Virus infection inhibitor, resin composition, master batch for molding synthetic resin, and virus infection inhibiting product

Abstract

Provided are: a virus infection inhibitor having excellent water resistance and an excellent virus infection inhibiting effect (antiviral properties) even after being wiped with water; and a virus infection inhibiting product using the virus infection inhibitor. The virus infection inhibitor of the present invention comprises an organic acid (A) having a solubility of 0.4 g / L or less in water at 25 DEG C, and preferably further comprises a compound having a salt having a sulfo group, and thus can maintain an excellent virus infection inhibiting effect even after being wiped with water, and can produce a virus infection inhibiting product having an excellent virus infection inhibiting effect.

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 Art

[0002] In recent years, in addition to the spread of seasonal influenza viruses, a new coronavirus (COVID-19) has been spreading around the world.

[0003] In addition, it has been confirmed that highly pathogenic avian influenza viruses have mutated and are infecting humans, and there are concerns about spore viruses with extremely high mortality rates, which has increased people's anxiety about viruses.

[0004] In view of these problems, Patent Document 1 proposes an antiviral synthetic resin composition containing 0.5 parts by weight or more of a sulfonic acid-based surfactant based on 100 parts by weight of the synthetic resin.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2016-128395 Summary of the invention

[0008] Technical problem to be solved by the invention

[0009] However, the antiviral synthetic resin composition has a problem of low water resistance and reduced antiviral property (viral infection inhibitory effect) after wiping with water.

[0010] The present invention provides a virus infection inhibitor that can maintain an excellent virus infection inhibitory effect even after wiping with water. The present invention provides a resin composition, a masterbatch for synthetic resin molding, and a virus infection inhibitory product using the virus infection inhibitor.

[0011] Solutions to technical problems

[0012] 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.

[0013] The resin composition of the present invention comprises a synthetic resin and the viral infection inhibitor.

[0014] The synthetic resin molding masterbatch of the present invention contains a synthetic resin and the viral infection inhibitor.

[0015] The viral infection inhibiting product of the present invention comprises a base material and the viral infection inhibiting agent.

[0016] Effects of the Invention

[0017] The virus infection inhibitor of the present invention contains an organic acid (A) having a water solubility of 0.4 g / L or less in water at 25° C., and therefore can maintain an excellent virus infection inhibitory effect even after wiping with water. DETAILED DESCRIPTION

[0018] The virus 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.

[0019] [Organic acid (A)]

[0020] 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 (hereinafter, sometimes simply referred to as “organic acid (A)”).

[0021] Since the virus infection inhibitor contains an organic acid (A) having a solubility of 0.4 g / L or less in water at 25° C. as an active ingredient, the virus infection inhibitor can remain well in a given place even after wiping with water, and can continuously exert an excellent virus infection inhibitory effect.

[0022] The solubility of the organic acid (A) in water at 25°C may be 0.4 g / L or less, and may also be a polymer. The organic acid (A) has a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] in the molecule, and may have only one of these functional groups or may have multiple functional groups. The total number of the functional groups (carboxyl group (-COOH), sulfonic group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphoric acid group [-OPO(OH)2]) in the organic acid (A) may be one or more. With respect to the organic acid (A), from the viewpoint of being able to further improve the effect of inhibiting viral infection of enveloped viruses and non-enveloped viruses, it is preferred to have a carboxyl group or a sulfonic group, and more preferably a carboxyl group.

[0023] The organic acid (A) preferably has a plurality of functional groups selected from carboxyl (-COOH), sulfonic (-SO3H), phosphonic acid [-P(=O)(OH)2] and phosphoric acid [-OPO(OH)2] in the molecule, more preferably including a carboxyl group in the plurality of functional groups, and more preferably having a plurality of carboxyl groups. When the organic acid (A) has a plurality of such functional groups, the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses can be further improved. It should be noted that the organic acid (A) preferably does not contain a salt of a sulfonic group in the molecule.

[0024] The organic acid (A) is not particularly limited as long as its solubility in water at 25° C. is 0.4 g / L or less and it has a carboxyl group (—COOH), a sulfonic group (—SO3H), a phosphonic acid group [—P(═O)(OH)2] or a phosphoric acid group [—OPO(OH)2] in the molecule. Examples thereof 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), and terephthalic acid (solubility: 0.02 g / L). L), methylenedisalicylic acid (solubility: 0 g / L), cis-Δ4-tetrahydrophthalic acid (solubility: 0 g / L), nonanoic acid (solubility: 0.28 g / L), capric acid (solubility: 0.15 g / L), lauric acid (solubility: 0.0048 g / L), myristic acid (solubility: 0 g / L), palmitic acid (solubility: 0 g / L), stearic acid (solubility: 0 g / L), myristoleic acid (solubility: 0 g / L), oleic acid (solubility: 0 g / L), ricinoleic acid (solubility: 0 g / L), etc., preferably alginic acid, isophthalic acid, and terephthalic acid. The solubility recorded in the brackets is the solubility of the organic acid (A) in water at 25°C. It should be noted that the organic acid (A) can be used alone or in combination of two or more.

[0025] When the organic acid (A) is a polymer, examples of the organic acid (A) include polymers having a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] in the side chain of a linear polymer. When the organic acid (A) is a polymer, a polymer having a carboxyl group or a sulfonic group is preferred from the viewpoint that the viral infection inhibitor exerts an excellent viral infection inhibitory effect.

[0026] Among the polymers having a carboxyl group (-COOH), a sulfone group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] 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, and a vinyl polymer is preferred.

[0027] There are no particular limitations on the polymers having a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] in the side chain of the linear polymer, and examples thereof include: polymers containing monomer components having a carboxyl group, polymers containing monomer components having a sulfonic group, polymers containing monomer components having a phosphonic acid group [-P(=O)(OH)2], polymers containing monomer components having a phosphoric acid group [-OPO(OH)2], and the like.

[0028] Examples of monomers having a carboxyl group include acrylic acid, methacrylic acid, acrylic acid, methacrylic acid, β-carboxyethyl (meth)acrylate, 5-carboxypentyl (meth)acrylate, mono(meth)acryloyloxyethyl succinate, ω-carboxypolycaprolactone mono(meth)acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, carboxybetaine monomers, etc., preferably acrylic acid and methacrylic acid. It should be noted that the monomers having a carboxyl group may be used alone or in combination of two or more.

[0029] Examples of the monomer having a sulfonic group include p-styrenesulfonic acid, m-styrenesulfonic acid, o-styrenesulfonic acid, acrylamide tert-butylsulfonic acid, vinylsulfonic acid, 2-(methacryloyloxy)ethanesulfonic acid, 3-(methacryloyloxy)propanesulfonic acid, 4-[(3-methacrylamidopropyl)dimethylammonio]butane-1-sulfonic acid, etc. The monomer having a sulfonic group may be used alone or in combination of two or more.

[0030] Examples of the monomer having a phosphonic acid group include vinylphosphonic acid, vinylphosphonic acid alkyl esters, etc. The monomer having a phosphonic acid group may be used alone or in combination of two or more.

[0031] Examples of the monomer having a phosphoric acid group include phosphoric acid monoacrylate, phosphoric acid diacrylate, phosphoric acid monomethacrylate, phosphoric acid dimethacrylate, 2-hydroxyethyl phosphoric acid methacrylate, etc. The monomer having a phosphoric acid group may be used alone or in combination of two or more.

[0032] When the organic acid (A) is a polymer, from the viewpoint of improving the viral infection inhibitory effect of the viral infection inhibitor, the total content of monomer components having a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] 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.

[0033] A polymer having a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] in the side chain of a linear polymer may include: a monomer component that can copolymerize with a monomer having a carboxyl group (-COOH), a sulfonic group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2].

[0034] Examples of the copolymerizable monomers include alkyl acrylates, alkyl methacrylates, vinyl alkyl ethers, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, sodium acrylate, acrylamide, methacrylamide, diacetone acrylamide, vinyltoluene, vinylpyridine, methyl methacrylate, sodium methacrylate, and hydroxyethyl methacrylate.

[0035] Polymers having a carboxyl group (-COOH), a sulfone group (-SO3H), a phosphonic acid group [-P(=O)(OH)2] or a phosphoric acid group [-OPO(OH)2] in the side chain of a linear polymer can be produced by a general free radical polymerization method.

[0036] 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 more preferably 0.15 g / L or less. In the organic acid (A), by making the solubility in water at 25°C 0.4 g / L or less, the virus infection inhibitor exhibits excellent water resistance, and can maintain an excellent virus infection inhibitory effect even after wiping with water. In addition, the affinity of the organic acid (A) and the synthetic resin is improved, and the virus infection inhibitor can be uniformly dispersed in the synthetic resin, and the carboxyl group (-COOH), sulfonic group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphoric acid group [-OPO(OH)2] in the organic acid (A) is easily exposed on the surface of the synthetic resin, thereby improving the virus infection inhibitory effect of the virus infection inhibitor.

[0037] The solubility of the organic acid (A) in water at 25°C is preferably 0.001 g / L or more, 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 group of the virus is enhanced, and the effect of inhibiting viral infection is enhanced.

