Antibacterial agent

Abstract

To provide a novel antibacterial agent.SOLUTION: An antibacterial agent contains a compound represented by the formula (1), wherein R1-R18 independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group, and n1 is an integer of 1-30.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel antimicrobial agent and an antimicrobial article containing the agent. [Background technology]

[0002] In recent years, interest in antibacterial agents has been increasing from the viewpoint of maintaining safety for the living environment and the human body. Antibacterial agents are used in a wide variety of applications, such as cosmetics, cleaning agents, paints, resins, and everyday items. Known antibacterial agents include organic antibacterial agents (e.g., Patent Document 1) and inorganic antibacterial agents (e.g., Patent Document 2), and as organic antibacterial agents, antibacterial agents in which organic compounds are coordinated to metal atoms have been developed (e.g., Patent Document 3). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 06-157014 [Patent Document 2] Japanese Patent Application Publication No. 10-316518 [Patent Document 3] JP 2023-94098 A Summary of the Invention [Problem to be solved by the invention]

[0004] As the demand for organic antibacterial agents is increasing, there is a need to develop new organic antibacterial agents.

[0005] It is therefore an object of the present invention to provide a novel antimicrobial agent and an antimicrobial article containing said agent. [Means for solving the problem]

[0006] Means of the Invention The present inventors have conducted extensive research to solve the above problems and have found that a specific compound represented by formula (1) is useful as an antibacterial agent, thereby completing the present invention. [1] Formula (1): [ka] [In the formula, R 1 ~R 18 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group, and n1 is an integer of 1 to 30. An antibacterial agent comprising a compound represented by the formula: [2] The antibacterial agent according to [1], wherein the compound represented by formula (1) has a number average molecular weight Mn of 900 to 14,000. [3] Formula (2): [ka] [In the formula, R 19 ~R 36 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group; n2 is an integer of 1 to 30; M is a transition metal or an ion thereof; m is an integer of 0 to 4; and each X independently represents a monodentate ligand, provided that when m is 2 or more, two or more Xs may combine together to form a polydentate ligand. The antibacterial agent according to [1] or [2], further comprising a compound represented by the following formula: [4] The antibacterial agent according to [3], wherein the content ratio of the compound represented by formula (1) to the compound represented by formula (2) is 99.9:0.1 to 0.1:99.9 in terms of molar ratio. [5] The antibacterial agent according to [3] or [4], wherein in formula (2), M is Pt, X is a halide, and m is 2. [6] The antibacterial agent according to any one of [1] to [5], which is an antibacterial agent against at least one species selected from the group consisting of bacteria and viruses. [7] An antibacterial article comprising the antibacterial agent according to any one of [1] to [6]. [8] The antibacterial article described in [7], further comprising resin and / or glass. [9] An antibacterial article according to [7] or [8], comprising a main body and a coating layer formed on at least a portion of the surface of the main body, the coating layer containing the antibacterial agent.

[10] The antibacterial article according to any one of [7] to [9], wherein the content of the antibacterial agent is 0.01 mass % or more based on the mass of the antibacterial article.

[11] The content of the antibacterial agent is within 1 cm of the surface of the article body. 2 The antibacterial article according to [9] or

[10] , wherein the antibacterial activity is 1 μmol or more per unit area. Effect of the Invention

[0007] According to the present invention, a novel antibacterial agent is provided. [Brief description of the drawings]

[0008] [Figure 1] 1 shows the CD spectra and UV-vis absorption spectra of the compounds obtained in Examples 1 and 2. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] Hereinafter, the embodiments of the present invention will be described in detail. Note that the scope of the present invention is not limited to the embodiments described here, and various modifications can be made without departing from the spirit of the present invention. Note that the upper and lower limit values ​​described in this specification can be arbitrarily combined to form a suitable numerical range.

[0010] [Antibacterial agents] The antibacterial agent of the present invention has the following formula (1): [ka] [In the formula, R 1 ~R 18 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group, and n1 is an integer of 1 to 30. The compound includes a compound represented by the formula (1).

[0011] The present inventors have been investigating the antibacterial activity of compound (1), and have unexpectedly found that compound (1) exhibits excellent antibacterial properties. It was surprising that compound (1) can exhibit excellent antibacterial properties even in the absence of metal coordination. Although the reason for this is unclear, it is presumed that compound (1) can effectively inhibit the enzyme activity in fungi and viruses.

[0012] <Compound (1)> In formula (1), R 1 ~R 18 Examples of the halogen atom in include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0013] In formula (1), R 1 ~R 18 In the formula, examples of the alkyl group include alkyl groups having 1 to 12 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-methyl-butyl, 3-methylbutyl, 2-ethyl-propyl, and n-hexyl. Among these, from the viewpoint of enhancing antibacterial properties, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. The alkyl groups can be used alone or in combination of two or more kinds.

[0014] In formula (1), R 1 ~R 18 Examples of the alkoxy group in include alkoxy groups having 1 to 12 carbon atoms, such as methoxy, ethoxy, propyloxy, isopropyloxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, and cyclohexyloxy. Among these, from the viewpoint of enhancing antibacterial properties, the alkoxy group is preferably an alkoxy group having 1 to 6 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, and even more preferably a methoxy or ethoxy group. The alkoxy groups can be used alone or in combination of two or more kinds.

[0015] In formula (1), R 1 ~R 18 In the formula, examples of the aryl group include aryl groups having 6 to 18 carbon atoms, such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and a biphenyl group. Among these, from the viewpoint of antibacterial properties, the aryl group is preferably an aryl group having 6 to 12 carbon atoms, and more preferably a phenyl group, a naphthyl group, or a biphenyl group. The aryl groups can be used alone or in combination of two or more kinds.

[0016] In formula (1), R 1 ~R 18 Examples of the aryloxy group in the formula (I) include aryloxy groups having 6 to 18 carbon atoms, such as a phenoxy group, a naphthyloxy group, and a biphenyloxy group, and preferably an aryloxy group having 6 to 12 carbon atoms. The aryloxy groups can be used alone or in combination of two or more kinds.

[0017] In formula (1), R 1 ~R 18 Examples of the aralkyl group in include aralkyl groups having 6 to 22 carbon atoms, such as benzyl and phenethyl, and preferably aralkyl groups having 6 to 14 carbon atoms. The aralkyl groups can be used alone or in combination of two or more kinds.

