Oil-in-water emulsion composition containing glycyrrhetinic acid

Abstract

To provide an oil-in-water emulsion composition that contains glycyrrhetinic acid and offers high storage stability.SOLUTION: An oil-in-water emulsion composition contains the following components (A), (B) and (C): (A) glycyrrhetinic acid, (B) N-acylamino acid diester, and (C) an anionic surfactant.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an oil-in-water emulsion composition containing glycyrrhetinic acid. [Background technology]

[0002] Glycyrrhetinic acid is widely used as an anti-inflammatory ingredient in cosmetic compositions or topical skin preparations. Although glycyrrhetinic acid is an amphiphilic substance, it is hardly soluble in water, and is usually dissolved in a large amount of alcohol such as ethanol and then added, or dissolved in an oily component and emulsified to be incorporated into cosmetic compositions or topical skin preparations.

[0003] Patent Document 1 discloses a skin preparation for external use that contains a hydroxylated phospholipid and an anti-inflammatory component consisting of glycyrrhetinic acid. An ester of an N-acylamino acid having a cholesteryl group or a phytosteryl group is used as a co-ingredients.

[0004] Patent Document 2 discloses an oily composition containing (a) N-lauroyl sarcosine isopropyl, (b) a poorly water-soluble oily component having a melting point of 40°C or lower, having one or more hydrogen-bonding groups in the molecule which are hydroxyl groups, carboxyl groups, amino groups, amide groups, urea groups, oxo groups or ether groups, and having a linear or branched carbon chain with 12 to 24 carbon atoms, and (c) glycyrrhetinic acid as an active ingredient that is poorly soluble in oil.

[0005] Patent Document 3 discloses a personal care composition comprising: a) a safe and effective amount of glycyrrhizinic acid and / or glycyrrhetinic acid; b) a safe and effective amount of a first active substance selected from the group consisting of N-acylamino acid compounds, hexamidine, cetylpyridinium chloride, ergothioneine, and combinations thereof; and c) a dermatologically acceptable carrier. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Patent Publication 2008-115109 [Patent Document 2] Patent No. 5989139 [Patent Document 3] Special table 2008-540670 Summary of the Invention [Problem to be solved by the invention]

[0007] Conventional emulsion or oil compositions containing glycyrrhetinic acid and a specific N-acylamino acid ester have sometimes had poor storage stability, such as the emulsion particles becoming coarse over time when the composition is stored, and / or the glycyrrhetinic acid or oil agent precipitating.

[0008] An object of the present invention is to provide an oil-in-water emulsion composition which contains glycyrrhetinic acid and has excellent storage stability. [Means for solving the problem]

[0009] The present invention encompasses the embodiments described below. Section 1. Components (A), (B) and (C) below: (A) glycyrrhetinic acid, (B) N-acyl amino acid diesters, and (C) Anionic surfactants 1. An oil-in-water emulsion composition comprising:

[0010] Section 2. Item 2. The oil-in-water emulsion composition according to Item 1, wherein the component (B) is a compound represented by the following formula (I): [ka] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 3 and R 4 each independently represents a linear, branched, or cyclic hydrocarbon group having 12 to 30 carbon atoms, m is an integer from 0 to 4.

[0011] Section 3. Item 2. The oil-in-water emulsion composition according to Item 1, wherein the component (B) is a compound represented by the following (I): [ka] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 3 and R 4 each independently represents a linear or branched hydrocarbon group having 12 to 20 carbon atoms, m is an integer from 0 to 4.

[0012] Section 4. Item 2. The oil-in-water emulsion composition according to Item 1, wherein the component (B) is a compound represented by the following formula (V): [ka] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 5 and R 6 one or both of R represents an alcohol residue of an alcohol group-containing terpenoid, 5 and R 6 When one of the above is an alcohol residue of the alcohol group-containing terpenoid, the other is an alcohol residue of a linear, branched, or cyclic hydrocarbon having 12 to 30 carbon atoms and an alcohol group, m is an integer from 0 to 4.

[0013] Section 5. 5. The oil-in-water emulsion composition according to claim 4, wherein the alcohol group-containing terpenoid is an alcohol group-containing triterpenoid. Section 6. 6. The oil-in-water emulsion composition according to claim 5, wherein the alcohol group-containing triterpenoid is an alcohol group-containing steroid. Section 7. 7. The oil-in-water emulsion composition according to claim 6, wherein the alcohol group-containing steroid is cholesterol or a phytosterol.

[0014] Section 8. 8. The oil-in-water emulsion composition according to any one of Items 1 to 7, wherein the component (C) is a compound represented by any one of the following (II) to (IV): [ka] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof; n is an integer from 1 to 10. [ka] (In the formula, R 1 is a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof; p is 0, 1, or 2; q is 0, 1, or 2, and p and q are not 0 at the same time.) [ka] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a carboxyl group, a sulfonic acid group, a sulfate group, a phosphate group, or a salt thereof; Y is a carboxyl group or a salt thereof, -NHR 5 (R 5 represents a hydrocarbon group having 1 to 20 carbon atoms and having at least one group selected from the group consisting of a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group, an -OH group, and an -SH group, Z-NR 6 -(R 6 represents a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group, an -O- group, or an -S- group, p is 0, 1, or 2; q is 0, 1, or 2, and p and q are not 0 at the same time.)

[0015] Section 9. 9. The oil-in-water emulsion composition according to claim 1, further comprising at least one compound selected from the group consisting of tocopherol and tocopherol derivatives. Section 10. 10. The oil-in-water emulsion composition according to any one of items 1 to 9, further comprising lecithin. Section 11. 11. The oil-in-water emulsion composition according to any one of items 1 to 10, further comprising a nonionic surfactant. Section 12. Item 12. A composition for external use on skin, comprising the oil-in-water emulsion composition according to any one of items 1 to 11. Section 13. Item 12. A composition for oral cavity comprising the oil-in-water emulsion composition according to any one of items 1 to 11. Effect of the Invention

[0016] According to the present invention, it is possible to provide an oil-in-water emulsion composition which contains glycyrrhetinic acid and has excellent storage stability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] In this specification, "comprise" is a concept that includes "consist essentially of" and "consist of". In the numerical ranges described in stages in this specification, the upper limit or lower limit of a certain numerical range can be arbitrarily combined with the upper limit or lower limit of the numerical range of another stage. In addition, in the numerical ranges described in this specification, the upper limit or lower limit of the numerical range may be replaced with a value shown in an example or a value that can be unambiguously derived from an example. Furthermore, in this specification, a numerical value connected with "~" means a numerical range that includes the numerical values ​​before and after "~" as the lower limit and upper limit.

