Classifications

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  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
  • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
• • A—HUMAN NECESSITIES
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
• • A—HUMAN NECESSITIES
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
• • A—HUMAN NECESSITIES
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
• • A—HUMAN NECESSITIES
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• • A—HUMAN NECESSITIES
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
  • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
  • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
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• • 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
  • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
  • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/005—Antimicrobial preparations
• • 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
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/10—General cosmetic use
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
  • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/52—Stabilizers
  • A61K2800/524—Preservatives

Definitions

• the present invention relates to a nanoemulsion with an antiseptic effect.
• Emulsification is known as a method for solubilizing poorly water-soluble substances used in pharmaceuticals, cosmetics, and foods. Through the emulsification process, the oral and percutaneous absorption efficiency of poorly water-soluble substances is improved, and the effect is particularly large in nanoemulsions with small emulsified particle diameters.
• An object of one aspect of the present invention is to provide a stable nanoemulsion in which putrefaction due to bacterial contamination is suppressed.
• a nanoemulsion according to one embodiment of the present invention is a nanoemulsion in which emulsified particles have an average particle size of 30 nm or less, a particle size distribution index of 0.14 or less, and does not contain emulsified particles of 100 nm or more.
• the present inventors attempted to solve the above problems by adding a preservative to the nanoemulsion developed by the present inventors, in which the emulsified particles have a nano-level particle size.
• Preservatives such as parabens and alkanediols (propylene glycol) are commonly used in emulsions (see Patent Document 2, etc.).
• these preservatives were added to the nanoemulsion, it was found that there was a problem that the stability of the emulsion could not be maintained. This was believed to be due to the very small particle size of the emulsified particles of the nanoemulsion.
• the present inventors have found that the above problems can be solved by using a specific preservative, and have completed the present invention.
• the nanoemulsion according to one embodiment of the present invention is a nanoemulsion in which the average particle size of emulsified particles is 30 nm or less, the particle size distribution index is 0.14 or less, and the nanoemulsion does not contain emulsified particles of 100 nm or more.
• nanoemulsion refers to an optically transparent or translucent microdroplet dispersion system with a particle size of several nanometers to several tens of nanometers, made of water, oil, and a surfactant.
• the microdroplets correspond to micelles, which will be described later, and are emulsified particles (emulsified particles) of a nanoemulsion.
• a nanoemulsion according to one embodiment of the present invention further comprises a sparingly water-soluble functional ingredient and a preservative in the microdroplet dispersion system. That is, a nanoemulsion according to one embodiment of the present invention comprises a surfactant component, an oil, a sparingly water-soluble functional component, an aqueous medium, and a preservative.
• a nanoemulsion according to one embodiment of the present invention is a nanoemulsion that has an average particle size of 30 nm or less, a particle size distribution index of 0.14 or less, and does not contain particles of 100 nm or more, and contains at least one selected from organic acids (salts) and biguanide compounds as a preservative.
• a nanoemulsion according to one embodiment herein comprises a surfactant component.
• the surfactant component is, but not limited to, for example, polyoxyalkylene alkyl ether; polyoxyalkylene alkenyl ether; polyoxyalkylene alkylphenyl ether; polyoxyethylene castor oil; sorbitan fatty acid ester and its alkylene oxide adduct; polyoxyalkylene fatty acid ester;
• the nanoemulsion contains at least one selected from the above-described nonionic surfactants as a main surfactant component.
• a main component is preferably 80% by weight or more, more preferably 85% by weight or more, still more preferably 90% by weight or more, particularly preferably 95% by weight or more, and most preferably 100% by weight, based on the total weight of the surfactant components contained in the nanoemulsion.
• the nanoemulsion contains at least one selected from polyoxyalkylene alkyl ethers, polyoxyalkylene alkenyl ethers, polyoxyethylene castor oil, alkylene oxide adducts of sorbitan fatty acid esters, and polyoxyethylene alkanoic acid hydrogenated castor oil as the main component of the surfactant component.
• polyoxyalkylene alkyl ethers examples include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxypropylene cetyl ether, polyoxypropylene isocetyl ether, polyoxypropylene stearyl ether, and polyoxyethylene behenyl ether.
• polyoxyalkylene alkenyl ethers examples include polyoxyethylene oleyl ether and polyoxypropylene oleyl ether.
• polyoxyalkylene alkylphenyl ether examples include polyoxyethylene octylphenyl ether.
• Polyoxyethylene castor oil is a compound obtained by addition polymerization of ethylene oxide to castor oil.
• the average number of added moles of ethylene oxide is not particularly limited, but is preferably 2-100, more preferably 10-50.
