Virus infection inhibitor, product for inhibiting virus infection, and method for producing product for inhibiting virus infection

Abstract

Provided is a virus infection inhibitor having excellent ethanol resistance, which has an excellent virus infection inhibiting effect (antiviral properties) even after contact with an ethanol solution for disinfection. This virus infection inhibitor comprises a compound of a salt having a sulfo group, an organic acid, and water, and is characterized in that a portion of the organic acid is present in a state that is insoluble in the water at 25 DEG C, and the solubility of the organic acid in the water at 25 DEG C is preferably 20 g / L or less.

Description

Technical Field

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

[0002] In recent years, in addition to the epidemic of seasonal influenza viruses, the new coronavirus (COVID-19) is spreading worldwide.

[0003] In addition, the highly pathogenic avian influenza virus has mutated and has been confirmed to be transmitted from person to person. In addition, there are concerns about the SARS virus with an extremely high mortality rate, and the sense of insecurity about viruses is increasing.

[0004] In view of these problems, Patent Document 1 proposes an RNA virus infection inhibitor containing an RNA virus infection inhibitor compound having at least one of substituents of a structural formula represented by a given general formula on a side chain of a linear polymer.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: WO2010 / 147165 Summary of the invention

[0008] Technical problem solved by the invention

[0009] On the other hand, even in the case of articles whose surfaces are treated with an RNA virus infection inhibitor, antiviral products such as antiviral films containing an RNA virus infection inhibitor, the surfaces of the antiviral products are usually disinfected with a disinfectant ethanol solution in order to remove viruses and prevent viral infection.

[0010] However, there is a problem that the antiviral activity of the RNA virus infection inhibitor is reduced when the antiviral product treated with the RNA virus infection inhibitor is disinfected with a disinfectant ethanol solution.

[0011] The present invention provides: a virus infection inhibitor having excellent ethanol resistance and having excellent virus infection inhibitory effect (antiviral property) after contact with a disinfectant ethanol solution (ethanol: 80 mass %, water: 20 mass %), a virus infection inhibitory product using the virus infection inhibitor, and a method for producing the same.

[0012] Technical means of solving problems

[0013] The virus infection inhibitor of the present invention comprises a compound having a salt of a sulfonic group, an organic acid and water, wherein a part of the organic acid is present in a state of being insoluble in the water at 25°C.

[0014] The water-based coating of the present invention contains the viral infection inhibitor.

[0015] The viral infection inhibiting product of the present invention comprises: a substrate; and a dried product of the viral infection inhibiting agent contained on the surface of the substrate.

[0016] The method for producing a virus infection inhibiting product of the present invention comprises: a step of allowing the virus infection inhibiting agent to adhere to the surface of a substrate; and a step of drying the virus infection inhibiting agent adhered to the surface of the substrate to produce a dried product.

[0017] Effects of the Invention

[0018] The virus infection inhibitor of the present invention contains a salt compound having a sulfonic group and an organic acid, and therefore has an excellent virus infection inhibitory effect on both enveloped viruses and non-enveloped viruses, and exhibits a virus infection inhibitory effect on various types of viruses.

[0019] The virus infection inhibitor of the present invention has excellent ethanol resistance, maintaining an excellent virus infection inhibitory effect (antiviral property) even after contact with a disinfectant ethanol solution, and maintains a stable virus infection inhibitory effect on various types of viruses for a long period of time. DETAILED DESCRIPTION

[0020] The virus infection inhibitor of the present invention comprises a compound having a salt of a sulfonic group, an organic acid and water, wherein a part of the organic acid is present in a water-insoluble state.

[0021] [Compound having a salt of a sulfonic group]

[0022] The compound having a sulfonic acid salt has a sulfonic acid group (-SO 3 H). Among the compounds having a sulfonic acid group, the salts derived from the sulfonic acid group (-SO 3 X: X is a metal element or NH 4 + ) has a molecular structure part that exerts a virus infection inhibitory effect. As for the salt compound having a sulfonic group, it has an excellent virus infection inhibitory effect against enveloped viruses. It should be noted that the salt compound having a sulfonic group may have a carboxyl group (-COOH), a phosphonic acid group [-P(=O)(OH) 2 ]、Phosphate group [-OPO(OH) 2 ], thiol group (-SH) and hydroxyl group (-OH).

[0023] The salt of the sulfonic group is not particularly limited, and examples thereof include sodium salt (-SO 3 Na), calcium salts [(-SO 3 -) 2 Ca2+ ], ammonium salt (-SO 3 -NH 4 + ), magnesium salts [(-SO 3 -) 2 Mg 2+ ], barium salts [(-SO 3 -) 2 Ba 2+ ], etc., preferably sodium salt (-SO 3 Na).

[0024] The compound having a salt of a sulfonic group is selected as an organic compound. In the present invention, an organic compound refers to a compound containing at least one (preferably two or more) carbon atoms and a carbon-hydrogen bond (CH bond) in a molecule.

[0025] When the salt compound having a sulfonic group is an organic compound, the affinity with the organic acid described below is improved, the salt compound having a sulfonic group is closer to the organic acid, the interaction between the salt compound having a sulfonic group and the organic acid is improved, and the viral infection inhibitory effect of both non-enveloped viruses (non-enveloped viruses) and enveloped viruses (enveloped viruses) is improved.

[0026] The compound of the salt having a sulfonic group preferably has an aromatic ring. When the compound of the salt having a sulfonic group has an aromatic ring, the affinity with the organic acid is improved, the compound of the salt having a sulfonic group is closer to the organic acid, the interaction between the compound of the salt having a sulfonic group and the organic acid is improved, and the virus infection inhibitory effect of both non-enveloped viruses (non-enveloped viruses) and enveloped viruses (enveloped viruses) is improved.

[0027] The aromatic ring may be a monocyclic aromatic ring or a monocyclic aromatic ring compounded and fused (fused aromatic ring). The aromatic ring is not particularly limited, and examples thereof include benzene ring, naphthalene ring, anthracene ring, biphenyl, phenoxyphenyl, etc., preferably benzene ring and naphthalene ring. In the case of the aromatic ring, any one or more hydrogen atoms in the aromatic ring and the fused aromatic ring are removed and bonded to other atoms through covalent bonds.

[0028] In the compound having a salt of a sulfonic group, the salt of a sulfonic group is preferably directly or indirectly bonded to an aromatic ring, and more preferably directly bonded to an aromatic ring. Due to the affinity of the aromatic ring of the compound having a salt of a sulfonic group with an organic acid, the compound having a salt of a sulfonic group is closer to the organic acid, and the synergistic effect of the salt of the sulfonic group of the compound having a salt of a sulfonic group and the organic acid can be improved, and the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses can be improved.

[0029] In the compound having a salt of a sulfonic group, when the salt of the sulfonic group is indirectly bonded to the aromatic ring, the salt of the sulfonic 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 and the organic acid in the compound having a salt of a sulfonic group, the salt of the sulfonic group and the aromatic ring are appropriately separated via the alkylene group, and the salt of the sulfonic group can be oriented in a more exposed state, so that the viral infection inhibitor exerts an excellent viral infection inhibitory effect.

