Amino acid derivative compositions and cosmetics formulated therefrom

Abstract

A composition characterized by containing an amino acid derivative represented by the following general formulas (A), (B), or (C) or a salt thereof, wherein the component represented by formula (A) is 75 to 95 mass%, the component represented by formula (B) is 5 to 20 mass%, and the component represented by formula (C) is 0 to 1.5 mass%; and a cosmetic base comprising the above composition, which has excellent moisturizing properties or functionality while solving the problems of odor retention or deterioration of usability, or a cosmetic formula incorporating the above composition (in the formulas, R1 represents a hydrogen atom or a side chain of an α-amino acid or a salt thereof, and R2 represents a hydrogen atom, an alkali metal, an ammonium, or an organic ammonium).

Description

Technology Field

[0001] The present invention relates to a composition comprising amino acid derivatives or salts thereof that are suitably used as raw materials for cosmetics, etc., combined in a specific ratio, and a cosmetic product formulated with the same. Background Technology

[0002] Amino acid derivatives are widely known as cosmetic ingredients with excellent functionality, and various studies have been conducted on them. For example, Japanese Patent Publication No. 5625914 (Patent Document 1) discloses an amino acid derivative that can provide a cosmetic composition with good affinity for skin and hair, high moisturizing properties, and good usability. However, when these amino acid derivatives are incorporated into a cosmetic composition in high proportions, odors derived from amino acids or a decrease in usability occur, so further improvement is required. Prior art literature

[0003] [Patent Document 1] Japanese Patent Publication No. 5625914 The problem to be solved

[0004] The present invention aims to solve the problems of odor absorption and reduced usability, and to provide an amino acid derivative composition having excellent moisturizing properties or a cosmetic formula containing the same. means of solving the problem

[0005] As a result of repeated diligent research to solve the above problem, the inventors discovered that a composition in which amino acid derivatives represented by the following general formulas (A) to (C) or their salts are combined in a specific ratio exhibits a superior moisturizing effect compared to using each of them individually. Furthermore, since a cosmetic composition containing the above amino acid derivatives or their salts possesses a superior moisturizing effect, it is possible to reduce the amount of the composition while maintaining an equivalent moisturizing effect, thereby resolving the problem of odor absorption or reduced usability derived from amino acid derivatives. The present invention is completed based on these findings.

[0006] The first of the present invention provides a composition characterized by containing an amino acid derivative represented by the following general formulas (A), (B), or (C) or a salt thereof, wherein the component represented by formula (A) is 75 to 95 mass%, the component represented by formula (B) is 5 to 20 mass%, and the component represented by formula (C) is 0 to 1.5 mass%.

[0007]

[0008]

[0009]

[0010] (Among the above equations (A), (B), and (C), R 1 represents a hydrogen atom or a side chain of an α-amino acid, and R 2 represents a hydrogen atom, an alkali metal, an ammonium, or an organic ammonium. Also, R in formula (A) 1 , R of Equation (B) 1 , and R of Equation (C) 1 is identical.)

[0011] The second aspect of the present invention is a composition characterized as not containing an amino acid derivative represented by the following general formula (D) or a salt thereof, or containing it in an amount of 0.1 mass% or less, as a preferred embodiment of the first aspect of the present invention, and is particularly preferred in that it has a high moisturizing effect.

[0012]

[0013] (R in food 1 represents a hydrogen atom or a side chain of an α-amino acid or their salt, and R 2 represents a hydrogen atom, alkali metal, ammonium, and organic ammonium.

[0014] The third aspect of the present invention is a composition characterized in that, as a preferred embodiment of the first or second aspect of the present invention, the amino acid is arginine or glycine. Arginine or glycine is preferred in that it provides an excellent texture when incorporated into a cosmetic product.

