can also be carried out in a suitable solvent, and examples of the solvent to be used include benzene, toluene, xylene and the like.
  • the reaction time is usually 2 to 12 hours, preferably 3 to 6 hours.
  • the reaction temperature is usually 80 to 160 ° C., preferably 115 to 140 ° C.
  • the N-acyl-N-alkylamino acid (i) has a so-called Schotten-Baumann reaction (special characteristic) in which a carboxylic acid halide (iii) is reacted with an amino acid (iv) under basic conditions as shown in the following formula, for example. It can be produced by a known method such as Japanese Patent Publication No. 51-38681).
  • Hal represents a halogen atom such as a chlorine atom, and other symbols are as defined above.
  • (A) is at least one compound selected from the group consisting of compound (1-1), compound (1-2), and salts thereof, or a salt thereof, and comprises compound (1-1) and a salt thereof.
  • a mixture of at least one selected from the group and at least one selected from the group consisting of the compound (1-2) and a salt thereof is preferable.
  • the content of the compound (1-1) or a salt thereof is usually 0 to 10 parts by weight, preferably 1 part by weight of the compound (1-2) or a salt thereof. Is 0.01 to 1 part by weight, more preferably 0.05 to 0.25 part by weight.
  • the content of (A) is usually 1 to 90% by weight, preferably 3 to 50% by weight, more preferably 5 to 20% by weight, based on the total amount of the composition. If it is content of this range, (B) can be solubilized or disperse
  • “solubilization” means increasing the solubility of a substance that is hardly soluble or insoluble in a solvent to form a uniform solution.
  • “dispersion” means that a hardly soluble or insoluble substance is finely dispersed in a solvent and uniformly dispersed in the solvent.
  • the hardly soluble substance in the present invention includes not only a substance hardly soluble in a solvent but also an insoluble substance, and has a solubility of 1% by weight or less with respect to water at 25 ° C. and / or Those having a solubility of 5% by weight or less with respect to liquid paraffin at 25 ° C. Preferably having a solubility of 0.0000001 to 1% by weight in water at 25 ° C. and / or having a solubility of 0.0000001 to 5% by weight in liquid paraffin at 25 ° C., more preferably in water at 25 ° C.
  • UV absorbers having poorly soluble or insoluble properties, ceramides, gelling agents, perfumes, self-tanning agents, bactericides, inorganic pigments and the like.
  • UV absorber examples include the following.
  • Benzoic acid type ultraviolet absorbers As benzoic acid type ultraviolet absorbers, paraaminobenzoic acid, ethyldihydroxypropylparaaminobenzoic acid, glycerylparaaminobenzoic acid, octyldimethylparaaminobenzoic acid, paradimethylaminobenzoic acid amyl, paradimethylamino Examples include 2-ethylhexyl benzoate, 2- [4- (diethylamino) -2-hydroxybenzoyl] benzoic acid hexyl ester, and the like.
  • anthranilic acid ultraviolet absorbers examples include homomenthyl-N-acetylanthranilate and methyl anthranilate (also known as methyl-O-aminobenzoate).
  • Salicylic acid ultraviolet absorbers examples include amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanol phenyl salicylate, and triethanolamine salicylate.
  • Benzophenone ultraviolet absorbers As benzophenone ultraviolet absorbers, 4- (2- ⁇ -glucopyranosyloxy) propoxy-2-hydroxybenzophenone, dihydroxydimethoxybenzophenone, dihydroxydimethoxybenzophenone sodium disulfonate, 2-hydroxy- 4-methoxybenzophenone, hydroxymethoxybenzophenonesulfonic acid and its trihydrate, sodium hydroxymethoxybenzophenonesulfonate, 2-hydroxy-4-methoxybenzophenone-5-sulfate, 2,2′-dihydroxy-4-methoxybenzophenone, 2, 4-dihydroxybenzophenone, 2,2'4,4'-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4 4'-dimethoxyphenyl benzophenone, 2-hydroxy -4-N-octoxybenzophenone and the like.
  • Cinnamic acid UV absorbers include 2-methoxyhexyl paramethoxycinnamate (also known as octyl paramethoxycinnamate) and mono-2-ethyl diparamethoxycinnamate.
