WO2013081192A1 - Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif - Google Patents

Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif Download PDF

Info

Publication number
WO2013081192A1
WO2013081192A1 PCT/JP2012/081727 JP2012081727W WO2013081192A1 WO 2013081192 A1 WO2013081192 A1 WO 2013081192A1 JP 2012081727 W JP2012081727 W JP 2012081727W WO 2013081192 A1 WO2013081192 A1 WO 2013081192A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
surfactant
salt
cosmetic
alkyl
Prior art date
Application number
PCT/JP2012/081727
Other languages
English (en)
Japanese (ja)
Inventor
愼二 黒田
瀧野　嘉延
冬美恵 大倉
Original Assignee
味の素株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 味の素株式会社 filed Critical 味の素株式会社
Priority to JP2013547266A priority Critical patent/JP5979154B2/ja
Publication of WO2013081192A1 publication Critical patent/WO2013081192A1/fr

Links

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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a cosmetic containing (A) a specific cysteine derivative or a salt thereof, and (B) a specific surfactant.
  • Patent Document 1 describes that a cysteine derivative obtained by esterifying L-2-methylthiazolidine-2,4-dicarboxylic acid or a salt thereof is useful as a whitening agent or the like.
  • Patent Document 2 describes that 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof has a whitening action.
  • these derivatives have not been put into practical use because they are easily decomposed and are not sufficiently stable.
  • An object of the present invention is to solve the problem of solubility of cysteine derivatives and to provide a cosmetic having excellent usability and transdermal absorbability.
  • the present invention is as follows.
  • a cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, and their 2.
  • the cosmetic according to 1 above which is at least one selected from salts.
  • the surfactant is a carboxylic acid type anionic surfactant, a sulfonic acid type anionic surfactant, a sulfate ester type anionic surfactant, an ether type nonionic surfactant, an ether ester type nonionic surfactant, or a quaternary ammonium.
  • the cosmetic according to 1 or 2 above which is at least one selected from a type cationic surfactant, an amino acid-based cationic surfactant, a betaine type amphoteric surfactant, and an aminocarboxylic acid type amphoteric surfactant. 4).
  • the surfactant is an N-acyl acidic amino acid salt, an N-acyl neutral amino acid salt, a fatty acid amino acid salt, an N-acyl N-methyltaurine salt, an alkylene oxide adduct of an alkyl sulfate, a polyoxyalkylene alkyl ether, 4.
  • the cosmetic according to any one of 1 to 3 above which is at least one selected from alkyl glucosides, polyoxyalkylene fatty acid esters, alkyl ammonium salts, and alkyl amide betaines.
  • Surfactant is cocoyl glutamate, cocoyl alanine salt, cocoyl sarcosine salt, coconut fatty acid arginine, cocoyl-N-methyl taurate, polyoxyethylene lauryl ether sulfate, polyoxyethylene oleyl ether, decylglucoside,
  • the above 1 which is at least one selected from PEG 60 hydrogenated castor oil, cetyltrimethylammonium chloride, cocoyl arginine ethyl ester PCA salt, cocamidopropyl betaine, amidopropyl betaine laurate, hydroxyalkyl (C12-14) hydroxyethyl sarcosine 4.
  • Cosmetics as described in any one of 3 to 3. 5.
  • the cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester or a salt thereof, and
  • the surfactant is an N-acyl acidic amino acid salt.
  • the present invention is a cosmetic containing (A) a specific cysteine derivative or a salt thereof and (B) a specific surfactant.
  • the cysteine derivative of the present invention is a cysteine derivative represented by the general formula (I) or a salt thereof.
  • X and Y are each independently OR 1 , NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group); Z represents a hydrogen atom or a C 1-22 alkyl group; W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group. ]
  • C 1-22 alkyl group means a linear or branched hydrocarbon group having 1 to 22 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, tert-octyl group, nonyl group , Isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tridecyl group, isotridecyl group, tetradecyl group, pentadecyl group, hexa
  • C 1-16 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group.
  • C 1-6 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group. Group, isopentyl group, hexyl group and the like.
  • the “C 1-22 alkoxy group” means a hydroxyl group substituted with the above “C 1-22 alkyl group”.
  • C 1-6 alkoxy group examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group and the like.
  • C 1-22 alkylamino group means an amino group substituted with the above “C 1-22 alkyl group”, and examples thereof include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, and butyl.
  • Amino group isobutylamino group, tert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, nonylamino group, decylamino group, undecylamino group, dodecylamino group, tridecylamino group, tetra
  • Examples include decylamino group, pentadecylamino group, hexadecylamino group, heptadecylamino group, octadecylamino group, nonadecylamino group, eicosylamino group, heneicosylamino group, docosylamino group and the like.
  • C 1-6 alkylamino group examples include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, tert-butylamino group, pentylamino group, and hexylamino group. Can be mentioned.
  • Halogen atom includes chlorine atom, bromine atom, fluorine atom and iodine atom.
  • X and Y are each independently OR 1 and NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group).
