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

Abstract

Provided is a new active oxygen scavenger.　An active oxygen scavenger according to the present disclosure is characterized by comprising an ozone-treated alcohol that has been treated with ozone by using 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. Reactive oxygen reacts with various components in the body's metabolic processes, and excessive amounts can cause cell damage (Non-Patent Document 1).

[0003] https: / / www.e-healthnet.mhlw.go.jp / information / food / e-04-003.html (Ministry of Health, Labour and Welfare, Health Information Site for Preventing Lifestyle-Related Diseases, accessed February 15, 2024)

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

[0005] Therefore, an object of the present disclosure is to provide a novel active oxygen scavenger, a method for scavenging active oxygen, and a method for producing the active oxygen scavenger.

[0006] In order to achieve the above object, the active oxygen scavenger of the present disclosure is characterized by containing an ozonated alcohol that has been ozonated with an oxygen allotrope-containing gas.

[0007] The method for eliminating active oxygen disclosed herein is characterized by including a reaction step of reacting an ozonated alcohol, which has been ozonated with an oxygen allotrope-containing gas, with active oxygen.

[0008] The method for producing an active oxygen scavenger of the present disclosure is characterized by including an ozone treatment step of ozone-treating an alcohol with an oxygen allotrope-containing gas.

[0009] According to the present disclosure, a novel active oxygen scavenger, a method for scavenging active oxygen, and a method for producing an active oxygen scavenger can be provided.

[0010] FIG. 1 is an ESR spectrum of OG200 of an example. FIG. 2 is an ESR spectrum of OG20 of an example. FIG. 3 is an ESR spectrum of OG4 of an example. FIG. 4 is a bar graph showing the active oxygen scavenging rate (%) calculated from the ESR spectra of FIGS. 1 to 3. FIG. 5 is an ESR spectrum of synthetic glycerin. FIG. 6 is an ESR spectrum of concentrated glycerin for cosmetics (Kao). FIG. 7 is an ESR spectrum of special-grade glycerin (Fujifilm Wako). FIG. 8 is an ESR spectrum of concentrated glycerin according to the Japanese Pharmacopoeia (Kao). FIG. 9 is an ESR spectrum of concentrated glycerin according to the Japanese Pharmacopoeia (Sakamoto Yakuhin Kogyo). FIG. 10 is a bar graph showing the active oxygen scavenging rate (%) calculated from the ESR spectra of FIGS. 5 to 9. FIG. 11 is an ESR spectrum of oxygen (O ２ 12 shows the ESR spectrum of Example 2, in which oxygen (O ２ 13 shows the ESR spectrum of Example 2, in which oxygen (O ２ 14 shows the ESR spectrum of Example 2, in which oxygen (O) in the air was used as the raw material and treated with ozone for 24 hours. ２ 15 shows the ESR spectrum of Example 3, in which oxygen (O) in the air was used as the raw material and treated with ozone for 3 hours. ２ 16 shows the ESR spectrum of Example 3, in which oxygen (O) in the air was treated with ozone for 6 hours. ２FIG. 17 is an ESR spectrum diagram of Example 1 in which oxygen concentrated by a PSA (oxygen concentrator) was used as a raw material and ozone treated for 3 hours. FIG. 18 is an ESR spectrum diagram of Example 1 in which oxygen concentrated by a PSA (oxygen concentrator) was used as a raw material and ozone treated for 6 hours. FIG. 19 is an ESR spectrum diagram of Example 1 in which oxygen concentrated by a PSA (oxygen concentrator) was used as a raw material and ozone treated for 24 hours. FIG. 20 is an ESR spectrum diagram of Example 1 in which oxygen concentrated by a PSA (oxygen concentrator) was used as a raw material and ozone treated for 96 hours. FIG. 21 is an ESR spectrum diagram of Example 1 in which oxygen concentrated by a PSA (oxygen concentrator) was used as a raw material and ozone treated for 96 hours. ２ FIG. 22 is a bar graph showing the active oxygen scavenging rate (%) for Examples 1 to 3, in which ozone treatment was performed using 100% glycerin solution, 50% glycerin aqueous solution, and 5% glycerin aqueous solution in Example 1, where the ozone treatment time was 24 hours. FIG. 23 is a bar graph showing the active oxygen scavenging rate (%) for Example 1, where the ozone treatment time was 24 hours, when a 100% glycerin solution, a 50% glycerin aqueous solution, and a 5% glycerin aqueous solution were used. FIG. 24 is a bar graph showing the active oxygen scavenging rate (%) for the glycerin aqueous solution treated with ozone for 96 hours in Example 1, before and after heating at 50°C for two weeks. FIG. 25 is a bar graph showing the active oxygen scavenging rate (%) for the glycerin aqueous solution treated with ozone for 96 hours in Example 1, before and after storing at room temperature for 3 to 24 hours. FIG. 26 is a graph showing the correlation between treatment time and pH in each of Examples 1 to 3.

