Aqueous dispersion composition and method for producing the same, as well as food, cosmetic and pharmaceutical

Abstract

To provide an aqueous dispersion composition containing a tetrahydrocurcuminoid, which ensures dispersion stability over the long term and suppresses precipitation and a method for producing the same, as well as foods, cosmetics and pharmaceuticals including the aqueous dispersion composition.SOLUTION: The present invention provides an aqueous dispersion composition that comprises solid particles containing a tetrahydrocurcuminoid, an aqueous medium, and a dispersion aid, wherein the dispersion aid contains at least one selected from phospholipids, saponins, sucrose fatty acid esters, polyglyceryl fatty acid esters, sorbitan fatty acid esters, polyoxyethylene phytosterols, polysaccharides, sugar derivatives, polyvinylpyrrolidone, polyvinyl alcohols, and enzyme-treated products, and a method for producing the same, as well as foods, cosmetics and pharmaceuticals including the aqueous dispersion composition.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to an aqueous dispersion composition containing solid particles containing tetrahydrocurcuminoids, a method for producing the same, and foods, cosmetics, and pharmaceuticals using the aqueous dispersion composition. [Background technology]

[0002] Tetrahydrocurcuminoids are reduced forms of curcuminoids, and are expected to have excellent antioxidant properties that suppress oxidative stress on cells, have beauty effects, and improve liver function, and are used in foods, pharmaceuticals, cosmetics, etc.

[0003] Patent Document 1 discloses a method for using tetrahydrocurcuminoids and a method for producing the same for controlling physiological and pathological events related to the skin and mucous membranes, and Patent Document 2 discloses cosmetics containing tetrahydrocurcumin. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2002-541205 [Patent Document 2] JP 2003-300861 A Summary of the Invention [Problem to be solved by the invention]

[0005] In order to broaden the options of application and use forms of tetrahydrocurcuminoids, there is a strong demand for preparing tetrahydrocurcuminoids in the form of an aqueous dispersion composition in which the tetrahydrocurcuminoids are dispersed in an aqueous medium. However, since tetrahydrocurcuminoids are in the form of poorly water-soluble solid particles, when preparing an aqueous dispersion composition, the tetrahydrocurcuminoid particles may precipitate in the aqueous dispersion composition, causing turbidity.

[0006] In addition, in order to maximize the pharmaceutical effects of tetrahydrocurcuminoid, it is important to make the tetrahydrocurcuminoid particles finer, increase the specific surface area, and improve the water solubility. However, in general, when the particle size in an aqueous dispersion becomes smaller, the specific surface area increases, and the aggregation force acts, which tends to make it difficult to ensure the dispersion stability of the particles. Therefore, there has been a demand for the development of a technology that can ensure the long-term dispersion stability of finely divided tetrahydrocurcuminoid particles in the form of an aqueous dispersion.

[0007] The present disclosure aims to provide an aqueous dispersion composition containing a tetrahydrocurcuminoid that can ensure dispersion stability over a long period of time and inhibit precipitation, a method for producing the same, and foods, cosmetics, and pharmaceuticals that use the aqueous dispersion composition. [Means for solving the problem]

[0008] The aqueous dispersion composition, its production method, food, cosmetic, and pharmaceutical composition according to the present disclosure may have the following configurations [1] to

[12] . [1] An aqueous dispersion composition comprising solid particles (A) containing at least tetrahydrocurcuminoid, a dispersing aid (B), and an aqueous medium (C), wherein the dispersing aid (B) contains at least one member selected from the group consisting of phospholipids, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene phytosterols, polysaccharides, sugar derivatives, polyvinylpyrrolidone, polyvinyl alcohol, and enzyme-treated products. [2] The aqueous dispersion composition according to [1], wherein the dispersing aid (B) contains at least one selected from the group consisting of lecithin, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, methylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, gum arabic, xanthan gum, γ-cyclodextrin, polyvinylpyrrolidone, polyvinyl alcohol, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin. [3] The aqueous dispersion composition according to [1] or [2], wherein the average particle size of the solid particles (A) containing tetrahydrocurcuminoid is 500 nm or less. [4] The aqueous dispersion composition according to any one of [1] to [3], wherein a mass ratio of the solid particles containing tetrahydrocurcuminoid (A) to the dispersion aid (B) is 1:1 to 2.5:1. [5] The aqueous dispersion composition according to any one of [1] to [4], wherein the solid particles (A) containing tetrahydrocurcuminoid are a product of wet milling or pulverization. [6] The solid particles (A) containing at least a tetrahydrocurcuminoid contain a tetrahydrocurcuminoid and a water-soluble organic solvent (D), and the water-soluble organic solvent (D) satisfies the following (i) to (iii): (i) The molecular weight is 100 to 350. (ii) Having a total of two or more functional groups consisting of hydroxyl groups and / or ester groups. (iii) The viscosity at 60°C is 2 to 150 mPa s. The aqueous dispersion composition according to [1], wherein the content of the water-soluble organic solvent (D) is 0.003 to 0.3 parts by mass per 100 parts by mass of the solid particles (A) containing tetrahydrocurcuminoid. [7] The aqueous dispersion composition according to [6], wherein the water-soluble organic solvent (D) contains at least one selected from the group consisting of diacetin, triacetin, tripropionin, tributyrin, triethyl citrate, and acetyltriethyl citrate. [8] The aqueous dispersion composition according to any one of [1] to [7], which is an aqueous dispersion composition treated with ultrasonic waves, a homogenizer, or a bead mill. [9] A food product comprising the aqueous dispersion composition according to any one of [1] to [8].

[10] A cosmetic preparation comprising the aqueous dispersion composition according to any one of [1] to [8].

[11] A pharmaceutical comprising the aqueous dispersion composition according to any one of [1] to [8].

[12] A method for producing the aqueous dispersion composition according to any one of [1] to [8], comprising: dispersing solid particles (A) containing tetrahydrocurcuminoid, a dispersion aid (B), and an aqueous medium (C) by ultrasonic dispersion, homogenizer dispersion, or bead mill dispersion to obtain the aqueous dispersion composition. Effect of the Invention

[0009] According to the present disclosure, it is possible to provide an aqueous dispersion composition containing a tetrahydrocurcuminoid, which can ensure dispersion stability over a long period of time and suppress precipitation, a method for producing the same, and foods, cosmetics, and pharmaceuticals using the aqueous dispersion composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The aqueous dispersion composition according to the present disclosure, its production method, and food, cosmetic, and pharmaceutical products will be described below. In this specification, the use of "to" indicating a range of values ​​means that the values ​​before and after it are included as the lower limit and upper limit. In the present specification, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range. In addition, in the present specification, the upper or lower limit of the numerical range may be replaced with a value shown in the examples. Furthermore, in this specification, the amount of each component contained in the aqueous dispersion composition means the total amount of the multiple substances when the composition contains multiple substances corresponding to each component, unless otherwise specified.

[0011] <Aqueous dispersion composition> The aqueous dispersion composition according to the present disclosure (hereinafter also referred to as the present composition) contains solid particles (A) containing tetrahydrocurcuminoids, an aqueous medium (C), and a specific dispersion aid (B), and may contain other additives as necessary. The dispersion aid (B) contains at least one selected from the group consisting of phospholipids, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene phytosterols, polysaccharides, sugar derivatives, polyvinylpyrrolidone, polyvinyl alcohol, and enzyme-treated products. The present composition having such a configuration can stably maintain the dispersion state of the solid particles containing the tetrahydrocurcuminoid for a long period of time, and can suppress changes in appearance such as color.

[0012] (Solid particles containing tetrahydrocurcuminoids (A)) The aqueous dispersion composition according to the present disclosure includes solid particles (A) containing tetrahydrocurcuminoids. Tetrahydrocurcumin, which is one of the tetrahydrocurcuminoids, is a reduced form of curcumin and has a higher antioxidant capacity than curcumin, and therefore has excellent pharmaceutical effects. In addition, tetrahydrocurcumin is colorless and odorless, and therefore is a material that overcomes the disadvantages of curcumin, especially in cases where coloring is a hindrance. Curcuminoids are oil-soluble polyphenols that are mainly found in high concentrations in turmeric and are also found in cardamom, cloves, cumin, pepper, coriander, paprika, mace, and the like, and representative compounds include curcumin, demethoxycurcumin, and bisdemethoxycurcumin. On the other hand, representative compounds of tetrahydrocurcuminoids include tetrahydrocurcumin, tetrahydrodemethoxycurcumin, and tetrahydrobisdemethoxycurcumin. Known methods for producing tetrahydrocurcuminoids include a method in which the aforementioned curcuminoids are used as a starting compound and hydrogenated using a metal catalyst, and a production method using microbial cells as disclosed in JP 2009-45008 A, and either production method is acceptable.

