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

Abstract

The present invention provides a virus infection inhibitor that exhibits an excellent virus infection inhibiting effect over a long period of time due to reduced shedding from a base material. This virus infection inhibiting agent is characterized by including, as an active ingredient, a virus infection inhibiting compound containing an alkoxysilyl structure or a silanol structure represented by a prescribed structural formula, and an acidic functional group or an anhydride group thereof in each molecule. Therefore, the virus infection inhibiting agent exhibits an excellent virus infection inhibiting effect and reduced shedding from the base material, and can impart an excellent virus infection inhibiting effect to the base material for a long period of time.

Description

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

[0001] The present invention relates to a virus infection inhibitor, a virus infection inhibitor liquid, a virus infection inhibitor paint, a masterbatch for synthetic resin molding, and a virus infection inhibitor product.

[0002] In recent years, in addition to the seasonal influenza virus epidemic, 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] Patent Document 1 states that (a) the critical micelle concentration at 25°C is 0.2 × 10 -3 mol / L or more 2.0×10 -3 mol / L or less, and a Krafft point of 5°C or less, and contains an anionic surfactant (hereinafter referred to as component (a)) having a sulfonic acid group, a sulfate ester group, or a salt of these substituents as an active ingredient.

[0005] Patent Document 2 discloses an envelope virus inactivator containing (a) an arylsulfonic acid or a salt thereof as an active ingredient, which may be substituted with one to three hydrocarbon groups having from 1 to 5 carbon atoms.

[0006] JP 2023-110871 A JP 2023-70880 A

[0007] However, the enveloped virus inactivators disclosed in Patent Documents 1 and 2 are insufficient in their effect of inactivating enveloped viruses, and there is a demand for a virus infection inhibitor that exhibits an excellent inactivation effect.

[0008] Furthermore, the envelope virus inactivators of Patent Documents 1 and 2 can be incorporated into various products to produce virus inactivation products. Virus inactivation products typically come into contact with human hands or are rubbed against other objects during use. Therefore, there is a problem in that the virus inactivation product contained in the virus inactivation product falls off, causing the virus inactivation effect to decrease within a short period of time.

[0009] The present invention provides a virus infection inhibitor that exhibits excellent virus infection inhibitory effects over a long period of time with reduced shedding from a substrate, as well as a virus infection inhibitor liquid, a virus infection inhibitor paint, a masterbatch for synthetic resin molding, and a virus infection inhibitor product that use the virus infection inhibitor.

[0010] The virus infection inhibitor of the present invention is characterized by containing, as an active ingredient, a virus infection inhibitory compound having, in its molecule, an alkoxysilyl structure represented by formula (1) or a silanol structure represented by formula (2) and a structure containing an acidic functional group or its anhydride group.

[0011] (However, in formula (1), R 1 is an alkyl group. In formulas (1) and (2), * denotes a bond and represents a single bond.

[0012] The viral infection inhibitor solution of the present invention is characterized by containing the viral infection inhibitor and a solvent.

[0013] The virus infection-preventing paint of the present invention is characterized by containing the virus infection-preventing agent, a solvent, and a binder resin.

[0014] The synthetic resin molding masterbatch of the present invention is characterized by containing the above-mentioned virus infection inhibitor and a synthetic resin.

[0015] The viral infection inhibitor of the present invention exhibits excellent viral infection inhibitory effects because it contains, as an active ingredient, a viral infection inhibitory compound having, in the molecule, an alkoxysilyl structure or a silanol structure and a structure containing an acidic functional group or an anhydride group thereof.

[0016] The alkoxysilyl structure or silanol structure of the virus infection inhibitor of the present invention forms a strong bond with the substrate, reducing the likelihood of it falling off from the substrate, and allowing the agent to impart an excellent virus infection inhibitory effect to the substrate over a long period of time.

[0017] In the numerical ranges described in stages in this specification, the upper or lower limit of a certain numerical range can be arbitrarily combined with the upper or lower limit of another numerical range. In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with a value shown in an example or a value that can be unambiguously derived from an example. In this specification, a numerical value connected with "to" means a numerical range that includes the numbers before and after "to" as the lower and upper limits.

[0018] [Virus infection-inhibiting compound] The virus infection-inhibiting agent contains, as an active ingredient, a virus infection-inhibiting compound having, in the molecule, an alkoxysilyl structure represented by formula (1) (hereinafter, sometimes simply referred to as "alkoxysilyl structure") or a silanol structure represented by formula (2) (hereinafter, sometimes simply referred to as "silanol structure"), and a structure containing an acidic functional group or its anhydride group. The virus infection-inhibiting compound may be used alone or in combination of two or more types. In formula (1), R 1 is an alkyl group. In this specification, * is a bond and means a single bond.

[0019]

[0020] (However, in formula (1), R 1 is an alkyl group. In formulas (1) and (2), * denotes a bond and represents a single bond.

[0021] The content of the viral infection-inhibiting 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.

[0022] The viral infection inhibitor exhibits excellent viral infection inhibitory effects by containing the viral infection inhibitory compound.

