Viral infection inhibitor, viral infection inhibitor product, and method for producing viral infection inhibitor product

Abstract

The present invention provides a viral infection inhibitor with excellent ethanol resistance, demonstrating an excellent viral infection inhibition effect (antiviral property) even after contact with an ethanol solution for disinfection. This viral infection inhibitor is characterized by containing a compound having a salt of a sulfo group, an organic acid, and water, wherein a portion of the organic acid is present in an undissolved state in the water at 25˚C. Preferably, the inhibitor is characterized in that the organic acid has a solubility of 20 g / L or less in water at 25˚C.

Description

[Technical Field]

[0001] The present invention relates to a virus infection inhibitor, a virus infection inhibitor product, and a method for producing the virus infection inhibitor product. [Background technology]

[0002] In recent years, in addition to seasonal influenza virus epidemics, the novel coronavirus (COVID-19) has become a global pandemic.

[0003] Furthermore, highly pathogenic avian influenza viruses have mutated and been confirmed to infect humans, and there are also concerns about the SARS virus, which has an extremely high mortality rate, so anxiety about viruses is only increasing.

[0004] To address these problems, Patent Document 1 proposes an agent for inhibiting RNA virus infection, which contains an RNA virus infection-inhibiting compound having at least one of the substituents of a structural formula represented by a specific general formula on the side chain of a linear polymer. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2010 / 147165 publication Summary of the Invention [Problem to be solved by the invention]

[0006] On the other hand, even in the case of antiviral products such as articles whose surfaces have been treated with an RNA virus infection inhibitor or antiviral films containing an RNA virus infection inhibitor, it is common to disinfect the surface of the antiviral product with a disinfectant ethanol solution to remove the virus and prevent viral infection.

[0007] However, when an antiviral product treated with the above-mentioned RNA virus infection inhibitor is disinfected with an ethanol solution for disinfection, there is a problem in that the antiviral activity of the RNA virus infection inhibitor is reduced.

[0008] The present invention provides a virus infection inhibitor with excellent ethanol resistance that exhibits excellent virus infection inhibitory effects (antiviral properties) even after contact with a disinfectant ethanol solution (ethanol: 80% by mass, water: 20% by mass), as well as a virus infection inhibitor product using this virus infection inhibitor and a method for producing the same. [Means for solving the problem]

[0009] The viral infection inhibitor of the present invention comprises a compound having a salt of a sulfo group, an organic acid, and water, and is characterized in that a portion of the organic acid is present in an insoluble state in the water at 25°C.

[0010] The water-based paint of the present invention is characterized by containing the above-mentioned virus infection inhibitor.

[0011] The viral infection prevention product of the present invention comprises: The composition is characterized by comprising a substrate and a dried product of the virus infection inhibitor contained on the surface of the substrate.

[0012] The method for producing a virus infection-preventing product of the present invention is characterized by comprising the steps of adhering the virus infection inhibitor to the surface of a substrate and drying the virus infection inhibitor adhered to the surface of the substrate to produce a dried product. [Effects of the Invention]

[0013] The viral infection inhibitor of the present invention contains a compound having a salt of a sulfo group and an organic acid, and therefore has an excellent viral infection inhibitory effect against both enveloped and non-enveloped viruses, and exhibits a viral infection inhibitory effect against various types of viruses.

[0014] The viral infection inhibitor of the present invention has excellent ethanol resistance, retaining excellent viral infection inhibitory effect (antiviral activity) even after contact with an ethanol solution for disinfection, and maintains its viral infection inhibitory effect against various types of viruses for a long period of time. DETAILED DESCRIPTION OF THE INVENTION

[0015] The viral infection inhibitor of the present invention comprises a compound having a salt of a sulfo group, an organic acid, and water, with a portion of the organic acid being insoluble in water.

[0016] [Compounds containing sulfo group salts] A compound having a salt of a sulfo group has a salt of a sulfo group (-SO3H) in the molecule. A compound having a salt of a sulfo group (-SO3X: ​​X is a metal element or NH4 + The compound exhibits a viral infection-inhibiting effect due to the molecular structure containing the sulfo group salt. The compound having a sulfo group salt has an excellent viral infection-inhibiting effect, particularly against enveloped viruses. The compound having a sulfo group salt may also have a carboxy group (-COOH), a phosphonic acid group [-P(=O)(OH)2], a phosphate group [-OPO(OH)2], a thiol group (-SH), and a hydroxy group (-OH).

[0017] The salt of the sulfo group is not particularly limited, and examples thereof include sodium salt (-SO3Na), calcium salt [(-SO3 - )2Ca 2+ ], ammonium salt (-SO3 - NH4 + ), magnesium salt [(-SO3 - )2Mg 2+ ], barium salts [(-SO3 - )2Ba 2+ and the like, with the sodium salt (-SO3Na) being preferred.

[0018] The compound having a salt of a sulfo group is preferably an organic compound. In the present invention, the organic compound refers to a compound containing at least one carbon atom (preferably two or more) and a carbon-hydrogen bond (C—H bond) in the molecule.

[0019] When the compound having a salt of a sulfo group is an organic compound, its affinity with the organic acid described below is improved, the compound having a salt of a sulfo group and the organic acid become closer, the interaction between the compound having a salt of a sulfo group and the organic acid is improved, and the viral infection-inhibiting effect against both non-enveloped viruses and enveloped viruses is improved.

[0020] The compound having a sulfo group salt preferably has an aromatic ring. When the compound having a sulfo group salt has an aromatic ring, the affinity with the organic acid is improved, the compound having a sulfo group salt and the organic acid are brought closer together, the interaction between the compound having a sulfo group salt and the organic acid is improved, and the viral infection-inhibiting effect against both enveloped viruses and non-enveloped viruses is improved.

[0021] The aromatic ring may be a monocyclic aromatic ring, or may be a condensed aromatic ring formed by combining monocyclic aromatic rings. The aromatic ring is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, biphenyl, and phenoxyphenyl, with a benzene ring and a naphthalene ring being preferred. The aromatic ring has one or more hydrogen atoms removed from either the aromatic ring or the condensed aromatic ring, and is bonded to other atoms via a covalent bond.

[0022] In the compound having a sulfo group salt, the sulfo group salt is preferably directly or indirectly bonded to an aromatic ring, more preferably directly bonded to the aromatic ring. The affinity between the aromatic ring of the compound having a sulfo group salt and the organic acid brings the compound having a sulfo group salt and the organic acid closer, thereby improving the synergistic effect between the sulfo group salt of the compound having a sulfo group salt and the organic acid, and thereby improving the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses.

[0023] In a compound having a salt of a sulfo group, when the salt of the sulfo group is indirectly bonded to an aromatic ring, the salt of the sulfo group is preferably bonded to the aromatic ring via an alkylene group (preferably a methylene group or an ethylene group) having 1 to 4 carbon atoms. While maintaining the affinity between the aromatic ring in the compound having a salt of a sulfo group and the organic acid, the alkylene group causes the salt of the sulfo group to be appropriately spaced from the aromatic ring, allowing the salt of the sulfo group to be oriented in a more exposed state, and the virus infection inhibitor exhibits an excellent virus infection inhibitory effect.

[0024] In the present invention, an alkylene group refers to a divalent atomic group generated by removing (abtracting) one hydrogen atom bonded to each of two different carbon atoms in an aliphatic saturated hydrocarbon, and includes both linear and branched atomic groups.