[0011] 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.

[0012] 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."

[0013] [1. Active oxygen scavenger and manufacturing method thereof] As described above, the active oxygen scavenger of the present disclosure is characterized by comprising an ozonated alcohol that has been ozonated with an oxygen allotrope-containing gas. Specifically, ozone is generated using the oxygen-containing gas contained in the oxygen allotrope-containing gas as a raw material, and the alcohol can be ozonated with the ozone. The ozonated alcohol is preferably ozonated glycerin. The structure of the ozonated alcohol is not particularly limited, but it preferably contains an oxygen-treated alcohol that has an active oxygen scavenging function. In the present disclosure, the structure of the ozonated alcohol that has 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.

[0014] In the present disclosure, oxygen allotropes include, for example, oxygen (O ２ ), ozone (O ３ ) and the like, with ozone being particularly preferred.

[0015] 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.

[0016] 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.

[0017] As described above, the method for producing an active oxygen scavenger of the present disclosure is characterized by including an oxygen treatment step in which an alcohol is treated with an oxygen allotrope. However, the active oxygen scavenger of the present disclosure is not limited to this production method and may be produced by any production method. The production method for the active oxygen scavenger of the present disclosure will be described in more detail below with examples.

[0018] In the following, an example of ozone oxidation using glycerin as the alcohol will be described. 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 oxygen 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.

[0019] The active oxygen scavenger of the present disclosure can be produced by a production method including, for example, a step of contacting glycerin with ozone, more specifically, a step of oxidizing glycerin by mixing glycerin with ozone (corresponding to the aforementioned "oxygen treatment 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.

[0020] 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.

[0021] 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.

[0022] The method for bringing the glycerin solution into gas-liquid contact with the ozone-containing gas is not particularly limited, and for example, a method is available 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 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 longer period of time.

[0023] [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 oxygen-treated alcohol having active oxygen scavenging function by, for example, allowing the oxygen-treated alcohol having active oxygen scavenging function to coexist with alcohol.

[0024] 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.

[0025] [3. Other Components] The active oxygen scavenger of the present disclosure may contain other components in addition to the oxygen-treated alcohol treated with an oxygen allotrope. 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 (e.g., water), alcohols, moisturizers, oils, softeners (emollients), surfactants (solubilizers, emulsifiers), salts, thickeners, pH adjusters, UV absorbers, drugs, buffers, colorants, preservatives, and fragrances.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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;

[0031] 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.

[0032] 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.).

[0033] 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.).

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, and t-butyl alcohol.

[0039] Examples of the polyhydric alcohol include the polyhydric alcohols described above.

[0040] 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.

[0041] Examples of oligosaccharides include sucrose, guanthianose, umbelliferose, lactose, planteose, isolychnoses, α,α-trehalose, raffinose, lychnoses, umbilicin, stachyose, verbascoses, and the like.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] [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.

[0050] 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.

[0051] 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, cosmetics, foods and beverages, oral compositions, and the like.

[0052] (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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] (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.

[0057] 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.

[0058] 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.

[0059] (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.

[0060] <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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] (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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] [Example 1] A glycerin solution containing ozone-treated glycerin was produced by ozone oxidation of glycerin. Furthermore, the active oxygen scavenging function of the produced ozone-treated glycerin solution was confirmed. This example corresponds to an example in which the 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.