  • Glyceryl hexanoate methyl 2,5-diisopropylcinnamate, ethyl 2,4-diisopropylcinnamate, methyl 2,4-diisopropylcinnamate, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl ) Anilino] -1,3,5-triazine, methyl bis (trimethylsiloxy) silylisopentyl trimethoxycinnamate, isopropyl dimethoxycinnamate ester mixture, ferulic acid, p-methoxyhydrocinnamic acid Diethanolamine salt, 3-methyl-4- [3,4,5-trimethoxycinnamate And methylbis (trimethylsiloxy) silyl] butyl.
  • benzoylmethane ultraviolet absorbers examples include 2-phenyl-benzimidazole-5-sulfuric acid, 4-isopropyldibenzoylmethane, 4-tert-butyl-4'-methoxydibenzoylmethane, etc. Is mentioned.
  • Triazine-based UV absorbers examples include bisresorcinyl triazines. Specifically, 2,4-bis-[ ⁇ 4- (2-ethylhexyloxy) -2-hydroxy ⁇ -Phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine (also known as bisethylhexyloxyphenol methoxyphenyltriazine), 2,4,6-tris ⁇ 4- (2-ethylhexyloxycarbonyl) ) Anilino ⁇ 1,3,5-triazine, 2,4,6-tris (4-biphenylyl) -1,3,5-triazine (1,3,5-triazine, 2,4,6-tris [1, 10-biphenyl] -4-yl) and the like.
  • Benzotriazole ultraviolet absorbers As benzotriazole ultraviolet absorbers, 2,2′-hydroxy-5-methylphenylbenzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole 2- (2′-hydroxy-5′-methylphenylbenzotriazole, 2,2′-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethyl) Butyl) phenol) (also known as methylenebisbenzotriazolyltetramethylbutylphenol) and the like.
  • benzotriazole ultraviolet absorbers 2,2′-hydroxy-5-methylphenylbenzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole 2- (2′-hydroxy-5′-methylphenylbenzotriazole, 2,2′-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethyl) But
  • Pyridazine derivative ultraviolet absorbers examples include pyridazine derivatives such as dimorpholinopyridazinone.
  • organic ultraviolet absorbers include phenylbenzimidazole sulfonic acid, drometrizole trisiloxane, terephthalylidene dicamphulsulfonic acid, dimethoxybenzylidene dioxoimidazolidinepropionate 2-ethylhexyl, 1- (3,4-Dimethoxyphenyl) -4,4-dimethyl-1,3-pentanedione, Polysilicone-15 (dimethicodiethylbenzalmalonate), Synoxate, 2-cyano-3,3-diphenylprop -2-Enoic acid 2-ethylhexyl ester (also known as octocrylene), 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one, dianisoylmethane, methyl-O-aminobenzoate, 2- Ethylhexyl-2-cyano-3,
  • UV absorbers 4-tert-butyl-4′-methoxydibenzoylmethane, octyl salicylate, bisethylhexyloxyphenol methoxyphenyltriazine, methylenebisbenzotriazolyltetramethylbutylphenol, phenylbenzimidazolesulfonic acid, poly Silicone-15, octocrylene, homomenthyl salicylate, 2- [4- (diethylamino) -2-hydroxybenzoyl] benzoic acid hexyl ester, 2-ethylhexyl paramethoxycinnamate, octyl triazone, 2-hydroxy-4-methoxybenzophenone Hydroxymethoxybenzophenonesulfonic acid and its trihydrate are preferred, such as 4-tert-butyl-4′-methoxydibenzoylmethane, 2-methoxyparacinnamic acid 2-e
  • the ceramide is a compound in which a sphingosine base is bonded with a long-chain saturated or monounsaturated fatty acid at its amino group to an acid amide, for example, ceramide 1, ceramide 2, ceramide 3, ceramide 4, ceramide 5, ceramide 6-II, Ceramide 7 etc. are mentioned.
  • gelling agent examples include dibutyl lauroyl glutamide, dibutyl ethyl hexanoyl glutamide, dextrin palmitate, 12-hydroxystearic acid and the like.
  • fragrances examples include ⁇ -isomethylionone, linalool, butylphenylmethylpropanal, benzyl salicylate, hexylcinnamal and the like.
  • Examples of the self-tanning agent include 3-hydroxy-4,5-dimethyl-5 (2H) -furanone.
  • bactericides include isopropylmethylphenol, chlorhexidine hydrochloride, benzethonium chloride, methylparaben, propylparaben, and the like.
  • inorganic pigments include colored pigments, extender pigments, pearlescent pigments, special functional pigments and special pigments.
