Water-dispersible powder composition and method for producing the same, food, cosmetic, and pharmaceutical

Abstract

The present invention provides a water-dispersible powder composition containing piperines that exhibits excellent redispersibility in water, ensures long-term dispersion stability, and suppresses precipitation, as well as a method for producing the same, and food products, cosmetics, and pharmaceuticals using the water-dispersible powder composition. [Solution] A water-dispersible powder composition comprising solid particles containing piperines and a dispersion aid, wherein the dispersion aid comprises at least one selected from phospholipids, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, acidic polysaccharides, cellulose derivatives, polyvinylpyrrolidone, and enzyme-treated products. Also, a method for producing the same, and foods, cosmetics, and pharmaceuticals using the same.

Description

Technical Field

[0001] The present disclosure relates to a water-dispersible powder composition, a method for producing the same, foods, cosmetics, and pharmaceuticals using the water-dispersible powder composition.

Background Art

[0002] Piperines are organic compounds classified as alkaloids contained in the fruits of Piper longum and black pepper, and are known to have various effects such as improving blood flow function, suppressing Parkinson's disease, enhancing energy metabolism, antibacterial and antioxidant effects. Patent Document 1 discloses a tea-based beverage containing piperines.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] In order to expand the options such as application uses and usage forms, a form of a water-dispersible powder composition in which solid particles of piperines are easily dispersed in an aqueous medium is desired. However, piperines are poorly water-soluble solid particles, and when trying to disperse them in water, the piperine particles immediately precipitate in the aqueous medium, and there are problems with water dispersibility.

[0005] Also, considering maximizing the pharmaceutical effects of piperines, it is important to refine piperine particles, increase the specific surface area, and improve water elution properties. However, generally, when the particle size of particles contained in an aqueous dispersion becomes small, due to the increase in the specific surface area, cohesive forces act, and it tends to be difficult to ensure the dispersion stability of the particles. Therefore, there has been a demand for the development of a water-dispersible powder composition that can ensure dispersion stability in the long term even for refined piperine particles.

[0006] This disclosure aims to provide a water-dispersible powder composition containing piperines that ensures dispersion stability over a long period and suppresses precipitation, a method for producing the same, and food products, cosmetics, and pharmaceuticals using the water-dispersible powder composition. [Means for solving the problem]

[0007] As a result of diligent research, the present inventors discovered that a water-dispersible powder composition that solves the above problems can be obtained by including solid particles containing piperines and a specific dispersing agent, leading to the present invention.

[0008] In other words, the present invention relates to a water-dispersible powder composition comprising solid particles (A) containing piperines and a dispersion aid (B), wherein the dispersion aid comprises at least one selected from phospholipids, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, acidic polysaccharides, cellulose derivatives, polyvinylpyrrolidone, and enzyme-treated products.

[0009] The present invention also relates to the water-dispersible powder composition wherein the dispersion aid (B) comprises at least one selected from lecithin, sucrose fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, hydroxypropyl methylcellulose, gum arabic, ghati gum, polyvinylpyrrolidone, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin.

[0010] Furthermore, the present invention relates to a water-dispersible powder composition in which the average particle size when the water-dispersible powder composition is redispersed in water is 500 nm or less.

[0011] Furthermore, the present invention relates to the water-dispersible powder composition wherein the mass ratio of solid particles (A) containing piperines and the dispersion aid (B) is 1:0.2 to 1:3.

[0012] The present invention also relates to the water-dispersible powder composition further comprising an excipient (C).

[0013] Furthermore, the present invention relates to the water-dispersible powder composition wherein the excipient (C) comprises at least one selected from disaccharides, sugar alcohols, starch, and starch derivatives.

[0014] Furthermore, the present invention relates to the water-dispersible powder composition in which the solid particles (A) containing piperines are a product of wet grinding and pulverization.

[0015] Furthermore, the present invention relates to a water-dispersible powder composition in which solid particles (A) containing piperines contain piperines and a water-soluble organic solvent (E), the water-soluble organic solvent (E) satisfies the following (i) to (iii), and the content of the water-soluble organic solvent (E) is 0.003 to 0.3 parts by mass per 100 parts by mass of the solid particles (A). (i) The molecular weight is between 90 and 350. (ii) Having at least two functional groups selected from the group consisting of hydroxyl groups, ester groups, and carboxyl groups. (iii) The viscosity at 60°C is 2 to 150 mPa·s.

[0016] Furthermore, the present invention relates to the water-dispersible powder composition wherein the water-soluble organic solvent (E) comprises at least one selected from the group consisting of diacetin, triacetin, lactic acid, trippropionine, tripbutyline, triethyl citrate, and acetyltriethyl citrate.

[0017] The present invention also relates to a method for producing a water-dispersible powder composition, comprising drying an aqueous dispersion containing solid particles (A) containing piperines, a dispersion aid (B), and an aqueous medium (D).

[0018] Furthermore, the present invention relates to a food product comprising the aforementioned water-dispersible powder composition.

[0019] Furthermore, the present invention relates to a cosmetic composition comprising the aforementioned water-dispersible powder composition.

[0020] Furthermore, the present invention relates to a pharmaceutical product containing the water-dispersible powder composition.

Advantages of the Invention

[0021] According to the present disclosure, it is possible to provide a water-dispersible powder composition containing piperines, a method for producing the same, foods, cosmetics, and pharmaceutical products that can ensure dispersion stability over a long period and suppress precipitation.

Embodiments for Carrying Out the Invention

[0022] Hereinafter, the water-dispersible powder composition, its production method, foods, cosmetics, and pharmaceutical products according to the present disclosure will be described. In this specification, "~" indicating a numerical range means including the numerical values described before and after as the lower limit value and the upper limit value. In the numerical ranges described step by step in this specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in other step-by-step descriptions. Also, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples. Furthermore, in this specification, the amount of each component contained in the water-dispersible powder composition means the total amount of the plurality of substances corresponding to each component in the composition, unless otherwise specified when a plurality of substances corresponding to each component are contained in the composition.

[0023] <Water-dispersible powder composition> The water-dispersible powder composition according to the present disclosure (hereinafter also referred to as this composition) contains solid particles containing piperines and a specific dispersion aid, and may contain other additives as needed. The dispersion aid includes at least one selected from phospholipids, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, polysaccharides, sugar derivatives, polyvinylpyrrolidone, and enzyme-treated products. This composition allows for easy dispersion of solid particles containing the piperines mentioned above in water, maintains the dispersion state of the solid particles stably for a long period of time, and suppresses precipitation and changes in appearance such as color.

[0024] (Solid particles containing piperines (A)) In this composition, "piperines" refers to piperine, its analogous compounds, and their derivatives, and includes at least one compound selected from the group consisting of these. Examples of the analogous compounds include piperanine, chavicine, isopiperine, and isochavicine. An example of the derivative is tetrahydropiperine. Piperines may consist of one type (for example, only piperine) or two or more types (for example, piperine and chavicine). However, from the viewpoint of expressing biofunctional effects, it is preferable that piperines include at least piperine or tetrahydropiperine. The total content ratio of piperine and tetrahydropiperine in piperines (or the content ratio of the compound included in this composition if only one of the two compounds is included in this composition) can be, for example, 50% to 100% by mass.

