Polymer

Abstract

To provide a novel compound that is useful as an antiviral agent as well as an antiviral material.SOLUTION: A polymer including a polymer chain having a repeating unit represented by the following formula (1A), wherein in formula (1A), R1 represents a hydrogen atom or a methyl group, Z1 represents -N+R2R3R4Yy- (R2 to R4 each independently represent an alkyl group, and Yy- represents a y-valent counter anion), and X1 represents a single bond or a divalent linking group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to polymers, and more particularly to polymers, antiviral agents, antiviral materials, antiviral methods, antibacterial agents, disinfectants, antibacterial materials, disinfectant materials, antibacterial methods, and disinfectant methods. [Background technology]

[0002] Viral infections can sometimes lead to severe symptoms such as bronchiolitis and pneumonia. In recent years, influenza viruses and coronaviruses have been wreaking havoc around the world. For this reason, in various fields such as daily necessities, medical supplies, cosmetics, and clothing, it is common to impart antiviral properties by applying or blending antiviral agents, or to mold articles using antiviral materials to create articles with antiviral properties. For example, ethanol is widely used to inactivate viruses, but has the problem of being highly volatile and therefore unsuitable for molding articles with antiviral properties. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2017 / 104676 Brochure Summary of the Invention [Problem to be solved by the invention]

[0004] On the other hand, a polymer having a polymer chain having a repeating unit provided by methacryloyloxyethylbenzyldimethylammonium chloride in a polyethyleneimine side chain has been reported as a polymer capable of inactivating Escherichia coli and Pseudomonas aeruginosa (Patent Document 1), but the antiviral activity of this polymer has not been reported so far. Therefore, the present inventors investigated the antiviral activity of the polymer described in Patent Document 1, but found no antiviral activity. Furthermore, a linear polymer having a repeating unit provided by methacryloyloxyethylbenzyldimethylammonium chloride had insufficient antibacterial activity against Pseudomonas aeruginosa when not modified with polyethyleneimine. An object of the present invention is to provide a novel compound useful as an antiviral agent or antiviral material. [Means for solving the problem]

[0005] As a result of extensive investigations, the present inventors have found that specific polymers having repeating units having a group that forms a trialkylammonium salt in a side chain have antiviral activity and are useful as antiviral agents and antiviral materials, and have completed the present invention.

[0006] That is, the present invention provides the following: <1> ~ <21> This provides: <1> A polymer (hereinafter also referred to as "specific polymer") having a polymer chain (hereinafter also referred to as "specific polymer chain") having a repeating unit represented by the following formula (1A) (hereinafter also referred to as "repeating unit (1A)"):

[0007] [ka]

[0008] [In formula (1A), R 1 represents a hydrogen atom or a methyl group, Z 1 -N + R 2 R 3 R 4 Y y- indicates (R 2 ~R 4 each independently represents an alkyl group, and Y y- indicates a counter anion with a y valence. X 1 represents a single bond or a divalent linking group.

[0009] <2> R in formula (1A) 2 ~R 4 At least one of the above is an alkyl group having 5 to 30 carbon atoms. <1> The polymer according to claim 1. <3> the polymerization ratio of the repeating unit represented by formula (1A) contained in the polymer chain is 3% by mass or more and 37% by mass or less of all repeating units contained in the polymer chain; <1> or <2> The polymer according to claim 1. <4> The polymer chain further has a repeating unit represented by the following formula (1B) (hereinafter also referred to as "repeating unit (1B)"): <1> ~ <3> The polymer according to any one of the preceding claims.

[0010] [ka]

[0011] [In formula (1B), R 5 represents a hydrogen atom or a methyl group, Z 2 is -NR 6 R 7 indicates (R 6 and R 7 each independently represents a substituted or unsubstituted hydrocarbon group; X 2 represents a single bond or a divalent linking group.

[0012] <5> The polymer chain further has a repeating unit represented by the following formula (2) (hereinafter also referred to as "repeating unit (2)"): <1> ~ <4> The polymer according to any one of the preceding claims.

[0013] [ka]

[0014] [In formula (2), R 9represents a hydrogen atom or a methyl group, A is an aromatic hydrocarbon group, -(C=O)OR 10 , -(C=O)NHR 11 , or -OR 12 (R 10 ~R 12 are each independently a hydrocarbon group or a group having a linear or cyclic ether structure.

[0015] <6> Furthermore, the polymer has a partial structure (excluding the polymer chain; hereinafter, this partial structure is also referred to as a "specific partial structure") derived from a compound containing a group represented by -NH- (hereinafter, this partial structure is also referred to as a "specific functional group"). <1> ~ <5> The polymer according to any one of the preceding claims. <7> The compound containing a group represented by -NH- is represented by the following formula (12) or (14): <6> The polymer according to claim 1.

[0016] [ka]

[0017] [In formula (12), R 26 represents a substituted or unsubstituted hydrocarbon group.

[0018] [ka]

[0019] [In formula (14), R 30 represents a substituted or unsubstituted divalent hydrocarbon group, or a substituted or unsubstituted divalent hydrocarbon group in which some of the carbon atoms have been replaced with ether bonds.

[0020] <8> It is a terminal non-amino-modified polymer. <1> ~ <5> The polymer according to any one of the preceding claims.

[0021] <9> <1> ~ <8> 1. An antiviral agent comprising, as an active ingredient, the polymer according to any one of the preceding items. <10> an antiviral agent selected from an anti-influenza virus agent and an anti-coronavirus agent; <9> The antiviral agent according to claim 1. <11> <1> ~ <8> 1. An antiviral material containing the polymer according to any one of the preceding items. <12> <1> ~ <8> 10. An antiviral method using the polymer according to any one of the preceding items.

[0022] <13> An antibacterial agent, a bactericide, or an antibacterial and bactericide (hereinafter collectively referred to as "antibacterial and / or bactericide"), <1> ~ <8> 10. An agent comprising the polymer according to any one of the above items as an active ingredient. <14> An antibacterial material, a bactericidal material, or an antibacterial and bactericidal material (hereinafter collectively referred to as "antibacterial and / or bactericidal material"), <1> ~ <8> A material containing the polymer according to any one of the above items. <15> An antibacterial method, a sterilization method, or an antibacterial and sterilization method (hereinafter, these are also collectively referred to as "antibacterial and / or sterilization methods"), <1> ~ <8> A method using the polymer according to any one of the above items.

[0023] <16> Used for antiviral purposes, <1> ~ <8> The polymer according to any one of the preceding claims. <17> For producing an antiviral agent, <1> ~ <8> Use of the polymer according to any one of the above items. <18> For producing antiviral materials, <1> ~ <8> Use of the polymer according to any one of the above items. <19> Used for antibacterial, sterilizing, or antibacterial and sterilizing purposes (hereinafter collectively referred to as "antibacterial and / or sterilizing"). <1> ~ <8> The polymer according to any one of the preceding claims. <20> For producing an antibacterial agent, a bactericide, or an antibacterial and bactericide, <1> ~ <8> Use of the polymer according to any one of the above items. <21> For producing an antibacterial material, a bactericidal material, or an antibacterial and bactericidal material, <1> ~ <8> Use of the polymer according to any one of the above items. [Effects of the Invention]

[0024] The polymer of the present invention has antiviral activity and is useful as an antiviral agent and an antiviral material. The polymer of the present invention also has antibacterial or bactericidal effect and is useful as an antibacterial and / or bactericidal agent and an antibacterial and / or bactericidal material. Furthermore, when applied to an article or the like, the polymer is unlikely to discolor the article or the like. DETAILED DESCRIPTION OF THE INVENTION

[0025] [Specific polymer] First, the specific polymer of the present invention will be described. The specific polymer of the present invention has a polymer chain having a repeating unit represented by the following formula (1A).

[0026] [ka]

[0027] [In formula (1A), R 1 represents a hydrogen atom or a methyl group, Z 1 -N + R 2 R 3 R 4 Y y- indicates (R 2 ~R 4 each independently represents an alkyl group, and Y y- indicates a counter anion with a y valence. X 1 represents a single bond or a divalent linking group.

[0028] Furthermore, the specific polymer chain preferably has a repeating unit represented by the following formula (1B) in addition to the repeating unit (1A) in order to enhance antiviral activity.

[0029] [ka]

[0030] [In formula (1B), R5 represents a hydrogen atom or a methyl group, Z 2 is -NR 6 R 7 indicates (R 6 and R 7 each independently represents a substituted or unsubstituted hydrocarbon group; X 2 represents a single bond or a divalent linking group.

[0031] (Repeating units (1A) and (1B)) Here, each symbol in formulas (1A) and (1B) will be explained. Z in formula (1A) 1 -N + R 2 R 3 R 4 Y y- Also, R 2 ~R 4 each independently represents an alkyl group, and Y y- indicates a y-valent counter anion. R 2 ~R 4 The alkyl group represented by the formula (1A) may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 30. In order to enhance the antiviral activity (particularly the antiviral activity against a wide range of viruses), 2 ~R 4 A more preferred embodiment is one in which at least one of the above is an alkyl group having 4 to 30 carbon atoms. In order to enhance antiviral activity (particularly antiviral activity against a wide range of viruses), the alkyl group having 4 to 30 carbon atoms is preferably an alkyl group having 5 to 30 carbon atoms, more preferably an alkyl group having 6 to 30 carbon atoms, even more preferably an alkyl group having 6 to 24 carbon atoms, still more preferably an alkyl group having 6 to 18 carbon atoms, and particularly preferably an alkyl group having 6 to 14 carbon atoms. R 2 ~R 4 When at least one of the alkyl groups represented by the formula (I) has 5 or more or 6 or more carbon atoms, the antiviral activity (particularly the anti-influenza virus activity) becomes even better.

[0032] R in formula (1A) 2 ~R 4 In order to enhance antiviral activity (especially against a wide range of viruses), R 2 is an alkyl group having 4 to 30 carbon atoms, and R 3 ~R 4 are each independently an alkyl group having 1 to 3 carbon atoms; R 2 ~R 3 are each independently an alkyl group having 4 to 30 carbon atoms, and R 4 is an alkyl group having 1 to 3 carbon atoms, R 2 ~R 4 are each independently an alkyl group having 4 to 30 carbon atoms, R 2 is an alkyl group having 4 to 30 carbon atoms, and R 3 ~R 4 are each independently an alkyl group having 1 to 3 carbon atoms. The alkyl group having 1 to 3 carbon atoms is preferably an alkyl group having 1 or 2 carbon atoms in order to enhance antiviral activity (particularly antiviral activity against a wide range of viruses). R in formula (1A) 2 ~R 4 The combination of 2 is an alkyl group having 4 to 30 carbon atoms, and R 3 ~R 4 However, when these groups are each independently an alkyl group having 1 to 3 carbon atoms, the antiviral activity (particularly anti-influenza virus activity) becomes even better.

[0033] R 2 ~R 4 Examples of the alkyl group represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decanyl group, an n-undecanyl group, and an n-dodecanyl group.

[0034] Y y- may be a monovalent or polyvalent counteranion, and may be a monoatomic or polyatomic anion. Examples of polyvalent counter anions include those derived from polyanionic compounds. Polyanionic compounds are organic or inorganic compounds that ionize when dissolved in water and assume two or more negative charges. Examples of polyanionic compounds include polymeric compounds such as gums and polyacrylic acid derivatives, and compounds known as chelating agents such as citric acid and its salts and EDTA. The monovalent counter anion is Cl. - , Br - , I - Halogen ions such as ClO4 - , BF4 - , CH3(C=O)O - , PF6 - and the like. Y y- As the counter anion, a monovalent to hexavalent counter anion (where y is an integer of 1 to 6) is preferred, a monovalent to trivalent counter anion (where y is an integer of 1 to 3) is more preferred, a monovalent counter anion is further preferred, and a halogen ion is particularly preferred.

[0035] Z in formula (1B) 2 is -NR 6 R 7 Also, R 6 and R 7 are each independently a substituted or unsubstituted hydrocarbon group. Here, in the present invention, the term "hydrocarbon group" is a concept that encompasses aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be linear, branched, or cyclic, and may be a saturated or unsaturated hydrocarbon group, and may have an unsaturated bond at either a terminal or a non-terminal.

