Antibacterial agent, and antibacterial and antiviral compositions using the same

Abstract

Provided are a novel antibacterial agent having a high safety and long-lasting effect, an antibacterial composition and an antiviral composition.　The antibacterial agent of the present invention is a formulation comprising the following components (A) and (B). (A) An amine or an ammonium compound having a hydrogen-bonding functional group (excluding an amino acid). (B) A carboxylic acid or a salt thereof.

Description

[Technical Field]

[0001] The present invention relates to an antibacterial agent, and an antibacterial composition and an antiviral composition using the same. [Background technology]

[0002] Various antibacterial agents have traditionally been used in a variety of fields to prevent bacterial contamination and decay, and to prevent and treat bacterial infections. In recent years, public health has become an increasingly important issue due to the prevalence of novel infectious diseases. Against this backdrop, there is a growing need for agents to maintain the cleanliness of the human body and surfaces that come into contact with the human body. While alcohol-based agents, such as ethanol, are typically used for these purposes, they present challenges, including difficulty for those with a constitutional intolerance to alcohol and poor long-term antibacterial activity due to their high volatility and lack of residual residue on surfaces. Chlorine-based agents, such as sodium hypochlorite water and hypochlorous acid water, are also used. However, sodium hypochlorite is strongly alkaline and is not recommended for use on the human body. Furthermore, there are limitations to its use, such as the generation of chlorine gas when mixed with acidic solutions. Furthermore, hypochlorous acid water has problems with poor long-term antibacterial activity due to poor storage stability and reduced effective chlorine concentration during use.

[0003] For these reasons, there is a demand for antibacterial agents that are safe, have low impact on the human body, are low volatile, and have long-lasting effects.

[0004] The present applicant has proposed organic ammonium salts (ionic liquids) having hydrogen-bonding functional groups in the cation or anion (Patent Documents 1 to 5). It has been discovered that these organic ammonium salts are hydrophilic, liquid at room temperature, and have excellent water retention and moisturizing properties. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-131974 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-131975 [Patent Document 3] Japanese Patent Application Publication No. 2019-023185 [Patent Document 4] International Publication No. 2020 / 166674 [Patent Document 5] International Publication No. 2020 / 166678 Summary of the Invention [Problem to be solved by the invention]

[0006] However, no studies have been conducted focusing on antibacterial performance, in particular, no studies have been conducted on combinations of amine or ammonium compounds with carboxylic acids or their salts suitable for this purpose, or on combinations of amines and anions that serve as cations of organic ammonium salts.

[0007] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel antibacterial agent, antibacterial composition, and antiviral composition that are highly safe and have a sustained effect. [Means for solving the problem]

[0008] In order to solve the above problems, the antibacterial agent of the present invention is characterized by being a blend of the following components (A) and (B): (A) Amine or ammonium compounds having a hydrogen-bonding functional group (excluding amino acids). (B) Carboxylic acid or its salt The antibacterial composition of the present invention contains the above antibacterial agent. The antiviral composition of the present invention contains the above-mentioned antibacterial agent. [Effects of the Invention]

[0009] The antibacterial agent, antibacterial composition, and antiviral composition of the present invention are highly safe and have excellent long-lasting effects. In addition, the antibacterial agent of the present invention is also excellent as a solvent for other components. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be described in detail below.

[0011] In the present invention, the term "blend" includes the blending of components (A) and (B) before preparing the final target blend, the synthesis of a salt formed by components (A) and (B) using components (A) and (B) as starting materials, and the blended salt, as well as the blending of the salt with other components such as water as needed. The blend of the present invention may be a mixture consisting of only components (A) and (B) (including the case of their salts), or it may be a composition containing components other than components (A) and (B) or their salts, such as a composition containing water, a composition to which additives are added during the production of the product, or a composition that is a cosmetic product or other product.

[0012] The antibacterial agent of the present invention is a blend of the following components (A) and (B), where component (A) is an amine or ammonium compound having a hydrogen-bonding functional group (excluding amino acids).

[0013] The skeleton of the amine compound in component (A) is not particularly limited, and examples thereof include amines (ammonia, primary amines, secondary amines, tertiary amines), guanidine, and cyclic amines such as imidazole, pyridine, pyrrolidine, piperidine, pyrroline, pyrazine, triazole, isoquinoline, oxazoline, thiazoline, morpholine, pyrimidine, piperazine, triazine, quinoline, indole, quinoxaline, and isoxazoline. Among these, amines, imidazole, pyridine, pyrrolidine, piperidine, and morpholine are preferred, and amines are more preferred. These may also contain substituents, etc., as described in the "Substituent" section below.

[0014] Among the ammonium compounds of component (A), salts of the above amine compounds or quaternized amine compounds can be mentioned.

[0015] Component (A) and the cation derived from component (A) may have an organic group as a substituent.

[0016] [Organic group] In this specification, the organic group essentially contains a carbon atom and may also contain at least one atom selected from the group consisting of a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a halogen atom. The atomic group contained in the organic group is not particularly limited, and examples thereof include hydrocarbon groups, heterocyclic groups, and the substituents described in the "Substituents" section below. For example, the substituents described in the "Substituents" section below may be substituted for hydrogen atoms in the hydrocarbon group, interrupt the hydrocarbon group, and / or be present at the base end of the hydrocarbon group, or form a condensed ring with an aromatic hydrocarbon group. The number of carbon atoms in the organic group is not particularly limited, and is, for example, 1 to 22, 1 to 18, 1 to 12, 1 to 8, or 1 to 4.

[0017] [Hydrocarbon group] In this specification, the hydrocarbon group is not particularly limited, but examples thereof include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and hydrocarbon groups that are combinations thereof. Depending on the context, the group may be monovalent or polyvalent, and examples of the monovalent saturated or unsaturated aliphatic hydrocarbon group include, but are not particularly limited to, linear or branched alkyl groups, alkenyl groups, alkynyl groups, and the like. The alkyl group may be linear or branched, and is not particularly limited to, for example, a methyl group, an ethan-1-yl group, a propan-1-yl group, a 1-methylethan-1-yl group, a butan-1-yl group, a butan-2-yl group, a 2-methylpropan-1-yl group, a 2-methylpropan-2-yl group, a pentan-1-yl group, a pentan-2-yl group, a hexane-1-yl group, a heptan-1-yl group, an octan-1-yl group, a 2-ethylhexan-1-yl group, a 1,1,3,3-tetramethylbutan-1-yl group, a nonan-1-yl group, a 2-ethylhexan-1-yl group, a 1,1,3,3-tetramethylbutan-1-yl group, a 2-methylpropan-2-yl group, a 2-methylpropan-1-yl group, a 2-methylpropan-2-yl group, a 2-methylpropan-1-yl group, a 2-methylhexan-1-yl group, a 1,1,3,3-tetramethylbutan-1-yl group, a 2-methylhex ... 1-yl group, decan-1-yl group, undecane-1-yl group, dodecane-1-yl group, tridecane-1-yl group, tetradecane-1-yl group, pentadecan-1-yl group, hexadecan-1-yl group, 2-hexyldecan-1-yl group, heptadecan-1-yl group, octadecan-1-yl group, nonadecan-1-yl group, icosan-1-yl group, henicosan-1-yl group, docosan-1-yl group, 4,8,12-trimethyltridecan-1-yl group, benzyl group, and α,α-dimethylbenzyl group.The alkenyl group may be linear or branched, and is not particularly limited to, but examples thereof include vinyl, prop-1-en-1-yl, allyl, isopropenyl, but-1-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 2-methylprop-2-en-1-yl, 1-methylprop-2-en-1-yl, pent-1-en-1-yl, pent-2-en-1-yl, pent-3-en-1-yl, and pent-4-en-1-yl. group, 3-methylbut-2-en-1-yl group, 3-methylbut-3-en-1-yl group, hex-1-en-1-yl group, hex-2-en-1-yl group, hex-3-en-1-yl group, hex-4-en-1-yl group, hex-5-en-1-yl group, 4-methylpent-3-en-1-yl group, 4-methylpent-3-en-1-yl group, hept-1-en-1-yl group, hept-6-en-1-yl group, oct-1-en-1-yl group, oct-7-en-1 -yl group, non-1-en-1-yl group, non-8-en-1-yl group, dec-1-en-1-yl group, dec-9-en-1-yl group, undec-1-en-1-yl group, undec-10-en-1-yl group, dodec-1-en-1-yl group, dodec-11-en-1-yl group, tridec-1-en-1-yl group, tridec-12-en-1-yl group, tetradec-1-en-1-yl group, tetradec-13-en-1-yl group, pentadec-1-en-1-yl group, Examples thereof include a pentadec-14-en-1-yl group, a hexadec-1-en-1-yl group, a hexadec-15-en-1-yl group, a heptadec-1-en-1-yl group, a heptadec-16-en-1-yl group, an octadec-1-en-1-yl group, an octadec-9-en-1-yl group, an octadec-17-en-1-yl group, a nonadec-1-en-1-yl group, an icos-1-en-1-yl group, a henicos-1-en-1-yl group, and a docos-1-en-1-yl group.The alkynyl group includes a straight-chain or branched-chain alkynyl group, and is not particularly limited to, but examples thereof include ethynyl, prop-1-yn-1-yl group, prop-2-yn-1-yl group, but-1-yn-1-yl group, but-3-yn-1-yl group, 1-methylprop-2-yn-1-yl group, pent-1-yn-1-yl group, pent-4-yn-1-yl group, hex-1 ... -yl group, hex-5-yn-1-yl group, hept-1-yn-1-yl group, hept-6-yn-1-yl group, oct-1-yn-1-yl group, oct-7-yn-1-yl group, non-1-yn-1-yl group, non-8-yn-1-yl group, dec-1-yn-1-yl group, dec-9-yn-1-yl group, undec-1-yn-1-yl group, undec-10 -yn-1-yl group, dodec-1-yn-1-yl group, dodec-11-yn-1-yl group, tridec-1-yn-1-yl group, tridec-12-yn-1-yl group, tetradec-1-yn-1-yl group, tetradec-13-yn-1-yl group, pentadec-1-yn-1-yl group, pentadec-14-yn-1-yl group, hexadec-1-yn-1-yl group group, hexadec-15-yn-1-yl group, heptadec-1-yn-1-yl group, heptadec-16-yn-1-yl group, octadec-1-yn-1-yl group, octadec-17-yn-1-yl group, nonadeca-1-yn-1-yl group, icos-1-yn-1-yl group, henicos-1-yn-1-yl group, docos-1-yn-1-yl group, and the like.

