Antibacterial composition

Abstract

To provide an antibacterial composition that exhibits enhanced antibacterial effects on gram-positive bacteria compared to the sole use of a diiodomethane compound while ensuring high storage stability of the diiodomethane compound.SOLUTION: An antibacterial composition disclosed herein contains a diiodomethane compound (A), a quaternary ammonium salt (B), and a cyclodextrin derivative (C). The ratio of the content of the cyclodextrin derivative (C) to the total content of the diiodomethane compound (A) and the quaternary ammonium salt (B), expressed by (C / (A+B)), is 6.00 or more.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to antimicrobial compositions. [Background technology]

[0002] Diiodomethyl-p-tolylsulfone (hereinafter also referred to as "DMTS") has conventionally been used as an active ingredient of antifungal agents (Patent Document 1). On the other hand, Staphylococcus aureus is a bacterium that normally resides on the skin and is known as a bad bacterium with strong pathogenicity (Patent Document 2). In healthy skin, no problems arise due to the normal biological defense mechanism, but it is known that if Staphylococcus aureus proliferates for some reason, it can cause skin diseases. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2018-193337 A [Patent Document 2] JP 2021-161034 A Summary of the Invention [Problem to be solved by the invention]

[0004] Conventional antifungal agents containing only DMTS as an active ingredient may not have sufficient effect of inhibiting bacterial growth (hereinafter also referred to as "antibacterial effect") against gram-positive bacteria (e.g., Staphylococcus aureus, Bacillus subtilis). Therefore, there is a demand for the development of an antibacterial composition that exhibits high antibacterial effect against gram-positive bacteria when it contains DMTS. Furthermore, in order to maintain high antibacterial performance for a long period of time and to improve handleability, there is a demand for the diiodomethane compound, which is the active ingredient, to be less likely to precipitate in water (i.e., the diiodomethane compound has excellent storage stability).

[0005] In view of the above circumstances, an object of one embodiment of the present disclosure is to provide an antibacterial composition that exhibits a higher antibacterial effect against Gram-positive bacteria than when a diiodomethane compound is used alone, and that has excellent storage stability of the diiodomethane compound. [Means for solving the problem]

[0006] Specific means for solving the above problems include the following aspects. <1> The composition contains a diiodomethane compound (A), a quaternary ammonium salt (B), and a cyclodextrin derivative (C), An antibacterial composition, wherein the ratio (C / (A+B)) of the content of the cyclodextrin derivative (C) to the sum of the content of the diiodomethane compound (A) and the content of the quaternary ammonium salt (B) is 6.00 or more. <2> The quaternary ammonium salt (B) includes at least one selected from the group consisting of benzalkonium chloride, benzethonium chloride, and cetylpyridinium chloride. <1> The antibacterial composition according to claim 1. <3> The diiodomethane compound (A) includes diiodomethyl-p-tolylsulfone. <1> or <2> The antibacterial composition according to claim 1. <4> The cyclodextrin derivative (C) includes a β-cyclodextrin derivative. <1> ~ <3> 13. An antibacterial composition according to any one of claims 1 to 12. <5> The β-cyclodextrin derivative includes methyl-β-cyclodextrin. <4> The antibacterial composition according to claim 1. Effect of the Invention

[0007] According to the present disclosure, there is provided an antibacterial composition that exhibits a higher antibacterial effect against Gram-positive bacteria than when a diiodomethane compound is used alone, and that has excellent storage stability of the diiodomethane compound. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] In the present disclosure, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In the present disclosure, when a plurality of substances corresponding to each component are present in the composition, the amount of each component in the composition means the total amount of the plurality of substances present in the composition, unless otherwise specified. In the numerical ranges described in stages in this disclosure, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. In the numerical ranges described in this disclosure, the upper or lower limit value of the numerical range may be replaced with a value shown in the examples. In this disclosure, combinations of preferred aspects are more preferred aspects. In the description of groups (atomic groups) in the present disclosure, a description without specifying whether substituted or unsubstituted encompasses both groups having no substituents and groups having a substituent.

[0009] (1) Antibacterial composition The antibacterial composition of the present disclosure contains a diiodomethane compound (A), a quaternary ammonium salt (B), and a cyclodextrin derivative (C). The ratio (C / (A+B)) of the content of the cyclodextrin derivative (C) to the total content of the diiodomethane compound (A) and the quaternary ammonium salt (B) (hereinafter, simply referred to as the "ratio (C / (A+B)")) is 6.00 or more.

[0010] In the present disclosure, the term "diiodomethane compound (A)" refers to benzene having a diiodomethyl group and its derivatives (for example, α,α-diiodoacetylbenzene derivatives, α,α-diiodomethylsulfonylbenzene derivatives). In the present disclosure, the term "quaternary ammonium salt (B)" refers to a salt consisting of an ammonium cation having four substituents and a counter ion (anion). At least two of the four substituents may form a cyclic structure together with the ammonium cation. In the present disclosure, the term "cyclodextrin derivative" refers to a cyclodextrin-based compound containing cyclodextrin or a derivative thereof, and includes cyclodextrin and cyclodextrin having a substituent.

[0011] The antibacterial composition of the present disclosure has the above-mentioned constitution, and therefore exhibits a higher antibacterial effect against gram-positive bacteria than when the diiodomethane compound is used alone, and the diiodomethane compound has excellent storage stability. The diiodomethane compound may be diiodomethyl-p-tolylsulfone. The gram-positive bacteria may be Staphylococcus aureus.

[0012] The form of the antibacterial composition is not particularly limited, and examples thereof include a solution (e.g., an aqueous or non-aqueous solution), a suspension (i.e., a slurry), a powder, a pellet, etc. The solution is obtained by dissolving the diiodomethane compound (A) in a solvent (D). Details of the solvent (D) will be described later.

