Skin cosmetic

Abstract

To provide a skin cosmetic that, after application, makes the skin smooth, free from any tight sensation, and soft to touch, such that the skin after the application is moisturized without a sticky feel.SOLUTION: A skincare cosmetic contains the following components (A), (B) and (C): (A) 1.5-10 mass% of an N-acetylglucosamine derivative represented by the general formula (1) in the figure, where R1 represents an alkyl group with 1-12 carbon atoms, and the stereostructure at the 1-position may be either α or β); (B) a polyhydric alcohol; and (C) water.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a skin cosmetic. [Background technology]

[0002] 2. Description of the Related Art Skin cosmetics that maintain the firmness and moisture of the skin and have an anti-aging effect on the skin have been investigated. For example, Patent Document 1 describes that N-acetylglucosamine derivatives have the effect of promoting hyaluronic acid production and can prevent skin aging. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2004 / 033474 Summary of the Invention [Problem to be solved by the invention]

[0004] Conventional cosmetics containing N-acetylglucosamine derivatives had issues with the feel when used, such as being sticky on the skin after application and having a strong squeaky feeling when touched with the fingers. [Means for solving the problem]

[0005] The present inventors have discovered that by using a combination of a specific N-acetylglucosamine derivative and a polyhydric alcohol, it is possible to obtain a skin cosmetic which, after application, leaves the skin feeling smooth and free of any squeaky feeling, softens the skin, moistens the skin, and is non-sticky.

[0006] The present invention comprises the following components (A), (B) and (C): (A) General formula (1):

[0007] [ka]

[0008] (In the formula, R 1 represents an alkyl group having 1 to 12 carbon atoms, and the stereostructure at the 1-position may be either α or β. 1.5 to 10 mass % of an N-acetylglucosamine derivative represented by the formula: (B) a polyhydric alcohol, (C)Water The present invention relates to a skin cosmetic composition comprising the above compound. Effect of the Invention

[0009] The skin cosmetic of the present invention leaves the skin smooth and soft without any squeaky feeling after application. In addition, the skin is moisturized without any stickiness after application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The N-acetylglucosamine derivative of component (A) used in the present invention is represented by the above general formula (1). 1 represents an alkyl group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and further preferably an alkyl group having 2 carbon atoms. In addition, the stereostructure at the 1-position may be either α or β.

[0011] These compounds can be synthesized using known glycosylation reactions. For example, as described in International Publication No. 2004 / 033474, mixed α- and β-glycosides can be produced by glycosylation of N-acetylglucosamine with alcohol under acid catalysis, and α and β can be isolated using a silica gel column. Furthermore, a single compound, β-glycoside, can be produced using the oxazoline synthesis method. Alternatively, it can be produced by condensing an acetohalogen derivative with an alcohol and then removing the protecting group, as described in Chemische Berichte, 86, 1331, (1953), or by using an enzyme such as chitinase to transfer sugar from an N-acetylglucosamine oligomer or polymer to an alkyl alcohol, as described in JP-A-5-244975.

[0012] The content of component (A) is 1.5 to 10 mass% of the total composition, preferably 1.8 to 9 mass%, more preferably 2 to 8 mass%, and even more preferably 3 to 5 mass%, from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing stickiness of the skin after application.

[0013] The polyhydric alcohol of component (B) is a compound having two or more hydroxyl groups in the molecule, and may be any of those commonly used in cosmetics. Examples of dihydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,3-butylene glycol, 1,3-propanediol, and pentanediol. Examples of trihydric alcohols include glycerin and trimethylolpropane. Examples of tetrahydric alcohols include diglycerin and erythritol. Examples of polyhydric alcohols having a valence of five or more include polyglycerins such as triglycerin; sugars and sugar alcohols such as glucose, maltose, maltose, sucrose, xylitol, sorbitol, maltitol, trehalose, glycosyl trehalose, methyl glucoside, ethyl glucoside, propylene glucoside, polyoxyethylene methyl glucoside, polyoxyethylene ethyl glucoside, and polyoxyethylene propylene glucoside.

[0014] As the polyhydric alcohol of component (B), from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing the stickiness of the skin after application, the following may be used: polyethylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,3-propanediol, pentanediol, glycerin, diglycerin, xylitol, sorbitol, maltitol, trehalose, glycosyl trehalose, methyl glucoside, ethyl glucoside, propylene glucoside, It is preferable that the surfactant contains one or more selected from the group consisting of polyethylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,3-propanediol, glycerin, diglycerin, xylitol, sorbitol, maltitol, glycosyl trehalose, and polyoxyethylene methyl glucoside, and it is even more preferable that the surfactant contains one or more selected from the group consisting of dipropylene glycol, 1,3-butylene glycol, and glycerin.