[0018] In formula (1), R 1 ~R 18 Examples of the aralkyloxy group in include aralkyloxy groups having 6 to 22 carbon atoms, such as benzyloxy and phenethyloxy, and preferably aralkyloxy groups having 6 to 14 carbon atoms. The aralkyloxy groups can be used alone or in combination of two or more kinds.

[0019] These R 1 ~R 18 Among them, from the viewpoint of enhancing antibacterial properties, R 1 ~R 18are each independently preferably at least one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, and an aryl group, more preferably at least one selected from the group consisting of a hydrogen atom, an alkyl group, and an alkoxy group, further preferably a hydrogen atom and / or an alkyl group, and particularly preferably a hydrogen atom. 1 ~R 18 are preferably all hydrogen atoms. 1 ~R 18 By appropriately changing the substituents of the formula (1), the color tone of the compound (1) can be changed.

[0020] In formula (1), n1 is an integer of 1 to 30. When n1 is 2 or more, n1 represents the number of repeating units. n1 is preferably 2 or more, more preferably 3 or more, even more preferably 4 or more, even more preferably 5 or more, particularly preferably 6 or more, and is preferably 25 or less, more preferably 20 or less, even more preferably 15 or less, even more preferably 10 or less, and particularly preferably 8 or less. When n1 is within the above range, the antibacterial property of the antibacterial agent can be improved. In particular, when compound (1) is in a polymer form where n1 is preferably 3 or more, 4 or more, 5 or more, or 6 or more, the antibacterial property of the antibacterial agent can be further improved. In addition, since compound (1) in a polymer form has good affinity (or compatibility) with resin, it is advantageous when mixing the antibacterial agent with a resin to form an antibacterial article or when applying the antibacterial agent to the surface of the article body made of resin. Note that when n1 is 2 or more, R 1 ~R 18 may be the same or different.

[0021] In a preferred embodiment of the present invention, in formula (1), R 1 ~R 18 is a hydrogen atom, and n1 is 3 to 10 (more preferably 4 to 9). An antibacterial agent containing such a compound (1) is likely to exhibit excellent antibacterial properties (or antibacterial action).

[0022] In one embodiment of the present invention, the number average molecular weight Mn of compound (1) is preferably 900 or more, more preferably 1300 or more, even more preferably 1700 or more, even more preferably 2100 or more, particularly preferably 2500 or more, especially more preferably 2900 or more, and is preferably 14000 or less, more preferably 12000 or less, even more preferably 10000 or less, even more preferably 8000 or less, especially preferably 6000 or less, especially more preferably 4000 or less, or 3500 or less. In addition, the weight average molecular weight Mw of compound (1) is preferably 1300 or more, more preferably 1800 or more, even more preferably 3400 or more, even more preferably 4200 or more, especially preferably 5000 or more, especially more preferably 5800 or more, and is preferably 30000 or less, more preferably 24000 or less, even more preferably 20000 or less, even more preferably 16000 or less, especially preferably 12000 or less, especially more preferably 8000 or less or 7000 or less. When the number average molecular weight Mn and / or weight average molecular weight Mw of the compound (1) are equal to or higher than the lower limit, the antibacterial properties of the antibacterial agent can be further improved. In addition, as described above, the affinity (or compatibility) with the resin can be increased when forming an article. When the number average molecular weight Mn and / or weight average molecular weight Mw of the compound (1) are equal to or lower than the upper limit, the antibacterial agent can flow easily during the manufacture or molding of an article, which makes it easier to increase productivity or moldability.

[0023] In one embodiment of the present invention, the molecular weight distribution (Mw / Mn), which is the ratio of the weight average molecular weight Mw to the number average molecular weight Mw of compound (1), is preferably 1.2 or more, more preferably 1.5 or more, and even more preferably 1.7 or more, and may be, for example, 1.8 or more or 2.0 or more. In addition, the molecular weight distribution (Mw / Mn) is preferably 4.0 or less, more preferably 3.5 or less, even more preferably 3.0 or less, and even more preferably 2.5 or less. When the molecular weight distribution (Mw / Mn) is in the above range, the antibacterial properties of the antibacterial agent can be further improved.

[0024] The number average molecular weight Mn, weight average molecular weight Mw and molecular weight distribution (Mn / Mw) can be determined by gel permeation chromatography (GPC) measurement and conversion into standard polystyrene, for example, by the method described in the Examples.

[0025] In one embodiment of the present invention, the compound (1) in the present invention may exhibit a positive Cotton effect in a CD (circular dichroism) absorption spectrum, preferably at a wavelength of 200 to 350 nm, more preferably at a wavelength of about 250 to 300 nm. The CD spectrum can be measured by a CD dispersometer, for example, by the method described in the Examples.

[0026] In one embodiment of the present invention, compound (1) may be in the R or S form, or may be a mixture of the R and S forms.

[0027] In one embodiment of the present invention, compound (1) is preferably a pigment, which can impart color to articles to which it is applied.

[0028] In one embodiment of the present invention, the content of compound (1) in the antibacterial agent of the present invention may be, for example, 0.001% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, 98% by mass or more, or 100% by mass, based on the mass of the antibacterial agent. When the content of compound (1) in the antibacterial agent is within the above range, the antibacterial properties of the antibacterial agent can be further improved.

[0029] In one embodiment of the present invention, the content of compound (1) in the antibacterial agent of the present invention may be, for example, 100% by mass or less, 98% by mass or less, 95% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 10% by mass or less, 5% by mass or less, 1% by mass or less, 0.1% by mass or less, 0.01% by mass or less, or 0.001% by mass or less, or 0.0001% by mass or more, based on the mass of the antibacterial agent. When the content of compound (1) in the antibacterial agent is within the above range, it may be advantageous for the antibacterial properties of the antibacterial agent.

[0030] <Method for producing compound (1)> The method for producing compound (1) is not particularly limited. For example, compound (1) can be produced by reacting a compound represented by formula (3) (also referred to as compound (3)) with a compound represented by formula (4) (also referred to as compound (4)). [ka] [In the formula, R 1 ~R 18 is R in the formula (1). 1 ~R 18 are synonymous]

[0031] Compound (1) can be produced by esterifying or polycondensing compound (3) and compound (4) by a conventional method. Examples of the polymerization method include melt polymerization, solution polymerization, and interfacial polymerization, and among these, solution polymerization is preferred.

[0032] In the reaction, the molar ratio of compound (3) to compound (4) is preferably 30:70 to 70:30, more preferably 40:60 to 60:40, even more preferably 45:55 to 55:45, still more preferably 48:52 to 52 to 48, and particularly preferably 50:50.