[0013] The ratio (C / (A+B)) of the content of the cyclodextrin derivative (C) to the total content of the diiodomethane compound (A) and the quaternary ammonium salt (B) is 6.00 or more. From the viewpoint of storage stability, the ratio (C / (A+B)) is preferably 6.50 or more, more preferably 6.90 or more. From the viewpoint of ease of handling, the ratio (C / (A+B)) is preferably 30.0 or less, more preferably 25.0 or less, even more preferably 20.0 or less, and particularly preferably 16.0 or less. Furthermore, according to the present disclosure, by setting the value of the ratio (C / (A+B)) within a predetermined range, not only is the storage stability of the antibacterial composition improved, but precipitation of the diiodomethane compound (A) is suppressed when the antibacterial composition is diluted with a solvent (i.e., the dilution stability of the antibacterial composition is improved). As a result, the handleability of the antibacterial composition is further improved. From the viewpoint of storage stability and dilution stability, the value of the ratio (C / (A+B)) is preferably 8.00 or more, more preferably 9.00 or more, even more preferably 10.00 or more, and particularly preferably 10.45 or more.

[0014] The value of the ratio (A / B) of the content of the diiodomethane compound (A) to the content of the quaternary ammonium salt (B) (hereinafter, simply referred to as the "ratio (A / B)") is not particularly limited, but from the viewpoint of storage stability, it is preferably 1.01 or more, and more preferably 1.02 or more. From the viewpoint of antibacterial effect or dilution stability, the value of the ratio (A / B) is preferably 99.0 or less, more preferably 9.00 or less, further preferably 2.00 or less, and particularly preferably 1.50 or less.

[0015] (1.1) Diiodomethane compounds (A) The antimicrobial compositions of the present disclosure contain a diiodomethane compound (A).

[0016] The diiodomethane compound (A) may be any known diiodomethane compound, but from the viewpoint of exhibiting a good antibacterial effect of the antibacterial composition, it is preferable that the diiodomethane compound (A) contains a compound (1) represented by the following general formula (1).

[0017] [ka]

[0018] In the general formula (1), R 1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, an alkylaminocarbonyl group having 2 to 7 carbon atoms, or a dialkylaminocarbonyl group having 3 to 13 carbon atoms; R 2 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms; and n represents 0 or 1. L1 represents a carbonyl group or a sulfonyl group.

[0019] R 1 The alkyl group having 1 to 6 carbon atoms represented by the following formula may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. R 1The alkyl group represented by the following formula (1) preferably has 1 to 3 carbon atoms, and more preferably 1 to 2 carbon atoms. R 1 Specific examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a cyclobutyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a cyclopentyl group, an n-hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, and a cyclohexyl group.

[0020] R 1 Specific examples of the acyl group having 1 to 7 carbon atoms represented by the formula (I) include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pentanoyl group, a pivaloyl group, a hexanoyl group, a heptanoyl group, and a benzoyl group.

[0021] R 1 The alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms represented by the following formula is preferably an alkoxy group having 1 to 6 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, and even more preferably an alkoxy group having 1 or 2 carbon atoms. The alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms may be a linear alkoxy group, a branched alkoxy group, or an alkoxy group having a cyclic structure, and is preferably a linear alkoxy group or a branched alkoxy group. Specific examples of the alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group, a cyclobutoxy group, an n-pentyloxy group, an isopentyloxy group, a 2-methylbutoxy group, a neopentyloxy group, a 1-ethylpropoxy group, a cyclopentyloxy group, an n-hexyloxy group, a 4-methylpentyloxy group, a 3-methylpentyloxy group, a 2-methylpentyloxy group, a 1-methylpentyloxy group, a 3,3-dimethylbutoxy group, a 2,2-dimethylbutoxy group, a 1,1-dimethylbutoxy group, a 1,2-dimethylbutoxy group, a 1,3-dimethylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, and a cyclohexyloxy group.

[0022] R 1 The alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms represented by the following formula is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably an alkyl group having 1 to 2 carbon atoms. The alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. Specific examples of the alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a cyclobutyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a cyclopentyl group, an n-hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, and a cyclohexyl group.

[0023] R 1 The two alkyl groups constituting the dialkylaminocarbonyl group having 3 to 13 carbon atoms represented by the following formula may be the same or different. The two alkyl groups may be bonded to each other to form a cyclic structure.

[0024] R 1 is preferably a hydrogen atom or an alkoxycarbonyl group having 2 to 7 carbon atoms, and more preferably a hydrogen atom or an ethoxycarbonyl group.

[0025] R 2 The alkyl group having 1 to 6 carbon atoms represented by the following formula may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. R 2 The alkyl group represented by the following formula (1) preferably has 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms, and further preferably 1 carbon atom. R 2Specific examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a cyclobutyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a cyclopentyl group, an n-hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, and a cyclohexyl group.

[0026] R 2 Specific examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0027] R 2 The substitution position of R is not particularly limited. 2 The substitution position of may be the ortho-position, meta-position, or para-position with respect to the carbon atom to which L1 is bonded in the benzene ring of general formula (1), and is preferably the para-position.

[0028] R 2 As the alkyl group, a methyl group or an ethyl group is preferable, and a methyl group is more preferable.

[0029] n represents 0 or 1, and is preferably 1.

[0030] L1 represents a carbonyl group or a sulfonyl group.

[0031] Examples of the diiodomethane compound (A) include diiodomethyl-p-tolylsulfone, diiodomethyl-o-tolylsulfone, diiodomethyl-m-tolylsulfone, diiodomethyl-p-chlorophenylsulfone, diiodomethyl-p-bromophenylsulfone, diiodomethyl-p-ethylphenylsulfone, diiodomethyl-p-propylphenylsulfone, diiodomethylphenylketone, diiodomethyl(4-methylphenyl)ketone, diiodomethyl(4-chlorophenyl)ketone, and methyl-2,2-diiodo-3-oxo-3-phenylpropionate. In particular, from the viewpoint of exhibiting a good antibacterial effect of the antibacterial composition, the diiodomethane compound (A) preferably contains at least one selected from the group consisting of diiodomethyl-p-tolylsulfone, diiodomethyl-o-tolylsulfone, diiodomethyl-m-tolylsulfone, and diiodomethyl-p-chlorophenylsulfone, and more preferably contains diiodomethyl-p-tolylsulfone (A-1) (hereinafter also referred to as "DMTS (A-1)").