[0015] Component (B) may be used alone or in combination with two or more kinds, and from the viewpoints of improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing stickiness of the skin after application, the content is preferably 4 to 40 mass % of the total composition, more preferably 5 to 35 mass %, even more preferably 6 to 30 mass %, and even more preferably 10 to 20 mass %.

[0016] In the present invention, the mass ratio (A) / (B) of component (A) to component (B) is preferably 0.05 to 1.8, more preferably 0.07 to 1.3, and even more preferably 0.14 to 0.5, from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing the stickiness of the skin after application.

[0017] In the present invention, the content of water in component (C) is preferably 30 to 90 mass% of the total composition, more preferably 35 to 88 mass%, and even more preferably 40 to 85 mass%, from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing stickiness of the skin after application.

[0018] The skin cosmetic preparation of the present invention may further contain (D) an oil agent that is liquid at 25°C, which can smooth the skin after application, reduce the squeaky feeling, improve the softness of the skin after application, improve the moist feeling of the skin after application, and reduce the stickiness of the skin after application. The term "liquid" refers to something that has fluidity, and includes a paste-like state. Examples of the oil agent of component (D) include hydrocarbon oils, ester oils, ether oils, higher alcohols, silicone oils, and higher fatty acids.

[0019] More specifically, examples of the hydrocarbon oil include squalane, liquid paraffin, liquid isoparaffin, light liquid isoparaffin, and heavy liquid isoparaffin. The hydrocarbon oil preferably contains one or more selected from squalane, liquid paraffin, liquid isoparaffin, and light liquid isoparaffin, more preferably contains one or more selected from squalane, liquid paraffin, and liquid isoparaffin, even more preferably contains one or more selected from squalane and liquid isoparaffin, and even more preferably contains squalane.

[0020] Ester oils include monoester oils, diester oils, triester oils and tetraester oils. Examples of monoester oils include monoesters of aliphatic or aromatic monocarboxylic or dicarboxylic acids having 2 to 24 carbon atoms. Specific examples include cetyl 2-ethylhexanoate, cetyl octanoate, isononyl isononanoate, isotridecyl isononanoate, hexyl laurate, isopropyl myristate, octyldodecyl myristate, myristyl myristate, 2-hexyldecyl myristate, isopropyl palmitate, octyl palmitate, 2-hexyldecyl palmitate, butyl stearate, isocetyl stearate, isocetyl isostearate, decyl oleate, octyl methoxycinnamate, hexyldecyl dimethyloctanoate, cetyl lactate, myristyl lactate, lanolin acetate, 2-ethylhexyl succinate, 2-hexyldecyl adipate, alkyl benzoate (C12 to C15), and jojoba oil. The monoester oil preferably contains one or more selected from isononyl isononanoate, isotridecyl isononanoate, and octyldodecyl myristate, more preferably contains one or more selected from isononyl isononanoate and octyldodecyl myristate, and even more preferably contains isononyl isononanoate.

[0021] Examples of diester oils include diesters of dicarboxylic acids having 3 to 18 carbon atoms, difatty acid esters of polyhydric alcohols, and the like. Specific examples include propylene glycol dicaprylate, neopentyl glycol dicaprate, glycol distearate, propylene glycol diisostearate, glyceryl monomyristate monoisostearate, glyceryl di-2-heptylundecanoate, di-2-ethylhexyl succinate, diisopropyl sebacate, diisostearyl malate, ethylene glycol di-2-ethylhexanoate, diisobutyl adipate, di-2-heptylundecyl adipate, di-2-ethylhexyl sebacate, phytosteryl / isostearyl / cetyl / stearyl / behenyl dimer dilinoleate, di(phytosteryl / octyldodecyl) lauroyl glutamate, and bis-ethoxydiglycol cyclohexane-1,4-dicarboxylate. The diester oil preferably contains one or more selected from propylene glycol dicaprylate and neopentyl glycol dicaprate, and more preferably contains neopentyl glycol dicaprate.

[0022] Examples of triester oils include tri-fatty acid esters of trivalent or higher polyhydric alcohols. Specific examples of such oils include glyceryl trimyristate, glyceryl triisopalmitate, glyceryl tri-2-heptylundecanoate, trimethylolpropane triethylhexanoate, trimethylolpropane trioctanoate, tri(caprylic / capric)glyceryl, trioleate, glyceryl tri-2-ethylhexanoate, and glyceryl triisostearate. Examples of such oils include olive oil, macadamia nut oil, meadowfoam oil, shea butter, castor oil, safflower oil, sunflower oil, avocado oil, canola oil, apricot kernel oil, rice germ oil, rice bran oil, and grape seed oil. The triester oil preferably contains one or more selected from caprylic / capric triglyceride, glyceryl tri-2-ethylhexanoate, and vegetable oils, more preferably contains one or more selected from caprylic / capric triglyceride, glyceryl tri-2-ethylhexanoate, olive oil, and jojoba oil, even more preferably contains one or more selected from glyceryl tri-2-ethylhexanoate and olive oil, and even more preferably contains glyceryl tri-2-ethylhexanoate.