[0023] Here, the viral infection inhibitory effect refers to the effect of eliminating or reducing the infectivity of a virus to a cell, or preventing the virus from proliferating in the cell even if it infects. Methods for confirming the presence or absence of such viral infectivity include, for example, ISO 18184 and JIS L1922 for textile products, and ISO 21702 for plastic products other than textile products and products with non-porous surfaces. Other methods include the plaque method and hemagglutination unit (HAU) measurement method described in "Medical and Pharmaceutical Virology" (first edition published in April 1990).

[0024] The viral infection-inhibiting effect of a viral infection inhibitor can be measured, for example, as follows: A viral infection-inhibiting paint is prepared by mixing a viral infection inhibitor containing 5 parts by mass of a viral infection-inhibiting compound with 95 parts by mass of an ultraviolet-curable acrylic paint. The viral infection-inhibiting paint is applied to a polyethylene film using a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0025] At 25°C, the coating layer was exposed to ultraviolet light with a wavelength of 365 nm at an integrated light intensity of 500 mJ / cm 2 The ultraviolet curing acrylic paint is cured by irradiating the paint so as to form a coating film having a thickness of 18 μm.

[0026] A test piece is prepared by cutting out a flat square piece of coating film with a side length of 5.0 cm. The surface of the coating film on the obtained test piece is wiped with a flat square piece of nonwoven fabric with a side length of 10 cm by moving the nonwoven fabric back and forth 10 times to obtain a test coating film.

[0027] The obtained test coating film is subjected to an antiviral test in accordance with ISO 21702. After the reaction, the virus suspension is subjected to the plaque method to measure the virus infectivity (common logarithm) (PFU / cm 2 ) is calculated.

[0028] A blank coating film 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 determined based on this blank coating film in the same manner as above. 2 ) is calculated.

[0029] The antiviral activity value is calculated by subtracting the viral infectivity of the test coating from the viral infectivity of the blank coating.

[0030] In addition, a resin composition is produced by melt-kneading and mixing a virus infection inhibitor containing 5 parts by mass of a virus infection-inhibiting compound with 95 parts by mass of a synthetic resin, and this resin composition is press-molded to produce a sheet-like synthetic resin molded product with an average thickness of 1 mm. The surface of the obtained synthetic resin molded product is wiped with a flat square nonwoven fabric measuring 10 cm on a side by moving the nonwoven fabric back and forth 10 times, and this synthetic resin molded product is used as a test specimen. A blank reference specimen is prepared in the same manner as above, except that it does not contain the virus infection inhibitor. The antiviral activity value may be calculated in the same manner as above using a test specimen and a blank reference specimen instead of the test coating and blank coating.

[0031] The antiviral activity value of the viral infection inhibitor 24 hours after the start of the reaction in an antiviral test in accordance with ISO 21702 is preferably 2.0 or more, more preferably 2.5 or more, and even more preferably 2.8 or more. Regardless of the type of virus being evaluated, it is preferable that the antiviral activity value be 2.0 or more for at least one type of virus.

[0032] An alkoxysilyl structure refers to a structure in which an alkoxy group is directly bonded to a silicon atom, as shown in formula (1). An alkoxy group refers to a group in which the hydrogen atom of a hydroxyl group (-OH) is substituted with an alkyl group. An alkyl group refers to the atomic group remaining after removing one hydrogen atom from an aliphatic saturated hydrocarbon, and may be either linear or branched. It is preferable that the hydrogen atom of the alkyl group is not substituted. The alkoxy group is not particularly limited, and examples include alkoxy groups having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group. The alkoxy group is preferably a methoxy group or an ethoxy group, and more preferably an ethoxy group.

[0033] The silanol structure is a structure in which a hydroxyl group (—OH) is directly bonded to a silicon atom, as shown in formula (2).

[0034] The viral infection-inhibiting compound has an alkoxysilyl structure represented by formula (1) or a silanol structure represented by formula (2) in its molecule, which allows the viral infection-inhibiting compound to form a strong bond with the substrate, reducing the virus infection inhibitor's detachment from the substrate and imparting an excellent viral infection-inhibiting effect to the substrate over a long period of time. The alkoxysilyl structure represented by formula (1) is hydrolyzed, as necessary, by moisture contained in the substrate or in the air to generate a silanol structure represented by formula (2), and this generated silanol structure forms a strong bond with the substrate.

[0035] Furthermore, although the viral infection inhibitory compound has an alkoxysilyl structure represented by formula (1) or a silanol structure represented by formula (2), this has almost no effect on the viral infection inhibitory effect exerted by the acidic functional group or its anhydride group described below, and the viral infection inhibitor exhibits excellent viral infection inhibitory effect.

[0036] The viral infection-inhibiting compound has a structure containing an acidic functional group or an anhydride group thereof, and exhibits excellent viral infection-inhibiting effects due to the acidic functional group or the anhydride group thereof.

[0037] The acidic functional group refers to a functional group capable of releasing hydrogen ions (protons) in an aqueous solution. The acidic functional group is preferably an H-type acidic functional group. Examples of the acidic functional group include a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), and a phosphonic acid group [-P(=O)(OH)2]. The carboxy group (-COOH) is preferred because it exhibits an excellent viral infection inhibitory effect without substantially interfering with the bonding action with the substrate exerted by the alkoxysilyl structure and silanol structure.

