WO2016098562A1 - SOLUBILIZING OR DISPERSING COMPOSITION FOR POORLY SOLUBLE OR INSOLUBLE SUBSTANCE HAVING π-CONJUGATED SYSTEM - Google Patents

SOLUBILIZING OR DISPERSING COMPOSITION FOR POORLY SOLUBLE OR INSOLUBLE SUBSTANCE HAVING π-CONJUGATED SYSTEM Download PDF

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WO2016098562A1
WO2016098562A1 PCT/JP2015/083372 JP2015083372W WO2016098562A1 WO 2016098562 A1 WO2016098562 A1 WO 2016098562A1 JP 2015083372 W JP2015083372 W JP 2015083372W WO 2016098562 A1 WO2016098562 A1 WO 2016098562A1
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water
soluble
insoluble
conjugated
component
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PCT/JP2015/083372
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French (fr)
Japanese (ja)
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梓 西野
敬司 市原
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グリコ栄養食品株式会社
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Priority to JP2016564762A priority Critical patent/JP6775423B2/en
Publication of WO2016098562A1 publication Critical patent/WO2016098562A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F21/00—Dissolving
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/05—Preparation or purification of carbon not covered by groups C01B32/15, C01B32/20, C01B32/25, C01B32/30
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins

Definitions

  • the present invention relates to a solubilized or dispersed composition of a ⁇ -conjugated system hardly soluble or insoluble substance. More specifically, the present invention relates to a composition having improved solubility or water dispersibility of a ⁇ -conjugated system poorly soluble or insoluble substance in water.
  • ⁇ -conjugated functional substances in which a plurality of double bonds are alternately connected with a single bond interposed therebetween are often used.
  • many of the substances used as dyes are ⁇ -conjugated substances.
  • polyphenols which are ⁇ -conjugated substances, have excellent antioxidant power and are expected to be effective in anti-arteriosclerosis, anti-allergy, blood flow enhancement, etc. It is recognized as an important component.
  • carbon materials such as carbon nanotubes, which are ⁇ -conjugated substances, are molecular devices that can be highly integrated, occluded materials of various gases such as hydrogen, and field emission displays (FEDs). It has been attracting attention as a functional substance such as a member for use, an electrode material, and an additive for resin molded products.
  • ⁇ -conjugated substances have the property of being easily self-assembled by ⁇ - ⁇ interaction, and there are many substances that are hardly soluble in water or insoluble and have low dispersibility in water. Therefore, for example, when using poorly soluble polyphenols in aqueous foods such as soft drinks, it is necessary to improve the solubility or dispersibility of the hardly soluble polyphenols.
  • a technique for uniformly dispersing an insoluble carbon material is indispensable.
  • a ⁇ -conjugated hardly soluble or insoluble substance is used in an aqueous system, it is required to improve the solubilizing ability or dispersing ability.
  • Patent Documents 1 to 4 are not applicable to ⁇ -conjugated substances in general, and a formulation to be solubilized or dispersed must be designed according to the kind of hardly soluble or insoluble substances.
  • ⁇ -conjugated materials There are limitations on applicable ⁇ -conjugated materials, and there are drawbacks in terms of versatility. Therefore, if technology capable of improving the solubilization ability or dispersibility is established without being restricted by the kind of a ⁇ -conjugated system insoluble or insoluble, various fields such as food, cosmetics, pharmaceuticals, chemistry, and electronics can be established. Can contribute to efficiency and technological innovation.
  • An object of the present invention is to provide a composition that improves the solubilization ability or water dispersibility of a ⁇ -conjugated system poorly soluble or insoluble substance in water.
  • the inventors of the present invention have made extensive studies to solve the above-mentioned problems.
  • carotenoid glycosides and / or crocetin are allowed to coexist with a poorly water-soluble or water-insoluble substance of a ⁇ -conjugated system, thereby making the ⁇ -conjugated system poorly water-soluble.
  • it has been found that the water solubilizing ability or water dispersibility of a water-insoluble substance can be remarkably improved.
  • the present invention has been completed by further studies based on such knowledge.
  • This invention provides the invention of the aspect hung up below.
  • Item 1 Solubilization or dispersion of a ⁇ -conjugated system poorly soluble or insoluble substance characterized by containing (i) a ⁇ -conjugated system poorly water-soluble or water-insoluble substance, and (ii) a carotenoid glycoside and / or crocetin. Composition.
  • the component (i) is selected from the group consisting of poorly water-soluble or water-insoluble polyphenols, poorly water-soluble or water-insoluble carotenoids, poorly water-soluble or water-insoluble carbon materials, poorly water-soluble or water-insoluble organic pigments, and poorly water-soluble or water-insoluble drugs.
  • composition according to Item 1 which is at least one selected from the group consisting of: Item 3.
  • Item 3. The composition according to Item 1 or 2, wherein the component (ii) is crocetin glycoside.
  • Item 4. Item 4. The composition according to any one of Items 1 to 3, wherein the component (ii) is crocin-3 and / or crocin.
  • Item 5. The composition according to any one of Items 1 to 4, comprising Gardenia yellow as the component (ii).
  • Item 6. Item 6.
  • Item 7. Item 6.
  • Item 8. A ⁇ -conjugated poorly water-soluble solubilizing or dispersing agent containing carotenoid glycoside and / or crocetin as active ingredients.
  • Item 9. Item 9.
  • Solubilizing or dissolving a ⁇ -conjugated poorly water-soluble or water-insoluble substance comprising the step of solubilizing or dispersing the ⁇ -conjugated poorly water-soluble or water-insoluble substance in water in the presence of a carotenoid glycoside and / or crocetin Decentralization method.
  • a carotenoid glycoside and / or crocetin Decentralization method.
  • the ability to solubilize a ⁇ -conjugated poorly water-soluble or water-insoluble substance in water or Water dispersibility can be improved.
  • polyphenols which are ⁇ -conjugated poorly water-soluble substances, are used in the field of food and medicine.
  • the bioabsorbability is increased and the functionality of polyphenols is increased. It can be easily enjoyed.
  • carbon nanotubes which are ⁇ -conjugated water-insoluble substances, are used in conductive films and conductive paints.
  • the improvement in quality and productivity can be achieved by improving the dispersibility of carbon nanotubes. It can contribute to improvement.
  • Experiment 1 the result of having observed the external appearance of the liquid agent containing the manufactured resveratrol is shown.
  • Test Example 2 the result of observing the appearance of a liquid preparation containing resveratrol produced is shown.
  • Test Example 3 the result of observing the appearance of the liquid preparation containing curcumin produced is shown.
  • Test Example 4 the result of observing the appearance of a liquid preparation containing quercetin produced is shown.
  • Test Example 5 the result of observing the appearance of the produced dispersion containing carbon nanotubes is shown.
  • Experiment 6 the result of having observed the external appearance of the liquid agent containing the manufactured resveratrol is shown.
  • Composition of the present invention is a composition for solubilization or dispersion of a ⁇ -conjugated system poorly soluble or insoluble substance, comprising (i) It contains a ⁇ -conjugated system poorly water-soluble or water-insoluble substance, and (ii) carotenoid glycoside and / or crocetin.
  • composition of the present invention will be described in detail.
  • ⁇ -conjugated system poorly water-soluble or water-insoluble substance (sometimes abbreviated as (i) component) Containing.
  • ⁇ -conjugated system means a state in which a plurality of double bonds are alternately connected with a single bond interposed therebetween.
  • substances having a ⁇ -conjugated system it is hardly soluble or insoluble in water.
  • a substance showing is used. More specifically, as a suitable example of a ⁇ -conjugated substance, a substance having a ⁇ -conjugated system containing at least three double bonds in the molecule (that is, at least a double bond, a single bond, and two A substance having a ⁇ -conjugated structure including a heavy bond, a single bond and a double bond in the molecule).
  • the atom constituting the ⁇ -conjugated system is not particularly limited, but usually includes carbon, oxygen, nitrogen and the like.
  • benzene a ⁇ -conjugated molecule consisting of three double bonds
  • pyridine a substance in which a ⁇ -conjugated system is formed of carbon and nitrogen atoms.
  • a pyrimidine ⁇ conjugated molecule composed of 3 double bonds
  • “slightly soluble” means that the amount of water required to dissolve 1 g or 1 mL of solute at 20 ° C. is 30 mL or more and less than 10000 mL. In the present invention, it is possible to improve solubilization or dispersibility even for a ⁇ -conjugated system poorly soluble substance having very low solubility in water. In view of the effect of the present invention, the amount of water required to dissolve 1 g or 1 mL at 20 ° C. as a ⁇ -conjugated hardly soluble substance is preferably 100 mL or more and less than 10,000 mL, more preferably 100 mL or more and less than 10,000 mL. What shows a poor solubility is mentioned.
  • insoluble means that the amount of water required to dissolve 1 g or 1 mL of solute at 20 ° C. is 10,000 ml or more.
  • the “insoluble” includes those that are completely insoluble in water.
  • the kind of the hardly soluble or insoluble material of the ⁇ -conjugated system used in the present invention is not particularly limited, and any solubilization or ability in water is required as long as improvement in dispersibility is required.
  • poorly soluble or insoluble polyphenols include flavonoids such as catechin, anthocyanin, hesperidin, luteolin, quercetin, rutin, daidzein, genistein; lignan, chlorogenic acid, coumarin, eugenol, sesamin, magnolol, cinnamic acid Phenylpropanoids such as caffeic acid, coumaric acid and ferulic acid; curcuminoids such as curcumin and shogaol; stilbenoids such as resveratrol; ellagic acid and the like. These poorly soluble or insoluble polyphenols may be used alone or in combination of two or more.
  • the hardly soluble or insoluble carotenoids include carotenes such as ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, and lycopene; actinioerythritol, canthaxanthin, capsorbine, astaxanthin, fucoxanthin, lutein, zeaxanthin, and capsanthin.
  • ⁇ -cryptoxanthin violaxanthin, derivatives thereof (monoester or diester with fatty acid, etc.), etc .
  • bixin ⁇ -8′-apo-carotenal (apocarotenal), ⁇ -12′-apo-carotenal And apocartoids such as derivatives thereof (such as esters with lower or higher alcohols).
  • apocarotenal apocarotenal
  • ⁇ -12′-apo-carotenal And apocartoids such as derivatives thereof (such as esters with lower or higher alcohols).
  • These poorly soluble or insoluble carotenoids may be used singly or in combination of two or more.
  • insoluble carbon material examples include fullerene, carbon nanotube, and graphene. These insoluble carbon materials may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the hardly soluble or insoluble organic pigments include porphyrin, phthalocyanine, oligo (p-) phenylene vinylene, oligo (p-) phenylene ethynylene, perylene, perylene bisimide, fluorene, anthracene, tetracene, pentacene, Examples include pyrene, azobenzene, stilbene, diallylethene, oligophenylene, oligothiophene, and oxal dyes.
  • the poorly soluble or insoluble drug may be a drug used for the diagnosis, prevention or treatment of a disease in a human or non-human animal, or may be an agrochemical.
  • drugs used for the diagnosis, prevention or treatment of diseases of humans or non-human animals for example, antitumor agents such as melphalan, taxol, dacarbazine, doxorubicin hydrochloride; penicillin, Antibiotics such as cephalexin, tetracycline, nystatin, chloramphenicol, tolnaftate; antipyretic analgesic / anti-inflammatory agents such as aspirin, aminopyrine, phenacetin, mefenamic acid, flufenamic acid, indomethacin; clinofibrate, clofibrate, fenofibrate, bezafibrate, cholestyramine Antihyperlipidemic agents such as ofloxacin, ciprof
  • the agricultural chemicals include, for example, sparingly soluble insecticides such as acrinathrin, azamethiphos, and azinephosmethyl; sparingly soluble fungicides such as azoxystrobin, benalaxyl, benomyl, and viteltanol; azaphenidine, tenylchlor, Examples include poorly soluble herbicides such as bifenox and sulfentrazone; and poorly soluble plant growth regulators such as 6-benzylaminopurine, flumetraline and forchlorfenuron. These poorly soluble or insoluble drugs may be used alone or in combination of two or more.
  • ⁇ -conjugated hardly soluble or insoluble substances may be used alone or in combination of two or more.
  • These ⁇ -conjugated hardly soluble or insoluble substances may be in a purified state or in a state where other components are mixed.
  • a poorly soluble or insoluble polyphenol is used as the conjugated hardly soluble or insoluble substance
  • a plant extract extracted from a plant containing the hardly soluble or insoluble polyphenol may be used.
  • red pepper dye paprika dye, paprika oleoresin
  • anato dye imo carotene
  • Dunaliella carotene carrot carotene
  • shrimp Natural pigments that contain sparingly soluble or insoluble carotenoids such as pigments, krill pigments, orange pigments, crab pigments, corn pigments, tomato pigments, palm oil carotene, phafia pigments, albacore pigments, hematococcus algae pigments, marigold pigments, etc. There may be.
  • ⁇ -conjugated hardly soluble or insoluble substances from the viewpoint of more effectively improving the water solubilization ability or water dispersibility, preferably poorly soluble or insoluble polyphenols, insoluble carbon materials, More preferred are resveratrol, curcumin, quercetin, and carbon nanotubes.
  • the content of the component (i) is not particularly limited, and may be appropriately set according to the form and use of the composition, the type of the component (i), etc. 00001 to 99.9% by weight, preferably 0.0001 to 99% by weight, and more preferably 0.001 to 90% by weight.
  • composition of the present invention contains a carotenoid glycoside and / or crocetin (also referred to as (ii) component) together with the component (i).
  • a carotenoid glycoside and / or crocetin also referred to as (ii) component
  • component also referred to as (ii) component
  • the type of carotenoid that is an aglycon is not particularly limited.
  • -Apocartoids such as apo-carotenal
  • xanthophylls such as actinioerythritol, canthaxanthin, capsorbin, astaxanthin, fucoxanthin, lutein, zeaxanthin, capsanthin, ⁇ -cryptoxanthin, violaxanthin and the like.
  • the sugar component added to the carotenoid glycoside may be a monosaccharide or an oligosaccharide such as a trisaccharide or a tetrasaccharide.
  • Specific examples of the sugar component include monosaccharides such as glucose and glucuronic acid; disaccharides such as gentiobiose, maltose, sucrose, lactose, glucuronosylglucose and glucuronosylglucuronic acid; gentithiotriose, maltotriose, Examples include trisaccharides such as raffinose, panose, glucuronosyl gentiobiose, and glucosyl gentiobiose.
  • monosaccharides and disaccharides are preferable, glucose and gentiobiose are more preferable, and gentiobiose is particularly preferable.
