Virus infection inhibitor, resin composition, and virus infection inhibitor product

Abstract

The present invention provides a viral infection inhibitor mostly capable of preventing yellowing of the inhibitor even when placed in a high-temperature environment. This viral infection inhibitor contains: a carrier which has a specific surface area of 1 to 1,000 m2 / g; and a viral infection inhibitory compound which is carried on the carrier and contains at least one kind of infection inhibitory functional group selected from the group consisting of a carboxyl group, a sulfo group, a primary amino group, a secondary amino group, and a tertiary amino group or a salt thereof, or a viral infection inhibitory compound which is carried on the carrier and contains a guanidine structure.

Description

[Technical Field]

[0001] The present invention relates to a virus infection inhibitor, a resin composition, and a virus infection inhibitor product. [Background technology]

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

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

[0004] In response to these problems, Patent Document 1 proposes an antiviral surface treatment agent comprising a paint containing an antiviral agent, which is calcium carbonate supported by a sulfonic acid surfactant, and the paint is an ultraviolet-curable paint or an electron beam-curable paint. [Prior art documents] [Patent documents]

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

[0006] However, the antiviral surface treatment agent has the problem of yellowing when placed in a high-temperature environment, and further has the problem of poor coatability of the paint due to the occurrence of aggregation when the antiviral surface treatment agent is contained in the paint.

[0007] The present invention provides a virus infection inhibitor that can largely prevent yellowing even when placed in a high-temperature environment (hereinafter, sometimes referred to as "yellowing resistance"), as well as a resin composition and a virus infection-inhibiting product that use the virus infection inhibitor.

[0008] The present invention provides a virus infection inhibitor that, when contained in a paint, can be uniformly dispersed in the paint without agglomeration, making it possible to prepare a paint having excellent coatability (hereinafter sometimes referred to as "coatability"). [Means for solving the problem]

[0009] The viral infection inhibitor of the present invention comprises: Specific surface area is 1 to 1000m 2 / g of a support; The composition comprises a viral infection-inhibiting compound supported on the support and containing at least one infection-inhibiting functional group selected from the group consisting of a carboxy group, a sulfo group, a primary amino group, a secondary amino group, and a tertiary amino group, or a salt thereof, or a viral infection-inhibiting compound supported on the support and containing a guanidine structure.

[0010] The resin composition of the present invention contains a synthetic resin and the virus infection inhibitor.

[0011] The viral infection-preventing product of the present invention comprises a substrate and the viral infection-preventing agent contained in the substrate. [Effects of the Invention]

[0012] Because the virus infection inhibitor of the present invention has the above-mentioned composition, it hardly yellows even when placed in a high-temperature environment, and does not aggregate even when mixed into a paint, making it possible to prepare a paint with excellent coatability.

[0013] The virus infection inhibitor of the present invention has excellent resistance to yellowing, and therefore can impart a virus infection inhibitory effect to a substrate while maintaining the appearance of the substrate, such as its color, without impairing the appearance of the substrate. DETAILED DESCRIPTION OF THE INVENTION

[0014] The viral infection inhibitor of the present invention comprises: Specific surface area is 1 to 1000m 2 / g of a support; a viral infection-inhibiting compound supported on the support and containing at least one infection-inhibiting functional group selected from the group consisting of a carboxy group, a sulfo group, a primary amino group, a secondary amino group, and a tertiary amino group, or a salt thereof, or a viral infection-inhibiting compound supported on the support and containing a guanidine structure.

[0015] [Viral infection inhibitor compound] The viral infection inhibitor of the present invention contains a viral infection inhibitory compound as an active ingredient. The viral infection inhibitory compound has, in its molecule, at least one infection-inhibiting functional group selected from the group consisting of a carboxy group (-COOH), a salt of a carboxy group, a sulfo group (-SO3H), a salt of a sulfo group, a primary amino group, a salt of a primary amino group, a secondary amino group, a salt of a secondary amino group, a tertiary amino group, and a salt of a tertiary amino group, or a guanidine structure.

[0016] The viral infection-inhibiting compound exerts a viral infection-inhibiting effect due to the infection-inhibiting functional group and the guanidine structural moiety, and has an excellent viral infection-inhibiting effect particularly against both enveloped and non-enveloped viruses.

[0017] The term "viral infection inhibitory effect" refers to the effect of eliminating or reducing the infectivity of viruses to cells, or preventing them from replicating in cells even if they infect. Examples of methods for determining whether or not a virus is infective include ISO 18184 and JIS L1922 for textile products, and ISO 21702 for plastics and non-porous surface products other than textiles. The Society of International Studies on Antimicrobial Articles (SIAA) certifies products that meet the safety and antiviral efficacy standards for antiviral finishing agents with an antiviral finish mark. The standard for antiviral efficacy is a difference (antiviral activity value) of 2.0 or more between the common logarithm of the viral infectivity titer of a blank product (product without antiviral finishing agent) and the common logarithm of the viral infectivity titer of a processed product (product with antiviral finishing agent added) in the ISO 21702 evaluation. Viral infection inhibitors are used as components of antiviral finishing agents, kneaded into resins, or added to surface coating agents such as paints, and are evaluated using the above evaluation method.

[0018] In the present invention, for example, when the viral infection inhibitory effect is evaluated under the following conditions, a product is defined as a viral infection inhibitor when the difference in the common logarithm of the viral infectivity value (antiviral activity value) between the blank product and the processed product is 2.0 or more. Regardless of the type of virus being evaluated, a product with a difference in the common logarithm of the viral infectivity value (antiviral activity value) of 2.0 or more for at least one type of virus is treated as a viral infection inhibitor.

[0019] For example, 50 mg of a virus infection inhibitor is added to 950 mg of a solvent-free ultraviolet-curable acrylic resin and mixed uniformly to prepare a coating. The resulting coating is applied to a polyethylene film to a thickness of 18 μm to form a coating layer. This coating layer is then irradiated with ultraviolet light at a wavelength of 365 nm at a dose of 500 mJ / cm. 2 The ultraviolet-curable acrylic resin is cured by irradiating the resin so as to form a coating film with a thickness of 18 μm, which is used as the test coating film.

[0020] The antiviral test of the obtained test coating film is carried out in accordance with ISO21702. For the virus suspension after the reaction, the virus infectivity of the test coating film is calculated by the plaque method. A blank coating film is prepared in the same manner as above except that no virus infection inhibitor is added, and the virus infectivity (common logarithm) (PFU / cm) is calculated in the same manner as above based on this blank coating film. 2 The difference in common logarithm of the virus infectivity titers (antiviral activity value) is calculated by subtracting the virus infectivity titer of the test coating film from the virus infectivity titer of the blank coating film.

[0021] Other methods include the plaque method and hemagglutination assay (HAU) as described in "Medical and Pharmaceutical Virology" (first published in April 1990).

[0022] The salt of the carboxy group (-COOH) is not particularly limited, and examples thereof include sodium salt (-COONa), calcium salt [(-COO - )2Ca 2+ ], ammonium salt (-COO - NH4 + ), magnesium salt [(-COO - )2Mg 2+ ], barium salts [(-COO - )2Ba 2+ and the like, and sodium salts are preferred.

[0023] The salt of the sulfo group (-SO3H) is not particularly limited, and examples thereof include sodium salt (-SO3Na), calcium salt [(-SO3 - )2Ca 2+ ], ammonium salt (-SO3 - NH4 + ), magnesium salt [(-SO3 - )2Mg 2+ ], barium salts [(-SO3 - )2Ba 2+ and the like, and sodium salts are preferred.

[0024] The viral infection-inhibiting compound having a carboxy group may have one or more carboxy groups in the molecule, and examples thereof include polymers having a carboxy group in the side chain of a linear polymer, mellitic acid, aconitic acid, citric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, fumaric acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like. Taric acid, methylenedisalicylic acid, cis-Δ4-tetrahydrophthalic acid, gluconic acid, mucic acid, 3,3'-thiodipropionic acid, 2,2'-thiodiglycolic acid, 3,3'-dithiodipropionic acid, 2,2'-dithiodiglycolic acid, 2,2'-dithiosalicylic acid, 4,4'-dithiodibutyric acid, 3-(dodecylthio)propionic acid, picolinic acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, Examples of suitable hydroxybenzoates include hydroxybenzoates, ...

[0025] In the polymer having a carboxy group in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers, polyesters, and polyurethanes are preferred, with vinyl polymers being more preferred.