[0023] Examples of tetraester oils include tetra-fatty acid esters of tetrahydric or higher polyhydric alcohols, and specific examples thereof include pentaerythrityl tetra(behenate / benzoate / ethylhexanoate), pentaerythrityl tetraethylhexanoate, pentaerythrityl tetraoctanoate, and pentaerythrityl tetra-2-ethylhexanoate.

[0024] From the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing stickiness of the skin after application, the ester oil preferably contains one or more types selected from monoester oil, diester oil, and triester oil, more preferably contains one or more types selected from monoester oil and triester oil, and even more preferably contains triester oil.

[0025] The ether oils include dialkyl ethers, specifically, dihexyl ether, dicaprylyl ether, cetyl-1,3-dimethylbutyl ether, and the like.

[0026] Examples of higher alcohols include those having a straight or branched alkyl or alkenyl group having 10 to 24 carbon atoms, such as lauryl alcohol, myristyl alcohol, isocetyl alcohol, isostearyl alcohol, 2-octyldodecanol, and oleyl alcohol.

[0027] Examples of silicone oils include volatile and non-volatile linear dimethylpolysiloxanes such as dimethylpolysiloxane (1cs), dimethylpolysiloxane (1.5cs), dimethylpolysiloxane (2cs), and dimethylpolysiloxane (6cs); branched siloxanes such as methyltrimethicone, tris(trimethylsilyl)methylsilane, and tetrakis(trimethylsilyl)silane; cyclic dimethylsiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane; and methylphenylpolysiloxanes such as diphenylsiloxyphenyl trimethicone. The silicone oil preferably contains one or more selected from linear dimethylpolysiloxane, branched siloxane, and methylphenylpolysiloxane, more preferably contains one or more selected from branched siloxane and methylphenylpolysiloxane, even more preferably contains one or more selected from tris(trimethylsilyl)methylsilane and methylphenylpolysiloxane, and even more preferably contains methylphenylpolysiloxane.

[0028] Examples of higher fatty acids include oleic acid, isostearic acid, and undecylenic acid.

[0029] The oil agent of component (D) preferably contains one or more oils selected from hydrocarbon oils, ester oils, ether oils, and silicone oils, and more preferably contains one or more oils selected from ester oils and silicone oils, from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing stickiness of the skin after application.

[0030] Component (D) can be used alone or in combination of two or more kinds. From the viewpoint of improving the softness of the skin after application and reducing stickiness of the skin after application, the content is preferably 0.1 to 20 mass%, more preferably 0.5 to 10 mass%, and even more preferably 3 to 5 mass% of the total composition.

[0031] The skin cosmetic of the present invention may further contain (E) a nonionic surfactant, which can reduce stickiness on the skin after application and improve emulsion stability. The nonionic surfactant of component (E) preferably has an HLB of 10 or more, more preferably an HLB of 11-18, even more preferably an HLB of 12-16, and even more preferably an HLB of 13-15, from the viewpoint of improving emulsion stability. Here, HLB (Hydrophilic-Lipophilic Balance) indicates the molecular weight of the hydrophilic group portion in the total molecular weight of the surfactant, and is calculated by Griffin's formula. When a surfactant is composed of two or more nonionic surfactants, the HLB of the mixed surfactant is calculated as follows. The HLB of the mixed surfactant is the phase arithmetic average of the HLB values ​​of each nonionic surfactant based on their blending ratio. Mixed HLB=Σ(HLBx×Wx) / ΣWx HLBx indicates the HLB value of nonionic surfactant X. Wx denotes the mass (g) of the nonionic surfactant X having a value of HLBx.

[0032] Examples of such nonionic surfactants include polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene alkanol ethers, polyglycerin fatty acid esters, sucrose fatty acid esters, etc. Among these, from the viewpoints of reducing stickiness on the skin after application and improving emulsion stability, it is preferable to contain one or more selected from polyoxyethylene hydrogenated castor oil and polyoxyethylene sorbitan fatty acid esters, and it is more preferable to contain polyoxyethylene hydrogenated castor oil.

