Cosmetic

Abstract

Provided is a cosmetic that is capable of increasing the permeability of an imidazolidinone derivative and a salt thereof to the skin.　A cosmetic according to the present disclosure comprises: at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by formula 1 and salts thereof; and at least one surfactant selected from the group consisting of amino acid surfactants and taurine surfactants. (In formula 1, R1 and R2 are each independently a hydrogen atom, a linear or branched alkyl group which has 1-4 carbon atoms and has 0-3 hydroxyl groups, or a cycloalkyl group which has 3-7 carbon atoms and has 0-5 hydroxy groups.)

Description

cosmetics

[0001] The present disclosure relates to cosmetics.

[0002] In recent years, imidazolidinone derivatives have been used in the field of cosmetics and the like.

[0003] Patent Document 1 describes a skin cream and a skin care emulsion containing an imidazolidinone derivative.

[0004] JP 2008-303186 A

[0005] For example, the stratum corneum, located at the outermost layer of the skin, is not only highly hydrophobic but also has a barrier function that prevents the penetration of foreign substances from the outside, making it difficult for water-soluble active ingredients applied to the skin to penetrate into the interior of the skin. For this reason, simply applying a drug to the skin tends to cause hydrophilic drug ingredients to remain on the surface of the skin, making it impossible to achieve a sufficient effect.

[0006] Among the drugs, imidazolidinone derivatives and their salts have a log P of about -1.5. ｏ／ｗ Since these components have high hydrophilicity, they are difficult to penetrate into the skin, and therefore, there has been a demand for a technology that allows such components to penetrate into the skin.

[0007] Therefore, an object of the present disclosure is to provide a cosmetic preparation that can enhance the skin permeability of imidazolidinone derivatives and salts thereof.

[0008] Aspect 1: A cosmetic comprising at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof, and at least one surfactant selected from the group consisting of amino acid surfactants and taurine surfactants: (In formula 1, R １ and R ２are each independently a hydrogen atom, a linear or branched alkyl group of 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or a cycloalkyl group of 3 to 7 carbon atoms having 0 to 5 hydroxyl groups.) <Aspect 2> The cosmetic according to Aspect 1, wherein the amino acid surfactant is an α-amino acid surfactant. <Aspect 3> The cosmetic according to Aspect 1, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut oil fatty acid amidopropyl betaine, sodium cocoyl glycinate, potassium cocoyl glutamate, and sodium coconut oil fatty acid methyl taurate. <Aspect 4> The cosmetic preparation according to any one of Aspects 1 to 3, wherein the imidazolidinone derivative is at least one selected from the group consisting of 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone. <Aspect 5> The cosmetic preparation according to any one of Aspects 1 to 4, wherein the mass ratio of the surfactant to the water-soluble drug is greater than 0.05. <Aspect 6> The cosmetic preparation according to any one of Aspects 1 to 5, wherein the content of the water-soluble drug is 0.1 mass% or more with respect to the total cosmetic preparation. <Aspect 7> A beauty method comprising applying the cosmetic preparation according to any one of Aspects 1 to 6 to skin. <Aspect 8> Use of at least one surfactant selected from the group consisting of amino acid surfactants and taurine surfactants as a transdermal penetration enhancer for at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof: (In formula 1, R １ and R ２are each independently a hydrogen atom, a linear or branched alkyl group of 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or a cycloalkyl group of 3 to 7 carbon atoms having 0 to 5 hydroxyl groups.) Aspect 9: The use according to Aspect 8, wherein the amino acid surfactant is an α-amino acid surfactant. Aspect 10: The use according to Aspect 8, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut oil fatty acid amidopropyl betaine, sodium cocoyl glycinate, potassium cocoyl glutamate, and sodium coconut oil fatty acid methyl taurate. Aspect 11: The use according to any one of Aspects 8 to 10, wherein the imidazolidinone derivative is at least one selected from the group consisting of 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone.

[0009] According to the present disclosure, it is possible to provide a cosmetic that can enhance the skin permeability of an imidazolidinone derivative and a salt thereof.