[0038] The solubility of the sodium salt of the 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 more preferably 1 g / L or more. The upper limit of the solubility of the sodium salt of the organic acid (A) in water at 25°C is not particularly limited. The solubility of the sodium salt of the organic acid (A) in water at 25°C is, for example, preferably 1000 g / L or less. Sometimes, the surface of the viral infection inhibiting product described later is disinfected with an aqueous sodium hypochlorite solution. In this case, a portion of the organic acid (A) is ionically bonded with sodium hypochlorite to form the sodium salt of the organic acid (A). When the solubility of the sodium salt of the organic acid (A) in water at 25°C is 0.3 g / L or more, the sodium salt of the organic acid (A) can be immediately dissolved in the aqueous sodium hypochlorite solution and removed, and the organic acid (A) that has not become a sodium salt can be effectively exposed, thereby maintaining the excellent viral infection inhibiting effect of the viral infection inhibitor.

[0039] It should be noted that, in the present invention, the solubility of an organic acid in water at 25°C refers to the mass of an organic acid dissolved in 1 L of water at 25°C. That is, the solubility of an organic acid in water at 25°C refers to the mass of an 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 Chemical Testing Guide No. 105 (Water Solubility).

[0040] In the present invention, the solubility of the sodium salt of an organic acid in water at 25°C refers to the mass of the sodium salt of an organic acid dissolved in 1 L of water at 25°C. That is, the solubility of the sodium salt of an organic acid in water at 25°C refers to the mass of the sodium salt of an organic acid in a saturated solution (25°C) containing 1 L of water. The solubility of the sodium salt of an organic acid in water at 25°C refers to a value measured at 25°C in accordance with OECD Chemical Testing Guide No. 105 (Water Solubility).

[0041] The pKa1 of the organic acid (A) at 25°C is more preferably 4.6 or less, and more preferably 3.8 or less. When the pKa1 of the organic acid (A) at 25°C is 4.6 or less, the interaction with the polar group of the virus is enhanced, and the virus infection inhibitory effect of the virus infection inhibitor is enhanced.

[0042] Here, in the present invention, the electrolyte HA is ionized into A - and H + When the ionization equilibrium equation (1) is taken, the acid dissociation constant Ka is defined by equation (2), and pKa is defined by the common logarithm of the reciprocal of the acid dissociation constant Ka (3).

[0043] In the present invention, when the organic acid is a polybasic acid, the polybasic acid is ionized in multiple stages, and pKa1 refers to a pKa calculated based on the ionization constant of the first stage.

[0044] [Mathematical formula 1]

[0045]

[0046] pKa=-logKa (3)

[0047] In the present invention, pKa1 of an organic acid at 25°C refers to a value measured by titration. Specifically, pKa1 can be determined by titrating an organic acid with sodium hydroxide at 25°C and measuring the pH at 25°C at the half-equivalent point (the point at which half the amount required for complete neutralization has been added).

[0048] When the organic acid (A) is a polymer, the organic acid (A) preferably comprises a cross-linked polymer. The solubility of the organic acid (A) in water at 25°C can be reduced, so that the virus infection inhibitor exhibits excellent water resistance, and can maintain an excellent virus infection inhibitory effect even after wiping with water. In addition, the affinity of the organic acid (A) and the synthetic resin is improved, so that the virus infection inhibitor can be uniformly dispersed in the synthetic resin, and the carboxyl group (-COOH), sulfonic group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphoric acid group [-OPO(OH)2] in the organic acid (A) is easily exposed on the surface of the synthetic resin, thereby improving the virus infection inhibitory effect of the virus infection inhibitor.

[0049] The method for cross-linking the polymer is not particularly limited and can be carried out by a general method. Examples of the method for cross-linking the polymer include: (1) a method in which a cross-linking aid and a peroxide are supplied to the polymer and the polymer is heated to cross-link the polymer; (2) a method in which a cross-linking agent is supplied to the polymer and the polymer is heated to cross-link the polymer, etc.

[0050] The crosslinking aid is not particularly limited, and examples thereof include divinylbenzene, trimethylolpropane trimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, triallyl trimellitate, triallyl isocyanurate, ethylvinylbenzene, neopentyl glycol dimethacrylate, triallyl 1,2,4-benzenetricarboxylate, 1,6-hexanediol dimethacrylate, lauryl methacrylate, stearyl methacrylate, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, etc. It should be noted that the crosslinking aid may be used alone or in combination of two or more.

[0051] The peroxide is not particularly limited, and examples thereof include 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, tert-butyl perbenzoate, cumene hydroperoxide, tert-butyl hydroperoxide, 1,1-di(tert-butylperoxy)-3,3,5-trimethylhexane, n-butyl-4,4-di(tert-butylperoxy)valerate, α,α'-bis(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3, tert-butylperoxyisopropylbenzene, etc. It should be noted that the peroxide may be used alone or in combination of two or more.

[0052] The crosslinking agent is not particularly limited, and a general-purpose crosslinking agent can be used, for example, epoxy crosslinking agents, isocyanate crosslinking agents, imine crosslinking agents, etc. The crosslinking agent may be used alone or in combination of two or more.

[0053] Examples of the isocyanate crosslinking agent include tolylene diisocyanate, naphthylene-1,5-diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, and trimethylolpropane-modified toluene diisocyanate.

[0054] Preferred examples of epoxy crosslinking agents include N,N′-(cyclohexane-1,3-diylbismethylene)bis(diglycidylamine) and N,N,N′,N′-tetraglycidyl-1,3-phenylenedi(methanamine).

[0055] In the case where the organic acid (A) contains a cross-linked polymer, the gel fraction of the organic acid (A) is preferably 65% ​​by mass or more, more preferably 70% by mass or more, and more preferably 75% by mass or more. The gel fraction of the organic acid (A) is preferably 99% by mass or less, more preferably 97% by mass or less, and more preferably 96% by mass or less. When the gel fraction of the organic acid (A) is 65% by mass or more, the virus infection inhibitor exhibits excellent water resistance and can maintain an excellent virus infection inhibitory effect even after wiping with water. In addition, the affinity of the organic acid (A) and the synthetic resin is improved, and the virus infection inhibitor can be uniformly dispersed in the synthetic resin, and the carboxyl group (-COOH), sulfonic group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphoric acid group [-OPO(OH)2] in the organic acid (A) is 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 mass % or less, the interaction between the organic acid (A) and the polar group of the virus is enhanced, and the effect of inhibiting viral infection is enhanced.

[0056] The gel fraction of the organic acid (A) refers to the value measured by the following method. Ag organic acid (A) is weighed, immersed in purified water at 60°C for 24 hours, the insoluble components are filtered out with a 200-mesh metal mesh, the residue on the metal mesh is vacuum dried at 80°C for 16 hours, the weight of the dried residue is measured (Bg), and the gel fraction of the organic acid (A) is calculated by the following formula.

[0057] Gel fraction of organic acid (A) (mass %) = (B / A) × 100

[0058] The organic acid (A) is preferably solid at 1 atmosphere (1013.25 hPa) and 25° C. When the organic acid (A) is solid at 1 atmosphere and 25° C., it is easily exposed on the surface of the processed virus infection inhibiting product such as a coating film, and is easily in contact with viruses, thereby improving the virus infection inhibiting effect.

[0059] [Organic acid (B)]

[0060] The virus infection inhibitor may contain an organic acid (B) (hereinafter, sometimes referred to as "organic acid (B)") having a solubility of more than 0.4 g / L in water at 25°C as an active ingredient. If the virus infection inhibitor contains an organic acid (B) as an active ingredient, the virus infection inhibitor can immediately show the virus infection inhibitor effect, and a fast-acting virus infection inhibitor effect can be imparted to a substrate, etc. In addition, when a substrate such as a coating film contains the virus infection inhibitor, even when the thickness of the substrate is relatively thick, an excellent virus infection inhibitor effect can be imparted to the virus infection inhibitor product.

[0061] The solubility of the organic acid (B) in water at 25°C may be greater than 0.4 g / L. The organic acid (B) has a carboxyl group (-COOH), a sulfonyl 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 may have multiple functional groups. The total number of the functional groups (carboxyl group (-COOH), sulfonyl group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphate group [-OPO(OH)2]) in the organic acid (B) may be one or more. Since the organic acid (B) can further improve the inhibitory effect on viral infection of enveloped viruses and non-enveloped viruses, it is preferred to have a carboxyl group or a sulfonyl group, and more preferably a carboxyl group.

[0062] The organic acid (B) preferably has a plurality of functional groups selected from carboxyl (-COOH), sulfonic (-SO3H), phosphonic [-P(=O)(OH)2] and phosphoric [-OPO(OH)2] in the molecule, more preferably contains a carboxyl group in the plurality of functional groups, and more preferably has a plurality of carboxyl groups. When the organic acid (B) has a plurality of such functional groups, the viral infection inhibitory effect on enveloped viruses and non-enveloped viruses can be further improved. In addition, the organic acid (B) preferably does not contain a salt of a sulfonic group in the molecule.

[0063] The organic acid (B) is not particularly limited as long as its solubility in water at 25° C. exceeds 0.4 g / L and it has a carboxyl group (—COOH), a sulfonic group (—SO3H), a phosphonic acid group [—P(═O)(OH)2] or a phosphoric acid group [—OPO(OH)2] in the molecule. Examples thereof include nitrilotriacetic acid (solubility: 1.3 g / L), ethylenediaminetetraacetic acid (solubility: 0.5 g / L), 1,3-propylenediaminetetraacetic acid (solubility: 9 g / L), (S,S)-ethylenediamine disuccinic acid trihydrate (solubility: 3.0 g / L), diethylenetriaminepentaacetic acid (solubility: 4.0 g / L), ethylenediaminetetra(methylenephosphonic acid) (solubility: 30 g / L), 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), heptanoic acid (solubility: 2.4 g / L), octanoic acid (solubility: 0.68 g / L), salicylic acid (solubility: 2.0 g / L), gallic acid hydrate (solubility: 11 g / L), benzilic acid (solubility: 1.4 g / L), 4-aminobenzoic acid (solubility: 6 g / L), nitrilotriacetic acid (solubility: 1.3 g / L), iminodiacetic acid (solubility: 24 g / L), polyacrylic acid (solubility exceeds 0.4 g / L), etc. Preferred are 1,3-propylenediaminetetraacetic acid, benzoic acid, and phthalic acid. The solubility described in parentheses is 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.