[0015] A composition containing an amino acid derivative or a salt thereof according to the present invention may be incorporated into a cosmetic. The fourth of the present invention is a cosmetic characterized by incorporating the compositions of the first to third of the present invention. The cosmetic of the fourth of the present invention is a cosmetic that exhibits a high moisturizing effect, reduces odor retention derived from amino acid derivatives, and provides an excellent user experience. Effects of the invention

[0016] The compositions of the present invention containing amino acid derivatives represented by general formulas (A) to (C) or their salts in a specific ratio exhibit superior moisturizing effects compared to each of them used alone. Therefore, cosmetic products formulated with these compositions can reduce the amount of amino acid derivatives or their salts used in the cosmetic product while maintaining a moisturizing effect equivalent to that of conventional amino acid derivatives or their salts used alone. From this, problems such as odor retention or reduced usability when amino acid derivatives or their salts are used in cosmetic products can be resolved. Specific details for implementing the invention

[0017] The following describes a form for carrying out the present invention, but the scope of the present invention is not limited to the form described below.

[0018] As for the amino acids of the raw materials (starting materials) for preparing the amino acid derivatives represented by the general formulas (A) to (C) described above or their salts constituting the composition of the present invention, examples include acidic amino acids such as aspartic acid and glutamic acid; neutral amino acids such as isoleucine, leucine, valine, glycine, alanine, serine, threonine, phenylalanine, asparagine, glutamine, tyrosine, tryptophan, methionine, and cysteine; and basic amino acids such as lysine, arginine, and histidine. Furthermore, basic amino acids or neutral amino acids are preferred, and arginine or glycine are even more preferred, as they are expected to exhibit an excellent texture when incorporated into a cosmetic product.

[0019] Amino acid derivatives represented by general formulas (A) to (C) constituting the composition of the present invention, or salts thereof, can be obtained by reacting said amino acids or their salts with glycidol (i.e., 2,3-epoxy-1-propanol) or 3-halo-1,2-propanediol, followed by acetalization and acid treatment. Additionally, said amino acids or their salts can be obtained by reacting said amino acids or their salts with 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolein or 4-halomethyl-2,2-dimethyl-1,3-dioxolein, followed by acid treatment.

[0020] In the reaction with glycidol, 3-halo-1,2-propanediol, 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolein, and 4-halomethyl-2,2-dimethyl-1,3-dioxolein, the pH during the reaction is preferably 8 to 12, and more preferably 8 to 11. In addition, as a pH adjusting agent during the reaction, examples include alkali agents such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, and potassium carbonate.

[0021] Examples of solvents used in the reaction include water, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, etc. As for the reaction temperature, it is preferable to carry out the reaction at 10°C to 90°C, and more preferable to carry out the reaction at 20°C to 80°C.

[0022] The compound synthesized by the above method can be purified by means such as column chromatography using silica gel or crystallization.

[0023] When carrying out a reaction between an amino acid or its salts and glycidol or 3-halo-1,2-propanediol, or by carrying out a reaction with various carbonyl compounds or dialkoxy compounds under acidic conditions, an intermediate of the amino acid derivative of the present invention having an acetal structure can be obtained.

[0024] Examples of carbonyl compounds used in the reaction include acetone, methyl ethyl ketone, diethyl ketone, cyclopentanone, cyclohexanone, formaldehyde, acetaldehyde, benzaldehyde, etc.

[0025] Examples of dialkoxy compounds used in the reaction include 2,2-dimethoxypropane, 2-methoxy-2-ethoxypropane, 2,2-diethoxypropane, α,α-dimethoxytoluene, etc.

[0026] The pH during the reaction is preferably 1 to 5, and more preferably 2 to 4. Examples of pH adjusting agents include acids such as p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, and sulfuric acid.

[0027] Examples of solvents used in the reaction include alcohol, acetone, tetrahydrofuran, etc. As for the reaction temperature, it is preferable to carry out the reaction at 0°C to 40°C, and more preferable to carry out the reaction at 10°C to 30°C.

[0028] The intermediate of the amino acid derivative of the present invention, which has an acetal structure introduced and synthesized by the above method, can be purified by means such as column chromatography using silica gel or crystallization.

[0029] In the intermediate of the amino acid derivative of the present invention having an acetal structure introduced by the above method, and in the reaction product of an amino acid or a salt thereof with 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolein or 4-halomethyl-2,2-dimethyl-1,3-dioxolein, by performing acid treatment under acidic conditions in the presence of water, an amino acid derivative represented by general formulas (A) to (C) constituting the composition of the present invention or a salt thereof can be obtained.

