Active oxygen scavenger, method for eliminating active oxygen, and method for producing active oxygen scavenger

Abstract

The invention provides a novel active oxygen scavenger with suppressed oxidizing power.　The active oxygen scavenger of the present disclosure is characterized by being manufactured by processing an active oxygen scavenger comprising an alcohol ozone-treated with an oxygen allotrope-containing gas.

Description

Active oxygen scavenger, active oxygen scavenging method, and method for producing active oxygen scavenger

[0001] The present disclosure relates to an active oxygen scavenger, a method for scavenging active oxygen, and a method for producing an active oxygen scavenger.

[0002] Reactive oxygen refers to a state in which oxygen has become radicals and is more activated than normal. When a large amount of reactive oxygen is released outside the cell, various cells, tissues, and humoral factors are damaged, causing an inflammatory reaction (Non-Patent Document 1).

[0003] Toshikazu Yoshikawa, Norimasa Yoshida, and Motoharu Kondo, "Inflammation and Active Oxygen and Free Radicals," JAPANESE JOURNAL OF INFLAMMATION REVIEW ARTICLE, VOL. 13, NO. 5, pp. 413-421 (published September 1993)

[0004] For these reasons, active oxygen scavengers have great industrial value.

[0005] However, if the oxidizing power of the active oxygen scavenger is too high, the applications of the active oxygen scavenger may be limited, for example, because it may become difficult to use it in combination with an agent that is weak to oxidation.

[0006] Therefore, an object of the present disclosure is to provide a novel active oxygen scavenger with reduced oxidizing power, a method for scavenging active oxygen, and a method for producing an active oxygen scavenger.

[0007] In order to achieve the above object, the active oxygen scavenger of the present disclosure is characterized in that it is obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas.

[0008] The method for eliminating active oxygen disclosed herein is characterized by including a reaction step of reacting an active oxygen scavenger obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas with active oxygen.

[0009] The method for producing an active oxygen scavenger of the present disclosure is characterized by including an ozone treatment step of ozone-treating alcohol with an oxygen allotrope-containing gas, and a processing step of processing the ozone-treated alcohol ozone-treated in the ozone treatment step.

[0010] According to the present disclosure, it is possible to provide a novel active oxygen scavenger with reduced oxidizing power, a method for scavenging active oxygen, and a method for producing an active oxygen scavenger.

[0011] FIG. 1 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of an example. FIG. 2 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of another example. FIG. 3 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 4 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 5 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 6 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 7 is a graph showing the oxidizing power of an active oxygen scavenger of an example. FIG. 8 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 9 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 10 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. FIG. 11 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. Fig. 12 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. Fig. 13 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. Fig. 14 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example. Fig. 15 is a graph showing the active oxygen scavenging rate of an active oxygen scavenger of yet another example.

[0012] In the present specification, when a compound has isomers such as tautomers or stereoisomers (e.g., geometric isomers, conformational isomers, and optical isomers), any of these isomers can be used in the present disclosure unless otherwise specified. Furthermore, in the present disclosure, when a substance can form a salt, the salt can also be used in the present disclosure unless otherwise specified. The salt may be an acid addition salt or a base addition salt. Furthermore, the acid that forms the acid addition salt may be an inorganic acid or an organic acid, and the base that forms the base addition salt may be an inorganic base or an organic base. The inorganic acid is not particularly limited, but examples thereof include sulfuric acid, phosphoric acid, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, hypofluorite acid, hypochlorous acid, hypobromous acid, hypoiodous acid, fluorite acid, chlorous acid, bromous acid, iodous acid, fluorine acid, chlorine acid, bromine acid, iodic acid, perfluorine acid, perchlorine acid, perbromine acid, and periodic acid. The organic acid is also not particularly limited, but examples thereof include p-toluenesulfonic acid, methanesulfonic acid, oxalic acid, p-bromobenzenesulfonic acid, carbonic acid, succinic acid, citric acid, benzoic acid, and acetic acid. The inorganic base is not particularly limited, but examples thereof include ammonium hydroxide, alkali metal hydroxides, alkaline earth metal hydroxides, carbonates, and bicarbonates, and more specifically, examples thereof include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium bicarbonate, potassium bicarbonate, calcium hydroxide, and calcium carbonate. The organic base is also not particularly limited, but examples thereof include ethanolamine, triethylamine, and tris(hydroxymethyl)aminomethane. The method for producing these salts is also not particularly limited, and they can be produced, for example, by adding the above-mentioned acid or base to the compound as appropriate using a known method.

[0013] The present disclosure will be described in more detail below with reference to examples. However, the present disclosure is not limited by the following explanation. Furthermore, the explanations in this disclosure can be mutually incorporated unless otherwise specified. In this specification, when the expression "~" is used, it is used to mean including the numerical or physical values ​​before and after it. In addition, in this specification, the expression "A and / or B" includes "A only," "B only," and "both A and B."

[0014] [1. Active oxygen scavenger and method for producing same] As described above, the active oxygen scavenger of the present disclosure is characterized in that it is obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas. Specifically, ozone treatment involves generating ozone using the oxygen-containing gas contained in the oxygen allotrope-containing gas as a raw material, and the alcohol can be ozone-treated with the ozone. The ozone-treated alcohol is preferably ozone-treated glycerin. The structure of the ozone-treated alcohol is not particularly limited, but it preferably contains an oxygen-treated alcohol having an active oxygen scavenging function. In the present disclosure, the structure of the ozone-treated alcohol having an active oxygen scavenging function is also not particularly limited, and any structure may be used as long as it has an active oxygen scavenging function.

[0015] In the present disclosure, the processing of the active oxygen scavenger containing ozone-treated alcohol can be, for example, heating, neutralization, reduction, etc. The processing is preferably heating from the viewpoint of simplicity, practicality, etc. Details will be described later.

[0016] In the present disclosure, oxygen allotropes include, for example, oxygen (O ２ ), ozone (O ３ ) and the like, with ozone being particularly preferred.

[0017] In the present disclosure, the alcohol may be a monohydric alcohol, a polyhydric alcohol, or a sugar alcohol, with a polyhydric alcohol being preferred. Furthermore, the alcohol may be a saturated alcohol or an unsaturated alcohol, may be linear, may contain a branched chain or not, may contain a cyclic structure or not, may be an aliphatic alcohol or an aromatic alcohol, and may be a natural or synthetic product. Examples of monohydric alcohols include monohydric alcohols having 1 to 30 carbon atoms, such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, and 2-methyl-2-propanol (tert-butyl alcohol). Other examples of monohydric alcohols include saturated aliphatic alcohols such as lauryl alcohol, myristyl alcohol, cetanol, cetearyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, etc., unsaturated aliphatic alcohols such as oleyl alcohol, etc., and branched chain aliphatic alcohols such as hexyldecanol, isostearyl alcohol, octyldodecanol, decyltetradecanol, etc. Examples of polyhydric alcohols include polyhydric alcohols having 1 to 30 carbon atoms. Examples of polyhydric alcohols include dihydric alcohols (e.g., ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, and octylene glycol); trihydric alcohols (e.g., glycerin and trimethylolpropane); tetrahydric alcohols (e.g., pentaerythritol such as 1,2,6-hexanetriol); pentahydric alcohols (e.g., xylitol); hexahydric alcohols (e.g., sorbitol and mannitol); polyhydric alcohol polymers (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, and polyglycerin);dihydric alcohol alkyl ethers (e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, etc.); dihydric alcohol alkyl ethers (e.g., diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, dihydric alcohol ether esters (e.g., ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate, etc.); glycerin monoalkyl ethers (e.g., xyl alcohol, selachyl alcohol, batyl alcohol, etc.);Examples of the sugar alcohol include sugar alcohols (e.g., sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch-decomposed sugars, maltose, xylitose, and alcohols derived from starch-decomposed sugars); glysolid; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl alcohol; POP-butyl ether; POP·POE-butyl ether; tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphate; POP·POE-pentaneerythritol ether, and polyglycerin, with glycerin being particularly preferred among these. Examples of the sugar alcohol include the sugar alcohols described above.