[0032] The diiodomethane compound (A) may be a commercially available product. Examples of commercially available products include "YOTOLU (registered trademark) DP95" (manufactured by Mitsui Chemicals, Inc., main component: DMTS (A-1)) and "YOTOLU (registered trademark) DP-CD" (manufactured by Mitsui Chemicals, Inc., main components: DMTS (A-1) and methyl-β-cyclodextrin).

[0033] (1.1.1) Content ratio The content of the diiodomethane compound (A) is not particularly limited as long as the ratio (C / (A+B)) falls within the above range, and is appropriately selected depending on the form of the antibacterial composition.

[0034] When the antibacterial composition is in the form of a solution, the content of the diiodomethane compound (A) is preferably 0.01 mass% to 10 mass%, more preferably 0.1 mass% to 5.0 mass%, and even more preferably 1.0 mass% to 3.0 mass%, relative to the total amount of the antibacterial composition. When the antibacterial composition is in the form of a powder, the content of the diiodomethane compound (A) is preferably 0.01% by mass to 99% by mass, more preferably 0.1% by mass to 40% by mass, and further preferably 5% by mass to 35% by mass, based on the total amount of the antibacterial composition. In the present disclosure, the content ratio of the diiodomethane compound (A) is considered to be the same as the addition ratio (blending ratio) of the diiodomethane compound (A).

[0035] (1.2) Quaternary ammonium salts (B) The antimicrobial composition of the present disclosure contains a quaternary ammonium salt (B).

[0036] Examples of the quaternary ammonium salt (B) include benzalkonium-type quaternary ammonium salts, alkylpyridinium chlorides, alkyltrimethylammonium halides, and dialkyldimethylammonium chlorides. Examples of the benzalkonium-type quaternary ammonium salt include benzalkonium chloride, benzethonium chloride, myristyldimethylbenzylammonium chloride, and stearyldimethylbenzylammonium chloride. Examples of the alkylpyridinium chloride include cetylpyridinium chloride and laurylpyridinium chloride. Examples of the alkyltrimethylammonium halide include lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, and stearyltrimethylammonium chloride. Examples of dialkyldimethylammonium chloride include dimethyldidecylammonium chloride, N-decyl-N-isononyldimethylammonium chloride, dioctyldimethylammonium chloride, dicetyldimethylammonium chloride, and dimethyldistearylammonium chloride. The quaternary ammonium salt (B) may contain at least one of a benzalkonium-type quaternary ammonium salt and an alkylpyridinium chloride.

[0037] Among these, from the viewpoint of exerting an excellent synergistic antibacterial effect, the quaternary ammonium salt (B) preferably contains at least one selected from the group consisting of benzalkonium chloride, benzethonium chloride, and cetylpyridinium chloride, and benzalkonium chloride is most preferable.

[0038] Benzalkonium chloride is [C6H5CH2N(CH3)2R] + Cl - It is a general term for compounds having the chemical structure represented by the formula: where R is an alkyl group having 8 to 18 carbon atoms, or mixtures of these compounds. Benzalkonium chloride, where R is an alkyl group having 12 to 14 carbon atoms, has the strongest bactericidal power. The "10% Benzalkonium Chloride Solution" manufactured by Fujifilm Wako Pure Chemical Corporation contains benzalkonium chloride, where R is an alkyl group having 12 to 14 carbon atoms, as its main ingredient.

[0039] The quaternary ammonium salt (B) may be a commercially available product. Commercially available products of benzalkonium chloride include "10% benzalkonium chloride solution" (manufactured by Fujifilm Wako Pharmaceutical Co., Ltd.), "Benzalkonium Chloride" (manufactured by Toronto Research Chemicals), and 50% benzalkonium chloride solution (manufactured by Toho Chemical Industry Co., Ltd.). Commercially available products of benzethonium chloride include "benzethonium chloride" (manufactured by Fujifilm Wako Pure Chemical Industries Co., Ltd.). Commercially available products of cetylpyridinium chloride include "hexadecylpyridinium chloride monohydrate" (manufactured by Fujifilm Wako Pure Chemical Industries Co., Ltd.).

[0040] (1.2.2) Content ratio The content of the quaternary ammonium salt (B) is not particularly limited as long as the ratio (C / (A+B)) falls within the above range, and is appropriately selected depending on the form of the antibacterial composition. When the antibacterial composition is in the form of a solution, the content of the quaternary ammonium salt (B) is preferably 0.01 mass% to 30 mass%, more preferably 0.1 mass% to 5 mass%, and even more preferably 0.3 mass% to 2 mass%, relative to the total amount of the antibacterial composition. When the antibacterial composition is in the form of a powder, the content of the quaternary ammonium salt (B) is preferably 0.01% by mass to 99% by mass, more preferably 0.5% by mass to 60% by mass, or 1% by mass to 30% by mass, relative to the total amount of the antibacterial composition. In the present disclosure, the content ratio of the quaternary ammonium salt (B) is considered to be the same as the addition ratio (blending ratio) of the quaternary ammonium salt (B).

[0041] (1.3) Cyclodextrin derivatives (C) The antimicrobial compositions of the present disclosure contain a cyclodextrin derivative (C).

[0042] The antibacterial composition further contains a cyclodextrin derivative (C), which makes it easier to form an inclusion compound. The inclusion compound may contain a diiodomethane compound (A) as a guest compound and a cyclodextrin derivative (C) as a host compound. The cyclodextrin derivative (C) has high solubility in water. Therefore, even if the diiodomethane compound (A) has low solubility in water (e.g., DMTS (A-1)), the inclusion compound has high solubility in water. As a result, the antibacterial composition can be used in the form of a solution. Therefore, the antibacterial composition is easier to handle.

[0043] Examples of the substituent in the cyclodextrin derivative (C) include an alkyl group and a hydroxyalkyl group. The alkyl group and the hydroxyalkyl group preferably have 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms, and further preferably 1 carbon atom.