[0026] Examples of polymers having a carboxy group in the side chain of a linear polymer include polymers containing a carboxy group-containing monomer as a monomer unit. The polymer containing a carboxy group-containing monomer as a monomer unit may be a homopolymer of the carboxy group-containing monomer, or a copolymer of the carboxy group-containing monomer and a monomer copolymerizable therewith. In polymers containing a carboxy group-containing monomer as a monomer unit, the content of the carboxy group-containing monomer is preferably 50 mol% or more, more preferably 75 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0027] The carboxyl group-containing monomer is not particularly limited, and examples thereof include acrylic acid, methacrylic acid, β-carboxyethyl (meth)acrylate, 5-carboxypentyl (meth)acrylate, succinic acid mono(meth)acryloyloxyethyl ester, ω-carboxypolycaprolactone mono(meth)acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and carboxybetaine-type monomers, with acrylic acid and methacrylic acid being preferred. The carboxyl group-containing monomers may be used alone or in combination of two or more. (Meth)acrylate refers to acrylate or methacrylate. (Meth)acryloyl refers to acryloyl or methacryloyl.

[0028] The viral infection-inhibiting compound containing a salt of a carboxy group may have one or more salts of a carboxy group in the molecule, and examples thereof include polymers having a salt of a carboxy group in the side chain of a linear polymer, salts of mellitic acid, salts of aconitic acid, salts of citric acid, salts of oxalic acid, salts of malonic acid, salts of succinic acid, salts of glutaric acid, salts of adipic acid, salts of pimelic acid, salts of suberic acid, salts of fumaric acid, salts of maleic acid, salts of itaconic acid, salts of citraconic acid, salts of mesaconic acid, salts of phthalic acid, salts of isophthalic acid, and salts of terephthalic acid. Salts of methylenedisalicylic acid, salts of cis-Δ4-tetrahydrophthalic acid, salts of gluconic acid, salts of mucic acid, salts of 3,3'-thiodipropionic acid, salts of 2,2'-thiodiglycolic acid, salts of 3,3'-dithiodipropionic acid, salts of 2,2'-dithiodiglycolic acid, salts of 2,2'-dithiosalicylic acid, salts of 4,4'-dithiodibutyric acid, salts of 3-(dodecylthio)propionic acid, salts of picolinic acid, salts of formic acid, salts of acetic acid, salts of propionic acid, salts of butyric acid, salts of valeric acid, salts of caproic acid, salts of enanthic acid, Salts of prylic acid, salts of pelargonic acid, salts of capric acid, salts of lauric acid, salts of crotonic acid, salts of glycolic acid, salts of lactic acid, salts of malic acid, salts of tartaric acid, salts of quinic acid, salts of salicylic acid, salts of benzoic acid, salts of vanillic acid, salts of gallic acid, salts of mandelic acid, salts of benzilic acid, salts of phloretic acid, salts of coumaric acid, salts of caffeic acid, salts of ferulic acid, salts of sinapic acid, salts of 4-aminobenzoic acid, salts of triglycolaminic acid, salts of ethylenediaminetetraacetic acid, salts of diethylenetriaminepentaacetic acid, salts of carboxymethylcellulose Examples of the carboxysucrose salt include salts of sucrose, salts of carboxymethylated chitosan, salts of carboxymethylated chitin, salts of carboxymethyldextran, salts of carboxymethyl-β-cyclodextrin, salts of carboxysucrose, salts of pectin, salts of xanthan gum, salts of alginic acid, salts of hyaluronic acid, salts of fulvic acid, salts of humic acid, salts of uronic acid, salts of arabinonic acid, salts of fructuronic acid, salts of tagaturonic acid, salts of glucuronic acid, salts of iduronic acid, salts of galacturonic acid, salts of mannuronic acid, and salts of guluronic acid.

[0029] In the polymer having a salt of a carboxy group in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers, polyesters, and polyurethanes are preferred, with vinyl polymers being more preferred.

[0030] Examples of polymers having a carboxyl group salt in the side chain of a linear polymer include polymers containing a carboxyl group salt-containing monomer as a monomer unit. The polymer containing a carboxyl group salt-containing monomer as a monomer unit may be a homopolymer of the carboxyl group salt-containing monomer, or a copolymer of the carboxyl group salt-containing monomer and a monomer copolymerizable therewith. In the polymer containing a carboxyl group salt-containing monomer as a monomer unit, the content of the carboxyl group salt-containing monomer is preferably 50 mol% or more, more preferably 75 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0031] The carboxyl group salt-containing monomer is a carboxyl group salt of a carboxyl group-containing monomer. Examples of the salt of the carboxyl group salt-containing monomer include sodium salt, calcium salt, ammonium salt, magnesium salt, barium salt, etc., and sodium salt is preferred. Note that the carboxyl group-containing monomer is the same as above, so the explanation will be omitted.

[0032] The viral infection-inhibiting compound containing a sulfo group may have one or more sulfo groups in the molecule, and examples thereof include linear polymers having sulfo groups in the side chains, polystyrene sulfonic acid, formamidine sulfinic acid, 3-aminobenzenesulfonic acid, hydroxybenzenesulfonic acid, m-xylene-4-sulfonic acid, 5-sulfosalicylic acid, sulfanilic acid, 2-amino-3,5-dimethylbenzenesulfonic acid, 1,3-phenylenediamine-4-sulfonic acid, sulfonated (styrene-divinylbenzene copolymer), carrageenan, sulfonated polyethersulfone, ligninsulfonic acid, and taurine.

[0033] In the polymer having a sulfo group in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers, polyesters, and polyurethanes are preferred, with vinyl polymers being more preferred.

[0034] Examples of polymers having a sulfo group in the side chain of a linear polymer include polymers containing a sulfo group-containing monomer as a monomer unit. In polymers containing a sulfo group-containing monomer as a monomer unit, the content of the sulfo group-containing monomer is preferably 50 mol% or more, more preferably 75 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0035] Examples of polymers containing a sulfo group-containing monomer as a monomer unit include polymers containing styrene sulfonic acid units, homopolymers of styrene sulfonic acid, styrene-styrene sulfonic acid copolymers, compounds in which the benzene rings of polystyrene have been sulfonated, and compounds in which the benzene rings of polymers containing a styrene component have been sulfonated.

[0036] The sulfo group-containing monomer is not particularly limited, and examples thereof include p-styrenesulfonic acid, m-styrenesulfonic acid, and o-styrenesulfonic acid.

[0037] The viral infection-inhibiting compound containing a salt of a sulfo group may have one or more salts of a sulfo group in the molecule, and examples thereof include linear alkylbenzenesulfonates, α-olefinsulfonates, alkyldiphenylethersulfonates, polyoxyalkylene alkyl ether sulfate ester salts, lauryl sulfate, polymers having a salt of a sulfo group in the side chain of a linear polymer, salts of polystyrenesulfonic acid, salts of formamidinesulfinic acid, salts of 3-aminobenzenesulfonic acid, salts of hydroxybenzenesulfonic acid, salts of m-xylene-4-sulfonic acid, salts of 5-sulfosalicylic acid, salts of sulfanilic acid, salts of 2-amino-3,5-dimethylbenzenesulfonic acid, salts of 1,3-phenylenediamine-4-sulfonic acid, salts of sulfonated (styrene-divinylbenzene copolymer), salts of carrageenan, salts of sulfonated polyethersulfone, and salts of ligninsulfonic acid.

[0038] Examples of linear alkylbenzenesulfonates include sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, ammonium dodecylbenzenesulfonate, magnesium dodecylbenzenesulfonate, barium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, ammonium tridecylbenzenesulfonate, sodium tetradecylbenzenesulfonate, and ammonium tetradecylbenzenesulfonate, with sodium dodecylbenzenesulfonate being preferred.

[0039] Examples of α-olefin sulfonates include C12 to C18 sodium olefin sulfonate, C12 to C18 calcium olefin sulfonate, C12 to C18 ammonium olefin sulfonate, C12 to C18 magnesium olefin sulfonate, and C12 to C18 barium olefin sulfonate, with C14 sodium tetradecene sulfonate being preferred.

[0040] Examples of alkyl diphenyl ether sulfonates include sodium salts, calcium salts, ammonium salts, magnesium salts, and barium salts of alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18. The alkyl group is a monovalent atomic group remaining after removing one hydrogen atom from an aliphatic saturated hydrocarbon.

[0041] In the polymer having a salt of a sulfo group in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers, polyesters, and polyurethanes are preferred, with vinyl polymers being more preferred.

