Virus infection inhibitor, virus infection-inhibiting liquid, virus infection-inhibiting coating material, master batch for synthetic resin molding, and virus infection-inhibiting product

Abstract

Provided is a virus infection inhibitor which is reduced in detachment from a substrate and which exhibits an excellent virus infection inhibiting effect over a long period of time. The virus infection inhibitor according to the present invention contains, as an active ingredient, a virus infection inhibiting compound that contains, in the molecule, an alkoxysilyl structure or a silanol structure represented by a specific structural formula, and that has an acidic functional group or an acid anhydride group thereof. An excellent virus infection inhibiting effect can be exhibited, shedding from a base material is reduced, and the excellent virus infection inhibiting effect is imparted to the base material for a long period of time.

Description

Technical Field

[0001] This invention relates to virus infection inhibitors, virus infection inhibitory solutions, virus infection inhibitory coatings, synthetic resin molding masterbatches, and virus infection inhibitory products. Background Technology

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

[0003] In addition, it has been confirmed that highly pathogenic avian influenza viruses can mutate and infect humans. Furthermore, the SARS virus, with its extremely high mortality rate, is also a cause for concern, leading to increasing anxiety about viruses.

[0004] Patent document 1 discloses an enveloped virus inactivating agent containing (a) a critical micelle concentration of 0.2 × 10⁻⁶ at 25°C. -3 mol / L or higher and 2.0 × 10 -3 Anionic surfactants with a concentration of less than mol / L and a temperature of less than 5°C, having a sulfonic acid group, a sulfate group, or a salt of these substituents (hereinafter referred to as component (a)) as active ingredients.

[0005] Patent document 2 discloses an enveloped virus inactivator containing (a) an aryl sulfonic acid or its salt, which is optionally substituted with a hydrocarbon group having a number of 1 to 5 carbon atoms of 1 to 3 or more as an active ingredient.

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: Japanese Patent Application Publication No. 2023-110871

[0009] Patent Document 2: Japanese Patent Application Publication No. 2023-70880 Summary of the Invention

[0010] The problem the invention aims to solve

[0011] However, the enveloped virus inactivating agents disclosed in Patent Documents 1 and 2 do not have sufficient inactivation effect on enveloped viruses, and there is a need for a virus infection inhibitor that can exert a superior inactivation effect.

[0012] Furthermore, regarding the enveloped virus inactivating agents of Patent Documents 1 and 2, virus-inactivated products can be manufactured by incorporating them into various articles. Virus-inactivated products typically come into contact with human hands or rub against other objects during use. Therefore, there is a possibility that the virus inactivating agent contained in the product may detach, leading to a temporary decrease in the virus inactivation effect.

[0013] This invention provides a virus infection inhibitor that can reduce detachment from the substrate and exert excellent virus infection inhibition effect over a long period of time, as well as a virus infection inhibition liquid, a virus infection inhibition coating, a synthetic resin molding masterbatch, and a virus infection inhibition article using the virus infection inhibitor.

[0014] Problem Solving Methods

[0015] The viral infection inhibitor of the present invention comprises a viral infection inhibitory compound as an active ingredient, which has an alkoxysilyl structure as shown in formula (1) or a silanol structure as shown in formula (2) in the molecule, and has a structure containing an acidic functional group or an anhydride group thereof.

[0016] [Chemical Formula 1]

[0017]

[0018] Wherein, R in equation (1) 1 It is an alkyl group. In formulas (1) and (2), * represents a bond arm and a single bond.

[0019] The virus infection inhibitor solution of the present invention comprises the above-mentioned virus infection inhibitor and solvent.

[0020] The virus infection inhibitory coating of the present invention comprises the above-mentioned virus infection inhibitor, solvent and binder resin.

[0021] The synthetic resin molding masterbatch of the present invention comprises the above-mentioned virus infection inhibitor and synthetic resin.

[0022] The effects of the invention

[0023] The viral infection inhibitor of the present invention exhibits excellent viral infection inhibition effect because it contains a viral infection inhibitory compound having an alkoxysilyl or silanol structure in the molecule and having a structure containing an acidic functional group or its anhydride group as the active ingredient.

[0024] The alkoxysilyl or silanol structure of the virus infection inhibitor of the present invention can form a strong bond with the substrate, thereby reducing detachment from the substrate and endowing the substrate with excellent virus infection inhibition effect over a long period of time. Detailed Implementation

[0025] In the numerical ranges described in stages in this specification, the upper or lower limit of a certain stage's numerical range can be arbitrarily combined with the upper or lower limits of other stages' numerical ranges. The upper or lower limit of the numerical range described in this specification can also be replaced with the values ​​shown in the embodiments or values ​​that can be unambiguously derived from the embodiments. In this specification, numerical values ​​connected by "~" refer to a numerical range including the values ​​before and after "~" as both the lower and upper limits.

[0026] [Viral infection inhibitory compounds]

[0027] Viral infection inhibitors contain a viral infection inhibitory compound as the active ingredient. This viral infection inhibitory compound has, in its molecule, an alkoxysilyl structure as shown in formula (1) (hereinafter sometimes simply referred to as the "alkoxysilyl structure") or a silanol structure as shown in formula (2) (hereinafter sometimes simply referred to as the "silanol structure"), and a structure containing an acidic functional group or its anhydride group. It should be noted that the viral infection inhibitory compound can be used alone or in combination of two or more. In formula (1), R... 1 It is an alkyl group. In this specification, * represents a bond arm and indicates a single bond.