  • the “C 1-22 alkyl group” represented by R 1 or R 2 is preferably a C 1-6 alkyl group, more preferably a methyl group, an ethyl group or an isopropyl group, still more preferably an ethyl group. is there.
  • X is preferably OR 1 (wherein R 1 is as defined above); more preferably OR 1 ′ (wherein R 1 ′ is a hydrogen atom or a C 1-6 alkyl group (preferably Represents a methyl group, an ethyl group, or an isopropyl group); and more preferably a hydroxyl group, a methoxy group, an ethoxy group, or an isopropoxy group, and even more preferably a hydroxyl group or a methoxy group.
  • Y is preferably OR 1 (wherein R 1 is as defined above), more preferably OR 1 ′ (wherein R 1 ′ is as defined above), More preferred is a hydroxyl group, a methoxy group, an ethoxy group or an isopropoxy group, and even more preferred is a hydroxyl group or a methoxy group.
  • Z represents a hydrogen atom or a C 1-22 alkyl group.
  • the “C 1-22 alkyl group” represented by Z is preferably a C 1-6 alkyl group, and more preferably a methyl group.
  • Z is preferably a hydrogen atom or a C 1-6 alkyl group, more preferably a hydrogen atom or a methyl group.
  • W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group.
  • the “C 1-22 alkyl group” represented by W is preferably a C 1-16 alkyl group, more preferably a methyl group, a nonyl group, or a pentadecyl group, and still more preferably a methyl group.
  • the “C 1-22 alkoxy group” represented by W is preferably a C 1-6 alkoxy group, more preferably a tert-butoxy group.
  • the “C 1-22 alkylamino group” represented by W is preferably a C 1-6 alkylamino group.
  • W is preferably a C 1-22 alkyl group or a C 1-22 alkoxy group, more preferably a C 1-16 alkyl group or a C 1-6 alkoxy group, still more preferably a methyl group, a nonyl group, A pentadecyl group and a tert-butoxy group are preferable, and a methyl group and a tert-butoxy group are particularly preferable.
  • cysteine derivative represented by the general formula (I) include N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid.
  • Acid 2-ethyl ester is preferable, and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester is more preferable.
  • Examples of the salt of the cysteine derivative of the present invention include a salt with an inorganic base and a salt with an organic base.
  • Examples of the salt with an inorganic base include sodium salt, potassium salt, calcium salt, magnesium salt, zinc salt, silver salt, ammonium salt and the like.
  • Examples of salts with organic bases include methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, tris (hydroxymethyl) methylamine, dicyclohexylamine, N, N′-dibenzylethylenediamine, and guanidine.
  • each salt can be obtained by reacting the cysteine derivative of the present invention with an inorganic base or an organic base.
  • cysteine derivative of the present invention can take various salt forms, but the effect of the present invention is great when the salt form is not taken.
  • the cysteine derivative of the present invention Since the cysteine derivative of the present invention has an inhibitory effect on black melanin production, it can be used as a whitening agent, or a preventive or therapeutic agent for spots. These uses utilize the property that the cysteine derivative of the present invention exhibits a stable dosage form, but is decomposed into cysteine relatively quickly by an enzyme such as acylase at the site of action after percutaneous absorption. Is.
  • the lower limit when the cysteine derivative of the present invention or a salt thereof is blended into a cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is more preferable, 0.1% by weight is more preferable, 0.5% by weight is more preferable, and 1% by weight. Is more preferable, and 2% by weight is more preferable.
  • the weight is the weight of the cysteine derivative part (free body).
  • the upper limit when the cysteine derivative of the present invention or a salt thereof is blended into a cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 12% by weight is even more preferred, 10% by weight is even more preferred, and 5% by weight is particularly preferred.
  • the weight is the weight of the cysteine derivative part (free body).
  • cysteine derivative (I) is not particularly limited, and is produced by combining known methods. be able to. Specifically, it can be synthesized by the following method, but is not limited thereto.
  • Compound (IV) which is a precursor of cysteine derivative (I), can be synthesized by the following Step 1, and then cysteine derivative (I) can be synthesized by Step 2.
  • Compound (IV) may or may not be purified as necessary.
  • Step 1 Cysteine or a compound represented by general formula (II) obtained by esterification or amidation of cysteine in advance (hereinafter abbreviated as compound (II) and the same applies to compounds represented by other formulas). ) To form a ring by reacting with compound (III) to obtain compound (IV)
  • Compound (IV) can be obtained by reacting compound (II) with compound (III) in water or an alcohol such as methanol or ethanol for 5 to 24 hours.
  • an alcohol such as methanol or ethanol for 5 to 24 hours.
  • cysteine ethyl ester can be obtained, for example, by reacting cysteine in ethyl alcohol in the presence of hydrochloric acid or thionyl chloride at room temperature for about 5 to 24 hours.
  • cysteine amide is a protected cysteine and an amine in the presence of a dehydrating condensing agent such as EDCI.HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride), methylene chloride, A compound obtained by reacting in a solvent such as N, N-dimethylformamide (DMF) at room temperature for 5 to 24 hours can be obtained by deprotection.