[0018] As used herein, a sulfonic acid group is -SO3H or -SO3-.

[0019] As used herein, a sulfate ester group is -O-SO3H or -O-SO3-.

[0020] In this specification, the phosphate group is a group represented by any of the following formulas (a1) to (a3).

[0021] [ka]

[0022] As used herein, a terpenoid is a compound that contains a five carbon isoprene unit.

[0023] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B) and (C): (A) glycyrrhetinic acid, (B) N-acyl amino acid diesters, and (C) Anionic surfactants Contains:

[0024] Component (A), glycyrrhetinic acid (CAS No. 471-53-4), is a compound having anti-inflammatory activity, and is incorporated as an active ingredient in the oil-in-water emulsion composition of the present invention.

[0025] [ka]

[0026] The amount of component (A) in the oil-in-water emulsion composition is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and more preferably 1% by mass or more. The amount of component (A) in the oil-in-water emulsion composition is preferably 30% by mass or less, and more preferably 10% by mass or less.

[0027] The N-acylamino acid diester of component (B) is an oily component used to improve the storage stability of the oil-in-water emulsion composition of the present invention containing glycyrrhetinic acid.

[0028] In one embodiment, component (B) is a compound represented by formula (I):

[0029] [ka]

[0030] In formula (I), R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 3 and R 4 each independently represents a linear, branched, or cyclic hydrocarbon group having 12 to 30 carbon atoms, m is an integer from 0 to 4.

[0031] R 1may be a saturated or unsaturated hydrocarbon group, and may be a straight or branched alkyl or alkenyl group having 5 to 23 carbon atoms. Examples of the acyl group of the acylamino acid ester include 2-ethylhexanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, behenoyl, oleoyl, isostearoyl, and linolenoyl groups, and preferably lauroyl. The acyl group may be derived from a mixed fatty acid, and is preferably a cocoyl fatty acid ester, palm oil fatty acid ester, palm kernel oil fatty acid ester, sunflower seed oil fatty acid ester, or macadamia nut oil fatty acid ester, and more preferably a cocoyl fatty acid ester or palm kernel oil fatty acid ester.

[0032] R 2 is preferably a methyl group or a hydrogen group, and more preferably a hydrogen group.

[0033] R 3 may be a saturated or unsaturated hydrocarbon group, and may be a linear, branched, or cyclic alkyl or alkenyl group having 12 to 30 carbon atoms. 3 represents a linear or branched hydrocarbon group having 12 to 20 carbon atoms. In another preferred embodiment, R 3 is a linear or branched alkyl or alkenyl group having 12 to 20 carbon atoms.

[0034] R 4 may be a saturated or unsaturated hydrocarbon group, and may be a linear, branched, or cyclic alkyl or alkenyl group having 12 to 30 carbon atoms. 4 represents a linear or branched hydrocarbon group having 12 to 20 carbon atoms. In another preferred embodiment, R 4 is a linear or branched alkyl or alkenyl group having 12 to 20 carbon atoms.

[0035] In one preferred embodiment, component (B) is a compound represented by the following formula (I):

[0036] [ka]

[0037] During the ceremony, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 3 and R 4 each independently represents a linear or branched hydrocarbon group having 12 to 20 carbon atoms, m is an integer from 0 to 4.

[0038] The N-acylamino acid diester of component (B) can be produced by condensing an amino acid having two carboxy groups with an acyl chloride in the presence of an alkali to obtain an N-acylamino acid, and then dehydrating and condensing the resulting N-acylamino acid with the corresponding alcohol in the presence of a base or acid, and optionally in the presence of a solvent. Glutamic acid is preferred as the amino acid having two carboxy groups in terms of ease of availability.

[0039] In another embodiment, component (B) is a compound represented by formula (V):

[0040] [ka]

[0041] In formula (V), R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, R 5 and R 6 one or both of R represents an alcohol residue of an alcohol group-containing terpenoid, 5 and R 6When one of the above is an alcohol residue of the alcohol group-containing terpenoid, the other is an alcohol residue of a linear, branched, or cyclic hydrocarbon having 12 to 30 carbon atoms and an alcohol group, m is an integer from 0 to 4.

[0042] R 1 may be a saturated or unsaturated hydrocarbon group, and may be a straight or branched alkyl or alkenyl group having 5 to 23 carbon atoms. Examples of the acyl group of the acylamino acid ester include 2-ethylhexanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, behenoyl, oleoyl, isostearoyl, and linolenoyl groups, and preferably lauroyl. The acyl group may be derived from a mixed fatty acid, and is preferably a cocoyl fatty acid ester, palm oil fatty acid ester, palm kernel oil fatty acid ester, sunflower seed oil fatty acid ester, or macadamia nut oil fatty acid ester, and more preferably a cocoyl fatty acid ester or palm kernel oil fatty acid ester.

[0043] R 2 is preferably a methyl group or a hydrogen group, and more preferably a hydrogen group.

[0044] Terpenoids are also called terpenes, and include hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, triterpenes, and tetraterpenes. Hemiterpenes include isoprene, monoterpenes include menthol and geraniol, sesquiterpenes include artemisinin and α-bisabolol, diterpenes include paclitaxel and gibberellin, triterpenes include lanosterol, cholesterol, phytosterols, saponins, squalane, squalene, glycyrrhetinic acid, oleanolic acid, ursolic acid, lupeol, and tetraterpenes include phytoene, carotenoids, and xanthophylls.

[0045] Among these terpenes, triterpenes are preferred. Among the terpenes, steroids are more preferred, and alcohol group-containing steroids are more preferred. Examples of steroids include cholesterol, phytosterols, strophanthidin, cholestanol, steroid hormones (such as testosterone and estradiol), cortisol, and aldosterone.

[0046] Among steroids, alcohol group-containing steroids are preferred, and sterols are more preferred. Sterols are a subgroup of steroids, and are steroid compounds that have a hydroxy group at the C3 position. Preferred sterols are cholesterol and phytosterols, including β-sitosterol, campesterol, stigmasterol, brassicasterol, etc.

[0047] In one embodiment, R 5 and R 6 are the alcohol residues of alcohol-containing terpenoids. In this case, R 5 and R 6 may be the same or different. In another embodiment, R 5 is the alcohol residue of an alcohol group-containing terpenoid, and R 6 is an alcohol residue of a linear, branched, or cyclic hydrocarbon having 12 to 30 carbon atoms and an alcohol group. 5 is a linear, branched, or cyclic hydrocarbon alcohol residue having 12 to 30 carbon atoms and an alcohol group; R 6 is the alcohol residue of the alcohol group-containing terpenoid. 5 and R 6 are both alcohol residues, and are bonded to adjacent -CO- and -O- to form an ester bond.