[0030] In the present invention, an alkylene group refers to a divalent atomic group produced by removing (pulling out) hydrogen atoms bonded to two different carbon atoms in an aliphatic saturated hydrocarbon, and includes both linear and branched atomic groups.

[0031] Examples of the alkylene group include a methylene group (—CH 2 -), ethylene (-CH 2 -CH 2 -), propylene [-CH(CH 3 )-CH 2 -], trimethylene [-CH 2 -CH 2 -CH 2 -], butylene, pentylene [-(CH 2 ) 5 -], hexamethylene, etc.

[0032] The compound having a salt of a sulfonic group is not particularly limited as long as it has one or more sulfonic groups in the molecule, and examples thereof include linear alkylbenzene sulfonates, α-olefin sulfonates, alkyl diphenyl ether sulfonates, polyoxyalkylene alkyl ether sulfate salts, and polymers having a salt of a sulfonic group on the side chain of a linear polymer.

[0033] Examples of the linear alkylbenzene sulfonate include sodium dodecylbenzene sulfonate, calcium dodecylbenzene sulfonate, ammonium dodecylbenzene sulfonate, magnesium dodecylbenzene sulfonate, barium dodecylbenzene sulfonate, sodium tridecylbenzene sulfonate, ammonium tridecylbenzene sulfonate, sodium tetradecylbenzene sulfonate, and ammonium tetradecylbenzene sulfonate. Sodium dodecylbenzene sulfonate is preferred.

[0034] In the present invention, an alkyl group refers to a monovalent atomic group remaining after removing one hydrogen atom from an aliphatic saturated hydrocarbon.

[0035] The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonate is preferably 10 or more, more preferably 11 or more, and more preferably 12 or more. The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonic acid is preferably 25 or less, more preferably 20 or less, and more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the compound having a salt of a sulfonic group and the organic acid are closer due to the affinity of the hydrophobic part derived from the alkyl group and the organic acid, and the synergistic effect of the salt of the sulfonic group of the compound having a salt of a sulfonic group and the organic acid can be enhanced, and the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses can be enhanced.

[0036] Examples of the α-olefin sulfonate include sodium C12-C18 olefin sulfonate, calcium C12-C18 olefin sulfonate, ammonium C12-C18 olefin sulfonate, magnesium C12-C18 olefin sulfonate, barium C12-C18 olefin sulfonate, and preferably sodium C14 tetradecene sulfonate.

[0037] The carbon number of the α-olefin in the α-olefin sulfonate is preferably 12 or more, preferably 14 or more. The carbon number of the α-olefin in the α-olefin sulfonate is preferably 22 or less, more preferably 18 or less. When the carbon number of the α-olefin is within the above range, the compound having a sulfonate salt and the organic acid are closer due to the affinity of the hydrophobic part derived from the α-olefin chain of the compound having a sulfonate salt with the organic acid, and the synergistic effect of the sulfonate salt of the compound having a sulfonate salt and the organic acid can be enhanced, and the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses can be enhanced.

[0038] Examples of the alkyl diphenyl ether sulfonate 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, and sodium dodecyl diphenyl ether sulfonate having C12 is preferred.

[0039] The number of carbon atoms in the alkyl group of the alkyl diphenyl ether sulfonate is preferably 8 or more, 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, more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the compound having a sulfonate salt and the organic acid are closer due to the affinity of the hydrophobic part derived from the alkyl group of the compound having a sulfonate salt with the organic acid, and the synergistic effect of the sulfonate salt of the compound having a sulfonate salt and the organic acid can be enhanced, and the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses can be enhanced.

[0040] In the polymer having a salt of a sulfonic group on a side chain of a linear polymer, the linear polymer is not particularly limited, and for example, a vinyl polymer, a polyester, and a polyurethane are preferred, and a vinyl polymer is preferred.

[0041] The polymer having a salt of a sulfonic group on the side chain of the 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.

[0042] In addition, the polymer having a salt of a sulfonic group on the side chain of the linear polymer is preferably a homopolymer or copolymer of a monomer having a salt of a sulfonic group. Examples of the monomer having a salt of a sulfonic group include sodium p-styrene sulfonate, sodium m-styrene sulfonate, sodium o-styrene sulfonate, calcium p-styrene sulfonate, calcium m-styrene sulfonate, calcium o-styrene sulfonate, ammonium p-styrene sulfonate, ammonium m-styrene sulfonate, ammonium o-styrene sulfonate, sodium naphthalene sulfonate, and calcium naphthalene sulfonate. Sodium styrene sulfonate is preferred, and sodium p-styrene sulfonate is more preferred from the perspective of less steric hindrance in the reactivity with viruses.

[0043] It should be noted that the monomer having a salt of a sulfonic group can form a copolymer with other monomers. Examples of copolymerizable monomers include alkyl acrylates, alkyl methacrylates, vinyl alkyl ethers, 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, vinyltoluene, xylenesulfonic acid, vinylpyridine, vinylsulfonic acid, vinyl alcohol, methyl methacrylate, sodium methacrylate, hydroxyethyl methacrylate, and the like, preferably styrene.

[0044] The polymer having a salt of a sulfonic group on the side chain of the linear polymer can be produced by a general method, for example, a method of subjecting a monomer having a salt of a sulfonic group to free radical polymerization, a method of subjecting a monomer having a salt of a sulfonic group to free radical polymerization with a monomer copolymerizable with the monomer, a method of neutralizing the sulfonic group of a polymer containing a monomer component having a sulfonic group using an alkali (e.g., sodium hydroxide, calcium hydroxide, potassium hydroxide, ammonium hydroxide, etc.), etc.

[0045] In the virus infection inhibitor, the content of the compound having the salt of the sulfonic group is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and more preferably 3 parts by mass or more, relative to the total amount of 100 parts by mass of the compound having the salt of the sulfonic group, the organic acid (the organic acid dissolved in water and the organic acid in the state of being insoluble in water) and water. When the content of the salt of the sulfonic group is 0.1 parts by mass or more, the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses can be further improved through the synergistic effect with the organic acid. The upper limit of the content of the compound having the salt of the sulfonic group is not particularly limited. From the perspective of the manufacturing cost of the virus infection inhibitor, the content of the compound having the salt of the sulfonic group is preferably 50 parts by mass or less, relative to the total amount of 100 parts by mass of the compound having the salt of the sulfonic group, the organic acid (the organic acid dissolved in water and the organic acid in the state of being insoluble in water) and water.

[0046] [Organic acid]

[0047] The virus infection inhibitor contains an organic acid. The virus infection inhibitor contains an organic acid, which promotes the release of the sulfonate salt in the compound having the sulfonate salt, thereby improving the virus infection inhibitor effect on non-enveloped viruses and enhancing the virus infection inhibitor effect on enveloped viruses and non-enveloped viruses.