[0042] The polymer having a sulfo group salt in the side chain of the linear polymer is not particularly limited, and examples thereof include a polymer containing a sulfo group salt-containing monomer containing a sulfo group salt as a monomer unit. In the polymer containing a sulfo group salt-containing monomer containing a sulfo group salt as a monomer unit, the content of the sulfo group salt-containing monomer is preferably 50 mol% or more, more preferably 75 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0043] Examples of polymers containing, as monomer units, sulfo group salt-containing monomers containing a salt of a sulfo group include polymers containing styrene sulfonate units, styrene sulfonate homopolymers, styrene-styrene sulfonate copolymers, sulfonates of compounds obtained by sulfonating the benzene rings of polystyrene, and sulfonates of compounds obtained by sulfonating the benzene rings of polymers containing a styrene component.

[0044] The salt-containing monomer of a sulfo group is not particularly limited, and examples include sodium p-styrenesulfonate, sodium m-styrenesulfonate, sodium o-styrenesulfonate, calcium p-styrenesulfonate, calcium m-styrenesulfonate, calcium o-styrenesulfonate, ammonium p-styrenesulfonate, ammonium m-styrenesulfonate, and ammonium o-styrenesulfonate. Sodium styrenesulfonate is preferred, and sodium p-styrenesulfonate is more preferred due to its less steric hindrance in reactivity with viruses.

[0045] At least one amino functional group selected from the group consisting of a primary amino group, a secondary amino group, and a tertiary amino group, or a salt of this amino functional group, preferably forms a cyclic skeleton, more preferably an alicyclic cyclic skeleton, since this improves the viral infection inhibitory effect of the viral infection inhibitor. It is preferable that the amino functional group or the salt of the amino functional group constitutes part of the alicyclic cyclic skeleton.

[0046] Here, a primary amino group refers to a monovalent substituent represented by -NH2. A secondary amino group refers to a divalent substituent (-NH-) resulting from removing (pulling out) one hydrogen atom from -NH2. A tertiary amino group refers to a trivalent substituent [≡N, formula (a)] resulting from removing (pulling out) two hydrogen atoms from -NH2. However, the amino functional group does not include a case where a keto group (>CO) is directly bonded to the nitrogen atom constituting the amino functional group. In formula (a), *1 to *3 are bonds and represent single bonds.

[0047] [ka]

[0048] The salt of the amino functional group is not particularly limited, but an acid addition salt is preferred. Examples of the acid for the acid addition salt include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, phosphorous acid, hydrobromic acid, maleic acid, malic acid, ascorbic acid, tartaric acid, lauric acid, stearic acid, palmitic acid, oleic acid, myristic acid, lauryl sulfuric acid, linolenic acid, and fumaric acid, and hydrochloride is preferred.

[0049] The viral infection-inhibiting compound having an amino functional group or a salt thereof may have one or more amino functional groups or salts thereof in the molecule, such as a polymer containing an amino functional group or a salt thereof in the side chain of a linear polymer.

[0050] In the polymer containing an amino functional group or a salt thereof in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymers and polyesters are preferred, with vinyl polymers being more preferred.

[0051] Examples of polymers containing an amino functional group or a salt thereof in the side chain of a linear polymer include polymers containing, as monomer units, amino functional group-containing monomers containing an amino functional group or a salt thereof. In polymers containing, as monomer units, amino functional group-containing monomers containing an amino functional group or a salt thereof, the content of the amino functional group-containing monomer is preferably 50 mol% or more, more preferably 75 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0052] The amino functional group-containing monomer containing an amino functional group or a salt thereof is not particularly limited, and examples thereof include 2-vinylpyridine, 4-vinylpyridine, vinylimidazole, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, t-butylaminoethyl (meth)acrylate, N-(aminoalkyl)acrylamide, N-(aminoalkyl)methacrylamide, a monomer obtained by reacting glycidyl (meth)acrylate with ammonia or dimethylamine, allylamine, diallylamine, methyldiallylamine, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, or salts of these amino functional groups. The amino functional group-containing monomer containing an amino functional group or a salt thereof may be used alone or in combination of two or more.

[0053] The viral infection-inhibiting compound having an amino functional group or a salt thereof in the molecule does not need to be a polymer. Examples of the viral infection-inhibiting compound having an amino functional group or a salt thereof in the molecule include chloromethylisothiazolinone, methylisothiazolinone, benzisothiazolinone, octylisothiazolinone, dichlorooctylisothiazolinone, bronopol, zinc pyrithione, benzalkonium, didecyldimethylammonium, carbendazim, diuron, iodopropynyl butylcarbamate, and thiabendazole.

[0054] When the viral infection-inhibiting compound is a polymer, it may be a homopolymer of a monomer having an infection-inhibiting functional group (infection-inhibiting functional group-containing monomer), or it may be a copolymer of an infection-inhibiting functional group-containing monomer and a monomer copolymerizable with this infection-inhibiting functional group-containing monomer.

[0055] The monomer copolymerizable with the infection-blocking functional group-containing monomer is not particularly limited, and examples thereof include alkyl acrylate, alkyl methacrylate, vinyl alkyl ether, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, acrylamide, methacrylamide, diacetone acrylamide, vinyl toluene, etc. The monomer copolymerizable with the infection-blocking functional group-containing monomer may be used alone or in combination of two or more.

[0056] The polymer that becomes the viral infection-inhibiting compound may be polymerized using a general-purpose polymerization method. For example, the viral infection-inhibiting compound can be obtained by polymerizing a monomer composition containing a monomer containing an infection-inhibiting functional group in the presence of a general-purpose radical polymerization initiator. Examples of the radical polymerization initiator include thermal cleavage radical polymerization initiators such as 1-hydroxycyclohexane-1-yl phenyl ketone, t-hexyl peroxypivalate, benzoyl peroxide, and azobisisobutyronitrile.

[0057] The viral infection-inhibiting compound also includes a compound having a guanidine structure in the molecule. The guanidine structure refers to a divalent atomic group having the structural formula shown in formula (b) below. Note that *4 and *5 are bonding groups and represent single bonds.

[0058] [ka]

[0059] Examples of viral infection-inhibiting compounds containing a guanidine structure in the molecule include a polymer having a structure represented by the following formula (1) (polyhexamethylene biguanide), an acid addition salt of a polymer having a structure represented by the following formula (2) (polyhexamethylene biguanide hydrochloride), polyhexamethylene guanidine, polyhexamethylene guanidine hydrochloride, and polyhexamethylene guanidine phosphate. Of these, an acid addition salt of a polymer having a structure represented by formula (1) is preferred, and a hydrochloride of a polymer having a structure represented by formula (1) [formula (2)] is more preferred. Here, n represents a repeating unit. n is a natural number of 2 or more. x represents the coefficient of added hydrochloric acid. In polyhexamethylene biguanide, the content of the structure represented by formula (1) is preferably 80 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%. In the hydrochloride salt of polyhexamethylene biguanide, the content of the structure represented by formula (2) is preferably 80 mol% or more, more preferably 90 mol% or more, more preferably 95 mol% or more, more preferably 99 mol% or more, and more preferably 100 mol%.

[0060] [ka]

[0061] [ka]

[0062] A viral infection-inhibiting compound containing at least one infection-inhibiting functional group selected from the group consisting of a carboxy group, a sulfo group, a primary amino group, a secondary amino group, and a tertiary amino group, or a salt thereof, and a viral infection-inhibiting compound containing a guanidine structure may be used in combination.

[0063] When the viral infection inhibiting compound contains a polymer, the weight-average molecular weight of the polymer is preferably at least 1000, more preferably at least 5000, more preferably at least 10000, and even more preferably at least 100000. When the weight-average molecular weight of the viral infection inhibiting compound is at least 1000, the yellowing resistance of the viral infection inhibitor can be improved, and when the viral infection inhibitor is attached to the surface of a substrate, the viral infection inhibiting effect can be more effectively exerted without impairing the appearance of the substrate, and the number of adsorption points with viruses per molecule of the viral infection inhibiting compound increases, strengthening the interaction between the viral infection inhibiting compound and viruses and improving the viral infection inhibiting effect of the viral infection inhibitor.

