WO2009154014A1 - Composition externe - Google Patents

Composition externe Download PDF

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Publication number
WO2009154014A1
WO2009154014A1 PCT/JP2009/052524 JP2009052524W WO2009154014A1 WO 2009154014 A1 WO2009154014 A1 WO 2009154014A1 JP 2009052524 W JP2009052524 W JP 2009052524W WO 2009154014 A1 WO2009154014 A1 WO 2009154014A1
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WO
WIPO (PCT)
Prior art keywords
acid
hair
poe
ether
thiothiazolidine
Prior art date
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PCT/JP2009/052524
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English (en)
Japanese (ja)
Inventor
幸生 滝沢
香織 澤村
英明 大城
喜治 田村
Original Assignee
日本理化学薬品株式会社
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Application filed by 日本理化学薬品株式会社 filed Critical 日本理化学薬品株式会社
Publication of WO2009154014A1 publication Critical patent/WO2009154014A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • 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

Definitions

  • the present invention relates to an external composition containing 2-thiothiazolidine-4-carboxylic acid or a derivative thereof or 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof or a salt thereof.
  • Active oxygen is a general term for superoxide, hydrogen peroxide, hydroxy radicals, singlet oxygen, and the like. Usually, in vivo, it is degraded and inactivated by enzymes such as superoxide dismutase (SOD) and catalase. However, with increasing stress and aging, their enzyme activity decreases, and active oxygen increases due to air pollution, radiation, ultraviolet rays, smoking, etc., and finally it is in a state where decomposition and inactivation in vivo are insufficient It will fall into.
  • SOD superoxide dismutase
  • catalase catalase
  • Non-Patent Document 1 So far, it has been reported that active oxygen promotes cross-linking of collagen and elastic fibers non-enzymatically (see, for example, Non-Patent Document 1). That is, the active oxygen remaining without being decomposed or inactivated induces undesirable skin aging symptoms such as rough skin, wrinkles and sagging. In order to alleviate this situation, it is considered useful to add an antioxidant to the external composition for skin.
  • Non-Patent Document 2 It has recently been clarified that active oxygen is involved not only in skin aging but also in hair damage. In addition, it has also been reported that it is possible to suppress the occurrence of hair splits and cuts by applying an antioxidative extract to the hair (see, for example, Non-Patent Document 2). That is, it seems that the blending of the antioxidant into the hair external composition is useful for alleviating hair damage.
  • This stain or pigmentation can be said to be a skin condition in which the balance of excessive production of melanin by stimulation of ultraviolet rays or active oxygen is lost.
  • Melanin is synthesized from tyrosine, a kind of amino acid, as a starting material.
  • the first reaction begins with a reaction in which tyrosine is oxidized to dopa and dopaquinone by an enzyme called tyrosinase. Thereafter, dopaquinone is converted into dihydroxyindole (DHI) by autooxidation through dopachrome, and again oxidized to tyrosinase to become black and insoluble melanin.
  • DHI dihydroxyindole
  • 2-thiothiazolidine-4-carboxylic acid is a phytotoxicity-reducing action (for example, refer to Patent Document 1) of a quaternary ammonium salt herbicide to plants, a bactericidal action against potato fungus (for example, (See Patent Document 2 or 3).
  • 2-methylthiazolidine-2,4-dicarboxylic acid has a mucolytic action (see, for example, Patent Document 4) and a hepatotoxicity-reducing action of paracetamol (see, for example, Patent Document 5). Furthermore, an anticancer action (see, for example, Patent Document 6 or 7) is shown.
  • compositions containing 2-thiothiazolidine-4-carboxylic acid are well known as combination preparations with agricultural chemicals and agricultural fungicides.
  • the idea of using it for a composition for external use such as skin cosmetics and hair cosmetics is not known at all, and is not actually carried out.
  • compositions containing 2-methylthiazolidine-2,4-dicarboxylic acid are known as mucolytic agents, hepatotoxicity-reducing actions or anticancer agents.
  • 2-thiothiazolidine-4-carboxylic acid the idea of using this compound in a composition for external use such as skin cosmetics and hair cosmetics is not known at all, and is not actually carried out.
  • the present invention provides skin cosmetics and hair that alleviate aging and damage using 2-thiothiazolidine-4-carboxylic acid or a derivative thereof or 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof or both. It is an object of the present invention to provide a composition for external use such as a cosmetic, and a composition for external use such as a hair cosmetic that changes the shape and color of the hair.
  • the composition for external use according to the present invention is one or more selected from the compound represented by the structural formula (Chemical Formula 1), the compound represented by the structural formula (Chemical Formula 2) or a salt thereof (provided that 1) and (Chemical Formula 2) both contain R 1 , R 2 and R 3 in the structural formula each representing a hydroxyl group, amino group, methoxy group or ethoxy group).
  • R 1 is a hydroxyl group, it is 2-thiothiazolidine-4-carboxylic acid.
