Aqueous dispersion of organic pigment and method for producing the same, and organic pigment-containing composition

Abstract

To provide an aqueous dispersion with superior dispersibility of an organic pigment and a method for producing the same.SOLUTION: An aqueous dispersion of an organic pigment comprises an organic pigment (A) in a dispersed state, the aqueous dispersion containing an enzyme-treated product (B), wherein the mass ratio of the organic pigment (A) to the enzyme-treated product (B) is 5:1 to 1:4.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to an aqueous dispersion of an organic dye and a method for making the same, and also to an organic dye-containing composition. [Background technology]

[0002] Organic pigments are available in a wide range of vivid colors and have excellent coloring power and transparency, making them widely used in printing inks, paints, rubber, plastics, paints, paper, textiles, cosmetics, food coloring, and other applications. To broaden the scope of applications for organic pigments, there is a demand for aqueous dispersions in which pigments are dispersed in aqueous media. For example, Patent Document 1 discloses an inkjet recording ink that contains a pigment, a surfactant, an organic solvent, enzyme-treated rutin, water, and the like, as an aqueous inkjet recording ink that has excellent weather resistance and ink ejection stability.

[0003] Patent Document 2 proposes a method for inhibiting fading of tar dyes, in which a composition containing a tar dye, a reducing sugar, an ascorbic acid, or a metal, is blended with at least one selected from the group consisting of isoquercitrin, enzyme-modified isoquercitrin, rutin, enzyme-modified rutin, bayberry extract, and rosemary extract. Patent Documents 3 to 5 will be described later. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-70510 [Patent Document 2] International Publication No. 2005 / 108503 [Patent Document 3] Japanese Patent Application Publication No. 10-70994 [Patent Document 4] Japanese Patent Application Publication No. 3-7593 [Patent Document 5] Japanese Patent Application Publication No. 5-194164 Summary of the Invention [Problem to be solved by the invention]

[0005] Methods for dispersing pigments in aqueous dispersions include adding a surfactant, using a hydrophilic resin as a dispersant, and modifying the pigment surface with hydrophilic groups. However, because pigments are insoluble in water, it is difficult to stably disperse them in an aqueous medium. There is a demand in the market for aqueous dispersions of pigments with excellent dispersibility. Note that while the above discussion focuses on the issues with organic pigments, similar issues can arise with organic colorants in general, including organic dyes.

[0006] The present disclosure has been made in view of the above background, and aims to provide an aqueous dispersion having excellent dispersibility for organic dyes, a method for producing the same, and an organic dye-containing composition. [Means for solving the problem]

[0007] As a result of extensive research, the present inventors have found that the problems of the present disclosure can be solved in the following aspects, and have thus completed the present disclosure. [1]: An aqueous dispersion in which an organic colorant (A) is dispersed, the aqueous dispersion containing an enzyme-treated product (B), and the mass ratio of the organic colorant (A) to the enzyme-treated product (B) is 5:1 to 1:4. [2]: The aqueous dispersion of an organic dye according to [1], wherein the enzyme-treated product (B) comprises at least one selected from enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, enzyme-treated hesperidin, enzyme-treated resveratrol, and enzyme-treated pterostilbene. [3]: The aqueous dispersion of an organic dye according to [1] or [2], wherein the organic dye (A) is a pigment. [4]: The aqueous dispersion of an organic dye according to [3], wherein the pigment comprises a compound having at least one skeleton selected from azo, phthalocyanine, anthraquinone, diketopyrrolopyrrole, isoindoline, isoindolinone, quinophthalone, quinacridone, perylene, thioindigo, triphenylmethane, and xanthene. [5]: The aqueous dispersion of an organic dye according to any one of [1] to [4], wherein the particle size distribution of the organic dye (A) in the aqueous dispersion is 10 to 1000 nm. [6]: An aqueous dispersion of the organic dye according to any one of [1] to [5], which is used for any of pharmaceuticals, oral care products, cosmetics, and foods. [7]: An aqueous dispersion of the organic dye according to any one of [1] to [5], which is used for printing ink applications. [8]: A method for producing an aqueous dispersion of an organic dye, comprising adding and mixing an organic dye (A) and an enzyme-treated product (B) in water so that the ratio of the organic dye (A) to the enzyme-treated product (B) is 5:1 to 1:4, and then performing a dispersion treatment using at least one of ultrasonic waves, a homogenizer, and a bead mill dispersion treatment. [9]: An organic dye-containing composition comprising an aqueous dispersion of the organic dye according to any one of [1] to [5], and a component selected from the group consisting of a pharmaceutical active ingredient, an oral care active ingredient, a cosmetic active ingredient, and a food active ingredient, or a component comprising a combination of two or more of the same and / or different types selected from the group. [Effects of the Invention]