[0071] (1) Production of an ozone-treated glycerin solution containing ozone-treated glycerin Concentrated glycerin and ozone were brought into gas-liquid contact to produce an ozone-treated glycerin solution containing ozone-treated glycerin as follows: Here, the concentrated glycerin refers to glycerin having a concentration of 98% by weight or more of the glycerin prescribed in the Japanese Pharmacopoeia.

[0072] A 50 L Teflon tank was used as the contact vessel. An air diffuser was installed at the bottom of the tank, allowing ozone to be supplied into the tank as fine bubbles. A silent discharge ozone generator capable of generating 100 g of ozone per hour was used, using high-concentration oxygen gas containing 90% or more by volume as the raw material.

[0073] 22 kg of the concentrated glycerin was placed in the tank, and the high-concentration oxygen gas was fed into the ozone generator at 20 L per minute to generate a gas containing ozone. The generated gas was then released into the tank through the air diffuser for a predetermined period of time, thereby obtaining a glycerin solution having ozone-treated glycerin dissolved therein.

[0074] (2) Confirmation of active oxygen scavenging function H ２ O ２The 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.

[0075] 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 ２ The 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 ２Only 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.

[0076] In the above (1), ozone was released into the tank for 5 days, resulting in ozone-treated glycerin (hereinafter sometimes referred to as "OG2000") having an oxidizing power of 2,000 ppm in terms of ozone concentration. Dilutions of this with water at 1 / 10, 1 / 100, and 1 / 500 will be hereinafter sometimes referred to as OG200, OG20, and OG4, respectively.

[0077] 1 to 3 show the ESR spectra of OG200, OG20, and OG4 measured by the measurement method (2) above. In FIG. 1, "OG1 / 10" is synonymous with OG200. In FIG. 2, "OG1 / 100" is synonymous with OG20. In FIG. 3, "OG1 / 500" is synonymous with OG4. The bar graph in FIG. 4 shows the active oxygen scavenging rate (%) calculated from these ESR spectra. This active oxygen scavenging rate value is an index representing the level of active oxygen scavenging function. Furthermore, the values ​​in FIG. 4 are values ​​where the active oxygen scavenging rate of OG200 is set to 100%. As shown in the figure, the active oxygen scavenging rate increased with increasing concentration of ozone-treated glycerin.

[0078] Next, the active oxygen scavenging rate of ozone-treated glycerin was compared with that of untreated glycerin. Specifically, the active oxygen scavenging rates of the following commercially available glycerin diluted 1 / 10 with water and OG200, which was obtained by diluting OG2000 with water 1 / 10, were compared using the measurement method (2) above. Test substances: Synthetic glycerin (Spectrum Co., Ltd.) Cosmetic concentrated glycerin (Kao Co., Ltd.) Japanese Pharmacopoeia concentrated glycerin (Kao Co., Ltd.) Japanese Pharmacopoeia concentrated glycerin (Sakamoto Pharmaceutical Co., Ltd.) Reagent grade glycerin (Fujifilm Wako Co., Ltd.) Ozone-treated glycerin 200 ppm

[0079] Figures 5 to 9 show ESR spectra of synthetic glycerin, cosmetic concentrated glycerin (Kao), special reagent grade glycerin (Fujifilm Wako), Japanese Pharmacopoeia concentrated glycerin (Kao), and Japanese Pharmacopoeia concentrated glycerin (Sakamoto Yakuhin Kogyo), respectively, measured by the measurement method (2) above. The ESR spectrum of OG200 is shown in Figure 1. The bar graph in Figure 10 shows the active oxygen scavenging rate (%) calculated from these ESR spectra. As shown in Figure 10, the active oxygen scavenging rate of untreated glycerin was extremely low compared to ozone-treated glycerin, confirming that ozone-treated glycerin has a high active oxygen scavenging function.