[0025] Examples of alkylene groups include methylene groups (-CH2-), ethylene groups (-CH2-CH2-), propylene groups [-CH(CH3)-CH2-], trimethylene groups [-CH2-CH2-CH2-], butylene groups, amylene groups [-(CH2)5-], and hexylene groups.

[0026] The compound having a salt of a sulfo group is not particularly limited as long as it has one or more salts of a sulfo group in the molecule, and examples thereof include linear alkylbenzene sulfonates, α-olefin sulfonates, alkyl diphenyl ether sulfonates, polyoxyalkylene alkyl ether sulfates, and polymers having a salt of a sulfo group in the side chain of a linear polymer.

[0027] Examples of linear alkylbenzenesulfonates include sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, ammonium dodecylbenzenesulfonate, magnesium dodecylbenzenesulfonate, barium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, ammonium tridecylbenzenesulfonate, sodium tetradecylbenzenesulfonate, and ammonium tetradecylbenzenesulfonate, with sodium dodecylbenzenesulfonate being preferred.

[0028] In the present invention, an alkyl group is a monovalent atomic group remaining after removing one hydrogen atom from an aliphatic saturated hydrocarbon.

[0029] The number of carbon atoms in the alkyl group of the linear alkylbenzenesulfonate is preferably 10 or more, more preferably 11 or more, and still more preferably 12 or more. The number of carbon atoms in the alkyl group of the linear alkylbenzenesulfonate is preferably 25 or less, more preferably 20 or less, and still more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the affinity between the hydrophobic portion derived from the alkyl group and the organic acid brings the compound having a salt of a sulfo group closer to the organic acid, thereby improving the synergistic effect between the sulfo salt of the compound having a salt of a sulfo group and the organic acid, and thereby improving the viral infection-inhibiting effect against both enveloped and non-enveloped viruses.

[0030] Examples of α-olefin sulfonates include C12 to C18 sodium olefin sulfonate, C12 to C18 calcium olefin sulfonate, C12 to C18 ammonium olefin sulfonate, C12 to C18 magnesium olefin sulfonate, and C12 to C18 barium olefin sulfonate, with C14 sodium tetradecene sulfonate being preferred.

[0031] The number of carbon atoms in the α-olefin of the α-olefin sulfonate is preferably 12 or more, and more preferably 14 or more. The number of carbon atoms in the α-olefin of the α-olefin sulfonate is preferably 22 or less, and more preferably 18 or less. When the number of carbon atoms in the α-olefin is within the above range, the affinity between the organic acid and the hydrophobic portion derived from the α-olefin chain of the compound having a salt of a sulfo group brings the compound having a salt of a sulfo group and the organic acid closer together, thereby improving the synergistic effect between the sulfo salt of the compound having a salt of a sulfo group and the organic acid, and thereby improving the viral infection-inhibiting effect against both enveloped and non-enveloped viruses.

[0032] Examples of alkyl diphenyl ether sulfonates include sodium salts, calcium salts, ammonium salts, magnesium salts and barium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, with sodium dodecyl diphenyl ether sulfonate having an alkyl group of C12 being preferred.

[0033] The number of carbon atoms in the alkyl group of the alkyl diphenyl ether sulfonate is preferably 8 or more, and more preferably 10 or more. The number of carbon atoms in the alkyl group of the alkyl diphenyl ether sulfonate is preferably 24 or less, and more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the affinity between the organic acid and the hydrophobic portion derived from the alkyl group of the compound having a salt of a sulfo group brings the compound having a salt of a sulfo group and the organic acid closer together, thereby improving the synergistic effect between the sulfo salt of the compound having a salt of a sulfo group and the organic acid, and thereby improving the viral infection-inhibiting effect against both enveloped and non-enveloped viruses.

[0034] In the polymer having a salt of a sulfo group in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers, polyesters, and polyurethanes are preferred, with vinyl polymers being preferred.

[0035] The polymer having a salt of a sulfo group in the side chain of a linear polymer is not particularly limited, and examples thereof include a polymer containing a styrene sulfonate component, a styrene sulfonate homopolymer, a styrene-styrene sulfonate copolymer, a sulfonate of a compound obtained by sulfonating the benzene ring of polystyrene, and a sulfonate of a compound obtained by sulfonating the benzene ring of a polymer containing a styrene component.

[0036] Furthermore, the polymer having a sulfo group salt in the side chain of the linear polymer is preferably a homopolymer or copolymer of a monomer having a sulfo group salt. Examples of the monomer having a sulfo group salt include sodium p-styrenesulfonate, sodium m-styrenesulfonate, sodium o-styrenesulfonate, calcium p-styrenesulfonate, calcium m-styrenesulfonate, calcium o-styrenesulfonate, ammonium p-styrenesulfonate, ammonium m-styrenesulfonate, ammonium o-styrenesulfonate, sodium naphthalenesulfonate, and calcium naphthalenesulfonate. Sodium styrenesulfonate is preferred, and sodium p-styrenesulfonate is more preferred because it has less steric hindrance in reactivity with viruses.

[0037] The monomer having a salt of a sulfo group may form a copolymer with another monomer. Examples of copolymerizable monomers include alkyl acrylate, alkyl methacrylate, vinyl alkyl ether, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, acrylic acid, sodium acrylate, methacrylic acid, maleic acid, fumaric acid, maleic anhydride, acrylamide, methacrylamide, diacetone acrylamide, vinyl toluene, xylene sulfonic acid, vinyl pyridine, vinyl sulfonic acid, vinyl alcohol, methyl methacrylate, sodium methacrylate, and hydroxyethyl methacrylate, with styrene being preferred.

[0038] A polymer having a salt of a sulfo group in the side chain of a linear polymer can be produced by a general method, such as a method of radically polymerizing a monomer having a salt of a sulfo group, a method of radically polymerizing a monomer having a salt of a sulfo group and a monomer copolymerizable with this monomer, or a method of neutralizing the sulfo group of a polymer containing a monomer component having a sulfo group with an alkali (e.g., sodium hydroxide, calcium hydroxide, potassium hydroxide, ammonium hydroxide, etc.).

[0039] In the viral infection inhibitor, the content of the compound having a sulfo group salt is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 3 parts by mass or more, relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water. When the content of the sulfo group salt is 0.1 parts by mass or more, the synergistic effect with the organic acid can further improve the viral infection inhibitory effect against enveloped viruses and non-enveloped viruses. There are no particular limitations on the upper limit of the content of the compound having a sulfo group salt, but from the viewpoint of the production cost of the viral infection inhibitor, it is preferably 50 parts by mass or less relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water.

[0040] [Organic acid] The viral infection inhibitor contains an organic acid, which promotes the release of a salt of a sulfo group in a compound having a salt of a sulfo group, thereby improving the viral infection inhibitory effect against non-enveloped viruses, and thereby improving the viral infection inhibitory effect against enveloped viruses and non-enveloped viruses.

[0041] Furthermore, compounds having a salt of a sulfo group can weaken the capsid (protein shell) of non-enveloped viruses, thereby improving the inhibitory effect of organic acids on viral infection with non-enveloped viruses.

[0042] In this way, the viral infection inhibitor contains a compound having a salt of a sulfo group and an organic acid, thereby improving the viral infection inhibitory effect against enveloped viruses and non-enveloped viruses.