[0048] In addition, the compound of the salt having a sulfonic group can weaken the capsid (protein shell) of non-enveloped viruses and enhance the virus infection inhibitory effect of organic acids on non-enveloped viruses.

[0049] As described above, the virus infection inhibitor contains a compound having a salt of a sulfonic group and an organic acid, and thus has an enhanced effect of inhibiting the infection of enveloped viruses and non-enveloped viruses.

[0050] The organic acid may be any organic compound that can promote the release of a part or all of the sulfonate salt in the compound having the sulfonate salt, and may be a polymer. The organic acid has a carboxyl group (-COOH), a sulfonate group (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ], and may have only one of these functional groups or may have multiple functional groups. The organic acid can further effectively maintain or promote the release of a part or all of the sulfonate salts in the compound having the sulfonate salt, and can further improve the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses, so it is preferred to have a carboxyl group.

[0051] The organic acid preferably has a plurality of carboxyl groups (-COOH), sulfonyl groups (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] and phosphate [-OPO(OH)2 ], more preferably a carboxyl group is included in the multiple functional groups, and more preferably a plurality of carboxyl groups are included. When the organic acid has a plurality of such functional groups, the release of a part or all of the sulfonyl salts in the compound having the sulfonyl salt can be further reliably maintained or promoted, and the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses can be further improved. It should be noted that the organic acid preferably does not contain a sulfonyl salt in the molecule.

[0052] As an organic acid, as long as the molecule has a carboxyl group (-COOH), a sulfonic group (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ], there is no particular limitation, for example, 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), dodecanedioic acid (solubility: 0 g / L), fumaric acid (solubility: 6.3 g / L), phthalic acid (solubility: 7.2 g / L), isophthalic acid (solubility: : 0.13g / L), terephthalic acid (solubility: 0.017g / L), methylenedisalicylic acid (solubility: 0g / L), cis-Δ4-tetrahydrophthalic acid (solubility: 0g / L), hexanoic acid (solubility: 11g / L), heptanoic acid (solubility: 2.4g / L), octanoic acid (solubility: 0.68g / L), nonanoic acid (solubility: 0.28g / L), capric acid (solubility: 0.15g / L), lauric acid ( Solubility: 0.0048g / L), myristic acid (solubility: 0g / L), palmitic acid (solubility: 0g / L), stearic acid (solubility: 0g / L), myristic acid (solubility: 0g / L), oleic acid (solubility: 0g / L), ricinoleic acid (solubility: 0g / L), salicylic acid (solubility: 2.0g / L), gallic acid hydrate (solubility: 11g / L), benzilic acid (solubility: 1.4g / L ), 4-aminobenzoic acid (solubility: 6 g / L), nitrilotriacetic acid (solubility: 1.3 g / L), polyacrylic acid (solubility: 250 g / L or more), 1,3-propylenediaminetetraacetic acid (solubility: 9 g / L), diethylenetriaminepentaacetic acid (solubility: 4 g / L), etc., preferably adipic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, nitrilotriacetic acid, 1,3-propylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid. The solubility recorded in the brackets is the solubility of the organic acid in water at 25°C. It should be noted that the organic acid can be used alone or in combination of two or more.

[0053] When the organic acid is a polymer, examples of the organic acid include linear polymers having a carboxyl group (-COOH), a sulfone group (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ] polymers, etc.

[0054] The side chains of linear polymers have carboxyl groups (-COOH), sulfonyl groups (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ] Among the polymers, the linear polymer is not particularly limited, and for example, a vinyl polymer, a polyester, or a polyurethane is preferred, and a vinyl polymer is more preferred.

[0055] As the side chains of linear polymers, there are carboxyl groups (-COOH), sulfonyl groups (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 The polymer containing the monomer component having a carboxyl group, the polymer containing the monomer component having a sulfonic group, the polymer containing the monomer component having a phosphonic acid group [-P(=O)(OH) 2 ] monomer component polymer, containing a phosphoric acid group [-OPO (OH) 2 ] polymers of monomer components, etc.

[0056] As the monomer having a carboxyl group, for example, acrylic acid, methacrylic acid, acrylic acid, methacrylic acid, (meth) acrylate β-carboxyethyl, (meth) acrylate 5-carboxypentyl, succinic acid mono(meth)acryloyloxyethyl, ω-carboxy polycaprolactone mono(meth)acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, carboxybetaine type monomers, etc. are mentioned, preferably acrylic acid and methacrylic acid. It should be noted that the monomer having a carboxyl group can be used alone or in combination of two or more.

[0057] Examples of the monomer having a sulfonic group include p-styrenesulfonic acid, m-styrenesulfonic acid, o-styrenesulfonic acid, acrylamide tert-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 sulfonic group may be used alone or in combination of two or more.

[0058] Examples of the monomer having a phosphonic acid group include vinylphosphonic acid, vinylphosphonic acid alkyl esters, etc. The monomer having a phosphonic acid group may be used alone or in combination of two or more.

[0059] Examples of the monomer having a phosphoric acid group include phosphoric acid monoacrylate, phosphoric acid diacrylate, phosphoric acid monomethacrylate, phosphoric acid dimethacrylate, 2-hydroxyethyl phosphoric acid methacrylate, etc. The monomer having a phosphoric acid group may be used alone or in combination of two or more.

[0060] When the organic acid is a polymer, the polymer has carboxyl groups (-COOH), sulfonic groups (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ] The total content of monomer components is preferably 50 mass % or more, more preferably 60 mass % or more, more preferably 70 mass % or more, more preferably 80 mass % or more, more preferably 90 mass % or more, more preferably 95 mass % or more, more preferably 99 mass % or more, more preferably 100 mass %.

[0061] The side chains of the linear polymers have carboxyl (-COOH), sulfonyl (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ], the polymer may contain a carboxyl group (-COOH), a sulfonic group (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ] monomers and copolymerizable monomer components.

[0062] Examples of the copolymerizable monomer include alkyl acrylates, alkyl methacrylates, vinyl alkyl ethers, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, sodium acrylate, acrylamide, methacrylamide, diacetone acrylamide, vinyltoluene, vinylpyridine, methyl methacrylate, sodium methacrylate, and hydroxyethyl methacrylate.

[0063] The side chains of the linear polymers have carboxyl (-COOH), sulfonyl (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2 ] polymers can be produced by general free radical polymerization methods.

[0064] In the viral infection inhibitor, a part of the organic acid exists in an insoluble state that is not dissolved in water at 25° C. That is, in the viral infection inhibitor, a part of the organic acid dissolves in water at 25° C., while a part of the organic acid exists in an insoluble state that is not dissolved in water. At 25° C., a part of the organic acid precipitates from water.