  • colored pigments, extender pigments, pearlescent pigments and special functional pigments are preferred.
  • the inorganic pigment surface-treated with the surface modifier etc. may be sufficient.
  • Specific examples include N ⁇ -lauroyl lysine, perfluoroalkyl phosphate diethanolamine, sodium metaphosphate, amino acids, acylated collagen, lecithin, metal soaps, acyl amino acid salts, methylhydrogenpolysiloxane and other silicon, polyacrylic acid, Examples thereof include inorganic pigments coated with chitosan, nylon powder, coloring pigments and the like. These inorganic pigments may be used alone or in combination of two or more depending on the purpose of use.
  • titanium dioxide zinc oxide
  • iron oxide Bengara
  • titanium oxide coated mica titanium oxide coated bismuth oxychloride
  • titanium oxide coated talc colored titanium oxide coated mica
  • fish scale foil aluminum powder
  • N ⁇ ⁇ Lauroyllysine is preferred.
  • the content of (B) is usually 0.1 to 60% by weight, preferably 1 to 30% by weight, more preferably 5 to 25% by weight, based on the total amount of the composition.
  • an ultraviolet absorber it is usually 0.1 to 60% by weight, preferably 1 to 30% by weight, more preferably 5 to 25% by weight, based on the total amount of the composition.
  • inorganic pigments it is usually 0.1 to 50% by weight, preferably 1 to 30% by weight, more preferably 3 to 20% by weight, based on the total amount of the composition. When the content is in this range, a hardly soluble substance can be blended in the composition at a high concentration.
  • an ultraviolet absorber or an inorganic pigment a wide range (UV-B region (290 to 320 nm) and UV-A) can be used. High ultraviolet blocking ability can be exhibited in the region (320 to 400 nm).
  • the weight ratio of (B) to (A) [(A) :( B)] is usually 1: 0.005 to 1:20 parts by weight, preferably 1: 0.01 to 1:10, More preferably, it is 1: 0.05 to 1: 5. Within this range, (B) can be solubilized or dispersed stably and uniformly.
  • composition of the present invention can be used as it is, but it can be produced by a conventional method by mixing known additives as required.
  • Additives include water-soluble ingredients, oil-based ingredients, powder ingredients, polymer ingredients, thickeners, tackifiers, film formers, pH adjusters, antioxidants, antiseptics, bactericides, preservatives, preservatives. Molds, moisturizers, skin protectants, refreshing agents, fragrances, coloring agents, pigments, chelating agents, lubricants, anti-inflammatory agents, antipruritic agents, blood circulation promoters, astringents, tissue repair promoters, antiperspirants, A penetrant, an amino acid, a nucleic acid, an organic acid, an inorganic salt, an animal or plant extract component, an enzyme, a vitamin, a pearling agent, a wetting agent, and the like can be appropriately blended as long as the effects of the invention are not inhibited.
  • composition of the present invention is not particularly limited, and examples thereof include cream, emulsion, lotion, powder, powder solid, oily solid, oily liquid, and paste.
  • the present invention also relates to a cosmetic containing the composition of the present invention.
  • the cosmetic of the present invention is not particularly limited, but an ultraviolet protective cosmetic is preferable.
  • basic cosmetics eg, lotion, milky lotion, makeup base, beauty liquid, night cream, pack, makeup remover (cleansing gel, etc.), lip balm, nail cream, etc.
  • makeup cosmetics eg, Foundation (solid, cream, liquid, etc.), sunscreen cream, BB cream, CC cream, concealer, lipstick, lip gloss, eye shadow, eyeliner, teak, mascara, bronzer, etc.
  • hair care cosmetics hair treatment ( E.g. hair treatment, out bath treatment, hair essence, split hair coat, etc.), hair styling agent (e.g.
  • shaving products for example, shaving cream, after-shave lotion, etc.
  • make-up cosmetics sunscreen cream, BB cream, CC cream, bronzer is preferable.
  • Cosmetic dosage forms include creams, solutions, lotions, emulsions, tinctures, aqueous gels, oily gels, aerosols, powders and the like.
  • composition of the present invention and a cosmetic containing the composition can be produced according to a conventional method.
  • Solubilizing agents are also included in the present invention.
  • the “solubilizing agent” of the present invention means a substance that increases the solubility in addition to a hardly soluble substance to make a uniform solution.