[0043] The organic acid may be any organic compound capable of promoting the release of some or all of the salts of sulfo groups in a compound having a salt of a sulfo group, and may be a polymer. The organic acid has a carboxy group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2], or a phosphate group [-OPO(OH)2] in the molecule, and may have only one of these functional groups or multiple types of functional groups. The organic acid preferably has a carboxy group, since this can more effectively maintain or promote the release of some or all of the salts of sulfo groups in a compound having a salt of a sulfo group, thereby further improving the viral infection inhibitory effect against enveloped and non-enveloped viruses.

[0044] The organic acid preferably has a plurality of functional groups selected from the group consisting of a carboxy group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2], and a phosphate group [-OPO(OH)2] in the molecule, more preferably a carboxy group among the plurality of functional groups, and even more preferably a plurality of carboxy groups. When the organic acid has a plurality of the above functional groups, it is possible to more reliably maintain or promote the release of some or all of the salts of the sulfo groups in the compound having a salt of the sulfo group, thereby further improving the viral infection inhibitory effect against enveloped and non-enveloped viruses. It is preferable that the organic acid does not contain a salt of the sulfo group in the molecule.

[0045] The organic acid is not particularly limited as long as it has a carboxy group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphate group [-OPO(OH)2] in the molecule, and examples thereof include adipic acid (solubility: 14 g / L), benzoic acid (solubility: 3.4 g / L), lauric acid (solubility: 0 g / L), azelaic acid (solubility: 2.4 g / L), sebacic acid (solubility: 0.25 g / L), and dodecanedioic acid (solubility: 0 g / L). ), fumaric acid (solubility: 6.3 g / L), phthalic acid (solubility: 7.2 g / L), isophthalic acid (solubility: 0.13 g / L), terephthalic acid (solubility: 0.017 g / L), methylenedisalicylic acid (solubility: 0 g / L), cis-Δ4-tetrahydrophthalic acid (solubility: 0 g / L), caproic acid (solubility: 11 g / L), enanthic acid (solubility: 2.4 g / L), caprylic acid (solubility: 0.68 g / L), pelargonic acid (solubility: 0.28 g / L) ), capric acid (solubility: 0.15 g / L), lauric acid (solubility: 0.0048 g / L), myristic acid (solubility: 0 g / L), palmitic acid (solubility: 0 g / L), stearic acid (solubility: 0 g / L), myristoleic acid (solubility: 0 g / L), oleic acid (solubility: 0 g / L), ricinoleic acid (solubility: 0 g / L), salicylic acid (solubility: 2.0 g / L), gallic acid hydrate (solubility: 11 g / L), benzilic acid (solubility: 1.4 g / L) ), 4-aminobenzoic acid (solubility: 6 g / L), triglycolaminic acid (solubility: 1.3 g / L), polyacrylic acid (solubility: 250 g / L or more), 1,3-propanediaminetetraacetic acid (solubility: 9 g / L), diethylenetriaminepentaacetic acid (solubility: 4 g / L), etc. are examples of organic acids, with adipic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, triglycolaminic acid, 1,3-propanediaminetetraacetic acid, and diethylenetriaminepentaacetic acid being preferred. The solubilities listed in parentheses are the solubility of the organic acid in water at 25°C. The organic acids may be used alone or in combination of two or more.

[0046] When the organic acid is a polymer, examples of the organic acid include a linear polymer having a carboxyl group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)], or a phosphate group [-OPO(OH)] on the side chain.

[0047] In the case of a polymer having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphate group [-OPO(OH)] in its side chain, the linear polymer is not particularly limited, and for example, vinyl polymer, polyester, or polyurethane is preferred, with vinyl polymer being more preferred.

[0048] The polymer having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphate group [-OPO(OH)] in the side chain of the linear polymer is not particularly limited, and examples thereof include a polymer containing a monomer component having a carboxy group, a polymer containing a monomer component having a sulfo group, a polymer containing a monomer component having a phosphonic acid group [-P(=O)(OH)], and a polymer containing a monomer component having a phosphate group [-OPO(OH)].

[0049] Examples of the monomer having a carboxy group include acrylic acid, methacrylic acid, acrylic acid, methacrylic acid, β-carboxyethyl (meth)acrylate, 5-carboxypentyl (meth)acrylate, succinic acid mono(meth)acryloyloxyethyl ester, ω-carboxypolycaprolactone mono(meth)acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and carboxybetaine type monomers, with acrylic acid and methacrylic acid being preferred. The monomer having a carboxy group may be used alone or in combination of two or more.

[0050] Examples of the monomer having a sulfo group include p-styrenesulfonic acid, m-styrenesulfonic acid, o-styrenesulfonic acid, acrylamido-t-butylsulfonic acid, vinylsulfonic acid, 2-(methacryloyloxy)ethanesulfonic acid, 3-(methacryloyloxy)propanesulfonic acid, 4-[(3-methacrylamidopropyl)dimethylammonio]butane-1-sulfonic acid, etc. The monomer having a sulfo group may be used alone or in combination of two or more kinds.

[0051] Examples of the monomer having a phosphonic acid group include vinylphosphonic acid, alkyl vinylphosphonate, etc. The monomer having a phosphonic acid group may be used alone or in combination of two or more kinds.

[0052] Examples of the monomer having a phosphoric acid group include monoacrylate phosphoric acid, diacrylate phosphoric acid, monomethacrylate phosphoric acid, dimethacrylate phosphoric acid, 2-hydroxyethyl methacrylic acid phosphoric acid, etc. The monomer having a phosphoric acid group may be used alone or in combination of two or more kinds.

[0053] When the organic acid is a polymer, the total content of monomer components having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphate group [-OPO(OH)] in the polymer is preferably 50% by mass or more, more preferably 60% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, more preferably 90% by mass or more, more preferably 95% by mass or more, more preferably 99% by mass or more, and more preferably 100% by mass.

[0054] A polymer having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphate group [-OPO(OH)] in the side chain of a linear polymer may contain a monomer component copolymerizable with a monomer having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphate group [-OPO(OH)].

[0055] Examples of the copolymerizable monomer include alkyl acrylate, alkyl methacrylate, vinyl alkyl ether, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, sodium acrylate, acrylamide, methacrylamide, diacetone acrylamide, vinyl toluene, vinyl pyridine, methyl methacrylate, sodium methacrylate, and hydroxyethyl methacrylate.

[0056] Linear polymers having a carboxyl group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2], or a phosphoric acid group [-OPO(OH)2] in the side chain can be produced by a general-purpose radical polymerization method.

[0057] In the virus infection inhibitor, a portion of the organic acid is not dissolved in water and exists in an insoluble state at 25° C. That is, in the virus infection inhibitor, a portion of the organic acid is dissolved in water at 25° C., while a portion of the organic acid is not dissolved in water and exists in an insoluble state in water. At 25° C., a portion of the organic acid precipitates in water.

[0058] The viral infection inhibitor exhibits an excellent viral infection inhibitory effect due to the interaction between the compound having a sulfo group salt and the organic acid. When used, the viral infection inhibitor is used in the form of a dried product produced by drying and removing water. If all of the organic acid in the viral infection inhibitor is dissolved, the compound having a sulfo group salt and the organic acid are likely to precipitate separately during the drying process of drying and removing water, which may result in a weakened interaction between the compound having a sulfo group salt and the organic acid.

