Ferulic acid solution, method for producing ferulic acid-containing particles, ferulic acid-containing particles, ultraviolet absorber, and cosmetic raw material

Abstract

To provide a ferulic acid solution that can inhibit the precipitation of ferulic acid, a method for producing a ferulic acid-containing particle using the ferulic acid solution, a ferulic acid-containing particle containing a dried material of the ferulic acid solution, an ultraviolet absorber comprising the ferulic acid-containing particle thereof, and a cosmetic raw material containing the ferulic acid-containing particle thereof.SOLUTION: The ferulic acid solution of the present invention contains ferulic acid, an alcohol having 2 or more and 3 or less carbon atoms, water, and a salt of a carboxyl group-containing compound or polyvinylpyrrolidone. A number average molecular weight of the polyvinylpyrrolidone is 1,000 or more and 20,000 or less. A compounding ratio of the salt of the carboxyl group-containing compound or a compounding ratio of the polyvinylpyrrolidone exceeds 3 mass%. A mass ratio of the alcohol to water (alcohol / water) is 1 or more.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a ferulic acid solution, a method for producing ferulic acid-containing particles, ferulic acid-containing particles, an ultraviolet absorber, and a cosmetic raw material. [Background technology]

[0002] Ferulic acid has been known to have ultraviolet absorbing properties, and therefore is used in various fields, such as as a cosmetic raw material.

[0003] On the other hand, when ferulic acid is used as a cosmetic raw material, first, ferulic acid is dissolved in a solvent to prepare a ferulic acid solution.

[0004] As a method for preparing a ferulic acid solution, for example, a method has been proposed in which ethanol and ferulic acid are mixed and heated at 60°C to prepare a ferulic acid solution with a solid content of 20% by mass (see, for example, Non-Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Non-Patent Document 1] The Journal of Chemical Thermodynamics Volume 103 December 2016 Pages 285-291 Summary of the Invention [Problem to be solved by the invention]

[0006] On the other hand, when the ferulic acid solution obtained by the method for preparing a ferulic acid solution of Non-Patent Document 1 is left at room temperature, ferulic acid precipitates, which causes a problem of reduced shelf life.

[0007] The present invention provides a ferulic acid solution capable of suppressing precipitation of ferulic acid, a method for producing ferulic acid-containing particles using the ferulic acid solution, ferulic acid-containing particles containing a dried product of the ferulic acid solution, an ultraviolet absorber containing the ferulic acid-containing particles, and a cosmetic raw material containing the ferulic acid-containing particles. [Means for solving the problem]

[0008] The present invention [1] is a ferulic acid solution containing ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and a salt of a carboxyl group-containing compound or polyvinylpyrrolidone, wherein the number average molecular weight of the polyvinylpyrrolidone is 1,000 to 20,000, the blending ratio of the salt of the carboxyl group-containing compound or the blending ratio of the polyvinylpyrrolidone exceeds 3 mass%, and the mass ratio of the alcohol to the water (alcohol / water) is 1 or more.

[0009] The present invention [2] includes the ferulic acid solution according to the above [1], in which the carboxyl group-containing compound further has a hydroxyl group.

[0010] The present invention [3] includes the ferulic acid solution according to [1] or [2] above, in which the blending ratio of the ferulic acid is 10% by mass or more.

[0011] The present invention [4] includes a method for producing ferulic acid-containing particles, which comprises mixing the ferulic acid solution described in any one of [1] to [3] above with inorganic particles, and drying the alcohol and water to obtain ferulic acid-containing particles.

[0012] The present invention [5] includes the method for producing ferulic acid-containing particles according to the above [4], in which the inorganic particles are silica particles.

[0013] The present invention [6] includes ferulic acid-containing particles, which include a dried product of the ferulic acid solution according to any one of the above [1] to [3] and inorganic particles.

[0014] The present invention [7] includes the ferulic acid-containing particles according to the above [6], in which the inorganic particles are silica particles.

[0015] The present invention [8] includes an ultraviolet absorber containing the ferulic acid-containing particles described in [6] or [7] above.

[0016] The present invention [9] includes a cosmetic raw material containing the ferulic acid-containing particles described in [6] or [7] above. [Effects of the Invention]

[0017] The ferulic acid solution of the present invention has a mass ratio of alcohol to water (alcohol / water) of at least 1. This ensures that ferulic acid can be dissolved.