  • the number of sugar components (monosaccharides and / or oligosaccharides) added to the carotenoid glycoside is not particularly limited, and a glycoside in which a sugar component (monosaccharide or oligosaccharide) is added at one location of the aglycone. It may be a glycoside in which sugar components (monosaccharide and / or oligosaccharide) are added at two positions of an aglycon.
  • sugar components (monosaccharides and / or oligosaccharides) in carotenoid glycosides from the viewpoint of more effectively improving the solubilization ability or water dispersibility of poorly soluble or insoluble substances of ⁇ -conjugated systems
  • the number is preferably 1.
  • the binding form between the aglycone and the sugar component is not particularly limited and varies depending on the type of aglycone to be used.
  • an ester bond, an O-glycoside bond, a C-glycoside bond, N-glycoside bond and the like can be mentioned.
  • the carotenoid glycoside may be a cis-trans isomer.
  • the crocetin used in the present invention may be either trans crocetin or cis crocetin, or a mixture thereof.
  • one type may be selected from carotenoid glycosides and crocetin, or two or more types may be used in combination.
  • xanthophyll glycosides and crocetin are preferably used from the viewpoint of more effectively improving the solubilization ability or water dispersibility of ⁇ -conjugated system insoluble or insoluble substances in water. More preferably xanthophyll glycoside and crocetin, more preferably crocetin glycoside and crocetin, particularly preferably crocetin digentiobiose glycoside [crocin-3 (crocetin-monogenthiobioside ester), crocin (crocetin- Digentiobioside ester)] and crocetin, most preferably crocin-3 and crocetin.
  • the hydroxyl group at the 1-position of the sugar is preferably ester-bonded to the carboxyl group of crocetin.
  • the carotenoid glycoside and / or crocetin may be in a purified state or in a state where other components are mixed.
  • a carotenoid glycoside when used as the component (ii), a natural pigment containing a carotenoid glycoside can be used.
  • gardenia yellow and saffron dyes contain crocin and crocin-3, so gardenia yellow and saffron dyes are sources of the component (ii), and are conjugated hardly soluble or insoluble water. Since the solubilization ability or water dispersibility can be improved, it can be suitably used in the composition of the present invention.
  • carotenoid glycoside and / or crocetin are not particularly limited, and those extracted from natural products such as plants, animals and microorganisms, those obtained by glycosylation of natural carotenoids or retinoids, fermentation Any of those obtained by a method or a synthesis method may be used.
  • the content of the component (ii) is not particularly limited, and the form and use of the composition, the type of (i) component to be solubilized or dispersed, the type of component (ii) to be used Depending on the above, it may be set appropriately, for example, 0.00001 to 99.9% by weight, preferably 0.0001 to 99% by weight, more preferably 0.001 to 90% by weight.
  • the ratio of the component (ii) to the component (i) is, for example, 0.00001 to 99.9 parts by weight, preferably 0.0001 to 99 parts by weight of the component (ii) per 100 parts by weight of the component (i). Parts, more preferably 0.001 to 90 parts by weight.
  • composition of the present invention may contain water as a dispersion medium for the component (i) and the component (ii).
  • the composition of the present invention includes an antioxidant, a thickener, a chelating agent, an emulsifying aid, a lower alcohol, a polyhydric alcohol, and a pH adjuster as necessary, as long as the effects of the present invention are not impaired.
  • an additive component such as a buffer may be included.
  • composition of the present invention may contain various components according to its form and use. For example, if the composition of the present invention is in the form of a food or drink product, food materials, nutritional components, and the like may be included. In addition, when the composition of the present invention is made into a pharmaceutical form, a pharmacological component, a pharmaceutically acceptable carrier, an additive, and the like may be included. In addition, when the composition of the present invention is made into a cosmetic form, a functional component, a cosmetically acceptable carrier, an additive, and the like may be included. Furthermore, when making the composition of this invention into a coating-material or a coating agent form, the resin binder etc. may be contained.
  • composition of the present invention can improve the solubilizing ability or dispersibility of ⁇ -conjugated system insoluble or insoluble substances in water without containing a surfactant, an emulsifier, a dispersant, etc. If necessary, a surfactant, an emulsifier, a dispersant and the like may be contained.
  • composition of the present invention may be a liquid containing water as a dispersion medium for the components (i) and (ii), and also removes water to form a semi-solid form such as a paste or a powder form. Alternatively, it may be in a solid form such as a granular form.
  • composition of the present invention may contain water (dispersion medium) together with the components (i) and (ii), and may be in a water-containing state in which the component (i) is solubilized or dispersed.
  • the composition of the present invention once the components (i) and (ii) coexist in the presence of water, the solubilizing ability or dispersibility of the component (i) is improved, and then dried or the like. Even if water is removed, the uniform dispersion of the component (i) is maintained. Therefore, as another embodiment of the composition of the present invention, the composition is produced using an aqueous raw material containing the component (i), the component (ii), and water, and is in a dry state in which water is removed by drying or the like. Also good.
  • composition of the present invention is not particularly limited as long as solubilization or uniform dispersion of the component (i) is required.
  • examples of the form of the composition of the present invention include foods and drinks, pharmaceuticals, and cosmetics.
  • sauces grilled meat sauce, grilled chicken sauce, grilled chicken sauce, dumpling sauce, dumpling sauce, etc.
  • Liquid seasonings of sauces (tonkatsu sauce, curry sauce, white sauce, demiglace sauce, tomato sauce, shrimp sauce, etc.), soups (kimchi hot pot soup, ramen soup, consommé soup, potage soup, clam chowder, etc.), and Processed foods using these liquid seasonings; dairy products such as yogurt and cheese; jams such as strawberry jam, apple jam, blueberry jam and marmalade; processed meat products such as ham, sausage and grilled pork; fish sausage and fish ham , Fish paste products such as fish paste, salmon, bamboo rings, hanpen, deep-fried Satsuma; salt Pickles, pickles such as pickles, miso pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles such as pickles, ume
  • cosmetics specifically, emulsions, creams, lotions, packs, essences, skin cleansers, makeup cosmetics and the like can be mentioned.
  • preparations for internal use such as tablets, granules, powders, capsules, soft capsules, syrups, liquids, etc .
  • for transdermal or transmucosal use such as external preparations, inhalants, suppositories, etc.
  • Formulations injections and the like.
  • the composition of the present invention contains a polyphenol and / or carotenoid as the component (i) and is provided in the form of a food, beverage, medicine, or cosmetic
  • the content of the polyphenol and / or carotenoid is used. What is necessary is just to set suitably in the range mentioned above according to the kind of polyphenol and / or carotenoid, the kind of product, etc. Specifically, it is 0.00001-50 weight%, Preferably it is 0.0001-45 weight%, More preferably Is 0.001 to 40% by weight.
  • the composition of the present invention contains a polyphenol and / or carotenoid as the component (i), it is used for blending the polyphenol and / or carotenoid during the production of the food, beverage, medicine, cosmetics, etc. May be provided as a food additive (food and beverage additive, pharmaceutical raw material, cosmetic additive, etc.).
  • a food additive food and beverage additive, pharmaceutical raw material, cosmetic additive, etc.
  • the composition of the present invention may be in a water-containing state or a dry state.
  • the content of polyphenol and / or carotenoid in the additive is appropriately determined within the above-described range according to the type of polyphenol and / or carotenoid used. Specifically, it may be 0.01 to 95% by weight, more preferably 0.05 to 90% by weight.
  • the composition of the present invention is applied as a dispersion of a carbon material such as a black coloring liquid or a conductive coating liquid; the black coloring liquid is applied.
  • a carbon material such as a black coloring liquid or a conductive coating liquid
  • the black coloring liquid is applied.
  • Colored members; conductive members coated with the conductive coating liquid electromagnetically shielding members used for conductive films, electrode members, electronic devices, etc.
  • the content of the carbon material may be appropriately set within the above-described range depending on the type of carbon material used, the use, etc. Is 0.001 to 20% by weight, preferably 0.01 to 10% by weight, more preferably 0.05 to 5% by weight.
  • the composition of the present invention when the composition of the present invention contains a carbon material as the component (i), it may be provided as an additive used for blending the carbon material at the time of manufacturing the products of the various forms. .
  • the compositions of the present invention may be either hydrated or dried.
  • the content of the carbon material in the additive may be appropriately set within the above-described range according to the type of the carbon material used, Specifically, it is 0.01 to 98% by weight, preferably 0.1 to 95% by weight, and more preferably 0.5 to 90% by weight.
  • examples of the form of the composition of the present invention include water-based paints and various products coated with the water-based paint.
  • the content of the organic pigment may be appropriately set within the above-mentioned range depending on the type of organic pigment to be used, application, etc. Is 0.00001 to 50% by weight, preferably 0.0001 to 45% by weight, more preferably 0.001 to 40% by weight.
  • composition of the present invention when the composition of the present invention contains an organic pigment as the component (i), it may be provided as an additive used for blending the organic pigment at the time of manufacturing the products of the various forms. .
  • the composition of the present invention when the composition of the present invention is provided as such an additive, it may be in a water-containing state or a dry state.
  • the content of the organic pigment in the additive may be appropriately set in the above-described range according to the type of the organic pigment used, Specifically, 0.0001 to 98% by weight, preferably 0.001 to 95% by weight, and more preferably 0.01 to 90% by weight.
  • composition (i) is a drug in the composition of the present invention
  • examples of the form of the composition of the present invention include pharmaceuticals (including those for humans and non-humans), agricultural chemicals and the like.
  • pharmaceuticals include internal preparations such as tablets, granules, powders, capsules, soft capsules, syrups, and liquids; transdermal or transmucosal preparations such as external preparations, inhalants, and suppositories; An injection agent etc. are mentioned.
  • specific examples of agricultural chemicals include liquids (including concentrated liquids), powders, granules and the like.
  • composition of the present invention contains a drug as the component (i) and is provided in the form of a pharmaceutical or agrochemical
  • the content of the drug is described above according to the type, dosage form, etc. of the drug used.
  • the amount may be appropriately set within the range, and specifically, 0.00001 to 98% by weight, preferably 0.0001 to 95% by weight, and more preferably 0.001 to 90% by weight.
  • the composition of the present invention contains a drug as the component (i), it is provided as an additive (such as a pharmaceutical raw material for agricultural chemicals) used for blending the drug when the pharmaceutical or agricultural chemical is manufactured. May be.
  • an additive such as a pharmaceutical raw material for agricultural chemicals
  • the composition of the present invention may be in a water-containing state or a dry state.
  • the content of the drug in the additive may be appropriately set within the above-described range depending on the type of drug used, etc. Is 0.0001 to 98% by weight, preferably 0.001 to 95% by weight, and more preferably 0.01 to 90% by weight.
  • composition of the manufacturing method of the present invention is a liquid
  • water may be prepared by adding other additive components are mixed according to component (i), (ii) component, and need .
  • component (i) and (ii) are added and mixed together in the presence of water, the component (i) is solubilized or stably dispersed in water.
  • polyphenol and / or carotenoid is used as component (i), it becomes solubilized by coexistence with component (ii), and when carbon material is used as component (i), Coexistence and stable dispersion.
  • component (i) When the component (i) is in the form of micelles with a surfactant or an emulsifier, coexistence with the component (ii) may result in insufficient solubility or dispersibility of ⁇ -conjugated system insoluble or insoluble substances. In addition, since it may take time until the solubilized state and the dispersed state become favorable, when the (i) component and the (ii) component are allowed to coexist in water during the production of the composition of the present invention.
  • the component (i) is desirably kept in a state in which micelles are not formed with a surfactant or an emulsifier.
  • composition of the present invention is semi-solid or solid
  • water is removed, and if necessary, semi-solid such as paste What is necessary is just to use for the shaping
  • composition of the present invention provided in the form of an additive, the composition of the present invention in the final product form (product in which the component (i) is adjusted to the concentration at the time of final use) is produced.
  • the component (ii) comprises a ⁇ -conjugated system
  • the component (ii) can also be used as a solubilizing or dispersing agent for a hardly soluble or insoluble substance of a ⁇ -conjugated system.
  • the solubilizing or dispersing agent of the present invention is added to various products containing a ⁇ -conjugated system poorly soluble or insoluble substance and water, so that the ⁇ -conjugated system poorly soluble or insoluble substance can be solubilized or dispersed in water. Used to improve performance.
  • the product to which the solubilizing or dispersing agent of the present invention is applied is not particularly limited as long as it contains a ⁇ -conjugated system poorly soluble or insoluble material and water. Products in the form, aqueous raw materials used in the manufacture of the products in the various forms described above, and the like.
  • component (ii) which is an active ingredient of the solubilizing or dispersing agent of the present invention, are as described above. Further, in the solubilizing or dispersing agent of the present invention, the kind of the slightly soluble or insoluble substance of the ⁇ -conjugated system to be solubilized or dispersed is as described above.
  • a method for solubilizing or dispersing a ⁇ -conjugated system hardly soluble or insoluble substance using the component (ii) is provided.
  • the type and amount of each component used are as described above.
  • Test example 1 A solution having the composition shown in Table 1 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
  • Test example 2 In Test Example 1, the effect of solubilizing resveratrol was observed in gardenia yellow, in order to evaluate which component contained in gardenia yellow contributes to solubilization of resveratrol. The following tests were conducted.
  • a solution having the composition shown in Table 3 was prepared. Specifically, a predetermined amount of crocin solution, crocin-3 solution, or purified water and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
  • FIG. 2 shows the results of observing the appearance of the obtained liquid agents (Examples 6 and 7, Comparative Example 4).
  • resveratrol could be solubilized by crocin or crocin-3.
  • Test example 3 A solution having the composition shown in Table 5 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of curcumin solution were added in this order, and the mixture was sufficiently stirred by vortexing.
  • Test example 4 A solution having the composition shown in Table 6 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of quercetin solution were added in this order, and the mixture was sufficiently stirred by vortexing.
  • Test Example 5 A dispersion having the composition shown in Table 7 was prepared. Specifically, a predetermined amount of gardenia yellow liquid or purified water and a predetermined amount of carbon nanotubes were added in this order and sufficiently stirred by vortexing.