[0059] Therefore, in the virus infection inhibitor, a portion of the organic acid is left in an insoluble state (precipitated state) in water, and the compound having a salt of a sulfo group that precipitates during the drying process of the water in the virus infection inhibitor is made to easily adhere to the surface of the insoluble (precipitated) organic acid, thereby more effectively expressing the interaction between the compound having a salt of a sulfo group and the organic acid, and thereby achieving excellent virus infection inhibitory effects even after contact with a disinfectant ethanol solution.

[0060] Furthermore, since the water-insoluble organic acid (organic acid precipitated in water) is a foreign substance in the virus infection inhibitor containing water, it is gradually pushed out to the surface of the dried product produced during the drying process of the virus infection inhibitor, and as a result, it tends to be present on the surface of the dried product produced by drying the virus infection inhibitor. As a result, the compound having a sulfo group salt and the organic acid, which are in a state where they can interact more effectively, are concentrated on the surface of the dried product, and the dried product exhibits excellent virus infection inhibitory effects even after contact with a disinfectant ethanol solution.

[0061] Furthermore, the virus infection inhibitor has a portion of the organic acid dissolved in water. In this way, by dissolving a portion of the organic acid in water, during the drying process of the virus infection inhibitor, the organic acid can be precipitated from the water with excellent adhesion to the substrate to which the dried product of the virus infection inhibitor is attached. Therefore, the dried product produced by drying the virus infection inhibitor exhibits excellent adhesion to the substrate and is firmly integrated with the surface of the substrate, and can stably impart an excellent virus infection inhibitory effect to the substrate for a long period of time, even if it comes into contact with a disinfectant ethanol solution.

[0062] In the virus infection inhibitor, a part of the organic acid is present in an insoluble state in water, and therefore the virus infection inhibitor usually appears cloudy.

[0063] The solubility of an organic acid in water at 25°C (solubility in water at 25°C) is preferably 20 g / L or less, more preferably 18 g / L or less. When the solubility of an organic acid in water at 25°C is 20 g / L or less, the affinity between the compound having a sulfo group salt and the organic acid is improved, the compound having a sulfo group salt and the organic acid become closer, and the synergistic effect between the sulfo group salt of the compound having a sulfo group salt and the organic acid can be improved, resulting in an improved viral infection inhibitory effect against both enveloped and non-enveloped viruses. The solubility of an organic acid in water at 25°C refers to the mass of the organic acid dissolved in 1 L of water. In other words, the solubility of an organic acid in water at 25°C refers to the mass of the organic acid in a saturated solution (25°C) containing 1 L of water.

[0064] The solubility of the organic acid in water at 25° C. is preferably 0.1 g / L or more, and more preferably 1 g / L or more. When the organic acid has a solubility in water at 25° C. of 0.1 g / L or more, the release of the salt of the sulfo group in the compound having the salt of the sulfo group is promoted when the organic acid comes into contact with an aqueous protein solution containing viruses, such as saliva or sputum, thereby improving the effect of inhibiting viral infection with non-enveloped viruses.

[0065] The solubility of organic acids in water at 25°C is the value measured at 25°C in accordance with OECD Chemicals Testing Guideline No. 105 (Water Solubility).

[0066] The organic acid preferably has a pKa1 of 4.6 or less, and more preferably 3.8 or less, at 25° C. When the organic acid has a pKa1 of 4.6 or less at 25° C., the synergistic effect of the sulfo group salt and the organic acid improves the viral infection inhibitory effect against enveloped viruses, and when the pKa1 is 3.8 or less, the release of the sulfo group salt is further promoted, causing protein denaturation by protons, improving the viral infection inhibitory effect against not only enveloped viruses but also non-enveloped viruses.

[0067] Here, in the present invention, the electrolyte HA is A - and H+ When an acid dissociates into ions and the ionization equilibrium is obtained as shown in equation (1), the acid dissociation constant Ka is defined by equation (2), and pKa is defined as the common logarithm (3) of the reciprocal of the acid dissociation constant Ka.

[0068] When the organic acid is a polyvalent acid, the polyvalent acid undergoes ionization in multiple stages, and pKa1 refers to the pKa calculated based on the ionization constant of the first stage.

[0069]

number

[0070] The pKa1 of an organic acid at 25°C is a value measured by titration. Specifically, the pKa1 can be determined by titrating the organic acid with sodium hydroxide at 25°C and measuring the pH at 25°C at the half-equivalent point (the point at which half the amount required to complete neutralization has been added dropwise).

[0071] When the organic acid is a polymer, the organic acid preferably includes a crosslinked polymer. A portion of the organic acid can be present in the virus infection inhibitor in a water-insoluble state, and the dried product produced from the virus infection inhibitor can maintain excellent virus infection inhibitory effect even after contact with a disinfectant ethanol solution.

[0072] The method for crosslinking a polymer is not particularly limited and may be carried out in a commonly used manner. Examples of the method for crosslinking a polymer include (1) a method in which a monomer is polymerized to obtain a polymer, and then a crosslinking aid and a peroxide are supplied to the polymer and heated to crosslink the polymer, and (2) a method in which a monomer is polymerized to obtain a polymer, and then a crosslinking agent is supplied to the polymer and heated to crosslink the polymer.

[0073] The crosslinking aid is not particularly limited, and examples thereof include divinylbenzene, trimethylolpropane trimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, trimellitic acid triallyl ester, triallyl isocyanurate, ethylvinylbenzene, neopentyl glycol dimethacrylate, 1,2,4-benzene tris-triallyl ester, 1,6-hexanediol dimethacrylate, lauryl methacrylate, stearyl methacrylate, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, etc. The crosslinking aids may be used alone or in combination of two or more.

[0074] The peroxide is not particularly limited, and examples thereof include 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, t-butyl perbenzoate, cumyl hydroperoxide, t-butyl hydroperoxide, 1,1-di(t-butylperoxy)-3,3,5-trimethylhexane, n-butyl-4,4-di(t-butylperoxy)valerate, α,α'-bis(t-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, t-butylperoxycumene, etc. The peroxides may be used alone or in combination of two or more.

[0075] The crosslinking agent is not particularly limited, and a general-purpose crosslinking agent can be used, for example, an epoxy-based crosslinking agent, an isocyanate-based crosslinking agent, an imine-based crosslinking agent, etc. The crosslinking agents may be used alone or in combination of two or more.

[0076] Examples of the isocyanate crosslinking agent include tolylene diisocyanate, naphthylene-1,5-diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, and trimethylolpropane-modified tolylene diisocyanate.

[0077] Preferred examples of epoxy crosslinking agents include N,N'-(cyclohexane-1,3-diylbismethylene)bis(diglycidylamine) and N,N,N',N'-tetraglycidyl-1,3-benzenedi(methanamine).

[0078] When the organic acid contains a crosslinked polymer, the gel fraction of the organic acid is preferably 65% ​​by mass or more, more preferably 70% by mass or more, and more preferably 75% by mass or more. The gel fraction of the organic acid is preferably 99% by mass or less, more preferably 97% by mass or less, and even more preferably 96% by mass or less. When the gel fraction of the organic acid is 65% by mass or more, a portion of the organic acid can be more reliably insoluble in water, and the dried product of the virus infection inhibitor can maintain its excellent virus infection inhibitory effect even after contact with a disinfectant ethanol solution. Moreover, since the crosslinked structure is imparted to the polymer, the crosslinked portion of the polymer is insoluble in the ethanol solution, while the non-crosslinked portion of the polymer can freely move, thereby efficiently adsorbing viruses and thereby exhibiting an excellent virus infection inhibitory effect even after contact with a disinfectant ethanol solution. When the gel fraction of the organic acid is 99% by mass or less, the adhesion of the dried product of the virus infection inhibitor to the substrate can be improved by dissolving a portion of the organic acid in water, and the excellent virus infection inhibitory effect imparted to the substrate can be stably maintained even after contact with a disinfectant ethanol solution.

