Ozone-treated glycerol and method for producing same, cosmetic, food and beverage, and oral composition

Abstract

Provided is an ozone-treated glycerol having an oxidizing power of 10-300 ppm in terms of ozone concentration. The ozone-treated glycerol is characterized by: (1) being an ozone-formed oxide obtained by oxidizing glycerol with ozone for one hour or more; (2) being a polyol dilution obtained by diluting, with a polyol, an ozone-treated glycerol having a high oxidizing power of 1,000 ppm or more in terms of ozone concentration; or (3) having one or more activities that promote the expression of involucrin, the production of filaggrin, the production of LC3-II, or the production of ceramide.

Description

Ozone-treated glycerin, its manufacturing method, and cosmetics, foods and beverages, and oral compositions

[0001] The present invention relates to ozone-treated glycerin, a method for producing ozone-treated glycerin, and cosmetics, foods and beverages, and oral compositions containing the ozone-treated glycerin.

[0002] Ozone-treated glycerin, which has been given oxidizing ability by ozone treatment, has been well known and is used in applications such as a disinfectant (see Patent Documents 1 to 3), a tooth whitening agent (see Patent Document 4), and an inducer of heat shock protein expression (see Patent Document 5).

[0003] Furthermore, as a result of further intensive research, the present inventors have proposed an oxidation reaction product (ozone-treated glycerin) containing a cyclic peroxide represented by the following chemical formula (I) (see Patent Document 6). The cyclic peroxide contained in this proposed ozone-treated glycerin is safer than hydrogen peroxide, has excellent water solubility, and is chemically more stable and easier to handle than radicals, etc., and therefore can be isolated and formulated into pharmaceutical preparations.

[0004] In the chemical formula (I), R １００ is a cyclic structure having 3 or more ring members, which may be saturated or unsaturated, may be an aromatic ring or a non-aromatic ring, may or may not have a heteroatom other than the oxygen atom in the chemical formula (I) in the cyclic structure, may be a single ring or a condensed ring, R １ is a substituent, and may be one, a plurality, or may not be present. When there are a plurality, they may be the same or different.

[0005] Japanese Patent Publication No. 2003-55107 Japanese Patent No. 4677192 Japanese Patent No. 5222344 Japanese Patent No. 6431251 Japanese Patent No. 6671832 International Publication No. 2023 / 022204

[0006] However, the ozone-treated glycerin described in Patent Document 6 has a high oxidizing power of 4,000 ppm in terms of hydrogen peroxide concentration. Furthermore, the examples in Patent Document 6 use ozone-treated glycerins with oxidizing powers of 4,000 ppm and 2,000 ppm in terms of hydrogen peroxide concentration. Therefore, there are concerns about the effects of the high oxidizing power of the ozone-treated glycerin described in Patent Document 6 on other components, and there is a problem in that it is difficult to incorporate an effective amount of the ozone-treated glycerin into multi-component systems such as cosmetics, foods and beverages, or oral compositions.

[0007] Furthermore, in the above Patent Documents 1 to 3, the inventions are based on antibacterial activity, which is primarily based on oxidative power. However, the manifestation of antibacterial activity can also lead to cytotoxicity and can destroy the skin bacterial flora, potentially causing skin problems. Therefore, these are unsuitable for use in cosmetics and the like, and no consideration has been given to setting optimal concentrations for use in cosmetics and the like.

[0008] The present invention has been made in view of the above-mentioned conventional technologies, and an object of the present invention is to provide ozone-treated glycerin with low oxidizing power that has few adverse effects even in multi-component systems such as cosmetics, foods and beverages, or oral compositions and that can exhibit excellent properties, a method for producing ozone-treated glycerin, and cosmetics, foods and beverages, and oral compositions that contain the ozone-treated glycerin.

[0009] Another object of the present invention is to discover the effectiveness at low concentrations in cosmetics, foods and beverages, and oral compositions that do not cause cytotoxicity, which has not been investigated until now, and to provide it not only as a raw material but also as a formulation for final products.

[0010] The ozone-treated glycerin according to the first embodiment of the present invention has an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, and is an ozone oxide obtained by oxidizing glycerin with ozone for one hour or more. In a preferred aspect of the ozone-treated glycerin according to the first embodiment of the present invention, the ozone-treated glycerin has at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity. In a preferred aspect of the ozone-treated glycerin according to the first embodiment of the present invention, the oxidizing power of 50 ppm to 200 ppm in terms of ozone concentration.

[0011] The ozone-treated glycerin according to the second embodiment of the present invention is a polyol dilution obtained by diluting high-oxidizing-power ozone-treated glycerin, having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration and an oxidizing power of 1,000 ppm or more in terms of ozone concentration, with a polyol. In a preferred aspect of the ozone-treated glycerin according to the second embodiment of the present invention, the ozone-treated glycerin has at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity. In a preferred aspect of the ozone-treated glycerin according to the second embodiment of the present invention, the oxidizing power in terms of ozone concentration is 50 ppm to 200 ppm. In a preferred aspect of the ozone-treated glycerin according to the second embodiment of the present invention, the polyol is at least one selected from glycerin, butylene glycol, propylene glycol, pentylene glycol, and polyethylene glycol. In a preferred aspect of the ozone-treated glycerin according to the second embodiment of the present invention, the polyol is glycerin.

[0012] The ozone-treated glycerin according to the third embodiment of the present invention has an oxidizing power, calculated as an ozone concentration, of 10 ppm to 300 ppm and has at least one of an involucrin expression-promoting activity, a filaggrin production-promoting activity, an LC3-II production-promoting activity, and a ceramide production-promoting activity. In a preferred aspect of the ozone-treated glycerin according to the third embodiment of the present invention, the oxidizing power, calculated as an ozone concentration, is 50 ppm to 200 ppm.

[0013] The cosmetic preparation of the present invention contains the ozone-treated glycerin according to any one of the first to third embodiments of the present invention.

[0014] The food or drink of the present invention contains the ozone-treated glycerin according to any one of the first to third embodiments of the present invention.

[0015] The oral composition of the present invention contains the ozone-treated glycerin according to any one of the first to third embodiments of the present invention.

[0016] The method for producing ozone-treated glycerin according to the first embodiment of the present invention is a method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, in which a glycerin solution is subjected to gas-liquid contact with a gas containing ozone for one hour or more. In a preferred aspect of the method for producing ozone-treated glycerin according to the first embodiment of the present invention, the glycerin solution has a glycerin concentration of 80 mass% or more. In a preferred aspect of the method for producing ozone-treated glycerin according to the first embodiment of the present invention, the glycerin solution is subjected to gas-liquid contact with a gas containing ozone for one hour to 16 hours. In a preferred aspect of the method for producing ozone-treated glycerin according to the first embodiment of the present invention, the oxidizing power of the method for producing ozone-treated glycerin according to the first embodiment of the present invention is 50 ppm to 200 ppm in terms of ozone concentration.

[0017] A second embodiment of the present invention relates to a method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, in which a glycerin solution is oxidized with ozone until the oxidizing power in terms of ozone concentration is 1,000 ppm or more, and the resulting high-oxidizing-power ozone-treated glycerin is diluted with a polyol. In a preferred aspect of the method for producing ozone-treated glycerin according to the first embodiment of the present invention, the glycerin solution has a glycerin concentration of 80% by mass or more. In a preferred aspect of the method for producing ozone-treated glycerin according to the second embodiment of the present invention, the oxidizing power in terms of ozone concentration is 50 ppm to 200 ppm. In a preferred aspect of the method for producing ozone-treated glycerin according to the second embodiment of the present invention, the polyol is at least one selected from glycerin, butylene glycol, propylene glycol, pentylene glycol, and polyethylene glycol. In a preferred aspect of the method for producing ozone-treated glycerin according to the second embodiment of the present invention, the polyol is glycerin.

[0018] According to the present invention, it is possible to provide ozone-treated glycerin, which has low oxidizing power and exhibits excellent properties even though it is a multi-component system and has few adverse effects, a method for producing ozone-treated glycerin, and cosmetics, foods and beverages, and oral compositions containing the ozone-treated glycerin. Furthermore, according to the present invention, it has been discovered that ozone-treated glycerin is effective in low concentration ranges as cosmetics, foods and beverages, and oral compositions without causing cytotoxicity, which has not been investigated until now, and it can be provided not only as a raw material but also as a formulation for final products.

