WO2022225049A1

WO2022225049A1 - Antibacterial agent, antibacterial composition using same and antiviral composition

Info

Publication number: WO2022225049A1
Application number: PCT/JP2022/018557
Authority: WO
Inventors: 亜紀良矢下; 大介中村; 和馬竹腰; 恒太郎金子; 功治河合
Original assignee: ミヨシ油脂株式会社
Priority date: 2021-04-23
Filing date: 2022-04-22
Publication date: 2022-10-27
Also published as: JPWO2022225049A1

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

Antibacterial agent and antibacterial composition and antiviral composition using the same

The present invention relates to an antibacterial agent and an antibacterial composition and an antiviral composition using the same.

Conventionally, various antibacterial agents have been used in various fields for the purpose of preventing bacterial contamination and putrefaction, and preventing and treating bacterial infections. In recent years, due to the epidemic of new infectious diseases, etc., interest in public health is increasing more and more. Against this backdrop of the times, there is a growing need for chemicals to keep the surfaces of the human body and parts that come into contact with the human body clean. Alcohol-based agents such as ethanol are usually used for these applications, but it is difficult for people who are physically sensitive to alcohol to use them. There is a problem that it is inferior to Chlorine-based chemicals such as sodium hypochlorite water and hypochlorous acid water are also used. There are restrictions on use, such as the generation of chlorine gas. In addition, hypochlorous acid water has problems such as poor long-term antibacterial properties due to poor storage stability and a decrease in effective chlorine concentration during use.

For this reason, antibacterial agents with excellent safety, low impact on the human body, low volatility, and long-lasting effects are desired.

The applicant proposed an organic ammonium salt (ionic liquid) having a hydrogen-bonding functional group in the cation or anion (Patent Documents 1 to 5). It has been found that this organic ammonium salt is hydrophilic, liquid at room temperature, and has excellent water-holding and moisturizing properties.

JP 2014-131974 A JP 2014-131975 A JP 2019-023185 A WO2020/166674 WO2020/166678

However, studies focused on antibacterial performance, in particular, studies of combinations of amines or ammonium compounds and carboxylic acids or salts thereof suitable for this task, and combinations of amines and anions that serve as cations of organic ammonium salts have not been made.

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. there is

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) an amine or ammonium compound having a hydrogen-bonding functional group (excluding amino acids);
(B) Carboxylic acid or salt thereof The antibacterial composition of the present invention contains the above antibacterial agent.
The antiviral composition of the present invention contains the above antibacterial agent.

The antibacterial agent, antibacterial composition, and antiviral composition of the present invention are highly safe and have excellent sustained effects. The antibacterial agent of the present invention is also excellent as a solvent for other ingredients.

The present invention will be described in detail below.

In the present invention, the term "formulation" includes blending components (A) and (B) until the final target formulation is prepared, and components (A) and (B) are used as starting materials. When synthesizing a salt formed by components (A) and (B) as a compound, and when the salt is mixed with other ingredients such as water as necessary to form a compound encompasses The formulation of the present invention may be a mixture consisting only of components (A) and (B) (including the case where they are salts), and components other than components (A) and (B) or their salts It may be a composition containing components, for example, a composition containing water, a composition to which additives are added when manufacturing a product, or a composition that is a product such as cosmetics.

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

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

Among the components (A), the ammonium compounds include salts of the above amine compounds and quaternary amine compounds.

The component (A) and the cation derived from the component (A) may have an organic group as a substituent.

[Organic group]
In the present specification, the organic group essentially has a carbon atom and may additionally contain at least one selected from a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a halogen atom. Although the atomic group contained in the organic group is not particularly limited, examples thereof include hydrocarbon groups, heterocyclic groups, and substituents described in the section [Substituents] below. For example, the substituents described in the "Substituents" column below replace hydrogen atoms of the hydrocarbon group, interrupt the hydrocarbon group, and/or are included at the base end of the hydrocarbon group, or include aromatic hydrocarbons. A group forming a condensed ring with a water group is also included.
The number of carbon atoms in the organic group is not particularly limited, but is, for example, 1-22, 1-18, 1-12, 1-8, or 1-4.