[0008] The present disclosure has the excellent effect of providing an aqueous dispersion having excellent dispersibility for organic dyes, a method for producing the same, and an organic dye-containing composition. DETAILED DESCRIPTION OF THE INVENTION

[0009] An example of an embodiment to which the present disclosure is applied will be described below. The present disclosure is not limited to this embodiment, and other embodiments may also fall within the scope of the present disclosure as long as they are consistent with the spirit of the present disclosure. Furthermore, each embodiment can be combined as desired. In this specification, a numerical range specified using "to" includes the numerical values ​​written before and after "to". The numerical values ​​specified in this specification are values ​​determined by the methods disclosed in the embodiments or examples. Furthermore, unless otherwise noted, each component may be used independently, either alone or in combination of two or more types.

[0010] 1. Aqueous dispersion of organic dyes The aqueous dispersion of an organic dye according to the present disclosure (hereinafter also referred to as the present dispersion) is an aqueous dispersion in which an organic dye (A) is dispersed. The present dispersion contains an enzyme-treated product (B). In the present dispersion, the mass ratio of the organic dye (A) to the enzyme-treated product (B) is 5:1 to 1:4.

[0011] Here, the enzyme-treated product (B) refers to a water-insoluble functional food ingredient to which sugar has been added by enzyme treatment. The enzyme-treated product (B) is also called a glycoside or a glycosyltransferase. The enzyme-treated product (B) has a structure derived from the functional food ingredient and a structure derived from sugar.

[0012] The organic dye (A) refers to a dye compound made of an organic compound that imparts color to an object by absorbing or emitting visible light, by structural color due to light interference, or by pearlescent luster.

[0013] As used herein, an aqueous dispersion refers to an aqueous medium containing an organic dye (A) at least a portion of which is dispersed in water in the form of particles. An organic dye (A) completely dissolved in water is not included in the aqueous dispersions of the present disclosure. On the other hand, even if a portion of the organic dye (A) is dissolved in water, if at least a portion of the organic dye (A) is dispersed in water in the form of particles, the dispersion is an aqueous dispersion of the present disclosure. Therefore, in the case of a soluble organic dye (A), depending on the concentration, the dispersion may or may not fall under the aqueous dispersion of the present disclosure. In addition to water, an organic solvent compatible with water may also be added as a medium.

[0014] Particulate organic pigments (A) tend to aggregate in aqueous media, resulting in the generation of coarse particles and the sedimentation of aggregates. Therefore, conventionally, resins or surfactants have been added as dispersing aids to coat the surfaces of organic pigment particles, improving the dispersibility of the organic pigment. However, existing resins and surfactants have insufficient dispersibility, and because they are chemically synthesized, they have issues with biocompatibility. This has limited the types of pigments that can be used, particularly in pharmaceutical, oral care, food, and cosmetic applications.

[0015] As a result of extensive research, the present inventors have found that the use of an aqueous dispersion in which the mass ratio of organic dye (A) to enzyme-treated product (B) is the above-mentioned specific ratio significantly improves the dispersibility and storage stability of the organic dye (A). This is believed to be because the functional food component-derived moiety of the enzyme-treated product (B) interacts with and adsorbs to the hydrophobic moiety of the organic dye (A), effectively preventing aggregation of the organic dye (A). Furthermore, the sugar-derived moiety of the enzyme-treated product (B) is believed to improve dispersibility in water. As a result, the generation of coarse particles is prevented and dispersibility is significantly improved. This dispersion has a structure derived from food components and a structure derived from sugar, resulting in excellent biocompatibility. Furthermore, since it is not derived from petroleum, it is suitable from the perspective of reducing environmental impact.