  • the solubilizer of the present invention can be produced according to a conventional method by appropriately blending only the compound or a salt thereof, or the above additives.
  • the content of the above-mentioned compound or a salt thereof in the solubilizer of the present invention is usually 1 to 90% by weight, preferably 5 to 50% by weight.
  • solubilizer of the present invention varies depending on the kind of the hardly soluble substance, it is usually 0.05 to 200 parts by weight, preferably 0.1 to 100 parts by weight, more preferably based on 1 part by weight of the hardly soluble substance.
  • the definitions of the above formulas (1-1) and (1-2) and hardly soluble substances are the same as described above.
  • the compound represented by the formula (1-1) and a salt thereof, and at least one compound selected from the group consisting of the compound represented by the formula (1-2) and a salt thereof, or a salt thereof, are sparingly soluble.
  • a method for solubilizing a hardly soluble substance including a step of coexisting a substance is also included in the present invention.
  • the method of the present invention varies depending on the kind of the hardly soluble substance, but usually 0.05 to 200 parts by weight, preferably 0.1 to 100 parts by weight of the above compound or a salt thereof with respect to 1 part by weight of the hardly soluble substance. Part, more preferably 0.2 to 20 parts by weight, can be solubilized.
  • the definitions of the above formulas (1-1) and (1-2) and hardly soluble substances are the same as described above.
  • a pigment dispersant is also included in the present invention.
  • the dispersant for inorganic pigments of the present invention can be produced according to a conventional method by appropriately blending only the compound or a salt thereof or the above additives.
  • the content of the compound or salt thereof in the inorganic pigment dispersant of the present invention is usually 1 to 90% by weight, preferably 5 to 50% by weight.
  • the dispersant for inorganic pigments of the present invention varies depending on the type of inorganic pigment, but is usually 0.05 to 200 parts by weight, preferably 0.1 to 100 parts by weight, more preferably based on 1 part by weight of the inorganic pigment. By mixing 0.2 to 20 parts by weight, the inorganic pigment can be uniformly and stably dispersed.
  • the dispersion method of the inorganic pigment including the step of allowing the inorganic pigment dispersant and the inorganic pigment to coexist is also included in the present invention.
  • the method of the present invention varies depending on the type of inorganic pigment, but the above compound or salt thereof is usually 0.05 to 200 parts by weight, preferably 0.1 to 100 parts by weight, based on 1 part by weight of the inorganic pigment. More preferably, it is possible to disperse uniformly and stably by coexisting 0.2 to 20 parts by weight.
  • the definitions of the above formulas (1-1) and (1-2) and the inorganic pigment are the same as described above.
  • the instrument used for the measurement of a compound is as follows. 1 H-NMR measurement: Bruker AVANCE III HD NMR Spectrometer ESI-MS measurement: LC-MS 2010 A (manufactured by Shimadzu Corporation)
  • Production Example 1 Production of 2LmbA-bg
  • Production Example 4 Production of a mixture of 2LmbA-bg and LmbA-bg (N-lauroyl-N-methyl- ⁇ -alanine 1,3-butylene glycol monoester)
  • the organic phase was collected and concentrated by vacuum decompression to obtain the desired product (yield 92%).
  • Production Example 5 Production of a mixture of 2LmbA-npg and LmbA-npg (N-lauroyl-N-methyl- ⁇ -alanine neopentyl glycol monoester)
  • the organic phase was collected and concentrated by vacuum decompression to obtain the desired product (yield 95%).
  • Production Example 6 Production of 2LS-bg Sulfuric acid (0.98 g, 0.01 mol) was added to a mixture of N-lauroylsarcosine (27.14 g, 0.1 mol) and 1,3-butylene glycol (4.96 g, 0.055 mol), and argon was added. The mixture was stirred at a bath temperature of 132 ° C. for 10 hours under an air stream. The product was diluted with ethyl acetate (50 mL) and washed twice with saturated aqueous sodium hydrogen carbonate (30 mL). The organic phase was further washed twice with ultrapure water (40 mL). The organic phase was collected and concentrated by vacuum under reduced pressure to give a crude product.
  • N-lauroylsarcosine 27.14 g, 0.1 mol
  • 1,3-butylene glycol 4.96 g, 0.055 mol
  • Production Example 7 Production method of 2LS-npg
  • Production Example 9 Production of a mixture of 2LS-bg and LS-bg (N-lauroyl sarcosine 1,3-butylene glycol monoester)
  • the compound was identified by a mass spectrometer (LC-MS) connected to liquid chromatography.
