Topical skin components

The combination of diallyl quaternary ammonium salt polymers and hydrating agents in skin care compositions enhances skin hydration and retention, addressing the inadequacies of conventional moisturizers.

JP7813838B2Active Publication Date: 2026-02-13POLA CHEMICAL INDUSTRIES INC
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Patent Information

Application Number
JP2024103750
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2024-06-27
Publication Date
2026-02-13
Estimated Expiration
2039-12-27

AI Technical Summary

Technical Problem

Conventional moisturizing agents in skin care cosmetics fail to provide sufficient hydration and retention, leading to a dry or tight skin feeling after application.

Method used

A composition comprising a diallyl quaternary ammonium salt polymer and/or copolymer, such as dimethyldiallylammonium chloride, combined with hydrating agents like alkyl glycosides, sucrose fatty acid esters, cellulose derivatives, and hyaluronic acid derivatives, to enhance skin hydration and retention.

Benefits of technology

The composition significantly improves the skin's hydration capacity by retaining hydrating agents for a longer period, providing a moisturized feeling, especially beneficial for skin cleansers.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

To provide a technique for further improving a water-holding ability of epidermis.SOLUTION: A skin external composition contains a polymer and / or copolymer of a diallyl quaternary ammonium salt, and a water-holding agent. Preferably, the water-holding agent is an alkyl glycoside represented by the general formula (1) in the figure, where N represents an integer from 2 to 7, each R independently represents a hydrogen atom or C1-3 alkyl group, and n represents an integer from 1 to 4.SELECTED DRAWING: Figure 3
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Description

[Technical Field]

[0001] The present invention relates to a composition for external use on the skin. [Background technology]

[0002] Compositions for topical application to the skin, such as skin care cosmetics, are expected to have an excellent feel on the skin after application. In particular, skin cleansers, such as facial cleansers and cleansing agents, are required to not only sufficiently remove dirt such as makeup cosmetics and sebum, but also to leave the skin feeling good after application. In particular, there is a demand for the products to leave the skin feeling moisturized without causing tightness after washing. For this reason, various moisturizing agents have been incorporated into topical skin compositions. Conventional moisturizing agents include oils and polymers that can form a film on the skin surface to inhibit water evaporation, and water-holding agents such as hyaluronic acid.

[0003] Recently, due to concerns about biological safety and environmental impact, various sugar-based surfactants have been proposed as renewable surfactants with low environmental impact, instead of conventional synthetic surfactants derived from petroleum. For example, isoprenoid chain polyglycosides disclosed in Patent Document 1 have been proposed as sugar-based surfactants with a Krafft temperature lower than room temperature and capable of widely controlling the balance between hydrophilicity and hydrophobicity. Furthermore, Patent Document 2 describes that an oil-in-water emulsion composition containing an alkyl glycoside has an excellent moisturizing effect.

[0004] Furthermore, cationic polymers such as polymers obtained using dimethyldiallylammonium chloride as a monomer are widely used in external skin preparations as components that impart smoothness to hair and the like. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 3882067 [Patent Document 2] Patent No. 6544956 Summary of the Invention [Problem to be solved by the invention]

[0006] In skin care cosmetic and other external compositions for skin application, it is desirable to provide a moisturizing feeling to the skin after application, but conventionally used moisturizers are not sufficient. In view of this situation, a technique for further improving the water-holding capacity of the epidermis is provided. [Means for solving the problem]

[0007] As a result of intensive research conducted by the inventors to solve the above problems, they discovered that certain polymers have the property of retaining components that improve the epidermis' water-holding capacity in the epidermis, and as a result they came to the realization that the epidermis' water-holding capacity can be further increased, leading to the completion of the present invention.

[0008] That is, the present invention is as follows. [1] A composition for external use on the skin, comprising a polymer and / or copolymer of a diallyl quaternary ammonium salt and a hydrating agent. [2] A composition for topical application to the skin, wherein the hydrating agent is selected from alkyl glycosides, sucrose fatty acid esters, cellulose and its derivatives, and hyaluronic acid and its derivatives. [3] The alkyl glycoside is an alkyl glycoside represented by the following general formula (1): The topical skin composition described in [2].

[0009] [ka] (In the formula, N represents an integer of 2 to 7, R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n represents an integer of 1 to 4.)