[0016] The adsorption of the enzyme-treated product (B) onto the organic dye (A) can be achieved in a manner in which the enzyme-treated product (B) partially or entirely coats the surface of the organic dye (A). Generally, the finer the organic dye (A), the more likely it is to aggregate. However, according to the aqueous dispersion of the present disclosure, the addition of the enzyme-treated product (B) can suppress aggregation of the organic dye (A). As a result, even when the organic dye (A) is finely divided, the dispersibility of the organic dye (A) is improved, resulting in excellent transparency. Therefore, the present dispersion is suitable for use as a printing ink for cosmetics or containers and packaging materials, which require excellent design. Furthermore, since the enzyme-treated product, which is biocompatible, is used, the dispersion is also suitable for use as a printing ink for containers and packaging materials that come into contact with food.

[0017] From the viewpoint of more effectively enhancing storage stability, the mass ratio of the organic dye (A) to the enzyme-treated product (B) is more preferably 3:1 to 1:3, and even more preferably 1:1 to 1:2. The amounts of the organic dye and the enzyme-treated product in the dispersion can be adjusted as desired.

[0018] The solid content of the dispersion can be appropriately designed, but the water content is preferably 60 to 99 mass%, more preferably 70 to 98 mass%, and even more preferably 75 to 95 mass%, based on 100 mass% of the dispersion. Each component will be described below.

[0019] [Organic dye (A)] In the aqueous dispersion of the present disclosure, the organic colorant (A) is at least partially particulate in water. Specific examples of the organic colorant (A) include pigments that are insoluble in solvents such as water and oil, and lake pigments in which water-soluble dyes are insolubilized by converting them into metal salts. Furthermore, even if a water-soluble dye is present at a concentration exceeding the solubility range, the dye will also be particulate and dispersed. Therefore, the organic colorant (A) may also contain a water-soluble dye. From the viewpoints of weather resistance and light resistance, the organic colorant (A) is preferably a pigment.

[0020] "Pigments" are colorants with a color index number of "Pigment" that are insoluble or have low solubility in water and generally have excellent water and light resistance. "Dyes" are colorants that are soluble or have high solubility in water, and many of them tend to fade when exposed to light for long periods of time. Pigments also include "lake pigments," which have reduced solubility by coordinating aluminum or calcium to dyes to form lakes.

[0021] The type of pigment is not limited, and known pigments can be used. It is preferable to use a compound having at least one skeleton selected from azo, phthalocyanine, anthraquinone, diketopyrrolopyrrole, isoindoline, isoindolinone, quinophthalone, quinacridone, perylene, thioindigo, triphenylmethane, and xanthene. Suitable examples include azo pigments, phthalocyanine pigments, quinacridone pigments, perylene pigments, perinone pigments, isoindoline pigments, isoindolinone pigments, dioxazine pigments, thioindigo pigments, anthraquinone pigments, indanthrene pigments, anthraquinone pigments, diketopyrrolopyrrole pigments, and quinophthalone pigments. Specific examples include pigments listed in the Color Index and the Organic Pigment Handbook (published by Color Office Co., Ltd. in 2006).

[0022] Lake pigments include acid dye lake pigments, which are dyes having an acidic group such as a sulfonic acid group or a carboxyl group in the molecule that have been laked with a metal salt such as aluminum, calcium, or barium, and basic dye lakes, which are dyes having an amino group or its derivative group in the molecule that have been laked with tannic acid, phosphotungstic acid, or phosphomolybdic acid. The skeleton of the parent dye can be azo dyes, disazo dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), quinoneimine dyes (oxazine dyes), Examples of dyes include thiazine dyes, azine dyes, polymethine dyes (oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, and rhodamine dyes. Specific dye structures are described in "New Edition Dye Handbook" (edited by the Society of Organic Synthetic Chemistry; Maruzen, 1970), "Color Index" (The Society of Dyes and Colorists), and "Dye Handbook" (edited by Okawara et al.; Kodansha, 1986).

[0023] For pharmaceutical, food, and cosmetic applications, legal dyes are preferred. Examples of legal dyes include those specified in the Ministry of Health, Labor, and Welfare Ordinance No. 30, "Ministerial Ordinance Specifying Tar Dyes Usable in Pharmaceuticals, etc." Examples include Red No. 2, Red No. 3, Red No. 102, Red No. 104 (1), Red No. 105 (1), Red No. 106, Red No. 201, Red No. 202, Red No. 227, Red No. 230 (1), Red No. 230 (2), Red No. 231, Red No. 232, Red No. 401, Red No. 503, Red No. 506, Yellow No. 4, Yellow No. 5, Yellow 201, Yellow No. 202 (1), Yellow No. 202 (2), and Yellow No. 5. 203, Yellow 401, Yellow 402, Yellow 403 (1), Yellow 406, Yellow 407, Orange 205, Orange 207, Orange 402, Green 3, Green 201, Green 205, Green 401, Green 402, Blue 1, Blue 2, Blue 202, Blue 203, Blue 205, Blue 403, Brown 201, Purple 201, Purple 401, and Black 401.