[0044] The cyclodextrin derivative (C) may be any of an α-cyclodextrin derivative, a β-cyclodextrin derivative, and a γ-cyclodextrin derivative, or a mixture thereof. Specific examples of the cyclodextrin derivative (C) include methyl-β-cyclodextrin, hydroxypropyl-β-cyclodextrin, methyl-γ-cyclodextrin, and methyl-α-cyclodextrin. Among these, from the viewpoint of facilitating the formation of an inclusion compound, it is preferable that the cyclodextrin derivative (C) contains a β-cyclodextrin derivative (that is, a β-cyclodextrin-based compound containing β-cyclodextrin or a derivative thereof). From the viewpoint of improving the solubility of the diiodomethane compound (A) in an aqueous solution, the β-cyclodextrin derivative preferably contains methyl-β-cyclodextrin or hydroxypropyl-β-cyclodextrin, and more preferably contains methyl-β-cyclodextrin.

[0045] The β-cyclodextrin derivative may be a commercially available product, such as "CAVASOL W7 M" (methyl-β-cyclodextrin, manufactured by CycloChem), "CAVASOL W7 HP" (hydroxypropyl-β-cyclodextrin, manufactured by CycloChem), "chemically modified cyclodextrin methyl-β-CD" (manufactured by Ensuikou Sugar Refining Co., Ltd.), "chemically modified cyclodextrin HP-β-CD" (manufactured by Ensuikou Sugar Refining Co., Ltd.), and "Celdex HP-β-CD" (manufactured by Nihon Shokuhin Kako Co., Ltd.).

[0046] (1.3.1) Content ratio The content of the cyclodextrin derivative (C) is not particularly limited as long as the ratio (C / (A+B)) falls within the above range, and is appropriately selected depending on the form of the antibacterial composition.

[0047] When the antibacterial composition is in the form of a solution or powder, the content of the cyclodextrin derivative (C) is not particularly limited and is appropriately selected depending on the application of the antibacterial composition, and is preferably in the following range. From the viewpoint of improving the solubility of the antibacterial composition in water, the content of the cyclodextrin derivative (C) is preferably 300% by mass to 3600% by mass, more preferably 600% by mass to 2700% by mass, and even more preferably 900% by mass to 2100% by mass, relative to the total mass of the diiodomethane compound (A) contained in the antibacterial composition. In the present disclosure, the content ratio of the cyclodextrin derivative (C) is regarded as being the same as the addition ratio (blending ratio) of the cyclodextrin derivative (C).

[0048] (1.4) Solvent The antibacterial composition of the present disclosure may further contain a solvent (D) as necessary, in addition to the diiodomethane compound (A), the quaternary ammonium salt (B) and the cyclodextrin derivative (C), or may not contain the solvent (D). By including the solvent (D), the antibacterial composition can be in the form of a solution, which makes the antibacterial composition easier to handle than an antibacterial composition in the form of a powder.

[0049] The solvent (D) may be an aqueous solvent or a non-aqueous solvent. The aqueous solvent may be any solvent containing water, such as water (e.g., purified water (hereinafter also referred to as "purified water (D-1)"), ion-exchanged water), physiological saline, etc.). The non-aqueous solvent may be any solvent not containing water, such as an organic solvent. Examples of the organic solvent include sulfur atom-containing solvents (e.g., dimethyl sulfoxide, etc.), monohydric alcohols (e.g., ethanol, isopropanol, benzyl alcohol, etc.), glycol-based solvents (e.g., ethylene glycol, diethylene glycol, polyethylene glycol, etc.) and derivatives thereof, glycerin-based solvents (e.g., glycerin, diglycerin, etc.) and derivatives thereof, cyclic organic solvents (e.g., N-methylpyrrolidone, N-ethylpyrrolidone, etc.), ester-based solvents (e.g., phthalic acid esters, adipic acid esters, sebacic acid esters, etc.), ketone-based solvents (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), aromatic solvents (e.g., methylnaphthalene, phenylxylylethane, alkylbenzene, etc.), aliphatic hydrocarbon solvents (e.g., normal paraffin, isoparaffin, etc.), etc. These solvents may be used alone or in combination of two or more.

[0050] (1.4.1) Content ratio The content of the solvent (D) is not particularly limited and is appropriately selected depending on the application of the antibacterial composition, and is preferably in the following range. Hereinafter, the case where the antibacterial composition further contains a solvent (D) will be described. The content of the solvent (D) is preferably 30% by mass to 99% by mass, more preferably 50% by mass to 99% by mass, and further preferably 50% by mass to 70% by mass, based on the total amount of the antibacterial composition. In the present disclosure, the content ratio of the solvent (D) is considered to be the same as the addition ratio (blending ratio) of the solvent (D).

[0051] When the solvent (D) is purified water (D-1), the content of the solvent (D) is preferably 50% by mass to 99% by mass, more preferably 60% by mass to 99% by mass, and even more preferably 90% by mass to 99% by mass, relative to the total amount of the antibacterial composition, from the viewpoint of further suppressing precipitation of the diiodomethane compound (A).

[0052] (1.5) Other ingredients The antibacterial composition of the present disclosure may further contain other components (E) as necessary in addition to the diiodomethane compound (A), the quaternary ammonium salt (B) and the cyclodextrin derivative (C), or may not contain other components (E). The other components (E) may be known components, such as surfactants, pH adjusters, antifoaming agents, rust inhibitors, viscosity adjusters (e.g., thickeners), sequestering agents (chelating agents), light stabilizers, ultraviolet absorbers, accelerators, adhesion promoters, fragrances, scale inhibitors, antistatic agents, resin binders, softening agents, antibacterial components, antiviral agents, other antifungal agents, etc. These other components may be blended alone or in combination of two or more.

[0053] (1.6) Preferred composition The antibacterial composition of the present disclosure contains a diiodomethane compound (A), a quaternary ammonium salt (B), a cyclodextrin derivative (C), and water, and the ratio (C / (A+B)) is 10.00 or more, and preferably the ratio (C / A) is 20.00 or more. This provides better storage stability for the diiodomethane compound (A). Furthermore, even if the content of water is 90 mass% or more relative to the total amount of the antibacterial composition, the diiodomethane compound (A) is unlikely to precipitate.