  • a dehydrating condensing agent such as EDCI.HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride)
  • methylene chloride methylene chloride
  • Cysteine derivative (I) can be synthesized by reacting compound (IV) with compound (V) or compound (V ′) in the presence or absence of a solvent and in the presence or absence of a base.
  • the solvent include THF (tetrahydrofuran), ethyl acetate, isopropyl acetate, acetonitrile, acetone, ethanol, methanol, dichloromethane, water, or a mixture thereof, preferably THF, ethyl acetate, isopropyl acetate, acetonitrile, acetone, Dichloromethane, water, or a mixture thereof.
  • the base examples include organic bases such as triethylamine, diisopropylethylamine, pyridine, N-methylmorpholine, and inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, and potassium acetate.
  • organic bases such as triethylamine, diisopropylethylamine, pyridine, N-methylmorpholine
  • inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, and potassium acetate.
  • the amount of compound (V) or compound (V ′) to be used is 1.0 to 5.0 mol, preferably 1.2 to 3.0 mol, per 1 mol of compound (IV).
  • the amount of base used is 1.0 to 5.0 mol, preferably 1.2 to 4.0 mol, per 1 mol of compound (IV).
  • the reaction temperature is ⁇ 10 to 100 ° C., preferably 0 to 90 ° C.
  • the reaction time is 1 hour to 48 hours, preferably 3 hours to 20 hours. Further, this may be converted to other cysteine derivatives (I) by esterification, amidation, hydrolysis or acid anhydride.
  • the surfactant which is the component (B) of the present invention includes an anionic surfactant (for example, a carboxylic acid type anionic surfactant, a sulfonic acid type anionic surfactant, a sulfate ester type anionic surfactant, a phosphate ester type).
  • Anionic surfactant for example, a carboxylic acid type anionic surfactant, a sulfonic acid type anionic surfactant, a sulfate ester type anionic surfactant, a phosphate ester type.
  • Anionic surfactant for example, ether type nonionic surfactant, ester type nonionic surfactant, ether ester type nonionic surfactant, amide type nonionic surfactant
  • cationic surfactant for example, a carboxylic acid type anionic surfactant, a sulfonic acid type anionic surfactant, a sulfate ester type anionic surfactant, a phosphat
  • Carboxylic acid type anionic surfactants include N-acyl acidic amino acid salts such as N-acyl glutamate and N-acyl aspartate (here, acyl means 10 to 26 carbon atoms, preferably 12 to 20 carbon atoms).
  • N-acylglycine salt for example, octanoyl group, decanoyl group, lauroyl group, myristoyl group, palmitoyl group, stearoyl group, behenyl group, oleoyl group or cocoyl group.
  • N-acyl alanine salts N-acyl sarcosine salts, N-acyl threonine salts and other N-acyl neutral amino acid salts; alkyl ether carboxylic acids; fatty acid salts and the like.
  • the sulfonic acid type anionic surfactant include N-acyl-N-methyltaurine salts and sulfosuccinic acid surfactants.
  • the sulfate ester type anionic surfactant include alkyl sulfates and their alkylene oxide adducts and fatty acid amide ether sulfates.
  • Examples of the phosphoric acid ester type anionic surfactant include alkyl phosphates and their alkylene oxide adducts.
  • ether type nonionic surfactant examples include polyoxyalkylene alkyl ethers, polyoxyalkylene cholesteryl ethers, alkyl glycosides, polyglycerin alkyl ethers and the like.
  • ester type nonionic surfactant examples include fatty acid esters, glycol fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters and the like.
  • polyoxyalkylene fatty acid esters polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbit fatty acid esters, polyoxyalkylene alkyl ether fatty acid esters, polyoxyalkylene glycerin fatty acid esters
  • examples include polyoxyalkylene glycerol pyroglutamic acid fatty acid esters, polyoxyalkylene hydrogenated castor oil pyroglutamic acid fatty acid esters, and the like.
  • the amide type nonionic surfactant include fatty acid alkanolamides.
  • cationic surfactant examples include quaternary ammonium type cationic surfactants such as aliphatic quaternary ammonium salts such as alkyl ammonium salts and dialkyl ammonium salts, and aromatic quaternary ammonium salts such as benzalkonium salts, N- Examples include amino acid-based cationic surfactants such as acyl arginine ester salts.
  • amphoteric surfactants include betaine-type amphoteric surfactants such as alkylbetaines, alkylamidobetaines, carboxybetaines, sulfobetaines, aminocarboxylic acid-type amphoteric surfactants, imidazoline-type amphoteric surfactants, and N-acylarginine.
  • N-acyl basic amino acid salts such as alkyloxyhydroxypropyl arginine salts.
  • the surfactant may be in the form of a salt.
  • the salt is not particularly limited, and specific examples of the salt with cation include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as magnesium and calcium, ammonium salts, monoethanolamine, diethanolamine, Organic amine salts such as triethanolamine, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, lysine, ornithine and arginine; and salts with anions Inorganic acid salts such as hydrochloric acid, sulfuric acid, carbonic acid, phosphoric acid, etc., organic acid salts such as acetic acid, tartaric acid, citric acid, p-toluenesulfonic acid, glycolic acid, malic acid, lactic acid, fatty acid, acidic amino acid, pyroglutamic acid, etc. Can be mentioned. These may be used alone or in combination of two or more.
  • the carboxylic acid type anionic surfactant, the sulfonic acid type anionic surfactant, and the sulfate ester type anionic interface from the viewpoint that the component (A) can be further dissolved, thereby improving the feeling of use.