[0018] The pH of the active oxygen scavenger of the present disclosure is not particularly limited, and may be, for example, 1.00 or more, 1.50 or more, 2.00 or more, 2.50 or more, 3.00 or more, 3.50 or more, 4.00 or more, 4.50 or more, 5.00 or more, or 5.50 or more, or may be, for example, 6.00 or less, 5.50 or less, 5.00 or less, 4.50 or less, 4.00 or less, 3.50 or less, 3.00 or less, 2.50 or less, 2.00 or less, or 1.50 or less, For example, 1.00 to 6.00, 1.00 to 5.50, 1.00 to 5.00, 1.00 to 4.50, 1.00 to 4.00, 1.00 to 3.50, 1.00 to 3.00, 1.00 to 2.50, 1.00 to 2.00, 1.00 to 1.50, 1.50 to 6.00, 1.50 to 5.50, 1.50 to 5.00, 1.50 to 4.50, 1.50 to 4.00, 1.50 to 3.50, 1.50 to 3.00, 1.50 to 2.50, 1.5 0 to 2.00, 2.00 to 6.00, 2.00 to 5.50, 2.00 to 5.00, 2.00 to 4.50, 2.00 to 4.00, 2.00 to 3.50, 2.00 to 3.00, 2.00 to 2.50, 2.50 to 6.00, 2.50 to 5.50, 2.50 to 5.00, 2.50 to 4.50, 2.50 to 4.00, 2.50 to 3.50, 2.50 to 3.00, 3.00 to 6.00, 3.00 to 5.50, 3.00 to 5.00, It may be 3.00 to 4.50, 3.00 to 4.00, 3.00 to 3.50, 3.50 to 6.00, 3.50 to 5.50, 3.50 to 5.00, 3.50 to 4.50, 3.50 to 4.00, 4.00 to 6.00, 4.00 to 5.50, 4.00 to 5.00, 4.00 to 4.50, 4.50 to 6.00, 4.50 to 5.50, 4.50 to 5.00, 5.00 to 6.00, 5.00 to 5.50, 5.50 to 6.00, etc.

[0019] As described above, the method for producing an active oxygen scavenger of the present disclosure is characterized by comprising an ozone treatment step of ozone-treating an alcohol with an oxygen allotrope-containing gas, and a processing step of processing the ozone-treated alcohol ozone-treated in the ozone treatment step. However, the active oxygen scavenger of the present disclosure is not limited to this production method and may be produced by any production method. Furthermore, the processing step is not particularly limited, and may be, for example, a heating step of heating the ozone-treated alcohol. Below, the method for producing an active oxygen scavenger of the present disclosure will be described in more detail using examples.

[0020] In the following, an example will be described in which glycerin is used as the alcohol, ozone oxidized, and the ozone-oxidized glycerin is further heated. However, as mentioned above, the following description is merely an example, and the method for producing the oxidation reaction product is not limited to the following description. For example, the following method can be carried out in the same manner using other alcohols instead of glycerin. The ozone treatment step can be carried out, for example, by using an oxygen allotrope other than ozone (e.g., O ２ In addition, for example, not only the type of alcohol and the method of oxygen treatment of the alcohol, but also the concentration of each substance, reaction temperature, reaction time, and other reaction conditions can be appropriately changed.

[0021] The active oxygen scavenger of the present disclosure can be produced by a production method including, for example, a step of oxidizing glycerin by contacting glycerin with ozone, more specifically, by mixing glycerin with ozone (corresponding to the aforementioned "ozone treatment step"), and an oxidation step of oxidizing the ozone-treated alcohol thus oxidized (corresponding to the aforementioned "processing step"). The step of oxidizing glycerin may be, for example, a step of bringing a glycerin solution into gas-liquid contact with a gas containing ozone to oxidize glycerin.

[0022] The concentration of the glycerin solution is not particularly limited. For example, the higher the glycerin concentration, the higher the concentration of ozone treatment that can be achieved in the glycerin solution. However, in the present disclosure, even a low glycerin concentration is sufficient. The concentration of the glycerin solution may be, for example, 1% by weight or more, 2% by weight or more, 3% by weight or more, 5% by weight or more, 10% by weight or more, 20% by weight or more, 30% by weight or more, 40% by weight or more, 50% by weight or more, etc., and the upper limit is not particularly limited, but may be, for example, 100% by weight (100% purity) glycerin. Examples of high-concentration glycerin solutions include glycerin solutions with a glycerin concentration of 75% or more. Specific examples include glycerin solutions with a glycerin concentration of 84 to 87% by weight as specified in the Japanese Pharmacopoeia. Concentrated glycerin solutions with a glycerin concentration of 98% by weight or more as specified in the Japanese Pharmacopoeia are more preferred, and purified glycerin solutions with a concentration of 98.5% by weight or more are even more preferred. In the glycerin solution, the solvent for glycerin is not particularly limited and is, for example, an aqueous solvent such as water.

[0023] The ozone concentration of the ozone-containing gas is not particularly limited, and may be, for example, a gas containing ozone at a high concentration. The method for producing the ozone-containing gas is not particularly limited, and for example, an ozone generator that generates ozone by silently discharging oxygen gas can be used. When oxygen gas is used, for example, a medical oxygen cylinder may be used, or oxygen gas produced by an oxygen generator may be used.

[0024] The method for bringing the glycerin solution into gas-liquid contact with the ozone-containing gas is not particularly limited, and examples thereof include a method in which a high-concentration (e.g., 98% by weight or more) glycerin solution is placed in a tank and the high-ozone-concentration gas is released into the tank as fine bubbles using an air diffuser. Specifically, for example, an ozone-treated glycerin solution having an equivalent hydrogen peroxide concentration of about 4000 ppm can be produced by aerating a gas having an ozone concentration of about 37,000 ppm into the concentrated glycerin solution for about 7 days. The aeration time is not particularly limited, and for example, an ozone-treated glycerin solution (active oxygen scavenger) containing a higher concentration of ozone-treated glycerin having active oxygen scavenging function can be produced by aerating the concentrated glycerin solution for a relatively long time.

[0025] The ozone-treated glycerin solution (active oxygen scavenger) thus produced can be further heated to produce the active oxygen scavenger of the present disclosure. This heating step corresponds to the "heating step," which is an example of the "processing step." In the present disclosure, "heating" refers to, for example, a process in which the temperature of the object to be heated is maintained at a temperature higher than 35°C. In the present disclosure, the heating temperature in the "heating step" is not particularly limited, but may be, for example, a temperature higher than 35°C as described above, or, for example, 40°C or higher, 50°C or higher, 80°C or higher, 90°C or higher, or 100°C or higher, or may be, for example, 290°C or lower, which is the boiling point of glycerin. In the present disclosure, the heating time in the "heating step" is not particularly limited, but may be, for example, 1 hour or more, 3 hours or more, 6 hours or more, 12 hours or more, or 24 hours or more. The reason why heating can suppress the oxidizing power of the active oxygen scavenger is not clear. Furthermore, in the present disclosure, after the "processing step (e.g., the "heating step")," the active oxygen scavenging function of the active oxygen scavenger may be the same as or may be increased compared to before the "processing step," or may be decreased compared to before the "processing step."