[0018] The ferulic acid solution contains a salt of a carboxyl group-containing compound or polyvinylpyrrolidone in an amount exceeding 3% by mass, which prevents ferulic acid from precipitating. As a result, the solution has excellent shelf life.

[0019] The method for producing ferulic acid-containing particles of the present invention uses the ferulic acid solution of the present invention, which allows for the production of ferulic acid-containing particles with excellent productivity.

[0020] The ferulic acid-containing particles of the present invention contain a dried product of the ferulic acid solution of the present invention, and therefore have excellent productivity.

[0021] The ultraviolet absorber of the present invention contains the ferulic acid-containing particles of the present invention, and therefore has excellent productivity.

[0022] The cosmetic raw material of the present invention contains the ferulic acid-containing particles of the present invention, and therefore has excellent productivity. DETAILED DESCRIPTION OF THE INVENTION

[0023] <Ferulic acid solution> The ferulic acid solution contains ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and a salt of a carboxyl group-containing compound, or polyvinylpyrrolidone. That is, the ferulic acid solution contains ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and a salt of a carboxyl group-containing compound, or ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and polyvinylpyrrolidone. Preferably, the ferulic acid solution consists of ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and a salt of a carboxyl group-containing compound, or ferulic acid, an alcohol having 2 to 3 carbon atoms, water, and polyvinylpyrrolidone.

[0024] [Ferulic acid] Ferulic acid is a component that has ultraviolet absorbing properties.

[0025] Ferulic acid includes structural isomers of trans-ferulic acid and cis-ferulic acid, and preferably trans-ferulic acid.

[0026] Furthermore, as will be described in detail later, ferulic acid is not modified (for example, esterified).

[0027] The blending ratio of ferulic acid (solid concentration of ferulic acid) relative to the ferulic acid solution is, from the viewpoint of improving ultraviolet absorbency, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 22% by mass or more, even more preferably 24% by mass or more, particularly preferably 26% by mass or more, most preferably 27% by mass or more, or even 28% by mass or more, and for example, 32% by mass or less, preferably 30% by mass or less.

[0028] [Alcohols with 2 to 3 carbon atoms] Examples of alcohols having 2 to 3 carbon atoms (hereinafter sometimes referred to as alcohols) include ethanol, 1-propanol, and 2-propanol. Ethanol is a preferred example of the alcohol. More preferably, the alcohol consists of ethanol.

[0029] The blending ratio of the alcohol relative to the ferulic acid solution is, for example, 30% by mass or more, preferably 40% by mass or more, and for example, 70% by mass or less.

[0030] Alcohols can be used alone or in combination of two or more types.

[0031] [water] Water is a solvent that dissolves ferulic acid.

[0032] The mixing ratio of water relative to the ferulic acid solution is, for example, 4% by mass or more, and for example, 40% by mass or less, preferably 30% by mass or less.

[0033] The mass ratio of alcohol to water (alcohol / water) is 1 or more, preferably more than 1, and is, for example, 20 or less, preferably 15 or less, more preferably 10 or less.

[0034] When the mass ratio is equal to or greater than the lower limit, ferulic acid can be reliably dissolved. In particular, ferulic acid can be reliably dissolved even when the concentration of ferulic acid is high (for example, 22% by mass or more and 32% by mass or less, the same applies hereinafter).

[0035] On the other hand, if the mass ratio is less than the lower limit, ferulic acid cannot be sufficiently dissolved.

[0036] [Salts of carboxyl group-containing compounds] The salt of the carboxyl group-containing compound is a component that inhibits precipitation of ferulic acid after dissolution of ferulic acid.

[0037] In the salt of the carboxyl group-containing compound, examples of the carboxyl group-containing compound include a compound containing a hydroxyl group and a carboxyl group, and a hydroxyl group-free carboxyl group-containing compound.

[0038] The hydroxyl group- and carboxyl group-containing compound is a compound containing a hydroxyl group in addition to a carboxyl group. Examples of the hydroxyl group- and carboxyl group-containing compound include glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, tartronic acid, glyceric acid, ascorbic acid, gluconic acid, salicylic acid, 4-hydroxymethylbenzoic acid, mandelic acid, and benzilic acid, and preferably lactic acid, citric acid, and ascorbic acid.

