External preparation for skin

Abstract

To provide an external preparation for skin that is applied to the skin after use of another external preparation for skin, thereby enhancing permeability of the previously applied external preparation for skin.SOLUTION: Provided is an external preparation for skin comprising following (A) to (D): (A) an oligomer ester composed of a dicarboxylic acid and polyglycerin having an average degree of polymerization of 2 or more and 15 or less, (B) betaine, (C) a phosphorylcholine group-containing polymer, and (D) a rice fermentation solution.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an external skin preparation that, when applied to the skin after the use of another external skin preparation, enhances the penetration of the previously applied external skin preparation. [Background technology]

[0002] In recent years, skin care preparations containing various active ingredients have been developed and are expected to be highly effective. To maximize the effectiveness of skin care preparations, it is preferable for them to penetrate the skin as much as possible. However, penetration into the skin is not easy due to the skin's barrier function.

[0003] Various formulations have been developed with the aim of improving skin permeability, for example, pre-treatment agents to be used before applying skin care formulations have been developed to promote percutaneous absorption (References 1 and 2). However, the permeability has not always been fully satisfactory. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2012-111722 [Patent Document 2] Japanese Patent Application Publication No. 2022-124939 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide an external skin preparation that, when applied to the skin after the use of another external skin preparation, enhances the penetration of the previously applied external skin preparation. [Means for solving the problem]

[0006] The present invention provides an external skin preparation containing the following (A) to (D): (A) an oligomer ester composed of a dicarboxylic acid and a polyglycerol having an average degree of polymerization of 2 to 15 (B) Betaine (C) Phosphorylcholine group-containing polymer (D) Rice fermentation liquid [Effects of the Invention]

[0007] When applied to the skin after the use of another external skin preparation, the external skin preparation of the present invention exerts the effect of enhancing the penetration of the previously applied external skin preparation. DETAILED DESCRIPTION OF THE INVENTION

[0008] Hereinafter, an embodiment of the present invention will be described.

[0009] [Oligomer ester composed of dicarboxylic acid and polyglycerol with an average degree of polymerization of 2 to 15] The dicarboxylic acid of the oligomer ester used in the present invention, which is composed of a dicarboxylic acid and a polyglycerol with an average degree of polymerization of 2 to 15, is not particularly limited as long as it has a linear, branched, or cyclic structure, but from the viewpoints of ease of synthesis and improving the effect, the number of carbon atoms in the dicarboxylic acid is preferably 2 or more, more preferably 8 or more, even more preferably 12 or more, and still more preferably 14 or more, and is preferably 26 or less, more preferably 24 or less, even more preferably 22 or less, and still more preferably 20 or less. From the same viewpoint, aliphatic dicarboxylic acids are preferred. Specific examples of dicarboxylic acids having from 2 to 26 carbon atoms include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 2,4-diethylpentanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, octadecanedioic acid, 8-ethyloctadecanedioic acid, eicosanediic acid, dimethyleicosanediic acid, cyclohexanedicarboxylic acid, etc. These dicarboxylic acids may be used alone or in appropriate combination of two or more.

[0010] Of these dicarboxylic acids, linear or branched dicarboxylic acids having from 14 to 22 carbon atoms are preferred, and linear dicarboxylic acids having from 14 to 20 carbon atoms are more preferred. Specifically, one or more selected from tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, octadecanedioic acid, 8-ethyloctadecanedioic acid, eicosanediic acid, and dimethyleicosanediic acid are preferred, and one or two selected from tetradecanedioic acid and eicosanediic acid are more preferred.

[0011] Furthermore, as the polyglycerin that forms an ester with a dicarboxylic acid, a polyglycerin having an average degree of polymerization calculated from the hydroxyl value of 2 to 15 is used. From the viewpoint of good solubility in aqueous components, the average degree of polymerization of the polyglycerin is preferably 8 or more, more preferably 9 or more, and is preferably 15 or less, more preferably 12 or less. Among these, polyglycerin containing a polyglycerin having an average degree of polymerization of 10 is preferred.