[0064] The solubility of the organic acid (B) in water at 25°C is more than 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. Among organic acids (B), by making the solubility in water at 25°C more than 0.4 g / L, the viral infection inhibitory effect brought about by the viral infection inhibitor can be immediately manifested, and a fast-acting viral infection inhibitory effect can be imparted to a substrate or the like.

[0065] Furthermore, when a virus infection inhibitor is contained in a base material such as a coating film, an excellent virus infection inhibitory effect can be imparted to the virus infection inhibitory product even when the thickness of the base material is thick.

[0066] When the virus infection inhibitor comprises a compound of an organic acid (A), an organic acid (B) and a salt having a sulfonic group, an excellent virus infection inhibitory effect can be more effectively imparted to the virus infection inhibitory product even when the thickness of the substrate is thick.

[0067] When the viral infection inhibitor contains an organic acid (B), the organic acid (B) has a relatively high hydrophilicity and is easily exposed immediately on the surface of a substrate containing the viral infection inhibitor, especially a substrate containing a synthetic resin, and the substrate containing the viral infection inhibitor (viral infection inhibitor product) immediately exhibits a viral infection inhibitory effect. The organic acid (B) is easily exposed immediately on the surface of a substrate containing the viral infection inhibitor, especially a substrate containing a synthetic resin, and therefore, even when the thickness of the substrate is relatively thick, it is possible to impart an excellent viral infection inhibitory effect to the substrate.

[0068] 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 the substrate containing the viral infection inhibitor can be reduced, and the excellent appearance of the substrate can be easily maintained.

[0069] The solubility of the sodium salt of the organic acid (B) in water at 25°C is preferably 1 g / L or more, more preferably 2 g / L or more, and more preferably 3 g / L or more. The upper limit of the solubility of the sodium salt of the organic acid (B) in water at 25°C is not particularly limited. The solubility of the sodium salt of the organic acid (B) in water at 25°C is, for example, preferably 800 g / L or less. Sometimes, the surface of the viral infection inhibiting product described later is disinfected with an aqueous sodium hypochlorite solution. In this case, a portion of the organic acid (B) is ionically bonded with sodium hypochlorite to form the sodium salt of the organic acid (B). When the solubility of the sodium salt of the organic acid (B) in water at 25°C is 1 g / L or more, the sodium salt of the organic acid (B) can be immediately dissolved in the aqueous sodium hypochlorite solution and removed, and the organic acid (B) that has not formed a sodium salt can be effectively exposed, thereby maintaining the excellent viral infection inhibiting effect of the viral infection inhibitor.

[0070] The pKa1 of the organic acid (B) at 25°C is more preferably 4.6 or less, and more preferably 4.3 or less. When the pKa1 of the organic acid (B) at 25°C is 4.6 or less, the interaction with the polar group of the virus is enhanced, and the virus infection inhibitory effect of the virus infection inhibitor is enhanced.

[0071] The organic acid (B) is preferably solid at 1 atmosphere (1013.25 hPa) and 25° C. When the organic acid (B) is solid at 1 atmosphere and 25° C., it is easily exposed on the surface of the processed virus infection inhibiting product such as a coating film, and is easily in contact with viruses, thereby improving the virus infection inhibiting effect.

[0072] [Compound having a salt of a sulfonic group]

[0073] The viral infection inhibitor preferably further contains a salt compound having a sulfonic group as an active ingredient.

[0074] The compound having a salt of a sulfonic group is a salt having a sulfonic group (-SO3H) in the molecule. Among the compounds having a salt of a sulfonic group, the salt containing a sulfonic group (-SO3X: ​​X is a metal ion or NH4 + ) in the molecular structure part, and exerts a virus infection inhibitory effect together with the organic acid (A) and the organic acid (B). The salt compound having a sulfonic group has an excellent virus infection inhibitory effect particularly on enveloped viruses.

[0075] Furthermore, if the virus infection inhibitor contains a compound of an organic acid (B) and a salt having a sulfonic group, an excellent virus infection inhibitory effect can be more effectively imparted to the virus infection inhibitory product even when the thickness of the substrate is thick.

[0076] It should be noted that the compound having a salt of a sulfonic group may have a carboxyl group (-COOH), a phosphonic acid group [-P(=O)(OH)2], a phosphoric acid group [-OPO(OH)2], a thiol group (-SH) and a hydroxyl group (-OH).

[0077] It should be noted that the salt of the 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+ ] etc., preferably sodium salt (-SO3Na).

[0078] The compound having a salt of a sulfonic group is preferably an organic compound. In the present invention, the organic compound refers to a compound containing at least one (preferably two or more) carbon atoms in the molecule and containing a carbon-hydrogen bond (CH bond).

[0079] When the salt compound having a sulfonic group is an organic compound, the affinity with the organic acid (A) and the organic acid (B) is improved, the salt compound having a sulfonic group is close to the organic acid (A) and the organic acid (B), the interaction between the salt compound having a sulfonic group and the organic acid (A) and the organic acid (B) is improved, and the viral infection inhibitory effect on both viruses without an envelope (non-enveloped viruses) and viruses with an envelope (enveloped viruses) is improved.

[0080] The compound of the salt having a sulfonic group preferably has an aromatic ring. When the compound of the salt having a sulfonic group has an aromatic ring, the affinity with the organic acid (A) and the organic acid (B) is improved, the compound of the salt having a sulfonic group is close to the organic acid (A) and the organic acid (B), the interaction between the compound of the salt having a sulfonic group and the organic acid (A) and the organic acid (B) is improved, and the inhibitory effect on viral infection of both enveloped viruses and non-enveloped viruses is improved.

[0081] The aromatic ring may be a monocyclic aromatic ring or a monocyclic aromatic ring compounded and fused (fused aromatic ring). The aromatic ring is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a biphenyl ring, a phenoxyphenyl ring, etc., preferably a benzene ring and a naphthalene ring. Among the aromatic rings, any one or more hydrogen atoms in the monocyclic aromatic ring and the fused aromatic ring are captured and bonded to other atoms through covalent bonds.

[0082] In the compound having a salt of a sulfonic group, the salt of a sulfonic group is preferably directly or indirectly bonded to an aromatic ring, and more preferably directly bonded to an aromatic ring. Due to the affinity of the aromatic ring of the compound having a salt of a sulfonic group with the organic acid (A) and the organic acid (B), the compound having a salt of a sulfonic group is close to the organic acid (A) and the organic acid (B), and the synergistic effect of the salt of the sulfonic group of the compound having a salt of a sulfonic group with the organic acid (A) and the organic acid (B) can be improved, and the inhibitory effect on viral infection of both enveloped viruses and non-enveloped viruses can be improved.

[0083] In the compound having a salt of a sulfonic group, when the salt of the sulfonic group is indirectly bonded to the aromatic ring, the salt of the sulfonic group is preferably bonded to the aromatic ring via an alkylene group having 1 to 4 carbon atoms (preferably a methylene group or an ethylene group). While maintaining the affinity of the aromatic ring in the compound having a salt of a sulfonic group with the organic acid (A) and the organic acid (B), the salt of the sulfonic group is in a state of being appropriately separated from the aromatic ring due to the alkylene group, and the salt of the sulfonic group can be oriented to a state of being further exposed, so that the viral infection inhibitor exerts an excellent viral infection inhibitory effect. It should be noted that as examples of the alkylene group having 1 to 4 carbon atoms, there can be mentioned: a methylene group [-CH2-], an ethylene group [-CH2-CH2-], a propylene group [-CH(CH3)-CH2-], a trimethylene group [-CH2-CH2-], a butylene group, and the like.

[0084] The compound having a salt of a sulfonic group is not particularly limited as long as it has one or more sulfonic groups in the molecule, and examples thereof include linear alkylbenzene sulfonates, α-olefin sulfonates, alkyl diphenyl ether sulfonates, polyoxyalkylene alkyl ether sulfate salts, and polymers having a salt of a sulfonic group in a side chain of a linear polymer.

[0085] The compound having a salt of a sulfonic group preferably has the effect of a surfactant. When the compound having a salt of a sulfonic group has the effect of a surfactant, it is easy to make the organic acid (A) and the organic acid (B) in the virus infection inhibitor exist outside. For example, in the virus infection inhibition product described later, it is easy to make the organic acid (A) and the organic acid (B) segregate, which can further improve the water resistance of the virus infection inhibition product (molded product). As such a compound having a salt of a sulfonic group having the effect of a surfactant, for example, linear alkylbenzene sulfonate, α-olefin sulfonate, alkyl diphenyl ether sulfonate, polyoxyalkylene alkyl ether sulfate salt, etc. can be cited. It should be noted that the effect of a surfactant refers to: adsorption or arrangement at the interface between gas-liquid, gas-solid, liquid-solid, liquid-liquid, and liquid-solid, so that the properties of its interface or surface are significantly changed.

[0086] Examples of the linear alkylbenzene sulfonate include sodium dodecylbenzene sulfonate, calcium dodecylbenzene sulfonate, ammonium dodecylbenzene sulfonate, magnesium dodecylbenzene sulfonate, barium dodecylbenzene sulfonate, sodium tridecylbenzene sulfonate, ammonium tridecylbenzene sulfonate, sodium tetradecylbenzene sulfonate, and ammonium tetradecylbenzene sulfonate. Sodium dodecylbenzene sulfonate is preferred.