[0065] The virus infection inhibitor exerts an excellent virus infection inhibitory effect through the interaction between the salt compound having a sulfonic group and the organic acid. When the virus infection inhibitor is used, it is used in the form of a dried product produced by drying and removing water. When the organic acid in the virus infection inhibitor is completely dissolved, the salt compound having a sulfonic group and the organic acid are easily precipitated separately during the drying process of drying and removing water, and as a result, the interaction between the salt compound having a sulfonic group and the organic acid is weakened.

[0066] Therefore, in the viral infection inhibitor, a part of the organic acid is allowed to exist in a water-insoluble state (precipitated state), and the salt compound having a sulfonic group precipitated during the water drying process in the viral infection inhibitor is easily attached to the surface of the organic acid in the insoluble state (precipitated state), so that the interaction between the salt compound having a sulfonic group and the organic acid is more effectively manifested, and an excellent viral infection inhibitory effect is still exerted after contact with the disinfectant ethanol solution.

[0067] Furthermore, since the organic acid in a water-insoluble state (organic acid precipitated from water) is a foreign substance in the water-containing viral infection inhibitor, it is squeezed out to the surface of the slowly generated dried product during the drying process of the viral infection inhibitor, and as a result, it is easy to exist on the surface of the dried product generated by drying the viral infection inhibitor. As a result, a state in which the interaction is more effectively exerted is obtained, and the salt compound having a sulfonic group and the organic acid are concentrated and exist on the surface of the dried product, and the dried product still exerts an excellent viral infection inhibitory effect after contact with the disinfectant ethanol solution.

[0068] In addition, in the virus infection inhibitor, a part of the organic acid is dissolved in water. In this way, a part of the organic acid is dissolved in water, and 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, as for the dried product generated by drying the virus infection inhibitor, it shows excellent adhesion to the substrate and is firmly integrated with the substrate surface, and even if there is contact with the disinfection ethanol solution, it can also stably give the substrate an excellent virus infection inhibition effect for a long time.

[0069] In the viral infection inhibitor, a part of the organic acid is present in a water-insoluble state, and therefore the viral infection inhibitor is usually in a white turbid state.

[0070] The solubility of the 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 the organic acid in water at 25°C is 20 g / L or less, the affinity of the compound having a salt of a sulfonic group to the organic acid is increased, the compound having a salt of a sulfonic group is closer to the organic acid, the synergistic effect of the salt of the sulfonic group and the organic acid of the compound having a salt of a sulfonic group can be increased, and the viral infection inhibitory effect against both enveloped viruses and non-enveloped viruses can be increased. It should be noted that the solubility of the organic acid in water at 25°C refers to the mass of the organic acid dissolved in 1L of water. That is, the solubility of the organic acid in water at 25°C refers to the mass of the organic acid in a saturated solution (25°C) containing 1L of water.

[0071] The solubility of the organic acid in water at 25° C. is preferably 0.1 g / L or more, more preferably 1 g / L or more. When the solubility of the organic acid in water at 25° C. is 0.1 g / L or more, when the organic acid comes into contact with an aqueous protein solution containing viruses such as saliva and sputum, the release of the salt of the sulfonic group in the compound having the salt of the sulfonic group is promoted, thereby improving the effect of inhibiting viral infection with non-enveloped viruses.

[0072] The solubility of an organic acid in water at 25°C refers to a value measured at 25°C based on OECD Chemical Testing Guideline No. 105 (Water Solubility).

[0073] The pKa1 of the organic acid at 25°C is more preferably 4.6 or less, and more preferably 3.8 or less. When the pKa1 of the organic acid at 25°C is 4.6 or less, the inhibitory effect on the viral infection of enveloped viruses is improved by the synergistic effect of the salt of the sulfonic group and the organic acid, and when it is 3.8 or less, the protein modification caused by protons occurs by further promoting the release of the salt of the sulfonic group, thereby improving the inhibitory effect on the viral infection of not only enveloped viruses but also non-enveloped viruses.

[0074] Here, in the present invention, the electrolyte HA is ionized into A- and H + When the ionization equilibrium equation (1) is obtained, the acid dissociation constant Ka is defined by equation (2), and pKa is defined by the common logarithm of the reciprocal of the acid dissociation constant Ka (3).

[0075] When the organic acid is a polybasic acid, the polybasic acid undergoes multi-step ionization, and pKa1 refers to a pKa calculated based on the ionization constant of the first step.

[0076] [Mathematical formula 1]

[0077]

[0078] pKa=-logKa (3)

[0079] The pKa1 of an organic acid at 25°C is a value measured by titration. Specifically, pKa1 can be determined by titrating an organic acid with sodium hydroxide at 25°C and measuring the pH at 25°C at a half-dosage point (a point at which half the amount for complete neutralization is added).

[0080] When the organic acid is a polymer, the organic acid preferably comprises a cross-linked polymer. A portion of the organic acid in the viral infection inhibitor may be present in a water-insoluble state, and the dried product produced from the viral infection inhibitor may maintain an excellent viral infection inhibitory effect even after contact with a disinfectant ethanol solution.

[0081] The method for cross-linking the polymer is not particularly limited and can be carried out in a general manner. Examples of the method for cross-linking the polymer include (1) a method in which a cross-linking aid and a peroxide are provided to the polymer and the polymer is heated to cross-link the polymer, and (2) a method in which a cross-linking agent is provided to the polymer and the polymer is heated to cross-link the polymer, etc.

[0082] As the crosslinking aid, there is no particular limitation, and examples thereof include divinylbenzene, trimethylolpropane trimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, triallyl trimellitate, triallyl isocyanurate, ethylvinylbenzene, neopentyl glycol dimethacrylate, 1,2,4-benzenetris triallyl ester, 1,6-hexanediol dimethacrylate, lauryl methacrylate, stearyl methacrylate, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, etc. It should be noted that the crosslinking aid may be used alone or in combination of two or more.

[0083] The peroxide is not particularly limited, and examples thereof include 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroperoxide, tert-butyl hydroperoxide, 1,1-di(tert-butylperoxy)-3,3,5-trimethylhexane, 4,4-di(tert-butylperoxy)valerate, n-butyl α,α′-bis(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3, tert-butylperoxyisopropylbenzene, etc. It should be noted that the peroxide may be used alone or in combination of two or more.

[0084] The crosslinking agent is not particularly limited, and a general-purpose crosslinking agent can be used, for example, epoxy crosslinking agents, isocyanate crosslinking agents, imine crosslinking agents, etc. The crosslinking agent can be used alone or in combination of two or more.

[0085] Examples of the isocyanate crosslinking agent include tolylene diisocyanate, 1,5-naphthalene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, and trimethylolpropane-modified toluene diisocyanate.

[0086] As the epoxy crosslinking agent, for example, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-1,3-phenylenedi(methanamine) and the like are preferred.