[0025] Piperines are found in the fruits and fruit spikes of plants belonging to the genus Piper in the family Piperaceae, such as longum, black pepper, and retrofractum. Piperine and chavicin are also known as pungent compounds. In this composition, dried or pulverized versions of these materials can be used as piperine-containing materials. Extracts obtained by extracting these plant materials using hot water or alcohol, or their dried powders, can also be suitably used. Thus, the piperines in this composition may be extracts from the aforementioned plant materials or commercially available products. Furthermore, the piperines may be compounds derived from natural products or synthetic products. In this composition, the origin of the plant materials is not particularly limited. When extracting, the plant (or its parts) used as the extraction material may be used in its original state, but from the viewpoint of improving extraction efficiency, it may be used in a pulverized state. Conventional known methods can be used as appropriate for extracting piperines.

[0026] Piperines are known to have various effects, including improving cold sensitivity and hypertension through vasodilation and improved blood flow, promoting energy metabolism and nutrient absorption through adrenaline release, aiding in weight loss, antibacterial, antiseptic, and insecticidal effects, suppressing Parkinson's disease, and improving bioavailability. For these reasons, various food products, cosmetics, and pharmaceuticals utilizing these functions have been developed. In the following, we may focus particularly on piperine among the piperines, but this composition is not limited to these embodiments.

[0027] A water-dispersible powder composition is preferred in which the average particle size of the solid particles (A) containing piperines when the water-dispersible powder composition is redispersed in water is 500 nm or less. If the particle size is 500 nm or less, dispersion stability is further improved, precipitation can be easily suppressed over a long period of time, and solubility is further improved due to the finer particles, which can also be expected to have pharmaceutical effects. Furthermore, from the viewpoint of suppressing precipitation, the average particle size of the solid particles (A) containing piperines when redispersed in water is more preferably 300 nm or less, and even more preferably 100 nm or less. From the viewpoint of easily ensuring the dispersion stability of the solid particles, it is preferable that the average particle size of the solid particles (A) containing piperines when redispersed in water is 50 nm or more. The method for measuring the average particle size of the solid particles (A) containing piperines when redispersed in water will be described later.

[0028] The solid particles contain piperines and may contain other components derived from the raw materials, but may also consist solely of piperines. Examples of other components derived from the raw materials include dietary fiber, protein, lipids, piperine hydrolysates, and low molecular weight organic compounds (for example, those extracted simultaneously during solvent extraction when high-purity piperine is prepared by solvent extraction). The piperine content in the solid particles is preferably 1% to 100% by mass. Furthermore, the content ratio of solid particles (especially piperines) in this composition can be set as appropriate, but from the viewpoint of design flexibility when formulating food products, pharmaceuticals, etc., it is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more. From the viewpoint of suppressing aggregation and precipitation of solid particles, the content ratio of solid particles (especially piperines) in this composition is preferably 50% by mass or less, and more preferably 30% by mass or less. The piperine content in this composition can be quantitatively analyzed by HPLC using conventionally known methods (e.g., Journal of Food Hygiene, Vol. 60, No. 5, pp. 134-143, 2019).

[0029] Here, the solid particles (A) in this composition are preferably wet-ground and pulverized products from the viewpoint of suppressing precipitation over a long period of time and achieving fine particle size.

[0030] Furthermore, the solid particles (A) containing piperines in this composition may be either crystalline or amorphous. The distinction between crystalline and amorphous solid particles is made by X-ray diffraction. Specifically, if a peak is present in the X-ray diffraction measurement results of the solid particles, the solid particles are determined to be crystalline particles; if no peak is present, the solid particles are determined to be amorphous particles. Generally, amorphous particles have improved water solubility compared to crystalline particles, but tend to have lower dispersion stability, such as precipitation, and may show decomposition in lightfastness tests, raising concerns about stability over time.

[0031] (Dispersing agent (B)) This composition contains a specific dispersing agent (B). The dispersing agent (B) comprises at least one selected from phospholipids, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, acidic polysaccharides, cellulose derivatives, polyvinylpyrrolidone, and enzyme-treated products. Among these, from the viewpoint of suppressing sedimentation over a long period, the dispersing agent (B) preferably comprises at least one selected from lecithin, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, hydroxypropyl cellulose, gum arabic, ghati gum, polyvinylpyrrolidone, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin.

[0032] The mass ratio of the solid particles (A) to the dispersing agent (B) is preferably 1:0.2 to 1:3, and more preferably 1:0.5 to 1:1.5, from the viewpoint of redispersibility in water and suppression of long-term sedimentation. It is thought that a higher concentration (content ratio) of solid particles (A) containing piperines in the water-dispersible powder composition increases the degree of freedom in formulation design during formulation. Also, depending on the type of dispersing agent (B), it may reduce the absorption of piperines, so it is desirable to use as little dispersing agent (B) as possible. However, when the amount of dispersing agent (B) is reduced, there is a trade-off with dispersion stability, so it is desirable to determine the amount to be used by appropriately assessing the required amount. The following describes each dispersing agent (B).

[0033] [phospholipids] Phospholipids, also known as phosphatides, include glycerophospholipids and sphingophospholipids. The phospholipid used in this composition may be either glycerophospholipids or sphingophospholipids. However, from the viewpoint of further improving the dispersibility of solid particles (A) containing piperines, glycerophospholipids are preferred, and among them, lecithin is more preferred.

[0034] Lecithin refers to phosphatidylcholine (hereinafter sometimes abbreviated as PC) itself, or a mixture containing at least phosphatidylcholine. A mixture containing at least phosphatidylcholine generally refers to a mixture that may contain, in addition to phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, N-acylphosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, lysophosphatidylcholine, lysophosphatidic acid, sphingomyelin, sphingoethanolamine, etc.

[0035] Lecithin can be derived from any plant or animal source, including soybeans and egg yolks. In addition, lecithin with improved purity through purification or distillation, or lecithin that has undergone various treatments, such as highly purified lecithin, fractionated lecithin, hydrogenated lecithin, and enzymatically hydrolyzed lecithin, can also be used.

[0036] Highly purified lecithin is lecithin that has been de-oiled and powdered using a solvent such as acetone. Examples of commercially available highly purified lecithin include Phosphoripon 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 Co., Ltd.), and Emalmetic 300 (trade name, manufactured by Lucas Meyer Cosmetics Co., Ltd.).

[0037] Fractionated lecithin is lecithin in which the content of specific phospholipids has been increased by utilizing differences in solubility in various solvents or by performing operations such as distillation, starting from highly purified lecithin. Examples of commercially available fractionated lecithin include Phosphorlipon 50 (containing 45% PC by mass), Phosphorlipon 85G (containing 80% PC by mass), Phosphorlipon 90G (containing 94% PC by mass) (all are trade names, manufactured by Lipoid Co., Ltd.), Emalmetic 900 (containing 50% PC by mass), Emalmetic 930 (containing 95% PC by mass) (all are trade names, manufactured by Lucas Meyer Cosmetics Co., Ltd.), SLP-PC70, SLP-PC90 (all are trade names, manufactured by Tsuji Oil Co., Ltd.), and others.

[0038] Hydrogenated lecithin is lecithin in which the fatty acid polyenoic acid in the lecithin structure is oxidized and then hydrogenated to improve photostability, converting it to saturated fatty acids. Although hydrogenated lecithin can be preferably used in pharmaceuticals such as cosmetics and topical skin preparations, it is difficult to use in food and beverages. Examples of commercially available hydrogenated lecithin include Emalmetic 320 (trade name, manufactured by Lucas Meyer Cosmetics) and SLP White H (trade name, manufactured by Tsuji Oil Co., Ltd.). Examples of commercially available lecithin with increased PC content and further hydrogenation treatment include Emalmetic 950 (trade name, manufactured by Lucas Meyer Cosmetics), SLP-PC92H (trade name, manufactured by Tsuji Oil Co., Ltd.), and Phosphorlipon 90H (trade name, manufactured by Lipoid Co., Ltd.).