[0030] The pH during the reaction is preferably 1 to 5, and more preferably 1 to 3. Examples of pH adjusting agents during the reaction include acids such as p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, and sulfuric acid.

[0031] Examples of solvents used in the reaction include water, alcohol, tetrahydrofuran, etc. As for the reaction temperature, it is preferable to carry out the reaction at 0°C to 40°C, and more preferable to carry out the reaction at 10°C to 30°C.

[0032] The amino acid derivatives represented by the general formulas (A) to (C) described above, or salts thereof, which constitute the composition of the present invention synthesized by the above method, can be purified by means such as column chromatography using silica gel or crystallization.

[0033] In addition, the above amino acid derivative may be in the form of a salt, and examples include sodium salt, potassium salt, calcium salt, alkylamine salt, hydrochloride, sulfate, phosphate, acetate, etc.

[0034] The mixing ratio of the composition of the present invention is such that component (A) is 75 to 95 mass%, component (B) is 5 to 20 mass%, and (C) is 0 to 1.5 mass%. Deviations from the above ratio are undesirable as they reduce the moisturizing effect, and a more preferred ratio is such that component (A) is 80 to 90 mass%, component (B) is 8 to 18 mass%, and component (C) is 0.5 to 1.5 mass%.

[0035] The composition containing general formulas (A) to (C) of the present invention preferably does not contain an amino acid derivative represented by general formula (D) or a salt thereof, or if it does contain it, the amount is 0.1 mass% or less. The above range is desirable in that it exhibits a particularly high moisturizing effect when incorporated into a cosmetic product.

[0036] The amino acid derivatives of the present invention or mixtures of their salts can be applied to cosmetics, and, provided that stability, etc. is not impaired, ingredients commonly used in cosmetics may be optionally included depending on the intended use.

[0037] Ingredients commonly used in cosmetics, such as oily components, polymer compounds like surfactants, emulsifiers, and thickeners, whitening agents, texture improvers, pharmaceuticals, ultraviolet absorbers, proteins, protein hydrolysates or derivatives thereof, amino acids or amino acid derivatives other than ingredients (A) to (C), antioxidants, metal ion chelating agents, pH adjusters, preservatives, moisturizers, pigments, colorants, fragrances, etc., may be appropriately incorporated.

[0038] Examples of oily components, polymer compounds such as surfactants, emulsifiers, and thickeners, whitening agents, texture improvers, pharmaceuticals, ultraviolet absorbers, proteins, protein hydrolysates or derivatives thereof, amino acids or amino acid derivatives other than components (A) to (C), antioxidants, metal ion chelating agents, pH adjusters, preservatives, humectants, pigments, colorants, fragrances, etc., are those identical to those described in WO 2022 / 080287.

[0039] The above ingredients used in conventional cosmetics may be used as a single type or in combination of two or more types.

[0040] Examples

[0041] The present invention will be specifically explained below with reference to synthesis examples and embodiments. However, the present invention is not limited to these synthesis examples and embodiments.

[0042] Synthesis Example 1: Synthesis of N-glyceryl arginine

[0043] Arginine (10.45 g), ion-exchanged water (75 ml), and sodium hydroxide (0.60 g) were added to a branched flask, and the temperature was raised to 40°C. Glycidol (1.11 g) was added over a period of 1 hour, followed by stirring for 3 hours. Afterward, 17% hydrochloric acid was added to neutralize the mixture, and then concentration was performed under reduced pressure. To the resulting residue (12.31 g), acetone (75 ml), sodium p-toluenesulfonic acid monohydrate (3.00 g), and 2,2-dimethoxypropane (9.00 g) were added, and the mixture was stirred overnight at room temperature. After adding a 25% aqueous sodium hydroxide solution, concentration was performed under reduced pressure. The obtained residue (20.54 g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 10:10:3 solution, concentrated under reduced pressure, and N-4-methyl-2,2-dimethyl-1,3-dioxoleneylarginine was obtained.