[0080] [Example 2] Instead of the silent discharge ozone generator of Example 1, an oxygen cylinder was used, and the oxygen (O ２ An oxygen-treated glycerin solution containing oxygen-treated glycerin was produced in the same manner as in (1) of Example 1, except that glycerin was treated with ozone using 2,4-dimethylaminobenzoate (D-glucan) as a raw material. Furthermore, the active oxygen scavenging function of the produced oxygen-treated glycerin solution was confirmed in the same manner as in (2) of Example 1. This example corresponds to an example in which an active oxygen scavenger according to the present disclosure was produced and used, as well as an example in which the active oxygen scavenging method according to the present disclosure was used, and further corresponds to an example in which the active oxygen scavenger production method according to the present disclosure was used.

[0081] [Example 3] Instead of the silent discharge ozone generator of Example 1, air was used, and the oxygen (O ２ An oxygen-treated glycerin solution containing oxygen-treated glycerin was produced in the same manner as in (1) of Example 1, except that glycerin was treated with ozone using 2,4-dimethylaminobenzoate (D-glucan) as a raw material. Furthermore, the active oxygen scavenging function of the produced oxygen-treated glycerin solution was confirmed in the same manner as in (2) of Example 1. This example corresponds to an example in which an active oxygen scavenger according to the present disclosure was produced and used, as well as an example in which the active oxygen scavenging method according to the present disclosure was used, and further corresponds to an example in which the active oxygen scavenger production method according to the present disclosure was used.

[0082] [Comparison of Active Oxygen Scavenging Rates in Examples 1 to 3] In Example 1, the treatment time with ozone was changed to 3 hours, 6 hours, 24 hours, and 96 hours, and oxygen-treated glycerin solutions (active oxygen scavengers) containing oxygen-treated glycerin were produced. Next, in Examples 2 and 3, oxygen (O ２ The treatment time in the oxygen-treated glycerin solution (active oxygen scavenger) was changed to 3 hours, 6 hours, and 24 hours, and the active oxygen scavenging rate (active oxygen scavenging function) of each of the oxygen-treated glycerin solutions was confirmed by the method described in (2) of Example 1. Figures 11 to 13 show the results of the treatment with oxygen (O ２ 14 to 16 show ESR spectra of Example 3 treated with air for treatment times of 3 hours, 6 hours, and 24 hours, respectively. FIGS. 17 to 20 show ESR spectra of Example 1 treated with ozone using a PSA (oxygen concentrator) for treatment times of 3 hours, 6 hours, 24 hours, and 96 hours, respectively. The active oxygen scavenging rates (%) calculated from these spectra were 34.2%, 70.9%, 65.0%, and 100%, respectively, for treatment times of 3 hours, 6 hours, 24 hours, and 96 hours, in the case of Example 1 treated with ozone using a PSA (oxygen concentrator). Oxygen (O ２ In Example 2, which was treated with ozone (PSA) for 3 hours, 6 hours, and 24 hours, the active oxygen scavenging rates (%) were 28.8%, 48.1%, and 79.7%, respectively. In Example 3, which was treated with air, the active oxygen scavenging rates (%) were 31.5%, 35.6%, and 60.8%, respectively. Note that these active oxygen scavenging rates (%) are relative values, with the active oxygen scavenging rate in Example 1, which was treated with ozone for 96 hours using a PSA (oxygen concentrator), taken as 100%. The bar graph in Figure 21 shows the active oxygen scavenging rates (%) of the samples treated with oxygen (O ２The graph shows the active oxygen scavenging rate (%) for Example 2, in which ozone treatment was performed using ozone-treated cellulose (cellulose acetate) as a raw material for 3, 6, and 24 hours. As shown in the figure, a high active oxygen scavenging rate (%) was obtained even with a short ozone treatment time, and the longer the ozone treatment time, the higher the active oxygen scavenging rate (%). The bar graph in Figure 22 also shows the active oxygen scavenging rate (%) for Examples 1 to 3 for a 24-hour treatment. As shown in the figure, a high active oxygen scavenging function was obtained regardless of whether an oxygen cylinder, PSA, or air was used as the ozone raw material supply source. Furthermore, in Example 1, in which ozone treatment was performed with PSA, the glycerin was replaced with a 50% glycerin aqueous solution and a 5% glycerin aqueous solution, and ozone treatment was performed, respectively. Figure 23 shows the active oxygen scavenging rate (%) for each of these samples when the ozone treatment time was 24 hours. As shown in the figure, the higher the glycerin concentration, the higher the active oxygen scavenging rate (%). However, even at a glycerin concentration of 5%, the active oxygen scavenging rate (%) was sufficiently high compared to untreated glycerin (see FIG. 12). Regarding the 96-hour treatment in Example 1, which yielded the highest active oxygen scavenging rate, the ozone-treated glycerin solution after 96 hours of treatment was further heated at 50°C for two weeks. As a result, as shown in the bar graph in FIG. 24, the active oxygen scavenging rate remained unchanged at 100% before and after heating. This confirmed that the ozone-treated glycerin, which has active oxygen scavenging function and is contained in the ozone-treated glycerin solution of this example, is extremely stable even under heating conditions at 50°C. Furthermore, as shown in the bar graph in FIG. 25, the same results were obtained when the solution was stored at room temperature for 3, 6, or 24 hours instead of heating at 50°C.