[0038] The structure containing an acidic functional group is preferably a structure containing a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], more preferably a structure containing a carboxy group (-COOH), more preferably a carboxy group (-COOH), a structure represented by the following formula (5-1) (succinic acid residue), a structure represented by the following formula (5-2) (phthalic acid residue), or a structure represented by the following formula (5-3) (maleic acid residue), more preferably a carboxy group (-COOH) or a structure represented by the formula (5-1) (succinic acid residue). These structures can further demonstrate the excellent virus infection inhibitory effect of the virus infection inhibitor while maintaining the excellent adhesion to substrates due to the alkoxysilyl structure and silanol structure.

[0039] In the formulas (5-1) to (5-3), one of the two carboxy groups (—COOH) is esterified to —COOR. 9 It may be as follows. 9 is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, with a methyl group or an ethyl group being preferred, and an ethyl group being more preferred. The alkyl group may be either linear or branched. It is preferred that the hydrogen atoms of the alkyl group are not substituted.

[0040]

[0041] The acidic functional group may be an anhydride group. The anhydride group reacts with the substrate or moisture in the air to hydrolyze, generating an acidic functional group and exhibiting a viral infection prevention effect. The anhydride group of the acidic functional group is preferably an anhydride group of a carboxy group (*-CO-O-CO-*). Note that the bonds * at both ends of the anhydride group are bonds and represent single bonds.

[0042] The anhydride group of the acidic functional group is preferably, for example, the structure represented by the following formula (6-1) (anhydride group of a succinic acid residue), the structure represented by the following formula (6-2) (anhydride group of a phthalic acid residue), or the structure represented by the following formula (6-3) (anhydride group of a maleic acid residue), and more preferably the structure represented by (6-1) (anhydride group of a succinic acid residue). The structures represented by formulas (6-1) to (6-3) allow the virus infection inhibitor to exhibit excellent virus infection inhibitory effects while maintaining excellent adhesion to substrates due to the alkoxysilyl structure and silanol structure.

[0043]

[0044] The number of acidic functional groups in the viral infection-inhibiting compound is preferably multiple (two or more), since this improves the viral infection-inhibiting effect of the viral infection-inhibiting agent. When the viral infection-inhibiting compound has multiple acidic functional groups, the acidic functional groups may be all of the same type, or may contain acidic functional groups of different types. Since this allows the proton-releasing ability of the acidic functional groups in the viral infection-inhibiting compound to be fully exerted, thereby improving the viral infection-inhibiting effect of the viral infection-inhibiting agent, it is preferable that the acidic functional groups are all of the same type, and more preferably that the acidic functional groups are all carboxy groups (-COOH).

[0045] Although the viral infection inhibitory compound has not been clearly elucidated, it is believed that the alkoxysilyl structure or the above-mentioned silanol structure firmly binds to the substrate and positions the acidic functional group on the outside, effectively capturing viruses and improving interaction with the viruses, and therefore the viral infection inhibitor exhibits excellent viral infection inhibitory effects.

[0046] The viral infection-inhibiting compound is preferably a compound having the structure shown in formula (3) or formula (4).

[0047]

[0048] The viral infection-inhibiting compound represented by formula (3) will be described. In formula (3), X 1 is a structure containing an acidic functional group or an anhydride group thereof. The acidic functional group is preferably a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], and more preferably a carboxy group (-COOH).

[0049] In formula (3), X 1 is preferably a structure containing one acidic functional group selected from the group consisting of a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H) and a phosphonic acid group [-P(=O)(OH)2], or an anhydride group of this functional group, more preferably a structure containing a carboxy group (-COOH) or an anhydride group of a carboxy group (-CO-O-CO-), more preferably a carboxy group (-COOH), a succinic acid residue [formula (5-1)] or an anhydride group of a succinic acid residue [formula (6-1)], and even more preferably a succinic acid residue [formula (5-1)] or an anhydride group of a succinic acid residue [formula (6-1)].

[0050] In formula (3), R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. The alkyl group is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, with a methyl group or an ethyl group being preferred, and an ethyl group being more preferred. The alkyl group may be either linear or branched. It is preferred that the hydrogen atoms of the alkyl group are not substituted. R 2 is preferably a hydrogen atom. 3is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and even more preferably an alkyl group having 1 to 3 carbon atoms.

[0051] In formula (3), a is an integer of 1 to 20. a is preferably 1 to 10, more preferably 2 to 8, and still more preferably 3 to 6, because this improves the viral infection inhibitory effect of the viral infection inhibitor.

[0052] In formula (3), b is an integer of 0 to 2. b is preferably 0 or 1, and more preferably 0, because this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0053] The viral infection-inhibiting compound represented by formula (3) is preferably a compound represented by the following formula (3-1) or an anhydride thereof [formula (3-2)], more preferably a compound represented by the following formula (3-3) or an anhydride thereof [formula (3-4)], and more preferably 3-trimethoxysilylpropylsuccinic acid [in formula (3-3), R 3 is a methyl group] or an anhydride thereof [in formula (3-4), R 3 is a methyl group], or 3-triethoxysilylpropylsuccinic acid [in formula (3-3), R 3 is an ethyl group] or an anhydride thereof [in formula (3-4), R 3 In the formulas (3-1) to (3-4), a and R are preferably an ethyl group. 3 is the same as that explained in equation (3).