[0039] Enzyme-hydrolyzed lecithin is lecithin obtained by selectively breaking down the ester bond of the fatty acid at position 2, which is normally attached to glycerol, using an enzyme. It is also called lysolecithin to distinguish it from regular lecithin. Representative examples of commercially available lysolecithin include SLP White Lyso and SLP-LPC70 (both brand names, manufactured by Tsuji Oil Co., Ltd.).

[0040] [Sucrose fatty acid ester] Sucrose fatty acid esters are obtained by the transesterification reaction of sucrose and fatty acid methyl. In this composition, the sucrose fatty acid ester is preferably a compound in which the fatty acid has 12 to 20 carbon atoms, more preferably a compound in which the fatty acid has 12 to 18 carbon atoms, even more preferably a compound in which the fatty acid has 14 to 16 carbon atoms, and particularly preferably a compound in which the fatty acid has 14 carbon atoms. By setting the number of carbon atoms of the fatty acid to 12 or more and 20 or less, the dispersion stability of the solid particles (A) containing piperines is further improved. 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, sucrose monostearate (cosmetic ingredient name: sucrose stearate) is preferred as the sucrose fatty acid ester.

[0041] Commercially available sucrose fatty acid esters can be used. An example of a commercially available sucrose fatty acid ester (product name) is "S-070" from Mitsubishi Chemical Corporation's "Ryoto (registered trademark) Sugar Ester" series [HLB (Hydrophilic-Lipophilic Balance value (catalog value): 1 or less, monoester (catalog value): approximately 0% by mass], "S-170" [HLB value (catalog value): approximately 1, monoester (catalog value): approximately 1% by mass], "S-270" [HLB value (catalog value): approximately 2, monoester (catalog value): approximately 10% by mass], "S-370" [HLB value (catalog value): approximately 3, monoester (catalog value): approximately 20% by mass], "S-370F" [HLB value (catalog value): approximately 3, monoester (catalog value): approximately 20% by mass], "S-570" [HLB value (catalog value): approximately 5, monoester (catalog value): approximately 30% by mass], "S-770" [HLB value (catalog value Examples include "S-970" (HLB value (catalog value): approximately 7, monoester (catalog value): approximately 40% by mass), "S-1170" (HLB value (catalog value): approximately 9, monoester (catalog value): approximately 50% by mass), "S-1170F" (HLB value (catalog value): approximately 11, monoester (catalog value): approximately 55% by mass), "S-1570" (HLB value (catalog value): approximately 15, monoester (catalog value): approximately 70% by mass), and "S-1670" (HLB value (catalog value): approximately 16, monoester (catalog value): approximately 75% by mass) (all of which are sucrose stearate esters). Furthermore, examples of commercially available sucrose fatty acid esters (product names) include "SS" from the "DK Ester (registered trademark)" series by Daiichi Kogyo Seiyaku Co., Ltd. [HLB value (catalog value): approximately 19, monoester (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): approximately 19, monoester (catalog value): 97% by mass]. Among these, as commercially available sucrose fatty acid esters (product names), at least one selected from the group consisting of "S-1170," "S-1170F," "S-1570," and "S-1670" from the "Ryoto® Sugar Ester" series, "SS," "F-160," "F140," and "F110" from the "DK Ester®" series, and "S-110," "S-160," and "S-190" from the "CosmeLike®" series is preferred. Furthermore, since the monoester content of sucrose fatty acid esters is high, at least one selected from "SS" from the "DK Ester®" series and "S-190" from the "CosmeLike®" series is particularly preferred as a commercially available sucrose fatty acid ester.

[0042] [Polyglycerin fatty acid ester] Polyglycerol fatty acid esters are produced by esterifying fatty acids to polyglycerol. While polyglycerol fatty acid esters are not particularly limited, the polyglycerol structure contained within them may be linear, branched, or cyclic. Examples of polyglycerol fatty acid esters that can be used in this composition include esters of polyglycerol with an average degree of polymerization of 2 or more and fatty acids having 8 to 18 carbon atoms. The average degree of polymerization of the polyglycerol that can be used in the preparation of the polyglycerol fatty acid ester 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 in the preparation of the polyglycerol fatty acid ester include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and linoleic acid. The fatty acid structure contained in the polyglycerol fatty acid ester preferably has at least one of a branched chain and an unsaturated carbon bond, for example, from the viewpoint of exhibiting a tendency for the composition to have better long-term stability.

[0043] A polyglycerol fatty acid ester may be a polyglycerol molecule with one type of fatty acid ester-bonded to it, or it may be a polyglycerol molecule with two or more types of fatty acids ester-bonded to it.

[0044] As for the polyglycerol fatty acid ester, it is preferable, for example, to include a fatty acid structure having at least one of a branched chain and an unsaturated carbon bond, and more preferably to include a fatty acid structure having either a branched chain or an unsaturated carbon bond, from the viewpoint of exhibiting a tendency for the composition to have better long-term stability.

[0045] Specific examples of polyglycerin fatty acid esters include polyglyceryl-6 laurate, polyglyceryl-6 myristate, polyglyceryl-6 stearate, polyglyceryl-6 isostearate, polyglyceryl-6 oleate, polyglyceryl-10 laurate, polyglyceryl-10 myristate, polyglyceryl-10 stearate, polyglyceryl-10 isostearate, polyglyceryl-10 oleate, and polyglyceryl-10 linoleate. Among these, the polyglycerin fatty acid ester is preferably at least one selected from the group consisting of polyglyceryl-6 oleate, polyglyceryl-10 oleate, polyglyceryl-10 linoleate, polyglyceryl-6 isostearate, and polyglyceryl-10 isostearate, and more preferably at least one selected from polyglyceryl-10 isostearate and polyglyceryl-10 oleate.

[0046] Commercially available polyglycerol fatty acid esters can be used. Examples of commercially available polyglycerin fatty acid esters include, for example, 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 Hexaglyn 4-B, NIKKOL Hexaglyn 5-S, NIKKOL Hexaglyn 5-O, and 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 include Decaglyn 10-SV, NIKKOL Decaglyn 10-IS, NIKKOL Decaglyn 10-OV, NIKKOL Decaglyn 10-MAC, and NIKKOL Decaglyn PR-20 (all are product names, manufactured by Nikko Chemicals Co., Ltd.). "NIKKOL" is a registered trademark of Nikko Chemicals Co., Ltd.

[0047] Furthermore, examples include Ryoto® Polyglycerides, 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® Q-17UL, Sunsoft Q-14S, Sunsoft A-141C (all trade names, Taiyo Kagaku Co., Ltd.), Poem® DO-100, Poem J-0021 (all trade names, Riken Vitamin Co., Ltd.), and others.

[0048] [Sorbitan fatty acid ester] Sorbitan fatty acid esters are compounds synthesized by the esterification reaction of sorbitol and fatty acids. Alternatively, they may be in the form of polyoxyethylene sorbitan fatty acid esters, obtained by adding ethylene oxide to sorbitan fatty acid esters.

[0049] Examples of sorbitan fatty acid esters include sorbitan monolaurate (Span 20) and sorbitan monooleate (Span 80).