[0019] FIG. 1 shows the DMSO-d ６ was used as a solvent and measured at a temperature of 300 K (27 °C). １ 1 H NMR spectrum of the reaction mixture (TLC 1 spot) of glycerin ozone oxidation. ６ was used as a solvent and measured at a temperature of 300 K (27 °C). １３ 3 shows the C NMR spectrum of the reaction mixture (TLC 1 spot) of glycerin ozone oxidation in DMSO-d６ was used as a solvent and measured at a temperature of 300 K (27 °C). １３ 4 shows the C DEPT135 NMR spectrum of the reaction mixture (TLC 1 spot) of glycerin ozone oxidation. ６ As a solvent, the COSY NMR spectrum was measured at a temperature of 300 K (27° C.). ６ 6 shows the HSQC NMR spectrum measured at a temperature of 300 K (27° C.) using DMSO-d ６ FIG. 7 shows the HMBC NMR spectrum measured at 300 K (27°C) using acetonitrile as a solvent. FIG. 7 shows the total ion chromatogram (ESI-negative mode) of the precision preparative LC (liquid chromatography) of a sample prepared (diluted) with acetonitrile to approximately 3% by mass of the reaction mixture (TLC 1 spot product) and a blank. FIG. 8 shows the mass spectrum of peaks F, G, and H (Fraction F, Fraction G, and Fraction H) in FIG. 7. FIG. 9 shows the results of an investigation into improved separation (improved separation conditions) in HILIC (high performance liquid chromatography). FIG. 10 shows the mass spectrum of peaks 1 to 3 in FIG. 9 (after improved separation). FIG. 11 shows the mass spectrum of peaks 4 to 6 in FIG. 9 (after improved separation). FIG. 12 shows the mass spectrum of peaks 7 and 8 in FIG. 9 (after improved separation). Fig. 13 shows the microscopic Raman spectrum of a sample of peak 2 (Mw = 180) in Fig. 9 and that of an ozonide standard. １ 15 is a H NMR spectrum of peak 2 (Mw=180) in FIG. １３ 16 shows the two-dimensional ( １ H- １３1C COSY NMR spectrum. FIG. 17 shows HILIC chromatograms of the TLC1 spot sample and glyceraldehyde dimer under the HILIC (high performance liquid chromatography) conditions of FIG. 9 together. FIG. 18 shows HILIC chromatograms of the TLC1 spot sample and glyceraldehyde dimer under reversed-phase HILIC (high performance liquid chromatography) conditions together. FIG. 19 is an enlarged view of a portion of FIG. 18. FIG. 20 shows ESR spectra of the TLC1 spot sample and peak 2 (Mw=180) in FIG. 9 together. FIG. 21 shows ESR spectra of ozonated methyl linolenate. FIG. 22 shows ESR spectra of peaks 1 to 8 in FIG. 9. FIG. 23 shows the results of measuring the activity of peaks 1 to 8 in FIG. 9 by chemiluminescence. Figure 24 is an explanatory diagram of the effects of untreated glycerin, diluted low-oxidizing power ozone-treated glycerin (OG200), and high-oxidizing power ozone-treated glycerin (OG2000) on the thickening properties of carboxyvinyl polymers. Figure 25A is an explanatory diagram of the effects of untreated glycerin, high-oxidizing power ozone-treated glycerin (OG2000), low-oxidizing power ozone-treated glycerin (OG200D), and diluted low-oxidizing power ozone-treated glycerin (OG200) on the discoloration of a carboxyvinyl polymer (Carbopol 980) solution. Figure 25B is an explanatory diagram of the effects of untreated glycerin, high-oxidizing power ozone-treated glycerin (OG2000), low-oxidizing power ozone-treated glycerin (OG200D), and diluted low-oxidizing power ozone-treated glycerin (OG200) on the discoloration of a carboxyvinyl polymer (Carbopol Ultrez 30) solution. Figure 26 is an explanatory diagram of the effects of untreated glycerin, high-oxidizing power ozone-treated glycerin (OG2000), low-oxidizing power ozone-treated glycerin (OG200D), and diluted low-oxidizing power ozone-treated glycerin (OG200) on the discoloration of xanthan gum solutions. Figure 27 is an explanatory diagram of the effects of diluted low-oxidizing power ozone-treated glycerin (OG200) and high-oxidizing power ozone-treated glycerin (OG2000) on filaggrin expression. Figure 28 is an explanatory diagram of the effects of diluted low-oxidizing power ozone-treated glycerin (OG200) and high-oxidizing power ozone-treated glycerin (OG2000) on CerS1 expression.Figure 29 is an explanatory diagram of the effects of diluted low-oxidizing-power ozone-treated glycerin (OG200) and low-oxidizing-power ozone-treated glycerin (OG200D) on CerS1 expression. Figure 30 is an explanatory diagram of the effects of diluted low-oxidizing-power ozone-treated glycerin (OG200) and high-oxidizing-power ozone-treated glycerin (OG2000) on LC3-II expression. Figure 31 is an explanatory diagram of the effects of diluted low-oxidizing-power ozone-treated glycerin (OG200) and high-oxidizing-power ozone-treated glycerin (OG2000) on Involucrin expression. Figure 32 is an explanatory diagram regarding the cell viability of diluted low-oxidizing-power ozone-treated glycerin (OG200) and untreated glycerin.

[0020] Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to these embodiments in any way.

[0021] (Ozone-Treated Glycerin of First Embodiment) The ozone-treated glycerin of the first embodiment has an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, and is an ozone oxide obtained by oxidizing glycerin with ozone for one hour or more.

[0022] Since ozone-treated glycerin has an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, it does not affect the functions of other components even when blended into multi-component systems such as cosmetics, and has a skin function improving function equal to or greater than that of high-oxidizing glycerin. This ozone-treated glycerin with an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration is sometimes referred to as low-oxidizing ozone-treated glycerin.

[0023] The ozone-treated glycerin of the first embodiment has an oxidizing power, calculated as an ozone concentration, of 10 ppm to 300 ppm, preferably 10 ppm to 250 ppm, more preferably 10 ppm to 200 ppm, even more preferably 30 ppm to 200 ppm, even more preferably 50 ppm to 200 ppm, particularly preferably 50 ppm to 150 ppm, and most preferably 50 ppm to 100 ppm. When the oxidizing power, calculated as an ozone concentration, is within the above range, the ozone-treated glycerin can be used in multi-component systems such as cosmetics, foods and beverages, or oral compositions without suffering from adverse effects due to high oxidizing power. The oxidizing power, calculated as an ozone concentration, of the ozone-treated glycerin can be measured, for example, by potassium iodide titration.

[0024] The ozone-treated glycerin of the first embodiment is an ozone oxide obtained by oxidizing glycerin with ozonation for one hour or more, preferably an ozone oxide obtained by oxidizing glycerin with ozonation for one to sixteen hours, more preferably an ozone oxide obtained by oxidizing glycerin with ozonation for one to fourteen hours, even more preferably an ozone oxide obtained by oxidizing glycerin with ozonation for three to fourteen hours, still more preferably an ozone oxide obtained by oxidizing glycerin with ozonation for three to twelve hours, particularly preferably an ozone oxide obtained by oxidizing glycerin with ozonation for five to twelve hours, and most preferably an ozone oxide obtained by oxidizing glycerin with ozonation for five to ten hours.

[0025] The ozone-treated glycerin according to the first embodiment preferably has at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity.

[0026] Involucrin is one of the components of the outer cell wall of the stratum corneum, and is used, for example, as an indicator of the early stage of differentiation of epidermal keratinocytes.

[0027] Filaggrin is a protein produced in epidermal granular cells and involved in skin barrier function. Filaggrin is a major protein constituting cells of the stratum corneum, the outermost layer of the skin, and functions to aggregate and bundle keratin fibers in the stratum corneum cells, strengthening the stratum corneum barrier. Filaggrin is biosynthesized as its precursor, profilaggrin. Profilagrin is a large protein with a molecular weight of approximately 400 kDa, consisting of 10 to 20 linked filaggrin molecules, which undergoes phosphorylation to form keratohyalin granules in granular cells. When granular cells migrate to stratum corneum cells, phosphorylated profilaggrin undergoes dephosphorylation and limited hydrolysis, resulting in degradation to filaggrin. Filaggrin promotes the fibrogenesis reaction of keratin fibers that progresses within stratum corneum cells. By promoting filaggrin production, skin diseases associated with decreased filaggrin production can be treated.

[0028] Ceramides are amide derivatives that account for approximately 50% of the intercellular lipids present in human skin (stratum corneum). Examples of ceramides include N-acylsphingosine (ceramide), N-acyldihydrosphingosine (dihydroceramide), and N-acylphytosphingosine (phytoceramide). Ceramides are known to act as signal transduction substances and regulate cell proliferation, differentiation, apoptosis, and the like.

[0029] LC3-II is one of the main markers of autophagy. Autophagy plays an important role in the body, promoting cellular metabolism and eliminating harmful substances such as waste products and unnecessary proteins accumulated within cells. Autophagy is known to decline with age, and abnormalities in autophagy are thought to be deeply involved in various aging-related diseases, such as cancer and neurodegenerative diseases, as well as skin aging and skin color determination.

[0030] The ozone-treated glycerin of the first embodiment can be suitably produced by the method for producing ozone-treated glycerin of the first embodiment described below.

[0031] (Method for Producing Ozone-Treated Glycerin According to a First Embodiment) A method for producing ozone-treated glycerin according to a first embodiment is a method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, in which a glycerin solution is brought into gas-liquid contact with a gas containing ozone for one hour or more.