[0079] The gel fraction of an organic acid is a value measured as follows: The organic acid is weighed in Ag, immersed in purified water at 60°C for 24 hours, the insoluble matter is filtered through a 200-mesh wire screen, the residue on the screen is vacuum-dried at 80°C for 16 hours, the weight of the dried residue is measured (Bg), and the gel fraction of the organic acid is calculated using the following formula: Gel fraction of organic acid (mass%) = (B / A) × 100

[0080] When the organic acid is a polymer, the weight-average molecular weight of the organic acid is preferably at least 3000, preferably at least 5000, more preferably at least 10000, and even more preferably at least 100000. When the weight-average molecular weight of the organic acid is 3000 or more, the number of adsorption points with viruses per molecule of the organic acid increases, the interaction between the organic acid and viruses becomes stronger, and the viral infection inhibitory effect of the viral infection inhibitor can be improved.

[0081] The weight-average molecular weight of the organic acid is preferably not more than 1,000,000, more preferably not more than 900,000, more preferably not more than 800,000, and even more preferably not more than 500,000. When the weight-average molecular weight of the organic acid is 1,000,000 or less, the aggregation tendency of the insoluble portion of the organic acid is reduced, resulting in a form that facilitates interaction between the organic acid and viruses, and improving the viral infection inhibitory effect of the viral infection inhibitor.

[0082] In the present invention, the weight average molecular weight of a polymer is a value measured by GPC (gel permeation chromatography) and converted into polystyrene. When the polymer is crosslinked, the weight average molecular weight of the polymer refers to the weight average molecular weight of the polymer before crosslinking.

[0083] For example, the measurement can be performed using the following measurement device and under the following measurement conditions. Gel permeation chromatograph: Waters, product name "2690 Separations Model" Column: Showa Denko Co., Ltd., product name "GPC KF-806L" Detector: differential refractometer Sample flow rate: 1 mL / min Column temperature: 40℃ Eluent: THF

[0084] The organic acid is preferably solid at 1 atmosphere (1013.25 hPa) and 25° C. If the organic acid is solid at 1 atmosphere and 25° C., it will be more likely to appear on the surface of the virus infection-preventing product, such as a processed coating film, and will be more likely to come into contact with viruses, improving the virus infection-preventing effect.

[0085] In the viral infection inhibitor, the content of the organic acid is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more, relative to 100 parts by mass of the total amount of the compound having a salt of a sulfo group, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water. When the content of the organic acid is 5 parts by mass or more, a portion of the organic acid is more likely to exist in an insoluble state, and the viral infection inhibitory effect against enveloped viruses and non-enveloped viruses can be further improved.

[0086] In the viral infection inhibitor, the upper limit of the content of the organic acid is not particularly limited, but from the viewpoint of the production cost of the viral infection inhibitor, it is preferably 70 parts by mass or less per 100 parts by mass of the total amount of the compound having a salt of a sulfo group, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water.

[0087] In the viral infection inhibitor, the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (organic acid dissolved in water and organic acid insoluble in water) (content of compound having a sulfo group salt / content of organic acid) is preferably 0.01 or more, more preferably 0.02 or more, more preferably 0.10 or more, and even more preferably 0.15 or more. In the viral infection inhibitor, the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (organic acid dissolved in water and organic acid insoluble in water) (content of compound having a sulfo group salt / content of organic acid) is preferably 1.7 or less, more preferably 1.6 or less, and even more preferably 1.55 or less. When the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (content of compound having a sulfo group salt / content of organic acid) is 0.01 or more, virus adsorption by the sulfo group generated by liberating the sulfo group salt in the compound having a sulfo group salt is promoted, and an excellent viral infection inhibitory effect is exhibited. When the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (content of the compound having a salt of a sulfo group / content of the organic acid) is 1.7 or less, the action of the compound having a salt of a sulfo group dissolved in water and the organic acid dissolved in water further improves the adhesion between the water-insoluble organic acid and the substrate, making it difficult for the dried product of the virus infection inhibitor to peel off from the substrate, and enabling the excellent virus infection inhibitory effect imparted to the substrate to be stably maintained even after contact with a disinfectant ethanol solution.

[0088] In the viral infection inhibitor, the water content is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, and even more preferably 80 parts by mass or less, relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water. When the water content is 95 parts by mass or less, a portion of the organic acid is more likely to exist in an insoluble state, thereby further improving the viral infection inhibitory effect against enveloped viruses and non-enveloped viruses. There is no particular limitation on the lower limit of the water content, but from the viewpoint of the production cost of the viral infection inhibitor, it is preferably 30 parts by mass or more relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (organic acid dissolved in water and organic acid insoluble in water), and water.

[0089] [Other ingredients] The virus infection inhibitor may contain additives such as dispersants, thickeners, antioxidants, and ultraviolet absorbers within limits that do not impair its physical properties.

[0090] Examples of dispersants include anionic surfactants (excluding compounds having a salt of a sulfo group in the molecule), cationic surfactants, nonionic surfactants, and amphoteric surfactants (excluding compounds having a salt of a sulfo group in the molecule). Anionic surfactants (excluding compounds having a salt of a sulfo group in the molecule) are preferred as dispersants because they improve the dispersibility of organic acids that are insoluble in water.

[0091] Examples of anionic surfactants (excluding compounds having a salt of a sulfo group in the molecule) include alkyl sulfate ester salts, alkyl ethoxy sulfate ester salts, and phosphate ester salts.

[0092] Cationic surfactants include, for example, fatty amine salts, quaternary ammonium salts, alkylpyridinium salts, and the like.

[0093] Examples of nonionic surfactants include polyoxyalkylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters (e.g., polyethylene glycol distearate, etc.), polyoxyethylene distyrenated phenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, fatty acid alkanolamides (e.g., coconut fatty acid dimethanolamide, coconut fatty acid diethanolamide, coconut fatty acid dipropanolamide, and other coconut fatty acid alkanolamides), fatty acid alkylolamides, alkylalkanolamides, acetylene glycol, oxyethylene adducts of acetylene glycol, and polyethylene glycol polypropylene glycol block copolymers.

[0094] Examples of amphoteric surfactants (excluding compounds having a salt of a sulfo group in the molecule) include tertiary amine oxides, betaines, and alkyl betaines.

[0095] The thickener may be a natural polymer compound or a synthetic polymer compound. Examples of natural polymer compounds include pectin, gelatin, carrageenan, xanthan gum, gum arabic, glucomannan, gellan gum, and alginic acid. Examples of synthetic polymer compounds include polyethylene glycol and polyvinyl alcohol.

[0096] [Virus infection inhibitor] The virus infection inhibitor contains a water-insoluble component (precipitated component). In the virus infection inhibitor, the insoluble component is almost entirely composed of organic acids that are insoluble in water. A portion of the water-insoluble component (precipitated component) may contain components other than organic acids.