  • Test Example 6 A solution having the composition shown in Table 8 was prepared. Specifically, a predetermined amount of 13-cis-crocetin solution, a predetermined amount of purified water, and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
  • Test Example 1 it was found that resveratrol can be solubilized by gardenia yellow, and in Test Example 2, resveratrol was solubilized by crocin-3 and / or Or it became clear that crocin contributed. Furthermore, in Test Examples 3 and 4, it was also revealed that curcumin and quercetin can be solubilized by gardenia yellow. This is because conjugated double bond moieties present in sparingly soluble polyphenols such as resveratrol, curcumin, quercetin, etc. attract crocin-3 and / or conjugated double bond moieties of crocin by ⁇ - ⁇ interaction. This is probably because accumulation of hardly soluble polyphenols was suppressed, and water solubility was further imparted by crocin-3 and / or the gentiobiose portion of crocin.
  • crocetin since the action of solubilizing resveratrol was also observed in crocetin, crocetin also has a water-solubilizing ability or water dispersibility of ⁇ -conjugated system insoluble or insoluble substances. It became clear that it could be improved.

Abstract

The purpose of the present invention is to provide a composition for enhancing the solubility in water or water dispersibility of a poorly soluble or insoluble substance having a π-conjugated system. By allowing carotenoid glycosides and/or crocetin to coexist with a poorly water-soluble or water-insoluble substance having a π-conjugated system, the solubility in water or water dispersibility of the poorly water-soluble or water-insoluble substance having a π-conjugated system can be greatly increased.

Description

π共役系の難溶性又は不溶性物質の可溶化又は分散化組成物Solubilized or dispersed composition of π-conjugated system poorly soluble or insoluble substance
　本発明は、π共役系の難溶性又は不溶性物質の可溶化又は分散化組成物に関する。より具体的には、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させた組成物に関する。 The present invention relates to a solubilized or dispersed composition of a π-conjugated system hardly soluble or insoluble substance. More specifically, the present invention relates to a composition having improved solubility or water dispersibility of a π-conjugated system poorly soluble or insoluble substance in water.
　食品、化粧料、医薬品、化学、電子等の分野において、複数の二重結合が単結合を挟んで交互に連なっている状態になっているπ共役系の機能性物質が多く利用さている。例えば、色素として利用されている物質の多くはπ共役系の物質である。また、食品分野では、π共役系の物質であるポリフェノールは、優れた抗酸化力を有しており、抗動脈硬化、抗アレルギー、血流増強等の効果が期待されるため、健康食品の重要な成分として認識されている。また、化学や電子分野では、π共役系の物質であるカーボンナノチューブ等の炭素材料は、超高集積化が可能な分子素子、水素を始めとする各種ガスの吸蔵材料、電界放出ディスプレー（ＦＥＤ）用部材、電極材料、樹脂成形品用添加材などの機能性物質として注目されている。 In fields such as food, cosmetics, pharmaceuticals, chemistry, and electronics, π-conjugated functional substances in which a plurality of double bonds are alternately connected with a single bond interposed therebetween are often used. For example, many of the substances used as dyes are π-conjugated substances. In addition, in the food field, polyphenols, which are π-conjugated substances, have excellent antioxidant power and are expected to be effective in anti-arteriosclerosis, anti-allergy, blood flow enhancement, etc. It is recognized as an important component. In the chemical and electronic fields, carbon materials such as carbon nanotubes, which are π-conjugated substances, are molecular devices that can be highly integrated, occluded materials of various gases such as hydrogen, and field emission displays (FEDs). It has been attracting attention as a functional substance such as a member for use, an electrode material, and an additive for resin molded products.
　一方、π共役系の物質は、π－π相互作用によって自己集合し易いという特性があり、水に対して難溶性のものや不溶性で水への分散能が低いものが多く存在している。そのため、例えば、難溶性のポリフェノールを、清涼飲料等の水性食品へ使用する場合には、難溶性のポリフェノールの可溶化又は分散性の向上を図ることが必要になる。また、カーボンナノチューブ等の炭素材料を利用して導電性皮膜を形成する場合には、不溶性の炭素材料を均一に分散させる技術が不可欠である。このように、π共役系の難溶性又は不溶性物質を水系で使用する場合には、可溶化能又は分散化能を向上させることが求められる。 On the other hand, π-conjugated substances have the property of being easily self-assembled by π-π interaction, and there are many substances that are hardly soluble in water or insoluble and have low dispersibility in water. Therefore, for example, when using poorly soluble polyphenols in aqueous foods such as soft drinks, it is necessary to improve the solubility or dispersibility of the hardly soluble polyphenols. In addition, when forming a conductive film using a carbon material such as carbon nanotube, a technique for uniformly dispersing an insoluble carbon material is indispensable. As described above, when a π-conjugated hardly soluble or insoluble substance is used in an aqueous system, it is required to improve the solubilizing ability or dispersing ability.
　従来、π共役系の難溶性又は不溶性物質の可溶化又は分散性の向上を図る技術は種々提案されている。例えば、難溶性のポリフェノールを水に分散させる技術としては、クルクミンをシクロデキストリンで包接する方法（特許文献１）、難水溶性のポリフェノール類に糖を付加する方法（特許文献２）等が報告されている。また、単層カーボンナノチューブを水に分散する方法としては、水溶性キシランを使用して樹脂及びカーボンナノチューブの分散安定性を図る方法（特許文献３）、カーボンナノチューブをβ１，３－グルカンと複合化させる方法（特許文献４）が報告されている。 Conventionally, various techniques for improving the solubilization or dispersibility of a π-conjugated poorly soluble or insoluble substance have been proposed. For example, as a technique for dispersing poorly soluble polyphenols in water, a method of including curcumin with cyclodextrin (Patent Document 1), a method of adding sugar to poorly water-soluble polyphenols (Patent Document 2), etc. have been reported. ing. In addition, as a method for dispersing single-walled carbon nanotubes in water, a method for achieving dispersion stability of resin and carbon nanotubes using water-soluble xylan (Patent Document 3), and carbon nanotubes are combined with β1,3-glucan The method (patent document 4) to make is reported.
　しかしながら、特許文献１～４の技術は、π共役系の物質全般に適用できるものではなく、難溶性又は不溶性の物質の種類に応じて、可溶化又は分散させる処方を設計しなければならず、適用可能なπ共役系の物質に制約があり、汎用性の点で欠点がある。そこで、π共役系の難溶性又は不溶性物質の種類によって制約を受けることなく、可溶化能又は分散性を向上させ得る技術を確立できれば、食品、化粧料、医薬品、化学、電子等の様々な分野における効率化・技術革新への貢献が期待できる。 However, the techniques of Patent Documents 1 to 4 are not applicable to π-conjugated substances in general, and a formulation to be solubilized or dispersed must be designed according to the kind of hardly soluble or insoluble substances. There are limitations on applicable π-conjugated materials, and there are drawbacks in terms of versatility. Therefore, if technology capable of improving the solubilization ability or dispersibility is established without being restricted by the kind of a π-conjugated system insoluble or insoluble, various fields such as food, cosmetics, pharmaceuticals, chemistry, and electronics can be established. Can contribute to efficiency and technological innovation.
特開２００６－１１１５３４号公報JP 2006-111534 A 特開２０１３－４２７１２号公報JP 2013-42712 A 特開２００７－２１７６８４号公報JP 2007-217684 A 特開２００５－１０４７６２号公報JP 2005-104762 A
　本発明の目的は、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させる組成物を提供することである。 An object of the present invention is to provide a composition that improves the solubilization ability or water dispersibility of a π-conjugated system poorly soluble or insoluble substance in water.
　本発明者等は、前記課題を解決すべく鋭意検討を行ったところ、π共役系の水難溶性又は水不溶性物質と共にカロテノイド配糖体及び／又はクロセチンを共存させることにより、π共役系の水難溶性又は水不溶性物質の水への可溶化能又は水分散性が格段に向上し得ることを見出した。本発明は、かかる知見に基づいて更に検討を重ねることにより完成したものである。 The inventors of the present invention have made extensive studies to solve the above-mentioned problems. As a result, carotenoid glycosides and / or crocetin are allowed to coexist with a poorly water-soluble or water-insoluble substance of a π-conjugated system, thereby making the π-conjugated system poorly water-soluble. Alternatively, it has been found that the water solubilizing ability or water dispersibility of a water-insoluble substance can be remarkably improved. The present invention has been completed by further studies based on such knowledge.
　即ち、本発明は、下記に掲げる態様の発明を提供する。
項１．　(i)π共役系の水難溶性又は水不溶性物質、及び(ii)カロテノイド配糖体及び／又はクロセチンを含有することを特徴とする、π共役系の難溶性又は不溶性物質の可溶化又は分散化用の組成物。
項２．　前記(i)成分が、水難溶性又は水不溶性ポリフェノール、水難溶性又は水不溶性カロテノイド、水難溶性又は水不溶性炭素材料、水難溶性又は水不溶性有機顔料、及び水難溶性又は水不溶性薬物よりなる群から選択される少なくとも１種である、項１に記載の組成物。
項３．　前記(ii)成分が、クロセチン配糖体である、項１又は２に記載の組成物。
項４．　前記(ii)成分が、クロシン－３及び／又はクロシンである、項１～３のいずれかに記載の組成物。
項５．　前記(ii)成分として、クチナシ黄色素を含む、項１～４のいずれかに記載の組成物。
項６．　前記(i)成分がポリフェノール及び／又はカロテノイドであり、飲食品、医薬品、化粧料、又はこれらの添加剤の形態である、項１～５のいずれかに記載の組成物。
項７．　前記(i)成分が炭素材料であり、当該炭素材料の分散液の形態である、項１～５のいずれかに記載の組成物。
項８．　カロテノイド配糖体及び／又はクロセチンを有効成分とする、π共役系の水難溶性の可溶化又は分散化剤。
項９．　水難溶性ポリフェノール及び／又はカロテノイドの可溶化剤である、項８に記載のπ共役系の水難溶性の可溶化又は分散化剤。
項１０．　炭素材料の分散化剤である、項８に記載のπ共役系の水難溶性の可溶化又は分散化剤。
項１１．　カロテノイド配糖体及び／又はクロセチンの存在下で、π共役系の水難溶性又は水不溶性物質を水に可溶化又は分散化させる工程を含む、π共役系の水難溶性又は水不溶性物質の可溶化又は分散化方法。
項１２．　カロテノイド配糖体及び／又はクロセチンの、π共役系の水難溶性の可溶化又は分散化剤としての使用。 That is, this invention provides the invention of the aspect hung up below.
Item 1. Solubilization or dispersion of a π-conjugated system poorly soluble or insoluble substance characterized by containing (i) a π-conjugated system poorly water-soluble or water-insoluble substance, and (ii) a carotenoid glycoside and / or crocetin. Composition.
Item 2. The component (i) is selected from the group consisting of poorly water-soluble or water-insoluble polyphenols, poorly water-soluble or water-insoluble carotenoids, poorly water-soluble or water-insoluble carbon materials, poorly water-soluble or water-insoluble organic pigments, and poorly water-soluble or water-insoluble drugs. Item 2. The composition according to Item 1, which is at least one selected from the group consisting of:
Item 3. Item 3. The composition according to Item 1 or 2, wherein the component (ii) is crocetin glycoside.
Item 4. Item 4. The composition according to any one of Items 1 to 3, wherein the component (ii) is crocin-3 and / or crocin.
Item 5. Item 5. The composition according to any one of Items 1 to 4, comprising Gardenia yellow as the component (ii).
Item 6. Item 6. The composition according to any one of Items 1 to 5, wherein the component (i) is a polyphenol and / or carotenoid and is in the form of a food or drink, a pharmaceutical product, a cosmetic, or an additive thereof.
Item 7. Item 6. The composition according to any one of Items 1 to 5, wherein the component (i) is a carbon material and is in the form of a dispersion of the carbon material.
Item 8. A π-conjugated poorly water-soluble solubilizing or dispersing agent containing carotenoid glycoside and / or crocetin as active ingredients.
Item 9. Item 9. The π-conjugated poorly water-soluble solubilizer or dispersant according to Item 8, which is a poorly water-soluble polyphenol and / or carotenoid solubilizer.
Item 10. Item 9. A π-conjugated poorly water-soluble solubilizing or dispersing agent according to Item 8, which is a dispersing agent for a carbon material.
Item 11. Solubilizing or dissolving a π-conjugated poorly water-soluble or water-insoluble substance, comprising the step of solubilizing or dispersing the π-conjugated poorly water-soluble or water-insoluble substance in water in the presence of a carotenoid glycoside and / or crocetin Decentralization method.
Item 12. Use of carotenoid glycoside and / or crocetin as a π-conjugated poorly water-soluble solubilizer or dispersant.
　本発明によれば、π共役系の水難溶性又は水不溶性物質と共に、カロテノイド配糖体及び／又はクロセチンを共存させることによって、π共役系の水難溶性又は水不溶性物質の水への可溶化能又は水分散性を向上させることができる。例えば、π共役系の水難溶性物質であるポリフェノールは、食品や医薬の分野において使用されており、本発明によってポリフェノールの可溶化能を向上させることにより、生体吸収性を高め、ポリフェノールの機能性を享受し易くすることができる。また、π共役系の水不溶性物質であるカーボンナノチューブは、導電性フィルムや導電性塗料等に使用されており、これらの技術分野でも、カーボンナノチューブの分散性の向上によって、品質向上や生産性の向上に寄与することができる。 According to the present invention, by making a carotenoid glycoside and / or crocetin coexist with a π-conjugated poorly water-soluble or water-insoluble substance, the ability to solubilize a π-conjugated poorly water-soluble or water-insoluble substance in water or Water dispersibility can be improved. For example, polyphenols, which are π-conjugated poorly water-soluble substances, are used in the field of food and medicine. By improving the solubilization ability of polyphenols according to the present invention, the bioabsorbability is increased and the functionality of polyphenols is increased. It can be easily enjoyed. In addition, carbon nanotubes, which are π-conjugated water-insoluble substances, are used in conductive films and conductive paints. In these technical fields, the improvement in quality and productivity can be achieved by improving the dispersibility of carbon nanotubes. It can contribute to improvement.