[0012] Examples of methods for producing an oligomeric ester of a dicarboxylic acid and a polyglycerol include the method described in JP 2007-137847 A. The degree of polymerization of the oligomeric ester of the present invention can be adjusted by the charging ratio of the dicarboxylic acid to the polyglycerol. From the viewpoint of preventing the viscosity of the oligomeric ester from becoming too high and improving the effect, the amount of the dicarboxylic acid relative to 1 molar equivalent of the polyglycerol is preferably 0.3 molar equivalents or more, more preferably 0.7 molar equivalents or more, and preferably 1.5 molar equivalents or less, more preferably 1.2 molar equivalents or less.

[0013] A suitable example of these oligomer esters is decaglyceryl (eicosanedioic acid / tetradecanedioic acid) liquid, which is an oligomer ester composed of tetradecanedioic acid and / or eicosanedioic acid and polyglycerol having an average degree of polymerization of 10. Commercially available oligomer esters can also be used, such as Neosolue-Aqua and Neosolue-AquaS (both manufactured by Nippon Fine Chemical Co., Ltd.).

[0014] The amount of the dicarboxylic acid and polyglycerin having an average degree of polymerization of 2 to 15 in the topical skin preparation of the present invention is preferably 0.008 to 6 mass %, more preferably 0.02 to 4 mass %, based on the total amount of the topical skin preparation.

[0015] [Betaine] The betaine used in the present invention is not particularly limited in terms of raw materials, production method, purification method, etc., as long as it is one that is commonly used in external skin preparations, etc. Commercially available products such as GENENCARE (registered trademark) OSMSBA (manufactured by Finnfeeds Finland), AQUADEW (registered trademark) AN-100 (manufactured by Ajinomoto Co., Inc.), and Aminocoat (registered trademark) (manufactured by Asahi Kasei Finechem Co., Ltd.) can also be used.

[0016] The amount of betaine to be incorporated into the topical skin preparation of the present invention is not particularly limited, but is preferably 0.01 to 20% by mass, more preferably 0.1 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total amount of the topical skin preparation.

[0017] [Phosphorylcholine group-containing polymer] The phosphorylcholine group-containing polymer used in the present invention can be any polymer typically used in topical skin preparations. One type may be used alone, or two or more types may be used in combination. Specific examples of such phosphorylcholine group-containing polymers include, by cosmetic ingredient name, Polyquaternium-51 (2-methacryloyloxyethyl phosphorylcholine-butyl methacrylate copolymer), Polyquaternium-65 (2-methacryloyloxyethylene phosphorylcholine-butyl methacrylate-sodium methacrylate copolymer), Polyquaternium-64 (2-methacryloyloxyethyl phosphorylcholine-2-hydroxy-3-methacryloyloxypropyltrimethylammonium copolymer), and Polyquaternium-61 (2-methacryloyloxyethyl phosphorylcholine-stearyl methacrylate copolymer). In terms of effectiveness, Polyquaternium-61 is preferred for use in the present invention. Commercially available products include LIPIDURE-NR, LIPIDURE-S, and LIPIDURE-NA (all manufactured by NOF Corporation).

[0018] The amount of the phosphorylcholine group-containing polymer to be incorporated into the topical skin preparation of the present invention is preferably 0.00001 to 5% by mass, more preferably 0.00001 to 1% by mass, based on the total amount of the topical skin preparation.

[0019] [Rice fermented liquid] The rice fermentation liquor used in the present invention is obtained by enzymatically hydrolyzing rice or rice bran, saccharifying it with koji, and fermenting it with yeast or yeast starter. Examples of fungi and yeasts used in fermentation include Aspergillus, Monascus, Saccharomyces, Lachancea, Tetragenococcus, Lactobacillus, and Leuconostoc. The rice fermentation liquor used in the present invention is preferably fermented with yeast of the genus Saccharomyces. Commercially available rice fermentation liquors obtained by these methods can also be used, including Kome Extract Koken MPN (manufactured by Koken Co., Ltd.), ASFERM PLUS (manufactured by SK Bioland), and Horus Ginjo Extract AL (manufactured by Horus Co., Ltd.).