[0010] [4] The composition for external use on skin according to any one of [1] to [3], wherein the diallyl quaternary ammonium salt is dimethyldiallylammonium chloride. [5] The composition for external use on the skin according to any one of [1] to [4], which contains the polymer and / or copolymer of the diallyl quaternary ammonium salt in an amount of 0.1 to 5% by mass based on the total mass of the composition. [6] The composition for external use on skin according to any one of [1] to [5], wherein the hydrating agent is contained in an amount of 0.01 to 1% by mass based on the total amount of the composition. [7] The composition for external use on skin according to any one of [1] to [6], wherein the mass ratio of the content of the diallyl quaternary ammonium salt polymer and / or copolymer to the content of the hydrating agent is 50:1 to 1:10. [8] The composition for external use on skin according to any one of [1 to [7]], which is a cleansing agent. [9] An agent for improving the skin retention of a hydrating agent, which contains a polymer and / or copolymer of a diallyl quaternary ammonium salt.

[10] The skin retention improver according to [9], wherein the diallyl quaternary ammonium salt is dimethyldiallylammonium chloride. [Effects of the Invention]

[0011] The skin retention improver of the present invention allows a hydrating agent to be retained in the epidermis for a longer period of time or in a larger amount. Therefore, a composition containing the skin retention improver of the present invention in combination with a hydrating agent can further improve the hydration capacity of the epidermis, and is therefore suitable as a topical skin composition with excellent moisturizing properties. In particular, since skin cleansers are in contact with the skin for a relatively shorter period of time than other skin care cosmetics, it is useful to be able to increase the hydration capacity of the skin (epidermis) in a short period of time and provide a moisturized feeling. [Brief explanation of the drawings]

[0012] [Figure 1] Graph showing the amount of Mal2Far in the supernatant when the amount of keratin powder was changed (100% was set when the amount of keratin powder was 0 mg / mL). [Figure 2] A graph showing the amount of dehydration per gram of keratin powder. [Figure 3]A graph showing the weight gain per gram of keratin powder. DETAILED DESCRIPTION OF THE INVENTION

[0013] The composition of the present invention contains a diallyl quaternary ammonium salt polymer and / or copolymer and a hydrating agent.

[0014] The diallyl quaternary ammonium salt polymer and / or copolymer refers to a polymer containing a diallyl quaternary ammonium salt as a monomer unit. Dimethyl diallyl ammonium chloride is more preferred as the diallyl quaternary ammonium salt. Examples of monomer units other than the diallyl quaternary ammonium salt include, but are not limited to, acrylic acid, methacrylic acid, acrylamide, and methacrylamide.

[0015] Specific examples of the polymer or copolymer of a diallyl quaternary ammonium salt include, for example, dimethyldiallylammonium chloride polymer (polydimethylmethylenepiperidinium chloride) (Polyquaternium-6), acrylic acid amide / dimethyldiallylammonium chloride copolymer (Polyquaternium-7), dimethyldiallylammonium chloride / acrylic acid copolymer (Polyquaternium-22), acrylic acid / diallyl quaternary ammonium salt / acrylamide copolymer (Polyquaternium-39), and the like, and these can be used alone or in combination. The molecular weight of these polymers or copolymers is not particularly limited, and may be of a size typically used in topical skin preparations such as cosmetics, for example, those having a molecular weight of 10,000 to 10,000,000 as measured by GPC under typical conditions.

[0016] The diallyl quaternary ammonium salt polymer or copolymer can retain the coexisting hydrating agent in the epidermis of the skin for a long period of time or in a large amount. Therefore, the present specification provides a new use of a diallyl quaternary ammonium salt polymer and / or copolymer to improve the skin retention of a hydrating agent. That is, another aspect of the present invention is an agent for improving the skin retention of a hydrating agent, which contains a diallyl quaternary ammonium salt polymer and / or copolymer.

[0017] The content of the diallyl quaternary ammonium salt polymer and / or copolymer in the composition of the present invention is preferably 0.01 to 5 mass %, more preferably 0.1 to 5 mass %, and even more preferably 0.2 to 1.0 mass % of the total composition. Furthermore, the content of the diallyl quaternary ammonium salt polymer and / or copolymer in the composition of the present invention is, in terms of the content of dimethyldiallylammonium chloride, the monomer contained in the polymer, preferably 0.01 to 5 mass%, more preferably 0.05 to 3.0 mass%, and even more preferably 0.1 to 1.0 mass%, of the total composition. By using the hydrating agent in such a range, it becomes easier to retain the hydrating agent in the epidermis (stratum corneum) for a longer period or in a larger amount.

[0018] The water-holding agent in the present invention is not particularly limited as long as it can hold (store, bind, hydrate) water, but preferred examples include alkyl glycosides, sucrose fatty acid esters, cellulose and its derivatives, and hyaluronic acid and its derivatives.