[0032] The glycerin concentration in the glycerin solution is not particularly limited and can be appropriately selected depending on the purpose. For example, a glycerin concentration of 50% by mass or more is preferred, more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and most preferably 98% by mass or more. Specifically, a glycerin solution of 84% by mass or more as specified in the Japanese Pharmacopoeia is preferred, a concentrated glycerin solution of 98% by mass or more as specified in the Japanese Pharmacopoeia is more preferred, and a purified glycerin solution of 98.5% by mass or more as specified in the Japanese Pharmacopoeia is even more preferred. The higher the glycerin concentration of the glycerin solution, the higher the concentration of ozone that can be treated. In the glycerin solution, the solvent for glycerin is not particularly limited and can be, for example, an aqueous solvent such as water.

[0033] The ozone-containing gas preferably has a high ozone concentration. The method for producing such a gas with a high ozone concentration is not particularly limited, and for example, a silent discharge ozone generator that generates ozone by silently discharging oxygen gas can be used. When oxygen gas is used, for example, a medical oxygen cylinder or oxygen produced by an oxygen generator can be used.

[0034] The method for bringing the glycerin solution into gas-liquid contact with the ozone-containing gas is not particularly limited, and for example, there is a method in which the glycerin solution is placed in a tank and the gas with a high ozone concentration is released into the tank as fine bubbles using an air diffuser. Specifically, by aerating a gas with an ozone concentration of 37,000 ppm into the concentrated glycerin solution for a predetermined period of time, it is possible to produce ozone-treated glycerin having an oxidizing power, calculated as an ozone concentration, of 10 ppm to 300 ppm.

[0035] The predetermined time for aeration (time for gas-liquid contact) is 1 hour or more, and is preferably, for example, 1 hour to 16 hours, 1 hour to 14 hours, 2 hours to 14 hours, 3 hours to 14 hours, 3 hours to 12 hours, 3 hours to 10 hours, or 5 hours to 10 hours.

[0036] (Ozone-treated glycerin of second embodiment) The ozone-treated glycerin of the second embodiment is a polyol dilution obtained by diluting high-oxidizing-power ozone-treated glycerin, which has an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration and an oxidizing power of 1,000 ppm or more in terms of ozone concentration, with a polyol.

[0037] The ozone-treated glycerin of the second embodiment is obtained by diluting the high-oxidizing-power ozone-treated glycerin with a polyol, and does not affect other components, and exhibits skin activation ability with minimal change in viscosity and color over time that is equal to or greater than that of the high-oxidizing-power ozone-treated glycerin, and further exhibits cell proliferation ability (cell viability) that is equal to or greater than that of untreated glycerin. Furthermore, the ozone-treated glycerin of the second embodiment preferably has at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity.

[0038] The ozone-treated glycerin of the second embodiment has an oxidizing power, calculated as an ozone concentration, of 10 ppm to 300 ppm, preferably 10 ppm to 250 ppm, more preferably 10 ppm to 200 ppm, even more preferably 30 ppm to 200 ppm, still more preferably 50 ppm to 200 ppm, particularly preferably 50 ppm to 150 ppm, and most preferably 50 ppm to 100 ppm.

[0039] The ozone-treated glycerin is a polyol dilution obtained by diluting high-oxidizing-power ozone-treated glycerin, having an oxidizing power, calculated as an ozone concentration, of 1,000 ppm or more, preferably 1,500 ppm or more, more preferably 2,000 ppm or more, and even more preferably 2,500 ppm or more, with a polyol until the oxidizing power, calculated as an ozone concentration, is 10 ppm to 300 ppm. The high-oxidizing-power ozone-treated glycerin can be produced by adjusting the gas-liquid contact time in accordance with the target oxidizing power in the method for producing ozone-treated glycerin of the first embodiment. For example, the gas-liquid contact time can be set to 24 hours or more, 2 days or more, 3 days or more, 4 days or more, 5 days or more, 6 days or more, or 7 days or more.

[0040] The polyol is preferably at least one selected from glycerin, butylene glycol, propylene glycol, pentylene glycol, and polyethylene glycol, more preferably glycerin, butylene glycol, propylene glycol, or pentylene glycol, and particularly preferably glycerin.

[0041] The ozone-treated glycerin of the second embodiment can be suitably produced by the method for producing ozone-treated glycerin of the second embodiment described below.

[0042] (Method for Producing Ozone-Treated Glycerin of Second Embodiment) The method for producing ozone-treated glycerin of the second embodiment is a method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, in which a glycerin solution is oxidized with ozone until the oxidizing power thereof becomes 1,000 ppm or more in terms of ozone concentration, to produce high-oxidizing-power ozone-treated glycerin, which is diluted with a polyol. The dilution method is not particularly limited, and a polyol diluted solution can be obtained by mixing the high-oxidizing-power ozone-treated glycerin and a polyol in a predetermined ratio and stirring the mixture.

[0043] (Ozone-treated glycerin of third embodiment) The ozone-treated glycerin of the third embodiment of the present invention has an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, and has at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity.

[0044] The ozone-treated glycerin of the third embodiment has an oxidizing power, calculated as an ozone concentration, of 10 ppm to 300 ppm, preferably 10 ppm to 250 ppm, more preferably 10 ppm to 200 ppm, even more preferably 30 ppm to 200 ppm, still more preferably 50 ppm to 200 ppm, particularly preferably 50 ppm to 150 ppm, and most preferably 50 ppm to 100 ppm.

[0045] The ozone-treated glycerin of the third embodiment can be suitably produced by the method for producing ozone-treated glycerin of the first or second embodiment described above.

[0046] The ozone-treated glycerin according to at least any one of the first to third embodiments preferably contains a cyclic peroxide represented by the following chemical formula (1) or a salt thereof.

[0047]

[0048] The cyclic peroxide represented by the above chemical formula (1) is represented by the following chemical formula (I): １１ is the case where all atoms are hydrogen atoms.

[0049] In the chemical formula (I), each R １１ may be the same or different and each represents a hydrogen atom, a hydroxyl group, a hydroxyalkyl group, or an alkyl group. The number of carbon atoms in the hydroxyalkyl group or alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. Examples of the alkyl group include a methyl group, an ethyl group, and a propyl group.

[0050] When the cyclic peroxide represented by the above chemical formula (1) can form a salt, 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.

[0051] 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, fluoric acid, chloric acid, bromic acid, iodic acid, perfluoric acid, perchloric acid, perbromic acid, periodic acid, etc. The organic acid is 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, acetic acid, etc.

[0052] The inorganic base is not particularly limited, but examples thereof include ammonium hydroxide, alkali metal hydroxides, alkaline earth metal hydroxides, carbonates, and hydrogen carbonates, and more specific examples thereof include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, calcium hydroxide, and calcium carbonate. The organic base is 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 a method in which the above-mentioned acid or base is appropriately added to the compound by a known method.

[0053] The method for producing the cyclic peroxide represented by the chemical formula (1) is not particularly limited, but it can be produced by ozone oxidation of glycerin. The cyclic peroxide represented by the chemical formula (1) may be used directly without being separated from the mixture after the reaction (e.g., the ozone-treated glycerin solution), or it may be used after being separated from the mixture after the reaction. The separation method is not particularly limited, but the cyclic peroxide represented by the chemical formula (1) can be separated from the mixture after the reaction by chromatography such as preparative thin-layer chromatography, for example.

[0054] (Cosmetics) The cosmetics of the present invention contain the ozone-treated glycerin of at least any one of the first to third embodiments of the present invention, and further contain other ingredients as necessary. Conventional high-oxidizing power ozone-treated glycerin can affect the functionality of multi-component cosmetics, particularly having a significant impact on thickening caused by water-soluble thickeners such as carboxyvinyl polymers or xanthan gum. However, the ozone-treated glycerin of at least any one of the first to third embodiments of the present invention can suppress thickening caused by water-soluble thickeners, causes little change in color tone, and has a high skin function improving function while having almost no effect on multi-component systems. The content of the ozone-treated glycerin of at least any one of the first to third embodiments in the cosmetics is not particularly limited and can be adjusted as appropriate.

[0055] <Other Components> The cosmetic composition of the present invention can be produced by appropriately blending other components, as needed, within the scope that does not impair the effects of the present invention, 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, water, and the like.

[0056] 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. These may be used alone or in combination of two or more.

[0057] 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.). These may be used alone or in combination of two or more.

[0058] 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; glycerin alkyl ethers, etc. These may be used alone or in combination of two or more.

[0059] 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, POE-glycerin triisostearate, etc.); 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.); Pluronic (registered trademark) products; 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 monopyrogulol, etc.); tamic 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;trioleyl phosphate, etc. These may be used alone or in combination of two or more.

[0060] 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 robur extract, Achillea millefolium extract, Melilot extract, etc. These may be used alone or in combination of two or more.

[0061] 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.). These may be used alone or in combination of two or more.

[0062] 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.); alginic acid-based polymers (e.g., sodium alginate, propylene glycol alginate, etc.); etc. These may be used alone or in combination of two or more.

[0063] 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 polyoxypropylene copolymers, highly polymerized polyethylene glycol, etc.); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, etc. These may be used alone or in combination of two or more.

[0064] Examples of thickeners include gum arabic, carrageenan, karaya gum, tragacanth gum, carob gum, quince seed (marmelo), casein, dextrin, gelatin, sodium pectinate, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethylcellulose, hydroxypropylcellulose, 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 (veegum), laponite, anhydrous silicic acid, etc. These may be used alone or in combination of two or more.

