Virus infection inhibition particles and virus infection inhibition products

Abstract

The present invention provides a virus infection inhibiting particle that can exert excellent virus infection inhibiting property. The virus infection inhibiting particle of the present invention comprises resin particles; and a virus infection inhibiting agent that is present on the surface of the resin particles and comprises a sulfonic acid compound having a sulfonic acid group and / or a sulfonic acid group derivative, so that the size can be easily adjusted and the particle can be dispersed in a substrate such as a synthetic resin or a fiber product, and the contact between the virus infection inhibiting agent and the virus can be fully ensured. Therefore, the virus infection inhibiting particle of the present invention exerts an excellent virus infection inhibiting effect.

Description

Technical Field

[0001] The present invention relates to virus infection inhibiting particles and virus infection inhibiting products. Background Art

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

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

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

[0005] Prior art literature

[0006] Patent Literature

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

[0008] Technical problem to be solved by the invention

[0009] However, the antiviral synthetic resin composition merely contains a sulfonic acid surfactant in the synthetic resin, and therefore the sulfonic acid surfactant cannot be dispersed in the synthetic resin while adjusting the size. Therefore, the sulfonic acid surfactant exists in the synthetic resin in the form of blocks of uneven size, and there is a problem that the contact between the sulfonic acid surfactant and the virus cannot be fully ensured, and the antiviral property of the sulfonic acid surfactant cannot be fully exerted.

[0010] The present invention provides virus infection inhibiting particles capable of exerting an excellent virus infection inhibiting effect.

[0011] Technical means to solve technical problems

[0012] The virus infection inhibitory particle of the present invention comprises: a resin particle; and a virus infection inhibitor present on the surface of the resin particle and comprising a sulfonic acid compound having a sulfonic acid group and / or a sulfonic acid group derivative.

[0013] The virus infection inhibiting product of the present invention comprises: a substrate and virus infection inhibiting particles contained in the substrate.

[0014] Effects of the Invention

[0015] In the virus infection inhibiting particles of the present invention, the virus infection inhibitor containing the sulfonic acid compound is present on the surface of the resin particles, so the size of the virus infection inhibitor can be easily adjusted and dispersed in a substrate such as a synthetic resin or a fiber product, and the contact between the virus infection inhibitor and the virus can be fully ensured. Therefore, the virus infection inhibiting particles of the present invention exert an excellent virus infection inhibiting effect. DETAILED DESCRIPTION

[0016] The virus infection inhibitory particles of the present invention include resin particles; and a virus infection inhibitor present on the surface of the resin particles and containing a sulfonic acid compound having a sulfonic acid group and / or a sulfonic acid derivative. That is, the virus infection inhibitor of the present invention contains a sulfonic acid compound having a sulfonic acid group and / or a sulfonic acid derivative as an active ingredient on the surface of the resin particles.

[0017] It is believed that when the conventional sulfonic acid surfactant is included in the synthetic resin, it is mostly present in the form of blocks. In the process of mixing the synthetic resin and the sulfonic acid surfactant, even if the block of the sulfonic acid surfactant is broken, it is difficult to adjust the size while breaking it, and it contains particularly large particles and particularly small particles, and is broken into uneven sizes.

[0018] As a result, it is believed that in the conventional viral infection inhibiting products obtained by dispersing sulfonic acid surfactants in synthetic resins, there are blocks of sulfonic acid surfactants having a height sufficient to come into contact with viruses and blocks of sulfonic acid surfactants having a height insufficient to come into contact with viruses on the surface of the product, and sometimes a sufficient viral infection inhibiting effect cannot be exerted.

[0019] The present invention has found that a virus infection inhibiting product obtained by using the virus infection inhibiting particles can exhibit an excellent virus infection inhibiting effect by allowing a virus infection inhibitor to be present on the surface of resin particles.

[0020] The principle is not clear yet, but it is speculated to be based on the following principle. The virus infection inhibition particles of the present invention allow the virus infection inhibitor to exist on the surface of the resin particles. It is believed that when the virus infection inhibition particles are contained in the synthetic resin, in the mixing process of the synthetic resin and the virus infection inhibition particles, the virus infection inhibition particles are mostly mixed in the form of primary particles or agglomerated states. In the mixing process, even if the virus infection inhibition particles temporarily become over-agglomerated lumps, they can be easily broken because the interaction between the primary particles constituting the agglomerated state is weak. As a result, the virus infection inhibition particles can be present in a uniform and appropriate size in the synthetic resin. Therefore, it is speculated that a large number of virus infection inhibition particles with a sufficient height to contact the virus can exist on the surface of the virus infection inhibition product, exerting an excellent virus infection inhibition effect. Therefore, the virus infection inhibition effect of the virus infection inhibitor can be fully exerted.

[0021] By pre-existing the virus infection inhibitor on the surface of the resin particles, the virus infection inhibitor can be uniformly dispersed in the base material described later without forming excessively aggregated lumps. Therefore, the surface area of ​​the virus infection inhibitor can be increased, and the virus infection inhibitor can fully exert its virus infection inhibitory effect.

[0022] [Resin particles]

[0023] The resin particles that allow the virus infection inhibitor to exist (preferably adhere) on the surface are not particularly limited as long as they do not hinder the virus infection inhibitor's virus infection inhibitor effect. Examples of synthetic resins that constitute the resin particles include: styrene resins, acrylic resins, polyurethane resins, vinyl chloride resins, ABS resins; synthetic rubbers such as styrene-butadiene rubber (SBR) and nitrile-butadiene rubber (NBR), etc., preferably styrene resins.