[0028] [Chemical Formula 2]

[0029]

[0030] (wherein, in equation (1), R) 1 It is an alkyl group. In formulas (1) and (2), * represents a bond arm and a single bond.

[0031] The content of the viral infection inhibitory 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.

[0032] Viral infection inhibitors exert excellent antiviral infection effects by containing the aforementioned antiviral infection compounds.

[0033] Here, viral infection inhibition refers to the elimination or reduction of viral infectivity to cells, or the inability to proliferate in cells even if infected. Methods for confirming the infectivity of such viruses include, for example, ISO 18184 and JIS L1922 for textile products, and ISO 21702 for plastics and non-porous surfaces. Other methods include the plaque assay and hemagglutination titer (HAU) assay described in "Medical / Pharmaceutical Virology" (first edition, April 1990).

[0034] The viral infection inhibition effect of the viral infection inhibitor can be determined, for example, according to the following points. A viral infection inhibitor coating is prepared by mixing 5 parts by weight of the viral infection inhibitor compound with 95 parts by weight of a UV-curable acrylic coating. Using a wire-bar coater #8, the viral infection inhibitor coating is applied to a polyethylene film to a thickness of 18 μm to form a coating layer.

[0035] The coating layer was applied at 25°C to achieve a cumulative light intensity of 500 mJ / cm². 2 The UV-curable acrylic coating is cured by irradiating it with ultraviolet light of 365nm wavelength to form a coating film with a thickness of 18μm.

[0036] Test pieces were prepared by cutting out planar squares with sides of 5.0 cm from the coating. The surface of the coating on the test piece was then wiped with a planar square of nonwoven fabric with sides of 10 cm, and the nonwoven fabric was moved back and forth 10 times to obtain the test coating.

[0037] The obtained test coatings were subjected to antiviral testing according to ISO 21702. For the resulting viral suspension, the viral infection titer (commonly logarithmic value) of the test coatings was calculated using the plaque method (PFU / cm³). 2 ).

[0038] Except for the absence of viral infection inhibitors, a blank coating was prepared following the same points as described above. Based on this blank coating, the viral infection titer (commonly logarithmic value) (PFU / cm³) was calculated following the same points as described above. 2 ).

[0039] The antiviral activity value is calculated by subtracting the viral infection titer of the test coating from the viral infection titer of the blank coating.

[0040] In addition, a viral infection inhibitor containing 5 parts by mass of a viral infection inhibitory compound was melt-blended with 95 parts by mass of a synthetic resin to produce a resin composition. This resin composition was then pressed to produce a sheet-like synthetic resin molded article with an average thickness of 1 mm. The surface of the resulting synthetic resin molded article was wiped with a non-woven fabric in a planar square shape with a side length of 10 cm, and this synthetic resin molded article served as the test subject. A blank reference body was prepared according to the same principles as described above, except that it did not contain a viral infection inhibitor. Alternatively, the test subject and blank reference body could be used instead of the test coating and blank coating, and the antiviral activity value was calculated according to the same principles as described above.

[0041] Regarding antiviral inhibitors, the antiviral activity value after 24 hours from the start of the reaction, according to the antiviral test of ISO 21702, is preferably 2.0 or higher, more preferably 2.5 or higher, and even more preferably 2.8 or higher. Regardless of the type of virus being evaluated, it is preferable that the antiviral activity value is 2.0 or higher in at least one virus.

[0042] An alkoxysilyl structure refers to a structure formed by directly bonding an alkoxy group to a silicon atom as shown in formula (1). An alkoxy group is a group in which the hydrogen atom of a hydroxyl group (-OH) is replaced by an alkyl group. An alkyl group is a group of atoms remaining after removing one hydrogen atom from an aliphatic saturated hydrocarbon, and can be in any form, either linear or branched. Preferably, the hydrogen atom of the alkyl group is not replaced. There are no particular limitations on the alkoxy group; examples include alkoxy groups with 1 to 5 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, and pentoxy. The alkoxy group is preferably methoxy or ethoxy, more preferably ethoxy.

[0043] The silanol structure refers to the structure formed by the direct bonding of hydroxyl groups (-OH) to silicon atoms as shown in formula (2).

[0044] Virus infection inhibitory compounds, by having an alkoxysilyl structure as shown in formula (1) or a silanol structure as shown in formula (2) in their molecules, can form a strong bond between the virus infection inhibitory compound and the substrate, reducing the detachment of the virus infection inhibitor from the substrate and endowing the substrate with excellent virus infection inhibition effect over a long period of time. The alkoxysilyl structure shown in formula (1) can be hydrolyzed as needed by moisture contained in the substrate or air to generate the silanol structure shown in formula (2), and a strong bond is formed between the compound and the substrate through the generated silanol structure.

[0045] In addition, although the virus infection inhibitory compound has the alkoxysilyl structure shown in formula (1) or the silanol structure shown in formula (2), it does not affect the virus infection inhibitory effect of the acidic functional group or its anhydride group described later. The virus infection inhibitor exhibits excellent virus infection inhibitory effect.

[0046] Virus infection inhibitory compounds have structures containing acidic functional groups or their anhydride groups. These compounds exhibit excellent antiviral infection effects based on their acidic functional groups or their anhydride groups.

[0047] An acidic functional group is a functional group that can release hydrogen ions (protons) in aqueous solution. The acidic functional group is preferably an H-type acidic functional group. Examples of acidic functional groups include carboxyl groups (-COOH), sulfonyl groups (-SO3H), and phosphonic acid groups [-P(=O)(OH)2], with carboxyl groups (-COOH) being preferred. This is because the carboxyl group (-COOH) exhibits excellent antiviral infection effects without significantly hindering the binding effect of the alkoxysilyl group and silanol group on the substrate.

