Virus infection inhibitors, resin compositions, masterbatches for synthetic resin molding, and virus infection inhibitor products

Abstract

The present invention provides a viral infection inhibitor having excellent water resistance and demonstrating excellent viral infection inhibition effect (antiviral) even after wiping with water and a viral infection inhibition product using the same. A viral infection inhibitor according to the present invention comprises an organic acid (A) having a solubility in water at 25°C not more than 0.4 g / L, and preferably further comprises a compound having a salt of a sulfo group. Accordingly, the viral infection inhibitor can maintain excellent viral infection inhibition effect even after wiping with water, and a viral infection inhibition product having excellent viral infection inhibition effect can be prepared.

Description

[Technical Field]

[0001] The present invention relates to a virus infection inhibitor, a resin composition, a masterbatch for synthetic resin molding, and a virus infection-inhibiting 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 antiviral synthetic resin composition containing 0.5 parts by weight or more of a sulfonic acid surfactant per 100 parts by weight of synthetic resin. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2016-128395 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the above antiviral synthetic resin composition has a problem in that it has low water resistance and its antiviral properties (viral infection prevention effect) decrease after wiping with water.

[0007] The present invention provides a virus infection inhibitor that can maintain excellent virus infection-inhibiting effect even after wiping with water. The present invention also provides a resin composition, a synthetic resin molding masterbatch, and a virus infection-inhibiting product that use the virus infection inhibitor. [Means for solving the problem]

[0008] The virus infection inhibitor of the present invention contains an organic acid (A) having a solubility in water at 25°C of 0.4 g / L or less.

[0009] The resin composition of the present invention is characterized by containing a synthetic resin and the above-mentioned virus infection inhibitor.

[0010] The synthetic resin molding masterbatch of the present invention is characterized by containing a synthetic resin and the virus infection inhibitor.

[0011] The viral infection-inhibiting product of the present invention is characterized by comprising a base material and the viral infection-inhibiting agent described above. [Effects of the Invention]

[0012] The virus infection inhibitor of the present invention contains an organic acid (A) having a solubility of 0.4 g / L or less in water at 25° C., and therefore can maintain excellent virus infection inhibitory effects even after wiping with water. DETAILED DESCRIPTION OF THE INVENTION

[0013] The viral infection inhibitor of the present invention contains, as an active ingredient, an organic acid (A) having a solubility in water at 25°C of 0.4 g / L or less.

[0014] [Organic acid (A)] The virus infection inhibitor contains, as an active ingredient, an organic acid (A) (hereinafter sometimes simply referred to as "organic acid (A)") having a solubility in water at 25°C of 0.4 g / L or less.

[0015] The virus infection inhibitor contains, as an active ingredient, an organic acid (A) having a solubility in water at 25°C of 0.4 g / L or less, so that the virus infection inhibitor can remain in place well even after wiping with water, and can continue to exert excellent virus infection inhibitory effects.

[0016] The organic acid (A) may have a solubility of 0.4 g / L or less in water at 25°C, and may be a polymer. The organic acid (A) has a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)2], or a phosphate group [-OPO(OH)2] in the molecule. The organic acid (A) may have only one of these functional groups or may have multiple functional groups. The total number of the functional groups (carboxy group (-COOH), sulfo group (-SOH), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2]) in the organic acid (A) may be one or more. The organic acid (A) preferably has a carboxy group or a sulfo group, and more preferably has a carboxy group, since this can further improve the viral infection-inhibiting effect against enveloped and non-enveloped viruses.

[0017] The organic acid (A) preferably has a plurality of functional groups selected from the group consisting of a carboxyl 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 carboxyl group among the plurality of functional groups, and even more preferably a plurality of carboxyl groups. When the organic acid (A) has a plurality of the above functional groups, the effect of inhibiting viral infection with enveloped and non-enveloped viruses can be further improved. It is preferable that the organic acid (A) does not contain a salt of a sulfo group in the molecule.

[0018] The organic acid (A) is not particularly limited as long as it has a solubility in water at 25°C of 0.4 g / L or less and has a carboxyl group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphate group [-OPO(OH)2] in the molecule. Examples of the organic acid (A) include alginic acid (solubility: 0 g / L), lauric acid (solubility: 0 g / L), sebacic acid (solubility: 0.25 g / L), dodecanedioic acid (solubility: 0 g / L), isophthalic acid (solubility: 0.13 g / L), terephthalic acid (solubility: 0.017 g / L), methylenediaminetetraacetic acid (solubility: 0.13 g / L), and methylparaben (solubility: 0.13 g / L). Examples of organic acids include phthalic acid (solubility: 0 g / L), cis-Δ4-tetrahydrophthalic acid (solubility: 0 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), and ricinoleic acid (solubility: 0 g / L). Alginic acid, isophthalic acid, and terephthalic acid are preferred. The solubilities listed in parentheses are the solubility of the organic acid (A) in water at 25°C. The organic acids (A) may be used alone or in combination.

[0019] When the organic acid (A) is a polymer, examples of the organic acid (A) include a polymer having 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 side chain of a linear polymer. When the organic acid (A) is a polymer, a polymer having a carboxy group or a sulfo group is preferred because the viral infection inhibitor will exhibit an excellent viral infection inhibitory effect.

[0020] In the case of a polymer having a carboxy group (-COOH), a sulfo group (-SOH), a phosphonic acid group [-P(=O)(OH)] or a phosphoric acid group [-OPO(OH)] in the side chain of the linear polymer, the linear polymer is not particularly limited, and for example, a vinyl polymer, a polyester or a polyurethane is preferred, with a vinyl polymer being preferred.

[0021] 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)].

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] When the organic acid (A) 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, because this improves the viral infection inhibitory effect of the viral infection inhibitor.

[0027] 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)].

[0028] 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.

[0029] 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.

[0030] The solubility of the organic acid (A) in water at 25°C is 0.4 g / L or less, preferably 0.3 g / L or less, more preferably 0.2 g / L or less, and still more preferably 0.15 g / L or less. When the organic acid (A) has a solubility in water at 25°C of 0.4 g / L or less, the virus infection inhibitor exhibits excellent water resistance and can maintain its excellent virus infection inhibitory effect even after wiping with water. Furthermore, the organic acid (A) has improved compatibility with synthetic resins, allowing the virus infection inhibitor to be uniformly dispersed in the synthetic resin and facilitating exposure of the carboxy group (-COOH), sulfo group (-SOH), phosphonic acid group [-P(=O)(OH)], or phosphate group [-OPO(OH)] of the organic acid (A) to the surface of the synthetic resin, thereby improving the virus infection inhibitory effect of the virus infection inhibitor.

[0031] The solubility of the organic acid (A) in water at 25° C. is preferably 0.001 g / L or more, and more preferably 0.01 g / L or more. When the solubility of the organic acid (A) in water at 25° C. is 0.001 g / L or more, the interaction between the organic acid (A) and the polar groups of viruses is improved, and the viral infection-inhibiting effect is improved.

[0032] The solubility of the sodium salt of organic acid (A) in water at 25°C is preferably 0.3 g / L or more, more preferably 0.5 g / L or more, and even more preferably 1 g / L or more. There is no particular upper limit to the solubility of the sodium salt of organic acid (A) in water at 25°C. The solubility of the sodium salt of organic acid (A) in water at 25°C is preferably, for example, 1000 g / L or less. The surface of a virus infection-inhibiting product described below may be disinfected with a sodium hypochlorite aqueous solution. In this case, a portion of the organic acid (A) ionically bonds with the sodium hypochlorite to form the sodium salt of organic acid (A). When the solubility of the sodium salt of organic acid (A) in water at 25°C is 0.3 g / L or more, the sodium salt of organic acid (A) can be immediately dissolved and removed in the sodium hypochlorite aqueous solution, effectively exposing the organic acid (A) that has not been converted into a sodium salt, thereby maintaining the excellent virus infection-inhibiting effect of the virus infection inhibitor.

[0033] In the present invention, the solubility of an organic acid in water at 25°C refers to the mass of the organic acid that dissolves in 1 L of water at 25°C. 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. The solubility of an organic acid in water at 25°C refers to a value measured at 25°C in accordance with OECD Chemicals Testing Guideline No. 105 (Water Solubility).