[0054] (1.7) Preferred composition The antibacterial composition of the present disclosure contains a diiodomethane compound (A), a quaternary ammonium salt (B), a cyclodextrin derivative (C), and water, and preferably has a ratio (C / (A+B)) of 10.00 or more, a ratio (C / A) of 20.00 or more, and a ratio (A / B) of 1.50 or less. This provides better storage stability for the diiodomethane compound (A). Furthermore, even if the content of water is 90 mass% or more relative to the total amount of the antibacterial composition, the diiodomethane compound (A) is less likely to precipitate. Furthermore, the antibacterial composition is less expensive to manufacture.

[0055] (1.7) Uses of the antibacterial composition The antibacterial composition of the present disclosure can be used for a variety of purposes without any particular limitation. The uses of the antibacterial composition include, for example, all of the components and products used as various industrial products and daily necessities. Specifically, the above-mentioned uses include, for example, agricultural fields (e.g., pesticides, etc.), forestry fields (e.g., wood preservatives, etc.), fishing fields (e.g., flotation devices, fishing gear, and water tanks, etc.), livestock fields (e.g., feed, feed troughs, and calf jackets, etc.), construction fields (e.g., interior building materials such as wallpaper, wall boards, wall materials, and flooring materials, paints, adhesives, filters, tiles, cement, concrete, termite and insect repellents for building materials, and materials such as wood, etc.), food fields (e.g., food preservatives, etc.), beverages, tobacco, and feed fields (e.g., water and tobacco, etc.), textile fields (e.g., clothing and bedding, etc.), pulp, paper, and paper products fields (e.g., packaging materials such as wrapping paper, etc.), chemical industry fields (e.g., metal processing fluids, cleaning agents, cooling water, surface treatment agents such as plating fluids, cutting fluids for plastics or glass (e.g., lens processing fluids), inks, printing toners, pharmaceuticals, cosmetics, toiletries, sanitary products, sterilization and disinfectants, deodorants, preservatives, detergents, etc.), plastic products (for example, resin molded bodies, films, and synthetic leather (for example, polyurethane-based synthetic leather), etc.), rubber products, tanned leather and related products, and fur (for example, leather, etc.), ceramics and stone and clay products (for example, ceramics such as tableware), electrical machinery and equipment (for example, household electrical appliances such as refrigerators and air conditioners, and their parts, etc.), transportation machinery and equipment (for example, automobiles and ships for logistics), precision machinery and equipment (for example, high-tech equipment and optical equipment), other product areas (for example, sporting goods, school supplies, writing ink, toys, miscellaneous goods such as plastic, and household goods), and medical and welfare services (for example, parts and products used in hospitals, nursing homes, and public facilities, etc.).

[0056] Among others, preferred applications of the antibacterial composition include interior building materials, paints, inks, printing toners, wallpaper, adhesives, metalworking fluids, surface treatment agents, cutting fluids for plastics or glass (e.g., lens processing fluids), molded articles (e.g., films, sheets, and plastic products (e.g., resin molded bodies and synthetic leather (e.g., polyurethane-based synthetic leather)), etc.), fibers (clothing, bedding, etc.), ceramics (tableware, etc.), paper and pulp products, detergents, deodorants, preservatives, and rubber products.

[0057] In other words, by processing the components, products, etc. in the fields exemplified above so that they contain the antibacterial composition of the present disclosure, it is possible to impart antibacterial effects to the components, products, etc.

[0058] (1.8) Formulation of antibacterial compositions The antibacterial composition of the present disclosure may be used for various applications after the antibacterial composition is formulated. By formulating and using the antibacterial composition, the antibacterial composition of the present disclosure may be more easily applied to the fields, components, products, etc. described above. The formulation obtained by formulation is not particularly limited, and various formulations such as water-based, powder-based, and solvent-based (for example, oil solutions, emulsions, solubilized preparations, wettable powders, flowable agents (suspensions in water, emulsions in water, etc.), microcapsules, powders, tablets, aerosols, and carbon dioxide gas formulations, etc.) are applicable. The antibacterial composition of the present disclosure can be formulated together with any component generally used in formulation. EXAMPLES

[0059] Hereinafter, the present disclosure will be described in more detail with reference to examples, but the present disclosure is not limited to the following examples as long as it does not deviate from the gist of the disclosure. In addition, unless otherwise specified, "parts" are based on mass.

[0060] [1] Preparation of antibacterial composition The products used in the Examples, Reference Examples and Comparative Examples are as follows.

[0061] (Diiodomethane compound (A)) · DMTS (A-1): "YOTOLU (registered trademark) DP95" manufactured by Mitsui Chemicals, Inc. (ingredients: diiodomethyl-p-tolylsulfone, form: powder) was used.

[0062] (Quaternary ammonium salt (B)) BAC (B-1): 50% benzalkonium chloride aqueous solution (manufactured by Toho Chemical Industry Co., Ltd.) was used. Note that the BAC (B-1) content (mass%) shown in Table 1 or Table 2 below does not mean the content as a 50% benzalkonium chloride aqueous solution, but means the content of the solid content (benzalkonium chloride).

[0063] (Cyclodextrin derivatives (C)) · MβCD (C-1): "CAVASOL (registered trademark) W7 M" (ingredient: methyl-β-cyclodextrin, form: powder) manufactured by CycloChem Co., Ltd. was used.

[0064] (Solvent (D)) ·Purified water (D-1): Purified water

[0065] [2] Examples, Comparative Examples and Reference Examples [2.1] Example 1 2.78 parts by mass of DMTS (A-1), 0.31 parts by mass of BAC (B-1), and 32.2 parts by mass of MβCD (C-1) were added to purified water (D-1) and mixed to obtain an antibacterial composition.

[0066] [2.2] Examples 2 to 9, Comparative Examples 1 to 2, Reference Example 1 Each antibacterial composition was obtained in the same manner as in Example 1, except that the composition of the antibacterial composition was as shown in Table 1 or Table 2 below.