[0024] The content of the organic colorant (A) is preferably 3 to 15% by mass relative to 100% by mass of the solid content of the dispersion. One or more types of organic colorant (A) are used. The hue of the organic colorant is not particularly limited.

[0025] The organic colorant (A) preferably has an optimum particle size distribution depending on the application. From the viewpoint of further improving the dispersibility of the dispersion and enhancing the stability over time, the particle size distribution is preferably 10 to 1,000 nm, more preferably 30 to 800 nm, and even more preferably 50 to 500 nm. The particle size distribution is a value measured by the method described below. The organic colorant (A) before dispersion can have a desired particle size distribution by adjusting the size, for example, by reducing the size of the grinding media in the disperser, adjusting the processing time, for example, by extending the processing time, or by classifying the particles using a filter or a centrifuge after grinding. These methods may be combined.

[0026] When the organic colorant (A) is dispersed in water, it tends to aggregate over time, resulting in a larger particle size distribution. Coarse particles may be generated and settle out, but by adjusting the mass ratio of the organic colorant (A) to the enzyme-treated product (B) to 5:1 to 1:4, an aqueous dispersion that exhibits excellent dispersibility of the organic colorant (A) over time can be provided.

[0027] [Enzyme-treated product (B)] The enzyme-treated product (B) plays a role in preventing aggregation of the organic colorant (A) in the present dispersion and in dispersing it well in water.

[0028] Specific examples of sugars to be added to the water-insoluble functional food ingredient to obtain the enzyme-treated product (B) include monosaccharides, amino sugars, and oligosaccharides. Examples of the monosaccharides include glucose, galactose, mannose, fructose, xylose, and arabinose. Examples of the amino sugars include N-acetylglucosamine, glucosamine, N-acetylgalactosamine, galactosamine, and laminaribiose. Examples of the oligosaccharides (including disaccharides) include trehalose, neotrehalose, maltose, cellobiose, gentiobiose, lactose, melibiose, rutinose, sucrose, turanose, vicianose, cellotriose, gentianose, isopanose, maltotriose, raffinose, lycotetraose, maltotetraose, maltopentaose, maltohexaose, and mannobiose. The biocompatible enzyme-treated product (B) is particularly suitable for use in medicine, oral care, food, and cosmetics.

[0029] Functional foods refer to foods that can provide a specific function to the living body, and include all types of health foods, such as foods for specified health uses (including conditional FOSHUs [foods for specified health uses]), foods with functional claims, health functional foods including foods with nutrient functions, foods for special dietary uses, dietary supplements, health supplements, supplements (in various dosage forms such as tablets, coated tablets, sugar-coated tablets, capsules, and liquids), beauty foods (such as diet foods), etc. Functional foods also include health foods to which health claims based on the food standards of Codex Alimentarius (the Joint FAO / WHO Commission on Food Standards) are applied.

[0030] Specific examples of functional food ingredients include polyphenols, catechins, anthocyanins, anthocyanidins, naringin, silibinin, isoflavones, steviol, glycyrrhizin, ellagic acid, citric acid, chlorogenic acid, malic acid, stevia, rutin, naringin, hesperidin, resveratrol, pterostilbene, sphingolipids, glycerin ester-based oils, fibrous proteins (collagen, elastin, etc.), coenzyme Q10, and culinary extracts. Examples include cumin, tocotrienols, carotenoids (α-carotene, β-carotene, lutein, lycopene, astaxanthin, zeaxanthin, cryptoxanthin, fucoxanthin, xanthophylls, etc.), docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), fat-soluble vitamins (vitamin A, vitamin D, vitamin E (tocopherol), vitamin K) and their derivatives, sesamin, α-lipoic acid, ferulic acid, and oryzanol. Among these, polyphenols are more preferred.