[0010] Fig. 1 is a graph showing the ratio of the cumulative permeation amount of examples containing various transdermal permeation enhancers to the cumulative permeation amount of Comparative Example 1 or Reference Comparative Example 1, which does not contain a transdermal permeation enhancer. Fig. 2 is a graph showing the cumulative permeation amount after 3 hours when various amino acid-based surfactants and taurine-based surfactants were used.

[0011] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present disclosure is not limited to the following embodiments, and various modifications can be made within the scope of the present invention.

[0012] The cosmetic composition of the present disclosure contains at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the above formula 1 and salts thereof (hereinafter, this may be referred to as the "specific water-soluble drug"), and at least one surfactant selected from the group consisting of amino acid-type surfactants and taurine-type surfactants (hereinafter, this may be referred to as the "specific surfactant").

[0013] Without being limited by the theory, the principle of action by which the cosmetic composition of the present disclosure can enhance the skin permeability (sometimes referred to as "transdermal permeability") of imidazolidinone derivatives and salts thereof is believed to be as follows.

[0014] The specific water-soluble drug of the present disclosure permeates the pseudo-skin membrane to some extent even without the use of a drug known as a skin permeation enhancer, as shown in Comparative Example 1 of Figures 1 and 2. Here, the pseudo-skin membrane used in the present disclosure has properties similar to those of skin, so if the drug permeates the pseudo-skin membrane, it can be said that the drug will also permeate the skin.

[0015] On the other hand, as shown in Comparative Examples 4 to 6 in Figure 1, when a drug such as urea or ethanol, which is known as a skin penetration enhancer, is used in combination with the specific water-soluble drug, the permeability of the specific water-soluble drug through the pseudo-skin membrane, i.e., the transdermal permeability, is not improved.

[0016] For example, lauryl betaine, an amino acid surfactant, can enhance the permeability into the pseudo-skin membrane, i.e., the transdermal permeability, even when used in combination with niacinamide (nicotinamide), a known water-soluble drug, as can be seen from the results of Reference Comparative Example 1 and Reference Example 1 in Figure 1. However, the present inventors unexpectedly discovered that when used in combination with a specific water-soluble drug, the permeability into the pseudo-skin membrane, i.e., the transdermal permeability, is improved by more than two times compared to niacinamide.

[0017] In other words, when it comes to increasing the permeability of a specific water-soluble drug into the skin, not all skin penetration enhancers are effective, and it is believed that only when an amino acid-type surfactant or a taurine-type surfactant is used in combination with a variety of other agents, some kind of interaction occurs and the permeability into the skin is specifically increased.

[0018] <<Cosmetic>> The cosmetic of the present disclosure contains at least one water-soluble drug (specific water-soluble drug) selected from the group consisting of imidazolidinone derivatives represented by the above formula 1 and salts thereof, and at least one surfactant (specific surfactant) selected from the group consisting of amino acid surfactants and taurine surfactants.

[0019] <Specific Water-Soluble Drug> In the present disclosure, the specific water-soluble drug refers to at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof. Such drugs can exhibit, for example, wrinkle improvement effects, SCCA1 inhibitory effects, etc.

[0020] In formula 1, R １ and R ２ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms and 0 to 3 hydroxyl groups, or a cycloalkyl group having 3 to 7 carbon atoms and 0 to 5 hydroxyl groups.

[0021] Among these, from the viewpoint of further improving skin permeability when used in combination with a specific surfactant, the imidazolidinone derivative is preferably at least one selected from the group consisting of 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone, and more preferably 1-(2-hydroxyethyl)-2-imidazolidinone (sometimes referred to as "hydroxyethylimidazolidinone").

[0022] The imidazolidinone derivative can be converted into an inorganic salt or an organic salt by a known method. The salt is not particularly limited. Examples of inorganic salts include hydrochloride, sulfate, phosphate, hydrobromide, sodium salt, potassium salt, magnesium salt, calcium salt, and ammonium salt. Examples of organic salts include acetate, lactate, maleate, fumarate, tartrate, citrate, methanesulfonate, p-toluenesulfonate, triethanolamine salt, diethanolamine salt, and amino acid salt.