[0026] [2. Alcohol] The active oxygen scavenger of the present disclosure may be, for example, an alcohol solution. As described above, glycerin is particularly preferred as the alcohol. The active oxygen scavenger of the present disclosure can stably maintain the ozone-treated alcohol having the active oxygen scavenging function by allowing the ozone-treated alcohol having the active oxygen scavenging function to coexist with alcohol, for example.

[0027] In the composition of the present disclosure, the content of the alcohol is, for example, 0.1 to 100 w / v %, preferably 40 to 100 w / v %, when the alcohol is glycerin.

[0028] [3. Other Components] The active oxygen scavenger of the present disclosure may contain other components in addition to the ozonated alcohol. The other components may be, for example, the alcohol, or other components added to a formulation to be applied to the skin. Specific examples of the other components include components added to topical skin preparations and cosmetics (including quasi-drugs). Examples of the components added to topical skin preparations include pharmaceutically acceptable carriers. Examples of the other components include components added when applied to the skin or transdermally, such as aqueous solvents such as water, alcohols, moisturizers, oils, softeners (emollients), surfactants (solubilizers, emulsifiers), salts, thickeners, pH adjusters, UV absorbers, pharmaceuticals, buffers, colorants, preservatives, and fragrances.

[0029] The active oxygen scavenger of the present disclosure may contain, as needed, other ingredients such as anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, moisturizers, water-soluble polymers, thickeners, film-forming agents, ultraviolet absorbers, sequestering agents, lower alcohols, polyhydric alcohols, oils, sugars, amino acids, organic amines, polymer emulsions, pH adjusters, skin nutrients, vitamins, plant extracts, antioxidants, antioxidant aids, fragrances, colorants, preservatives, disinfectants, and water.

[0030] Examples of cationic surfactants include alkyltrimethylammonium salts (e.g., stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, etc.); alkylpyridinium salts (e.g., cetylpyridinium chloride, etc.); distearyldimethylammonium chloride, dialkyldimethylammonium salts; poly(N,N'-dimethyl-3,5-methylenepiperidinium) chloride; alkyl quaternary ammonium salts; alkyldimethylbenzylammonium salts; alkylisoquinolinium salts; dialkylmorphonium salts; POE-alkylamines; alkylamine salts; polyamine fatty acid derivatives; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride, etc.

[0031] Examples of amphoteric surfactants include imidazoline-based amphoteric surfactants (e.g., 2-undecyl-N,N,N-(hydroxyethylcarboxymethyl)-2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, etc.); betaine-based surfactants (e.g., lauryldimethylaminoacetic acid betaine, alkyl betaine, alkylamido betaine, alkyl sulfobetaine, etc.); and the like.

[0032] Examples of lipophilic nonionic surfactants include sorbitan fatty acid esters (e.g., sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, diglycerol sorbitan penta-2-ethylhexylate, diglycerol sorbitan tetra-2-ethylhexylate, etc.); glycerin polyglycerin fatty acids (e.g., glycerin monocottonseed oil fatty acid, glycerin monoerucate, glycerin sesquioleate, glycerin monostearate, glycerin α,α'-oleic acid pyroglutamate, glycerin monostearate malate, etc.); propylene glycol fatty acid esters (e.g., propylene glycol monostearate, etc.); hydrogenated castor oil derivatives; and glycerin alkyl ethers.

[0033] Examples of hydrophilic nonionic surfactants include POE-sorbitan fatty acid esters (e.g., POE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate, POE-sorbitan tetraoleate, etc.); POE-sorbitol fatty acid esters (e.g., POE-sorbitol monolaurate, POE-sorbitol monooleate, POE-sorbitol pentaoleate, POE-sorbitol monostearate, etc.); POE-glycerin fatty acid esters (e.g., POE-glycerin monostearate, POE-monooleates such as POE-glycerin monoisostearate and POE-glycerin triisostearate; POE-fatty acid esters (for example, POE-distearate, POE-monodioleate, ethylene glycol distearate, etc.); POE-alkyl ethers (for example, POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, POE-cholestanol ether, etc.); Pluronics (Pluronic is a registered trademark); POE. POP-alkyl ethers (e.g., POE·POP-cetyl ether, POE·POP-2-decyltetradecyl ether, POE·POP-monobutyl ether, POE·POP-hydrogenated lanolin, POE·POP-glycerin ether, etc.); tetraPOE·tetraPOP-ethylenediamine condensates (e.g., Tetronic, etc.); POE-castor oil hydrogenated castor oil derivatives (e.g., POE-castor oil, POE-hydrogenated castor oil, POE-hydrogenated castor oil monoisostearate, POE-hydrogenated castor oil triisostearate, POE-hydrogenated castor oil monopyrolate, glutamic acid monoisostearate diester, POE-hydrogenated castor oil maleic acid, etc.); POE-beeswax / lanolin derivatives (for example, POE-sorbitol beeswax, etc.); alkanolamides (for example, coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide, cocamide methyl monoethanolamide, etc.); POE-propylene glycol fatty acid esters; POE-alkylamines; POE-fatty acid amides; diethylene glycol laurate; sucrose fatty acid esters; alkylethoxydimethylamine oxide;Examples include trioleyl phosphate;

[0034] Examples of moisturizing agents include glycerin, sugar alcohols, polyethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carboxylate, alkylene oxide derivatives, short-chain soluble collagen, diglycerin (EO)PO adduct, Rosa illustrator extract, Achillea millefolium extract, and Melilot extract.

[0035] Examples of natural water-soluble polymers include plant-derived polymers (e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (marmelo), algae colloid (cassowia extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial-derived polymers (e.g., xanthan gum, dextran, succinoglucan, pullulan, etc.); and animal-derived polymers (e.g., collagen, casein, albumin, gelatin, etc.).

[0036] Examples of semi-synthetic water-soluble polymers include starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methyl cellulose, ethyl cellulose, methylhydroxypropyl cellulose, hydroxyethyl cellulose, sodium cellulose sulfate, hydroxypropyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, crystalline cellulose, cellulose powder, etc.); and alginic acid-based polymers (e.g., sodium alginate, propylene glycol alginate, etc.).

[0037] Examples of synthetic water-soluble polymers include vinyl polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene polymers (e.g., polyethylene glycol 20,000, 40,000, 60,0000 polyoxyethylene polypropylene copolymers, highly polymerized polyethylene glycol, etc.); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, etc.

[0038] Examples of thickeners include gum arabic, carrageenan, karaya gum, tragacanth gum, carob gum, quince seed, casein, dextrin, gelatin, sodium pectinate, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethyl cellulose, hydroxypropyl cellulose, PVA, PVM, PVP, sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, dialkyldimethylammonium cellulose sulfate, xanthan gum, magnesium aluminum silicate, bentonite, hectorite, magnesium silicate A1 (Bee Gum), laponite, and anhydrous silicic acid.