　なお、限定的な解釈を望むものではないが、本発明によって、π共役系の水難溶性又は水不溶性物質の水への可溶化能又は水分散性が向上するメカニズムは、後述する試験例１～６の結果に基づけば、次のように類推される。π共役系の水難溶性又は水不溶性物質は、π－π相互作用によって自己集合し易く、水への溶解性が劣る要因になっている。一方、カロテノイド配糖体及びクロセチンにも共役二重結合が存在している。このカロテノイド配糖体及びクロセチンの共役二重結合部分がπ共役系の水難溶性又は水不溶性物質の表面にπ－π相互作用によって引き付けられ、その結果、π共役系の水難溶性又は水不溶性物質同士の集積を阻害し、更にカロテノイド配糖体の糖成分及びクロセチンのカルボキシル基によって水溶性が付与される。その結果、π共役系の水難溶性又は水不溶性物質の水への可溶化能又は水分散性が向上すると考えられる。 Although not intended to be limited to interpretation, the mechanism by which the present invention improves the solubilizing ability or water dispersibility of π-conjugated system poorly water-soluble or water-insoluble substances in water is described in Test Examples 1 to Based on the result of 6, it can be inferred as follows. A π-conjugated system poorly water-soluble or water-insoluble substance is easily self-assembled by a π-π interaction, which is a factor of poor solubility in water. On the other hand, conjugated double bonds also exist in carotenoid glycosides and crocetin. The conjugated double bond part of this carotenoid glycoside and crocetin is attracted to the surface of the π-conjugated system poorly water-soluble or water-insoluble substance by π-π interaction. As a result, the π-conjugated system poorly water-soluble or water-insoluble substance In addition, water solubility is imparted by the sugar component of the carotenoid glycoside and the carboxyl group of crocetin. As a result, it is considered that the water-solubilizing ability or water dispersibility of a π-conjugated system poorly water-soluble or water-insoluble substance is improved.
試験例１において、製造したレスベラトロールを含む液剤の外観を観察した結果を示す。In Experiment 1, the result of having observed the external appearance of the liquid agent containing the manufactured resveratrol is shown. 試験例２において、製造したレスベラトロールを含む液剤の外観を観察した結果を示す。In Test Example 2, the result of observing the appearance of a liquid preparation containing resveratrol produced is shown. 試験例３において、製造したクルクミンを含む液剤の外観を観察した結果を示す。In Test Example 3, the result of observing the appearance of the liquid preparation containing curcumin produced is shown. 試験例４において、製造したケルセチンを含む液剤の外観を観察した結果を示す。In Test Example 4, the result of observing the appearance of a liquid preparation containing quercetin produced is shown. 試験例５において、製造したカーボンナノチューブを含む分散液の外観を観察した結果を示す。In Test Example 5, the result of observing the appearance of the produced dispersion containing carbon nanotubes is shown. 試験例６において、製造したレスベラトロールを含む液剤の外観を観察した結果を示す。In Experiment 6, the result of having observed the external appearance of the liquid agent containing the manufactured resveratrol is shown.
１．π共役系の難溶性又は不溶性物質の可溶化又は分散化組成物
　本発明の組成物は、π共役系の難溶性又は不溶性物質の可溶化又は分散化用の組成物であって、(i)π共役系の水難溶性又は水不溶性物質、及び(ii)カロテノイド配糖体及び／又はクロセチンを含有することを特徴とする。以下、本発明の組成物について詳述する。 1. Composition of the present invention is a composition for solubilization or dispersion of a π-conjugated system poorly soluble or insoluble substance, comprising (i) It contains a π-conjugated system poorly water-soluble or water-insoluble substance, and (ii) carotenoid glycoside and / or crocetin. Hereinafter, the composition of the present invention will be described in detail.
(i)π共役系の水難溶性又は水不溶性物質
　本発明は、水に可溶化又は分散させる対象物として、π共役系の水難溶性又は水不溶性物質（(i)成分と略記することもある）を含有する。 (i) π-conjugated system poorly water-soluble or water-insoluble substance In the present invention, as an object to be solubilized or dispersed in water, π-conjugated system poorly water-soluble or water-insoluble substance (sometimes abbreviated as (i) component) Containing.
　「π共役系」とは、複数の二重結合が単結合を挟んで交互に連なっている状態を意味し、本発明では、π共役系を有する物質の内、水に対して難溶性又は不溶性を示す物質が使用される。より具体的には、π共役系の物質の好適な例として、分子内に少なくとも３つの二重結合を含むπ共役系を有している物質（即ち、少なくとも、二重結合・単結合・二重結合・単結合・二重結合を含むπ共役系構造を分子内に有している物質）が挙げられる。また、π共役系を構成する原子としては、特に制限されないが、通常、炭素、酸素、窒素等が挙げられる。例えば、π共役系が炭素原子のみで形成されている物質としてベンゼン（３つの二重結合からなるπ共役系分子）、π共役系が炭素原子と窒素原子で形成されている物質としてピリジン（３つの二重結合からなるπ共役系分子）及びピリミジン（３つの二重結合からなるπ共役系分子）、π共役系が炭素原子と酸素原子で形成されている物質として桂皮酸（５つの二重結合からなるπ共役系分子）が挙げられる。 “Π-conjugated system” means a state in which a plurality of double bonds are alternately connected with a single bond interposed therebetween. In the present invention, among substances having a π-conjugated system, it is hardly soluble or insoluble in water. A substance showing is used. More specifically, as a suitable example of a π-conjugated substance, a substance having a π-conjugated system containing at least three double bonds in the molecule (that is, at least a double bond, a single bond, and two A substance having a π-conjugated structure including a heavy bond, a single bond and a double bond in the molecule). In addition, the atom constituting the π-conjugated system is not particularly limited, but usually includes carbon, oxygen, nitrogen and the like. For example, benzene (a π-conjugated molecule consisting of three double bonds) is a substance in which a π-conjugated system is formed of only carbon atoms, and pyridine (3 is a substance in which a π-conjugated system is formed of carbon and nitrogen atoms. Cinnamic acid (5 double bonds) as a substance in which a π conjugated system is formed of carbon atoms and oxygen atoms, and a pyrimidine (π conjugated molecule composed of 3 double bonds) A π-conjugated molecule composed of a bond).
　本発明において、「難溶性」とは、２０℃において、溶質１ｇ又は１ｍＬを溶かすに要する水の量が、３０ｍＬ以上１００００ｍｌ未満であることを意味する。本発明では、水への溶解度が非常に低いπ共役系の難溶性物質に対しても、可溶化又は分散性の向上を図ることができる。かかる本発明の効果を鑑みれば、π共役系の難溶性物質として、２０℃において、１ｇ又は１ｍＬを溶かすに要する水の量が、好ましくは１００ｍＬ以上１００００ｍｌ未満、更に好ましくは１０0０ｍＬ以上１００００ｍｌ未満である難溶性を示すものが挙げられる。 In the present invention, “slightly soluble” means that the amount of water required to dissolve 1 g or 1 mL of solute at 20 ° C. is 30 mL or more and less than 10000 mL. In the present invention, it is possible to improve solubilization or dispersibility even for a π-conjugated system poorly soluble substance having very low solubility in water. In view of the effect of the present invention, the amount of water required to dissolve 1 g or 1 mL at 20 ° C. as a π-conjugated hardly soluble substance is preferably 100 mL or more and less than 10,000 mL, more preferably 100 mL or more and less than 10,000 mL. What shows a poor solubility is mentioned.
　また、本発明において、「不溶性」とは、２０℃において、溶質１ｇ又は１ｍＬを溶かすに要する水の量１００００ｍｌ以上であることを意味する。当該「不溶性」には、水に全く溶けないものも包含される。 In the present invention, “insoluble” means that the amount of water required to dissolve 1 g or 1 mL of solute at 20 ° C. is 10,000 ml or more. The “insoluble” includes those that are completely insoluble in water.
　本発明で使用されるπ共役系の難溶性又は不溶性物質の種類については、特に制限されず、水への可溶化又能は分散性の向上が求められているものであればよいが、例えば、難溶性又は不溶性のポリフェノール、難溶性又は不溶性のカロテノイド、不溶性の炭素材料、難溶性又は不溶性の有機顔料、難溶性又は不溶性の薬物等が挙げられる。 The kind of the hardly soluble or insoluble material of the π-conjugated system used in the present invention is not particularly limited, and any solubilization or ability in water is required as long as improvement in dispersibility is required. , Hardly soluble or insoluble polyphenols, hardly soluble or insoluble carotenoids, insoluble carbon materials, hardly soluble or insoluble organic pigments, hardly soluble or insoluble drugs, and the like.
　難溶性又は不溶性のポリフェノールとしては、具体的には、カテキン、アントシアニン、ヘスペリジン、ルテオリン、ケルセチン、ルチン、ダイゼイン、ゲニスティン等のフラボノイド類；リグナン、クロロゲン酸、クマリン、オイゲノール、セサミン、マグノロール、桂皮酸、コーヒー酸、クマル酸、フェルラ酸等のフェニルプロパノイド類；クルクミン、ショウガオール等のクルクミノイド類；レスベラトロール等のスチルベノイド類；エラグ酸等が挙げられる。これらの難溶性又は不溶性のポリフェノールは、１種単独で使用してもよく、また２種以上を組み合わせて使用してもよい。 Specific examples of poorly soluble or insoluble polyphenols include flavonoids such as catechin, anthocyanin, hesperidin, luteolin, quercetin, rutin, daidzein, genistein; lignan, chlorogenic acid, coumarin, eugenol, sesamin, magnolol, cinnamic acid Phenylpropanoids such as caffeic acid, coumaric acid and ferulic acid; curcuminoids such as curcumin and shogaol; stilbenoids such as resveratrol; ellagic acid and the like. These poorly soluble or insoluble polyphenols may be used alone or in combination of two or more.
　難溶性又は不溶性のカロテノイドとしては、具体的には、α－カロテン、β－カロテン、γ－カロテン、リコペン等のカロテン；アクチニオエリスリトール、カンタキサンチン、カプソルビン、アスタキサンチン、フコキサンチン、ルテイン、ゼアキサンチン、カプサンチン、β－クリプトキサンチン、ビオラキサンチン、これらの誘導体（脂肪酸とのモノエステル体又はジエステル体等）等のキサントフィル；ビキシン、β－８’－アポ－カロテナール（アポカロテナール）、β－１２’－アポ－カロテナール、これらの誘導体（低級又は高級アルコールとのエステル体等）等のアポカルテノイド等が挙げられる。これらの難溶性又は不溶性のカロテノイドは、１種単独で使用してもよく、また２種以上を組み合わせて使用してもよい。 Specific examples of the hardly soluble or insoluble carotenoids include carotenes such as α-carotene, β-carotene, γ-carotene, and lycopene; actinioerythritol, canthaxanthin, capsorbine, astaxanthin, fucoxanthin, lutein, zeaxanthin, and capsanthin. , Β-cryptoxanthin, violaxanthin, derivatives thereof (monoester or diester with fatty acid, etc.), etc .; bixin, β-8′-apo-carotenal (apocarotenal), β-12′-apo-carotenal And apocartenoids such as derivatives thereof (such as esters with lower or higher alcohols). These poorly soluble or insoluble carotenoids may be used singly or in combination of two or more.
　不溶性の炭素材料としては、具体的には、フラーレン、カーボンナノチューブ、グラフェン等が挙げられる。これらの不溶性の炭素材料は、１種単独で使用してもよく、また２種以上を組み合わせて使用してもよい。 Specific examples of the insoluble carbon material include fullerene, carbon nanotube, and graphene. These insoluble carbon materials may be used individually by 1 type, and may be used in combination of 2 or more type.
　難溶性又は不溶性の有機顔料としては、具体的には、ポルフィリン、フタロシアニン、オリゴ（ｐ－）フェニレンビニレン、オリゴ（ｐ－）フェニレンエチニレン、ペリレン、ペリレンビスイミド、フルオレン、アントラセン、テトラセン、ペンタセン、ピレン、アゾベンゼン、スチルベン、ジアリルエテン、オリゴフェニレン、オリゴチオフェン、オキザール系色素等が挙げられる。 Specific examples of the hardly soluble or insoluble organic pigments include porphyrin, phthalocyanine, oligo (p-) phenylene vinylene, oligo (p-) phenylene ethynylene, perylene, perylene bisimide, fluorene, anthracene, tetracene, pentacene, Examples include pyrene, azobenzene, stilbene, diallylethene, oligophenylene, oligothiophene, and oxal dyes.