[0031] Specific examples of enzymes include pectinases, cellulases, xylanases, amylases, mannanases, glucosidases, hemicellulases, chitinases, α- and β-glucuronidases, and α- and β-glucanases.

[0032] The enzyme-treated product (B) can be produced by known methods. For example, the enzyme-treated product (B) can be produced by the methods described in Patent Documents 3 to 5. Suitable examples of the enzyme-treated product (B) include enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, enzyme-treated hesperidin, enzyme-treated resveratrol (resveratrol glycoside), quercetin glycoside, and enzyme-treated pterostilbene.

[0033] Commercially available enzyme-treated rutin includes, for example, "αG Rutin H," "αG Rutin P," and "αG Rutin PS" (all trade names, manufactured by Toyo Sugar Refining Co., Ltd.). Commercially available enzyme-treated naringin includes, for example, "αG Naringin H" (trade name, manufactured by Toyo Sugar Refining Co., Ltd.). Commercially available enzyme-treated hesperidin includes, 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 includes, 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.).

[0034] The content of the enzyme-treated product (B) is preferably 1 to 20% by mass relative to 100% by mass of the solid content of the dispersion. One or more types of enzyme-treated product (B) are used.

[0035] [Other additives] The present dispersion may contain any component, such as an inorganic pigment, an antioxidant, an organic pigment dispersant, a surfactant, an organic solvent, an antifoaming agent, an antistatic agent, a wax, a pH adjuster, a preservative, or a thickener, within the scope of the present disclosure.

[0036] [Application] Although the dispersion is an aqueous medium, it exhibits excellent dispersibility of the organic colorant (A) over time, making it suitable for use in a wide range of applications where the organic colorant (A) is used as an aqueous medium. The dispersion is suitable for use in printing inks and paints. The dispersion is also suitable for use in pharmaceuticals, cosmetics, and foods. For cosmetic applications, a legal colorant whose safety has been confirmed under the Pharmaceutical Affairs Law is used.

[0037] 2. Method for producing aqueous dispersion of organic dye The aqueous dispersion of the present disclosure can be prepared by applying shear force to a mixture containing an organic colorant (A), an enzyme-treated product (B), and water to mechanically micronize the particles of the organic colorant (A). While there are no particular restrictions on the device used to apply the shear force, any of ultrasonic, homogenizer, and bead mill dispersion treatment methods is preferred. Among these, bead mill dispersion treatment is particularly preferred from the viewpoint of particle micronization.

[0038] Ultrasonic dispersion is a method of crushing and dispersing particles by the force of cavitation generated by immersing an ultrasonic wave-emitting tip in a liquid. Commercially available ultrasonic dispersion machines include the UH-50, UH-50F, UH-300, UH-600, UH-600S, and UH-600SH (all trade names, manufactured by MST Corporation), and the PSF-600, PSF-1200, and RUS-600TCVP (all trade names, manufactured by Nippon Seiki Seisakusho Co., Ltd.).

[0039] Homogenizer dispersion methods can be broadly categorized into agitator homogenizers and high-pressure homogenizers. Agitator homogenizers are devices that entrain powder into a liquid by rotating agitator blades at high speed, while simultaneously dispersing the particles through the cutting action of the blades. Commercially available agitator homogenizers include the Clearmix W Motion CLM-1.7 / 5.5W and Clear SS5-100 (both trade names) manufactured by M Technique Co., Ltd., and the Adihomomixer 2M and HV-M (trade names) manufactured by Primix Corporation. High-pressure homogenizers are devices that pressurize the material to be pulverized to high or ultra-high pressure and pulverize and disperse it by the shear force generated when it passes through a slit (gap), and include devices generally known as 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.).

[0040] Bead mill dispersion is a method in which various components (organic dye, enzyme-treated product) are mixed in an aqueous medium, and coarse particles or aggregates (agglomerated particles) are pulverized, refined, and dispersed by the collision force between the beads. During this process, the particle surfaces of the organic dye (A) are coated with the enzyme-treated product (B). This improves the stability of the aqueous dispersion and facilitates long-term suppression of sedimentation. These dispersion methods can be carried out appropriately 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.