[0039] Examples of the ultraviolet absorber include benzoic acid-based ultraviolet absorbers (e.g., para-aminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N,N-dipropoxy PABA ethyl ester, N,N-diethoxy PABA ethyl ester, N,N-dimethyl PABA ethyl ester, N,N-dimethyl PABA butyl ester, N,N-dimethyl PABA ethyl ester, etc.); anthranilic acid-based ultraviolet absorbers (e.g., homomenthyl-N-acetylanthranilate, etc.); salicylic acid-based ultraviolet absorbers (e.g., amyl salicylate, , menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanol phenyl salicylate, etc.); cinnamic acid-based ultraviolet absorbers (e.g., octyl methoxycinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropyl cinnamate, methyl-2,4-diisopropyl cinnamate, propyl-p-methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate, ethoxycinnamate, octyl-p-methoxycinnamate (2-ethylhexyl-p-methoxycinnamate), 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, glyceryl mono-2-ethylhexanoyl-di-paramethoxycinnamate, etc.); benzophenone-based ultraviolet absorbers (for example, 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, benzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone, etc.);Examples include 3-(4'-methylbenzylidene)-d,l-camphor, 3-benzylidene-d,l-camphor; 2-phenyl-5-methylbenzoxazole; 2,2'-hydroxy-5-methylphenylbenzotriazole; 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole; 2-(2'-hydroxy-5'-methylphenylbenzotriazole; dibenzalazine; dianisoylmethane; 4-methoxy-4'-t-butyldibenzoylmethane; 5-(3,3-dimethyl-2-norbornylidene)-3-pentan-2-one, dimorpholinopyridazino; 2-ethylhexyl-2-cyano-3,3-diphenylacrylate; 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-(1,3,5)-triazine, and the like.

[0040] Examples of sequestering agents include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, and trisodium ethylenediaminehydroxyethyltriacetate.

[0041] Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, and t-butyl alcohol.

[0042] Examples of the polyhydric alcohol include the polyhydric alcohols described above.

[0043] Examples of monosaccharides include trioses (e.g., D-glyceryl aldehyde, dihydroxyacetone, etc.); tetraoses (e.g., D-erythrose, D-erythrulose, D-threose, erythritol, etc.); pentoses (e.g., L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc.); hexoses (e.g., D-glucose, D-talose, D-busicose, D-galactose, D-fructose, L-galactose, L- heptoses (e.g., aldoheptose, heptose, etc.); octose (e.g., octulose, etc.); deoxysugars (e.g., 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L-mannose, etc.); aminosugars (e.g., D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.); uronic acids (e.g., D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid, etc.), etc.

[0044] Examples of oligosaccharides include sucrose, guanthianose, umbelliferose, lactose, planteose, isolychnoses, α,α-trehalose, raffinose, lychnoses, umbilicin, stachyose, verbascoses, and the like.

[0045] Examples of polysaccharides include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, mucoitin sulfate, guar gum, dextran, keratosulfate, locust bean gum, succinoglucan, and caronic acid.

[0046] Examples of amino acids include neutral amino acids (e.g., threonine, cysteine, etc.) and basic amino acids (e.g., hydroxylysine, etc.). Examples of amino acid derivatives include sodium acyl sarcosine (sodium lauroyl sarcosine), acyl glutamate, sodium acyl β-alanine, glutathione, pyrrolidone carboxylic acid, etc.

[0047] Examples of organic amines include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-methyl-1-propanol, etc. Examples of polymer emulsions include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacrylic alkyl ester emulsion, polyvinyl acetate resin emulsion, natural rubber latex, etc.

[0048] Examples of pH adjusters include buffers such as citric acid, lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate. Examples of vitamins include vitamin A, B1, B2, B6, C, E, and derivatives thereof, pantothenic acid and derivatives thereof, biotin, etc. Examples of antioxidants include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, and gallic acid esters.

[0049] Examples of antioxidant aids include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, cephalin, hexametaphosphate, phytic acid, and ethylenediaminetetraacetic acid.

[0050] Other ingredients that can be added include, for example, preservatives (ethylparaben, butylparaben, chlorphenesin, phenoxyethanol, etc.); disinfectants (for example, isopropylmethylphenol, benzalkonium chloride, benzethonium chloride, chlorhexidine gluconate, etc.); anti-inflammatory agents (for example, glycyrrhizinic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (for example, placenta extract, saxifrage extract, arbutin, etc.); various extracts (for example, Phellodendron bark, Coptis chinensis, Lithospermum root, Peony root, Swertia japonica, Birch, sage, Loquat, Carrot, Aloe vera, Mallow, Iris, Grape, Job's tears, Loofah, Lily, Saffron, Cnidium officinalis, Angelica acutiloba coriander, St. John's wort, Ononis, garlic, capsicum, tangerine peel, angelica acutiloba, seaweed, etc.), activators (for example, royal jelly, photosensitizers, cholesterol derivatives, etc.); blood circulation promoters (for example, nonylic acid warenylamide, nicotinic acid benzyl ester, nicotinic acid β-butoxyethyl ester, capsaicin, zingerone, cantharides tincture, ichthammol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthine, γ-oryzanol, etc.); antiseborrheic agents (for example, sulfur, thianthol, etc.); anti-inflammatory agents (for example, tranexamic acid, thiotaurine, hypotaurine, etc.), etc.

[0051] Furthermore, sequestering agents such as disodium edetate, trisodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, malic acid, etc., caffeine, tannin, verapamil, tranexamic acid or a derivative thereof, various herbal extracts such as licorice, Chinese quince, and Chinese prickly pear, drugs such as tocopherol acetate, glycyrrhesic acid, glycyrrhizic acid or a derivative thereof or a salt thereof, whitening agents such as vitamin C, magnesium ascorbyl phosphate, ascorbic acid glucoside, arbutin, and kojic acid, amino acids such as arginine and lysine or a derivative thereof, and sugars such as fructose, mannose, erythritol, trehalose, and xylitol may also be appropriately blended.

[0052] [4. Dosage Form, Usage, and Use] The active oxygen scavenger of the present disclosure may be, for example, solid or liquid. Examples of the form of the composition of the present disclosure include dosage forms such as oral agents and injections, dosage forms such as tablets and capsules, lotions, emulsions such as lotions and creams, oils, gels, ointments, packs, cleansers, etc.

[0053] The subject of use of the active oxygen scavenger of the present disclosure may be, for example, a human or a non-human animal. The active oxygen scavenger of the present disclosure may be used, for example, on the skin of the subject. The amount of the composition of the present disclosure to be used is not particularly limited, and may be an amount normally used depending on the dosage form of the active oxygen scavenger of the present disclosure.

[0054] The active oxygen scavenger of the present disclosure can be suitably used in, for example, external preparations for skin such as cosmetics. However, the uses of the active oxygen scavenger of the present disclosure are not limited thereto, and the active oxygen scavenger can be used in, for example, pharmaceuticals, medical devices, cosmetics, foods and beverages, oral compositions, and the like.

[0055] (Drug) The dosage form of the pharmaceutical of the present disclosure is not particularly limited. When the composition of the present disclosure is administered in vivo, it may be administered orally or parenterally. Examples of parenteral administration include intravenous injection (intravenous administration), intramuscular injection (intramuscular administration), transdermal administration, subcutaneous administration, intradermal administration, enteral administration, rectal administration, vaginal administration, nasal administration, pulmonary administration, intraperitoneal administration, and topical administration.