[0018] As the saturated or unsaturated alicyclic hydrocarbon group, a saturated alicyclic hydrocarbon group is preferable, and although not particularly limited, examples thereof include monovalent groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and groups containing alicyclic residues such as residues thereof.

[0019] The aromatic hydrocarbon group is not particularly limited, but examples thereof include a phenyl group, a naphthyl group, an anthracenyl group, and groups containing aromatic ring residues such as these residues. The aromatic hydrocarbon group may form a fused ring together with the substituents described below under [Substituents]. The monovalent aromatic hydrocarbon group is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 2,4,5-trimethylphenyl group, a 2,4,6-trimethylphenyl group, a 4-ethylphenyl group, a 4-propylphenyl group, a 4-isopropylphenyl group, a 4-butylphenyl group, a 4-tert-butylphenyl group, a 4-pentylphenyl group, a 4-tert-pentylphenyl group, a 2,4-bis(4-tert-pentyl)phenyl group, a 1,1,3,3-tetramethylbutylphenyl group, a 2-methyl-5-tert-butylphenyl group, a 4-pentylphenyl group, a 4-hexylphenyl group, a 4-heptylphenyl group, a 4- Examples thereof include an octylphenyl group, a 4-nonylphenyl group, a 4-decanylphenyl group, a 4-undecylphenyl group, a 4-dodecylphenyl group, a 4-tridecylphenyl group, a 4-tetradecylphenyl group, a 4-pentadecylphenyl group, a 4-hexadecylphenyl group, a 4-heptadecylphenyl group, a 4-octadecylphenyl group, a 4-biphenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, a 4-methoxyphenyl group, a 2-ethoxyphenyl group, a 3-ethoxyphenyl group, a 4-ethoxyphenyl group, a 2-chlorophenyl group, a 2-fluorophenyl group, a 4-fluorophenyl group, a 2-trifluoromethylphenyl group, a 4-trifluoromethylphenyl group, a 4-hydroxyphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group.

[0020] Examples of the divalent hydrocarbon group include groups in which one hydrogen atom has been removed from the above groups.

[0021] [Substituent] The substituent is not particularly limited, and examples thereof include hydrocarbon groups, oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, halogens, etc. The substituent also includes groups to which these substituents are bonded.

[0022] Examples of the hydrocarbon group include those listed above under [Hydrocarbon group].

[0023] The oxygen-containing group is not particularly limited, but examples thereof include a hydroxyl group, an alkoxy group, an acetoxy group, an acetyl group, an aldehyde group, a carboxy group, a carboxylate group, a urea group, a urethane group, an amide group, an imide group, an ether group, a carbonyl group, an ester group, an oxazole group, a morpholine group, a carbamate group, a carbamic acid group, a carbamoyl group, a polyoxyethylene group, a tocopheryl group, a chroman group, a dihydropyran group, a glyceryl group, and a glyceryl ether group.

[0024] The nitrogen-containing group is not particularly limited, but examples thereof include a cyano group, a cyanato group, an isocyanate group, a nitro group, a nitroalkyl group, an amide group, a urea group, a urethane group, an imide group, a carbodiimide group, an azo group, a pyridyl group, an imidazole group, a pyrrolidyl group, a piperidyl group, a pyrrolyl group, a pyrazyl group, a triazole group, an isoquinolyl group, an oxazolyl group, a thiazolyl group, a morpholyl group, a guanidyl group, a pyrimidyl group, a piperazyl group, a triazyl group, a quinolyl group, an indole group, a quinoxalyl group, an isoxazolyl group, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium group, and an aminoalkyl group.

[0025] The sulfur-containing group is not particularly limited, but examples thereof include a sulfate group, a sulfonyl group, a sulfonic acid group, a mercapto group, a thioether group, a thiocarbonyl group, a thiourea group, a thiocarboxy group, a thiocarboxylate group, a dithiocarboxy group, a dithiocarboxylate group, a sulfate ester, a thiophene group, a thiazole group, a thiol group, a sulfo group, a sulfide group, a disulfide group, a thioester group, a thioamide group, a thiocarbamate group, a dithiocarbamate group, and esters thereof.

[0026] The phosphorus-containing group is not particularly limited, but examples thereof include a phosphate group, a phosphite group, a phosphonic acid group, a phosphinic acid group, a phosphonous acid group, a phosphinous acid group, a pyrophosphate group, a phosphate ester group, a phosphite ester group, a phosphonic acid ester group, a pyrophosphate group, and ester groups thereof.

[0027] Halogens include fluorine, chlorine, bromine and iodine.

[0028] Examples of the organic group include hydrocarbon groups which may have a substituent and in which the hydrocarbon moiety may contain an oxygen atom. For the hydrocarbon group, see the description in the above section on "Hydrocarbon Group." The hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group (such as an alkyl group). The alkyl group may be, for example, a linear or branched group having 1 to 22, 4 to 22, 8 to 22, or 12 to 22 carbon atoms, or a linear or branched group having 1 to 18, 1 to 12, or 1 to 4 carbon atoms.

[0029] The hydrocarbon group may have a substituent, and the substituent is not particularly limited, but examples thereof include those listed in the [Substituent] section above. Among the substituents, those having an oxygen-containing group are preferred, and among these, a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, an ether group, and an alkoxy group are preferred. Among these, a hydroxyl group, a carboxyl group, a carboxylate group, an ether group, and an alkoxy group are more preferred, and a hydroxyl group is particularly preferred.

[0030] The hydrocarbon moiety may contain an oxygen atom, and in this case, the hydrocarbon moiety contains the above-mentioned oxygen-containing group, which may form or contain, for example, an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group, an ester bond, an amide bond, a urea bond, or a urethane bond, although this is not particularly limited. Therefore, in the present invention, the phrase "the hydrocarbon moiety contains an oxygen atom" includes cases where the hydrocarbon moiety is interrupted by a group that may also contain a heteroatom such as a nitrogen atom as an atomic group containing an oxygen atom, or where such a group is contained at the base end, or where a hydrogen atom is substituted.

[0031] In order to enhance the effects of the present invention, component (A) has one or more functional group-introducible atoms (atoms contained in the basic chemical structure, such as nitrogen atoms or carbon atoms forming a ring together with the nitrogen atoms) substituted with an organic group having a hydrogen-bonding functional group. Alternatively, the hydrogen atom directly bonded to the nitrogen atom constitutes the hydrogen-bonding functional group.

[0032] In the organic group having the hydrogen-bonding functional group, the hydrogen-bonding functional group is not particularly limited, and examples thereof include the above-mentioned oxygen-containing group, nitrogen-containing group, sulfur-containing group, phosphorus-containing group, and a hydrogen atom directly bonded to nitrogen, with the oxygen-containing group being preferred.

[0033] From the viewpoints of affinity for water and affinity for organic and inorganic materials that can bond or coordinate with the hydrogen-bonding functional group, the hydrogen-bonding functional group contained in component (A) is preferably a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, an ether group, an alkoxy group, or a hydrogen atom directly bonded to nitrogen. Among these, a hydroxyl group, a carboxyl group, a carboxylate group, an ether group, an alkoxy group, or a hydrogen atom directly bonded to nitrogen is more preferred, a hydroxyl group, a carboxyl group, a carboxylate group, or a hydrogen atom directly bonded to nitrogen is even more preferred, a hydroxyl group, a carboxyl group, or a hydrogen atom directly bonded to nitrogen is particularly preferred, and a hydroxyl group or a hydrogen atom directly bonded to nitrogen is most preferred. A preferred example of an organic group having a hydrogen-bonding functional group is a hydrocarbon group having a hydrogen-bonding functional group. For example, organic groups having a hydrogen-bonding functional group include hydrocarbon groups containing a hydroxyl group (hydroxy hydrocarbon groups), hydrocarbon groups containing a carboxyl group (carboxy hydrocarbon groups), hydrocarbon groups containing a hydroxyl group and a carboxyl group (hydroxycarboxy hydrocarbon groups), hydrocarbon groups containing a carboxylate group, hydrocarbon groups containing an ester group, hydrocarbon groups containing an ether group, and hydrocarbon groups containing an alkoxy group.

[0034] From the standpoint of safety, it is preferable that the component (A) has one or more hydroxyl groups, and the hydrocarbon moiety is linear or branched, and the hydrocarbon moiety has a hydroxy hydrocarbon group which may contain an oxygen atom.

[0035] Examples of the hydrocarbon group include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and hydrocarbon groups formed by combining these groups. Common hydrocarbon groups can be used. Among the hydrocarbon groups, saturated aliphatic hydrocarbon groups are preferred. Examples of the hydrocarbon group include those described in the "Hydrocarbon Group" section below.

[0036] For example, although not particularly limited, the hydroxyhydrocarbon group has one or more hydroxyl groups, and the hydrocarbon moiety is preferably linear or branched and has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.