　難溶性又は不溶性の薬物としては、ヒト又は非ヒト動物の疾患の診断、予防又は治療目的で使用される薬物であってもよく、また農薬であってもよい。難溶性又は不溶性の薬物の内、ヒト又は非ヒト動物の疾患の診断、予防又は治療目的で使用される薬物としては、例えば、メルファラン、タキソール、ダカルバジン、塩酸ドキソルビシン等の抗腫瘍剤；ペニシリン、セファレキシン、テトラサイクリン、ナイスタチン、クロラムフェニコール、トルナフテート等の抗生物質；アスピリン、アミノピリン、フェナセチン、メフェナム酸、フルフェナム酸、インドメタシン等の解熱鎮痛消炎剤；クリノフィブラート、クロフィブラート、フェノフィブラート、ベザフィブラート、コレスチラミン等の抗高脂血症剤；オフロキサシン、塩酸シプロフロキサシン、トシル酸トスフロキサシン、ノルフロキサシン等の抗菌剤；フェノバルビタール、グルテチミド、メタカロン等の催眠鎮静剤；ジアゼパム、ロラゼパム、オキサゾラム等の精神安定剤；フェニトイン、フェノバルビタール、カルバマゼピン、プリミドン、フェナセミド等の抗てんかん剤；ノキシプチリン、フェネルジン等の抗うつ剤；マレイン酸イルソグラジン、オメプラゾール、ランソプラゾール等の消化器系疾患治療剤；フマル酸クレマスチン、塩酸シプロヘプタジン、塩酸フェキソフェナジン等のアレルギー性疾患治療剤；アラセプリル、塩酸ニカルジピン、フェロジピン等の高血圧治療剤；クロフィブラート、シンフィブラート、ニコモール等の動脈硬化治療剤；酢酸トコフェロール、ニコチン酸ベンジルエステル、トラゾリン等の血行促進剤；トルブタミド、グリベンクラミド、グリクラジド、トログリタゾン、エパルレスタット等の糖尿病治療剤；ヘキセストロール、エストリオール、安息香酸エストラジオール等のホルモン剤；フルタミド、ビカルタミド等の抗アンドロゲン剤；強心用薬剤；ピンドロール、ナドロール、塩酸アロチノロール等の不整脈用薬剤；ポリチアジド、クロルタリドン、トリアムテレン等の利尿用薬剤；塩酸ジブカイン、アミノ安息香酸エチル、塩酸プロカイン等の局所麻酔剤；駆虫薬；抗不整脈薬；抗凝固剤；抗ヒスタミン剤；抗ムスカリン剤；抗マイコバクテリア剤；免疫抑制剤；抗甲状腺薬；抗ウィルス剤；不安緩和性鎮静薬；収れん薬；β－アドレナリン受容体遮断薬；心筋変力作用剤；造影剤；コルチコステロイド；咳抑制剤；診断用イメージング剤；利尿剤；ドパミン作用剤；血止め薬；脂質調整剤；筋肉弛緩薬；副交感神経作用薬；甲状腺カルシトニン及びビホスホネート；プロスタグラジン；放射性医薬；性ホルモン；刺激剤；食欲抑制剤；交感神経作用薬；甲状腺剤；血管拡張剤；キサンテン等が挙げられる。また、難溶性又は不溶性の薬物の内、農薬としては、例えば、アクリナトリン、アザメチホス、アジンホスメチル等の難溶性殺虫物質；アゾキシストロビン、ベナラキシル、ベノミル、ビテルタノール等の難溶性殺菌物質；アザフェニジン、テニルクロール、ビフェノックス、スルフェントラゾン等の難溶性除草物質；６－ベンジルアミノプリン、フルメトラリン、ホルクロルフェニュロン等の難溶性植物生長調節物質を例示することができる。これらの難溶性又は不溶性の薬物は、１種単独で使用してもよく、また２種以上を組み合わせて使用してもよい。 The poorly soluble or insoluble drug may be a drug used for the diagnosis, prevention or treatment of a disease in a human or non-human animal, or may be an agrochemical. Among the hardly soluble or insoluble drugs, as drugs used for the diagnosis, prevention or treatment of diseases of humans or non-human animals, for example, antitumor agents such as melphalan, taxol, dacarbazine, doxorubicin hydrochloride; penicillin, Antibiotics such as cephalexin, tetracycline, nystatin, chloramphenicol, tolnaftate; antipyretic analgesic / anti-inflammatory agents such as aspirin, aminopyrine, phenacetin, mefenamic acid, flufenamic acid, indomethacin; clinofibrate, clofibrate, fenofibrate, bezafibrate, cholestyramine Antihyperlipidemic agents such as ofloxacin, ciprofloxacin hydrochloride, tosufloxacin tosylate, norfloxacin, etc .; hypnotic sedatives such as phenobarbital, glutethimide, metacaron; diazepa Tranquilizers such as lorazepam and oxazolam; antiepileptic agents such as phenytoin, phenobarbital, carbamazepine, primidone, and phenacemide; antidepressants such as noxiptillin and phenelzine; therapeutic agents for digestive system diseases such as irsogladine maleate, omeprazole, and lansoprazole Therapeutic agents for allergic diseases such as clemastine fumarate, cyproheptadine hydrochloride, fexofenadine hydrochloride; therapeutic agents for hypertension such as alacepril, nicardipine hydrochloride, felodipine; therapeutic agents for arteriosclerosis such as clofibrate, simfibrate, nicomol; tocopherol acetate, nicotine Blood circulation promoters such as acid benzyl ester and trazoline; Antidiabetics such as tolbutamide, glibenclamide, gliclazide, troglitazone, epalrestat; Hexestrow Hormonal agents such as estradiol and estradiol benzoate; antiandrogenic agents such as flutamide and bicalutamide; cardiotonic agents; arrhythmic agents such as pindolol, nadolol and arotinolol hydrochloride; diuretics such as polythiazide, chlorthalidone and triamterene; dibucaine hydrochloride Anesthesia drugs; antiarrhythmic agents; anticoagulants; anticoagulants; antihistamines; antimuscarinic agents; antimycobacterial agents; immunosuppressive agents; antithyroid agents; antiviral agents; Sedatives; astringents; β-adrenergic receptor blockers; myocardial inotropic agents; contrast agents; corticosteroids; cough suppressants; diagnostic imaging agents; diuretics; Muscle relaxants; parasympathomimetics; thyroid calcitonin and biphos Sulfonate; prostaglandin; radiopharmaceuticals; hormones; stimulants; appetite suppressants; sympathomimetics; thyroid; vasodilators; xanthene, and the like. Among the hardly soluble or insoluble drugs, the agricultural chemicals include, for example, sparingly soluble insecticides such as acrinathrin, azamethiphos, and azinephosmethyl; sparingly soluble fungicides such as azoxystrobin, benalaxyl, benomyl, and viteltanol; azaphenidine, tenylchlor, Examples include poorly soluble herbicides such as bifenox and sulfentrazone; and poorly soluble plant growth regulators such as 6-benzylaminopurine, flumetraline and forchlorfenuron. These poorly soluble or insoluble drugs may be used alone or in combination of two or more.
　これらのπ共役系の難溶性又は不溶性物質は、１種単独で使用してもよく、また２種以上を組み合わせて使用してもよい。 These π-conjugated hardly soluble or insoluble substances may be used alone or in combination of two or more.
　これらのπ共役系の難溶性又は不溶性物質は、精製された状態であってもよいが、他の成分が混在する状態のものであってもよい。例えば、共役系の難溶性又は不溶性物質として、難溶性又は不溶性のポリフェノールを使用する場合であれば、難溶性又は不溶性のポリフェノールを含む植物から抽出された植物抽出物であってもよい。また、共役系の難溶性又は不溶性物質として、難溶性又は不溶性のカロテノイドを使用する場合であれば、トウガラシ色素（パプリカ色素、パプリカオレオレジン）、アナトー色素、イモカロテン、デュナリエラカロテン、ニンジンカロテン、エビ色素、オキアミ色素、オレンジ色素、カニ色素、トウモロコシ色素、トマト色素、パーム油カロテン、ファフィア色素、ベニノキ末色素、ヘマトコッカス藻色素、マリーゴールド色素等の、難溶性又は不溶性のカロテノイドを含む天然色素であってもよい。 These π-conjugated hardly soluble or insoluble substances may be in a purified state or in a state where other components are mixed. For example, if a poorly soluble or insoluble polyphenol is used as the conjugated hardly soluble or insoluble substance, a plant extract extracted from a plant containing the hardly soluble or insoluble polyphenol may be used. In addition, when a sparingly soluble or insoluble carotenoid is used as a conjugated difficultly soluble or insoluble substance, red pepper dye (paprika dye, paprika oleoresin), anato dye, imo carotene, Dunaliella carotene, carrot carotene, shrimp Natural pigments that contain sparingly soluble or insoluble carotenoids such as pigments, krill pigments, orange pigments, crab pigments, corn pigments, tomato pigments, palm oil carotene, phafia pigments, albacore pigments, hematococcus algae pigments, marigold pigments, etc. There may be.
　これらのπ共役系の難溶性又は不溶性物質の中でも、水への可溶化能又は水分散性をより一層効果的に向上させるという観点から、好ましくは難溶性又は不溶性のポリフェノール、不溶性の炭素材料、更に好ましくはレスベラトロール、クルクミン、ケルセチン、カーボンナノチューブが挙げられる。 Among these π-conjugated hardly soluble or insoluble substances, from the viewpoint of more effectively improving the water solubilization ability or water dispersibility, preferably poorly soluble or insoluble polyphenols, insoluble carbon materials, More preferred are resveratrol, curcumin, quercetin, and carbon nanotubes.
　本発明の組成物において、(i)成分の含有量については、特に制限されず、当該組成物の形態や用途、(i)成分の種類等に応じて適宜設定すればよいが、例えば０．００００１～９９．９重量％、好ましくは０．０００１～９９重量％、更に好ましくは０．００１～９０重量％が挙げられる。 In the composition of the present invention, the content of the component (i) is not particularly limited, and may be appropriately set according to the form and use of the composition, the type of the component (i), etc. 00001 to 99.9% by weight, preferably 0.0001 to 99% by weight, and more preferably 0.001 to 90% by weight.
(ii)カロテノイド配糖体及び／又はクロセチン
　本発明の組成物は、前記(i)成分と共に、カロテノイド配糖体及び／又はクロセチン（(ii)成分と表記することもある）を含有する。このように、共役系の難溶性又は不溶性物質と共にカロテノイド配糖体及び／又はクロセチンを共存させることによって、共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させることが可能になる。 (ii) Carotenoid glycoside and / or crocetin The composition of the present invention contains a carotenoid glycoside and / or crocetin (also referred to as (ii) component) together with the component (i). In this way, by making a carotenoid glycoside and / or crocetin coexist with a conjugated hardly soluble or insoluble substance, the solubilizing ability or water dispersibility of the conjugated difficultly soluble or insoluble substance in water is improved. Is possible.
　本発明で使用されるカロテノイド配糖体において、アグリコンであるカロテノイドの種類については、特に制限されないが、例えば、クロセチン、ミコラジシン、ビキシン、β－８’－アポ－カロテナール（アポカロテナール）、β－１２’－アポ－カロテナール等のアポカルテノイド；アクチニオエリスリトール、カンタキサンチン、カプソルビン、アスタキサンチン、フコキサンチン、ルテイン、ゼアキサンチン、カプサンチン、β－クリプトキサンチン、ビオラキサンチン等のキサントフィル等が挙げられる。 In the carotenoid glycoside used in the present invention, the type of carotenoid that is an aglycon is not particularly limited. -Apocartenoids such as apo-carotenal; xanthophylls such as actinioerythritol, canthaxanthin, capsorbin, astaxanthin, fucoxanthin, lutein, zeaxanthin, capsanthin, β-cryptoxanthin, violaxanthin and the like.
　カロテノイド配糖体に付加している糖成分は、単糖類であっても、三糖類、四糖類等のオリゴ糖類であってもよい。当該糖成分として、具体的には、グルコース、グルクロン酸等の単糖類；ゲンチオビオース、マルトース、スクロース、ラクトース、グルクロノシルグルコース、グルクロノシルグルクロン酸等の二糖類；ゲンチオトリオース、マルトトリオース、ラフィノース、パノース、グルクロノシルゲンチオビオース、グルコシルゲンチオビオース等の三糖類等が挙げられる。これらの糖成分の中でも、好ましくは単糖類、二糖類、更に好ましくはグルコース、ゲンチオビオース、特に好ましくはゲンチオビオースが挙げられる。 The sugar component added to the carotenoid glycoside may be a monosaccharide or an oligosaccharide such as a trisaccharide or a tetrasaccharide. Specific examples of the sugar component include monosaccharides such as glucose and glucuronic acid; disaccharides such as gentiobiose, maltose, sucrose, lactose, glucuronosylglucose and glucuronosylglucuronic acid; gentithiotriose, maltotriose, Examples include trisaccharides such as raffinose, panose, glucuronosyl gentiobiose, and glucosyl gentiobiose. Among these sugar components, monosaccharides and disaccharides are preferable, glucose and gentiobiose are more preferable, and gentiobiose is particularly preferable.
　また、カロテノイド配糖体において糖成分（単糖及び／又はオリゴ糖）の付加数については、特に制限されず、アグリコンの１カ所に糖成分（単糖又はオリゴ糖）が付加されている配糖体であっても、アグリコンの２カ所に糖成分（単糖及び／又はオリゴ糖）が付加されている配糖体であってもよい。π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性をより一層効果的に向上させるという観点から、カロテノイド配糖体において糖成分（単糖及び／又はオリゴ糖）の付加数が１であることが好ましい。 In addition, the number of sugar components (monosaccharides and / or oligosaccharides) added to the carotenoid glycoside is not particularly limited, and a glycoside in which a sugar component (monosaccharide or oligosaccharide) is added at one location of the aglycone. It may be a glycoside in which sugar components (monosaccharide and / or oligosaccharide) are added at two positions of an aglycon. Addition of sugar components (monosaccharides and / or oligosaccharides) in carotenoid glycosides from the viewpoint of more effectively improving the solubilization ability or water dispersibility of poorly soluble or insoluble substances of π-conjugated systems The number is preferably 1.
　また、カロテノイド配糖体において、アグリコンと糖成分との結合形態については、特に制限されず、使用するアグリコンの種類に応じて異なるが、例えば、エステル結合、Ｏ－グリコシド結合、Ｃ-グリコシド結合、Ｎ－グリコシド結合等が挙げられる。また、カロテノイド配糖体は、シス－トランス異性体であってもよい。 Further, in the carotenoid glycoside, the binding form between the aglycone and the sugar component is not particularly limited and varies depending on the type of aglycone to be used. For example, an ester bond, an O-glycoside bond, a C-glycoside bond, N-glycoside bond and the like can be mentioned. The carotenoid glycoside may be a cis-trans isomer.
　また、本発明で使用されるクロセチンとしては、トランスクロセチン又はシスクロセチンのいずれか一方でもよく、またこれらの混合物であってもよい。 Also, the crocetin used in the present invention may be either trans crocetin or cis crocetin, or a mixture thereof.
　本発明の組成物において、(ii)成分として、カロテノイド配糖体及びクロセチンの中から１種を選択して使用してもよく、また２種以上を組み合わせて使用してもよい。 In the composition of the present invention, as the component (ii), one type may be selected from carotenoid glycosides and crocetin, or two or more types may be used in combination.
　これらの(ii)成分の中でも、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性をより一層効果的に向上させるという観点から、好ましくはキサントフィル配糖体及びクロセチン、更に好ましくはキサントフィル配糖体及びクロセチン、より好ましくはクロセチン配糖体及びクロセチン、特に好ましくはクロセチンのジゲンチオビオース配糖体［クロシン－３（クロセチン－モノゲンチオビオシドエステル）、クロシン（クロセチン－ジゲンチオビオシドエステル）］及びクロセチン、最も好ましくはクロシン－３及びクロセチンが挙げられる。また、前記クロセチン配糖体及びクロセチンのゲンチオビオース配糖体では、糖の１位の水酸基がクロセチンのカルボキシル基とエステル結合していることが好ましい。 Among these (ii) components, xanthophyll glycosides and crocetin are preferably used from the viewpoint of more effectively improving the solubilization ability or water dispersibility of π-conjugated system insoluble or insoluble substances in water. More preferably xanthophyll glycoside and crocetin, more preferably crocetin glycoside and crocetin, particularly preferably crocetin digentiobiose glycoside [crocin-3 (crocetin-monogenthiobioside ester), crocin (crocetin- Digentiobioside ester)] and crocetin, most preferably crocin-3 and crocetin. In the crocetin glycoside and the gentiobiose glycoside of crocetin, the hydroxyl group at the 1-position of the sugar is preferably ester-bonded to the carboxyl group of crocetin.
　カロテノイド配糖体及び／又はクロセチンは、精製された状態であってもよいが、他の成分が混在する状態のものであってもよい。例えば、(ii)成分としてカロテノイド配糖体を用いる場合には、カロテノイド配糖体を含む天然色素を利用することもできる。特に、クチナシ黄色素及びサフラン色素には、クロシン及びクロシン－３が含まれているので、クチナシ黄色素及びサフラン色素は前記(ii)成分の供給源となり、共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させ得るため、本発明の組成物において好適に使用することができる。 The carotenoid glycoside and / or crocetin may be in a purified state or in a state where other components are mixed. For example, when a carotenoid glycoside is used as the component (ii), a natural pigment containing a carotenoid glycoside can be used. In particular, gardenia yellow and saffron dyes contain crocin and crocin-3, so gardenia yellow and saffron dyes are sources of the component (ii), and are conjugated hardly soluble or insoluble water. Since the solubilization ability or water dispersibility can be improved, it can be suitably used in the composition of the present invention.