  • R 1 is an amino group, a methoxy group, or an ethoxy group
  • 2-thiothiazolidine-4-carboxylic acid Described as a derivative.
  • R 2 and R 3 are hydroxyl groups, is a 2-methyl-2,4-dicarboxylic acid, R 2 and R 3 is other than hydroxyl groups, a combination of R 2 and R 3 2- Described as a derivative of methylthiazolidine-2,4-dicarboxylic acid.
  • one or more of these are preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass, and still more preferably 0.5 to 2% by mass. It contains.
  • the external composition according to the present invention is, for example, a skin external preparation or a skin cosmetic. It is also a hair cosmetic.
  • One or more selected from 2-thiothiazolidine-4-carboxylic acid or a derivative thereof or 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof or a salt thereof contained in the composition for external use of the present invention Has an excellent active oxygen scavenging effect, tyrosinase inhibitory effect, and reducing effect.
  • the composition for external use of the present invention has an anti-aging effect due to an antioxidant effect, a whitening effect due to a tyrosinase inhibitory effect, and further in skin keratin due to a reducing effect
  • Skin external preparations or cosmetics that have the effect of improving acne vulgaris by removing old keratin accompanying disulfide bond cleavage, accelerating turnover and emollient, or acne bacteria removal by its bactericidal action, and hair damage Prevents hair cosmetics, and also permanents, curling agents, and hair straighteners due to the reduction effect of disulfide bonds It can be a useful external composition such as a hair dye or hair dye.
  • the 2-thiothiazolidine-4-carboxylic acid or derivative thereof contained in the composition for external use of the present invention is represented by the structural formula (Formula 1).
  • R 1 in the structural formula of (Chemical Formula 1) is a hydroxyl group, an amino group, a methoxy group, or an ethoxy group, and there are a total of four types of compounds having the structural formula of (Chemical Formula 1).
  • R 1 is a hydroxyl group or a methoxy group or an ethoxy group
  • compounds wherein R 1 is a hydroxyl group that is, 2-thio-thiazolidine-4-carboxylic acid is more preferable.
  • 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof contained in the composition for external use of the present invention is represented by the structural formula (Formula 2).
  • R 2 in the structural formula of (Chemical Formula 2) is a hydroxyl group, an amino group, a methoxy group, or an ethoxy group
  • R 3 is also a hydroxyl group, an amino group, a methoxy group, or an ethoxy group
  • (Chemical Formula 2) There are a total of 16 compounds having the structural formula.
  • R 2 is a hydroxyl group
  • a combination of R 3 is a hydroxyl group or a methoxy group or an ethoxy group or an amide group, or R 2 is a methoxy group
  • R 3 is preferably a compound of a combination of a hydroxyl group, among them
  • R 2 is A compound in which R3 is a hydroxyl group in combination with a hydroxyl group is more preferable. More preferred are compounds wherein R 2 and R 3 are hydroxyl groups, ie 2-methylthiazolidine-2,4-dicarboxylic acid.
  • the 2-thiothiazolidine-4-carboxylic acid or its derivative or 2-methylthiazolidine-2,4-dicarboxylic acid or its derivative in the present invention may be either an optically active substance or a racemic substance.
  • the salt include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as magnesium and calcium, salts with inorganic bases such as ammonia, or general organic bases such as methylamine, ethylamine, dimethylamine and trimethylamine, or Examples thereof include salts with basic amino acids such as arginine, lysine and ornithine.
  • a salt of 2-thiothiazolidine-4-carboxylic acid (or a derivative thereof) and a salt of 2-methylthiazolidine-2,4-dicarboxylic acid (or a derivative thereof) may be added as a salt
  • 2-methylthiazolidine-2,4-dicarboxylic acid (or a derivative thereof) and a component that forms a salt with them are blended separately.
  • a salt may be formed.
  • 2-thiothiazolidine-4-carboxylic acid (or a derivative thereof) and a component that forms a salt with it may be blended separately to form a salt in the composition.
  • 2-methylthiazolidine-2,4-dicarboxylic acid (or a derivative thereof) and a component that forms a salt with it may be blended separately to form a salt in the composition.
  • 2-thiothiazolidine-4-carboxylic acid can be easily derived from L-cystine as described in Non-Patent Document 3, for example. Further, 2-methylthiazolidine-2,4-dicarboxylic acid can be easily derived from L-cysteine as described in Non-Patent Document 4, for example.
  • composition for external use of the present invention is generally used externally.
  • the component used as a composition can be added in the range which does not inhibit the effect of this invention.