[0039] The hydroxyl-free carboxyl group-containing compound is a compound that contains a carboxyl group but does not contain a hydroxyl group. Examples of the hydroxyl-free carboxyl group-containing compound include acetic acid, butyric acid, and oxalic acid.

[0040] As the carboxyl group-containing compound, a hydroxyl group- and carboxyl group-containing compound is preferably used, from the viewpoint of further suppressing the precipitation of ferulic acid.

[0041] In addition, examples of salts of carboxyl group-containing compounds include sodium salts and calcium salts, and preferably sodium salts.

[0042] The salt of the carboxyl group-containing compound is preferably a sodium salt of a hydroxyl group- and carboxyl group-containing compound. More preferably, the salt of the carboxyl group-containing compound is a sodium salt of lactic acid, a sodium salt of citric acid, or a sodium salt of ascorbic acid. Particularly preferably, the salt of the carboxyl group-containing compound is a sodium salt of lactic acid or a sodium salt of ascorbic acid, from the viewpoint of improving ultraviolet absorption.

[0043] The blending ratio of the salt of the carboxyl group-containing compound to the ferulic acid solution is more than 3% by mass, preferably 4% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, particularly preferably 9% by mass or more, and for example, 20% by mass or less, preferably 15% by mass or less, more preferably 12% by mass or less.

[0044] If the blending ratio of the salt of the carboxyl group-containing compound exceeds the above lower limit, the precipitation of ferulic acid can be suppressed, resulting in excellent storage stability.

[0045] On the other hand, if the blending ratio of the salt of the carboxyl group-containing compound is below the lower limit, the precipitation of ferulic acid cannot be suppressed, and as a result, the shelf life is reduced.

[0046] Furthermore, if the blending ratio of the salt of the carboxyl group-containing compound is equal to or less than the above upper limit, a highly concentrated ferulic acid solution can be prepared.

[0047] The salts of the carboxyl group-containing compounds can be used alone or in combination of two or more kinds.

[0048] [Polyvinylpyrrolidone] Polyvinylpyrrolidone is a component that inhibits precipitation of ferulic acid after dissolution of ferulic acid.

[0049] The number average molecular weight of polyvinylpyrrolidone is 1,000 or more, preferably 5,000 or more, more preferably 8,000 or more, and 20,000 or less, preferably 15,000 or less, more preferably 12,000 or less.

[0050] When the number average molecular weight of polyvinylpyrrolidone is equal to or greater than the above lower limit and equal to or less than the above upper limit, precipitation of ferulic acid can be suppressed.

[0051] The number average molecular weight of polyvinylpyrrolidone can be measured by gel permeation chromatography.

[0052] Alternatively, commercially available polyvinylpyrrolidone may be used, such as PVP10 (manufactured by Strem Chemicals Inc.).

[0053] The blending ratio of polyvinylpyrrolidone to the ferulic acid solution exceeds 3% by mass, preferably 4% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, particularly preferably 9% by mass or more, and for example, 20% by mass or less, preferably 15% by mass or less, more preferably 12% by mass or less.

[0054] If the blending ratio of polyvinylpyrrolidone exceeds the above lower limit, the precipitation of ferulic acid can be suppressed, resulting in excellent storage stability.

[0055] On the other hand, if the blending ratio of polyvinylpyrrolidone is below the lower limit, the precipitation of ferulic acid cannot be suppressed, and as a result, the shelf life is reduced.

[0056] Furthermore, if the blending ratio of polyvinylpyrrolidone is equal to or less than the upper limit, a highly concentrated ferulic acid solution can be prepared.

[0057] As described above, the ferulic acid solution contains ferulic acid, alcohol, water, and a salt of a carboxyl group-containing compound or polyvinylpyrrolidone. The ferulic acid solution preferably does not contain polyvinylpyrrolidone and contains ferulic acid, alcohol, water, and a salt of a carboxyl group-containing compound. The ferulic acid solution more preferably contains ferulic acid, alcohol, water, and a salt of a carboxyl group-containing compound, and particularly preferably contains ferulic acid, alcohol, water, and a salt of a hydroxyl group- and carboxyl group-containing compound.