　また、カロテノイド配糖体及び／又はクロセチンは、その由来や製法については、特に制限されず、植物、動物、微生物等の天然物から抽出されたもの、天然カロテノイド又はレチノイドを配糖化したもの、発酵法や合成法により得られたもの等のいずれであってもよい。 The origin and production method of carotenoid glycoside and / or crocetin are not particularly limited, and those extracted from natural products such as plants, animals and microorganisms, those obtained by glycosylation of natural carotenoids or retinoids, fermentation Any of those obtained by a method or a synthesis method may be used.
　本発明の組成物において、(ii)成分の含有量については、特に制限されず、当該組成物の形態や用途、可溶化又は分散させる(i)成分の種類、使用する(ii)成分の種類等に応じて適宜設定すればよいが、例えば０．００００１～９９．９重量％、好ましくは０．０００１～９９重量％、更に好ましくは０．００１～９０重量％が挙げられる。 In the composition of the present invention, the content of the component (ii) is not particularly limited, and the form and use of the composition, the type of (i) component to be solubilized or dispersed, the type of component (ii) to be used Depending on the above, it may be set appropriately, for example, 0.00001 to 99.9% by weight, preferably 0.0001 to 99% by weight, more preferably 0.001 to 90% by weight.
　また、(i)成分に対する(ii)成分の比率としては、例えば、(i)成分１００重量部当たり、(ii)成分が０．００００１～９９．９重量部、好ましくは０．０００１～９９重量部、更に好ましくは０．００１～９０重量部が挙げられる。 The ratio of the component (ii) to the component (i) is, for example, 0.00001 to 99.9 parts by weight, preferably 0.0001 to 99 parts by weight of the component (ii) per 100 parts by weight of the component (i). Parts, more preferably 0.001 to 90 parts by weight.
他の成分
　本発明の組成物は、前記(i)成分の及び(ii)成分の分散媒として水を含有してもよい。また、本発明の組成物には、本発明の効果を妨げない範囲で、必要に応じて、酸化防止剤、増粘剤、キレート剤、乳化助剤、低級アルコール、多価アルコール、ｐＨ調整剤、緩衝剤等の添加成分を含んでいてもよい。 Other Components The composition of the present invention may contain water as a dispersion medium for the component (i) and the component (ii). In addition, the composition of the present invention includes an antioxidant, a thickener, a chelating agent, an emulsifying aid, a lower alcohol, a polyhydric alcohol, and a pH adjuster as necessary, as long as the effects of the present invention are not impaired. In addition, an additive component such as a buffer may be included.
　更に、本発明の組成物は、その形態や用途に応じた各種成分が含まれていてもよい。例えば、本発明の組成物を飲食品形態にする場合であれば、食品素材、栄養成分等が含まれていてもよい。また、本発明の組成物を医薬形態にする場合であれば、薬理成分、薬学的に許容される担体や添加剤等が含まれていてもよい。また、本発明の組成物を化粧料形態にする場合であれば、機能性成分、香粧学的に許容される担体や添加剤等が含まれていてもよい。更に、本発明の組成物を塗料やコーティング剤形態にする場合、樹脂バインダー等が含まれていてもよい。 Furthermore, the composition of the present invention may contain various components according to its form and use. For example, if the composition of the present invention is in the form of a food or drink product, food materials, nutritional components, and the like may be included. In addition, when the composition of the present invention is made into a pharmaceutical form, a pharmacological component, a pharmaceutically acceptable carrier, an additive, and the like may be included. In addition, when the composition of the present invention is made into a cosmetic form, a functional component, a cosmetically acceptable carrier, an additive, and the like may be included. Furthermore, when making the composition of this invention into a coating-material or a coating agent form, the resin binder etc. may be contained.
　また、本発明の組成物は、界面活性剤、乳化剤、分散剤等を含まなくとも、π共役系の難溶性又は不溶性物質の水への可溶化能又は分散性を向上させることができるが、必要に応じて、界面活性剤、乳化剤、分散剤等が含まれていてもよい。 In addition, the composition of the present invention can improve the solubilizing ability or dispersibility of π-conjugated system insoluble or insoluble substances in water without containing a surfactant, an emulsifier, a dispersant, etc. If necessary, a surfactant, an emulsifier, a dispersant and the like may be contained.
形態
　本発明の組成物は、前記(i)成分及び(ii)成分の分散媒として水を含む液状であってもよく、また、水分を除去し、ペースト状等の半固体状や、粉末状、顆粒状等の固体状にしてもよい。 Forms The composition of the present invention may be a liquid containing water as a dispersion medium for the components (i) and (ii), and also removes water to form a semi-solid form such as a paste or a powder form. Alternatively, it may be in a solid form such as a granular form.
　本発明の組成物は、前記(i)成分及び(ii)成分と共に水（分散媒）を含み、前記(i)成分が可溶化又は分散している含水状態であってもよい。 The composition of the present invention may contain water (dispersion medium) together with the components (i) and (ii), and may be in a water-containing state in which the component (i) is solubilized or dispersed.
　また、本発明の組成物は、水存在下で前記(i)成分及び(ii)成分を一旦共存させると、前記(i)成分の可溶化能又は分散性が向上し、その後、乾燥等によって水を除去しても、前記(i)成分の均一な分散が維持される。従って、本発明の組成物の他の一態様として、前記(i)成分、(ii)成分、及び水を含む水性原料を用いて製造され、乾燥等によって水が除去された乾燥状態であってもよい。 Further, the composition of the present invention, once the components (i) and (ii) coexist in the presence of water, the solubilizing ability or dispersibility of the component (i) is improved, and then dried or the like. Even if water is removed, the uniform dispersion of the component (i) is maintained. Therefore, as another embodiment of the composition of the present invention, the composition is produced using an aqueous raw material containing the component (i), the component (ii), and water, and is in a dry state in which water is removed by drying or the like. Also good.
　本発明の組成物の形態については、前記(i)成分の可溶化又は均一な分散が求められているものであれば特に制限されない。 The form of the composition of the present invention is not particularly limited as long as solubilization or uniform dispersion of the component (i) is required.
　例えば、前記(i)成分がポリフェノール及び／又はカロテノイドの場合であれば、本発明の組成物の形態として、飲食品、医薬品、化粧料等が挙げられる。 For example, when the component (i) is polyphenol and / or carotenoid, examples of the form of the composition of the present invention include foods and drinks, pharmaceuticals, and cosmetics.
　より具体的には、飲食品としては、錠剤、顆粒剤、粉剤、カプセル剤、ソフトカプセル剤等のサプリメント；タレ類（焼肉のタレ、焼き鳥のタレ、蒲焼きのタレ、餃子のタレ、団子のタレ等）、ソース類（とんかつソース、カレーソース、ホワイトソース、デミグラスソース、トマトソース、エビチリソース等）、スープ類（キムチ鍋スープ、ラーメンスープ、コンソメスープ、ポタージュスープ、クラムチャウダー等）の液状調味料、及びこれらの液状調味料を用いた加工食品；ヨーグルト、チーズ等の乳製品；イチゴジャム、リンゴジャム、ブルーベリージャム、マーマレード等のジャム類；ハム、ソーセージ、焼き豚等の畜肉加工品；魚肉ソーセージ、魚肉ハム、魚肉すり身、蒲鉾、竹輪、はんぺん、薩摩揚げ等の水産練り製品；塩漬け、味噌漬け、粕漬け、麹漬け、浅漬け、糠漬け、酢漬け、もろみ漬け、梅漬け、福神漬、しば漬等の漬物類；うどん、ソバ、冷麦、そうめん、中華そば、スパゲッティ、マカロニ、ビーフン、はるさめ等の麺類；ゼリー、ガム、チョコレート、ソフトキャンディー、ハードキャンディー、ビスケット、クッキー、クラッカー、おかき、煎餅、膨化スナック等の菓子類；アイスクリーム、ソフトクリーム、シャーベット、氷菓等の冷菓類；清涼飲料、乳飲料、乳酸菌飲料、炭酸飲料、果汁飲料、野菜飲料、野菜・果実飲料、粉末飲料、ゼリー飲料、コーヒー飲料、紅茶飲料、緑茶飲料、スポーツ飲料、栄養飲料アルコール飲料等の飲料類等の飲食品原料が挙げられる。 More specifically, as food and drink, supplements such as tablets, granules, powders, capsules, soft capsules; sauces (grilled meat sauce, grilled chicken sauce, grilled chicken sauce, dumpling sauce, dumpling sauce, etc.) ), Liquid seasonings of sauces (tonkatsu sauce, curry sauce, white sauce, demiglace sauce, tomato sauce, shrimp sauce, etc.), soups (kimchi hot pot soup, ramen soup, consommé soup, potage soup, clam chowder, etc.), and Processed foods using these liquid seasonings; dairy products such as yogurt and cheese; jams such as strawberry jam, apple jam, blueberry jam and marmalade; processed meat products such as ham, sausage and grilled pork; fish sausage and fish ham , Fish paste products such as fish paste, salmon, bamboo rings, hanpen, deep-fried Satsuma; salt Pickles, pickles such as pickles, miso pickles, pickles, pickles, pickles, pickles, pickles, pickles, pickles such as pickles, ume pickles, fukujin pickles, shiba pickles; udon, buckwheat, cold wheat, somen noodles, Chinese soba, spaghetti, macaroni, rice noodles, harusame Noodles such as jelly, gum, chocolate, soft candy, hard candy, biscuits, cookies, crackers, rice crackers, rice crackers, puffed snacks, etc .; frozen confectionery such as ice cream, soft cream, sorbet, ice confectionery; soft drinks, Foods and beverages such as milk beverages, lactic acid bacteria beverages, carbonated beverages, fruit juice beverages, vegetable beverages, vegetable and fruit beverages, powdered beverages, jelly beverages, coffee beverages, tea beverages, green tea beverages, sports beverages, nutritional beverages and alcoholic beverages Raw materials.
　また、化粧料としては、具体的には乳液、クリーム、化粧水（ローション）、パック、美容液、皮膚洗浄剤、メーキャップ化粧料等が挙げられる。 Further, as cosmetics, specifically, emulsions, creams, lotions, packs, essences, skin cleansers, makeup cosmetics and the like can be mentioned.
　また、医薬品としては、具体的には、錠剤、顆粒剤、粉剤、カプセル剤、ソフトカプセル剤、シロップ剤、液剤等の内服用製剤；外用剤、吸入剤、坐剤等の経皮又は経粘膜用製剤；注射剤等が挙げられる。 As pharmaceuticals, specifically, preparations for internal use such as tablets, granules, powders, capsules, soft capsules, syrups, liquids, etc .; for transdermal or transmucosal use such as external preparations, inhalants, suppositories, etc. Formulations; injections and the like.
　本発明の組成物が、前記(i)成分としてポリフェノール及び／又はカロテノイドを含み、飲食品、医薬品、又は化粧料の形態で提供される場合、ポリフェノール及び／又はカロテノイドの含有量については、使用するポリフェノール及び／又はカロテノイドの種類、製品の種類等に応じて前述する範囲で適宜設定すればよいが、具体的には０．００００１～５０重量％、好ましくは０．０００１～４５重量％、更に好ましくは０．００１～４０重量％が挙げられる。 When the composition of the present invention contains a polyphenol and / or carotenoid as the component (i) and is provided in the form of a food, beverage, medicine, or cosmetic, the content of the polyphenol and / or carotenoid is used. What is necessary is just to set suitably in the range mentioned above according to the kind of polyphenol and / or carotenoid, the kind of product, etc. Specifically, it is 0.00001-50 weight%, Preferably it is 0.0001-45 weight%, More preferably Is 0.001 to 40% by weight.
　また、本発明の組成物は、前記(i)成分としてポリフェノール及び／又はカロテノイドを含む場合には、前記飲食品、医薬品、化粧料等の製造時に、ポリフェノール及び／又はカロテノイドを配合するために使用される添加剤（飲食品添加剤、医薬原料、化粧料添加剤等）として提供してもよい。本発明の組成物は、このような添加剤として提供される場合、含水状態又は乾燥状態のいずれであってもよい。本発明の組成物がこのような添加剤として提供される場合、当該添加剤におけるポリフェノール及び／又はカロテノイドの含有量については、使用するポリフェノール及び／又はカロテノイドの種類等に応じて前述する範囲で適宜設定すればよいが、具体的には０．０１～９５重量％、更に好ましくは０．０５～９０重量％が挙げられる。 Further, when the composition of the present invention contains a polyphenol and / or carotenoid as the component (i), it is used for blending the polyphenol and / or carotenoid during the production of the food, beverage, medicine, cosmetics, etc. May be provided as a food additive (food and beverage additive, pharmaceutical raw material, cosmetic additive, etc.). When the composition of the present invention is provided as such an additive, it may be in a water-containing state or a dry state. When the composition of the present invention is provided as such an additive, the content of polyphenol and / or carotenoid in the additive is appropriately determined within the above-described range according to the type of polyphenol and / or carotenoid used. Specifically, it may be 0.01 to 95% by weight, more preferably 0.05 to 90% by weight.
　また、例えば、前記(i)成分が炭素材料の場合であれば、本発明の組成物の形態として、黒色着色液、導電性コーティング液等の炭素材料の分散液；当該黒色着色液が塗布された着色部材；当該導電性コーティング液が塗布された導電性部材（導電性フィルム、電極部材、電子機器等に使用される電磁遮蔽部材）等が挙げられる。本発明の組成物がこのような形態で提供される場合、炭素材料の含有量については、使用する炭素材料の種類、用途等に応じて前述する範囲で適宜設定すればよいが、具体的には０．００１～２０重量％、好ましくは０．０１～１０重量％、更に好ましくは０．０５～５重量％が挙げられる。 Further, for example, if the component (i) is a carbon material, the composition of the present invention is applied as a dispersion of a carbon material such as a black coloring liquid or a conductive coating liquid; the black coloring liquid is applied. Colored members; conductive members coated with the conductive coating liquid (electromagnetic shielding members used for conductive films, electrode members, electronic devices, etc.) and the like. When the composition of the present invention is provided in such a form, the content of the carbon material may be appropriately set within the above-described range depending on the type of carbon material used, the use, etc. Is 0.001 to 20% by weight, preferably 0.01 to 10% by weight, more preferably 0.05 to 5% by weight.