[0013] The solid particles contain tetrahydrocurcuminoids and may contain other components derived from the raw materials, but may be composed only of tetrahydrocurcuminoids. Examples of other components derived from the raw materials include dietary fiber, proteins, lipids, and decomposition products of tetrahydrocurcuminoids. The content of tetrahydrocurcuminoids in the solid particles is preferably 1% by mass to 100% by mass.

[0014] Representative examples of commercially available solid particles (A) containing tetrahydrocurcuminoid include white curcuminoid, tetrahydrocurcuminoid CG (Sabinsa Japan Corporation), etc. Tetrahydrocurcuminoid CG is a solid particle containing a total of three compounds, namely, tetrahydrocurcumin and its derivatives.

[0015] In the present composition, the average particle size of the solid particles containing tetrahydrocurcuminoid in the aqueous dispersion is preferably 500 nm or less. If the average particle size of the solid particles containing tetrahydrocurcuminoid is 500 nm or less, the dispersion stability of the solid particles containing tetrahydrocurcuminoid in the present composition is improved, and precipitation can be easily suppressed for a long period of time. In addition, the solubility is further improved by the fineness, and a pharmaceutical effect can be expected. In addition, from the viewpoint of suppressing precipitation, the average particle size of the solid particles containing tetrahydrocurcuminoid is more preferably 300 nm or less, and even more preferably 100 nm or less. If it is less than 50 nm, it becomes extremely difficult to ensure the dispersion stability of the solid particles, so the average particle size is preferably 50 nm or more. The method for measuring the average particle size of the solid particles containing tetrahydrocurcuminoid will be described later.

[0016] The content of solid particles (particularly tetrahydrocurcuminoid) in the present composition can be appropriately set, but is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, from the viewpoint of design freedom in the formulation of foods, medicines, etc. On the other hand, from the viewpoint of inhibiting aggregation and precipitation of solid particles, the content of solid particles (particularly tetrahydrocurcuminoid) in the present composition is preferably 20% by mass or less, more preferably 15% by mass or less. The content of tetrahydrocurcuminoid in the present composition can be quantitatively analyzed by HPLC using a conventional method.

[0017] Here, the solid particles in the present composition are preferably wet-grinding products from the viewpoint of long-term precipitation suppression.In addition, the method of dispersing the solid particles in the present composition is preferably ultrasonic treatment (ultrasonic dispersion), homogenizer treatment (homogenizer dispersion) or bead mill dispersion, which will be described later in detail.Therefore, the present composition is preferably ultrasonic dispersion, homogenizer dispersion or bead mill dispersion using the above solid particles, the aqueous medium described later, the dispersion assistant, and other additives as necessary.

[0018] In addition, the solid particles containing tetrahydrocurcuminoid in the present composition may be either crystalline particles or amorphous particles. The distinction between crystalline particles and amorphous particles is performed by X-ray diffraction. Specifically, in the measurement results of the solid particles by X-ray diffraction, if there is a peak, the solid particles are determined to be crystalline particles, and if there is no peak, the solid particles are determined to be amorphous particles. In general, amorphous particles have improved water solubility compared to crystalline particles, but they tend to have reduced dispersion stability such as precipitation, and also tend to have concerns about stability over time, such as decomposition observed in light resistance tests.

[0019] (Aqueous medium (C)) The aqueous medium (C) contains at least water, and may consist of water. The water is not particularly limited and may be appropriately selected depending on the purpose of use. For example, tap water, natural water, purified water, distilled water, mineral water, alkaline ionized water, deep sea water, ion-exchanged water, pure water, ultrapure water such as Milli-Q water, etc. may be used. Milli-Q water is ultrapure water obtained by a Milli-Q water production apparatus, which is an ultrapure water production apparatus manufactured by Merck Millipore Co. Among them, preferred examples of water used in the dispersion composition of the present invention include purified water, distilled water, ion-exchanged water, pure water, Milli-Q water, and the like, from the viewpoint of having fewer impurities.

[0020] The blending ratio of the aqueous medium in the present composition can be appropriately set, but is preferably 95% by mass or less, more preferably 90% by mass or less, from the viewpoint of design freedom when formulating foods, medicines, etc. From the viewpoint of inhibiting aggregation and precipitation of solid particles, the blending ratio of the aqueous medium in the present composition is preferably 60% by mass or more, more preferably 75% by mass or more.

[0021] The aqueous medium may contain, in addition to water, at least one component selected from the group consisting of a solvent that can be uniformly mixed with water or that can be dissolved in water, such as a water-soluble organic solvent, a pH adjuster, and a preservative.

[0022] The water-soluble organic solvent refers to an organic solvent having a solubility in water of 10 (g / 100 g-H2O) or more at 25° C. From the viewpoint of being able to stably maintain the dispersion of solid particles, the solubility in water of the organic solvent is preferably 30 (g / 100 g-H2O) or more, and more preferably 50 (g / 100 g-H2O) or more.

[0023] Examples of the water-soluble organic solvent include methanol, ethanol, 1-propanol, 2-propanol, 2-butanol, acetone, tetrahydrofuran, acetonitrile, methyl ethyl ketone, dipropylene glycol monomethyl ether, methyl acetate, methyl acetoacetate, N-methylpyrrolidone, dimethyl sulfoxide, ethylene glycol, 1,3-butanediol, 1,4-butanediol, propylene glycol, diethylene glycol, triethylene glycol, glycerin, etc. When the aqueous medium contains a water-soluble organic solvent, only one type of water-soluble organic solvent may be used, or two or more types may be used in combination.

[0024] The content of the water-soluble organic solvent in the aqueous medium can be appropriately selected depending on the purpose. From the viewpoint of ease of application to a living body, the content of the water-soluble organic solvent in the aqueous medium is preferably 40% by mass or less, more preferably 1% by mass to 20% by mass. In addition, an embodiment in which the aqueous medium does not contain a water-soluble organic solvent is also preferable.

[0025] (Dispersing agent (B)) The composition contains a specific dispersing aid (B). The dispersing aid contains at least one selected from the group consisting of phospholipids, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene phytosterols, polysaccharides, sugar derivatives, polyvinylpyrrolidone, polyvinyl alcohol, and enzyme-treated products. Among these, from the viewpoint of long-term suppression of precipitation, it is preferable that the dispersing aid (B) contains at least one selected from the group consisting of lecithin, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, methylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, gum arabic, xanthan gum, γ-cyclodextrin, polyvinylpyrrolidone, polyvinyl alcohol, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin.

[0026] The content of the dispersing aid (B) in the present composition (when two or more dispersing aids are used in combination, the total amount) can be appropriately selected depending on the purpose, but from the viewpoint of ensuring stability, it is preferably 1% by mass or more, more preferably 2.5% by mass or more, and even more preferably 5% by mass or more. In addition, from the viewpoint of design freedom when formulating foods, pharmaceuticals, etc., the content of the dispersing aid in the present composition is preferably 20% by mass or less, more preferably 10% by mass or less.

[0027] The content mass ratio of the solid particles (A) containing tetrahydrocurcuminoid to the dispersing aid (B) is preferably 1:1 to 2.5:1, more preferably 1:1 to 1.5:1, from the viewpoint of suppressing sedimentation for a long period of time. The dispersion aid is preferably as small as possible in amount because the higher the concentration of the solid particles containing tetrahydrocurcuminoid in the composition, the greater the degree of freedom in formulation design during formulation, and because there is a concern that the type of dispersion aid may adversely affect the absorbability of tetrahydrocurcuminoid. However, since there is a trade-off with dispersion stability, it is necessary to determine the amount of dispersion aid appropriately. Each dispersion aid will be described below.

[0028] (Phospholipids) Phospholipids are also called phosphatides, and include glycerophospholipids and sphingophospholipids. The phospholipids used in the present composition may be either glycerophospholipids or sphingophospholipids. However, from the viewpoint of further improving the dispersibility of solid particles containing tetrahydrocurcuminoid, glycerophospholipids are preferred, and lecithin and the like are more preferred.

[0029] Lecithin refers to phosphatidylcholine (hereinafter sometimes abbreviated as PC) itself or a mixture containing at least phosphatidylcholine. A mixture containing at least phosphatidylcholine is generally a mixture that may contain, in addition to phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, N-acylphosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, lysophosphatidylcholine, lysophosphatidic acid, sphingomyelin, sphingoethanolamine, etc.