[0064] The weight-average molecular weight of the polymer contained in the virus infection inhibitory compound is preferably no greater than 1,500,000, more preferably no greater than 1,000,000, more preferably no greater than 900,000, more preferably no greater than 800,000, and more preferably no greater than 500,000. When the weight-average molecular weight of the virus infection inhibitory compound is 1,500,000 or less, the yellowing resistance of the virus infection inhibitor can be improved, and when the virus infection inhibitor is attached to the surface of a substrate, the virus infection inhibitory effect can be more effectively exerted without impairing the appearance of the substrate, and the cohesion tendency of the virus infection inhibitor is reduced, improving coatability.

[0065] In the present invention, the weight average molecular weight of the polymer is a value measured by GPC (gel permeation chromatography) and converted into polystyrene.

[0066] For example, the measurement can be performed using the following measurement device and under the following measurement conditions. Gel permeation chromatograph: Waters, product name "2690 Separations Model" Column: Showa Denko Co., Ltd., product name "GPC KF-806L" Detector: differential refractometer Sample flow rate: 1 mL / min Column temperature: 40℃ Eluent: THF

[0067] The viral infection-inhibiting compound is preferably formed into particles. The D90 particle size of the viral infection-inhibiting compound is preferably 2 μm or more, more preferably 2.5 μm or more, more preferably 3 μm or more, and more preferably 3.5 μm or more. The D90 particle size of the viral infection-inhibiting compound is preferably 25 μm or less, more preferably 22 μm or less, more preferably 20 μm or less, more preferably 18 μm or less, more preferably 16 μm or less, more preferably 14 μm or less, and more preferably 12 μm or less. When the D90 particle size is 2 μm or more, the surface area of ​​the entire viral infection-inhibiting compound is reduced, the agglomeration of the viral infection inhibitor is reduced, and the coatability is improved. This results in a form that facilitates interaction between the viral infection-inhibiting compound and viruses, thereby improving the viral infection-inhibiting effect of the viral infection inhibitor. A D90 particle size of 25 μm or less prevents aggregation of the virus infection inhibitor and increases the surface area, facilitating contact with viruses and improving the virus infection inhibitor's virus infection inhibitory effect. It also easily scatters visible light, suppresses discoloration of the virus infection inhibitor compound, and improves the yellowing resistance of the virus infection inhibitor. Furthermore, the number of coarse particles is reduced, improving the coatability of the virus infection inhibitor.

[0068] As described below, the D90 particle size of the viral infection-inhibiting compound is the particle size (90% cumulative particle size) at which the cumulative frequency (cumulative from particles with small particle sizes) in a volume-based particle size distribution measured by laser scattering method is 90%. By adjusting the D90 particle size of the viral infection-inhibiting compound to the above-mentioned range and adjusting the particle sizes of large particles in the viral infection-inhibiting compound to a predetermined range, the inclusion of coarse particles in the viral infection-inhibiting compound is reduced. The viral infection-inhibiting compound has infection-inhibiting functional groups on its surface, and by adjusting the particle size of the viral infection-inhibiting compound to the above-mentioned range, the amount of infection-inhibiting functional groups or guanidine structures present on the surface of the viral infection-inhibiting compound is adjusted, imparting an excellent viral infection-inhibiting effect to the viral infection inhibitor and reducing interactions between the infection-inhibiting functional groups and / or guanidine structures, thereby improving the yellowing resistance of the viral infection inhibitor.

[0069] The D50 particle size of the viral infection-inhibiting compound 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-inhibiting compound is preferably 14 μm or less, more preferably 12 μm or less, and more preferably 11 μm or less.

[0070] By setting the D50 particle size and D90 particle size of the viral infection-inhibiting compound within the above-mentioned ranges, the inclusion of coarse particles having particle sizes significantly different from the D50 particle size in the viral infection-inhibiting compound can be reduced, and the particle size of the viral infection-inhibiting compound can be made more appropriate.

[0071] Furthermore, by adjusting the particle size of the virus infection-inhibiting compound to a more appropriate range, the amount of infection-inhibiting functional groups and guanidine structures present on the surface of the virus infection-inhibiting compound can be more appropriately adjusted, more effectively imparting an excellent virus infection-inhibiting effect to the virus infection inhibitor, and also making it easier for visible light to be scattered, thereby suppressing discoloration of the virus infection-inhibiting compound and improving the yellowing resistance of the virus infection inhibitor.Furthermore, since the number of coarse particles is reduced, the coatability of the virus infection inhibitor can be improved.

[0072] The D90 particle size and D50 particle size of a viral infection-inhibiting compound refer to the particle sizes (90% cumulative particle size and 50% cumulative particle size) at which the cumulative frequency (cumulative from particles with small particle sizes) in the volume-based particle size distribution measured by laser scattering method is 90% and 50%, respectively. When a viral infection-inhibiting compound contains multiple types of viral infection-inhibiting compounds, the D90 particle size and D50 particle size of the viral infection-inhibiting compound are values ​​measured based on the entire viral infection-inhibiting compound.

[0073] [Support] The virus infection inhibitor contains the virus infection inhibitor compound, and the virus infection inhibitor compound has a specific surface area of ​​1 to 1000 m 2 / g of the support.

[0074] Specific surface area is 1 to 1000m 2 The support, which has a mass of 10 ...

[0075] Furthermore, by supporting the viral infection-inhibiting compound in the pore structure of a support having a specific surface area within a predetermined range, the interaction between the infection-inhibiting functional groups and / or guanidine structures of the viral infection-inhibiting compound can be reduced, improving the yellowing resistance of the viral infection inhibitor and reducing the coagulation tendency of the viral infection inhibitor, thereby improving its coatability.

[0076] Furthermore, by attaching the viral infection inhibitor compound to the surface of a support having a predetermined specific surface area, the viral infection inhibitor can be dispersed uniformly on the substrate described below without forming clumps, thereby increasing the surface area of ​​the viral infection inhibitor, ensuring sufficient contact between the viral infection inhibitor and the virus, and allowing the viral infection inhibitor to fully exert its viral infection inhibitory effect.

[0077] The carrier to which the viral infection-inhibiting compound is attached on its surface is not particularly limited as long as it does not inhibit the viral infection-inhibiting effect of the viral infection-inhibiting agent. The particles include resin particles and inorganic particles. The particles may be used alone or in combination of two or more types.

[0078] Examples of synthetic resins constituting the resin particles include styrene-based resins, acrylic-based resins, urethane-based resins, vinyl chloride-based resins, ABS resins, and synthetic rubbers such as styrene-butadiene rubber (SBR) and nitrile-butadiene rubber (NBR). Of these, styrene-based resins are preferred, and polystyrene is more preferred.

[0079] The styrene-based resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, styrene-based monomers such as styrene, methylstyrene, ethylstyrene, i-propylstyrene, dimethylstyrene, chlorostyrene, and bromostyrene, and copolymers containing, as monomer units, a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer.

[0080] Examples of vinyl monomers copolymerizable with styrene-based monomers include acrylic monomers such as acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, acrylic acid esters (methyl acrylate, ethyl acrylate, butyl acrylate, etc.), methacrylic acid esters (methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc.), maleic anhydride, and acrylamide.

[0081] The acrylic resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, acrylic monomers such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and pentyl (meth)acrylate, and copolymers containing, as monomer units, an acrylic monomer and one or more vinyl monomers copolymerizable with the acrylic monomer. Note that (meth)acrylate means acrylate or methacrylate.

[0082] Examples of vinyl monomers copolymerizable with acrylic monomers include acrylonitrile, methacrylonitrile, maleic anhydride, and acrylamide.

[0083] The inorganic material constituting the inorganic particles is not particularly limited, and examples thereof include silica, zeolite, diatomaceous earth, kaolin, hydrotalcite, calcium carbonate, calcium citrate, magnesium carbonate, aluminum hydroxide, magnesium hydroxide, titanium oxide, and talc.

[0084] The synthetic resin constituting the resin particles preferably contains an aromatic ring, which attracts the hydrophobic moiety of the viral infection-inhibiting compound attached to the surface of the resin particles and orients the infection-inhibiting functional group and guanidine structure outward, thereby enabling the viral infection-inhibiting agent to more effectively exert its viral infection-inhibiting effect.

[0085] The aromatic ring may be a monocyclic aromatic ring, or may be a fused monocyclic aromatic ring (fused aromatic ring). The aromatic ring is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, biphenyl, and phenoxyphenyl. The aromatic ring has one or more hydrogen atoms removed from either the aromatic ring or the fused aromatic ring, and is bonded to other atoms via a covalent bond.