• Examples of the polyoxyethylene castor oil include NIKKOL CO-3, NIKKOL CO-10, NIKKOL CO-35 (Nikko Chemicals); EMALEX C-20, EMALEX C-30, EMALEX C-40, EMALEX C-50 (Nippon Emulsion); and Kolliphor EL (BASF).
• sorbitan fatty acid esters examples include sorbitan monooleate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monopalmitate, sorbitan monolaurate, sorbitan trioleate, sorbitan tristearate, sorbitan sesquistearate, sorbitan sesquioleate, sorbitan sesquiisostearate, and sorbitan coconut oil fatty acid.
• alkylene oxide adducts of sorbitan fatty acid esters include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monoisostearate, polyoxyethylene sorbitan monococonut oil fatty acid, polyoxyethylene sorbitan tristearate, and polyoxyethylene sorbitan trioleate.
• Polyoxyalkylene fatty acid esters include, for example, both polyoxyalkylene mono-fatty acid esters and polyoxyalkylene di-fatty acid esters.
• polyoxyalkylene mono fatty acid esters include polyethylene glycol mono fatty acid esters such as polyethylene glycol monooleate, polyethylene glycol monostearate, and polyethylene glycol monolaurate; propylene glycol monostearate, propylene glycol monolaurate, propylene glycol monooleate, and the like propylene glycol mono fatty acid esters.
• polyoxyethylene hydrogenated castor oil of alkanoic acid examples include polyoxyethylene hydrogenated castor oil isostearate, polyoxyethylene hydrogenated castor oil stearate, and polyoxyethylene hydrogenated castor oil laurate.
• the nanoemulsion according to one embodiment of the present invention may contain at least one surfactant, and may contain two or more surfactants.
• a stable nanoemulsion can be provided by containing the surfactant.
• the content of the surfactant component contained in the nanoemulsion according to one embodiment of the present invention is not particularly limited as long as it is an amount capable of forming a nanoemulsion, but is preferably 10.0 to 49.9% by weight, more preferably 12.0 to 35.0% by weight, and even more preferably 20.0 to 29.0% by weight, relative to the total weight of the nanoemulsion.
• the content of the surfactant component contained in the nanoemulsion is 12.0% by weight or more, the average particle size will be sufficiently small, which is preferable. Moreover, if the content of the surfactant component contained in the nanoemulsion is 29.0% by weight or less, the viscosity of the nanoemulsion becomes small, which is preferable.
• a nanoemulsion according to one embodiment of the present invention comprises oil.
• the oil is not particularly limited as long as it is usually used for food, medicine, and cosmetics.
• Naturally derived oils such as fruit oil, kaya oil, rice bran oil, paulownia oil, canola oil, safflower oil, kukui nut oil, grapeseed oil, hazelnut oil, sunflower oil, rosehip oil, pistachio nut oil, palm oil (coconut oil), and vegetable squalane; Synthetic oils such as paraffin may be mentioned.
• the naturally-derived oil is more preferable because it is a vegetable oil.
• the oils are more preferably soybean oil, medium-chain fatty acid triglycerides, squalane, triethylhexanoin, coconut oil (coconut oil), bergamot oil, rosehip oil, and almond oil, and more preferably squalane and medium-chain fatty acid triglycerides. Only one type of the oil may be used, or two or more types may be used in combination. In addition, it is more preferable that the oil has a freezing point of 25° C. or lower.
• Vegetable oils containing a large amount of wax components such as palm oil and jojoba oil, which may solidify at room temperature (25° C.), beef tallow, lard, etc., are not preferable because they may impair the stability of the emulsion.
• the use of the oil is preferable because a stable nanoemulsion can be obtained.
• the content of the oil contained in the nanoemulsion according to one embodiment of the present invention is not particularly limited as long as it is an amount capable of forming a nanoemulsion, but is preferably 0.5 to 5.4% by weight, more preferably 1.5 to 5.0% by weight, and even more preferably 2.0 to 3.5% by weight, relative to the total weight of the nanoemulsion.
• the content of the oil contained in the nanoemulsion is 0.5% by weight or more, the poorly water-soluble functional ingredient can be stably dissolved, which is preferable. Moreover, if the content of the oil contained in the nanoemulsion is 5.4% by weight or less, the average particle size of the nanoemulsion is sufficiently small, which is preferable.
• a nanoemulsion according to one embodiment of the present invention comprises a sparingly water-soluble functional ingredient.
• a nanoemulsion according to an embodiment of the present invention may be used in combination with a plurality of poorly water-soluble components.