[0030] Lecithin can be derived from any animal or plant, including soybean and egg yolk. In addition, due to the physiological activity of phospholipids themselves and the need for more advanced emulsifiers, lecithin whose purity has been improved by purification or distillation as described below, or lecithin that has been subjected to various treatments, such as highly purified lecithin, fractionated lecithin, hydrogenated lecithin, and enzymatically decomposed lecithin, can also be used.

[0031] Soybean lecithin is produced by drying and refining the soybean cake by-product of the 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, but because it is inexpensive, paste-type lecithin is mostly used, especially in the food industry.

[0032] Highly refined lecithin is lecithin that has been deoiled and powdered using a solvent such as acetone. Examples of commercially available highly refined lecithin products include Phospholipon 20 (trade name, manufactured by Lipoid Co., Ltd.), Lesion P (trade name, manufactured by Riken Vitamin Co., Ltd.), SLP-White (trade name, manufactured by Tsuji Oil Mills Co., Ltd.), and Emulmetic 300 (trade name, manufactured by Lucas Meyer Cosmetics Co., Ltd.).

[0033] Fractionated lecithin is lecithin that has a high content of specific phospholipids from highly purified lecithin by utilizing the difference in solubility in various solvents or by performing operations such as distillation. Examples of commercially available fractionated lecithin include Phospholipon 50 (containing 45% by mass of PC), Phospholipon 85G (containing 80% by mass of PC), Phospholipon 90G (containing 94% by mass of PC) (all trade names, manufactured by Lipoid Co., Ltd.), Emulmetic 900 (containing 50% by mass of PC), Emulmetic 930 (containing 95% by mass of PC) (all trade names, manufactured by Lucas Meyer Cosmetics Co., Ltd.), SLP-PC70, SLP-PC90 (all trade names, manufactured by Tsuji Oil Co., Ltd.), etc.

[0034] Hydrogenated lecithin is lecithin that has been converted to saturated fatty acids by oxidizing fatty acid polyenoic acids in the lecithin structure and carrying out hydrogenation treatment to improve photostability. Hydrogenated lecithin can be preferably used in cosmetics, skin external preparations, and other pharmaceuticals, but is difficult to use in food and beverages. Examples of commercially available hydrogenated lecithin include Emulmetic 320 (trade name, manufactured by Lucas Meyer Cosmetics Co., Ltd.) and SLP White H (trade name, manufactured by Tsuji Oil Mills Co., Ltd.). Examples of commercially available lecithin with increased PC content and further hydrogenated treatment include Emulmetic 950 (trade name, manufactured by Lucas Meyer Cosmetics Co., Ltd.), SLP-PC92H (trade name, manufactured by Tsuji Oil Mills Co., Ltd.), and Phospholipon 90H (trade name, manufactured by Lipoid Co., Ltd.).

[0035] Enzymatically decomposed lecithin is lecithin obtained by selectively decomposing the ester bond of fatty acid at the second position, which is usually bonded to glycerin, with an enzyme, and is also called lysolecithin to distinguish it from normal lecithin. Compared to unmodified lecithin, lysolecithin has improved water solubility and generally improved emulsifying power. The enzymatic decomposition treatment for preparing lysolecithin is usually performed on paste-like lecithin as a raw material, and the lecithin after the enzymatic decomposition treatment is highly refined to obtain lysolecithin, but there is also a method of obtaining lysolecithin by performing the enzymatic decomposition treatment on fractionated lecithin. Representative examples of commercially available lysolecithin include SLP White Lyso and SLP-LPC70 (both trade names, manufactured by Tsuji Oil Co., Ltd.).

[0036] Another type of enzyme-treated lecithin is obtained by decomposing the ester bond between phosphoric acid and base. By carrying out a process to decompose the ester bond between phosphoric acid and base, the base is removed from the phospholipid, and the phospholipid becomes phosphatidic acid, which exhibits strong anionic properties. Examples of commercially available enzyme-treated lecithin include PA Nagase and Lysophospholipid Nagase H (both trade names, manufactured by Nagase Chemtex Corporation).

[0037] (saponin) Saponin is a general term for glycosides composed of sapogenin and sugar. It is found in various plants, including Sanponsou. It is a white amorphous powder and, because it is amphiphilic, dissolves when mixed with water and exhibits surface activity.

[0038] (Sucrose fatty acid ester) The sucrose fatty acid ester is obtained by transesterification of sucrose and fatty acid methyl. The sucrose fatty acid ester in the present composition is preferably a compound having a fatty acid carbon number of 12 to 20, more preferably a compound having a carbon number of 12 to 18, further preferably a compound having a carbon number of 14 to 16, and particularly preferably a compound having a carbon number of 14. By controlling the carbon number of the fatty acid to be 12 or more and 18 or less, the dispersion stability of the solid particles containing tetrahydrocurcuminoid is further improved.

[0039] Specific examples of sucrose fatty acid esters include sucrose dioleate, sucrose distearate, sucrose dipalmitate, sucrose dimyristate, sucrose dilaurate, sucrose monooleate, sucrose monostearate, sucrose monopalmitate, sucrose monomyristate, and sucrose monolaurate. Among these, the sucrose fatty acid ester is preferably sucrose monostearate (the ingredient name in cosmetics: sucrose stearate).

[0040] As the sucrose fatty acid ester, commercially available products can be used. Examples of commercially available sucrose fatty acid esters include "S-070" [HLB (Hydrophilic-Lipophilic) ester] from the "Ryoto (registered trademark) Sugar Ester" series by Mitsubishi Chemical Corporation. Balance value (catalog value): 1 or less, monoester body (catalog value): approx. 0% by mass; S-170 [HLB value (catalog value): approx. 1, monoester body (catalog value): approx. 1% by mass; S-270 [HLB value (catalog value): approx. 2, monoester body (catalog value): approx. 10% by mass; S-370 [HLB value (catalog value): approx. 3, monoester body (catalog value): approx. 20% by mass; S-370F [HLB value (catalog value): approx. 3, monoester body (catalog value): approx. 20% by mass; S-570 [HLB value (catalog value): approx. 5, monoester body (catalog value): approx. 30% by mass; S-770 [HLB value (catalog value ): about 7, monoester (catalog value): about 40% by mass; "S-970" [HLB value (catalog value): about 9, monoester (catalog value): about 50% by mass; "S-1170" [HLB value (catalog value): about 11, monoester (catalog value): about 55% by mass; "S-1170F" [HLB value (catalog value): about 11, monoester (catalog value): about 55% by mass; "S-1570" [HLB value (catalog value): about 15, monoester (catalog value): about 70% by mass; "S-1670" [HLB value (catalog value): about 16, monoester (catalog value): about 75% by mass] (all sucrose stearate esters). Other examples include "SS" from Daiichi Kogyo Seiyaku's "DK Ester (registered trademark)" series [HLB value (catalog value): about 19, monoester form (catalog value): 97% by mass], "F-160", "F-140", "F-110", "F-90", "F-70", "F-50", "F-20W", "F-10", "FA-10E", and "S-10", "S-50", "S-70", "S-110", "S-160", and "S-190" from the "Cosmelike (registered trademark)" series [HLB value (catalog value): about 19, monoester form (catalog value): 97% by mass], and the like. Among these, as commercially available sucrose fatty acid esters, at least one selected from the group consisting of "S-1170", "S-1170F", "S-1570", and "S-1670" of the "Ryoto (registered trademark) Sugar Ester" series, "SS", "F-160", "F140", and "F110" of the "DK Ester (registered trademark)" series, and "S-110", "S-160", and "S-190" of the "Cosmelike (registered trademark)" series is preferred. In addition, since the content of monoesters in the sucrose fatty acid esters is high, at least one selected from the group consisting of "SS" of the "DK Ester (registered trademark)" series and "S-190" of the "Cosmelike (registered trademark)" series is particularly preferred as a commercially available sucrose fatty acid ester.

[0041] (Polyglycerol fatty acid ester) Polyglycerol fatty acid esters are produced by esterifying fatty acids to polyglycerol. The polyglycerol fatty acid esters are not particularly limited, but the polyglycerol structure contained in the polyglycerol fatty acid esters may be linear, branched, or cyclic. Examples of polyglycerol fatty acid esters that can be used in the present composition include esters of polyglycerol having an average degree of polymerization of 2 or more and fatty acids having 8 to 18 carbon atoms. The average degree of polymerization of polyglycerol that can be used to prepare polyglycerol fatty acid esters is preferably 2 or more, and more preferably 2 to 10. Examples of fatty acids having 8 to 18 carbon atoms that can be used to prepare polyglycerol fatty acid esters include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, etc.