[0097] At 25°C, the content of insoluble matter in the virus infection inhibitor is preferably 1 part by mass or more, more preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more, relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (the organic acid dissolved in water and the organic acid insoluble in water), and water. When the content of insoluble matter is 1 part by mass or more, the interaction between the compound having a sulfo group salt and the organic acid is improved, thereby allowing the dried product of the virus infection inhibitor to maintain its excellent virus infection inhibitory effect even after contact with a disinfectant ethanol solution. The upper limit of the content of insoluble matter in the virus infection inhibitor at 25°C is not particularly limited, but from the viewpoint of coatability, it is preferably 70 parts by mass or less, relative to 100 parts by mass of the total amount of the compound having a sulfo group salt, the organic acid (the organic acid dissolved in water and the organic acid insoluble in water), and water.

[0098] At 25°C, the content of the organic acid in the insoluble matter of the virus infection inhibitor is preferably 10% by mass or more, more preferably 20% by mass or more, more preferably 30% by mass or more, more preferably 40% by mass or more, more preferably 50% by mass or more, more preferably 60% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, more preferably 90% by mass or more, more preferably 95% by mass or more, more preferably 98% by mass or more, more preferably 99% by mass or more, and more preferably 100% by mass. When the content of the organic acid is 10% by mass or more, the interaction between the compound having a sulfo group salt and the organic acid is improved, so that the dried product of the virus infection inhibitor can maintain its excellent virus infection inhibitory effect even after contact with a disinfectant ethanol solution. At 25°C, the upper limit of the content of the organic acid in the insoluble matter of the virus infection inhibitor is not particularly limited.

[0099] The content of insoluble matter in the virus infection inhibitor at 25°C is measured as follows. First, the mass of only the Type 5C filter paper conforming to JIS P3801 is measured. Next, 100 g of the virus infection inhibitor is suction filtered through the filter paper, and the filter paper is dried at 120°C for 2 hours. The total dry mass of the filter paper and the insoluble matter remaining on the surface of the dried filter paper is measured. The mass of the insoluble matter in the virus infection inhibitor is determined by subtracting the mass of the filter paper from this total mass. Note that the filter paper after suction filtration contains compounds with sulfo group salts and organic acids dissolved in water. These dissolved matters precipitate as the filter paper dries and are included in the total dry mass. However, the mass of the dissolved matter dissolved in water is extremely small compared to the mass of the insoluble matter in the virus infection inhibitor, and therefore does not affect the content of insoluble matter in the virus infection inhibitor.

[0100] At 25°C, the D90 particle size of the insoluble matter contained in the virus infection inhibitor is preferably 1 μm or more, more preferably 2 μm or more, more preferably 3 μm or more, and more preferably 4 μm or more. At 25°C, the D90 particle size of the insoluble matter contained in the virus infection inhibitor is preferably 25 μm or less, more preferably 22 μm or less, more preferably 20 μm or less, more preferably 18 μm or less, more preferably 16 μm or less, more preferably 14 μm or less, and more preferably 12 μm or less. When the D90 particle size is 1 μm or more, the surface area of ​​the organic acid that accounts for the majority of the insoluble matter is reduced, the agglomeration tendency of the insoluble matter of the organic acid is reduced, and the virus infection inhibitor and the virus interact more easily, thereby improving the virus infection inhibitory effect of the virus infection inhibitor. When the D90 particle size is 25 μm or less, the surface area is increased, facilitating contact with the virus, thereby improving the virus infection inhibitory effect of the virus infection inhibitor. Furthermore, the dried product of the virus infection inhibitor can be adhered more uniformly to the surface of the substrate, and the virus infection inhibitory effect can be imparted to the substrate in a more uniform state.

[0101] As described below, the D90 particle size of the insoluble matter contained in the virus infection inhibitor at 25°C is the particle size (90% cumulative particle size) at which the cumulative frequency (cumulative from smallest particles) in a volume-based particle size distribution determined by laser scattering method is 90%. By adjusting the D90 particle size of the insoluble matter in the virus infection inhibitor to preferably 1 to 25 μm, the inclusion of coarse particles in the organic acid, which accounts for the majority of the insoluble matter, is reduced. Organic acids contain functional groups in their molecules [carboxyl group (-COOH), sulfo group (-SO3H), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2]]. By adjusting the D90 particle size of the insoluble matter, which accounts for the majority of the organic acid, to fall within the above range, the amount of these functional groups present in the organic acid is adjusted, thereby imparting excellent virus infection inhibitory effects to the virus infection inhibitor.

[0102] At 25°C, the D50 particle size of the insoluble matter contained in the virus infection inhibitor is preferably 0.5 μm or more, more preferably 1 μm or more, more preferably 1.5 μm or more, and more preferably 2.0 μm or more.At 25°C, the D50 particle size of the insoluble matter contained in the virus infection inhibitor is preferably 20 μm or less, more preferably 18 μm or less, more preferably 14 μm or less, more preferably 12 μm or less, and more preferably 11 μm or less.

[0103] In the virus infection inhibitor, it is preferable to set the D50 particle size of the insoluble matter within the above-mentioned range (preferably 0.5 to 20 μm) and the D90 particle size to 1 to 25 μm, thereby reducing the inclusion of coarse particles with particle sizes significantly different from the D50 particle size in the insoluble matter, which is mostly made up of organic acids, and making the particle size of the insoluble matter more appropriate.

[0104] By adjusting the particle size of the insoluble matter to a more appropriate range, the amount of the above-mentioned functional groups present on the surface of the organic acid that accounts for the majority of the insoluble matter can be more appropriately adjusted, thereby more effectively imparting an excellent virus infection inhibitory effect to the virus infection inhibitor.

[0105] The D90 and D50 particle sizes of the insoluble matter refer to the particle sizes (90% cumulative particle size and 50% cumulative particle size) at which the cumulative frequency (cumulative from small particles) in the volume-based particle size distribution determined by laser scattering method is 90% and 50%, respectively.

[0106] The virus infection inhibitor contains a compound having a sulfo group salt and an organic acid (excluding compounds having a sulfo group salt) as active ingredients. The method for producing the virus infection inhibitor is not particularly limited, and the virus infection inhibitor can be produced by supplying the compound having a sulfo group salt and the organic acid (excluding compounds having a sulfo group salt) to water and uniformly mixing them in a conventional manner. In the obtained virus infection inhibitor, the compound having a sulfo group salt is substantially all (preferably all) dissolved in water, while the organic acid is partially dissolved in water, while the remainder is insoluble and does not dissolve in water. The dried product obtained by drying the virus infection inhibitor to remove water exhibits excellent virus infection inhibitory effects, and retains excellent virus infection inhibitory effects (antiviral properties) even after contact with a disinfectant ethanol solution, and has excellent ethanol resistance.

[0107] The term "viral infection inhibitory effect" refers to the effect of eliminating or reducing the infectivity of viruses to cells, or preventing them from replicating within the cells even if they infect. Examples of methods for determining whether or not a virus is infective include ISO 18184 and JIS L1922 for textile products, and ISO 21702 for plastics and non-porous surface products other than textiles. The Society of International Studies on Antimicrobial Articles (SIAA) certifies products that meet the safety and antiviral efficacy standards for antiviral finishing agents with an antiviral finish mark. The standard for antiviral efficacy is a difference (antiviral activity value) of 2.0 or more between the common logarithm of the viral infectivity titer of a blank product (product without antiviral finishing agent) and the common logarithm of the viral infectivity titer of a processed product (product with antiviral finishing agent added) in the ISO 21702 evaluation. The viral infection inhibitor is used as an antiviral finishing agent. The viral infection inhibitor may be added to a surface coating agent such as a paint and used, and is evaluated using the above evaluation method.