[0048] The structure containing acidic functional groups is preferably a structure containing a carboxyl group (-COOH), a sulfonyl group (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], more preferably a structure containing a carboxyl group (-COOH), even more preferably a structure containing a carboxyl group (-COOH), the structure shown in formula (5-1) below (succinic acid residue), the structure shown in formula (5-2) below (phthalic acid residue), or the structure shown in formula (5-3) below (maleic acid residue), even more preferably a carboxyl group (-COOH) or the structure shown in formula (5-1) (succinic acid residue). These structures can maintain excellent adhesion to the substrate based on alkoxysilyl and silanol structures while enabling the virus infection inhibitor to further exhibit excellent virus infection inhibition effects.

[0049] In formulas (5-1) to (5-3), one of the two carboxyl groups (-COOH) can undergo esterification to form -COOR. 9 R 9 Preferably, the alkyl group is an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and most preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group is not particularly limited, and examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc., with methyl or ethyl being preferred, and ethyl being more preferred. The alkyl group can be in any form, either straight-chain or branched. Preferably, the hydrogen atoms of the alkyl group are not substituted.

[0050] [Chemical Formula 3]

[0051]

[0052] The acidic functional group can also be an anhydride group. The anhydride group reacts with the substrate or moisture in the air and hydrolyzes to generate the acidic functional group, thereby exhibiting an inhibitory effect on viral infection. The anhydride group of the acidic functional group is preferably a carboxyl anhydride group (*-CO-O-CO-*). It should be noted that the * at both ends of the anhydride group represents a bonding arm and a single bond.

[0053] The anhydride group of the acidic functional group is preferably, for example, the structure shown in (6-1) below (an anhydride group of succinic acid residue), the structure shown in (6-2) below (an anhydride group of phthalic acid residue), or the structure shown in (6-3) below (an anhydride group of maleic acid residue), and more preferably the structure shown in (6-1) (an anhydride group of succinic acid residue). The structures shown in formulas (6-1) to (6-3) can maintain excellent adhesion to the substrate based on the alkoxysilyl structure and the silanol structure, while enabling the virus infection inhibitor to exhibit a superior virus infection inhibition effect.

[0054] [Chemical Formula 4]

[0055]

[0056] Regarding the number of acidic functional groups in the viral infection inhibitory compound, multiple (two or more) are preferred for improving the viral infection inhibitor's inhibitory effect. When the viral infection inhibitory compound has multiple acidic functional groups, the acidic functional groups may be of the same type or may include different types of acidic functional groups. Since the proton-releasing ability of the acidic functional groups in the viral infection inhibitory compound can be fully utilized to improve the viral infection inhibitor's inhibitory effect, it is preferable that only the same type of acidic functional group is present, and more preferably only a carboxyl group (-COOH).

[0057] Regarding viral infection inhibitory compounds, although not explicitly stated, it can be assumed that the alkoxysilyl structure or the aforementioned silanol structure is strongly bonded to the substrate and that the acidic functional groups are positioned externally to effectively capture viruses, thereby enhancing the interaction with viruses and thus enabling the viral infection inhibitor to exert excellent viral infection inhibitory effects.

[0058] As a viral infection inhibitory compound, it is preferred to have a compound having the structure shown in formula (3) or formula (4).

[0059] [Chemical Formula 5]

[0060]

[0061] The viral infection inhibitory compound represented by formula (3) will be described. In formula (3), X 1 The structure contains an acidic functional group or its anhydride group. The acidic functional group is preferably a carboxyl group (-COOH), a sulfonyl group (-SO3H), or a phosphonic group [-P(=O)(OH)2], and more preferably a carboxyl group (-COOH).

[0062] In equation (3), since it will enhance the viral infection suppression effect of the viral infection inhibitor, therefore X 1Preferably, it contains an acidic functional group selected from carboxyl (-COOH), sulfonyl (sulfonic acid group) (-SO3H) and phosphonic acid group [-P(=O)(OH)2] or an anhydride group of such functional group, more preferably a structure containing carboxyl (-COOH) or an anhydride group of carboxyl (-CO-O-CO-), more preferably a carboxyl (-COOH), succinic acid residue [Formula (5-1)] or an anhydride group of succinic acid residue [Formula (6-1)], more preferably a succinic acid residue [Formula (5-1)] or an anhydride group of succinic acid residue [Formula (6-1)].

[0063] In equation (3), R 2 and R 3 Each alkyl group is independently composed of hydrogen atoms or 1 to 10 carbon atoms, preferably alkyl groups with 1 to 5 carbon atoms, more preferably alkyl groups with 1 to 3 carbon atoms. The alkyl group is not particularly limited, and examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc., preferably methyl or ethyl, more preferably ethyl. The alkyl group can be in any form, either straight-chain or branched. Preferably, the hydrogen atoms of the alkyl group are not substituted. 2 Preferably, it contains hydrogen atoms. R 3 Preferably, it is 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.

[0064] In equation (3), a is an integer from 1 to 20. Since it will improve the viral infection suppression effect of the viral infection inhibitor, a is preferably 1 to 10, more preferably 2 to 8, and even more preferably 3 to 6.

[0065] In equation (3), b is an integer from 0 to 2. Since it can further reduce the shedding of virus infection inhibitors from the substrate and impart excellent virus infection inhibition effect to the substrate for a longer period of time, b is preferably 0 or 1, more preferably 0.