[0056] The dosage form of the pharmaceutical product of the present disclosure is not particularly limited and can be appropriately determined depending on, for example, the administration form. Examples of the dosage form include liquid and solid forms. Specific examples of the dosage form include oral administration preparations such as modified-release preparations (enteric-coated preparations, sustained-release preparations, etc.), capsules, oral liquids (elixirs, suspensions, emulsions, perfumes, lemonades, etc.), syrups (syrup preparations, etc.), granules (effervescent granules, fine granules, etc.), powders, tablets (orally disintegrating tablets, chewable tablets, effervescent tablets, dispersible tablets, dissolving agents, coated tablets, etc.), pills, and oral jellies; oral administration preparations such as oral tablets (gums, sublingual tablets, troches, drops, buccal tablets, adhesive tablets, etc.), oral sprays, oral semisolid preparations, and mouthwashes; injections (implant injections, sustained-release injections, infusions (infusion preparations, etc.), freeze-dried injections, powder injections, pre-filled syringes, nasal preparations such as nasal drops (nasal liquid preparations, nasal powder preparations, etc.); rectal preparations such as suppositories, rectal semisolid preparations, and enemas; vaginal preparations such as vaginal suppositories and vaginal tablets; skin preparations such as external liquid preparations (spirits, liniments, lotions, etc.), creams, gels, external solid preparations (external powder preparations, etc.), sprays (external aerosol preparations, pump sprays, etc.), patches (tapes, poultices, etc.), and ointments. When the composition of the present disclosure is administered orally, the dosage form may be, for example, a tablet, a coated tablet, a pill, fine granules, granules, powder, capsule, liquid, syrup, emulsion, suspension, etc. When the composition of the present disclosure is administered parenterally, the dosage form may be, for example, an injection preparation, an intravenous drip preparation, etc. When the composition of the present disclosure is administered transdermally, the dosage form may be, for example, a patch, an ointment, an ointment, a cream, a lotion, or other topical agent.

[0057] The pharmaceutical product of the present disclosure may contain, for example, an additive as needed. When the composition of the present disclosure is used as a medicine or pharmaceutical composition, the additive preferably comprises a pharmaceutically acceptable additive or a pharmaceutically acceptable carrier. The additive is not particularly limited, and examples thereof include base raw materials, excipients, colorants, lubricants, binders, disintegrants, stabilizers, preservatives, pH adjusters, flavoring agents such as fragrances, etc.

[0058] Examples of the excipient include sugar derivatives such as lactose, sucrose, glucose, mannitol, and sorbitol; starch derivatives such as corn starch, potato starch, alpha starch, and dextrin; cellulose derivatives such as crystalline cellulose; organic excipients such as gum arabic; dextran; and pullulan; silicate derivatives such as light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, and magnesium aluminometasilicate; phosphates such as calcium hydrogen phosphate; carbonates such as calcium carbonate; and sulfates such as calcium sulfate. Examples of the lubricant include metal stearates such as stearic acid, calcium stearate, and magnesium stearate; talc; polyethylene glycol; and hydrogenated vegetable oil. Examples of the flavoring agent include flavorings such as cocoa powder, peppermint, aromatic powder, peppermint oil, borneol, and cinnamon powder, as well as sweeteners and acidulants. Examples of the binder include hydroxypropyl cellulose, hydroxypropylmethyl cellulose, polyvinylpyrrolidone, macrogol, etc. Examples of the disintegrant include cellulose derivatives such as carboxymethyl cellulose and carboxymethyl cellulose calcium; chemically modified starches and chemically modified celluloses such as carboxymethyl starch, carboxymethyl starch sodium, and cross-linked polyvinylpyrrolidone; examples of the stabilizer include parahydroxybenzoic acid esters such as methylparaben and propylparaben; alcohols such as chlorobutanol, benzyl alcohol, and phenylethyl alcohol; benzalkonium chloride; phenols such as phenol and cresol; thimerosal; dehydroacetic acid; sorbic acid, etc. The pH adjuster can be appropriately determined, for example, depending on the desired pH. Specifically, when adjusting the pH to the acidic side, acidic substances such as acetic acid, lactic acid, phosphoric acid, tartaric acid, citric acid, ascorbic acid, hydrochloric acid, gluconic acid, and sulfuric acid can be used as the pH adjuster. When adjusting the pH to the basic side, the pH adjuster may be, for example, a basic substance such as potassium hydroxide, sodium hydroxide, calcium hydroxide, magnesium hydroxide, monoethanolamine, diethanolamine, triethanolamine, etc. The pH adjuster may be, for example, one type, or two or more types may be used in combination.

[0059] (Cosmetics) The cosmetics of the present disclosure have excellent safety, stability, and usability, and are therefore suitable for use as skin (skin care) cosmetics and / or hair (hair care) cosmetics. Examples of skin care cosmetics include skin cosmetics such as lotions, emulsions, creams, serums, and packs, cleansers, facial cleansers, UV protection agents, makeup, base cosmetics such as base lotions and makeup base creams, foundations in various dosage forms such as emulsions, oil-based, and solids, makeup cosmetics such as eye colors and cheek colors, and body cosmetics such as hand creams, leg creams, neck creams, and body lotions.

[0060] Examples of hair care cosmetics include shampoos such as oil shampoo, cream shampoo, conditioning shampoo, anti-dandruff shampoo, hair color shampoo, and rinse-in-one shampoo; rinse, treatment, hair pack, hair foam, hair mousse, hair spray, hair mist, hair wax, hair gel, water grease, setting lotion, color lotion, hair tonic, hair liquid, pomade, hair gel, hair blow dryer, split end coat, hair oil, permanent wave agent, straight perm agent, oxidation hair dye, hair bleach, hair color pre-treatment, hair color after-treatment, perm pre-treatment, perm after-treatment, hair manicure, and hair growth agent.

[0061] The cosmetic compositions of the present disclosure are preferably applied to humans, but can also be applied to animals other than humans as long as the respective functional effects are achieved.

[0062] (Food and Beverage) The food and beverage of the present disclosure contains, for example, the reactive oxygen scavenger of the present disclosure and further contains other ingredients as needed. For example, the ozone-treated glycerin contained in the reactive oxygen scavenger of the present disclosure has high safety performance while having little effect on multiple components. Here, food and beverage refers to products that are unlikely to pose a risk to human health and are ingested orally or via gastrointestinal administration in normal social life, and are not limited to administrative classifications such as food, medicine, or quasi-drug. Therefore, the term "food and beverage" in this embodiment broadly includes orally ingested general foods, health foods (functional food and beverage), health functional foods (foods for specified health uses, foods with nutrient functions), quasi-drugs, medicines, etc. The content of the ozone-treated glycerin in the food and beverage is not particularly limited and can be adjusted as appropriate.

[0063] <Other ingredients> The other ingredients contained in the food and beverage products of the present disclosure are not particularly limited and can be appropriately selected according to the purpose from among auxiliary raw materials, additives, or other ingredients used in the production of ordinary food and beverage products. Examples include glucose, fructose, sucrose, maltose, sorbitol, stevioside, rubusoside, corn syrup, lactose, oligosaccharides, xylitol, trehalose, palatinose, aspartame, acesulfame potassium, sucralose, saccharin salts, citric acid, tartaric acid, malic acid, succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, sodium erythorbate, glycerin, propylene glycol, glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, gum arabic, carrageenan, casein, gelatin, pectin, agar, B vitamins, nicotinamide, calcium pantothenate, amino acids, calcium salts, colorants, flavorings, preservatives, and the like. These may be used alone or in combination of two or more. The amount of the other components is not particularly limited and can be appropriately selected depending on the purpose.