[0034] In the present invention, the solubility of a sodium salt of an organic acid in water at 25°C refers to the mass of the sodium salt of the organic acid that dissolves in 1 L of water at 25°C. In other words, the solubility of a sodium salt of an organic acid in water at 25°C refers to the mass of the sodium salt of the organic acid in a saturated solution (25°C) containing 1 L of water. The solubility of a sodium salt of an organic acid in water at 25°C refers to a value measured at 25°C in accordance with OECD Chemicals Testing Guideline No. 105 (Water Solubility).

[0035] The organic acid (A) preferably has a pKa1 of 4.6 or less, and more preferably 3.8 or less, at 25° C. When the organic acid (A) has a pKa1 of 4.6 or less at 25° C., the interaction with the polar group of the virus is improved, and the viral infection inhibitory effect of the viral infection inhibitor is improved.

[0036] Here, in the present invention, the electrolyte HA is A - and H + When an acid dissociates into HCl and the ionization equilibrium equation (1) is obtained, 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.

[0037] In the present invention, 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.

[0038]

number

[0039] In the present invention, the pKa1 of an organic acid at 25° C. refers to a value measured by titration. Specifically, the pKa1 can be determined by titrating an organic acid and 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 for complete neutralization has been added dropwise).

[0040] When the organic acid (A) is a polymer, it preferably contains a crosslinked polymer. This can reduce the solubility of the organic acid (A) in water at 25°C, allowing the virus infection inhibitor to exhibit excellent water resistance and maintain its excellent virus infection inhibitory effect even after wiping with water. Furthermore, the organic acid (A) improves compatibility with synthetic resins, allowing the virus infection inhibitor to be uniformly dispersed in the synthetic resin, and also makes it easier for the carboxy group (-COOH), sulfo group (-SO3H), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2] in the organic acid (A) to be exposed on the surface of the synthetic resin, thereby improving the virus infection inhibitory effect of the virus infection inhibitor.

[0041] 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.

[0042] 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-benzenetricarboxylic acid 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.

[0043] 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.

[0044] 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.

[0045] Examples of the isocyanate crosslinking agent include tolylene diisocyanate, naphthylene-1,5-diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, and trimethylolpropane-modified tolylene diisocyanate.

[0046] 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).

[0047] When the organic acid (A) contains a crosslinked polymer, the gel fraction of the organic acid (A) is preferably 65% ​​by mass or more, more preferably 70% by mass or more, and even more preferably 75% by mass or more. The gel fraction of the organic acid (A) 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 (A) is 65% by mass or more, the virus infection inhibitor exhibits excellent water resistance and can maintain its excellent virus infection inhibitory effect even after wiping with water. Furthermore, the organic acid (A) has improved compatibility with synthetic resins, allowing the virus infection inhibitor to be uniformly dispersed in the synthetic resin. Furthermore, the carboxy group (-COOH), sulfo group (-SOH), phosphonic acid group [-P(=O)(OH)], or phosphate group [-OPO(OH)] of the organic acid (A) to be easily exposed on the surface of the synthetic resin, thereby improving the virus infection inhibitory effect of the virus infection inhibitor. When the gel fraction of the organic acid (A) is 99% by mass or less, the interaction between the organic acid (A) and the polar groups of the virus is improved, and the viral infection-preventing effect is improved.

[0048] The gel fraction of organic acid (A) is a value measured as follows: Organic acid (A) is weighed out 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 organic acid (A) is calculated using the following formula: Gel fraction of organic acid (A) (mass%) = (B / A) × 100

[0049] The organic acid (A) is preferably solid at 1 atmosphere (1013.25 hPa) and 25° C. If the organic acid (A) is solid at 1 atmosphere and 25° C., it will be more likely to appear on the surface of the viral infection-preventing product, such as a processed coating film, and will be more likely to come into contact with viruses, improving the viral infection-preventing effect.

[0050] [Organic acid (B)] The virus infection inhibitor may contain, as an active ingredient, an organic acid (B) having a solubility in water at 25°C of more than 0.4 g / L (hereinafter, sometimes simply referred to as "organic acid (B)"). When the virus infection inhibitor contains organic acid (B) as an active ingredient, the virus infection inhibitor's virus infection inhibitory effect can be immediately exerted, and a fast-acting virus infection inhibitory effect can be imparted to a substrate or the like. Furthermore, when the virus infection inhibitor is contained in a substrate such as a coating film, an excellent virus infection inhibitory effect can be imparted to the virus infection inhibitor product even when the substrate is thick.

[0051] The organic acid (B) may have a solubility in water at 25°C of more than 0.4 g / L. The organic acid (B) 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 functional groups. The total number of the functional groups (carboxy group (-COOH), sulfo group (-SO3H), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2]) in the organic acid (B) may be one or multiple. The organic acid (B) preferably has a carboxy group or a sulfo group, and more preferably a carboxy group, because this can further improve the viral infection-inhibiting effect against enveloped and non-enveloped viruses.

[0052] The organic acid (B) preferably has a plurality of functional groups selected from the group consisting of a carboxyl 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 carboxyl group among the plurality of functional groups, and even more preferably a plurality of carboxyl groups. When the organic acid (B) has a plurality of the above functional groups, the effect of inhibiting viral infection against enveloped and non-enveloped viruses can be further improved. It is preferable that the organic acid (B) does not contain a salt of a sulfo group in the molecule.

[0053] The organic acid (B) is not particularly limited as long as it has a solubility in water at 25°C of more than 0.4 g / L and contains a carboxyl group (-COOH), a sulfo group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphate group [-OPO(OH)2] in the molecule. Examples of the organic acid (B) include triglycolaminic acid (solubility: 1.3 g / L), ethylenediaminetetraacetic acid (solubility: 0.5 g / L), 1,3-diaminopropanetetraacetic acid (solubility: 9 g / L), (S,S)-ethylenediaminedisuccinic acid trihydrate (solubility: 3.0 g / L), diethylenetriaminepentaacetic acid (solubility: 4.0 g / L), ethylenediaminetetra(methylenephosphonic acid) (solubility: 30 g / L), and benzoic acid (solubility: 3.4 g / L). , phthalic acid (solubility: 7.2 g / L), azelaic acid (solubility: 2.4 g / L), fumaric acid (solubility: 6.3 g / L), phthalic acid (solubility: 7.2 g / L), caproic acid (solubility: 11 g / L), enanthic acid (solubility: 2.4 g / L), caprylic acid (solubility: 0.68 g / L), salicylic acid (solubility: 2.0 g / L), gallic acid hydrate (solubility Examples of organic acids include organic acids (B) with a solubility of 11 g / L, benzilic acid (solubility: 1.4 g / L), 4-aminobenzoic acid (solubility: 6 g / L), triglycolaminic acid (solubility: 1.3 g / L), iminodiacetic acid (solubility: 24 g / L), and polyacrylic acid (solubility exceeding 0.4 g / L). 1,3-diaminopropanetetraacetic acid, benzoic acid, and phthalic acid are preferred. The solubilities shown in parentheses are the solubility of the organic acid (B) in water at 25°C. The organic acid (B) may be used alone or in combination of two or more.

[0054] The solubility of the organic acid (B) in water at 25° C. exceeds 0.4 g / L, preferably 1 g / L or more, more preferably 2 g / L or more, and more preferably 3 g / L or more. When the organic acid (B) has a solubility in water at 25° C. of more than 0.4 g / L, the viral infection inhibitor can immediately exert its viral infection inhibitory effect, and a fast-acting viral infection inhibitory effect can be imparted to a substrate or the like.

[0055] Furthermore, when a viral infection inhibitor is contained in a substrate such as a coating film, even if the substrate is thick, the viral infection inhibitor product can be imparted with an excellent viral infection inhibitory effect.

[0056] When the viral infection inhibitor contains an organic acid (A), an organic acid (B), and a compound having a salt of a sulfo group, the viral infection inhibitor product can be more effectively imparted with excellent viral infection inhibitory effects even when the substrate is thick.

[0057] When the virus infection inhibitor contains an organic acid (B), the organic acid (B) is relatively hydrophilic and readily exposed on the surface of the substrate containing the virus infection inhibitor, particularly a substrate containing a synthetic resin, so that the substrate (virus infection-inhibiting product) containing the virus infection inhibitor immediately exhibits a virus infection-inhibiting effect. Because the organic acid (B) readily exposes on the surface of the substrate containing the virus infection inhibitor, particularly a substrate containing a synthetic resin, it is possible to impart an excellent virus infection-inhibiting effect to the substrate even when the substrate is thick.