[0087] The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonate is preferably 10 or more, more preferably 11 or more, and more preferably 12 or more. The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonic acid is preferably 25 or less, more preferably 20 or less, and more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the compound having a salt with a sulfonic group is close to the organic acid (A) and the organic acid (B) due to the affinity of the hydrophobic part derived from the alkyl group and the organic acid (A) and the organic acid (B), and the synergistic effect of the salt of the compound having a sulfonic group with the organic acid (A) and the organic acid (B) can be enhanced, and the inhibitory effect on both enveloped viruses and non-enveloped viruses can be enhanced.

[0088] Examples of the α-olefin sulfonate include sodium C12-C18 olefin sulfonate, calcium C12-C18 olefin sulfonate, ammonium C12-C18 olefin sulfonate, magnesium C12-C18 olefin sulfonate, barium C12-C18 olefin sulfonate, and the like. Sodium C14 tetradecene sulfonate is preferred.

[0089] The carbon number of the α-olefin in the α-olefin sulfonate is preferably 12 or more, more preferably 14 or more. The carbon number of the α-olefin in the α-olefin sulfonate is preferably 22 or less, more preferably 18 or less. When the carbon number of the α-olefin is within the above range, the compound having a sulfonate salt and the organic acid (A) and the organic acid (B) are close due to the affinity of the hydrophobic part derived from the α-olefin chain of the compound having a sulfonate salt with the organic acid (A) and the organic acid (B), and the synergistic effect of the sulfonate salt of the compound having a sulfonate salt with the organic acid (A) and the organic acid (B) can be enhanced, and the viral infection inhibitory effect on both enveloped viruses and non-enveloped viruses can be enhanced.

[0090] Examples of the alkyl diphenyl ether sulfonate include sodium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, calcium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, ammonium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, magnesium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, and barium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18. Sodium dodecyl diphenyl ether sulfonate having an alkyl group of C12 is preferred.

[0091] The number of carbon atoms in the alkyl diphenyl ether sulfonate is preferably 8 or more, more preferably 10 or more. The number of carbon atoms in the alkyl diphenyl ether sulfonate is preferably 24 or less, more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the compound having a sulfonate salt and the organic acid (A) and the organic acid (B) are close due to the affinity of the hydrophobic part derived from the alkyl group of the compound having a sulfonate salt with the organic acid (A) and the organic acid (B), and the synergistic effect between the sulfonate salt of the compound having a sulfonate salt and the organic acid (A) and the organic acid (B) can be enhanced, and the inhibitory effect on both enveloped viruses and non-enveloped viruses can be enhanced.

[0092] In the polymer having a salt of a sulfonic group in a side chain of the linear polymer, the linear polymer is not particularly limited, but is preferably a vinyl polymer, polyester, or polyurethane, and preferably a vinyl polymer.

[0093] The polymer having a salt of a sulfonic group in a 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.

[0094] In addition, the polymer having a salt of a sulfonic group in the side chain of the linear polymer is preferably a homopolymer or copolymer of a monomer having a salt of a sulfonic group. Examples of the monomer having a salt of a sulfonic group include sodium p-styrene sulfonate, sodium m-styrene sulfonate, sodium o-styrene sulfonate, calcium p-styrene sulfonate, calcium m-styrene sulfonate, calcium o-styrene sulfonate, ammonium p-styrene sulfonate, ammonium m-styrene sulfonate, ammonium o-styrene sulfonate, sodium naphthalene sulfonate, and calcium naphthalene sulfonate. Sodium styrene sulfonate is preferred, and sodium p-styrene sulfonate is more preferred from the perspective of less steric hindrance in the reactivity with viruses.

[0095] It should be noted that the monomer having a salt of a sulfonic group can form a copolymer with other monomers. Examples of copolymerizable monomers include alkyl acrylates, alkyl methacrylates, vinyl alkyl ethers, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, acrylic acid, sodium acrylate, methacrylic acid, maleic acid, fumaric acid, maleic anhydride, acrylamide, methacrylamide, diacetone acrylamide, vinyltoluene, xylenesulfonic acid, vinylpyridine, vinylsulfonic acid, vinyl alcohol, methyl methacrylate, sodium methacrylate, hydroxyethyl methacrylate, and the like, preferably styrene.

[0096] A polymer having a salt of a sulfonic group in the side chain of a linear polymer can be produced by a general method, for example: a method of subjecting a monomer having a salt of a sulfonic group to free radical polymerization; a method of subjecting a monomer having a salt of a sulfonic group and a monomer copolymerizable with the monomer to free radical polymerization; a method of neutralizing the sulfonic group of a polymer containing a monomer component having a sulfonic group using an alkali (such as sodium hydroxide, calcium hydroxide, potassium hydroxide, ammonium hydroxide, etc.), etc.

[0097] In the virus infection inhibitor, when only the organic acid (A) is included as the organic acid, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is preferably 1 or less, more preferably 0.7 or less, more preferably 0.6 or less, and more preferably 0.5 or less. In the virus infection inhibitor, when only the organic acid (A) is included as the organic acid, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is preferably 0.005 or more, more preferably 0.01 or more, and more preferably 0.02 or more. If the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is 1 or less, in the virus infection inhibitor, the proportion of the organic acid (A) with relatively small solubility becomes large, so that an excellent virus infection inhibitory effect can be stably exerted. If the mass ratio of the content of the compound having a salt of a sulfon group to the content of the organic acid (A) (content of the compound having a salt of a sulfon group / content of the organic acid (A)) is 0.005 or more, the adsorption of the sulfonate group generated by freeing the sulfonate group in the compound having a salt of a sulfon group to the virus is promoted, thereby exhibiting an excellent effect of inhibiting viral infection.

[0098] In the virus infection inhibitor, when organic acid (A) and organic acid (B) are included as organic acids, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is preferably 1 or less, more preferably 0.9 or less, more preferably 0.8 or less, and more preferably 0.7 or less. In the virus infection inhibitor, when organic acid (A) and organic acid (B) are included as organic acids, the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is preferably 0.005 or more, more preferably 0.01 or more, and more preferably 0.02 or more. If the mass ratio of the content of the compound having a salt of a sulfonic group to the content of the organic acid (A) (the content of the compound having a salt of a sulfonic group / the content of the organic acid (A)) is 1 or less, the proportion of the organic acid (A) with relatively low solubility in the virus infection inhibitor becomes large, so that an excellent virus infection inhibitory effect can be stably exerted. If the mass ratio of the content of the compound having a salt of a sulfon group to the content of the organic acid (A) (content of the compound having a salt of a sulfon group / content of the organic acid (A)) is 0.005 or more, the adsorption of the sulfonate group generated by freeing the sulfonate group in the compound having a salt of a sulfon group to the virus is promoted, thereby exhibiting an excellent effect of inhibiting viral infection.

[0099] In the virus infection inhibitor, when the organic acid (A) and the organic acid (B) are included as organic acids, the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (the content of the organic acid (B) / the content of the organic acid (A)) is preferably 2 or less, more preferably 1.6 or less, more preferably 1.2 or less, and more preferably 1 or less. In the virus infection inhibitor, when the organic acid (A) and the organic acid (B) are included as organic acids, the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (the content of the organic acid (B) / the content of the organic acid (A)) is preferably 0.1 or more, more preferably 0.2 or more, and more preferably 0.3 or more. When the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (the content of the organic acid (B) / the content of the organic acid (A)) is 2 or less, the virus infection inhibitor exhibits excellent water resistance and can maintain an excellent virus infection inhibitory effect even after wiping with water. When the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (content of the organic acid (B) / content of the organic acid (A)) is 0.1 or more, the viral infection inhibitory effect brought about by the viral infection inhibitor can be immediately manifested, and a fast-acting viral infection inhibitory effect can be imparted to a substrate, etc.

[0100] [Viral infection inhibitors]

[0101] When the viral infection inhibitor is in a particulate form, the D90 particle size of the viral infection inhibitor is more preferably 2 μm or more, more preferably 3 μm or more, and more preferably 4 μm or more. The D90 particle size of the viral 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 viral infection inhibitor is included in the substrate and used, it is easy to expose the viral infection inhibitor on the surface of the substrate, and the viral infection inhibitory effect is improved. When the D90 particle size is 25 μm or less, the processability when the viral infection inhibitor is included in the substrate and used is improved and the surface area is increased to make it easy to contact with the virus, which can improve the viral infection inhibitory effect of the viral infection inhibitor. In addition, the viral infection inhibitor can be more evenly attached to the surface of the substrate, and the viral infection inhibitory effect can be imparted to the substrate in a more uniform state.

[0102] As described later, the D90 particle size of the viral infection inhibitor is the particle size (90% cumulative particle size) at which the accumulation of frequencies in the volume-based particle size distribution based on the laser scattering method (accumulation of particles with small particle sizes) becomes 90%. By preferably adjusting the D90 particle size of the viral infection inhibitor to 2 to 25 μm, the presence of coarse particles in the viral infection inhibitor is reduced. The organic acid (A) and the organic acid (B) have functional groups [carboxyl (-COOH), sulfone (-SO3H), phosphonic acid [-P(=O)(OH)2] or phosphoric acid [-OPO(OH)2] in the molecule. By adjusting the D90 particle size of the viral infection inhibitor to the range, the processability is improved when the viral infection inhibitor is included in the substrate and used, and the substrate can be given an excellent viral infection inhibition effect.