[0042] The polyglycerol fatty acid ester may be one in which one type of fatty acid is ester-bonded to one molecule of polyglycerol, or may be one in which two or more types of fatty acids are ester-bonded to one molecule of polyglycerol.

[0043] As the polyglycerol fatty acid ester, for example, from the viewpoint that the temporal stability of the present composition tends to be superior, it is preferable that the polyglycerol fatty acid ester contains a fatty acid structure having at least one of a branched chain and an unsaturated carbon bond, and it is more preferable that the polyglycerol fatty acid ester contains a fatty acid structure having either a branched chain or an unsaturated carbon bond.

[0044] Preferred examples of polyglycerol fatty acid esters that can be used in the present composition include hexaglycerol monooleate, hexaglycerol monostearate, hexaglycerol monopalmitate, hexaglycerol monomyristate, hexaglycerol monolaurate, decaglycerol monooleate, decaglycerol monostearate, decaglycerol monopalmitate, decaglycerol monomyristate, decaglycerol monolaurate, etc. Among these, more preferred examples include decaglycerol monooleate (HLB=12), decaglycerol monostearate (HLB=12), decaglycerol monopalmitate (HLB=13), decaglycerol monomyristate (HLB=14), decaglycerol monolaurate (HLB=16), etc.

[0045] As the polyglycerol fatty acid ester, commercially available products can be used. Examples of commercially available polyglycerol fatty acid esters include NIKKOL DGMS, NIKKOL DGMO-CV, NIKKOL DGMO-90V, NIKKOL DGDO, NIKKOL DGMIS, NIKKOL DGTIS, NIKKOL Tetraglyn 1-SV, NIKKOL Tetraglyn 1-O, NIKKOL Tetraglyn 3-S, NIKKOL Tetraglyn 5-S, NIKKOL Tetraglyn 5-O, NIKKOL Hexaglyn 1-L, NIKKOL Hexaglyn 1-M, NIKKOL Hexaglyn 1-SV, NIKKOL Hexaglyn 1-O, NIKKOL Hexaglyn 3-S, NIKKOL Hexaglyn4-B, NIKKOL Hexaglyn 5-S, NIKKOL Hexaglyn 5-O, NIKKOL Hexaglyn PR-15,NIKKOL Decaglyn 1-L,NIKKOL Decaglyn 1-M,NIKKOL Decaglyn 1-SV,NIKKOL Decaglyn 1-50SV,NIKKOL D ecaglyn 1-ISV,NIKKOL Decaglyn 1-O,NIKKOL Decaglyn 1-OV,NIKKOL Decaglyn 1-LN,NIKKOL Decaglyn 2-SV,NIKKOL Decaglyn 2-ISV,NIKKOL Decaglyn 3-SV,NIKKOL Decaglyn 3-OV,NIKKOL Decaglyn 5-SV,NIKKOL Decaglyn 5-HS,NIKKOL Decaglyn 5-IS,NIKKOL Decaglyn 5-OV,NIKKOL Decaglyn 5-OR,NIKKOL Decaglyn 7-S,NIKKOL Decaglyn 7-O,NIKKOL Examples of such products include Decaglyn 10-SV, NIKKOL Decaglyn 10-IS, NIKKOL Decaglyn 10-OV, NIKKOL Decaglyn 10-MAC, and NIKKOL Decaglyn PR-20 (all of which are trade names, manufactured by Nikko Chemicals Co., Ltd.). Note that "NIKKOL" is a registered trademark of Nikko Chemicals Co., Ltd.

[0046] Further examples include Ryoto (registered trademark) Polyglycerol L-7D, L-10D, M-7D, M-10D, P-8D, SWA-10D, SWA-15D, SWA-20D, S-24D, S-28D, O-15D, O-50D, B-70D, B-100D, ER-60D, LOP-120DP, DS13W, DS3, HS11, HS9, TS4, TS2, DL15, DO13 (all trade names, Mitsubishi Chemical Corporation), Sunsoft (registered trademark) Q-17UL, Sunsoft Q-14S, Sunsoft A-141C (all trade names, Taiyo Kagaku Co., Ltd.), Poem (registered trademark) DO-100, Poem J-0021 (all trade names, Riken Vitamin Co., Ltd.), and the like.

[0047] (sorbitan fatty acid ester) Sorbitan fatty acid esters are compounds synthesized by esterification reaction of sorbitol and fatty acids. They may also be in the form of polyoxyethylene sorbitan fatty acid esters, which are ethylene oxide added to sorbitan fatty acid esters.

[0048] Examples of sorbitan fatty acid esters include sorbitan monolaurate (Span 20) and sorbitan monooleate (Span 80).

[0049] The most representative polyoxyethylene sorbitan fatty acid esters are commercially available Tween surfactants. Examples of polyoxyethylene sorbitan fatty acid esters include polyoxyethylene sorbitan monolaurate (Polyoxyethylene Sorbitan Monolaurate Examples of such polyoxyethylene sorbitan monopalmitate include Tween 20, Polyoxyethylene Sorbitan Monopalmitate (Tween 40), Polyoxyethylene Sorbitan Monostearate (Tween 60), and Polyoxyethylene Sorbitan Monooleate (Tween 80).

[0050] (Polyoxyethylene phytosterol) Polyoxyethylene phytosterol (POE phytosterol) is a compound represented by the following general formula (I). RO-(EO) n -H General formula (I) In general formula (I), R represents a phytosteryl group, EO represents an ethylene oxide group, and n represents 5 to 60. From the viewpoint of further improving the dispersion stability of the solid particles, n is preferably in the range of 10 to 50, and more preferably in the range of 10 to 30. As the POE phytosterol, a POE phytosterol containing a polyoxypropylene group (POP) or a polyoxybutylene group (POB) in addition to a polyoxyethylene group in the hydrophilic partial structure may be used as long as the effects of the present disclosure are not impaired. Examples of POE phytosterol include POE phytosterol ether, POE / POP phytosterol ether, POE / POP / POB phytosterol ether, POE / POB phytosterol ether, etc. POE phytosterol ether is also available as a commercially available product, and specific examples of commercially available products include the NIKKOL series BPS-5, BPS-10, BPS-20, and BPS-30 (all of which are trade names, manufactured by Nikko Chemicals).

[0051] (polysaccharide) As polysaccharides, acidic polysaccharides, neutral polysaccharides, basic polysaccharides, etc. derived from plants, seaweed, or microorganisms are preferably applicable. Examples of acidic polysaccharides include pectin, sodium alginate, potassium alginate, gum arabic, xanthan gum, gellan gum, tragacanth gum, inulin, carrageenan, polygalacturonic acid, agar, polyphyllan, funoran, furceran, etc. Examples of neutral polysaccharides include tamarind seed gum, guar gum, locust bean gum, starch, pullulan, laminaran, konjac mannan, etc. Examples of basic polysaccharides include chitosan. Among these, it is preferable to use at least one of gum arabic and xanthan gum from the viewpoint of long-term dispersion stability.

[0052] (sugar derivative) Examples of sugar derivatives include cellulose derivatives. Examples of cellulose derivatives include etherified cellulose, in which a portion of the hydroxyl groups of glucose constituting cellulose is etherified. Specific examples of the etherified cellulose include methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethyl cellulose, carboxymethyl cellulose, and carboxymethyl cellulose salts. Here, examples of the carboxymethyl cellulose salts include alkali metal carboxymethyl cellulose salts such as sodium carboxymethyl cellulose, and alkaline earth metal carboxymethyl cellulose salts such as calcium carboxymethyl cellulose. Representative examples of commercially available cellulose derivatives include HPC-SSL, HPC-SL, and HPC-L (all trade names, manufactured by Nisso Shoji Co., Ltd.).

[0053] In addition to cellulose derivatives, cyclodextrins can also be used as sugar derivatives. Cyclodextrins are oligosaccharides in which glucose units are linked in a ring via α-1,4 bonds, and are also called cyclic oligosaccharides due to their structure. Cyclodextrins with 6, 7, and 8 glucose units are called α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin, respectively. Among these sugar derivatives, it is preferable to use at least one selected from methyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose and γ-cyclodextrin from the viewpoint of long-term dispersion stability.