• “poorly water-soluble” means “sparingly soluble,” “extremely soluble,” and “almost insoluble” as defined in the Japanese Pharmacopoeia, and means that the solubility in water at 20°C is 10 mg/ml or less. More preferably, “poorly water-soluble” means “extremely soluble” and “almost insoluble” defined in the Japanese Pharmacopoeia, and means that the solubility in water at 20°C is 1 mg/ml or less. Since the poorly water-soluble functional ingredient has low solubility in water, it can be dispersed in an aqueous medium by dissolving it in the oil to form a nanoemulsion. The poorly water-soluble functional ingredient is preferably poorly water-soluble and fat-soluble.
• the term "functional ingredient” is not particularly limited as long as it is an ingredient that has some kind of function.
• the “functional ingredient” does not necessarily have to be solid at room temperature, and can be used in liquid form.
• Examples of “functional ingredients” that are liquid at room temperature include jojoba oil and squalane. Multiple oils may be included in the nanoemulsion if "functional ingredient” also applies to oils. In such a case, highly functional oils correspond to "functional ingredients”.
• one type of oil may be included as both the "functional ingredient” and the "oil”.
• the "weight ratio of the surfactant component to the oil” and “the weight ratio of the surfactant component to the total weight of the oil and the poorly water-soluble functional component” described below both mean “the weight ratio of the surfactant component to the one type of oil.”
• ingredients that are absorbed into the body and produce various functional effects include, for example, ingredients that have pharmacological activity used for suppressing, diagnosing, mitigating, treating, curing or preventing diseases or pathological conditions, and ingredients that provide predetermined nutritional or health benefits to the living body.
• poorly water-soluble functional ingredients which are poorly absorbed by the body as they are, are significantly effective in the composition of the present invention.
• the functional ingredient having pharmacological activity is an ingredient used in pharmaceuticals and the like.
• examples of poorly water-soluble functional ingredients having pharmacological activity include, but are not limited to, paclitaxel, cyclosporine, indomethacin, terfenadine, furosemide, acetazolamide, colistin, mebendazole, albendazole, nilotinib, lormetazepam, ibuprofen, mefinamic acid, ketoprofen, and bromazepam.
• ingredients that provide nutritional or health benefits include ingredients used in foods for special uses, foods with health claims (foods for specified health uses, foods with nutrient function claims), functional foods, dietary supplements, health supplements, nutrient-enriched foods, nutritionally adjusted foods, and supplements.
• examples of such poorly water-soluble functional ingredients include coenzyme Q10 (hereinafter sometimes referred to as CoQ10 in this specification), ⁇ -oryzanol, curcumin, tocotrienol, testosterone, menthol, carotenoids ( ⁇ -carotene, ⁇ -carotene, lutein, lycopene, astaxanthin, zeaxanthin, cryptoxanthin, fucoxanthin, xanthophyll, etc.), resveratrol, and docosahexaene.
• DHA eicosapentaenoic acid
• EPA fat-soluble vitamins
• vitamin A vitamin D
• vitamin E tocopherol
• vitamin K sesamin
• ⁇ -lipoic acid saw palmetto extract
• saw palmetto extract oleic acid, lauric acid, myristic acid, linoleic acid, palmitic acid
• St. John's wort hypericin
• royal jelly decenoic acid
• hesperidin nobiletin, quercetin, kaempferol, myricitrin , catechin, daidzein, glycitein, genistein, myricetin, stilbene, and the like, and combinations of two or more thereof.
• the ingredients that provide nutritional or health benefits include, for example, ingredients used in cosmetics, such as skin-improving ingredients, moisturizing ingredients, anti-aging ingredients, hair-restoring ingredients, and hair-growth ingredients.
• Poorly water-soluble functional ingredients include, for example, coenzyme Q10, ⁇ -oryzanol, curcumin, tocotrienol, carotenoids ( ⁇ -carotene, ⁇ -carotene, lutein, lycopene, astaxanthin, zeaxanthin, cryptoxanthin, fucoxanthin, xanthophyll, etc.), resveratrol, docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), fat-soluble vitamins (vitamin A, Vitamin D, vitamin E (tocopherol), vitamin K), ascorbyl tetrahexyldecanoate, ethylhexyl methoxycinnamate, sesamin, and alpha-
• the functional ingredients also include ingredients used as coating agents in industrial fields such as printing, such as coloring ingredients.
• examples of such poorly water-soluble functional ingredients include coenzyme Q10, curcumin, and carotenoids ( ⁇ -carotene, ⁇ -carotene, lutein, lycopene, astaxanthin, zeaxanthin, cryptoxanthin, fucoxanthin, xanthophyll, etc.), and combinations of two or more thereof.