[0083] [Comparison of pH in Examples 1 to 3] The correlation between treatment time and pH in each of Examples 1 to 3 is shown in the graph of FIG. 26. In the graph, the horizontal axis represents treatment time, and the vertical axis represents pH. The pH was measured after diluting each glycerin solution 10 times with water. Also, in the graph, "O2 bomb synthesis G" represents the pH measured using oxygen (O ２) represents Example 2, in which ozone treatment was performed using oxygen in a cylinder as the raw material. "Air-Synthetic G" represents Example 3, in which ozone treatment was performed using oxygen in the air as the raw material. "PSA-Synthetic G" represents Example 1, in which ozone treatment was performed using a PSA (oxygen concentrator). "PSA-50% Synthetic G" represents Example 1, in which synthetic glycerin was diluted 50% with water and then ozone treatment was performed. "PSA-5% Synthetic G" represents Example 1, in which synthetic glycerin was diluted 5% with water and then ozone treatment was performed. "PSA-Sakamoto G" represents Example 1, in which the synthetic glycerin was replaced with glycerin manufactured by Sakamoto Pharmaceutical Industry. As shown in the figure, the pH was within the range of 1.00 to 5.00 in all cases.

[0084] 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.

[0085] <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 comprising 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 ozone-treated alcohol is ozone-treated glycerin. (Appendix 3) The active oxygen scavenger according to appendix 1 or 2, wherein the ozone-treated alcohol comprises an ozone-treated alcohol having an active oxygen scavenging function. (Appendix 4) A method for scavenging active oxygen, comprising a reaction step of reacting active oxygen with a stain-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas. (Appendix 5) The method for scavenging active oxygen according to appendix 4, wherein the reaction step is a step of reacting the active oxygen scavenger according to any one of appendices 1 to 3 with active oxygen. (Appendix 6) A method for producing an active oxygen scavenger, comprising an ozone treatment step of ozone-treating alcohol with an oxygen allotrope-containing gas. (Appendix 7) The method according to appendix 6, wherein the alcohol is glycerin.

[0086] As described above, the present disclosure provides a novel active oxygen scavenger, an active oxygen scavenging method, 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.

[0087] This application claims priority based on Japanese Patent Application No. 2024-023291, filed on February 19, 2024, the disclosure of which is incorporated herein in its entirety by reference.

Claims

1. An active oxygen scavenger, characterized by containing an ozone-treated alcohol that has been ozone-treated with an oxygen allotrope-containing gas.

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

3. The active oxygen scavenger according to claim 1 or 2, wherein the ozone-treated alcohol comprises an ozone-treated alcohol having an active oxygen scavenging function.

4. A method for eliminating active oxygen, comprising a reaction step of reacting an ozone-treated alcohol, which has been ozone-treated with an oxygen allotrope-containing gas, with active oxygen.

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

6. A method for producing an active oxygen scavenger, comprising an ozone treatment step of treating alcohol with an oxygen allotrope-containing gas.

7. The method of claim 6, wherein the alcohol is glycerin.

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