[0054] (Polyvinylpyrrolidone) Polyvinylpyrrolidone (PVP) is a non-ionic water-soluble polymer compound obtained by polymerizing N-vinyl-2-pyrrolidone. Polyvinylpyrrolidone is a white powder that absorbs moisture from the air well (up to about 18% by mass). Commercially available polyvinylpyrrolidone can be used as appropriate. Polyvinylpyrrolidone can be obtained, for example, by synthesizing N-vinyl-2-pyrrolidone from acetylene, ammonia, and formaldehyde, and then polymerizing it in the presence of an oxidizing agent or the like.

[0055] (Polyvinyl alcohol) Polyvinyl alcohol is known as a water-soluble synthetic resin. In the present composition, a conventionally known polyvinyl alcohol can be appropriately used. Polyvinyl alcohol can be produced, for example, by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate monomer.

[0056] (Enzyme-treated product) In the present composition, enzyme-treated products can be used as dispersing aids.Typical examples of enzyme-treated products include enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin and enzyme-treated hesperidin.As enzyme-treated products, conventionally known products can be used.For example, enzyme-treated products can be used that are manufactured by the methods described in JP-A-10-70994, JP-A-3-7593, JP-A-5-194164, etc. Commercially available enzyme-treated rutin products include, for example, "αG Rutin H," "αG Rutin P," and "αG Rutin PS" (all trade names, manufactured by Toyo Sugar Refining Co., Ltd.). An example of a commercially available enzyme-treated naringin product is "αG Naringin H" (product name, manufactured by Toyo Sugar Refining Co., Ltd.). Commercially available enzyme-treated hesperidin products include, for example, "αG hesperidin H," "αG hesperidin PS," "αG hesperidin PA-T," and "αG hesperidin PA-LE" (all trade names, manufactured by Toyo Sugar Refining Co., Ltd.), and "Hayashibara Hesperidin S" (trade name, manufactured by Hayashibara Co., Ltd.). Commercially available enzyme-treated stevia products include, for example, "αG Sweet P," "αG Sweet PX," "αG Sweet PA," and "αG Sweet H" (all trade names, manufactured by Toyo Sugar Refining Co., Ltd.).

[0057] (Other additives) The composition may contain other additives depending on the intended use, etc., within the scope of not impairing the effects of the present disclosure. Usable additives include substances listed in the 49th Edition of the Food Additives Usage Standards Handbook (Japan Food Sanitation Association), Pharmaceutical Additives Standards 2018 (Yakuji Nipposha), and Cosmetic Ingredients Guide 7th Edition (Yakuji Nipposha).

[0058] <Method for producing aqueous dispersion composition> The present composition can be prepared by applying shear force to a mixture containing solid particles (A) containing tetrahydrocurcuminoid, a dispersion aid (B), and an aqueous medium (C) to mechanically disperse the solid particles containing tetrahydrocurcuminoid to prepare a dispersion containing the solid particles containing tetrahydrocurcuminoid. There is no particular restriction on the shear force application device used to apply the shear force, but any of the following methods is preferred: ultrasonic dispersion, homogenizer dispersion, or bead mill dispersion. Among these, bead mill dispersion is particularly preferred from the viewpoint of particle micronization.

[0059] Ultrasonic dispersion is a method to disintegrate and disperse particles by cavitation generated by immersing an ultrasonic tip in liquid. Commercially available ultrasonic separators include UH-50UH-50F, UH-300, UH-600, UH-600S, UH-600SH (all trade names, MST Corporation), PSF-600, PSF-1200, RUS-600TCVP (all trade names, Nippon Seiki Seisakusho Co., Ltd.), etc.

[0060] Homogenizer dispersion can be roughly classified into stirring type homogenizer, high pressure type homogenizer and the like. Agitator homogenizers are devices that entrain powder into liquid by rotating agitator blades at high speeds, while dispersing the particles by the cutting action of the blades. Commercially available agitator homogenizers include Clearmix W Motion CLM-1.7 / 5.5W and Clear SS5-100 (both trade names) manufactured by M Technique Co., Ltd., and Adihomobixer Type 2M and HV-M (trade names) manufactured by Primix Corporation. A high-pressure homogenizer refers to a device that pressurizes the object to be pulverized to high or ultra-high pressure and pulverizes and disperses it by the shear force generated when it passes through a slit (gap), and generally includes devices called high-pressure homogenizers and ultra-high-pressure homogenizers. Examples of high-pressure homogenizer devices include Starburst (trade name, Sugino Machine Co., Ltd.), NanoVeida (trade name, Yoshida Kikai Kogyo Co., Ltd.), and Microfluidizer M-110E / H (trade name, Mizuho Kogyo Co., Ltd.).

[0061] Bead mill dispersion is a method in which various components (solid particles, dispersion aid, etc.) are mixed in a solvent (aqueous medium), and coarse particles or aggregates (aggregated particles) are pulverized, refined, and dispersed by the collision force between the beads. In this case, the particle surfaces are coated with a dispersion aid (resin or surfactant). This improves the stability of the aqueous dispersion composition, making it easier to suppress sedimentation for a long period of time. These dispersion methods can be appropriately carried out under conventionally known conditions. For example, bead mill dispersion can be carried out for 0.1 to 20 hours using (zirconia) beads with a diameter of 0.1 to 0.5 mm.

[0062] Commercially available bead mills can be used. Commercially available bead mills that can be used to prepare the present composition include Star Mill Nano Getter, Star Mill ZRS, Star Mill LMZ, Agitator Mill LMK (all trade names, Ashizawa Finetech Co., Ltd.), Spike Mill, Mighty Mill, Mighty Mill Mark II, Key Mill (all trade names, Inoue Seisakusho Co., Ltd.), Apex Mill, Super Apex Mill, Ultra Apex Mill (all trade names, Hiroshima Metal & Machinery Co., Ltd.), San Examples of such mills include the SLG, Ready Mill (RMV-03), Nano Ready Mill (RMV-03), Ultra Viscomill (UVM), Ultra-X Viscomill (UVX), New Viscomill (NVM) (all trade names, manufactured by Imex Co., Ltd.), SC Mill, MSC Mill, Attritor, Fine Mill (all trade names, manufactured by Nippon Coke and Engineering Co., Ltd.), Annular Gap Bead Mill (trade name, manufactured by Eurotech Co., Ltd.), DYNO-MILL ECM, DYNO-MILL NPM-NANO Performance Mill (all trade names, manufactured by Shinmaru Enterprise Co., Ltd.), and MicroMediaX1 (trade name, manufactured by Buhler Co., Ltd.).

[0063] From the viewpoint of long-term dispersion stability and suppression of sedimentation, the solid particles (A) are preferably wet-milled and pulverized products. By using the wet-milled and pulverized products, it is possible to prepare fine solid particle powder containing tetrahydrocurcuminoid, and by using the fine solid particles, it is possible to prepare a finer aqueous dispersion. It is desirable to microparticulate the primary particle diameter of the solid particles to 5 to 300 nm. A method for measuring the primary particle diameter of the solid particles will be described later. The wet-milled and pulverized solid particles can be obtained, for example, through the following steps: step (a) of mechanically kneading a material to be treated containing tetrahydrocurcuminoid, a water-soluble inorganic salt, and a water-soluble organic solvent (D) together, and step (b) of removing the water-soluble inorganic salt and the water-soluble organic solvent (D) after step (a).

[0064] (Water-soluble inorganic salts) The water-soluble inorganic salts have the effect of grinding and microparticulating the material to be treated. By using water-soluble inorganic salts, it is possible to remove them by washing. Examples of inorganic salts that can be used include sodium chloride, potassium chloride, ammonium chloride, sodium sulfate, magnesium sulfate, potassium sulfate, calcium sulfate, sodium malate, sodium citrate, disodium citrate, sodium dihydrogen citrate, potassium dihydrogen citrate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, and dipotassium hydrogen phosphate. Among these, sodium chloride is preferable. The amount of the water-soluble inorganic salt to be added is not particularly limited, but from the viewpoints of treatment efficiency and production efficiency, it is preferable to use 50 to 2000 parts by mass, and more preferably 300 to 1000 parts by mass, per 100 parts by mass of the material to be treated. The water-soluble inorganic salt may be used alone or in combination of two or more kinds.

