Virus infection inhibitors and virus infection inhibitor products

Abstract

To provide a viral infection inhibitor that is effective in inhibiting viral infection.SOLUTION: A viral infection inhibitor comprises a viral infection inhibitory compound comprising a carboxy group and having a pKa1 of 5.5 or less and a weight average molecular weight of 3000 or more, so that it exhibits excellent viral infection inhibitory effect on both viruses with or without an envelope, exhibiting viral infection inhibitory effect on various kinds of viruses.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a virus infection inhibitor 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] To address these problems, Patent Document 1 proposes an antiviral synthetic resin composition containing 0.5 parts by mass or more of a sulfonic acid surfactant per 100 parts by mass of synthetic resin. [Prior art documents] [Patent documents]

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

[0006] However, the above-mentioned antiviral synthetic resin composition merely contains a sulfonic acid surfactant in a synthetic resin, and the sulfonic acid surfactant does not have sufficient antiviral properties (viral infection inhibitory effect), and therefore a virus infection inhibitor with excellent virus infection inhibitory effect is desired.

[0007] The present invention provides a virus infection inhibitor that can exert an excellent virus infection inhibitory effect. [Means for solving the problem]

[0008] The viral infection inhibitor of the present invention is characterized by containing a viral infection inhibitory compound that contains a carboxy group or a salt thereof, has a pKa1 of 5.5 or less, and has a weight-average molecular weight of 3,000 or more.

[0009] The viral infection prevention product of the present invention comprises: A substrate; The virus infection inhibitor is contained in the base material. [Effects of the Invention]

[0010] The viral infection inhibitor of the present invention contains a viral infection inhibitory compound that contains a carboxy group or a salt thereof, has a pKa1 of 5.5 or less, and has a weight-average molecular weight of 3000 or more, and therefore has excellent viral infection inhibitory effects against both enveloped and non-enveloped viruses, and exhibits viral infection inhibitory effects against a variety of viruses. DETAILED DESCRIPTION OF THE INVENTION

[0011] The viral infection inhibitor of the present invention contains a viral infection inhibitory compound that contains a carboxy group or a salt thereof, has a pKa1 of 5.5 or less, and has a weight-average molecular weight of 3,000 or more.

[0012] [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 a carboxy group (-COOH) or a salt thereof in the molecule. The viral infection inhibitory compound exerts a viral infection inhibitory effect due to the molecular structure portion containing the carboxy group or a salt thereof. The viral infection inhibitory compound has an excellent viral infection inhibitory effect, particularly against enveloped viruses.

[0013] The salt of the carboxy group contained in the viral infection-inhibiting compound is not particularly limited, and examples thereof include sodium salt (-COONa), calcium salt [(-COON- )2Ca 2+ ], ammonium salt (-COO - NH4 + ), magnesium salt [(-COO - )2Mg 2+ ], barium salts [(-COO - )2Ba 2+ ] etc.

[0014] The term "viral infection inhibitory effect" refers to the effect of eliminating or reducing the infectivity of a virus to a cell, or of preventing the virus from replicating in the cell even if it infects. Examples of methods for confirming the infectivity of such a virus include ISO 18184 and JIS L 1922 for textile products, and ISO 21702 for plastics and non-porous surface products other than textile products. Other methods include the plaque method and hemagglutination assay (HAU) method described in "Medical and Pharmaceutical Virology" (first published April 1990).

[0015] The pKa1 of the viral infection inhibitory compound is 5.5 or less, preferably 5.0 or less, and more preferably 4.7 or less. When the pKa1 of the viral infection inhibitory compound is 5.5 or less, the viral infection inhibitory effect of the viral infection inhibitor is improved. When the viral infection inhibitory compound is a polyvalent acid, the viral infection inhibitory compound undergoes multi-stage ionization, and pKa1 refers to the pKa calculated based on the ionization constant of the first stage. Here, the electrolyte HA is H + and A - When an acid dissociates into alkane and reaches ionization equilibrium (1), the acid dissociation constant Ka is defined by equation (2), and pKa is defined as the common logarithm (3) of the reciprocal of the acid dissociation constant Ka.