• the functional ingredients also include ingredients used as insecticides, such as DDT (dichlorodiphenyltrichloroethane), tebufenpyrad, and fenoxycarb.
• DDT dichlorodiphenyltrichloroethane
• tebufenpyrad tebufenpyrad
• fenoxycarb ingredients used as insecticides, such as DDT (dichlorodiphenyltrichloroethane), tebufenpyrad, and fenoxycarb.
• the content of the poorly water-soluble functional ingredient contained in the nanoemulsion according to one embodiment of the present invention is not particularly limited, but is preferably 0.1 to 5.0% by weight, more preferably 0.2 to 4.5% by weight, and even more preferably 0.20 to 3.5% by weight, relative to the total weight of the nanoemulsion.
• the content of the poorly water-soluble functional ingredient contained in the nanoemulsion is 0.1% by weight or more, because the concentration of the poorly water-soluble ingredient does not decrease and the effect is exhibited. Moreover, if the content of the poorly water-soluble functional ingredient contained in the nanoemulsion is 4.5% by weight or less, the poorly water-soluble ingredient is less likely to precipitate and separate, which is preferable.
• a nanoemulsion according to one embodiment of the present invention contains at least one preservative selected from organic acids (salts) and biguanide compounds as a preservative.
• preservative means an agent used to inhibit microbial growth and prevent spoilage of nanoemulsion.
• organic acid (salt) means at least one of an organic acid and/or a salt thereof, that is, an organic acid, a salt thereof, and a mixture thereof.
• the organic acid (salt) is not particularly limited as long as it has an antiseptic effect.
• organic acids in such organic acids (salts) include sorbic acid, propionic acid, benzoic acid, acetic acid, lactic acid, citric acid, succinic acid, fumaric acid, and dehydroacetic acid.
• salts of organic acids include sodium salts, potassium salts, aluminum salts and calcium salts of the above organic acids.
• these organic acids or salts thereof may be used alone, or two or more of them may be used in combination.
• the organic acid (salt) is more preferably at least one selected from sorbic acid and its salts, and benzoic acid and its salts, still more preferably at least one selected from sodium sorbate, potassium sorbate, sodium benzoate and potassium benzoate, and most preferably at least one selected from potassium sorbate and sodium benzoate.
• the nanoemulsion containing the organic acid (salt) as an antiseptic is more preferably acidic.
• the pH of the nanoemulsion is preferably 7.0 or less, more preferably 6.5 or less, and even more preferably 6.0 or less.
• the nanoemulsion according to one embodiment of the present invention contains an organic acid (salt) as a preservative
• the nanoemulsion more preferably further contains a pH adjuster to adjust the pH to the above range.
• the pH adjuster is also not particularly limited, and examples thereof include acids such as citric acid and phosphoric acid.
• the pH adjuster is preferably contained in the form of a pH buffer such as citric acid-sodium citrate buffer and phosphate buffered saline.
• the content of the organic acid (salt) is preferably 0.05 wt% to 1.3 wt%, more preferably 0.10 wt% to 1.3 wt%, more preferably 0.20 wt% to 1.0 wt%, still more preferably 0.35 wt% to 0.50 wt%, relative to the total weight of the nanoemulsion.
• the content of the organic acid (salt) is 0.05% by weight or more, the antiseptic performance of the nanoemulsion is improved, which is preferable.
• the content of the organic acid (salt) is 1.3% by weight or less, the organic acid (salt) does not precipitate and the stability of the nanoemulsion is not impaired, which is preferable.
• the organic acid (salt) is at least one selected from potassium sorbate, sodium dehydroacetate and sodium benzoate
• the content of potassium sorbate is preferably 0.05% to 0.50% by weight, more preferably 0.10% to 0.50% by weight, still more preferably 0.10% to 0.30% by weight, particularly preferably 0.20% to 0.30% by weight, relative to the total weight of the nanoemulsion.
• the content of sodium dehydroacetate is preferably 0.10% to 0.60% by weight, more preferably 0.25% to 0.60% by weight, more preferably 0.25% to 0.50% by weight, relative to the total weight of the nanoemulsion;
• the content of sodium benzoate is preferably 0.10% to 0.80% by weight, more preferably 0.20% to 0.70% by weight, More preferably 0.24 wt % to 0.60 wt %, particularly preferably 0.36 wt % to 0.60 wt %.
• these biguanide-based compounds may be used alone, or two or more of them may be used in combination.