[0044] In addition, 5% hydrochloric acid (3.83g) was added to N-4-methyl-2,2-dimethyl-1,3-dioxoleinylarginine (0.75g), and stirring was performed overnight at room temperature. Afterward, a 25% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. Subsequently, the obtained residue (0.56g) was subjected to silica gel column chromatography, eluted with a chloroform / methanol / ion-exchanged water = 10:10:3 solution, and concentrated under reduced pressure to obtain N-glycerylarginine (yield 22.8%) represented by the following structure.

[0045] Regarding the obtained product, mass spectrometry, 1 H-NMR, 13 C-NMR measurements were performed, and it was confirmed that the product is N-glycerylarginine represented by the following structural formula. Furthermore, in the synthesis examples described below, the products obtained were subjected to the same measurements, and it was confirmed that they are amino acid derivatives represented by the structural formulas and compound names shown in each synthesis example. Mass analysis of the products obtained in the synthesis examples below, 1 H-NMR and 13 The C-NMR measurement results are shown in Tables 1 to 3.

[0046]

[0047] Synthesis Example 2: Synthesis of N,N-Diglyceryl Arginine

[0048] Arginine (2.09 g), ion-exchanged water (15 ml), and sodium hydroxide (0.96 g) were added to a branched flask, and the temperature was raised to 40°C. Glycidol (1.78 g) was added over a period of 1 hour, followed by stirring for 3 hours. Afterward, 17% hydrochloric acid was added to neutralize the mixture, and then concentration was performed under reduced pressure. To the resulting residue (5.11 g), acetone (40 ml), sodium p-toluenesulfonic acid monohydrate (1.00 g), and 2,2-dimethoxypropane (5.50 g) were added, and the mixture was stirred overnight at room temperature. After adding a 25% aqueous sodium hydroxide solution, concentration was performed under reduced pressure. The obtained residue (11.38 g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 7:4:0.5 solution. Concentration was performed under reduced pressure to obtain N,N-di-(4-methyl-2,2-dimethyl-1,3-dioxoleinyl)arginine.

[0049] In addition, 5% hydrochloric acid (2.00g) was added to N,N-di-(4-methyl-2,2-dimethyl-1,3-dioxoleinyl)arginine (0.20g), and stirring was performed overnight at room temperature. Afterward, a 25% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. Subsequently, the obtained residue (0.39g) was subjected to silica gel column chromatography, eluted with a chloroform / methanol / ion-exchanged water = 10:10:3 solution, and concentrated under reduced pressure to obtain N,N-diglycerylarginine (yield 11.0%) represented by the following structure.

[0050]

[0051] Synthesis Example 3: Synthesis of N-(O-glyceryl)glyceryl arginine

[0052] Arginine (0.66 g) and ion-exchanged water (2.2 ml) were added to a branched flask, and the temperature was raised to 50°C. Then, 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolein (0.72 g) was added over 15 minutes, followed by stirring for 1.5 hours, and concentration was performed under reduced pressure. The obtained residue (1.48 g) was subjected to silica gel column chromatography, eluted with methanol, and concentrated under reduced pressure to obtain N-(O-4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glyceryl arginine.

[0053] In addition, 5% hydrochloric acid (1.00g) was added to N-(O-4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glyceryl arginine (0.36g), and stirring was performed overnight at room temperature. Afterward, a 25% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. The obtained residue (0.31g) was subjected to silica gel column chromatography, eluted with methanol, and concentrated under reduced pressure to obtain N-(O-glyceryl)glyceryl arginine (yield 90.0%) represented by the following structure.

[0054]

[0055] Synthesis Example 4: Synthesis of N-glycerylglycine

[0056] Glycine (10.0 g), ion-exchanged water (30 ml), N,N-dimethylformamide (10 ml), sodium hydroxide (2.40 g), and 4-chloromethyl-2,2-dimethyl-1,3-dioxolein (9.79 g) were added to a branched flask and stirred overnight under 80°C conditions. Afterward, 17% hydrochloric acid was added to neutralize the mixture, and then concentrated under reduced pressure. The resulting residue (23.01 g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 6:4:1 solution, concentrated under reduced pressure, and N-4-methyl-2,2-dimethyl-1,3-dioxolein monoglycine was obtained.