[0016]

number

[0017] The pKa1 of a viral infection-inhibiting compound is a value measured by titration. Specifically, the pKa1 can be determined by titrating the viral infection-inhibiting compound 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 dropwise).

[0018] When the viral infection inhibiting compound contains a salt of a carboxy group, the pKa1 of the viral infection inhibiting compound is the pKa1 of the viral infection inhibiting compound measured by the above-mentioned method after converting the salt of the carboxy group to a carboxy group. Examples of a method for converting a salt of a carboxy group to a carboxy group include mixing the viral infection inhibiting compound with a 1 mol% aqueous hydrochloric acid solution, converting all of the salt of the carboxy group contained in the viral infection inhibiting compound to a carboxy group, and then removing the hydrochloric acid and water by a commonly used method such as freeze-drying.

[0019] The viral infection-inhibiting compound contains a polymer, and the weight-average molecular weight of the polymer is at least 3000, preferably at least 5000, more preferably at least 10000, and even more preferably at least 100000. When the weight-average molecular weight of the viral infection-inhibiting compound is 3000 or more, whitening and yellowing of the viral infection inhibitor can be reduced, 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.

[0020] The weight-average molecular weight of the polymer contained in the viral infection-inhibiting compound is preferably not more than 1,000,000, more preferably not more than 900,000, more preferably not more than 800,000, and even more preferably not more than 500,000. When the weight-average molecular weight of the viral infection-inhibiting compound is 1,000,000 or less, yellowing of the viral infection inhibitor can be reduced, 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 aggregation tendency of the viral infection-inhibiting compound is reduced, resulting in a form that facilitates interaction between the viral infection-inhibiting compound and viruses, and improving the viral infection-inhibiting effect of the viral infection inhibitor.

[0021] 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.

[0022] 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

[0023] The pH of the viral infection inhibiting compound is preferably 2 or higher, more preferably 3 or higher, and more preferably 4 or higher. The pH of the viral infection inhibiting compound is preferably 12 or lower, more preferably 11 or lower, more preferably 10 or lower, more preferably 9 or lower, more preferably 6 or lower, more preferably 5 or lower, and more preferably 4.5 or lower. When the pH of the viral infection inhibiting compound is 2 or higher, the viral infection inhibiting effect of the viral infection inhibitor is improved. When the pH of the viral infection inhibiting compound is 12 or lower, the viral infection inhibiting effect against non-enveloped viruses is improved. The pH of the viral infection inhibiting compound refers to the pH value at 25°C of a solution obtained by adding 0.5 g of the viral infection inhibiting compound to 99.5 g of purified water and mixing uniformly.

[0024] The viral infection-inhibiting compound having a carboxy group or a salt thereof may have one or more carboxy groups or salts thereof in the molecule, and examples thereof include polymers having a carboxy group or a salt thereof in the side chain of a linear polymer, carboxymethylcellulose or a salt thereof, carboxymethylated chitosan or a salt thereof, carboxymethylated chitin or a salt thereof, carboxymethyldextran or a salt thereof, carboxymethyl-β-cyclodextrin or a salt thereof, carboxysucrose or a salt thereof, pectin or a salt thereof, xanthan gum or a salt thereof, alginic acid or a salt thereof, hyaluronic acid or a salt thereof, fulvic acid or a salt thereof, and humic acid or a salt thereof.

[0025] In the polymer having a carboxy group or a salt thereof in the side chain of a linear polymer, the linear polymer is not particularly limited, and for example, vinyl polymer, polyester, and polyurethane are preferred, with vinyl polymer being more preferred.

[0026] Examples of polymers having a carboxy group or a salt thereof in the side chain of a linear polymer include polymers containing, as a monomer unit, a carboxy group derivative-containing monomer containing a carboxy group or a salt thereof. The polymer containing a carboxy group derivative-containing monomer as a monomer unit may be a homopolymer of the carboxy group derivative-containing monomer, or a copolymer of the carboxy group derivative-containing monomer and a monomer copolymerizable therewith.

[0027] The carboxyl group derivative-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, carboxybetaine type monomers or salts thereof, with acrylic acid, methacrylic acid, sodium acrylate and sodium methacrylate being preferred. The carboxyl group derivative-containing monomer may be used alone or in combination of two or more.