• the content of polyaminopropyl biguanide is preferably 0.002 wt% to 1.00 wt%, more preferably 0.003 wt% to 0.10 wt%, still more preferably 0.005 wt% to 0.05 wt%, particularly preferably 0.005 wt% to 0.01 wt%, relative to the total weight of the nanoemulsion. If the content of polyaminopropyl biguanide is 0.002% by weight or more, the antiseptic performance of the nanoemulsion is improved, which is preferable. If the content of polyaminopropyl biguanide is 1.00% by weight or less, it is preferable because the change in color tone of the nanoemulsion is small.
• a nanoemulsion according to one embodiment of the invention comprises an aqueous medium.
• the aqueous medium is not particularly limited as long as it contains water, and examples thereof include water, bubble water, fruit juice, vegetable juice, soft drinks, milk, yogurt drinks, soy milk, tea drinks, sports drinks, and nutritional drinks.
• the "water” may be, for example, so-called water such as ultrapure water (MilliQ (registered trademark) water), distilled water, ion-exchanged water, or various buffers such as phosphate buffer solution, physiological saline, and 5% glucose aqueous solution. Only one type of the aqueous medium may be used, or two or more types may be used in combination.
• the content of the aqueous medium contained in the nanoemulsion according to one embodiment of the present invention is not particularly limited as long as it is an amount capable of forming a nanoemulsion, but is preferably 50 to 89.3% by weight, more preferably 60 to 83.5% by weight, and even more preferably 70 to 80.0% by weight, relative to the total weight of the nanoemulsion.
• the nanoemulsion can be suitably formed, which is preferable. Moreover, if the content of the aqueous medium contained in the nanoemulsion is 89.3% by weight or less, the concentration of the poorly water-soluble functional ingredient does not become too low, which is preferable.
• the nanoemulsion may further contain additives other than the components described above, if necessary, as long as the effects of the present invention are not impaired.
• additives include, for example, antioxidants, colorants, perfumes, thickeners, antifoaming agents, and the like.
• the weight ratio of the surfactant component to the oil is preferably 2.80 or more and 240 or less, more preferably 4.50 or more and 240 or less, and even more preferably 6.50 or more and 240 or less.
• the weight ratio of the surfactant component to the total weight of the oil and the poorly water-soluble functional component is preferably 2.60 or more and 200 or less, more preferably 4.00 or more and 200 or less, and further preferably 5.20 or more and 200 or less.
• the weight ratio of the oil to the poorly water-soluble functional ingredient is preferably [-0.38 x (LogP of the poorly water-soluble functional ingredient) + 5.169] or more and 2000 or less.
• the lower limit of the weight ratio of the oil to the poorly water-soluble functional ingredient (oil/slightly water-soluble functional ingredient) is more preferably [-0.38 x (LogP of poorly water-soluble functional ingredient) + 5.9] or more, and still more preferably [-0.38 x (LogP of poorly water-soluble functional ingredient) + 6.7] or more.
• the lower limit of the weight ratio of the oil to the sparingly water-soluble functional ingredient is preferably [-0.38 x (LogP of the sparingly water-soluble functional ingredient) + 5.169] or more, because the amount of oil for stably dissolving the sparingly water-soluble functional ingredient is sufficient, and a nanoemulsion with excellent stability can be realized.
• logP is the common logarithm of the 1-octanol/water or buffer solution partition coefficient of a chemical substance, and the flask according to the OECD GUIDELINE FOR THE TESTING OF CHEMICALS, "Partition Coefficient (n-octanol/water): Shake Flask Method” It means the value measured by shaking method.
• the weight ratio of the oil to the slightly water-soluble functional ingredient is preferably [-4.955 x (LogP of the slightly water-soluble functional ingredient) + 23.56] or more and 2000 or less.
• the lower limit of the weight ratio of the oil to the slightly water-soluble functional ingredient (oil/slightly water-soluble functional ingredient) is more preferably [ ⁇ 4.955 ⁇ (LogP of the slightly water-soluble functional ingredient)+26] or more, and still more preferably [ ⁇ 4.955 ⁇ (LogP of the slightly water-soluble functional ingredient)+29] or more.
• the lower limit of the weight ratio of the oil to the water-slightly water-soluble functional ingredient is [ ⁇ 4.955 ⁇ (LogP of the slightly water-soluble functional ingredient)+23.56] or more.
• said surfactant component and said oil form micelles. That is, the poorly water-soluble functional ingredient dissolved in the oil is surrounded by the surfactant ingredient with the hydrophobic group inside to form a micelle. These micelles are the emulsified particles of the nanoemulsion.