[0087] In the case where the organic acid contains a cross-linked 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 more preferably 96% by mass or less. When the gel fraction of the organic acid is 65% by mass or more, a part of the organic acid can be further reliably present in a water-insoluble state, and after contacting with the disinfection ethanol solution, the dried product of the virus infection inhibitor can maintain an excellent virus infection inhibitory effect. In addition, a cross-linked structure is imparted to the polymer, so the cross-linked part of the polymer is insoluble in the ethanol solution, and the non-cross-linked part of the polymer can freely perform molecular motion, so by efficiently adsorbing the virus, it is possible to still exert an excellent virus infection inhibitory effect after contacting with the disinfection 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 part of the organic acid in water, and even after contacting with the disinfection ethanol solution, the excellent virus infection inhibitory effect imparted to the substrate can be stably maintained.

[0088] The gel fraction of an organic acid is a value measured as follows: an organic acid Ag is weighed, immersed in purified water at 60°C for 24 hours, and the insoluble components are filtered through a 200-mesh gold mesh, and the residue on the gold mesh is vacuum dried at 80°C for 16 hours to measure the weight of the dry residue (B g), and the gel fraction of the organic acid is calculated by the following formula.

[0089] Gel fraction of organic acid (mass %) = (B / A) × 100

[0090] When the organic acid is a polymer, the weight average molecular weight of the organic acid is preferably 3000 or more, preferably 5000 or more, more preferably 10000 or more, and more preferably 100000 or more. When the weight average molecular weight of the organic acid is 3000 or more, the adsorption points of the organic acid and the virus increase per molecule, the interaction between the organic acid and the virus becomes stronger, and the virus infection inhibitory effect of the virus infection inhibitor can be improved.

[0091] The weight average molecular weight of the organic acid is preferably 1,000,000 or less, more preferably 900,000 or less, more preferably 800,000 or less, and more preferably 500,000 or less. When the weight average molecular weight of the organic acid is 1,000,000 or less, the cohesion of the insoluble components in the organic acid is reduced, and as a result, the organic acid and the virus are in a form that easily interacts with each other, thereby improving the virus infection inhibitory effect of the virus infection inhibitor.

[0092] It should be noted that in the present invention, the weight average molecular weight of the polymer is a value measured by GPC (gel permeation chromatography) in terms of polystyrene. It should be noted that when the polymer is cross-linked, the weight average molecular weight of the polymer refers to the weight average molecular weight of the polymer before cross-linking.

[0093] For example, the measurement can be performed using the following measuring apparatus and measuring conditions.

[0094] Gel Permeation Chromatograph: Waters Corporation, trade name "2690 Separations Model"

[0095] Column: Showa Denko K.K. trade name "GPC KF-806L"

[0096] Detector: Differential Refractometer

[0097] Sample flow rate: 1mL / min

[0098] Column temperature: 40°C

[0099] Eluent: THF

[0100] The organic acid is preferably solid at 1 atmosphere (1013.25 hPa) and 25° C. When the organic acid is solid at 1 atmosphere and 25° C., it is easy to appear on the surface of the processed coating film or other virus infection inhibiting product, and is easy to contact with the virus, thereby improving the virus infection inhibiting effect.

[0101] 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 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 sulfonic group, the organic acid (the organic acid soluble in water and the organic acid in a water-insoluble state), and water. When the content of the organic acid is 5 parts by mass or more, a part of the organic acid is likely to exist in an insoluble state, and the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses can be further improved.

[0102] In the viral infection inhibitor, the upper limit of the content of the organic acid is not particularly limited. From the viewpoint of the manufacturing cost of the viral infection inhibitor, the content of the organic acid is preferably 70 parts by mass or less relative to 100 parts by mass of the total amount of the salt compound having a sulfonic group, the organic acid (the organic acid soluble in water and the organic acid in a water-insoluble state) and water.

[0103] In the virus infection inhibitor, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (the organic acid dissolved in water and the organic acid in a water-insoluble state) (the content of the compound having a salt of a sulfonic group / the content of the organic acid) is preferably 0.01 or more, more preferably 0.02 or more, more preferably 0.10 or more, and more preferably 0.15 or more. In the virus infection inhibitor, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (the content of the compound having a salt of a sulfonic group / the content of the organic acid) is preferably 1.7 or less, more preferably 1.6 or less, and more preferably 1.55 or less. When the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (the content of the compound having a salt of a sulfonic group / the content of the organic acid) is 0.01 or more, the adsorption of the sulfonic group generated by freeing the salt of the sulfonic group in the compound having a salt of a sulfonic group to the virus is promoted, and an excellent virus infection inhibitory effect is exhibited. When the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (content of the compound having a salt of a sulfonic group / content of the organic acid) is 1.7 or less, the adhesion between the organic acid in a water-insoluble state and the substrate is further improved by the action of the compound having a salt of a sulfonic group dissolved in water and the organic acid dissolved in water, and the dried product of the viral infection inhibitor becomes difficult to peel off from the substrate, and the excellent viral infection inhibitory effect imparted to the substrate can be stably maintained even after contact with an ethanol solution for disinfection.

[0104] In the virus infection inhibitor, the water content is preferably 95 parts by weight or less, more preferably 90 parts by weight or less, and more preferably 80 parts by weight or less, relative to 100 parts by weight of the total amount of the compound having a salt of a sulfonic group, the organic acid (an organic acid soluble in water and an organic acid in a water-insoluble state) and water. When the water content is 95 parts by weight or less, a part of the organic acid is likely to exist in an insoluble state, which can further improve the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses. The lower limit of the water content is not particularly limited. From the perspective of the manufacturing cost of the virus infection inhibitor, the water content is preferably 30 parts by weight or more relative to 100 parts by weight of the total amount of the compound having a salt of a sulfonic group, the organic acid (an organic acid soluble in water and an organic acid in a water-insoluble state) and water.

[0105] [Other ingredients]

[0106] The virus infection inhibitor may contain additives such as a dispersant, a thickener, an antioxidant, and an ultraviolet absorber within a range that does not impair its physical properties.

[0107] Examples of the dispersant include surfactants such as anionic surfactants (excluding compounds having a salt of a sulfonic group in the molecule), cationic surfactants, nonionic surfactants, and amphoteric surfactants (excluding compounds having a salt of a sulfonic group in the molecule). From the perspective of improving the dispersibility of the organic acid in a water-insoluble state, the dispersant is preferably an anionic surfactant (excluding compounds having a salt of a sulfonic group in the molecule).

[0108] Examples of the anionic surfactant (excluding compounds having a salt having a sulfonic group in the molecule) include alkyl sulfate ester salts, alkyl ethoxy sulfate ester salts, and phosphoric acid ester salts.

[0109] Examples of the cationic surfactant include fatty amine salts, quaternary ammonium salts, and alkylpyridinium salts.

[0110] Examples of the nonionic surfactant include polyoxyalkylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters (e.g., polyethylene glycol distearate), polyoxyethylene distyrenated phenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerol fatty acid esters, polyoxyethylene glycerol fatty acid esters, polyglycerol fatty acid esters, sucrose fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, fatty acid alkanolamides (e.g., coconut oil fatty acid dimethanolamide, coconut oil fatty acid diethanolamide, coconut oil fatty acid dipropanolamide and other coconut oil fatty acid alkanolamides), fatty acid alkylolamides, alkyl alkanolamides, acetylene glycol, ethylene oxide addition products of acetylene glycol, and polyethylene glycol-polypropylene glycol block copolymers.