[0028] The monomer copolymerizable with the carboxyl group derivative-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, vinyl pyridine, etc. The monomer copolymerizable with the carboxyl group derivative-containing monomer may be used alone or in combination of two or more.

[0029] The polymer contained in 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 carboxyl group derivative-containing monomer 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.

[0030] It is preferable that the virus infection-inhibiting compound does not contain an aromatic ring in the molecule. If the virus infection-inhibiting compound does not contain an aromatic ring, whitening of the virus infection inhibitor can be reduced, and when the virus infection inhibitor is attached to the surface of a substrate, the virus infection-inhibiting effect can be more effectively exhibited without impairing the appearance of the substrate. Furthermore, if the virus infection-inhibiting compound does not contain an aromatic ring, the bulkiness of the virus infection-inhibiting compound is reduced, so that the molecular structure portion containing a carboxy group or a salt thereof can efficiently interact with viruses, thereby exhibiting an excellent virus infection-inhibiting effect.

[0031] 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.

[0032] The viral infection-inhibiting compound preferably does not contain a sulfonic acid group (-SO3H, H-type sulfonic acid group) or a salt of a sulfonic acid group in the molecule, and more preferably does not contain a sulfonic acid group or a salt of a sulfonic acid group in the molecule. If the viral infection-inhibiting compound does not contain a sulfonic acid group or a salt of a sulfonic acid group in the molecule, preferably does not contain a sulfonic acid group or a salt of a sulfonic acid group in the molecule, whitening of the viral infection inhibitor can be reduced, 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. Furthermore, if the viral infection-inhibiting compound does not contain a sulfonic acid group or a salt of a sulfonic acid group in the molecule, preferably does not contain a sulfonic acid group or a salt of a sulfonic acid group in the molecule, the number of highly electronegative oxygen atoms in the molecule is reduced, thereby reducing the aggregation tendency of the viral infection-inhibiting compound, and the molecular structural portion containing a carboxy group or a salt thereof can efficiently interact with viruses, thereby exerting an excellent viral infection-inhibiting effect.

[0033] The salt of sulfonic acid group is not particularly limited, and examples thereof include sodium salt (-SO3Na), calcium salt [(-SO3 - )2Ca 2+ ], ammonium salt (-SO3 - NH4 + ), magnesium salt [(-SO3 - )2Mg 2+ ], barium salts [(-SO3 - )2Ba 2+ ] etc.

[0034] The total content of carboxy groups and carboxy salts in the viral infection inhibitory compound is preferably 5 mmol / g or more, preferably 7 mmol / g or more, preferably 9 mmol / g or more, and preferably 11 mmol / g or more. The content of carboxy groups and carboxy salts in the viral infection inhibitory compound is preferably 20 mmol / g or less, preferably 18 mmol / g or less, preferably 17 mmol / g or less, and preferably 16 mmol / g or less. When the total content of carboxy groups and carboxy salts in the viral infection inhibitory compound is 5 mmol / g or more, the viral infection inhibitory effect of the viral infection inhibitor is improved. When the total content of carboxy groups and carboxy salts in the viral infection inhibitory compound is 20 mmol / g or less, the aggregation tendency of the viral infection inhibitory compound is reduced, resulting in a form that facilitates interaction between the viral infection inhibitory compound and the virus, and the viral infection inhibitory effect of the viral infection inhibitor is improved.

[0035] The total content of carboxy groups and carboxy salts in the viral infection inhibitory compound refers to a value measured by titration. Specifically, approximately 1 g (Ag) of the dried viral infection inhibitory compound is weighed out, 200 mL of purified water is added to the viral infection inhibitory compound, and titration is performed at 25°C with 0.1 mol / L aqueous sodium hydroxide solution. The amount of aqueous sodium hydroxide consumed (B mL) up to the half-equivalent point (the point at which half the amount required for complete neutralization has been added dropwise) is determined, and the content of carboxy groups (mmol / g) in the viral infection inhibitory compound is calculated using the following formula. When the viral infection inhibitory compound contains a salt of a carboxy group, the viral infection inhibitory compound is mixed with a 1 mol% aqueous hydrochloric acid solution to convert all of the salts of the carboxy groups contained in the viral infection inhibitory compound to carboxy groups, and the content of carboxy groups in the viral infection inhibitory compound is measured as described above. The resulting content of carboxy groups (mmol / g) is taken as the total content of carboxy groups and carboxy salts (mmol / g). Carboxylic acid content (mmol / g) = 0.1 x A / B