[0037] Here, when the hydrocarbon moiety contains an oxygen atom, the oxygen atom forms, for example, an ether bond, a carbonyl group, an ester bond, an amide bond, a urea bond, or a urethane bond in the hydrocarbon moiety. Therefore, in the present invention, the phrase "the hydrocarbon moiety contains an oxygen atom" includes cases where the hydrocarbon moiety is interrupted by a group that may also contain a heteroatom such as a nitrogen atom as an atomic group containing an oxygen atom, or where the hydrocarbon moiety contains such a group at its base end, or where a hydrogen atom is substituted.

[0038] Examples of the hydroxy hydrocarbon group include saturated or unsaturated aliphatic hydrocarbon groups having one or more hydroxy groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and hydrocarbon groups that are combinations of these. Saturated aliphatic hydrocarbon groups having one hydroxy group (such as a monohydroxyalkyl group) and saturated aliphatic hydrocarbon groups having two or more hydroxy groups (such as a polyhydroxyalkyl group) are preferred, and they may contain the oxygen-containing group.

[0039] The saturated aliphatic hydrocarbon group having one hydroxy group (monohydroxyalkyl group) is not particularly limited, and examples thereof include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropan-1-yl group, a 2-hydroxypropan-1-yl group, a 3-hydroxypropan-1-yl group, a 1-hydroxypropan-2-yl group, a 2-hydroxypropan-2-yl group, a 2-hydroxymethylpropan-2-yl group, a 2-hydroxyethylpropan-2-yl group, a 1-hydroxybutan-1 ...methylpropan-2-yl group, a 2-hydroxyethylpropan-2-yl group, a 1-hydroxybutan-1-yl group, a 2-hydroxymethylpropan-2-yl group, a 2-hydroxymethylpropan-2-yl group, a 2-hydroxymethylpropan-2-yl group, a 2-hydroxymethylpropan-2- Dihydroxybutan-1-yl group, 3-hydroxybutan-1-yl group, 4-hydroxybutan-1-yl group, 1-hydroxy-2-methylpropan-1-yl group, 2-hydroxy-2-methylpropan-1-yl group, 3-hydroxy-2-methylpropan-1-yl group, 1-hydroxybutan-2-yl group, 2-hydroxybutan-2-yl group, 3-hydroxybutan-2-yl group, 4-hydroxybutan-2-yl group, 1-hydroxy-2-methylpropan-2-yl group, 5-hydroxypentan-1-yl group, 2-hydroxymethylpentan-2-yl group 1-hydroxy-2-methylpropan-2-yl group, 1-hydroxy-3-methylbutan-2-yl group, 2-hydroxyethylpentan-2-yl group, 6-hydroxyhexan-1-yl group, 7-hydroxyheptan-1-yl group, 8-hydroxyoctan-1-yl group, 9-hydroxynonan-1-yl group, 10-hydroxydecan-1-yl group, 2-methyl-1-hydroxypropan-2-yl group, 2-methyl-1-propan-2-yl group, 1-hydroxy-2-methylpropan-2-yl group, 1-hydroxy-3-methylbutan-2-yl group, 2-hydroxy-2-methylpropan-2-yl group, 2-hydroxy-2-methylbutan- 2-yl group, 2-ethyl-2-hydroxybutan-2-yl group, 2-hydroxy-3-methylpentan-2-yl group, 3-ethyl-2-hydroxypentan-2-yl group, 2-ethyl-1-hydroxy-3-methylbutan-2-yl group, 1-hydroxy-3-methyl-2-(1-methylethyl)butan-2-yl group, 2-ethyl-1-hydroxypentan-2-yl group, 1-hydroxy-2-propylpentan-2-yl group, 4-ethyl-3-hydroxyhexan-4-yl group, 3-ethyl-2-hydroxy-2-methylpentan-3-yl group,Examples of the monohydroxyalkyl group include a 2-ethyl-1-hydroxyhexan-2-yl group, a 1-hydroxy-2-propylhexan-2-yl group, a 2-ethyl-1-hydroxyheptan-2-yl group, a 2-ethyl-1-hydroxy-4-methylpentan-2-yl group, a 1-hydroxy-2-(1-methylethyl)pentan-2-yl group, and a 3-ethyl-4-hydroxyheptan-3-yl group. The monohydroxyalkyl group preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms.

[0040] The saturated aliphatic hydrocarbon group having two or more hydroxy groups (polyhydroxyalkyl group) is not particularly limited, but examples thereof include di-, tri-, tetra-, penta-, hexa-, hepta-, or octahydroxyalkyl groups. Specific examples thereof include, but are not particularly limited to, dihydroxyethyl groups such as 1,2-dihydroxyethyl groups; dihydroxypropan-1-yl groups such as 1,2-dihydroxypropan-1-yl groups and 2,3-dihydroxypropan-1-yl groups; dihydroxypropan-2-yl groups such as 1,2-dihydroxypropan-2-yl groups and 1,3-dihydroxypropan-2-yl groups; trihydroxypropan-1-yl groups; tri ... Hydroxypropan-2-yl group; dihydroxybutan-1-yl groups such as 1,2-dihydroxybutan-1-yl group, 1,3-dihydroxybutan-1-yl group, 1,4-dihydroxybutan-1-yl group, 2,3-dihydroxybutan-1-yl group, 2,4-dihydroxybutan-1-yl group, and 3,4-dihydroxybutan-1-yl group; 1,2,3 trihydroxybutan-1-yl group, 1,2,4 trihydroxybutan-1-yl group, 1,3,4 trihydroxybutan-1-yl group, and 2,3,4 Trihydroxybutan-1-yl groups such as trihydroxybutan-1-yl group; tetrahydroxybutan-1-yl group; dihydroxy-2-methylpropan-1-yl groups such as 1,2-dihydroxy-2-methylpropan-1-yl group, 1,3-dihydroxy-2-methylpropan-1-yl group, and 2,3-dihydroxy-2-methylpropan-1-yl group; trihydroxy-2-methylpropan-1-yl group; tetrahydroxy-2-methylpropan-1-yl group; 1,2-dihydroxybutan-2-yl dihydroxybutan-2-yl groups such as 1,3-dihydroxybutan-2-yl group, 1,4-dihydroxybutan-2-yl group, 2,3-dihydroxybutan-2-yl group, 2,4-dihydroxybutan-2-yl group, and 3,4-dihydroxybutan-2-yl group; tetrahydroxybutan-2-yl group; 1,3-dihydroxy-2-methylpropan-2-yl group, 1,3-dihydroxy-2-ethylpropan-2-yl group, and 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group;Tetrahydroxybutan-2-yl group; 1,3-dihydroxy-2-methylpropan-2-yl group, 1,3-dihydroxy-2-ethylpropan-2-yl group, 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group, 1,2-dihydroxypropan-3-yl group, 1,1-dihydroxybutan-2-yl group, 1,1-dihydroxypentan-2-yl group, 1,1-dihydroxy-5-methylhexan-2-yl group, 1,1-dihydroxy Examples of suitable polyhydroxyalkyl groups include hydroxypropan-2-yl group, 1,1-dihydroxy-4-(-4-hydroxyphenyl)butan-2-yl group, di-, tri-, tetra-, or pentahydroxypentan-1-yl group, di-, tri-, tetra-, penta-, or hexahydroxyhexan-1-yl group, di-, tri-, tetra-, penta-, hexa-, or heptahydroxyheptan-1-yl group, and di-, tri-, tetra-, penta-, hexa-, hepta-, or octahydroxyoctan-1-yl group. The polyhydroxyalkyl group preferably has 2 to 8 hydroxyl groups, more preferably 2 to 6 hydroxyl groups. The alkyl group preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Preferred examples of branched polyhydroxyalkyl groups include those represented by the following formula:

[0041] [ka]

[0042] (In the formula, R 7 represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms), or a linear hydroxyalkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms).

[0043] The group of the above formula is not particularly limited, but examples thereof include 1,2-dihydroxypropan-1-yl group, 2,3-dihydroxypropan-1-yl group, 1,2-dihydroxypropan-2-yl group, 1,3-dihydroxypropan-2-yl group, trihydroxypropan-1-yl group, trihydroxypropan-2-yl group, trihydroxypropan-1-yl group, trihydroxypropan-2-yl group, 1,2-dihydroxybutan-1-yl group, 1,3-dihydroxybutan-1-yl group, 1,4-dihydroxybutan-1-yl group, 2,3 -dihydroxybutan-1-yl group, 2,4-dihydroxybutan-1-yl group, 3,4-dihydroxybutan-1-yl group, 1,2,3-trihydroxybutan-1-yl group, 1,2,4-trihydroxybutan-1-yl group, 1,3,4-trihydroxybutan-1-yl group, 2,3,4-trihydroxybutan-1-yl group, tetrahydroxybutan-1-yl group, 1,2-dihydroxy-2-methylpropan-1-yl group, 1,3-dihydroxy-2-methylpropan-1-yl group, 2,3-dihydroxy-2-methylpropan-1-yl group, trihydroxybutan-1-yl group, trihydroxy-2-methylpropan-1-yl group, tetrahydroxy-2-methylpropan-1-yl group, 1,2-dihydroxybutan-2-yl group, 1,3-dihydroxybutan-2-yl group, 1,4-dihydroxybutan-2-yl group, 2,3-dihydroxybutan-2-yl group, 2,4-dihydroxybutan-2-yl group, 3,4-dihydroxybutan-2-yl group, tetrahydroxybutan-2-yl group, 1,3-dihydroxy-2-methylpropan-2-yl group, 1,3-dihydroxy-2-ethylpropan-2-yl group, 1,3- Dihydroxy-2-hydroxymethylpropan-2-yl group, tetrahydroxybutan-2-yl group, 1,3-dihydroxy-2-methylpropan-2-yl group, 1,3-dihydroxy-2-ethylpropan-2-yl group, 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group, 1,2-dihydroxypropan-3-yl group, 1,1-dihydroxybutan-2-yl group, 1,1-dihydroxypentan-2-yl group, 1,1-dihydroxy-5-methylhexan-2-yl group, 1,1-dihydroxypropan-2-yl group, 1,Examples of the hydroxyl group include a 1-dihydroxy-4-(-4-hydroxyphenyl)butan-2-yl group, a di-, tri-, tetra-, or pentahydroxypentan-1-yl group, a di-, tri-, tetra-, penta-, or hexahydroxyhexan-1-yl group, a di-, tri-, tetra-, penta-, hexa-, or heptahydroxyheptan-1-yl group, and a di-, tri-, tetra-, penta-, hexa-, hepta-, or octahydroxyoctan-1-yl group.