[0058] The solubility of the organic acid (B) in water at 25° C. is preferably 20 g / L or less, more preferably 18 g / L or less, more preferably 16 g / L or less, more preferably 14 g / L or less, more preferably 12 g / L or less, and more preferably 10 g / L or less. When the solubility of the organic acid (B) in water at 25° C. is 20 g / L or less, discoloration of the surface of a substrate containing the virus infection inhibitor can be reduced, making it easier to maintain the excellent appearance of the substrate.

[0059] The solubility of the sodium salt of organic acid (B) in water at 25°C is preferably 1 g / L or more, more preferably 2 g / L or more, and even more preferably 3 g / L or more. There is no particular upper limit to the solubility of the sodium salt of organic acid (B) in water at 25°C. The solubility of the sodium salt of organic acid (B) in water at 25°C is preferably, for example, 800 g / L or less. The surface of a virus infection-inhibiting product described below may be disinfected with a sodium hypochlorite aqueous solution. In this case, a portion of the organic acid (B) ionically bonds with the sodium hypochlorite to form the sodium salt of organic acid (B). If the solubility of the sodium salt of organic acid (B) in water at 25°C is 1 g / L or more, the sodium salt of organic acid (B) can be immediately dissolved and removed in the sodium hypochlorite aqueous solution, effectively exposing the organic acid (B) that has not been converted into a sodium salt, thereby maintaining the excellent virus infection-inhibiting effect of the virus infection inhibitor.

[0060] The organic acid (B) preferably has a pKa1 of 4.6 or less, and more preferably 4.3 or less, at 25° C. When the organic acid (B) has a pKa1 of 4.6 or less at 25° C., the interaction with the polar group of the virus is improved, and the viral infection inhibitory effect of the viral infection inhibitor is improved.

[0061] The organic acid (B) is preferably a solid at 1 atmosphere (1013.25 hPa) and 25° C. If the organic acid (B) is a 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.

[0062] [Compounds containing sulfo group salts] The virus infection inhibitor preferably further contains a compound having a salt of a sulfo group as an active ingredient.

[0063] 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 ion or NH4 +The compound having a salt of a sulfo group exhibits an excellent viral infection inhibitory effect, particularly against enveloped viruses, due to the molecular structure containing the organic acid (A) and the organic acid (B).

[0064] Furthermore, when the viral infection inhibitor contains a compound having an organic acid (B) and a salt of a sulfo group, the viral infection inhibitor product can be more effectively imparted with excellent viral infection inhibitory effects even when the substrate is thick.

[0065] The compound having a salt of a sulfo group 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).

[0066] The salt of sulfonic acid 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.

[0067] 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.

[0068] When the compound having a sulfo group salt is an organic compound, the affinity with the organic acid (A) and the organic acid (B) is improved, the compound having a sulfo group salt is closer to the organic acid (A) and the organic acid (B), the interaction between the compound having a sulfo group salt and the organic acid (A) and the organic acid (B) is improved, and the viral infection inhibitory effect against both non-enveloped viruses and enveloped viruses is improved.

[0069] 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 (A) and the organic acid (B) is improved, the compound having a sulfo group salt is closer to the organic acid (A) and the organic acid (B), the interaction between the compound having a sulfo group salt and the organic acid (A) and the organic acid (B) is improved, and the viral infection inhibitory effect against both enveloped and non-enveloped viruses is improved.

[0070] 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 monocyclic aromatic ring or the condensed aromatic ring, and is bonded to other atoms via a covalent bond.

[0071] 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 (A) and the organic acid (B) brings the compound having a sulfo group salt closer to the organic acid (A) and the organic acid (B), thereby improving the synergistic effect between the sulfo group salt of the compound having a sulfo group salt and the organic acid (A) and the organic acid (B), and improving the viral infection inhibitory effect against both enveloped and non-enveloped viruses.

[0072] In a compound having a sulfo group salt, when the sulfo group salt is indirectly bonded to an aromatic ring, the sulfo group salt is preferably bonded to the aromatic ring via an alkylene group having 1 to 4 carbon atoms (preferably a methylene group or an ethylene group). While maintaining the affinity between the aromatic ring in the compound having a sulfo group salt and the organic acid (A) and the organic acid (B), the alkylene group allows the sulfo group salt to be appropriately spaced from the aromatic ring, allowing the sulfo group salt to be oriented in a more exposed state, resulting in the viral infection inhibitor exhibiting excellent viral infection inhibitory effects. Examples of alkylene groups having 1 to 4 carbon atoms include a methylene group [-CH2-], an ethylene group [-CH2-CH2-], a propylene group [-CH(CH3)-CH2-], a trimethylene group [-CH2-CH2-CH2-], and a butylene group.

[0073] 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.

[0074] The compound having a sulfo group salt preferably has surfactant properties. When the compound having a sulfo group salt has surfactant properties, the organic acid (A) and the organic acid (B) in the virus infection inhibitor are more likely to be present on the outside. For example, in a virus infection inhibitory product described below, the organic acid (A) and the organic acid (B) are more likely to segregate, further improving the water resistance of the virus infection inhibitory product (molded article). Examples of compounds having a sulfo group salt with surfactant properties include linear alkylbenzene sulfonates, α-olefin sulfonates, alkyl diphenyl ether sulfonates, and polyoxyalkylene alkyl ether sulfate salts. The surfactant properties refer to the ability to adsorb or arrange at interfaces between gas and liquid, gas and solid, liquid and solid, liquid and liquid, and liquid and solid, thereby significantly changing the properties of the interface or surface.

[0075] 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.

[0076] 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 (A) and the organic acid (B) brings the compound having a salt of a sulfo group closer to the organic acid (A) and the organic acid (B), thereby improving the synergistic effect between the sulfo salt of the compound having a salt of a sulfo group and the organic acid (A) and the organic acid (B), and improving the viral infection inhibitory effect against both enveloped and non-enveloped viruses.

[0077] 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.

[0078] 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 hydrophobic portion derived from the α-olefin chain of the compound having a salt of a sulfo group and the organic acid (A) and organic acid (B) brings the compound having a salt of a sulfo group closer to the organic acid (A) and organic acid (B), thereby improving the synergistic effect between the sulfo group salt of the compound having a salt of a sulfo group and the organic acid (A) and organic acid (B), and improving the viral infection inhibitory effect against both enveloped and non-enveloped viruses.

[0079] Examples of alkyl diphenyl ether sulfonates include sodium salts of alkyl diphenyl ether sulfonic acids having a C6 to C18 alkyl group, calcium salts of alkyl diphenyl ether sulfonic acids having a C6 to C18 alkyl group, ammonium salts of alkyl diphenyl ether sulfonic acids having a C6 to C18 alkyl group, magnesium salts of alkyl diphenyl ether sulfonic acids having a C6 to C18 alkyl group, and barium salts of alkyl diphenyl ether sulfonic acids having a C6 to C18 alkyl group, with sodium dodecyl diphenyl ether sulfonate having a C12 alkyl group being preferred.

[0080] 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 hydrophobic portion derived from the alkyl group of the compound having a salt of a sulfo group and the organic acid (A) and the organic acid (B) brings the compound having a salt of a sulfo group closer to the organic acid (A) and the organic acid (B), thereby improving the synergistic effect between the sulfo group salt of the compound having a salt of a sulfo group and the organic acid (A) and the organic acid (B), and improving the viral infection inhibitory effect against both enveloped and non-enveloped viruses.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.).

[0086] When the viral infection inhibitor contains only organic acid (A) as the organic acid, the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (A) (content of compound having a sulfo group salt / content of organic acid (A)) is preferably 1 or less, more preferably 0.7 or less, more preferably 0.6 or less, and even more preferably 0.5 or less. When the viral infection inhibitor contains only organic acid (A) as the organic acid, the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (A) (content of compound having a sulfo group salt / content of organic acid (A)) is preferably 0.005 or more, more preferably 0.01 or more, and even more preferably 0.02 or more. When the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (A) (content of compound having a sulfo group salt / content of organic acid (A)) is 1 or less, the proportion of organic acid (A), which has relatively low solubility, is increased in the viral infection inhibitor, and therefore excellent viral infection inhibitory effects can be stably exerted. When the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (A) (content of the compound having a salt of a sulfo group / content of the organic acid (A)) is 0.005 or more, the adsorption of viruses by the sulfo groups generated by liberating the salt of the sulfo group in the compound having a salt of a sulfo group is promoted, and an excellent effect of inhibiting viral infection is exhibited.