[0048] R 5 and R 6 The number of carbon atoms in the alcohol residue of the alcohol-containing terpenoid constituting either one or both of the above is preferably 12 to 40.

[0049] R 5 and R 6 The alcohol residue of the alcohol group-containing terpenoid constituting either one or both of the above is preferably the alcohol residue of an alcohol group-containing triterpenoid. The alcohol group-containing triterpenoid is preferably an alcohol group-containing steroid. The alcohol group-containing steroid is preferably a cholesterol or phytosterol group.

[0050] Examples of the component (B) represented by formula (V) include di(cholesteryl / octyldodecyl) lauroyl glutamate (trade name "ELDEW CL202", manufactured by Ajinomoto Co., Inc.), di(cholesteryl / behenyl / octyldodecyl) lauroyl glutamate (trade name "ELDEW CL301", manufactured by Ajinomoto Co., Inc.), and di(phytosteryl / behenyl / octyldodecyl) lauroyl glutamate (trade name "ELDEW PS304", manufactured by Ajinomoto Co., Inc.).

[0051] The component (B) may be one type, or two or more types may be combined.

[0052] From the viewpoint of storage stability of the oil-in-water emulsion composition, the ratio of component (A) to component (B) in the oil-in-water emulsion composition is preferably component (A):component (B)=1:5 to 1:30 by mass, and more preferably 1:10 to 1:20.

[0053] The amount of component (B) in the oil-in-water emulsion composition is not particularly limited, but from the viewpoints of promoting emulsification and the storage stability of the oil-in-water emulsion composition, it is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 30% by mass or less, more preferably 20% by mass or less.

[0054] Component (C) is a compound represented by any one of the following (II) to (IV).

[0055] [ka]

[0056] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof; n is an integer from 1 to 10.

[0057] [ka]

[0058] (In the formula, R 1 is a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof; p is 0, 1, or 2; q is 0, 1, or 2; And p and q are not 0 at the same time.)

[0059] [ka]

[0060] (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrogen group, X represents a carboxyl group, a sulfonic acid group, a sulfate group, a phosphate group, or a salt thereof; Y is a carboxyl group or a salt thereof, -NHR 5 (R 5represents a hydrocarbon having 1 to 20 carbon atoms and having a group selected from the group consisting of a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group, an -OH group, and an -SH group, Z-NR 6 -(R 6 represents a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group, an -O- group, or an -S- group, p is 0, 1, or 2; q is 0, 1, or 2, and p and q are not 0 at the same time.)

[0061] In formula (II), R 1 R may be a saturated or unsaturated hydrocarbon group, and may be a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms. 1 is preferably a straight or branched alkyl group having 12 to 23 carbon atoms. R 2 is preferably a methyl group or a hydrogen group, and more preferably a methyl group.

[0062] When X is a salt of a sulfonic acid group, a sulfate ester group, or a phosphate ester group, such salts include alkali metal (such as sodium) salts and alkaline earth metal (such as magnesium and calcium) salts.

[0063] X is preferably a salt of a sulfonic acid group.

[0064] Preferred compounds represented by formula (II) include, but are not limited to, sodium salts of amides of long-chain fatty acids having 12 or more carbon atoms and N-methyltaurine, such as sodium stearoyl methyltaurine, sodium lauryl methyltaurine, and sodium myristoyl methyltaurine.

[0065] In formula (III), R 1 R may be a saturated or unsaturated hydrocarbon group, and may be a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms. 1is preferably a straight or branched alkyl group having 12 to 23 carbon atoms.

[0066] R 2 is preferably a methyl group or a hydrogen group, and more preferably a methyl group.

[0067] When X is a salt of a sulfonic acid group, a sulfate group, or a phosphate group, such salts include salts of alkali metals (such as sodium) and salts of alkaline earth metals (such as magnesium and calcium). X is preferably a salt of a sulfonic acid group.

[0068] In formula (IV), R 1 R may be a saturated or unsaturated hydrocarbon group, and may be a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms. 1 is preferably a straight or branched alkyl group having 12 to 23 carbon atoms.

[0069] R 2 is preferably a methyl group or a hydrogen group, and more preferably a hydrogen group.

[0070] When X is a salt of a carboxyl group, a sulfonic acid group, a sulfate group, or a phosphate group, such salts include salts of alkali metals (such as sodium) and salts of alkaline earth metals (such as magnesium and calcium). X is preferably a carboxyl group or a sodium salt thereof.

[0071] Y is a hydrocarbon group having 1 to 20 carbon atoms and at least one substituent. At least one of the hydrogen atoms bonded to the carbon of the hydrocarbon group having 1 to 20 carbon atoms is substituted with a substituent. The substituent can be a carboxyl group or a salt thereof, -NHR 5 (R 5 is at least one group selected from the group consisting of a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group), an -OH group, and an -SH group. An example of a salt of a carboxyl group is a sodium salt. The number of substituents is not particularly limited, but is preferably one or two.

[0072] It is preferred that only the hydrogen bonded to the carbon at one end of the hydrocarbon group, or only the hydrogen bonded to the carbon at both ends of the hydrocarbon group, be substituted with a substituent.

[0073] Z-NR 6 -(R 6 is preferably a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen group, and more preferably --NH--.

[0074] The component (C) may be one type, or two or more types may be combined.

[0075] The amount of component (C) in the oil-in-water emulsion composition is not particularly limited, but from the viewpoint of preventing particle coarsening during preparation and storage of the oil-in-water emulsion composition, the amount is preferably 0.1 to 10 mass%, more preferably 0.3 to 8 mass%, and even more preferably 0.5 to 5 mass%.

[0076] The oil-in-water emulsion composition of the present invention can contain, as oily components, fats and oils, hydrocarbons, waxes, esters, fatty acids, higher alcohols, sterols, oil-soluble polymers, oil-soluble pigments, oil-soluble proteins, oil-soluble vitamins, and the like.

[0077] The oil-in-water emulsion composition of the present invention preferably contains at least one compound selected from the group consisting of tocopherol and tocopherol derivatives, and in particular, it is preferable to use tocopherol or a tocopherol derivative in combination. Examples of the tocopherol derivative include tocopherol acetate, tocopherol nicotinate, tocopherol succinate, tocopherol ascorbate, and tocopherol phosphate, with tocopherol acetate being particularly preferred. Commercially available tocopherol and tocopherol derivatives can be used.