[0057] In addition, 5% hydrochloric acid (2.80g) was added to N-4-methyl-2,2-dimethyl-1,3-dioxolene glycine (0.54g), and stirring was performed overnight at room temperature. Afterward, a 1% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. Subsequently, the obtained residue (0.79g) was subjected to silica gel column chromatography, eluted with a chloroform / methanol / ion-exchanged water = 6:4:1 solution, and concentrated under reduced pressure to obtain N-glycerylglycine (yield 21.2%) represented by the following structure.

[0058]

[0059] Synthesis Example 5: Synthesis of N,N-Diglycerylglycine

[0060] Glycine (2.50 g), ion-exchanged water (10 ml), and sodium hydroxide (4.00 g) were added to a branched flask, and the temperature was raised to 40°C. Then, glycidol (7.41 g) was added over a period of 1 hour, followed by stirring for 3 hours. After adding 17% hydrochloric acid to neutralize the mixture, concentration was performed under reduced pressure. To the resulting residue (18.28 g), acetone (200 ml), sodium p-toluenesulfonic acid monohydrate (4.75 g), and 2,2-dimethoxypropane (50.00 g) were added. The mixture was stirred overnight at room temperature, and after adding a 1% aqueous sodium hydroxide solution, concentration was performed under reduced pressure. The obtained residue (23.97 g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 10:3:0.3 solution, concentrated under reduced pressure, and N,N-di-(4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glycine was obtained.

[0061] In addition, 5% hydrochloric acid (0.60g) was added to N,N-di-(4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glycine (0.18g), and stirring was performed overnight at room temperature. Afterward, a 1% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. The obtained residue (0.36g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 6:4:1 solution, and then concentrated under reduced pressure to obtain N,N-diglycerylglycine (yield 30.2%) represented by the following structure.

[0062]

[0063] Synthesis Example 6: Synthesis of N-(O-glyceryl)glycerylglycine

[0064] Glycine (0.38 g), 25% aqueous sodium hydroxide solution (0.16 g), and ion-exchanged water (1.5 ml) were added to a branched flask, and the temperature was raised to 50°C. Then, 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolein (0.94 g) was added over 15 minutes, followed by stirring for 3 hours and concentration under reduced pressure. The obtained residue (1.17 g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 5:4:0.4 solution, concentrated under reduced pressure, and N-(O-4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glycerylglycine was obtained.

[0065] In addition, 5% hydrochloric acid (2.00g) was added to N-(O-4-methyl-2,2-dimethyl-1,3-dioxoleinyl)glycerylglycine (0.53g), and stirring was performed overnight at room temperature. Afterward, a 1% aqueous sodium hydroxide solution was added to neutralize the mixture, and then concentration was performed under reduced pressure. The obtained residue (0.42g) was subjected to silica gel column chromatography and eluted with a chloroform / methanol / ion-exchanged water = 1:1:0.1 solution, and then concentrated under reduced pressure to obtain N-(O-glyceryl)glycerylglycine (yield 91.0%) represented by the following structure.

[0066]

[0067] Mass analysis of the products obtained in Synthesis Examples 1 to 6 was performed using LCMS-2020 (manufactured by Shimadzu Seisakusho Co., Ltd.). The measurement results are shown in Table 1.

[0068] Synthetic Example Number ionization Actual value 1 [M+H] + 249.3 2 [M+H] + 323.4 3 [M+H] + 323.4 4 [M+H] + 150.2 5 [M+H] + 224.2 6 [M+H] + 224.2

[0069] Ionization was performed using the electrospray ionization method (ESI).

[0070] Of the products obtained in Synthesis Examples 1 to 6 1H-NMR was performed using the JNM-ECS400 (manufactured by Nippon Denshi Co., Ltd.). The measurement results are shown in Table 2.