[0033] In addition, in the polyoxyethylene hydrogenated castor oil, the average number of added moles of polyoxyethylene chains constituting the polyoxyethylene hydrogenated castor oil is preferably 25 to 100, more preferably 35 to 85, even more preferably 40 to 75, even more preferably 55 to 65, and particularly preferably 60, from the viewpoints of reducing stickiness on the skin after application and improving emulsion stability.

[0034] In the polyoxyethylene sorbitan fatty acid ester, from the viewpoints of reducing stickiness on the skin after application and improving emulsion stability, the average number of added moles of polyoxyethylene chains constituting the polyoxyethylene sorbitan fatty acid ester is preferably 10 to 30, more preferably 15 to 25, and even more preferably 20. In the polyoxyethylene sorbitan fatty acid ester, from the viewpoints of reducing stickiness on the skin after application and improving emulsion stability, the number of carbon atoms in the alkyl group constituting the polyoxyethylene sorbitan fatty acid ester is preferably 8 to 25, more preferably 10 to 20, and even more preferably 12 to 18.

[0035] The nonionic surfactant of component (E) can be used alone or in combination of two or more kinds. From the viewpoint of reducing stickiness on the skin after application, the content is preferably 0.1 to 5 mass % of the total composition, more preferably 0.5 to 3 mass %, and even more preferably 0.8 to 1.5 mass %.

[0036] In the present invention, the mass ratio (A) / (D) of component (A) to component (D) is preferably 0.1 to 90, more preferably 0.2 to 16, even more preferably 0.6 to 1.6, and even more preferably 0.8 to 1.3, from the viewpoints of smoothing the skin after application, reducing the squeaky feeling, improving the softness of the skin after application, improving the moist feeling of the skin after application, and reducing the stickiness of the skin after application.

[0037] In addition to the above-mentioned components, the skin cosmetic of the present invention may contain components that are usually used in cosmetics, such as surfactants other than component (E), oils other than component (D), polymeric compounds, antioxidants, fragrances, preservatives, pH adjusters, sequestering agents, blood circulation promoters, cooling agents, antiperspirants, germicides, skin activators, moisturizers other than component (B), and cooling agents.

[0038] The skin cosmetic of the present invention can be produced according to a conventional method. For example, the skin cosmetic can be obtained by mixing components (A), (B) and (C) under heating and then cooling to room temperature. Furthermore, when an oil is contained, for example, the skin cosmetic can be obtained by heating and mixing components (A), (B), and (C) and the other components excluding the oil, cooling to room temperature, and further mixing with the oil.

[0039] The skin cosmetic of the present invention is preferably a water-based cosmetic, and is suitable as an aqueous cosmetic or an oil-in-water emulsion cosmetic. For example, it can be used as a skin cosmetic such as a skin lotion, emulsion, serum, cream, or other skin care cosmetic, and is suitable as a skin lotion, serum, or cream, and is more suitable as a skin lotion or serum. EXAMPLES

[0040] Manufacturing Example 1 N-acetylglucosamine derivatives (in the general formula (1), R 1 Preparation of compounds with 2 carbon atoms: 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranoside was dissolved in anhydrous chloroform, trimethylsilyl trifluoromethanesulfonate was added, and the mixture was stirred at 25°C. Chloroform was added to the reaction mixture, which was then washed with a saturated aqueous solution of sodium bicarbonate. The chloroform layer was then dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was dissolved in dichloroethane, and ethanol and (±)-camphor-10-sulfonic acid were added, followed by stirring at 60°C. Chloroform was added to the reaction mixture, which was then washed with a saturated aqueous solution of sodium bicarbonate. The chloroform layer was then dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was finally isolated using silica gel column chromatography to obtain a purified product. This was dissolved in a mixed solvent of methanol and 1,4-dioxane, and a catalytic amount of a sodium methylate methanol solution was added, followed by stirring at 25°C. The reaction mixture was neutralized, and the solvent was then distilled off. Finally, the residue obtained was crystallized from water to give the N-acetylglucosamine derivative (R 1 The compound having 2 carbon atoms was obtained as white crystals.

[0041] Example 1, Comparative Examples 1-2 Skin cosmetics (lotions) were prepared with the compositions shown in Table 1, and were evaluated for smoothness, softness, moist feeling, and non-stickiness of the skin. The results are also shown in Table 1.

[0042] (Manufacturing method) Components (A), (B) and (C) were mixed at 40°C and then cooled to 25°C to obtain a skin cosmetic (lotion).