[0064] The food and drink products are not particularly limited, and specific examples thereof include beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks (including concentrated concentrates and powders for adjusting these beverages); frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba noodles, udon noodles, vermicelli, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; sweets such as candy, chewing gum, candies, gum, chocolate, candy tablets, snacks, biscuits, jelly, jam, cream, and baked goods; processed seafood and livestock foods such as kamaboko, ham, and sausage; dairy products such as processed milk and fermented milk; oils and fats and oil-based foods such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressing; condiments such as sauces and dressings; soups, stews, salads, side dishes, and pickles; and various other forms of health and nutritional supplements; tablets, capsules, and energy drinks.

[0065] The food and drink products may be in the form of any known food or pharmaceutical product, such as a powder, capsule, granule, tablet, liquid, or other oral pharmaceutical form. Ordinary food products may be in the form of jelly, syrup, candy, gum, soft drinks, supplements, or other known food forms, or may be mixed in a predetermined amount with other known foods.

[0066] The method of ingesting the food or drink is not particularly limited and can be appropriately selected depending on the purpose, and examples thereof include oral administration, parenteral administration, gastrointestinal administration, etc. Among these, oral administration is preferred.

[0067] The foods and beverages of the present disclosure are preferably applied to humans, but can also be applied to animals other than humans as long as their respective functional effects are achieved.

[0068] (Oral Composition) The oral composition of the present disclosure contains, for example, the reactive oxygen scavenger of the present disclosure, and further contains other components as necessary. For example, the ozonated glycerin contained in the reactive oxygen scavenger of the present disclosure has high safety performance and has almost no effect on other components. The content of the ozonated glycerin in the oral composition is not particularly limited and can be adjusted as appropriate.

[0069] The application form of the oral composition is not particularly limited, and can be used as, for example, a pharmaceutical, a quasi-drug, or a cosmetic. Known uses of the oral composition can be appropriately adopted. Examples of uses include chewing agents, oral dissolving agents, oral disintegrating agents, tongue care agents, mouth fresheners, toothpastes, mouthwashes, gargles, liquid dentifrices, biofilm dispersants, anti-halitosis agents, gum massage agents, oral moisturizing agents, tongue coating removers, oral application agents, oral disinfectants, throat disinfectants, oral throat agents, periodontal disease treatment agents, denture adhesives, denture coating agents, denture stabilizers, denture preservatives, denture cleaners, and implant care agents.

[0070] The dosage form of the oral composition is not particularly limited, and for example, by containing a solvent such as water or alcohol, it can be applied to ointments, pastes, sprays, gels, liquids, suspensions, gums, etc.

[0071] The oral composition may contain other components in addition to the components described above depending on the intended application, form, use, etc. Examples of other components include antibacterial agents, anti-inflammatory agents, fragrances, humectants, abrasives, alcohols, thickeners, sweeteners, medicinal components, colorants, stabilizers, and pH adjusters. Known components that are incorporated into oral compositions can be used as other components. The oral composition may contain only one of the above other components alone, or may contain two or more of them in combination.

[0072] Next, examples of the present disclosure will be described. However, the present disclosure is not limited by the following examples. Commercially available reagents were used according to their protocols unless otherwise specified. In the following examples, when the concentration of a solution is expressed as "%", it is by weight (w / v) unless otherwise specified.

[0073] Example 1 A glycerin solution containing ozone-treated glycerin was produced by ozone oxidation of glycerin. The ozone-treated glycerin solution was heated to produce an active oxygen scavenger of the present disclosure. Furthermore, the active oxygen scavenging function of the produced active oxygen scavenger was confirmed. This example corresponds to an example in which an active oxygen scavenger of the present disclosure was produced and used, as well as an example in which the active oxygen scavenging method of the present disclosure was used, and further corresponds to an example in which the active oxygen scavenger production method of the present disclosure was used.

[0074] (1) Production of an Ozone-Treated Glycerin Solution Containing Ozone-Treated Glycerin Synthetic glycerin and ozone were brought into gas-liquid contact to produce an ozone-treated glycerin solution containing ozone-treated glycerin as follows.

[0075] A 50 L Teflon tank was used as the contact tank. An air diffuser was installed at the bottom of the tank so that ozone-containing gas could be supplied into the tank as fine bubbles. Oxygen (O ２ ) and its O ２ was used as the raw material, and a silent discharge ozone generator capable of generating 100 g of ozone per hour was used.

[0076] 22 kg of the concentrated glycerin was placed in the tank, and the ozone generator was charged with oxygen (O ２ ) was fed into the tank to generate a gas containing ozone, and the generated gas was released into the tank through the air diffuser for 96 hours to obtain a glycerin solution in which ozone-treated glycerin was dissolved.

[0077] (2) Heating of ozonated glycerin solution The ozonated glycerin solution prepared in (1) above was heated at 50°C for 14 days (2 weeks) to prepare the active oxygen scavenger of the present disclosure. This step corresponds to the "processing step (heating step)" of the present disclosure.

[0078] (3) Confirmation of active oxygen scavenging function H ２ O ２ The ESR spectrum of the OH radicals generated by the Fenton reaction-DMPO spin trapping method was measured. Furthermore, various samples (test substances) were added and mixed, and ESR measurements were performed, and the active oxygen scavenging activity of the samples was evaluated by comparing the spectral intensities of DMPO-OH. In the following, "OG" stands for ozonated glycerin.

[0079] Experimental conditions: ESR device: EMX-nano (Bruker) OG or H ２ O ２ When used alone: ​​DMPO 5 μL, purified water 140 μL, 1 mmol / L FeSO ４ 20 μL Sample 20 μL OG and H ２ O ２ (1:1) mixed sample: DMPO 5 μL, purified water 120 μL, 1 mmol / L FeSO ４ 20 μL Sample 40 μL If the sample does not have a spectrum, [Sample + H ２ O ２ mix (sample and H ２ O ２ a mixture of] and [H ２ O ２ ] and the spectrum was compared. If the sample contains a spectrum such as DMPO-OH, ２ O ２ mix]-[Sample] spectrum (spectral subtraction processing) and [H ２ O ２ The active oxygen scavenging rate was calculated from these results. When the OG concentration was high, the six-line spectrum of OG and H ２ O ２The apparent spectral intensity changes in the area where the four-line spectrum of the DMPO-OH derivative overlaps. ２ O ２ By subtracting the spectrum of [OG] from the spectrum of [mix], [OG+H ２ O ２ mix] H in the sample ２ O ２ Only the spectrum of [OG+H ２ O ２ When the spectrum of [OG] was subtracted from the spectrum of [mix], correction was made so that the spectral intensity of the first line from the left of the 6-line OG spectrum was the same.

[0080] [Example 2] As a raw material of ozone-containing gas, oxygen (O ２ ) was replaced with air, and the oxygen (O ２ An ozone-treated glycerin solution containing ozone-treated glycerin was produced in the same manner as in (1) of Example 1, except that glycerin was ozone-treated using 1,2-dimethylaminobenzoate (Dimethylaminobenzoate) as a raw material. The ozone-treated glycerin solution was heated in the same manner as in (2) of Example 1 to produce an active oxygen scavenger of the present disclosure. Furthermore, the active oxygen scavenging function of the produced active oxygen scavenger was confirmed in the same manner as in (3) of Example 1. This example corresponds to an example in which an active oxygen scavenger of the present disclosure was produced and used, as well as an example in which the active oxygen scavenging method of the present disclosure was used, and further corresponds to an example in which the active oxygen scavenger production method of the present disclosure was used.