[0036] The aliphatic hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms (preferably 1 to 12). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decanyl, n-undecanyl, and n-dodecanyl groups. The alicyclic hydrocarbon group is preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms (preferably 3 to 12 carbon atoms), and more preferably a cycloalkyl group having 3 to 20 carbon atoms (preferably 3 to 12 carbon atoms). Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Furthermore, the aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms (preferably 6 to 10), more preferably an aryl group having 6 to 20 carbon atoms (preferably 6 to 10), or an aralkyl group having 7 to 20 carbon atoms (preferably 7 to 16). Here, in the present invention, the term "aryl group" refers to a monocyclic to tricyclic aromatic hydrocarbon group, and examples thereof include a phenyl group, a naphthyl group, a biphenyl group, and an anthranyl group. Specific examples of the aralkyl group include a benzyl group, a phenethyl group, an α-methylbenzyl group, and a 2-phenylpropan-2-yl group. Among these, R 6 and R 7 In order to enhance antiviral activity, the hydrocarbon group in is preferably an alkyl group having 1 to 12 carbon atoms (more preferably 1 to 3, particularly preferably 1 or 2), and particularly preferably a methyl group, an ethyl group, an n-propyl group, or an isopropyl group. In addition, R 6 and R 7 Examples of the substituent in include a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, and an alkoxy group having 1 to 6 carbon atoms.

[0037] In formulas (1A) to (1B), X 1 , X 2 Examples of the divalent linking group represented by the formula include a methylene group, an alkylene group, an arylene group, -(C=O)OR 13 -(*), -(C=O)NHR14 -(*) or -ArR 15 -(*) (wherein Ar represents an arylene group, and * represents the same as Z 1 , Z 2 In the present invention, examples of the "arylene group" include a phenylene group, a naphthylene group, and a phenanthrenylene group. 13 ~R 15 are each independently a methylene group, an alkylene group, or an alkyleneoxyalkylene group.

[0038] X 1 , X 2 and R 13 ~R 15 The alkylene group represented by the formula (I) is preferably an alkylene group having 2 to 10 carbon atoms (preferably 2 to 6, more preferably 2 to 4 carbon atoms). The alkylene group may be linear or branched, and specific examples thereof include an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. The alkylene group contained in the alkyleneoxyalkylene group is preferably the same as the alkylene group described above. 2-4 Alkyleneoxy C 2-4 Alkylene groups are preferred, and specific examples include ethyleneoxyethylene groups.

[0039] X 1 , X 2 From the viewpoint of ease of production of the specific polymer, -(C=O)OR 13 -(*), -(C=O)NHR 14 -(*) or -ArR 15 -(*) is preferred, and -(C=O)OR 13 -(*) is particularly preferred. 13 ~R 15 As the alkylene group, an alkylene group having 2 to 6 carbon atoms (more preferably 2 to 4 carbon atoms) is particularly preferred.

[0040] (Repeating unit (2)) In order to enhance antiviral activity (particularly antiviral activity against a wide range of viruses), the specific polymer chain preferably has a repeating unit represented by the following formula (2) in addition to the repeating unit (1A). The specific polymer chain may have both the repeating unit (1B) and the repeating unit (2) in addition to the repeating unit (1A).

[0041] [ka]

[0042] [In formula (2), R 9 represents a hydrogen atom or a methyl group, A is an aromatic hydrocarbon group, -(C=O)OR 10 , -(C=O)NHR 11 , or -OR 12 (R 10 ~R 12 are each independently a hydrocarbon group or a group having a linear or cyclic ether structure.

[0043] In A of the above formula (2), the aromatic hydrocarbon group is preferably an aryl group having 6 to 20 carbon atoms (more preferably 6 to 10 carbon atoms), and a phenyl group is particularly preferred. In addition, in A of the above formula (2), R 10 ~R 12 represents a hydrocarbon group or a group having a chain or cyclic ether structure. This hydrocarbon group can be any of the above R 6 , R 7 In addition to the same groups as those shown above, examples of the hydrocarbon groups include alicyclic hydrocarbon groups such as saturated condensed polycyclic hydrocarbon groups, saturated bridged ring hydrocarbon groups, saturated spiro hydrocarbon groups, and saturated cyclic terpene hydrocarbon groups. 10 ~R 12The hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms (preferably 1 to 15, more preferably 1 to 10), an aryl group having 6 to 20 carbon atoms (preferably 6 to 14), an aralkyl group having 7 to 20 carbon atoms (preferably 7 to 16), or an alicyclic hydrocarbon group having 3 to 20 carbon atoms (preferably 4 to 15), and more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethylhexyl group, an isodecyl group, a dodecyl group, a phenyl group, a benzyl group, a phenylethyl group, a cyclohexyl group, a cyclohexenyl group, a tert-butylcyclohexyl group, a decahydro-2-naphthyl group, a tricyclo[5.2.1.0] 2,6 ]Decan-8-yl group, adamantyl group, dicyclopentenyl group, pentacyclopentadecanyl group, tricyclopentenyl group, and isobornyl group are particularly preferred.

[0044] On the other hand, R 10 ~R 12 As the group having a chain ether structure in the formula (3), a group represented by the following formula (3) is preferred.

[0045] [ka]

[0046] [In formula (3), R 16 each independently represents an alkylene group having 2 to 4 carbon atoms, R 17 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group, n represents an integer from 2 to 150; "*" indicates a bond.

[0047] R 16 may be composed of two or more types of alkylene groups, and is preferably an ethylene group and / or a propylene group. R 17The alkyl group having 1 to 6 carbon atoms in the formula (I) is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 or 2 carbon atoms. The alkyl group may be linear or branched, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. R 17 The aryl group in is preferably a phenyl group. The aryl group may be substituted with an α-cumyl group or the like. R 17 is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. n is preferably an integer of 2 to 20, more preferably an integer of 2 to 10, and particularly preferably an integer of 2 to 5.

[0048] Also, R 10 ~R 12 As the group having a cyclic ether structure in the above, a group represented by the following formula (4) is preferred.

[0049] [ka]

[0050] [In formula (4), R 18 represents a methylene group or an alkylene group having 2 to 12 carbon atoms, CE represents a cyclic ether group which may have an alkyl group as a substituent, "*" indicates a bond.

[0051] In the above formula (4), R 18 R is preferably a methylene group or an alkylene group having 2 to 6 carbon atoms. The alkylene group may be linear or branched. 18 Specific examples of the alkyl group include a methylene group, an ethylene group, an ethane-1,1-diyl group, a trimethylene group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a tetramethylene group, a butane-1,2-diyl group, a butane-1,3-diyl group, a pentamethylene group, and a hexamethylene group.

[0052] In the above formula (4), CE is preferably a cyclic ether group having 3 to 7 atoms constituting the ring, and specific examples thereof include cyclic ether groups represented by the following formulas (i) to (viii).

[0053] [ka]

[0054] [In formulas (i) to (viii), "*" represents R 18 indicates that the bond is bonded to

[0055] In the present invention, the above R 10 ~R 12 As the group, a hydrocarbon group is preferred in order to enhance antiviral activity, antibacterial / bactericidal activity, and compatibility with resins such as polypropylene, ABS resin (acrylonitrile-butadiene-styrene copolymer resin), and polyurethane during processing of antiviral materials.

[0056] The specific polymer chain may have a repeating unit other than the repeating units (1A), (1B), and (2) (hereinafter also referred to as "other repeating units"). Examples of such repeating units include a repeating unit derived from a vinyl monomer having an anionic group, a repeating unit derived from any of the compound group α (monomers 1 to 18) of the following formula, a repeating unit derived from a compound represented by the following formula (20), a repeating unit derived from 4-vinylpyridine, and salts thereof.

[0057] [ka]

[0058] [ka]

[0059] Examples of the anionic group include a carboxyl group, a sulfonic acid group, a phosphate group, and a hydroxyl group exhibiting anionic properties. Among these, a carboxyl group and a sulfonic acid group are preferred, and a carboxyl group is more preferred. Specific examples of suitable vinyl monomers having an anionic group include (meth)acrylic acid, maleic acid, maleic anhydride, styrenesulfonic acid, 2-(meth)acrylamido-2-methylpropanesulfonic acid, allylsulfonic acid, vinylsulfonic acid, (meth)acrylsulfonic acid, sulfopropyl (meth)acrylate, mono[2-(meth)acryloyloxyethyl] succinate, ω-carboxypolycaprolactone mono(meth)acrylate, p-vinylbenzoic acid, p-hydroxystyrene, and p-hydroxy-α-methylstyrene, as well as vinyl monomers having an acidic group and their salts. These may be used alone or in combination of two or more. Among these, (meth)acrylic acid, maleic acid, and maleic anhydride are preferred. Other examples of monomers constituting the other repeating units include N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide; (meth)acrylic acid esters having a hydroxyl group such as 2-hydroxyethyl (meth)acrylate, glycerol mono(meth)acrylate and 4-hydroxyphenyl (meth)acrylate; and (meth)acrylamide monomers such as (meth)acrylamide and N-methylolacrylamide. The specific polymer chain may have one or more types of the other repeating units. In the present invention, the term "(meth)acrylate" means "acrylate or methacrylate."

[0060] The polymerization ratio of the repeating unit (1A) contained in the specific polymer chain is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, and particularly preferably 10% by mass or more, of all repeating units contained in the specific polymer chain in order to improve antiviral activity, antibacterial / bactericidal activity, and handleability during production of antiviral materials, etc., and is preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 37% by mass or less, and particularly preferably 33% by mass or less, of all repeating units contained in the specific polymer chain in order to improve antiviral activity and water solubility. Specific ranges include preferably 1% by mass or more and 80% by mass or less, more preferably 3% by mass or more and 70% by mass or less, even more preferably 3% by mass or more and 37% by mass or less, even more preferably 5% by mass or more and 37% by mass or less, and particularly preferably 10% by mass or more and 33% by mass or less. When the polymerization ratio of the repeating unit (1A) contained in the specific polymer chain is 37% by mass or less or 33% by mass or less, the antiviral activity (especially anti-influenza virus activity) becomes even better. In addition, the antiviral material becomes more soluble in water, which results in excellent handling during production of the antiviral material, etc.

[0061] The polymerization ratio of the repeating unit (1B) contained in the specific polymer chain is preferably 4% by mass or more, more preferably 8% by mass or more, even more preferably 12% by mass or more, and particularly preferably 20% by mass or more, of all repeating units contained in the specific polymer chain to enhance antiviral activity and solubility in reaction solvents, and is preferably 55% by mass or less, more preferably 50% by mass or less, and particularly preferably 47% by mass or less, of all repeating units contained in the specific polymer chain to facilitate contact with viruses and bacteria. Specific ranges are preferably 4% by mass or more and 55% by mass or less, more preferably 8% by mass or more and 50% by mass or less, even more preferably 12% by mass or more and 50% by mass or less, and particularly preferably 20% by mass or more and 47% by mass or less, of all repeating units contained in the specific polymer chain.

[0062] The total polymerization ratio of the repeating unit (1A) and the repeating unit (1B) contained in the specific polymer chain is preferably 1 to 99 mass%, more preferably 5 to 80 mass%, even more preferably 10 to 70 mass%, and particularly preferably 30 to 60 mass%, of all repeating units contained in the specific polymer chain, in order to facilitate contact with viruses and bacteria. In order to enhance solubility in the reaction solvent, the total polymerization ratio of the repeating unit (2) is preferably 1 to 99 mass%, more preferably 10 to 85 mass%, even more preferably 20 to 70 mass%, and particularly preferably 35 to 55 mass%, of all repeating units contained in the specific polymer chain.

[0063] The mass ratio of the polymerization rate of the repeating unit (1A) to the total polymerization rate of the repeating unit (1A) and the repeating unit (1B) [(1A) / ((1A)+(1B))] is preferably 0.1 or more, more preferably 0.2 or more, and particularly preferably 0.3 or more in order to enhance antiviral activity, antibacterial / fungicidal activity, and to facilitate contact with viruses and bacteria; and is preferably 0.9 or less, more preferably 0.8 or less, and particularly preferably 0.7 or less in order to enhance antiviral activity and water solubility. Specifically, the range is preferably 0.1 or more and 0.9 or less, more preferably 0.2 or more and 0.8 or less, and particularly preferably 0.3 or more and 0.7 or less. When the mass ratio [(1A) / ((1A)+(1B))] is 0.7 or less, the antiviral activity (especially anti-influenza virus activity) is further improved. In addition, the compound is easily soluble in water, which results in excellent handling during the production of antiviral materials, etc.

[0064] Furthermore, in order to improve handleability during the production of antiviral materials and the like, the mass ratio of the total polymerization ratio of the repeating unit (2) to the polymerization ratio of the repeating unit (1A) [(2) / (1A)] is preferably from 0.1 to 10, more preferably from 0.5 to 7.5, even more preferably from 0.9 to 4, still more preferably from 1 to 3, and particularly preferably from 1.2 to 2.7.