[0054]

[0055] The viral infection-inhibiting compound represented by formula (4) will now be described.

[0056]

[0057] In formula (4), X 2 and X 3are each independently a structure containing an acidic functional group or an anhydride group thereof. The acidic functional group is preferably a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], and more preferably a carboxy group (-COOH). 2 and X 3 may be the same or different.

[0058] In formula (4), X 2 and X 3 is preferably a structure containing one acidic functional group selected from the group consisting of a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), and a phosphonic acid group [-P(=O)(OH)2], or an anhydride group of this acidic functional group, more preferably a structure containing a carboxy group (-COOH) or an anhydride group of a carboxy group (-CO-O-CO-), and even more preferably a structure containing a succinic acid residue [formula (5-1)] or a structure containing an anhydride group of a succinic acid residue [formula (6-1)], because this improves the viral infection inhibitory effect of the viral infection inhibitor.

[0059] In formula (4), R 4 is a hydrogen atom, a hydroxyl group (—OH) or an alkyl group having 1 to 10 carbon atoms, preferably a hydroxyl group or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydroxyl group or an alkyl group having 1 to 3 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 6 is a hydrogen atom, a hydroxyl group (—OH) or an alkyl group having 1 to 10 carbon atoms, preferably a hydroxyl group or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydroxyl group or an alkyl group having 1 to 3 carbon atoms. 7 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 4 , R 5 , R 6 and R 7In the formula (I), the alkyl group is not particularly limited and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, with methyl or ethyl being preferred, and ethyl being more preferred. The alkyl group may be either linear or branched. It is preferred that the hydrogen atoms of the alkyl group are not substituted. R 4 , R 5 , R 6 and R 7 When any two or more of R are alkyl groups, they may be the same or different. 4 and R 6 is preferably a hydroxyl group, since this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time. 5 and R 7 is preferably a hydrogen atom, since this further reduces the dropping off of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0060] In formula (4), c is 0 or 1, and 0 is preferred because this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0061] In formula (4), e is 0 or 1, and 0 is preferred because this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0062] In formula (4), d is an integer of 1 to 100, and is preferably 1 to 80, and more preferably 1 to 40, since this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0063] The viral infection-inhibiting compound represented by formula (4) is preferably a compound represented by the following formula (4-1a) or formula (4-1b), and more preferably a compound represented by the following formula (4-2a) or formula (4-2b). 4 ~R 7 and d are the same as those explained in equation (4).

[0064]

[0065] In formula (4-1a) and formula (4-1b), s is an integer of 1 to 20. s is preferably an integer of 1 to 7, and more preferably an integer of 1 to 5, because this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0066] In formula (4-1a) and formula (4-1b), q is an integer of 1 to 20. q is preferably an integer of 1 to 7, and more preferably an integer of 1 to 5, because this further reduces the detachment of the virus infection inhibitor from the substrate and allows the substrate to be provided with an excellent virus infection inhibitory effect for a longer period of time.

[0067] The viral infection-inhibiting compound may be a polymer compound. The viral infection-inhibiting compound is preferably a chain polymer having an alkoxysilyl structure or a silanol structure and an acidic functional group or an anhydride group thereof on the side chain of the chain polymer.

[0068] When the viral infection-inhibiting compound is a chain polymer having an alkoxysilyl structure or a silanol structure and an acidic functional group or an anhydride group thereof in the side chain, the alkoxysilyl structure or the silanol structure and the acidic functional group or an anhydride group thereof can be incorporated into the substrate in a state in which the alkoxysilyl structure or the silanol structure and the acidic functional group or anhydride group thereof are arranged along the main chain, and the compound can impart an excellent viral infection-inhibiting effect to the substrate while forming a strong bond to the substrate. The acidic functional group is preferably a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], and more preferably a carboxy group (-COOH).

[0069] The acidic functional group or anhydride group thereof is preferably an acidic functional group selected from the group consisting of a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), and a phosphonic acid group [-P(=O)(OH)2], or a structure containing an anhydride group of this functional group, because this improves the viral infection inhibitory effect of the viral infection inhibitor; more preferably a structure containing a carboxy group (-COOH) or an anhydride group of a carboxy group (-CO-O-CO-); more preferably a carboxy group (-COOH), a succinic acid residue [formula (5-1)], or an anhydride group of a succinic acid residue [formula (6-1)]; and even more preferably a succinic acid residue [formula (5-1)] or an anhydride group of a succinic acid residue [formula (6-1)].

[0070] As the viral infection-inhibiting compound which is a chain polymer, a polymer represented by formula (7-1) or formula (7-2) is more preferred.

[0071] In formulas (7-1) and (7-2), n is the number of repeating units and is an integer of 1 to 1000, m is the number of repeating units and is an integer of 1 to 1000, and p is the number of repeating units and is an integer of 1 to 1000. 8 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. The alkyl group is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. A methyl group or an ethyl group is preferred, and an ethyl group is more preferred. The alkyl group may be either linear or branched. It is preferred that the hydrogen atom of the alkyl group is not substituted. In formulas (7-1) and (7-2), —Si(OR 8 The three groups and the carbon atoms of the main chain are linked by a chain polymer (for example, vinyl polymer, polyalkylene oxide, polyurethane, polyester, etc.).