[0087] When the viral infection inhibitor contains organic acid (A) and organic acid (B) as the organic acids, the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (A) (content of the compound having a salt of a sulfo group / content of the organic acid (A)) is preferably 1 or less, more preferably 0.9 or less, more preferably 0.8 or less, and even more preferably 0.7 or less. When the viral infection inhibitor contains organic acid (A) and organic acid (B) as the organic acids, the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (A) (content of the compound having a salt of a sulfo group / content of the organic acid (A)) is preferably 0.005 or more, more preferably 0.01 or more, and even more preferably 0.02 or more. When the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (A) (content of the compound having a sulfo group salt / content of the organic acid (A)) is 1 or less, the proportion of the organic acid (A), which has relatively low solubility, is increased in the viral infection inhibitor, allowing for a stable and excellent viral infection inhibitory effect.When the mass ratio of the content of the compound having a sulfo group salt to the content of the organic acid (A) (content of the compound having a sulfo group salt / content of the organic acid (A)) is 0.005 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, resulting in the development of an excellent viral infection inhibitory effect.

[0088] When the virus infection inhibitor contains organic acid (A) and organic acid (B) as the organic acids, the mass ratio of the content of organic acid (B) to the content of organic acid (A) (organic acid (B) content / organic acid (A) content) is preferably 2 or less, more preferably 1.6 or less, more preferably 1.2 or less, and even more preferably 1 or less. When the virus infection inhibitor contains organic acid (A) and organic acid (B) as the organic acids, the mass ratio of the content of organic acid (B) to the content of organic acid (A) (organic acid (B) content / organic acid (A) content) is preferably 0.1 or more, more preferably 0.2 or more, and even more preferably 0.3 or more. When the mass ratio of the content of organic acid (B) to the content of organic acid (A) (organic acid (B) content / organic acid (A) content) is 2 or less, the virus infection inhibitor exhibits excellent water resistance and can maintain its excellent virus infection inhibitory effect even after wiping with water. When the mass ratio of the content of organic acid (B) to the content of organic acid (A) (content of organic acid (B) / content of organic acid (A)) is 0.1 or more, the viral infection inhibitor can immediately exhibit its viral infection inhibitory effect, and can impart an immediate viral infection inhibitory effect to a substrate or the like.

[0089] [Virus infection inhibitor] When the virus infection inhibitor is particulate, the D90 particle size of the virus infection inhibitor is preferably 2 μm or more, more preferably 3 μm or more, and more preferably 4 μm or more. The D90 particle size of the virus infection inhibitor is preferably 25 μm or less, more preferably 22 μm or less, and more preferably 21 μm or less. When the D90 particle size is 2 μm or more, when the virus infection inhibitor is incorporated into a substrate, the virus infection inhibitor is easily exposed to the substrate surface, improving the virus infection inhibitory effect. When the D90 particle size is 25 μm or less, when the virus infection inhibitor is incorporated into a substrate, the processability is improved and the surface area is increased, facilitating contact with viruses, thereby improving the virus infection inhibitory effect of the virus infection inhibitor. Furthermore, the virus infection inhibitor can be more uniformly attached to the substrate surface, allowing the substrate to be imparted with a more uniform virus infection inhibitory effect.

[0090] As described below, the D90 particle size of the virus infection inhibitor 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 virus infection inhibitor to preferably 2 to 25 μm, the inclusion of coarse particles in the virus infection inhibitor is reduced. Organic acid (A) and organic acid (B) each have a functional group in their molecule [carboxy group (-COOH), sulfo group (-SO3H), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2]]. Adjusting the D90 particle size of the virus infection inhibitor to the above range improves processability when the virus infection inhibitor is incorporated into a substrate and provides the substrate with excellent virus infection inhibitory effects.

[0091] When the viral infection inhibitor is particulate, the D50 particle size of 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. The D50 particle size of 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.

[0092] In the viral infection inhibitor, by setting the D50 particle size within the above-mentioned range (preferably 0.5 to 20 μm) and the D90 particle size to 2 to 25 μm, the inclusion of coarse particles with particle sizes significantly different from the D50 particle size in the viral infection inhibitor can be reduced, and the particle size of the viral infection inhibitor can be made more appropriate.

[0093] Furthermore, by adjusting the particle size of the virus infection inhibitor to a more appropriate range, the amount of functional groups present on the surface of the particulate virus infection inhibitor can be more appropriately adjusted, more effectively imparting the virus infection inhibitor with excellent virus infection inhibitory effects.

[0094] The D90 particle size and D50 particle size of a virus infection inhibitor refer to the particle sizes (90% cumulative particle size and 50% cumulative particle size) at which the cumulative frequency (cumulative from particles with small particle sizes) in the volume-based particle size distribution determined by laser scattering method is 90% and 50%, respectively.

[0095] The viral infection inhibitor contains an organic acid (A) (excluding compounds having a salt of a sulfo group) as an active ingredient. The viral infection inhibitor contains an organic acid (B) (excluding compounds having a salt of a sulfo group) as an active ingredient, if necessary. The viral infection inhibitor contains a compound having a salt of a sulfo group as an active ingredient, if necessary. The viral infection inhibitor is produced by a method that is not particularly limited. When the viral infection inhibitor contains an organic acid (A) and a compound having a salt of a sulfo group and / or an organic acid (B), the viral infection inhibitor can be produced by uniformly mixing the compound having a salt of a sulfo group and / or the organic acid (B) (excluding compounds having a salt of a sulfo group) with the organic acid (A) (excluding compounds having a salt of a sulfo group) in a conventional manner.

[0096] The obtained virus infection inhibitor not only exhibits an excellent virus infection inhibitory effect, but also retains an excellent virus infection inhibitory effect (antiviral activity) even after wiping with water, and has excellent water resistance.

[0097] When the obtained virus infection inhibitor contains the organic acid (B), the virus infection inhibitor can immediately exhibit an excellent virus infection inhibitory effect. Furthermore, when the virus infection inhibitor is incorporated into a substrate, the virus infection inhibitor can exhibit an excellent virus infection inhibitory effect even when the substrate is thick.

[0098] 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.

[0099] Other methods include the plaque method and hemagglutination assay (HAU) as described in "Medical and Pharmaceutical Virology" (first published in April 1990).

[0100] 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 titer between a blank product and a processed product (antiviral activity value) 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 titer between a blank product and a processed product (antiviral activity value) of 2.0 or more for at least one type of virus is considered to be a viral infection inhibitor.

[0101] A coating composition was prepared by adding 30 mg of the virus infection inhibitor to 970 mg of a solvent-free ultraviolet-curable acrylic resin (manufactured by Coattec Co., Ltd., product name "AI-N2") and uniformly mixing. The resulting coating composition was applied to a polyethylene film to a thickness of 18 μm using a wire bar coater #8, and then irradiated with an integrated light dose of 500 mJ / cm using a UV conveyor device, iGrantage [manufactured by iGraphics Co., Ltd., "ECS301G1", irradiator reflector: cold mirror condenser type, UV lamp: H03-L31 (emission length: 365 nm)]. 2 The ultraviolet curing acrylic resin is cured by applying ultraviolet light to form a coating film with a thickness of 18 μm, which is used as the test coating film (processed coating film).

[0102] The antiviral test of the obtained test coating film is carried out in accordance with ISO21702. For the virus suspension 24 hours after the start of the reaction, the virus infectivity (common logarithm value) of the test coating film is calculated by the plaque method. A blank coating film is prepared in the same manner as above except that no virus infection inhibitor is added, and the virus infectivity (common logarithm value) (PFU / cm) is calculated in the same manner as above based on this blank coating film. 2 The difference in common logarithm of the virus infectivity titers (antiviral activity value) is calculated by subtracting the virus infectivity titer of the test coating film from the virus infectivity titer of the blank coating film.

[0103] The virus infection inhibitor has an inhibitory effect on various viruses, and exhibits excellent inhibitory effect on both enveloped and non-enveloped viruses.