[0019] Alkyl glycosides are sugar residues to which alkyl groups are linked via ether bonds. Here, the sugar residue is preferably selected from galactose, xylose, mannose, lyxose, arabinose, fructose, maltose, xylobiose, isomaltose, cellobiose, lactose, gentiobiose, maltotriose, isomaltotriose, cellotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, isomaltotetraose, isomaltopentaose, isomaltohexaose, and isomaltoheptase. The alkyl group preferably has 8 to 24 carbon atoms, more preferably 10 to 20 carbon atoms, and even more preferably 10 to 16 carbon atoms, and may be branched.

[0020] The alkyl glycoside in the present invention is more preferably an alkyl glycoside represented by the following general formula (1).

[0021] [ka]

[0022] In general formula (1), N represents an integer of 2 to 7. R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a methyl group. n represents an integer of 1 to 4, preferably 2 or 3, and more preferably 2. In other words, the alkyl glycoside represented by general formula (1) has a structure in which the hydroxyl group at the 1-position of the terminal sugar of the oligosaccharide is bonded (condensed) with an aliphatic alcohol. The aliphatic alcohol is preferably an aliphatic alcohol having 12 to 20 carbon atoms, more preferably 12 to 16 carbon atoms, and even more preferably 15 carbon atoms, which may be branched.

[0023] The sugar residue in the alkyl glycoside represented by general formula (1) is the hydrophilic part. Sugar residues include maltose, maltotriose, maltotetraose, maltopentaose, maltohexaose, and maltoheptaose, with maltose and maltotriose being more preferred.

[0024] In general formula (1), the fatty chain is the hydrophobic portion of the alkyl glycoside of the present invention. The fatty chain portion may or may not be branched, but preferably has a branched chain. That is, in general formula (1), R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group.

[0025] The alkyl glycoside according to the present invention is more preferably a compound represented by the following general formula (2).

[0026] [ka]

[0027] In the general formula (2), N represents an integer of 2 to 7. n represents an integer of 1 to 4, more preferably 2 or 3, and even more preferably 2. Examples of compounds encompassed by general formula (2) include, but are not limited to, Mal2Far (a glycoside of maltose and hexahydrofarnesol), Mal3Far (a glycoside of maltotriose and hexahydrofarnesol), and Mal3Phyt (a glycoside of maltotriose and hexahydrophytol).

[0028] As shown in the Reference Examples below, the alkyl glycosides according to the present invention can bind (adsorb) to keratin, the main component of the stratum corneum. Such binding is reversible and occurs within a short period of time. Furthermore, in the stratum corneum to which the alkyl glycoside according to the present invention is bound, the water-holding capacity is improved and the amount of water retained is increased, so that an improvement in the skin's barrier function is also expected.

[0029] The alkyl glycosides of the present invention can be obtained by various well-known methods, such as glycosylation methods using sugar bromides, glycosylation methods using sugar fluorides, glycosylation methods using trichloroacetimidate, and glycosylation methods using acetylated sugars. More specific examples include the synthesis processes described in Japanese Patent Nos. 3882067, 4817435, and 5207420, as well as JP-A Nos. 2013-129660 and 2012-17318.

[0030] Other hydrating agents besides alkyl glycosides include sucrose fatty acid esters, cellulose and its derivatives, hyaluronic acid and its derivatives, and the like. Examples of sucrose fatty acid esters include mono-, di-, or triesters of sucrose with fatty acids having 8 to 18 carbon atoms. More specifically, preferred examples include, but are not limited to, sucrose polylaurate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose distearate, and sucrose stearate. Preferred examples of cellulose and its derivatives include, but are not limited to, cellulose, hydroxypropylmethylcellulose, and hydroxyethylcellulose. Preferred examples of hyaluronic acid and its derivatives include, but are not limited to, hyaluronic acid, acetyl hyaluronic acid, and the like.

[0031] The content of the hydrating agent in the composition of the present invention is preferably 0.01 to 1 mass %, more preferably 0.05 to 1 mass %, of the total composition. By using it in such a range, the amount of water held by the epidermis (stratum corneum) can be easily increased.

[0032] The mass ratio of the contents of the diallyl quaternary ammonium salt polymer and / or copolymer to the hydrating agent in the composition of the present invention is preferably 50:1 to 1:10, more preferably 50:1 to 1:5, and even more preferably 30:1 to 1:1. By incorporating a combination of ingredients in such ranges, it becomes easier to further improve the skin retention of the hydrating agent.