[0078] When the oil-in-water emulsion composition of the present invention contains at least one compound selected from the group consisting of tocopherol and tocopherol derivatives, the content of the compound in the oil-in-water emulsion composition is preferably 0.01% by mass to 5% by mass, and more preferably 0.1% by mass to 1% by mass.

[0079] The oil-in-water emulsion composition of the present invention may contain a phospholipid. Examples of the phospholipid include glycerophospholipid and sphingophospholipid.

[0080] Glycerophospholipids are compounds having a glycerophosphate backbone and a fatty acid ester, a long-chain alkyl ether, or a vinyl ether as a lipophilic group, and examples thereof include phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphadiylinositol, phosphatidylinositol polyphosphate, phosphatidylglycerol, diphosphatidylglycerol (cardiolipin), phosphatidic acid, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylserine, lysophosphatidylinositol, lysophosphatidylglycerol, and lysophosphatidic acid.

[0081] Sphingophospholipids are compounds that have a long-chain base such as sphingosine or phytosphingosine or a long-chain fatty acid and phosphoric acid or phosphonic acid, and examples thereof include ceramide 1-phosphate derivatives (such as sphingomyelin) and ceramide 1-phosphonic acid derivatives (such as ceramide aminoethylphosphonic acid).

[0082] When the oil-in-water emulsion composition of the present invention contains a phospholipid, the phospholipid is preferably lecithin in terms of promoting emulsification. Lecithin is a type of glycerophospholipid, and soybean lecithin and egg yolk lecithin obtained from soybeans and egg yolk are industrially produced and commercially available.

[0083] Soybean lecithin is produced by drying and refining the by-product of soybean oil refining process. Normally, paste-type lecithin with a phospholipid content of 70% or less by mass contains about 30% by mass of soybean crude oil, and because it is inexpensive, this paste-type lecithin is mostly used, especially in the food industry. In recent years, due to the physiological activity of phospholipids themselves and the need for more advanced emulsifiers, technologies such as advanced purification, fractionation, and enzymatic decomposition have been added, and various lecithin groups with different performance and functions have been produced.

[0084] Highly refined lecithin is obtained by deoiling the above-mentioned paste-like lecithin using a solvent such as acetone and powdering it, and generally has a lecithin content of 90% by mass or more. Examples of this highly refined lecithin include Phospholipon 20 (Lipoid), Lesion P (Riken Vitamin Co., Ltd.), SLP White (Tsuji Oil Mills Co., Ltd.), and Emulmetic 300 (Lucas Meyer Cosmetics).

[0085] Fractionated lecithin is obtained by increasing the content of specific phospholipids by utilizing the difference in solubility in various solvents or by performing operations such as distillation on the above-mentioned highly purified lecithin, and generally, products with increased phosphatidylcholine content are commercially available. Examples of fractionated lecithin with increased phosphatidylcholine content include Phospholipon 85G (PC content: 80% by mass), Phospholipon 90G (PC content: 94% by mass), Lipoid P75 (PC content: 68-73%), Lipoid P100 (PC content: 90% or more) (all from Lipoid Co., Ltd.), Emermetic 900 (PC content: 50% by mass), Emermetic 930 (PC content: 95% by mass) (all from Lucas Meyer Cosmetics Co., Ltd.), SLP-PC70, SLP-PC90 (all from Tsuji Oil Mills Co., Ltd.), etc.

[0086] By containing lecithin, the transparency and stability over time of the oil-in-water emulsion composition are further improved. From the viewpoint of the transparency and stability over time of the oil-in-water emulsion composition, the lecithin in the present invention is preferably fractionated lecithin.

[0087] The content of phospholipid or lecithin in the oil-in-water emulsion composition of the present invention is preferably 0.1% by mass to 10% by mass, more preferably 0.2% by mass to 8% by mass, and even more preferably 1% by mass to 4% by mass. By making the content of phospholipid 0.1% by mass or more, the emulsion stability of the oil-in-water emulsion composition tends to be better. In addition, by making the content of phospholipid 10% by mass or less, the excess phospholipid does not separate from the oily component to form a phospholipid dispersion in water, and the emulsion stability of the oil-in-water emulsion composition is obtained.

[0088] The oil-in-water emulsion composition of the present invention may further contain a nonionic surfactant. Examples of nonionic surfactants include glycerin fatty acid esters, organic acid monoglycerides, polyglycerin fatty acid esters, propylene glycol fatty acid esters, polyglycerin condensed ricinoleic acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, and esters of polyoxyethylene sorbitan fatty acid esters, POE (polyoxyethylene) cetyl ether, POE oleyl ether, POE castor oil ether, POE hydrogenated castor oil ether, POE phytosterol ether, and the like. The nonionic surfactant may be one type, or two or more types may be combined.

[0089] From the viewpoints of emulsifiability and stability over time, the nonionic surfactant is more preferably a polyglycerol fatty acid ester, a sorbitan fatty acid ester, a sucrose fatty acid ester, or a polyoxyethylene sorbitan fatty acid ester, and most preferably the nonionic surfactant is a polyglycerol fatty acid ester.

[0090] The polyglycerol fatty acid ester is preferably an ester of polyglycerol having an average degree of polymerization of 2 or more (preferably 6 to 15, more preferably 8 to 10) and a fatty acid having 8 to 18 carbon atoms (e.g., a fatty acid selected from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, and linoleic acid).

[0091] Preferred examples of polyglycerol fatty acid esters include hexaglycerol monooleate, hexaglycerol monostearate, hexaglycerol monopalmitate, hexaglycerol monomyristate, hexaglycerol monolaurate, decaglycerol monooleate, decaglycerol monostearate, decaglycerol monoisostearate, decaglycerol monopalmitate, decaglycerol monomyristate, decaglycerol monolaurate, etc. Among these, more preferred are decaglycerol monooleate (HLB=12), decaglycerol monostearate (HLB=12), decaglycerol monopalmitate (HLB=13), decaglycerol monomyristate (HLB=14), decaglycerol monolaurate (HLB=16), etc. These polyglycerol fatty acid esters can be used alone or in combination of two or more kinds.

[0092] The sucrose fatty acid ester preferably has a fatty acid carbon number of 12 or more, more preferably 12 to 20. Preferred examples of sucrose fatty acid ester include sucrose dioleate, sucrose distearate, sucrose dipalmitate, sucrose dimyristate, sucrose dilaurate, sucrose monooleate, sucrose monostearate, sucrose monopalmitate, sucrose monomyristate, and sucrose monolaurate, and among these, sucrose monooleate, sucrose monostearate, sucrose monopalmitate, sucrose monomyristate, and sucrose monolaurate are more preferred. In the present invention, these sucrose fatty acid esters can be used alone or in combination of two or more.