  • Activators, ether type nonionic surfactants, ether ester type nonionic surfactants, quaternary ammonium type cationic surfactants, amino acid type cationic surfactants, betaine type amphoteric surfactants, and aminocarboxylic acid type amphoteric surfactants Is preferred.
  • the lower limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is further preferable, 0.1% by weight is still more preferable, 0.5% by weight is even more preferable, and 1% by weight. % Is particularly preferred.
  • the upper limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 14% by weight is even more preferred, 12% by weight is even more preferred, and 10% by weight is particularly preferred.
  • A) / (B) 1/30000 to 20/1 ( g / g), preferably 1/10000 to 5/1 (g / g), more preferably 1/10000 to 1/1 (g / g), and even more preferably 1/1000.
  • the above ratio is calculated based on the weight of the cysteine derivative portion (free body).
  • the cosmetics of the present invention usually contain various components that can be used in cosmetics (including pharmaceutical external preparations and quasi drugs) to inhibit the effects of the present invention. You may mix
  • oily components amino acids, amino acid derivatives, lower alcohols, polyhydric alcohols, sugar alcohols and alkylene oxide adducts thereof, water-soluble polymers, bactericides and antibacterial agents, anti-inflammatory agents, analgesics, antifungal agents, Keratin softener, skin colorant, hormone agent, UV absorber, hair restorer, whitening agent, antiperspirant and astringent active ingredient, sweat deodorant, vitamin agent, vasodilator, crude drug, pH adjuster, viscosity adjustment Agents, pearlizing agents, natural fragrances, synthetic fragrances, pigments, antioxidants, preservatives, fats and waxes, silicone compounds, perfume oils and the like.
  • the cosmetic of the present invention can be obtained by appropriately mixing and stirring the constituent components. It can also be appropriately heated to 40 ° C to 90 ° C.
  • cosmetics is a concept including quasi drugs.
  • It can take arbitrary forms, such as liquid form, paste form, gel form, solid form, and powder form.
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid N-acetyl-cysteinylpyruvic acid; hereinafter sometimes abbreviated as N-Ac-CP
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester obtained by the same operation as in Synthesis Example 1 was dissolved in a mixed solvent of methanol (120 ml) and water (120 ml), and 2N NaOH. (182.4 ml) was added. The reaction was heated with stirring at 100 ° C. for 4 hours and at 80 ° C. overnight under an argon atmosphere. After allowing the reaction solution to cool to room temperature, AMBERLITEIR 120B H AG (about 250 g) was added to adjust the pH of the solution to 1 to 2.
  • surfactant carboxylic acid type anionic surfactant, sulfonic acid type anionic surfactant, sulfate ester type anionic surfactant, ether type nonionic surfactant, ether ester type nonionic surfactant, quaternary ammonium type cation
  • the effect was confirmed in the surfactant, the amino acid cationic surfactant, the betaine type amphoteric surfactant, and the aminocarboxylic acid type amphoteric surfactant.
  • N-acyl acidic amino acid salt N-acyl neutral amino acid salt
  • fatty acid amino acid salt N-acyl N-methyl taurine salt
  • alkylene oxide adduct of alkyl sulfate alkylene oxide adduct of alkyl sulfate
  • polyoxyalkylene alkyl ether alkyl glucoside
  • polyoxyalkylene alkylene oxide adduct of alkyl sulfate
  • alkyl sulfate polyoxyalkylene alkyl ether
  • alkyl glucoside polyoxyalkylene
  • compositions of Examples and Comparative Examples were prepared at the ratios shown in Tables 2 and 3, and added at the top of the cup of a three-dimensional skin model placed in a 12-well plate at 200 ⁇ l / cup, and at the bottom at 1 ml / well of PBS (Phosphate-buffered saline) was added and allowed to stand at 37 ° C. for 5 hours. After standing, the lower solution was collected, and the cysteine derivative concentration (T 1 ) was measured using HPLC.
  • PBS Phosphate-buffered saline
  • the transdermal absorbability was evaluated according to the following criteria in comparison with the obtained cysteine derivative concentration (T 0 ) by adding an aqueous solution (Comparative Example 3 or Comparative Example 5) to the upper part of the skin model cup and conducting the same experiment. . Note that an EPI-200X three-dimensional skin model manufactured by Kurabo Industries Co., Ltd. was used for this transdermal absorbability evaluation.
  • BG 1,3 butylene glycol
  • PG propylene glycol
  • DPG dipropylene glycol
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate
  • the cosmetics of the present invention were found to be excellent in use feeling and transdermal absorbability. As a result, it has become possible to provide cosmetics that are more effective than conventional whitening cosmetics.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention s'attaque au problème de proposer un produit cosmétique qui résout des problèmes avec la solubilité des dérivés de cystéine et qui présente une sensation de peau supérieure et une absorbabilité transdermique supérieure. A cet effet, selon l'invention, un produit cosmétique est proposé qui contient (A) un dérivé de cystéine spécifique ou un sel de celui-ci et (B) un agent tensio-actif.
PCT/JP2012/081727 2011-11-30 2012-11-30 Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif WO2013081192A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2013547266A JP5979154B2 (ja) 2011-11-30 2012-11-30 システイン誘導体および界面活性剤を含有する化粧料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-262162 2011-11-30
JP2011262162 2011-11-30