[0065] 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.);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) Examples of such compounds include 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; and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-(1,3,5)-triazine. These compounds may be used alone or in combination of two or more.

[0066] 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, trisodium ethylenediaminehydroxyethyltriacetate, etc. These may be used alone or in combination of two or more.

[0067] Examples of lower alcohols include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol, etc. These may be used alone or in combination of two or more.

[0068] 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, octylene glycol, etc.); trihydric alcohols (e.g., glycerin, trimethylolpropane, etc.); tetrahydric alcohols (e.g., pentaerythritol such as 1,2,6-hexanetriol, etc.); pentahydric alcohols (e.g., xylitol, etc.); hexahydric alcohols (e.g., sorbitol, mannitol, etc.); polyhydric alcohol polymers (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, etc.); 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, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol butyl ether, etc.); 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 di succinate, 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.); sugar alcohols (e.g., sorbitol, maltitol, maltotriol, etc.); Examples of suitable sugars include maltose, mannitol, sucrose, erythritol, glucose, fructose, starch-decomposed sugars, maltose, xylitose, starch-decomposed sugar-reduced alcohols, etc.; 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. These may be used alone or in combination of two or more.

[0069] 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- mannose, D-tagatose, etc.); heptoses (e.g., aldoheptose, heprose, 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.). These may be used alone or in combination of two or more.

[0070] Examples of oligosaccharides include sucrose, gunthianose, umbelliferose, lactose, planteose, isolychnoses, α,α-trehalose, raffinose, lychnoses, umbilicin, stachyose, verbascoses, etc. These may be used alone or in combination of two or more.

[0071] 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, keratosulfuric acid, locust bean gum, succinoglucan, and caronic acid. These may be used alone or in combination of two or more.

[0072] Examples of amino acids include neutral amino acids (e.g., threonine, cysteine, etc.); basic amino acids (e.g., hydroxylysine, etc.). Examples of amino acid derivatives include acyl sarcosine sodium (sodium lauroyl sarcosine), acyl glutamate, acyl β-alanine sodium, glutathione, pyrrolidone carboxylic acid, etc. These may be used alone or in combination of two or more.

[0073] Examples of organic amines include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol. These may be used alone or in combination of two or more. Examples of polymer emulsions include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacrylic alkyl ester emulsion, polyvinyl acetate resin emulsion, and natural rubber latex. These may be used alone or in combination of two or more.

[0074] Examples of pH adjusters include buffers such as citric acid, lactic acid-sodium lactate, citric acid-sodium citrate, succinic acid-sodium succinate, etc. These may be used alone or in combination of two or more.

[0075] Vitamins include, for example, vitamins A and B １ , B ２ , B ６ , C, E or derivatives thereof, pantothenic acid or derivatives thereof, biotin, etc. These may be used alone or in combination of two or more.

[0076] Examples of antioxidants include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, etc. These may be used alone or in combination of two or more.

[0077] Examples of antioxidant aids include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, cephalin, hexametaphosphate, phytic acid, ethylenediaminetetraacetic acid, etc. These may be used alone or in combination of two or more.

[0078] Specific examples of other ingredients that can be added include preservatives (e.g., ethylparaben, butylparaben, chlorphenesin, phenoxyethanol, etc.); disinfectants (e.g., isopropylmethylphenol, benzalkonium chloride, benzethonium chloride, chlorhexidine gluconate, etc.); anti-inflammatory agents (e.g., glycyrrhizinic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (e.g., placenta extract, saxifrage extract, arbutin, etc.); various extracts (e.g., 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 rhizome, Ginger Cucumber, St. John's wort, Ononis, garlic, chili pepper, 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.). These may be used alone or in combination of two or more.

[0079] Further, sequestering agents such as edetate disodium, edetate trisodium, 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 laurel; 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, ascorbyl glucoside, arbutin, and kojic acid; amino acids or derivatives thereof such as arginine and lysine; and sugars such as fructose, mannose, erythritol, trehalose, and xylitol, etc. may also be appropriately blended. These may be used alone or in combination of two or more.

[0080] The cosmetic of the present invention has excellent safety, stability, and usability, and is suitable for use as a skin (skin care) cosmetic and / or a hair (hair care) cosmetic. Examples of skin care cosmetics include skin cosmetics such as lotions, emulsions, creams, serums, and packs, cleansers, facial washes, UV protection agents, makeup, base cosmetics such as base lotions and makeup base creams, foundations in various dosage forms such as emulsions, oils, 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.

[0081] 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.

[0082] The cosmetic composition of the present invention is preferably applied to humans, but can also be applied to animals other than humans as long as the respective functional effects are achieved.

[0083] (Food and drink) The food and drink of the present invention contains the ozone-treated glycerin of at least one of the first to third embodiments of the present invention, and further contains other ingredients as necessary. The ozone-treated glycerin of at least one of the first to third embodiments of the present invention has high safety performance while having little effect on the multi-component food and drink. Here, "food and drink" refers to a food or drink that is ingested orally or via gastrointestinal administration in normal social life and is unlikely to pose a risk to human health. It is not limited to administrative classifications such as food, medicine, or quasi-drug. Therefore, "food and drink" in this embodiment broadly includes orally ingested general foods, health foods (functional food and drink), health functional foods (foods for specified health uses, foods with nutrient functions), quasi-drugs, medicines, etc. The content of the ozone-treated glycerin of at least one of the first to third embodiments in the food and drink is not particularly limited and can be adjusted as appropriate.

[0084] <Other Ingredients> The other ingredients are not particularly limited and can be appropriately selected depending on the purpose from auxiliary raw materials, additives, or other ingredients that are commonly used in the production of foods and beverages. 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, and preservatives. 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.

[0085] 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, tablet candies, 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.

[0086] 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.

[0087] The method of ingestion of 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.

[0088] The food and drink of the present invention is preferably applied to humans, but can also be applied to animals other than humans as long as the respective functional effects are achieved.

[0089] (Oral composition) The oral composition of the present invention contains the ozone-treated glycerin of at least any one of the first to third embodiments of the present invention, and further contains other components as necessary. At least any one of the ozone-treated glycerin of the first to third embodiments of the present invention has high safety performance and has almost no effect on the oral composition, which is a multi-component system. The content of at least any one of the ozone-treated glycerin of the first to third embodiments in the oral composition is not particularly limited and can be adjusted as appropriate.

[0090] 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.

[0091] 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.

[0092] The oral composition may contain other components in addition to the components described above depending on the intended application, form, use, etc. Examples of the 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 the other components. The oral composition may contain one of the above other components alone or two or more of them in combination.

[0093] Examples of the present invention will be described below, but the present invention is not limited to these examples. The content of each component is in mass % unless otherwise specified. In the following examples, the oxidizing power of ozone-treated glycerin converted into ozone concentration was measured as follows.

[0094] <Measurement of Oxidizing Power> The oxidizing power of the ozone-treated glycerin solution was measured by potassium iodide titration. Specifically, potassium dihydrogen phosphate (KH ２ P.O. ４ ) 17.90 g and disodium hydrogen phosphate (Na ２ HPO ４ ・12H ２ 17.14 g of potassium iodide (KI) was added and dissolved, and then 25.00 g of potassium iodide (KI) was added and dissolved. The resulting solution was diluted to 500 g with purified water to prepare a potassium iodide absorption solution. Next, sodium thiosulfate (Na ２ S ２ O ３0.32 g of ozone-treated glycerin solution was diluted with purified water to a final weight of 400 g and dissolved in purified water to prepare sodium thiosulfate. Furthermore, 0.22 g of starch was added to 20 g of purified water and boiled to dissolve, preparing a starch aqueous solution. Next, 50 g of potassium iodide absorption solution was added to approximately 1 g (1.00-1.20 g) of the ozone-treated glycerin solution, and the mixture was stirred for 10 minutes on a stirrer set at 300 rpm and 0°C. After stirring, 0.2 ml of starch aqueous solution was added. Using a funnel, the sodium thiosulfate solution was slowly added dropwise to the mixture after the addition of the starch aqueous solution until the mixture became colorless and transparent. The oxidizing power of the sample was calculated based on the following formula (A): O = (St × 24 × T) / S (A) O: oxidizing power of sample (ppm) St: concentration of sodium thiosulfate in sodium thiosulfate solution (mmol / l) S: amount of sample (g) T: titration amount of sodium thiosulfate solution (ml)

[0095] (Ozone-Treated Glycerin Production Example 1) High-concentration glycerin and ozone were brought into gas-liquid contact to produce high-oxidizing power ozone-treated glycerin. A 50-L Teflon (registered trademark) tank was used as the contact vessel. An air diffuser was installed on the bottom of the tank so that ozone could be supplied into the tank as fine bubbles. A silent discharge ozone generator (manufactured by Mediplus Pharmaceutical Co., Ltd.) capable of generating 100 g of ozone per hour using oxygen at a concentration of 90% by volume or more as the raw material was used as the ozone generator. 22 kg of high-concentration glycerin (glycerin at a concentration of 98% by mass or more as specified in the Japanese Pharmacopoeia) was placed in the tank, and 20 L of oxygen was fed into the silent discharge ozone generator at a rate of 20 L per minute. The generated ozone-containing gas was released from the air diffuser into the tank for 5 days (aeration conditions), yielding ozone-treated glycerin (hereinafter sometimes referred to as "OG2000") with an oxidizing power of 2,000 ppm in terms of ozone concentration. The obtained "OG2000" contained the cyclic peroxide represented by the above general formula (1), as will be described later.