[0058] Furthermore, the ferulic acid solution is substantially free of other solvents (e.g., polar solvents) other than alcohol and water. If the ferulic acid solution is substantially free of other solvents (polar solvents), safety is improved when the ferulic acid solution is used as a cosmetic raw material. Note that, "the ferulic acid solution is substantially free of other solvents (polar solvents)" means that the blending ratio of other solvents (polar solvents) relative to the ferulic acid solution is, for example, 1% by mass or less, preferably 0.1% by mass or less, more preferably 0.01% by mass or less, and even more preferably 0% by mass.

[0059] [Method of producing ferulic acid solution] The method for producing a ferulic acid solution includes a first step of mixing ferulic acid, alcohol, and water to prepare a mixed solution, and a second step of adding a salt of a carboxyl group-containing compound or polyvinylpyrrolidone to the mixed solution.

[0060] (1st step) In the first step, a mixed solution is prepared. Specifically, ferulic acid, alcohol, and water are mixed and heated.

[0061] The heating temperature is 60°C or higher, preferably 65°C or higher.

[0062] If the heating temperature is equal to or higher than the lower limit, ferulic acid can be reliably dissolved.

[0063] The upper limit of the heating temperature is a temperature below the boiling point of the alcohol. For example, when the alcohol is ethanol, the upper limit of the heating temperature is 78°C or lower, preferably 70°C or lower.

[0064] Furthermore, from the viewpoint of ensuring that ferulic acid is dissolved, the heating time is, for example, 1 minute or more, preferably 5 minutes or more, and, for example, 120 minutes or less, preferably 60 minutes or less, more preferably 30 minutes or less, and even more preferably 20 minutes or less.

[0065] Furthermore, the blending ratio of ferulic acid, the blending ratio of alcohol, and the blending ratio of water are not particularly limited as long as the blending ratios of each relative to the ferulic acid solution in the second step described below are the blending ratios described above.

[0066] This prepares a mixed solution.

[0067] (2nd process) In the second step, a salt of a carboxyl group-containing compound or polyvinylpyrrolidone is added to the mixture, and the mixture is heated.

[0068] The heating temperature and heating time are the same as those in the first step described above.

[0069] This produces a ferulic acid solution.

[0070] [Action and effect] The ferulic acid solution has a mass ratio of alcohol to water (alcohol / water) of 1 or more. This allows ferulic acid to be reliably dissolved. In particular, ferulic acid can be reliably dissolved even at high concentrations.

[0071] Specifically, ferulic acid is known to have ultraviolet absorbing properties, and therefore is used in various fields, such as as a cosmetic raw material.

[0072] On the other hand, when ferulic acid is used as a cosmetic raw material, first, ferulic acid is dissolved in a solvent to prepare a ferulic acid solution.

[0073] At this time, in order to improve the ultraviolet absorption properties of the ferulic acid solution, it has been considered to prepare a highly concentrated ferulic acid solution, but since ferulic acid is poorly soluble, it is not possible to prepare a highly concentrated ferulic acid solution.

[0074] On the other hand, in order to prepare a high-concentration ferulic acid solution, for example, esterification of ferulic acid has been considered, but when ferulic acid is esterified, there is a problem in that the ultraviolet absorption property is reduced.

[0075] Another approach has been considered to make ferulic acid water-soluble by converting it into a sodium salt in advance, but the sodium salt of ferulic acid has the drawback of being unstable under alkaline conditions.

[0076] In addition, in order to prepare a highly concentrated ferulic acid solution, for example, dissolving ferulic acid in a polar solvent has been considered. However, a ferulic acid solution containing a polar solvent has the drawback of being less safe when used as a cosmetic raw material.

[0077] In contrast, the mass ratio of alcohol to water (alcohol / water) is equal to or greater than 1. Therefore, even if the ferulic acid has a high concentration, it can be reliably dissolved.

[0078] Furthermore, ferulic acid is not modified (e.g., esterified), and therefore, problems caused by modification (e.g., reduced ultraviolet absorbency, instability under alkaline conditions) can be suppressed.

[0079] In addition, the ferulic acid solution is substantially free of polar solvents, making it highly safe.

[0080] The ferulic acid solution contains a salt of a carboxyl group-containing compound or polyvinylpyrrolidone in an amount exceeding 3% by mass, which prevents ferulic acid from precipitating. As a result, the solution has excellent shelf life.