[0066] As the virus infection inhibitory compound represented by formula (3), it is preferably the compound represented by formula (3-1) below or its anhydride [formula (3-2)], more preferably the compound represented by formula (3-3) below or its anhydride [formula (3-4)], and even more preferably 3-trimethoxysilylpropylsuccinic acid [in formula (3-3), R 3 [Methyl] or its anhydride [in formula (3-4), R] 3 [Methyl] or 3-triethoxysilylpropylsuccinic acid [in formula (3-3), R] 3 [Ethyl] or its anhydride [in formula (3-4), R] 3 [Ethyl]. It should be noted that in formulas (3-1) to (3-4), a and R 3 The same as those described in equation (3).

[0067] [Chemical Formula 6]

[0068]

[0069] The virus infection inhibitory compound shown in formula (4) will be described.

[0070] [Chemical Formula 7]

[0071]

[0072] In equation (4), X 2 and X 3 Each of these structures independently comprises an acidic functional group or its anhydride group. Preferably, the acidic functional group is a carboxyl group (-COOH), a sulfonyl group (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], more preferably a carboxyl group (-COOH). It should be noted that X 2 and X 3 They can be the same or different.

[0073] In equation (4), since it will enhance the viral infection suppression effect of the viral infection inhibitor, therefore X 2 and X 3 Preferably, the structure contains an acidic functional group selected from carboxyl (-COOH), sulfonyl (sulfonic acid group) (-SO3H) and phosphonic acid group [-P(=O)(OH)2], or an anhydride group of the acidic functional group; more preferably, the structure contains a carboxyl (-COOH) or an anhydride group of the carboxyl (-CO-O-CO-); even more preferably, the structure contains a succinic acid residue [Formula (5-1)] or an anhydride group containing a succinic acid residue [Formula (6-1)].

[0074] In equation (4), R 4 It 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, preferably a hydroxyl group or an alkyl group having 1 to 3 carbon atoms. R 5 It is an alkyl group having 1 to 10 hydrogen atoms or carbon atoms, preferably an alkyl group having 1 to 5 hydrogen atoms or carbon atoms, and more preferably an alkyl group having 1 to 3 hydrogen atoms or carbon atoms. R 6 It 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, preferably a hydroxyl group or an alkyl group having 1 to 3 carbon atoms. R 7 It is an alkyl group having 1 to 10 hydrogen atoms or carbon atoms, preferably an alkyl group having 1 to 5 hydrogen atoms or carbon atoms, and more preferably an alkyl group having 1 to 3 hydrogen atoms or carbon atoms. R 4 R 5 R 6 and R 7In this context, the alkyl group is not particularly limited, and examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl, with methyl or ethyl being preferred, and ethyl being more preferred. The alkyl group can be in any form, either straight-chain or branched. Preferably, the hydrogen atoms of the alkyl group are not substituted. 4 R 5 R 6 and R 7 When any of the components are alkyl groups, they can be the same or different. Because it can further reduce the detachment of virus infection inhibitors from the substrate and impart excellent virus infection inhibition effects to the substrate for a longer period, R... 4 and R 6 Preferably, it contains hydroxyl groups. Because it can further reduce the shedding of viral infection inhibitors from the substrate and impart excellent viral infection inhibition to the substrate for a longer period, R... 5 and R 7 Hydrogen atoms are preferred.

[0075] In equation (4), c is 0 or 1. Since it can further reduce the shedding of virus infection inhibitors from the substrate and impart excellent virus infection inhibition effect to the substrate for a longer period of time, it is preferred to be 0.

[0076] In equation (4), e is 0 or 1. Since it can further reduce the shedding of virus infection inhibitors from the substrate and impart excellent virus infection inhibition effect to the substrate for a longer period of time, it is preferred to be 0.

[0077] In equation (4), d is an integer from 1 to 100. Since it can further reduce the shedding of the virus infection inhibitor from the substrate and impart excellent virus infection inhibition effect to the substrate for a longer period of time, it is more preferably 1 to 80, and more preferably 1 to 40.

[0078] As the viral infection inhibitory compound represented by formula (4), the preferred compound is the one represented by formula (4-1a) or formula (4-1b), and more preferably the one represented by formula (4-2a) or formula (4-2b). It should be noted that in formulas (4-1a) and (4-1b), R... 4 ~R 7 And d are the same as those described in equation (4).

[0079] [Chemical Formula 8]

[0080]

[0081] In formulas (4-1a) and (4-1b), s is an integer from 1 to 20. Since it can further reduce the shedding of viral infection inhibitors from the substrate and impart excellent viral infection inhibition effect to the substrate for a longer period of time, s is preferably an integer from 1 to 7, and more preferably an integer from 1 to 5.

[0082] In formulas (4-1a) and (4-1b), q is an integer from 1 to 20. Since it can further reduce the shedding of viral infection inhibitors from the substrate and impart excellent viral infection inhibition effect to the substrate for a longer period of time, q is preferably an integer from 1 to 7, and more preferably an integer from 1 to 5.

[0083] Virus infection inhibitory compounds can also be polymeric compounds. Preferably, the virus infection inhibitory compounds are chain polymers, and the side chains of the chain polymers have alkoxysilyl or silanol structures, and acidic functional groups or their anhydride groups.

[0084] If the virus infection inhibitory compound is a chain polymer and has an alkoxysilyl or silanol structure and an acidic functional group or an anhydride group on its side chain, it can be contained in the substrate with the alkoxysilyl or silanol structure and the acidic functional group or anhydride group arranged along the main chain, thereby imparting excellent virus infection inhibitory effect to the substrate while forming a strong bond with it. The acidic functional group is preferably a carboxyl group (-COOH), a sulfonyl group (-SO3H), or a phosphonic acid group [-P(=O)(OH)2], more preferably a carboxyl group (-COOH).