[0104] 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.

[0105] Examples of non-enveloped viruses include adenovirus, norovirus, rotavirus, human papillomavirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, poliovirus, and rhinovirus.

[0106] The viral infection inhibitor is preferably used by being present (e.g., attached or supported) on the surface of the base particle. When the viral infection inhibitor contains an organic acid (A) and a compound having a salt of a sulfo group, the compound having a salt of a sulfonic acid group and / or the organic acid (A) may be used by being present (e.g., attached or supported) on the surface of the base particle. When the viral infection inhibitor contains an organic acid (A), an organic acid (B), and a compound having a salt of a sulfo group, any or all of the compound having a salt of a sulfonic acid group, the organic acid (A), and the organic acid (B) may be used by being present (e.g., attached or supported) on the surface of the base particle.

[0107] By having at least one of the active ingredients of the virus infection inhibitor present on the surface of the base particle, the virus infection inhibitor can be dispersed uniformly in the substrate (described below) without forming clumps, which increases the surface area of ​​the virus infection inhibitor, ensuring sufficient contact between the virus and the virus, and allowing the virus infection inhibitor to fully exert its virus infection inhibitory effect.

[0108] The base particles are not particularly limited as long as they do not inhibit the virus infection inhibitory effect of the virus infection inhibitor. Resin particles and inorganic particles are preferred as base particles. Examples of synthetic resins constituting the resin particles include styrene-based resins, acrylic resins, urethane-based resins, vinyl chloride-based resins, ABS resins, and synthetic rubbers such as styrene-butadiene rubber (SBR) and nitrile-butadiene rubber (NBR). The resin particles preferably contain acrylic resins or styrene-based resins, more preferably styrene-based resins, and more preferably polystyrene. The synthetic resins may be used alone or in combination of two or more.

[0109] The content of the acrylic resin in the resin particles is preferably 50% 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, and more preferably 100% by mass.

[0110] The content of the styrene-based resin in the resin particles is preferably 50% 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, and more preferably 100% by mass.

[0111] The styrene-based resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, styrene-based monomers such as styrene, methylstyrene, ethylstyrene, i-propylstyrene, dimethylstyrene, chlorostyrene, and bromostyrene, and copolymers containing, as monomer units, a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer.

[0112] Examples of vinyl monomers copolymerizable with styrene-based monomers include acrylic monomers such as acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, acrylic acid esters (e.g., methyl acrylate, ethyl acrylate, butyl acrylate, etc.), methacrylic acid esters (e.g., methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc.), maleic anhydride, and acrylamide.

[0113] The synthetic resin constituting the resin particles preferably contains an aromatic ring, which attracts the hydrophobic portion of the organic acid (and the compound having a salt of a sulfonic acid group) attached to the surface of the resin particles and orients the carboxyl group (-COOH), sulfo group (-SO3H), phosphonic acid group [-P(=O)(OH)2], or phosphate group [-OPO(OH)2] of the organic acid outward, thereby enabling the virus infection inhibitor to more effectively exert its virus infection inhibitory effect.

[0114] The inorganic material constituting the inorganic particles is not particularly limited, and examples thereof include silica, silica gel, zeolite, hydrotalcite, calcium carbonate, calcium citrate, magnesium carbonate, magnesium hydroxide, diatomaceous earth, kaolin, talc, aluminum hydroxide, titanium oxide, calcium phosphate, calcium sulfate, magnesium carbonate, zinc oxide, manganese oxide, iron oxide, aluminum oxide, barium sulfate, zirconium oxide, tungsten oxide, zirconium phosphate, zirconium carbide, glass, calcium silicate, aluminum silicate, silicon carbide, activated carbon, tobermorite, montmorillonite, bentonite, iron, tin, aluminum, zinc, copper, titanium, nickel, various alloys, etc. The inorganic materials may be used alone or in combination of two or more.

[0115] The D50 particle diameter of the base particles is preferably 0.1 μm or more, more preferably 1 μm or more. The D50 particle diameter of the base particles is preferably 30 μm or less, more preferably 15 μm or less. When the D50 particle diameter of the base particles is 0.1 μm or more, the surface area of ​​the base particles is reduced, the agglomeration of the viral infection inhibitor is reduced, and the viral infection inhibitor and the virus interact more easily, improving the viral infection inhibitory effect. When the D50 particle diameter of the base particles is 30 μm or less, aggregation of the viral infection inhibitor is prevented and the surface area is increased, facilitating contact with the virus, improving the viral infection inhibitory effect of the viral infection inhibitor.

[0116] The D50 particle size of each base particle refers to the particle size (50% cumulative particle size) at which the cumulative frequency (cumulative from particles with small particle sizes) in the volume-based particle size distribution measured by laser scattering method is 50%. When the base particle contains multiple types of base particles, the D50 particle size of the base particle is the value measured based on the entire base particle.

[0117] The amount of the viral infection inhibitor attached to the base particles is preferably 1 part by mass or more, more preferably 5 parts by mass or more, more preferably 7 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the base particles. When the amount of the viral infection inhibitor attached is 1 part by mass or more, the viral infection inhibitor can be uniformly attached to the surface of the base particles, allowing the viral infection inhibitor to more effectively exert its viral infection inhibitory effect.

[0118] The amount of viral infection inhibitor attached to the base particles is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the base particles. When the amount of viral infection inhibitor attached is 50 parts by mass or less, the viral infection inhibitor does not bond to itself, and the viral infection inhibitor is efficiently distributed on the surface of the base particles, improving the viral infection inhibitory effect.

[0119] The manner in which the viral infection inhibitor, the compound having a salt of a sulfonic acid group, the organic acid (A) or the organic acid (B) is attached to the surface of the base particles is not particularly limited. For example, the adhesive strength of the viral infection inhibitor, the compound having a salt of a sulfonic acid group, the organic acid (A) or the organic acid (B) itself may be used, or a binder resin may be used to adhere the viral infection inhibitor, the compound having a salt of a sulfonic acid group, the organic acid (A) or the organic acid (B) to the surface of the base particles. However, since this allows the viral infection inhibitor to effectively exert its viral infection inhibitory effect, it is preferred that the viral infection inhibitor be attached to the surface of the base particles by the adhesive strength of the viral infection inhibitor, the compound having a salt of a sulfonic acid group, the organic acid (A) or the organic acid (B) itself.

[0120] The virus infection inhibitor is used by being contained in a base material to which it is desired to impart a virus infection inhibitory effect, and the base material containing the virus infection inhibitor exhibits a virus infection inhibitory effect as a virus infection inhibitory product.

[0121] The substrate to be loaded with the virus infection inhibitor is not particularly limited as long as it can contain the virus infection inhibitor, and examples include synthetic resin molded products such as films, paints, coating films, wallpaper, decorative sheets, flooring materials, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), interior and interior materials for vehicles (for example, cars, airplanes, ships, etc.) (seats, child seats, and the foams that make up these), kitchen supplies, baby products, and building interior materials.

[0122] The synthetic resin constituting the synthetic resin molded article is not particularly limited, and examples thereof include thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylonitrile styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefin, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyether ether ketone, thermoplastic polyimide, polyamideimide, etc.), thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin, silicone resin, polyurethane, thermosetting polyimide, etc.). The synthetic resins may be used alone or in combination of two or more.

[0123] The virus infection inhibitor may be used by kneading it into a synthetic resin. A method for kneading the virus infection inhibitor into a synthetic resin involves mixing the virus infection inhibitor with a synthetic resin as a raw material to prepare a resin composition, and using this resin composition to obtain a virus infection-inhibiting product in a desired shape as a molded article by a general-purpose synthetic resin molding method. Examples of general-purpose synthetic resin molding methods include extrusion molding, injection molding, and blow molding. A resin composition containing a synthetic resin and the virus infection inhibitor may be used as a synthetic resin molding masterbatch, and the synthetic resin as a raw material may be mixed with the synthetic resin molding masterbatch to produce a virus infection-inhibiting product as a molded article by a general-purpose synthetic resin molding method.

[0124] In the viral infection-preventing product, the content of the viral infection inhibitor is preferably 1 part by mass or more, more preferably 2 parts by mass or more, and more preferably 3 parts by mass or more, per 100 parts by mass of the base material. In the viral infection-preventing product, the content of the viral infection inhibitor is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and more preferably 6 parts by mass or less, per 100 parts by mass of the base material.