[0050] The most representative polyoxyethylene sorbitan fatty acid esters are commercially available Tween-type surfactants. Examples of polyoxyethylene sorbitan fatty acid esters include polyoxyethylene sorbitan monolaurate (Tween 20), polyoxyethylene sorbitan monopalmitate (Tween 40), polyoxyethylene sorbitan monostearate (Tween 60), and polyoxyethylene sorbitan monooleate (Tween 80).

[0051] [Acidic polysaccharide] Polysaccharides are a general term for high-molecular-weight compounds formed by the polymerization of numerous monosaccharide molecules through glycosidic bonds. Examples include natural polysaccharides derived from plants, seaweed, or microorganisms, and include acidic polysaccharides, neutral polysaccharides, and basic polysaccharides. Acidic polysaccharides used in this composition include pectin, sodium alginate, potassium alginate, gum arabic, xanthan gum, ghati gum, gellan gum, tragacanth gum, inulin, carrageenan, polygalacturonic acid, agar, polyphyllan, funoran, and furceran. Neutral polysaccharides include tamarind seed gum, guar gum, locust bean gum, starch, pullulan, laminaran, and konjac mannan.

[0052] [Cellulose derivatives] Examples of cellulose derivatives include etherified cellulose, in which some of the hydroxyl groups of the glucose constituting cellulose are etherified. Specifically, examples of etherified cellulose include methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, and carboxymethylcellulose salts. Here, examples of carboxymethylcellulose salts include alkali metal salts of carboxymethylcellulose such as sodium carboxymethylcellulose, and alkaline earth metal salts of carboxymethylcellulose such as calcium carboxymethylcellulose. Among these, hydroxypropylcellulose is preferred from the viewpoint of long-term dispersion stability.

[0053] [Polyvinylpyrrolidone] Polyvinylpyrrolidone (PVP) is a nonionic, water-soluble polymer compound obtained by polymerizing N-vinyl-2-pyrrolidone. Polyvinylpyrrolidone is a white powder that readily absorbs moisture from the air (up to approximately 18% by mass). Commercially available polyvinylpyrrolidone can be used as appropriate. For example, polyvinylpyrrolidone can be obtained by synthesizing N-vinyl-2-pyrrolidone from acetylene, ammonia, and formaldehyde, and then polymerizing it in the presence of an oxidizing agent.

[0054] [Enzyme-treated product] In this composition, an enzyme-treated product can be used as a dispersion aid (B). Typical examples of enzyme-treated products include enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin. Conventionally known enzyme-treated products can be used. For example, as the enzyme-treated product, one produced by the method described in Japanese Patent Publication No. 10-70994, Japanese Patent Publication No. 3-7593, Japanese Patent Publication No. 5-194164, etc., can be used. Examples of commercially available enzyme-treated rutin include "αG Rutin H," "αG Rutin P," and "αG Rutin PS" (all brand names, manufactured by Toyo Sugar Refining Co., Ltd.). Examples of commercially available enzyme-treated hesperidin include "αG Hesperidin H," "αG Hesperidin PS," "αG Hesperidin PA-T," and "αG Hesperidin PA-LE" (all are brand names, manufactured by Toyo Sugar Refining Co., Ltd.). Examples of commercially available enzyme-treated stevia include "αG Sweet P," "αG Sweet PX," "αG Sweet PA," and "αG Sweet H" (all product names, manufactured by Toyo Sugar Refining Co., Ltd.). Examples of commercially available enzyme-treated naringin include "Narinvid" (product name, manufactured by Hayashibara Co., Ltd.) and "αG Naringin H" (product name, manufactured by Toyo Sugar Refining Co., Ltd.).

[0055] [Other additives] This composition may contain other additives depending on the intended use, as long as the effects of this disclosure are not impaired. Examples of usable additives include substances listed in the 49th edition of the Handbook of Standards for the Use of Food Additives (Japan Food Hygiene Association), the 2018 Pharmaceutical Additives Standards (Yakuji Nippo Co., Ltd.), and the 7th edition of the Cosmetic Ingredients Guide (Yakuji Nippo Co., Ltd.).

[0056] <Method for producing a water-dispersible powder composition> The water-dispersible powder composition of the present invention can be prepared by preparing an aqueous dispersion containing solid particles (A) containing piperines as a precursor, a dispersion aid (B), and an aqueous medium (D), and then drying the aqueous dispersion and removing the water. Because the water-dispersible powder composition of the present invention contains a dispersion aid (B) in the powder, it exhibits excellent water dispersibility in the state of a powder redispersion liquid obtained by mixing the powder with water.

[0057] (Aqueous medium (D)) The aqueous medium (D) contains at least water and may consist of water. The water is not particularly limited and can be appropriately set 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 MilliQ water, etc., can all be used. Milli-Q water is ultrapure water obtained using the Milli-Q water production system, which is an ultrapure water production system manufactured by Merck Millipore. Among these, purified water, distilled water, ion-exchanged water, pure water, and Milli-Q water are preferred as the water used in the dispersion composition of the present invention, from the viewpoint of having few impurities.

[0058] The aqueous medium (D) may contain, in addition to water, at least one component selected from the group consisting of a solvent that can be homogeneously mixed with water or dissolved in water, such as a water-soluble organic solvent, a pH adjuster, and a preservative.

[0059] The aforementioned water-soluble organic solvent refers to an organic solvent with a solubility of 10 g / 100 g-H2O or more in water at 25°C. From the viewpoint of being able to stably maintain the dispersion of solid particles, an organic solvent with a solubility of 30 g / 100 g-H2O or more is preferred, and an organic solvent with a solubility of 50 g / 100 g-H2O or more is more preferred.

[0060] Examples of the aforementioned water-soluble organic solvents 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, and glycerin. When the aqueous medium (D) contains a water-soluble organic solvent, only one water-soluble organic solvent may be used, or two or more may be used in combination.

[0061] The content of the water-soluble organic solvent in the aqueous medium (D) can be appropriately selected depending on the purpose. From the viewpoint of ease of bioapplication, the content of the water-soluble organic solvent is preferably 40% by mass or less in the aqueous medium, and more preferably 1% to 20% by mass. Furthermore, an embodiment in which the aqueous medium does not contain the water-soluble organic solvent is also preferred.

[0062] An aqueous dispersion, which is a precursor to a water-dispersible powder composition, can be prepared by applying shear force to a mixture containing solid particles (A) containing piperines, a dispersion aid (B), and an aqueous medium (D). This process mechanically refines the solid particles (A) containing piperines, thereby preparing a dispersion containing piperines. There are no particular restrictions on the shear force application device used, but ultrasonic dispersion, homogenizer dispersion, or bead mill dispersion are preferred. Among these, bead mill dispersion is particularly preferred from the viewpoint of particle refinement.

[0063] Ultrasonic dispersion is a method of breaking down and dispersing particles using the force of cavitation generated by immersing an ultrasonic-emitting tip in a liquid. Commercially available ultrasonic dispersers include the UH-50, UH-50F, UH-300, UH-600, UH-600S, UH-600SH (all product names, manufactured by MST Corporation), PSF-600, PSF-1200, RUS-600TCVP (all product names, manufactured by Nippon Seiki Seisakusho Co., Ltd.).