[0096] (Ozone-treated Glycerin Production Example 2) A low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG300D") having an oxidizing power of 300 ppm in terms of ozone concentration was obtained in the same manner as in Ozone-treated Glycerin Production Example 1, except that the aeration conditions in Ozone-treated Glycerin Production Example 1 were changed to 16-hour release. The obtained "OG300D" contained the cyclic peroxide represented by the above general formula (1), similar to the above "OG2000".

[0097] (Ozone-treated Glycerin Production Example 3) A low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG200D") having an oxidizing power of 200 ppm in terms of ozone concentration was obtained in the same manner as in Ozone-treated Glycerin Production Example 1, except that the aeration conditions in Ozone-treated Glycerin Production Example 1 were changed to 12-hour release. The obtained "OG200D" contained the cyclic peroxide represented by the above general formula (1), similar to the above "OG2000".

[0098] (Ozone-treated Glycerin Production Example 4) A low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG100D") having an oxidizing power of 100 ppm in terms of ozone concentration was obtained in the same manner as in Ozone-treated Glycerin Production Example 1, except that the aeration conditions in Ozone-treated Glycerin Production Example 1 were changed to 8-hour release. The obtained "OG100D" contained the cyclic peroxide represented by the above general formula (1), similar to the above "OG2000".

[0099] (Ozone-treated Glycerin Production Example 5) A low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG50D") having an oxidizing power of 50 ppm in terms of ozone concentration was obtained in the same manner as in Ozone-treated Glycerin Production Example 1, except that the aeration conditions in Ozone-treated Glycerin Production Example 1 were changed to 4-hour release. The obtained "OG50D" contained the cyclic peroxide represented by the above general formula (1), similar to the above "OG2000".

[0100] (Ozone-Treated Glycerin Production Example 6) The "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with high-concentration glycerin (untreated glycerin with a concentration of 98% by mass or more according to the Japanese Pharmacopoeia) at room temperature to an oxidizing power of 200 ppm in terms of ozone concentration, to obtain diluted low-oxidizing-power ozone-treated glycerin (hereinafter sometimes referred to as "OG200"). The obtained "OG200" contained the cyclic peroxide represented by the above general formula (1), just like the above "OG2000".

[0101] (Ozone-Treated Glycerin Production Example 7) "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with high-concentration glycerin (untreated glycerin with a concentration of 98% by mass or more according to the Japanese Pharmacopoeia) at room temperature to an oxidizing power of 100 ppm in terms of ozone concentration, to obtain diluted low-oxidizing-power ozone-treated glycerin (hereinafter sometimes referred to as "OG100"). The obtained "OG100", like the above "OG2000", contained the cyclic peroxide represented by the above general formula (1).

[0102] (Ozone-Treated Glycerin Production Example 8) The "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with high-concentration glycerin (untreated glycerin with a concentration of 98% by mass or more according to the Japanese Pharmacopoeia) at room temperature to an oxidizing power of 50 ppm in terms of ozone concentration, to obtain diluted low-oxidizing-power ozone-treated glycerin (hereinafter sometimes referred to as "OG50"). The obtained "OG50", like the above "OG2000", contained the cyclic peroxide represented by the above general formula (1).

[0103] (Ozone-Treated Glycerin Production Example 9) "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with butylene glycol at room temperature to an oxidizing power of 200 ppm in terms of ozone concentration, to obtain a diluted low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG200B"). The obtained "OG200B" contained the cyclic peroxide represented by the above general formula (1), just like the above "OG2000".

[0104] (Ozone-Treated Glycerin Production Example 10) The "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with propylene glycol at room temperature to an oxidizing power of 200 ppm in terms of ozone concentration, to obtain diluted low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG200P"). The obtained "OG200P" contained the cyclic peroxide represented by the above general formula (1), similar to the above "OG2000".

[0105] (Ozone-Treated Glycerin Production Example 11) The "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with pentylene glycol at room temperature to an oxidizing power of 200 ppm in terms of ozone concentration, to obtain a diluted low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG200PN"). The obtained "OG200PN" contained the cyclic peroxide represented by the above general formula (1), just like the above "OG2000".

[0106] (Ozone-Treated Glycerin Production Example 12) The "OG2000" obtained in Ozone-Treated Glycerin Production Example 1 was diluted with polyethylene glycol at room temperature to an oxidizing power of 200 ppm in terms of ozone concentration, to obtain diluted low-oxidizing-power ozone-treated glycerin (hereinafter, sometimes referred to as "OG200PE"). The obtained "OG200PE" contained the cyclic peroxide represented by the above general formula (1), just like the above "OG2000".

[0107] <Analysis of Reaction Mixture> Glycerin was removed from the ozone-treated glycerin solution produced in Production Example 1 of Ozone-Treated Glycerin using a silica gel column to obtain a reaction mixture (hereinafter sometimes referred to as "TLC 1 spot product").

[0108] The NMR spectrum of the reaction mixture (TLC 1 spot) was measured using DMSO-d ６ The measurements were carried out at a temperature of 300 K (27°C) using the solvent. The spectra are shown in Figures 1 to 6. １ 1 H NMR spectrum. １３ 3 is a C NMR spectrum diagram. １３FIG. 4 is a C DEPT135 NMR spectrum. FIG. 4 is a COSY NMR spectrum. FIG. 5 is an HSQC NMR spectrum. FIG. 6 is an HMBC NMR spectrum. As shown in FIGS. 1 to 6, complex peaks were observed, suggesting that the TLC1 spot product was a mixture of multiple substances. Furthermore, according to LCMS, this TLC1 spot product contained components with m / z=198,203.

[0109] <Separation and Analysis of Reaction Mixture> The reaction mixture (TLC 1 spot product) was diluted with acetonitrile to approximately 3% by mass, and the filtrate obtained by filtering through a membrane filter was subjected to LC measurement to optimize the separation conditions. Next, the mass of the peak observed in the LC measurement under the optimized conditions was confirmed, and precision fractionation of Mw = 180 (peak 2) was performed. The obtained fraction solution was then freeze-dried, and the dried fraction was subjected to microscopic LR measurement and various NMR measurements. The measurement equipment (analyzer) and measurement conditions are as follows.

[0110] [Measuring equipment (analyzer)] 1) Precision preparative LC: Waters, ACQUITY UPLC H-class Bio 2) Microscope LR: SNOM / AFM / Raman complex machine alpha300RSA manufactured by WITec 3) NMR: Bruker Biospin, AVANCE III-600 with Cryo Probe

[0111] [Measurement conditions] 1) Precision preparative LC Column: Shodex Asahipak NH ２ P-50 (4.6 mmφ×250 mm, 5 μm) Eluent composition: water / acetonitrile system Gradient time (min): 0 5 15 20 Water: 5 10 50 50 Acetonitrile: 95 90 50 50 Flow rate: 1.0 mL / min Detector: MS (QDa) Column temperature: 40°C Injection volume: 50 μL Ionization method: ESI (NEG.) Measurement mass range (m / z): 50 to 500 2) Microscope LR Excitation wavelength: 532 nm Measurement wavenumber range: approximately 125 to 3800 cm －１Objective lens: ×100 Detector: EMCCD 3) NMR observation frequency: 600 MHz ( １ H), 150MHz ( １３ C) Measurement solvent: methanol-d ４ Measurement temperature: 300 K Chemical shift standard: Measurement solvent [3.30 ppm ( １ H), 49.80ppm ( １３ C) ]

[0112] FIG. 7 shows total ion chromatograms (ESI-negative mode) obtained by the precision preparative LC (liquid chromatography) of a sample prepared by diluting the reaction mixture (TLC1 spot product) with acetonitrile to approximately 3% by mass, and a blank. In FIG. 7, the vertical axis represents intensity, and the horizontal axis represents retention time (minutes). In FIG. 7, the lower row of "Synthetic OG" is a chromatogram of the TLC1 spot product sample, and the upper row is a chromatogram of the blank (acetonitrile). As shown in the figure, components A to L were confirmed in the TLC1 spot product. Components A to L were separated and examined for coloration using potassium iodide starch test paper. Component H showed the strongest coloration.

[0113] Figure 8 also shows the mass spectra of peaks F, G, and H (F fraction, G fraction, and H fraction) in Figure 7. In Figure 8, the vertical axis represents intensity, and the horizontal axis represents mass-to-charge ratio (m / z). As shown in the figure, it was confirmed that peak F had Mw = 180, peak G had Mw = 226, and peak H had Mw = 256.