[0085] As an acidic functional group or its anhydride group, since it can enhance the antiviral effect of the viral infection inhibitor, it is preferred to have a structure containing an acidic functional group selected from carboxyl (-COOH), sulfonyl (sulfonic acid group) (-SO3H) and phosphonic acid group [-P(=O)(OH)2] or an anhydride group of such functional group, more preferably a structure containing carboxyl (-COOH) or an anhydride group of carboxyl (-CO-O-CO-), more preferably a carboxyl (-COOH), succinic acid residue [Formula (5-1)] or an anhydride group of succinic acid residue [Formula (6-1)], more preferably an anhydride group of succinic acid residue [Formula (5-1)] or an anhydride group of succinic acid residue [Formula (6-1)].

[0086] As a viral infection inhibitory compound that is a chain-like polymer, it is more preferably a polymer represented by formula (7-1) or formula (7-2).

[0087] In equations (7-1) and (7-2), n is the number of repeating units, an integer from 1 to 1000; m is the number of repeating units, an integer from 1 to 1000; and p is the number of repeating units, an integer from 1 to 1000. R 8The alkyl group is an alkyl group having 1 to 10 hydrogen atoms or carbon atoms, preferably an alkyl group having 1 to 5 hydrogen atoms or carbon atoms, and more preferably an alkyl group having 1 to 3 hydrogen atoms or carbon atoms. There is no particular limitation on the alkyl group; examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc., preferably methyl or ethyl, more preferably ethyl. The alkyl group can be in any form, either straight-chain or branched. Preferably, the hydrogen atoms of the alkyl group are not substituted. In formulas (7-1) and (7-2), -Si(OR) 8 The 3-base group is bonded to the carbon atoms of the main chain through chain polymers (e.g., vinyl polymers, polyoxyethylene, polyurethane, polyester, etc.).

[0088] When the virus infection inhibitory compound is a chain polymer, its number-average molecular weight is preferably 100,000 or less, more preferably 50,000 or less, and even more preferably 10,000 or less. When the virus infection inhibitory compound is a chain polymer, its number-average molecular weight is preferably 1,000 or more, more preferably 2,000 or more, and even more preferably 5,000 or more. If the number-average molecular weight of the chain polymer is 100,000 or less, the aggregation of the virus infection inhibitory compound can be suppressed, increasing the surface area and facilitating contact with the virus, thereby improving the virus infection inhibitory effect. If the number-average molecular weight of the chain polymer is 1,000 or more, the virus infection inhibitory compound and the virus can be adsorbed at multiple points, thus improving the virus infection inhibitory effect.

[0089] [Chemical Formula 9]

[0090]

[0091] Regarding the pH of a 0.5% by mass aqueous solution of the virus infection inhibitory compound at 25°C, a pH of 4.5 or lower is preferred because it easily maintains the acidity of the acidic functional groups of the virus infection inhibitory compound and improves the virus infection inhibitory effect. The pH of a 0.5% by mass aqueous solution of the virus infection inhibitory compound refers to the pH value of an aqueous solution prepared by adding 0.5g of the virus infection inhibitory compound to 99.5g of purified water and mixing them uniformly at 25°C. When the concentration of the saturated aqueous solution of the virus infection inhibitory compound at 25°C is less than 0.5% by mass, it refers to the pH of a suspension at 25°C containing 0.5 parts by mass of the virus infection inhibitory compound and 99.5 parts by mass of water, where the virus infection inhibitory compound is dissolved in water to reach saturation.

[0092] When the viral infection inhibitory compound does not contain repeating units, the molecular weight of the viral infection inhibitory 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. If the molecular weight of the viral infection inhibitory compound is 1000 or less, the viral infection inhibitory effect is improved.

[0093] The pKa1 of the viral infection inhibitory 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. If the pKa1 of the viral infection inhibitory compound is 4.5 or less, the viral infection inhibitory effect is improved.

[0094] When the virus infection inhibitory compound is a polybasic acid, its ionization occurs in multiple stages, and pKa1 refers to the pKa calculated based on the ionization constant of the first stage. Here, the electrolyte HA ionizes into H+. + and A - When ionization equilibrium is achieved (A), the acid dissociation constant Ka is defined by equation (B), and pKa is defined by the negative common logarithm of the acid dissociation constant Ka (C).

[0095] [Mathematical Expression 1]

[0096]

[0097] The pKa1 of a viral infection inhibitory compound is a value determined by titration. Specifically, the pKa1 can be calculated by titrating the viral infection inhibitory compound with sodium hydroxide at 25°C and measuring the pH at 25°C at the half-equivalence point (the point where half the amount of neutralized compound has been added).

[0098] The amount of acidic functional groups in the viral infection inhibitory 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. If the amount of acidic functional groups in the viral infection inhibitory compound is 3 mmol / g or more, the viral infection inhibitory effect is improved.

[0099] It should be noted that the amount of acidic functional groups in the virus infection inhibitory compound refers to the value measured by titration. Specifically, approximately 1 g (W1 g) of the dried virus infection inhibitory compound is accurately weighed, 200 mL of purified water is added to the compound, and titration is performed using a 0.1 mol / L sodium hydroxide aqueous solution at 25 °C. The amount of sodium hydroxide aqueous solution consumed (W2 mL) up to the half-equivalence point (the point where half of the neutralized amount has been added) is calculated, and the amount of acidic functional groups in the virus infection inhibitory compound (mmol / g) is calculated using the following formula.