[0065] The polymerization rate and copolymerization ratio can be calculated by measuring the peak reduction rate of the quaternary ammonium reagent using high performance liquid chromatography or by pyrolysis gas chromatography. For example, in Synthesis Example 1 described below, the peaks derived from DAMA, MMA, nBMA, and EHMA can be identified and quantified from the peak fragments of each chromatogram to calculate the copolymerization ratio. An example of the measurement conditions is shown below. The copolymerization ratio can also be measured by NMR. <Confirmation of polymer composition ratio> Apparatus: Pyrolysis gas chromatogram mass spectrometer (pyrolysis section: Pyrofoil sampler JPS-350 manufactured by Japan Analytical Industry Co., Ltd., gas chromatograph section: Agilent Technologies 7890A GC System, mass spectrometer section: Agilent Technologies 5975 inert XL Mass Selective detector) Column: BPX-5 Temperature: Pyrolysis temperature 590°C x 5 seconds, column inlet 280°C, column temperature (starting at 50°C, increasing by 10°C per minute to 350°C) Flow rate: He 1.0mL / min. Ionization method: Electron ionization method (EI method) Detection unit: MS quadrupole, Aux-2

[0066] The specific polymer chain may have one or more types of repeating unit (1A), and may also have one or more types of repeating unit (1B) and repeating unit (2).

[0067] When the specific polymer chain has the repeating unit (1B) or the repeating unit (2) in addition to the repeating unit (1A), the specific polymer chain may be either a block copolymer or a random copolymer, and is not particularly limited. However, in order to facilitate contact with viruses and bacteria, and to improve antiviral activity, antibacterial / sterilizing activity, and handleability during production of antiviral materials, etc., it is preferably a random copolymer.

[0068] The molecular weight of the specific polymer chain is, in terms of polystyrene equivalent weight average molecular weight Mw measured by gel permeation chromatography (GPC, mobile phase: tetrahydrofuran), preferably 10,000 or less, more preferably 100 to 5,000, even more preferably 300 to 3,000, and particularly preferably 500 to 2,500. The ratio (Mw / Mn) of Mw of the specific polymer chain to Mn, in terms of polystyrene equivalent, measured by GPC (mobile phase: tetrahydrofuran) is preferably 1.0 to 1.8, more preferably 1.0 to 1.7, and particularly preferably 1.1 to 1.5.

[0069] The content of the specific polymer chain is preferably from 40% by mass to 99% by mass, more preferably from 45% by mass to 97% by mass, and particularly preferably from 50% by mass to 95% by mass, based on the total amount of the specific polymer. The content of the specific polymer chain can be measured by pyrolysis gas chromatography or the like. For example, in Synthesis Example 1 described below, the peaks corresponding to the specific polymer and the specific polymer chain can be identified and quantified from the fragments of the peaks in each chromatogram, and the content of the specific polymer chain can be calculated. An example of measurement conditions is shown below. The content of the specific polymer chain can also be measured by NMR. <Confirmation of polymer composition ratio> Apparatus: Pyrolysis gas chromatogram mass spectrometer (pyrolysis section: Pyrofoil sampler JPS-350 manufactured by Japan Analytical Industry Co., Ltd., gas chromatograph section: Agilent Technologies 7890A GC System, mass spectrometer section: Agilent Technologies 5975 inert XL Mass Selective detector) Column: BPX-5 Temperature: Pyrolysis temperature 590°C x 5 seconds, column inlet 280°C, column temperature (starting at 50°C, increasing by 10°C per minute to 350°C) Flow rate: He 1.0mL / min. Ionization method: Electron ionization method (EI method) Detection unit: MS quadrupole, Aux-2

[0070] The specific polymers of the present invention can be broadly classified into terminally modified polymers and terminally unmodified polymers. In this specification, a "terminally modified polymer" refers to a polymer having a specific polymer chain whose terminals are modified, and a "terminally unmodified polymer" refers to a polymer having a specific polymer chain whose terminals are not modified. In addition, in this specification, a polymer having a specific polymer chain whose terminal does not have a partial structure derived from a compound having an amino group bonded thereto is referred to as a "terminally unamino-modified polymer." Surprisingly, the specific polymer of the present invention, even in the case of such a non-amino-terminated polymer, exhibits excellent antiviral activity and antibacterial and bactericidal activity. Furthermore, when the polymer is a non-amino-terminated polymer, deliquescence and the accompanying wetting and solidification are less likely to occur, and the polymer exhibits excellent handling properties during production of antiviral materials and excellent storage stability.

[0071] (Specific partial structure) Furthermore, one embodiment of the specific polymer of the present invention includes a polymer having, in addition to the specific polymer chain, a partial structure (excluding the polymer chain) derived from a compound containing a group represented by -NH-. When the specific polymer of the present invention has the specific partial structure, it becomes more soluble in organic solvents and is more easily applicable to a wide range of uses. When the specific polymer of the present invention has a specific partial structure, it is preferable that the specific polymer chain has its end bonded to the specific partial structure, and particularly preferably that the end bonded to an N atom derived from a specific functional group in the specific partial structure. Furthermore, the specific polymer chain preferably has a divalent group formed by ring-opening of a cyclic ether group, and more preferably has a divalent group formed by ring-opening of a cyclic ether group at the end of the polymer chain from the viewpoint of high reactivity. Furthermore, the specific polymer preferably has a divalent group formed by ring-opening of the cyclic ether group bonded to the specific partial structure, and particularly preferably has a divalent group formed by ring-opening of the cyclic ether group bonded to an N atom derived from a specific functional group in the specific partial structure. The divalent group formed by ring-opening of a cyclic ether group is preferably a divalent group formed by ring-opening of a cyclic ether group having 3 to 7 ring atoms, more preferably a divalent group formed by ring-opening of a cyclic ether group represented by formulas (i-2) to (viii-2), and particularly preferably a divalent group formed by ring-opening of a cyclic ether group represented by formula (i-2) (ring-opened epoxy group). The divalent groups formed by ring-opening of a cyclic ether group represented by formulas (i-2) to (iv-2) are specifically represented by the following formulas (i-3) to (iv-3).

[0072] [ka]

[0073] [In each formula, "*" indicates a bond bonding to the repeating unit (1A) (or to the repeating unit (1A), (1B), or (2) if the specific polymer chain has the repeating unit (1B) and / or the repeating unit (2)), and "**" indicates a bond bonding to the N atom derived from a specific functional group in a specific partial structure.]

[0074] Furthermore, when the specific polymer of the present invention has a specific partial structure, the repeating unit (1) (when the specific polymer chain has the repeating unit (1B) and / or the repeating unit (2), the repeating unit (1A), (1B) or (2)) and the divalent group formed by ring-opening of a cyclic ether group may be bonded via a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted divalent hydrocarbon group, and a substituted or unsubstituted divalent hydrocarbon group having two or more carbon atoms and having one or more bonds selected from an ether bond, an ester bond, and an amide bond between carbon atoms. The number of carbon atoms in the "divalent hydrocarbon group" and "divalent hydrocarbon group having 2 or more carbon atoms" is preferably 2 to 12, and more preferably 4 to 10. Furthermore, the "divalent hydrocarbon group" and "divalent hydrocarbon group having 2 or more carbon atoms" are preferably alkanediyl groups. The alkanediyl group may be linear or branched. Specific examples of the alkanediyl group include methane-1,1-diyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, and pentane-1,1-diyl. Examples of the substituent in the divalent hydrocarbon group include a di-C group such as a dimethylamino group, a diethylamino group, and a diisopropylamino group. 1-4 Examples include alkylamino groups. The divalent linking group is preferably a group having one or more bonds selected from an ether bond, an ester bond, and an amide bond between carbon atoms of a substituted or unsubstituted divalent hydrocarbon group having two or more carbon atoms, and more preferably a group having an ester bond between carbon atoms of a substituted or unsubstituted divalent hydrocarbon group having two or more carbon atoms. The number of ester bonds contained in this group may be one or more. Specific examples include those represented by the following formula:

[0075] [ka]

[0076] (In the above formula, "*" indicates a bond.)

[0077] Here, the specific partial structure will be described in detail. The specific partial structure is a partial structure derived from a compound containing a specific functional group. However, the specific partial structure does not include a specific polymer chain. The specific partial structure is preferably a residue obtained by removing some or all of the hydrogen atoms derived from the specific functional group from the compound. As the compound containing a specific functional group, in order to enhance antiviral activity and antibacterial / bactericidal activity, a compound containing at least one specific functional group selected from a primary amino group, a secondary amino group, a carbamoyl group (-C(=O)-NH2), and an amide bond (-C(=O)-NH-) is preferred, a compound containing at least one selected from a primary amino group, a secondary amino group, and a carbamoyl group is more preferred, a compound containing at least one selected from a primary amino group and a secondary amino group is even more preferred, and a compound containing a primary amino group is particularly preferred. If the specific partial structure is a partial structure derived from a compound containing a primary amino group, discoloration of the liquid or sheet when added to a solvent or when added to a solvent and then the sheet is immersed in the solvent is suppressed. For example, in the antiviral, antibacterial, and sterilizing field, colors that give a hygienic impression are preferred, such as antiviral, antibacterial, and disinfectant synthetic detergents being clear in color and antiviral and antibacterial sheets being white in color, but if the specific partial structure is a partial structure derived from a compound containing a primary amino group, it becomes easier to produce antiviral agents, antiviral materials, antibacterial and / or disinfectant agents, and antibacterial and / or disinfectant materials in colors that give a hygienic impression. Furthermore, the compound containing a specific functional group may be a compound containing one specific functional group in the molecule or a compound containing multiple specific functional groups in the molecule, but a compound containing one or two specific functional groups in the molecule is preferred.

[0078] The specific partial structure may be derived from a low molecular weight (non-polymer type) compound or a high molecular weight (polymer type) compound, but is preferably derived from a low molecular weight (non-polymer type) compound in order to suppress a change in color tone of the target object when applied as an antiviral agent, antiviral material, etc. As the high molecular weight (polymer type) compound, a high molecular weight (polymer type) amine compound is preferred, and a multi-branched high molecular weight amine compound is more preferred. When the amine compound is a multi-branched polymer, the specific polymer becomes a multi-branched star polymer having a specific partial structure as a core portion and specific polymer chains as arms. The weight-average molecular weight of the polymer type amine compound is preferably 100 or more, more preferably 150 or more, and is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, and particularly preferably 1500 or less. Furthermore, when the compound containing a specific functional group is a compound containing at least one selected from a primary amino group and a secondary amino group, the specific partial structure may be such that some or all of the amino groups derived from the compound containing the specific functional group are converted into organic ammonium salts.

[0079] Examples of compounds containing the specific functional group include polyaziridine polymers; polyaziridine polymer modifications such as alkyl isocyanate-modified or alkylene oxide-modified polyaziridine polymers; monoamine compounds such as aliphatic monoamine compounds, alicyclic monoamine compounds, polyoxyalkylene monoamine compounds, and aromatic monoamine compounds; diamine compounds such as aliphatic diamine compounds, alicyclic diamine compounds, polyoxyalkylenediamine compounds, and aromatic diamine compounds; biguanide compounds (either low molecular weight (non-polymer) or high molecular weight (polymer)); amino acids; amino acid derivatives; peptides; amino sugars; polyamino sugars; H2 receptor antagonists (e.g., cimetidine, ranitidine hydrochloride, famotidine); antiviral drugs (e.g., anti-influenza virus drugs, anti-coronavirus drugs), and other antibacterial drugs. The specific polymer may have one or more specific partial structures derived from these. Among these, in order to improve antiviral activity, antibacterial / bactericidal activity, and ease of handling during production of antiviral materials, etc., preferred compounds containing a specific functional group are polyaziridine polymers, modified polyaziridine polymers, monoamine compounds, diamine compounds, biguanide compounds, amino acids, amino acid derivatives, peptides, amino sugars, polyamino sugars, H2 receptor antagonists, antiviral agents, and antibacterial agents, and monoamine compounds and diamine compounds are more preferred in order to suppress color changes in the target substance when used as an antiviral agent, antiviral material, etc. Furthermore, the specific polymer of the present invention has excellent antiviral activity, antibacterial / bactericidal activity, even when the specific partial structure is a partial structure derived from a monoamine compound or a diamine compound. As described above, the weight-average molecular weight of the polyaziridine polymer is preferably 100 or more, more preferably 150 or more, and is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, and particularly preferably 1500 or less. As described above, when the compound containing a specific functional group is a polyaziridine polymer, the specific polymer becomes a multi-branched star polymer having the specific partial structure as a core moiety and the specific polymer chains as arms.

[0080] The polyaziridine polymer may be one having a repeating unit represented by the following formula (11).

[0081] [ka]

[0082] [In formula (11), R 21 represents a hydrogen atom or a bond bonding to another repeating unit (11), R 22 ~R 25 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group. However, R 22 and R 23 When both are hydrocarbon groups, R 22 and R 23may be joined together to form a ring, and R 22 and R 24 When both are hydrocarbon groups, R 22 and R 24 may be joined together to form a ring, and R 24 and R 25 When both are hydrocarbon groups, R 24 and R 25 may be joined together to form a ring.

[0083] R 21 is a bond bonding to another repeating unit (11), the formula (11) is specifically represented by the following formula (11-2). 21 Preferably, the repeating unit has both a hydrogen atom and a trivalent repeating unit represented by formula (11-2).