[0114] Furthermore, Figure 9 shows the results of an investigation into the improvement of separation (improvement of separation conditions) in HILIC (high performance liquid chromatography). In Figure 9, the vertical axis represents intensity, and the horizontal axis represents retention time (minutes), as in Figures 17 to 19. In Figure 9, the upper row is a chromatogram before separation improvement (under the same conditions as in Figure 2-10), and the lower row is a chromatogram after separation improvement. As shown in the figure, peaks 1 to 8 were observed after separation improvement. The molecular weights of each peak were confirmed to be the molecular weights shown in Figure 9 using mass spectrometry, which will be described later.

[0115] Figure 10 shows the mass spectra (after improved separation) of peaks 1 to 3 in Figure 9. In Figure 10, the upper row is the mass spectrum of peak 1, the middle row is the mass spectrum of peak 2, and the lower row is the mass spectrum of peak 3. As shown in the figure, it was confirmed that peak 1 had Mw = 196, peak 2 had Mw = 180, and peak 3 had Mw = 240.

[0116] Figure 11 shows the mass spectra (after improved separation) of peaks 4 to 6 in Figure 9. In Figure 11, the upper row is the mass spectrum of peak 4, the middle row is the mass spectrum of peak 5, and the lower row is the mass spectrum of peak 6. As shown in the figure, it was confirmed that peak 4 had Mw = 240, peak 5 had Mw = 240, and peak 6 had Mw = 226.

[0117] Figure 12 shows the mass spectra (after improved separation) of peaks 7 and 8 in Figure 9. In Figure 12, the upper part is the mass spectrum of peak 7, and the lower part is the mass spectrum of peak 8. As shown in the figure, it was confirmed that both peaks 7 and 8 had Mw = 256.

[0118] FIG. 13 also shows the micro-Raman spectra of a sample obtained by separating peak 2 (Mw=180) in FIG. 9 and of an ozonide standard (ozonized oleic acid). In FIG. 13, the vertical axis represents intensity, and the horizontal axis represents Raman shift (1 / cm). As shown in FIG. 13, peak 2 (Mw=180) exhibited a micro-Raman spectrum similar to that of ozonide, and therefore it was presumed to exhibit a structure similar to that of ozonide. Furthermore, the micro-Raman spectrum of peak 2 (Mw=180) exhibited a pattern different from that of peroxide, and therefore it was presumed that peak 2 (Mw=180) was not a peroxide. Peak 2 (Mw=180) was confirmed to be the cyclic peroxide by NMR, which will be described later.

[0119] FIG. 14 shows the peak 2 (Mw=180) in FIG. １ The H NMR spectrum is shown. The measurement solvent was methanol-d ４ (CD ３ In the figure, the upper spectrum is an enlarged view of the lower spectrum around 3.4 to 4.9 ppm. １Based on the H NMR assignments, the Mw=180, and other instrumental analysis data, it was demonstrated that the structure of the oxidation reaction product of peak 2 (Mw=180) was a cyclic peroxide represented by the following chemical formula (1). １ In the H NMR spectrum, the peaks indicated by symbols A to F were assigned to the peaks of hydrogen bonded to the carbon atoms indicated by the same symbols A to F in the following chemical formula (1) shown in Figure 14. It is also presumed that a small amount of glycerin, the raw material, remained, and its peak was also detected.

[0120]

[0121] FIG. 15 shows the peak 2 (Mw=180) in FIG. １３ The C NMR spectrum is shown. The measurement solvent was methanol-d ４ (CD ３ In Figure 15, the upper spectrum is an enlarged view of the lower spectrum around 60 to 105 ppm. １３ Based on the C NMR assignment, the Mw=180, and other instrumental analysis data, it was demonstrated that the structure of the oxidation reaction product of peak 2 (Mw=180) was the cyclic peroxide represented by the above chemical formula (1). １３ In the C NMR spectrum, the peaks indicated by symbols A to F were assigned to the peaks of carbon atoms indicated by the same symbols A to F in the above chemical formula (1) shown in Figure 15. It is also presumed that a small amount of glycerin, the raw material, remained and its peak was also detected.

[0122] FIG. 16 shows the two-dimensional ( １ H- １３ The C COSY NMR spectrum is shown. The measurement solvent was methanol-d ４ (CD ３OD) was used. Based on this 2D NMR assignment, the fact that Mw = 180, and other instrumental analysis data, it was demonstrated that the structure of the oxidation reaction product of peak 2 (Mw = 180) was a cyclic peroxide represented by the above-mentioned chemical formula (1). In the 2D NMR spectrum diagram of FIG. 16, the peaks indicated by symbols A to F were respectively assigned to the peaks of carbon atoms and hydrogen atoms bonded to those carbon atoms represented by the same symbols A to F in the above-mentioned chemical formula (1) shown in FIG. 16. It is also presumed that a small amount of the raw material glycerin remained, and that its peak was also detected.

[0123] Figure 17 also shows HILIC (high performance liquid chromatography) chromatograms of the TLC1 spot product and glyceraldehyde dimer under the HILIC conditions of Figure 9. In Figure 17, the "synthetic OG" in the upper row is a HILIC chromatogram of the TLC1 spot product. The lower row is a HILIC chromatogram with glyceraldehyde dimer. As shown in the figure, glyceraldehyde dimer was not detected under the HILIC conditions of Figure 9.

[0124] Figure 18 also shows HILIC chromatograms of the TLC1 spot product and glyceraldehyde dimer under reversed-phase HILIC (high-performance liquid chromatography) conditions. Figure 19 shows an enlarged view of a portion of Figure 18. In Figures 18 and 19, the "synthetic OG" in the upper row is a HILIC chromatogram of the TLC1 spot product. The lower row is a HILIC chromatogram with glyceraldehyde dimer. As shown, under reversed-phase HILIC conditions, separation of the components of the TLC1 spot product was not confirmed. This is thought to be due to the weak retention of the column, resulting in a fast elution time for the TLC1 spot product. Meanwhile, the retention time of glyceraldehyde dimer was slightly different from that of the TLC1 spot product (synthetic OG). From this, it is inferred that the TLC1 spot product did not contain glyceraldehyde dimer.

[0125] Figure 20 also shows the ESR spectrum of the TLC1 spot sample and peak 2 (Mw = 180) in Figure 9. In Figure 20, the vertical axis represents intensity and the horizontal axis represents magnetic flux density (G). Water was used as the measurement solvent. As shown in the figure, the spectra of the TLC1 spot sample and peak 2 (Mw = 180) component in Figure 9 almost completely overlap, and the peak positions are almost completely identical in both cases. Both the TLC1 spot sample and peak 2 (Mw = 180) component in Figure 9 showed the spectrum of DMPO (spin trap agent) characterized by six lines. This spectral pattern is similar to that of ozonide.

[0126] Figure 21 shows the ESR spectrum of ozonized methyl linolenate. Acetone was used as the measurement solvent. Ozonized methyl linolenate is well known. As shown in the figure, the ESR spectrum of ozonized methyl linolenate shows a spectrum in the presence of DMPO (a spin trapping agent) that features six lines characteristic of ozonides. This spectral pattern is similar to the patterns of the TLC1 spot and peak 2 (Mw = 180) in Figure 20.

[0127] Figure 22 shows the ESR spectrum of peaks 1 to 8 in Figure 9. Water was used as the measurement solvent. The top ESR spectrum is of a blank (solvent only) for comparison. As shown in the figure, it was confirmed that all of the components of peaks 1 to 8 have radical activity.

[0128] The graph in Figure 23 shows the results of measuring the activity of peaks 1 to 8 in Figure 9 by chemiluminescence. In this figure, the vertical axis represents the luminescence intensity (relative intensity) at all wavelengths. The numbers "1" to "8" on the horizontal axis represent the fractions of peaks 1 to 8. The numbers below each number represent the molecular weight of each fraction as confirmed by mass spectrometry. As shown in the figure, it was confirmed that components other than the one with a molecular weight of 180 were produced that showed activity by chemiluminescence.

[0129] <Effect on Thickeners> Previous studies have shown that high-oxidizing power ozone-treated glycerin (OG2000, oxidizing power equivalent to 2,000 ppm in ozone concentration) significantly affects the thickening effect of various thickeners, making it difficult to incorporate into multi-component systems such as cosmetics. Therefore, the present inventors used "Carbopol 980" (manufactured by Lubrizol) or "Carbopol Ultrez 30" (alkyl-modified, manufactured by Lubrizol) as carboxyvinyl polymers (carbomers), which are thickeners commonly used in cosmetics, to study the applicability of low-oxidizing power ozone-treated glycerin (OG200D) and diluted low-oxidizing power ozone-treated glycerin (OG200). The results are shown in Figure 24.

[0130] In FIG. 24 , "3-980," "3-30," "30-980," and "30-30" refer to the following: "3-980": A 3% by mass aqueous solution of the sample (untreated glycerin, high-oxidizing power ozone-treated glycerin (OG2000), or diluted low-oxidizing power ozone-treated glycerin (OG200)) was added with 0.4% by mass of Carbopol 980 and stirred, and finally the pH was adjusted to the recommended value with KOH. "3-30": A 3% by mass aqueous solution of the sample was added with 0.4% by mass of Carbopol Ultrez 30 and stirred, and finally the pH was adjusted to the recommended value with KOH. "30-980": A 30% by mass aqueous solution of the sample was added with 0.4% by mass of Carbopol 980 and stirred, and finally the pH was adjusted to the recommended value with KOH. "30-30": 0.4% by mass of Carbopol Ultrez 30 was added to an aqueous solution containing 30% by mass of the sample, and the solution was stirred, and finally the pH was adjusted to the recommended level with KOH.