[0100] Acidic functional group content (mmol / g) = 0.1 × W1 / W2

[0101] The solubility of the virus infection inhibitory 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 even more preferably 20 g / L or less. If the solubility of the virus infection inhibitory compound in water at 25°C is 500 g / L or less, then the virus infection inhibitory compound has a higher affinity for the virus than for water, and the virus infection inhibitory effect is improved.

[0102] It should be noted that the solubility of the virus infection inhibitory compound in water at 25°C refers to the mass (g) of the virus infection inhibitory compound in a saturated aqueous solution obtained by dissolving the virus infection inhibitory compound in 1 L of water. The solubility of the virus infection inhibitory compound in water at 25°C is the value measured at 25°C according to OECD Chemicals Testing Guide No. 105 (Water Solubility).

[0103] [Viral infection inhibitor]

[0104] Viral infection inhibitors contain viral infection-inhibiting compounds as active ingredients. There are no particular limitations on the manufacturing method of viral infection inhibitors; they can be manufactured by mixing common additives with viral infection-inhibiting compounds according to general principles.

[0105] Next, we will explain the key points for using the aforementioned viral infection inhibitors. Viral infection inhibitors exert their inhibitory effect on various viruses through the action of viral infection-inhibiting compounds, exhibiting excellent inhibitory effects on both enveloped and non-enveloped viruses.

[0106] Examples of enveloped viruses include: influenza viruses (e.g., influenza A, influenza B, etc.), rubella virus, Ebola virus, coronaviruses [e.g., SARS virus, novel coronavirus (SARS-CoV-2)], measles virus, varicella-zoster virus, herpes simplex virus, mumps virus, arbovirus, RS virus, hepatitis viruses (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever virus, HIV, rabies virus, Hantavirus, dengue virus, Nipah virus, Lyssa virus, etc.

[0107] Examples of non-enveloped viruses include: feline calicivirus, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, Coxsackievirus, human parvovirus, encephalomyelitis virus, rhinovirus, etc.

[0108] Viral infection inhibitors can be incorporated into a substrate to which a viral infection inhibition effect is desired, thus constituting a viral infection inhibition article. The substrate containing the viral infection inhibitor, as a viral infection inhibition article, exhibits a viral infection inhibition effect. The manner in which the viral infection inhibitor is incorporated into the substrate is not particularly limited; examples include: mixing the viral infection inhibitor into the substrate, attaching the viral infection inhibitor to the surface of the substrate, and incorporating the viral infection inhibitor into the substrate. Because viral infection inhibitors have excellent adhesion to substrates, they exhibit particularly superior effects when attached to the surface of the substrate.

[0109] A viral infection inhibitor solution is prepared by dissolving or dispersing a viral infection inhibitor in a solvent, and then applied to a substrate, thereby allowing the viral infection inhibitor to adhere to the substrate surface. It should be noted that additives such as water-based solvents, oils, emulsions, and suspending agents can also be added to the viral infection inhibitor solution as needed.

[0110] It should be noted that, for example, the solvents mentioned above include: water (preferably ion-exchanged water), alcohols (methanol, ethanol, propanol, etc.), hydrocarbons (toluene, xylene, methylnaphthalene, kerosene, cyclohexane, etc.), and ethers (diethyl ether, tetrahydrofuran, diethyl ether ... Alkane, ketones (acetone, methyl ethyl ketone, etc.), amides (N,N-dimethylformamide, etc.), preferably water or alcohol.

[0111] The content of the viral infection inhibitor in 100% by mass of the viral infection inhibitor solution is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more. The content of the viral infection inhibitor in 100% by mass of the viral infection inhibitor solution is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

[0112] As a substrate to contain viral infection inhibitors, there are no particular limitations as long as it can contain viral infection inhibitors. Examples include: synthetic resin molded bodies, coatings, wallpaper, decorative sheets, flooring materials, fibers, fiber products (fabricated fabrics, non-woven fabrics, woven fabrics), interior products and interior materials for transportation vehicles (such as cars, airplanes, ships, etc.) (seats, child seats and the foams that make them up), kitchenware, baby products, building interior materials, etc.

[0113] The synthetic resins constituting the molded synthetic resin body are not particularly limited, but can include, for example: thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefins, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyetheretherketone, thermoplastic polyimide, polyamide-imide, etc.), and thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea-formaldehyde resin, unsaturated polyester resin, alkyd resin, silicone resin, polyurethane, thermosetting polyimide, etc.). It should be noted that synthetic resins can be used alone or in combination of two or more.

[0114] Viral infection inhibitors can be compounded into synthetic resins for use. Even when compounded with viral infection inhibitors, the inhibitors exhibit excellent adhesion to the synthetic resin on the surface of the resulting molded article, maintaining excellent viral infection inhibition effects for a long period. One method for compounding viral infection inhibitors into synthetic resins is to mix the inhibitors with the synthetic resin used as a raw material to prepare a resin composition, and then use this resin composition to obtain a viral infection inhibitor article of the desired shape using a common synthetic resin molding method. Examples of common synthetic resin molding methods include extrusion molding, injection molding, and blow molding. Alternatively, a synthetic resin and a viral infection inhibitor can be mixed to prepare a synthetic resin molding masterbatch, which can then be mixed with the synthetic resin used as a raw material and molded using a common synthetic resin molding method to manufacture a viral infection inhibitor article.

[0115] 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 even 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 even more preferably 10% by mass or less.

[0116] The content of virus infection inhibitor in 100% by mass of synthetic resin molding masterbatch is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 50% by mass or more. The content of virus infection inhibitor in 100% by mass of synthetic resin molding masterbatch is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.