[0111] Examples of the amphoteric surfactant (excluding compounds having a salt having a sulfonic group in the molecule) include tertiary amine oxides, betaines, and alkyl betaines.

[0112] As the thickener, it can be a natural polymer compound or a synthetic polymer compound. As the natural polymer compound, for example, pectin, gelatin, carrageenan, xanthan gum, gum arabic, glucomannan, gellan gum, alginic acid, etc. can be mentioned. As the synthetic polymer compound, for example, polyethylene glycol, polyvinyl alcohol, etc. can be mentioned.

[0113] [Viral infection inhibitors]

[0114] The virus infection inhibitor contains a water-insoluble component (precipitated component). In the virus infection inhibitor, the insoluble component is almost entirely composed of an organic acid that exists in a water-insoluble state. A portion of the water-insoluble component (precipitated component) may contain components other than the organic acid.

[0115] At 25°C, the content of the insoluble components 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 more preferably 20 parts by mass or more, relative to the total amount of 100 parts by mass of the compound having a salt of a sulfonic group, the organic acid (the organic acid dissolved in water and the organic acid in a water-insoluble state) and water. When the content of the insoluble components is 1 part by mass or more, the dried product of the virus infection inhibitor can maintain an excellent virus infection inhibitory effect even after contact with the ethanol solution for disinfection by increasing the interaction between the compound having a salt of a sulfonic group and the organic acid. At 25°C, the upper limit of the content of the insoluble components in the virus infection inhibitor is not particularly limited. From the viewpoint of coating properties, the content of the insoluble components in the virus infection inhibitor is preferably 70 parts by mass or less, relative to the total amount of 100 parts by mass of the compound having a salt of a sulfonic group, the organic acid (the organic acid dissolved in water and the organic acid in a water-insoluble state) and water.

[0116] At 25° C., the content of the organic acid in the insoluble components of the virus infection inhibitor is more 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, 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 dry substance of the virus infection inhibitor can maintain an excellent virus infection inhibitory effect even after contact with the disinfectant ethanol solution by increasing the interaction between the compound having a salt of a sulfonic group and the organic acid. At 25° C., the upper limit of the content of the organic acid in the insoluble components of the virus infection inhibitor is not particularly limited.

[0117] At 25°C, the content of insoluble components in the virus infection inhibitor is a value obtained by measuring in the following manner. First, only the mass of the filter paper based on 5 types C of JIS P3801 is measured. Next, after filtering 100g of the virus infection inhibitor through the filter paper, the filter paper is dried at 120°C for 2 hours, and the insoluble components remaining on the surface of the dried filter paper and the total dry mass of the filter paper are measured. By removing only the mass of the filter paper from the total mass, the mass of the insoluble components in the virus infection inhibitor is obtained. It should be noted that the filter paper after suction filtration contains compounds and organic acids with sulfonic acid salts that are soluble in water. These soluble components are precipitated with the drying of the filter paper and are included in the total dry mass. The mass of the soluble components dissolved in water is very small compared to the mass of the insoluble components in the virus infection inhibitor, so it has no effect on the content of the insoluble components in the virus infection inhibitor.

[0118] At 25°C, the D90 particle size of the insoluble components 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 components 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 occupies most of the insoluble components becomes smaller, reducing the cohesion of the insoluble components of the organic acid, and the virus infection inhibitor and the virus become a form that is easy to interact with each other, thereby improving the virus infection inhibitor effect of the virus infection inhibitor. When the D90 particle size is 25 μm or less, the surface area can be increased and it is easy to contact with the virus, thereby improving the virus infection inhibitor effect of the virus infection inhibitor. Furthermore, the dried substance of the virus infection inhibitor can be more evenly attached to the surface of the substrate, and the virus infection inhibitor effect can be imparted to the substrate in a more uniform state.

[0119] At 25°C, the D90 particle size of the insoluble components contained in the virus infection inhibitor is the particle size (90% cumulative particle size) at which the accumulation of frequencies in the volume-based particle size distribution based on the laser scattering method (accumulation of particles with smaller particle sizes) is 90%, as described below. By preferably adjusting the D90 particle size of the insoluble components in the virus infection inhibitor to 1 to 25 μm, the presence of coarse particles in the organic acid that accounts for most of the insoluble components is reduced. The organic acid has functional groups [carboxyl (-COOH), sulfone (-SO 3 H), phosphonic acid [-P(=O)(OH) 2 ] or phosphate group [-OPO(OH) 2]], by adjusting the D90 particle size of the insoluble component in which the organic acid occupies a large part to the above range, the amount of the functional group present in the organic acid is adjusted, thereby imparting an excellent viral infection inhibitory effect to the viral infection inhibitor.

[0120] At 25° C., the D50 particle size of the insoluble components contained in the viral 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 components contained in the viral 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.

[0121] In viral infection inhibitors, it is preferred that the D50 particle size of the insoluble component is within the above range (preferably 0.5 to 20 μm) and the D90 particle size is adjusted to 1 to 25 μm. This can reduce the presence of coarse particles having a particle size that is significantly different from the D50 particle size in the insoluble component in which organic acids account for the majority, thereby making the particle size of the insoluble component a more appropriate size.

[0122] Furthermore, by adjusting the particle size of the insoluble component to a more appropriate range, the amount of the functional groups present on the surface of the organic acid that accounts for most of the insoluble component is more appropriately adjusted, thereby more effectively imparting an excellent viral infection inhibitory effect to the viral infection inhibitor.

[0123] The D90 particle size and D50 particle size of the insoluble component refer to the particle sizes (90% cumulative particle size and 50% cumulative particle size) where the cumulative frequency (cumulative frequency derived from particles with smaller particle sizes) in the volume-based particle size distribution based on the laser scattering method is 90% and 50%, respectively.

[0124] The virus infection inhibitor contains a compound having a salt of a sulfonic group and an organic acid (excluding the compound having a salt of a sulfonic group) as active ingredients. The method for manufacturing the virus infection inhibitor is not particularly limited. The virus infection inhibitor can be manufactured by adding a compound having a salt of a sulfonic group and an organic acid (excluding the compound having a salt of a sulfonic group) to water and uniformly mixing them in a general manner. In the obtained virus infection inhibitor, substantially all (preferably all) of the compound having a salt of a sulfonic group dissolves in water, a portion of the organic acid dissolves in water, and the remaining portion does not dissolve in water and exists in an insoluble state. In addition, the dried product obtained by drying the virus infection inhibitor and removing water exerts an excellent virus infection inhibitory effect, and has an excellent virus infection inhibitory effect (antiviral property) even after contact with an ethanol solution for disinfection, and has excellent ethanol resistance.