  • powder components liquid fats and oils, solid fats and oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicone, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, Moisturizer, water-soluble polymer compound, thickener, film agent, sequestering agent, lower alcohol, polyhydric alcohol, saccharides, amino acids, organic amines, synthetic resin emulsion, pH adjuster, skin nutrient, vitamin , Antioxidants, whitening agents, fragrances, water and the like can be appropriately blended as necessary. Two or more of these may be blended. Although the specific example of the component which can be mix
  • the powder component examples include mica, kaolin, calamine, magnesium carbonate, calcium phosphate, rice starch, sericite, muscovite, phlogopite, synthetic mica, sauroite, biotite, gold, silver, platinum, talc, hydroxyapatite, Silica, aluminum silicate and magnesium silicate, barium sulfate, zinc oxide, aluminum oxide, zirconium oxide, titanium oxide, yellow iron oxide, carbon black, fullerene, nanodiamond, tourmaline, ultramarine, bitumen, black iron oxide, chromium oxide, hydroxide Chrome, Bengala, Manganese violet, Cobalt violet, Mica titanium, Bismuth oxychloride, Fish scale foil, Silk powder, Polyamide resin powder (nylon powder), Polyethylene powder, Polymethylmethacrylate powder, Polystyrene powder, Copolymerization of styrene and acrylic acid Body resin powder, benzoguanamine resin powder, organic powder of cellulose powder, metal powder
  • Red No. 405 Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401 or Blue No. 404, Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red 230 No., red 401, red 505, orange 205, yellow 4, yellow 5, yellow 202, yellow 203, green 3 or blue 1, etc., organic pigments such as zirconium, barium or aluminum lake, And natural pigments such as chlorophyll and ⁇ -carotene.
  • liquid fats examples include amanine oil, almond oil, avocado oil, olive oil, kayak oil, cucumber oil, candlenut oil, grape seed oil, sesame oil, wheat germ oil, rice bran oil, soybean oil, tea oil, camellia oil, corn Oil, rapeseed oil, persic oil, pearl oil, jojoba oil, pistachio oil, castor oil, sunflower oil, meadow foam oil, peanut oil, orange luffy oil, triglycerin, trioctanoic acid glycerin, triisopalmitic acid glycerin, etc. It is done.
  • solid fat examples include cacao butter, palm oil, horse fat, hydrogenated palm oil, palm oil, beef tallow, sheep fat, hydrogenated beef tallow, palm kernel oil, pork fat, beef bone fat, owl kernel oil, hydrogenated oil, cattle Leg fat, mole, hardened castor oil and the like.
  • waxes examples include beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ibota wax, whale wax, montan wax, nuka wax, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugar cane wax, lanolin fatty acid isopropyl, hexyl laurate, and reduced lanolin.
  • hydrocarbon oil examples include liquid paraffin, ozokerite, squalene, pristane, paraffin, ceresin, petrolatum, microcrystalline wax, and the like.
  • higher fatty acids include arachidonic acid, isostearic acid, underesylenic acid, oleic acid, stearic acid, sebacic acid, palmitic acid, behenic acid, myristic acid, lauric acid, lanolin fatty acid, linoleic acid, linolenic acid, eicosapentaenoic acid ( EPA) and docosahexaenoic acid (DHA).
  • arachidonic acid isostearic acid, underesylenic acid, oleic acid, stearic acid, sebacic acid, palmitic acid, behenic acid, myristic acid, lauric acid, lanolin fatty acid, linoleic acid, linolenic acid, eicosapentaenoic acid ( EPA) and docosahexaenoic acid (DHA).
  • Examples of the higher alcohol include linear alcohols such as lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, monostearyl glycerin ether (batyl alcohol), 2-decyltetradecinol, lanolin
  • Examples thereof include branched chain alcohols such as alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, and octyldodecanol.
  • Synthetic ester oils include, for example, isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl dimethyloctanoate, cetyl lactate, Myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearylate, ethylene glycol di-2-ethylhexylate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, Diisostearyl malate, glycerin di-2-heptylundecanoate, trimethylolpropane tri-2
  • silicone examples include chain polysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, and methylhydrogenpolysiloxane, cyclic polysiloxanes such as decamethylpolysiloxane, dodecamethylpolysiloxane, and tetramethyltetrahydrogenpolysiloxane, Examples thereof include silicone resin and silicone rubber forming a three-dimensional network structure.
  • anionic surfactant examples include soap bases, fatty acid soaps such as sodium laurate and sodium palmitate, higher alkyl sulfates such as sodium lauryl sulfate and lauryl sulfate K, POE lauryl sulfate triethanolamine, and POE lauryl sulfate.
  • Alkyl ether sulfates such as sodium, N-acyl sarcosine acids such as sodium lauroyl sarcosine, N-myristoyl-N-methyl taurine sodium, coconut oil fatty acid methyl tauride sodium, lauryl methyl tauride sodium and other higher fatty acid amide sulfonic acids Salts, phosphate ester salts such as sodium POE oleyl ether phosphate, POE stearyl ether phosphate, sodium di-2-ethylhexylsulfosuccinate, monolauroyl monoe Sulfosuccinates such as sodium olamide polyoxyethylene sulfosuccinate and sodium lauryl polypropylene glycol sulfosuccinate, sodium linear dodecyl benzene sulfonate, triethanolamine linear dodecyl benzene sulfonate, alkyl benzene sulfonates such as linear dode
  • Sulfated oil POE alkyl ether carboxylic acid, POE alkyl allyl ether carboxylate, ⁇ -olefin sulfonate, high Secondary fatty acid ester sulfonate, secondary alcohol sulfate, higher fatty acid alkylolamide sulfate, sodium lauroyl monoethanolamide sodium succinate, ditriethanolamine N-palmitoyl aspartate, sodium caseinate and the like.