[0081] Specifically, when a ferulic acid solution is left at room temperature (25°C), ferulic acid precipitates. This causes a problem of reduced shelf life. Furthermore, when the ferulic acid solution is highly concentrated, the precipitation becomes more pronounced.

[0082] On the other hand, this ferulic acid solution contains a salt of a carboxyl group-containing compound or polyvinylpyrrolidone, and the blending ratio of these exceeds 3% by mass. Therefore, even if the ferulic acid solution is left at room temperature (25°C), precipitation of ferulic acid can be suppressed. As a result, it has excellent storage stability.

[0083] [Variations] In the above description, the method for producing a ferulic acid solution comprises a first step of mixing ferulic acid, alcohol, and water to prepare a mixed solution, and a second step of blending a salt of a carboxyl group-containing compound or polyvinylpyrrolidone with the mixed solution. However, a ferulic acid solution can also be produced by mixing ferulic acid, alcohol, water, and a salt of a carboxyl group-containing compound or polyvinylpyrrolidone all at once and heating the mixture (e.g., heating to 60°C or higher).

[0084] <Ferrulic acid-containing particles> The ferulic acid-containing particles include a dried product of the ferulic acid solution and inorganic particles.

[0085] [Inorganic particles] Examples of inorganic particles include those commonly used in cosmetics, such as talc, mica (natural and synthetic), sericite, kaolin, silica, calcium carbonate, aluminum oxide, zinc oxide, and titanium oxide. From the viewpoint of oil absorption, silica particles are preferred as inorganic particles.

[0086] The inorganic particles have an average particle size of, for example, 0.02 μm or more and, for example, 50 μm or less.

[0087] The inorganic particles can be used alone or in combination of two or more kinds.

[0088] [Method of manufacturing ferulic acid-containing particles] The method for producing ferulic acid-containing particles involves mixing the ferulic acid solution with inorganic particles, and then drying off the alcohol and water to obtain ferulic acid-containing particles.

[0089] More specifically, this method includes a third step of mixing the ferulic acid solution with inorganic particles, and a fourth step of drying the alcohol and water to obtain ferulic acid-containing particles.

[0090] (3rd step) In the third step, the ferulic acid solution is mixed with inorganic particles.

[0091] (4th step) In the fourth step, the alcohol and water are dried to obtain ferulic acid-containing particles.

[0092] Specifically, the alcohol and water are dried using a vacuum dryer at, for example, 40°C or higher, preferably 50°C or higher, or, for example, 60°C or lower, for, for example, 12 hours or more, preferably 18 hours or more, or, for example, 48 hours or less, preferably 36 hours or less.

[0093] This results in ferulic acid-containing particles containing the dried ferulic acid solution and inorganic particles. More specifically, in the ferulic acid-containing particles, the dried product is supported on inorganic particles.

[0094] [Action and effect] The ferulic acid-containing particles include a dried product of the ferulic acid solution and inorganic particles.

[0095] In other words, the ferulic acid-containing particles contain a dried product of a ferulic acid solution, which has excellent storage stability, and therefore has excellent productivity. In particular, if the ferulic acid solution has a high concentration, it also has excellent ultraviolet absorption properties.

[0096] In addition, the method for producing ferulic acid-containing particles includes mixing the ferulic acid solution with inorganic particles, and then drying the alcohol and water to obtain ferulic acid-containing particles.

[0097] In other words, this method for producing ferulic acid-containing particles uses a ferulic acid solution with excellent storage stability. Therefore, ferulic acid-containing particles can be produced with excellent productivity. In particular, if the ferulic acid solution has a high concentration, ferulic acid-containing particles with excellent ultraviolet absorption can be produced.

[0098] <UV absorber> The ultraviolet absorber contains the ferulic acid-containing particles. Therefore, it has excellent productivity. In particular, when it contains ferulic acid-containing particles obtained using a high-concentration ferulic acid solution, it also has excellent ultraviolet absorption properties.