[0084] [ka]

[0085] [In formula (11-2), R 22 ~R 25 is R in Equation (11). 22 ~R 25 is equivalent to

[0086] R 22 ~R 25 The hydrocarbon group represented by the above R 6 and R 7 Similarly to the above, R is a concept that encompasses aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be linear, branched, or cyclic, and may be a saturated or unsaturated hydrocarbon group, and may have an unsaturated bond at either a terminal or a non-terminal position. 22 ~R 25The hydrocarbon group represented by the formula (I) is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 4). Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Also, R 22 and R 23 , R 22 and R 24 , R 24 and R 25 Examples of the ring that may be formed by each of the above include cycloalkane rings having 3 to 10 carbon atoms, such as a cyclohexane ring, a methylcyclohexane ring, a cycloheptane ring, and a cyclooctane ring. R 22 ~R 25 Examples of the substituent in the formula include an alkyl group having 1 to 6 carbon atoms and a halogen atom.

[0087] Specific examples of polyaziridine polymers include polyethyleneimine, polypropyleneimine, poly(2,2-dimethylaziridine), poly(2,3-dimethylaziridine), poly(2,2,3,3-tetramethylaziridine), poly(2-ethylaziridine), poly(2-hexylaziridine), poly(7-azabicyclo[4.1.0]heptane), poly(1-azaspiro[2.5]octane), poly(1-methyl-7-azabicyclo[4.1.0]heptane), poly(3-methyl-7-azabicyclo[4.1.0]heptane), etc. Among these, polyethyleneimine and polypropyleneimine are preferred, and polyethyleneimine is particularly preferred.

[0088] As the monoamine compound, in order to suppress a change in color tone of the target substance when it is used as an antiviral agent, antiviral material, etc., a monofunctional amine having one primary amino group is preferred, and one represented by the following formula (12) is more preferred. Furthermore, the specific polymer of the present invention has excellent antiviral activity and antibacterial and bactericidal activity even when the specific partial structure is a partial structure derived from the one represented by the following formula (12).

[0089] [ka]

[0090] [In formula (12), R 26 represents an organic group (preferably a substituted or unsubstituted hydrocarbon group, more preferably a substituted or unsubstituted hydrocarbon group having 2 to 20 carbon atoms).

[0091] Examples of the organic group include substituted or unsubstituted hydrocarbon groups, and substituted or unsubstituted hydrocarbon groups having two or more carbon atoms and having one or more bonds selected from ether bonds, ester bonds, and amide bonds between carbon atoms. Of these, substituted or unsubstituted hydrocarbon groups are preferred. The above-mentioned "hydrocarbon group" and "hydrocarbon group having 2 or more carbon atoms" preferably have 30 or less carbon atoms, more preferably 20 or less carbon atoms, even more preferably 2 to 20 carbon atoms, and particularly preferably 4 to 16 carbon atoms.

[0092] R 26 The "hydrocarbon group" in the above R 6 and R 7 Similarly to the above, the term "aliphatic hydrocarbon group" is a concept that encompasses aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be linear, branched, or cyclic, and may be a saturated or unsaturated hydrocarbon group, and may have an unsaturated bond at either a terminal or a non-terminal. Examples of the hydrocarbon group include an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group, with an alkyl group being preferred. The number of carbon atoms in the alkyl group is preferably 30 or less, more preferably 20 or less, still more preferably 2 to 20, and particularly preferably 4 to 16. The alkyl group may be linear or branched. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and a 2-butyloctyl group. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, more preferably 3 to 12. Specific examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 10. Examples include a phenyl group, a naphthyl group, a biphenyl group, and an anthranyl group. The number of carbon atoms in the aralkyl group is preferably 7 to 20, more preferably 7 to 16. Examples include a benzyl group, a phenethyl group, an α-methylbenzyl group, and a 2-phenylpropan-2-yl group.

[0093] Also, R 26 The "hydrocarbon group" in the formula (I) may have a substituent. Examples of the substituent include a halogen atom and a hydroxy group.

[0094] Specific examples of monoamine compounds include ethylamine, isopropylamine, 3-chloro-n-propylamine, n-butylamine, isobutylamine, tert-butylamine, n-octylamine, 2-ethylhexylamine, 2-butyl-n-octan-1-amine, cyclohexylamine, phenylamine, and benzylamine, and among these, 2-ethylhexylamine is preferred.

[0095] As the diamine compound, in order to suppress a change in color tone of an object when used as an antiviral agent, antiviral material, etc., a compound having two primary amino groups is preferred, and one represented by the following formula (13) or (14) is more preferred, and one represented by the following formula (14) is even more preferred. Furthermore, the specific polymer of the present invention has excellent antiviral activity and antibacterial and bactericidal activity even when the specific partial structure is a partial structure derived from one represented by the following formula (13) or (14).

[0096] [ka]

[0097] [In formula (13), R 27 represents a single bond, an ether bond, an amide bond, an ester bond, a thio group, or a divalent organic group, R 28 and R 29 each independently represents a substituted or unsubstituted hydrocarbon group, p and q each independently represent an integer of 0 to 4; However, R 27 is a divalent organic group, and at least one of p and q is an integer of 0 to 3, then R 27 may form a condensed ring with the adjacent phenylene group.

[0098] [ka]

[0099] [In formula (14), R 30 represents a divalent organic group.

[0100] In equation (13), R 27 represents a single bond, an ether bond, an amide bond, an ester bond, a thio group, or a divalent organic group. Among these, a single bond, an ether bond, a thio group, or a divalent organic group is preferred, and a divalent organic group is more preferred.

[0101] R in equation (13) 27 , R in Equation (14) 30 The divalent organic group represented by the formula (I) is more preferably a substituted or unsubstituted divalent hydrocarbon group, a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group is substituted with one or more bonds selected from an ether bond, an amide bond, an ester bond, and a thio group, or a substituted or unsubstituted divalent nitrogen-containing heterocyclic group, and even more preferably a substituted or unsubstituted divalent hydrocarbon group, a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group is substituted with one or more bonds selected from an ether bond and an ester bond, or a substituted or unsubstituted divalent nitrogen-containing heterocyclic group.

[0102] Among the above, R in formula (13) 27As the alkyl group, a substituted or unsubstituted divalent hydrocarbon group, or a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group is substituted with one or more bonds selected from an ether bond and an ester bond is more preferable, and a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group is substituted with an ester bond is particularly preferable. Furthermore, R in equation (14) 30 As the alkyl group, a substituted or unsubstituted divalent hydrocarbon group, a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group has been replaced with an ether bond, or a substituted or unsubstituted divalent nitrogen-containing heterocyclic group is more preferable, and a substituted or unsubstituted divalent hydrocarbon group, or a group in which a portion of the carbon atoms of the substituted or unsubstituted divalent hydrocarbon group has been replaced with an ether bond is particularly preferable.

[0103] Examples of a substituted or unsubstituted divalent hydrocarbon group in which some of the carbon atoms have been replaced by an ether bond include -(R g O) t R h A group represented by - is preferred. where R g and R h are each independently a divalent hydrocarbon group (preferably an alkanediyl group) having 1 to 8 carbon atoms (preferably an alkanediyl group), and t is an integer of 1 to 12 (preferably an integer of 1 to 8, more preferably an integer of 1 to 4). g and R h Examples of the alkanediyl group represented by the formula (I) include a methane-1,1-diyl group, an ethane-1,1-diyl group, an ethane-1,2-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-1,3-diyl group, and a propane-2,2-diyl group. When t is an integer of 2 to 12, t R g may be the same or different. Such a -(R g O) t R hSpecific examples of the group represented by - include -CH2-O-CH2-, -(CHO)2-CH2-, -CH2CH2-O-CH2CH2-, -(CH2CH2O)2-CH2CH2-, -(CH2CH2O)3-CH2CH2-, -(CH2CH2O)4-CH2CH2-, -(CH2CHCH3O)2-CH2CHCH3-, -(CH2CHCH3O)3-CH2CHCHCH3-, -(CH2CHCH3O)4-CH2CHCH3-, and the like.

[0104] Furthermore, R in equation (13) 27 , R in Equation (14) 30 The number of carbon atoms in the divalent organic group represented by the formula (I) is preferably 1 to 50, more preferably 2 to 40, still more preferably 3 to 30, and particularly preferably 5 to 20. In addition, in a group in which some of the carbon atoms of a substituted or unsubstituted divalent hydrocarbon group are substituted with one or more ether bonds, amide bonds, ester bonds, and thio groups, the number of ether bonds, amide bonds, ester bonds, and thio groups may be one or more. R in equation (13) 27 , R in Equation (14) 30 The "divalent hydrocarbon group" in the above may be any of a divalent aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group, and a divalent aromatic hydrocarbon group. It may also be a divalent group formed by linking these groups together (for example, a divalent group formed by linking a divalent aliphatic hydrocarbon group and a divalent alicyclic hydrocarbon group). The number of carbon atoms in the divalent aliphatic hydrocarbon group is preferably 1 to 50, more preferably 2 to 40, even more preferably 3 to 30, and particularly preferably 5 to 20. The divalent aliphatic hydrocarbon group may be linear or branched. The divalent aliphatic hydrocarbon group may have an unsaturated bond in the molecule, but is preferably an alkanediyl group. Specific examples of the alkanediyl group include methane-1,1-diyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, pentane-1,1-diyl, and pentane-1,2-diyl. group, pentane-1,3-diyl group, pentane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,1-diyl group, hexane-1,2-diyl group, hexane-1,3-diyl group, hexane-1,4-diyl group, hexane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, and decane-1,10-diyl group. The number of carbon atoms in the divalent alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 16, still more preferably 3 to 12, and particularly preferably 3 to 8. Specific examples include cycloalkylene groups such as cyclopropylene, cyclobutylene, cyclopentylene, and cyclohexylene. Examples of the divalent group in which a divalent aliphatic hydrocarbon group and a divalent alicyclic hydrocarbon group are linked together include a divalent group in which a methane-1,1-diyl group and a cyclohexylene group are linked together, and a divalent group in which an ethane-1,2-diyl group and a cyclohexylene group are linked together. The number of carbon atoms in the divalent aromatic hydrocarbon group is preferably 6 to 18, and more preferably 6 to 12. Specific examples include a phenylene group, a naphthylene group, a phenanthrene group, an anthrylene group, and a fluorenylene group (a divalent group derived from a fluorene ring). The number of carbon atoms in the divalent nitrogen-containing heterocyclic group is preferably 4 to 18, and more preferably 4 to 10. Specific examples include a pyridinylene group (a divalent group derived from a pyridine ring), a pyrimidinylene group (a divalent group derived from a pyrimidine ring), an acridinylene group (a divalent group derived from an acridine ring), and a divalent group derived from a carbazole ring. The bonding site of the divalent alicyclic hydrocarbon group, the bonding site of the divalent aromatic hydrocarbon group, and the bonding site of the divalent nitrogen-containing heterocyclic group may be on any carbon atom on the ring. R in equation (13) 27 , R in Equation (14) 30 Examples of the substituent in include a halogen atom and a carboxyl group.

[0105] In equation (13), R 28 and R 29 R are each independently a substituted or unsubstituted hydrocarbon group. 28 and R 29 The hydrocarbon group represented by the above R 6 and R 7 Similarly to the above, R is a concept that encompasses aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be linear, branched, or cyclic, and may be a saturated or unsaturated hydrocarbon group, and may have an unsaturated bond at either a terminal or a non-terminal. 28 and R 29 The hydrocarbon group represented by is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 4). Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. 28 and R 29 The substituent in the formula (I) can be, for example, a halogen atom. In formula (13), p and q each independently represent an integer of 0 to 4. p and q are preferably 0 or 1, and more preferably 0. When p is an integer of 2 to 4, p R 28 may be the same or different, and when q is an integer of 2 to 4, q R29 may be the same or different.

[0106] Specific examples of the diamine compound include bis(4-aminophenylethyl) adipate, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 4,4'-diaminodiphenyl ether, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 9,9-bis(4-aminophenyl)fluorene, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4'-(p-phenylenediisopropylidene)bisaniline, 4,4'-(m-phenylenediisopropylidene)bisaniline, 1,4-bis(4-aminophenoxy)phenyl ... ) benzene, 4,4'-bis(4-aminophenoxy)biphenyl, 1-(4-aminophenyl)-2,3-dihydro-1,3,3-trimethyl-1H-inden-5-amine, 1-(4-aminophenyl)-2,3-dihydro-1,3,3-trimethyl-1H-inden-6-amine, ethylenediamine, 1,3-propanediamine, tetramethylenediamine, hexamethylenediamine, 4-(2-aminoethyl)cyclohexylamine, 1,11-diamino-3,6,9-trioxaundecane, p-phenylenediamine, 1,5-diaminonaphthalene, 2,7-diaminofluorene, 3,5-diaminobenzoic acid, 2,6-diaminopyridine, 3,4-diaminopyridine, 2,4-diaminopyrimidine, 3,6-diaminoacridine, 3,6-diaminocarbazole, and the like.