[0065] (Water-soluble organic solvent (D)) The water-soluble organic solvent (D) used in the wet grinding and pulverizing treatment of solid particles must function to wet the poorly water-soluble material to be treated and the water-soluble inorganic salt, and must dissolve (be miscible) in water, but not substantially dissolve the water-soluble inorganic salt used. Furthermore, it is preferable that the water-soluble organic solvent used in the wet grinding and pulverizing treatment satisfies the following (i) to (iii). That is, (i) The molecular weight is 100 to 350. (ii) Having a total of two or more functional groups consisting of hydroxyl groups and / or ester groups. (iii) The viscosity at 60°C is 2 to 150 mPa s. The water-soluble organic solvent satisfies all of the above conditions. If the viscosity is high, the viscosity of the mixture of solid particles and inorganic salt increases, the movement of the inorganic salt as a grinding agent is hindered, and the effect of microparticulating the solid particles cannot be sufficiently obtained. The viscosity of the water-soluble organic solvent in the present specification is a value measured using a cone-plate type rotational viscometer (viscometer: TVE-20L manufactured by Toki Sangyo Co., Ltd.) in accordance with the provisions of JIS Z 8803.

[0066] Examples of the water-soluble organic solvent (D) that can be used in the wet grinding and pulverizing process include glycerin, propylene glycol, polyethylene glycol, dipropylene glycol, diethylene glycol, 2-ethyl-1,3-hexanediol, 2,4-diethyl-1,5-pentanediol, monoacetin, diacetin, triacetin, tripropionin, tributyrin, 2-methylpentane-2,4-diol, 2-butyl-2-ethyl-1,3-propanediol, 1,5-pentanediol, 1,6-hexanediol, 1,2,6-hexanetriol, triethyl citrate, and acetyltriethyl citrate. Examples of water-soluble organic solvents that satisfy the above (i) to (iii) include 2-ethyl-1,3-hexanediol (16.6 mPa·s), 2,4-diethyl-1,5-pentanediol (67.2 mPa·s), monoacetin (13. 7 mPa·s), diacetin (8.2 mPa·s), triacetin (4.1 mPa·s), tripropionin (2.7 mPa·s), tributyrin (3.3 mPa·s), 2-methylpentane-2,4-diol (5.8 mPa·s), 2-butyl-2-ethyl-1,3-propanediol (43.7 mPa·s), 1,5-pentanediol (20.9 mPa·s), 1,6-hexanediol (25.2 mPa·s), 1,2,6-hexanetriol (137.6 mPa·s), triethyl citrate (35.2 mPa·s), and acetyltriethyl citrate (53.7 mPa·s).

[0067] The amount of the water-soluble organic solvent to be added is not particularly limited, but is preferably 5 to 1000 parts by mass, more preferably 50 to 500 parts by mass, per 100 parts by mass of the material to be treated. The water-soluble organic solvent may be used alone or in combination of two or more kinds. The use of a solvent other than the water-soluble organic solvent in the present invention is not excluded within the scope of the present invention. However, from the viewpoint of effectively increasing the microparticulation of solid particles containing tetrahydrocurcuminoid, it is preferable to substantially use the water-soluble organic solvent in the present invention.

[0068] (Step (a)) In the wet grinding and pulverizing method of the present invention, the kneading device used for mechanically kneading and grinding the material to be treated can be used without any particular limitation as long as it has the ability to knead and disperse the material to be treated, the water-soluble inorganic salt, and the water-soluble organic solvent by mechanical means. Examples of the kneading device include kneaders, two-roll mills, three-roll mills, ball mills, attritors, horizontal sand mills, vertical sand mills, Fret mills, Huber-Maller, and disc blade kneading and dispersing machines. Using these, the processing conditions and the like can be appropriately adjusted according to the desired degree of micronization. The water-soluble inorganic salt acts as a grinding aid, and the hardness of the water-soluble inorganic salt is utilized to grind the material to be treated during kneading. By optimizing the kneading conditions (temperature, rotation speed, etc.), solid particles containing tetrahydrocurcuminoids with a narrow and sharp particle size distribution can be obtained.

[0069] (Step (b)) After the kneading and grinding of the solid particles containing tetrahydrocurcuminoids is completed, the water-soluble inorganic salt and the water-soluble organic solvent used in the kneading and grinding are removed to obtain the desired solid particles containing tetrahydrocurcuminoids. Specifically, the mixture of the material to be treated, the water-soluble inorganic salt, and the water-soluble organic solvent is homogenized in the solvent using a stirring blade, dissolver, homogenizer, etc., and then the water-soluble inorganic salt and the water-soluble solvent are removed by filtration and washing with water.

[0070] The solvent used to homogenize the mixture is not particularly limited as long as it is a solvent in which the water-soluble inorganic salt and the water-soluble organic solvent are easily dissolved, and the ground material is difficult to dissolve, and is a physiologically acceptable solvent. The solvent is preferably water, but solvents other than water can also be used. Examples of solvents other than water include mixtures of water and organic solvents such as acetic acid, methanol, and ethanol. The filtration method is not particularly limited, and can be a known method that is usually used to filter organic compound contents. Examples of the filtration method include reduced pressure filtration, pressure filtration, and ultrafiltration membrane method.

[0071] After removing the water-soluble inorganic salt and the water-soluble organic solvent, a drying treatment is performed, whereby the solvent used for removing the salt and the like can be removed from the obtained treated material. The drying method is not particularly limited, and can be performed by a method usually used for drying organic compounds. Examples of the drying method include reduced pressure drying, freeze drying, spray drying, freeze spray drying, and the like. The drying temperature and drying time in the drying are not particularly limited, but in order to maintain the chemical stability of the treated material and prevent secondary aggregation of particles, it is preferable to perform the drying at a low temperature, and it is preferable to perform the drying by the freeze drying method, spray drying method, or freeze spray drying method.

[0072] In addition, in order to prevent drying and aggregation during preparation of the wet-milled pulverized product, the aqueous dispersion may be prepared using the wet-milled product in a water-containing state after removing the water-soluble inorganic salt and the water-soluble organic solvent.

[0073] In the wet-grinding product of the present invention, the water-soluble organic solvent preferably remains in a specific range. The remaining amount is preferably in the range of 0.003 to 0.3 parts by mass of the water-soluble organic solvent (D) used in the wet-grinding process per 100 parts by mass of the solid particles containing tetrahydrocurcuminoid contained in the aqueous dispersion composition. This is because the water-soluble organic solvent remains in a specific range, which has the effect of suppressing the aggregation of the finely divided solid particles containing tetrahydrocurcuminoid. From the viewpoint of the remaining amount, a water-soluble organic solvent that does not have a functional group of a hydroxyl group and has a total of two or more ester groups is more preferable. This is because the hydroxyl group promotes aggregation by hydrogen bonding. Considering these factors comprehensively, among the water-soluble organic solvents described above, diacetin, triacetin, tripropionin, tributyrin, triethyl citrate, and acetyltriethyl citrate are preferable.

[0074] <Method for measuring the average particle size of solid particles containing tetrahydrocurcuminoids in an aqueous dispersion> The average particle size of solid particles in the aqueous dispersion can be measured by known methods such as dynamic light scattering and laser diffraction scattering, but the value obtained by dynamic light scattering is used in the present composition. Examples of particle size measuring devices using dynamic light scattering include Zetasizer Nano (trade name, manufactured by Malvern) and MicrotracUPA (trade name, manufactured by Nikkiso Co., Ltd.). As described above, in the present composition, the average particle size of the solid particles containing tetrahydrocurcuminoid is desirably 500 nm or less. The average particle size of the particles may be the particle size (D50) that is 50% of the cumulative size in the cumulative particle size distribution based on the number of particles.

[0075] <Food, cosmetics, medicines and quasi-drugs> The present composition can be used as an ingredient for foods, cosmetics, medicines and quasi-drugs, and can be contained therein.

[0076] Examples of foods (food and beverages) that can contain the present composition include general foods such as edible oils (salad oils), confectioneries (gum, candy, caramel, chocolate, cookies, snacks, jelly, gummy candies, candy tablets, etc.), noodles (soba, udon, ramen, etc.), dairy products (milk, ice cream, yogurt, etc.), seasonings (miso, soy sauce, etc.), soups, beverages (juice, coffee, black tea, green tea, carbonated drinks, sports drinks, etc.), as well as health foods (tablets, capsules, etc.) and nutritional supplements (nutritional drinks, etc.).

[0077] These foods can be blended with various ingredients depending on the type. For example, food ingredients such as glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, sodium erythorbate, glycerin, propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, gum arabic, carrageenan, casein, gelatin, pectin, agar, vitamin B, nicotinamide, calcium pantothenate, amino acids, calcium salts, colorings, flavorings, and preservatives can be used.