[0071] Synthetic example number Measurement conditions Chemical shift δ (ppm) 1 400MHz,D2O 1.53-1.74(2H, m), 1.82-2.00(2H, m), 3.18(1H, t), 3.20(2H, t), 3.50-3.72(4H, m), 4.00(1H, m) 2 400MHz,D2O 1.75(2H, m), 1.90(2H, m), 3.25(1H, t), 3.27(2H, t), 3.51-3.67(8H, m), 3.90(1H, br), 4.11(1H, br) 3 400MHz,D2O 1.59-1.80(4H, br), 3.19(1H, t), 3.20(2H, t), 3.48-3.64(8H, m), 3.88(2H, m) 4 400MHz, CD3OD 3.05(1H, dd), 3.21(1H, dd), 3.53-3.62(4H, m), 3.94(1H, m) 5 400MHz, CD3OD 3.26-3.33(4H, m), 3.39-3.62(8H, m), 3.76(1H, dd), 3.87(1H, m), 3.90(1H, dd), 4.05(1H, br) 6 400MHz, CD3OD 3.08(1H, dd), 3.18(1H, dd), 3.46-3.61(8H, m), 3.79(1H, m), 4.05(1H, m)

[0072] Of the products obtained in Synthesis Examples 1 to 6 13 C-NMR was performed using the JNM-ECS400 (manufactured by Nihon Denshi Co., Ltd.). The measurement results are shown in Table 3.

[0073] Synthetic Example Number Measurement conditions Chemical shift δ (ppm) 1 100MHz, D2O 23.9, 26.5, 40.5, 48.9, 49.0, 63.3, 67.1, 156.7, 173.2 2 100MHz,D2O 25.2, 25.8, 40.8, 49.0, 55.5, 62.5, 63.2, 63.3, 70.4, 70.4, 156.8, 172.1 3 100MHz,D2O 25.7, 26.3, 40.7, 48.9, 55.4, 63.3, 67.8, 156.7, 171.9 4 100MHz, CD3OD 50.7, 51.5, 65.2, 68.6, 171.3 5 100MHz, CD3OD 58.6, 59.6, 65.1, 68.1, 170.7 6 100MHz, CD3OD 51.1, 51.9, 64.2, 67.2, 72.0, 74.0, 74.8, 171.9

[0074] Test Example 1 [Moisture Test]

[0075] Each sample prepared in the ratios shown in Examples 1 to 12 and Comparative Examples 1 to 6 listed in Tables 4 and 5 below was vacuum dried, and approximately 40 mg (this weight is referred to as W0) of each was placed in a weighing bottle (diameter 3.6 cm, height excluding lid 1.8 cm). Each sample placed in the weighing bottle was placed inside a humidity and temperature incubator (LTI-1200, manufactured by Tokyo Rikakikai Co., Ltd.) under conditions of a temperature of 25°C and a humidity of 75%. The weight was measured periodically, and the sample was left to stand until sufficient moisture was absorbed and there was no change in weight. After that, it was transferred to an environment with a temperature of 25℃ and a humidity of 20% (into a sealed container filled with a saturated potassium acetate solution at the bottom), and from the weight after 24 hours (let this weight be W1), the moisture content Δ(g / g) per 1g of dry sample was calculated using the following formula.

[0076] (W1-W0) / W0

[0077] Example number Synthesis Example 1 (%) Synthesis Example 2 (%) Synthesis Example 3 (%) Water retention Δ (g / g) Comparison 1 100 0 0 0.060 Comparison 2 0 100 0 0.045 Comparison 3 0 0 100 0.028 1 90 10 0 0.080 2 80 20 0 0.091 3 90 9.5 0.5 0.081 4 80 19.5 0.5 0.088 5 90 9.0 1.0 0.072 6 80 19.0 1.0 0.074

[0078] Example number Synthesis Example 4 (%) Synthesis Example 5 (%) Synthesis Example 6 (%) Moisture retention Δ (g / g) Comparison 4 100 0 0 0.040 Comparison 5 0 100 0 0.033 Comparison 6 0 0 100 0.019 7 90 10 0 0.068 8 80 20 0 0.073 9 90 9.5 0.5 0.066 10 80 19.5 0.5 0.071 11 90 9.0 1.0 0.062 12 80 19.0 1.0 0.068

[0079] As shown in Tables 4 and 5, it has become clear that in a composition containing the amino acid derivatives of general formulas (A) to (C) or their salts mixed in a specific ratio, a superior moisturizing effect (moisture retention) is exhibited compared to the case of the amino acid derivatives of general formulas (A) to (C) or their salts alone. That is, in a composition containing the amino acid derivatives of the present invention or their salts, it is possible to reduce the amount of the amino acid derivatives or their salts while maintaining the moisturizing ability in the cosmetic, thereby suppressing odor absorption or deterioration of the user experience derived from the amino acid derivatives.