[0125] It should be noted that the virus infection inhibitory effect refers to the effect of making the virus lose or reduce its infectivity to cells or preventing it from proliferating in cells even if infected. As a method for confirming the presence or absence of such viral infectivity, for example, ISO18184 and JIS L1922 can be cited in fiber products, and ISO21702 can be cited in plastics other than fiber products and products with non-porous surfaces. As far as the Antimicrobial Products Technology Agreement (SIAA) is concerned, the antiviral processing mark is certified for products that meet the safety standards of antiviral processing agents and certain antiviral effect standards. The standard for antiviral effect is: in the evaluation of ISO21702, the difference (antiviral activity value) between the common logarithm of the virus infection titer of the blank product (no additives of the antiviral processing agent) and the common logarithm of the virus infection titer of the processed product (additives of the antiviral processing agent) is 2.0 or more. Virus infection inhibitors are used as antiviral processing agents. Virus infection inhibitors can be added to surface coating agents such as paints for use and evaluated by the above evaluation method.

[0126] In the present invention, for example, when evaluating the virus infection inhibitory effect under the following conditions, a product having a difference in the common logarithmic value of the virus infection titer between a blank product (blank coating) and a processed product (test coating) (antiviral activity value) of 2.0 or more is defined as a virus infection inhibitor. At this time, regardless of the type of virus to be evaluated, in at least one virus, a product having a difference in the common logarithmic value of the virus infection titer between a blank product and a processed product (antiviral activity value) of 2.0 or more is treated as a virus infection inhibitor.

[0127] 10 parts by weight of a virus infection inhibitor calculated as solid content (calculated as the total amount of a compound having a salt of a sulfonic group and an organic acid) and 90 parts by weight of a water-based coating (for example, an acrylic emulsion, a solid content of an adhesive component: 40% by mass, a solvent: water) calculated as solid content and an adhesive component are uniformly mixed to prepare a water-based coating. In the obtained water-based coating, a water-based coating is selected so that a part of the organic acid exists in a water-insoluble state. After applying the obtained water-based coating to a polyester film, it is 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.

[0128] A flat square cotton cloth [JIS L0803 standard adjacent fabric for testing (Golden towel (fine white cloth) No. 3)] with a side length of 6 cm was impregnated with 0.5 mL of a disinfecting ethanol solution (ethanol: 80% by mass, water: 20% by mass), and the cotton cloth was attached to the friction element of a friction tester type I (for example, manufactured by Imoto Seisakusho Co., Ltd.). Next, the surface of the obtained coating film was subjected to a pressure of 40 g / cm 2The cotton cloth was rubbed back and forth 400 times and dried at room temperature to prepare a test coating film. The cotton cloth was replaced with a new cotton cloth soaked in 0.5 mL of a disinfecting ethanol solution every 100 times.

[0129] The obtained test coating was subjected to an antiviral test in accordance with ISO 21702. The virus infection titer (common logarithm value) of the test coating was calculated by the plaque method for the virus suspension after the reaction.

[0130] A blank coating was prepared in the same manner as described above except that no virus infection inhibitor was contained. Based on the blank coating, the virus infection titer (common logarithm) (PFU / cm 2 ).

[0131] The antiviral activity value was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0132] In addition, the plaque method and hemagglutination titer (HAU) measurement method described in "Medical Virology" (first edition published in April 1990) can be cited.

[0133] The virus infection inhibitor has a virus infection inhibitory effect on various viruses through the synergistic effect of the compound having a salt of a sulfonic group and the organic acid (excluding the compound having a salt of a sulfonic group), and exerts an excellent virus infection inhibitory effect on both enveloped viruses and non-enveloped viruses. As for the virus infection inhibitor, a part of the organic acid is present in a water-insoluble state (precipitated state), so it has excellent ethanol resistance that still has an excellent virus infection inhibitory effect (antiviral property) even after contact with an ethanol solution for disinfection. Furthermore, the virus infection inhibitor can be dried so that the obtained dried product is firmly adhered to the substrate, and the excellent virus infection inhibitory effect can be stably imparted to the substrate.

[0134] Examples of enveloped viruses include influenza virus (e.g., type A, type B, etc.), rubella virus, Ebola virus, coronavirus [e.g., SARS virus, novel coronavirus (SARS-CoV-2)], measles virus, varicella / herpes zoster virus, herpes simplex virus, mumps virus, arbovirus, RS virus, hepatitis virus (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever virus, HIV, rabies virus, Hanta virus, dengue virus, Nipah virus, lyssa virus, etc.

[0135] Examples of the non-enveloped virus include adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, and rhinovirus.

[0136] In the case of a virus infection inhibitor, after coating the surface of a substrate to be provided with a virus infection inhibitory effect, water contained in the virus infection inhibitor is evaporated and removed to form a dried product, and the dried product is integrated with the surface of the substrate. The substrate with the dried product attached to the surface exhibits a virus infection inhibitory effect as a virus infection inhibitory product.

[0137] Examples of the substrate to which the dried article of the virus infection inhibitor is attached include synthetic resin molded bodies, wallpapers, decorative sheets, floor materials, fiber products (woven fabrics, nonwoven fabrics, knitted fabrics), daily necessities and interior materials (seats, child seats, and foams constituting these) for vehicles (e.g., cars, airplanes, ships, etc.), kitchen supplies, baby products, and building interior materials.

[0138] The building interior material is not particularly limited, and examples thereof include floor materials, wallpapers, ceiling materials, paints, door handles, switches, switch covers, wax, and the like.

[0139] The vehicle interior products and vehicle interior materials are not particularly limited, and examples thereof include seats, child seats, seat belts, car mats, seat covers, doors, roof materials, floor mats, door trims, instrument panels, consoles, glove boxes, hanging rings, armrests, and the like.

[0140] Virus infection inhibitors can be used in water-based coatings. When the virus infection inhibitor is supplied to the water-based coating and used, the water-based coating contains water as a solvent. Therefore, when the water-based coating contains the virus infection inhibitor, it is preferably contained in the water-based coating containing the virus infection inhibitor in a proportion so that a part of the organic acid is insoluble in water and exists in an insoluble state. In addition, after the water-based coating containing the virus infection inhibitor is applied to the substrate, the dried substance of the virus infection inhibitor is generated by evaporation and removal of water, and the dried substance is integrated with the surface of the substrate. The substrate with the dried substance attached to the surface exhibits a virus infection inhibition effect as a virus infection inhibition product.

[0141] Water-based paint is a paint that uses an aqueous solvent containing water as the main component (preferably more than 50% by mass of water in the solvent). Water-based paint contains an aqueous solvent and a binder component. Water-based paint can contain additives such as pigments, curing agents, extenders, fillers, anti-aging agents, thickeners, etc. within the range that does not damage its physical properties. It should be noted that as a method for making the water-based paint contain a virus infection inhibitor, for example, a method of supplying the virus infection inhibitor and the water-based paint to a dispersing device and uniformly mixing them can be cited. It should be noted that as a dispersing device, for example, a high-speed mill, a ball mill, a sand mill, etc. can be cited.