[0041] Commercially available bead mills can be used. Commercially available bead mills that can be used to prepare the dispersion include Star Mill Nano Getter, Star Mill ZRS, Star Mill LMZ, and Agitator Mill LMK (all trade names, Ashizawa Finetech Co., Ltd.), Spike Mill, Mighty Mill, Mighty Mill Mark II, and Key Mill (all trade names, Inoue Seisakusho Co., Ltd.), Apex Mill, Super Apex Mill, and Ultra Apex Mill (all trade names, Hiroshima Metal & Machinery Co., Ltd.), and San Examples of such mills include the Glue Grinder (SLG), Ready Mill (RMV-03), Nano Ready Mill (RMV-03), Ultra Viscomill (UVM), Ultra-X Viscomill (UVX), New Viscomill (NVM) (all trade names, Imex Co., Ltd.), SC Mill, MSC Mill, Attritor, Fine Mill (all trade names, Nippon Coke and Engineering Co., Ltd.), annular gap bead mill (trade name, Eurotech Co., Ltd.), DYNO-MILL ECM, DYNO-MILL NPM-NANO Performance Mill (all trade names, Shinmaru Enterprise Co., Ltd.), and MicroMediaX1 (trade name, Buhler Co., Ltd.).

[0042] 3.Organic pigment-containing composition The organic dye-containing composition of the present disclosure (hereinafter also referred to as the present composition) contains the aqueous dispersion of the present disclosure and an active ingredient. Suitable examples of the active ingredient include a pharmaceutical active ingredient, an oral care active ingredient, a cosmetic active ingredient, andThe composition contains a component selected from the group consisting of active ingredients for foods, or a combination of two or more of the same and / or different components selected from the group. It is important to prepare an aqueous dispersion of the composition and then mix it with the other active ingredients described above. By preparing an aqueous dispersion, the dispersibility of the organic colorant (A) is enhanced, and then by mixing other ingredients, high dispersion of the organic colorant (A) can be achieved. The composition may be mixed with an active ingredient after concentrating or diluting the dispersion, within the scope of the present disclosure. Furthermore, the dispersion may be dried by spray drying, freeze drying, or other processes, and then mixed with an active ingredient to prepare an organic colorant-containing composition.

[0043] Any known active pharmaceutical ingredient, active oral care ingredient, active cosmetic ingredient, or active food ingredient can be used.

[0044] According to the present composition, the dispersibility of the organic colorant (A) can be significantly improved by preparing the composition via the present dispersion. [Example]

[0045] 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.

[0046] <Raw materials> The organic dye (A) and the enzyme-treated product (B) used in this example are shown below. <Organic dye (A)> A-1: Phthalocyanine (PB15:3): Toyocolor "LIONOL BLUE 7919" A-2: Azo (PY12): Toyocolor "LIONOL YELLOW 1209" A-3: Azo-Calcium Lake (PR57, Red No. 202): Clariant "Graphtol Rubine L6B" A-4: Azo·Al Lake (Yellow No. 5): "FD&C Yellow No. 6" manufactured by Benifuji Chemical Industry Co., Ltd. A-5: Anthraquinone (PR177): "Cinilex Red SR3C" manufactured by CINIC A-6: Diketopyrrolopyrrole (PR254): DIC "Irgazin Red L 3660 HD" A-7: Isoindoline (PY185): DIC "Paliotol Yellow D1155" A-8: Isoindolinone (PY109): DIC "Irgazin Yellow 1030" A-9: Quinophthalone (PY138): DIC "Paliotol Yellow K0961HD" A-10: Quinacridone (PR122): DIC "FASTOGEN Super Magenta RGT" A-11: Perylene (PR179): Clariant "Hostperm Red P2GL" A-12: Thioindigo (Red No. 226): "D&C Red No. 30" manufactured by Benifuji Chemical Industry Co., Ltd. A-13: Triphenylmethane (Green No. 3): "FD&C Green No. 3" manufactured by Benifuji Chemical Industry Co., Ltd. A-14: Xanthene Al Lake (Red No. 104) "D&C Red No. 28" manufactured by Benifuji Chemical Industry Co., Ltd. <Enzyme-treated products (B), etc.> B-1: Enzyme-treated stevia: αG Sweet PA (Toyo Sugar Refining Co., Ltd.) B-2: Enzyme-treated rutin: αG Rutin H (Toyo Sugar Refining Co., Ltd.) B-3: Enzyme-treated naringin: αG naringin H (manufactured by Toyo Sugar Refining Co., Ltd.) B-4: Enzyme-modified hesperidin: Hayashibara Hesperidin S (Hayashibara Co., Ltd.) B-5: Enzyme-treated resveratrol: Patent No. 5938834, Example 1 B-6: Enzyme-treated pterostilbene: Patent WO2018 / 034327A1 Experimental Example 4 Z-1: Surfactant: Demol EP (Kao Corporation) Z-2: Resin: Polyvinyl alcohol (Tokyo Chemical Industry Co., Ltd.) The water used was ion-exchanged water.