[0093] The sorbitan fatty acid ester preferably has a fatty acid carbon number of 8 or more, more preferably 12 or more. Preferred examples of the sorbitan fatty acid ester include sorbitan monocaprylate, sorbitan monolaurate, sorbitan monostearate, sorbitan sesquistearate, sorbitan tristearate, sorbitan isostearate, sorbitan sesquiisostearate, sorbitan oleate, sorbitan sesquioleate, sorbitan trioleate, etc. These sorbitan fatty acid esters can be used alone or in combination of two or more.

[0094] The polyoxyethylene sorbitan fatty acid ester preferably has a fatty acid carbon number of 8 or more, more preferably 12 or more. The length of ethylene oxide of polyoxyethylene (number of moles added) is preferably 2 to 100, more preferably 4 to 50. Preferable examples of polyoxyethylene sorbitan fatty acid ester include polyoxyethylene sorbitan monocaprylate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan sesquistearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan isostearate, polyoxyethylene sorbitan sesquiisostearate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan sesquioleate, polyoxyethylene sorbitan trioleate, and the like.

[0095] The content of the nonionic surfactant in the oil-in-water emulsion composition of the present invention is preferably 0.5% by mass to 30% by mass, more preferably 1% by mass to 20% by mass, and even more preferably 2% by mass to 15% by mass. The content of the nonionic surfactant of 0.5% by mass or more is preferable in that it improves the solubility of a predetermined amount of glycyrrhetinic acid derivative and makes it easy to lower the interfacial tension between the oil phase and the water phase. In addition, the content of the nonionic surfactant of 30% by mass or less is preferable in that the amount of the nonionic surfactant is not excessive.

[0096] The oil-in-water emulsion composition of the present invention preferably contains water. From the viewpoint of preservative properties during storage, the amount of water is preferably 20% by mass to 75% by mass, and more preferably 20% by mass to 50% by mass, based on the total amount of the oil-in-water emulsion composition.

[0097] In addition to the above-mentioned components, the emulsion composition of the present invention may contain additive components that are commonly used in the fields of food, cosmetics, etc., depending on the form of the composition.

[0098] For example, other additive components include monosaccharides or polysaccharides such as glucose, sucrose, kappa carrageenan, locust bean gum, guar gum, hydroxypropyl guar gum, xanthan gum, karaya gum, tamarind seed polysaccharide, gum arabic, tragacanth gum, hyaluronic acid, sodium hyaluronate, sodium chondroitin sulfate, and dextrin; sugar alcohols such as sorbitol, mannitol, maltitol, lactose, maltotriitol, and xylitol; inorganic salts such as sodium chloride and sodium sulfate; proteins with a molecular weight of over 5000 such as casein, albumin, methylated collagen, hydrolyzed collagen, water-soluble collagen, and gelatin; and acetyl groups such as glycine, alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, cystine, methionine, lysine, hydroxylysine, arginine, histidine, phenylalanine, tyrosine, tryptophan, proline, hydroxyproline, and acetylhydroxyproline. amino acids and their derivatives; synthetic polymers such as carboxyvinyl polymers, sodium polyacrylate, polyvinyl alcohol, polyethylene glycol, and ethylene oxide-propylene oxide block copolymers; water-soluble cellulose derivatives such as hydroxyethyl cellulose and methyl cellulose; flavonoids (catechin, anthocyanin, flavones, isoflavones, flavans, flavanones, rutin), ascorbic acid or its derivatives (ascorbic acid, sodium ascorbate, potassium ascorbate, calcium ascorbate, L-ascorbic acid phosphate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, ascorbyl sulfate, disodium ascorbyl sulfate, and ascorbyl-2-glucoside), tocotrienol and its derivatives, phenolic acids (chlorogenic acid, ellagic acid, gallic acid, and propyl gallate), lignans, curcumins, coumarins, and hydroxystilbenes including pterostilbene. These added ingredients may be included based on their function, for example, as functional ingredients, excipients, viscosity modifiers, radical scavengers, and the like.

[0099] The aqueous component of the oil-in-water emulsion composition of the present invention may also contain polyhydric alcohols, water-soluble salts, polysaccharides, proteins, pH adjusters, antioxidants, preservatives, colorants, fragrances, and the like.

[0100] The oil-in-water emulsion composition of the present invention may also contain, as an oily component, fats and oils, hydrocarbons, waxes, esters, fatty acids, higher alcohols, polymers, oil-soluble dyes, oil-soluble proteins, and the like.

[0101] The method for producing the oil-in-water emulsion composition of the present invention is not particularly limited, and it can be produced according to a known method. For example, a production method including: a) dissolving an aqueous component in water or an aqueous medium to obtain an aqueous composition; b) mixing or dissolving an oil component to obtain an oil composition; and c) mixing the aqueous composition and the oil composition under stirring to emulsify and disperse, thereby obtaining an oil-in-water emulsion composition is preferred.

[0102] The mass ratio of the oily composition to the aqueous composition in the emulsion dispersion is not particularly limited, but the ratio (mass%) of the oily composition / aqueous composition is preferably 0.1 / 99.9 to 50 / 50, more preferably 0.5 / 99.5 to 30 / 70, and even more preferably 1 / 99 to 20 / 80. By making the ratio of the oily composition / aqueous composition 0.1 / 99.9 or more, the active ingredient is not reduced, so that practical problems of the oil-in-water emulsion composition tend not to occur, which is preferable. In addition, by making the ratio (mass%) of the oily composition / aqueous composition 50 / 50 or less, the surfactant concentration relative to the dispersed phase (oil phase) is not diluted, and the stability over time of the oil-in-water emulsion composition is maintained, which is preferable.

[0103] The emulsification dispersion may be a one-step emulsification operation, but it is preferable to carry out two or more steps of emulsification operations in order to obtain uniform and fine emulsion particles. Specifically, in addition to a one-step emulsification operation using a normal emulsification device that utilizes shearing action (for example, a stirrer or impeller stirring, a homomixer, a continuous flow type shear device, etc.), it is particularly preferable to use two or more types of emulsification devices in combination, such as a method of emulsifying through a high-pressure homogenizer or an ultrasonic disperser. By using a high-pressure homogenizer, the emulsion can be made into more uniform fine particle droplets. In addition, the emulsion dispersion may be carried out multiple times in order to obtain droplets with a more uniform particle size. The emulsification dispersion can be carried out with ordinary skill by those skilled in the art with reference to known techniques such as Patent No. 5989139.