[0117] Virus infection inhibitors can be bonded to fibers, which serve as substrates, and thus contained within the fibers. A method for bonding a virus infection inhibitor to a fiber will be described. Examples of methods for bonding a virus infection inhibitor to a fiber include: (1) dissolving or dispersing a virus infection inhibitor in a solvent to prepare a virus infection inhibitor solution, and then impregnating the fiber with the virus infection inhibitor solution; (2) coating or spraying the aforementioned virus infection inhibitor solution onto the surface of the fiber; (3) impregnating the fiber with an adhesive resin formed by dissolving or dispersing the aforementioned virus infection inhibitor, thereby bonding the virus infection inhibitor to the fiber through the adhesive resin; (4) coating or spraying the adhesive resin formed by dissolving or dispersing the aforementioned virus infection inhibitor onto the surface of the fiber, thereby bonding the virus infection inhibitor to the fiber through the adhesive resin, etc. It should be noted that in methods (1) and (2) above, the virus infection inhibitor solution may also contain an adhesive resin. The solvent is the same as described above, therefore, the description is omitted.

[0118] As an adhesive resin, there is no particular limitation as long as it can bond the viral infection inhibitor to the fiber surface. Examples of adhesive resins include: one-component urethane resins, two-component urethane resins and other urethane resins, silicone resins, acrylic resins, urethane acrylate resins, polyester resins, unsaturated polyester resins, alkyd resins, vinyl acetate resins, vinyl chloride resins, epoxy resins, epoxy acrylate resins and other adhesive resins, with urethane resins being preferred.

[0119] As coatings, conventionally known coatings can be used, such as oil-based coatings (e.g., varnishes, oil-based varnishes, etc.), cellulose coatings, synthetic resin coatings, etc. Coatings also include photocurable coatings that polymerize and form binder resin components when exposed to radiation such as ultraviolet light.

[0120] Coatings generally contain binder resins and solvents. The binder resins and solvents are the same as those mentioned above, so descriptions are omitted. Coatings may also contain additives such as pigments, plasticizers, curing agents, thickeners, fillers, anti-aging agents, thickeners, and surfactants, to a extent that does not impair their physical properties. It should be noted that, as a method for producing a virus-inhibiting coating by containing a virus infection inhibitor, examples include: supplying the virus infection inhibitor and the coating to a dispersion device and mixing them until homogeneous. It should be noted that examples of dispersion devices include, for example, high-speed mills, ball mills, and sand mills.

[0121] The content of the virus infection inhibitor in 100% by mass of the virus infection inhibitor coating is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more. The content of the virus infection inhibitor in 100% by mass of the virus infection inhibitor coating is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

[0122] There are no specific limitations on interior building materials; examples include flooring materials, wallpaper, ceiling materials, paint, door handles, switches, switch covers, wax, etc.

[0123] There are no specific limitations on vehicle interior products and materials, but examples include: seats, child seats, seat belts, car floor mats, seat covers, doors, headliner materials, floor mats, door panels, dashboards, consoles, glove boxes, grab handles, armrests, etc.

[0124] Example

[0125] The present invention will be described in more detail below using examples, but the present invention is not limited thereto. The specific numerical values ​​such as proportions (including proportions), physical property values, and parameters used in the following description can be replaced with the corresponding upper limit values ​​(defined in the form of "below" or "less than") or lower limit values ​​(defined in the form of "above" or "more than") of the proportions (including proportions), physical property values, and parameters described in the "Method for Solving the Problem" and "Detailed Embodiments" sections.

[0126] The following compounds were prepared as viral infection inhibitory compounds that are effective components for inhibiting viral infection.

[0127] [Viral infection inhibitory compounds]

[0128] ·3-Trimethoxysilylpropylsuccinic anhydride [in formula (3-4), R 3 [Methyl] (manufactured by Shin-Etsu Chemical Co., Ltd., trade name "X-12-967C")

[0129] ·3-Trimethoxysilylpropylsuccinic acid [in formula (3-3), R 3 [Methyl]

[0130] ·3-Triethoxysilylpropylsuccinic anhydride [in formula (3-4), R 3 [Ethyl]

[0131] ·3-Triethoxysilylpropylsuccinic acid [in formula (3-3), R 3 [Ethyl]

[0132] [Chemical Formula 10]

[0133]

[0134] The compound shown in formula (4-2)

[0135] [Chemical Formula 11]

[0136]

[0137] A mixture of 55% by mass of 2-[3-triethoxysilylpropyl]succinate monoethyl ester [Formula (8-1)] and 45% by mass of 3-[3-triethoxysilylpropyl]succinate monoethyl ester [Formula (8-2)].

[0138] [Chemical Formula 12]

[0139]

[0140] [Other compounds]

[0141] ·Succinic acid

[0142] Phthalic acid

[0143] Citric acid

[0144] Salicylic acid

[0145] For the virus infection inhibitory compounds, the molecular weight, pKa1 at 25°C, pH of a 0.5% (w / w) aqueous solution at 25°C, solubility in water at 25°C, and amount of acidic functional groups were determined according to the above criteria, and the results are shown in Table 1. It should be noted that in the table, "pKa1 at 25°C", "pH of a 0.5% (w / w) aqueous solution at 25°C", "solubility in water at 25°C", and "acidic functional group amount" are respectively denoted as "pKa1", "pH", "solubility", and "acidic functional group amount". In the table, "<X" (X is a numerical value) means "less than X". In the table, ">X" (X is a numerical value) means "greater than X".