[0125] In a virus infection-preventing product having a coating film containing a virus infection inhibitor containing organic acids (A) and (B), the ratio of the coating film thickness (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. The ratio of the coating film thickness (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) is preferably 12 or less, more preferably 10 or less, and even more preferably 8 or less. A ratio of the coating film thickness (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) of 1 or more is preferred because it can prevent appearance defects such as streaks from occurring on the coating film surface during coating film processing. A ratio of the coating film thickness (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) of 12 or less exposes the virus infection inhibitor at the coating film surface, imparting excellent virus infection-preventing effects to the coating film.

[0126] [Masterbatch for synthetic resin molding] The synthetic resin molding masterbatch contains a synthetic resin and a virus infection inhibitor. Only one type of synthetic resin may be used, or two or more types may be used in combination. The synthetic resin may be a thermoplastic resin or a thermosetting resin, but a thermoplastic resin is preferred. Examples of thermoplastic resins include polyolefin resin, polyvinyl chloride resin, polyamide resin, polycarbonate resin, polystyrene resin, polyester resin, acrylonitrile-butadiene-styrene resin (ABS resin), polyethylene terephthalate (PET), polyurethane resin, and polymethyl methacrylate (PMMA).

[0127] When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of the synthetic resin in the masterbatch for synthetic resin molding is preferably 10% by mass or more, more preferably 20% by mass or more. When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of the synthetic resin in the masterbatch for synthetic resin molding is preferably 80% by mass or less, more preferably 60% by mass or less.

[0128] When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of the virus infection inhibitor in the masterbatch for synthetic resin molding is preferably 10% by mass or more, more preferably 15% by mass or more. When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of the virus infection inhibitor in the masterbatch for synthetic resin molding is preferably 80% by mass or less, more preferably 70% by mass or less.

[0129] When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 10% by mass or more, more preferably 15% by mass or more. When the virus infection inhibitor contains only organic acid (A) as the organic acid, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 80% by mass or less, more preferably 70% by mass or less.

[0130] When the virus infection inhibitor contains organic acid (A) and organic acid (B) as organic acids, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 2% by mass or more, and more preferably 3% by mass or more. When the virus infection inhibitor contains organic acid (A) and organic acid (B) as organic acids, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 40% by mass or less, and more preferably 35% by mass or less. When the virus infection inhibitor contains organic acid (A) and organic acid (B) as organic acids, the content of organic acid (B) in the masterbatch for synthetic resin molding is preferably 1% by mass or more, and more preferably 2% by mass or more. When the virus infection inhibitor contains organic acid (A) and organic acid (B) as organic acids, the content of organic acid (B) in the synthetic resin molding masterbatch is preferably 40% by mass or less, more preferably 35% by mass or less, more preferably 30% by mass or less, more preferably 28% by mass or less, more preferably 26% by mass or less, and more preferably 24% by mass or less.

[0131] The total content of the organic acid (A) and the organic acid (B) in the synthetic resin molding masterbatch is preferably 10% by mass or more, more preferably 15% by mass or more, and is preferably 80% by mass or less, more preferably 70% by mass or less, more preferably 60% by mass or less, and still more preferably 50% by mass or less.

[0132] The content of the compound having a salt of a sulfo group in the masterbatch for synthetic resin molding is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more. The content of the compound having a salt of a sulfo group in the masterbatch for synthetic resin molding is preferably 30% by mass or less, and more preferably 25% by mass or less.

[0133] When the virus infection inhibitor is used in a masterbatch for synthetic resin molding, the virus infection inhibitor preferably contains an organic acid (A) that is solid at 200°C under 1 atmosphere (0.101 MPa), more preferably contains an organic acid (A) that is solid at 210°C under 1 atmosphere (0.101 MPa), and even more preferably contains an organic acid (A) that is solid at 220°C under 1 atmosphere (0.101 MPa).When the virus infection inhibitor is used in a masterbatch for synthetic resin molding, the virus infection inhibitor preferably contains an organic acid (B) that is solid at 190°C under 1 atmosphere (0.101 MPa), more preferably contains an organic acid (B) that is solid at 200°C under 1 atmosphere (0.101 MPa), and even more preferably contains an organic acid (B) that is solid at 220°C under 1 atmosphere (0.101 MPa). When molding using a synthetic resin molding masterbatch, a process of heating and melting the synthetic resin molding masterbatch may be performed. When organic acids (A) and (B) that remain solid even at the above temperatures are included, deterioration of the virus infection inhibitor and discoloration of the resulting molded article are more likely to be suppressed. Examples of the organic acid (A) include alginic acid (melting point: 300°C at 1 atmosphere (0.101 MPa)), isophthalic acid (melting point: 345°C at 1 atmosphere (0.101 MPa)), and terephthalic acid (melting point: 300°C at 1 atmosphere (0.101 MPa)). Examples of the organic acid (B) include 1,3-diaminopropanetetraacetic acid (melting point (thermal decomposition temperature): 237°C at 1 atmosphere (0.101 MPa)) and phthalic acid (melting point: 191°C at 1 atmosphere (0.101 MPa)).

[0134] Here, "being solid at Y°C under 1 atmosphere (0.101 MPa)" means that the melting point (or the sublimation point and thermal decomposition temperature in the case of a compound that does not have a melting point) is not below Y°C.

[0135] The resin composition, particularly the synthetic resin molding masterbatch, preferably further contains a surfactant. The surfactant is not particularly limited, and examples thereof include anionic surfactants (excluding anionic surfactants containing a salt of a sulfo group), cationic surfactants, nonionic surfactants, and amphoteric surfactants, with anionic surfactants and nonionic surfactants being preferred. When the synthetic resin molding masterbatch further contains a surfactant, it becomes easier to segregate the organic acid on the surface of the resulting virus infection-preventing product (molded article), thereby further improving the water resistance of the virus infection-preventing product (molded article).

[0136] The anionic surfactant is not particularly limited, and examples thereof include alkyl phosphates such as sodium dodecyl phosphate, potassium dodecyl phosphate, sodium stearyl phosphate, and potassium stearyl phosphate; polyoxyethylene alkyl ether phosphate ester salts such as polyoxyethylene (3) lauryl ether sodium phosphate and polyoxyethylene (3) lauryl ether potassium phosphate; and polyoxyethylene alkyl phenyl ether phosphates such as polyoxyethylene (3) lauryl phenyl ether sodium phosphate and polyoxyethylene (3) lauryl phenyl ether potassium phosphate.

[0137] The nonionic surfactant is not particularly limited, and examples thereof include polyoxyalkylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters (e.g., polyethylene glycol distearate, etc.), 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 alkylolamides, alkylalkanolamides, acetylene glycol, oxyethylene adducts of acetylene glycol, and polyethylene glycol polypropylene glycol block copolymers, with polyoxyethylene fatty acid esters being preferred.

[0138] The amphoteric surfactant is not particularly limited, and examples thereof include alkylaminoacetic acid betaine, alkylamidopropyl betaine, sulfobetaine, alkylamino(mono- or di-)propionate, imidazolinium betaine, alkylamine oxide, alkylaminoethylglycine, alkyldi(aminoethyl)glycine, glycine n-(3-aminopropyl) C10-16 derivative, alkylpolyaminoethylglycine, alkyl-β-alanine, alkyldiethanolamine, polyoxyalkylene alkylamine, and oxyethylene adduct surfactant of diamine.

[0139] The content of the surfactant in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, and is preferably 40% by mass or less, more preferably 30% by mass or less.

[0140] When the resin composition contains a surfactant, the mass ratio of the surfactant content to the organic acid (A) content (surfactant content / organic acid (A) content) in the resin composition is preferably 0.05 or more, more preferably 0.1 or more, and more preferably 0.2 or more. When the resin composition contains a surfactant, the mass ratio of the surfactant content to the organic acid (A) content (surfactant content / organic acid (A) content) in the resin composition is preferably 1 or less, more preferably 0.5 or less, more preferably 0.4 or less, and more preferably 0.3 or less. When the mass ratio of the surfactant content to the organic acid (A) content (surfactant content / organic acid (A) content) in the resin composition is within the above range, the water resistance of the virus infection-preventing product (molded product) can be easily improved.