[0081] [Example 3] As a raw material of ozone-containing gas, oxygen (O ２An ozone-treated glycerin solution containing ozone-treated glycerin was produced in the same manner as in (1) of Example 1, except that instead of the ozone-treated glycerin, a high-concentration oxygen gas containing 90% or more by volume of oxygen concentrated by an oxygen concentrator (PSA) was used, and glycerin was ozone-treated using this as a raw material. The ozone-treated glycerin solution was heated in the same manner as in (2) of Example 1 to produce an active oxygen scavenger of the present disclosure. Furthermore, the active oxygen scavenging function of the produced active oxygen scavenger was confirmed in the same manner as in (3) of Example 1. This example corresponds to an example in which an active oxygen scavenger of the present disclosure was produced and used, as well as an example in which the active oxygen scavenging method of the present disclosure was used, and further corresponds to an example in which the active oxygen scavenger production method of the present disclosure was used.

[0082] Examples 4 to 9: Active oxygen scavengers were produced in the same manner as in Examples 1 to 3, except that in the heating step (2) of Examples 1 to 3, heating was performed at 40°C for 4 weeks (28 days) instead of 2 weeks (14 days) at 50°C. Active oxygen scavengers were also produced in the same manner as in Examples 1 to 3, except that in the heating step (2) of Examples 1 to 3, heating was performed at 90°C for 6 hours instead of 2 weeks (14 days) at 50°C. Active oxygen scavengers were also produced in the same manner as in Example 1 (3). These examples correspond to examples in which an active oxygen scavenger of the present disclosure was produced and used, as well as examples in which the active oxygen scavenging method of the present disclosure was used, and also correspond to examples in which the method of producing an active oxygen scavenger of the present disclosure was used.

[0083] Examples 10-12 An active oxygen scavenger of the present disclosure was produced in the same manner as in Example 3, except that concentrated glycerin was used instead of the synthetic glycerin used in Example 3 (Example 10). Here, concentrated glycerin refers to glycerin with a concentration of 98% by weight or more. An active oxygen scavenger was also produced in the same manner as in Example 10, except that in the heating step (2), heating was performed at 40°C for 4 weeks (28 days) instead of 2 weeks (14 days) at 50°C (Example 11). An active oxygen scavenger was also produced in the same manner as in Example 10, except that in the heating step (2), heating was performed at 90°C for 6 hours instead of 2 weeks (14 days) at 50°C (Example 12). Furthermore, the active oxygen scavenging function of the produced active oxygen scavenger was confirmed in the same manner as in Example 1 (3). This example corresponds to an example in which the reactive oxygen scavenger of the present disclosure was produced and used, as well as an example in which the reactive oxygen scavenging method of the present disclosure was used, and further corresponds to an example in which the reactive oxygen scavenger of the present disclosure was produced and used.

[0084] [Reference Example] An active oxygen scavenger (ozone-treated glycerin solution) was produced in the same manner as in Example 1, except that the heating step (2) was not performed. The active oxygen scavenging function of the produced ozone-treated glycerin solution was confirmed in the same manner as in Example 1 (3).

[0085] Figure 1 shows the active oxygen scavenging rate (%) of active oxygen scavengers produced using an oxygen cylinder. From left to right, they are Reference Example (no heating step), Example 1 (heated at 50°C for 2 weeks), and Example 4 (heated at 40°C for 4 weeks). As shown in the figure, the active oxygen scavenging rate after the heating step was higher than before the heating step. In Figure 1 and Figures 2 to 15 described below, the vertical axis is the active oxygen scavenging rate (%) in all cases except for Figure 7.

[0086] Figure 2 shows the active oxygen scavenging rate (%) of the active oxygen scavenger produced using air. From left to right, they are Reference Example (no heating step), Example 2 (heated at 50°C for 2 weeks), and Example 5 (heated at 40°C for 4 weeks). As shown in the figure, the active oxygen scavenging rate after the heating step was higher than before the heating step.

[0087] Figure 3 shows the active oxygen scavenging rate (%) of the active oxygen scavenger produced using a PSA (oxygen concentrator). From left to right, they are Reference Example (no heating step), Example 3 (heated at 50°C for 2 weeks), and Example 6 (heated at 40°C for 4 weeks). As shown in the figure, the active oxygen scavenging rate was maintained at the same level even after the heating step as before the heating step.

[0088] The graphs in Figures 4 and 5 show that the active oxygen scavenging rate (%) was maintained or increased after heating at 50°C for two weeks. In Figure 4, the left side shows the active oxygen scavenger of Reference Example, which was produced in the same manner as in Example 3 (using synthetic glycerin and heating at 50°C for two weeks in the heating step) except that the heating step was not performed, and the right side shows the active oxygen scavenger of Example 3. In Figure 5, the left side shows the active oxygen scavenger of Reference Example, which was produced in the same manner as in Example 10 (using concentrated glycerin and heating at 50°C for two weeks in the heating step) except that the heating step was not performed, and the right side shows the active oxygen scavenger of Example 10. As shown in Figure 4, the active oxygen scavenging rate was maintained after the heating step in Example 3. As shown in Figure 5, the active oxygen scavenging rate increased after the heating step in Example 10.

[0089] FIG. 6 shows that the active oxygen scavenging rate was maintained or increased after heating at 40°C for 4 weeks. In FIG. 6, "Synthetic O2B" is the active oxygen scavenger of the Example (Example 1) or Reference Example, which was produced using synthetic glycerin and an oxygen cylinder. "Synthetic Air" is the active oxygen scavenger of the Example (Example 2) or Reference Example, which was produced using synthetic glycerin and air. "Synthetic PSA" is the active oxygen scavenger of the Example (Example 3) or Reference Example, which was produced using synthetic glycerin and an oxygen concentrator. "Synthetic 50% PSA" is the active oxygen scavenger of the Reference Example, which was produced using synthetic glycerin and an oxygen concentrator, diluted 2-fold (by mass) with glycerin and then heated at 50°C for 2 weeks. As shown by the numerical values ​​in FIG. 6, the active oxygen scavenging rate was maintained or increased after heating at 40°C for 4 weeks.

[0090] Figure 7 shows that the oxidizing power was suppressed after heating. In Figure 7, the vertical axis represents the oxidizing power (relative value). The oxidizing power was measured by potassium iodide titration using a potassium iodide absorption solution, a starch aqueous solution, and a sodium thiosulfate aqueous solution. The potassium iodide absorption solution was a 500g solution prepared by dissolving 17.90g of potassium dihydrogen phosphate (KH2PO4), 17.14g of disodium hydrogen phosphate (Na2HPO4·12H2O), and 25.00g of potassium iodide (KI) in purified water. The starch aqueous solution was prepared by dissolving approximately 0.22g of starch in approximately 20g of purified water and boiling. In Figure 7, "O2 Cylinder Synthetic G" represents Examples (Examples 1 and 4) and a Reference Example produced using synthetic glycerin and an oxygen cylinder. "Air-Synthetic G" represents Examples (Examples 2 and 5) and a Reference Example produced using synthetic glycerin and air. "PSA-Synthetic G" represents examples (Examples 3 and 6) and a Reference Example produced using synthetic glycerin and an oxygen concentrator. "PSA-Synthetic G" represents examples (Examples 11 and 12) and a Reference Example produced using concentrated glycerin and an oxygen concentrator manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. From left to right, the examples are a Reference Example (no heating, "immediately after"), an Example heated at 50°C for two weeks, and an Example heated at 40°C for four weeks. As shown in the figure, in all examples, the oxidizing power was significantly suppressed after the heating process compared to before the heating process.