[0033] The reaction may be carried out in the presence or absence of a solvent, but is preferably carried out in the presence of a solvent. When a solvent is used, the solvent is not particularly limited as long as it does not affect the reaction, and examples thereof include ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, and cyclohexanone; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as dimethyl ether (DME), tetrahydrofuran, and dimethoxyethane; chlorine-containing solvents such as dichloromethane (methylene chloride), chloroform, and chlorobenzene; amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide (DMF); sulfur-containing solvents such as dimethylsulfone, dimethylsulfoxide (DMSO), and sulfolane; pyrrolidone solvents such as N-methylpyrrolidone; and combinations thereof. Among these, chlorine-containing solvents are preferred from the viewpoint of solubility.

[0034] The reaction may include a base to liberate hydrogen chloride that may be produced, such as tertiary amines such as triethylamine, tri-n-butylamine, benzyldimethylamine, etc., of which triethylamine is preferred.

[0035] The reaction may be carried out in the presence of a catalyst. As the catalyst, various catalysts (e.g., metal complexes, etc.) used in the production of polyesters can be used, and as the metal catalyst, for example, a metal compound containing an alkali metal, an alkaline earth metal, a transition metal, a metal of Group 13 of the periodic table, a metal of Group 14 of the periodic table, a metal of Group 15 of the periodic table, etc. can be used. As the metal compound, alkoxides, organic acid salts, inorganic acid salts, metal oxides, etc. can be used.

[0036] The reaction can be carried out in air or in an inert gas (e.g., rare gas such as nitrogen or argon) atmosphere, and may be carried out under normal pressure, reduced pressure, or increased pressure. The reaction temperature can be selected depending on the polymerization method, etc. In the solution polymerization method, the reaction may be carried out at, for example, 10 to 40°C, preferably room temperature (e.g., 25°C). The reaction time may be any time that allows esterification or polycondensation to be completed, and may be, for example, 30 minutes to 48 hours, preferably 1 hour to 36 hours, and more preferably 6 hours to 24 hours.

[0037] After the reaction, the compound (1) may be isolated (separated and purified) by a conventional method, such as filtration, concentration, extraction, crystallization, recrystallization, column chromatography, or a combination of these methods. In a preferred embodiment, the compound (1) is isolated by concentrating the solvent, dissolving the compound in a small amount of a good solvent, adding a poor solvent, and filtering and drying the resulting precipitate. Compound (1) may be identified by, for example, NMR measurement, IR measurement, DART / MALDI measurement, or the like, and may be identified by, for example, the method described in the Examples.

[0038] <Compound (2)> The antibacterial agent of the present invention includes, in addition to compound (1), a compound represented by the following formula (2): [ka] [In the formula, R 19 ~R 36 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group; n2 is an integer of 1 to 30; M is a transition metal or an ion thereof; m is an integer of 0 to 4; and each X independently represents a monodentate ligand, provided that when m is 2 or more, two or more Xs may combine together to form a polydentate ligand. When the antibacterial agent of the present invention further contains compound (2), the antibacterial properties can be further enhanced.

[0039] In formula (2), R 19 ~R 36The halogen atom, alkyl group, alkoxy group, aryl group, aryloxy group, aralkyl group, and aralkyloxy group in the formula (1) are each 1 ~R 18 The halogen atom, alkyl group, alkoxy group, aryl group, aryloxy group, aralkyl group, and aralkyloxy group in R are exemplified by those exemplified above. Preferred halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, aralkyl groups, and aralkyloxy groups, and preferred R 19 ~R 36 Also, R in the above formula (1) 1 ~R 18 is the same as:

[0040] In formula (2), n2 is an integer of 1 to 30. When n2 is 2 or more, n2 represents the number of repeating units. The preferred value of n2 is the same as n1 in formula (1). When n2 is 2 or more, R 19 ~R 36 , M, X and m may be the same or different.

[0041] In formula (2), M represents a transition metal or an ion thereof. Examples of transition metals include silver (Ag), platinum (Pt), zinc (Zn), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), and copper (Cu). Among these, from the viewpoint of enhancing antibacterial properties, it is preferable that M is platinum (Pt) or an ion thereof.

[0042] m is an integer of 0 to 4, and represents the number of X coordinated (or bonded) to M. m can be appropriately selected depending on the coordination number of M. In one embodiment of the present invention, m is preferably 1 to 3, and more preferably 2.

[0043] Each X independently represents a monodentate ligand, provided that when m is 2 or more, two or more Xs may combine together to form a polydentate ligand. Examples of monodentate ligands include hydroxo(OH - ), thiolate (SR - ), Fluoro(F- ), Chloro(Cl - ), Bromo(Br - ), iodine (I - ), cyanate (CN - ), thiocyanato (SCN - ), isothiocyanate (NCS - ), Nitro(NO2 - ) and the like. Polydentate ligands include bidentate ligands and tridentate ligands. Ligands that can be both monodentate and bidentate ligands include carboxylate (RCOO - ) (R: 1 to 20 alkyl group). Among these, from the viewpoint of enhancing antibacterial properties, X is preferably a monodentate ligand, and more preferably a halide. When m is 2 or more and X is a monodentate ligand, multiple Xs may be the same or different.

[0044] In a preferred embodiment of the present invention, in formula (2), M is Pt, X is a halide, and m is 2. In a preferred embodiment of the present invention, in formula (2), R 19 ~R 36 is a hydrogen atom, n2 is 3 to 10 (more preferably 4 to 9), M is Pt, X is a halide, and m is 2. An antibacterial agent containing such a compound (2) can exhibit excellent antibacterial properties (or antibacterial action).

[0045] The number average molecular weight Mn, weight average molecular weight Mw and molecular weight distribution (Mw / Mn) of compound (2) can be selected from the ranges of the number average molecular weight Mn, weight average molecular weight Mw and molecular weight distribution (Mw / Mn) of compound (1) described above, and preferred ranges can also be selected from the same ranges.

[0046] In one embodiment of the present invention, the compound (2) in the present invention may be one that exhibits UV-vis absorption attributable to LMCT, preferably at a wavelength of 350 to 500 nm, more preferably at a wavelength of 400 to 450 nm, in the UV-vis (ultraviolet-visible) spectrum. In addition, the compound (2) in the present invention may be one that exhibits a positive Cotton effect, preferably at a wavelength of 200 to 350 nm, more preferably at a wavelength of 250 to 300 nm, in the CD (circular dichroism) absorption spectrum. In addition, the compound (2) in the present invention may be one that exhibits a negative Cotton effect, preferably at a wavelength of 300 to 370 nm, preferably at a wavelength of 320 to 340 nm. The UV-vis spectrum can be measured by a UV-vis spectrophotometer, and the CD spectrum can be measured by a CD dispersometer, for example, by the method described in the Examples.