[0064] Homogenizer dispersion can be broadly classified into types such as agitated homogenizers and high-pressure homogenizers. A stirring homogenizer is a device that incorporates powder into a liquid by rapidly rotating stirring blades, while simultaneously dispersing the particles through the cutting action of the blades. Examples of commercially available stirring homogenizers include the M-Technique CreaMix W Motion CLM-1.7 / 5.5W and Crea SS5-100 (both product names), and the Primix Adihomomixer 2M and HV-M (product names). A high-pressure homogenizer is a device that crushes and disperses a material to be crushed by applying high or ultra-high pressure and generating shear force as it passes through slits (gaps). This generally includes devices called high-pressure homogenizers and ultra-high-pressure homogenizers. Examples of high-pressure homogenizer devices include Starburst (product name, Sugino Machine Co., Ltd.), NanoVeida (product name, Yoshida Machinery Industry Co., Ltd.), and Microfluidizer M-110E / H (product name, Mizuho Industries Co., Ltd.).

[0065] Bead mill dispersion is a method of mixing various components (solid particles, dispersion aids, etc.) in a solvent (aqueous medium) and crushing, micronizing, and dispersing coarse particles or aggregates (aggregated particles) through collision forces between beads. In this process, the particle surface is coated with a dispersion aid (resin or surfactant). This improves the stability of the aqueous dispersion composition and facilitates the suppression of long-term precipitation. These dispersion methods can be carried out under conventionally known conditions as appropriate. For example, bead mill dispersion can be performed using (zirconia) beads with a diameter of 0.1 to 0.5 mm for 0.1 to 20 hours.

[0066] Commercially available bead mills can be used. Commercially available bead mills that can be used to prepare this composition include Star Mill Nano Getter, Star Mill ZRS, Star Mill LMZ, Agitator Mill LMK (all trade names, Ashizawa Fine Tech 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.), and Sun Examples include Dog Grinder (SLG), Ready Mill (RMV-03), Nano Ready Mill (RMV-03), Ultra Viscomill (UVM), Ultra-X Viscomill (UVX), New Viscomill (NVM) (all product names, manufactured by AIMEX Co., Ltd.), SC Mill, MSC Mill, Attrita, Fine Mill (all product names, manufactured by Nippon Coke Industries Co., Ltd.), Annular Gap Bead Mill (product name, manufactured by Eurotech Co., Ltd.), Dyno Mill ECM, DYNO-MILL NPM-NANO Performance Mill (all product names, manufactured by Shinmaru Enterprise Co., Ltd.), MicroMediaX1 (product name, manufactured by Bühler Co., Ltd.), and others.

[0067] Any known method can be used to dry the aqueous dispersion, including, for example, vacuum drying, freeze-drying, spray drying, and freeze-spray drying. During drying, it is preferable to add an excipient (C) to the dispersion to maintain the shape of the powder, prevent scattering, and suppress drying aggregation.

[0068] (Excipient (C)) Excipients (C) can be those known for use in food, cosmetics, pharmaceuticals, and quasi-drugs, but typical examples include monosaccharides, disaccharides, sugar alcohols, oligosaccharides, starch and its derivatives, and inorganic salts. Examples of monosaccharides include glucose, fructose, galactose, and xylose; examples of disaccharides include sucrose, lactose, maltose, trehalose, sucrose, cellobiose, and lactucrose; examples of sugar alcohols include mannitol, sorbitol, maltitol, erythritol, lactitol, and xylitol; examples of oligosaccharides include isomaltoligosaccharide, fructooligosaccharide, galactooligosaccharide, and xylooligosaccharide; examples of starch and its derivatives include starch, carboxymethyl starch, dextrin, cyclodextrin, dextran, and pullulan; and examples of inorganic salts include calcium carbonate, calcium sulfate, calcium phosphate, and calcium stearate. Among these, disaccharides, sugar alcohols, and starch and its derivatives are preferred from the viewpoint of powder dispersion.

[0069] (Wet grinding and pulverizing process) The solid particles (A) containing piperines are preferably wet-ground and pulverized from the viewpoint of particle refinement. Using wet-ground and pulverized materials makes it possible to produce fine solid particle powder containing piperines, and using these finely ground solid particles makes it possible to prepare a water-dispersible powder in which fine particles are dispersed when redispersed in water. The primary particle size of the solid particles (A) containing piperines is preferably reduced to 50-300 nm. The method for measuring the primary particle size of the solid particles (A) containing piperines will be described later. A wet grinding and pulverizing treatment product of solid particles (A) can be obtained, for example, through the following steps: a step (a) in which the material to be treated containing piperines, a water-soluble inorganic salt, and a water-soluble organic solvent are mechanically kneaded together; and a step (b) in which the water-soluble inorganic salt and water-soluble organic solvent are removed after step (a).

[0070] [Water-soluble inorganic salts] The above-mentioned water-soluble inorganic salts have the effect of grinding and micronizing the material to be treated. Because water-soluble salts are used, they can be removed by washing. Examples of usable inorganic salts 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 preferred. The amount of water-soluble inorganic salt added is not particularly limited, but from the viewpoint of processing 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 processed. Furthermore, the water-soluble inorganic salt may be used as a single type or in combination of multiple types.

[0071] [Water-soluble organic solvent (E)] The water-soluble organic solvent used in the wet grinding and pulverization treatment of solid particles (A) containing piperines must function to wet the poorly water-soluble material to be treated and the water-soluble inorganic salt, and must dissolve (mix) in water but not substantially dissolve the water-soluble inorganic salt used. Furthermore, the water-soluble organic solvent used in the wet grinding and pulverization treatment is preferably a water-soluble organic solvent (E) that satisfies the following (i) to (iii). That is, (i) The molecular weight is between 90 and 350. (ii) Having at least two functional groups selected from the group consisting of hydroxyl groups, ester groups, and carboxyl groups. (iii) The viscosity at 60°C is 2 to 150 mPa·s. This satisfies all of the above conditions. If the viscosity is high, the viscosity of the mixture of solid particles (A) containing piperines and inorganic salt increases, inhibiting the movement of the inorganic salt, which is the grinding agent, and preventing sufficient micronization effect of the solid particles (A) containing piperines from being obtained. The viscosity of the water-soluble organic solvent in the specification of this application is the value measured using a conical plate type rotational viscometer (viscometer manufactured by Toki Sangyo Co., Ltd.: TVE-20L) in accordance with the provisions of JIS Z 8803.

[0072] Examples of water-soluble organic solvents that can be used in wet grinding and pulverization processes include glycerin, propylene glycol, polyethylene glycol, dipropylene glycol, diethylene glycol, lactic acid, 2-ethyl-1,3-hexanediol, 2,4-diethyl-1,5-pentanediol, monoacetin, diacetin, triacetin, trippropionine, triptylin, 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 (E) that satisfy the above (i) to (iii) include lactic acid (21.3 mPa·s), 2-ethyl-1,3-hexanediol (16.6 mPa·s), and 2 Examples include 4-diethyl-1,5-pentanediol (67.2 mPa·s), monoacetin (13.7 mPa·s), diacetin (8.2 mPa·s), triacetin (4.1 mPa·s), trippropionine (2.7 mPa·s), triptyline (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).

[0073] The amount of water-soluble organic solvent added is not particularly limited, but it is preferable to use 5 to 1000 parts by mass, and more preferably 50 to 500 parts by mass, per 100 parts by mass of the material to be treated. Furthermore, the water-soluble organic solvent may be of a single type or multiple types may be used in combination. The use of solvents other than the water-soluble organic solvent (E) in the present invention is not excluded without departing from the spirit of the present invention. However, from the viewpoint of effectively increasing the micronization of solid particles (A) containing piperines, it is substantially preferable to use the water-soluble organic solvent (E) in the present invention.