[0078] In addition, these foods contain, for example, antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced glutathione, tocotrienol, vitamin A derivatives, lycopene, lutein, astaxanthin, zeaxanthin, fucoxanthin, uric acid, ubiquinone, coenzyme Q10, folic acid, garlic extract, allicin, sesamin, lignans, catechins, isoflavones, chalcones, tannins, flavonoids, coumarins, isocoumarins, blueberry extract), health food ingredients (vitamin A, vitamin B1, vitamin B2, vitamin B6, vitamin B12, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B10, vitamin B11, vitamin B12, vitamin B13, vitamin B14, vitamin B15, vitamin B16, vitamin B17, vitamin B18, vitamin B19, vitamin B20, vitamin B21, vitamin B22, vitamin B23, vitamin B24, vitamin B25, vitamin B26, vitamin B27, vitamin B28, vitamin B30, vitamin B31, vitamin B32, vitamin B33, vitamin B34, vitamin B35, vitamin B36, vitamin B37, vitamin B38, vitamin B40, vitamin B41, vitamin B42, vitamin B43, vitamin B44, vitamin B45, vitamin B46, vitamin B47, vitamin B50, vitamin B51, vitamin B52, vitamin B63, vitamin B64, vitamin B65, vitamin B66, vitamin B67, vitamin B68, vitamin B69, vitamin B70, vitamin B71, vitamin B72, vitamin B73, vitamin B74, vitamin B75, vitamin B76, vitamin B77, vitamin B78, vitamin B79, vitamin B81, vitamin B91, vitamin B92, vitamin B93, vitamin B94, vitamin B95, C, VD, VE, VP, choline, niacin, pantothenic acid, calcium folate, EPA, oligosaccharides, dietary fiber, squalene, soy lecithin, taurine, dunaliella, protein, octacosanol, DHA, egg yolk lecithin, linoleic acid, lactoferrin, magnesium, zinc, chromium, selenium, potassium, heme iron, oyster meat extract, chitosan, chitin oligosaccharides, collagen, chondroitin, turmeric, licorice, wolfberry, cinnamon bark, hawthorn, ginger, reishi mushroom, clam extract, soft-shelled turtle, licorice, wolfberry, cinnamon bark, hawthorn, ginger, reishi mushroom, plantain, chamomile, Chamomile, dandelion, hibiscus, honey, bolen, royal jelly, lime, lavender, rose hips, rosemary, sage, bifidobacteria, faecalis bacteria, lacrys, wheat germ oil, sesame oil, perilla oil, soybean oil, medium chain fatty acids, agaricus, ginkgo leaf extract, turmeric, chondroitin, brown rice germ extract, lychee, onion, DHA, EPA, DPA, sweet tea, cordyceps sinensis, garlic, bee larvae, papaya, pu-erh, propolis, megusuri tree, arbutus mushroom, royal jelly, saw palmetto, hyaluronic acid, collagen, GABA, harp Seal oil, shark cartilage, glucosamine, lecithin, phosphatidylserine, Panax notoginseng, mulberry leaves, soybean extract, echinacea, Eleuthero, barley extract, olive leaves, olive fruit, gymnema, banaba, salacia, garcinia, chitosan, St. John's wort, jujube, carrot, passion flower, broccoli, placenta, pearl barley, grape seeds, peanut husks, bilberry, black cohosh, milk thistle, bay laurel, sage, rosemary, rafuma, black vinegar, bitter melon, maca, safflower, flax, oolong tea, flower thorns, caffeine, capsaicin,Xylooligosaccharides, glucosamine, buckwheat, citrus, dietary fiber, protein, prunes, spirulina, young barley leaves, nucleic acid, yeast, shiitake mushrooms, plum flesh, amino acids, deep-sea shark extract, noni, oyster meat, soft-shelled turtle, champignon, plantain, acerola, pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, pheshimakobu, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chaste tree, L-cysteine, red wine leaves, mi It can also contain other ingredients such as reddish brown, horsetail, biotin, centella asiatica, haskap, pycnogenol, butterbur, rhubarb, clove, rosemary, catechin, pu-erh, citric acid, brewer's yeast, melilot, black ginger, ginger, zedoary, nattokinase, monascus, tocotrienol, lactoferrin, cinnamon, tartary buckwheat, cocoa, yuzu seed extract, perilla fruit extract, lychee seed extract, evening primrose extract, black rice extract, α-lipoic acid, and green coffee bean extract.

[0079] The content of the present composition in food can be appropriately set, but from the viewpoint of disease prevention and health maintenance, it is preferably 1 to 30 mass %, and more preferably 1 to 20 mass %.

[0080] Examples of cosmetic forms in which the present composition can be blended include milk lotion, soap, facial cleanser, bath additives, cream, milk lotion, skin lotion, cologne, shaving cream, shaving lotion, cosmetic oil, suntan / sunscreen lotion, face powder, foundation, perfume, pack, nail cream, enamel, enamel remover, eyebrow ink, blusher, eye cream, eye shadow, mascara, eyeliner, lipstick, lip balm, shampoo, conditioner, hair dye, dispersion, cleanser, etc.

[0081] In addition to the composition, the cosmetic preparation may contain oils, higher alcohols, fatty acids, ultraviolet absorbers, powders, pigments, surfactants, polyhydric alcohols, sugars, polymers, physiologically active ingredients, solvents, antioxidants, fragrances, preservatives, and the like, as long as the effects of the present disclosure are not impaired.

[0082] Furthermore, the present composition can be added as an ingredient to medicines (including pharmaceuticals and quasi-drugs), and can be in the form of, for example, liquids, poultices, lotions, ointments, tinctures, creams, and liquids for external use. Examples of ingredients that can be included in the drug other than the composition include excipients (glucose, lactose, sucrose, sodium chloride, starch, calcium carbonate, kaolin, crystalline cellulose, cacao butter, hardened vegetable oil, kaolin, talc, etc.), binders (distilled water, saline, ethanol water, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, potassium phosphate, polyvinylpyrrolidone, etc.), disintegrants (sodium alginate, agar, sodium bicarbonate, calcium carbonate, sodium lauryl sulfate, stearate monoglyceride, starch, lactose, powdered gum arabic, gelatin, ethanol, etc.), disintegration inhibitors (sucrose, stearin, cacao butter, hydrogenated oil, etc.), absorption enhancers (quaternary ammonium base, sodium lauryl sulfate, etc.), adsorbents (glycerin, starch, lactose, kaolin, bentonite, silicic acid, etc.), lubricants (purified talc, stearates, polyethylene glycol, etc.), etc. EXAMPLES

[0083] The present disclosure will be described below based on examples, but the present disclosure is not limited thereto. In the examples, "parts" and "%" represent "parts by mass" and "% by mass", respectively.

[0084] (Measurement of primary particle size) The primary particle diameter of the obtained solid particles containing tetrahydrocurcuminoid was determined by measuring the primary particle diameter of the solid particles containing tetrahydrocurcuminoid in the observation sample at 100,000 times magnification using a transmission electron microscope (JEM-1200EX manufactured by JEOL Ltd.) and using the average value. Note that when the particle shape is not spherical, the major axis and minor axis were measured, and the value calculated by (major axis + minor axis) / 2 was used as the particle diameter.

[0085] (Measurement of residual water-soluble organic solvents) The residual water-soluble organic solvent in the obtained solid particles containing tetrahydrocurcuminoid was quantified by gas chromatography, and the residual amount of the water-soluble organic solvent was calculated based on 100 parts by mass of the solid particles containing tetrahydrocurcuminoid. The gas chromatography conditions are shown below. Separation equipment: Shimadzu GC2010 Column: DM-5MS (30m x 0.25mm x 0.25μm Film, Agilent Technologies) Carrier gas: He Pressure: 120.0kPa ·Total flow rate: 50.0ml / min Column flow rate: 1.77ml / min ·Line velocity: 49.0cm / sec Purge flow rate: 3.0ml / min Column temperature: 80℃ for 4 minutes, then heat up in 16 minutes and hold at 320℃ for 5 minutes. Injection Mode: Split-less Mode Injection volume: 1μL

[0086] The mass spectrometer conditions are as follows: Measuring equipment: Shimadzu GC2010 Interface temperature: 250℃ Ion source temperature: 200℃ Measurement Mode: Scan Mode Measurement range: m / z= 30-500 Measurement time: 5~20min Event duration: 0.5sec

[0087] [Preparation of finely divided tetrahydrocurcuminoid solid particles THC-1 (solid particles (A) obtained by wet milling)] First, tetrahydrocurcuminoid fine solid particles were prepared as solid particles. Specifically, the following materials were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 50°C for 8 hours. -Tetrahydrocurcuminoid-containing processed material White Curcuminoid (product name, manufactured by Sabinsa Japan Corporation): 100 parts by weight, Water-soluble inorganic salts Sodium chloride: 1000 parts by mass, Water-soluble organic solvents Diacetin: 150 parts by weight. Next, this kneaded material was put into 10 liters of water and stirred for 1 hour to form a slurry, which was then filtered and washed repeatedly to remove sodium chloride and diacetin, and then freeze-dried to obtain 97 parts by mass of tetrahydrocurcuminoid fine solid particles THC-1, which was a wet-milled product. The primary particle size of the obtained tetrahydrocurcuminoid fine solid particles THC-1 was 230 nm, and the amount of remaining water-soluble organic solvent was 0.010 parts by mass per 100 parts by mass of the tetrahydrocurcuminoid fine solid particles.