[0107] The biguanide compound may be any compound having at least one biguanide skeleton in the molecule, and may be a low molecular weight compound containing one biguanide skeleton, or a compound having multiple repeating units containing a biguanide skeleton, such as polyhexamethylene biguanide. Among these, low molecular weight compounds containing one biguanide skeleton are preferred in order to enhance antiviral activity and antibacterial / fungicidal activity. Examples of low molecular weight compounds containing one biguanide skeleton include those represented by the following formula (15):

[0108] [ka]

[0109] [In formula (15), R 31 represents an organic group.

[0110] R 31 The organic group represented by the formula (I) is preferably a substituted or unsubstituted hydrocarbon group. R 31 The hydrocarbon group represented by the above R 6 and R 7 Similarly to the above, the term "aliphatic hydrocarbon group" is a concept that encompasses aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be linear, branched, or cyclic, and may be a saturated or unsaturated hydrocarbon group, and may have an unsaturated bond at either a terminal or a non-terminal. The aliphatic hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 6, and particularly preferably 1 to 4 carbon atoms). Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. The alicyclic hydrocarbon is preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms (preferably 3 to 12), and more preferably a cycloalkyl group having 3 to 20 carbon atoms (preferably 3 to 12). Specific examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms (preferably 6 to 10), and more preferably an aryl group having 6 to 20 carbon atoms (preferably 6 to 10), and an aralkyl group having 7 to 20 carbon atoms (preferably 7 to 16). The aryl group refers to a monocyclic to tricyclic aromatic hydrocarbon group, such as a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, etc. Specific examples of the aralkyl group include a benzyl group, a phenethyl group, an α-methylbenzyl group, a 2-phenylpropan-2-yl group, etc. Among these, R 31 The hydrocarbon group in is preferably an alkyl group having 1 to 12 carbon atoms (more preferably 1 to 6, particularly preferably 1 to 4), or an aryl group having 6 to 10 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. In addition, R 31 Examples of the substituent in the formula (I) include an alkyl group having 1 to 6 carbon atoms (such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group), a halogen atom, and an alkoxy group having 1 to 6 carbon atoms.

[0111] Specific preferred examples of biguanide compounds include ethylbiguanide, 1-butylbiguanide, 1-octadecylbiguanide, phenylbiguanide, 1-o-tolylbiguanide, 1-p-tolylbiguanide, 1-(2-phenylethyl)biguanide, 1-(2,3-xylyl)biguanide, and 1-(4-methoxyphenyl)biguanide.

[0112] The amino acids and amino acid derivatives include known amino acids and amino acid derivatives. Antiviral drugs include oseltamivir and acyclovir. Peptides and antibacterial drugs include known oligopeptides, polypeptides, peptide structures, and antibiotics containing primary and secondary amino groups. The amino acid derivative is preferably an N-acylamino acid, more preferably an N-alkanoylamino acid. The alkanoyl group in the N-alkanoylamino acid is preferably an alkanoyl group having 2 to 10 carbon atoms, more preferably an alkanoyl group having 2 to 6 carbon atoms. Specific examples of the alkanoyl group include an acetyl group and a propionyl group. The amino acid derivative is particularly preferably an N-acetylamino acid. Specific examples of amino acids, amino acid derivatives, peptides, and antibacterial agents include lysine, glycine, alanine, glutamine, glutamic acid, N-acetyl-L-glutamine, N-acetyl-L-glutamic acid, polylysine, glycylglycine, glycylsarcosine, glutathione, L-alanyl-L-glutamine, daptomycin, vancomycin, colistin, ampicillin, cefditoren pivoxil, cephalosporin C, aztreonam, tigemonam, strepmycin, gentamicin, arbekacin, minocycline, tosflosaxin, trimethoprim, sulfamethoxazole, acyclovir, valacyclovir, lamivudine, and nystatin. Examples of amino sugars and polyamino sugars include glucosamine, galactosamine, mannosamine, hexosamine, chitosan, and the like.

[0113] The content of the specific partial structure is preferably from 1 to 60% by mass, more preferably from 3 to 55% by mass, and particularly preferably from 5 to 50% by mass, based on the total amount of the specific polymer. The mass ratio of the content of the specific polymer chain to the content of the specific partial structure is preferably from 40 / 60 to 99 / 1, more preferably from 45 / 55 to 97 / 3, and particularly preferably from 50 / 50 to 95 / 5. The content of the specific partial structure can be measured by pyrolysis gas chromatography or the like.

[0114] Next, a method for producing the specific polymer will be described. The specific polymer can be produced by appropriately combining known methods described in WO2016 / 013370 pamphlet, WO2017 / 104676 pamphlet, and the like. For example, when producing a terminally unmodified polymer, (step 1-1) a monomer that provides the repeating unit (1B) is polymerized (together with a monomer that provides the repeating unit (2) as needed), and (step 1-2) the polymer having the repeating unit (1B) obtained in step 1-1 is reacted with a haloalkane such as chlorobutane, chlorooctane, or chlorododecane. Alternatively, a terminally unmodified polymer can also be produced by a method including a step of (step 2-1) polymerizing a monomer that provides the repeating unit (1A) (together with a monomer that provides the repeating unit (1B) and a monomer that provides the repeating unit (2) as needed).

[0115] Furthermore, when a polymer having a specific partial structure is produced as the specific polymer, it can be produced, for example, by a method including the following steps 3-1 to 3-3. (Step 3-1) A step of polymerizing a monomer that provides the repeating unit (1B) (together with a monomer that provides the repeating unit (2) as needed) using a polymerization initiator having a cyclic ether group in the molecule or a chain transfer agent having a cyclic ether group in the molecule. (Step 3-2) A step of contacting the cyclic ether group-containing polymer obtained in Step 3-1 with a compound containing a specific functional group to react the cyclic ether group with the specific functional group. (Step 3-3) A step of reacting the repeating unit (1B) and the polymer containing the specific partial structure obtained in Step 3-2 with a haloalkane such as chlorobutane, chlorooctane, or chlorododecane.

[0116] The polymerization reactions in steps 1-1, 2-1, and 3-1 are preferably living polymerizations. As the living polymerization method, known methods such as living radical polymerization and living anionic polymerization can be used.

[0117] Examples of the monomer that provides the repeating unit (1A) include (meth)acryloylaminopropyltrimethylammonium chloride, (meth)acryloylaminopropyldimethyl n-octylammonium chloride, (meth)acryloylaminopropyl n-butyldimethylammonium chloride, (meth)acryloylaminopropyldimethyldodecylammonium chloride, (meth)acryloylaminopropyltriethylammonium chloride, (meth)acryloylaminopropyldiethyl n-octylammonium chloride, (meth)acryloylaminopropyl n-butyldiethylammonium chloride, (meth)acryloylaminopropyldiethyldodeca Examples of suitable ammonium chloride include (meth)acryloyloxyethyl trimethyl ammonium chloride, (meth)acryloyloxyethyl dimethyl n-octyl ammonium chloride, (meth)acryloyloxyethyl n-butyl dimethyl ammonium chloride, (meth)acryloyloxyethyl dimethyl dodecyl ammonium chloride, (meth)acryloyloxyethyl triethyl ammonium chloride, (meth)acryloyloxyethyl diethyl n-octyl ammonium chloride, (meth)acryloyloxyethyl n-butyl diethyl ammonium chloride, and (meth)acryloyloxyethyl diethyl dodecyl ammonium chloride.

[0118] Examples of monomers that provide the repeating unit (1B) include dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, diethylaminopropyl (meth)acrylate, and the corresponding (meth)acrylamides.

[0119] Among the monomers that give the repeating unit (2), examples of the monomer that gives the repeating unit (2) in which A is an aromatic hydrocarbon group include styrene and α-methylstyrene. 10 ~R 12 Examples of monomers that give the repeating unit (2) in which is a hydrocarbon group include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, cyclohexenyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] (meth)acrylic acid esters such as decan-8-yl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, decahydro-2-naphthyl (meth)acrylate, and pentacyclopentadecanyl (meth)acrylate; (meth)acrylamides corresponding thereto; and vinyl ethers such as ethyl vinyl ether. 10 ~R 12is a group having a chain or cyclic ether structure, examples of the monomer that gives the repeating unit (2) include polyethylene glycol (n=2 to 10) methyl ether (meth)acrylate, polypropylene glycol (n=2 to 10) methyl ether (meth)acrylate, polyethylene glycol (n=2 to 10) ethyl ether (meth)acrylate, polypropylene glycol (n=2 to 10) ethyl ether (meth)acrylate, polyethylene glycol (n=2 to 10) mono(meth)acrylate, polypropylene glycol (n=2 to 10) mono(meth)acrylate Examples of the esters include (meth)acrylic acid esters having a chain or cyclic ether structure, such as acrylate, ethylene oxide-modified (meth)acrylate of para-cumylphenol, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-[(meth)acryloyloxymethyl]oxetane, 3-[(meth)acryloyloxymethyl]-3-ethyloxetane, and tetrahydrofurfuryl (meth)acrylate; (meth)acrylamides corresponding to these; and vinyl ethers, such as 3-(vinyloxymethyl)-3-ethyloxetane. These may be used alone or in combination of two or more.

[0120] Furthermore, examples of monomers that provide repeating units other than the repeating unit (1) and the repeating unit (2) include (meth)acrylic acid, maleic acid, maleic anhydride, styrenesulfonic acid, 2-(meth)acrylamido-2-methylpropanesulfonic acid, allylsulfonic acid, vinylsulfonic acid, (meth)acrylicsulfonic acid, sulfopropyl(meth)acrylate, succinic acid mono[2-(meth)acryloyloxyethyl], ω-carboxypolycaprolactone mono(meth)acrylate, and p-vinylbenzoic acid. Examples of suitable monomers include vinyl monomers having an acidic group such as p-hydroxystyrene and p-hydroxy-α-methylstyrene; N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide; (meth)acrylic acid esters having a hydroxyl group such as 2-hydroxyethyl (meth)acrylate, glycerol mono(meth)acrylate and 4-hydroxyphenyl (meth)acrylate; and (meth)acrylamide monomers such as (meth)acrylamide and N-methylolacrylamide. These may be used alone or in combination of two or more.

[0121] A polymerization initiator having a cyclic ether group in the molecule or a chain transfer agent having a cyclic ether group in the molecule can be synthesized as follows. That is, a lithium dialkylamide such as lithium diisopropylamide is reacted with a fatty acid alkyl ester such as methyl isobutyrate to obtain an ester enolate, and this ester enolate is then reacted with a compound having a cyclic ether group and an unsaturated bond such as glycidyl (meth)acrylate. Alternatively, a lithium dialkylamide such as lithium diisopropylamide can be reacted with a compound having a cyclic ether group and an unsaturated bond such as glycidyl (meth)acrylate.

[0122] As the compound containing the specific functional group, those compounds mentioned as those that give the specific partial structure may be used. Step 3-2 may be carried out in the presence of an organic phosphorus compound. The organic phosphorus compound is preferably triphenylphosphine or a derivative thereof, such as triphenylphosphine, tris(3-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, tris(3,5-dimethylphenyl)phosphine, diphenyl(pentafluorophenyl)phosphine, tris(pentafluorophenyl)phosphine, tris(4-chlorophenyl)phosphine, or tris[4-(methylthio)phenyl]phosphine. These compounds may be used alone or in combination of two or more.

[0123] The steps may be carried out in the presence or absence of a solvent, which may include water; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, and t-butyl alcohol; ethylene glycol derivatives such as ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether; propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and propylene glycol monomethyl ether. ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone, diisobutyl ketone, and cyclohexanone; esters such as ethyl acetate, butyl acetate, isobutyl acetate, ethyl lactate, and γ-butyl lactone; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, hexamethylphosphoric triamide, 1,3-dimethyl-2-imidazoline, N,N'-dimethylpropylene urea, tetramethyl urea, and N-methylpyrrolidone; sulfoxides such as dimethyl sulfoxide; aromatic hydrocarbons such as toluene, xylene, and nitrobenzene; and ethers such as tetrahydrofuran, 1,3-dioxolane, diethyl ether, and morpholine. These may be used alone or in combination of two or more. In each of the above steps, the isolation of each reaction product may be carried out, as necessary, by an appropriate combination of conventional means such as filtration, washing, drying, recrystallization, reprecipitation, dialysis, centrifugation, extraction with various solvents, neutralization, chromatography, etc.

[0124] The specific polymer of the present invention has antiviral activity and is useful as an antiviral agent and an antiviral material. The polymer of the present invention also has antibacterial or bactericidal effect and is useful as an antibacterial and / or bactericidal agent and an antibacterial and / or bactericidal material. Furthermore, when applied to an article or the like, the polymer is unlikely to discolor the article or the like.