[0104] The emulsion particles contained in the oil-in-water emulsion composition of the present invention preferably have an average particle size of 150 nm or less. This can improve not only the transparency of the appearance of the emulsion composition but also its stability. Furthermore, if the average particle size of the emulsion particles is 150 nm or less, the permeability of the emulsion particles can be improved when the emulsion composition is applied to the skin, scalp, etc., and the active ingredient can be more effectively permeated into the skin, scalp, etc.

[0105] The average particle size of the emulsion particles means the volume average particle size of the emulsion particles present in the oil-in-water emulsion composition.

[0106] The average particle size of the emulsion particles contained in the oil-in-water emulsion composition of the present invention is preferably 5 nm to 150 nm, more preferably 10 nm to 100 nm.

[0107] The average particle size of the emulsion particles contained in the oil-in-water emulsion composition of the present invention can be determined by a known method such as an electron microscope, centrifugal sedimentation method, liquid exclusion chromatography method, laser scattering diffraction method, or dynamic light scattering method. In view of accuracy and ease of measurement, it is preferable to measure using the dynamic light scattering method.

[0108] The oil-in-water emulsion composition of the present invention can be used for any purpose, but can be suitably used in cosmetics, quasi-drugs, medicines, etc. Specifically, it can be suitably used as hair cosmetics such as shampoos, rinses, and conditioners; skin cosmetics such as face washes, cleansing cosmetics, lotions, milky lotions, beauty creams, base cosmetics, sunscreen cosmetics, packs, and massage cosmetics; and external medicines such as ointments and creams containing various drugs.

[0109] The oil-in-water emulsion composition of the present invention may be in any form, such as a liquid, emulsion, gel, spray, or mousse.

[0110] Generally, lotions and beauty essences are required to be transparent and stable over time.

[0111] In this specification, "stability over time" can be evaluated by measuring the change in turbidity before and after the passage of time, the rate of change in average particle size, or both.

[0112] The present invention also provides a skin topical composition containing the oil-in-water emulsion composition of the present invention. The skin topical composition may be a cosmetic, a quasi-drug, or a pharmaceutical.

[0113] The skin topical composition of the present invention may be in the form of the emulsion composition described above. The skin topical composition of the present invention may contain other additive components that are commonly used in the fields of food and cosmetics, etc., in addition to the components described for the oil-in-water emulsion composition, depending on the form of the composition. Such an additive component includes, for example, a water-soluble polymer, which is added to increase the dispersion stability of the aqueous phase and improve the high-temperature and low-temperature stability.

[0114] The water-soluble polymer can be cationic water-soluble polymer, nonionic water-soluble polymer, or amphoteric water-soluble polymer.The water-soluble polymer is preferably not anionic water-soluble polymer, and is preferably nonionic water-soluble polymer, because of transparency and stability over time when used as a skin topical composition.Anionic water-soluble polymer may affect the stability of emulsion composition due to interaction with coexisting materials such as lecithin.

[0115] Examples of nonionic water-soluble polymers include acrylic acid derivatives (hydroxyethyl acrylate-methoxyethyl acrylate copolymers, polyacrylic acid amides, etc.), vinylpyrrolidone derivatives (polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, etc.), polyoxyalkylene glycol derivatives (polyethylene glycol, polypropylene glycol, etc.), cellulose derivatives (methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, etc.), associative nonionic polymers (hydrophobically modified polyether urethane, hydrophobically modified cellulose derivatives, etc.), polysaccharides and their derivatives (guar gum, locust bean gum, dextran, etc.), etc. Preferably, the water-soluble polymer includes at least one selected from the group consisting of cellulose derivatives and polyether urethane.

[0116] These water-soluble polymers can be used alone or in appropriate combination of two or more kinds.

[0117] The content of the water-soluble polymer in the composition for external use on skin is preferably 0.05% by mass or more, more preferably 0.1% by mass or more. The upper limit is preferably 4% by mass or less, more preferably 2% by mass or less. The specific content range is preferably 0.05 to 4% by mass, more preferably 0.1 to 2% by mass.

[0118] Examples of other additive components include polyhydric alcohols such as glycerin and 1,3-butylene glycol; monosaccharides such as kappa carrageenan, locust bean gum, guar gum, hydroxypropyl guar gum, xanthan gum, karaya gum, tamarind seed polysaccharide, gum arabic, acacia gum, Alcaligenes polysaccharide (also called "Alcaciaran"), tragacanth gum, gellan gum, native gellan gum, hyaluronic acid, sodium hyaluronate, sodium chondroitin sulfate, dextrin, and inulin. or polysaccharides; sugar alcohols such as sorbitol, mannitol, maltitol, lactose, maltotriitol, and xylitol; inorganic salts such as sodium chloride and sodium sulfate; proteins with a molecular weight of over 5000 such as casein, albumin, methylated collagen, hydrolyzed collagen, water-soluble collagen, and gelatin; glycine, alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, cystine, methionine, lysine, hydroxylysine, arginine, histidine, and phenylalanine. , tyrosine, tryptophan, proline, hydroxyproline, acetylhydroxyproline, and other amino acids and derivatives thereof; synthetic polymers such as carboxyvinyl polymer, sodium polyacrylate, polyvinyl alcohol, polyethylene glycol, and block copolymers of ethylene oxide and propylene oxide; water-soluble cellulose derivatives such as hydroxyethyl cellulose and methyl cellulose; flavonoids such as catechin, anthocyanin, flavon, isoflavone, flavan, flavanone, and rutin; ascorbic acid or derivatives thereof such as ascorbic acid, sodium ascorbate, potassium ascorbate, calcium ascorbate, L-ascorbic acid phosphate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, ascorbyl sulfate, disodium ascorbyl sulfate, and ascorbyl-2-glucoside; tocotrienol and derivatives thereof; and phenols such as chlorogenic acid, ellagic acid, gallic acid, propyl gallate, lignans, curcumins, coumarins, pterostilbene, and hydroxystilbene.

[0119] The topical skin composition of the present invention can also contain other additives that are typically used in such applications, such as pH adjusters, pH buffers, UV absorbers, preservatives, fragrances, colorants, excipients, viscosity adjusters, and radical scavengers.

[0120] The skin external composition of the present invention can also contain various ingredients based on their functions, such as emollients, treatment agents, lubricants, moisturizers, hair growth agents, hair care agents, hair growth agents, anti-hair graying agents, anti-aging agents, antioxidants, fragrances, colorants, antiperspirants, cooling agents, refreshing agents, warming agents, etc.

[0121] The skin external composition of the present invention may further contain, as pharmaceutical ingredients, hair restorers, hair tonics, hair growth agents, antibiotics, bactericides, anti-inflammatory agents, anti-allergic agents, and the like.