  • cationic surfactant examples include alkyltrimethylammonium salts such as stearyltrimethylammonium chloride and lauryltrimethylammonium chloride, distearyldimethylammonium dialkyldimethylammonium chloride, and poly (N, N′-dimethyl-3,5-methylene chloride).
  • alkyltrimethylammonium salts such as stearyltrimethylammonium chloride and lauryltrimethylammonium chloride, distearyldimethylammonium dialkyldimethylammonium chloride, and poly (N, N′-dimethyl-3,5-methylene chloride).
  • alkyl pyridinium salts such as cetyl pyridinium chloride, alkyl quaternary ammonium salts, alkyl dimethyl benzyl ammonium salts, alkyl isoquinolinium salts, dialkyl morpholinium salts, POE alkyl amines, alkyl amine salts, polyamine fatty acid derivatives Amyl alcohol fatty acid derivatives, benzalkonium chloride, benzethonium chloride and the like.
  • alkyl pyridinium salts such as cetyl pyridinium chloride, alkyl quaternary ammonium salts, alkyl dimethyl benzyl ammonium salts, alkyl isoquinolinium salts, dialkyl morpholinium salts, POE alkyl amines, alkyl amine salts, polyamine fatty acid derivatives Amyl alcohol fatty acid derivatives, benzalkonium chloride, benzethonium chloride and the like.
  • amphoteric surfactants examples include 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium Imidazoline-based amphoteric surfactants such as salt, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkylbetaine, amide betaine, sulfobetaine, etc. Can be given.
  • lipophilic nonionic surfactant examples include sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, penta-2 -Sorbitan fatty acid esters such as diglycerol sorbitan ethylhexylate, diglycerol sorbitan tetra-2-ethylhexylate, mono cottonseed oil fatty acid glycerin, glyceryl monoerucate, glyceryl sesquioleate, glyceryl monostearate, ⁇ , ⁇ '-oleic acid pyro Glycerol polyglycerin fatty acids such as glyceryl glutamate, glyceryl monostearate malate, and propylene glycol fats such as propylene glycol monostearate Examples include acid esters, hydrogen
  • hydrophilic nonionic surfactants examples include POE sorbitan monooleate, POE sorbitan monostearate, POE sorbitan monooleate, POE sorbitan fatty acid esters such as POE sorbitan tetraoleate, POE sorbitan monolaurate, and POE sorbitol.
  • POE glycerin fatty acid esters such as monooleate, POE sorbite pentaoleate, POE sorbite fatty acid esters such as POE sorbite monostearate, POE glycerin monostearate, POE glycerin monoisostearate, POE glycerin triisostearate, POE fatty acid esters such as POE monooleate, POE distearate, POE monodiolate, ethylene glycol stearate, POE lauryl POE alkyl ethers such as ether, POE oleyl ether, POE stearyl ether, POE behenyl ether, POE2-octyldodecyl ether, POE cholestanol ether, POE alkyl such as POE octyl phenyl ether, POE nonyl phenyl ether, POE dinonyl phenyl ether P
  • Tetraonic Tetra POE / Tetra POP ethylenediamine condensates POE castor oil, POE hydrogenated castor oil, POE cured POE castor oil hardened castor oil derivatives such as POE castor oil monoisostearate, POE hydrogenated castor oil triisostearate, POE cured castor oil monopyroglutamic acid monoisostearic acid diester, POE cured castor oil maleic acid, POE such as POE sorbite beeswax Beeswax lanolin derivatives, alkanolamides such as coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide, POE propylene glycol fatty acid ester, POE alkylamine, POE fatty acid amide, sucrose fatty acid ester, POE nonylphenyl formaldehyde condensate , Alkylethoxydimethylamine oxide, trioleyl phosphate, and
  • humectant examples include polyethylene glycol, propylene glycol, dipropylene glycol, glycerin, polyglycerin, 1,3-butylene glycol, 1,2-hexanediol, 1,2-pentanediol, polyoxyethylene glycerin (26E.
  • polyoxyethylene methyl glucoside polyoxyethylene methyl glucoside, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salt, dl-pyrrolidonecarboxylic acid
  • acids include acid salts, short-chain soluble collagen, diglycerin (EO) PO adducts, Izayoi rose extract, yarrow extract, and merirot extract.