[0044] Among the above polyhydroxyalkyl groups, 2,3-dihydroxypropan-1-yl group, 1,3-dihydroxypropan-2-yl group, 1,3-dihydroxy-2-ethylpropan-2-yl group, 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group, and pentahydroxyhexan-1-yl group are preferred, and from the standpoint of antibacterial properties, 1,3-dihydroxy-2-ethylpropan-2-yl group and 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group are more preferred.

[0045] From the viewpoint of safety, when component (A) has a monohydroxyalkyl group, triethanolamine and diethanolamine are preferred, with triethanolamine being particularly preferred.

[0046] Furthermore, from the viewpoints of safety and ease of use, it is preferable to use as a raw material (e.g., acid, base) for component (A) a compound listed in the Standards for Quasi-drug Raw Materials (Standards for Quasi-drug Additives), Standards for Quasi-drug Additives, Japanese Pharmacopoeia (JP), Standards for Quasi-drugs Other Than the JP (JP), Standards for Pharmaceutical Additives Other Than the JP (JP), Pharmaceutical Additives Standards (Pharmacopoeia Standards), and Official Specification of Food Additives (Food Additives). Although not particularly limited, monoethanolamine, diethanolamine, triethanolamine, 2-amino-2-hydroxymethyl-1,3-propanediol, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, monoisopropanolamine, diisopropanolamine, triisopropanolamine, 2-acetamidoethanolamine, N-lauryldiethanolamine, and dimethyloctadecylamine are preferred, and of these, triethanolamine and 2-amino-2-hydroxymethyl-1,3-propanediol are more preferred from the viewpoint of low odor.

[0047] In component (A), one or more of the sites in component (A) where a functional group can be introduced (atoms contained in the chemical structure that forms the basic skeleton, such as nitrogen sites or carbon sites that form a ring together with nitrogen) may be substituted with an organic group that does not have a hydrogen-bonding functional group. Examples of such organic groups include hydrocarbon groups. Examples of hydrocarbon groups include alkyl groups. The alkyl group is preferably a linear or branched group having 1 to 18 carbon atoms, more preferably a linear or branched group having 1 to 12 carbon atoms, even more preferably a linear or branched group having 1 to 8 carbon atoms, and even more preferably a linear or branched group having 1 to 4 carbon atoms.

[0048] When component (A) is an ammonium compound, the anion is not particularly limited, and examples thereof include hydroxide anions, halogen-based anions, sulfur-based anions, phosphorus-based anions, cyanide-based anions, boron-based anions, fluorine-based anions, nitrogen oxide-based anions, and carboxylate-based anions, with hydroxide anions being preferred.

[0049] When the amine or ammonium compound of component (A) is an amine compound, said component (A) is preferably an amine compound represented by the following formula (I).

[0050] [ka]

[0051] (In the formula, R 1 each independently represents a hydroxyhydrocarbon group having one or more hydroxyl groups and a linear or branched hydrocarbon moiety having 1 to 22 carbon atoms, which hydrocarbon moiety may contain an oxygen atom; R 2 are each independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and m is an integer of 0 to 3.

[0052] In the formula (I), m is preferably an integer of 1 to 3.

[0053] In the formula (I), all R 2 is preferably a hydrogen atom.

[0054] In the formula (I), the hydroxyhydrocarbon group is preferably such that the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon.

[0055] In the formula (I), R 1 It is preferable that at least one of the above has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0056] In the formula (I), R 1 It is preferable that at least one of the above has two or more hydroxyl groups, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0057] In the formula (I), R 1It is preferable that at least one of the above has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0058] At least any combination of the above preferred examples shown in formula (I) can be a more preferred embodiment.

[0059] In the formula (I), R 1 has one hydroxyl group, the hydrocarbon portion is a linear hydroxy hydrocarbon group having 1 to 6 carbon atoms, and R 2 is preferably a hydrogen atom, and m is preferably an integer of 1 to 3. In the formula (I), R 1 has 2 or 3 hydroxyl groups, the hydrocarbon moiety is a branched hydroxy hydrocarbon group having 2 to 6 carbon atoms, and R 2 is preferably a hydrogen atom and m is an integer of 1. In the formula (I), R 1 has 2 to 6 hydroxyl groups, the hydrocarbon portion is a linear hydroxy hydrocarbon group having 2 to 6 carbon atoms, and R 2 is preferably a hydrogen atom and m is an integer of 1.

[0060] When the amine or ammonium compound of component (A) is an ammonium compound, component (A) is preferably an ammonium compound represented by the following formula (II).

[0061] [ka]

[0062] (In the formula, R 3 each independently represents a hydroxyhydrocarbon group having one or more hydroxyl groups and a linear or branched hydrocarbon moiety having 1 to 22 carbon atoms, which hydrocarbon moiety may contain an oxygen atom; R 4are each independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and n is an integer of 0 to 4. - indicates an anion.)

[0063] In the formula (II), X - The anion represented by the formula (I) is preferably a hydroxide ion.

[0064] In the formula (II), n is preferably an integer of 1 to 4.

[0065] In the formula (II), all R 4 is preferably a hydrogen atom.

[0066] In the formula (II), the hydroxyhydrocarbon group is preferably such that the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon.

[0067] In the formula (II), R 3 At least one of the above has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is preferably a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0068] In the formula (II), R 3 It is preferable that at least one of the above has two or more hydroxyl groups, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0069] In the formula (II), R 3 It is preferable that at least one of the above has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0070] At least any combination of the above preferred examples shown in formula (II) can be a more preferred embodiment.

[0071] In the formula (II), R 3 has one hydroxyl group, the hydrocarbon portion is a hydroxy hydrocarbon group having 1 to 3 carbon atoms, and R 4 is a hydrocarbon group having 1 to 3 carbon atoms, and n is preferably an integer of 1. In the formula (II), R 4 is a hydrocarbon group having 1 to 4 carbon atoms, and n is preferably an integer of 0.

[0072] In one preferred embodiment of the antibacterial agent of the present invention, the organic ammonium salt formed by component (A) and component (B) is also used.

[0073] Preferably, the component (B) contains an organic ammonium salt formed by a cation derived from the component (A) which may have a cationic residue, and an anion derived from the anionic residue of the component (B). The cation is preferably an ammonium cation.

[0074] In the present invention, the residue in component (B) refers to an atom or atomic group (radical) that has no charge; those that have a charge and become cations are called cationic residues, and those that become anions are called anionic residues.

[0075] In the present invention, the carboxylic acid or salt thereof of component (B) has a cationic residue and an anionic residue. The cationic residue is a hydrogen atom or a group (atomic group) that bonds with the nitrogen atom of component (A) to form a hydrogen-bonding functional group or an organic group. Preferably, the acid of component (B) is a compound composed of hydrogen, which becomes a proton, and an anionic residue.

[0076] In the present invention, the organic ammonium salt is an organic cation having a nitrogen atom as the ionic center or NH4 + , and organic anions. In particular, it includes organic cations and organic anions, where the term "organic" means including the elements carbon and hydrogen.

[0077] The cation derived from the component (A) is ammonium cation (NH + cations derived from cyclic amines, such as, but not limited to, imidazolium cations, pyridinium cations, pyrrolidinium cations, piperidinium cations, pyrrolinium cathine, pyrazinium cations, triazolium cations, isoquinolinium cations, oxazolinium cations, thiazolinium cations, morpholinium cations, pyrimidinium cations, piperazinium cations, triazinium cations, quinolinium cations, indolinium cations, quinoxalinium cations, and isoxazolium cations, and cationic amino acids. Among these, ammonium cations, imidazolium cations, pyridinium cations, pyrrolidinium cations, piperidinium cations, and morpholinium cations are preferred, and ammonium cations are more preferred.

[0078] The cation of the organic ammonium salt formed by the components (A) and (B) is preferably a cation represented by the following formula (III): When component (A) is an ammonium compound, its cation is also preferably a cation represented by the following formula (III):

[0079] [ka]

[0080] (In the formula, R 5 each independently represents a hydroxyhydrocarbon group having one or more hydroxyl groups and a linear or branched hydrocarbon moiety having 1 to 22 carbon atoms, which hydrocarbon moiety may contain an oxygen atom; R 6 are each independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and o is an integer of 0 to 4.

[0081] In the formula (III), o is preferably an integer of 1 to 4.

[0082] In the formula (III), all R 6 is preferably a hydrogen atom.

[0083] In the formula (III), the hydroxyhydrocarbon group is preferably such that the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon.

[0084] In the formula (III), R 5 It is preferable that at least one of the above has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0085] In the formula (III), R 5 It is preferable that at least one of the above has two or more hydroxyl groups, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0086] In the formula (III), R 5 It is preferable that at least one of the above has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon of the hydrocarbon moiety which may contain an oxygen atom is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.