[0131] As is clear from Figure 24, untreated glycerin and diluted low-oxidizing-power ozone-treated glycerin (OG200) exhibited almost the same behavior and did not significantly affect the thickening of the carboxyvinyl polymer. However, high-oxidizing-power ozone-treated glycerin (OG2000) exhibited a viscosity-lowering effect even at 3 mass%, and a significant viscosity reduction was observed at 30 mass%. In addition, low-oxidizing-power ozone-treated glycerin (OG200D) exhibited results similar to those of diluted low-oxidizing-power ozone-treated glycerin (OG200).

[0132] Figure 25A shows the results of observing the color tone after 14 days at 50°C in a 30% by weight aqueous solution of the sample, which was prepared in the same manner as in Figure 24, by adding 0.4% by weight of "Carbopol 980" and stirring, and finally adjusting the pH to the recommended level with KOH. Figure 25B shows the results of observing the color tone after 14 days at 50°C in a 30% by weight aqueous solution of the sample, which was prepared in the same manner as in Figure 24, by adding 0.4% by weight of "Carbopol Ultrez 30" and stirring, and finally adjusting the pH to the recommended level with KOH. Figures 25A and 25B show that untreated glycerin and diluted low-oxidizing-power ozone-treated glycerin (OG200) showed almost no coloring (colorless), while the low-oxidizing-power ozone-treated glycerin (OG200D) was slightly yellow, and the high-oxidizing-power ozone-treated glycerin (OG2000) showed yellowing.

[0133] Next, the change in viscosity over time was observed under the same conditions as in Figure 25A. The results are shown in Table 1.

[0134] From the results in Table 1, it can be seen that there was almost no change in viscosity over time for untreated glycerin (30-G) and diluted low-oxidizing-power ozone-treated glycerin (30-OG200). A slight decrease in viscosity over time was observed for low-oxidizing-power ozone-treated glycerin (30-OG200D). On the other hand, a very significant change in viscosity was observed for high-oxidizing-power ozone-treated glycerin (30-OG2000).

[0135] The same study was also carried out on xanthan gum (Keltrol CG LAX-T, manufactured by CP Kelco Inc.). The results are shown in FIG. 26 and Table 2.

[0136]

[0137] Figure 26 shows, from the left, untreated glycerin, high-oxidizing-power ozone-treated glycerin (OG2000), low-oxidizing-power ozone-treated glycerin (OG200D), and diluted low-oxidizing-power ozone-treated glycerin (OG200), each at 30% by mass, with a xanthan gum concentration of 1% by mass. As shown in Figure 26, significant yellowing was observed in the high-oxidizing-power ozone-treated glycerin (OG2000). A slight yellowing was observed in the low-oxidizing-power ozone-treated glycerin (OG200D), while no discoloration was observed in the untreated glycerin or diluted low-oxidizing-power ozone-treated glycerin (OG200). Furthermore, from the results in Table 2, it was observed that the high-oxidizing-power ozone-treated glycerin (30-OG2000) showed a large change in viscosity over time, but the viscosity changes of the untreated glycerin (30-G), the low-oxidizing-power ozone-treated glycerin (30-OG200D), and the diluted low-oxidizing-power ozone-treated glycerin (30-OG200) were within the acceptable range.

[0138] <Filaggrin Expression> The present inventors investigated the effects of diluted low-oxidizing-potency ozone-treated glycerin (OG200) and high-oxidizing-potency ozone-treated glycerin (OG2000) on the expression of filaggrin, a protein produced in epidermal granular cells and involved in skin barrier function. Cells: Keratinocyte cells (HEKn) Culture medium: EpiLife+HKGS (inoculation, treatment) Inoculation amount: 5 x 10 ４ Cells / well (12 wells) Treatment: OG200, OG2000 0.5% by mass Treatment time: 24 hours Cells were inoculated and cultured for 24 hours, then treated, and cultured for another 24 hours. The amount of filaggrin (profilaggrin) produced by the recovered cells was measured by Western blotting. The results are shown in Figure 27.

[0139] From Figure 27, it was confirmed that both diluted low-oxidizing-power ozone-treated glycerin (OG200) and high-oxidizing-power ozone-treated glycerin (OG2000) were effective in inducing filaggrin. Despite being a 10-fold dilution of OG2000, OG200 showed a remarkable effect equal to or greater than that of OG2000. Surprisingly, 0.5% of OG200 was 1 ppm, compared to 10 ppm at 0.5% of OG2000. Furthermore, low-oxidizing-power ozone-treated glycerin (OG200D) showed results similar to those of OG200.

[0140] <CerS1 Expression> The present inventors investigated the effects of diluted low-oxidizing-potency ozone-treated glycerin (OG200), low-oxidizing-potency ozone-treated glycerin (OG200D), and high-oxidizing-potency ozone-treated glycerin (OG2000) on the expression of ceramide synthase 1 (CerS1), a ceramide synthase. Cells: Keratinocyte cells (HEKn) Medium: EpiLife+HKGS (inoculation, treatment) Inoculation amount: 5 x 10 ４ Cells / well (12 wells) Treatment: OG2000, OG200, and OG200D at 0.5% by mass each Treatment time: 24 hours Cells were inoculated and cultured for 24 hours, then treated and cultured for another 24 hours. The amount of CerS1 mRNA in the recovered cells was measured by qPCR. The results are shown in Figures 28 and 29.

[0141] It can be seen from Figure 28 that the expression level of CerS1 in OG200 is about 1.3 times higher than that in OG2000. Also, it can be seen from Figure 29 that the expression level of CerS1 in OG200 is higher than that in OG200D.

[0142] <LC3-II Expression> The present inventors investigated the expression of LC3-II, which is known as a major marker of autophagy. Treatment was performed using diluted low-oxidizing-potency ozone-treated glycerin (OG200) and high-oxidizing-potency ozone-treated glycerin (OG2000) at 0.5% by mass, similar to the filaggrin study described above. The amount of LC3-II mRNA in the recovered cells was measured by qPCR. The results are shown in Figure 30.

[0143] Figure 30 shows that diluted low-oxidizing-power ozone-treated glycerin (OG200) expressed more LC3-II than high-oxidizing-power ozone-treated glycerin (OG2000). Surprisingly, 0.5% by mass of OG200 was 1 ppm, compared with 10 ppm for 0.5% by mass of OG200. Furthermore, low-oxidizing-power ozone-treated glycerin (OG200D) showed similar results to OG200.

[0144] <Involucrin Expression> The present inventors investigated the expression of involucrin, one of the components of the outer cell wall of the stratum corneum. Treatment was performed using diluted low-oxidizing-potency ozone-treated glycerin (OG200) and high-oxidizing-potency ozone-treated glycerin (OG2000) at 0.5% by mass, similar to the filaggrin study described above. The amount of involucrin in the recovered cells was measured by Western blotting. The results are shown in Figure 31.

[0145] 31 shows that the diluted low-oxidizing-power ozone-treated glycerin (OG200) also expressed a higher amount of involucrin than the high-oxidizing-power ozone-treated glycerin (OG2000). Surprisingly, 0.5% by mass of OG200 was 1 ppm, compared to 10 ppm at 0.5% by mass of OG200. The low-oxidizing-power ozone-treated glycerin (OG200D) showed similar results to OG200.

[0146] <Cell viability> The present inventors investigated the effect of diluted low-oxidizing power ozone-treated glycerin (OG200) on viable cells. Cells: keratinocyte cells (HEKn) Medium: EpiLife+HKGS (inoculation, treatment) Inoculation amount: 5 x 10 ３ Cells / well (96 wells) Treatment: Untreated glycerin, diluted low-oxidizing power ozone-treated glycerin (OG200) (0.1 mass%, 0.5 mass%, 1 mass%, 2 mass%, 4 mass%) Treatment time: 72 hours Cells were inoculated and cultured for 24 hours, then treated, and cultured for another 72 hours, after which the cell count was measured. The results are shown in Figure 32.

[0147] As shown in Figure 32, the diluted low-oxidizing-power ozone-treated glycerin (OG200) showed cell viability almost equal to or greater than that of untreated glycerin. Surprisingly, the concentration of OG200 was 0.1% by mass, which was 0.2 ppm. Furthermore, the low-oxidizing-power ozone-treated glycerin (OG200D) showed similar results to OG200.

[0148] <Formulation Examples of Cosmetics> Formulation examples of cosmetics containing the ozone-treated glycerin of the present invention (OG300, OG300D, OG200, OG200D, OG200B, OG200P, OG200PN, OG200PE, OG100, OG100D, OG50, or OG50D) are shown below.