[0047] In one embodiment of the present invention, the content of compound (2) in the antibacterial agent of the present invention may be, for example, 99.999% by mass or less, 99.99% by mass or less, 99.9% by mass or less, 99% by mass or less, 98% by mass or less, 95% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 10% by mass or less, 5% by mass or less, 1% by mass or less, 0.1% by mass or less, 0.01% by mass or less, or 0.001% by mass or less, or 0.0001% by mass or more, based on the mass of the antibacterial agent. When the content of compound (2) in the antibacterial agent is within the above range, it may be advantageous for the antibacterial properties of the antibacterial agent.

[0048] In one embodiment of the present invention, the content of compound (2) in the antibacterial agent of the present invention may be, for example, 0.001% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 98% by mass or more, or 99.9% by mass or less, based on the mass of the antibacterial agent. When the content of compound (2) in the antibacterial agent is within the above range, the antibacterial property is likely to be enhanced.

[0049] In one embodiment of the present invention, the content ratio of compound (1) to compound (2) in the antibacterial agent (the former:the latter) is, in terms of enhancing the antibacterial properties of the antibacterial agent, preferably 99.9:0.1 to 0.1:99.9, more preferably 99:1 to 1:99, even more preferably 2:98 to 90:10, even more preferably 3:97 to 70:30, particularly preferably 4:96 to 50:50, especially preferably 5:95 to 30:70, and especially more preferably 6:94 to 20:80, in terms of molar ratio.

[0050] In one embodiment of the present invention, the content ratio of compound (1) to compound (2) in the antibacterial agent (the former:the latter) is, in terms of enhancing the antibacterial properties of the antibacterial agent, preferably 99.9:0.1 to 0.1:99.9, more preferably 99:1 to 1:99, even more preferably 98:2 to 10:90, still more preferably 97:3 to 30:70, particularly preferably 96:4 to 50:50, especially preferably 95:5 to 70:30, and especially still more preferably 94:6 to 80:20, in terms of molar ratio.

[0051] In one embodiment of the present invention, the content ratio of compound (1) to compound (2) in the antibacterial agent (the former:the latter) is, in terms of enhancing the antibacterial properties of the antibacterial agent, preferably 99.9:0.1 to 0.1:99.9, more preferably 99:1 to 1:99, even more preferably 90:10 to 10:90, still more preferably 80:20 to 20:80, particularly preferably 70:30 to 30:70, especially preferably 60:40 to 40:60, and especially more preferably 55:45 to 45:55, in terms of molar ratio.

[0052] <Method for producing compound (2)> The method for producing compound (2) is not particularly limited, but may be a method for producing compound (2) by reacting compound (1) with a compound represented by the following formula (5): [ka] [In the formula, k is an integer of 0 to 4, m+k is an integer of 0 to 6, each Y independently represents a monodentate ligand, provided that when k is 2 or more, two or more Ys may combine together to form a polydentate ligand, and M, X, and m are defined as M, X, and m in the formula (2).] The compound (5) can be produced by reacting the compound represented by the formula (5) with the compound represented by the formula (5):

[0053] k is an integer of 0 to 4, and represents the number of Y coordinated (or bonded) to M. k can be appropriately selected depending on the coordination number of M and the number of X. In one embodiment of the present invention, k is preferably 1 to 3, and more preferably 2. Furthermore, m+k is an integer of 0 to 6, and in one embodiment of the present invention, m+k is preferably an integer of 3 to 5, and more preferably 4.

[0054] Y is not particularly limited as long as it is capable of ligand exchange with the N atom of the bipyridine ring in formula (2), that is, Y is detached from X and the N atom of the bipyridine ring in formula (2) can be coordinated to X, and examples of the solvent include the ligands exemplified above for X and solvents capable of coordinating to M. As the solvent, for example, a solvent capable of ligand exchange may be appropriately selected from the solvents exemplified above, and from the viewpoint of easy ligand exchange, a sulfur-containing solvent such as dimethyl sulfoxide (DMSO), which is a weak Lewis base, can be preferably used.

[0055] In the reaction, the molar ratio of compound (2) to compound (5) is preferably 30:70 to 70:30, more preferably 40:60 to 60:40, even more preferably 45:55 to 55:45, still more preferably 48:52 to 52 to 48, and particularly preferably 50:50. When the amounts of compound (2) to compound (5) are within the above ranges, compound (2) is likely to be obtained in high yield.

[0056] The reaction can be carried out in the presence of a solvent. The solvent can be appropriately selected from the above-mentioned examples, and from the viewpoint of reactivity, a sulfur-containing solvent is preferable, and DMSO is more preferable. In addition, when Y is a solvent, it is more preferable to select the same solvent as Y.

[0057] The reaction can be carried out in air or in an inert gas (e.g., rare gas such as nitrogen or argon) atmosphere, and is preferably carried out in an inert gas atmosphere. The reaction may be carried out under normal pressure, reduced pressure, or increased pressure. The reaction temperature can be appropriately selected depending on the type of M and ligand, and is preferably 20 to 100°C, more preferably 40 to 90°C, and even more preferably 60 to 80°C. The reaction time can be selected depending on the reaction temperature, and is, for example, 30 minutes to 48 hours, preferably 5 hours to 36 hours, and more preferably 10 hours to 30 hours.

[0058] After the reaction, the compound (2) may be isolated (separated and purified) by a conventional method, for example, a separation means such as filtration, concentration, extraction, crystallization, recrystallization, column chromatography, or a combination of these, and in a preferred embodiment, a poor solvent may be added, and the resulting precipitate may be filtered and dried. Compound (2) can be identified by NMR measurement, IR measurement, DART / MALDI measurement, UV-vis measurement, CD measurement, or the like, and may be identified by the method described in the Examples, for example.