[0087] R of the cation represented by formula (III) 6 When at least one of the groups is a hydrogen atom, the proton corresponding to the hydrogen atom preferably originates from the component (B).

[0088] At least any combination of the above preferred examples shown in formula (III) can be a more preferred embodiment.

[0089] In the antibacterial agent of the present invention, component (B) is a carboxylic acid or a salt thereof. The carboxylic acid is an organic acid having at least one carboxyl group (—COOH) in the molecule and may have an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, a hydrocarbon group, or the like. Examples of carboxylic acids include, but are not limited to, saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof having a hydrocarbon group and a carboxyl group. Examples include saturated aliphatic carboxylic acids, unsaturated aliphatic carboxylic acids, saturated or unsaturated alicyclic carboxylic acids, aromatic carboxylic acids, saturated aliphatic hydroxycarboxylic acids, unsaturated aliphatic hydroxycarboxylic acids, saturated or unsaturated alicyclic hydroxycarboxylic acids, aromatic hydroxycarboxylic acids, carbonyl carboxylic acids, alkyl ether carboxylic acids, and halogen carboxylic acids (the carbon number of the carboxylic acids listed below includes the carbon atoms of the carboxyl group).

[0090] The saturated aliphatic carboxylic acid comprises a linear or branched saturated aliphatic hydrocarbon group and one or more carboxy groups, and preferably has 1 to 22 carbon atoms. Examples of saturated aliphatic carboxylic acids include saturated aliphatic monocarboxylic acids with one carboxy group and saturated aliphatic dicarboxylic acids with two carboxy groups. The saturated aliphatic monocarboxylic acid comprises a linear or branched saturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms. Specific examples include, but are not limited to, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, heneicosylic acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, and isostearic acid. The saturated aliphatic dicarboxylic acid comprises a linear or branched saturated aliphatic hydrocarbon group and two carboxy groups, and preferably has 2 to 22 carbon atoms. Specific examples include, but are not limited to, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid.

[0091] The unsaturated aliphatic carboxylic acid comprises a linear or branched unsaturated aliphatic hydrocarbon group and one or more carboxy groups, and preferably has 3 to 22 carbon atoms. Examples of unsaturated aliphatic carboxylic acids include unsaturated aliphatic monocarboxylic acids with one carboxy group and unsaturated aliphatic dicarboxylic acids with two carboxy groups. The unsaturated aliphatic monocarboxylic acid comprises a linear or branched unsaturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms. Specific examples of the carboxylic acid include, but are not limited to, acrylic acid, methacrylic acid, crotonic acid, octenoic acid, nonenoic acid, decenoic acid, undecenoic acid, undecylenic acid, dodecenoic acid, tridecenoic acid, tetradecenoic acid, myristoleic acid, pentadecenoic acid, hexadecenoic acid, palmitoleic acid, sapienic acid, heptadecenoic acid, octadecenoic acid, oleic acid, elaidic acid, vaccenic acid, nonadecenoic acid, icosenoic acid, gadoleic acid, henicosenic acid, docosenoic acid, erucic acid, octadienoic acid, nonadienoic acid, decadienoic acid, undecadienoic acid, dodecadienoic acid, tridecenoic acid, tetradecenoic acid, myristoleic acid, pentadecenoic acid, hexadecenoic acid, palmitoleic acid, sapienoic acid, heptadecenoic acid, octadecenoic acid, oleic acid, elaidic acid, vaccenic acid, nonadecenoic acid, icosenoic acid, gadoleic acid, henicosenic acid, docosenoic acid, erucic acid, octadienoic acid, nonadienoic acid, decadienoic acid, undecadienoic acid, dodecadienoic acid, tetradeceno ... Ridecadienoic acid, tetradecadienoic acid, pentadecadienoic acid, hexadecadienoic acid, heptadecadienoic acid, octadecadienoic acid, linoleic acid, nonadecadienoic acid, icosadienoic acid, henicosadienoic acid, docosadienoic acid, octatrienoic acid, nonatrienoic acid, decatrienoic acid, undecatrienoic acid, dodecatrienoic acid, tridecatrienoic acid, tetradecatrienoic acid, pentadecatrienoic acid, hexadecatrienoic acid, heptadecatrienoic acid, octadecatrienoic acid, linolenic acid, eleostearic acid, nonadecatrienoic acid, icosatrienoic acid, mead Acid, dihomo-γ-linolenic acid, henicosatrienoic acid, docosatrienoic acid, decatetraenoic acid, undecatetraenoic acid, dodecatetraenoic acid, tridecatetraenoic acid, tetradecatetraenoic acid, pentadecatetraenoic acid, hexadecatetraenoic acid, hexadecatetraenoic acid, heptadecatetraenoic acid, octadecatetraenoic acid, stearidonic acid, nonadecatetraenoic acid, icosatetraenoic acid, arachidonic acid, henicosatetraenoic acid, docosatetraenoic acid, adrenic acid, undecapentaenoic acid, dodecapentaenoic acid, tridecapentaenoic acid, tetra Examples of the carboxylic acid include decapentaenoic acid, pentadecapentaenoic acid, hexadecapentaenoic acid, heptadecapentaenoic acid, octadecapentaenoic acid, bosseopentaenoic acid, nonadecapentaenoic acid, eicosapentaenoic acid, henicosapentaenoic acid, docosapentaenoic acid, sardine acid, tridecahexaenoic acid, tetradecahexaenoic acid, pentadecahexaenoic acid, hexadecahexaenoic acid, heptadecahexaenoic acid, octadecahexaenoic acid, bosseohexaenoic acid, nonadecahexaenoic acid, eicosahexaenoic acid, henicosahexaenoic acid, and docosahexaenoic acid. The unsaturated aliphatic dicarboxylic acid comprises a linear or branched unsaturated aliphatic hydrocarbon group and two carboxy groups, and preferably has 1 to 22 carbon atoms. Specific examples include, but are not limited to, maleic acid and fumaric acid.

[0092] The saturated or unsaturated alicyclic carboxylic acid is composed of a non-aromatic saturated or unsaturated carbon ring and one or more carboxy groups, and preferably has a carbon number of 6 to 20. Among these, a saturated alicyclic carboxylic acid having a cyclohexane ring skeleton is preferred. Examples of saturated or unsaturated alicyclic carboxylic acids include saturated or unsaturated alicyclic monocarboxylic acids with one carboxy group, and saturated or unsaturated alicyclic dicarboxylic acids with two carboxy groups. The saturated or unsaturated alicyclic monocarboxylic acid is not particularly limited, but examples thereof include cyclohexanecarboxylic acid. The saturated or unsaturated alicyclic dicarboxylic acid is not particularly limited, but examples thereof include cyclohexanedicarboxylic acid and tetrahydrophthalic acid.

[0093] The aromatic carboxylic acid is composed of a single ring or multiple rings having aromaticity and one or more carboxylic acids, and preferably has a carbon number of 6 to 20. Among these, aromatic carboxylic acids having a benzene ring skeleton are preferred. Examples of aromatic carboxylic acids include aromatic monocarboxylic acids with one carboxy group, aromatic dicarboxylic acids with two carboxy groups, and aromatic tricarboxylic acids with three carboxy groups. The aromatic monocarboxylic acid is not particularly limited, but examples thereof include benzoic acid, cinnamic acid, toluic acid, xylyl acid, hemellitic acid, mesitylene acid, prenitylic acid, mesitic acid, cumic acid, anisic acid, and veratric acid. The aromatic dicarboxylic acid is not particularly limited, but examples thereof include phthalic acid, isophthalic acid, and terephthalic acid. The aromatic tricarboxylic acid is not particularly limited, but examples thereof include trimesic acid, hemimellitic acid, and trimellitic acid.

[0094] The saturated aliphatic hydroxycarboxylic acid comprises a linear or branched saturated aliphatic hydrocarbon group, one or more carboxy groups, and one or more hydroxyl groups, and preferably has 2 to 24 carbon atoms. Of these, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and 1 to 5 hydroxyl groups are preferred. Examples of saturated aliphatic hydroxycarboxylic acids include saturated aliphatic hydroxymonocarboxylic acids having one carboxy group, and saturated aliphatic hydroxydi- or tricarboxylic acids having two or three carboxy groups. The saturated aliphatic hydroxymonocarboxylic acid preferably has 2 to 20 carbon atoms, more preferably 2 to 7 carbon atoms, and preferably has 1 to 5 hydroxyl groups. Specific examples include, but are not limited to, glycolic acid, lactic acid, glyceric acid, hydroxyacetic acid, hydroxybutyric acid, 2-hydroxydecanoic acid, 3-hydroxydecanoic acid, 12-hydroxystearic acid, dihydroxystearic acid, cerebronic acid, leucinic acid, mevalonic acid, pantoic acid, gluconic acid, galactonic acid, mannonic acid, arabinonic acid, fructuronic acid, tagaturonic acid, and aldonic acid. The saturated aliphatic hydroxydicarboxylic acid preferably has 4 to 24 carbon atoms and is composed of a linear or branched saturated aliphatic hydrocarbon group, two carboxy groups, and one or more hydroxyl groups. Of these, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and 1 to 4 hydroxyl groups are preferred. Specific examples include, but are not limited to, tartronic acid, malic acid, tartaric acid, and citramalic acid. The saturated aliphatic hydroxytricarboxylic acid preferably has 4 to 24 carbon atoms and is composed of a linear or branched saturated aliphatic hydrocarbon group, three carboxy groups, and one or more hydroxyl groups. Of these, saturated aliphatic hydroxytricarboxylic acids having 2 to 7 carbon atoms and 1 to 4 hydroxyl groups are preferred. Specific examples include, but are not limited to, citric acid and isocitric acid.