[0047] [Example 1] Five parts of a phthalocyanine pigment (manufactured by Toyocolor Co., Ltd., product name: "LIONOL BLUE 7919") A-1 as the organic colorant (A), five parts of enzyme-treated stevia (manufactured by Toyo Sugar Refining Co., Ltd., product name: αG Sweet PA) B-1 as the enzyme-treated product (B), and 90 parts of purified water were mixed together. Then, ultrasonic irradiation was performed for two hours using an ultrasonic device (manufactured by Yamato Scientific Co., Ltd., product name: "LUH150") to obtain aqueous dispersion S-1.

[0048] [Example 2] Aqueous dispersion S-2 was obtained in the same manner as in Example 1, except that the ultrasonic device used in Example 1 was replaced with 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.

[0049] [Example 3] Aqueous dispersion S-3 was obtained in the same manner as in Example 1, except that the ultrasonic device in Example 1 was replaced with 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.

[0050] [Example 4] An aqueous dispersion S-4 was obtained in the same manner as in Example 1, except that the ultrasonic device used in Example 1 was replaced with 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 dispersion was carried out for 3 hours, followed by filtration through a filter with a pore size of 5.0 μm.

[0051] [Examples 5 to 27, Comparative Examples 1 to 4] Aqueous dispersions S-5 to S-27 and Comparative Examples 1 to 4 were obtained in the same manner as in Example 4, except that the raw materials and contents were changed as shown in Table 1.

[0052] <Particle size distribution of aqueous dispersion> The particle size distribution of the aqueous dispersions of each Example and Comparative Example was evaluated. The particle size distribution (D50: 50% median diameter) of the organic colorant (A) in the aqueous dispersion was measured using a particle size distribution analyzer (MicrotracUPA manufactured by Nikkiso Co., Ltd.). Measurements were taken immediately after preparation of the aqueous dispersion (24 hours after ink preparation) and after storage for 7 and 30 days in an environment of 25°C and 60% RH.

[0053] <Storage stability of aqueous dispersion> The aqueous dispersions of each Example and Comparative Example were stored for 7 days in an environment of 25°C and 60% RH. After storage, they were visually inspected for sedimentation and evaluated for sedimentation stability according to the following criteria. The evaluation results are shown in Table 1. ·Evaluation criteria for sedimentation stability ++: No visible change in appearance. +: Turbidity is observed visually. NG: Less than the above + rating, and precipitation and / or separation is confirmed by visual inspection.

[0054] [Table 1]

[0055] As shown in Comparative Example 1, an aqueous dispersion using a surfactant as a dispersant exhibited sedimentation and separation after 7 days, confirming that it had a problem with storage stability. Similarly, an aqueous dispersion using a resin as a dispersant exhibited sedimentation and separation after 7 days, confirming that it had a problem with storage stability. Furthermore, even when an enzyme-treated product (B) was used as a dispersant, if the content of the enzyme-treated product (B) relative to the organic dye (A) was low, sedimentation and separation occurred after 7 days, as shown in Comparative Example 3, confirming that it had a problem with storage stability. Furthermore, if the content of the enzyme-treated product (B) relative to the organic dye (A) was too high, sedimentation and separation occurred after 7 days, as shown in Comparative Example 4, confirming that it had a problem with storage stability. On the other hand, as shown in Examples 1 to 27, the aqueous dispersions of the present disclosure were confirmed to have excellent particle size distribution and excellent storage stability after 7 days.