[0125] As used herein, the term "antiviral" refers to an action that reduces or eliminates the activity of a virus and eliminates its ability to infect host cells. Viruses include all types of viruses, regardless of the type of nucleic acid (RNA, DNA) or whether they are enveloped or not. Viruses that have an envelope and RNA as their nucleic acid include influenza viruses (types A and B), avian influenza viruses, coronaviruses, SARS coronaviruses, SARS coronavirus-2, MERS coronaviruses, feline coronaviruses, canine coronaviruses, respiratory syncytial viruses; mumps viruses, Lassa viruses, dengue viruses, rubella viruses, and human immunodeficiency viruses. Examples of viruses that have an envelope and DNA as nucleic acid include human herpesvirus, vaccinia virus, and hepatitis B virus. Examples of non-enveloped viruses that have RNA as nucleic acid include norovirus, poliovirus, echovirus, hepatitis A virus, hepatitis E virus, rhinovirus, astrovirus, rotavirus, coxsackievirus, enterovirus, and sapovirus. Examples of non-enveloped viruses that have DNA as nucleic acid include adenovirus, B19 virus, papovavirus, human papillomavirus, and canine parvovirus. Among these, the specific polymer of the present invention is suitable for antiviral effects against enveloped viruses, more suitable for antiviral effects against enveloped viruses having RNA as nucleic acid, further suitable for antiviral effects against viruses selected from influenza viruses, coronaviruses, SARS coronaviruses, and SARS coronavirus-2, and particularly suitable for antiviral effects against viruses selected from influenza viruses and coronaviruses.

[0126] Furthermore, fungi are broadly classified into bacteria and fungi, and the specific polymer of the present invention is particularly useful for inhibiting the growth of bacteria, including gram-positive and gram-negative bacteria. Examples of Gram-positive bacteria include bacteria of the genus Propionibacterium or Cutibacterium; bacteria of the genus Corynebacterium such as Corynebacterium xerosis; Staphylococcus bacteria such as Staphylococcus aureus; bacteria of the genus Mycobacterium such as Mycobacterium avium and Mycobacterium tuberculosis; bacteria of the genus Listeria; bacteria of the genus Bacillus such as Bacillus subtilis; and bacteria of the genus Alicyclobacillus. Examples of Gram-negative bacteria include Escherichia bacteria such as Escherichia coli, Salmonella bacteria, Vibrio bacteria, Pseudomonas bacteria such as Pseudomonas aeruginosa, Acinetobacter bacteria such as Acinetobacter baumannii, and Klebsiella bacteria such as Klebsiella pneumoniae. The compound is also effective against drug-resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) and carbapenem-resistant Enterobacteriaceae.

[0127] Therefore, the specific polymer of the present invention can be used as an antiviral agent, antiviral material, antibacterial and / or bactericidal agent, or antibacterial and / or bactericidal material, either as is or in combination with other components as necessary. Furthermore, the specific polymer of the present invention can be used for antiviral, antibacterial, and / or bactericidal purposes, and can also be used to produce an antiviral agent, antibacterial and / or bactericidal agent. Furthermore, examples of the subject of the above-mentioned "use" include, in addition to articles, humans, non-human animals, specimens derived from humans or non-human animals, etc. Among these, the specific polymer of the present invention is suitable for antiviral, antibacterial, and / or sterilizing purposes for articles. For example, even when the specific polymer is used to form threads or nonwoven fabrics, antiviral, antibacterial, and / or sterilizing properties are exhibited. When used in humans or non-human animals, the use is preferably non-therapeutic (non-medical) use. Examples of the above-mentioned items include medical supplies such as medical equipment and medical instruments (e.g., masks, surgical gowns, surgical drapes, blood bags, wound dressings, catheters, infusion tubes, blood bags, dressings, implants, etc.); clothing; daily necessities such as toilet supplies, kitchen supplies, cosmetics, bathroom supplies, and hygiene products (e.g., contact lenses, shower curtains, bathtubs, toothbrushes, diapers, bed sheets, towels, trash cans, corner sinks, chairs, etc.); home appliances such as computers, air conditioners, and refrigerators; interior walls and flooring materials for homes, hospitals, elderly care facilities, food factories, and interior paints for these; operating parts (touch panels, touch screens, etc.) of devices (smartphones, tablet devices, car navigation systems, etc.); packaging materials for food and beverages and medical instruments (e.g., plastic bottles, etc.); building materials such as wallpaper, tiles, and doorknobs; and ship hulls. It should be noted that the term "non-therapeutic" does not include medical procedures, i.e., methods of operating, treating, or diagnosing humans, and more specifically, does not include methods of operating, treating, or diagnosing humans by a physician, medical professional, or a person under the direction of a physician.

[0128] [Antiviral agents, antibacterial and / or bactericidal agents, antiviral materials, antibacterial and / or bactericidal materials] The antiviral agent and the antibacterial and / or bactericidal agent of the present invention contain a specific polymer as an active ingredient. The antiviral material and the antibacterial and / or bactericidal material of the present invention contain a specific polymer. The content of the specific polymer is 10% of the total amount of the antiviral, antibacterial and / or disinfectant. -8 The content is preferably from 0.0001 to 5% by mass, more preferably from 0.005 to 1% by mass, and particularly preferably from 0.001 to 0.1% by mass.

[0129] The antiviral material, antibacterial and / or bactericidal material of the present invention contains a specific polymer, and is a material in any form such as a solution, dispersion, gel, capsule, pellet, film, sheet, fiber, or thread, in which the specific polymer is used in combination with other components. For example, the specific polymer can be used in combination with solvents such as water and organic solvents; surfactants such as anionic, cationic, and nonionic surfactants; thickeners such as gelatin, polysaccharides, and cellulose; and curable monomers such as polyfunctional acrylates and polyfunctional epoxy compounds to form antiviral coating materials, and antibacterial and / or sterilizing coating materials. From the viewpoints of blend stability and functional expression, it is preferable to use the specific polymer by blending it with aqueous coating materials disclosed in, for example, JP-A Nos. 2004-10779, 2008-248014, 9-111151, and 2012-149141. Antiviral coating materials and antibacterial and / or bactericidal coating materials can be used, for example, as coating materials for medical supplies such as medical devices and medical implements; coating materials for daily necessities such as toilet supplies and kitchen utensils; coating materials for home appliances such as personal computers, air conditioners, and refrigerators; interior walls and flooring materials for homes, interior paints for hospitals, elderly care facilities, food factories, etc., as well as coating materials for ship hulls and touch screen panels.

[0130] Furthermore, by blending specific polymers with organic polymer materials such as polyolefins, polyurethanes, ABS, polystyrene, polycarbonates, polyesters, polyamides, acrylic polymers, vinyl chloride, silicones, and cellulose, or by surface-treating molded articles made from these organic polymer materials or inorganic materials such as metals and ceramics with the specific polymers, materials such as plastics, films, fibers, threads, rubber, ceramics, and glass that have been imparted with antiviral properties, or materials such as plastics, films, fibers, threads, rubber, ceramics, and glass that have been imparted with antibacterial and / or bactericidal properties, can be obtained. Such materials can be used, for example, in medical supplies such as masks, surgical gowns, surgical drapes, blood bags, and wound dressings; everyday items such as bed sheets, towels, trash cans, corner sinks, and chairs; and touch panel devices such as smartphones, tablets, and car navigation systems. They can also be used as building materials such as wallpaper, tiles, and doorknobs; and packaging materials for food and beverages and medical devices (such as plastic bottles).

[0131] [Antiviral, antibacterial and / or disinfectant methods] The antiviral, antibacterial and / or sterilizing method of the present invention uses a specific polymer. The method is not particularly limited, but examples include a method including a step of applying a liquid composition containing a specific polymer and a solvent to the surface of an object, thereby imparting antiviral, antibacterial, and / or bactericidal properties to the object. In this case, the liquid composition containing the specific polymer can be blended with a solvent as well as a surfactant, a thickener, a curable monomer, etc. Typical application methods include spray coating, coater coating, dipping, brush coating, and roll coating. Examples of the object include substrates such as films, resin substrates, fibers, threads, ceramics, metals, glass, and wood; interiors such as walls, floors, and ceilings; medical devices such as catheters, infusion tubes, blood bags, and dressings; and tableware or kitchen utensils such as tableware. The content of the specific polymer is 10% by weight based on the total amount of the liquid composition. -8The content is preferably from 0.0001 to 5% by mass, more preferably from 0.005 to 1% by mass, and particularly preferably from 0.001 to 0.1% by mass.

[0132] Furthermore, it is also possible to impart antiviral, antibacterial, and / or bactericidal properties to an object, or to inactivate viruses or sterilize the object, by a method including a step of spraying the liquid composition containing the specific polymer onto the object using a spray, etc. In this case, the liquid composition containing the specific polymer may contain, in addition to a solvent, a surfactant, a fragrance, etc.

[0133] Furthermore, a method including a step of cleaning an object using a cleaning agent containing the specific polymer can be used to clean the object and also to inactivate viruses or to provide antibacterial and / or sterilizing properties. The form of the cleaning agent is not particularly limited, and it may be solid or liquid. In addition to the solvent, the cleaning agent may contain surfactants, fragrances, and the like, as described above.

[0134] Furthermore, a method including the step of immersing an object such as a contact lens in a liquid composition containing the specific polymer can be used to inactivate viruses or sterilize / disinfect the object. A method including the step of impregnating a nonwoven fabric with the liquid composition containing the specific polymer and wiping the object can also be used to inactivate viruses or sterilize the object. In this case, the liquid composition containing the specific polymer can contain, in addition to a solvent, a surfactant, a fragrance, an enzyme, a buffer solution, etc.

[0135] Furthermore, by using a method including a step of blending a specific polymer with an organic polymer material, it is possible to produce materials such as plastics, films, fibers, threads, and rubber that have been given antiviral, antibacterial, and / or bactericidal properties.

[0136] Furthermore, by adding the specific polymer of the present invention to a composition for producing a three-dimensional object such as an implant, it is possible to produce an object imparted with antiviral, antibacterial, or bactericidal properties. Furthermore, the surface of an object produced as described above may be coated with a coating material containing the specific polymer of the present invention. Hereinafter, a method for producing an object will be described using a medical implant as an example, but the use of the specific polymer of the present invention is not limited to these examples and may also be applied to any object used as a device.

[0137] For example, medical implants are produced by additive manufacturing (AM) of a dental treatment site (e.g., an affected area) using a radiological tomography method such as a CT scan or a nuclear magnetic resonance imaging (MRI) to obtain three-dimensional information about the shape of the site. Based on this information, a molded object with a shape suitable for treatment is manufactured by AM. Adding the specific polymer of the present invention to the composition from which the molded object is made can impart antiviral, antibacterial, or bactericidal properties to the molded object. For example, molded objects can be produced by a molding method such as (a) laser-based powder molding (powder sintering), (b) powder deposition modeling, (c) fused deposition modeling, (d) lamination layer manufacturing, or (e) stereolithography. Examples of embodiments include adding the specific polymer of the present invention to the composition used in these molding methods.

[0138] (a) Examples of laser-based powder shaping methods include three-dimensional powder shaping (laser-based powder sintering layer-by-layer shaping). Specifically, according to this method, powder containing the specific polymer of the present invention and having an average particle size of 0.001 to 0.3 mm is applied to a support so as to accurately correspond to a predetermined distance and thickness, based on the dimensional information of a three-dimensional model designed in advance using CAD or the like. If necessary, the powder surface may be smoothed using a wiper or the like. Next, a laser such as a carbon dioxide laser is applied to the powder in accordance with the model, melting and solidifying it. This process is repeated while moving the support vertically, thereby forming an object corresponding to the model. The laser used in this shaping method is not particularly limited, and examples include infrared lasers, carbon dioxide lasers, solid-state lasers such as YAG lasers, and excimer lasers. The output power and aperture of these lasers are appropriately selected depending on the biocompatible material used, the shape of the object, and other factors.

[0139] (b) Powder deposition methods include a deposition method, which utilizes inkjet technology used in printers to continuously drip droplets of heated, melted wax or other liquids and deposit and solidify them; a binder method, which ejects a binder from an inkjet head onto metal powder, ceramic powder, starch powder, or gypsum powder to adhere the powders together for layered manufacturing; and a photocuring method, which ejects a resin powder from an inkjet head and then cures it with light. The specific polymer of the present invention can be added to the above-mentioned droplets or powder. For example, multiple cross-sectional views of the affected area are prepared using a radiation-based tomography method such as a CT scan or nuclear magnetic resonance imaging (MRI), and a thin layer (e.g., approximately 0.1 μm) of powder is applied to a sheet. A solidifying agent (e.g., collagen, chondroitin sulfate, hyaluronic acid, elastin, etc.) is sprayed onto the sheet in accordance with the cross-sectional view using an inkjet printer or the like, thereby fixing the powder to the sheet. This process is repeated for each cross-sectional view, and the resulting sheets are stacked to produce a desired shaped object.