  • Examples of natural water-soluble polymers include gum arabic, gum tragacanth, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (gypsum extract), starch (rice, corn, potato, Wheat), plant polymers such as glycyrrhizic acid, microbial polymers such as xanthan gum, dextran, succinoglucan and pullulan, and animal polymers such as collagen, casein, albumin and gelatin.
  • semi-synthetic water-soluble polymers include starch polymers such as carboxymethyl starch and methylhydroxypropyl starch, methylcellulose, nitrocellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose, Examples thereof include cellulose polymers such as sodium carboxymethyl cellulose (CMC), crystalline cellulose and cellulose powder, and alginic acid polymers such as sodium alginate and propylene glycol alginate.
  • starch polymers such as carboxymethyl starch and methylhydroxypropyl starch, methylcellulose, nitrocellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose
  • examples thereof include cellulose polymers such as sodium carboxymethyl cellulose (CMC), crystalline cellulose and cellulose powder, and alginic acid polymers such as sodium alginate and propylene glycol alginate
  • Examples of the synthetic water-soluble polymer include vinyl polymers such as polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer (Carbopol), polyethylene glycol 20,000, 4,000,000, 600,000. Polyoxyethylene polymer such as polyoxyethylene polyoxypropylene copolymer copolymer polymer, acrylic polymer such as sodium polyacrylate, polyethyl acrylate, polyacrylamide, polyethyleneimine, cationic polymer, etc. It is done.
  • vinyl polymers such as polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer (Carbopol), polyethylene glycol 20,000, 4,000,000, 600,000.
  • Polyoxyethylene polymer such as polyoxyethylene polyoxypropylene copolymer copolymer polymer, acrylic polymer such as sodium polyacrylate, polyethyl acrylate, polyacrylamide, polyethyleneimine, cationic polymer, etc.
  • inorganic water-soluble polymer examples include bentonite, aluminum / magnesium silicate, laponite, hectorite, and anhydrous silicic acid.
  • thickeners examples include gum arabic, carrageenan, caraya gum, gum tragacanth, carob gum, quince seed (malmello), casein, dextrin, gelatin, sodium pectate, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethylcellulose, hydroxypropyl Cellulose, PVA, PVM, PVP, sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, cellulose dialkyldimethylammonium sulfate, xanthan gum, aluminum silicate / magnesium, bentonite, hectorite and the like.
  • sequestering agent examples include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate Sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid and the like.
  • lower alcohols examples include methanol, ethanol, propanol, isopropanol, isobutyl alcohol, and t-butyl alcohol.
  • polyhydric alcohol examples include ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol.
  • Tetrahydric alcohol pentahydric alcohol such as xylitol, hexahydric alcohol such as sorbitol, mannitol, diethylene glycol, dipropylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, diglyceride Polyethylene glycol, triglycerin, tetraglycerin, polyglycerin and other polyhydric alcohol polymers, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, Divalent alcohol alkyl ethers such as ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibuty
  • monosaccharides include tricarbon sugars such as D-glyceryl aldehyde and dihydroxyacetone, tetracarbon sugars such as D-erythrose, D-erythrulose, D-threose and erythritol, L-arabinose, D-xylose and L-lyxose.
  • tricarbon sugars such as D-glyceryl aldehyde and dihydroxyacetone
  • tetracarbon sugars such as D-erythrose, D-erythrulose, D-threose and erythritol
  • L-arabinose D-xylose and L-lyxose.
  • Pentoses such as D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, D-glucose, D-talose, D-bucose, D-galactose, D-fructose, L-galactose, Hexasaccharides such as L-mannose and D-tagatose, heptoses such as aldheptose and heptose, octoses such as octose, 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L -Deoxy sugars such as mannose, D-glucosamine, D-galactosamine, sialic acid, amino Uronic acid, amino sugar such as muramic acid, D- glucuronic acid, D- mannuronic acid, L- guluronic acid, D- galacturonic acid, uronic acids such as L
  • oligosaccharides include sucrose, gentianose, umbelliferose, lactose, planteose, isoliquinoses, ⁇ , ⁇ -trehalose, raffinose, lycnose, stachyose, and Verbose course.
  • polysaccharide examples include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guar gum, dextran, kerato sulfate. , Locust bean gum, succinoglucan, caronic acid and the like.
  • amino acids for example, neutral amino acids such as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tryptophan, cystine, cysteine, methionine, proline, hydroxyproline, acidic amino acids such as aspartic acid, glutamic acid, asparagine, glutamine, and Examples include basic amino acids such as arginine, histidine, lysine and hydroxylysine.
  • amino acid derivatives include acyl sarcosine sodium (lauroyl sarcosine sodium), acyl glutamate, acyl ⁇ -alanine sodium, glutathione, pyrrolidone carboxylic acid and the like.
  • organic amines examples include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol. Can be given.
  • Examples of the synthetic resin emulsion include an acrylic resin emulsion, a polyethyl acrylate emulsion, an acrylic resin liquid, a polyacryl alkyl ester emulsion, and a polyvinyl acetate resin emulsion.