[Hydrocarbon group]
In the present specification, the hydrocarbon group is not particularly limited, and examples include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof. A hydrocarbon group etc. are mentioned. Depending on the context, it may be monovalent or polyvalent, and examples of monovalent saturated or unsaturated aliphatic hydrocarbon groups include, but are not limited to, linear or branched alkyl groups, alkenyl groups and alkynyl groups. etc. Alkyl groups include linear or branched chains, but are not particularly limited, and examples thereof include methyl, ethane-1-yl, propan-1-yl, 1-methylethan-1-yl, butane-1- yl group, butan-2-yl group, 2-methylpropan-1-yl group, 2-methylpropan-2-yl group, pentan-1-yl group, pentan-2-yl group, hexan-1-yl group , heptane-1-yl group, octan-1-yl group, 2-ethylhexan-1-yl group, 1,1,3,3-tetramethylbutan-1-yl group, nonan-1-yl group, decane -1-yl group, undecane-1-yl group, dodecane-1-yl group, tridecane-1-yl group, tetradecane-1-yl group, pentadecane-1-yl group, hexadecane-1-yl group, 2- hexyldecane-1-yl group, heptadecan-1-yl group, octadecane-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, α,α-dimethylbenzyl group and the like. Alkenyl groups include linear or branched chains, and are not particularly limited, but examples include vinyl, prop-1-en-1-yl, allyl, isopropenyl, but-1-en-1-yl. group, but-2-en-1-yl group, but-3-en-1-yl group, 2-methylprop-2-en-1-yl group, 1-methylprop-2-en-1-yl group, pent-1-en-1-yl group, pent-2-en-1-yl group, pent-3-en-1-yl group, 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, octa-1-en-1-yl group, octa-7-en-1-yl group, non-1-ene -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, tetradeca-1-en-1-yl group, tetradeca-13-en-1-yl group, pentadeca-1-en-1-yl group, pentadec-14-en-1-yl group, hexadecaco -1-en-1-yl group, hexadec-15-en-1-yl group, heptadecan-1-en-1-yl group, heptadedec-16-en-1-yl group, octadec-1-en-1 -yl group, octadec-9-en-1-yl group, octadec-17-en-1-yl group, nonadecan-1-en-1-yl group, icosa-1-en-1-yl group, henicosa- 1-en-1-yl group, docos-1-en-1-yl group and the like. Alkynyl groups include straight or branched chains, and are not particularly limited and include, but are not limited to, ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, 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-yn-1-yl group, hex-5-yn-1-yl group, hept-1-yn-1-yl group, hept-6-yn-1-yl group, octa-1-yne -1-yl group, octa-7-yn-1-yl group, non-1-yn-1-yl group, non-8-yn-1-yl group, deca-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, tetradeca-1-yn-1-yl group, tetradeca-13-yn-1-yl group, pentadeca -1-yn-1-yl group, pentadeca-14-yn-1-yl group, hexadec-1-yn-1-yl group, hexadec-15-yn-1-yl group, heptadeca-1-yn-1 -yl group, heptadeca-16-yn-1-yl group, octadec-1-yn-1-yl group, octadec-17-yn-1-yl group, nonadeca-1-yn-1-yl group, icosa- 1-yn-1-yl group, henicosa-1-yn-1-yl group, docos-1-yn-1-yl group and the like.

The saturated or unsaturated alicyclic hydrocarbon group is preferably a saturated alicyclic hydrocarbon group and is not particularly limited. Examples of monovalent groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo A heptyl group, a cyclooctyl group, and a group containing an alicyclic residue such as those residues are included.