[0059] <Antibacterial agent> The antibacterial agent of the present invention contains compound (1) and can therefore exhibit excellent (or high) antibacterial properties. The antibacterial agent of the present invention can also contain compound (2) in addition to compound (1), and such an antibacterial agent can also exhibit excellent (or high) antibacterial properties. In this specification, antibacterial means sterilization, disinfection, bacteriostatic, sterilizing, preserving, and sanitizing against bacteria, fungi, or viruses. An antibacterial agent can have the effect of, for example, killing or eradicating bacteria and fungi, or inhibiting the development, growth or proliferation of bacteria and fungi, or inactivating or inhibiting the proliferation of viruses.

[0060] Examples of bacteria include, but are not limited to, gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, Moraxella, and Legionella; and gram-positive bacteria such as Staphylococcus aureus and Clostridium bacteria. Examples of fungi include, but are not limited to, yeasts such as Candida, Rhodotorula, and baker's yeast; and molds such as red mold and black mold. Examples of viruses include, but are not limited to, influenza virus, feline calicivirus, coronavirus, SARS, MARS, norovirus, AIDS virus, and Ebola virus. These may be used alone or in combination of two or more kinds.

[0061] The antibacterial agent of the present invention is preferably an antibacterial agent against at least one species selected from the group consisting of bacteria and viruses, and can exhibit excellent antibacterial action against bacteria and / or viruses.

[0062] Among the above bacteria and viruses, bacteria are more preferable from the viewpoint of exhibiting high antibacterial properties, and at least one selected from the group consisting of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus is even more preferable, with Escherichia coli being particularly preferable.

[0063] In one embodiment of the present invention, the antibacterial agent of the present invention has antibacterial activity against bacteria or viruses (preferably E. coli) of preferably 90% or more, more preferably 99% or more, even more preferably 99.9% or more, and even more preferably 99.99% or more, and may be, for example, 99.999% or more. The antibacterial activity can be evaluated by making the antibacterial agent contain bacteria or viruses, or by bringing bacteria or viruses into contact with an antibacterial article that has been antibacterially treated, and can be carried out, for example, by the method described in the Examples.

[0064] The antibacterial agent of the present invention may further contain additives within a range that does not impair the effects of the present invention. Examples of additives include surfactants, dispersants, thickeners, pH adjusters, antioxidants, moisturizers, colorants, UV absorbers, stabilizers, fragrances, flame retardants, lubricants, solvents (e.g., the solvents exemplified above), antibacterial agents other than compound (1) and compound (2), and the like. These additives can be used alone or in combination of two or more. The content of the additives is not particularly limited, but is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and even more preferably 1% by mass or less, based on the mass of the antibacterial agent, and is usually 0% by mass or more, for example, 0.1% by mass or more.

[0065] The form of the antibacterial agent of the present invention is not particularly limited, and may be, for example, a liquid, cream, ointment, gel, wax, or spray.

[0066] The antibacterial agent can be used in applications that require antibacterial properties. Examples include, but are not limited to, daily necessities (e.g., clothing, bedding such as sheets, packaging materials, architectural interior materials such as curtains and wallpapers, sanitary products such as masks, all daily necessities such as towels, vehicle interior materials, etc.); detergent applications (e.g., detergents, fabric softeners, dishwashing agents, hard surface detergents, etc.); cosmetics applications (e.g., shampoos, rinses, cosmetics, antiperspirants, etc.); paints; fibers; nonwoven fabrics; filters; wood preservatives; cement admixtures; etc.

[0067] [Antibacterial articles] The present invention includes an antibacterial article comprising the antibacterial agent of the present invention. The antibacterial article of the present invention can exhibit excellent antibacterial properties (or high antibacterial properties) because it comprises the antibacterial agent of the present invention.

[0068] The antibacterial article of the present invention may contain only the antibacterial agent of the present invention, or may contain other components in addition to the antibacterial agent of the present invention. In a preferred embodiment of the present invention, the antibacterial agent of the present invention preferably further contains a resin or glass. Specific examples include an antibacterial article (1) formed only from the antibacterial agent; an antibacterial article (also referred to as antibacterial article (2)) formed from an antibacterial composition containing a resin and / or glass and an antibacterial agent; and an antibacterial article (also referred to as antibacterial article (3)) formed by applying an antibacterial agent to at least a part of the surface of the article body.

[0069] In one embodiment of the present invention, the antibacterial article (1) can be obtained by molding the antibacterial agent by a conventional molding method, which is not particularly limited and includes, for example, injection molding, injection compression molding, extrusion molding, transfer molding, blow molding, pressure molding, casting molding, and the like.

[0070] In one embodiment of the present invention, the antibacterial article (2) can be obtained by molding the antibacterial composition by a conventional molding method. The molding method is not particularly limited, and the conventional molding methods exemplified above can be used. The antibacterial composition can be prepared by mixing a resin and / or glass, an antibacterial agent, and, if necessary, the additives exemplified above.

[0071] In one embodiment of the present invention, the content of the antibacterial agent may be, for example, 0.001% by mass or more, 0.01% by mass or more, or 0.03% by mass or more based on the mass of the antibacterial article, and is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, particularly preferably 0.7% by mass or more, and particularly preferably 1.0% by mass or more. When the content of the antibacterial agent is equal to or more than the lower limit, the antibacterial property of the antibacterial article can be further improved. Furthermore, since the antibacterial agent of the present invention is an organic substance (preferably a polymer) and is compatible with resin, a relatively large amount (for example, 0.5% by mass or more) can be mixed with the resin in a mixed form, and the antibacterial property can be further improved. The content of the antibacterial agent is usually 100% by mass or less, based on the mass of the antibacterial article. When the antibacterial article contains components other than the antibacterial agent (preferably resin and / or glass, etc.), the content can be appropriately selected depending on the application, and may be preferably 90% by mass or less, 70% by mass or less, 50% by mass or less, or 30% by mass or less, more preferably 10% by mass or less or 5% by mass or less, and even more preferably 3% by mass or less.

[0072] In one embodiment of the present invention, when the antibacterial article contains a resin or glass, the content of the antibacterial agent is, for example, 0.001 parts by mass or more, preferably 0.01 parts by mass or more or 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.3 parts by mass or more, even more preferably 0.5 parts by mass or more, particularly preferably 0.7 parts by mass or more, and particularly preferably 1.0 parts by mass or more, relative to 100 parts by mass of the resin and / or glass. The content of the antibacterial agent may be preferably 950 parts by mass or less, 500 parts by mass or less, 300 parts by mass or less, 150 parts by mass or less, or 50 parts by mass or less, more preferably 20 parts by mass or less or 10 parts by mass or less, and even more preferably 5 parts by mass or less, relative to 100 parts by mass of the resin and / or glass. When the content of the antibacterial agent is equal to or more than the lower limit, the antibacterial property of the antibacterial article can be further improved. When the content of the antibacterial agent is equal to or less than the upper limit, the properties of the resin or glass are easily exhibited.