[0033] The composition of the present invention has the effect of improving the skin retention of the hydrating agent due to the action of the diallyl quaternary ammonium salt polymer and / or copolymer, thereby enhancing the hydration capacity of the skin (epidermis).For this reason, it is particularly preferable to apply it to the skin externally.

[0034] The composition for external use on the skin is preferably in the form of a cosmetic or a quasi-drug, more preferably a skin care cosmetic, even more preferably a cleanser, and more specifically, examples thereof include cleansing agents, facial washes, body soaps, and hand soaps. The dosage form of the composition of the present invention is not particularly limited, and preferred examples include liquid dosage forms such as lotions and essences, oil dosage forms, gel dosage forms, solid dosage forms, and emulsion dosage forms such as lotions and creams.

[0035] The composition of the present invention can be produced according to a conventional method.

[0036] The composition of the present invention may optionally contain other ingredients commonly used in cosmetics, provided that the effects of the present invention are not impaired. Examples of such optional ingredients include alcohols, ethers, powders, oils, moisturizers, surfactants, sequestering agents, pearlescent agents, amino acids, organic amines, polymer emulsions, pH adjusters, vitamins, antioxidants, preservatives, water-soluble polymers, fragrances, and various active ingredients.

[0037] Examples of alcohols include dihydric alcohols such as ethylene glycol, 1,3-butylene glycol, trimethylene glycol, 1,2-butylene glycol, propylene glycol, dipropylene glycol, propanediol, 1,2-pentanediol, 3-methyl-1,3-butanediol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, and octylene glycol; trihydric alcohols such as trimethylolpropane; tetrahydric alcohols such as pentaerythritol; pentahydric alcohols such as xylitol; polyhydric alcohol polymers such as triglycerin, tetraglycerin, and polyglycerin; sugar alcohols such as starch hydrolysis sugar reduced alcohols; and polyglycerin. alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, and ethylene glycol isopropyl ether; alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, and dipropylene glycol butyl ether; glycerin monoalkyl ethers such as xyl alcohol, selachyl alcohol, and batyl alcohol; Alcohol polymers such as diethylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, and polyethylene glycol; Examples include glycerol; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl alcohol; POP-butyl ether; POP·POE-butyl ether; tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphate; POP·POE-pentaneerythritol ether, etc.

[0038] In addition to the above alcohols, ethers include: Examples of the ethylene glycol dimethyl ether include ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and propylene glycol monophenyl ether acetate.

[0039] The powder may be spherical, needle-like, plate-like, or any other suitable shape, and examples thereof include inorganic powders (e.g., talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, lepidolite, biotite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, etc.) , barium silicate, calcium silicate, magnesium silicate, strontium silicate, tungstate metal salts, magnesium, silica, alumina, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, boron nitride, etc.); organic powders (e.g., polyamide resin powder (nylon powder), polyethylene powder, poly(methyl meth)acrylate powder, polystyrene powder, styrene-acrylic acid copolymer resin powder, silicone resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.); metal soaps (e.g., mica, Zinc stearate, calcium palmitate, aluminum stearate); inorganic white pigment (e.g., titanium dioxide, zinc oxide, etc.); inorganic red pigments (e.g., iron oxide (red iron oxide), iron titanate, etc.); inorganic brown pigments (e.g., gamma-iron oxide, etc.); inorganic yellow pigments (e.g., yellow iron oxide, ochre, etc.); inorganic black pigments (e.g., black iron oxide, low-order titanium oxide, etc.); inorganic purple pigments (e.g., mango violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, Prussian blue, etc.); pearl pigments (e.g., titanium dioxide-coated mica, titanium dioxide-coated bismuth oxychloride, titanium dioxide-coated talc, colored titanium dioxide-coated mica, bismuth oxychloride, fish scales, etc.) foil, etc.); metal powder pigments (e.g., aluminum powder, copper powder, etc.); organic pigments such as zirconium, barium, or aluminum lake (e.g., organic pigments such as Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 226, Red No. 228, Red No. 405, Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401, and Blue No. 404, Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3, and Blue No. 1); natural pigments (e.g., chlorophyll, beta-carotene, etc.), etc.

[0040] Examples of oil agents include silicone oil, polar oil, natural oil, and hydrocarbon oil.

[0041] Silicone oils include dimethylpolysiloxane (dimethicone), cyclopentasiloxane, decamethylcyclopentasiloxane, caprylyl methicone, dimethicone / vinyl dimethicone crosspolymer, and dimethicone / phenyl vinyl dimethicone crosspolymer. - etc.