[0067] [3] Evaluation [3.1] Manufacturing evaluation The antibacterial compositions immediately after production of each of the Examples, Comparative Examples, and Reference Examples were analyzed by high performance liquid chromatography under the following analytical conditions. As a result, the content of DMTS (A-1) contained in the antibacterial composition immediately after production (hereinafter also referred to as the "content of DMTS immediately after production") and the content of BAC (B-1) contained in the antibacterial composition immediately after production (hereinafter also referred to as the "content of BAC immediately after production") were measured. "Immediately after production" refers to the time before 5 hours have elapsed since DMTS (A-1), BAC (B-1), and MβCD (C-1) were added to purified water (D-1) and mixed.

[0068] <Analysis conditions> Column: YMC-Pack ODS-A (150 x 6 mm) manufactured by YMC Corporation Mobile phase: acetonitrile:H2O (0.1% trifluoroacetic acid) = 5:5 → 10:0 Over 15 min, retention 10 min, flow rate 0.5 mL / min ·Temperature: 40℃ Detection wavelength: 254nm

[0069] The DMTS content immediately after production was calculated from the DMTS content immediately after production and the DMTS (A-1) content calculated from the amount of the raw materials charged for the antibacterial composition (hereinafter also referred to as the "theoretical DMTS content") according to the following formula (2). The closer the DMTS content immediately after production is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., almost all of the charged DMTS is clathrated). The calculation results are shown in Tables 1 and 2.

[0070] Equation (2): DMTS content immediately after production = (DMTS content immediately after production / theoretical DMTS content) x 100

[0071] [3.2] Post-storage evaluation The antibacterial compositions of each Example, Comparative Example, and Reference Example were placed in a light-shielding bottle on the day of production and stored at 50°C for 3 weeks. The antibacterial compositions after storage at 50°C were analyzed by high performance liquid chromatography under the same analytical conditions as those for the above-mentioned evaluation at the time of production. As a result, a chromatogram was obtained in which the peak of DMTS (A-1) and the peak of BAC (B-1) were separated. The content ratios (mass%) of DMTS (A-1) and BAC (B-1) contained in the antibacterial compositions of each Example, Comparative Example, and Reference Example immediately after production and after storage at 50°C were calculated by the absolute calibration curve method using samples with known concentrations prepared in advance. The supernatant of each sample immediately after production and after storage at 50°C was collected and analyzed.

[0072] The storage stability of DMTS was calculated by the following formula (3) using the DMTS content immediately after production and the DMTS (A-1) content in the antibacterial composition after storage at 50°C (hereinafter also referred to as "DMTS after storage at 50°C"). The calculation results are shown in Tables 1 and 2. The closer the DMTS storage stability is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., DMTS is dispersed in the antibacterial composition). The acceptable storage stability of DMTS is 90% or more.

[0073] Equation (3): Storage stability of DMTS = (DMTS content after storage at 50°C / DMTS content immediately after production) x 100

[0074] The storage stability of BAC was calculated by the following formula (4) using the content of BAC immediately after production and the content of BAC (B-1) in the antibacterial composition after storage at 50°C (hereinafter also referred to as "BAC after storage at 50°C"). The closer the storage stability of BAC is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., the more the BAC is dispersed in the antibacterial composition). The calculation results are shown in Tables 1 and 2.

[0075] Equation (4): Storage stability of BAC = (BAC content after storage at 50°C / BAC content immediately after production) x 100

[0076] [3.3] Dilution stability evaluation [3.3.1] Dilution stability evaluation (10-fold dilution) Purified water (D-1) was added to the antibacterial composition immediately after production of each Example, Comparative Example, and Reference Example so that the content ratio of each component was diluted 10 times to obtain a 10-fold diluted antibacterial composition (hereinafter also referred to as "antibacterial composition (10-fold diluted)"). The content ratio of purified water (D-1) in the antibacterial composition (10-fold diluted) was 90 mass% or more with respect to the total amount of the antibacterial composition (10-fold diluted). The antibacterial composition (10-fold diluted) was placed in a transparent bottle on the day of production and stored overnight at room temperature. The antibacterial composition (10-fold diluted) after dilution and storage was analyzed using a high performance liquid chromatography method under the same analytical conditions as those for the above-mentioned evaluation at the time of production. The content ratios (mass%) of DMTS (A-1) and BAC (B-1) contained in the antibacterial composition (10-fold diluted) immediately after production and after dilution and storage of each Example, Comparative Example, and Reference Example were calculated by an absolute calibration curve method using samples with known concentrations prepared in advance. The supernatant of each sample was collected immediately after production and after dilution and storage, and analyzed.

[0077] The dilution stability of DMTS (10 times) was calculated from the content of DMTS (A-1) in the antibacterial composition (10 times diluted) after dilution and storage (hereinafter also referred to as the "content of DMTS (10 times diluted) after dilution and storage") and the content of DMTS immediately after production, according to the following formula (5). The closer the dilution stability of DMTS (10 times) is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., the more DMTS is dispersed in the antibacterial composition (10 times diluted)). The calculation results are shown in Tables 1 and 2.

[0078] Equation (5): Dilution stability of DMTS (10-fold dilution) = [DMTS content after dilution and storage (10-fold dilution) / (DMTS content immediately after manufacture × 10 (i.e., theoretical content of DMTS after dilution))] × 100

[0079] The dilution stability of BAC (10 times) was calculated from the content of BAC (B-1) in the antibacterial composition (10 times diluted) after dilution and storage (hereinafter also referred to as "content of BAC (10 times diluted) after dilution and storage") and the content of BAC immediately after production, according to the following formula (6). The closer the dilution stability of BAC (10 times) is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., the more the BAC is dispersed in the antibacterial composition (10 times diluted)). The calculation results are shown in Tables 1 and 2.

[0080] Equation (6): Dilution stability of BAC (10-fold dilution) = [Content of BAC (10-fold dilution) after dilution storage / (Content of BAC immediately after manufacture × 10) (i.e., theoretical content of BAC after dilution)] × 100

[0081] [3.3.2] Dilution stability evaluation (50-fold dilution) The 50-fold diluted antibacterial composition (hereinafter also referred to as "dilution stability evaluation (50-fold dilution)") was analyzed in the same manner as the dilution stability evaluation (10-fold dilution), except that purified water was added to the antibacterial composition immediately after production so that the content ratio of each component was diluted 50 times. The content ratio of purified water (D-1) in the antibacterial composition (50-fold dilution) was 99 mass% relative to the total amount of the antibacterial composition (50-fold dilution).