[0023] The amount of the specific water-soluble drug is not particularly limited, but from the viewpoint of further improving skin permeability when used in combination with the specific surfactant, it is preferably 0.1 mass% or more, 0.3 mass% or more, 0.5 mass% or more, 0.7 mass% or more, 1.0 mass% or more, or 1.5 mass% or more relative to the total amount of the cosmetic. There is no particular upper limit to the amount, and it can be, for example, 10 mass% or less, 8.0 mass% or less, 5.0 mass% or less, or 3.0 mass% or less.

[0024] <Specific surfactant> In the present disclosure, the specific surfactant refers to at least one surfactant selected from the group consisting of amino acid surfactants and taurine surfactants. This specific surfactant can enhance the permeability of the specific water-soluble drug into the skin, and can therefore be used as a transdermal penetration enhancer for the specific water-soluble drug.

[0025] In the present disclosure, the term "amino acid surfactant" refers to a surfactant having a structure derived from an amino acid. Here, "amino acid" is a general term for organic compounds having an amino group and a carboxy group.

[0026] The amino acid surfactant is preferably an α-amino acid surfactant, from the viewpoint of further improving the skin permeability when used in combination with a specific water-soluble drug.

[0027] Specific examples of the amino acid surfactant include lauryl betaine, coconut oil fatty acid amidopropyl betaine, cocoyl glycine salts (e.g., sodium cocoyl glycinate), cocoyl glutamate salts (e.g., potassium cocoyl glutamate), 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, cocamidopropyl betaine, lauramidopropyl betaine, cocobetaine, cocoamphoacetates (e.g., sodium cocoamphoacetate), lauroamphoacetates (e.g., sodium lauroamphoacetate), stearoyl glutamate, myristoyl glutamate, and lauryl glutamate. These may be used alone or in combination of two or more.

[0028] In the present disclosure, the term "taurine-type surfactant" refers to a surfactant having a structure derived from taurine.

[0029] Examples of taurine-type surfactants include surfactants having a structure derived from acyltaurine or acylmethyltaurine (ie, N-acyl-N-methyltaurine).

[0030] Specifically, at least one selected from the group consisting of caproyl taurine, lauroyl taurine, myristoyl taurine, palmitoyl taurine, stearoyl taurine, oleoyl taurine, cocoyl taurine, methyl taurine, coconut oil fatty acid methyl taurine, palm kernel oil fatty acid methyl taurine, hydrogenated palm kernel oil fatty acid methyl taurine, beef tallow fatty acid methyl taurine, hydrogenated beef tallow fatty acid methyl taurine, caproyl methyl taurine, lauroyl methyl taurine, myristoyl methyl taurine, palmitoyl methyl taurine, stearoyl methyl taurine, oleoyl methyl taurine, cocoyl methyl taurine, methyl taurine cocoyl methyl taurine, and salts thereof can be mentioned. Among them, coconut oil fatty acid methyl taurine and its salts are preferred from the viewpoint of further improving skin permeability when used in combination with a specific water-soluble drug. Examples of salts include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts, zinc salts, iron salts, ammonium salts, salts with basic amino acids such as arginine, lysine, histidine, and ornithine, and salts with amines such as monoethanolamine, diethanolamine, and triethanolamine. Of these, alkali metal salts are preferred, and sodium salts are more preferred.

[0031] The blending amount of the specific surfactant can be, for example, 0.05% by mass or more, more than 0.05% by mass, 0.07% by mass or more, 0.1% by mass or more, or more than 0.1% by mass, relative to the total amount of the cosmetic, and can be 8.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, 3.0% by mass or less, 1.0% by mass or less, 0.7% by mass or less, 0.5% by mass or less, or 0.3% by mass or less.