Publications (1)

Publication Number Publication Date
WO2013081192A1 true WO2013081192A1 (fr) 2013-06-06

Family

ID=48535627

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/081727 WO2013081192A1 (fr) 2011-11-30 2012-11-30 Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif

Country Status (2)

Country Link
JP (1) JP5979154B2 (fr)
WO (1) WO2013081192A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2013081193A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体およびアルコールを含有する化粧料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004517063A (ja) * 2000-11-17 2004-06-10 ロレアル ２−オキソチアゾリジン−４−カルボン酸誘導体の剥離促進剤としての使用
JP2009227660A (ja) * 2008-02-28 2009-10-08 Ajinomoto Co Inc システイン誘導体
WO2009154014A1 (fr) * 2008-06-19 2009-12-23 日本理化学薬品株式会社 Composition externe
WO2011149093A1 (fr) * 2010-05-28 2011-12-01 味の素株式会社 Dérivé de cystéine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013081146A1 (fr) * 2011-11-30 2013-06-06 味の素株式会社 Produit cosmétique antirides
EP2786741B1 (fr) * 2011-11-30 2018-12-26 Ajinomoto Co., Inc. Produit cosmétique de blanchiment de la peau
WO2013081193A1 (fr) * 2011-11-30 2013-06-06 味の素株式会社 Produit cosmétique contenant un dérivé de cystéine et un alcool