[0024] There are no particular limitations on the styrene-based resins, and examples thereof include: homopolymers or copolymers containing, as monomer units, styrene, methylstyrene, ethylstyrene, isopropylstyrene, dimethylstyrene, chlorostyrene, bromostyrene and other styrene-based monomers; copolymers containing, as monomer units, a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer; and the like.

[0025] Examples of the vinyl monomer copolymerizable with the styrene-based monomer include acrylic monomers such as acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, acrylic acid esters (methyl acrylate, ethyl acrylate, butyl acrylate, etc.), methacrylate esters (methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc.), maleic anhydride, and acrylamide.

[0026] The synthetic resin constituting the resin particles preferably contains an aromatic ring. The aromatic ring plays a role in attracting the hydrophobic part of the sulfonic acid compound present on the surface of the resin particles and orienting the hydrophilic sulfonic acid group and / or sulfonic acid group derivative outward, thereby more effectively exerting the viral infection inhibitory effect of the viral infection inhibitor.

[0027] It should be noted that the virus infection inhibitory effect refers to the effect of eliminating or reducing the infectivity of the virus to the cell, or preventing the virus from proliferating in the cell even if infected. As a method for confirming the presence or absence of such virus infectivity, for example, ISO18184 and JIS L1922 can be cited for fiber products, and ISO21702 can be cited for plastics other than fiber products and products with non-porous surfaces. The Antimicrobial Products Technology Association (SIAA) certifies the antiviral processing mark for products that meet the safety standards of antiviral processing agents and certain antiviral effect standards. The standard for antiviral effect is: in the evaluation of ISO21702, the difference (antiviral activity value) between the common logarithm of the virus infection titer of the blank product (antiviral processing agent without additives) and the common logarithm of the virus infection titer of the processed product (antiviral processing agent additives) is 2.0 or more. The virus infection inhibitor is used as a component of the antiviral processing agent, mixed in a resin or added to a surface coating agent such as a paint, and is evaluated by the above evaluation method.

[0028] In the present invention, for example, when evaluating the virus infection inhibitory effect under the following conditions, a product whose difference in the common logarithmic value of the virus infection titer between the blank product and the processed product (antiviral activity value) is 2.0 or more is defined as a virus infection inhibitor. At this time, regardless of the type of virus to be evaluated, in at least one virus, a product whose difference in the common logarithmic value of the virus infection titer between the blank product and the processed product (antiviral activity value) is 2.0 or more is treated as a virus infection inhibitor.

[0029] 50 mg of a virus infection inhibitor was added to 950 mg of a solvent-free ultraviolet curable acrylic resin (trade name "Teslack 2328" manufactured by Hitachi Chemical Co., Ltd.) and uniformly mixed to prepare a coating. The obtained coating was applied on a polyester film and then irradiated with a light intensity of 512 mJ / cm using a UV delivery device EYE GRANDAGE (manufactured by EYE GRAPHICS Co., Ltd., irradiator reflector: cold mirror condenser type, UV lamp: H03-L31 (light emission length 250 mm)). 2 The ultraviolet rays were irradiated to cure the ultraviolet curable acrylic resin to form a coating film with a film thickness of 15 μm to prepare a test coating film.

[0030] The antiviral test of the obtained test film was carried out according to ISO21702. The virus infection titer of the test film was calculated by the plaque method for the virus suspension after the reaction. A blank film was prepared in the same manner as described, except that the virus infection inhibitor was not included, and the virus infection titer (common logarithm) (PFU / cm 2 ). The difference in the common logarithmic values ​​of the virus infection titers (antiviral activity value) was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0031] In addition, the plaque method and hemagglutination titer (HAU) measurement method described in "Medical Virology" (first edition published in April 1990) can be cited.

[0032] The aromatic ring may be a monocyclic aromatic ring or a ring formed by combining and condensing monocyclic aromatic rings (condensed aromatic ring). The aromatic ring is not particularly limited, and examples thereof include benzene ring, naphthalene ring, anthracene ring, biphenyl, phenoxyphenyl, etc., preferably benzene ring and naphthalene ring. In the case of the aromatic ring, any one or more hydrogen atoms in the aromatic ring and the condensed aromatic ring are removed and bonded to other atoms through covalent bonds.

[0033] The resin particles can be primary particles, preferably primary particles are condensed and integrated to form condensed particles. Condensed particles refer to particles formed by the condensation and integration of more than 5 primary particles. It should be noted that, regarding the judgment of whether it is a condensed particle, an enlarged photo of the resin particles is taken using an electron microscope (magnification 500 times), and in the photo, it is judged whether the primary particles are condensed and integrated, and the particles formed by the condensation and integration of more than 5 primary particles are used as condensed particles. If condensed particles are formed by the condensation and integration of primary particles, sufficient concave and convex can be formed on the surface of the condensed particles. If the condensed particles are formed with sufficient concave and convex, the surface area of ​​the condensed particles becomes larger, and the virus infection inhibitor can be present on the surface of the condensed particles in a manner that its surface area becomes larger, so that the virus infection inhibitor is in sufficient contact with the virus, and the virus infection inhibitor can effectively exert the virus infection inhibitor The effect of inhibiting the virus infection.