　また、本発明の組成物が、前記(i)成分として炭素材料を含む場合には、前記各種形態の製品の製造時に、炭素材料を配合するために使用される添加剤として提供してもよい。本発明の組成物は、このような添加剤として提供される場合、含水又は乾燥のいずれであってもよい。本発明の組成物がこのような添加剤として提供される場合、当該添加剤における炭素材料の含有量については、使用する炭素材料の種類等に応じて前述する範囲で適宜設定すればよいが、具体的には０．０１～９８重量％、好ましくは０．１～９５重量％、更に好ましくは０．５～９０重量％が挙げられる。 Further, when the composition of the present invention contains a carbon material as the component (i), it may be provided as an additive used for blending the carbon material at the time of manufacturing the products of the various forms. . When provided as such additives, the compositions of the present invention may be either hydrated or dried. When the composition of the present invention is provided as such an additive, the content of the carbon material in the additive may be appropriately set within the above-described range according to the type of the carbon material used, Specifically, it is 0.01 to 98% by weight, preferably 0.1 to 95% by weight, and more preferably 0.5 to 90% by weight.
　また、例えば、前記(i)成分が有機顔料の場合であれば、本発明の組成物の形態として、水系塗料、当該水系塗料が塗布された各種製品等が挙げられる。本発明の組成物がこのような形態で提供される場合、有機顔料の含有量については、使用する有機顔料の種類、用途等に応じて前述する範囲で適宜設定すればよいが、具体的には０．００００１～５０重量％、好ましくは０．０００１～４５重量％、更に好ましくは０．００１～４０重量％が挙げられる。 Also, for example, when the component (i) is an organic pigment, examples of the form of the composition of the present invention include water-based paints and various products coated with the water-based paint. When the composition of the present invention is provided in such a form, the content of the organic pigment may be appropriately set within the above-mentioned range depending on the type of organic pigment to be used, application, etc. Is 0.00001 to 50% by weight, preferably 0.0001 to 45% by weight, more preferably 0.001 to 40% by weight.
　また、本発明の組成物が、前記(i)成分として有機顔料を含む場合には、前記各種形態の製品の製造時に、有機顔料を配合するために使用される添加剤として提供してもよい。本発明の組成物は、このような添加剤として提供される場合、含水状態又は乾燥状態のいずれであってもよい。本発明の組成物がこのような添加剤として提供される場合、当該添加剤における有機顔料の含有量については、使用する有機顔料の種類等に応じて前述する範囲で適宜設定すればよいが、具体的には０．０００１～９８重量％、好ましくは０．００１～９５重量％、更に好ましくは０．０１～９０重量％が挙げられる。 Further, when the composition of the present invention contains an organic pigment as the component (i), it may be provided as an additive used for blending the organic pigment at the time of manufacturing the products of the various forms. . When the composition of the present invention is provided as such an additive, it may be in a water-containing state or a dry state. When the composition of the present invention is provided as such an additive, the content of the organic pigment in the additive may be appropriately set in the above-described range according to the type of the organic pigment used, Specifically, 0.0001 to 98% by weight, preferably 0.001 to 95% by weight, and more preferably 0.01 to 90% by weight.
　また、本発明の組成物が、前記(i)成分が薬物の場合であれば、本発明の組成物の形態として、医薬品(ヒト用、非ヒト用を含む)、農薬等が挙げられる。医薬品としては、具体的には、錠剤、顆粒剤、粉剤、カプセル剤、ソフトカプセル剤、シロップ剤、液剤等の内服用製剤；外用剤、吸入剤、坐剤等の経皮又は経粘膜用製剤；注射剤等が挙げられる。また、農薬としては、具体的には、液剤（濃縮液剤を含む）、粉末剤、顆粒剤等が挙げられる。 In the case where the composition (i) is a drug in the composition of the present invention, examples of the form of the composition of the present invention include pharmaceuticals (including those for humans and non-humans), agricultural chemicals and the like. Specific examples of pharmaceuticals include internal preparations such as tablets, granules, powders, capsules, soft capsules, syrups, and liquids; transdermal or transmucosal preparations such as external preparations, inhalants, and suppositories; An injection agent etc. are mentioned. Specific examples of agricultural chemicals include liquids (including concentrated liquids), powders, granules and the like.
　本発明の組成物が、前記(i)成分として薬物を含み、医薬品又は農薬の形態で提供される場合、当該薬物の含有量については、使用する薬物の種類、剤型等に応じて前述する範囲で適宜設定すればよいが、具体的には０．００００１～９８重量％、好ましくは０．０００１～９５重量％、更に好ましくは０．００１～９０重量％が挙げられる。 When the composition of the present invention contains a drug as the component (i) and is provided in the form of a pharmaceutical or agrochemical, the content of the drug is described above according to the type, dosage form, etc. of the drug used. The amount may be appropriately set within the range, and specifically, 0.00001 to 98% by weight, preferably 0.0001 to 95% by weight, and more preferably 0.001 to 90% by weight.
　また、本発明の組成物は、前記(i)成分として薬物を含む場合には、前記医薬品又は農薬の製造時に、薬物を配合するために使用される添加剤（医薬原料農薬原料等）として提供してもよい。本発明の組成物は、このような添加剤として提供される場合、含水状態又は乾燥状態のいずれであってもよい。本発明の組成物がこのような添加剤として提供される場合、当該添加剤における薬物の含有量については、使用する薬物の種類等に応じて前述する範囲で適宜設定すればよいが、具体的には０．０００１～９８重量％、好ましくは０．００１～９５重量％、更に好ましくは０．０１～９０重量％が挙げられる。 In addition, when the composition of the present invention contains a drug as the component (i), it is provided as an additive (such as a pharmaceutical raw material for agricultural chemicals) used for blending the drug when the pharmaceutical or agricultural chemical is manufactured. May be. When the composition of the present invention is provided as such an additive, it may be in a water-containing state or a dry state. When the composition of the present invention is provided as such an additive, the content of the drug in the additive may be appropriately set within the above-described range depending on the type of drug used, etc. Is 0.0001 to 98% by weight, preferably 0.001 to 95% by weight, and more preferably 0.01 to 90% by weight.
製造方法
　本発明の組成物が液状の場合であれば、水に、(i)成分、(ii)成分、及び必要に応じて他の添加成分を添加し、混合することによって調製することができる。水存在下で、前記(i)成分及び(ii)成分を添加してこれらを共存させて混合すると、(i)成分が水中で可溶化又は安定に分散した状態になる。(i)成分としてポリフェノール及び／又はカロテノイドを使用した場合には、(ii)成分との共存によって可溶化状態になり、(i)成分として炭素材料を使用した場合には(ii)成分との共存によって安定に分散した状態になる。 In the case the composition of the manufacturing method of the present invention is a liquid, water, may be prepared by adding other additive components are mixed according to component (i), (ii) component, and need . When the components (i) and (ii) are added and mixed together in the presence of water, the component (i) is solubilized or stably dispersed in water. When polyphenol and / or carotenoid is used as component (i), it becomes solubilized by coexistence with component (ii), and when carbon material is used as component (i), Coexistence and stable dispersion.
　(i)成分が界面活性剤や乳化剤等でミセルを形成している状態で(ii)成分と共存させると、π共役系の難溶性又は不溶性物質の可溶化や分散性が不十分になったり、可溶化状態や分散状態が良好になるまでに時間を要したりする場合があるため、本発明の組成物の製造時に、水中で(i)成分と(ii)成分を共存させる際には、(i)成分は界面活性剤や乳化剤等でミセルを形成していない状態にしておくことが望ましい。 When the component (i) is in the form of micelles with a surfactant or an emulsifier, coexistence with the component (ii) may result in insufficient solubility or dispersibility of π-conjugated system insoluble or insoluble substances. In addition, since it may take time until the solubilized state and the dispersed state become favorable, when the (i) component and the (ii) component are allowed to coexist in water during the production of the composition of the present invention. The component (i) is desirably kept in a state in which micelles are not formed with a surfactant or an emulsifier.
　また、本発明の組成物が半固体状又は固体状の場合であれば、前記方法で液状の本発明の組成物を製造した後に、水を除去し、必要に応じて、ペースト状等の半固体状や、粉末状、顆粒状等の固体状にする成型処理に供すればよい。 In addition, if the composition of the present invention is semi-solid or solid, after the liquid composition of the present invention is produced by the above method, water is removed, and if necessary, semi-solid such as paste What is necessary is just to use for the shaping | molding process made into solid forms, such as solid form, powder form, and granular form.
　更に、添加剤形態で提供された本発明の組成物を使用することによって、最終製品形態（(i)成分が最終使用時の濃度に調整されている製品）である本発明の組成物を製造することもできる。 Furthermore, by using the composition of the present invention provided in the form of an additive, the composition of the present invention in the final product form (product in which the component (i) is adjusted to the concentration at the time of final use) is produced. You can also
２．π共役系の難溶性又は不溶性物質の可溶化又は分散化剤、及びπ共役系の難溶性又は不溶性物質の可溶化又は分散化方法
　前述するように、前記(ii)成分は、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させるため、π共役系の難溶性又は不溶性物質の可溶化又は分散化剤として使用することもできる。 2. Solubilizing or dispersing agent for π-conjugated system poorly soluble or insoluble material, and π-conjugated system poorly soluble or insoluble material solubilizing or dispersing method As described above, the component (ii) comprises a π-conjugated system In order to improve the solubilization ability or water dispersibility of a hardly soluble or insoluble substance in water, it can also be used as a solubilizing or dispersing agent for a hardly soluble or insoluble substance of a π-conjugated system.
　本発明の可溶化又は分散化剤は、π共役系の難溶性又は不溶性物質と水を含む各種製品に添加して、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させる目的で使用される。本発明の可溶化又は分散化剤の適用対象となる製品としては、π共役系の難溶性又は不溶性物質と水を含んでいることを限度として特に制限されないが、具体的には、前述する各種形態の製品、前述する各種形態の製品の製造に使用される水性原料等が挙げられる。 The solubilizing or dispersing agent of the present invention is added to various products containing a π-conjugated system poorly soluble or insoluble substance and water, so that the π-conjugated system poorly soluble or insoluble substance can be solubilized or dispersed in water. Used to improve performance. The product to which the solubilizing or dispersing agent of the present invention is applied is not particularly limited as long as it contains a π-conjugated system poorly soluble or insoluble material and water. Products in the form, aqueous raw materials used in the manufacture of the products in the various forms described above, and the like.
　本発明の可溶化又は分散化剤の有効成分である(ii)成分の種類、使用態様等については、前記の通りである。また、本発明の可溶化又は分散化剤において、可溶化又は分散化の対象となるπ共役系の難溶性又は不溶性物質の種類等についても前記の通りである。 The type and usage of component (ii), which is an active ingredient of the solubilizing or dispersing agent of the present invention, are as described above. Further, in the solubilizing or dispersing agent of the present invention, the kind of the slightly soluble or insoluble substance of the π-conjugated system to be solubilized or dispersed is as described above.
　また、本発明の一態様では、前記(ii)成分を使用したπ共役系の難溶性又は不溶性物質の可溶化又は分散化方法が提供される。当該可溶化又は分散化方法において、使用する各成分の種類や使用量等については前記の通りである。 Also, in one embodiment of the present invention, a method for solubilizing or dispersing a π-conjugated system hardly soluble or insoluble substance using the component (ii) is provided. In the solubilization or dispersion method, the type and amount of each component used are as described above.
　以下、実施例を挙げて本発明を更に詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
試験例１
　表１に示す組成の液剤を調製した。具体的には、所定量のクチナシ黄色素液、所定量の精製水、及び所定量のレスベラトロール液をこの順で添加し、ボルテックスにて十分に撹拌した。 Test example 1
A solution having the composition shown in Table 1 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　得られた液剤の外観を観察した結果を図１に示す。図１から明らかなように、レスベラトロールとクチナシ黄色素を共存させた場合には、レスベラトロールが可溶化できていた。 The result of observing the appearance of the obtained liquid is shown in FIG. As is clear from FIG. 1, resveratrol was solubilized when resveratrol and gardenia yellow were coexisted.
　次に、得られた液剤（実施例１～３及び比較例１～３）を５０００ｒｐｍで５分間遠心分離した後に、上清をＨＰＬＣに供し、可溶化しているレスベラトロール量の測定を行った。得られた結果を表２に示す。この結果からも、クチナシ黄色素によってレスベラトロールが可溶化できていることが確認された。 Next, after the obtained solutions (Examples 1 to 3 and Comparative Examples 1 to 3) were centrifuged at 5000 rpm for 5 minutes, the supernatant was subjected to HPLC, and the amount of resveratrol solubilized was measured. It was. The obtained results are shown in Table 2. From this result, it was confirmed that resveratrol was solubilized by gardenia yellow.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
試験例２
　前記試験例１において、クチナシ黄色素にはレスベラトロールを可溶化する作用が認められたので、クチナシ黄色素に含まれるどの成分がレスベラトロールの可溶化に寄与しているかを評価するために、以下の試験を行った。 Test example 2
In Test Example 1, the effect of solubilizing resveratrol was observed in gardenia yellow, in order to evaluate which component contained in gardenia yellow contributes to solubilization of resveratrol. The following tests were conducted.
　表３に示す組成の液剤を調製した。具体的には、所定量のクロシン液、クロシン－３液、又は精製水と、所定量のレスベラトロール液とをこの順で添加し、ボルテックスにて十分に撹拌した。 A solution having the composition shown in Table 3 was prepared. Specifically, a predetermined amount of crocin solution, crocin-3 solution, or purified water and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　得られた液剤（実施例６、７、比較例４）の外観を観察した結果を図２に示す。図２から明らかなように、クロシン又はクロシン－３によってレスベラトロールを可溶化できていた。 FIG. 2 shows the results of observing the appearance of the obtained liquid agents (Examples 6 and 7, Comparative Example 4). As is clear from FIG. 2, resveratrol could be solubilized by crocin or crocin-3.
　次に、得られた液剤を５０００ｒｐｍで５分間遠心分離した後に、上清をHPLCに供し、可溶化しているレスベラトロール量の測定を行った。得られた結果を表４に示す。この結果からも、クロシン又はクロシン－３によってレスベラトロールが可溶化できていることが確認された。特に、クロシン－３は、低濃度でも、レスベラトロールを効率的に可溶化できることが明らかとなった（実施例８及び１１）。 Next, after the obtained liquid was centrifuged at 5000 rpm for 5 minutes, the supernatant was subjected to HPLC, and the amount of resveratrol solubilized was measured. Table 4 shows the obtained results. This result also confirmed that resveratrol could be solubilized by crocin or crocin-3. In particular, crocin-3 was found to be able to efficiently solubilize resveratrol even at low concentrations (Examples 8 and 11).