[0042] Polar oils include synthetic ester oils such as isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, 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-ethylhexylate, trimethylolpropane triisostearate, pentaneerythritol tetra-2-ethylhexylate, ... Glyceryl 2-ethylhexanoate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, glycerin trimyristate, tri-2-heptylundecanoic acid glyceride, castor oil fatty acid methyl ester, oleic acid oil, cetostearyl alcohol, acetoglyceride, 2-heptylundecyl palmitate, diisobutyl adipate, N-lauroyl Examples of suitable oleic acid surfactants include 2-octyldodecyl L-glutamate, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, ethyl acetate, butyl acetate, amyl acetate, triethyl citrate, and octyl methoxycinnamate.

[0043] Examples of natural oils include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, camellia oil, castor oil, linseed oil, safflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, Japanese kaya oil, rice bran oil, Chinese tung oil, Japanese tung oil, jojoba oil, germ oil, sunflower oil, triglycerin, glycerin trioctanoate, and glycerin triisopalmitate.

[0044] Examples of hydrocarbon oils include isododecane, isohexadecane, squalane, hydrogenated poly(C6-12)olefin, and hydrogenated polyisobutene.

[0045] Examples of moisturizing agents include chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO)PO adduct, Rosa robur extract, yarrow extract, and melilot extract.

[0046] Surfactants include anionic surfactants, cationic surfactants, amphoteric surfactants, and nonionic surfactants.

[0047] Examples of anionic surfactants include fatty acid soaps (e.g., sodium laurate, sodium palmitate, etc.); higher alkyl sulfates (e.g., sodium lauryl sulfate, potassium lauryl sulfate, etc.); alkyl ether sulfates (e.g., POE triethanolamine lauryl sulfate, POE sodium lauryl sulfate, etc.); N-acyl sarcosinates (e.g., sodium lauroyl sarcosinate, etc.); higher fatty acid amide sulfonates (e.g., sodium N-myristoyl-N-methyl taurate, sodium coconut oil fatty acid methyl tauride, sodium lauryl methyl tauride, etc.); phosphate salts (sodium POE oleyl ether phosphate, sodium POE stearyl ether phosphate, etc.); sulfosuccinates (e.g., sodium di-2-ethylhexyl sulfosuccinate, sodium monolauroyl monoethanolamide polyoxyethylene sulfosuccinate, sodium lauryl polypropylene glycol sulfosuccinate, etc.); sodium carboxylate, etc.); alkylbenzenesulfonates (e.g., sodium linear dodecylbenzenesulfonate, triethanolamine linear dodecylbenzenesulfonate, linear dodecylbenzenesulfonic acid, etc.); higher fatty acid ester sulfate salts (e.g., sodium hydrogenated coconut oil fatty acid glycerin sulfate, etc.); N-acylglutamates (e.g., monosodium N-lauroylglutamate, disodium N-stearoylglutamate, monosodium N-myristoyl-L-glutamate, etc.); sulfated oils (e.g., turmeric oil, etc.); POE alkyl ether carboxylic acids; POE alkyl allyl ether carboxylate salts; α-olefin sulfonates; higher fatty acid ester sulfonates; secondary alcohol sulfate salts; higher fatty acid alkylolamide sulfate salts; sodium lauroylmonoethanolamide succinate; ditriethanolamine N-palmitoyl aspartate; sodium caseinate, etc.

[0048] Examples of cationic surfactants include alkyltrimethylammonium salts (e.g., stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.); alkylpyridinium salts (e.g., cetylpyridinium chloride, etc.); distearyldimethylammonium chloride dialkyldimethylammonium salts; poly(N,N'-dimethyl-3,5-methylenepiperidinium chloride); alkyl quaternary ammonium salts; alkyldimethylbenzylammonium salts; alkylisoquinolinium salts; dialkylmorphonium salts; POE alkylamines; alkylamine salts; polyamine fatty acid derivatives; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride, etc.

[0049] Examples of amphoteric surfactants include imidazoline-based amphoteric surfactants (e.g., 2-undecyl-N,N,N-(hydroxyethylcarboxymethyl)-2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt, etc.); betaine-based surfactants (e.g., 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkyl betaine, amido betaine, sulfobetaine, etc.).