  • pH adjuster examples include buffers such as lactic acid-sodium lactate and citric acid-sodium citrate.
  • vitamins examples include vitamins A, B1, B2, B6, E or derivatives thereof, pantothenic acid or derivatives thereof, biotin, and the like.
  • antioxidant or antioxidant examples include ascorbic acid, sodium ascorbate, ascorbyl stearate, ascorbyl palmitate, ascorbyl dipalmitate, magnesium ascorbate phosphate, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocotrienol, ⁇ -tocotrienol, ⁇ -tocotrienol, ⁇ -tocotrienol, tocopherol acetate, natural vitamin E, tocopherol nicotinate, Trolox, N-acetylcysteine, ⁇ -lipoic acid, dehydrolipoic acid, uric acid, dihydroxy Toluene, butylhydroxyanisole, dibutylhydroxytoluene, erythorbic acid, sodium erythorbate, gallic acid, propyl gallate, tannic acid, catechin, co Heic acid, ferulic acid, protocatechuic acid, or
  • whitening agents include arbutin, ellagic acid, chamomile ET, t-AMCHA, tranexamic acid, ascorbic acid, sodium ascorbate, ascorbyl stearate, ascorbyl palmitate, ascorbyl dipalmitate, magnesium ascorbate, ascorbic acid 2-glucoside, Examples include ethyl ascorbate, acetyltyrosine, retinoic acid, linoleic acid, lucinol, hydroquinone, kojic acid, chamomile extract, jux extract, cucumber extract, licorice extract, aloe extract, placenta extract, and lumpuyan extract.
  • flavors include animal flavors, plant flavors, synthetic flavors, and blended flavors.
  • compositions for external use include antiseptic / bactericides, UV absorbers, anti-fading agents, acne agents, anti-dandruff / itching agents, antiperspirant deodorants, burn agents, anti-ticks / lice agents, keratin Softeners, dry skin drugs, antiviral agents, transdermal absorption enhancers, hormones, peptides, proteins, astringents, anti-inflammatory agents, refreshing / stimulating agents, antibiotics, antifungal agents, hair restorers, etc. Can be mentioned.
  • composition for external use one or more selected from 2-thiothiazolidine-4-carboxylic acid (or a derivative thereof) or 2-methylthiazolidine-2,4-dicarboxylic acid (or a derivative thereof) or a salt thereof
  • the total concentration of two or more kinds is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass. More preferably, the content is 0.5 to 2.0% by mass.
  • An active ingredient to be blended into a cosmetic product usually enhances the intended effect according to the addition concentration, but when the concentration exceeds a certain concentration, the effect often remains unchanged even if the addition amount is increased.
  • the upper limit is approximately 5% by mass for those used on the skin and 10% by mass for those used on the hair. That is, also in the present invention, one or two kinds selected from 2-thiothiazolidine-4-carboxylic acid (or a derivative thereof), 2-methylthiazolidine-2,4-dicarboxylic acid (or a derivative thereof) or a salt thereof. If the total concentration exceeds 10% by mass, the desired effect according to the amount added cannot be obtained, which is economically disadvantageous. On the other hand, if the total concentration is less than 0.01% by mass, the added amount is too small and the effect is difficult to obtain.
  • the dosage form of the external composition of the present invention is arbitrary, and is a solution system, a solubilization system, an emulsification system, an oil liquid system, a gel system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system.
  • a wide variety of dosage forms can be taken according to the intended product by blending one or more of the above optional blending components and the essential components of the present invention.
  • the external composition of the present invention refers to cosmetics, pharmaceuticals, quasi-drugs, those applied to the outer skin (including the scalp) or hair, and its use is arbitrary.
  • lotion, emulsion, Facial cosmetics and foundations such as creams and packs
  • makeup cosmetics such as lipsticks and eye shadows
  • sunscreens and body cosmetics for the purpose of preventing UV rays, aromatic cosmetics, hair care agents, permanent agents, curling agents, hair dyes Etc. can be used.
  • Example 1 Whether 2-thiothiazolidine-4-carboxylic acid-containing external composition and 2-methylthiazolidine-2,4-dicarboxylic acid-containing external composition have radical scavenging ability at a practical level as cosmetics was confirmed.
  • the radical scavenging ability at a practical level refers to a radical scavenging rate of 50% or more.
  • the radical scavenging ability was confirmed as follows. DPPH (1,1-diphenyl-2-picrylhydrazyl) was dissolved in ethanol to prepare a 1 mM solution concentration. Furthermore, the test compound was dissolved in water and adjusted to a 0.5 or 1.0 w / v% solution concentration to obtain a test compound solution.