[0108] In the present invention, when the viral infection inhibitory effect is evaluated under the following conditions, for example, a product is defined as a viral infection inhibitor if the difference in the common logarithm of the viral infectivity (antiviral activity value) between a blank product (blank coating) and a processed product (test coating) is 2.0 or more. Regardless of the type of virus being evaluated, a product with a difference in the common logarithm of the viral infectivity (antiviral activity value) of 2.0 or more for at least one type of virus is treated as a viral infection inhibitor.

[0109] A water-based paint is prepared by uniformly mixing 10 parts by weight of the virus infection inhibitor (based on solids content, calculated as the total weight of the compound having a sulfo group salt and the organic acid) with 90 parts by weight of an aqueous paint (e.g., acrylic emulsion, binder component solids content: 40% by mass, solvent: water) based on solids content, calculated as the binder component. The water-based paint is selected so that a portion of the organic acid is present in an insoluble state in water. The resulting water-based paint is applied to a polyester film, dried at room temperature for 1 hour, and then dried at 120°C for 1 hour to form a coating film with a thickness of 10 μm.

[0110] A flat square cotton cloth with sides of 6 cm [JIS L0803-compliant test attachment white cotton (Kanakin No. 3)] is soaked with 0.5 mL of disinfectant ethanol solution (ethanol: 80% by mass, water: 20% by mass), and the cotton cloth is attached to the friction element of a friction tester Type I (for example, manufactured by Imoto Manufacturing Co., Ltd.). Next, the surface of the obtained coating film is pressed against the surface of the test piece at a pressure of 40 g / cm. 2 Rub the cotton cloth back and forth 400 times with a cloth wiper, dry it at room temperature, and then use it as the test coating. After every 100 strokes, replace the cotton cloth with a new one soaked in 0.5 mL of disinfectant ethanol solution.

[0111] The antiviral test of the obtained test coating film was carried out in accordance with ISO 21702. For the virus suspension after the reaction, the virus infectivity titer (common logarithm value) of the test coating film was calculated by the plaque method.

[0112] A blank coating was prepared in the same manner as above, except that no virus infection inhibitor was added, and the virus infectivity (common logarithm) (PFU / cm) was calculated based on this blank coating in the same manner as above. 2 ) is calculated.

[0113] The antiviral activity value is calculated by subtracting the viral infectivity of the test coating from the viral infectivity of the blank coating.

[0114] Other methods include the plaque method and hemagglutination assay (HAU) as described in "Medical and Pharmaceutical Virology" (first published in April 1990).

[0115] The virus infection inhibitor has a virus infection inhibitory effect against various viruses due to the synergistic effect of a compound having a sulfo group salt and an organic acid (excluding compounds having a sulfo group salt), and exhibits excellent virus infection inhibitory effect against both enveloped and non-enveloped viruses. Because the virus infection inhibitor has a portion of the organic acid present in a water-insoluble state (precipitated state), it has excellent ethanol resistance, which means it has excellent virus infection inhibitory effect (antiviral property) even after contact with a disinfectant ethanol solution. Furthermore, the dried product obtained by drying the virus infection inhibitor can be firmly adhered to a substrate, allowing it to stably impart an excellent virus infection inhibitory effect to the substrate.

[0116] Examples of enveloped viruses include influenza viruses (e.g., influenza A, B, etc.), rubella viruses, Ebola viruses, coronaviruses (e.g., SARS virus, novel coronavirus (SARS-CoV-2)), measles viruses, varicella-zoster viruses, herpes simplex viruses, mumps viruses, arboviruses, respiratory syncytial viruses, hepatitis viruses (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever viruses, AIDS viruses, rabies viruses, hantaviruses, dengue viruses, Nipah viruses, and lyssaviruses.

[0117] Examples of non-enveloped viruses include adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, and rhinovirus.

[0118] The virus infection inhibitor is applied to the surface of a substrate to which a virus infection inhibitor effect is to be imparted, and then the water contained in the virus infection inhibitor is evaporated and removed to produce a dried product, which is then integrated into the surface of the substrate. The substrate with the dried product attached to its surface exhibits a virus infection inhibitor effect as a virus infection inhibitor product.

[0119] Examples of substrates onto which the dried virus infection inhibitor can be attached include synthetic resin molded products, wallpaper, decorative sheets, flooring materials, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), daily necessities and interior materials for vehicles (e.g., cars, airplanes, ships, etc.) (seats, child seats, and the foams that make up these), kitchenware, baby products, and building interior materials.

[0120] The building interior materials are not particularly limited, and examples thereof include flooring materials, wallpaper, ceiling materials, paints, doorknobs, switches, switch covers, wax, and the like.

[0121] The vehicle interior goods and materials are not particularly limited, and examples thereof include seats, child seats, seat belts, car mats, seat covers, doors, ceiling materials, floor mats, door trim, instrument panels, consoles, glove boxes, handrails, and the like.

[0122] The virus infection inhibitor may be supplied to a water-based paint for use. When the virus infection inhibitor is supplied to a water-based paint for use, the water-based paint contains water as a solvent. Therefore, when the virus infection inhibitor is contained in a water-based paint, it is preferable that the water-based paint containing the virus infection inhibitor contains the organic acid in a proportion such that a portion of the organic acid does not dissolve in water and exists in an insoluble state. Then, after the water-based paint containing the virus infection inhibitor is applied to a substrate, a dried product of the virus infection inhibitor is produced by evaporating and removing the water, and this dried product is integrated with the surface of the substrate. The substrate with the dried product attached to its surface exhibits a virus infection inhibitory effect as a virus infection inhibitory product.

[0123] A water-based paint is a paint that uses an aqueous solvent containing water as the main component (preferably 50% by mass or more of water in the solvent). The water-based paint contains an aqueous solvent and a binder component. The water-based paint may contain additives such as pigments, curing agents, extenders, fillers, antioxidants, and thickeners, as long as the additives do not impair the properties of the water-based paint. Examples of methods for incorporating a virus infection inhibitor into a water-based paint include a method in which the virus infection inhibitor and the water-based paint are supplied to a dispersing device and mixed uniformly. Examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill. [Example]

[0124] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

[0125] [Preparation of cross-linked polyacrylic acid 1-4] A polyacrylic acid solution was prepared by adding an epoxy-based crosslinking agent (sorbitol polyglycidyl ether, Nagase ChemteX Corporation, trade name "Denacol EX-614B") to an aqueous solution of polyacrylic acid (Nippon Shokubai Co., Ltd., trade name "Aqualic HL-415", weight-average molecular weight: 10,000) and mixing uniformly. The contents of polyacrylic acid and epoxy-based crosslinking agent in the polyacrylic acid solution are shown in Table 1.

[0126] The polyacrylic acid solution was heated to 120° C. for 90 minutes to crosslink the polyacrylic acid and then dried to obtain crosslinked polyacrylic acid.

[0127] [Table 1]

[0128] (Examples 1 to 19, Comparative Examples 1 to 3) A viral infection inhibitor was prepared by supplying the types of compounds having a salt of a sulfo group and organic acids shown in Table 2 to water and mixing them uniformly. The contents of the compounds having a salt of a sulfo group, organic acids, and water in the viral infection inhibitor are shown in Table 2. In Table 2, "compounds having a salt of a sulfo group" are referred to as "salt compounds."