[0056] Example 28: Cosmetic Use The following composition was mixed to prepare a cosmetic (emulsion foundation). ·Aqueous dispersion S-22: 10.2 parts by mass 25.6 Stearic acid: 1.75 parts by weight Nonionic surfactant (PEG-12 laurate): 5.0 parts by mass Glycerin tri-2-ethylhexanoate: 3.0 parts by mass Butylparaben: 0.1 parts by weight ·PEG-200: 1.0 parts by mass Carboxymethylcellulose sodium salt: 0.1 parts by mass Methylparaben: 0.2 parts by weight Triethanolamine: 0.7 parts by mass Aluminum magnesium silicate: 1.0 parts by mass ·Purified water: 76.95 parts by mass It was confirmed that the obtained cosmetic preparation had no defects in appearance such as sedimentation / cloudiness.

[0057] Example 29: Tablet formulation use A color dispersion was prepared by mixing 160 parts by weight of hydroxypropyl methylcellulose, 16 parts by weight of polyvinylpyrrolidone (weight average molecular weight: approximately 40,000), 16 parts by weight of titanium oxide, 0.6 parts by weight of aqueous dispersion S-22, and 1400 parts by weight of water. Next, 1000 g of circular plain tablets made by a conventional method and consisting of acetaminophen, lactose, crystalline cellulose, and magnesium stearate were placed in a pan coating device (manufactured by Freund Corporation). The plain tablets were heated while the color dispersion was sprayed into the device, and the water in the color dispersion (aqueous dispersion) was evaporated to obtain tablets (solid compositions) coated with the coating composition. The coating amount of the color dispersion was 5% by weight of the plain tablets. It was confirmed that the obtained tablet formulation had no abnormalities in appearance and good tablets were obtained.

[0058] As shown in Example 28, the aqueous dispersion of the present disclosure yielded a cosmetic preparation free from defects in appearance such as precipitation / turbidity, and was therefore confirmed to be suitable for use in cosmetics. Furthermore, as shown in Example 29, the aqueous dispersion of the present disclosure yielded a tablet preparation free from defects in appearance, and was therefore confirmed to be suitable for use in coloring tablet preparations. [Industrial Applicability]

[0059] The aqueous dispersion of the present disclosure can be used for various purposes. For example, it can be used to prepare food supplements, probiotics, medical foods, nutritional supplements, foods containing functional ingredients, cosmetics, pharmaceuticals, quasi-drugs, etc. for humans and / or animals. The aqueous dispersion of the present disclosure can also be used to prepare various inks, including printing inks.

Claims

1. An aqueous dispersion in which an organic colorant (A) is dispersed, An aqueous dispersion of an organic colorant containing an enzyme-treated product (B), wherein the mass ratio of the organic colorant (A) to the enzyme-treated product (B) is 5:1 to 1:

4.

2. 2. An aqueous dispersion of an organic dye according to claim 1, wherein the enzyme-treated product (B) comprises at least one selected from enzyme-treated stevia, enzyme-treated rutin, enzyme-treated naringin, enzyme-treated hesperidin, enzyme-treated resveratrol, and enzyme-treated pterostilbene.

3. 2. The aqueous dispersion of an organic dye according to claim 1, wherein the organic dye (A) is a pigment.

4. 4. The aqueous dispersion of an organic dye according to claim 3, wherein the pigment comprises a compound having at least one skeleton selected from azo, phthalocyanine, anthraquinone, diketopyrrolopyrrole, isoindoline, isoindolinone, quinophthalone, quinacridone, perylene, thioindigo, triphenylmethane, and xanthene.

5. 2. The aqueous dispersion of an organic dye according to claim 1, wherein the particle size distribution of the organic dye (A) in the aqueous dispersion is 10 to 1,000 nm.

6. 6. The aqueous dispersion of the organic dye according to claim 1, which is used for any of pharmaceuticals, oral care products, cosmetics, and foods.

7. 6. An aqueous dispersion of the organic dye according to claim 1, which is used for printing ink applications.

8. A method for producing an aqueous dispersion of an organic dye, comprising adding and mixing an organic dye (A) and an enzyme-treated product (B) in water so that the ratio of the organic dye (A) to the enzyme-treated product (B) is 5:1 to 1:4, and then performing a dispersion treatment using at least one of ultrasonic waves, a homogenizer, and a bead mill dispersion treatment.

9. An aqueous dispersion of the organic dye according to any one of claims 1 to 5; An organic pigment-containing composition comprising an ingredient selected from the group consisting of pharmaceutical active ingredients, oral care active ingredients, cosmetic active ingredients, and food active ingredients, or a combination of two or more of the same and / or different ingredients selected from the group.

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