[0099] <Cosmetic ingredients> The cosmetic raw material contains the ferulic acid-containing particles. Therefore, it has excellent productivity. In particular, when it contains ferulic acid-containing particles obtained using a high-concentration ferulic acid solution, it also has excellent ultraviolet absorption properties. [Example]

[0100] The present invention will be described in more detail below with reference to examples and comparative examples. It should be noted that the present invention is in no way limited to these examples and comparative examples. The specific numerical values ​​of the blending ratios (content ratios), physical property values, parameters, etc. used in the following description can be replaced with the corresponding upper limit values ​​(numeric values ​​defined as "equal to or less than" or "less than") or lower limit values ​​(numeric values ​​defined as "equal to or greater than" or "exceeding") of the blending ratios (content ratios), physical property values, parameters, etc. described in the "Description of the Invention" above.

[0101] <Ingredient details> Screw cap vial (20 mL): Maruem Mighty Vial (No. 5) Screw cap vial (50 mL): Maruem Mighty Vial (No. 7) Hanil mixer: HANIL LAB.MIXER LM-110T, manufactured by Hanil Electronics Co., Ltd. Vacuum low-temperature dryer: VOS451-SD, cooling trap device UT-1000, diaphragm type vacuum pump EVP-1200, manufactured by Tokyo Rikakikai Co., Ltd. Ferulic acid: Ferulic acid, manufactured by Tsuno Rice Fine Chemicals Co., Ltd., serial number F09348 Ethanol: Ethanol (99.5), special grade reagent, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Water: Distilled water, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Sodium lactate: Sodium lactate (50%), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Sodium citrate: Trisodium citrate dihydrate, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Sodium ascorbate: L(+)-sodium ascorbate, special reagent grade, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Ascorbic acid: L(+)-ascorbic acid, special reagent grade, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. PVP10: Polyvinylpyrrolidone, number average molecular weight 10,000, trade name "PVP10", manufactured by Strem Chemicals Inc. PVOH: Polyvinyl alcohol, degree of polymerization approximately 500, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Tocopherol: (±)-α-tocopherol, Wako Grade 1, Fujifilm Wako Pure Chemical Industries, Ltd. PEG2000: Polyethylene glycol 2000, Wako Grade 1, Fujifilm Wako Pure Chemical Industries, Ltd. Glycerin: Reagent grade, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. OVEIL GR1: Silica, product name "OVEIL GR1", manufactured by Mizusawa Industrial Chemicals, Ltd.

[0102] <Production of ferulic acid solution> Examples 1 to 18 and Comparative Examples 1 to 16 (1st step) Ferulic acid, ethanol, and water were added to a screw cap bottle (20 mL) according to the formulations in Tables 1 to 3, and the bottle was then closed and heated with shaking in a hot bath at 65°C for 10 minutes. This dissolved the ferulic acid, preparing a mixed solution containing ferulic acid, ethanol, and water. Tables 1 to 3 also show the proportion (amount of active ingredient) of each component relative to the ferulic acid solution.

[0103] (2nd process) A salt of a carboxyl group-containing compound or polyvinylpyrrolidone was added to the mixed solution according to the formulations in Tables 1 to 3, and the mixture was heated with shaking for 10 minutes to produce a ferulic acid solution.

[0104] <Production of ferulic acid-containing particles> (3rd step) Examples 19 to 21 According to the formulation in Table 4, ferulic acid, ethanol, water, and a salt of a carboxyl group-containing compound were added to a screw cap bottle (50 mL), the bottle was capped, and the bottle was heated to 65°C with shaking. This produced a ferulic acid solution. Next, 30.0 g of OVEIL GR1 was added to a honey mixer, and a portion of the ferulic acid solution was added dropwise and stirred for 30 seconds. This dropwise addition and stirring process was repeated six times.

[0105] (4th step) The mixture was dried overnight in a low-temperature vacuum dryer at 50° C. This dried the alcohol and water, and yielded ferulic acid-containing particles.

[0106] Comparative Example 17 30.0 g of OVEIL GR1 and 7.5 g of ferulic acid powder were added to a honey mixer, stirred, and then dried overnight in a vacuum low-temperature dryer at 50° C. This yielded ferulic acid-containing particles.

[0107] <Evaluation> [Precipitation of ferulic acid in ferulic acid solution] The ferulic acid solutions of each Example and Comparative Example were observed for precipitation of ferulic acid. Specifically, the ferulic acid solutions were left at room temperature (25°C), and the precipitation of ferulic acid was visually observed and evaluated based on the following criteria. The results are shown in Tables 1 to 3. (standard) 〇: Ferulic acid did not precipitate even after being left for 24 hours. △: Ferulic acid precipitated after being left for 4 hours. ×: Ferulic acid precipitated from the beginning. Not dissolved: Ferulic acid did not dissolve.