[0020] The amount of rice fermentation liquor in the topical skin preparation of the present invention is preferably 0.0001 to 10% by mass, more preferably 0.001 to 5% by mass, based on the total amount of the topical skin preparation. A content of less than 0.0001% by mass may not provide sufficient effects. If the content of rice fermentation liquor exceeds 10% by mass, the amino acids contained in the liquor may precipitate or discolor over time.

[0021] In addition to the above-mentioned components, the topical skin preparation of the present invention may contain optional components used in ordinary cosmetics and quasi-drugs to the extent that the effects of the present invention are not impaired. Specific examples of such components include ultraviolet absorbers, ultraviolet scattering agents, oils, surfactants, thickeners, preservatives, fragrances, pigments, moisturizers, antioxidants, anti-inflammatory agents, and antibacterial agents.

[0022] The formulation of the external skin preparation of the present invention is not particularly limited, and may be any of aqueous, oil-based, emulsion-type, and the like.

[0023] The topical skin preparation of the present invention can be prepared by a conventional method. [Example]

[0024] The present invention will be described in more detail below with reference to examples, but the scope of the present invention is not limited thereto. In the following examples, the blending amounts are expressed in mass % unless otherwise specified.

[0025] [Permeability evaluation] 10 μL of the topical skin preparation shown in Table 1 was dropped onto a Strat-M (registered trademark) membrane for transdermal diffusion testing (manufactured by Merck) and uniformly applied with a finger wearing a finger cot. Then, 10 μL of the Examples and Comparative Examples shown in Table 2 was dropped onto the membrane and uniformly applied with a finger wearing a finger cot. If any liquid remained on the surface of the membrane, it was gently removed by pressing with tissue paper. Next, the membrane was cut into 1 mm wide pieces, and the cross section was observed with a digital microscope (manufactured by Keyence Corporation, model number VHX-5000). The penetration of the dye was visually confirmed and evaluated as follows. Comparative Example 11 was a case where nothing was applied after the topical skin preparation shown in Table 1 was applied. The results are shown in Tables 2 and 3.

[0026] [Evaluation criteria] Penetration Very good:◎ Good:〇 Bad:△ Very bad: ×

[0027] The topical skin preparation to be applied first was prepared by a conventional method using the formulation shown in Table 1, and topical skin preparations serving as examples of the present invention and comparative examples were prepared by the formulations shown in Tables 2 and 3.

[0028] [Table 1]

[0029] [Table 2]

[0030] [Table 3]

[0031] As shown in Tables 2 and 3, it was confirmed that when the topical skin preparation of the present invention is applied to the skin after the use of other topical skin preparations, it has the effect of increasing the permeability of the previously applied topical skin preparation.

[0032] [Example 2] Cream (1) Squalane 10.0 (mass%) (2) Stearic acid 2.0 (3) Hydrogenated palm kernel oil 0.5 (4) Hydrogenated soybean phospholipid 0.1 (5) Cetyl alcohol 3.6 (7) Lipophilic Glyceryl Monostearate 2.0 (8) Glycerin 10.0 (9) (Eicosanedioic acid / Tetradecanedioic acid) Polyglyceryl-10 1.5 (10) Betaine 5.0 (11) Polyquaternium-61 0.1 (12) Rice fermentation liquid 1.2 (13) Phenoxyethanol 0.2 (14) Arginine (20% by weight aqueous solution) 15.0 (15) Sodium Hyaluronate 0.5 (16) Purified water (total amount: 100) (17) Carboxyvinyl polymer (1% by mass aqueous solution) 15.0