[0036] The virus infection inhibitor preferably does not contain a sulfonic acid group or a salt of a sulfonic acid group, and more preferably does not contain a sulfonic acid group or a salt of a sulfonic acid group. The virus infection inhibitor contains a virus infection inhibitory compound, but preferably does not contain a compound having a sulfonic acid group in the molecule or a compound having a salt of a sulfonic acid group in the molecule, and more preferably does not contain a compound having a sulfonic acid group in the molecule and a compound having a salt of a sulfonic acid group in the molecule. When the virus infection inhibitor does not contain a compound having a sulfonic acid group in the molecule or a compound having a salt of a sulfonic acid group in the molecule (preferably does not contain a compound having a sulfonic acid group in the molecule and a compound having a salt of a sulfonic acid group in the molecule), whitening of the virus infection inhibitor can be reduced, 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.

[0037] The compound having a sulfonic acid group in the molecule may be any compound having a sulfonic acid group in the molecule, and the compound having a salt of a sulfonic acid group in the molecule may be any compound having a salt of a sulfonic acid group in the molecule.

[0038] Examples of compounds having a sulfonic acid group in the molecule include linear alkylbenzenesulfonic acids (such as dodecylbenzenesulfonic acid), α-olefinsulfonic acids (such as C12 to C18 olefinsulfonic acids), alkyldiphenylethersulfonic acids, and polymers having a sulfonic acid group in the side chain of a linear polymer (such as a vinyl polymer).

[0039] Examples of compounds having a salt of a sulfonic acid group in the molecule include linear alkylbenzene sulfonates (e.g., sodium dodecylbenzene sulfonate, calcium dodecylbenzene sulfonate, ammonium dodecylbenzene sulfonate, etc.), α-olefin sulfonates (e.g., sodium C12 to C18 olefin sulfonate, calcium C12 to C18 olefin sulfonate, ammonium C12 to C18 olefin sulfonate, etc.), alkyl diphenyl ether sulfonates (e.g., sodium sulfonate, calcium sulfonate, ammonium sulfonate of alkyl phenyl ethers having an alkyl group of C6 to C18, etc.), polyoxyalkylene alkyl ether sulfate, lauryl sulfate, and polymers having a salt of a sulfonic acid group in the side chain of a linear polymer (e.g., vinyl polymer, etc.).

[0040] The viral infection inhibitor contains a viral infection inhibitory compound, but the method for producing the viral infection inhibitor is not particularly limited, and the viral infection inhibitor can be produced by mixing the viral infection inhibitory compound with compounds to be added as needed in a conventional manner.

[0041] 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.

[0042] 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.

[0043] Examples of non-enveloped viruses include feline calicivirus, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, poliovirus, and rhinovirus.

[0044] The virus infection inhibitor may be used by adhering (supporting) it to the surface of particles. By adhering the virus infection inhibitor compound to the surface of particles, the virus infection inhibitor can be dispersed uniformly in the substrate described below without forming clumps. Therefore, the surface area of ​​the virus infection inhibitor can be increased, sufficient contact between the virus infection inhibitor and the virus can be ensured, and the virus infection inhibitor's virus infection inhibitory effect can be fully exerted.

[0045] The particles to which the virus infection inhibitor is attached to the surface are not particularly limited as long as they do not inhibit the virus infection inhibitory effect of the virus infection inhibitor. Particles include resin particles and inorganic particles. The particles may be used alone or in combination of two or more types.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] Examples of vinyl monomers copolymerizable with acrylic monomers include acrylonitrile, methacrylonitrile, maleic anhydride, and acrylamide.