• the average particle size of the emulsified particles is preferably 30 nm or less, more preferably 18 nm or less. If the average particle size of the emulsified particles is 30 nm or less, the absorption efficiency of the slightly water-soluble functional ingredient into the living body can be improved, which is preferable. In addition, a transparent nanoemulsion can be obtained due to the small average particle size of the emulsified particles.
• the “average particle size of emulsified particles” refers to a value measured using Zetasizer Nano ZS (manufactured by Malvern Institutes) in the measurement mode “size-small-vol-cell ⁇ 1.SOP”.
• the PDI (particle size distribution index) of the emulsified particles is preferably 0.14 or less.
• the PDI (particle size distribution index) of the emulsified particles is 0.14 or less, a nanoemulsion having excellent stability including many emulsified particles having an average particle diameter of 30 nm or less of the emulsified particles excellent in bioabsorbability can be realized, which is preferable.
• "PDI (particle size distribution index) of the emulsified particles” refers to a value measured by "size-small-vol-cell x 1.SOP" using Zetasizer Nano ZS (manufactured by Malvern Institutes).
• PDI (Polydispersity Index) is also referred to as particle size distribution index, particle size distribution index, polydispersity or polydispersity index.
• the nanoemulsion is preferably a monodisperse dispersion that does not contain particles (sub-peaks) of 100 nm or more. If the nanoemulsion does not contain particles (sub-peaks) of 100 nm or more and is a monodisperse dispersion in which the homogeneity of the particle size of the emulsified particles is improved, it is preferable because a nanoemulsion that is transparent, excellent in bioabsorbability, and excellent in stability can be realized.
• the method for producing the nanoemulsion according to one embodiment of the present invention is not particularly limited, but for example, it can be produced by a production method including a mixing step of mixing the surfactant component, the oil, and the poorly water-soluble functional component, an aqueous medium addition step of mixing the composition obtained by the mixing step with an aqueous medium, and a preservative addition step of adding a preservative to the composition obtained by the aqueous medium addition step.
• the surfactant component, the oil, and the poorly water-soluble functional component are preferably mixed so that the weight ratio of the surfactant component to the oil is 2.80 or more and 240 or less, and the weight ratio of the surfactant component to the total weight of the oil and the poorly water-soluble functional component is 2.60 or more and 200 or less.
• the order of mixing the surfactant component, the oil, and the poorly water-soluble functional component is not particularly limited, and all may be mixed at the same time, the surfactant component and the oil may be mixed and then the poorly water-soluble functional component may be mixed, the oil may be mixed after the surfactant component and the poorly water-soluble functional component are mixed, or the surfactant component may be mixed after the oil and the poorly water-soluble functional component are mixed. May be mixed.
• the method for mixing the components is not particularly limited as long as it is a method that can uniformly dissolve the surfactant component, the oil, and the poorly water-soluble functional component.
• the method of mixing and stirring each component can be mentioned.
• each component can be uniformly dissolved without applying a particularly strong shearing force.
• each component can be uniformly dissolved by stirring using a magnetic stirrer.
• the temperature at which each component is mixed is not particularly limited, but the liquid temperature is more preferably 20°C or higher and 90°C or lower, and more preferably 30°C or higher and 75°C or lower.
• the step of mixing the composition obtained by the mixing step with an aqueous medium is a step of adding the aqueous medium to the composition obtained by the mixing step.
• the aqueous medium may be added all at once, or may be added in several portions while stirring.
• the method of mixing the composition obtained in the mixing step and the aqueous medium is not particularly limited as long as it is a method capable of dispersing the composition as emulsified particles in the aqueous medium.
• a method of mixing and stirring the composition and the aqueous medium can be used.
• the composition can be dispersed as emulsified particles in the aqueous medium without applying a particularly strong shearing force.
• the composition and the aqueous medium can be stirred using, for example, a magnetic stirrer.
• the temperature at which the composition and the aqueous medium are mixed is not particularly limited, but the liquid temperature is more preferably 20°C or higher and 90°C or lower, and more preferably 30°C or higher and 75°C or lower.
• the preservative addition step is a step of adding a preservative to the composition obtained by the aqueous medium addition step.
• the aqueous medium may be added all at once, or may be added in several portions while stirring.
• the method of adding the preservative to the composition obtained by the aqueous medium addition step is not particularly limited, and examples include a method of mixing and stirring the composition and the preservative.
• the composition and the preservative can be stirred using, for example, a magnetic stirrer.
• the temperature at which the composition and the preservative are mixed is not particularly limited, but the liquid temperature is preferably 5°C or higher and 55°C or lower, more preferably 10°C or higher and 50°C or lower.