[0103] When the viral infection inhibitor is in the form of particles, 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.

[0104] In a viral infection inhibitor, by setting the D50 particle size within the range (preferably 0.5 to 20 μm) and the D90 particle size to 2 to 25 μm, it is possible to reduce the presence of coarse particles having a particle size that greatly deviates from the D50 particle size in the viral infection inhibitor, thereby making the particle size of the viral infection inhibitor a more appropriate size.

[0105] Furthermore, by adjusting the particle size of the viral infection inhibitor to a more appropriate range, the amount of functional groups present on the surface of the particulate viral infection inhibitor can be more appropriately adjusted, thereby more effectively imparting an excellent viral infection inhibitory effect to the viral infection inhibitor.

[0106] The D90 particle size and D50 particle size of the viral infection inhibitor are particle sizes (90% cumulative particle size and 50% cumulative particle size) where the cumulative frequency (cumulative frequency derived from particles with small particle sizes) in the volume-based particle size distribution based on the laser scattering method is 90% and 50%, respectively.

[0107] The virus infection inhibitor contains an organic acid (A) (excluding compounds having salts of a sulfonic group) as an active ingredient. The virus infection inhibitor contains an organic acid (B) (excluding compounds having salts of a sulfonic group) as an active ingredient as needed. The virus infection inhibitor contains a compound having a salt of a sulfonic group as an active ingredient as needed. The method for producing the virus infection inhibitor is not particularly limited. When the virus infection inhibitor contains an organic acid (A), and a compound having a salt of a sulfonic group and / or an organic acid (B), the compound having a salt of a sulfonic group and / or the organic acid (B) (excluding compounds having salts of a sulfonic group) and the organic acid (A) (excluding compounds having salts of a sulfonic group) can be uniformly mixed in a general manner to produce the virus infection inhibitor.

[0108] The obtained virus infection inhibitor exhibits an excellent virus infection inhibitory effect, has an excellent virus infection inhibitory effect (antiviral property) even after wiping with water, and has excellent water resistance.

[0109] When the obtained virus infection inhibitor contains an organic acid (B), the virus infection inhibitor can immediately show an excellent virus infection inhibitory effect. In addition, when it is contained in a substrate and used, even when the thickness of the substrate is thick, it can also show an excellent virus infection inhibitory effect.

[0110] It should be noted that the virus infection inhibitory effect refers to the effect of eliminating or reducing the infectivity of the virus to the cell, or even if infected, it cannot proliferate in the cell. As a method for confirming the presence or absence of such viral infectivity, ISO18184 and JIS L1922 can be cited for fiber products, and ISO21702 can be cited for plastics other than fiber products and products with non-porous surfaces. The Antimicrobial Products Technology Agreement (SIAA) certifies the antiviral processing mark for products that meet the safety of antiviral processing agents and certain antiviral effect standards. The standard for the antiviral effect is that the difference (antiviral activity value) between the common logarithm of the virus infection titer of the blank product (no additives of the antiviral processing agent) and the common logarithm of the virus infection titer of the processed product (additives of the antiviral processing agent) in the evaluation of ISO21702 is 2.0 or more. Virus infection inhibitors are used as antiviral processing agents. Virus infection inhibitors can be added to surface coating agents such as paints and used, and evaluated by the evaluation method.

[0111] In addition, the plaque method and the hemagglutination titer (HAU) measurement method described in "Medical Virology" (first edition published in April 1990) can be cited.

[0112] In the present invention, when evaluating the virus infection inhibitory effect under the following conditions, for example, a product having a difference in the common logarithmic value of the virus infection titer between the blank product and the processed product (antiviral activity value) of 2.0 or more is defined as a virus infection inhibitor. At this time, regardless of the type of virus evaluated, a virus having a difference in the common logarithmic value of the virus infection titer between the blank product and the processed product (antiviral activity value) of 2.0 or more in at least one virus is treated as a virus infection inhibitor.

[0113] 30 mg of the virus infection inhibitor was added to 970 mg of a solvent-free ultraviolet curable acrylic resin (trade name "AI-N2" manufactured by COATTECH) and uniformly mixed to prepare a coating composition. The obtained coating composition was applied to a polyethylene film with a thickness of 18 μm using a wire bar coater #8, and then the film was coated using a UV conveyor device EYE GRANDAGE [EYE GRAPHICS Co., Ltd. "ECS301G1 Irradiator reflector: cold mirror condenser type, UV lamp: H03-L31 (luminous length: 365nm)], cumulative light intensity irradiated to the coating composition 500mJ / cm 2 The ultraviolet rays were applied to cure the ultraviolet curing acrylic resin to form a coating film with a film thickness of 18 μm as a test coating film (processed coating film).

[0114] The obtained test coating was subjected to an antiviral test according to ISO21702. For the virus suspension after 24 hours from the start of the reaction, the virus infection titer (common logarithm) of the test coating was calculated by the plaque method. A blank coating was prepared in the same manner as described, except that the virus infection inhibitor was not included, and the virus infection titer (common logarithm) (PFU / cm 2 ). The difference in the common logarithmic values ​​of the virus infection titers (antiviral activity value) was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0115] The virus infection inhibitor has a virus infection inhibitory effect on various viruses, and exhibits an excellent virus infection inhibitory effect on both enveloped viruses and non-enveloped viruses.

[0116] Examples of enveloped viruses include influenza virus (e.g., type A, type B, etc.), rubella virus, Ebola virus, coronavirus [e.g., SARS virus, novel coronavirus (SARS-CoV-2)], measles virus, varicella-zoster virus, herpes simplex virus, mumps virus, arbovirus, RS virus, hepatitis virus (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever virus, HIV, rabies virus, Hanta virus, dengue virus, Nipah virus, lyssa virus, etc.

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

[0118] The virus infection inhibitor is preferably present (e.g., attached or carried) on the surface of the base particles for use. When the virus infection inhibitor comprises an organic acid (A) and a compound having a salt of a sulfonic group, the compound having a salt of a sulfonic group and / or the organic acid (A) can be present (e.g., attached or carried) on the surface of the base particles for use. When the virus infection inhibitor comprises an organic acid (A), an organic acid (B) and a compound having a salt of a sulfonic group, any one or all of the compound having a salt of a sulfonic group, the organic acid (A) or the organic acid (B) can be present (e.g., attached or carried) on the surface of the base particles for use.

[0119] By making at least one of the active ingredients of the virus infection inhibitor present on the surface of the base particles, the virus infection inhibitor can be uniformly dispersed on the base material described later without forming a mass. Therefore, the surface area of ​​the virus infection inhibitor can be increased, the contact between the virus infection inhibitor and the virus can be fully ensured, and the virus infection inhibitor can fully exert its virus infection inhibitory effect.

[0120] As the base particles, there is no particular limitation as long as the virus infection inhibitor does not hinder the virus infection inhibitor's ...

[0121] 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.

[0122] 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.

[0123] The styrene-based resin is not particularly limited, and examples thereof include homopolymers or copolymers containing as monomer units a styrene-based monomer such as styrene, methylstyrene, ethylstyrene, isopropylstyrene, dimethylstyrene, chlorostyrene, bromostyrene, etc.; and copolymers containing as monomer units a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer.

[0124] Examples of the vinyl monomer copolymerizable with the styrene-based monomer include acrylic monomers such as acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, acrylic acid esters (e.g., methyl acrylate, ethyl acrylate, butyl acrylate, etc.), methacrylate esters (e.g., methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc.), maleic anhydride, and acrylamide.

[0125] The synthetic resin constituting the resin particles preferably contains an aromatic ring. The aromatic ring attracts the hydrophobic part of the organic acid (and the compound having a salt of a sulfonic acid group) attached to the surface of the resin particles, plays a role in orienting the carboxyl group (-COOH), sulfonic group (-SO3H), phosphonic acid group [-P(=O)(OH)2] or phosphoric acid group [-OPO(OH)2] of the organic acid to the outside, and can more effectively exert the virus infection inhibitory effect of the virus infection inhibitor.

[0126] As the inorganic material constituting the inorganic particles, there is no particular limitation, and for example, there can be mentioned: silicon dioxide, 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. It should be noted that the inorganic material can be used alone or in combination of two or more.

[0127] The D50 particle size of the base particles is preferably 0.1 μm or more, more preferably 1 μm or more. The D50 particle size of the base particles is preferably 30 μm or less, more preferably 15 μm or less. If the D50 particle size of the base particles is 0.1 μm or more, the surface area of ​​the base particles becomes smaller, the cohesion of the viral infection inhibitor decreases, and the viral infection inhibitor becomes a form in which the viral infection inhibitor and the virus easily interact, and the viral infection inhibition effect is improved. If the D50 particle size of the base particles is 30 μm or less, the aggregation of the viral infection inhibitor is prevented and the surface area is increased to facilitate contact with the virus, and the viral infection inhibition effect of the viral infection inhibitor is improved.

[0128] The D50 particle size of the base particles refers to the particle size (50% cumulative particle size) at which the cumulative frequency in the volume-based particle size distribution based on the laser scattering method (cumulative starting from particles with a small particle size) reaches 50%. When the base particles include multiple base particles, the D50 particle size of the base particles is a value measured based on the base particles as a whole.

[0129] The amount of the virus 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 more preferably 10 parts by mass or more relative to 100 parts by mass of the base particles. When the amount of the virus infection inhibitor attached is 1 part by mass or more, the virus infection inhibitor can be uniformly attached to the surface of the base particles, and the virus infection inhibitor effect can be more effectively exerted.