[0122] In addition, the content of ethanol in the composition for external use on the skin of the present invention is preferably 10% by mass or less based on the total mass of the composition for external use on the skin. This allows the composition for external use on the skin of the present invention to reduce irritation to the skin. From the viewpoint of reducing irritation to the skin, the content of ethanol in the composition for external use on the skin of the present invention is more preferably 0 to 1% by mass, even more preferably 0 to 0.5% by mass, and particularly preferably 0 to 0.1% by mass based on the total mass of the composition for external use on the skin.

[0123] The composition for external use on the skin of the present invention can contain a sufficient amount of active ingredient to exert an effect and can be stored in a refrigerator, so that it can be used as a cosmetic or ointment, and is preferably used as a cosmetic for the face or scalp.

[0124] Examples of skin external compositions include skin lotions, beauty essences, milky lotions, creams, masks, packs, hair washing cosmetics, fragrance cosmetics, liquid body cleansers, UV care cosmetics, deodorant cosmetics, oral care cosmetics, etc. (in the case of cosmetics), etc. In addition, these are not necessarily limited to those used by humans, and are also suitable for use as skin external preparations for animals such as pets.

[0125] The emulsion composition of the present invention is particularly suitable for use in aqueous cosmetics that require transparency. Lotions and beauty essences are generally required to have transparency, and are required to remain transparent and stable even after changes over time.

[0126] The skin topical composition of the present invention can be produced according to a known method. For example, the above-mentioned oil-in-water emulsion composition can be obtained by diluting it with purified water or the like so that the amount of the emulsion composition is 0.001% by mass to 50% by mass, etc., based on the total mass of the skin topical composition. From the viewpoint of suppressing the turbidity of the cosmetic, it is preferable to reduce the amount of the oil-in-water emulsion composition blended in the cosmetic. From this viewpoint, the amount of the oil-in-water emulsion composition blended in the cosmetic of the present invention is preferably 30% by mass or less, more preferably 20% by mass or less, based on the total mass of the cosmetic.

[0127] The following examples are intended for illustrative purposes only and are not intended to limit the scope of the present invention in any way. Unless otherwise specified, reagents are commercially available or are obtained or prepared according to conventional techniques or procedures known in the art. EXAMPLES

[0128] Test Example 1 Preparation of oil-in-water emulsion compositions of Examples 1 to 18 and Comparative Examples 1 to 4 1. Preparation of oil-in-water emulsion composition 1.00 g of β-glycyrrhetinic acid (Maruzen Pharmaceutical Co., Ltd.), 20.00 g of dihexyldecyl lauroyl glutamate (AMIER LG1600, manufactured by Nippon Emulsion Co., Ltd.), 10.00 g of isostearyl alcohol (Lisonol 18SP, manufactured by Kokyu Alcohol Kogyo Co., Ltd.), and 4.00 g of 1,3-butylene glycol (Daicel Corporation) were mixed and dissolved with stirring at 90°C, and this was used as oil phase composition-1. On the other hand, 2.00 g of soybean lecithin (Tsuji Oil Mills: SLP-PC70), 8.00 g of polyglyceryl oleate (10) (Nikko Chemicals: Decaglyn-1OV), 1.00 g of sodium stearoyl methyl taurate (Nikko Chemicals: SMT), 22.00 g of concentrated glycerin (Kao Corporation), and 32.00 g of purified water were mixed and dissolved (dispersed) with stirring at 70°C, and this was used as aqueous phase composition-1. The oil phase composition-1 and the aqueous phase composition-1, each dissolved, were crudely emulsified in a TK homomixer (manufactured by Primix) at 1000 rpm for 15 minutes at 60° C. This crude emulsion-1 was passed three times through an ultra-high pressure dispersing device (Starburst Mini, manufactured by Sugino Machine Co., Ltd.) at a pressure of 200 MPa while maintaining the temperature at 60° C. to prepare the oil-in-water emulsion composition of Example 1, which is a fine emulsion. The emulsion compositions of Examples 2 to 18 and Comparative Examples 1 to 4 were prepared in the same manner as the emulsion composition of Example 1 according to Table 1. However, the raw materials used here were as follows. Dioctyldecyl lauroyl glutamate (AMITER LG1800, manufactured by Nippon Emulsion Co., Ltd.) · Phytosteryl / octyldodecyl lauroyl glutamate (Ajinomoto Co., Inc.: ELDEW PS203) Hexyldecyl myristoyl methylaminopropionate (AMITER MA-HD, manufactured by Nippon Emulsion Co., Ltd.) Lauroyl sarcosine isopropyl (Ajinomoto Co., Inc.: ELDEW SL205) · Di(cholesteryl / octyldodecyl) lauroyl glutamate: (Ajinomoto Co., Inc., ELDEW CL202) Lauroyl glutamate di(cholesteryl / behenyl / octyldodecyl): (Ajinomoto Co., Inc., ELDEW CL301) Lauroyl glutamate di(phytosteryl / behenyl / octyldodecyl): Ajinomoto Co., Inc., ELDEW PS304) Myristoyl sarcosine sodium (Nikko Chemicals Co., Ltd.: Sarcosinate MN) Sodium dilauroyl glutamate lysine (Asahi Kasei Finechem Corporation: Pellicer L30) (Table 1 shows the pure product equivalent) DL-α-tocopherol acetate (manufactured by Mitsubishi Chemical Corporation)

[0129] 2. Evaluation of oil-in-water emulsion compositions Each of the oil-in-water emulsion compositions of the Examples and Comparative Examples was evaluated for the following items. (1) Initial turbidity (transparency) Turbidity can be a problem, especially when used in products that require transparency, such as lotions. Turbidity is evaluated by the turbidity when diluted. The turbidity was evaluated by diluting the oil-in-water emulsion prepared by the above method 100 times with purified water and measuring the absorbance (scattering intensity) at a wavelength of 600 nm using a spectrophotometer (V-750 manufactured by JASCO Corporation). The sample was placed in a quartz glass cell with an optical path length of 10 mm. (2) Storage stability The above emulsions were each placed in a 6 ml glass vial and stored in a sealed state at 40° C. for one month, after which the vial was opened and the contents were diluted in the same manner as above, and the turbidity was measured to determine the difference from the initial turbidity. (3) Observation of the state of preserved emulsion The emulsion dispersion state of the above-mentioned stored emulsion was observed to evaluate the presence or absence of separation (precipitation or floating) and its degree. If separation was observed, it was marked as × and the storage temperature conditions were also noted. (4) Overall evaluation Based on the initial turbidity, storage stability, and observation of the state of the stored emulsion, each emulsion composition was evaluated according to the following criteria. ⊚: No separation phenomenon was observed during storage, the turbidity change was 0.06 or less, and the initial turbidity was 0.15 or less. ○: No separation phenomenon was observed during storage, and the change in turbidity was 0.1 or less. △: No separation phenomenon was observed during storage, and the turbidity change was greater than 0.1. ×: Phase separation such as precipitation or oil separation is observed during storage.