• the preservative addition step does not necessarily have to be performed after the aqueous medium addition step, and the preservative may be added in the mixing step of mixing the oil and the poorly water-soluble functional ingredient, or in the aqueous medium addition step of mixing the composition obtained by the mixing step and the aqueous medium.
• the present invention also includes pharmaceuticals, functional foods, cosmetics, coating agents, or pesticides containing the nanoemulsion according to one embodiment of the present invention.
• One embodiment of the present invention includes the following configurations.
• the nanoemulsion according to [1] which contains at least one selected from sorbic acid and its salts, benzoic acid and its salts, and dehydroacetic acid and its salts as the organic acid (salt), and further contains a pH adjuster.
• the organic acid (salt) contains at least one selected from potassium sorbate, sodium benzoate and sodium dehydroacetate, the content of potassium sorbate is 0.05% by weight to 0.50% by weight relative to the total weight of the nanoemulsion, the content of sodium benzoate is 0.10% by weight to 0.80% by weight relative to the total weight of the nanoemulsion, and the content of sodium dehydroacetate is 0.10% by weight to 0.10% by weight relative to the total weight of the nanoemulsion.
• the surfactant component contains at least one selected from polyoxyalkylene alkyl ethers, polyoxyalkylene alkenyl ethers, polyoxyethylene castor oil, alkylene oxide adducts of sorbitan fatty acid esters, and polyoxyethylene alkanoic acid hydrogenated castor oil.
• the presence or absence of sub-peaks was determined from the particle size distribution map obtained as the measurement result. When there are sub-peaks, the measurement results are automatically output as Peak-2, Peak-3, and the like.
• Method A (Preservative property of nanoemulsion)
• 20 g of the nanoemulsion was placed in a sterilized vial and inoculated with 0.2 mL of the test bacterial solution (kitchen wastewater).
• the sample inoculated with the test bacterial solution was stored at 30°C, and the number of viable bacteria was measured on the 21st day.
• Evaluation criteria are as follows. A: The viable count on the 21st day is less than 0.01% of the viable count after inoculation.
• ⁇ The viable count on the 21st day is 0.01% or more and less than 100% of the viable count after seeding.
• x The viable count on the 21st day is 100% or more of the viable count after inoculation.
• Method B 20 g of the nanoemulsion was placed in a sterilized vial, and 0.15 mL each of five types of test bacterial solutions, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida, and Aspergillus niger, was inoculated. The obtained 5 samples were stored at 22.5° C., and the viable cell count was measured on the 28th day. Evaluation criteria are as follows. A: The viable cell count on the 28th day of all the 5 types of test bacteria is less than 0.01% of the viable cell count after inoculation.
• At least one of the 5 types of test bacteria has a viable count on day 28 of 0.01% or more and less than 100% of the viable count after seeding, and the viable count on day 28 is 100% or more after seeding.
• the viable cell count on the 28th day of at least one of the five test strains is 100% or more of the viable cell count after inoculation.
• Citric acid monohydrate and trisodium citrate dihydrate were mixed with ion-exchanged water so that the pH was 5.6 and the sum of the concentrations of citric acid and sodium citrate was 0.1 mol/L.
• Example 1 Polyoxyethylene (9) oleyl ether and polyoxyethylene (7) lauryl ether as surfactants, squalane as oil, and ⁇ -oryzanol as sparingly water-soluble component were weighed into a beaker so that the weight ratios shown in Table 1 were obtained. The mixture in the weighed beaker was stirred using a magnetic stirrer at 70° C. with a magnetic stirrer until all the poorly water-soluble functional ingredients were uniformly dissolved to obtain a viscous liquid nanoemulsion preparation composition.
• Example 11 A nanoemulsion was prepared in the same manner as in Example 1, except that sodium benzoate and potassium sorbate were used as preservatives, and the weight ratio of each component was changed to the weight ratio shown in Table 1. The resulting nanoemulsion was evaluated. Table 1 shows the results.
• Example 1 A nanoemulsion was prepared in the same manner as in Example 1, except that no preservative was added and the weight ratio of each component was changed to the weight ratio shown in Table 1. The resulting nanoemulsion was evaluated. Table 1 shows the results.
• the weight ratio is 0.36% or more and 0.59% or less by weight
• potassium sorbate is used and the weight ratio is 0.20% or more and 0.30% or less and the pH is 5.5 or less
• sodium dehydroacetate is used and the weight ratio is 0.25% or more and 0.50% or less and the pH is 6.0 or less
• the number of viable bacteria on the 21st day in Method A is sown. It was less than 0.01% of the viable cell count after seeding.