[0050] Nonionic surfactants include polyether-modified silicones (e.g., polyethylene glycol-10 dimethicone, polyethylene glycol-12 dimethicone, etc.); polyglycerin-modified silicones (e.g., polyglyceryl-3 disiloxane dimethicone, polyglyceryl-3 polydimethylsiloxyethyl dimethicone, etc.); sorbitan fatty acid esters (e.g., sorbitan monooleate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, penta-2 2-ethylhexyl diglycerol sorbitan, tetra-2-ethylhexyl diglycerol sorbitan, etc.); glycerin fatty acids (e.g., mono-cottonseed oil fatty acid glycerin, monoerucate glycerin, sesquioleate glycerin, monostearate glycerin, α,α'-oleic acid pyroglutamic acid glycerin, monostearate malate, etc.); propylene glycol fatty acid esters (e.g., propylene glycol monostearate, etc.); POE castor oil / hydrogenated castor oil derivatives (POE castor oil, POE hydrogenated castor oil, etc.); and non-hydrophilic nonionic surfactants such as glycerin alkyl ethers. Also, polyglycerol fatty acid esters (e.g., polyglyceryl monooleate, polyglyceryl monostearate, etc.); POE sorbitan fatty acid esters (e.g., POE sorbitan monooleate, POE sorbitan monostearate, POE sorbitan tetraoleate, etc.); POE sorbit fatty acid esters (e.g., POE sorbit monolaurate, POE sorbit monooleate, POE sorbit pentaoleate, POE sorbit monostearate, etc.); POE glycerin fatty acid esters (e.g., POE monooleates such as POE glycerin monostearate, POE glycerin monoisostearate, POE glycerin triisostearate, etc.); POE fatty acid esters (e.g., POE distearate, POE monodioleate, ethylene glycol distearate, etc.);POE alkyl ethers (e.g., POE lauryl ether, POE oleyl ether, POE stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, POE cholestanol ether, etc.); POE alkyl phenyl ethers (e.g., POE nonylphenyl ether, etc.); Pluronic types (e.g., Pluronic, etc.); POE·POP alkyl ethers (e.g., POE·POP cetyl ether, POE·POP-2-decyltetradecyl ether, POE·POP monobutyl ether, POE·POP hydrogenated lanolin, POE·POP glycerin ether, etc.); tetra POE-tetra-POP ethylenediamine condensates (e.g., Tetronic, etc.); POE castor oil hydrogenated castor oil derivatives (e.g., POE castor oil, POE hydrogenated castor oil, POE hydrogenated castor oil monoisostearate, POE hydrogenated castor oil triisostearate, POE hydrogenated castor oil monopyroglutamic acid monoisostearate diester, POE hydrogenated castor oil maleic acid, etc.); POE beeswax and lanolin derivatives (e.g., POE sorbitan beeswax, etc.); alkanolamides (e.g., coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide, etc.); POE propylene glycol fatty acid esters; POE alkylamines; POE fatty acid amides; sucrose fatty acid esters; other alkyl glycosides; alkylethoxydimethylamine oxide; and hydrophilic nonionic surfactants such as trioleyl phosphate.

[0051] Examples of sequestering agents include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, edetate disodium, edetate trisodium, edetate tetrasodium, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, and ethylenediaminehydroxyethyltriacetate trisodium salt.

[0052] Examples of pearlescent agents include glycol distearate and titanium mica.

[0053] Examples of the amino acid include neutral amino acids (e.g., threonine, cysteine, etc.); basic amino acids (e.g., hydroxylysine, etc.); and the amino acid derivatives include, for example, acyl sarcosine sodium (sodium lauroyl sarcosine), acyl sarcosine sodium (sodium lauroyl sarcosine), Examples of the anti-inflammatory agent include glutamic acid salts, acyl β-alanine sodium, glutathione, and pyrrolidone carboxylic acid.

[0054] Examples of organic amines include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol.

[0055] Examples of polymer emulsions include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacrylic alkyl ester emulsion, polyvinyl acetate resin emulsion, and natural rubber latex.

[0056] Examples of pH adjusters include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.

[0057] Vitamins include, for example, vitamins A, B1, B2, B6, C, E and their derivatives. , pantothenic acid and its derivatives, biotin, etc.

[0058] Examples of antioxidants include tocopherols, dibutylhydroxytoluene (BHT), butylhydroxyanisole, pyrosulfite, gallic acid ester, phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, cephalin, hexametaphosphate, phytic acid, and ethylenediaminetetraacetic acid.

[0059] Examples of preservatives include parabens and phenoxyethanol.