  • Condition column for liquid chromatography YMC-Pack ODS-A, flow rate: 1 mL / min, temperature: 40 ° C, solvent: 30 mM aqueous solution of methanol / formic acid (9/1) ESI-MS (positive) m / z 619.3 [2LS-bg + Na] + , m / z 366.5 [LS-bg + Na] +
  • Production Example 10 Production of a mixture of 2LS-npg and LS-npg (N-lauroyl sarcosine, neopentyl glycol monoester)
  • Production Example 11 Mixture of 3LS-tmp (N-lauroyl sarcosine trimethylol propane triester), 2LS-tmp (N-lauroyl sarcosine trimethylol propane diester) and LS-tmp (N-lauroyl sarcosine trimethylol propane monoester) Manufacturing
  • Production Example 12 3LmbA-pent (N-lauroyl-N-methyl- ⁇ -alanine pentaerythritol triester), 2LmbA-pent (N-lauroyl-N-methyl- ⁇ -alanine pentaerythritol diester) and LmbA-pent (N -Lauroyl-N-methyl- ⁇ -alanine pentaerythritol monoester)
  • P-Toluenesulfonic acid monohydrate (1.9 g, 0.01 mol) was added to a mixture of N-lauroyl-N-methyl- ⁇ -alanine (28.52 g, 0.1 mol) and pentaerythritol (7.5 g, 0.055 mol). The mixture was stirred at a bath temperature of 130 ° C. for 4 hours under an argon stream. The product was diluted with ethyl acetate (50 mL) and washed twice with saturated aqueous sodium hydrogen carbonate (30 mL). The organic phase was further washed twice with saturated brine (40 mL) and then once with ultrapure water (40 mL).
  • Production Example 14 Production of 3LmbA-tmp (N-lauroyl-N-methyl- ⁇ -alanine trimethylolpropane triester)
  • the compound was identified by a mass spectrometer (LC-MS) connected to liquid chromatography.
  • Production Example 17 Production of 2C10mbA-bg (N-decanoyl-N-methyl- ⁇ -alanine 1,3-butylene glycol diester)
  • the numerical value obtained by dividing the amount of liquid paraffin added at this time by 100 is defined as the flow point (FP) of the oil or compound. Since the smaller the difference between the flow point and the wet point, the better the dispersibility (Industrial and Engineering Chemistry, 1946, 18 (1), 26-31), the pigment dispersibility is determined by the difference between the flow point and the wet point. The difference was evaluated. That is, in Table 1 below, when the difference between the flow point and the wet point is less than 10, ⁇ (very preferable), ⁇ (preferred) when 10 or more and less than 22 ⁇ (less preferable) when 22 or more and less than 30; X (not preferable) when 30 or more Displayed.
  • the oil agents in the table are SL-205: Lauroyl sarcosine isopropyl (Ajinomoto Co., Inc.), Finsolv TN: Alkyl benzoate (C12-15) (Innospec Active Chemicals LLC), Neosol MP: Dine neopentanoic acid methylpentanediol (Nippon Seiki) And TCG-M: tri (caprylic acid / capric acid) glyceryl (manufactured by Higher Alcohol Industry Co., Ltd.).
  • Test Example 2 Evaluation of solubilization ability In order to investigate the solubilizing power of the compounds or oils listed in Table 2, 50 mg of poorly soluble molecule 4-tert-butyl-4′-methoxydibenzoylmethane (Parsol 1789) was added to 100 mg of various compounds or oils. And stirred at room temperature for 24 hours. Thereafter, insoluble matters were precipitated by a centrifuge (20 minutes, 13000 rpm), and the supernatant was collected. 3 mg of the collected supernatant was dissolved in 1 mL of an organic solvent (methanol) and analyzed by HPLC.
  • an organic solvent methanol
  • Test Example 3 Evaluation of squeaky feeling during use About the squeaky feeling of various compounds or oils in Table 2 in which Parsol 1789, which is a poorly soluble UV absorber, was dissolved at 10 wt%, the specialized panelists (5 persons) Evaluation was performed. Based on the average evaluation score of panelists, the squeaky feeling during use was evaluated as follows.
  • the average score of professional panelists is 2.4 or higher. 1.5 to less than 2.4 ⁇ , 0.5 to less than 1.5 Less than 0.5 x It was. The results are shown in Table 2.