[0072] When the viral infection-inhibiting compound is a chain polymer, the number average molecular weight of the viral infection-inhibiting compound is preferably 100,000 or less, more preferably 50,000 or less, and more preferably 10,000 or less. When the viral infection-inhibiting compound is a chain polymer, the number average molecular weight of the viral infection-inhibiting compound is preferably 1,000 or more, more preferably 20,000 or more, and more preferably 5,000 or more. When the number average molecular weight of the viral infection-inhibiting compound that is a chain polymer is 100,000 or less, aggregation of the viral infection-inhibiting compound is suppressed, increasing the surface area and facilitating contact with the virus, thereby improving the viral infection-inhibiting effect of the viral infection inhibitor. When the number average molecular weight of the viral infection-inhibiting compound that is a chain polymer is 1,000 or more, the viral infection-inhibiting compound and the virus can be adsorbed at multiple points, improving the viral infection-inhibiting effect.

[0073]

[0074] The pH of a 0.5 mass% aqueous solution of the viral infection-inhibiting compound at 25°C is preferably 4.5 or less, since this allows the acidity of the acidic functional groups of the viral infection-inhibiting compound to be easily maintained and improves the viral infection-inhibiting effect of the viral infection inhibitor. The pH of a 0.5 mass% aqueous solution of the viral infection-inhibiting compound refers to the pH value at 25°C of an aqueous solution obtained by adding 0.5 g of the viral infection-inhibiting compound to 99.5 g of purified water and uniformly mixing them to form an aqueous solution. When the concentration of the viral infection-inhibiting compound in a saturated aqueous solution at 25°C is less than 0.5 mass%, the pH is the pH at 25°C of a suspension containing 0.5 parts by mass of the viral infection-inhibiting compound and 99.5 parts by mass of water, in which the viral infection-inhibiting compound has dissolved in water to its solubility and reached a saturated state.

[0075] When the viral infection-inhibiting compound does not contain a repeating unit, the molecular weight of the viral infection-inhibiting compound is preferably 1000 or less, more preferably 800 or less, more preferably 600 or less, more preferably 500 or less, more preferably 460 or less, more preferably 450 or less, more preferably 400 or less, and more preferably 350 or less. When the molecular weight of the viral infection-inhibiting compound is 1000 or less, the viral infection-inhibiting effect of the viral infection inhibitor is improved.

[0076] The pKa1 of the viral infection inhibiting compound at 25° C. is preferably 4.5 or less, more preferably 4.4 or less, more preferably 4.3 or less, more preferably 4.2 or less, and more preferably 4.0 or less. When the pKa1 of the viral infection inhibiting compound is 4.5 or less, the viral infection inhibiting effect of the viral infection inhibitor is improved.

[0077] When the viral infection inhibiting compound is a polyvalent acid, the viral infection inhibiting compound undergoes multi-stage ionization, and pKa1 refers to the pKa calculated based on the ionization constant of the first stage. + and A - When an acid dissociates into HCl and HCl to reach ionization equilibrium (A), the acid dissociation constant Ka is defined by formula (B), and pKa is defined as the common logarithm (C) of the reciprocal of the acid dissociation constant Ka.

[0078]

[0079] The pKa1 of the viral infection-inhibiting compound refers to 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).

[0080] The amount of acidic functional groups in the viral infection-inhibiting compound is preferably 3 mmol / g or more, more preferably 3.5 mmol / g or more, more preferably 4 mmol / g or more, and even more preferably 6 mmol / g or more. When the amount of acidic functional groups in the viral infection-inhibiting compound is 3 mmol / g or more, the viral infection-inhibiting effect of the viral infection inhibitor is improved.

[0081] The amount of acidic functional groups in the viral infection-inhibiting compound refers to a value measured by titration. Specifically, approximately 1 g (W1g) of the dried viral infection-inhibiting compound is weighed out, 200 mL of purified water is added to the viral infection-inhibiting compound, and titration is performed at 25°C using 0.1 mol / L aqueous sodium hydroxide solution. The amount of aqueous sodium hydroxide solution consumed (W2mL) 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 amount of acidic functional groups (mmol / g) in the viral infection-inhibiting compound is calculated using the following formula: Amount of acidic functional groups (mmol / g) = 0.1 x W1 / W2

[0082] The solubility of the viral infection-inhibiting compound in water at 25° C. is preferably 500 g / L or less, more preferably 100 g / L or less, more preferably 80 g / L or less, and still more preferably 20 g / L or less. When the solubility of the viral infection-inhibiting compound in water at 25° C. is 500 g / L or less, the viral infection-inhibiting compound has an improved affinity for viruses rather than water molecules, and the viral infection-inhibiting effect of the viral infection inhibitor is improved.

[0083] The solubility of the viral infection-inhibiting compound in water at 25°C refers to the mass (g) of the viral infection-inhibiting compound in a saturated aqueous solution obtained by dissolving the viral infection-inhibiting compound in 1 L of water. The solubility of the viral infection-inhibiting compound in water at 25°C refers to a value measured at 25°C in accordance with OECD Chemicals Testing Guideline No. 105 (Water Solubility).