[0060] Examples of water-soluble polymers include plant-based polymers (e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (marmelo), algae colloid (cassow extract), starch (coconut oil), and the like. (corn, potato, wheat), glycyrrhizic acid); microbial polymers (e.g. natural water-soluble polymers such as xanthan gum, dextran, succinoglucan, pullulan, etc.; animal polymers (e.g., collagen, casein, albumin, gelatin, etc.); semi-synthetic water-soluble polymers such as starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (hydroxypropylmethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylcellulose, hydroxypropylmethylcellulose stearoxy ether, sodium cellulose sulfate, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder, etc.); alginic acid-based polymers (e.g., sodium alginate, propylene glycol alginate, etc.), etc. Examples include synthetic water-soluble polymers such as vinyl polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene polymers (e.g., polyethylene glycol 20,000, 40,000, 60,000, etc.); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; and cationic polymers.

[0061] Examples of various active ingredients include anti-inflammatory agents (e.g., glycyrrhizinic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (e.g., placenta extract, saxifrage extract, arbutin, etc.); various extracts (e.g., Phellodendron bark, Coptis chinensis, Lithospermum root, Peony, Swertia japonica, Birch, sage, Loquat, Carrot, Aloe, Mallow, Iris, Grape, Job's tears, Luffa, Lily, Saffron, Cnidium rhizome, Angelica acutiloba, St. John's wort, Ononis, Garlic, Capsicum annuum, Tangerine peel, Angelica acutiloba, Seaweed, etc.), activators (e.g., Royal jelly, , photosensitizers, cholesterol derivatives, etc.); blood circulation promoters (e.g., nonylic acid valenylamide, nicotinic acid benzyl ester, nicotinic acid β-butoxyethyl ester, capsaicin, zingerone, cantharides tincture, ichthammol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthine, γ-oryzanol, etc.); antiseborrheic agents (e.g., sulfur, thianthol, etc.); anti-inflammatory agents (e.g., tranexamic acid, thiotaurine, hypotaurine, etc.), etc. [Example]

[0062] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples as long as it does not depart from the gist of the invention.

[0063] <Reference Example 1> Examination of the binding between keratin and alkyl glycosides The following procedure was used to examine whether alkyl glycoside (Mal2Far) binds to keratin, the main component of the stratum corneum. Keratin powder (Keratin from wool K0044, Tokyo Chemical Industry Co., Ltd.) was placed in 2 mL Eppendorf tubes at 1.2, 6, 12, or 60 mg each, and 1.2 mL of a 0.5 mg / mL Mal2Far solution was added and incubated at 40°C for 3 hours. The Eppendorf tubes were centrifuged (15,000 rpm, room temperature, 3 minutes, 3 times), and 1 mL of the supernatant was collected. The amount of Mal2Far not bound to the keratin powder in the supernatant was quantified using Corona HPLC. The HPLC conditions were as follows: Column: Atlantis T3 (100 x 3.0 mm, 3.5 μm) Solvent: A: water, B: acetonitrile Gradient: B 10% (-30 min) → 10% (0 min) → 98% (30 min) → 98% (35 min) Detection: Corona CAD Flow rate: 0.3 mL / min Column temperature: 40℃ Syringe washing: 50% acetonitrile aqueous solution Inject: 1 μL

[0064] The results are shown in Figure 1. The amount of Mal2Far in the supernatant decreased in a keratin powder amount-dependent manner, indicating that Mal2Far bound to the keratin powder.

[0065] <Reference Example 2> Examination of water-holding ability of keratin bound with alkyl glycosides The water-holding ability of keratin bound with alkyl glycoside (Mal2Far) was examined by the following procedure. The weights of Petri dishes 1 to 3 were measured in advance. Approximately 150 mg of keratin powder was weighed into Petri dish 1, and 3 mL of a 0.5 mg / mL Mal2Far aqueous solution was added. Approximately 150 mg of keratin powder was weighed into Petri dish 2, and 3 mL of water was added. 3 mL of a 0.5 mg / mL Mal2Far aqueous solution was added to Petri dish 3. Petri dishes 1 to 3 were incubated at 40°C for 10 minutes, then placed in a desiccator and dried overnight under reduced pressure. The weight of each Petri dish (including its contents) after drying was measured, and the amount of dehydration per 1 g of keratin powder was calculated. The amount of dehydration per 1 g of keratin powder was calculated using the following formula:

[0066]

number

[0067] The results are shown in Figure 2. The keratin powder with added Mal2Far exhibited less water evaporation than the keratin powder without added Mal2Far, indicating that the water-holding capacity of the stratum corneum to which Mal2Far was adsorbed was improved.