[0034] In addition, if the resin particles are condensed particles, when the virus infection inhibition particles are included in the synthetic resin and used, the virus infection inhibition particles are easy to protrude to the surface of the synthetic resin, and the virus infection inhibition effect of the virus infection inhibitor can be fully exerted. This mechanism is not yet clear, but the concavo-convex surface of the condensed particles is different from the concavo-convex surface formed on the primary particle, and is formed by connecting a part of the surface of the primary particle. Therefore, it is believed that the concavo-convex concave portion of the surface of the condensed particles is deeper than the concavo-convex surface of the primary particle, and the synthetic resin is difficult to enter the concave portion, so the adaptability between the condensed particles and the synthetic resin is reduced, and as a result, the condensed particles are easy to protrude to the surface of the synthetic resin.

[0035] The average particle size of the resin particles (primary particles) is preferably 20 μm or less, more preferably 10 μm or less, more preferably 5 μm or less, and more preferably 4 μm or less. The average particle size of the resin particles is preferably 1 μm or more. When the average particle size of the resin particles is 20 μm or less, it is preferred that the surface area of ​​the virus infection inhibitor that can come into contact with the virus is increased. If the average particle size of the resin particles is 1 μm or more, when the virus infection inhibitor particles are included in a synthetic resin for use, it is easy for the virus infection inhibitor particles to protrude from the surface of the synthetic resin. It should be noted that the resin particles of the primary particles are sometimes referred to as "resin particles (primary particles)."

[0036] The average particle size of the agglomerated particles is preferably 10 μm or more, more preferably 25 μm or more, more preferably 30 μm or more, more preferably 35 μm or more, and more preferably 40 μm or more. The average particle size of the agglomerated particles is preferably 90 μm or less, more preferably 70 μm or less, more preferably 60 μm or less, and more preferably 55 μm or less. When the average particle size of the agglomerated particles is 90 μm or less, when the virus infection inhibitory particles are included in the synthetic resin for use, the surface area of ​​the agglomerated particles protruding from the surface of the synthetic resin can be increased, and the surface area of ​​the virus infection inhibitor that can contact the virus is increased, so it is preferred. If the average particle size of the resin particles is 10 μm or more, when the virus infection inhibitory particles are included in the synthetic resin for use, it is easy for the virus infection inhibitory particles to protrude from the surface of the synthetic resin.

[0037] The average particle size of the resin particles (primary particles) refers to the arithmetic mean diameter in the volume-based particle size distribution measured by the laser diffraction / scattering method. The average particle size of the resin particles (primary particles) can be measured by wet measurement using, for example, a measuring device based on the laser diffraction / scattering method commercially available from Horiba Seisakusho under the trade name "LA-950V2".

[0038] The average particle size of the agglomerated particles refers to the arithmetic mean diameter in the volume-based particle size distribution measured by the laser diffraction / scattering method. The average particle size of the agglomerated particles can be measured by dry measurement using a measuring device based on the laser diffraction / scattering method commercially available from SEISHIN ENTERPRISE under the trade name "SEISHI LMS-30".

[0039] The content of the agglomerated particles in the virus infection inhibiting particles is preferably 30% or more, more preferably 40% or more, more preferably 50% or more, more preferably 60% or more, more preferably 70% or more, more preferably 80% or more, more preferably 90% or more, and more preferably 95% or more. If the content of the agglomerated particles is 30% or more, when the virus infection inhibiting particles are included in a synthetic resin for use, the virus infection inhibiting particles are easily protruded to the surface of the synthetic resin.

[0040] The content of agglomerated particles in the virus infection inhibition particles is determined according to the following method. Take 1 g of virus infection inhibition particles as a sample. Use an electron microscope to take an electron microscope photo of the sample at 500 times. In the electron microscope photo, arbitrarily determine the measurement range of a square with a side of 10 cm. Within the measurement range, the total number of virus infection inhibition particles and the number of agglomerated particles are measured by visual observation and calculated based on the following formula. It should be noted that the total number of virus infection inhibition particles refers to the total number of virus infection inhibition particles that include combined particles formed by the aggregation of 2 to 4 primary particles in addition to primary particles and agglomerated particles. It should be noted that the number of primary particles that constitute agglomerated particles and combined particles is not included in the total number of virus infection inhibition particles.

[0041] Content of Aggregated Particles in Virus Infection Inhibitory Particles (%)

[0042] =100×(number of agglomerated particles) / (total number of virus infection inhibition particles)

[0043] [Sulfonic acid compounds]

[0044] The virus infection inhibitor particles are composed of a virus infection inhibitor containing a sulfonic acid compound as an active ingredient on the surface of the resin particles. The virus infection inhibitor containing a sulfonic acid compound as an active ingredient is preferably attached to the surface of the resin particles. The virus infection inhibitor containing a sulfonic acid compound as an active ingredient is preferably attached and integrated to the surface of the resin particles.

[0045] The sulfonic acid compound has a sulfonic acid group (-SO3H) and / or a sulfonic acid group derivative (hereinafter, the sulfonic acid group and the sulfonic acid derivative are sometimes collectively referred to as "a group derived from sulfonic acid") in the molecule. The sulfonic acid compound is derived from a molecular structure portion containing a sulfonic acid group (-SO3H) and / or a sulfonic acid group derivative and exerts a viral infection inhibitory effect.

[0046] The sulfonic acid group derivative is not particularly limited, and examples thereof include salts of sulfonic acid group, and esterified products such as -SO3CH3 and -SO3C2H5. Among them, salts of sulfonic acid group are preferred.