[0088] [Preparation of finely divided tetrahydrocurcuminoid solid particles THC-2 to 4 (solid particles (A) obtained by wet milling)] Tetrahydrocurcuminoid micronized solid particles THC-2 to THC-4 were prepared in the same manner as for the preparation of tetrahydrocurcuminoid micronized solid particle THC-1, except that the type of tetrahydrocurcuminoid-containing material to be treated (product name, etc.), type / parts by mass of water-soluble organic solvent, parts by mass of sodium chloride, and kneading conditions were changed to those shown in Table 1.

[0089] [Table 1]

[0090] <Evaluation of Aqueous Dispersion Composition> Next, an aqueous dispersion composition was prepared using solid particles containing tetrahydrocurcuminoid, and the particle size distribution of the obtained aqueous dispersion composition was evaluated. The particle size distribution was measured by measuring the average particle size (D50: 50% median size) of the solid particles containing tetrahydrocurcuminoid in the aqueous dispersion composition using a particle size distribution measuring device ("MicrotracUPA" manufactured by Nikkiso Co., Ltd.).

[0091] <Evaluation of storage stability of aqueous dispersion composition> The aqueous dispersion composition thus prepared was stored for 7 days in an environment of temperature: 25°C and relative humidity: 60%RH, and after storage, the average particle size (D50: 50% median size) was measured to evaluate the stability of the average particle size in the aqueous dispersion composition. In addition, after storage for 7 days, the presence or absence of sedimentation was visually confirmed, and the sedimentation stability was evaluated according to the following evaluation criteria. The evaluation results are shown in Tables 2 and 3. · Evaluation criteria for sedimentation stability ○: No visible sedimentation △: Some settling ×: Sedimentation occurred

[0092] [Example 1] The following materials were mixed and subjected to ultrasonic irradiation for 2 hours using an ultrasonic device (manufactured by Yamato Scientific Co., Ltd., product name: "LUH150") to obtain an aqueous dispersion composition S-1. Solid particles containing tetrahydrocurcuminoids White curcuminoid (product name, manufactured by Sabinsa Japan Corporation): 5 parts by weight, Dispersion aid Polyglycerol fatty acid ester (manufactured by Mitsubishi Chemical Corporation, product name: Ryoto Polyglycerol M-7D): 5 parts by mass, ·Aqueous medium Purified water: 90 parts by mass.

[0093] [Example 2] An aqueous dispersion composition S-2 was obtained in the same manner as in Example 1, except that the dispersion method was changed from the ultrasonic device to a stirring homogenizer (manufactured by M Technique Co., Ltd., product name: "Clearmix CLM-0.8S") and the homogenization process was carried out for 2 hours.

[0094] [Example 3] An aqueous dispersion composition S-3 was obtained in the same manner as in Example 1, except that the dispersion method was changed from the ultrasonic device to a high-pressure homogenizer (manufactured by Sugino Machine Ltd., product name: "Starburst Mini") and high-pressure homogenization treatment at 100 MPa was performed 10 times.

[0095] [Example 4] The dispersion method was changed from the ultrasonic device to an Eiger mill (manufactured by Eiger Japan, product name: "Mini Model M-250 MKII") using zirconia beads with a diameter of 0.5 mm. After dispersing for 3 hours, the mixture was filtered through a filter with a pore size of 5.0 μm. The same procedure as in Example 1 was repeated to obtain an aqueous dispersion composition S-4.

[0096] [Examples 5 to 31, Comparative Examples 1 and 2] Aqueous dispersion compositions S-5 to S-33 were prepared in the same manner as in Example 4, except that the solid particles containing tetrahydrocurcuminoid, the type (product name, etc.) and parts by weight of the dispersion aid, and the parts by weight of the aqueous medium were changed to those shown in Table 2 or Table 3. In Examples 24 to 31, two types of dispersion aids were used in combination, and in Comparative Examples 1 and 2, no dispersion aid was used.

[0097] [Table 2]

[0098] [Table 3]

[0099] From Tables 2 and 3, it was found that the use of a specific dispersion aid can maintain the dispersion stability of solid particles containing tetrahydrocurcuminoids for a long period of time and suppress precipitation. Among the dispersion aids, polyglycerol fatty acid esters, sucrose fatty acid esters, lecithin, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinylpyrrolidone, and enzyme-treated products gave particularly good results. It was also found that a finer aqueous dispersion can be prepared by subjecting solid particles containing tetrahydrocurcuminoids to a wet grinding and pulverizing process. [Industrial Applicability]

[0100] The present composition can be used in various applications, such as foods, cosmetics, pharmaceuticals, and quasi-drugs, utilizing an aqueous dispersion composition containing solid particles containing tetrahydrocurcuminoid.

Claims

1. An aqueous dispersion composition comprising at least tetrahydrocurcuminoid-containing solid particles (A), a dispersion aid (B), and an aqueous medium (C), The aqueous dispersion composition, wherein the dispersing aid (B) contains at least one selected from the group consisting of phospholipids, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene phytosterols, polysaccharides, sugar derivatives, polyvinylpyrrolidone, polyvinyl alcohol, and enzyme-treated products.

2. The aqueous dispersion composition according to claim 1, wherein the dispersion aid (B) contains at least one selected from the group consisting of lecithin, saponin, sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, methylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, gum arabic, xanthan gum, γ-cyclodextrin, polyvinylpyrrolidone, polyvinyl alcohol, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin.

3. The aqueous dispersion composition according to claim 1 , wherein the solid particles (A) containing tetrahydrocurcuminoid have an average particle size of 500 nm or less.

4. 2. The aqueous dispersion composition according to claim 1, wherein a mass ratio of the tetrahydrocurcuminoid-containing solid particles (A) to the dispersion aid (B) is 1:1 to 2.5:

1.

5. The aqueous dispersion composition according to claim 1 , wherein the solid particles (A) containing tetrahydrocurcuminoid are a wet milled product.

6. The solid particles (A) containing at least a tetrahydrocurcuminoid contain a tetrahydrocurcuminoid and a water-soluble organic solvent (D), The water-soluble organic solvent (D) satisfies the following (i) to (iii), (i) The molecular weight is 100 to 350. (ii) It has a total of two or more functional groups consisting of hydroxyl groups and / or ester groups. (iii) The viscosity at 60°C is 2 to 150 mPa·s.

2. The aqueous dispersion composition according to claim 1, wherein a content of the water-soluble organic solvent (D) is 0.003 to 0.3 parts by mass per 100 parts by mass of the tetrahydrocurcuminoid-containing solid particles (A).

7. 7. The aqueous dispersion composition according to claim 6, wherein the water-soluble organic solvent (D) contains at least one selected from the group consisting of diacetin, triacetin, tripropionin, tributyrin, triethyl citrate, and acetyltriethyl citrate.

8. 2. The aqueous dispersion composition according to claim 1, which is a product treated with an ultrasonic wave, a homogenizer, or a bead mill.

9. A food product comprising the aqueous dispersion composition according to any one of claims 1 to 8.

10. A cosmetic preparation comprising the aqueous dispersion composition according to any one of claims 1 to 8.

11. A pharmaceutical comprising the aqueous dispersion composition according to any one of claims 1 to 8.

12. A method for producing the aqueous dispersion composition according to any one of claims 1 to 8, comprising the steps of: A method for producing an aqueous dispersion composition, comprising dispersing solid particles (A) containing tetrahydrocurcuminoid, a dispersing aid (B), and an aqueous medium (C) by ultrasonic dispersion, homogenizer dispersion, or bead mill dispersion to obtain an aqueous dispersion composition.

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