[0086] The mass ratio of the viral infection inhibitory compound to the support (mass of viral infection inhibitory compound / mass of support) is preferably 0.01 or more, more preferably 0.02 or more, more preferably 0.05 or more, more preferably 0.07 or more, more preferably 0.1 or more, more preferably 0.2 or more, and more preferably 0.25 or more. The mass ratio of the viral infection inhibitory compound to the support (mass of viral infection inhibitory compound / mass of support) is preferably 10 or less, more preferably 7 or less, more preferably 5 or less, and more preferably 4 or less. When the mass ratio of the viral infection inhibitory compound to the support (mass of viral infection inhibitory compound / mass of support) is 0.05 or more, the viral infection inhibitor can be uniformly adhered to the surface of the support, allowing the viral infection inhibitor to exert its viral infection inhibitory effect more effectively, and the viral infection inhibitor can be uniformly dispersed in the coating material without agglomeration, resulting in excellent coatability of the viral infection inhibitor. When the mass ratio of the viral infection inhibitor compound to the support (mass of viral infection inhibitor compound / mass of support) is 10 or less, the viral infection inhibitor compounds do not bond to each other, and the viral infection inhibitor is efficiently arranged on the surface of the resin particles, thereby improving the viral infection inhibitory effect and improving the yellowing resistance of the viral infection inhibitor.

[0087] The method for supporting the viral infection inhibiting compound on the surface of the support is not particularly limited, and may be, for example, by relying on the adhesive strength of the viral infection inhibiting compound, or by adhering the viral infection inhibiting compound to the surface of the support using a binder resin. However, since this allows the viral infection inhibiting effect of the viral infection inhibitor to be effectively exerted, it is preferable that the viral infection inhibiting compound be attached to the surface of the support by the adhesive strength of the viral infection inhibiting compound itself.

[0088] The specific surface area of ​​the support is 1m 2 / g or more, and 50m 2 / g or more is preferable, and 100m 2 / g or more is more preferable, and 200m 2 / g or more is more preferable. 2 / g or less, and 2 / g or less is preferable, and 700m 2 / g or less is preferable, and 600m 2 / g or less is more preferable, and 500m 2 / g or less is more preferable, and 400m 2 / g or less. 2 When the specific surface area of ​​the support is 1000 m / g or more, the virus infection inhibitor compound can be dispersed within the pore structure of the support and supported, improving contact between the virus infection inhibitor and the virus, thereby improving the virus infection inhibitory effect of the virus infection inhibitor and improving the yellowing resistance of the virus infection inhibitor. 2 / g or less, the interaction between the carriers is reduced, the contact between the virus infection inhibitor and the virus is improved, the virus infection inhibitory effect of the virus infection inhibitor is improved, and the coagulation tendency of the virus infection inhibitor is reduced, improving the coatability.

[0089] The specific surface area of ​​the support refers to a value measured by the BET method in accordance with JIS Z8830.

[0090] The D50 particle size of the support is preferably 0.1 μm or more, more preferably 0.2 μm or more, more preferably 1 μm or more, and more preferably 2 μm or more. The D50 particle size of the support is preferably 200 μm or less, more preferably 100 μm or less, more preferably 80 μm or less, more preferably 60 μm or less, more preferably 40 μm or less, more preferably 20 μm or less, and more preferably 10 μm or less.

[0091] When the D50 particle size of the support is 0.1 μm or more, the virus infection inhibitory compound can be dispersed and supported within the pore structure of the support, improving contact between the virus infection inhibitor and the virus and improving the virus infection inhibitory effect of the virus infection inhibitor. Furthermore, the virus infection inhibitor is efficiently arranged on the surface of the resin particles without bonding to itself, improving the virus infection inhibitory effect and improving the yellowing resistance of the virus infection inhibitor.

[0092] When the D50 particle size of the support is 200 μm or less, visible light is easily scattered, discoloration of the virus infection inhibitor compound can be suppressed, and the yellowing resistance of the virus infection inhibitor can be improved. Furthermore, the number of coarse particles can be reduced, which can improve the coatability of the virus infection inhibitor.

[0093] The D50 particle size of a support refers to the particle size (50% cumulative particle size) at which the cumulative frequency (cumulative from particles with small particle sizes) in the volume-based particle size distribution measured by the laser scattering method is 50%. When the support contains multiple types of supports, the D50 particle size of the support is a value measured based on the entire support.

[0094] [Virus infection inhibitor] The virus infection inhibitor comprises a support having a specific surface area within a predetermined range and a predetermined virus infection-inhibiting compound supported on the support. The method for producing the virus infection inhibitor is not particularly limited, and the virus infection inhibitor can be produced by supporting the virus infection-inhibiting compound on the support in a general manner.

[0095] In the viral infection inhibitor, the total amount of the support and the viral infection inhibitor compound supported on this support 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, and more preferably 99% by mass or more.

[0096] The viral infection inhibitor has an inhibitory effect on various viruses due to the action of the viral infection inhibitor compound, and exhibits excellent viral infection inhibitory effect on both enveloped and non-enveloped viruses.

[0097] Examples of enveloped viruses include influenza viruses (e.g., influenza A, B, etc.), rubella viruses, Ebola viruses, coronaviruses (e.g., SARS virus, novel coronavirus (SARS-CoV-2)), measles viruses, varicella-zoster viruses, herpes simplex viruses, mumps viruses, arboviruses, respiratory syncytial viruses, hepatitis viruses (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever viruses, AIDS viruses, rabies viruses, hantaviruses, dengue viruses, Nipah viruses, and lyssaviruses.

[0098] Examples of non-enveloped viruses include feline calicivirus, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, and rhinovirus.

[0099] The virus infection inhibitor is used by being contained in a base material to which it is desired to impart a virus infection inhibitory effect, and the base material containing the virus infection inhibitor exhibits a virus infection inhibitory effect as a virus infection inhibitory product.

[0100] Furthermore, since the virus infection inhibitor has excellent resistance to yellowing, a substrate containing the virus infection inhibitor can maintain its original appearance for a long period of time without yellowing due to the virus infection inhibitor.

[0101] The substrate to be loaded with the virus infection inhibitor is not particularly limited as long as it can contain the virus infection inhibitor, and examples include synthetic resin molded products, paints, wallpaper, decorative sheets, flooring materials, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), interior and interior materials for vehicles (e.g., cars, airplanes, ships, etc.) (seats, child seats, and the foams that make up these), kitchenware, baby products, and building interior materials.

[0102] The synthetic resin constituting the synthetic resin molded article is not particularly limited, and examples thereof include thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylonitrile styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefin, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyether ether ketone, thermoplastic polyimide, polyamideimide, etc.), thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin, silicone resin, polyurethane, thermosetting polyimide, etc.). The synthetic resins may be used alone or in combination of two or more.

[0103] The virus infection inhibitor may be used by kneading it into a synthetic resin. A method for kneading the virus infection inhibitor into a synthetic resin involves mixing the virus infection inhibitor with a synthetic resin raw material to prepare a resin composition, and using this resin composition to obtain a virus infection-inhibiting product in a desired shape as a molded article by a general-purpose synthetic resin molding method. Examples of general-purpose synthetic resin molding methods include extrusion molding, injection molding, and blow molding. A synthetic resin and the virus infection inhibitor may be included in a synthetic resin molding masterbatch, which may be mixed with the synthetic resin raw material, and the virus infection-inhibiting product may be produced as a molded article by a general-purpose synthetic resin molding method.

[0104] In the viral infection-preventing product, the content of the viral infection inhibitor is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more, per 100 parts by mass of the base material. In the viral infection-preventing product, the content of the viral infection inhibitor is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, and more preferably 7 parts by mass or less, per 100 parts by mass of the base material.

[0105] [Masterbatch for synthetic resin molding] The synthetic resin molding masterbatch contains a synthetic resin and a virus infection inhibitor. Only one type of synthetic resin may be used, or two or more types may be used in combination. The synthetic resin may be a thermoplastic resin or a thermosetting resin, but a thermoplastic resin is preferred. Examples of thermoplastic resins include polyolefin resin, polyvinyl chloride resin, polyamide resin, polycarbonate resin, polystyrene resin, polyester resin, acrylonitrile-butadiene-styrene resin (ABS resin), polyethylene terephthalate (PET), polyurethane resin, and polymethyl methacrylate (PMMA).

[0106] The content of the synthetic resin in the masterbatch for synthetic resin molding is preferably 10% by mass or more, more preferably 20% by mass or more, and is preferably 80% by mass or less, more preferably 60% by mass or less.