[0082] The dilution stability of DMTS (50-fold dilution) was calculated from the content of DMTS (A-1) in the antibacterial composition (50-fold dilution) after dilution and storage (hereinafter also referred to as "content of DMTS (50-fold dilution) after dilution and storage") and the content of DMTS immediately after production according to the following formula (7). The closer the dilution stability of DMTS (50-fold) is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., the more DMTS is dispersed in the antibacterial composition (50-fold dilution)). The calculation results are shown in Tables 1 and 2.

[0083] Equation (7): Dilution stability of DMTS (50-fold dilution) = [DMTS content after dilution and storage (50-fold dilution) / (DMTS content immediately after manufacture × 50) (i.e., theoretical content of DMTS after dilution)] × 100

[0084] The dilution stability of BAC (50-fold dilution) was calculated from the content of BAC (B-1) in the antibacterial composition (50-fold dilution) after dilution and storage (hereinafter also referred to as "content of BAC (50-fold dilution) after dilution and storage") and the content of BAC immediately after production, according to the following formula (8). The closer the dilution stability of BAC (50-fold) is to 100%, the less precipitates and the like are generated in the antibacterial composition (i.e., the more the BAC is dispersed in the antibacterial composition (50-fold dilution)). The calculation results are shown in Tables 1 and 2.

[0085] Equation (8): Dilution stability of BAC (50-fold dilution) = [Content of BAC (50-fold dilution) after dilution storage / (BAC content immediately after manufacture × 50) (i.e., theoretical content of BAC after dilution)] × 100

[0086] [Table 1]

[0087] [Table 2]

[0088] [3.4] Evaluation of antibacterial effect The antibacterial effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0089] [3.4.1] MIC test (bacteria) [3.4.1.1] Culture media, etc. In the antibacterial test, the following LB (Lysogeny Broth) medium was used. LB medium was prepared by dissolving 25 g of "Difco LB Broth Miller (Luria-Bertani)" (manufactured by Becton, Dickinson and Company) in 1000 mL of distilled water.

[0090] [3.4.1.2] Preculture In the MIC test method (bacteria), the following bacterial species (a1) to (b3) were used. The bacterial species (a1) to (b3) were test bacterial species cultured at 35°C for 24 hours using LB medium that had been autoclaved at 121°C for 20 minutes. Bacterial species (a1): Staphylococcus aureus (NBRC 12732, provided by National Institute of Technology and Evaluation, Staphylococcus aureus) Bacterial species (a2): Bacillus subtilis (NBRC 13719, distributing agency National Institute of Technology and Evaluation, Bacillus subtilis) Bacterial species (b1): Escherichia coli (NBRC 3972, provided by National Institute of Technology and Evaluation, E. coli)

[0091] [3.4.1.3] Sample preparation The antibacterial compositions of Examples 1 to 9, Comparative Examples 1 and 2, and Reference Example 1 were added to LB medium sterilized by autoclaving at 121° C. for 20 minutes to prepare 12 two-fold dilution series on a multi-well plate with the maximum concentration of the active ingredient being 1000 ppm, thereby obtaining culture media containing the antibacterial compositions. The "maximum concentration of active ingredient" in the MIC test method (bacteria) refers to the ratio (mass %) of the total mass of the antibacterial composition-containing medium (A+B) calculated from the blending amounts of the diiodomethane compound (A) and the quaternary ammonium salt (B) to the total mass of the antibacterial composition-containing medium.

[0092] [3.4.1.4] Bacterial liquid preparation The test bacterial species was suspended in LB medium that had been autoclaved at 121° C. for 20 minutes, and the suspension was adjusted to have an OD (Optical Density) of 1.0 to 2.0. This gave a bacterial solution.

[0093] [3.4.1.5] MIC measurement (bacteria) 2 μL of a bacterial solution of the bacterial species shown in Table 3 was inoculated into 100 μL of each of the dilution series of the antibacterial composition-containing medium, and cultured at 35° C. for 18 to 24 hours. The growth of bacteria was confirmed by visual inspection, and the minimum dilution concentration at which no bacteria grew was taken as the MIC value. When the medium containing the antibacterial composition was clear, it was determined that no bacteria grew. The measurement results are shown in Table 3. The detection limit of the MIC test (bacteria) is 0.49 ppm.

[0094] MIC tests (bacteria) were performed a total of three times. When the MIC values ​​measured in three MIC tests (bacteria) were different, the maximum and minimum of the three MIC values ​​are listed in the format of "minimum to maximum" in Table 3. For example, "0.98 to 1.95" in Table 1 indicates that the minimum MIC value was 0.98 ppm and the maximum MIC value was 1.95 ppm among the three tests. When the MIC values ​​of three MIC tests (bacteria) were different and some MIC values ​​were outside the measurement range, and the numerical value could not be specified, the maximum value of the three MIC values ​​was stated in the format of "≦maximum value." For example, "≦0.49" in Table 1 indicates that the maximum MIC value of the three tests was 0.49 ppm.

[0095] [3.4.2] Theoretical MIC (bacteria) The presence or absence of synergistic effects was examined using Colby's formula (Colby, SR, Weeds, Vol. 15, pp. 20-22, 1967) shown in the following formula (9). In detail, the theoretical MIC value of the two-drug mixture (i.e., the antibacterial composition containing the diiodomethane compound (A) and the quaternary ammonium salt (B)) was calculated using the measured MIC value of each single agent (i.e., the antibacterial composition containing each of the diiodomethane compound (A) and the quaternary ammonium salt (B)) according to the following formula (9). The calculated theoretical MIC values ​​are shown in Table 3. The fact that the measured MIC value of an antibacterial composition is lower than the theoretical MIC value indicates that the effect of the two-drug mixture exceeds the additive effect, i.e., there is a synergistic effect (i.e., a high antibacterial effect).