• the viable count on day 21 in method A is less than 0.01% of the viable count after seeding
• the viable count on day 28 of at least one of the five types of test bacteria in method B is between 0.01% and less than 100% of the viable count after seeding, and there are no bacteria whose viable count on day 28 is 100% or more of the viable count after seeding.
• Example 16 A nanoemulsion was prepared in the same manner as in Example 1, except that polysorbate 80 was used as the surfactant instead of polyoxyethylene (9) oleyl ether and polyoxyethylene (7) lauryl ether, medium-chain fatty acid triglyceride was used instead of squalane as the oil, coenzyme Q10 was used instead of ⁇ -oryzanol as the slightly water-soluble functional component, and the weight ratio of each component was changed to the weight ratio shown in Table 2. The resulting nanoemulsion was evaluated. Table 2 shows the results.
• Example 2 A nanoemulsion was prepared in the same manner as in Example 16, except that no preservative was added and the weight ratio of each component was changed to the weight ratio shown in Table 2. The resulting nanoemulsion was evaluated. Table 2 shows the results.
• Example 19-20 A nanoemulsion was prepared in the same manner as in Example 17, except that polyaminopropylpiguanide was used as a preservative, polyoxyethylene (35) castor oil was used instead of polyoxyethylene (9) oleyl ether and polyoxyethylene (7) lauryl ether as a surfactant, coenzyme Q10 was used instead of ⁇ -oryzanol as a sparingly water-soluble functional component, and the weight ratio of each component was changed to the weight ratio shown in Table 3. The resulting nanoemulsion was evaluated. Table 3 shows the results.
• Example 3 A nanoemulsion was prepared in the same manner as in Example 19, except that no preservative was added and the weight ratio of each component was changed to the weight ratio shown in Table 3. The resulting nanoemulsion was evaluated. Table 3 shows the results.
• a stable nanoemulsion having an antiseptic effect can be obtained when polyaminopropylbiguanide is included as the biguanide-based compound, preferably 0.005% to 0.03% by weight relative to the total weight of the nanoemulsion.
• Some of the comparative examples include nanoemulsions that do not contain poorly water-soluble functional ingredients, but the presence or absence of poorly water-soluble functional ingredients does not affect the evaluation of antiseptic properties, so antiseptic properties can be evaluated regardless of the presence of poorly water-soluble functional ingredients.
• Example 21 A nanoemulsion was prepared in the same manner as in Example 1, except that potassium sorbate was used instead of sodium benzoate as a preservative, PEG-50 hydrogenated castor oil isostearate was used as a surfactant instead of polyoxyethylene (9) oleyl ether and polyoxyethylene (7) lauryl ether, triethylhexanoin was used as an oil instead of squalane, and the weight ratio of each component was changed to the weight ratio shown in Table 5. The resulting nanoemulsion was evaluated. Table 5 shows the results.
• Example 22 A nanoemulsion was prepared in the same manner as in Example 21, except that rice bran oil was used instead of triethylhexanoin as the oil, and the weight ratio was changed to the weight ratio shown in Table 5. The resulting nanoemulsion was evaluated. Table 5 shows the results.
• Example 24 A nanoemulsion was prepared in the same manner as in Example 23, except that potassium sorbate was used as a preservative instead of sodium benzoate, rice bran oil was used instead of triethylhexanoin as an oil, and the weight ratio was changed to the weight ratio shown in Table 5. The resulting nanoemulsion was evaluated. Table 5 shows the results.
• Example 25 A nanoemulsion was prepared in the same manner as in Example 24, except that potassium sorbate was used as a preservative, resveratrol was used instead of coenzyme Q10 as a poorly water-soluble functional ingredient, and the weight ratio of each ingredient was changed to the weight ratio shown in Table 5. The resulting nanoemulsion was evaluated. Table 5 shows the results.
• Example 26 A nanoemulsion was prepared in the same manner as in Example 25, except that no poorly water-soluble functional ingredient was added. The resulting nanoemulsion was evaluated. Table 5 shows the results.
• the content of the sodium benzoate or the potassium sorbate is 0.30% by weight with respect to the total weight of the nanoemulsion, and the pH is 6.0 or less, it can be seen that a stable nanoemulsion having an antiseptic effect can be obtained.
• a composition for preparing a nanoemulsion and a nanoemulsion according to an embodiment of the present invention have antiseptic properties and excellent stability due to the above-described configuration. Therefore, it can be suitably used in the commercialization and sale of nanoemulsions in cosmetics, pharmaceuticals, foods, industrial fields, and the like.

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