[0047] The salt of the sulfonic acid group is not particularly limited, and examples thereof include sodium sulfonate salts, calcium sulfonate salts, ammonium sulfonate salts, magnesium sulfonate salts, and barium sulfonate salts. Among them, sodium sulfonate salts are preferred.

[0048] The sulfonic acid compound is preferably an organic compound. In the present invention, the "organic compound" refers to a compound containing at least one (preferably two or more) carbon atoms in the molecule and containing a carbon-hydrogen bond (CH bond).

[0049] When the sulfonic acid compound is an organic compound, the sulfonic acid compound has hydrophobicity in the organic chain part (hydrophobic part) represented by the carbon-hydrogen bond part. The organic chain part of the sulfonic acid compound has excellent affinity with the resin particles, while the group derived from the sulfonic acid, which has lower affinity than the organic chain part, tends to be oriented outward with respect to the resin particles, and can more effectively exert the virus infection inhibitory effect.

[0050] Furthermore, since the hydrophilic sulfonic acid group of the sulfonic acid compound tends to face outward, its compatibility with synthetic resins is reduced, and as a result, it tends to appear on the surface of the synthetic resin, and the virus infection inhibitory effect of the sulfonic acid compound can be more effectively exerted.

[0051] The sulfonic acid compound preferably has an aromatic ring. If the sulfonic acid compound has an aromatic ring, the sulfonic acid compound is firmly attached to the surface of the resin particles due to its affinity with the synthetic resin constituting the resin particles, thereby suppressing the detachment of the sulfonic acid compound, and the virus infection inhibition particles can maintain excellent virus infection inhibition effects for a long time. It should be noted that the aromatic ring is the same as the aromatic ring described in the resin particles, so the description is omitted. The aromatic ring in the synthetic resin constituting the resin particles and the aromatic ring in the sulfonic acid compound may be the same or different.

[0052] In the sulfonic acid compound, the group derived from the sulfonic acid is preferably directly or indirectly bonded to the aromatic ring, and more preferably directly bonded to the aromatic ring. Due to the affinity between the aromatic ring in the sulfonic acid compound and the synthetic resin constituting the resin particles, the aromatic ring in the sulfonic acid compound is attracted to the synthetic resin constituting the resin particles. At this time, since the group derived from the sulfonic acid is hydrophilic, the aromatic ring is attracted to the synthetic resin constituting the resin particles with the group derived from the sulfonic acid facing outward. As a result, the group derived from the sulfonic acid is easily in a state of facing outward, and the virus infection inhibitory particles exert an excellent virus infection inhibitory effect.

[0053] In the sulfonic acid compound, when the group derived from sulfonic acid is indirectly bonded to the aromatic ring, the group derived from sulfonic acid is preferably bonded to the aromatic ring via an alkylene group (preferably a methylene group or an ethylene group) having 1 to 4 carbon atoms. When the aromatic ring in the sulfonic acid compound is attracted to the synthetic resin of the resin particles, the group derived from sulfonic acid caused by the alkylene group is separated from the aromatic ring, and the group derived from sulfonic acid can be oriented to be exposed further outward, so that the virus infection inhibitory particles exert an excellent virus infection inhibitory effect.

[0054] In addition, when the synthetic resin and the sulfonic acid compound constituting the resin particles both have aromatic rings, the aromatic rings of the synthetic resin constituting the resin particles and the aromatic rings of the sulfonic acid compound attract each other. As a result, the hydrophilic groups derived from the sulfonic acid are more easily exposed to the outside, which can further enhance the viral infection inhibition effect of the viral infection inhibition particles.

[0055] The sulfonic acid compound is not particularly limited as long as it has any one or both of a sulfonic acid group and a sulfonic acid derivative in the molecule, and examples thereof include linear alkylbenzene sulfonic acid, linear alkylbenzene sulfonate, α-olefin sulfonic acid, alkyl diphenyl ether sulfonic acid, alkyl diphenyl ether sulfonate, α-olefin sulfonate, polyoxyalkylene alkyl ether sulfate, and a polymer having a sulfonic acid-derived group in a side chain of a linear polymer.

[0056] Examples of the linear alkylbenzenesulfonic acid include dodecylbenzenesulfonic acid, decylbenzenesulfonic acid, undecylbenzenesulfonic acid, tridecylbenzenesulfonic acid, and tetradecylbenzenesulfonic acid.

[0057] Examples of the linear alkylbenzene sulfonate include sodium dodecylbenzene sulfonate, calcium dodecylbenzene sulfonate, ammonium dodecylbenzene sulfonate, magnesium dodecylbenzene sulfonate, barium dodecylbenzene sulfonate, sodium decylbenzene sulfonate, ammonium decylbenzene sulfonate, sodium undecylbenzene sulfonate, ammonium decylbenzene sulfonate, sodium undecylbenzene sulfonate, ammonium undecylbenzene sulfonate, sodium tridecylbenzene sulfonate, ammonium tridecylbenzene sulfonate, sodium tetradecylbenzene sulfonate, and ammonium tetradecylbenzene sulfonate. Sodium dodecylbenzene sulfonate is preferred.

[0058] The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonic acid and the linear alkylbenzene sulfonate is preferably 10 or more, more preferably 11 or more, and more preferably 12 or more. The number of carbon atoms in the alkyl group of the linear alkylbenzene sulfonic acid is preferably 25 or less, more preferably 20 or less, and more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the hydrophobic part derived from the alkyl group and the resin particles are attracted to each other due to their affinity, so that the hydrophilic group derived from the sulfonic acid is easily directed to the outside, and as a result, the virus infection inhibitory particles exert an excellent virus infection inhibitory effect.