[0074] (Step (a)) In the wet grinding and crushing method of the present invention, the kneading apparatus used to mechanically knead and grind the material to be processed can be used without particular limitations, as long as it has the ability to knead and disperse the material to be processed, water-soluble inorganic salts, and water-soluble organic solvents by mechanical means. Examples of such kneading apparatuses include kneaders, two-roll mills, three-roll mills, ball mills, attritors, horizontal sand mills, vertical sand mills, fret mills, Huber maulers, and disc blade kneading and dispersing machines. Using these, the processing conditions can be appropriately adjusted according to the desired degree of fineness. The water-soluble inorganic salt acts as a crushing aid, and the material to be processed is crushed by utilizing the high hardness of the water-soluble inorganic salt during kneading. By optimizing the kneading conditions (temperature, rotation speed, etc.), solid particles (A) containing piperines with a narrow and sharp particle size distribution can be obtained.

[0075] (Step (b)) After the kneading and grinding of solid particles (A) containing piperines is complete, the water-soluble inorganic salt and water-soluble organic solvent used in the kneading and grinding process are removed to obtain the desired solid particles (A) containing piperines. Specifically, the mixture of the material to be treated, water-soluble inorganic salt, and water-soluble organic solvent is made homogenized in a solvent using a stirring blade, dissolver, homogenizer, etc., and then the water-soluble inorganic salt and water-soluble solvent are removed by filtration and washing with water.

[0076] 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 water-soluble organic solvent dissolve easily, and in which the ground material to be treated does not dissolve easily, and is physiologically acceptable. Water is preferred as the solvent, but other solvents can also be used. Examples of solvents other than water include mixtures of water with organic solvents such as acetic acid, methanol, and ethanol. Furthermore, the filtration method is not particularly limited and can be carried out by known methods commonly used to filter out organic compounds. Examples of filtration methods include vacuum filtration, pressure filtration, and ultrafiltration membrane filtration.

[0077] After removing water-soluble inorganic salts and water-soluble organic solvents, the solvents used to remove salts and other substances can be removed from the resulting treated material by performing a drying treatment. The drying method is not particularly limited and can be carried out using methods commonly used for drying organic compounds. Examples of drying methods include vacuum drying, freeze-drying, spray drying, and freeze-spray drying. The drying temperature and drying time are not particularly limited, but in order to maintain the chemical stability of the treated material and prevent secondary aggregation of particles, drying is preferably carried out at a low temperature, and freeze-drying, spray drying, and freeze-spray drying are preferred.

[0078] Furthermore, in order to prevent drying and agglomeration during the preparation of the wet-grinding process, the aqueous dispersion may be prepared using the wet-grinding process material in its hydrated state after the removal of water-soluble inorganic salts and water-soluble organic solvents.

[0079] Furthermore, in the wet grinding and pulverizing treatment product of the present invention, it is preferable that the water-soluble organic solvent (E) remains within a specific range. Preferably, the amount of water-soluble organic solvent (E) used in the wet grinding and pulverizing treatment is in the range of 0.003 to 0.3 parts by mass per 100 parts by mass of solid particles (A) containing piperines. This is because the retention of the water-soluble organic solvent (E) within a specific range has the effect of suppressing the aggregation of the finely ground solid particles (A) containing piperines. From the viewpoint of residue, a water-soluble organic solvent that does not have hydroxyl and carboxyl functional groups and has a total of two or more ester groups is more preferable. This is because hydroxyl and carboxyl groups promote aggregation through hydrogen bonding. Considering all of these factors, among the water-soluble organic solvents (E) described above, diacetin, triacetin, trippropionine, triplyline, triethyl citrate, and acetyltriethyl citrate are desirable.

[0080] <Method for measuring the average particle size of solid particles (A) containing piperines in aqueous dispersions and powder redispersions> The average particle size of solid particles (A) containing piperines in aqueous dispersions and powder redispersions can be measured by known methods such as dynamic light scattering and laser diffraction scattering, but in this specification, values ​​obtained by dynamic light scattering are used. Examples of particle size measuring devices using dynamic light scattering include Zetasizer Nano (trade name, manufactured by Malvern) and MicrotracUPA (trade name, Microtrac-Bell Co., Ltd.). As described above, it is desirable that the average particle size of solid particles (A) containing piperines in aqueous dispersions and powder redispersions be 500 nm or less. The average particle size of the particles may be the particle size that represents 50% of the cumulative particle size distribution based on the number of particles (d50).

[0081] <Food, cosmetics, pharmaceuticals, and quasi-drugs> This composition can be used as an ingredient in food products, cosmetics, pharmaceuticals, and quasi-drugs, and can be included in these products.

[0082] Examples of foods (foods and beverages) that incorporate this composition include edible oils (salad oil), confectionery (gum, candy, caramel, chocolate, cookies, snacks, jelly, gummies, tablets, etc.), noodles (soba, udon, ramen, etc.), dairy products (milk, ice cream, yogurt, etc.), seasonings (miso, soy sauce, etc.), soups, beverages (juice, coffee, tea, carbonated drinks, sports drinks, etc.), as well as health foods (tablets, capsules, etc.) and nutritional supplements (nutritional drinks, etc.).

[0083] These foods can be formulated with various ingredients depending on their 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, B vitamins, nicotinamide, calcium pantothenate, amino acids, calcium salts, colorants, flavorings, and preservatives can be used.

[0084] Furthermore, these foods contain, for example, antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced glutathione, tocotrienols, 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 (vitamins A, B1, B2, B6, B12, V C, VD, VE, VP, choline, niacin, pantothenic acid, folic acid calcium, 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 extract, chitosan, chitin oligosaccharides, collagen, chondroitin, turmeric, licorice, goji berry, cinnamon, hawthorn, ginger, reishi mushroom, clam extract, soft-shelled turtle, licorice, goji berry, cinnamon, hawthorn, ginger, reishi mushroom, plantain, chamomile, Chamomile, dandelion, hibiscus, honey, bollen, royal jelly, lime, lavender, rosehip, rosemary, sage, bifidobacteria, Enterococcus faecalis, Lacris, wheat germ oil, sesame oil, perilla oil, soybean oil, medium-chain fatty acids, Agaricus, ginkgo biloba extract, turmeric, chondroitin, brown rice germ extract, reishi mushroom, onion, DHA, EPA, DPA, sweet tea, cordyceps, garlic, bee larvae, papaya, pu-erh tea, propolis, Megusuri tree, Yabushitake mushroom, royal jelly, saw palmetto, hyaluronic acid, collagen, GABA, herbs Seal oil, shark cartilage, glucosamine, lecithin, phosphatidylserine, Panax notoginseng, mulberry leaf, soybean extract, echinacea, Eleutherococcus senticosus, barley extract, olive leaf, olive fruit, Gymnema, Banaba, Salacia, Garcinia, chitosan, St. John's wort, jujube, carrot, passionflower, broccoli, placenta, Job's tears, grape seeds, peanut husks, bilberry, black cohosh, milk thistle, bay leaf, sage, rosemary, Rhodiola rosea, black vinegar, bitter melon, maca, safflower, flax, oolong tea, flower thorn, caffeine, capsaicin,Xylooligosaccharides, glucosamine, buckwheat, citrus, dietary fiber, protein, prunes, spirulina, barley grass, nucleic acids, yeast, shiitake mushrooms, plum pulp, amino acids, deep-sea shark extract, noni, oyster meat, soft-shelled turtle, champignon, psyllium, acerola, pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, Phellinus linteus, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chaste tree, L-cysteine, red wine leaf, mi Ingredients such as red onion, horsetail, biotin, Centella asiatica, haskap, pycnogenol, butterbur, rhubarb, clove, rosemary, catechin, pu-erh tea, citric acid, brewer's yeast, melilot, black ginger, ginger, turmeric, nattokinase, red yeast rice, tocotrienol, lactoferrin, cinnamon, buckwheat, cocoa, yuzu seed extract, perilla seed extract, lychee seed extract, evening primrose extract, black rice extract, alpha-lipoic acid, and green coffee bean extract can also be included.