[0080] Example 13 Toner

[0081] Cosmetic water is prepared by mixing the raw materials (1) to (6) of the composition shown in Table 6 while stirring well. In addition, in the tables after Table 6, the amount of mixture is indicated in parts by mass.

[0082] No Ingredient name Mixing amount 1 Amino acid derivative composition of Example 2 7.0 2 ethanol 8.0 3 citric acid 0.01 4 Sodium citrate 0.015 5 Potassium glycyrrhizinate 0.03 6 purified water Remaining * 1

[0083] *1: Refers to the amount required to make the total mixing amount 100 parts by mass. The same applies to the following table.

[0084] Example 14 Emulsion

[0085] The raw materials of the oil phase (1) to (9) and the raw materials of the aqueous phase (10) to (13) of the composition shown in Table 7 are each heated to 70°C to dissolve them, and the oil phase and aqueous phase are prepared. Then, the oil phase is added to the aqueous phase to perform preliminary emulsification, and after uniformly emulsifying with a homogenizer, the liquid is prepared by cooling to room temperature while stirring well.

[0086] No Ingredient name Mixing amount 1 Isostearyl palmitate 5.0 2 Jojoba 2.0 3 Dimethylpolysiloxane 2.0 4 Cetanol 1.0 5 stearic acid 1.5 6 wax 2.5 7 Paraffin wax 2.5 8 Monostearic acid polyoxyethylene (20) sorbitan 1.2 9 Tetraoleic acid polyoxyethylene (40) sorbitol 1.5 10 Propylene glycol 10.0 11 Composition of Example 6 3.0 12 antiseptic Appropriate amount 13 purified water leftover

[0087] Example 15 Cream

[0088] The raw materials of the oil phase (1) to (5) and the raw materials of the aqueous phase (6) to (10) of the composition shown in Table 8 are each heated to 70°C to dissolve them, and the oil phase and aqueous phase are prepared. Then, the oil phase is added to the aqueous phase to perform preliminary emulsification, and after uniformly emulsifying with a homogenizer, the cream is prepared by cooling to room temperature while stirring well.

[0089] No Ingredient name Mixing amount 1 Squalein 9.0 2 vaseline 6.0 3 Stearyl alcohol 5.0 4 Polyoxyethylene (25) cetyl ether 2.5 5 Glyceryl monostearate 1.5 6 Composition of Example 8 2.0 7 glycerin 6.0 8 antiseptic Appropriate amount 9 pH adjuster Appropriate amount 10 purified water leftover

Claims

Claim 1 A composition characterized by containing an amino acid derivative represented by the following general formulas (A), (B), or (C) or a salt thereof, wherein the component represented by formula (A) is 75 to 95 mass%, the component represented by formula (B) is 5 to 20 mass%, and the component represented by formula (C) is 0 to 1.5 mass%. (Among the above equations (A), (B), and (C), R 1 represents a hydrogen atom or a side chain of an α-amino acid or their salt, and R 2 represents a hydrogen atom, an alkali metal, an ammonium, or an organic ammonium. R in formula (A) 1 , R of Equation (B) 1 and R of Equation (C) 1 is identical.) Claim 2 A composition according to claim 1, characterized in that it does not contain an amino acid derivative represented by the following general formula (D) or a salt thereof, or if it does contain it, the amount is 0.1 mass% or less. (R in food 1 represents a hydrogen atom or a side chain of an α-amino acid or their salt, and R 2 represents a hydrogen atom, alkali metal, ammonium, and organic ammonium. Claim 3 A composition according to claim 1 or 2, characterized in that the amino acid is arginine or glycine. Claim 4 A cosmetic product characterized by incorporating a composition described in any one of claims 1 to 3.

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