[0032] The specific surfactant can function as a percutaneous penetration enhancer for the specific water-soluble drug. Therefore, from the viewpoint of further improving the skin permeability when used in combination with the specific water-soluble drug, the mass ratio of the specific surfactant to the specific water-soluble drug is preferably more than 0.05, 0.07 or more, 0.10 or more, or 0.15 or more, and is preferably 5.0 or less, 4.0 or less, 3.0 or less, 2.0 or less, 1.5 or less, 1.0 or less, 0.70 or less, 0.50 or less, or 0.40 or less.

[0033] <Water> The cosmetic preparation of the present disclosure may contain water. There are no particular limitations on the water, as long as it can dissolve the specific water-soluble drug described above. For example, water used in cosmetics can be used. Examples of such water include ion-exchanged water, purified water, distilled water, ultrapure water, and tap water.

[0034] The amount of water to be blended is not particularly limited and can be adjusted appropriately depending on, for example, the formulation used in the cosmetic (e.g., a single aqueous phase, or an oil-in-water or water-in-oil emulsion), etc. Specifically, the amount of water to be blended can be, for example, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 45% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75% by mass or more, or 80% by mass or more relative to the total amount of the cosmetic, or can be less than 100% by mass, 99% by mass or less, 98% by mass or less, 95% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, or 50% by mass or less.

[0035] <Optional Components> The cosmetic composition of the present disclosure may contain various components as appropriate, provided that they do not adversely affect the effects of the present disclosure. Examples of the various components include surfactants other than the specific surfactants described above (e.g., anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants), thickeners, moisturizers, dispersants, water-soluble polymers, film-forming agents, sequestering agents, lower alcohols (e.g., ethanol), polyhydric alcohols (e.g., glycerin), higher alcohols, various extracts, sugars, amino acids, organic amines, polymer emulsions, chelating agents, UV absorbers, pH adjusters, skin nutrients, vitamins, water-soluble agents other than the specific water-soluble agents described above (e.g., niacinamide), buffers, preservatives, antioxidants, stabilizers, propellants, fillers, cooling agents, pigments, dyes, coloring materials, fragrances, and oils. The optional components may be used alone or in combination of two or more.

[0036] In some embodiments, the cosmetic composition of the present disclosure can include an alkylene oxide derivative represented by the following formula 2. When such a derivative is used in combination with a specific surfactant, the skin permeability of a specific water-soluble drug can be further improved.

[0037] In formula 2, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, m and n are the average number of moles of oxyalkylene groups and oxyethylene groups added, respectively, where 1≦m≦70 and 1≦n≦70. The proportion of oxyethylene groups to the total of oxyalkylene groups having 3 to 4 carbon atoms and oxyethylene groups is 20 to 80 mass%. The oxyalkylene groups having 3 to 4 carbon atoms and oxyethylene groups may be added in a block or random manner. R ａ and R ｂ are the same or different hydrocarbon groups having 1 to 4 carbon atoms or hydrogen atoms, and R ａ and R ｂ The ratio of the number of hydrogen atoms to the number of hydrocarbon groups is 0.15 or less.

[0038] Specific examples of AO include an oxypropylene group, an oxybutylene group, an oxyisobutylene group, an oxytrimethylene group, and an oxytetramethylene group. Of these, an oxypropylene group and an oxybutylene group are preferred.

[0039] The range of m, which is the average number of moles of oxyalkylene groups having 3 to 4 carbon atoms, is preferably 2≦m≦20. The range of n, which is the average number of moles of oxyethylene groups added, is preferably 2≦n≦20. In addition, the range of (m+n) is preferably 8 to 100 from the viewpoint of stickiness, etc.

[0040] The order in which EO and AO are added in Formula 2 is not particularly limited, and they may be added in a block or random manner. When added in a block, EO and AO may be added in a two-stage block or in a three-stage or more block. It is preferable that EO and AO are added in a random manner.

[0041] R ａ and R ｂ are hydrocarbon groups having 1 to 4 carbon atoms or hydrogen atoms, and may be the same or different. Examples of hydrocarbon groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups. Of these, methyl and ethyl groups are preferred.