[0085] Examples of cosmetic products that incorporate this composition include lotions, soaps, facial cleansers, bath additives, creams, lotions, toners, colognes, shaving creams, shaving lotions, cosmetic oils, sunscreens, face powders, foundations, perfumes, face masks, nail creams, nail polish, nail polish removers, eyebrow pencils, blushes, eye creams, eyeshadows, mascaras, eyeliners, lipsticks, lip balms, shampoos, conditioners, hair dyes, dispersions, and cleansing products.

[0086] Furthermore, in addition to the present composition, the above cosmetic composition may contain oils, higher alcohols, fatty acids, UV absorbers, powders, pigments, surfactants, polyhydric alcohols / sugars, polymers, physiologically active ingredients, solvents, antioxidants, fragrances, preservatives, etc., to the extent that they do not impair the effects of the present disclosure.

[0087] Furthermore, this composition can be added as an ingredient to pharmaceuticals (including pharmaceuticals and quasi-drugs), and can be used in dosage forms such as liquids, poultices, lotions, ointments, tinctures, creams, and topical solutions. Other raw materials that can be included in the chemical in question besides this composition include, for example, excipients (glucose, lactose, sucrose, sodium chloride, starch, calcium carbonate, kaolin, crystalline cellulose, cocoa butter, hydrogenated vegetable oil, kaolin, talc, etc.), binders (distilled water, physiological 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, monoglyceride stearate, starch, lactose, acacia powder, gelatin, ethanol, etc.), disintegration inhibitors (sucrose, stearin, cocoa butter, hydrogenated oil, etc.), absorption enhancers (quaternary ammonium base, sodium lauryl sulfate, etc.), adsorbents (glycerin, starch, lactose, kaolin, bentonite, silicic acid, etc.), and lubricants (purified talc, stearate, polyethylene glycol, etc.).

[0088] The dosage of the above-mentioned drugs and cosmetics may vary depending on the method of administration, the patient's condition, and the patient's age, but adults can usually be administered 0.5 to 5 mg of the active ingredient per day, and children can usually be administered 0.5 to 3 mg. The mixing ratio of this composition in the above-mentioned drugs may be determined as appropriate depending on the dosage form. [Examples]

[0089] The present disclosure will be described below based on examples, but will not be limited thereto. In the examples, "parts" and "%" refer to "parts by mass" and "% by mass," respectively.

[0090] The present disclosure will be described below based on examples, but will not be limited thereto. In the examples, "parts" and "%" refer to "parts by mass" and "% by mass," respectively.

[0091] (Measurement of the primary particle size of solid particle (A)) The primary particle diameter of solid particles (A) was determined by measuring the primary particle diameter of solid particles (A) in the observed sample at 100,000x magnification using a transmission electron microscope (JEOL Ltd. "JEM-1200EX"), and using the average value. If the particle shape was not spherical, the major and minor axes were measured, and the particle diameter was calculated using (major axis + minor axis) / 2.

[0092] (Measurement of residual water-soluble organic solvents) The residual water-soluble organic solvent in solid particles (A) containing at least one selected from the group consisting of resveratrol and its analogs was quantified by gas chromatography, and the amount of residual water-soluble organic solvent per 100 parts by mass of solid particles (A) was determined. The gas chromatography conditions are shown below. • Separation equipment: Shimadzu Corporation GC2010 • Column: DM-5MS (30m x 0.25mm x 0.25μm Film, Agilent Technologies) • Carrier gas: He • Pressure: 120.0 kPa ·Total flow rate: 50.0ml / min Column flow rate: 1.77 ml / min ·Line velocity: 49.0cm / sec • Purge flow rate: 3.0 ml / min • Column temperature: Hold at 80°C for 4 minutes, then increase temperature for 16 minutes, and hold at 320°C for 5 minutes. Injection Mode: Split-less Mode Injection volume: 1μL

[0093] The conditions for the mass spectrometer are as follows: • Measuring instrument: Shimadzu Corporation GC2010 Interface temperature: 250℃ Ion source temperature: 200℃ • Measurement mode: Scan Mode Measurement range: m / z = 30-500 • Measurement time: 5-20 min • Event duration: 0.5 sec

[0094] (Evaluation of average particle size of aqueous dispersions and powder redispersions of water-dispersible powder compositions) Using a particle size distribution analyzer (product name: MicrotracUPA, manufactured by Microtrac-Bell Co., Ltd.), the particle size (50% median diameter) of dispersed particles contained in aqueous dispersions and powder redispersion solutions of water-dispersible powder compositions was measured and defined as the average particle size.

[0095] [Example of preparation] <Preparation of piperine-based refined solid particles, P-1> First, we prepared finely ground solid particles of piperine compounds. 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. • Materials containing piperines Bioperine (product name, manufactured by Sabinsa Japan Corporation): 100 parts by mass, • Water-soluble inorganic salts Sodium chloride: 1000 parts by mass, • Water-soluble organic solvents Diacetin: 150 parts by mass. Next, this mixture was added to 10 liters of water and stirred for 1 hour to form a slurry. After repeated filtration and washing with water to remove sodium chloride and diacetin, freeze-drying was performed to obtain 98 parts by mass of piperine-derived fine solid particles P-1, which was a wet grinding and pulverizing treatment product. The primary particle size of the obtained piperine-derived fine solid particles P-1 was 230 nm, and the amount of residual water-soluble organic solvent was 0.010 parts by mass per 100 parts by mass of fine solid particles.

[0096] <Preparation of piperine-based refined solid particles, P-2 to P-5> Piperine-containing micronized solid particles P-2 to P-5 were prepared using the same method as for piperine-containing micronized solid particles P-1, except that the type of material to be treated (product name, manufacturer name, etc.), the type / parts by mass of water-soluble organic solvent, the parts by mass of sodium chloride, and the kneading conditions were changed to those listed in Table 1 below. The primary particle size and residual water-soluble organic solvent content of each micronized solid particle, as measured by transmission electron microscopy, are shown in Table 1.

[0097] [Table 1]

[0098] <Preparation of aqueous dispersion S-1> The following materials were mixed and subjected to ultrasonic irradiation for 2 hours using an ultrasonic device (Yamato Scientific Co., Ltd., product name: "LUH150") to obtain aqueous dispersion S-1. • Solid particles containing piperines (A) Bioperine (product name, manufactured by Sabinsa Japan Co., Ltd., piperine): 5 parts by mass, • Dispersing agent (B) Polyglycerin fatty acid ester (manufactured by Mitsubishi Chemical Corporation, product name: Ryoto Polyglycerin M-7D): 5 parts by mass • Excipient (C) Lactose (manufactured by Viatris Healthcare, product name: Whey): 15 parts by mass ·Aqueous medium (D) Purified water: 75 parts by mass.

[0099] <Preparation of aqueous dispersion S-2> Aqueous dispersion composition S-2 was obtained in the same manner as aqueous dispersion S-1, except that the dispersion device was changed from the ultrasonic device described above to a stirring homogenizer (manufactured by M-Technique, product name: "Cleamix CLM-0.8S") and the homogenization treatment was performed for 2 hours.