[0033] [Example 3] Emulsion (1) Squalane 10.0 (mass%) (2) Methylphenylpolysiloxane 4.0 (3) Hydrogenated palm kernel oil 0.5 (4) Hydrogenated soybean phospholipid 0.1 (5) Polyoxyethylene monostearate Sorbitan (20E.O.) 1.3 (6) Sorbitan monostearate 1.0 (7) Glycerin 4.0 (8) (Eicosanedioic acid / Tetradecanedioic acid) Polyglyceryl-10 0.1 (9) Betaine 7.0 (10) Polyquaternium-61 0.001 (11) Rice fermentation liquid 3.0 (12) Niacinamide 6.0 (13) Phenoxyethanol 0.2 (14) Carboxyvinyl polymer (1% by mass aqueous solution) 10.0 (15) Sodium Hyaluronate 0.1 (16) Purified water (total amount: 100) (17) L-arginine (1% by mass aqueous solution) 20.0

[0034] [Example 4] Lotion (1) Ethanol 15.0 (mass%) (2) Polyoxyethylene (40E.O.) hydrogenated castor oil 0.3 (3)Fragrance 0.1 (4) Purified water (total amount: 100) (5) Citric acid 0.02 (6) Sodium citrate 0.1 (7) Glycerin 1.0 (8) (Eicosanedioic acid / Tetradecanedioic acid) Polyglyceryl-10 2.0 (9) Betaine 1.0 (10) Polyquaternium-61 0.5 (11) Rice fermentation liquid 0.01 (12) Hydroxyethyl cellulose 0.1 (13) Sodium hyaluronate 0.3

[0035] [Example 5] Beauty serum (1) Purified water, the amount (mass%) of which the total amount is 100 (2) Glycerin 10.0 (3) Sucrose fatty acid ester 1.3 (4) Carboxyvinyl polymer (1% by mass aqueous solution) 17.5 (5) Sodium alginate (1% by mass aqueous solution) 15.0 (6) Polyglyceryl monolaurate 1.0 (7) Sodium hyaluronate 0.1 (8) (Eicosanedioic acid / Tetradecanedioic acid) Polyglyceryl-10 1.0 (9) Betaine 3.0 (10) Polyquaternium-61 1.5 (11) Rice fermentation liquid 0.5 (12) Niacinamide 3.5 (13) Macadamia nut oil fatty acid phytosteryl 3.0 (14) N-Lauroyl-L-glutamic acid Di(phytosteryl-2-octyldodecyl) 2.0 (15) Hydrogenated Palm Oil 2.0 (16) Squalane (derived from olives) 1.0 (17) Behenyl alcohol 0.75 (18) Beeswax 1.0 (19) Jojoba oil 1.0 (20) 1,3-butylene glycol 10.0 (21) L-arginine (10% by mass aqueous solution) 2.0

[0036] [Example 7] Makeup base cream (1) Squalane 10.0 (mass%) (2) Cetyl alcohol 2.0 (3) Glycerin tri-2-ethylhexanoate 2.5 (4) Lipophilic glyceryl monostearate 1.0 (5) Propylene glycol 11.0 (6) Sucrose fatty acid ester 1.3 (7) Purified water (total amount: 100) (8) Titanium dioxide 1.0 (9) Bengala 0.1 (10) Yellow iron oxide 0.4 (11)Fragrance 0.1 (12) (Eicosanedioic acid / Tetradecanedioic acid) Polyglyceryl-10 3.0 (13) Betaine 0.5 (14) Polyquaternium-61 1.0 (15) Rice Fermentation Liquid 2.0

Claims

[Claim 1] A topical skin preparation containing the following (A) to (D): (A) an oligomer ester composed of a dicarboxylic acid and a polyglycerol with an average degree of polymerization of 2 to 15 (B) Betaine (C) Phosphorylcholine group-containing polymer (D) Rice fermentation liquid

Images