[0068] Example 1: Examination of the effect of the composition of the present invention on the water-holding capacity of keratin powder 2 The effect of the composition of the present invention on the water-holding ability of the stratum corneum was examined by the following procedure. The compositions shown in Table 1 were prepared by conventional methods. Keratin powder was weighed in 0 mg or approximately 150 mg amounts into pre-weighed petri dishes. 3 mL of an aqueous solution prepared by diluting the composition of the Example or Comparative Example contained in each petri dish 10 times with water was added to each dish, and the dish was incubated at 40°C for 10 minutes. After incubation, each petri dish was placed in a desiccator and dried overnight under reduced pressure. The weight of each petri dish (including its contents) after drying was measured, and the weight increase per 1 g of keratin powder was calculated in the same manner as in Reference Example 2, where the amount of dehydration was calculated.

[0069] [Table 1]

[0070] The results are shown in Figure 3. The keratin powder to which the composition of Example 1 was added had a higher viscosity than the keratin powders of Comparative Examples 1 to 3. The water was less likely to evaporate than with the keratin powder to which the composition had been added, and a significant increase in water retention was observed. This indicates that the composition of the present invention further improves the water retention capacity of the stratum corneum. [Industrial Applicability]

[0071] The skin retention improver of the present invention allows a hydrating agent to be retained in the epidermis for a longer period of time or in a larger amount. Therefore, a composition containing the skin retention improver of the present invention in combination with a hydrating agent can further improve the hydration capacity of the epidermis, and is therefore suitable as a topical skin composition with excellent moisturizing properties. In particular, since skin cleansers are in contact with the skin for a relatively shorter time than other skin care cosmetics, the ability to increase the hydration capacity of the skin (epidermis) in a short period of time and impart a moisturizing feel is extremely useful industrially.

Claims

1. A composition for external use on the skin containing a polymer and / or copolymer of a diallyl quaternary ammonium salt and a hydrating agent, the diallyl quaternary ammonium salt is dimethyldiallylammonium chloride, The hydrating agent is an alkyl glycoside represented by the following general formula (2): 【Chemistry 1】 (In the formula, N represents an integer of 2 to 7, and n represents an integer of 1 to 4.) The composition contains the diallyl quaternary ammonium salt polymer and / or copolymer in an amount of 0.01 to 5% by mass based on the total mass of the composition, A composition for external use on skin, containing the hydrating agent in an amount of 0.01 to 1% by mass based on the total amount of the composition.

2. The hydrating agent is a glycoside of maltose and hexahydrofarnesol (Mal) represented by the general formula (2): 2 The composition for external use on skin according to claim 1, wherein the composition is a hydroxybenzoate (HPO4)-3- ...

3. The topical skin composition according to claim 1 or 2, wherein the polymer and / or copolymer of a diallyl quaternary ammonium salt is one or more selected from the group consisting of polyquaternium-39, polyquaternium-7, and polyquaternium-6.

4. The composition for external use on skin according to any one of claims 1 to 3, wherein the polymer and / or copolymer of the diallyl quaternary ammonium salt is contained in an amount of 0.1 to 5% by mass based on the total amount of the composition.

5. The composition for external use on skin according to any one of claims 1 to 4, wherein the polymer and / or copolymer of the diallyl quaternary ammonium salt is contained in an amount of 0.2 to 1.0% by mass based on the total mass of the composition.

6. The composition for external use on skin according to any one of claims 1 to 5, wherein the hydrating agent is contained in an amount of 0.05 to 1% by mass based on the total amount of the composition.

7. The composition for external use on skin according to any one of claims 1 to 6, wherein the mass ratio of the content of the diallyl quaternary ammonium salt polymer and / or copolymer to the content of the hydrating agent is 50:1 to 1:

10.

8. The composition for external use on skin according to any one of claims 1 to 7, which is a cleanser.

9. A skin retention improver for a hydrating agent, comprising a polymer and / or copolymer of a diallyl quaternary ammonium salt, the diallyl quaternary ammonium salt is dimethyldiallylammonium chloride, The hydrating agent is an alkyl glycoside represented by the following general formula (2): 【Chemistry 2】 (In the formula, N represents an integer of 2 to 7, and n represents an integer of 1 to 4.) The diallyl quaternary ammonium salt polymer and / or copolymer is contained in an amount of 0.01 to 5% by mass based on the total amount of the skin retention improver, The skin retention improver contains the hydrating agent in an amount of 0.01 to 1% by mass based on the total amount of the skin retention improver.

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