[0142] Example

[0143] Hereinafter, the present invention is more specifically described using Examples, but the present invention is not limited thereto.

[0144] [Preparation of cross-linked polyacrylic acids 1 to 4]

[0145] An epoxy crosslinking agent (sorbitol polyglycidyl ether, NAGASECHEMTEX trade name "DENACOL EX-614B") was added to an aqueous solution of polyacrylic acid (trade name "AQUALIC HL-415" manufactured by NIPPON SHOKUBAI, weight average molecular weight: 10,000) and uniformly mixed to prepare a polyacrylic acid solution. The contents of polyacrylic acid and epoxy crosslinking agent in the polyacrylic acid solution are shown in Table 1.

[0146] The polyacrylic acid solution was heated at 120° C. for 90 minutes to crosslink the polyacrylic acid and simultaneously dry the crosslinked polyacrylic acid to obtain crosslinked polyacrylic acid.

[0147] [Table 1]

[0148]

[0149] (Examples 1 to 19, Comparative Examples 1 to 3)

[0150] A compound having a salt of a sulfonic group and an organic acid of the types shown in Table 2 were supplied to water and uniformly mixed to prepare a virus infection inhibitor. The contents of the compound having a salt of a sulfonic group, the organic acid, and water in the virus infection inhibitor are shown in Table 2. It should be noted that in Table 2, "a compound having a salt of a sulfonic group" is represented as "a salt compound".

[0151] For the organic acids used in the preparation of viral infection inhibitors, the melting point at 1 atmosphere (1013.25 hPa), the solubility in water at 25°C (g / L), the pKa1 at 25°C, the molecular weight (in the case of polymers, the weight average molecular weight before crosslinking) and the gel fraction (mass %) are shown in Table 2.

[0152] In addition, in Table 2, "solubility in water at 25°C" and "pKa1 at 25°C" are simply expressed as "solubility" and "pKa1", respectively.

[0153] For the obtained viral infection inhibitor, the content (mass %) of the insoluble component existing in a water-insoluble state (precipitated state) at 25°C, and the D50 particle size (μm) and D90 particle size (μm) of the insoluble component existing in a water-insoluble state are shown in Table 2.

[0154] For the obtained virus infection inhibitor, the content of the organic acid in the insoluble component 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 the organic acid in the insoluble component exceeded 90% by mass.

[0155] It should be noted that in Table 2, the amount of the insoluble component present in a water-insoluble state is simply expressed as "insoluble component". The D50 particle size and D90 particle size of the insoluble component present in a water-insoluble state are respectively described in the columns of "D50 particle size (μm)" and "D90 particle size (μm)" in the "Details of insoluble component". The content of the organic acid in the insoluble component present in a water-insoluble state (precipitated state) is described in the column of "Content of organic acid (% by mass)" in the "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".

[0156] 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.

[0157] (Antiviral test)

[0158] 10 parts by weight of the virus infection inhibitor in terms of solid component conversion (total conversion of the compound with a sulfonic group-containing salt and the organic acid) was uniformly mixed with 90 parts by weight of an aqueous coating (acrylic emulsion, manufactured by Showa Denko K.K., trade name "POLYSOL AM-200", solid component of the binder component: 40% by mass, solvent: water) in terms of solid component conversion of the binder component to prepare an aqueous coating. In the obtained aqueous coating, a part of the organic acid exists in a water-insoluble state. After the obtained aqueous coating was applied to 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.

[0159] A square cotton cloth with a side length of 6 cm [JIS L0803 test standard lining fabric cotton (Kanekin (fine white cloth) No. 3)] was impregnated with 0.5 mL of a disinfectant ethanol solution (ethanol: 80% by mass, water: 20% by mass), and the cotton cloth was installed on the friction element of a friction testing machine type I (manufactured by Imoto Seisakusho Co., Ltd.). Next, the surface of the obtained coating film was rubbed back and forth 400 times under a pressure of 40 g / cm 2 and dried at room temperature to prepare a test coating film. It should be noted that the cotton cloth was replaced with a new cotton cloth impregnated with 0.5 mL of the disinfectant ethanol solution every 100 round trips.

[0160] The obtained test coating was subjected to an antiviral test in accordance with ISO 21702. The virus infection titer (common logarithm value) of the test coating was calculated by the plaque method for the virus suspension after the reaction.

[0161] A blank coating was prepared in the same manner as described above except that no virus infection inhibitor was contained. Based on the blank coating, the virus infection titer (common logarithm) (PFU / cm 2 The virus infection titer (common logarithm value) of the blank coating is 6.5 PFU / cm 2 .

[0162] The antiviral activity value was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0163] [Table 2]

[0164]

[0165] Industrial Applicability

[0166] The virus infection inhibitor of the present invention can produce a virus infection inhibitory product that exhibits an excellent virus infection inhibitory effect. The virus infection inhibitory product has excellent ethanol resistance, which still exhibits an excellent virus infection inhibitory effect (antiviral property) after contact with a disinfectant ethanol solution, and can maintain a stable virus infection inhibitory effect on various types of viruses for a long time.

[0167] (CROSS-REFERENCE TO RELATED APPLICATIONS)

[0168] This application claims priority based on 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 virus infection inhibitor comprising: a compound having a salt of a sulfonic group, an organic acid and water, A part of the organic acid exists in a state of being insoluble in the water at 25°C.

2. The viral infection inhibitor according to claim 1, wherein The solubility of the organic acid in water at 25° C. is 20 g / L or less.

3. The viral infection inhibitor according to claim 1 or 2, wherein The content of the insoluble component at 25° C. is 1 part by mass or more based on 100 parts by mass of the total amount of the compound having a salt of a sulfonic group, the organic acid, and the water.

4. The viral infection inhibitor according to claim 1 or 2, wherein The mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (the content of the compound having a salt of a sulfonic group / the content of the organic acid) is 0.01 to 1.

7.

5. The viral infection inhibitor according to claim 1 or 2, wherein The organic acid has a carboxyl group.

6. The viral infection inhibitor according to claim 1 or 2, wherein The organic acid has a pKa1 of 4.6 or less at 25°C.

7. The viral infection inhibitor according to claim 1 or 2, wherein The organic acid comprises a cross-linked polymer.

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

9. The viral infection inhibitor according to claim 1 or 2, wherein The D90 particle size of the insoluble component at 25°C is 1 to 25 μm.

10. The viral infection inhibitor according to claim 1 or 2, wherein The compound of the salt having a sulfonic group has an aromatic ring.

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

12. A viral infection inhibition product comprising: substrate; and A dried product of the viral infection inhibitor according to claim 1 or 2, contained on the surface of the substrate.

13. A method for producing a viral infection inhibition product, comprising: 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 attached to the surface of the substrate to produce a dried product.

Images