[0141] When the resin composition contains a surfactant and organic acids (A) and (B) as organic acids, the mass ratio of the surfactant content to the total content of organic acids (A) and (B) in the resin composition (surfactant content / total content of organic acids (A) and (B)) is preferably 0.05 or more, more preferably 0.1 or more, and more preferably 0.2 or more. When the resin composition contains a surfactant, the mass ratio of the surfactant content to the total content of organic acids (A) and (B) in the resin composition (surfactant content / total content of organic acids (A) and (B)) is preferably 1 or less, more preferably 0.5 or less, more preferably 0.4 or less, and more preferably 0.3 or less. In the resin composition, when the mass ratio of the surfactant content to the total content of the organic acid (A) and the organic acid (B) (surfactant content / total content of the organic acid (A) and the organic acid (B)) is within the above range, the water resistance of the virus infection-preventing product (molded article) is easily improved, and the virus infection-preventing effect of the virus infection inhibitor can be immediately exhibited.

[0142] The synthetic resin molding masterbatch is preferably in the form of resin pellets because of its excellent moldability. By melting and molding the resin pellets, a virus infection-preventing product (molded product) with excellent virus infection-preventing effects can be obtained.

[0143] The shape of the resin pellets is not particularly limited, and examples include spherical, cylindrical, and prismatic shapes. From the viewpoint of pellet shape stability, a cylindrical shape is preferred. The maximum length dimension of the resin pellets is preferably 1 mm or more, more preferably 3 mm or more. The maximum length dimension of the resin pellets is preferably 10 mm or less, more preferably 7 mm or less.

[0144] The synthetic resin molding masterbatch can be used by mixing with other resin materials. The other resin materials may be resin pellets. The synthetic resin molding masterbatch and the other resin materials are mixed to obtain a mixed resin material, and then the mixed resin material is molded to obtain a virus infection-preventing product (molded product) with excellent virus infection-preventing effect.

[0145] As the paint, conventionally known paints are used, and examples thereof include oil-based paints (e.g., mixed paints, oil varnishes, etc.), cellulose paints, synthetic resin paints, etc. The paint may contain additives such as pigments, plasticizers, hardeners, extenders, fillers, antioxidants, thickeners, surfactants, etc., within the range that does not impair its physical properties. Incidentally, examples of methods for incorporating the virus infection inhibitor into the paint include a method in which the virus infection inhibitor and the paint are supplied to a dispersing device and uniformly mixed. Incidentally, examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill.

[0146] 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.

[0147] 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. [Example]

[0148] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

[0149] [Preparation of cross-linked polyacrylic acid 1 and 2] 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 (parts by mass) of polyacrylic acid and epoxy-based crosslinking agent in the polyacrylic acid solution are shown in Table 1.

[0150] 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. The gel fraction of crosslinked polyacrylic acid 1 was 85.4% by mass. The gel fraction of crosslinked polyacrylic acid 2 was 99.5% by mass.

[0151] [Table 1]

[0152] (Example 1 19 , Comparative Examples 1 to 5 See Examples 1-15 ) A particulate viral infection inhibitor was prepared by uniformly mixing the compounds having a salt of a sulfo group (salt compounds), organic acid (A), and organic acid (B) of the types shown in Table 2. The contents of the compounds having a salt of a sulfo group (salt compounds), organic acid (A), and organic acid (B) in the viral infection inhibitor are shown in Table 3.

[0153] In the viral infection inhibitor, the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (A) (content of the compound having a salt of a sulfonic acid group / content of the organic acid (A)) is shown in Table 3.

[0154] Table 3 shows the mass ratio of the content of organic acid (B) to the content of organic acid (A) (content of organic acid (B) / content of organic acid (A)) in the viral infection inhibitor.

[0155] In the tables, "compounds having a salt of a sulfo group" are expressed as "salt compounds." The mass ratio of the content of compounds having a salt of a sulfo group to the content of organic acid (A) (content of compounds having a salt of a sulfonic acid group / content of organic acid (A)) is expressed as "salt compounds / organic acid (A)." The mass ratio of the content of organic acid (B) to the content of organic acid (A) (content of organic acid (B) / content of organic acid (A)) is expressed as "organic acid (B) / organic acid (A)."

[0156] Table 2 shows the melting points at 1 atmosphere (1013.25 hPa), solubility in water at 25°C (g / L), pKa1 at 25°C, and molecular weights of organic acids (A) and (B) used to prepare the viral infection inhibitors.

[0157] The solubilities (g / L) of the sodium salts of organic acid (A) and organic acid (B) used to prepare the viral infection inhibitor in water at 25°C are shown in the "Solubility of Na salt" column of Table 2.

[0158] In the tables, "melting point at 1 atmosphere (1013.25 hPa)," "solubility in water at 25°C," and "pKa1 at 25°C" are simply referred to as "melting point," "solubility," and "pKa1," respectively. For cross-linked polyacrylic acid, "thermal decomposition temperature" is listed instead of the melting point. For fumaric acid, "sublimation temperature" is listed instead of the melting point. If "melting point" or "molecular weight" could not be measured in the tables, it is listed as "not measurable." For 1,3-diaminopropanetetraacetic acid, "thermal decomposition temperature" is listed instead of the melting point. In the tables, ">Z" (Z is a number) means greater than Z.

[0159] The D50 particle size (μm) and D90 particle size (μm) of the obtained viral infection inhibitor are shown in Table 3.

[0160] The obtained viral infection inhibitor was subjected to an antiviral test using influenza virus (enveloped virus) and / or feline calicivirus (non-enveloped virus). The results are shown in Table 4.

[0161] [Antiviral test] The initial activity value, activity value after water resistance test, immediate activity value and activity value after treatment with sodium hypochlorite were measured in the following manner, and the results are shown in Tables 4 and 5.

[0162] (initial activity value) A coating composition was prepared by mixing 3 parts by mass of the virus infection inhibitor with 97 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec Co., Ltd. under the trade name "AI-N2"), and the coating composition was applied to a polyethylene film using a wire bar coater #8 to form a coating layer with a thickness of 18 μm.

[0163] Using a UV conveyor device (Eye Graphics "ECS301G1"), ultraviolet light with a wavelength of 365 nm was applied to the coating layer at 25°C with an integrated light intensity of 500 mJ / cm. 2 The ultraviolet-curable acrylic paint was cured by irradiating it so as to form a test coating film with a thickness of 18 μm.

[0164] An antiviral test of the obtained test coating film was carried out in accordance with ISO 21702. For the virus suspension 24 hours after the start of the reaction, the virus infectivity titer (common logarithm value) of the test coating film was calculated by the plaque method.

[0165] 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.

[0166] The antiviral activity value (initial activity value) was calculated by subtracting the virus infectivity value of the test coating film from the virus infectivity value of the blank coating film.

[0167] (Activity value after water resistance test (18μm)) A coating composition was prepared by mixing 3 parts by mass of the virus infection inhibitor with 97 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec Co., Ltd. under the trade name "AI-N2"), and the coating composition was applied to a polyethylene film using a wire bar coater #8 to form a coating layer with a thickness of 18 μm.

[0168] Using a UV conveyor device (Eye Graphics "ECS301G1"), ultraviolet light with a wavelength of 365 nm was applied to the coating layer at 25°C with an integrated light intensity of 500 mJ / cm. 2 The ultraviolet-curable acrylic paint was cured by irradiating it so as to form a coating film with a thickness of 18 μm.

[0169] The resulting coating film was subjected to a water resistance test in accordance with the SIAA's water resistance test for water resistance category 1. Except for the fact that the water adhering to the coating film surface after the water resistance test was removed by blotting with a cloth to prepare a test coating film, an antiviral test was conducted in the same manner as for the initial activity value, and the antiviral activity value after the water resistance test [activity value after water resistance test (18 μm)] was calculated.

[0170] (Fast-acting activity value) The antiviral activity value (immediate activity value) was calculated in the same manner as the measurement method for the initial activity value, except that the virus infectivity value (common logarithm value) of the test coating film was calculated by the plaque method for the virus suspension 10 minutes after the start of the reaction. The virus infectivity value (common logarithm value) of the blank coating film was 6.5 PFU / cm. 2 It was.