[0073] In one embodiment of the present invention, the antibacterial article (3) includes an article body and a coating layer formed on at least a part of the surface of the article body, and the coating layer includes the antibacterial agent. The article body preferably includes resin and / or glass. The article body may also include the antibacterial agent. Specific examples of the antibacterial article (3) include a method in which an antibacterial agent is applied to a part or all of the surface of the article body by a conventional coating method and dried as necessary; and a method in which the article body and the coating layer are simultaneously formed by injection molding (e.g., two-color molding) or extrusion molding (e.g., co-extrusion molding) capable of forming two or more layers. The coating method is not particularly limited, and a conventional method can be used, for example, a spray method, a wire bar coating method, a roll coating method such as reverse coating or gravure coating, a die coating method, a comma coating method, a lip coating method, a spin coating method, a screen coating method, a fountain coating method, a dipping method, a drip molding method, and the like.

[0074] In one embodiment of the present invention, the content of the antibacterial agent in the coating layer is preferably 30% by mass or more, more preferably 50% by mass or more, even more preferably 70% by mass or more, still more preferably 90% by mass or more, particularly preferably 95% by mass or more, and may be 100% by mass, based on the mass of the coating layer. When the content of the antibacterial agent in the coating layer is equal to or more than the lower limit, the antibacterial property of the antibacterial article can be further improved.

[0075] In one embodiment of the present invention, the thickness of the coating layer is not particularly limited, but is preferably 0.1 μm to 2 mm, and more preferably 1 μm to 500 μm. When the thickness of the coating layer is equal to or greater than the lower limit, antibacterial properties can be improved, and when the thickness is equal to or less than the upper limit, peeling from the article body can be easily suppressed. The thickness of the coating layer can be measured by a conventional method, for example, using a thickness meter.

[0076] In one embodiment of the present invention, the content of the antibacterial agent is 1 cm 2 on the surface of the article body 2The content of the antibacterial agent may be, for example, 0.2 μmol or more, preferably 1 μmol, 5 μmol or more, or 8 μmol or more, more preferably 15 μmol or more, even more preferably 30 μmol or more, even more preferably 60 μmol or more, particularly preferably 100 μmol or more, especially more preferably 130 μmol or more, and especially more preferably 150 μmol or more. When the content of the antibacterial agent is equal to or more than the lower limit, the antibacterial property of the antibacterial article can be further improved. The content of the antibacterial agent is, for example, 0.2 μmol or more per 1 cm of the surface of the article body. 2 The content of the antibacterial agent may be, for example, 1000 μmol or less, preferably 800 μmol or less, and more preferably 500 μmol or less per unit area. When the content of the antibacterial agent is equal to or less than the above upper limit, peeling from the article body is easily suppressed.

[0077] The resin contained in the antibacterial article is not particularly limited and can be appropriately selected depending on the application, molding method, amount of antibacterial agent, etc., and includes thermoplastic resins, thermosetting resins, etc. Examples of thermoplastic resins include polyvinyl alcohol resins, polystyrene resins, polyolefin resins (polyethylene resins, polypropylene resins, etc.), acrylic resins, halogen-containing resins (polyvinyl chloride resins, etc.), polyvinyl ester resins, thermoplastic polyurethane resins, polyester resins, polyamide resins, polyether resins, polycarbonate resins, polysulfone resins, thermoplastic polyimide resins, thermoplastic elastomers, etc. Examples of thermosetting resins include epoxy resins, thermosetting polyurethane resins, silicone resins, thermosetting polyimide resins, urea resins, melamine resins, phenol resins, furan resins, unsaturated polyester resins, and copolymers of monomer components constituting these resins. The resins can be used alone or in combination of two or more. Among these, the resin is preferably a thermoplastic resin, and is preferably at least one selected from the group consisting of olefin resins, ABS resins (copolymers of acrylonitrile, butadiene and styrene), and polycarbonate resins. Such suitable resins have good compatibility with the antibacterial agent of the present invention and are easily dispersed (preferably uniformly dispersed) in the resin, so that the obtained antibacterial article is likely to exhibit antibacterial action. In addition, the resin has good applicability to the surface of the article body, so that a highly antibacterial coating layer can be formed. The resin contained in the antibacterial article may be in the form of fibers.

[0078] The form of the antibacterial article (or the article itself) is not particularly limited and may be appropriately selected depending on the application. For example, the antibacterial article may be a household product, a commercial product, an industrial product, or the like, or may be any of the applications of the antibacterial agent listed above.

[0079] The antibacterial agent of the present invention is a novel antibacterial agent and can have excellent antibacterial properties (or antibacterial action). Further, the antibacterial article of the present invention is also a novel antibacterial article and can have high antibacterial properties (or antibacterial action) because it contains the antibacterial agent of the present invention. Therefore, the antibacterial agent and antibacterial article of the present invention can be applied to various uses that require antibacterial action. The present invention can contribute to the achievement of 3 goals (health and well-being for all people) and 9 goals (build the foundation for industry and technological innovation) among the 17 goals of the Sustainable Development Goals (SDGs) established by the United Nations.

Examples

[0080] Hereinafter, the present invention will be described more specifically based on Examples and Comparative Examples, but the present invention is not limited to the following Examples.

[0081] <Measurement of molecular weight and molecular weight distribution> The number average molecular weight, weight average molecular weight, and molecular weight distribution of the compounds (1A) and (2A) obtained in the Examples were measured using GPC under the following conditions. (Pretreatment method) To each of the compounds (1A) and (2A), DMF (containing 10 mM LiBr) was added to a concentration of 0.1% by mass and dissolved to obtain a measurement solution. (Measurement conditions) Measuring device: "GPC System" manufactured by JASCO Corporation Analysis software: "ChromNAV" manufactured by JASCO Corporation Eluent: DMF (containing 10 mM LiBr) Injection volume: 100 μL Flow rate: 1 mL / min Measurement temperature: 40°C Column: "Shodex (registered trademark) LF-804" manufactured by Resonac Co., Ltd. Detector: "UV-4570" manufactured by JASCO Corporation Molecular weight standard: Standard polystyrene