[0107] The content of the virus infection inhibitor in the synthetic resin molding masterbatch is preferably 10% by mass or more, more preferably 15% by mass or more, and is preferably 80% by mass or less, more preferably 70% by mass or less.

[0108] The resin composition, particularly the masterbatch for synthetic resin molding, preferably further contains a surfactant. The surfactant is not particularly limited and examples thereof include anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants, with anionic surfactants and nonionic surfactants being preferred. When the masterbatch for synthetic resin molding further contains a surfactant, the virus infection-inhibiting compound is more likely to segregate on the surface of the resulting virus infection-inhibiting product (molded article), further enhancing the virus infection-inhibiting effect of the virus infection-inhibiting product (molded article).

[0109] The anionic surfactant is not particularly limited, and examples thereof include alkyl phosphates such as sodium dodecyl phosphate, potassium dodecyl phosphate, sodium stearyl phosphate, and potassium stearyl phosphate; polyoxyethylene alkyl ether phosphate salts such as polyoxyethylene (3) lauryl ether sodium phosphate and polyoxyethylene (3) lauryl ether potassium phosphate; polyoxyethylene alkyl phenyl ether phosphates such as polyoxyethylene (3) lauryl phenyl ether sodium phosphate and polyoxyethylene (3) lauryl phenyl ether potassium phosphate; alkyl benzene sulfonates (e.g., sodium dodecyl benzene sulfonate, potassium dodecyl benzene sulfonate, ammonium dodecyl benzene sulfonate, and triethanolammonium dodecyl benzene sulfonate); α-olefin sulfonates; alkyl diphenyl ether sulfonates; and polyoxyalkylene alkyl ether sulfate salts, among which alkyl benzene sulfonates are preferred.

[0110] The nonionic surfactant is not particularly limited, and examples thereof include polyoxyalkylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters (e.g., polyethylene glycol distearate, etc.), polyoxyethylene distyrenated phenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, fatty acid alkanolamides (e.g., coconut fatty acid dimethanolamide, coconut fatty acid diethanolamide, coconut fatty acid dipropanolamide, and other coconut fatty acid alkanolamides), fatty acid alkylolamides, alkylalkanolamides, acetylene glycol, oxyethylene adducts of acetylene glycol, polyethylene glycol polypropylene glycol block copolymers, and the like, of which polyoxyethylene distyrenated phenyl ethers, polyoxyethylene fatty acid esters, and fatty acid alkanolamides are preferred.

[0111] The amphoteric surfactant is not particularly limited, and examples thereof include alkylaminoacetic acid betaine, alkylamidopropyl betaine, sulfobetaine, alkylamino(mono- or di-)propionate, imidazolinium betaine, alkylamine oxide, alkylaminoethylglycine, alkyldi(aminoethyl)glycine, glycine n-(3-aminopropyl) C10-16 derivative, alkylpolyaminoethylglycine, alkyl-β-alanine, alkyldiethanolamine, polyoxyalkylene alkylamine, and oxyethylene adduct surfactant of diamine.

[0112] The content of the surfactant in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, and is preferably 40% by mass or less, more preferably 30% by mass or less.

[0113] The virus infection inhibitor used in the resin composition, particularly the synthetic resin molding masterbatch, preferably contains an antioxidant. By containing an antioxidant in the virus infection inhibitor, yellowing of the synthetic resin during molding using the synthetic resin molding masterbatch or in the resulting molded product (virus infection-preventing product) can be reduced.

[0114] The antioxidant is not particularly limited and examples thereof include monophenol-based antioxidants, bisphenol-based antioxidants, amine-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, etc., with phenol-based antioxidants and bisphenol-based antioxidants being preferred. The antioxidants may be used alone or in combination of two or more.

[0115] Examples of monophenol-based antioxidants include dibutylhydroxytoluene (BHT), dibutylhydroxyanisole (BHA), octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate, 2-[1-(2-hydroxy-3,5-di-tert-pentylphenyl)ethyl]-4,6-di-tert-pentylphenyl acrylate, 4,4'-butylidenebis

[0033] Examples include (3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol), tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane, and 3,9-bis[2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)-propionyloxy)-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5,5]undecane, and dibutylhydroxytoluene (BHT) and di-dibutylhydroxyanisole (BHA) are preferred because they provide excellent resistance to yellowing of the resulting molded articles.

[0116] Examples of bisphenol-based antioxidants include 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 3,9-bis[1,1-dimethyl-2-[β-(3-t-butyl-4-hydroxy-5-methylphenol] [phenyl)propionyloxy]ethyl]2,4,8,10-tetraoxaspiro[5.5]undecane, 2,2'-dihydroxy-3,3'-di(α-methylcyclohexyl)-5,5'-dimethyldiphenylmethane, etc., and 2,2'-methylenebis(4-methyl-6-t-butylphenol) and 4,4'-thiobis(3-methyl-6-t-butylphenol) are preferred because they provide excellent yellowing resistance to the resulting molded articles.

[0117] The melting point of the antioxidant is preferably 200°C or lower, more preferably 170°C or lower, and even more preferably 100°C or lower. The melting point of the antioxidant is preferably 50°C or higher, more preferably 60°C or higher. When the melting point of the antioxidant is 200°C or lower, the antioxidant melts during molding using a synthetic resin molding masterbatch, increasing the degree of miscibility between the virus infection inhibitor containing the antioxidant and the synthetic resin, thereby reducing yellowing of the synthetic resin during molding or in the resulting molded product (virus infection-inhibiting product). When the melting point of the antioxidant is 50°C or higher, the handleability of the virus infection inhibitor containing the antioxidant at room temperature is improved, which is preferable. The melting point of the antioxidant refers to the temperature measured in accordance with JIS K0064:1992.

[0118] The content of the antioxidant in the virus infection inhibitor is preferably 0.1% by mass or more, more preferably 1% by mass or more, and the content of the surfactant in the virus infection inhibitor is preferably 5% by mass or less, more preferably 4% by mass or less.

[0119] The synthetic resin molding masterbatch is preferably in the form of resin pellets because of its excellent moldability. By melting and molding the resin pellets, a virus infection-preventing product (molded product) with excellent virus infection-preventing effects can be obtained.

[0120] The shape of the resin pellets is not particularly limited, and examples include spherical, cylindrical, and prismatic shapes. From the viewpoint of pellet shape stability, a cylindrical shape is preferred. The maximum length dimension of the resin pellets is preferably 1 mm or more, more preferably 3 mm or more. The maximum length dimension of the resin pellets is preferably 10 mm or less, more preferably 7 mm or less.

[0121] The synthetic resin molding masterbatch can be used by mixing with other resin materials. The other resin materials may be resin pellets. The synthetic resin molding masterbatch and the other resin materials are mixed to obtain a mixed resin material, and then the mixed resin material is molded to obtain a virus infection-preventing product (molded product) with excellent virus infection-preventing effect.

[0122] As the paint, conventionally known paints are used, for example, oil-based paints (e.g., mixed paints, oil varnishes, etc.), cellulose paints, synthetic resin paints, etc. The paint also includes photocurable paints that polymerize upon irradiation with radiation such as ultraviolet light to produce a binder component.

[0123] Because the virus infection inhibitor has excellent coating properties, it can be uniformly dispersed in the paint, and the coating film produced from this paint exhibits a generally uniform virus infection prevention effect overall.

[0124] Because the virus infection inhibitor has excellent resistance to yellowing, a coating film formed from a paint containing the virus infection inhibitor does not yellow over a long period of time, and therefore, an article having a coating film formed on its surface can maintain its appearance over a long period of time.

[0125] The paint may contain additives such as pigments, plasticizers, curing agents, extenders, fillers, antioxidants, thickeners, and surfactants, as long as the additives do not impair the paint's physical properties. Examples of methods for incorporating the virus infection inhibitor into the paint include a method in which the virus infection inhibitor and the paint are supplied to a dispersing device and mixed uniformly. Examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill.

[0126] The building interior materials are not particularly limited, and examples thereof include flooring materials, wallpaper, ceiling materials, paints, doorknobs, switches, switch covers, wax, and the like.