[0146] (Examples 1-6 and Comparative Examples 1-4)

[0147] Virus infection inhibitors containing 100% by mass of the virus infection inhibitory compounds shown in Table 1 as active ingredients were prepared. It should be noted that, for ease of explanation, the compounds of Comparative Examples 1-4 are described in the "Virus Infection Inhibitory Compounds" column.

[0148] [Antiviral test]

[0149] The antiviral activity values ​​were determined according to the following criteria, and the results are shown in Table 1.

[0150] (Initial activity value)

[0151] A virus infection inhibitor was prepared by mixing 10 parts by weight of a virus infection inhibitor with 90 parts by weight of a UV-curable acrylic coating (trade name "AI-N2" manufactured by COAT TECH). The virus infection inhibitor coating was applied to a polyethylene film with a thickness of 18 μm using a wire bar coater #8, forming a coating layer.

[0152] Using a UV transmission device (EYE GRAPHICS "ECS301G1"), the coating layer was subjected to light at 25°C to achieve a cumulative light intensity of 500 mJ / cm². 2 The UV-curable acrylic coating was cured by irradiating it with ultraviolet light of 365nm wavelength, forming a test coating film with a thickness of 18μm.

[0153] Antiviral tests were conducted on the obtained test coatings according to ISO 21702. For the viral suspension that had been in place for 24 hours since the start of the reaction, the viral infection titer of the test coatings (commonly logarithmic value) was calculated using the plaque method.

[0154] Except for the absence of viral infection inhibitors, a blank coating was prepared according to the same criteria as described above. Based on this blank coating, the viral infection titer (common logarithmic value) (PFU / cm³) was calculated according to the same criteria as described above. 2 The viral infection titer (commonly logarithmic value) of the blank coating was 6.5 PFU / cm³. 2 .

[0155] The antiviral activity value (initial activity value) was calculated by subtracting the viral infection titer of the test coating from the viral infection titer of the blank coating.

[0156] (Activeness value after durability test)

[0157] The virus infection inhibitory coating was prepared according to the same criteria as when determining the initial activity value, and the UV-curable acrylic coating was cured to form a coating film with a thickness of 18 μm.

[0158] 0.5 mL of purified water (25°C) was poured into a 6 cm square piece of cotton cloth [according to the test cloth provided with JIS L0803 (Kanakin No. 3)]. The cotton cloth was then placed on the friction head of a Type I friction testing machine (manufactured by Imoto Co., Ltd.). A friction test was performed at 20 g / cm². 2 After applying pressure to the surface of the resulting coating and rubbing it back and forth 100 times, the coating was dried at room temperature to produce a test coating. In addition to using this test coating, the antiviral activity value (durable activity value) was calculated according to the same criteria as the initial activity value.

[0159]

[0160] Industrial applicability

[0161] The viral infection inhibitor of the present invention has excellent viral infection inhibition effect. By incorporating the viral infection inhibitor into a substrate to which the viral infection inhibition effect is desired, a viral infection inhibition article with excellent viral infection inhibition effect can be manufactured.

[0162] (Cross-reference to related applications)

[0163] 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 comprising a viral infection inhibitory compound as an active ingredient, said viral infection inhibitory compound having an alkoxysilyl structure as shown in formula (1) or a silanol structure as shown in formula (2) in the molecule, and having a structure containing an acidic functional group or an anhydride group thereof. ， in, R in equation (1) 1 It is an alkyl group, and * in formulas (1) and (2) are all bonding arms and represent single bonds.

2. The viral infection inhibitor according to claim 1, wherein, The virus infection inhibitory compound has the structure shown in formula (3). ， In equation (3), X 1 For structures containing acidic functional groups or their anhydride groups, R 2 and R 3 Each is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R 2 and R 3 Choose either the same or different, where a is an integer from 1 to 20 and b is an integer from 0 to 2.

3. The viral infection inhibitor according to claim 1, wherein, The virus infection inhibitory compound has the structure shown in formula (4). ， In equation (4), X 2 and X 3 For structures containing acidic functional groups or their anhydride groups, R 4 R is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms. 5 R is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 6 R is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms. 7 It is an alkyl group with 1 to 10 hydrogen atoms or carbon atoms, where c is 0 or 1, d is an integer from 1 to 100, and e is 0 or 1.

4. The viral infection inhibitor according to claim 1, wherein, The virus infection inhibitory compound is a chain polymer, and the side chain of the chain polymer has the alkoxysilyl structure or the silanol structure, and the structure containing acidic functional groups or their anhydride groups.

5. The viral infection inhibitor according to any one of claims 1 to 4, wherein, The acidic functional group is a carboxyl group (-COOH), a sulfonyl group (-SO3H), or a phosphonic group [-P(=O)(OH)2].

6. The viral infection inhibitor according to any one of claims 1 to 4, wherein, The acidic functional group is a carboxyl group (-COOH).

7. The viral infection inhibitor according to any one of claims 1 to 4, wherein, The structure containing an acidic functional group or its anhydride group is a carboxyl 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 viral infection inhibitory solution, comprising: The viral infection inhibitor according to any one of claims 1 to 4, and Solvent.

9. A virus infection inhibitory coating, comprising: Virus infection inhibitors as described in any one of claims 1 to 4 Solvents, and Adhesive resin.

10. A masterbatch for molding synthetic resin, comprising: The viral infection inhibitor according to any one of claims 1 to 4, and Synthetic resins.

11. A viral infection inhibitory article comprising: Substrate, and The viral infection inhibitor contained in any one of claims 1 to 4.

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