  • Test Example 4 Evaluation of Improvement of UV Blocking Ability of Inorganic Pigment by Addition of Compound or Oil Agent
  • inorganic pigments titanium dioxide, TTO-55N, manufactured by Ishihara Sangyo Co., Ltd.
  • TTO-55N titanium dioxide
  • the powder mixed with the compound was added to liquid paraffin (Molesco White P-55, manufactured by Moresco) at a ratio of 1 wt%, vortexed for 1 minute, further shaken by hand for 15 seconds, and then vortexed for 15 seconds.
  • the sample thus obtained was transferred to a quartz cell having an optical path length of 1 mm, and the transmittance at a wavelength between 280 nm and 600 nm was measured.
  • FIG. 1 shows the UV blocking ability of inorganic pigments when various compounds or various oils are added.

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Abstract

La présente invention concerne une composition, spécifiquement une composition cosmétique, incluant (A) au moins un composé ou sel de celui-ci choisi dans le groupe constitué par les composés répondant à la formule (1-1) et les sels de ceux-ci et les composés répondant à la formule (1-2) et les sels de ceux-ci [dans les formules, chaque symbole est tel que défini dans la description], et (B) une substance faiblement soluble, où la composition inclut les substances faiblement solubles sous une forme solubilisée ou dispersée de façon stable, et présente une sensation agréable lors de l'utilisation par inhibition de la rigidité.
PCT/JP2017/010126 2016-03-14 2017-03-14 Composition cosmétique Ceased WO2017159656A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110698664A (zh) * 2018-07-09 2020-01-17 广东华润涂料有限公司 固体颗粒分散剂及其制备方法以及含有该分散剂的固体颗粒的分散体

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50105580A (fr) * 1973-09-11 1975-08-20
JPH11246841A (ja) * 1998-02-27 1999-09-14 Ajinomoto Co Inc 紫外線吸収性組成物
JP2000007942A (ja) * 1998-04-22 2000-01-11 Ajinomoto Co Inc 無機顔料組成物
WO2006120923A1 (fr) * 2005-05-11 2006-11-16 Idemitsu Kosan Co., Ltd. Composition d’huile pour machine réfrigérante et compresseur et appareil réfrigérant employant tous les deux ladite composition
JP2008195624A (ja) * 2007-02-08 2008-08-28 Nippon Emulsion Kk 油性基剤
JP2012031216A (ja) * 2010-06-29 2012-02-16 Jx Nippon Oil & Energy Corp 油剤組成物および加工液組成物
JP2014122343A (ja) * 2012-12-21 2014-07-03 Afton Chemical Corp 摩擦修正剤および清浄剤を含む添加剤組成物
WO2016060194A1 (fr) * 2014-10-17 2016-04-21 味の素株式会社 Composé d'ester d'alcool polyhydrique et d'acide acylaminé

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50105580A (fr) * 1973-09-11 1975-08-20
JPH11246841A (ja) * 1998-02-27 1999-09-14 Ajinomoto Co Inc 紫外線吸収性組成物
JP2000007942A (ja) * 1998-04-22 2000-01-11 Ajinomoto Co Inc 無機顔料組成物
WO2006120923A1 (fr) * 2005-05-11 2006-11-16 Idemitsu Kosan Co., Ltd. Composition d’huile pour machine réfrigérante et compresseur et appareil réfrigérant employant tous les deux ladite composition
JP2008195624A (ja) * 2007-02-08 2008-08-28 Nippon Emulsion Kk 油性基剤
JP2012031216A (ja) * 2010-06-29 2012-02-16 Jx Nippon Oil & Energy Corp 油剤組成物および加工液組成物
JP2014122343A (ja) * 2012-12-21 2014-07-03 Afton Chemical Corp 摩擦修正剤および清浄剤を含む添加剤組成物
WO2016060194A1 (fr) * 2014-10-17 2016-04-21 味の素株式会社 Composé d'ester d'alcool polyhydrique et d'acide acylaminé

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110698664A (zh) * 2018-07-09 2020-01-17 广东华润涂料有限公司 固体颗粒分散剂及其制备方法以及含有该分散剂的固体颗粒的分散体
CN110698664B (zh) * 2018-07-09 2022-12-09 广东华润涂料有限公司 固体颗粒分散剂及其制备方法以及含有该分散剂的固体颗粒的分散体

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