[0059] Examples of the α-olefin sulfonic acid include C12 to C18 α-olefin sulfonic acids, and C14 tetradecene sulfonic acid is preferred.

[0060] Examples of the α-olefin sulfonate include C12-C18 sodium α-olefin sulfonate, C12-C18 calcium α-olefin sulfonate, C12-C18 ammonium α-olefin sulfonate, C12-C18 magnesium α-olefin sulfonate, C12-C18 barium α-olefin sulfonate, and preferably C14 sodium tetradecene sulfonate.

[0061] The carbon number of the α-olefin in the α-olefin sulfonic acid and the α-olefin sulfonate is preferably 12 or more, more preferably 14 or more. The carbon number of the α-olefin in the α-olefin sulfonic acid and the α-olefin sulfonate is preferably 22 or less, more preferably 18 or less. When the carbon number of the α-olefin is within the above range, the hydrophobic part derived from the α-olefin chain of the sulfonic acid compound and the resin particles are attracted to each other due to their affinity, so that the hydrophilic group derived from the sulfonic acid is easily directed outward, and as a result, the virus infection inhibitory particles exert an excellent virus infection inhibitory effect.

[0062] Examples of the alkyl diphenyl ether sulfonic acid include alkyl diphenyl ether sulfonic acids having an alkyl group of C6 to C18, and C12 dodecyl diphenyl ether sulfonic acid is preferred.

[0063] Examples of the alkyl diphenyl ether sulfonate include sodium salts, calcium salts, ammonium salts, magnesium salts, barium salts, and the like of alkyl phenyl ethers whose alkyl groups are C6 to C18, and sodium dodecyl diphenyl ether sulfonate of C12 is preferred.

[0064] The number of carbon atoms in the alkyl diphenyl ether sulfonic acid and the alkyl diphenyl ether sulfonate is preferably 8 or more, more preferably 10 or more. The number of carbon atoms in the alkyl diphenyl ether sulfonic acid and the alkyl diphenyl ether sulfonate is preferably 24 or less, more preferably 18 or less. When the number of carbon atoms in the alkyl group is within the above range, the hydrophobic part of the alkyl group derived from the sulfonic acid compound and the resin particles are attracted to each other due to their affinity, so that the hydrophilic group derived from the sulfonic acid is easily directed outward, and as a result, the virus infection inhibitory particles exert an excellent virus infection inhibitory effect.

[0065] Among the polymers having a sulfonic acid-derived group in a side chain of the linear polymer, the linear polymer is not particularly limited, but is preferably a vinyl polymer, a polyester, or a polyurethane, and preferably a vinyl polymer.

[0066] The polymer having a group derived from sulfonic acid on the side chain of the linear polymer is not particularly limited, and examples thereof include a polymer containing a styrenesulfonic acid component, a polymer containing a styrenesulfonic acid derivative component, a sulfonic acid derivative of a polymer containing a styrenesulfonic acid component, a copolymer containing a styrenesulfonate component and a styrenesulfonic acid derivative component, a styrenesulfonic acid homopolymer, a styrenesulfonate homopolymer, a styrenesulfonic acid derivative homopolymer, a styrene-styrenesulfonate copolymer, a styrene-styrenesulfonic acid copolymer, a compound obtained by sulfonating the benzene ring of polystyrene, a sulfonic acid derivative of a compound obtained by sulfonating the benzene ring of polystyrene, a compound obtained by sulfonating the benzene ring of a polymer containing a styrene component, and a sulfonic acid derivative of a compound obtained by sulfonating the benzene ring of a polymer containing a styrene component.

[0067] In addition, the polymer having a group derived from sulfonic acid in the side chain of the linear polymer is preferably a homopolymer or copolymer of a monomer having a group derived from sulfonic acid. As the monomer having a group derived from sulfonic acid, for example, p-styrenesulfonic acid, m-styrenesulfonic acid, o-styrenesulfonic acid, sodium p-styrenesulfonate, sodium m-styrenesulfonate, sodium o-styrenesulfonate, calcium p-styrenesulfonate, calcium m-styrenesulfonate, calcium o-styrenesulfonate, ammonium p-styrenesulfonate, ammonium m-styrenesulfonate, ammonium o-styrenesulfonate, ethyl p-styrenesulfonate, ethyl m-styrenesulfonate, ethyl o-styrenesulfonate, 4-vinylbenzoic acid, sodium 4-vinylbenzoate, methyl 4-vinylbenzoate, 4-vinylaniline, aminostyrene hydrochloride, N-acetylaminostyrene, N-benzoylaminostyrene, naphthalenesulfonic acid, sodium naphthalenesulfonate, calcium naphthalenesulfonate, etc. are mentioned, preferably sodium styrenesulfonate, and more preferably sodium p-styrenesulfonate from the aspect of less steric hindrance in the reactivity with viruses.

[0068] It should be noted that the monomer having a group derived from sulfonic acid can form a copolymer with other monomers. Examples of copolymerizable monomers include alkyl acrylates, alkyl methacrylates, vinyl alkyl ethers, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, 2-vinylnaphthalene, styrene, acrylonitrile, acrylic acid, sodium acrylate, methacrylic acid, maleic acid, fumaric acid, maleic anhydride, acrylamide, methacrylamide, diacetone acrylamide, vinyl toluene, xylene sulfonic acid, vinyl pyridine, vinyl sulfonic acid, vinyl alcohol, methyl methacrylate, sodium methacrylate, hydroxyethyl methacrylate, and the like, preferably styrene.