[0171] (Activity value after water resistance test (35μm)) The antiviral activity value after the water resistance test [activity value after water resistance test (35 μm)] was calculated in the same manner as for the activity value after the water resistance test (18 μm), except that the coating composition was applied to a polyethylene film to a thickness of 35 μm using a wire bar coater #8 to form a coating layer, and the ultraviolet-curable acrylic paint was cured to form a coating film with a thickness of 35 μm.

[0172] (Activity value after sodium hypochlorite treatment) A coating composition was prepared by mixing 3 parts by mass of the virus infection inhibitor with 97 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec Co., Ltd. under the trade name "AI-N2"), and the coating composition was applied to a polyethylene film using a wire bar coater #8 to form a coating layer with a thickness of 18 μm.

[0173] Using a UV conveyor device (Eye Graphics "ECS301G1"), ultraviolet light with a wavelength of 365 nm was applied to the coating layer at 25°C with an integrated light intensity of 500 mJ / cm. 2 The ultraviolet-curable acrylic paint was cured by irradiating it so as to form a coating film with a thickness of 18 μm.

[0174] A flat square cotton cloth measuring 6 cm on a side [JIS L0803-compliant test cloth (Kanakin No. 3), cotton] was impregnated with 0.5 mL of a 0.05% by mass aqueous solution of sodium hypochlorite (25°C), and the cotton cloth was attached to the friction element of a friction tester, Type I (manufactured by Imoto Machinery Co., Ltd.). The surface of the resulting coating film was rubbed with a pressure of 40 g / cm. 2 After 400 strokes, the surface of the coating was washed with a neutral detergent. The coating was dried at room temperature to prepare a test coating. The cotton cloth was replaced with a new cotton cloth soaked in a 0.05% by mass aqueous solution of sodium hypochlorite every 100 strokes.

[0175] The obtained test coating film was subjected to an antiviral test in the same manner as for the initial activity value, and the antiviral activity value (activity value after treatment with sodium hypochlorite) was calculated.

[0176] (whitening) Test coatings were prepared in the same manner as for measuring the initial activity value. The resulting test coatings were evaluated for whitening resistance in accordance with JIS A 1454, Test Method for Polymer-Based Flooring Materials: Stain Resistance Test. In a test room at 23°C and 50% relative humidity, 2 mL of purified water was dropped onto the test coating surface, covered with a watch glass, and allowed to stand for 24 hours. The water was then removed with a household neutral detergent, and the surface of the test coating was wiped with industrial alcohol and allowed to stand in the test room for 1 hour. The haze of the test coatings was evaluated in accordance with JIS K 7361. The haze value (%) was measured using a haze meter (HM-150, manufactured by Murakami Color Research Laboratory) at a room temperature of 25°C and a relative humidity of 40%. The higher the haze value, the greater the degree of whitening (discoloration) of the coating surface.

[0177] [Table 2]

[0178] [Table 3]

[0179] [Table 4]

[0180] [Table 5]

[0181] [Masterbatch for synthetic resin molding] (Example 12~19 , Comparative Example 6 See Example 15 ) A particulate viral infection inhibitor was prepared by uniformly mixing the compounds having a salt of a sulfo group (salt compounds), organic acids (A) and organic acids (B) of the types shown in Table 6. The contents of the compounds having a salt of a sulfo group (salt compounds), organic acids (A) and organic acids (B) in the viral infection inhibitor are shown in Table 7.

[0182] In the viral infection inhibitor, the mass ratio of the content of the compound having a salt of a sulfo group to the content of the organic acid (A) (content of the compound having a salt of a sulfonic acid group / content of the organic acid (A)) is shown in Table 7.

[0183] Table 7 shows the mass ratio of the content of organic acid (B) to the content of organic acid (A) (content of organic acid (B) / content of organic acid (A)) in the viral infection inhibitor.

[0184] Table 7 shows the D50 particle size (μm) and D90 particle size (μm) of the obtained viral infection inhibitor.

[0185] A masterbatch for synthetic resin molding was prepared by mixing 50 parts by mass of the obtained virus infection inhibitor, 40 parts by mass of polypropylene (trade name "Novatec PP BC6C" manufactured by Japan Polypropylene Corporation) as a synthetic resin, and 10 parts by mass of a surfactant listed in Table 8. In Table 8, "polypropylene" is abbreviated as "PP."

[0186] For Example 28, 60 parts by mass of the obtained virus infection inhibitor and 40 parts by mass of polypropylene (trade name "Novatec PP BC6C", manufactured by Japan Polypropylene Corporation) as a synthetic resin were mixed to prepare a masterbatch for synthetic resin molding.

[0187] Using a Laboplastomill (manufactured by Toyo Seiki Seisakusho, trade name "3S-150"), the obtained synthetic resin molding masterbatch and separately prepared polypropylene (manufactured by Japan Polypropylene Corporation, trade name "Novatec PP BC6C") were mixed in a blending ratio of 1:9 (by mass) and kneaded for 5 minutes at 180°C. Next, the obtained resin composition was press-molded to obtain a sheet-shaped resin molded product (average thickness 1 mm, content of virus infection inhibitor: 5% by mass) as a virus infection-inhibiting product.

[0188] The initial activity value, activity value after water resistance test, and immediate activity value of the obtained virus infection-preventing product were measured using the same test method as for the above coating film, and the results are shown in Table 9. The activity value after water resistance test is shown in the column "Activity value after water resistance test (1 mm)." The initial activity value, activity value after water resistance test, and immediate activity value were measured in the same manner as above, except that a sheet-shaped resin molded product was used instead of the test coating film, and a blank sheet-shaped resin molded product (blank sheet) was prepared using polypropylene (manufactured by Japan Polypropylene Corporation, trade name "Novatec PP BC6C") (no surfactant was used), and this blank sheet was used instead of the blank coating film.

[0189] [Table 6]

[0190] [Table 7]

[0191] [Table 8]

[0192] [Table 9] [Industrial Applicability]

[0193] The virus infection inhibitor of the present invention contains an organic acid (A) having a solubility of 0.4 g / L or less in water at 25°C, and therefore can maintain its excellent virus infection inhibitory effect even after wiping with water. The virus infection inhibitor has an excellent virus infection inhibitory effect against both enveloped and non-enveloped viruses, and exerts a virus infection inhibitory effect against a variety of viruses.

[0194] By incorporating the virus infection inhibitor of the present invention into a substrate, an excellent virus infection inhibitory effect can be imparted to the substrate.

[0195] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority based on Japanese Patent Application No. 2022-142160 filed on September 7, 2022, Japanese Patent Application No. 2022-144910 filed on September 12, 2022, and Japanese Patent Application No. 2023-091659 filed on June 2, 2023, the disclosures of which are incorporated herein by reference in their entirety.

Claims

1. A virus infection inhibitor comprising, as an active ingredient, an organic acid (A) having a solubility in water at 25°C of 0.4 g / L or less, wherein the organic acid (A) is isophthalic acid or terephthalic acid, and wherein the virus infection inhibitor is in particulate form.

2. 2. The virus infection inhibitor according to claim 1, further comprising a compound having a salt of a sulfo group as an active ingredient.

3. The virus infection inhibitor according to claim 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 (A) (content of the compound having a salt of a sulfonic acid group / content of the organic acid (A)) is 1 or less.

4. A virus infection inhibitor as described in claim 1 or claim 2, characterized in that the D90 particle size of the virus infection inhibitor is 2 to 25 μm.

5. 3. The virus infection inhibitor according to claim 1, further comprising an organic acid (B) having a solubility in water at 25°C of more than 0.4 g / L as an active ingredient.

6. A resin composition comprising a synthetic resin and the virus infection inhibitor according to claim 1 or 2.

7. 7. The resin composition according to claim 6, further comprising a surfactant.

8. 7. The resin composition according to claim 6, further comprising, as an active ingredient, an organic acid (B) having a solubility in water at 25°C of more than 0.4 g / L.

9. A masterbatch for synthetic resin molding, comprising a synthetic resin and the virus infection inhibitor according to claim 1 or 2.

10. 10. The synthetic resin molding masterbatch according to claim 9, further comprising a surfactant.

11. 10. The synthetic resin molding masterbatch according to claim 9, further comprising, as an active ingredient, an organic acid (B) having a solubility in water at 25°C of more than 0.4 g / L.

12. A virus infection-preventing product comprising a substrate and the virus infection-preventing agent according to claim 1 or 2 contained in the substrate.

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