[0130] The amount of the virus 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 more preferably 20 parts by mass or less relative to 100 parts by mass of the base particles. When the amount of the virus infection inhibitor attached is 50 parts by mass or less, the virus infection inhibitors do not bind to each other, and the virus infection inhibitors are effectively configured on the surface of the base particles, and the virus infection inhibitory effect is improved.

[0131] There is no particular limitation on the method for attaching the virus infection inhibitor, the compound having a sulfonic acid salt, the organic acid (A) or the organic acid (B) to the surface of the base particles. For example, the adhesion of the virus infection inhibitor, the compound having a sulfonic acid salt, the organic acid (A) or the organic acid (B) itself can be utilized, or a binder resin can be used to adhere the virus infection inhibitor, the compound having a sulfonic acid salt, the organic acid (A) or the organic acid (B) to the surface of the base particles. From the viewpoint of being able to effectively exert the virus infection inhibitory effect of the virus infection inhibitor, it is preferred to utilize the adhesion of the virus infection inhibitor, the compound having a sulfonic acid salt, the organic acid (A) or the organic acid (B) itself to attach the virus infection inhibitor to the surface of the base particles.

[0132] The viral infection inhibitor is contained in a base material to be provided with a viral infection inhibitory effect and used, and the base material containing the viral infection inhibitor exhibits the viral infection inhibitory effect as a viral infection inhibitory product.

[0133] The substrate containing the viral infection inhibitor is not particularly limited as long as it can contain the viral infection inhibitor, and examples thereof include synthetic resin molded bodies such as films, coatings, coatings, wallpapers, decorative sheets, flooring materials, fiber products (woven fabrics, non-woven fabrics, knitted fabrics), interior products and interior materials for vehicles (such as cars, airplanes, ships, etc.) (seats, child seats and foam bodies constituting them, etc.), kitchen supplies, baby products, and building interior materials.

[0134] The synthetic resin constituting the synthetic resin molded body 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, polyether sulfone, polyarylate, polyether ether ketone, thermoplastic polyimide, polyamide-imide, etc.), thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea-formaldehyde resin, unsaturated polyester resin, alkyd resin, polysiloxane resin, polyurethane, thermosetting polyimide, etc.), etc. It should be noted that the synthetic resin may be used alone or in combination of two or more.

[0135] The virus infection inhibitor can also be mixed into a synthetic resin for use. As a method for mixing the virus infection inhibitor into a synthetic resin, the virus infection inhibitor can be mixed into a synthetic resin as a raw material to prepare a resin composition, and the resin composition is used to obtain a virus infection inhibiting product of a desired shape in the form of a molded product by a general synthetic resin molding method. As a general synthetic resin molding method, for example, extrusion molding, injection molding, blow molding, etc. can be cited. The resin composition containing a synthetic resin and a virus infection inhibitor can also be used as a masterbatch for synthetic resin molding, and the synthetic resin molding masterbatch is mixed into the synthetic resin as a raw material, and the virus infection inhibiting product is manufactured as a molded product using a general synthetic resin molding method.

[0136] In the viral infection inhibiting 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, relative to 100 parts by mass of the substrate. In the viral infection inhibiting 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, relative to 100 parts by mass of the substrate.

[0137] For a virus infection inhibiting product in which a virus infection inhibitor containing an organic acid (A) and an organic acid (B) as an organic acid is contained in a coating film, the ratio of the thickness of the coating film (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 more preferably 3 or more. The ratio of the thickness of the coating film (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 more preferably 8 or less. When the ratio of the thickness of the coating film (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) is 1 or more, it is possible to suppress the appearance defects such as streaks on the surface of the coating film when processing the coating film, so it is preferred. When the ratio of the thickness of the coating film (film thickness) to the D50 particle size of the virus infection inhibitor (film thickness / D50 particle size) is 12 or less, the virus infection inhibitor can be exposed on the surface of the coating film, giving the coating film an excellent virus infection inhibiting effect.

[0138] [Masterbatch for synthetic resin molding]

[0139] The masterbatch for synthetic resin molding comprises a synthetic resin and a virus infection inhibitor. The synthetic resin may be used alone or in combination of two or more. The synthetic resin may be a thermoplastic resin or a thermosetting resin, preferably a thermoplastic resin. Examples of thermoplastic resins include polyolefin resins, polyvinyl chloride resins, polyamide resins, polycarbonate resins, polystyrene resins, polyester resins, acrylonitrile-butadiene-styrene resins (ABS resins), polyethylene terephthalate (PET), polyurethane resins, and polymethyl methacrylate (PMMA).

[0140] When the viral infection inhibitor contains only organic acid (A) as the organic acid, the content of the synthetic resin in the synthetic resin molding masterbatch is preferably 10% by mass or more, more preferably 20% by mass or more. When the viral infection inhibitor contains only organic acid (A) as the organic acid, the content of the synthetic resin in the synthetic resin molding masterbatch is preferably 80% by mass or less, more preferably 60% by mass or less.

[0141] When the viral infection inhibitor contains only organic acid (A) as an organic acid, the content of the viral infection inhibitor in the synthetic resin molding masterbatch is preferably 10% by mass or more, more preferably 15% by mass or more. When the viral infection inhibitor contains only organic acid (A) as an organic acid, the content of the viral infection inhibitor in the synthetic resin molding masterbatch is preferably 80% by mass or less, more preferably 70% by mass or less.

[0142] When the viral infection inhibitor contains only an organic acid (A) as an organic acid, the content of the organic acid (A) in the synthetic resin molding masterbatch is preferably 10% by mass or more, more preferably 15% by mass or more. When the viral infection inhibitor contains only an organic acid (A) as an organic acid, the content of the organic acid (A) in the synthetic resin molding masterbatch is preferably 80% by mass or less, more preferably 70% by mass or less.

[0143] In the case where organic acid (A) and organic acid (B) are included as organic acids in the virus infection inhibitor, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 2% by mass or more, more preferably 3% by mass or more. In the case where organic acid (A) and organic acid (B) are included as organic acids in the virus infection inhibitor, the content of organic acid (A) in the masterbatch for synthetic resin molding is preferably 40% by mass or less, more preferably 35% by mass or less. In the case where organic acid (A) and organic acid (B) are included as organic acids in the virus infection inhibitor, the content of organic acid (B) in the masterbatch for synthetic resin molding is preferably 1% by mass or more, more preferably 2% by mass or more. In the case where organic acid (A) and organic acid (B) are included as organic acids in the virus infection inhibitor, the content of organic acid (B) in the masterbatch for synthetic resin molding 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, more preferably 24% by mass or less.

[0144] 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. The total content of the organic acid (A) and the organic acid (B) in the synthetic resin molding masterbatch is preferably 80% by mass or less, more preferably 70% by mass or less, more preferably 60% by mass or less, more preferably 50% by mass or less.

[0145] The content of the compound having a salt of a sulfonic group in the masterbatch for synthetic resin molding is more preferably 1% by mass or more, more preferably 5% by mass or more, and more preferably 8% by mass or more. The content of the compound having a salt of a sulfonic group in the masterbatch for synthetic resin molding is preferably 30% by mass or less, and more preferably 25% by mass or less.

[0146] 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 1 atmosphere (0.101 MPa) and 200°C, more preferably contains an organic acid (A) that is solid at 1 atmosphere (0.101 MPa) and 210°C, and more preferably contains an organic acid (A) that is solid at 1 atmosphere (0.101 MPa) and 220°C. 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 1 atmosphere (0.101 MPa) and 190°C, more preferably contains an organic acid (B) that is solid at 1 atmosphere (0.101 MPa) and 200°C, and more preferably contains an organic acid (B) that is solid at 1 atmosphere (0.101 MPa) and 220°C. When a masterbatch for synthetic resin molding is used for molding, sometimes the masterbatch for synthetic resin molding is heated and melted. In the case of containing an organic acid (A) and an organic acid (B) that are solid even at the temperature, it is easy to suppress the deterioration of the virus infection inhibitor and the discoloration of the obtained molded product. As the organic acid (A) as described above, for example, alginic acid (melting point 300°C at 1 atmosphere (0.101 MPa)), isophthalic acid (melting point 345°C at 1 atmosphere (0.101 MPa)), terephthalic acid (melting point 300°C at 1 atmosphere (0.101 MPa)), etc. can be cited. As such an organic acid (B), for example, 1,3-propylenediaminetetraacetic acid (melting point (thermal decomposition temperature) 237°C at 1 atmosphere (0.101 MPa)), phthalic acid (melting point 191°C at 1 atmosphere (0.101 MPa)), etc. can be cited.

[0147] In addition, "solid at Y°C under 1 atmosphere (0.101 MPa)" means that the melting point (the sublimation point and thermal decomposition temperature in the case of a compound having no melting point) does not exist at Y°C or less.

[0148] The resin composition, in particular the masterbatch for synthetic resin molding, preferably further comprises a surfactant. As the surfactant, there is no particular limitation, and examples thereof include anionic surfactants (anionic surfactants not including salts containing sulfonic groups), cationic surfactants, nonionic surfactants, amphoteric surfactants, etc., preferably anionic surfactants and nonionic surfactants. When the masterbatch for synthetic resin molding further comprises a surfactant, it is easy to make the organic acid segregate on the surface of the obtained virus infection inhibition product (molded body), which can further improve the water resistance of the virus infection inhibition product (molded product).