[0100] <Preparation of aqueous dispersion S-3> Aqueous dispersion composition S-3 was obtained in the same manner as aqueous dispersion S-1, except that the dispersion device was changed from the ultrasonic device described above to a high-pressure homogenizer (manufactured by Sugino Machine Co., Ltd., product name: "Starburst Mini"), and high-pressure homogenization treatment at 100 MPa was performed 10 times.

[0101] <Preparation of aqueous dispersion S-4> Aqueous dispersion composition S-4 was obtained in the same manner as aqueous dispersion S-1, except that the dispersion device was changed from the above 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, and the mixture was dispersed for 3 hours, followed by filtration through a filter with a pore size of 5.0 μm.

[0102] <Preparation of aqueous dispersions S-5~22> Aqueous dispersions S-5 to S-22 were prepared using the same method as S-4, except that the solid particles containing piperines, the type of dispersion aid (product name, manufacturer name, etc.), and the mass parts were changed to those listed in Table 2.

[0103] [Table 2]

[0104] <Evaluation of average particle size of aqueous dispersions> The particle size (50% median diameter) of dispersed particles contained in the aqueous dispersion was measured using a particle size distribution analyzer (product name: MicrotracUPA, manufactured by Nikkiso Co., Ltd.) and was defined as the average particle size. The results are shown in Table 3.

[0105] <Preparation of water-dispersible powder compositions> [Example 1] 150 parts by mass of aqueous dispersion S-1 were freeze-dried using a freeze-dryer (FDU-1200, manufactured by Tokyo Rikakikai Co., Ltd.) to obtain powder composition F-1. The moisture content of the obtained powder composition was measured using a Karl Fischer moisture meter and was found to be 3.2% by mass.

[0106] [Examples 2-5, 7, 8, 10-12, 17, 18, Comparative Examples 1, 2] The powder composition was prepared using the same method as in Example 1, except that the type of aqueous dispersion was changed to one of those listed in Table 3. The results for moisture content are also shown in Table 3.

[0107] [Example 6] 150 parts by mass of aqueous dispersion S-6 were subjected to spray drying using a spray dryer (GB-210, manufactured by Yamato Scientific Co., Ltd.) to obtain powder composition F-6. The moisture content of the obtained powder composition was measured using a Karl Fischer moisture meter and was found to be 2.1% by mass.

[0108] [Examples 9, 13-16, 19, 20] The powder composition was prepared using the same method as in Example 6, except that the type of aqueous dispersion was changed to one of those listed in Table 3. The results for moisture content are also shown in Table 3.

[0109] <Evaluation of water redispersibility of water-dispersible powder compositions> The redispersibility of the prepared powder composition in water was evaluated. 100 parts by mass of water was added to a beaker, and 0.1 parts by mass of the powder composition was added. The mixture was stirred at 500 rpm for 1 hour using a stirring blade to prepare a powder redispersion solution in which the particles in the powder composition were dispersed in water. The powder redispersion solution was evaluated by visually checking the sedimentation of the particles and by evaluating the average particle size using a particle size distribution analyzer (MicrotracUPA, manufactured by Nikkiso Co., Ltd.). The visual evaluation criteria were as follows. • Criteria for evaluating sedimentation A: No subsidence observed visually. B: Slight sedimentation, suspended state C: Sedimentation occurs, but the supernatant becomes clear after standing.

[0110] <Evaluation of dispersion stability of water-dispersible powder compositions and powder redispersion solutions> The prepared powder redispersion solution was stored for 30 days at a temperature of 40°C and a relative humidity of 60%RH. The average particle size (50% median diameter) of the dispersed particles contained in the powder redispersion solution was measured to evaluate its dispersion stability. The measurement results are shown in Table 3. It should be noted that the smaller the change in the average particle size of the dispersed particles in the powder redispersion solution before and after long-term storage, the better the dispersion stability of the composition.

[0111] [Table 3]

[0112] Visual inspection of the powder redispersion solution revealed that Comparative Examples 1 and 2, which used raw material powders of piperine and tetrahydropiperine, settled in water and did not redisperse, whereas the powder composition of the present invention showed redispersibility in water without settling. Regarding the average particle size, the powder composition of the present invention showed similar values ​​in the aqueous dispersion and the powder redispersion solution, indicating that the particles in the redispersion solution reproduce the dispersed particle state in the dispersion. From the viewpoint of redispersibility, among the dispersion aids, polyglycerin fatty acid ester, sucrose fatty acid ester, lecithin, hydroxypropyl cellulose, gum arabic, ghati gum, and enzyme-treated hesperidin showed particularly good results. Furthermore, from the viewpoint of average particle size, wet grinding treatment tended to result in finer particles. As described above, the powder composition of the present invention is a powder composition with small particle size and excellent water redispersibility. [Industrial applicability]

[0113] This composition can be used in a variety of applications, including food products, cosmetics, pharmaceuticals, and quasi-drugs, utilizing a water-dispersible powder containing piperines.

Claims

1. The product comprises solid particles (A) containing piperines and a dispersion aid (B), The dispersion aid is a water-dispersible powder composition comprising at least one selected from phospholipids, sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters, acidic polysaccharides, cellulose derivatives, polyvinylpyrrolidone, and enzyme-treated products.

2. The water-dispersible powder composition according to claim 1, wherein the dispersion aid (B) comprises at least one selected from lecithin, sucrose fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, hydroxypropyl methylcellulose, gum arabic, ghati gum, polyvinylpyrrolidone, enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, and enzyme-treated hesperidin.

3. The water-dispersible powder composition according to claim 1, wherein the average particle size when the water-dispersible powder composition is redispersed in water is 500 nm or less.

4. The water-dispersible powder composition according to claim 1, wherein the mass ratio of solid particles (A) containing piperines to the dispersing aid (B) is 1:0.2 to 1:

3.

5. The water-dispersible powder composition according to claim 1, further comprising an excipient (C).

6. The water-dispersible powder composition according to claim 5, wherein the excipient (C) comprises at least one selected from disaccharides, sugar alcohols, starch, and starch derivatives.

7. The water-dispersible powder composition according to claim 1, wherein the solid particles (A) containing piperines are a product of wet grinding and pulverization.

8. The solid particles (A) containing piperines contain piperines and a water-soluble organic solvent (E), and the water-soluble organic solvent (E) satisfies the following (i) to (iii): The water-dispersible powder composition according to claim 1, wherein the content of the water-soluble organic solvent (E) is 0.003 to 0.3 parts by mass per 100 parts by mass of the solid particles (A). (i) The molecular weight is between 90 and 350. (ii) Having at least two functional groups selected from the group consisting of hydroxyl groups, ester groups, and carboxyl groups. (iii) The viscosity at 60°C is 2 to 150 mPa·s.

9. The water-dispersible powder composition according to claim 8, wherein the water-soluble organic solvent (E) comprises at least one selected from the group consisting of diacetin, triacetin, lactic acid, trippropionine, tripbutyline, triethyl citrate, and acetyltriethyl citrate.

10. A method for producing a water-dispersible powder composition, comprising drying an aqueous dispersion containing solid particles (A) containing piperines, a dispersion aid (B), and an aqueous medium (D).

11. A food product comprising the water-dispersible powder composition according to any one of claims 1 to 9.

12. A cosmetic comprising the water-dispersible powder composition according to any one of claims 1 to 9.

13. A pharmaceutical product comprising the water-dispersible powder composition according to any one of claims 1 to 9.

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