[0127] The vehicle interior goods and materials are not particularly limited, and examples thereof include seats, child seats, seat belts, car mats, seat covers, doors, ceiling materials, floor mats, door trim, instrument panels, consoles, glove boxes, handrails, and the like. [Example]

[0128] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

[0129] Polymers 1 to 10, citric acid, N-[1-[2-(dodecylamino)ethylamino]ethyl]glycine, and N-[1-[2-(dodecylamino)ethylamino]ethyl]glycine hydrochloride were prepared as viral infection-inhibiting compounds. When the viral infection-inhibiting compounds were polymers, the weight-average molecular weights were shown in the "Weight-average molecular weight" column of Tables 1 to 3. For convenience, the molecular weight of citric acid was listed in the "Weight-average molecular weight" column. For convenience, the "guanidine structure" of the viral infection-inhibiting compounds was listed in the "Viral infection-inhibiting functional group" column.

[0130] [Viral infection inhibitor compound] Polymer 1 (polystyrene sulfonic acid, formula (3), product name "Versa-TL72" manufactured by Nouryon) Polymer 2 (polyacrylic acid, formula (4), manufactured by Nippon Shokubai Co., Ltd., trade name "HL-415") Citric acid Polymer 3 (polyallylamine, formula (5), manufactured by Nittobo Medical Co., Ltd., trade name "PAA-15C") Polymer 4 (diallylamine hydrochloride polymer, formula (6), manufactured by Nittobo Medical Co., Ltd., trade name "PAS-21CL") Polymer 5 (diallylamine polymer, formula (7), manufactured by Nittobo Medical Co., Ltd., trade name "PAS-21") Polymer 6 (copolymer of allylamine hydrochloride and diallylamine hydrochloride, formula (8), manufactured by Nittobo Medical Co., Ltd., trade name "PAA-D19-JCl") Polymer 7 (copolymer of diallylamine hydrochloride and maleic acid, formula (9), manufactured by Nittobo Medical Co., Ltd., trade name "PAS-410C") Polymer 8 (copolymer of diallylamine hydrochloride and maleic acid, formula (9), manufactured by Nittobo Medical Co., Ltd., trade name "PAS-411C") Polymer 9 (methyldiallylamine hydrochloride polymer, formula (10), manufactured by Nittobo Medical Co., Ltd., trade name "PAS-M-1") Polymer 10 (polyhexamethylene biguanide hydrochloride, formula (2), Lonza, trade name "VANTOCIL TG") N-[1-[2-(dodecylamino)ethylamino]ethyl]glycine (trade name "Levon S" manufactured by Sanyo Chemical Industries, Ltd.) (in the table, this is referred to as "dodecylaminoethylaminoethylglycine") N-[1-[2-(dodecylamino)ethylamino]ethyl]glycine hydrochloride (manufactured by Sanyo Chemical Industries, Ltd., trade name "Levon T-2") (in the table, this is referred to as "dodecylaminoethylaminoethylglycine hydrochloride")

[0131] [ka]

[0132] In the formulas (3) to (10), n, m, and p represent repeating units and are natural numbers of 2 or more.

[0133] [ka]

[0134] Among the structural formulas shown above, the structural formula expressed as formula (11) means a random copolymer, alternating copolymer, or block copolymer of a monomer unit M1 and a monomer unit M2. n, m, and p represent repeating units and are natural numbers of 2 or more. In formulas (1) to (11), n, m, and p simply represent repeating units. In formulas (1) to (11), n, m, and p each have an independent value. In formula (2), x is the coefficient of added hydrochloric acid.

[0135] [ka]

[0136] [Support (particles)] Silica particles 1 (manufactured by Fuji Silysia Pharmaceuticals, product name "SYLOSPHERE C-1504") Silica particles 2 (manufactured by Admattex Co., Ltd., product name "SO-C1") Silica particles 3 (manufactured by Admattex Co., Ltd., product name "SO-C6") Silica particles 4 (manufactured by Fuji Silysia Pharmaceuticals, product name "SYLYSIA 250") Silica particles 5 (manufactured by Fuji Silysia Pharmaceuticals, product name "SYLYSIA 730") Silica particles 6 (AGC Si-Tech Co., Ltd., product name "Sunsphere H-51") Zeolite particles (manufactured by Tosoh Corporation, product name "930NHA") Diatomaceous earth particles (Hayashi Kasei Co., Ltd., product name "Radiolite 100") Kaolin particles (BASF product name "Satintone 5HB") Calcium carbonate particles 1 (manufactured by Sankyo Seifun Co., Ltd., product name "Escalon #200") Calcium carbonate particles 2 (manufactured by Sankyo Seifun Co., Ltd., product name "Escalon (A)") Talc particles (product name "Micro Ace P-8" manufactured by Nippon Talc Co., Ltd.) Aluminum hydroxide particles (Showa Denko product name "A-43-L") Titanium oxide particles (manufactured by Ishihara Sangyo Kaisha, Ltd., product name "PT-301") Hydrotalcite particles 1 (Mg4Al2(OH) 12 CO3·3H2O, Mg-Al type, manufactured by Sakai Chemical Industry Co., Ltd. (product name "HT-1") Hydrotalcite particles 2 (Mg6Al2(OH) 16 CO3·mH2O, Mg-Al type, Sakai Chemical Industry Co., Ltd. (product name "HT-6") Hydrotalcite particles 3 (Mg 4.5 Al2(OH) 13 CO3·3.5H2O, Mg-Al type, manufactured by Sakai Chemical Industry Co., Ltd. (product name "HT-P") Hydrotalcite particles 4 (Mg 3.5 Zn 0.5 Al2(OH) 12 CO3·3H2O, Mg-Zn-Al type, manufactured by Sakai Chemical Industry Co., Ltd. (product name "HT-7") Acrylic resin particles 1 (manufactured by Sekisui Plastics Co., Ltd., product name "MBP-8HP") Acrylic resin particles 2 (manufactured by Sekisui Plastics Co., Ltd., product name "MBP-8")

[0137] [Antioxidants] [Monophenolic antioxidant] Dibutylhydroxytoluene (BHT) Dibutylhydroxyanisole (BHA) [Bisphenol-based antioxidants] Bisphenol-based antioxidant 1 (2,2'-methylenebis(4-methyl-6-tert-butylphenol), product name "Nocrac NS-6" manufactured by Ouchi Shinko Chemical Industry Co., Ltd.) Bisphenol-based antioxidant 2 (4,4'-thiobis(3-methyl-6-tert-butylphenol), product name "Nocrac 300" manufactured by Ouchi Shinko Chemical Industry Co., Ltd.)

[0138] (Examples 1 to 31, Comparative Example 11) Water was prepared in an amount 7 times the total mass of the viral infection-inhibiting compound and the support. The types of viral infection-inhibiting compound and support (particles) shown in Tables 1 and 2 were added to the water and mixed uniformly to prepare a dispersion. The particles used as the support had the D50 particle size and specific surface area shown in Tables 1 and 2. The mass ratio of the viral infection-inhibiting compound to the support added to the water (mass of viral infection-inhibiting compound / mass of support) is shown in the "Compound / Support" column in Tables 1 and 2.

[0139] Next, the dispersion was powdered using a spray dryer at an atomizer rotation speed of 20,000 rpm, and the entire amount of the virus infection inhibitory compound was attached (supported) to the surface of the support.Then, using a jet mill (manufactured by Nisshin Engineering, product name "SJ-500"), the support was pulverized under operating conditions of a raw material supply rate of 1 kg / h and a compressed air pressure of 0.75 MPa, and a support with the virus infection inhibitory compound supported (attached) on its surface was obtained as a virus infection inhibitor.

[0140] A coating composition (virus infection-preventing product) was prepared by mixing 5 parts by mass of the virus infection inhibitor shown in Tables 1 and 2 with 95 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec Co., Ltd., product name "AI-N2") The coating composition was applied to a polyethylene film using a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0141] Using a UV conveyor device (Eye Graphics "ECS301G1"), ultraviolet light with a wavelength of 365 nm was applied to the coating layer at 25°C with an integrated light intensity of 500 mJ / cm. 2 The ultraviolet-curable acrylic paint was cured by irradiating it so as to form a coating film with a thickness of 18 μm.

[0142] (Comparative Example 1) The viral infection-inhibiting compound shown in the "Type" column of Table 2 was used without being supported on a support. Specifically, the viral infection-inhibiting compound (polymer 1) was pulverized using a jet mill (manufactured by Nisshin Engineering, product name "SJ-500") under operating conditions of a raw material supply rate of 1 kg / h and a compressed air pressure of 0.75 MPa to obtain particles of the viral infection-inhibiting compound. A coating composition (viral infection-inhibiting product) was prepared by mixing 5 parts by mass of the viral infection-inhibiting compound (polymer 1) shown in Table 2 with 95 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec, product name "AI-N2"). This coating composition was used to form a coating film with a thickness of 18 μm in the same manner as in Example 1.