[0043] (Evaluation method) (1) Skin smoothness: Three expert evaluators applied each skin cosmetic to the cheeks, blended it in, and then evaluated the smoothness of the skin when touched with the fingers according to the following criteria. Smoothness refers to the ability to easily stop the fingers from touching the skin with the fingers and the absence of any squeaky feeling. The results were expressed as the total score of the three evaluators. <Evaluation criteria> 4: Feels smooth. 3: Feels slightly smooth. 2: Almost no feeling of smoothness. 1: No feeling of smoothness at all.

[0044] (2) Skin softness: Three expert evaluators applied each skin cosmetic to the cheek, smoothed it over, and then pressed the skin with their fingers to evaluate the softness of the skin according to the following criteria. The results were shown as the total score given by the three evaluators. <Evaluation criteria> 4: It feels soft. 3: Feels slightly soft. 2: Hardly any feeling of softness. 1: No feeling of softness at all.

[0045] (3) Moisturizing skin: Three expert evaluators applied each skin cosmetic to the cheek, rubbed it in, and then evaluated the moist feeling when touching the skin with their fingers according to the following criteria. The results were shown as the total score given by the three evaluators. <Evaluation criteria> 4: Feels moist. 3: Feels slightly moist. 2: Almost no moist feeling. 1: No moisturizing sensation at all.

[0046] (4) No stickiness on the skin: Three expert evaluators applied each skin cosmetic to the cheek, rubbed it in, and then evaluated the lack of stickiness when touching the skin with their fingers according to the following criteria. The results were shown as the total score given by the three evaluators. <Evaluation criteria> 4: Does not feel sticky. 3: Almost no stickiness. 2: Feels slightly sticky. 1: Stickiness is clearly felt.

[0047] [Table 1]

[0048] *1: 1,3-butylene glycol; 1,3-butylene glycol (manufactured by Daicel Corporation), *2: Glycerin; concentrated glycerin for cosmetics (manufactured by Sakamoto Pharmaceutical Industry Co., Ltd.)

[0049] Examples 2 to 6, Comparative Example 3 A skin cosmetic (serum (O / W emulsion composition)) having the composition shown in Table 2 was produced, and the smoothness, softness, moist feeling, and non-stickiness of the skin were evaluated in the same manner as in Example 1. The results are also shown in Table 2.

[0050] (Manufacturing method) Components (A), (B), (C) and the other components except for the oil were mixed at 40°C, then cooled to 25°C, and the oil was further mixed in to obtain a skin cosmetic preparation (serum (O / W emulsion composition)).

[0051] [Table 2]

[0052] *3: Dipropylene glycol; Dipropylene glycol FG (SK picglobal), *4: Methylphenylpolysiloxane; KF-56A (manufactured by Shin-Etsu Chemical Co., Ltd.), *5: Glyceryl triethylhexanoate; Exepar TGO (Kao Corporation), *6: Polyoxyethylene hydrogenated castor oil (60E.O.); Emanon CH-60(K) (Kao Corporation), HLB14, *7: Carboxyvinyl polymer; Synthalen K (manufactured by 3V Sigma), *8: Potassium hydroxide; Caustic potash (manufactured by Toagosei Co., Ltd.), *9: Disodium edetate; Clewat N (manufactured by Nagase & Co., Ltd.), *10: Phenoxyethanol; Hysorb EPH (manufactured by Toho Chemical Industry Co., Ltd.)

[0053] Prescription Examples 1-10 All of the skin cosmetics shown in Tables 3 to 12 leave the skin feeling smooth and free of any squeaky feeling after application, giving a soft feeling to the skin, and providing a moist feeling to the skin without any stickiness after application.

[0054] [Table 3]

[0055] [Table 4]

[0056] [Table 5]

[0057] [Table 6]

[0058] [Table 7]

[0059]

Table 8

[0060]

Table 9

[0061]

Table 10

[0062]

Table 11

[0063]

Table 12

Claims

1. The following components (A), (B), and (C): (A) General formula (1): 【Chemistry 1】 (In the formula, R １ (This represents an alkyl group having 1 to 12 carbon atoms, and the stereostructure at position 1 can be either α or β.) N-acetylglucosamine derivative represented by 1.5 to 10% by mass, (B) Polyhydric alcohols, (C) Water A skin cosmetic containing [a specific ingredient].

2. The skin cosmetic composition according to claim 1, wherein the content of component (B) is 4 to 40% by mass.

3. The skin cosmetic composition according to claim 1 or 2, wherein the mass ratio (A) / (B) of component (A) to component (B) is 0.05 to 1.

8.

4. Furthermore, the skin cosmetic composition according to claim 1 or 2, further comprising (D) a liquid oil at 25°C.

5. Furthermore, the skin cosmetic composition according to claim 1 or 2, further comprising (E) a nonionic surfactant.

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