[0082] <CD and UV-vis spectrum measurement> The CD spectra and UV-vis spectra of the compounds (1A) and (2A) obtained in the examples were measured using a CD and UV-vis measurement device under the following conditions. Measurement equipment: Circular dichroism spectrometer (JASCO Corporation, "J-820") Scan speed: 100 nm / min Slit width: Automatic setting Bandwidth: 1nm Sampling interval: 0.5 nm Optical path length: 1cm Solution concentration: Solvent DMF, 0.01 mM

[0083] [Example 1] In a glass container, 141 mg (0.500 mmol) of compound (3A) (2,2'-bipyridine-4,4'-dicarboxydichloride), 10.0 mL of methylene chloride, 5.00 mL of triethylamine, and 143 mg (0.500 mmol) of compound (4A) ((R)-1,1'-bi-2-naphthol) were added and stirred overnight at room temperature. Next, the solvent was distilled off under reduced pressure, and the residue was dissolved in a small amount of methylene chloride and added to 2-propanol. Thereafter, the precipitated solid was filtered off using a membrane filter (pore size: 1.0 μm) and dried under reduced pressure to obtain 165 mg of compound (1A) as an orange solid. Compound (1A) was identified by NMR and IR. Compound (1A) was the R-form. [ka]

[0084] 1 H-NMR(400MHz,DMSO-d6):δ6.91-8.21(br,18H) IR(KBr):3444,3094,1743,1621,1591,1556,1506,1471,1431,1413,1390,1314,1297,1232,1204,1156, 1144,1100,1023,973,950,888,805,775,734,704,671,622,579,559,519,499,488,454,443,420,403(cm -1 ).

[0085] Compound (1A) had a number average molecular weight of 3,100, a weight average molecular weight of 6,510, and a molecular weight distribution of 2.1.

[0086] [Example 2] In a glass container, 99.1 mg (0.200 mmol) of compound (1A) and 84.5 mg (0.200 mmol) of compound (5A) (Pt(DMSO)2Cl2) were added, and the atmosphere in the container was replaced with argon. Then, dimethyl sulfoxide (20 mL) was added, and the mixture was stirred at 65°C for 24 hours. After that, the reaction solution was poured into diethyl ether, and the precipitated solid was filtered off using a membrane filter (pore size: 1.0 μm), and dried under reduced pressure to obtain 110 mg of an orange solid compound. It was confirmed that the obtained compound was compound (2A) by NMR, IR, CD, and UV-vis absorption spectra (shown in Figure 1). It was also confirmed that a small amount of compound (1A) was contained. [ka]

[0087] 1 H-NMR (400MHz, DMSO-d6): δ 7.09-7.10 (m, 12H, binaphthyl ring), 8.94-9.52 (m, 6H, bipyridine ring) IR(KBr):3404,3039,1742,1620,1590,1557,1507,1455,1431,1400,1362,1279,1202,1157,1 131,1094,1024,970,950,888,804,774,750,719,694,663,623,579,519,491,452,421,404(cm -1 ).

[0088] In the CD and UV-vis absorption spectra of compound (1A) and compound (2A), compound (2A) showed UV-vis absorption attributable to LMCT in the vicinity of 400-450 nm (see the lower diagram of Figure 1), confirming the coordination of platinum. In addition, both compound (1A) and compound (2A) showed a positive Cotton effect in the vicinity of 250-300 nm, and compound (2A) further showed a negative Cotton effect in the vicinity of 330 nm (see the upper diagram of Figure 1). It is presumed that only compound (2A) showed a negative Cotton effect because the rotation of the bipyridine moiety was suppressed and the conformation was fixed due to the coordination of platinum. Also, 1 In 1 H-NMR, the signal derived from bipyridine in compound (2A) was observed on the lower magnetic field side than the signal derived from bipyridine in compound (1), suggesting the coordination of platinum.

[0089] The compound (2A) had a number average molecular weight of 3,100, a weight average molecular weight of 5,580, and a molecular weight distribution of 1.8.

[0090] [Comparative Example 1] Bipyridine was used as the antibacterial agent.

[0091] Antibacterial agent 1 consisting of compound (1) obtained in Example 1, antibacterial agent 2 consisting of compound (2) (containing a small amount of compound (1)) obtained in Example 2, and antibacterial agent 3 consisting of bipyridine in Comparative Example 1 were used to evaluate the antibacterial properties by the following method.

[0092] [Antibacterial evaluation] (Preparation of E. coli solution) Escherichia coli NBRC3301 (K12 strain) was cultured in TSB liquid medium with shaking at 120 rpm at 37°C for 15 hours until it reached stationary phase to prepare a preculture solution. A portion of the preculture solution was then collected in TSB liquid medium and cultured with shaking at 120 rpm at 37°C for 2 hours until it reached mid-logarithmic growth phase to prepare a main culture solution. The main culture solution was then centrifuged (4000 rpm, 3 minutes, room temperature) to precipitate the E. coli, which was then separated from the liquid medium. Phosphate-buffered saline (PBS) was added to the precipitated E. coli to wash the E. coli and remove metabolites and unnecessary organic matter of E. coli. Next, the E. coli was adjusted to a constant concentration with PBS to obtain an E. coli solution.

[0093] (Antibacterial effect test) 300 μL of the obtained E. coli liquid was taken, and the antibacterial agent 1 of Example 1, the antibacterial agent 2 of Example 2, or the antibacterial agent 3 of Comparative Example 1 was added thereto so as to be 0.05 mmol, and then the antibacterial treatment was performed for 1 hour in an aluminum block thermostatic chamber at 30° C. to obtain a treated liquid. The E. coli liquid to which no antibacterial agent was added and which was not antibacterial treated was used as a control. After the treatment, the treated liquid and the control were serially diluted with PBS, and 100 μL of the diluted liquid was spread on a TSB agar medium and cultured at 37° C. for 14 hours. The number of colonies (the number of E. coli) was measured by a colony count method (a method of serially diluting and counting the number of bacteria). The above operation was performed twice, and the average colony number was calculated by averaging. The number of bacteria was calculated by dividing the number of colonies measured in each sample by the dilution rate and then multiplying by 10 (1 mL / 100 μL (amount of the seeded bacteria liquid)), and the average number of bacteria was calculated by dividing the sum of the number of bacteria from the same sample by the number of samples.