[0069] A polymer having a sulfonic acid-derived group in a side chain of a linear polymer can be produced by a general method, for example: a method of subjecting a monomer having a sulfonic acid-derived group to free radical polymerization; a method of subjecting a monomer having a sulfonic acid-derived group to free radical polymerization with a monomer capable of copolymerizing with the monomer; a method of neutralizing the sulfonic acid of a polymer containing a monomer component having a sulfonic acid-derived group using an alkali (such as sodium hydroxide, calcium hydroxide, potassium hydroxide, ammonium hydroxide, etc.), etc.

[0070] The virus infection inhibitory particles have a virus infection inhibitory effect on various viruses, and show a high virus infection inhibitory effect on RNA viruses.

[0071] Examples of RNA viruses include feline calicivirus, mammalian orthoreovirus of the Reoviridae family, Colorado tick fever virus, human parainfluenza virus 1 and 3 of the Paramyxoviridae family, measles virus, mumps virus, human parainfluenza virus 2 and 4, Hendra virus, Nipah virus, human RS (Respiratory syncytial) virus, rabies virus of the Rhabdoviridae family, vesicular stomatitis virus, Marburg virus of the Filoviridae family, Zaire ebolavirus, Sudan ebolavirus, Borna disease virus of the Bornaviridae family, influenza A virus, influenza B virus, influenza C virus of the Orthomyxoviridae family, La Crosse virus of the Bunyaviridae family, Rift Valley virus, and other viruses. Valley fever virus, Crimean-Congo hemorrhagic fever virus, Hantavirus, Sin Nom bre virus, Lassa virus of Arenaviridae, lymphocytic choriomeningitis virus, Junin virus, poliovirus of Picornaviridae, coxsackie A virus, coxsackie B virus, echovirus, enterovirus, human rhinovirus, hepatitis A virus, human parecho virus 1, 2, Norovirus of Caliciviridae, Sapporo virus, human astrovirus of Astroviridae, Coronaviridae iridae), SARS-related coronavirus, coronavirus (COVID-19), Japanese encephalitis virus, yellow fever virus, dengue virus, tick-borne encephalitis virus, West Nile virus, hepatitis C virus, Eastern equine encephalitis virus, chikungunya virus, rubella virus, human T-cell leukemia virus, human immunodeficiency virus 1 of the Retroviridae, etc.

[0072] [Viral infection inhibitory particles]

[0073] The virus infection suppressing particles are obtained by allowing a virus infection suppressing agent including a sulfonic acid compound to be present on the surface of resin particles.

[0074] In the present invention, for example, when evaluating the virus infection inhibitory effect under the following conditions, particles whose difference in the common logarithmic value of the virus infection titer between the blank and the processed product (antiviral activity value) is 2.0 or more are defined as virus infection inhibitory particles. At this time, regardless of the type of virus to be evaluated, particles whose difference in the common logarithmic value of the virus infection titer between the blank and the processed product (antiviral activity value) is 2.0 or more in at least one virus are treated as virus infection inhibitory particles.

[0075] The virus infection inhibitory particles in an amount of 50 mg of the virus infection inhibitor in the virus infection inhibitory particles were supplied to 950 mg of a solvent-free ultraviolet curable acrylic resin (trade name "Teslack 2328" manufactured by Hitachi Chemical Co., Ltd.) and uniformly mixed to prepare a coating. The obtained coating was applied on a polyester film, and then irradiated with a light intensity of 512 mJ / cm using a UV conveying device EYEGRANDAGE [manufactured by EYE GRAPHICS Co., Ltd., irradiator reflector: cold mirror condenser type, UV lamp: H03-L31 (light emission length 250 mm)]. 2 The ultraviolet rays were irradiated to cure the ultraviolet curable acrylic resin to form a coating film with a film thickness of 15 μm as a test coating film.

[0076] The antiviral test of the obtained test film was carried out according to ISO21702. The virus infection titer of the test film was calculated by the plaque method for the virus suspension after the reaction. A blank film was prepared in the same manner as described except that the virus infection inhibitor was not included, and the virus infection titer (common logarithm) (PFU / cm 2 ). The difference in the common logarithmic values ​​of the virus infection titers (antiviral activity value) was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0077] The content of the sulfonic acid compound in the viral infection inhibitor is preferably 50% by mass or more, more preferably 60% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, more preferably 90% by mass or more, more preferably 95% by mass or more, more preferably 99% by mass or more, and more preferably 100% by mass.

[0078] The amount of the sulfonic acid compound present in 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, more preferably 10 parts by mass or more, more preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and more preferably 40 parts by mass or more, relative to 100 parts by mass of the resin particles. If the amount of the sulfonic acid compound present is 1 part by mass or more, the amount of the virus infection inhibitor on the resin particles increases, and thus an excellent virus infection inhibitory effect can be imparted to the virus infection inhibitory particles.

[0079] The amount of the sulfonic acid compound present in the resin particles is preferably 100 parts by mass or less, more preferably 80 parts by mass or less, more preferably 60 parts by mass or less, more preferably 55 parts by mass or less, and more preferably 40 parts by mass or less, relative to 100 parts by mass of the resin particles. When the amount of the sulfonic acid compound present is 100 parts by mass or less, the viral infection inhibitor is effectively present on the surface of the resin particles, the surface area of ​​the viral infection inhibitor can be increased, and the viral infection inhibitor particles can exhibit excellent viral infection inhibitory effects.