[0042] R ａ and R ｂ may each be the same hydrocarbon group or a hydrogen atom, or may contain a mixture of hydrocarbon groups and hydrogen atoms, or may contain a mixture of different hydrocarbon groups. ａ and R ｂ The ratio Y / X of the number of hydrogen atoms (Y) to the number of hydrocarbon groups (X) is 0.15 or less, preferably 0.06 or less.

[0043] The alkylene oxide derivative of the above formula 2 can be produced by a known method, for example, by addition polymerization of ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms to a compound having a hydroxyl group, followed by an etherification reaction with an alkyl halide in the presence of an alkali catalyst.

[0044] The blending amount of the alkylene oxide derivative of the above formula 2 is not particularly limited, and can be, for example, 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more relative to the total amount of the cosmetic, and can also be 20% by mass or less, 17% by mass or less, 15% by mass or less, 13% by mass or less, 10% by mass or less, 8.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, or 3.0% by mass or less.

[0045] From the viewpoint of further improving skin permeability when used in combination with a specific water-soluble drug, the mass ratio of the alkylene oxide derivative of the above formula 2 to the specific water-soluble drug is preferably 0.5 or more, 0.7 or more, 1.0 or more, 1.5 or more, or 2.0 or more, and is also preferably 20 or less, 15 or less, 12 or less, 10 or less, or 8.0 or less.

[0046] <Skin permeability of specific water-soluble drug> The skin permeability of the specific water-soluble drug in the cosmetic composition of the present disclosure can be evaluated, for example, from the results of a cumulative permeation test described below using a simulated skin film. The simulated skin film has properties similar to those of skin. Therefore, such a cumulative permeation test can simulate the drug's permeation through the skin.

[0047] (Cumulative permeation amount of specific water-soluble drug) In some embodiments, the cosmetic composition of the present disclosure has a cumulative permeation amount of 5.0 μg / cm after 3 hours in such a cumulative permeation test. ２ Above, 7.0μg / cm ２ Above, 10.0μg / cm ２ Above, 13.0μg / cm ２ or more, or 15.0 μg / cm ２ The upper limit of the cumulative permeation amount is not particularly limited, and for example, it is 100 μg / cm ２ Below, 80.0μg / cm２ Below, 60.0μg / cm ２ or less, or 55.0 μg / cm ２ It can be as follows:

[0048] (Ratio Relating to Cumulative Permeation Amount of Specific Water-Soluble Drug) In some embodiments, the cosmetic preparation of the present disclosure can achieve a ratio of the cumulative permeation amount of the cosmetic preparation containing the specific surfactant to the cumulative permeation amount of the cosmetic preparation not containing the specific surfactant, with respect to the cumulative permeation amount after 3 hours in such a cumulative permeation test, of more than 1.5, 1.7 or more, 2.0 or more, 2.3 or more, or 2.5 or more. The upper limit of this ratio is not particularly limited, and can be, for example, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9.0 or less, or 8.0 or less. Here, in the present disclosure, a "cosmetic preparation not containing the specific surfactant" refers to a cosmetic preparation that has substantially the same composition as a cosmetic preparation containing the specific surfactant, except for the absence of the specific surfactant. Furthermore, the term "substantially" is intended to mean that it is acceptable to incorporate a predetermined amount (e.g., 0.2% by mass) of a surfactant that does not act as a skin penetration enhancer (e.g., the nonionic surfactant "PPG-13 decyltetradeceth-24") into the entire cosmetic preparation not containing the specific surfactant. If a cosmetic does not contain a surfactant, the specific water-soluble drug will be repelled by the simulated skin membrane and the surface of the skin, which may make it difficult to conduct a good comparative experiment. Therefore, it is permissible to blend a specified amount of a surfactant that does not act as a skin penetration enhancer into a cosmetic that does not contain a specific surfactant.