[0094] The results of measurement by the colony count method in Examples 1 and 2 and Comparative Example 1 are shown in Table 1. The antibacterial activity was calculated as the digit of the decrease in the average colony number based on the average colony number (E. coli number) of the control obtained. <Antibacterial> Less than one digit: 10% or less 1 digit or more but less than 2 digits: 90% or more but less than 99% 2 to 3 digits: 99% to 99.9% Between 3 and 4 digits: Between 99.9% and 99.99% Between 4 and 5 digits: Between 99.99% and 99.999% 5 digits or more: 99.999% or more <Evaluation> Over 99.9%...◎ Between 99% and 99.9%... Between 90% and 99%...△ Less than 90%...×

[0095] [Table 1]

[0096] As shown in Table 1, antibacterial agent 1 of Example 1 had an antibacterial activity of 99.99% or more, and antibacterial agent 2 of Example 2 had an antibacterial activity of 99.999% or more, and was evaluated as excellent as an antibacterial agent, with an × rating. In contrast, antibacterial agent 3 of Comparative Example 1 had an antibacterial activity of 10% or less, and was evaluated as poor as an antibacterial agent.

[0097] [Example 3] The compound (1) and compound (2) produced as described above are mixed to prepare an antibacterial agent having a molar ratio of compound (1) to compound (2) of 1:99, 10:90, 75:25, 50:50, 25:75, 90:10, or 99:1. These antibacterial agents exhibit excellent antibacterial properties.

[0098] [Example 4] (Production of goods) The antibacterial agent 1 obtained in Example 1 is dissolved in DMSO to prepare an antibacterial agent solution. The antibacterial agent solution is applied to the surface of the article body made of polypropylene resin in an amount of 167 μmol / cm 2 and drying to obtain an antibacterial article having an antibacterial treated surface.

[0099] (Preparation of E. coli solution) An E. coli liquid is obtained in the same manner as described above in (Preparation of E. coli liquid).

[0100] (Antibacterial effect test) A liquid of E. coli is dropped onto an article whose surface has been treated for antibacterial purposes, the dropped portion is covered with a film, and the antibacterial treated portion is contacted with the liquid of E. coli for 1 hour at room temperature. The liquid of E. coli is then collected, and the collected liquid of E. coli is serially diluted with PBS, and 100 μL of the diluted liquid is spread on a TSB agar medium and cultured at 37° C. for 14 hours. The number of colonies is counted by the colony count method (a method of counting the number of bacteria by serial dilution) as described above. The above operation is performed twice, and the average number of colonies is calculated by averaging, and the antibacterial properties can be evaluated by the same method as above.

[0101] [Example 5] Surface coverage is 8μmol / cm 2 An antibacterial article is obtained in the same manner as in Example 4, except that the above-mentioned change is made so that the antibacterial effect test is carried out.

[0102] [Example 6] Surface coverage is 0.2μmol / cm 2 An antibacterial article is obtained in the same manner as in Example 4, except that the above-mentioned change is made so that the antibacterial effect test is carried out.

[0103] [Example 7] An antibacterial agent 4 is prepared in which the content ratio of compound (1) to compound (2) is 1:9. An antibacterial article is obtained in the same manner as in Example 5, except that antibacterial agent 4 is used instead of antibacterial agent 1, and an antibacterial effect test is performed.

[0104] [Table 2]

[0105] [Example 8] (Production of goods) The antibacterial composition is obtained by adding the antibacterial agent 1 obtained in Example 1 to a propylene resin so that the amount of the antibacterial agent 1 becomes 1.0 mass% relative to the mass of the antibacterial composition. The obtained antibacterial composition is molded by injection molding to obtain an antibacterial article.

[0106] An antibacterial effect test is carried out in the same manner as in Example 5, except that the antibacterial article of Example 8 is used instead of the antibacterial article of Example 5.

[0107] [Example 9] An antibacterial article is obtained in the same manner as in Example 8, except that the amount of antibacterial agent 1 added is changed to 0.05% by mass, and an antibacterial effect test is carried out.

[0108] [Example 10] An antibacterial article is obtained in the same manner as in Example 8, except that the amount of antibacterial agent 1 added is changed to 0.001% by mass, and an antibacterial effect test is carried out.

[0109] [Example 11] An antibacterial article is obtained in the same manner as in Example 8, except that antibacterial agent 4 obtained in Example 7 is used instead of antibacterial agent 1 and the amount added is changed to 0.5 mass %, and an antibacterial effect test is performed.

[0110] [Table 3]

[0111] [Example 12] The antibacterial effect test is carried out in the same manner as in Example 8, except that the antibacterial agent 1 obtained in Example 1 is molded by injection molding to obtain an antibacterial article.

[0112] [Example 13] The antibacterial effect test is carried out in the same manner as in Example 8, except that the antibacterial agent 4 obtained in Example 7 is molded by injection molding to obtain an antibacterial article. [Table 4]

Claims

1. The following formula (1): 【Chemistry 1】 [In the formula, R １ ~R １８ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group, and n1 is an integer of 1 to 30. An antibacterial agent comprising a compound represented by the formula:

2. The antibacterial agent according to claim 1, wherein the compound represented by formula (1) has a number average molecular weight Mn of 900 to 14,000.

3. The following formula (2): 【Chemistry 2】 [In the formula, R １９ ~R ３６ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, or an aralkyloxy group; n2 is an integer of 1 to 30; M is a transition metal or an ion thereof; m is an integer of 0 to 4; and each X is independently a monodentate ligand, provided that when m is 2 or more, two or more Xs may combine together to form a polydentate ligand. The antibacterial agent according to claim 1 , further comprising a compound represented by the formula:

4. The antibacterial agent according to claim 3, wherein the content ratio of the compound represented by formula (1) to the compound represented by formula (2) is 99.9:0.1 to 0.1:99.9 in terms of molar ratio.

5. The antibacterial agent according to claim 3 , wherein in formula (2), M is Pt, X is a halide, and m is 2.

6. The antibacterial agent according to claim 1, which is an antibacterial agent against at least one species selected from the group consisting of bacteria and viruses.

7. An antibacterial article comprising the antibacterial agent according to any one of claims 1 to 6.

8. The antimicrobial article of claim 7 , further comprising resin and / or glass.

9. The antibacterial article according to claim 7 , comprising: a body; and a coating layer formed on at least a portion of the surface of the body, the coating layer including the antibacterial agent.

10. The antibacterial article according to claim 7 , wherein the content of the antibacterial agent is 0.01% by mass or more based on the mass of the antibacterial article.

11. The content of the antibacterial agent is 1 cm2 on the surface of the article body. ２ The antibacterial article according to claim 9, wherein the concentration is 1 μmol or more per unit area.

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