[0051] The inorganic material constituting the inorganic particles is not particularly limited, and examples thereof include zeolite, hydrotalcite, calcium carbonate, calcium citrate, magnesium carbonate, and magnesium hydroxide.

[0052] 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 carboxyl groups outward, thereby enabling the viral infection-inhibiting agent to more effectively exert its viral infection-inhibiting effect.

[0053] 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.

[0054] The amount of the viral infection inhibitor attached to the resin particles is preferably 1 part by mass or more, more preferably 5 parts by mass or more, more preferably 7 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the resin particles. When the amount of the viral infection inhibitor attached is 1 part by mass or more, the viral infection inhibitor can be uniformly attached to the surface of the resin particles, and the viral infection inhibitor can more effectively exert its viral infection inhibitory effect.

[0055] The amount of the viral infection-inhibiting compound attached to the resin particles is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin particles. When the amount of the viral infection-inhibiting compound attached is 50 parts by mass or less, the viral infection-inhibiting compounds do not bond to each other, and the viral infection-inhibiting compounds are efficiently distributed on the surface of the resin particles, improving the viral infection-inhibiting effect.

[0056] The method for adhering the virus infection inhibitor to the surface of the resin particles is not particularly limited, and may be, for example, by relying on the adhesive strength of the virus infection inhibitor, or by using a binder resin to adhere the virus infection inhibitor to the surface of the resin particles. However, since this allows the virus infection inhibitor to effectively exert its virus infection inhibitory effect, it is preferable that the virus infection inhibitor compound be adhered to the surface of the resin particles by the adhesive strength of the virus infection inhibitor compound itself.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] The paint may contain additives such as pigments, plasticizers, curing agents, extenders, fillers, antioxidants, tackifiers, surfactants, etc., within the scope of not impairing the paint's physical properties. Incidentally, examples of methods for incorporating the virus infection inhibitor into the paint include a method in which the virus infection inhibitor and the paint are supplied to a dispersing device and uniformly mixed. Incidentally, examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill.

[0061] 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.

[0062] 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]

[0063] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

[0064] As viral infection inhibitory compounds, carboxy group-containing compounds 1 to 6, carboxy group salt-containing compounds, sulfonic acid salt-containing compounds 1 and 2, and aminoalkyl group-containing compounds were prepared, and these viral infection inhibitory compounds were used as viral infection inhibitors.

[0065] [Preparation of particles of carboxy group-containing compounds 1 to 4 and carboxy group salt-containing compounds] An acrylic monomer solution was obtained by mixing the predetermined amounts of acrylic acid, sodium acrylate, and methyl acrylate shown in Table 1. A predetermined amount of 1-hydroxycyclohexan-1-yl phenyl ketone (manufactured by IGM Resins BV, trade name "Omnirad 184") as a radical polymerization initiator was added to the obtained acrylic monomer solution and dissolved therein to prepare a raw material composition.

[0066] The raw material composition was applied to a polyethylene film using a wire bar coater #14 to form a coating layer with a thickness of 35 μm. Using a UV conveyor device (manufactured by Eye Graphics Co., Ltd., product name "ECS301G1"), ultraviolet light with a wavelength of 365 nm was applied to the coating layer at 25°C with an integrated light dose of 2000 mJ / cm. 2 Radical polymerization was carried out by irradiating the solution so that the temperature was such ...

[0067] The viral infection-inhibiting compound was coarsely crushed using a roll press device (Seishin Enterprise Co., Ltd., product name "150 type") at an operating condition of 25 rpm and a pressure of 25 tons, and then crushed using a jet mill device (Nisshin Engineering Co., Ltd., product name "SJ-500") at an operating condition of a viral infection-inhibiting compound supply rate of 1 kg / h and a compressed air pressure of 0.75 MPa to obtain particles of the viral infection-inhibiting compound (carboxy group-containing compounds 1 to 4 and carboxy group salt-containing compounds).