[0049] <Form and Shape of Cosmetics> The formulation of the cosmetics of the present disclosure is not particularly limited. However, from the viewpoint of the skin penetration of the specific water-soluble drug, a single aqueous phase form, or an oil-in-water or water-in-oil emulsion form is preferred, and a single aqueous phase form is more preferred. Each of these formulations can be appropriately prepared by conventional methods using known materials such as oil, emulsifier, and water as needed. Here, in the present disclosure, the term "single aqueous phase" refers to a single phase essentially composed of an aqueous phase. Furthermore, "substantially" means that, for example, oil (e.g., an oil-soluble UV absorber) may be solvated or solubilized with alcohol or the like and incorporated into the aqueous phase to a small extent, but does not include oil droplets (emulsified particles) emulsified with a surfactant or the like, as contained in an oil-in-water emulsion composition.

[0050] The form of the cosmetic of the present disclosure is not particularly limited, and may be in the form of, for example, a milky lotion, a cream, or a liquid.

[0051] The product form of the cosmetics of the present disclosure is not particularly limited, and examples thereof include skin care cosmetics such as serum, lotion, moisturizing gel, massage gel, emulsion, and cream; facial cosmetics such as packs; makeup cosmetics such as foundation and eye shadow; sunscreen cosmetics (sunscreen agents); body cosmetics; skin cleansers such as makeup removers and body shampoos; hair cosmetics such as hair liquid, hair tonic, hair conditioner, shampoo, rinse, and hair growth agents; shaving cosmetics such as shaving cream, pre-shave lotion, and after-shave lotion; ointments, etc.

[0052] <<Application Area of ​​Cosmetic>> The cosmetic of the present disclosure can be applied to any part of the body, for example, any part of the skin surface (body surface). Specifically, it can be applied appropriately to the skin surface of, for example, the face (lips, eyes, eyelids, cheeks, forehead, between the eyebrows, nose, etc.), head (scalp), ears, hands, arms, neck, legs, feet, chest, abdomen, back, etc. Here, skin also includes nails, which are hardened due to changes in the keratin layer of the skin epidermis.

[0053] A cosmetic method using the cosmetic preparation of the present disclosure includes applying the cosmetic preparation described above to the skin. Note that in this disclosure, the term "cosmetic method" refers to a method of applying the cosmetic preparation of the present disclosure to the skin to improve and beautify the condition of the skin, and is different from methods of surgery, treatment, or diagnosis for humans.

[0054] The cosmetic preparation for use in the beauty treatment method of the present disclosure is not particularly limited, and examples thereof include skin care cosmetic preparations such as beauty serums, lotions, moisturizing gels, massage gels, emulsions, and creams. The cosmetic preparations may be used alone or in combination of two or more. The cosmetic preparations may also be used by impregnating a face mask or the like.

[0055] The present invention will be described in more detail below with reference to test examples and examples, but the present invention is not limited thereto. Unless otherwise specified, the blending amounts are expressed in mass %.

[0056] Test Examples 1 to 4 The following evaluations were carried out using each sample obtained by the manufacturing method described below, and the results are summarized in Tables 1 to 4 and Figures 1 and 2. Note that, in each table and Figure 1, the "ratio of cumulative permeation amount" means, for the comparative examples and examples, the ratio of the cumulative permeation amount after 3 hours for each example to the cumulative permeation amount after 3 hours for Comparative Example 1, and for Reference Comparative Example 1 and Reference Example 1 in Table 1 and Figure 1, it means the ratio of the cumulative permeation amount after 3 hours for Reference Example 1 to the cumulative permeation amount after 3 hours for Reference Comparative Example 1.

[0057] <Evaluation of Cosmetics> (Cumulative Permeation Test) Regarding the permeability of drugs, the permeability of specific water-soluble drugs through a simulated skin membrane was evaluated using a diffusion cell array system (manufactured by Ikeda Rika Co., Ltd., hereinafter referred to as "diffusion cell") suitable for screening.

[0058] For the diffusion cell, 0.785 cm ２A diffusion cell array system with an effective permeation area of ​​1000 nm was used. The pseudo-skin membrane, which is the permeable membrane placed in the diffusion cell, was a Strat-M™ membrane (manufactured by Merck Millipore) cut with a punch to match the outer diameter of the donor cell that constitutes the diffusion cell. The pseudo-skin membrane was thoroughly hydrated by immersion in physiological phosphate buffer solution (PBS) before being placed in the diffusion cell.