  • test compound solution To 1 mL of the test compound solution, 5 mL of ethanol and 0.27 mL of DPPH solution were added and mixed. Then, it was left at room temperature for 20 minutes to prepare a test solution. Separately, 1 mL of water was mixed with 5 mL of ethanol and 0.27 mL of DPPH solution. Then, it was left at room temperature for 20 minutes to obtain a blank test solution. Absorbances A T and A B at a wavelength of 520 nm were measured for the test solution and the blank test solution. The DPPH radical scavenging rate of the test compound was calculated by the following formula (Equation 1) to determine the DPPH radical scavenging ability.
  • Equation 1 The DPPH radical scavenging rate of the test compound was calculated by the following formula (Equation 1) to determine the DPPH radical scavenging ability.
  • Example 2 Does the composition for external use containing 2-thiothiazolidine-4-carboxylic acid and the composition for external use containing 2-methylthiazolidine-2,4-dicarboxylic acid have hydrogen peroxide scavenging ability at a practical level as cosmetics? Confirmation was made.
  • the hydrogen peroxide scavenging ability at a practical level refers to when the hydrogen peroxide scavenging rate is 50% or more.
  • the hydrogen peroxide scavenging ability was confirmed as follows. Phenol and 4-aminoantipyrine were dissolved in 1M Tris buffer (pH 8.0), respectively, and adjusted to 40 mM and 8 mM solution concentrations, respectively.
  • peroxidase was dissolved in 1M Tris buffer (pH 8.0) to prepare a solution concentration of about 3125 U / mL. Further, 1 mL each of the phenol solution, the 4-aminoantipyrine solution, and the peroxidase solution prepared as described above and 7 mL of 1M Tris buffer (pH 8.0) were mixed to obtain a coloring solution. Diethylenetriaminepentaacetic acid was dissolved in phosphate buffer PBS ( ⁇ ) to prepare a 0.5 mM solution concentration. Furthermore, the test compound was dissolved in water and adjusted to a 0.5 or 1.0 w / v% solution concentration to obtain a test compound solution.
  • test compound solution 0.4 mL
  • a 1 mM hydrogen peroxide solution 0.4 mL
  • a coloring solution 0.4 mL
  • the same operation was performed with 0.4 mL of diethylenetriaminepentaacetic acid solution instead of the test compound solution.
  • the same operation was performed with 0.4 mL of water instead of the hydrogen peroxide solution as a reagent blank.
  • the hydrogen peroxide scavenging rate of the test compound was calculated by the following formula (Equation 2) to determine the hydrogen peroxide scavenging ability.
  • Equation 2 The hydrogen peroxide scavenging rate of the test compound was calculated by the following formula (Equation 2) to determine the hydrogen peroxide scavenging ability.
  • Equation 2 both 2-thiothiazolidine-4-carboxylic acid-containing external composition and 2-methylthiazolidine-2,4-dicarboxylic acid-containing external composition are practical enough at 1.0 w / v%. It showed a level of hydrogen peroxide scavenging ability.
  • the composition for external use containing 2-methylthiazolidine-2,4-dicarboxylic acid showed a practical level of hydrogen peroxide scavenging ability even at 0.5 w / v%.
  • Example 3 Whether 2-thiothiazolidine-4-carboxylic acid-containing external composition and 2-methylthiazolidine-2,4-dicarboxylic acid-containing external composition have the ability to inhibit tyrosinase activity at a practical level as cosmetics I confirmed that.
  • the practical level of tyrosinase activity inhibition ability refers to the time when the tyrosinase activity inhibition rate is 50% or more.
  • the tyrosinase activity inhibition ability was confirmed as follows. Tyrosinase and tyrosine were each dissolved in 0.67 M phosphate buffer (pH 6.8) to prepare solution concentrations of 50 U / mL and 0.03 w / v%, respectively.
  • test compound was dissolved in water and adjusted to a 0.5 w / v% solution concentration to obtain a test compound solution.
  • 1.2 mL of tyrosine solution and tyrosinase solution were added to 1.2 mL of the test compound solution and mixed. Then, it heated at 30 degreeC for 30 minutes, and was set as the test solution.
  • 1.2 mL each of tyrosine solution and tyrosinase solution was added to 1.2 mL of water and mixed. Then, it heated at 30 degreeC for 30 minutes, and was set as the blank test solution.
  • Absorbances A T and A B at a wavelength of 475 nm were measured for the test solution and the blank test solution.
  • the tyrosinase activity inhibition rate of the test compound was calculated by the following formula (Equation 3), and tyrosinase inhibitory ability was determined.
  • Equation 3 The tyrosinase activity inhibition rate of the test compound was calculated by the following formula (Equation 3), and tyrosinase inhibitory ability was determined.
  • Equation 3 both 2-thiothiazolidine-4-carboxylic acid-containing external composition and 2-methylthiazolidine-2,4-dicarboxylic acid-containing external composition are sufficiently practical at 0.5 w / v%. Showed the ability to inhibit tyrosinase activity.