[0129] Table 2 shows the melting point at 1 atmosphere (1013.25 hPa), solubility in water at 25°C (g / L), pKa1 at 25°C, molecular weight (weight average molecular weight before crosslinking in the case of polymers), and gel fraction (mass%) of the organic acids used to prepare the viral infection inhibitors.

[0130] In Table 2, "solubility in water at 25°C" and "pKa1 at 25°C" are simply expressed as "solubility" and "pKa1", respectively.

[0131] For the obtained virus infection inhibitor, the content (mass%) of insoluble matter present in a water-insoluble state (precipitated state) at 25°C, as well as the D50 particle size (μm) and D90 particle size (μm) of the insoluble matter present in a water-insoluble state are shown in Table 2.

[0132] For the obtained virus infection inhibitors, the content of organic acids in the insoluble matter present in a water-insoluble state (precipitated state) at 25°C is shown in Table 2. In the virus infection inhibitors of Examples 1 to 19, the content of organic acids in the insoluble matter exceeded 90 mass%.

[0133] In Table 2, the amount of the insoluble component present in a water-insoluble state was simply denoted as "insoluble component". The D50 particle size and D90 particle size of the insoluble component present in a water-insoluble state were described in the columns of "D50 particle size (μm)" and "D90 particle size (μm)" in "Details of insoluble component", respectively. The content of the organic acid in the insoluble component present in a water-insoluble state (precipitated state) was described in the column of "Content of organic acid (mass%)" in "Details of insoluble component". In Table 2, "<Y" (Y is a number) means "less than Y". ">Y" (Y is a number) means "greater than Y".

[0134] For the obtained virus infection inhibitor, an antiviral test was conducted using influenza virus (enveloped virus) and feline calicivirus (non-enveloped virus), and the results are shown in Table 1.

[0135] (Antiviral test) 10 parts by weight of the virus infection inhibitor in terms of solid content (total amount conversion of the compound having a sulfo group salt and the organic acid) and 90 parts by weight of an aqueous paint (acrylic emulsion, manufactured by Showa Denko K.K., trade name "Polyzol AM-200", solid content of binder component: 40 mass%, solvent: water) in terms of binder component as solid content were uniformly mixed to prepare an aqueous paint. A part of the organic acid was present in a water-insoluble state in the obtained aqueous paint. After applying the obtained aqueous paint on a polyester film, it was dried at room temperature for 1 hour and further dried at 120 °C for 1 hour to form a coating film with a film thickness of 10 μm.

[0136] A cotton cloth [attached white cloth for test conforming to JIS L0803, cotton (Kanakin No. 3)] in a planar square shape with a side of 6 cm was impregnated with 0.5 mL of a disinfectant ethanol solution (ethanol: 80 mass%, water: 20 mass%), and the cotton cloth was attached to the friction element of a friction tester type I (manufactured by Imoto Seisakusho Co., Ltd.). Next, the surface of the obtained coating film was frictionally rubbed 400 times back and forth under a pressure of 40 g / cm 2 and dried at room temperature to obtain a test coating film. The cotton cloth was replaced with a new cotton cloth impregnated with 0.5 mL of the disinfectant ethanol solution every 100 reciprocations.

[0137] The obtained test coating film was subjected to an antiviral test in accordance with ISO 21702. After the reaction, the virus suspension was subjected to the plaque method to calculate the virus infectivity titer (common logarithm value) of the test coating film.

[0138] A blank coating was prepared in the same manner as above, except that no virus infection inhibitor was added, and the virus infectivity (common logarithm) (PFU / cm) was calculated based on this blank coating in the same manner as above. 2 The virus infectivity titer (common logarithm) of the blank coating was 6.5 PFU / cm 2 It was.

[0139] The antiviral activity value was calculated by subtracting the viral infectivity of the test coating from the viral infectivity of the blank coating.

[0140] [Table 2] [Industrial Applicability]

[0141] The virus infection inhibitor of the present invention can be used to produce a virus infection inhibitory product that exhibits excellent virus infection inhibitory effects. The virus infection inhibitory product has excellent ethanol resistance, retains excellent virus infection inhibitory effects (antiviral properties) even after contact with a disinfectant ethanol solution, and maintains its virus infection inhibitory effects against various types of viruses for a long period of time.

[0142] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority to Japanese Patent Application No. 2022-134596, filed on August 26, 2022, the disclosure of which is incorporated herein by reference in its entirety.

Claims

1. A composition comprising a compound having a salt of a sulfo group, an organic acid, and water, The organic acid is a compound that does not contain a salt of a sulfo group in the molecule and has a carboxy group (—COOH), the organic acid has a solubility in water at 25°C of 20 g / L or less; the content of the organic acid is 5 parts by mass or more and 70 parts by mass or less, relative to 100 parts by mass of the total amount of the compound having a salt of a sulfo group, the organic acid, and the water; A virus infection inhibitor characterized in that a portion of the organic acid is present in an insoluble state in the water at 25°C.

2. The virus infection inhibitor described in Claim 1, characterized in that the compound having a salt of a sulfo group includes at least one selected from the group consisting of linear alkylbenzene sulfonate, α-olefin sulfonate, alkyl diphenyl ether sulfonate, and a polymer having a salt of a sulfo group in the side chain of a linear polymer.

3. 3. The virus infection inhibitor according to claim 1, wherein the content of insoluble matter at 25°C is 1 part by mass or more per 100 parts by mass of the total amount of the compound having a salt of a sulfo group, the organic acid, and the water.

4. The virus infection inhibitor according to claim 1 or 2, characterized in that the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (content of the compound having a salt of a sulfo group / content of the organic acid) is 0.01 to 1.

7.

5. 3. The virus infection inhibitor according to claim 1, wherein the organic acid has a plurality of carboxy groups.

6. 3. The virus infection inhibitor according to claim 1, wherein the organic acid has a pKa1 of 4.6 or less at 25°C.

7. 3. The virus infection inhibitor according to claim 1, wherein the organic acid contains a cross-linked polymer.

8. 8. The virus infection inhibitor according to claim 7, wherein the organic acid has a gel fraction of 65 to 99% by mass.

9. 3. The virus infection inhibitor according to claim 1, wherein the D90 particle size of the insoluble matter at 25° C. is 1 to 25 μm.

10. 3. The virus infection inhibitor according to claim 1, wherein the compound having a salt of a sulfo group has an aromatic ring.

11. 2. The virus infection inhibitor according to claim 1, wherein the organic acid is at least one compound selected from the group consisting of adipic acid, benzoic acid, lauric acid, azelaic acid, sebacic acid, dodecanedioic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, methylenedisalicylic acid, cis-Δ4-tetrahydrophthalic acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, myristoleic acid, oleic acid, ricinoleic acid, salicylic acid, gallic acid hydrate, benzilic acid, 4-aminobenzoic acid, triglycolaminic acid, polyacrylic acid, 1,3-propanediaminetetraacetic acid, diethylenetriaminepentaacetic acid, and linear polymers having a carboxy group in the side chain.

12. A water-based paint comprising the virus infection inhibitor according to claim 1 or 2.

13. A substrate; A virus infection-preventing product comprising the dried virus infection inhibitor according to claim 1 or 2 contained on the surface of the substrate.

14. A step of attaching the virus infection inhibitor according to claim 1 or 2 to the surface of a substrate; and a step of drying the virus infection inhibitor adhered to the surface of the substrate to produce a dried product.

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