[0059] The receiver cell of the diffusion cell was filled with PBS, and the pseudo-skin membrane was firmly fixed between the receiver cell and the donor cell using a cell clamp to prevent air from getting in. The diffusion cell was placed on a hot plate to maintain the surface temperature of the pseudo-skin membrane at approximately 32°C, which corresponds to the surface temperature of the skin, and the PBS in the receiver cell was allowed to acclimate for approximately 1 hour while being stirred with a stirrer bar.

[0060] The sample was applied to the simulated skin membrane in a limited open area, which is similar to the actual application method. The applied amount was 10 μg / cm ２ The sample was uniformly applied to the simulated skin membrane so that the PBS was measured. Three hours after application, the PBS was collected from the receiver cell. The amount of the specific water-soluble drug in the collected PBS was quantified using an HPLC system equipped with an LC-MS detector, and the cumulative permeation amount was calculated.

[0061] Test Example 1: Effect of various components used together with a specific water-soluble drug on transdermal permeability In Test Example 1, the effect of various components used together with a specific water-soluble drug on transdermal permeability was investigated. The results are summarized in Table 1 and Figure 1. The cumulative permeation amount is the average value of values ​​obtained by measuring three times for each sample. Furthermore, Reference Comparative Example 1 and Reference Example 1 are examples for reference evaluation of the effect of a specific surfactant on water-soluble drugs other than the specific water-soluble drug.

[0062] Comparative Example 1 Hydroxyethylimidazolidinone, a specific water-soluble drug, and PPG-13 decyltetradeceth-24, a surfactant, were added to ion-exchanged water in the blending ratios shown in Table 1, and the mixture was stirred and mixed with a stirrer to prepare a single aqueous phase composition.

[0063] (Comparative Examples 2 to 6, Example 1, Reference Comparative Example 1, and Reference Example 1) Single aqueous phase compositions of Comparative Examples 2 to 6, Example 1, Reference Comparative Example 1, and Reference Example 1 were prepared in the same manner as Comparative Example 1, except that the components and blending amounts were changed as shown in Table 1.

[0064]

[0065] (Results) As is clear from the results in Table 1 and Figure 1, it was confirmed that the composition of Example 1 containing a specific water-soluble drug and a specific surfactant can improve the permeability of the specific water-soluble drug into the pseudo-skin membrane, i.e., transdermal permeability, by more than two times compared to the composition of Comparative Example 1 prepared using a surfactant that does not act as a skin penetration enhancer.

[0066] Furthermore, from the results of the ratio of cumulative permeation amounts in Reference Comparative Example 1 and Reference Example 1, when the specific surfactant of the present disclosure is used in comparison with another water-soluble drug (niacinamide) that is not included in the specific water-soluble drug of the present disclosure, the permeability of the water-soluble drug into the pseudo-skin membrane is improved by only 1.5 times.From this result, it can be said that the combination of the specific water-soluble drug and the specific surfactant specifically improves the permeability into the pseudo-skin membrane, i.e., transdermal permeability.

[0067] Furthermore, although components known as transdermal penetration enhancers were used in Comparative Examples 2 to 6, it was found that such components did not improve the permeability through the pseudo-skin membrane, i.e., transdermal permeability. In other words, it was found that not all components known as transdermal penetration enhancers are equally effective for the specific water-soluble drug of the present disclosure.

[0068] Test Example 2: Effect of Different Blending Ratios of Specific Surfactant on Transdermal Penetration In Test Example 2, the effect of different blending ratios of specific surfactant on transdermal penetration was investigated. The results are summarized in Table 2. The cumulative permeation amount is the average of the values ​​obtained by measuring twice for each sample. For reference, Table 2 also lists the results of Example 1 and Comparative Example 1.

[0069] Examples 2 to 4 Single aqueous phase compositions of Examples 2 to 4 were prepared in the same manner as in Example 1, except that the blending amounts were changed as shown in Table 2.