[0091] 8 shows the active oxygen scavenging rate (%) of the Reference Example and Examples produced using synthetic glycerin and an oxygen cylinder. From the left, the figures show no heating step (Reference Example), heating at 50°C for 2 weeks (Example 1), heating at 40°C for 4 weeks (Example 4), and heating at 90°C for 6 hours (Example 7). As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0092] 9 shows the active oxygen scavenging rate (%) of the Reference Example and Examples produced using synthetic glycerin and air. From the left, the figures show no heating step (Reference Example), heating at 50°C for 2 weeks (Example 2), heating at 40°C for 4 weeks (Example 5), and heating at 90°C for 6 hours (Example 8). As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0093] 10 shows the active oxygen scavenging rate (%) of the Reference Example and Examples produced using synthetic glycerin and an oxygen concentrator. From the left, the figures show no heating step (Reference Example), heating at 50°C for 2 weeks (Example 3), heating at 40°C for 4 weeks (Example 6), and heating at 90°C for 6 hours (Example 9). As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0094] 11 shows the active oxygen scavenging rate (%) of the Reference Example and Examples produced using concentrated glycerin and an oxygen concentrator. From the left, the figures show no heating step (Reference Example), heating at 50°C for 2 weeks (Example 10), heating at 40°C for 4 weeks (Example 11), and heating at 90°C for 6 hours (Example 12). As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0095] 12 shows the active oxygen scavenging rate (%) of the Reference Example active oxygen scavenger produced using synthetic glycerin and an oxygen concentrator, diluted twice (50%, by mass) with glycerin, and the Example active oxygen scavenger produced by heating the diluted active oxygen scavenger. From the left, the active oxygen scavenger is shown as follows: no heating step (Reference Example), heating at 50°C for 2 weeks, heating at 40°C for 4 weeks, and heating at 90°C for 6 hours. As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0096] 13 shows the active oxygen scavenging rate (%) of the Reference Example active oxygen scavenger produced using synthetic glycerin and an oxygen concentrator, diluted 20 times (5%, by mass) with glycerin, and the Example active oxygen scavenger produced by heating the diluted active oxygen scavenger. From the left, the active oxygen scavenger is shown as follows: no heating step (Reference Example), heating at 50°C for 2 weeks, heating at 40°C for 4 weeks, and heating at 90°C for 6 hours. As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0097] 14 shows the active oxygen scavenging rate (%) of the Reference Example active oxygen scavenger produced using synthetic glycerin and an oxygen concentrator diluted 4 times (25%, by mass) with glycerin, and the Example active oxygen scavenger produced by heating the Reference Example active oxygen scavenger. From the left, the active oxygen scavenger is shown as follows: no heating step (Reference Example), heating at 50°C for 2 weeks, and heating at 40°C for 4 weeks. As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0098] 15 shows the active oxygen scavenging rate (%) of the Reference Example active oxygen scavenger produced using synthetic glycerin and an oxygen concentrator, diluted with glycerin to 85% (mass ratio), and the Example active oxygen scavenger produced by heating the diluted active oxygen scavenger. From the left, the active oxygen scavenger is shown as follows: no heating step (Reference Example), heating at 50°C for 2 weeks, and heating at 40°C for 4 weeks. As shown in the figure, in all Examples, the active oxygen scavenging rate increased after the heating step compared to before the heating step (Reference Example).

[0099] Furthermore, even when the synthetic glycerin and concentrated glycerin used as raw materials in the Examples and Reference Examples were heated at 50°C for 2 weeks or at 40°C for 4 weeks without ozone treatment, their active oxygen scavenging function as active oxygen scavengers was not confirmed, unlike ozone-treated glycerin.

[0100] Although the present disclosure has been described above with reference to the embodiments and examples, the present disclosure is not limited to the above-described embodiments and examples. Various modifications that can be understood by those skilled in the art can be made to the configuration and details of the present disclosure within the scope of the present invention.

[0101] <Appendix> Some or all of the above-described embodiments and examples may be described as, but are not limited to, the following appendices. (Appendix 1) An active oxygen scavenger obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas. (Appendix 2) The active oxygen scavenger according to Appendix 1, wherein the processing is heating. (Appendix 3) The active oxygen scavenger according to Appendix 1 or 2, wherein the ozone-treated alcohol is ozone-treated glycerin. (Appendix 4) The active oxygen scavenger according to any one of Appendixes 1 to 3, wherein the ozone-treated alcohol comprises an ozone-treated alcohol having an active oxygen scavenging function. (Appendix 5) A method for scavenging active oxygen, comprising a reaction step of reacting an active oxygen scavenger obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas with active oxygen. (Appendix 6) The method for scavenging active oxygen according to Appendix 5, wherein the reaction step is a step of reacting the active oxygen scavenger according to any one of Appendixes 1 to 4 with active oxygen. (Appendix 7) A method for producing an active oxygen scavenger, comprising: an ozone treatment step of ozone-treating an alcohol with an oxygen allotrope-containing gas; and a processing step of processing the ozone-treated alcohol ozone-treated in the ozone treatment step. (Appendix 8) The production method according to Appendix 7, wherein the processing step is a heating step of heating the ozone-treated alcohol. (Appendix 9) The production method according to Appendix 7 or 8, wherein the alcohol is glycerin.

[0102] As described above, the present disclosure provides a novel active oxygen scavenger with reduced oxidizing power, a method for scavenging active oxygen, and a method for producing the active oxygen scavenger. The active oxygen scavenger of the present disclosure has an active oxygen scavenging function and is therefore extremely useful in fields such as pharmaceuticals, cosmetics, foods and beverages, and oral compositions.

[0103] This application claims priority based on Japanese Patent Application No. 2024-089472, filed May 31, 2024, the disclosure of which is incorporated herein in its entirety by reference.

Claims

1. An active oxygen scavenger characterized by being obtained by processing an active oxygen scavenger containing ozone-treated alcohol which has been ozone-treated with an oxygen allotrope-containing gas.

2. The active oxygen scavenger according to claim 1, wherein the processing is heating.

3. The active oxygen scavenger according to claim 1 or 2, wherein the ozonated alcohol is ozonated glycerin.

4. The active oxygen scavenger according to any one of claims 1 to 3, wherein the ozonated alcohol comprises an ozonated alcohol having an active oxygen scavenging function.

5. A method for eliminating active oxygen, comprising a reaction step of reacting an active oxygen scavenger obtained by processing an active oxygen scavenger containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas with active oxygen.

6. The method for scavenging active oxygen according to claim 5, wherein the reaction step is a step of reacting the active oxygen scavenger according to any one of claims 1 to 4 with active oxygen.

7. A method for producing an active oxygen scavenger, comprising: an ozone treatment step of ozone-treating an alcohol with an oxygen allotrope-containing gas; and a processing step of processing the ozone-treated alcohol obtained in the ozone treatment step.

8. The method according to claim 7, wherein the processing step is a heating step of heating the ozone-treated alcohol.

9. The method according to claim 7 or 8, wherein the alcohol is glycerin.

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