[0096] Equation (9): MIC theoretical value = C A ×Ratio(A / B)+C B×(1-ratio(A / B))

[0097] In formula (9), “C A " indicates the measured MIC value of the diiodomethane compound (A) alone. B " indicates the measured MIC value of the quaternary ammonium salt (B) alone.

[0098] [3.5] Evaluation of antifungal effect The antifungal effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0099] [3.5.1] MIC test (mold) 3.5.1.1 Culture media and detergent solutions In the MIC test (mold), the following PDA (Potato Dextrose Agar) medium, PDB (Potato Dextrose Broth) medium, and surfactant solution were used. PDA medium was prepared by dissolving 39 g of "Difco Potato Dextrose Agar" (Becton Dickinson and Company) in 1000 mL of distilled water and adding 1 mL of chloramphenicol (Fujifilm Wako Pure Chemical Industries, special grade reagent) diluted to 50 mg / mL with ethanol. PDB medium was prepared by dissolving 24 g of "Difco Potato Dextrose Broth" (Becton Dickinson and Company) in 1000 mL of distilled water and adding 1 mL of chloramphenicol (Fujifilm Wako Pure Chemical Industries, special grade reagent) diluted to 50 mg / mL with ethanol. The surfactant solution was prepared by dissolving 8.5 g of "sodium chloride" (special grade reagent, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 0.5 mL of "polyoxyethylene (20) sorbitan monooleate" (molecular biology grade, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in 1000 mL of distilled water.

[0100] [3.5.1.2] Preculture The following mold species (c1) was used in the MIC test (mold). The mold species (c1) was a test mold species cultured at 25°C for 7 days or more using PDA medium that had been autoclaved at 121°C for 20 minutes. Mold species (c1): Aspergillus niger (NBRC 105649, provided by National Institute of Technology and Evaluation, Aspergillus niger)

[0101] [3.5.1.3] Sample preparation The antibacterial compositions of Examples 1, 5 to 9, Comparative Examples 1 and 2, and Reference Example 1 were added to PDB media sterilized by autoclaving at 121°C for 20 minutes to prepare 11 two-fold dilution series with the maximum concentration of the active ingredient being 100 ppm, thereby obtaining media containing the antibacterial compositions. The "maximum concentration of active ingredient" in the MIC test method (mold) refers to the ratio (mass %) of the total mass of the antibacterial composition-containing medium (A+B) calculated from the blending amounts of the diiodomethane compound (A) and the quaternary ammonium salt (B) to the total mass of the antibacterial composition-containing medium.

[0102] [3.5.1.4] Mold solution preparation The test mold species was suspended in a surfactant solution that had been autoclaved at 121°C for 20 minutes, and the number of spores was determined to be 1 x 10 using a hemocytometer. 5 / mL~100×10 5 / mL. This gave a mold solution.

[0103] [3.5.1.5] MIC measurement (mold) 100 μL of mold liquid of the mold species listed in Table 3 was inoculated into 2 mL of each of the dilution series of the prepared antibacterial composition-containing medium, and cultured at 25° C. for 7 days. Mold growth was confirmed by visual inspection, and the minimum dilution concentration at which no mold growth occurred was taken as the MIC value. When no clumps of mold hyphae were visually observed in the medium containing the antibacterial composition, it was determined that no mold growth occurred. The measurement results are shown in Table 3. The detection limit of the MIC test (mold) is 0.1 ppm.

[0104] MIC tests (mold) were performed a total of two times. When the MIC values ​​measured in the two MIC tests (molds) were different, they were reported in the same format as the MIC test for bacteria (bacteria).

[0105] [Table 3]

[0106] In Table 3, "S. aureus" indicates Staphylococcus aureus, "B. subtilis" indicates Bacillus subtilis, and "E. coli" indicates Escherichia coli.

[0107] In Comparative Examples 1 and 2, the ratio (C / (A+B)) was not 6.00 or more. Therefore, the storage stability of DMTS in Comparative Examples 1 and 2 was not 90% or more. As a result, it was found that the antibacterial compositions of Comparative Examples 1 and 2 exhibited a higher antibacterial effect against gram-positive bacteria than when the diiodomethane compound was used alone, and that they were not antibacterial compositions having excellent storage stability of the diiodomethane compound.

[0108] The antibacterial compositions of Examples 1 to 9 contained a diiodomethane compound (A), a quaternary ammonium salt (B), and a cyclodextrin derivative (C). The ratio (C / (A+B)) was 6.00 or more. Therefore, the storage stability of DMTS in Examples 1 to 9 was 90% or more. Furthermore, in Examples 1 to 9, as shown in Table 3, the actually measured MIC values ​​against Staphylococcus aureus (a1) were lower than the theoretical MIC values. In other words, it was found that a synergistic effect was present, and a higher antibacterial effect against Staphylococcus aureus (a1) was shown than in Reference Example 1. As a result, it was found that the antibacterial compositions of Examples 1 to 9 exhibit a higher antibacterial effect against gram-positive bacteria than when the diiodomethane compound is used alone, and are antibacterial compositions having excellent storage stability of the diiodomethane compound.

Claims

1. The composition contains a diiodomethane compound (A), a quaternary ammonium salt (B), and a cyclodextrin derivative (C), An antibacterial composition, wherein the ratio (C / (A+B)) of the content of the cyclodextrin derivative (C) to the sum of the content of the diiodomethane compound (A) and the content of the quaternary ammonium salt (B) is 6.00 or more.

2. 2. The antibacterial composition according to claim 1, wherein the quaternary ammonium salt (B) comprises at least one selected from the group consisting of benzalkonium chloride, benzethonium chloride, and cetylpyridinium chloride.

3. The antibacterial composition according to claim 1 or claim 2, wherein the diiodomethane compound (A) comprises diiodomethyl-p-tolylsulfone.

4. The antibacterial composition according to claim 1 or 2, wherein the cyclodextrin derivative (C) comprises a β-cyclodextrin derivative.

5. 5. The antimicrobial composition of claim 4, wherein the β-cyclodextrin derivative comprises methyl-β-cyclodextrin.

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