[0070]

[0071] (Results) The results in Table 2 show that even if the amount of the specific surfactant is lowered or increased compared to Example 1, the permeability of the specific water-soluble drug into the pseudo-skin membrane, i.e., transdermal permeability, can be significantly increased.

[0072] Test Example 3: Effect of different blending ratios of specific water-soluble drug on transdermal permeability In Test Example 3, the effect of different blending ratios of specific water-soluble drug on transdermal permeability was examined. The results are summarized in Table 3. The cumulative permeation amount is the average of the values ​​obtained by measuring twice for each sample. For reference, Table 3 also lists the results of Example 1 and Comparative Example 1.

[0073] (Examples 5 to 6 and Comparative Examples 7 to 8) Single aqueous phase compositions of Examples 5 to 6 and Comparative Examples 7 to 8 were prepared in the same manner as in Example 1 or Comparative Example 1, except that the blending amounts were changed as shown in Table 3.

[0074]

[0075] (Results) The results in Table 3 show that even if the amount of the specific water-soluble drug is lowered or increased compared to Example 1, the permeability of the specific water-soluble drug into the pseudo-skin membrane, i.e., transdermal permeability, can be significantly increased.

[0076] Test Example 4: Effect of Different Types of Specific Surfactants on Transdermal Permeability In Test Example 4, the effect of different types of specific surfactants on transdermal permeability was investigated. The results are summarized in Table 4 and Figure 2. The cumulative permeation amount is the average of values ​​obtained by measuring each sample three times.

[0077] Examples 7 to 10 Single aqueous phase compositions of Examples 7 to 10 were prepared in the same manner as in Example 1, except that the ingredients and amounts were changed as shown in Table 4.

[0078]

[0079] (Results) From the results in Table 4 and FIG. 2, it was found that amino acid type surfactants and taurine type surfactants can significantly increase the permeability of a specific water-soluble drug through the pseudo-skin membrane, i.e., transdermal permeability.

Claims

1. At least one water-soluble agent selected from the group consisting of an imidazolidinone derivative represented by the following formula (1) and a salt thereof, and At least one surfactant selected from the group consisting of an amino acid type surfactant and a taurine type surfactant, A cosmetic containing the same. 【Chemical Formula 1】 (In formula (1), R １ and R ２ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms and having 0 to 3 hydroxyl groups, or a cycloalkyl group having 3 to 7 carbon atoms and having 0 to 5 hydroxyl groups.)

2. The cosmetic according to claim 1, wherein the amino acid type surfactant is an α-amino acid type surfactant.

3. The cosmetic according to claim 1, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut oil fatty acid amide propyl betaine, sodium cocoamphoacetate, potassium cocoamphoacetate, and sodium methyl taurine coconut oil fatty acid.

4. The cosmetic according to any one of claims 1 to 3, wherein the imidazolidinone derivative is at least one selected from the group consisting of 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone.

5. The cosmetic according to any one of claims 1 to 3, wherein the mass ratio of the surfactant to the water-soluble agent is more than 0.

05.

6. The cosmetic according to any one of claims 1 to 3, wherein the content of the water-soluble agent is 0.1% by mass or more based on the whole cosmetic.

7. A beauty method comprising applying the cosmetic according to any one of claims 1 to 3 to the skin.

8. Use of at least one surfactant selected from the group consisting of amino acid-type surfactants and taurine-type surfactants as a percutaneous penetration enhancer for at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof. 【Chemical formula 2】 (In formula 1, R １ and R ２ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms and having 0 to 3 hydroxyl groups, or a cycloalkyl group having 3 to 7 carbon atoms and having 0 to 5 hydroxy groups.)

9. The use according to claim 8, wherein the amino acid-type surfactant is an α-amino acid-type surfactant.

10. The use according to claim 8, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut oil fatty acid amidopropyl betaine, sodium cocooyl glycinate, potassium cocooyl glutamate, and sodium methyl taurine coconut oil fatty acid.

11. The use according to any one of claims 8 to 10, wherein the imidazolidinone derivative is at least one selected from the group consisting of 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone.

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