[0084] [Virus infection inhibitor] The virus infection inhibitor contains a virus infection inhibitory compound as an active ingredient. The method for producing the virus infection inhibitor is not particularly limited, and the virus infection inhibitor can be produced by mixing the virus infection inhibitory compound with general-purpose additives as needed in a general manner.

[0085] Next, the usage of the virus infection inhibitor will be described. The virus infection inhibitor has a virus infection inhibitory effect against various viruses due to the action of the virus infection inhibitor compound, and exhibits excellent virus infection inhibitory effect against both enveloped and non-enveloped viruses.

[0086] Examples of enveloped viruses include influenza viruses (e.g., types A and B), 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), yellow fever viruses, AIDS viruses, rabies viruses, hantaviruses, dengue viruses, Nipah viruses, and lyssaviruses.

[0087] Examples of non-enveloped viruses include feline calicivirus, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, and rhinovirus.

[0088] The virus infection inhibitor is used, for example, by being contained in a substrate to which it is desired to impart a virus infection inhibitory effect, thereby constituting a virus infection inhibitory product. The substrate containing the virus infection inhibitor exhibits a virus infection inhibitory effect as a virus infection inhibitory product. The form in which the virus infection inhibitor is contained in the substrate is not particularly limited, and examples include a form in which the virus infection inhibitor is mixed into the substrate, a form in which the virus infection inhibitor is adhered to the surface of the substrate, and a form in which the virus infection inhibitor is kneaded into the substrate. The virus infection inhibitor has excellent adhesion to the substrate, and therefore exhibits particularly excellent effects when the virus infection inhibitor is adhered to the surface of the substrate.

[0089] The virus infection inhibitor can be adhered to the surface of a substrate by dissolving or dispersing the virus infection inhibitor in a solvent to prepare a virus infection inhibitory liquid, and then applying the virus infection inhibitory liquid to the substrate. The virus infection inhibitory liquid may contain additives such as water-soluble solvents, oils, emulsions, and suspensions, as needed.

[0090] Examples of the solvent include water (preferably ion-exchanged water), alcohols (methyl alcohol, ethyl alcohol, propyl alcohol, etc.), hydrocarbons (toluene, xylene, methylnaphthalene, kerosene, cyclohexane, etc.), ethers (diethyl ether, tetrahydrofuran, dioxane, etc.), ketones (acetone, methyl ethyl ketone, etc.), and amides (N,N-dimethylformamide, etc.), with water or alcohols being preferred.

[0091] The content of the virus infection inhibitor in 100% by mass of the virus infection inhibiting solution is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and more preferably 1% by mass or more. The content of the virus infection inhibitor in 100% by mass of the virus infection inhibiting solution is preferably 20% by mass or less, more preferably 15% by mass or less, and more preferably 10% by mass or less.

[0092] The substrate to be incorporated with the virus infection inhibitor is not particularly limited as long as it is capable of incorporating the virus infection inhibitor, and examples include synthetic resin molded products, paints, wallpaper, decorative sheets, flooring materials, fibers, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), interior and interior materials for vehicles (for example, cars, airplanes, ships, etc.) (seats, child seats, and foams that constitute these), kitchenware, baby products, and building interior materials.

[0093] The synthetic resin constituting the synthetic resin molded body is not particularly limited, and examples thereof include thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylonitrile styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefin, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyether ether ketone, thermoplastic polyimide, polyamide imide, etc.), thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin, silicone resin, polyurethane, thermosetting polyimide, etc.). The synthetic resins may be used alone or in combination of two or more.

[0094] The virus infection inhibitor may be kneaded into a synthetic resin. Even when the virus infection inhibitor is kneaded into the synthetic resin, the virus infection inhibitor has excellent adhesion to the synthetic resin on the surface of the resulting molded article, remains on the surface of the molded article for a long period of time, and maintains excellent virus infection-inhibiting effect. A method for kneading the virus infection inhibitor into a synthetic resin involves mixing the virus infection inhibitor with a raw synthetic resin to prepare a resin composition, and using this resin composition to obtain a virus infection-inhibiting product of a desired shape as a molded article by a general-purpose synthetic resin molding method. Examples of general-purpose synthetic resin molding methods include extrusion molding, injection molding, and blow molding. The synthetic resin and the virus infection inhibitor may be mixed to form a masterbatch for synthetic resin molding, and this masterbatch may be mixed with the raw synthetic resin to produce a virus infection-inhibiting product as a molded article by a general-purpose synthetic resin molding method.

[0095] The content of the virus infection inhibitor in 100% by mass of the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, and more preferably 5% by mass or more. The content of the virus infection inhibitor in 100% by mass of the resin composition is preferably 20% by mass or less, more preferably 15% by mass or less, and more preferably 10% by mass or less.

[0096] The content of the virus infection inhibitor in 100% by mass of the masterbatch for synthetic resin molding is preferably 20% by mass or more, more preferably 30% by mass or more, and more preferably 50% by mass or more. The content of the virus infection inhibitor in 100% by mass of the masterbatch for synthetic resin molding is preferably 80% by mass or less, more preferably 70% by mass or less, and more preferably 60% by mass or less.