[0149] The anionic surfactant is not particularly limited, and examples thereof include alkyl phosphates such as sodium lauryl phosphate, potassium lauryl phosphate, sodium stearyl phosphate, potassium stearyl phosphate, polyoxyethylene (3) lauryl ether sodium phosphate, potassium polyoxyethylene (3) lauryl ether phosphate, and polyoxyethylene alkyl ether phosphate ester salts such as sodium polyoxyethylene (3) lauryl ether phosphate and potassium polyoxyethylene (3) lauryl ether phosphate, and polyoxyethylene alkyl phenyl ether phosphates such as sodium polyoxyethylene (3) lauryl phenyl ether phosphate and potassium polyoxyethylene (3) lauryl phenyl ether phosphate.

[0150] 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), sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerol fatty acid esters, polyoxyethylene glycerol fatty acid esters, polyglycerol fatty acid esters, sucrose fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, fatty acid alkanolamides, alkyl alkanolamides, acetylene glycols, oxyethylene adducts of acetylene glycols, polyethylene glycol polypropylene glycol block copolymers, and the like. Polyoxyethylene fatty acid esters are preferred.

[0151] 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, alkylβ-alanine, alkyldiethanolamine, polyoxyalkylene alkylamine, and diamine oxyethylene addition type surfactants.

[0152] The content of the surfactant in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more. The content of the surfactant in the resin composition is preferably 40% by mass or less, more preferably 30% by mass or less.

[0153] When the resin composition includes a surfactant, in the resin composition, the mass ratio of the content of the surfactant relative to the content of the organic acid (A) (the content of the surfactant / the content of the organic acid (A)) is preferably 0.05 or more, more preferably 0.1 or more, and more preferably 0.2 or more. When the resin composition includes a surfactant, in the resin composition, the mass ratio of the content of the surfactant relative to the content of the organic acid (A) (the content of the surfactant / the content of the organic acid (A)) 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 content of the surfactant relative to the content of the organic acid (A) (the content of the surfactant / the content of the organic acid (A)) is within the range, the water resistance of the virus infection inhibition product (molded product) can be easily improved.

[0154] In the case where the resin composition includes a surfactant and an organic acid (A) and an organic acid (B) as an organic acid, in the resin composition, the mass ratio of the content of the surfactant relative to the total content of the organic acid (A) and the organic acid (B) (the content of the surfactant / the total content of the organic acid (A) and the organic acid (B)) is preferably 0.05 or more, more preferably 0.1 or more, and more preferably 0.2 or more. When the resin composition includes a surfactant, in the resin composition, the mass ratio of the content of the surfactant relative to the total content of the organic acid (A) and the organic acid (B) (the content of the surfactant / the total content of the organic acid (A) and the organic acid (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 content of the surfactant relative to the total content of the organic acid (A) and the organic acid (B) (the content of the surfactant / the total content of the organic acid (A) and the organic acid (B)) is within the range, it is easy to improve the water resistance of the virus infection inhibition product (molded product), and the virus infection inhibition effect brought by the virus infection inhibitor can be immediately shown.

[0155] The masterbatch for synthetic resin molding is preferably a resin pellet from the viewpoint of excellent moldability. By melting and molding the resin pellet, a virus infection inhibiting product (molded product) having excellent virus infection inhibiting effect can be obtained.

[0156] The shape of the resin particles is not particularly limited, and spherical, cylindrical, and prismatic shapes can be cited. From the viewpoint of the stability of the particle shape, cylindrical shapes are preferred. The maximum length direction dimension of the resin particles is preferably 1 mm or more, more preferably 3 mm or more. The maximum length direction dimension of the resin particles is preferably 10 mm or less, more preferably 7 mm or less.

[0157] The synthetic resin molding masterbatch can be mixed with other resin materials. Other resin materials can also be resin particles. The synthetic resin molding masterbatch is mixed with the other resin materials to obtain a mixed resin material, and the mixed resin material is molded to obtain a virus infection inhibition product (molded product) with excellent virus infection inhibition effect.

[0158] As the coating, a coating known in the past can be used, for example, oily coatings (such as blended coatings, oil varnishes, etc.), cellulose coatings, synthetic resin coatings, etc. can be cited. In the coating, additives such as pigments, plasticizers, curing agents, extenders, fillers, anti-aging agents, thickeners, surfactants, etc. can be included within the range that does not damage its physical properties. It should be noted that as a method for including a viral infection inhibitor in the coating, for example, a method of supplying the viral infection inhibitor and the coating to a dispersing device and uniformly mixing them can be cited. It should be noted that as a dispersing device, for example, a high-speed mill, a ball mill, a sand mill, etc. can be cited.

[0159] The building interior material is not particularly limited, and examples thereof include floor materials, wallpapers, ceiling materials, paints, door handles, switches, switch covers, wax, and the like.

[0160] The vehicle interior products and vehicle interior materials are not particularly limited, and examples thereof include seats, child seats, seat belts, seat cushions, seat covers, doors, ceiling materials, floor mats, door trims, instrument panels, consoles, glove boxes, hanging rings, and armrests.

[0161] Example

[0162] Hereinafter, the present invention will be described in more detail using Examples, but the present invention is not limited thereto.

[0163] [Preparation of cross-linked polyacrylic acids 1 and 2]

[0164] An epoxy crosslinking agent (sorbitol polyglycidyl ether, Nagase Chemtex Co., Ltd., trade name "Denacol EX-614B") was added to an aqueous solution of polyacrylic acid (trade name "AQUALIC HL-415," weight average molecular weight: 10,000) and mixed uniformly to prepare a polyacrylic acid solution. The contents (parts by mass) of polyacrylic acid and epoxy crosslinking agent in the polyacrylic acid solution are shown in Table 1.

[0165] The polyacrylic acid solution was heated at 120° C. for 90 minutes to crosslink the polyacrylic acid and 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.

[0166] [Table 1]

[0167]

[0168] (Examples 1 to 25, Comparative Examples 1 to 5)

[0169] The salt compound having a sulfonic group (salt compound), organic acid (A) and organic acid (B) of the types shown in Table 2 were uniformly mixed to prepare a particle-shaped virus infection inhibitor. The contents of the salt compound having a sulfonic group (salt compound), organic acid (A) and organic acid (B) in the virus infection inhibitor are shown in Table 3.

[0170] Table 3 shows the mass ratio of the content of the compound having a salt of a sulfonic acid 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)) in the viral infection inhibitor.

[0171] Table 3 shows the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (content of the organic acid (B) / content of the organic acid (A)) in the viral infection inhibitor.

[0172] In the table, "compound having a salt of a sulfonic acid group" is referred to as "salt compound." The mass ratio of the content of the compound having a salt of a sulfonic acid 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 referred to as "salt compound / organic acid (A)." The mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (content of the organic acid (B) / content of the organic acid (A)) is referred to as "organic acid (B) / organic acid (A)."

[0173] 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 weight of organic acids (A) and (B) used in the preparation of viral infection inhibitors.

[0174] The solubility (g / L) of the sodium salts of the organic acid (A) and the organic acid (B) used in the preparation of the viral infection inhibitor in water at 25° C. is shown in the “Solubility of Na Salt” column of Table 2.

[0175] It should be noted that in the table, "melting point at 1 atmosphere (1013.25hPa)", "solubility in water at 25°C" and "pKa1 at 25°C" are abbreviated as "melting point", "solubility" and "pKa1", respectively. For cross-linked polyacrylic acid, "thermal decomposition temperature" is recorded instead of melting point. For fumaric acid, "sublimation temperature" is recorded instead of melting point. In the "melting point" and "molecular weight" in the table, if it cannot be measured, it will be recorded as "unable to measure." For 1,3-propylenediaminetetraacetic acid, "thermal decomposition temperature" is recorded instead of melting point. In the table, ">Z" (Z is a numerical value) means greater than Z.

[0176] Table 3 shows the D50 particle size (μm) and D90 particle size (μm) of the obtained virus infection inhibitors.

[0177] The obtained virus infection inhibitors were subjected to antiviral tests using influenza virus (enveloped virus) and / or feline calicivirus (non-enveloped virus). The results are shown in Table 4.

[0178] [Antiviral test]

[0179] The initial activity value, the activity value after the water resistance test, the quick-acting activity value and the activity value after the sodium hypochlorite treatment were measured according to the following method, and the results are shown in Tables 4 and 5.

[0180] (Initial activity value)

[0181] 3 parts by mass of a virus infection inhibitor and 97 parts by mass of an ultraviolet curable acrylic paint (trade name "AI-N2" manufactured by COAT TECH) were mixed to prepare a coating composition. The coating composition was applied to a polyethylene film with a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0182] A UV conveyor device ("ECS301G1" manufactured by Eye Graphics) was used to apply light to the coating layer at 25°C at a cumulative amount of 500 mJ / cm 2 The ultraviolet curing acrylic paint was cured by irradiating ultraviolet rays with a wavelength of 365 nm to form a test coating film with a thickness of 18 μm.

[0183] The obtained test coating was subjected to an antiviral test in accordance with ISO 21702. The virus infection titer (common logarithm value) of the test coating was calculated by the plaque method for the virus suspension 24 hours after the start of the reaction.

[0184] A blank coating was prepared in the same manner as above except that the virus infection inhibitor was not contained, and the virus infection titer (common logarithm) (PFU / cm 2 The virus infection titer (common logarithm value) of the blank coating is 6.5 PFU / cm 2 .