[0068] [Preparation of polystyrene particles with particles of carboxyl group-containing compound 2 attached to the surface] Five parts by mass of particles of carboxy group-containing compound 2 and 10 parts by mass of polystyrene resin particles (primary particles) having an average particle size of 4 μm were added to 100 parts by mass of water, and the mixture was powdered using a spray dryer at an atomizer rotation speed of 20,000 rpm. The entire amount of carboxy group-containing compound 2 particles was then attached (supported) to the surface of the polystyrene particles. The mixture was then pulverized using a jet mill (manufactured by Nisshin Engineering, trade name "SJ-500") at a raw material feed rate of 1 kg / h and a compressed air pressure of 0.75 MPa, yielding polystyrene particles with particles of carboxy group-containing compound 2 attached to their surfaces. In Table 2, "polystyrene particles with particles of carboxy group-containing compound 2 attached to their surfaces" is referred to as "particle-attached carboxy group-containing compound 2."

[0069] [Preparation of particles of carboxy group-containing compound 5] Adipic acid (manufactured by Tokyo Chemical Industry Co., Ltd., trade name "Adipic Acid") was coarsely crushed using a roll press (manufactured by Seishin Enterprise Co., Ltd., trade name "150 Model") at a rotation speed of 25 rpm and a pressure of 25 tons, and then crushed using a jet mill (manufactured by Nisshin Engineering, trade name "SJ-500") at a supply rate of the viral infection-inhibiting compound of 1 kg / h and a compressed air pressure of 0.75 MPa to obtain particles of the viral infection-inhibiting compound (carboxy group-containing compound 5). For convenience, the molecular weight of adipic acid is shown in the "weight average molecular weight" column of Table 2.

[0070] [Preparation of particles of carboxy group-containing compound 6] Particles of a viral infection-inhibiting compound (carboxyl group-containing compound 6) were obtained in the same manner as for producing particles of carboxyl group-containing compound 5, except that capric acid (trade name "Decanoic Acid" manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of adipic acid. For convenience, the molecular weight of capric acid is shown in the "Weight average molecular weight" column of Table 2.

[0071] [Preparation of particles of sulfonic acid salt-containing compound 1] Particles of a viral infection-inhibiting compound (sulfonic acid salt-containing compound 1) were obtained in the same manner as for producing particles of carboxy group-containing compound 5, except that sodium polystyrene sulfonate (not containing carboxy groups or carboxy group salts, product name "Versa-TL 502" manufactured by Nouryon) was used instead of adipic acid.

[0072] [Preparation of particles of sulfonic acid salt-containing compound 2] Particles of a viral infection-inhibiting compound (sulfonic acid salt-containing compound 2) were obtained in the same manner as for producing particles of carboxy group-containing compound 5, except that sodium lauryl sulfate (containing neither a carboxy group nor a salt of a carboxy group, product name "EMAL 10PT" manufactured by Kao Corporation) was used instead of adipic acid. For convenience, the molecular weight of sodium lauryl sulfate is shown in the "weight average molecular weight" column of Table 2.

[0073] [Preparation of particles of aminoalkyl group-containing compounds] Particles of a viral infection-inhibiting compound (aminoalkyl group-containing compound) were obtained in the same manner as for producing particles of carboxy group-containing compound 5, except that an aminoalkyl group-containing compound (not containing a carboxy group or a salt of a carboxy group, not containing a sulfonic acid group or a salt of a sulfonic acid group, product name "Eudragit EPO" manufactured by Evonik Nutrition & Care GmbH) was used instead of adipic acid.

[0074] The weight-average molecular weight, total content of carboxy groups and salts of carboxy groups (total content of carboxy groups and their salts), pKa1 and pH of the viral infection-inhibiting compounds are shown in Table 2.

[0075] (Examples 1 to 5 and Comparative Examples 1 to 5) A coating composition was prepared by mixing a virus infection inhibitor containing 3 parts by mass of the particulate virus infection-inhibiting compound shown in Table 2, prepared as described above, with 97 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 form a coating layer with a thickness of 18 μm.

[0076] 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.

[0077] Example 6 A coating composition was prepared by mixing the virus infection inhibitor (containing 3 parts by mass of carboxyl group-containing compound 2) containing polystyrene particles with carboxyl group-containing compound 2 attached to the surface, prepared as described above, with 97 parts by mass of an ultraviolet-curable acrylic coating (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 form a coating layer with a thickness of 18 μm.

[0078] 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.