[0097] The virus infection inhibitor may be incorporated into fibers by, for example, adhering to a fiber serving as a base material. A method for adhering the virus infection inhibitor to fibers will now be described. Examples of methods for adhering the virus infection inhibitor to fibers include: (1) dissolving or dispersing the virus infection inhibitor in a solvent to prepare a virus infection inhibitory liquid, and then impregnating fibers with the virus infection inhibitory liquid to impregnate the fibers with the virus infection inhibitory liquid; (2) applying or spraying the virus infection inhibitory liquid to the surface of fibers; (3) immersing fibers in a binder resin in which the virus infection inhibitor is dissolved or dispersed, and adhering the virus infection inhibitor to the fibers with the binder resin; and (4) applying or spraying the binder resin in which the virus infection inhibitor is dissolved or dispersed to the surface of fibers, and adhering the virus infection inhibitor to the fibers with the binder resin. In the methods (1) and (2), a binder resin may be incorporated into the virus infection inhibitory liquid. The solvent is the same as described above, and therefore further explanation is omitted.

[0098] The binder resin is not particularly limited as long as it can fix the virus infection inhibitor to the fiber surface. For example, examples of the binder resin include urethane-based resins such as one-component urethane resins and two-component urethane resins, silicone-based resins, acrylic resins, urethane acrylate resins, polyester resins, unsaturated polyester resins, alkyd resins, vinyl acetate resins, vinyl chloride resins, epoxy resins, and epoxy acrylate resins, with urethane-based resins being preferred.

[0099] 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. Paints also include photocurable paints that polymerize upon irradiation with radiation such as ultraviolet light to produce a binder resin component.

[0100] Paints generally contain a binder resin and a solvent. The binder resin and solvent are the same as those described above, and therefore further explanation is omitted. The paint may contain additives such as pigments, plasticizers, curing agents, extenders, fillers, antioxidants, thickeners, and surfactants, as long as the additives do not impair the paint's physical properties. Examples of methods for preparing a virus infection inhibitor paint by incorporating a virus infection inhibitor into the paint include a method in which the virus infection inhibitor and the paint are supplied to a dispersing device and mixed uniformly. Examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill.

[0101] The content of the virus infection inhibitor in 100% by mass of the virus infection inhibitor paint is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and more preferably 1% by mass or more. The content of the virus infection inhibitor in 100% by mass of the virus infection inhibitor paint is preferably 20% by mass or less, more preferably 15% by mass or less, and more preferably 10% by mass or less.

[0102] 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.

[0103] 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.

[0104] The present invention will be described in more detail below using examples, but the present invention is not limited thereto. Specific numerical values ​​of the blending ratios (content ratios), physical property values, parameters, etc. used in the following description can be replaced with the upper limit values ​​(numeric values ​​defined as "equal to or less than") or lower limit values ​​(numeric values ​​defined as "equal to or greater than") of the blending ratios (content ratios), physical property values, parameters, etc. described in the "Summary of the Invention" and the "Description of the Invention".

[0105] The following compounds were prepared as viral infection inhibitory compounds that serve as active ingredients of viral infection inhibitors.

[0106] [Viral infection-inhibiting compound] 3-trimethoxysilylpropylsuccinic anhydride [in formula (3-4), R 3 is a methyl group] (trade name "X-12-967C" manufactured by Shin-Etsu Chemical Co., Ltd.) 3-trimethoxysilylpropylsuccinic acid [in formula (3-3), R 3 is a methyl group] 3-triethoxysilylpropylsuccinic anhydride [in formula (3-4), R 3 is an ethyl group] 3-triethoxysilylpropylsuccinic acid [in formula (3-3), R 3 is an ethyl group]

[0107]

[0108] A compound represented by formula (4-2)

[0109]

[0110] A mixture of 55% by mass of 2-[3-triethoxysilylpropyl]succinic acid monoethyl ester [formula (8-1)] and 45% by mass of 3-[3-triethoxysilylpropyl]succinic acid monoethyl ester [formula (8-2)]

[0111]

[0112] [Other compounds] Succinic acid Phthalic acid Citric acid Salicylic acid

[0113] The molecular weight, pKa at 25°C, pH of a 0.5% by mass aqueous solution at 25°C, solubility in water at 25°C, and amount of acidic functional groups of the viral infection-inhibiting compound were measured as described above, and the results are shown in Table 1. In the table, "pKa at 25°C," "pH of a 0.5% by mass aqueous solution at 25°C," "solubility in water at 25°C," and "amount of acidic functional groups" are represented as "pKa," "pH," "solubility," and "amount of acidic functional groups," respectively. In the table, "<X" (X is a numerical value) means "smaller than X." In the table, ">X" (X is a numerical value) means "greater than X."

[0114] (Examples 1 to 6 and Comparative Examples 1 to 4) Viral infection inhibitors were prepared containing, as active ingredients, 100% by mass of the viral infection inhibitor compounds shown in Table 1. For convenience, the compounds of Comparative Examples 1 to 4 are listed in the "Viral infection inhibitor compound" column.