  • Example 5 Often, sulfur-containing compounds are problematic due to their unpleasant and strong pungent odor. Therefore, a sensory test was conducted on the odor of 2-thiothiazolidine-4-carboxylic acid or 2-methylthiazolidine-2,4-dicarboxylic acid used in the present invention.
  • the sensory test of odor was performed as follows. A sensory test by olfaction was performed by 14 monitor men and women (9 men and 5 women) randomly selected by weighing 0.5 g of each test compound. The evaluation was a five-level evaluation, and the average score of 14 people was shown.
  • 2-thiothiazolidine-4-carboxylic acid or 2-methylthiazolidine-2,4-dicarboxylic acid used in the present invention has no odor problem.
  • Example 6 Whether the composition for external use containing 2-thiothiazolidine-4-carboxylic acid and the composition for external use containing 2-methylthiazolidine-2,4-dicarboxylic acid have stability at a practical level as cosmetics Confirmed.
  • the test compound was dissolved in water and adjusted to a 5.0 w / v% solution concentration to obtain a test compound solution. Like the test compound, it has radical scavenging ability, hydrogen peroxide scavenging ability, tyrosinase activity inhibiting ability, and L-cysteine compounded in cosmetics etc. is dissolved in water as a comparative compound in the same manner to a 5.0 w / v% solution concentration. A comparative compound solution was prepared.
  • a 1.0 w / v% test compound solution was prepared and allowed to stand at 40 ° C. and 75% RH for a certain time, and the content of the test compound was measured by HPLC.
  • the content of the test compound immediately after preparation is 100%, the content after standing for 24 hours is 90% or more for both 2-thiothiazolidine-4-carboxylic acid solution and 2-methylthiazolidine-2,4-dicarboxylic acid solution. there were. Further, regarding the 2-thiothiazolidine-4-carboxylic acid solution, the content did not decrease even after being allowed to stand for 1 month.

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Abstract

La présente invention concerne une composition externe qui peut être utilisée en tant que préparation externe pour la peau ou en tant que cosmétique qui possède un excellent effet d’élimination de l’oxygène actif, un effet d’inhibition de la tyrosinase et un effet réducteur et qui exerce une fonction antivieillissement basée sur l’effet antioxydant et une fonction de blanchiment basée sur l’effet d’inhibition de la tyrosinase, un cosmétique capillaire qui empêche les cheveux d’être endommagés, et un agent pour permanente, un agent qui boucle les cheveux, un agent de lissage des cheveux indisciplinés, un colorant capillaire et ainsi de suite, lesquels sont basés sur l’effet réducteur sur une liaison disulfure.  L’invention concerne une composition externe caractérisée par la présence d’un ou de plusieurs éléments choisis parmi l’acide 2-thiothiazolidine-4-carboxylique représenté par la formule chimique (1) ou un dérivé de celui-ci et l’acide 2-méthylthiazolidine-2,4-dicarboxylique représenté par la formule chimique (2) ou un dérivé de celui-ci ou un sel de celui-ci.
PCT/JP2009/052524 2008-06-19 2009-02-16 Composition externe WO2009154014A1 (fr)

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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
WO2013081192A1 (fr) * 2011-11-30 2013-06-06 味の素株式会社 Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif
CN116285096A (zh) * 2022-12-16 2023-06-23 沪金(苏州)实业有限公司 一种长效抗菌聚丙烯盛装容器及制造方法

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KR101496795B1 (ko) 2010-05-28 2015-03-02 아지노모토 가부시키가이샤 시스테인 유도체
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KR101628589B1 (ko) 2011-11-30 2016-06-08 아지노모토 가부시키가이샤 미백 화장료
WO2013081146A1 (fr) * 2011-11-30 2013-06-06 味の素株式会社 Produit cosmétique antirides
JP6222888B2 (ja) * 2011-12-22 2017-11-01 ホーユー株式会社 毛髪及び皮膚外用剤組成物、並びに非治療的な美容方法
CN103800215A (zh) * 2014-03-07 2014-05-21 澳宝化妆品（惠州）有限公司 一种皮肤防晒组合物
KR102383798B1 (ko) * 2014-11-26 2022-04-07 나노리소스 주식회사 항산화 나노다이아몬드 제조방법 및 이를 포함하는 조성물
US10933010B2 (en) 2015-05-11 2021-03-02 Hayashibara Co., Ltd. External dermal agent
EP4123013A1 (fr) * 2020-03-16 2023-01-25 Ajinomoto Co., Inc. Procédé de culture de cellules animales

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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
WO2013081192A1 (fr) * 2011-11-30 2013-06-06 味の素株式会社 Produit cosmétique contenant un dérivé de cystéine et un agent tensio-actif
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CN116285096A (zh) * 2022-12-16 2023-06-23 沪金(苏州)实业有限公司 一种长效抗菌聚丙烯盛装容器及制造方法
CN116285096B (zh) * 2022-12-16 2024-03-26 沪金(苏州)实业有限公司 一种长效抗菌聚丙烯盛装容器及制造方法

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