[0095] The unsaturated aliphatic hydroxycarboxylic acid comprises a linear or branched saturated aliphatic hydrocarbon group, one or more carboxy groups, and one or more hydroxyl groups, and preferably has a carbon number of 3 to 22. Specific examples include, but are not limited to, ricinoleic acid, ricinoleic acid, and ricinelaic acid.

[0096] The saturated or unsaturated alicyclic hydroxycarboxylic acid preferably has 4 to 20 carbon atoms and is composed of a non-aromatic saturated or unsaturated carbon ring, one or more carboxy groups, and one or more hydroxy groups. Among these, saturated alicyclic hydroxycarboxylic acids with a 6-membered ring skeleton having 1 to 4 hydroxy groups are preferred. Specific examples include, but are not limited to, hydroxycyclohexanecarboxylic acid, dihydroxycyclohexanecarboxylic acid, quinic acid (1,3,4,5-tetrahydroxycyclohexanecarboxylic acid), shikimic acid, glucuronic acid, galacturonic acid, mannuronic acid, iduronic acid, and guluronic acid. Cyclic lactones having a hydroxyl group are also preferably used. Specific examples include, but are not limited to, ascorbic acid and erythorbic acid.

[0097] The aromatic hydroxycarboxylic acid preferably has a carbon number of 6 to 20 and is composed of an aromatic single ring or multiple rings, one or more carboxy groups, and one or more hydroxy groups. Among these, aromatic carboxylic acids having a benzene ring skeleton and 1 to 5 hydroxy groups are preferred, and specific examples thereof include, but are not limited to, salicylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxymethylbenzoic acid, vanillic acid, syringic acid, protocatechuic acid, gentisic acid, orselliic acid, mandelic acid, benzilic acid, atrolactic acid, phloretic acid, coumaric acid, umbellic acid, caffeic acid, ferulic acid, sinapic acid, cresotic acid, chlorogenic acid, and rosmarinic acid.

[0098] The carbonyl carboxylic acid is a carboxylic acid having 3 to 22 carbon atoms and a carbonyl group in the molecule, and is preferably a carbonyl carboxylic acid having 1 or 2 carbonyl groups and 3 to 7 carbon atoms. Specific examples include, but are not limited to, pyruvic acid and ketobutyric acid.

[0099] The alkyl ether carboxylic acid is a carboxylic acid having 2 to 22 carbon atoms and an ether group in the molecule, including a polyoxyalkylene alkyl ether carboxylic acid, and is preferably an alkyl carboxylic acid having 2 to 12 carbon atoms and 1 or 2 ether groups. Specific examples include, but are not limited to, methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, and ethoxybutyric acid.

[0100] The halogen carboxylic acid is preferably a halogen carboxylic acid having 2 to 22 carbon atoms. Specific examples include, but are not limited to, halogen-substituted halogen carboxylic acids such as trifluoroacetic acid, trichloroacetic acid, tribromoacetic acid, pentafluoropropionic acid, pentachloropropionic acid, pentabromopropionic acid, perfluorononanoic acid, perchlorononanoic acid, and perbromononanoic acid.

[0101] Examples of the salt of carboxylic acid in component (B) include salts of the anion of the above carboxylic acid and a cation (such as an alkali metal cation, alkaline earth metal cation, or ammonium cation).

[0102] Among the carboxylic acids or salts thereof of component (B), carboxylic acids are preferred, and from the viewpoint of antibacterial properties, carboxylic acids having a carboxyl group and a hydroxyl group are more preferred, and those having two or more carboxyl groups and a hydroxyl group are even more preferred. From the viewpoint of affinity with organic and inorganic materials, carboxylic acids having a hydroxyl group are one of the preferred embodiments.

[0103] Furthermore, from the viewpoint of safety and use, it is preferable to use as a raw material for component (B) a compound listed in the Standards for Quasi-drug Raw Materials (Standards for Quasi-drug Additives), Standards for Quasi-drug Additives, Japanese Pharmacopoeia (JP), Standards for Quasi-drugs Other than the JP (JP), Standards for Pharmaceutical Additives (Pharmacopoeia), Standards for Pharmaceutical Additives (Pharmacopoeia), and Official Specification of Food Additives (Food Additives). Examples of such compounds include, but are not limited to, acetic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, lactic acid, glycolic acid, succinic acid, citric acid, hydrochloric acid, fumaric acid, phosphoric acid, ascorbic acid, malic acid, tartaric acid, and salts thereof.

[0104] The antibacterial agent of the present invention may be a blend of only components (A) and (B), or may be a composition containing components (A) and (B).

[0105] In the antibacterial agent of the present invention, the molar ratio of component (A) to component (B) is not particularly limited and can be 1:99 to 99:1, preferably 1:9 to 9:1, more preferably 1:5 to 5:1, even more preferably 1:3 to 3:1, particularly preferably 1:2 to 2:1, and most preferably 1:1.

[0106] In particular, when component (B) is a polybasic acid, the blend of components (A) and (B) may be such that the valence of component (A) is equivalent to or less than equivalent to the valence of component (B) (when component (B) is a polybasic acid, it may be a partially neutralized salt or a completely neutralized salt), and less than equivalent is preferred from the viewpoint of antibacterial performance.

[0107] For example, when component (B) is a dibasic acid and component (A) has a valence of 1, the molar ratio of component (A) to component (B) can be 1:1 to 2:1. Two or more types of component (A) may be used. From the viewpoint of antibacterial performance, a compound having an unneutralized carboxyl group is preferred, and the molar ratio of component (A) to component (B) is preferably 1:1.

[0108] On the other hand, in terms of antibacterial performance, it is preferable that the ratio of the total number of amino groups to the total number of carboxy groups in component (A) and component (B) (total number of amino groups / total number of carboxy groups) is less than 1.

[0109] When component (A) and component (B) form an organic ammonium salt, it is preferable that component (A) or component (B) has one or more carboxy groups that are not involved in salt formation in addition to the carboxylate group generated by dissociation of a hydrogen ion from the carboxy group of component (A) or component (B), and it is more preferable that component (B) has one or more carboxy groups that are not involved in salt formation.

[0110] In the antibacterial agent of the present invention, the mixture of component (A) and component (B) or the salt of component (A) and component (B) may be in an anhydrous state (anhydride), or may be a hydrate that has absorbed moisture from the air. A hydrate refers to a compound that absorbs water and reaches a saturated moisture content when left in air at 25°C. A compound that does not absorb water when left in air at 25°C is an anhydrous compound.

[0111] The antibacterial agent of the present invention, a mixture of components (A) and (B) or a salt of (A) and (B), may be either a liquid or a solid at 25°C in the anhydride or hydrate form. For example, if the antibacterial agent of the present invention is liquid at 25°C, it will remain liquid when the solvent evaporates after spraying or applying the liquid containing the antibacterial agent to the area of ​​use, thereby exhibiting effectiveness over a wide area and preventing problems in use such as precipitation of crystals or aggregation and solidification. Furthermore, if the antibacterial agent is liquid at 25°C, it can be used as an antibacterial solvent or base when used with other additives. From these perspectives, it is preferable that the anhydride and / or hydrate be liquid at 25°C.

[0112] When the surface of an object on which the antibacterial agent of the present invention is used has functional groups that interact with and bond to hydrogen-bonding functional groups, such as oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and metals, the antibacterial agent of the present invention will interact with and bond to the hydrogen-bonding functional groups of component (A) and / or component (B), allowing the antibacterial agent of the present invention to adhere well to the object for a long period of time and exert its effect.

[0113] In a preferred embodiment of the combination of component (A) and component (B), from the standpoint of antibacterial activity and safety, component (A) is preferably an amine compound having a saturated aliphatic hydrocarbon group with one or more straight-chain or branched-chain hydroxy groups, more preferably having a monohydroxyalkyl or polyhydroxyalkyl group having 1 to 6 carbon atoms, and even more preferably triethanolamine, 2-amino-2-hydroxymethyl-1,3-propanediol, or 2-amino-2-ethyl-1,3-propanediol, and component (B) is preferably a saturated aliphatic hydroxycarboxylic acid (such as lactic acid, malic acid, citric acid, or tartaric acid), more preferably a saturated aliphatic hydroxydi- or tricarboxylic acid (such as malic acid, citric acid, or tartaric acid). In a preferred embodiment of the combination of component (A) and component (B), from the standpoint of antibacterial activity and safety, component (A) is an amine compound having a saturated aliphatic hydrocarbon group with one or more linear or branched hydroxy groups, and component (B) is a saturated aliphatic hydroxycarboxylic acid (lactic acid, malic acid, citric acid, tartaric acid, etc.). In a preferred embodiment of the combination of component (A) and component (B), from the standpoint of antibacterial properties and safety, component (A) is an amine compound having a monohydroxyalkyl group or polyhydroxyalkyl group having 1 to 6 carbon atoms, and component (B) is a saturated aliphatic hydroxydi- or tricarboxylic acid (such as malic acid, citric acid, or tartaric acid). In a preferred embodiment of the combination of component (A) and component (B), from the standpoint of antibacterial activity and safety, component (A) is triethanolamine, 2-amino-2-hydroxymethyl-1,3-propanediol, or 2-amino-2-ethyl-1,3-propanediol, and component (B) is malic acid, citric acid, or tartaric acid.

[0114] The antibacterial agent of the present invention is preferably a salt of components (A) and (B) from the viewpoint that it does not volatilize even in a low humidity environment and remains to maintain the antibacterial effect for a long period of time.