[0080] The sulfonic acid compound is present on the surface of the resin particles. The method for making the sulfonic acid compound present on the surface of the resin particles is not particularly limited. For example, the adhesive force of the sulfonic acid compound itself may be utilized, or the sulfonic acid compound may be adhered to the surface of the resin particles using a binder resin. From the viewpoint of being able to effectively exert the viral infection inhibitory effect of the sulfonic acid-derived group of the sulfonic acid compound, it is preferred to adhere the sulfonic acid compound to the surface of the resin particles by utilizing the adhesive force of the sulfonic acid compound itself.

[0081] When the resin particles (primary particles) are aggregated and integrated to form aggregated particles, the resin particles are preferably integrated with each other through a sulfonic acid compound. When the resin particles (primary particles) are integrated with each other through a sulfonic acid compound, the virus invading between the resin particles (primary particles) can be effectively inactivated by the virus infection inhibitor, and the virus infection inhibition effect of the virus infection inhibition particle can be improved.

[0082] The virus infection inhibitory particles are contained in a substrate to which a virus infection inhibitory effect is to be imparted and used, and the substrate containing the virus infection inhibitory particles exhibits the virus infection inhibitory effect as a virus infection inhibitory product.

[0083] The substrate containing the virus infection inhibiting particles is not particularly limited as long as it can contain the virus infection inhibiting particles, and examples thereof include: synthetic resin moldings, coatings, wallpapers, decorative sheets, floor materials, fiber products (woven fabrics, non-woven fabrics, knitted fabrics), interior products and interior materials (seats, child seats and foam bodies constituting them, etc.) for vehicles (such as cars, airplanes, ships, etc.), kitchen supplies, baby products, building interior materials, etc.

[0084] As the coating, conventionally known coatings can be used, for example, oily coatings (such as mixed coatings, oil varnishes, etc.), cellulose coatings, synthetic resin coatings, etc. can be cited. The coating can contain additives such as pigments, plasticizers, curing agents, extenders, fillers, anti-aging agents, tackifiers, surfactants, etc. within the range that does not damage its physical properties. It should be noted that as a method for including virus infection inhibiting particles in the coating, for example, a method of supplying virus infection inhibiting particles and coating to a dispersing device and uniformly mixing them can be cited. Examples of dispersing devices include high-speed mills, ball mills, and sand mills.

[0085] The building interior material is not particularly limited, and examples thereof include floor materials, wallpapers, ceiling materials, paints, door handles, switches, switch covers, wax, and the like.

[0086] The vehicle interior products and vehicle interior materials are not particularly limited, and examples thereof include seats, child seats, seat belts, car mats, seat covers, doors, roof materials, floor mats, door trims, instrument panels, consoles, glove boxes, hanging rings, armrests, and the like.

[0087] The virus infection inhibiting particles can be used by being included in the substrate by, for example, mixing with a synthetic resin constituting the substrate. The virus infection inhibiting particles can be used by being included in a coating. The virus infection inhibiting particles can be used by being attached and integrated onto the surface of the substrate using a synthetic resin.

[0088] The virus infection inhibiting particles can be easily sized and dispersed in a synthetic resin, and thus can be dispersed in a substrate with an adjusted size or a uniform size, including when mixed into a synthetic resin constituting a coating or a substrate. Therefore, a large number of virus infection inhibiting particles having a sufficient height for contacting viruses can be present on the surface of the product in the substrate, and an excellent virus infection inhibiting effect can be imparted to the virus infection inhibiting product.

[0089] In particular, when the resin particles constituting the virus infection inhibitory particles form aggregated particles, the virus infection inhibitory particles are easily protruded onto the surface of the synthetic resin, and the virus infection inhibitory effect can be fully exerted.

[0090] Example

[0091] Hereinafter, the present invention will be described in more detail using Examples, but the present invention is not limited thereto.

[0092] (Examples 1 to 18)

[0093] A virus infection inhibitor containing the sulfonic acid compound shown in Table 1 at 100% by mass and resin particles (primary particles) having an average particle size shown in Table 1 are supplied in 100 parts by mass of water in an amount shown in Table 1, and the mixture is powdered using a spray dryer at an atomizer speed shown in Table 1, so that the total amount of the virus infection inhibitor is attached (loaded) on the surface of the resin particles to obtain virus infection inhibitor particles.

[0094] (Comparative Example 1)

[0095] Virus infection inhibitory particles were obtained in the same manner as in Example 1 except that the virus infection inhibitor containing 100% by mass of polyoxyethylene lauryl ether was used instead of the sulfonic acid compound so as to be 5 parts by mass based on 100 parts by mass of water.

[0096] (Comparative Example 2)

[0097] 5 parts by mass of a virus infection inhibitor containing 100% by mass of the sulfonic acid compound shown in Table 1 was supplied to 100 parts by mass of water, and the mixture was powderized using a spray dryer at an atomizer rotation speed shown in Table 1 to obtain virus infection inhibitory particles. The virus infection inhibitory particles are formed by agglomerating the sulfonic acid compound, so the surface area of ​​the sulfonic acid compound is small.

[0098] The average particle size (μm) of aggregated particles contained in the obtained virus infection inhibiting particles and the content (%) of aggregated particles in the virus infection inhibiting particles were measured according to the above-mentioned methods. The results are shown in Table 1.