[0115] [Antiviral Test] The antiviral activity value was measured in the following manner, and the results are shown in Table 1.

[0116] (Initial activity value) A virus infection-preventing paint was prepared by mixing 10 parts by mass of the virus infection-preventing agent and 90 parts by mass of an ultraviolet-curing acrylic paint (manufactured by Coattec Co., Ltd., product name "AI-N2") The virus infection-preventing paint was applied to a polyethylene film using a wire bar coater #8 to a thickness of 18 μm to form a coating layer.

[0117] 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 dose of 500 mJ / cm. 2 The ultraviolet-curable acrylic paint was cured by irradiating the paint so as to form a test coating film having a thickness of 18 μm.

[0118] The obtained test coating film was subjected to an antiviral test in accordance with ISO 21702. For the virus suspension 24 hours after the start of the reaction, the virus infectivity titer (common logarithm value) of the test coating film was calculated by the plaque method.

[0119] A blank coating film 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 determined based on this blank coating film in the same manner as above. 2 The virus infectivity titer (common logarithm) of the blank coating film was calculated as 6.5 PFU / cm 2 It was.

[0120] The antiviral activity value (initial activity value) was calculated by subtracting the viral infectivity value of the test coating film from the viral infectivity value of the blank coating film.

[0121] (Activity Value After Durability Test) A virus infection-preventing paint was prepared in the same manner as in measuring the initial activity value, and the ultraviolet-curable acrylic paint was cured to form a coating film with a thickness of 18 μm.

[0122] A flat square cotton cloth measuring 6 cm on a side [JIS L0803-compliant test white cloth (Kanakin No. 3) for cotton] was impregnated with 0.5 mL of purified water (25°C), and the cotton cloth was attached to the friction element of a friction tester Type I (manufactured by Imoto Machinery Co., Ltd.). The surface of the resulting coating film was pressed against the surface of the test piece at a pressure of 20 g / cm. 2 After 100 reciprocating rubs at 100°C, the coating film was dried at room temperature to obtain a test coating film. Except for using this test coating film, the antiviral activity value (durable activity value) was calculated in the same manner as for the initial activity value.

[0123]

[0124] The virus infection inhibitor of the present invention has an excellent virus infection inhibitory effect. By incorporating the virus infection inhibitor into a base material to which a virus infection inhibitory effect is to be imparted, a virus infection inhibitor product having an excellent virus infection inhibitory effect can be produced.

[0125] (Cross-reference to related applications) This application claims priority based on Japanese Patent Application No. 2023-185316, filed on October 30, 2023, the disclosure of which is incorporated herein by reference in its entirety.

Claims

1. A viral infection inhibitor characterized by containing as an active ingredient a viral infection-inhibiting compound having in its molecule an alkoxysilyl structure represented by formula (1) or a silanol structure represented by formula (2), and a structure containing an acidic functional group or an anhydride group thereof. (In the formula (1), R 1 is an alkyl group. In formulas (1) and (2), * denotes a bond and means a single bond.

2. The virus infection inhibitor according to claim 1, characterized in that the virus infection inhibitor compound has a structure represented by formula (3). (In the formula (3), X 1 is a structure containing an acidic functional group or an anhydride group thereof, R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 2 and R 3 may be the same or different. a is an integer from 1 to 20, and b is an integer from 0 to 2.

3. The virus infection inhibitor according to claim 1, characterized in that the virus infection inhibitor compound has a structure represented by formula (4). (In the formula (4), X 2 and X 3 is a structure containing an acidic functional group or an anhydride group thereof, R 4 is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 6 is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms. 7 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; c is 0 or 1; d is an integer from 1 to 100; and e is 0 or 1.

4. The virus infection inhibitor described in claim 1, characterized in that the virus infection inhibitor compound is a chain polymer, and the side chain of the chain polymer has the alkoxysilyl structure or the silanol structure and a structure containing the acidic functional group or its anhydride group.

5. A virus infection inhibitor described in any one of claims 1 to 4, characterized in that the acidic functional group is a carboxy group (-COOH), a sulfo group (sulfonic acid group) (-SO3H), or a phosphonic acid group [-P(=O)(OH)2].

6. A virus infection inhibitor according to any one of claims 1 to 4, characterized in that the acidic functional group is a carboxy group (-COOH).

7. The virus infection inhibitor according to any one of claims 1 to 4, characterized in that the structure containing the acidic functional group or its anhydride group is a carboxy group (-COOH), a succinic acid residue, an anhydride group of a succinic acid residue, a maleic acid residue, an anhydride group of a maleic acid residue, a phthalic acid residue, or an anhydride group of a phthalic acid residue.

8. A virus infection inhibitor solution comprising the virus infection inhibitor according to any one of claims 1 to 4 and a solvent.

9. A virus infection preventing paint comprising the virus infection preventing agent according to any one of claims 1 to 4, a solvent, and a binder resin.

10. A masterbatch for synthetic resin molding, comprising the virus infection inhibitor according to any one of claims 1 to 4 and a synthetic resin.

11. A virus infection preventing product comprising a base material and the virus infection preventing agent according to any one of claims 1 to 4 contained in the base material.

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