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004517063A (ja) * 2000-11-17 2004-06-10 ロレアル ２−オキソチアゾリジン−４−カルボン酸誘導体の剥離促進剤としての使用
JP2009227660A (ja) * 2008-02-28 2009-10-08 Ajinomoto Co Inc システイン誘導体
WO2009154014A1 (fr) * 2008-06-19 2009-12-23 日本理化学薬品株式会社 Composition externe
WO2011149093A1 (fr) * 2010-05-28 2011-12-01 味の素株式会社 Dérivé de cystéine

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CREMONESI, G. ET AL.: "Asymmetric synthesis of 1,3-thiazolidine-derived spiro-p-lactams via a Staudinger reaction between chiral ketenes and imines", TETRAHEDRON:ASYMMETRY, vol. 16, 2005, pages 3371 - 3379 *
NALLET, J. P. ET AL.: "Synthesis of a Series of Hexitol and Aminodeoxyhexitol Mononitrate Derivatives Containing a Sulfur Group and Pharmacological Evaluation on Isolated Rat Aortas", EUR. J. ORG. CHEM., 1998, pages 933 - 943 *
SCHUBERT, M. P.: "Reactions of Semimercaptals With Amino Compounds", J.BIOLOGICAL CHEM., vol. 121, 1937, pages 539 - 548 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2013081193A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体およびアルコールを含有する化粧料

Also Published As

Publication number Publication date
JP5979154B2 (ja) 2016-08-24
JPWO2013081192A1 (ja) 2015-04-27

Similar Documents

Publication Publication Date Title
EP2786741B1 (fr) Produit cosmétique de blanchiment de la peau
US6010708A (en) Cosmetics and N-acylamino acid composition
EP2813488B1 (fr) Dérivé d'acide aminé basique de type ion amphotère
KR101496795B1 (ko) 시스테인 유도체
CN103282348A (zh) 使用雷琐辛衍生物使角蛋白材料脱色的方法
KR20090118948A (ko) 시나핀산 유도체의 용도 및 그러한 유도체를 포함하는 조성물
JP3424930B2 (ja) Ｎ−アシルグルタミン誘導体
JPH11279040A (ja) 皮膚外用剤
JP5994789B2 (ja) シワ防止化粧料
JP5979155B2 (ja) システイン誘導体およびアルコールを含有する化粧料
JP5979154B2 (ja) システイン誘導体および界面活性剤を含有する化粧料
KR102068635B1 (ko) 3,4,5-트리메톡시 신남산 에스테르 유도체와 그 제조방법 및 이를 포함하는 피부 미백용 조성물
CA2902333C (fr) Compositions cosmetiques contenant des amides tricyclodecanes
JP2011178733A (ja) Ｎ−長鎖アシル酸性アミノ酸ジエステル化合物及びこれを用いた化粧料及び洗浄料
EP3176150B1 (fr) Dérivé (acyle à chaîne moyenne)acide aminé basique
CA2903023C (fr) Compositions photoprotectrices contenant des amides tricyclodecanes
JP2013542232A (ja) １２−［（１２−ヒドロキシオクタデカノイル）オキシ］オクタデカン酸を含有するリーブオン型の非固形皮膚コンディショニング組成物
KR100532786B1 (ko) 아미노산 유도체, 이를 함유하는 조성물 및 이러한 조성물을 함유하는 제제
WO1994021591A1 (fr) Preparation dermatologique et nouveau derive d'acide benzoique
KR101491728B1 (ko) 비타민 c와 비타민 b3의 컨쥬게이트 및 그를 포함하는 항산화제
KR20190024334A (ko) 아실글리시네이트 제조방법 및 그것을 이용한 인체세정용 조성물
JP3712676B2 (ja) 外用剤組成物
KR100656071B1 (ko) 구형의 라멜라 구조를 형성하는 피부 세정제 조성물
WO2024028511A1 (fr) Composition avec résistance à l'eau améliorée
JP4150738B2 (ja) 外用剤組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12853653

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2013547266

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12853653

Country of ref document: EP

Kind code of ref document: A1