[0140] (c) The molten material deposition method includes a method in which the shape of the object to be manufactured is determined based on information about the affected area obtained by a tomography method using radiation such as a CT scan, or by nuclear magnetic resonance imaging (MRI), and then a thermoplastic resin (e.g., polycarbonate resin) to which the specific polymer of the present invention has been added is heated and continuously discharged (e.g., discharged in a linear shape) from a nozzle in a molten state while being scanned with an XY plotter or the like to melt the resin, and the molten resin is extruded, solidified, and layered on a surface. In this method, the resins adhere to each other before hardening.

[0141] (d) Lamination lamination includes a method in which, similar to (c) melt deposition method, the shape of the object to be produced is determined based on information about the affected area, and adhesive-coated sheet materials are stacked and pressed together (for example, by thermocompression) with a roller or the like, and unnecessary portions of the contour are cut off with a laser, knife, or the like, and this process is repeated to produce a film of the desired shape. An example of this method is an embodiment in which the specific polymer of the present invention is added to the adhesive or sheet.

[0142] (e) Stereolithography includes a method for producing a three-dimensional object by curing a liquid photocurable resin layer by layer using a light beam such as a laser and laminating the resin. This method can easily produce complex shapes and objects with high dimensional accuracy. In one embodiment of this method, the specific polymer of the present invention is added to a liquid photocurable resin. [Example]

[0143] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. The abbreviations for the raw materials used in the examples are as follows: THF: tetrahydrofuran GMA: Glycidyl methacrylate MMA: Methyl methacrylate nBMA: normal butyl methacrylate EHMA: 2-ethylhexyl methacrylate DAMA: dimethylaminoethyl methacrylate PGMEA: Propylene glycol monomethyl ether acetate

[0144] (Measurement conditions for Mw and Mw / Mn) The Mw and Mn measured in each of the following synthesis examples are values ​​measured in terms of polystyrene by gel permeation chromatography according to the following specifications. Device: GPC-104 (Showa Denko K.K.) Column: Three LF-604 columns and one KF-602 column were used. Mobile phase: THF Temperature: 40℃ Flow rate: 0.6mL / min.

[0145] (Synthesis Example 1: Synthesis of polymer) According to the following synthesis route, a polymer having a partial structure derived from 2-ethylhexylamine and repeating units derived from DAMA, MMA, nBMA, and EHMA, some of which are quaternary ammonium-modified (quaternary ammonium-modified polymer terminally modified with a partial structure derived from 2-ethylhexylamine) was synthesized.

[0146] [ka]

[0147] [ka]

[0148] Specifically, 125 mL of THF, 1.25 g of lithium chloride, and 3.1 g of methyl isobutyrate were added to a 300 mL flask and cooled to -60 °C. Then, 15.0 mL of a solution of lithium diisopropylamide in THF / heptane / ethylbenzene (volume ratio: 1 / 1 / 1) (lithium diisopropylamide: 2.0 mol / L) was added and stirred for 15 minutes. Next, 4.3 g of GMA was added and stirred for 15 minutes. After that, a mixture of 11.0 g of MMA, 2.5 g of nBMA, 9.0 g of EHMA, and 27.5 g of DAMA was added dropwise, and the reaction was continued for 1 hour. After confirming the disappearance of the monomer by gas chromatography, 1.8 g of methanol was added and stirred for 10 minutes. The reaction temperature was then raised to 25 °C over 2 hours, and 125 mL each of water and ethyl acetate were added for washing, followed by phase separation. The aqueous layer was removed, and the mixture was concentrated under reduced pressure to obtain a 40% by weight PGMEA solution. In this way, a random copolymer pc-1 having terminal epoxy groups and repeating units derived from DAMA, MMA, nBMA, and EHMA was obtained. The resulting polymer had a weight-average molecular weight (Mw) of 2020 and a molecular weight distribution (Mw / Mn) of 1.21.

[0149] Next, 3.1 g of 2-ethylhexylamine, 0.2 g of triphenylphosphine, and 30.0 g of propylene glycol monomethyl ether were added to 100.0 g of the resulting 40% by weight polymer solution, and the mixture was reacted at 60°C for 30 hours to react polymer pc-1 with 2-ethylhexylamine. Next, 14.2 g of chlorooctane was added, followed by gentle stirring. The temperature of the polymer solution was raised to 85°C and maintained at this temperature for 40 hours, partially converting the dimethylamino groups derived from DAMA to quaternary ammonium. High-performance liquid chromatography (HPLC) of the reaction solution confirmed a 70% reduction in the peak derived from chlorooctane. In this way, a polymer was obtained containing a partial structure derived from 2-ethylhexylamine and repeating units derived from DAMA, MMA, nBMA, and EHMA, some of which were converted to quaternary ammonium. The resulting polymer is designated "Polymer (C-1)."

[0150] (Synthesis Example 2: Synthesis of polymer) A polymer was obtained in the same manner as in Synthesis Example 1, except that 8.9 g of chlorobutane was used instead of the chlorooctane used in Synthesis Example 1. The obtained polymer was designated "Polymer (C-2)".

[0151] (Synthesis Example 3: Synthesis of polymer) A polymer was obtained in the same manner as in Synthesis Example 1, except that the amounts of the monomers used in Synthesis Example 1 were changed to 7.5 g of MMA, 5.0 g of nBMA, 7.5 g of EHMA, and 30.0 g of DAMA (the polymer corresponding to polymer pc-1 was designated polymer pc-2), and that chlorooctane was replaced with 21.4 g of chlorododecane. The obtained polymer was designated "Polymer (C-3)." The Mw (weight average molecular weight) of polymer pc-2 was 2080, and the Mw / Mn (molecular weight distribution) was 1.19.

[0152] (Synthesis Example 4: Synthesis of polymer) According to the following synthesis route, a polymer having repeating units derived from DAMA, MMA, nBMA, and EHMA in the polyethyleneimine side chain, some of which are quaternary ammonium-modified (quaternary ammonium-modified polymer terminally modified with a partial structure derived from polyethyleneimine) was synthesized.

[0153] [ka]

[0154] [ka]

[0155] Specifically, 125 mL of THF and 1.25 g of lithium chloride were added to a 300 mL flask and cooled to -60 °C. Then, 15.0 mL of a solution of lithium diisopropylamide in THF / heptane / ethylbenzene (volume ratio: 1 / 1 / 1) (lithium diisopropylamide: 2.0 mol / L) was added and stirred for 15 minutes. Next, 4.3 g of GMA was added and stirred for 15 minutes. After that, a mixture of 7.5 g of MMA, 5.0 g of nBMA, 7.5 g of EHMA, and 30.0 g of DAMA was added dropwise, and the reaction was continued for 1 hour. After confirming the disappearance of the monomer by gas chromatography, 1.8 g of methanol was added and stirred for 10 minutes. The reaction temperature was then raised to 25 °C over 2 hours, and 125 mL each of water and ethyl acetate were added for washing, followed by phase separation. The aqueous layer was removed, and the mixture was concentrated under reduced pressure to obtain a 40% by mass PGMEA solution. In this way, a random copolymer pc-2' having terminal epoxy groups and repeating units derived from DAMA, MMA, nBMA, and EHMA was obtained. The Mw (weight average molecular weight) of the resulting polymer was 2160, and the Mw / Mn (molecular weight distribution) was 1.22.

[0156] Next, 3.1 g of polyethyleneimine 600, 0.2 g of triphenylphosphine, and 30.0 g of propylene glycol monomethyl ether were added to 100.0 g of the resulting 40% by weight polymer solution, and the mixture was reacted at 60°C for 30 hours to react polymer pc-2' with polyethyleneimine 600. Next, 15.5 g of chlorooctane was added, followed by gentle stirring. The temperature of the polymer solution was raised to 85°C and maintained at this temperature for 40 hours, resulting in partial conversion of the dimethylamino groups derived from DAMA to quaternary ammonium. The reaction solution was analyzed by high-performance liquid chromatography, confirming a 40% reduction in the peak derived from chlorooctane. In this way, a polymer was obtained having repeating units derived from DAMA, MMA, nBMA, and EHMA in the polyethyleneimine side chains, some of which were converted to quaternary ammonium. The resulting polymer is designated "Polymer (C-4)."

[0157] (Synthesis Examples 5 to 9: Polymer Synthesis) Polymers were obtained in the same manner as in Synthesis Example 1, except that the 2-ethylhexylamine used in Synthesis Example 1 was changed to 3.4 g of 4-(2-aminoethyl)cyclohexylamine (Synthesis Example 5), 4.6 g of 1,11-diamino-3,6,9-trioxaundecane (Synthesis Example 6), 8.1 g of famotidine (Synthesis Example 7), 4.4 g of 2-butyl-n-octan-1-amine (Synthesis Example 8), or 3.1 g of n-octylamine (Synthesis Example 9). The obtained polymers were designated "Polymer (C-5)", "Polymer (C-6)", "Polymer (C-7)", "Polymer (C-8)", and "Polymer (C-9)", respectively.

[0158] (Synthesis Example 10: Synthesis of Polymer) A polymer was obtained in the same manner as in Synthesis Example 1, except that the amount of 2-ethylhexylamine used in Synthesis Example 1 was changed to 0.9 g. The obtained polymer was designated "Polymer (C-10)".

[0159] (Synthesis Examples 11 to 12: Synthesis of Polymers) Polymers were obtained in the same manner as in Synthesis Example 1, except that the amounts of chlorooctane used in Synthesis Example 1 were changed to 5.7 g (Synthesis Example 11) and 22.7 g (Synthesis Example 12). The obtained polymers were designated "Polymer (C-11)" and "Polymer (C-12)".

[0160] (Comparative Synthesis Example 1: Synthesis of Polymer) A polymer was obtained in the same manner as in Synthesis Example 1, except that 12.1 g of benzyl chloride was used instead of the chlorooctane used in Synthesis Example 1. The obtained polymer was designated "Polymer (P-1)".

[0161] (Comparative Synthesis Example 2: Synthesis of Polymer) A polymer was obtained in the same manner as in Synthesis Example 1, except that the chlorooctane used in Synthesis Example 1 was replaced with 12.1 g of benzyl chloride and the 2-ethylhexylamine was replaced with 14.4 g of polyethyleneimine 600. The obtained polymer was designated "Polymer (P-2)".

[0162] (Synthesis Example 13: Synthesis of polymer (non-amino-terminated polymer)) A 300 mL flask was charged with 125 mL of THF, 1.25 g of lithium chloride, and 3.1 g of methyl isobutyrate and cooled to -60°C. Then, 15.0 mL of a solution of lithium diisopropylamide in THF / heptane / ethylbenzene (volume ratio: 1 / 1 / 1) (lithium diisopropylamide: 2.0 mol / L) was added and stirred for 15 minutes. A mixture of 11.0 g of MMA, 2.5 g of nBMA, 9.0 g of EHMA, and 27.5 g of DAMA was added dropwise, and the reaction was continued for 1 hour. Gas chromatography was then performed to confirm the disappearance of the monomer, after which 1.8 g of methanol was added and the mixture was stirred for 10 minutes. The reaction temperature was then raised to 25°C over 2 hours, and 125 mL each of water and ethyl acetate was added for washing, followed by phase separation and removal of the aqueous layer. The mixture was then concentrated under reduced pressure to obtain a 40% by mass PGMEA solution. In this way, a random copolymer pc-3 having repeating units derived from DAMA, MMA, nBMA, and EHMA was obtained. The resulting polymer had a weight average molecular weight (Mw) of 1830 and a molecular weight distribution (Mw / Mn) of 1.21.

[0163] Next, 14.2 g of chlorooctane was added to 100.0 g of the resulting 40% by weight polymer solution. The mixture was then gently stirred, and the temperature of the polymer solution was raised to 85°C. This temperature was maintained for 40 hours, resulting in partial conversion of the dimethylamino groups derived from DAMA to quaternary ammonium. The reaction solution was analyzed by high-performance liquid chromatography, confirming that the peak derived from chlorooctane had decreased by 40%. In this way, a polymer was obtained containing repeating units derived from DAMA, MMA, nBMA, and EHMA, some of which were converted to quaternary ammonium. The resulting polymer is designated "Polymer (C-13)."

[0164] (Comparative Synthesis Example 3: Synthesis of Polymer) A polymer was obtained in the same manner as in Synthesis Example 13, except that 12.1 g of benzyl chloride was used instead of the chlorooctane used in Synthesis Example 13. The obtained polymer was designated "Polymer (P-3)".