[0185] The antiviral activity value (initial activity value) was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0186] (Activity value after water resistance test (18μm))

[0187] 3 parts by mass of a virus infection inhibitor and 97 parts by mass of an ultraviolet curable acrylic paint (trade name "AI-N2" manufactured by COAT TECH) were mixed to prepare a coating composition. The coating composition was applied to a polyethylene film with a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0188] A UV conveyor device ("ECS301G1" manufactured by Eye Graphics) was used to apply light to the coating layer at 25°C at a cumulative amount of 500 mJ / cm 2 The ultraviolet curing acrylic paint was cured by irradiating ultraviolet rays with a wavelength of 365 nm to form a coating film with a thickness of 18 μm.

[0189] The obtained coating film was subjected to a water resistance test according to the water resistance test of water resistance zone 1 given by SIAA. The antiviral test was conducted in the same manner as the initial activity value, except that the water attached to the coating film surface after the water resistance test was removed by absorbing with a cloth to prepare the test coating film, and the antiviral activity value after the water resistance test [activity value after water resistance test (18 μm)] was calculated.

[0190] (Fast-acting activity value)

[0191] For the virus suspension after 10 minutes from the start of the reaction, the virus infection titer (common logarithm value) of the test coating was calculated by the plaque method. In addition, the antiviral activity value (rapid-acting activity value) was calculated in the same way as the determination method of the initial activity value. It should be noted that the virus infection titer (common logarithm value) of the blank coating was 6.5 PFU / cm 2 .

[0192] (Activity value after water resistance test (35μm))

[0193] The coating composition was applied to a polyethylene film in a thickness of 35 μm using a wire bar coater #8 to form a coating layer, and the ultraviolet curable acrylic coating was cured to form a coating film with a thickness of 35 μm. In addition, the antiviral activity value after the water resistance test [activity value after water resistance test (35 μm)] was calculated in the same manner as the activity value after the water resistance test (18 μm).

[0194] (Activity value after sodium hypochlorite treatment)

[0195] 3 parts by mass of a virus infection inhibitor and 97 parts by mass of an ultraviolet curable acrylic paint (trade name "AI-N2" manufactured by COAT TECH) were mixed to prepare a coating composition. The coating composition was applied to a polyethylene film with a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0196] A UV conveyor device ("ECS301G1" manufactured by Eye Graphics) was used to apply light to the coating layer at 25°C at a cumulative amount of 500 mJ / cm 2 The ultraviolet curing acrylic paint was cured by irradiating ultraviolet rays with a wavelength of 365 nm to form a coating film with a thickness of 18 μm.

[0197] 0.5 mL of 0.05 mass % sodium hypochlorite aqueous solution (25° C.) was infiltrated into a flat square cotton cloth (white cotton cloth for testing according to JIS L0803 (fine white cloth (Kanakin) No. 3)) with a side of 6 cm, and the cotton cloth was attached to the friction piece of a friction tester type I (manufactured by Imoto Seisakusho Co., Ltd.). The surface of the obtained coating film was subjected to a pressure of 40 g / cm 2 After 400 reciprocating rubbings, the surface of the coating was cleaned with a neutral detergent. The coating was dried at room temperature to prepare a test coating. It should be noted that the cotton cloth was replaced with a new cotton cloth impregnated with a 0.05 mass % sodium hypochlorite aqueous solution every 100 reciprocating rubbings.

[0198] 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 sodium hypochlorite treatment) was calculated.

[0199] (Albino)

[0200] The test coating film was prepared in the same manner as when the initial activity value was determined. For the obtained test coating film, the whitening property evaluation was carried out according to the stain resistance test of JIS A1454 polymer parquet material test method. In a test room at a temperature of 23°C and a relative humidity of 50%, 2 mL of purified water was dripped onto the surface of the test coating film, covered with a watch glass, and left to stand for 24 hours. Then, it was removed with a household neutral detergent, and then the surface of the test coating film was wiped with industrial alcohol and left to stand in the test room for 1 hour. The haze of the test coating film was evaluated according to JIS K7361. The haze is measured by using a haze meter (trade name "HM-150" manufactured by Murakami Color Technology Research Institute Co., Ltd.) at room temperature of 25°C and a relative humidity of 40% (%). The larger the haze value, the greater the degree of whitening (degree of discoloration) of the coating surface.

[0201] [Table 2]

[0202]

[0203] [Table 3]

[0204]

[0205] [Table 4]

[0206]

[0207] [Table 5]

[0208]

[0209] [Masterbatch for synthetic resin molding]

[0210] (Examples 26 to 34, Comparative Example 6)

[0211] The salt compound having a sulfonic group (salt compound), organic acid (A) and organic acid (B) of the types shown in Table 6 were uniformly mixed to prepare a particle-shaped virus infection inhibitor. The contents of the salt compound having a sulfonic group (salt compound), organic acid (A) and organic acid (B) in the virus infection inhibitor are shown in Table 7.

[0212] Table 7 shows the mass ratio of the content of the compound having a salt of a sulfonic acid 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)) in the viral infection inhibitor.

[0213] Table 7 shows the mass ratio of the content of the organic acid (B) to the content of the organic acid (A) (content of the organic acid (B) / content of the organic acid (A)) in the viral infection inhibitor.

[0214] Table 7 shows the D50 particle size (μm) and D90 particle size (μm) of the obtained virus infection inhibitor.

[0215] 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 Co., Ltd.) as a synthetic resin, and 10 parts by mass of the surfactant listed in Table 8 were mixed to prepare a masterbatch for synthetic resin molding. In addition, in Table 8, "polypropylene" is indicated as "PP."

[0216] In 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 CO., LTD.) as a synthetic resin were mixed to prepare a masterbatch for synthetic resin molding.

[0217] The obtained synthetic resin molding masterbatch was mixed with a separately prepared polypropylene (JAPAN POLYPROPYLENE, trade name "NOVATEC PP BC6C") using LABO PLASTOMILL (manufactured by Toyo Seiki Co., Ltd. under the trade name "3S-150") at a mixing ratio of 1:9 (mass ratio), and kneaded for 5 minutes at 180° C. Next, the obtained resin composition was press-molded to obtain a sheet-like resin molded product (average thickness 1 mm, content of the virus infection inhibitor: 5 mass%) as a virus infection inhibitor product.

[0218] The obtained virus infection inhibiting product was tested for initial activity, activity after water resistance test and quick-acting activity by the same test method as the coating film, and the results are shown in Table 9. The activity after water resistance test is recorded in the column "Activity after water resistance test (1 mm)". It should be noted that a sheet-like resin molded product was used instead of the test coating film, a blank sheet-like resin molded product (blank sheet) was prepared using polypropylene (trade name "NOVATEC PP BC6C" manufactured by JAPAN POLYPROPYLENE Co., Ltd.) (no surfactant was used), and the blank sheet was used instead of the blank coating film. In addition, the initial activity, activity after water resistance test and quick-acting activity were measured according to the above method.

[0219] [Table 6]

[0220]

[0221] [Table 7]

[0222]

[0223] [Table 8]

[0224]

[0225] [Table 9]

[0226]

[0227] Industrial Applicability

[0228] 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 thus can maintain an excellent virus infection inhibitory effect even after wiping with water. The virus infection inhibitor has an excellent virus infection inhibitory effect on both enveloped viruses and non-enveloped viruses, and exerts a virus infection inhibitory effect on various viruses.

[0229] 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.

[0230] (CROSS REFERENCE TO RELATED APPLICATIONS)

[0231] 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, and the disclosure of the present application is incorporated into this specification by reference to the entireties thereof.

Claims

1. A viral infection inhibitor, comprising: An organic acid (A) having a solubility in water at 25°C of 0.4 g / L or less.

2. The viral infection inhibitor according to claim 1, further comprising: A compound having a salt of a sulfonic group.

3. The viral infection inhibitor according to claim 2, wherein The mass ratio of the content of the compound having a salt of a sulfonic acid 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. The viral infection inhibitor according to any one of claims 1 to 3, wherein The organic acid (A) has a pKa1 of 4.6 or less at 25°C.

5. The viral infection inhibitor according to any one of claims 1 to 4, wherein The organic acid (A) has a carboxyl group or a sulfone group.

6. The viral infection inhibitor according to any one of claims 1 to 5, wherein The organic acid (A) is at least one organic acid selected from the group consisting of alginic acid, isophthalic acid, terephthalic acid, and a polymer having a carboxyl group.

7. The viral infection inhibitor according to any one of claims 1 to 5, wherein The organic acid (A) is a polymer having a sulfonic group. 8 . The viral infection inhibitor according to claim 1 , which is in the form of particles and has a D90 particle size of 2 to 25 μm.

9. The viral infection inhibitor according to any one of claims 1 to 8, wherein The solubility of the sodium salt of the organic acid (A) in water at 25° C. is 1 g / L or more.

10. The viral infection inhibitor according to any one of claims 1 to 9, further comprising: An organic acid (B) having a solubility in water at 25°C exceeding 0.4 g / L.

11. A resin composition comprising: Synthetic resin, and The viral infection inhibitor according to any one of claims 1 to 10.

12. The resin composition according to claim 11, further comprising: Surfactant.

13. The resin composition according to claim 11 or 12, further comprising: An organic acid (B) having a solubility in water at 25°C exceeding 0.4 g / L.

14. A masterbatch for synthetic resin molding, comprising: Synthetic resin, and The viral infection inhibitor according to any one of claims 1 to 10.

15. The synthetic resin molding masterbatch according to claim 14, further comprising: Surfactant. 16 . The synthetic resin molding masterbatch according to claim 14 , further comprising an organic acid (B) having a solubility in water at 25° C. exceeding 0.4 g / L.

17. A viral infection inhibition product comprising: Base material, and The viral infection inhibitor according to any one of claims 1 to 10 contained in the substrate.

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