[0115] The form of the antibacterial agent is not particularly limited, but may be, for example, a liquid, solid, gel, cream, or the like.

[0116] The antibacterial agent of the present invention may contain a solvent and other components in addition to components (A) and (B). The solvent is not particularly limited, but examples thereof include water, methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, isoprene glycol, hexylene glycol, glycerin, benzyl alcohol, oleyl alcohol, methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, ethyl ether, acetone, toluene, hexane, heptane, paraffin, and acetonitrile. These may be used alone or in combination of two or more.

[0117] (Antibacterial composition, antiviral composition) The antibacterial composition or antiviral composition of the present invention contains the antibacterial agent of the present invention described above.

[0118] When producing the antibacterial composition or antiviral composition of the present invention, the antibacterial agent of the present invention, which has been previously blended with components (A) and (B), may be mixed with a solvent, other components, etc., or components (A) and (B) may be blended before the antibacterial composition is produced.

[0119] The form of the antibacterial composition of the present invention is not particularly limited, and may be, for example, liquid, solid, gel, or the like, or may not be fluid, and can be appropriately selected depending on the application and purpose. Furthermore, the form of the antibacterial composition is not particularly limited, and examples thereof include a solution in which components (A) and (B) are diluted in a solvent, a mixture with other components, and the like. Examples of the form of the antibacterial composition include additives added during the production of these, and solvents of existing antibacterial agents, antiviral agents, disinfectants, and the like.

[0120] The antibacterial composition or antiviral composition of the present invention contains the antibacterial agent of the present invention as an essential component, and may contain other components within the range that does not impair the effects of the present invention. Examples of other components include, but are not limited to, the above-mentioned solvents, existing antibacterial agents other than the antibacterial agent of the present invention, antiviral agents, disinfectants, and other agents effective against bacteria and viruses, surfactants (anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), resins, ultraviolet absorbers (including organic and inorganic types), fragrances, moisturizers, metal oxides, neutralizing agents, pH adjusters, colorants, antioxidants, corrosion inhibitors, rust inhibitors, metal deactivators, antifoaming agents, etc. These may be used alone or in combination of two or more.

[0121] The contents of components (A) and (B) in the antibacterial composition or antiviral composition of the present invention are not particularly limited, and are, for example, 1 to 100 mass % or 10 to 90 mass % relative to the total amount of the composition.

[0122] These organic ammonium salts are nonvolatile, and liquid compounds, in particular, can be coated uniformly at high concentrations after the volatile components evaporate, thereby providing effective and sustained antibacterial properties. They also function as solvents for existing agents effective against bacteria and viruses, such as antibacterial agents, antiviral agents, and disinfectants. This allows existing antibacterial agents, antiviral agents, disinfectants, etc. to be formulated at higher concentrations. Furthermore, even solid agents can be maintained in a dissolved state for a sustained period and can coat the surface of an object uniformly. Therefore, in addition to the antibacterial properties of the antibacterial agent of the present invention, the effects of existing antibacterial agents, antiviral agents, disinfectants, etc. can be fully exerted. Furthermore, a synergistic effect can be expected between the formulation of the present invention and existing antibacterial agents, antiviral agents, and disinfectants, providing antibacterial and antiviral properties at lower concentrations.

[0123] The existing antibacterial agents are not particularly limited, but include, for example, parahydroxybenzoic acid esters such as methylparaben and their sodium salts, benzoic acid and its salts, salicylic acid and its salts, sorbic acid and its salts, dehydroacetic acid and its salts, chlorcresol, resorcinol, pantothenyl ethyl ether benzoate, isopropylmethylphenol (cymen-5-ol), cetylpyridinium chloride, photosensitizers, phenol, sodium lauryldiaminoethylglycine, benzalkonium chloride, benzethonium chloride, chlorhexidine and its salts, orthophenylphenol and its salts, chloroxylenol, chlorphenesin, alkylisoquinolinium bromide, thianthol, thymol, trichlorocarbanilide, parachlorophenone, ol, halocarban, hinokitiol, pyrithione zinc, piroctone olamine, butylcarbamic acid iodide propynyl polyaminopropyl biguanide, methylisothiazolinone, paradimethylaminostyrylheptylmethylthiazolium iodide, beta-lactam antibiotics (penicillins, cephems, carbapenems, monobactams, penems), aminoglycoside antibiotics, lincomycin antibiotics, fosfomycin antibiotics, tetracycline antibiotics, chloramphenicol antibiotics, macrolide antibiotics, ketolide antibiotics, polypeptide constituents, glycopeptide antibiotics, streptogramin antibiotics, quinolone antibiotics, sulfonamides, oxazolidinone antibacterial agents, etc. Drugs effective against the viruses include, but are not limited to, sodium linear alkylbenzenesulfonate, alkylglycoside, alkylamine oxide, benzalkonium chloride, benzethonium chloride, dialkyldimethylammonium chloride, polyoxyethylene alkyl ether, potassium fatty acid, sodium fatty acid, chlorhexidine gluconate, polyhexamethylene biguanide, o-phthalaldehyde (phthalal), glutaraldehyde (glutaral), povidone iodine, sodium hypochlorite, and peracetic acid.

[0124] The amount of the above-mentioned existing antibacterial agents, antiviral agents, disinfectants, and other agents that are effective against bacteria and viruses is not particularly limited, although it depends on the compatibility with the antibacterial agent of the present invention and the solubility in the solvent, and can be 0.01% by mass to 10% by mass of the antibacterial composition, and the mass ratio to the antibacterial agent of the present invention can be 1:99 to 99:1.

[0125] The mixture of components (A) and (B) or the salt of (A) and (B) incorporated into the antibacterial agent of the present invention is non-volatile. Therefore, when the antibacterial composition is used, the volatile components contained in the antibacterial composition, such as water and alcohol, evaporate, increasing the concentration of existing agents effective against bacteria and viruses, such as antibacterial agents, antiviral agents, and disinfectants. Therefore, the antibacterial composition can exert its effects even at a low concentration when used.

[0126] Although the embodiments of the present invention have been described above, the present invention is not limited to these embodiments and various modifications are possible within the scope of the present invention. Furthermore, at least any combination of the above-mentioned preferred examples shown in formula (I), the above-mentioned preferred examples shown in formula (II), and the above-mentioned preferred examples shown in formula (III) may be more preferred embodiments based on the results of the Examples. At least any combination of the above-mentioned preferred examples shown in formulas (I) to (III) may be more preferred embodiments based on the results of the Examples. Furthermore, combinations of these with the above-mentioned preferred examples shown in the anions, combinations of these with the properties of a mixture of components (A) and (B) or a salt of (A) and (B), and combinations of these with the preferred examples of the polymer compound may be more preferred embodiments based on the results of the Examples. [Example]

[0127] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0128] The following reagents were used for minimum inhibitory concentration (MIC) measurements and halo tests. Staphylococcus aureus NBRC15035 strain: NITE Potassium lactate: Fujifilm Wako Pure Chemical Industries, Ltd. Culture medium: Muller-Hinton broth: Becton, Dickinson and Company Medium L - "Daigo" medium for reconstitution of dried products: Fujifilm Wako Pure Chemical Industries, Ltd. Calcium chloride: Fujifilm Wako Pure Chemical Magnesium chloride: Fujifilm Wako Pure Chemical Industries, Ltd. Sodium chloride: Fujifilm Wako Pure Chemical Skim milk: Snow Brand Megmilk Meat extract: Solabia Biokar Diagnostics Peptone: Solabia Biokar Diagnostics Sodium chloride: Fujifilm Wako Pure Chemical Agar: Fujifilm Wako Pure Chemical

[0129] 1. Preparation of the compound (salt) The formulations (salts) of Examples 1 to 8 and 21 to 43 were prepared by the method described in JP 2019-023185 A, and their states at 25°C were confirmed (Tables 1A to 1D).

[0130] 2. Antibacterial evaluation of the compound (salt) 1 (minimum inhibitory concentration) The minimum inhibitory concentrations (MICs) of Examples 1 to 8, 21 to 43, and Comparative Examples 1, 8, and 9 shown in Tables 1A to 1D, 2A, and 2B against Staphylococcus aureus were measured using the broth microdilution method (described in the standard method of the Japanese Society of Chemotherapy) to confirm the antibacterial activity of each compound (salt). Compound (salt) concentrations of 250, 200, 150, 100, 50, 25, 12.5, 8, 4, 2, 0.8, 0.4, 0.2, 0.1, and 0.05 mg / mL were evaluated, and the MICs are shown in Tables 1A to 1D. A lower MIC value indicates better antibacterial activity.

[0131] From the results in Tables 1A to 1D, Examples 1 to 8 and 21 to 43 showed higher antibacterial activity than Comparative Examples 1, 8, and 9, with MICs of 4 mg / mL to 100 mg / mL. Sodium lactate and disodium malate in Comparative Examples 8 and 9 failed to inhibit bacterial growth even at a concentration of 250 mg / mL. When Examples 1, 2, and 6 were compared with the formulations of the same component (B) in Comparative Examples 1 and 8, it was confirmed that Examples 1, 2, and 6, which have a hydrogen-bonding functional group (hydroxyl group) in component (A), have high antibacterial activity. Furthermore, when Examples 1 and 21 and 22, Example 2 and Examples 3 to 5, and Example 6 and Examples 7 and 8 of the same component (A), it was confirmed that the formulations (salts) having two or more carboxylate groups in component (B) and, further, when Examples 3 and 7 of the same component (B) were compared, it was confirmed that the R 7 However, the compound (salt) containing alkyl group component (A) tended to have high antibacterial activity.