[0099] The obtained virus infection inhibitory particles were subjected to an antiviral test using influenza virus. The results are shown in Table 1.

[0100] (Antiviral test)

[0101] 50 mg of the virus infection inhibitor was added to 950 mg of a solvent-free ultraviolet curable acrylic resin (product name "Teslack 2328" manufactured by Hitachi Chemical Co., Ltd.), and uniformly mixed at 15000 rpm for 30 seconds using a stirring device (product name "POLYTRON HOMOGENIZER PT3100D" manufactured by KINE MATICA Co., Ltd.) to prepare a coating. After the obtained coating was applied on a polyester film, the coating was irradiated with a light intensity of 512 mJ / cm using a UV conveying device EYE GRANDAGE (manufactured by EYE GRAPHICS Co., Ltd., irradiator reflector: cold mirror condenser type, UV lamp: H03-L31 (light emission length 250 mm)). 2The ultraviolet rays were used to cure the ultraviolet curable acrylic resin to form a coating film with a thickness of 15 μm. It should be noted that the virus infection inhibitory particles were changed to use virus infection inhibitory particles containing 50 mg of the virus infection inhibitor in the virus infection inhibitory particles instead of 50 mg of the virus infection inhibitor.

[0102] The surface of the obtained coating film was impregnated with 1 mL of water into a flat square nonwoven fabric (trade name "KIMWIPE S-200" manufactured by NIPPON PAPER CRECIA) with a side of 10 cm, and the coating film surface was repeatedly rubbed 10 times with the nonwoven fabric to prepare a test coating film.

[0103] The obtained test coating was subjected to an antiviral test in accordance with ISO 21702. The virus infection titer of the test coating was calculated by a plaque method using the virus suspension after the reaction.

[0104] A blank coating was prepared in the same manner as described above except that the virus infection inhibitory particles were not included. Based on the blank coating, the virus infection titer (common logarithm) (PFU / cm 2 The virus infection titer (common logarithm value) of the blank coating is 6.5 PFU / cm 2 .

[0105] The antiviral activity value was calculated by subtracting the virus infection titer of the test coating from the virus infection titer of the blank coating.

[0106] In the antiviral test conducted in the examples, in the method for measuring the virus infection titer described in the "Specifications for Carrying Out the Invention", the surface of the coating film was wiped with a nonwoven fabric impregnated with water, and the coating film after wiping was used as the test coating film.

[0107] Since the surface of the coating film is wiped with the nonwoven fabric, the virus infection inhibition effect of the coating film is reduced. That is, in the examples, the virus test is performed under more stringent conditions. The antiviral activity value obtained in the examples is lower than the antiviral activity value obtained by the measurement method described in the "Specific Implementation Method". Therefore, when the antiviral activity value obtained in the antiviral test of the examples is 2 or more, it can be judged that the virus infection inhibition particles have a virus infection inhibition effect.

[0108] [Table 1]

[0109]

[0110] Industrial Applicability

[0111] The virus infection inhibitory particles of the present invention can easily adjust the size of the virus infection inhibitor and disperse it in a substrate such as a synthetic resin or a fiber product, and can fully ensure the contact between the virus infection inhibitor and the virus. Therefore, the virus infection inhibitory particles of the present invention can produce a virus infection inhibitory product having an excellent virus infection inhibitory effect.

[0112] (CROSS-REFERENCE TO RELATED APPLICATIONS)

[0113] This application claims priority based on Japanese Patent Application No. 2021-040824 filed on March 12, 2021, the disclosure of which is incorporated into this specification by reference in its entirety.

Claims

1. A virus infection inhibiting particle comprising: Resin particles; and A virus infection inhibitor present on the surface of the resin particles and comprising a sulfonic acid compound having a sulfonic acid group and / or a sulfonic acid group derivative, The average particle size of the primary particles of the resin particles is 1 μm or more and 20 μm or less. The sulfonic acid compound includes at least one sulfonic acid compound selected from linear alkylbenzene sulfonic acid, linear alkylbenzene sulfonate, α-olefin sulfonic acid, alkyldiphenyl ether sulfonic acid, alkyldiphenyl ether sulfonate, α-olefin sulfonate, polyoxyalkylene alkyl ether sulfate, and a polymer having a sulfonic acid-derived group on a side chain of a linear polymer.

2. The virus infection inhibitory particle according to claim 1, wherein The sulfonic acid compound adheres to the surface of the resin particles.

3. The virus infection inhibitory particle according to claim 1 or 2, wherein The amount of the sulfonic acid compound present in the resin particles is 1 part by mass or more and 100 parts by mass or less relative to 100 parts by mass of the resin particles.

4. The virus infection inhibitory particle according to claim 1 or 2, wherein The resin particles include aggregated particles in which resin particles serving as primary particles are aggregated and integrated.

5. The virus infection inhibitory particle according to claim 1 or 2, wherein The sulfonic acid compound has an aromatic ring.

6. The virus infection inhibitory particle according to claim 1 or 2, wherein The average particle size of the primary resin particles is 10 μm or less.

7. The virus infection inhibitory particle according to claim 4, wherein The average particle size of the agglomerated particles is 20~75μm.

8. The virus infection inhibitory particle according to claim 4, wherein The content of the aggregated particles in the virus infection inhibitory particles is 30% or more.

9. A viral infection inhibition product comprising: substrate; and The virus infection inhibitory particle according to any one of claims 1 to 8, which is contained in the substrate.

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