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
試験例３
　表５に示す組成の液剤を調製した。具体的には、所定量のクチナシ黄色素液、所定量の精製水、及び所定量のクルクミン液をこの順で添加し、ボルテックスにて十分に撹拌した。 Test example 3
A solution having the composition shown in Table 5 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of curcumin solution were added in this order, and the mixture was sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
　得られた液剤（実施例１２～１４及び比較例５～７）の外観を観察した結果を図３に示す。図３から明らかなように、クルクミンとクチナシ黄色素を共存させた場合には、クルクミンの沈殿の発生を抑制できており、可溶化されていた。 The results of observing the appearance of the obtained liquid agents (Examples 12 to 14 and Comparative Examples 5 to 7) are shown in FIG. As is apparent from FIG. 3, when curcumin and gardenia yellow were coexistent, the occurrence of curcumin precipitation could be suppressed and solubilized.
試験例４
　表６に示す組成の液剤を調製した。具体的には、所定量のクチナシ黄色素液、所定量の精製水、及び所定量のケルセチン液をこの順で添加し、ボルテックスにて十分に撹拌した。 Test example 4
A solution having the composition shown in Table 6 was prepared. Specifically, a predetermined amount of gardenia yellow liquid, a predetermined amount of purified water, and a predetermined amount of quercetin solution were added in this order, and the mixture was sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000006
Figure JPOXMLDOC01-appb-T000006
　得られた液剤（実施例１５～１７及び比較例８～１０）の外観を観察した結果を図４に示す。図４から明らかなように、ケルセチンについても、クチナシ黄色素を共存させることによって、沈殿の発生を抑制して可溶化できていた。 The results of observing the appearance of the obtained liquid agents (Examples 15 to 17 and Comparative Examples 8 to 10) are shown in FIG. As apparent from FIG. 4, quercetin was also solubilized by suppressing the occurrence of precipitation by coexisting gardenia yellow.
試験例５
　表７に示す組成の分散液を調製した。具体的には、所定量のクチナシ黄色素液又は精製水と、所定量のカーボンナノチューブとをこの順で添加し、ボルテックスにて十分に撹拌した。 Test Example 5
A dispersion having the composition shown in Table 7 was prepared. Specifically, a predetermined amount of gardenia yellow liquid or purified water and a predetermined amount of carbon nanotubes were added in this order and sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000007
　次いで、得られた分散液（実施例１８～１９及び比較例１１～１２）を５０００ｒｐｍで５分間遠心分離し、外観の観察を行った。得られた結果を図５に示す。この結果からも、クチナシ黄色素によってカーボンナノチューブの分散性が著しく向上することが確認された。 Next, the obtained dispersions (Examples 18 to 19 and Comparative Examples 11 to 12) were centrifuged at 5000 rpm for 5 minutes, and the appearance was observed. The obtained results are shown in FIG. From these results, it was confirmed that the dispersibility of the carbon nanotubes was remarkably improved by gardenia yellow.
試験例６
　表８に示す組成の液剤を調製した。具体的には、所定量の１３－シス－クロセチン液、所定量の精製水、及び所定量のレスベラトロール液をこの順で添加し、ボルテックスにて十分に撹拌した。 Test Example 6
A solution having the composition shown in Table 8 was prepared. Specifically, a predetermined amount of 13-cis-crocetin solution, a predetermined amount of purified water, and a predetermined amount of resveratrol solution were added in this order, and the mixture was sufficiently stirred by vortexing.
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000008
　得られた液剤（実施例２０～２２及び比較例１３～１５）の外観を観察した結果を図６に示す。図６から明らかなように、クロセチンを使用しても、レスベラトロールを可溶化できることが明らかとなった。 The results of observing the appearance of the obtained liquid agents (Examples 20 to 22 and Comparative Examples 13 to 15) are shown in FIG. As apparent from FIG. 6, it was revealed that resveratrol can be solubilized even when crocetin is used.
　次に、得られた液剤（実施例２０～２２及び比較例１３）を５０００ｒｐｍで５分間遠心分離した後に、上清をHPLCに供し、可溶化しているレスベラトロール量の測定を行った。得られた結果を表９に示す。この結果からも、クロセチンによってレスベラトロールが可溶化できていることが確認された。 Next, after the obtained solutions (Examples 20 to 22 and Comparative Example 13) were centrifuged at 5000 rpm for 5 minutes, the supernatant was subjected to HPLC, and the amount of resveratrol solubilized was measured. Table 9 shows the obtained results. This result also confirmed that resveratrol was solubilized by crocetin.
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000009
総合考察
　前記試験例１において、クチナシ黄色素によってレスベラトロールを可溶化できることが認められ、更に、前記試験例２において、レスベラトロールの可溶化には、クチナシ黄色素中のクロシン－３及び／又はクロシンが寄与していることが明らかになった。更に、試験例３及び４において、クチナシ黄色素によってクルクミンやケルセチンを可溶化できることも明らかとなった。これは、レスベラトロール、クルクミン、ケルセチン等の難溶性のポリフェノールに存在する共役二重結合部分が、クロシン－３及び／又はクロシンの共役二重結合部分をπ－π相互作用によって引き付け、その結果、難溶性のポリフェノール同士の集積が抑制され、更にクロシン－３及び／又はクロシンのゲンチオビオース部分により水溶性が付与されたことによると考えられる。 General Consideration In Test Example 1, it was found that resveratrol can be solubilized by gardenia yellow, and in Test Example 2, resveratrol was solubilized by crocin-3 and / or Or it became clear that crocin contributed. Furthermore, in Test Examples 3 and 4, it was also revealed that curcumin and quercetin can be solubilized by gardenia yellow. This is because conjugated double bond moieties present in sparingly soluble polyphenols such as resveratrol, curcumin, quercetin, etc. attract crocin-3 and / or conjugated double bond moieties of crocin by π-π interaction. This is probably because accumulation of hardly soluble polyphenols was suppressed, and water solubility was further imparted by crocin-3 and / or the gentiobiose portion of crocin.
　また、前記試験例５では、クチナシ黄色素によってカーボンナノチューブの水分散性の向上が認められた。カーボンナノチューブは、難溶性のポリフェノールと同様に、π共役系の物質であることを考慮すると、前記試験例３で認められたカーボンナノチューブの水分散性の向上は、(1)クチナシ黄色素に含まれるカロテノイド配糖体（クロシン－３やクロシン等）の共役二重結合部分が、カーボンナノチューブに存在する共役二重結合部分にπ－π相互作用によって引き付けられ、カーボンナノチューブ同士の集積が抑制できたこと、(2)カーボンナノチューブに引き付けられたカロテノイド配糖体（クロシン－３やクロシン等）の糖部分が親水性の付与に寄与したこと、によると合理的に推論される。 In Test Example 5, the water dispersibility of the carbon nanotubes was improved by gardenia yellow. Considering that carbon nanotubes are π-conjugated substances as well as poorly soluble polyphenols, the improvement in water dispersibility of carbon nanotubes observed in Test Example 3 is included in (1) Gardenia yellow The conjugated double bond part of carotenoid glycosides (such as crocin-3 and crocin) is attracted to the conjugated double bond part present in the carbon nanotube by π-π interaction, and the accumulation of carbon nanotubes can be suppressed. It is reasonably inferred that (2) the sugar moiety of the carotenoid glycoside (crocin-3, crocin, etc.) attracted to the carbon nanotube contributed to imparting hydrophilicity.
　更に、試験例６では、クロセチンにもレスベラトロールを可溶化する作用が認められたことから、クロセチンにも、π共役系の難溶性又は不溶性物質の水への可溶化能又は水分散性を向上させ得ることが明らかとなった。 Furthermore, in Test Example 6, since the action of solubilizing resveratrol was also observed in crocetin, crocetin also has a water-solubilizing ability or water dispersibility of π-conjugated system insoluble or insoluble substances. It became clear that it could be improved.

Claims (12)

  1. 　(i)π共役系の水難溶性又は水不溶性物質、及び(ii)カロテノイド配糖体及び／又はクロセチンを含有することを特徴とする、π共役系の難溶性又は不溶性物質の可溶化又は分散化用の組成物。 Solubilization or dispersion of a π-conjugated system poorly soluble or insoluble substance characterized by containing (i) a π-conjugated system poorly water-soluble or water-insoluble substance, and (ii) a carotenoid glycoside and / or crocetin. Composition.
  2. 　前記(i)成分が、水難溶性又は水不溶性ポリフェノール、水難溶性又は水不溶性カロテノイド、水難溶性又は水不溶性炭素材料、水難溶性又は水不溶性有機顔料、及び水難溶性又は水不溶性薬物よりなる群から選択される少なくとも１種である、請求項１に記載の組成物。 The component (i) is selected from the group consisting of poorly water-soluble or water-insoluble polyphenols, poorly water-soluble or water-insoluble carotenoids, poorly water-soluble or water-insoluble carbon materials, poorly water-soluble or water-insoluble organic pigments, and poorly water-soluble or water-insoluble drugs. The composition according to claim 1, wherein the composition is at least one kind.
  3. 　前記(ii)成分が、クロセチン配糖体である、請求項１又は２に記載の組成物。 The composition according to claim 1 or 2, wherein the component (ii) is crocetin glycoside.
  4. 　前記(ii)成分が、クロシン－３及び／又はクロシンである、請求項１～３のいずれかに記載の組成物。 The composition according to any one of claims 1 to 3, wherein the component (ii) is crocin-3 and / or crocin.
  5. 　前記(ii)成分として、クチナシ黄色素を含む、請求項１～４のいずれかに記載の組成物。 The composition according to any one of claims 1 to 4, comprising gardenia yellow as the component (ii).
  6. 　前記(i)成分がポリフェノール及び／又はカロテノイドであり、飲食品、医薬品、化粧料、又はこれらの添加剤の形態である、請求項１～５のいずれかに記載の組成物。 The composition according to any one of claims 1 to 5, wherein the component (i) is a polyphenol and / or carotenoid and is in the form of a food or drink, a pharmaceutical product, a cosmetic, or an additive thereof.
  7. 　前記(i)成分が炭素材料であり、当該炭素材料の分散液の形態である、請求項１～５のいずれかに記載の組成物。 The composition according to any one of claims 1 to 5, wherein the component (i) is a carbon material and is in the form of a dispersion of the carbon material.
  8. 　カロテノイド配糖体及び／又はクロセチンを有効成分とする、π共役系の水難溶性の可溶化又は分散化剤。 Π-conjugated poorly water-soluble solubilizer or dispersant containing carotenoid glycoside and / or crocetin as active ingredients.
  9. 　水難溶性ポリフェノール及び／又はカロテノイドの可溶化剤である、請求項８に記載のπ共役系の水難溶性の可溶化又は分散化剤。 The π-conjugated poorly water-soluble solubilizer or dispersant according to claim 8, which is a poorly water-soluble polyphenol and / or carotenoid solubilizer.
  10. 　炭素材料の分散化剤である、請求項８に記載のπ共役系の水難溶性の可溶化又は分散化剤。 The π-conjugated poorly water-soluble solubilizer or dispersant according to claim 8, which is a carbon material dispersant.
  11. 　カロテノイド配糖体及び／又はクロセチンの存在下で、π共役系の水難溶性又は水不溶性物質を水に可溶化又は分散化させる工程を含む、π共役系の水難溶性又は水不溶性物質の可溶化又は分散化方法。 Solubilizing or dissolving a π-conjugated poorly water-soluble or water-insoluble substance, comprising the step of solubilizing or dispersing the π-conjugated poorly water-soluble or water-insoluble substance in water in the presence of a carotenoid glycoside and / or crocetin Decentralization method.
  12. 　カロテノイド配糖体及び／又はクロセチンの、π共役系の水難溶性の可溶化又は分散化剤としての使用。 Use of carotenoid glycoside and / or crocetin as a π-conjugated poorly water-soluble solubilizer or dispersant.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020122706A1 (en) * 2018-12-12 2020-06-18 Universiti Malaya A method of producing functionalized graphene nanofluid

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0693199A (en) * 1991-10-03 1994-04-05 T Hasegawa Co Ltd Antifading agent for gardenian yellow color
JP2002060693A (en) * 2000-08-21 2002-02-26 Nippe Home Products Co Ltd Natural paint for wood
WO2003084352A1 (en) * 2002-04-11 2003-10-16 Kyowa Hakko Kogyo Co., Ltd. Liquid food/drink containing fat-soluble vitamin and method of stabilizing fat-soluble vitamin
JP2004222649A (en) * 2003-01-24 2004-08-12 Taiyo Kagaku Co Ltd Agent for preventing color fading of colorant
JP2007215465A (en) * 2006-02-16 2007-08-30 Riken Vitamin Co Ltd Asthenopia improving composition
JP2008092869A (en) * 2006-10-12 2008-04-24 Toyo Seito Kk Flavonoid composition, method for producing the same and use of the composition

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201101669D0 (en) * 2011-01-31 2011-03-16 Ip Science Ltd Carotenoid particles and uses thereof
JP2015536319A (en) * 2012-10-16 2015-12-21 ウィリアム・マーシュ・ライス・ユニバーシティ Improved nanovector-based drug delivery system to overcome drug resistance
JP5934840B2 (en) * 2013-09-25 2016-06-15 グリコ栄養食品株式会社 Emulsifiable preparations of fat-soluble substances

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0693199A (en) * 1991-10-03 1994-04-05 T Hasegawa Co Ltd Antifading agent for gardenian yellow color
JP2002060693A (en) * 2000-08-21 2002-02-26 Nippe Home Products Co Ltd Natural paint for wood
WO2003084352A1 (en) * 2002-04-11 2003-10-16 Kyowa Hakko Kogyo Co., Ltd. Liquid food/drink containing fat-soluble vitamin and method of stabilizing fat-soluble vitamin
JP2004222649A (en) * 2003-01-24 2004-08-12 Taiyo Kagaku Co Ltd Agent for preventing color fading of colorant
JP2007215465A (en) * 2006-02-16 2007-08-30 Riken Vitamin Co Ltd Asthenopia improving composition
JP2008092869A (en) * 2006-10-12 2008-04-24 Toyo Seito Kk Flavonoid composition, method for producing the same and use of the composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020122706A1 (en) * 2018-12-12 2020-06-18 Universiti Malaya A method of producing functionalized graphene nanofluid

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