[0132] 3. Antibacterial evaluation of the compound (salt) 2 (halo test 1) A halo test was conducted using Staphylococcus aureus with reference to JIS L1902. A 21mm diameter Kiriyama funnel filter paper (manufactured by Kiriyama Seisakusho) was used as the test piece, and the filter paper was placed on a culture medium containing the bacteria. 100µL of a compound (salt) aqueous solution (Examples 9-11, Comparative Examples 2-4) with the concentration shown in Tables 2A and 2B was then dropped onto the filter paper. Cultivation was then carried out, and the presence or absence of a halo was visually confirmed. The presence or absence of a halo is shown in Tables 2A and 2B.

[0133] 4. Evaluation of adhesion and antibacterial properties of the formulation (salt) 3 (halo test 2) 4-1.Adhesion evaluation 100 μL of the compound (salt) aqueous solution (Examples 9 to 11) with the concentration shown in Tables 2A and 2B was dropped onto a 21 mm diameter Kiriyama funnel filter paper and vacuum dried at 60°C for 8 hours. The adhesion rate of the sample was calculated from the change in weight of the filter paper (Tables 2A and 2B). As a blank test, 100 μL of water was dropped onto the filter paper and vacuum dried, and the weight change before and after the operation was measured and used as a correction value. A: Weight of attached sample = Weight of filter paper after drying (mg) - Weight of filter paper before test (mg) + Correction value (1.15mg) B: Weight of applied sample = Weight (mg) of 100 μL of aqueous solution × Concentration (mass%) / 100 Adhesion rate (%)=100×A / B

[0134] 4-2.Hello Exam 2 A halo test was conducted using Staphylococcus aureus in accordance with JIS L1902. The test pieces were sterilized in advance, had the aqueous solution of the compound described in 4-1 above dripped onto them, and then vacuum dried at 60°C for 8 hours. After the test, the presence or absence of a halo was visually confirmed, and the presence or absence of a halo is shown in Tables 2A and 2B.

[0135] From the results of Halo Test 1, it was found that ethanol, which is widely known to have bactericidal and antibacterial effects, volatilized during cultivation and was therefore unable to exhibit antibacterial effects, and no halo was observed. On the other hand, halo was observed for the formulations of the Examples. This suggests that the formulations of the present invention, being non-volatile, remain attached to the filter paper without volatilizing, and are therefore able to exert antibacterial effects for a long period of time.

[0136] In Halo Test 2, ethanol volatilized and did not adhere to the filter paper, whereas the compound of the example has hydrogen-bonding functional groups and therefore adheres well to the filter paper, which also has hydrogen-bonding functional groups. It was confirmed that the compound's antibacterial properties persisted for a long period of time even after heating and vacuum drying due to its non-volatility.

[0137] 5. Evaluation of solubility and stability of poorly soluble substances in the formulation Antibacterial compositions were prepared by dissolving 1.0, 0.5, or 0.25% by mass of 4-methylparaben (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as paraben) which is a poorly water-soluble antibacterial agent, in a 50% by mass aqueous solution of the compound (salt) shown in Tables 3A and B (50% by mass aqueous solution of potassium lactate in Examples 12 to 18 and Comparative Example 5, and water only in Comparative Example 6) at 80°C. The compositions were then left to stand at 25°C for 24 hours under sealed conditions, and the appearance of each antibacterial composition was visually inspected and the solubility was evaluated according to the following criteria (Tables 3A and B). ◎: 1.0 mass% or more, no crystal precipitation, clear solution 〇: 0.5% by mass or more and less than 1.0% by mass No crystal precipitation, clear solution △: 0.25% by mass or more and less than 0.5% by mass No crystal precipitation, clear solution ×: Less than 0.25% by mass Crystal precipitation or cloudiness

[0138] The same procedure was performed on the antiviral substances known to be effective against viruses, namely polyoxyethylene alkyl ether (Pelletex 2465 manufactured by Miyoshi Oil & Fats), alkyl glycoside (n-octyl β-D-glucopyranoside manufactured by Tokyo Chemical Industry Co., Ltd.), benzalkonium chloride (benzalkonium chloride manufactured by Nacalai Tesque), benzethonium chloride (benzethonium chloride manufactured by Tokyo Chemical Industry Co., Ltd.), and o-phthalaldehyde (phthalaldehyde manufactured by Fujifilm Wako Pure Chemical Industries Co., Ltd.), and their solubility was evaluated using the above criteria (Table 3A and B).

[0139] The blend (salt) of the present invention was able to dissolve poorly water-soluble antibacterial agents and other antiviral substances well, and an antibacterial composition was obtained. When Examples 13-14 of the component (B) were compared with Examples 16-18, the R 7 However, it was confirmed that the alkyl group component (A) tends to have high solubility in the compound (salt) paraben.

[0140] 6. Antibacterial evaluation of antibacterial composition (minimum inhibitory concentration) Examples 19 and 20, which were prepared to contain the same amounts of the blends of components (A) and (B) and paraben shown in Tables 4A and B, respectively, and Comparative Example 8, which contained only paraben, were evaluated using the same test method as in 2. above, with a paraben concentration of 1.0 mg / mL (the antibacterial compositions of Examples 19 and 20 had a total of 2.0 mg / mL of antibacterial agent), and the presence or absence of antibacterial activity was evaluated based on the presence or absence of bacterial growth.

[0141] Paraben or the compound (salt) alone in Comparative Example 1 and Reference Examples 1 and 2 at 1 mg / mL did not exhibit antibacterial properties, but in Examples 19 and 20, in which paraben and the compound (salt) were mixed at 1 mg / mL each to produce antibacterial compositions with a total of 2 mg / mL, the antibacterial effect of paraben was added to the antibacterial effect of the compound (salt), and the composition as a whole exhibited antibacterial properties.

[0142] In other words, by adding another additive to the compound (salt) of the present invention, the effect of that additive can be imparted to a composition containing the compound (salt) of the present invention. For example, a composition obtained by adding (dissolving) the antiviral substance of 5. will have antiviral properties in addition to antibacterial properties.

[0143] 7. Stability evaluation of antibacterial compositions A 50% by mass aqueous solution of Formulation 4 or 8 and a 0.25% by mass solution of paraben (additive) were dissolved in water, and the solution was placed in an open-topped sample bottle and allowed to stand at 50° C. for 48 hours. After the test, the appearance of each antibacterial composition was visually inspected.

[0144] When water alone was used, the water evaporated and paraben crystals precipitated. On the other hand, in the 50% by mass aqueous solutions of Formulations 4 and 8, the liquid did not completely evaporate and no crystal precipitation was observed. The compositions of the present invention maintain the solubility of the additives due to the non-volatility of the formulation (salt) of the present invention, and have good stability, allowing the formulation (salt) and additives to efficiently exert their effects for a long period of time.

[0145] 8. Evaluation of the durability of antibacterial compositions 300 μL of each compound (salt) was applied to an unsterilized 21 mm diameter Kiriyama funnel filter paper, placed in an open-top petri dish, and left to stand for one week in a room with a lot of people coming and going. The applied surface was placed on an agar medium of the same composition as used in 3. so that it was in contact with the agar medium, and cultured at 37°C for one day. The filter paper was then removed, and cultured at 37°C for another day, after which bacterial growth was confirmed visually. Example 44: 50% by weight tromethamine / citric acid (compound No. 4) aqueous solution Comparative Example 10: Water Comparative Example 11: 70% by mass ethanol aqueous solution (Formulation No. 10)

[0146] Comparing Example 44 with Comparative Examples 10 and 11, no bacterial growth was observed in Example 44, but bacterial growth was confirmed in Comparative Examples 10 and 11. Furthermore, comparing Comparative Examples 10 and 11, growth of a greater amount of bacterial cells was confirmed in Comparative Example 10. In Comparative Example 10, the growth of bacteria that were originally attached to the filter paper and bacteria that adhered during standing was confirmed, while in Comparative Example 11, the bacteria that were attached to the filter paper were inactivated by the bactericidal action of ethanol, but it is thought that the bacteria that adhered after the ethanol evaporated were confirmed. On the other hand, in Example 44, since the formulation of the present invention was non-volatile, the formulation adhered to the paper in a high concentration after the water evaporated, and it is thought that the antibacterial effect was maintained, so that the growth of bacteria was not confirmed. Therefore, it was suggested that the compound of the present invention is nonvolatile and therefore remains attached to the filter paper without volatilizing, thereby exhibiting antibacterial effects for a long period of time.

[0147] [Table 1A]

[0148] [Table 1B]

[0149] [Table 1C]

[0150] [Table 1D]

[0151] [Table 2A]

[0152] [Table 2B]

[0153] [Table 3A]

[0154] Table 3B

[0155] Table 4A

[0156] Table 4B

Claims

1. An antibacterial agent which is a blend of the following components (A) and (B). (A) Monoethanolamine, diethanolamine, triethanolamine, or 2-amino-2-hydroxymethyl-1,3-propanediol (B) saturated aliphatic hydroxycarboxylic acid

2. The antibacterial agent described in claim 1, wherein component (B) is lactic acid, malic acid, citric acid, or tartaric acid.

3. An antibacterial agent as described in claim 1, wherein component (B) is a saturated aliphatic hydroxy di- or tricarboxylic acid.

4. The antibacterial agent described in claim 3, wherein component (B) is malic acid, citric acid, or tartaric acid.

5. An antibacterial agent comprising an organic ammonium salt formed by a cation derived from the component (A) according to claim 1, which may have a proton of the component (B) according to claim 1, and a carboxy anion derived from the component (B).

6. 2. The antibacterial agent according to claim 1, wherein the mixture of components (A) and (B) or the salt of components (A) and (B) is a liquid at 25°C in the form of an anhydride and / or a hydrate.

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