[0108] [UV absorption] The ultraviolet absorbance of the ferulic acid-containing particles of each Example and Comparative Example was measured. Specifically, a 6.5 cm x 6.5 cm piece was cut out of a 1 mm thick transparent PET partition plate, and a 5 cm diameter circle was cut out from the center. Next, a Transpore Tape surgical tape (1527-2) manufactured by 3M was applied so that the circle was hidden. Next, a white surgical tape (1534-2) manufactured by 3M was placed on top of the tape, and 20 ± 1 mg of ferulic acid-containing particles (powder) was evenly placed on the adhesive surface. The SPF and UVA values ​​were measured at nine random points using a Labsphere SPF analyzer UV-2000S. The results are shown in Table 4.

[0109] <Consideration> (ferulic acid solution) It is clear that Examples 1 to 18, in which the mass ratio of alcohol to water (alcohol / water) is 1 or more, can reliably dissolve ferulic acid. On the other hand, it is clear that Comparative Examples 6, 11, and 14, in which the mass ratio is less than 1, cannot dissolve ferulic acid.

[0110] Furthermore, it is clear that Examples 1 to 18, which contain a salt of a carboxyl group-containing compound or polyvinylpyrrolidone, are able to inhibit precipitation of ferulic acid, and as a result, have excellent storage stability. On the other hand, it is clear that Comparative Examples 1 to 6, which do not contain a salt of a carboxyl group-containing compound or polyvinylpyrrolidone, are unable to inhibit precipitation of ferulic acid, and as a result, have reduced storage stability.

[0111] Furthermore, it is clear that Examples 1 to 18, in which the blending ratio of the salt of the carboxyl group-containing compound or the blending ratio of polyvinylpyrrolidone exceeds 3% by mass, are able to suppress precipitation of ferulic acid. As a result, it is clear that they have excellent storage stability. On the other hand, it is clear that Comparative Examples 7 to 10, 12, and 13, in which the blending ratio of the salt of the carboxyl group-containing compound or the blending ratio of polyvinylpyrrolidone is 3% by mass or less, are unable to suppress precipitation of ferulic acid. As a result, it is clear that they have poor storage stability.

[0112] (ferulic acid-containing particles) It is clear that Examples 19 to 21 obtained using a ferulic acid solution have superior ultraviolet absorption properties compared to Comparative Example 17, which does not use a ferulic acid solution. Furthermore, it is clear that Examples 19 to 21 obtained using a ferulic acid solution have superior productivity because they are obtained using a ferulic acid solution with excellent storage stability.

[0113] [Table 1]

[0114] [Table 2]

[0115] [Table 3]

[0116] [Table 4]

Claims

1. Ferulic acid and an alcohol having 2 to 3 carbon atoms; Water and a salt of a carboxyl group-containing compound or polyvinylpyrrolidone, The number average molecular weight of the polyvinylpyrrolidone is 1,000 or more and 20,000 or less, the blending ratio of the salt of the carboxyl group-containing compound or the blending ratio of the polyvinylpyrrolidone exceeds 3 mass%; a mass ratio of the alcohol to the water (alcohol / water) of 1 or more; A ferulic acid solution, wherein the salt of the carboxyl group-containing compound comprises a salt of a hydroxyl group-containing compound and a carboxyl group-containing compound.

2. The ferulic acid solution according to claim 1, wherein the blending ratio of the ferulic acid is 10% by mass or more.

3. A method for producing ferulic acid-containing particles, comprising mixing the ferulic acid solution according to claim 1 or 2 with inorganic particles, and then drying the alcohol and water to obtain ferulic acid-containing particles.

4. The method for producing ferulic acid-containing particles according to claim 3, wherein the inorganic particles are silica particles.

5. Ferulic acid-containing particles comprising a dried product of the ferulic acid solution according to claim 1 or 2 and inorganic particles.

6. The ferulic acid-containing particles according to claim 5 , wherein the inorganic particles are silica particles.

7. An ultraviolet absorber comprising the ferulic acid-containing particles according to claim 5 or 6.

8. A cosmetic raw material comprising the ferulic acid-containing particles according to claim 5 or 6.

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