[0149] Formulation Example 1 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG300D: 1.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0150] Formulation Example 2 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG200: 1.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0151] Formulation Example 3 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG200B: 1.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0152] Formulation Example 4 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG200P: 1.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0153] Formulation Example 5 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG100D: 3.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0154] Formulation Example 6 All-in-one gel 1,3-butylene glycol (BG): 10.0% by mass Glycerin: 5.0% by mass Diglycerin: 4.0% by mass OG50: 5.0% by mass Squalane: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0155] Formulation Example 7 All-in-one gel (rich type) OG300: 1.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0156] Formulation Example 8 All-in-one gel (rich type) OG200D: 3.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0157] Formulation Example 9 All-in-one gel (rich type) OG200PN: 3.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0158] Formulation Example 10 All-in-one gel (rich type) OG200PE: 3.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0159] Formulation Example 11 All-in-one gel (rich type) OG100: 5.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0160] Formulation Example 12 All-in-one gel (rich type) OG50D: 5.0% by mass 1,3-butylene glycol (BG): 7.0% by mass Diglycerin: 4.0% by mass Squalane: 1.0% by mass Argan oil: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Dipropylene glycol (DPG): 0.1% by mass Preservative: appropriate amount Purified water: remaining amount total: 100.0% by mass

[0161] Formulation Example 13 - High concentration serum - Purified water: 98.4% by mass OG200: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Total: 100.0% by mass

[0162] Formulation Example 14 - High concentration serum - Purified water: 98.4% by mass OG200D: 1.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Total: 100.0% by mass

[0163] Formulation Example 15 - High concentration serum - Purified water: 96.4% by mass OG100: 3.0% by mass Carbomer: 0.4% by mass Potassium hydroxide: 0.2% by mass Total: 100.0% by mass

[0164] Formulation Example 16 - Lotion - Purified water: 97.9% by mass OG200: 1.0% by mass Hyaluronic acid: 1.0% by mass Xanthan gum: 0.1% by mass Total: 100.0% by mass

[0165] Formulation Example 17 - Lotion - Purified water: 95.9% by mass OG100D: 3.0% by mass Hyaluronic acid: 1.0% by mass Xanthan gum: 0.1% by mass Total: 100.0% by mass

[0166] <Formulation examples of foods and beverages> Formulation examples of foods and beverages containing the ozone-treated glycerin of the present invention (OG300, OG300D, OG200, OG200D, OG200B, OG200P, OG200PN, OG200PE, OG100, OG100D, OG50, or OG50D) are shown below.

[0167] Formulation Example 1 A tablet having the following composition was produced by a conventional method: OG300D: 1.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0168] Formulation Example 2 Tablets having the following composition were produced by a conventional method: OG200: 3.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0169] Formulation Example 3 Tablets having the following composition were produced by a conventional method: OG200B: 3.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0170] Formulation Example 4 A tablet having the following composition was produced by a conventional method: OG200P: 3.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0171] Formulation Example 5 A tablet having the following composition was produced by a conventional method: OG100D: 5.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0172] Formulation Example 6 A tablet having the following composition was produced by a conventional method: OG50D: 7.0 mg Dolomite (containing 20% ​​calcium and 10% magnesium): 83.4 mg Casein phosphopeptide: 16.7 mg Maltitol: 136.8 mg Collagen: 12.7 mg Sucrose fatty acid ester: 12.0 mg

[0173] Formulation Example 7 An oral liquid formulation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG300: 0.5% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0174] Formulation Example 8 An oral liquid formulation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG200D: 1.0% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0175] Formulation Example 9 An oral liquid formulation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG200PN: 1.0% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0176] Formulation Example 10 An oral liquid formulation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG200PE: 1.0% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0177] Formulation Example 11 An oral liquid preparation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG100: 1.5% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0178] Formulation Example 12 An oral liquid preparation having the following composition was produced by a conventional method. <Composition per ampoule (100 mL)> OG50: 2.0% by mass, Sorbitol: 12.0% by mass, Sodium benzoate: 0.1% by mass, Flavoring: 1.0% by mass, Calcium sulfate: 0.5% by mass, Purified water: Remaining amount (100% by mass)

[0179] <Formulation examples of oral compositions> Formulation examples of oral compositions containing the ozone-treated glycerin of the present invention (OG300, OG300D, OG200, OG200D, OG200B, OG200P, OG200PN, OG200PE, OG100, OG100D, OG50, or OG50D) are shown below.

[0180] Formulation Example 1 Toothpaste OG300D 0.5% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0181] Formulation Example 2 Toothpaste OG200 1.0% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0182] Formulation Example 3 Toothpaste OG200B 1.0% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0183] Formulation Example 4 Toothpaste OG200P 1.0% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0184] Formulation Example 5 Toothpaste OG100D 2.0% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0185] Formulation Example 6 Toothpaste OG50 5.0% by mass, anhydrous silicic acid 15.0% by mass, propylene glycol 5.0% by mass, xanthan gum 1.1% by mass, sodium alginate 0.6% by mass, sodium polyacrylate 0.3% by mass, sodium lauroyl methyl taurate 0.4% by mass, isopropyl methyl phenol 0.1% by mass, sodium fluoride 0.3% by mass, methyl parahydroxybenzoate 0.2% by mass, sodium saccharin 0.05% by mass, flavoring 1.5% by mass, appropriate amount of sodium citrate, remaining purified water total 100.00% by mass

[0186] Formulation Example 7 - Mouthwash - OG300 0.5% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

[0187] Formulation Example 8 - Mouthwash - OG200D 1.0% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

[0188] Formulation Example 9 - Mouthwash - OG200PN 1.0% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

[0189] Formulation Example 10 - Mouthwash - OG200PE 1.0% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

[0190] Formulation Example 11 - Mouthwash - OG100 2.0% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

[0191] Formulation Example 12 - Mouthwash - OG50D 5.0% by mass, cetylpyridinium chloride 0.05% by mass, glycerin 5.0% by mass, propylene glycol 5.0% by mass, polyoxyethylene (60) hydrogenated castor oil 1.0% by mass, sucralose 0.05% by mass, saccharin sodium 0.01% by mass, flavoring 0.1% by mass, citric acid 0.05% by mass, sodium citrate 0.2% by mass, purified water remaining total 100.00% by mass

Claims

1. Ozone-treated glycerin, characterized in that the oxidizing power in terms of ozone concentration is 10 ppm to 300 ppm and that it is an ozone oxide obtained by oxidizing glycerin with ozone for one hour or more.

2. Ozone-treated glycerin characterized by being a polyol dilution obtained by diluting high-oxidizing power ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration and an oxidizing power of 1,000 ppm or more in terms of ozone concentration with a polyol.

3. Ozone-treated glycerin characterized by having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, and having at least one of involucrin expression-promoting activity, filaggrin production-promoting activity, LC3-II production-promoting activity, and ceramide production-promoting activity.

4. The ozone-treated glycerin according to claim 1 or 2, which has at least one of an involucrin expression-promoting activity, a filaggrin production-promoting activity, an LC3-II production-promoting activity, and a ceramide production-promoting activity.

5. The ozone-treated glycerin according to claim 1, which is an ozone oxide obtained by oxidizing glycerin with ozone for 1 to 16 hours.

6. The ozone-treated glycerin according to any one of claims 1 to 4, which has an oxidizing power in terms of ozone concentration of 50 ppm to 200 ppm.

7. The ozone-treated glycerin according to claim 2, wherein the polyol is at least one selected from the group consisting of glycerin, butylene glycol, propylene glycol, pentylene glycol, and polyethylene glycol.

8. The ozonated glycerin of claim 7, wherein the polyol is glycerin.

9. A cosmetic preparation containing the ozone-treated glycerin according to any one of claims 1 to 8.

10. A food or drink containing the ozone-treated glycerin according to any one of claims 1 to 8.

11. An oral composition comprising the ozone-treated glycerin according to any one of claims 1 to 8.

12. A method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm in terms of ozone concentration, characterized by subjecting a glycerin solution to gas-liquid contact with an ozone-containing gas for one hour or more.

13. A method for producing ozone-treated glycerin having an oxidizing power of 10 ppm to 300 ppm, calculated as an ozone concentration, comprising oxidizing a glycerin solution with ozone until the oxidizing power of the ozone concentration is 1,000 ppm or more, and diluting the resulting high-oxidizing ozone-treated glycerin with a polyol.

14. The method for producing ozone-treated glycerin according to any one of claims 12 to 13, wherein the glycerin solution has a glycerin concentration of 80% by mass or more.

15. The method for producing ozone-treated glycerin according to claim 12 or 14, wherein the glycerin solution is brought into gas-liquid contact with the ozone-containing gas for 1 to 16 hours.

16. The method for producing ozone-treated glycerin according to any one of claims 12 to 14, wherein the oxidizing power in terms of ozone concentration is 50 ppm to 200 ppm.

17. The method for producing ozone-treated glycerin according to any one of claims 13 to 16, wherein the polyol is at least one selected from the group consisting of glycerin, butylene glycol, propylene glycol, pentylene glycol, and polyethylene glycol.

18. The method for producing ozone-treated glycerin according to claim 17, wherein the polyol is glycerin.

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