[0079] The resulting coating film was subjected to a water spray test and a thermal stability test as described below, and the results are shown in Table 2.

[0080] The virus infection inhibitors containing the virus infection inhibitory compounds were subjected to antiviral tests using influenza virus (enveloped virus) and feline calicivirus (non-enveloped virus). The results are shown in Table 2.

[0081] (Water injection test) The coating film was subjected to a water spray test in accordance with JIS K7227, and the haze of the coating film after the water spray test was evaluated in accordance with JIS K 7361. The haze value (%) was measured using a haze meter ("HM-150" manufactured by Murakami Color Research Laboratory Co., Ltd.) in an environment of room temperature of 25°C and relative humidity of 40%. The water spray test was carried out at a temperature of the test layer of 40°C±2°C for a test time of 24 hours.

[0082] (Thermal stability test) The coating film was subjected to a thermal stability test in accordance with JIS K 7212, and the difference in yellow index (ΔYI) between before and after the thermal stability test was measured (ΔYI = yellow index of coating film after thermal stability test - yellow index of coating film before thermal stability test). The test temperature in the thermal stability test was 250°C, and the test time was 10 minutes.

[0083] (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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] The antiviral activity value was calculated by subtracting the viral infectivity of the test coating from the viral infectivity of the blank paint.

[0088] [Table 1]

[0089] [Table 2]

Claims

1. a virus infection-inhibiting compound that contains at least a carboxy group and has a pKa1 of 5.5 or less, a total content of the carboxy group and a salt of the carboxy group of 13.1 to 15 mmol / g, and a weight-average molecular weight of 3,000 or more; 0.5 g of the viral infection-inhibiting compound is added to 99.5 g of purified water and mixed uniformly, the pH of the resulting solution at 25°C is 4.5 or less, A virus infection inhibitor characterized by being contained in a base material to which a virus infection inhibitory effect is to be imparted.

2. 2. The virus infection inhibitor according to claim 1, wherein the virus infection inhibitor compound has a weight-average molecular weight of 3,000 to 1,000,000.

3. The composition contains a viral infection-inhibiting compound that contains at least a carboxy group and has a pKa1 of 5.5 or less, a total content of the carboxy group and a salt of the carboxy group of 5 to 20 mmol / g, does not contain an aromatic ring, and has a weight-average molecular weight of 3,000 or more; 0.5 g of the viral infection-inhibiting compound is added to 99.5 g of purified water and mixed uniformly, the pH of the resulting solution at 25°C is 4.5 or less, A virus infection inhibitor characterized by being contained in a base material to which a virus infection inhibitory effect is to be imparted.

4. The present invention comprises a viral infection-inhibiting compound that contains at least a carboxy group, has a pKa1 of 5.5 or less, has a total content of carboxy groups and carboxy salts of 5 to 20 mmol / g, does not contain a sulfonic acid group, and has a weight-average molecular weight of 3,000 or more, 0.5 g of the viral infection-inhibiting compound is added to 99.5 g of purified water and mixed uniformly, the pH of the resulting solution at 25°C is 4.5 or less, A virus infection inhibitor characterized by being contained in a base material to which a virus infection inhibitory effect is to be imparted.

5. 5. The virus infection inhibitor according to claim 1, which does not contain a compound having a sulfonic acid group.

6. a virus infection-inhibiting compound that contains at least a carboxy group and has a pKa1 of 5.5 or less, a total content of the carboxy group and a salt of the carboxy group of 5 to 20 mmol / g, and a weight-average molecular weight of 3,000 or more; 0.5 g of the viral infection-inhibiting compound is added to 99.5 g of purified water and mixed uniformly, the pH of the resulting solution at 25°C is 4.5 or less, The viral infection-inhibiting compound is attached to the surface of the particle, A virus infection inhibitor characterized by being contained in a base material to which a virus infection inhibitory effect is to be imparted.

7. 7. The virus infection inhibitor according to claim 6, wherein the particles are acrylic resin particles, styrene resin particles, or inorganic particles.

8. A substrate; A virus infection-preventing product comprising the virus infection-preventing agent according to any one of claims 1 to 7 contained in the base material.

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