[0143] (Comparative Examples 2 to 9) The viral infection-inhibiting compound shown in the "Type" column of Table 2 was used without being supported on a support. Specifically, the viral infection-inhibiting compound obtained by freeze-drying was coarsely pulverized using a roll press (Seishin Enterprise Co., Ltd., product name "150 Type") at a rotation speed of 25 rpm and a pressure of 25 tons. This was then pulverized using a jet mill (Nisshin Engineering, product name "SJ-500") at a raw material feed rate of 1 kg / h and a compressed air pressure of 0.75 MPa to obtain particles of the viral infection-inhibiting compound. A coating composition was prepared by mixing 5 parts by mass of the viral infection-inhibiting compound shown in the "Type" column of Table 2 with 95 parts by mass of an ultraviolet-curable acrylic paint (Coattec Co., Ltd., product name "AI-N2"). This coating composition was used to form a coating film with a thickness of 18 μm in the same manner as in Example 1.

[0144] (Comparative Example 10) The viral infection-inhibiting compound shown in the "Type" column of Table 2 was used without being supported on a support. Specifically, the viral infection-inhibiting compound was freeze-dried to obtain a paste of the viral infection-inhibiting compound. A coating composition was prepared by mixing 5 parts by mass of the viral infection-inhibiting compound shown in the "Type" column of Table 2 with 95 parts by mass of an ultraviolet-curable acrylic paint (manufactured by Coattec Co., Ltd., product name "AI-N2"). This coating composition was used to form a coating film with a thickness of 18 μm in the same manner as in Example 1.

[0145] The obtained coating film was subjected to an antiviral test, and measurements of yellowing resistance and coating properties were carried out in the following manner. The results are shown in Tables 1 and 2.

[0146] (Antiviral test) A test piece was prepared by cutting out a flat square piece with each side measuring 5.0 cm from the coating film.

[0147] The surface of the coating film on the obtained test piece was soaked in 1 mL of water with a flat square nonwoven fabric (manufactured by Nippon Paper Crecia Co., Ltd., product name "Kimwipe S-200") with each side measuring 10 cm, and the coating film surface was wiped with the nonwoven fabric by moving it back and forth 10 times to obtain a test coating film.

[0148] The obtained test coating film was subjected to antiviral tests against influenza virus and feline calicivirus in accordance with ISO 21702. The virus infectivity of the test coating film was calculated by the plaque method for the virus suspension after the reaction.

[0149] A blank coating was prepared in the same manner as above, except that no virus infection inhibitor was added, and the virus infectivity (common logarithm) (PFU / cm) was calculated based on this blank coating in the same manner as above. 2 The virus infectivity titer (common logarithm) of the blank coating was 6.5 PFU / cm 2 It was.

[0150] The antiviral activity value was calculated by subtracting the viral infectivity of the test coating from the viral infectivity of the blank paint.

[0151] (yellowing resistance) A durability test was conducted at 120°C for 1,000 hours on test coatings obtained in the same manner as the antiviral test. The yellow index of the test coatings before and after the test was measured using a spectrophotometer (Konica Minolta "CM-5") in accordance with ASTM E313-73. The yellow index before the test was subtracted from the yellow index after the test to calculate the yellowing index (ΔYI). The smaller the ΔYI value, the less yellowing there was after the test, and the higher the yellowing resistance.

[0152] [Coatability] The depth at which streaks appeared on the coating composition was measured using a grind gauge in accordance with JIS K5600-2-5, and the maximum streak depth was used to evaluate the coating properties. The smaller the maximum streak depth, the higher the dispersibility of the virus infection inhibitor in the coating material, and the better the coatability of the virus infection inhibitor.

[0153] [Masterbatch for synthetic resin molding] (Examples 32 to 46, Comparative Example 12) Water was prepared in an amount 7 times the total mass of the viral infection-inhibiting compound and the carrier. The viral infection-inhibiting compound and the carrier (particles) shown in Table 3 were added in predetermined amounts to the water and mixed uniformly to prepare a dispersion. The particles used as the carrier had the D50 particle size and specific surface area shown in Table 3.

[0154] Next, the dispersion was powdered using a spray dryer at an atomizer rotation speed of 20,000 rpm, and the entire amount of the virus infection-inhibiting compound was attached (supported) to the surface of the support.Then, using a jet mill (manufactured by Nisshin Engineering, product name "SJ-500"), the mixture was pulverized under operating conditions of a raw material supply rate of 1 kg / h and a compressed air pressure of 0.75 MPa, to obtain a support with the virus infection-inhibiting compound supported (attached) on its surface.The mass ratio of the virus infection-inhibiting compound to the support (mass of the virus infection-inhibiting compound / mass of the support) is shown in the "Compound / Support" column of Table 3.

[0155] In Examples 32 to 40 and Comparative Example 12, the obtained support was used as a virus infection inhibitor. In Examples 41 to 46, an antioxidant was added to the obtained support and mixed uniformly to prepare a virus infection inhibitor. The amounts of the virus infection inhibitory compound, support, and antioxidant in the virus infection inhibitor were adjusted to be as shown in Table 3.

[0156] 50 parts by mass of the obtained virus infection inhibitor and 50 parts by mass of polypropylene (manufactured by Japan Polypropylene Corporation, trade name "Novatec PP BC6C") were uniformly melt-kneaded and mixed to prepare a masterbatch for synthetic resin molding.

[0157] The obtained synthetic resin molding masterbatch and separately prepared polypropylene (PP, manufactured by Japan Polypropylene Corporation, trade name "Novatec PP BC6C") were melt-kneaded in a mass ratio of 1:9 at 180°C for 5 minutes to prepare a resin composition.

[0158] The obtained resin composition was press-molded to obtain a sheet-shaped resin molded product having an average thickness of 1 mm as a viral infection-preventing product.

[0159] The obtained viral infection-preventing product was subjected to an antiviral test using the same test method as for the coating film to measure its antiviral activity value, and the results are shown in Table 3.

[0160] The yellowing resistance of the obtained virus infection-preventing product was measured in the same manner as for the coating film, and the results are shown in Table 3.

[0161] [Table 1]

[0162] [Table 2]

[0163] [Table 3] [Industrial Applicability]

[0164] The virus infection inhibitor of the present invention can be used to produce a coating material having excellent coatability, and can produce a coating material that produces a coating film that hardly yellows even when placed in a high-temperature environment and has excellent virus infection-inhibiting effects.

[0165] The virus infection inhibitor of the present invention has excellent resistance to yellowing, and therefore it is possible to produce a virus infection inhibitor product that maintains the appearance of the substrate, such as its color, and has excellent virus infection inhibitory effect.

[0166] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority based on Japanese Patent Application No. 2022-128501 filed on August 10, 2022, and Japanese Patent Application No. 2022-176594 filed on November 2, 2022, the disclosures of which are incorporated herein by reference in their entirety.

Claims

1. Specific surface area is 1 to 1000 m 2 / g of a support; a viral infection-inhibiting compound which is a polymer containing a secondary amino group or a guanidine structure and which is supported on the support;

2. 2. The virus infection inhibitor according to claim 1, wherein the D50 particle size of the carrier is 0.1 to 200 μm.

3. A viral infection inhibitor as described in claim 1 or claim 2, characterized in that the mass ratio of the viral infection inhibitory compound to the support (mass of the viral infection inhibitory compound / mass of the support) is 0.02 to 10.

4. The specific surface area of ​​the support is 50 to 1000 m 2 3. The virus infection inhibitor according to claim 1, wherein the antiviral activity is 0.01g / g.

5. 3. The virus infection inhibitor according to claim 1, wherein the virus infection inhibitor compound is a polymer having a weight-average molecular weight of 1,000 or more.

6. 3. The virus infection inhibitor according to claim 1, wherein the virus infection inhibitor compound is a polymer having a secondary amino group.

7. 3. The virus infection inhibitor according to claim 1, further comprising an antioxidant.

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

9. 9. The resin composition according to claim 8, which is used as a masterbatch for synthetic resin molding.

10. 10. The resin composition according to claim 9, wherein the virus infection inhibitor contains an antioxidant.

11. 11. The resin composition according to claim 10, wherein the antioxidant has a melting point of 200°C or less.

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

13. 13. The virus infection prevention product according to claim 12, wherein the substrate is a paint.

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