[0165] Table 1 shows the copolymerization ratio (mass %) of each monomer, Mw, and Mw / Mn in polymer pc-1, polymer pc-2, polymer pc-2′, and polymer pc-3. Table 2 shows the amount of each compound used in synthesizing the polymers (C-1) to (C-13) and (P-1) to (P-3) and the DAMA quaternary ammonium conversion rate of each polymer.

[0166] [Table 1]

[0167] [Table 2]

[0168] <Test Example 1: Antiviral Test> To measure the antiviral activity value of the polymer, a 0.1% by mass aqueous solution was prepared and exposed to influenza virus (H3N2 type) for 2 minutes, and the infectivity titer was calculated. That is, 1.1 g of each polymer (C-1 to C-13, P-1 to P-3, pc-1) was weighed out and diluted to 1000 g with sterile water to obtain an aqueous solution with a polymer concentration of 0.11% by mass. 0.9 mL of this aqueous solution and a virus concentration of 3.1 × 10 8 The mixture was mixed with 0.1 mL of a virus suspension (PFU / mL) at 25°C and allowed to stand for 2 minutes. This was used as the test solution. The reaction was then stopped by adding 9 mL of SCDLP medium to 1 mL of the test solution to obtain a reaction stop solution. Next, 1 mL of this reaction stop solution was measured and serially diluted 10-fold with EMEM. The virus infectivity per 0.1 mL of the reaction stop solution was measured by plaque assay, and the virus infectivity per 1 mL of the test solution was calculated. Next, the virus used was changed from influenza virus (H3N2 type) to SARS-CoV-2 (Omicron strain), and the virus concentration was increased to 3.1 × 10 8 PFU / mL to 2.3 × 10 8 The virus infectivity titer for anti-coronavirus activity was calculated using the same procedure as above, except that it was changed to PFU / mL. Next, the virus infectivity was calculated in the same manner as above, except that the virus used was changed from influenza virus (H3N2 type) to influenza virus (H1N1 type). The antiviral activity was evaluated according to the following criteria. The blank refers to the viral infectivity measured using sterilized water instead of the aqueous polymer solution. The results are shown in Table 3.

[0169] (Anti-influenza virus (H3N2, H1N1), anti-coronavirus) Virus infectivity is 1 / 100 or less compared to the blank: A Viral infectivity is more than 1 / 100 and less than 1 / 10 of the blank: B Virus infectivity is more than 1 / 10 of the blank: C

[0170] (Antiviral comprehensive evaluation) Both anti-influenza virus and anti-coronavirus rated "A": Overall rating A Both anti-influenza virus and anti-coronavirus rated "A" or "B" (excluding cases where both rated "A"): Overall rating B At least one of the anti-influenza virus and anti-coronavirus properties has a rating of "C": Overall rating C

[0171] <Test Example 2: Antibacterial and disinfectant test> (Preparation of liquid medium) 30.4 g of medium (Mueller Hinton II) was weighed out and dissolved in 800 mL of sterilized water, and the solution was autoclaved at 121°C and 2 atmospheres for 15 minutes. (Preparation of bacterial solution) The following bacteria (1) to (4) were each suspended in 1 mL of the liquid medium obtained in the above "Preparation of liquid medium" and the OD600 was measured. The bacterial count was 1 x 10 8 Each bacterial solution was prepared by adding liquid medium so that the number of bacteria reached cfu / mL. (1) MRSA (methicillin-resistant S. aureus strains) (2) S. aureus (NBRC12732) (3) E. coli (NBRC3972) (4) Pseudomonas aeruginosa (NBRC106052) (measurement) Each polymer (C-1 to C-13, P-1 to P-3, pc-1) was mixed with water to prepare a 10 mg / mL polymer aqueous solution. 102.4 μL of the polymer aqueous solution was added to 897.6 μL of the prepared liquid medium, resulting in a polymer concentration of 1024 μg / mL. This solution was diluted two-fold in the wells of a 96-well plate to prepare a dilution series ranging from 1024 μg / mL to 0.015625 μg / mL. Next, 5 μL of the bacterial solution was added to each well, and the mixture was incubated at 37°C for 16 hours. The turbidity of each well was visually determined to confirm the growth of bacteria. The concentrations of the dilution series at which it was visually judged that there was no turbidity and that the solution was antibacterial and sterilized are shown in Table 3.

[0172] <Test Example 3: Hue Evaluation> Each polymer was precipitated in hexane, and the precipitate was filtered and dried. A 20% by weight aqueous solution of the polymer was then prepared using ion-exchanged water. The chromaticity values ​​(1 to 18) of this aqueous solution were visually determined at 25°C using a Gardner color meter (product name: Liquid Color Standard, manufactured by BYK-Gardner) and evaluated according to the following criteria. The results are shown in Table 3.

[0173] (Hue evaluation standard) Chromaticity value 1~6: AAA Chromaticity value 7~9: AA Chromaticity value 10~12:A Chromaticity value 13~15:B Chromaticity value 16~18:C

[0174] <Test Example 4: Evaluation of Solubility> Each polymer was mixed with butyl acetate to a concentration of 20% by mass, and the turbidity was visually confirmed after 10 minutes. In the same manner, each polymer was mixed with water to a concentration of 20% by mass, and the turbidity was visually confirmed after 10 minutes had elapsed. The solubility in butyl acetate and water was evaluated by assigning a grade of "A" to samples that showed no turbidity, "B" to samples that showed partial turbidity, and "C" to samples that were mostly turbid and had precipitates. The results are shown in Table 3.

[0175] <Test Example 5: Evaluation of Difficulty in Deliquescence> Polymers C-13 and P-1 were reprecipitated with acetone and then dried at 40°C for 10 hours to obtain powder. This powder was left in the air for 15 minutes, after which its condition was visually inspected. Powders that were fluid were rated "A," while those that were solidified and lacked fluidity were rated "C." The results are shown in Table 3.

[0176] <Test Example 6: Antiviral and antibacterial tests of yarn and nonwoven fabric using polymer> (Preparation of pellets for spinning) To prepare the yarns, polypropylene pellets containing each polymer were prepared. That is, using a small twin-screw extruder (product name: KZ-30MG-NH, manufactured by Technovel Co., Ltd.), polypropylene (product name: Y2005GP, manufactured by Prime Polymer Co., Ltd.) was melted with each polymer at 190°C and injected to obtain polypropylene pellets containing 20% ​​by mass of each polymer.

[0177] (spinning) The polypropylene pellets obtained above were spun using an air-cooled multifilament spinning machine (product name: CMF-2E1H, manufactured by Chubu Machine Co., Ltd.). The specific procedure was as follows. Prime Polymer Y2005GP and polypropylene pellets were mixed to a polymer content of 0.1% by mass. The mixture was spun at an extrusion temperature of 200°C and a throughput rate of 1.4 kg / hr. 24 0.5 mm diameter fibers were bundled and wound at 400 m / min to obtain a filament. The resulting filament was then stretched using a laboratory twisting machine (product name: SD-4, Shimadzu Corporation). The 24 bundled fibers were twisted at a stretching speed of 157 m / min while directly heating the filament with a planar heater at a surface temperature of 110°C, resulting in a strong knot between the 24 fibers. This resulted in a filament for evaluation of antiviral and antibacterial properties.

[0178] (Production of pellets for nonwoven fabric production) Polypropylene pellets containing 10% by mass of each polymer were produced using a small twin-screw extruder (product name: TEM-26SS, manufactured by Shibaura Machine Co., Ltd.). The polypropylene used was HL512FB manufactured by Borealis, and the temperature of the extruder cylinder (inside the kneader) was set to 170°C. The screw rotation speed of the extruder was set to 130 rpm, and the feeder (rotary valve at the outlet) rotation speed was set to 7.7 rpm so that the discharge rate was 5.0 kg / h.

[0179] (Production of nonwoven fabric) The pellets for nonwoven fabric preparation obtained above were made into a nonwoven fabric using a melt-blowing machine (product name: MB-T00, manufactured by Shinwa Kogyo Co., Ltd.) so that the content of each polymer in the finished nonwoven fabric would be 0.1% by mass. The gear pump rotation speed was 10.5 rpm, the collection distance was 175 mm, the collector speed was 3.54 m / min, the hot air volume was 500 l / min, and the basis weight was 30 g / m 2 A nonwoven fabric was produced.

[0180] (evaluation) The evaluation of the yarn and non-woven fabric was carried out in accordance with JIS 1922 (virus) and JIS 1902 (antibacterial), and the antiviral activity value Mv and antibacterial activity value A were calculated by the following methods. For the evaluation of antiviral properties, H3N2 influenza virus was used, and for the evaluation of antibacterial properties, S. aureus (NBRC 12732), E. coli (NBRC 3972), and Pseudomonas aeruginosa (NBRC 106052) were used respectively. The results are shown in Table 3. The evaluation criteria are as shown in the "Antibacterial Activity Value Evaluation Criteria" and "Antiviral Activity Value Evaluation Criteria".

[0181] <Mv: Antiviral activity value> Mv = log(Va) - log(Vc) log(Va): Common logarithm of the virus infectivity titer (PFU / specimen) of the standard cloth immediately after inoculation log(Vc): Common logarithm of the virus infectivity titer (PFU / specimen) of the antiviral processed product after standing for 2 hours

[0182] <A: Antibacterial activity value> Antibacterial activity value (A) = (logCt - logC0) - (logTt - logT0) = F - G

[0183] F: Growth value of the standard cloth (F = logCt - logC0) G: Growth value of the antibacterial processed sample (G = logTt - logT0) ​​​​​​​​​​​​​​​​​

[0185] (Antiviral activity evaluation criteria) Antiviral activity value of yarn and nonwoven fabric containing 0.1% by mass of polymer is "3 or more": Rating AA Antiviral activity value of yarn and nonwoven fabric containing 0.1% by mass of polymer is "2 or more but less than 3": Evaluation A Antiviral activity value of yarn and nonwoven fabric containing 0.1% by mass of polymer is "less than 2": Evaluation C

[0186] [Table 3]

Claims

1. A polymer having a polymer chain having a repeating unit represented by the following formula (1A): 【Chemistry 1】 [In formula (1A), R 1 represents a hydrogen atom or a methyl group, Z 1 is -N + R 2 R 3 R 4 Y y- (R 2 ~R 4 each independently represents an alkyl group; Y y- represents a y-valent counter anion.) X 1 represents a single bond or a divalent linking group.

2. R in formula (1A) 2 ~R 4 2. The polymer according to claim 1, wherein at least one of the following is an alkyl group having 5 to 30 carbon atoms:

3. 2. The polymer according to claim 1, wherein the polymerization ratio of the repeating unit represented by formula (1A) contained in the polymer chain is 3% by mass or more and 37% by mass or less of all repeating units contained in the polymer chain.

4. The polymer according to claim 1 , wherein the polymer chain further comprises a repeating unit represented by the following formula (1B): 【Chemistry 2】 [In formula (1B), R ５ represents a hydrogen atom or a methyl group, Z ２ is -NR ６ R ７ (R ６ and R ７ each independently represents a substituted or unsubstituted hydrocarbon group. X ２ represents a single bond or a divalent linking group.

5. The polymer according to claim 1 , wherein the polymer chain further comprises a repeating unit represented by the following formula (2): 【Transformation 3】 [In formula (2), R ９ represents a hydrogen atom or a methyl group, A is an aromatic hydrocarbon group, -(C=O)OR １０ , -(C=O)NHR １１ , or -OR １２ (R １０ ~R １２ each independently represents a hydrocarbon group or a group having a linear or cyclic ether structure.

6. The polymer according to claim 1, further comprising a partial structure (excluding the polymer chain) derived from a compound containing a group represented by —NH—.

7. The polymer according to claim 6, wherein the compound containing a group represented by —NH— is represented by the following formula (12) or (14): 【Chemistry 4】 [In formula (12), R ２６ represents a substituted or unsubstituted hydrocarbon group. 【Transformation 5】 [In formula (14), R ３０ represents a substituted or unsubstituted divalent hydrocarbon group, or a substituted or unsubstituted divalent hydrocarbon group in which some of the carbon atoms have been replaced with ether bonds.

8. The polymer according to claim 1, which is a terminally non-amino-modified polymer.

9. An antiviral agent comprising the polymer according to any one of claims 1 to 8 as an active ingredient.

10. The antiviral agent according to claim 9, which is an antiviral agent selected from an anti-influenza virus agent and an anti-coronavirus agent.

11. An antiviral material containing the polymer according to any one of claims 1 to 8.

12. An antiviral method using the polymer according to any one of claims 1 to 8.

13. An antibacterial agent, a bactericide, or an antibacterial and bactericide, which contains the polymer according to any one of claims 1 to 8 as an active ingredient.

14. An antibacterial, bactericidal or antibacterial and bactericidal material, comprising the polymer according to any one of claims 1 to 8.

15. An antibacterial method, a sterilization method, or an antibacterial and sterilization method, which uses the polymer according to any one of claims 1 to 8.

Images