[0130] [Table 1]

[0131] Test Example 2 The emulsion compositions of Examples 1, 12, 13, 14, 15, and 17 prepared in Test Example 1 were mixed with other ingredients by stirring in the following compositions to prepare external skin compositions 1 to 6, respectively. Purified water 73.9 g Non-ionic polymer liquid (90SH15000) 1.1 g Propanediol 4 g 10 g glycerin Pentylene glycol 2 g Phenoxyethanol 0.5g Ethylhexylglycerin 0.1g Hydroxylated lecithin (Lecithinol SH50) 0.1g Cyclohexane-1,4 dicarboxylic acid bisethoxydiglycol (Neosolute-Aqulio) 0.1g PEG60 hydrogenated castor oil (Emanon HC60) 0.1g 1,3 Butylene Glycol 5 g Serine 0.01g Emulsion composition of Table 1 12 g (Examples 1, 12, 13, 14, 15 and 17) with purified water up to 120 g The present skin external use compositions 1 to 6 all had low turbidity (high transparency) immediately after preparation, and showed extremely small changes in turbidity after storage, which was favorable.

[0132] Test Example 3 The emulsion compositions of Examples 1, 12, 13, 14, 15, and 17 prepared in Test Example 1 were mixed with other ingredients by stirring in the following compositions to prepare oral compositions 1 to 6, respectively. Sorbitol 5 g 5 g glycerin Propylene glycol 4 g Citric acid 0.1g Sodium citrate 0.3g Polyoxyethylene (60) hydrogenated castor oil 0.3g Sodium lauroyl methyl taurate 0.3g Ethyl paraoxybenzoate 0.2g Cetylpyridinium chloride 0.05g Sodium saccharin 0.001g Fragrance (spearmint oil) 0.1g Emulsion composition of Table 1 5 g (Examples 1, 12, 13, 14, 15 and 17) with purified water up to 100 g All of the oral compositions 1 to 6 had low turbidity (high transparency) immediately after preparation, and when visually inspected after storage at 50°C in a sealed container for one month, no precipitate or turbidity was observed, and the composition was in good condition.

Claims

1. The following components (A), (B), and (C): (A) Glycyrrhetinic acid, (B) N-acyl amino acid diesters, and (C) Anionic surfactant An oil-in-water emulsion composition containing the following:

2. The oil-in-water emulsion composition according to claim 1, wherein component (B) is a compound represented by the following formula (I). 【Chemistry 1】 (In the formula, R 1 This represents a straight-chain or branched-chain hydrocarbon group having 5 to 23 carbon atoms. R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. R 3 and R 4 Each of these independently represents a linear, branched, or cyclic hydrocarbon group having 12 to 30 carbon atoms. m is an integer between 0 and 4.

3. The oil-in-water emulsion composition according to claim 1, wherein component (B) is the compound shown in (I) below. 【Chemistry 2】 (In the formula, R 1 This represents a straight-chain or branched-chain hydrocarbon group having 5 to 23 carbon atoms. R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. R 3 and R 4 Each of these independently represents a linear or branched hydrocarbon group having 12 to 20 carbon atoms, and m is an integer from 0 to 4.

4. The oil-in-water emulsion composition according to claim 1, wherein component (B) is a compound represented by the following formula (V). 【Transformation 3】 (In the formula, R 1 represents a linear or branched hydrocarbon group having 5 to 23 carbon atoms, R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. R 5 and R 6 Either one or both of these represent an alcohol residue of an alcohol group-containing terpenoid, R 5 and R 6 If either of them is an alcohol residue of the alcohol group-containing terpenoid, the other is an alcohol residue of a linear, branched, or cyclic hydrocarbon having 12 to 30 carbon atoms and containing an alcohol group. m is an integer between 0 and 4.

5. The oil-in-water emulsion composition according to claim 4, wherein the alcohol group-containing terpenoid is an alcohol group-containing triterpenoid.

6. The oil-in-water emulsion composition according to claim 5, wherein the alcohol group-containing triterpenoid is an alcohol group-containing steroid.

7. The oil-in-water emulsion composition according to claim 6, wherein the alcohol group-containing steroid is cholesterol or phytosterol.

8. The oil-in-water emulsion composition according to claim 1, wherein component (C) is a compound represented by any of (II) to (IV) below. 【Chemistry 4】 (In the formula, R 1 This represents a straight-chain or branched-chain hydrocarbon group having 5 to 23 carbon atoms. R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt of any of these. n is an integer between 1 and 10. 【Transformation 5】 (In the formula, R 1 These are straight-chain or branched hydrocarbon groups having 5 to 23 carbon atoms. R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. X represents a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt of any of these. p is 0, 1, or 2, q is 0, 1, or 2, and (p and q are not both zero at the same time.) 【Transformation 6】 (In the formula, R 1 This represents a straight-chain or branched-chain hydrocarbon group having 5 to 23 carbon atoms. R 2 This represents a hydrocarbon group or hydrogen group having 1 to 3 carbon atoms. X represents a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof. Y is a carboxyl group or a salt thereof, -NHR 5 (R 5 This refers to a hydrocarbon group having 1 to 20 carbon atoms having at least one group selected from the group consisting of a hydrocarbon group or hydrogen group having 1 to 10 carbon atoms, an -OH group, and an -SH group. Z is -NR 6 -(R 6 This represents a hydrocarbon group or hydrogen group having 1 to 10 carbon atoms, an -O- group, or an -S- group. p is 0, 1, or 2, q is 0, 1, or 2, and (p and q are not both zero at the same time.)

9. The oil-in-water emulsion composition according to claim 1, further comprising at least one compound selected from the group consisting of tocopherol and tocopherol derivatives.

10. The oil-in-water emulsion composition according to claim 1, further comprising lecithin.

11. The oil-in-water emulsion composition according to claim 1, further comprising a nonionic surfactant.

12. A cosmetic composition containing the oil-in-water emulsion composition according to any one of claims 1 to 11.

13. A topical skin composition containing the oil-in-water emulsion composition according to any one of claims 1 to 11.

14. An oral composition containing the oil-in-water emulsion composition according to any one of claims 1 to 11.

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