The aromatic hydrocarbon group is not particularly limited, but includes, for example, a phenyl group, a naphthyl group, an anthracenyl group, and groups containing aromatic ring residues such as residues thereof. A condensed ring may be formed together with the substituents described in [Substituent] below. Examples of monovalent aromatic hydrocarbon groups include, but are not limited to, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5 -dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group, 4-ethylphenyl group, 4-propyl phenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, 4-pentylphenyl group, 4-tert-pentylphenyl group, 2,4-bis(4-tert-pentyl)phenyl group, 1,1,3,3-tetramethylbutylphenyl group, 2-methyl-5-tert-butylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 4-heptylphenyl group, 4-octylphenyl group, 4-nonylphenyl group, 4-decanylphenyl group, 4-undecylphenyl group, 4-dodecylphenyl group, 4-tridecylphenyl group, 4-tetradecylphenyl group, 4-pentadecylphenyl group, 4 -hexadecylphenyl group, 4-heptadecylphenyl group, 4-octadecylphenyl group, 4-biphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3- ethoxyphenyl group, 4-ethoxyphenyl group, 2-chlorophenyl group, 2-fluorophenyl group, 4-fluorophenyl group, 2-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-hydroxyphenyl group, 1 -naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group and the like.

Examples of divalent hydrocarbon groups include groups obtained by removing one hydrogen atom from the above groups.

[Substituent]
Examples of the substituent include, but are not limited to, hydrocarbon groups, oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and halogens. Substituents also include groups to which these substituents are bonded.

Examples of the hydrocarbon group include those listed in the above [hydrocarbon group].

Examples of oxygen-containing groups include, but are not limited to, hydroxyl groups, alkoxy groups, acetoxy groups, acetyl groups, aldehyde groups, carboxyl groups, carboxylate groups, urea groups, urethane groups, amide groups, imide groups, ether groups, carbonyl group, ester group, oxazole group, morpholine group, carbamate group, carbamic acid group, carbamoyl group, polyoxyethylene group, tocopheryl group, chroman group, dihydropyran group, glyceryl group, glyceryl ether group and the like.

Examples of nitrogen-containing groups include, but are not limited to, cyano groups, cyanato groups, isocyanate groups, nitro groups, nitroalkyl groups, amide groups, urea groups, urethane groups, imide groups, carbodiimide groups, azo groups, pyridyl groups, imidazole group, pyrrolidyl group, piperidyl group, pyrrolyl group, pyrazyl group, triazole group, isoquinolyl group, oxazolyl group, thiazolyl group, morpholyl group, guanidyl group, pyrimidyl group, piperazyl group, triazyl group, quinolyl group, indole group, quinoxalyl group , an isoxazolyl group, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium group, an aminoalkyl group and the like.

Examples of sulfur-containing groups include, but are not limited to, sulfuric acid group, sulfonyl group, sulfonic acid group, mercapto group, thioether group, thiocarbonyl group, thiourea group, thiocarboxy group, thiocarboxylate group, dithiocarboxy group, Dithiocarboxylate group, sulfate ester, thiophene group, thiazole group, thiol group, sulfo group, sulfide group, disulfide group, thioester group, thioamide group, thiocarbamate group, dithiocarbamate group and esters thereof.

Examples of phosphorus-containing groups include, but are not limited to, phosphoric acid group, phosphorous acid group, phosphonic acid group, phosphinic acid group, phosphonous acid group, phosphinic acid group, pyrophosphate group, phosphate ester group, Phosphate ester group, phosphonate ester group, pyrophosphate group, ester group thereof and the like.

　Halogen includes fluorine, chlorine, bromine, and iodine.

Examples of the organic group include hydrocarbon groups that may have a substituent and whose hydrocarbon portion may contain an oxygen atom. As for the hydrocarbon group, the contents described in the above [Hydrocarbon group] column are referred to. 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, 1 to 22, 4 to 22, 8 to 22, or 12 to 22 carbon atoms, linear or branched, and may have 1 to 18, 1 to 12, or 1 to 18 carbon atoms. 4 may be linear or branched.

The hydrocarbon group may have a substituent, and the substituent is not particularly limited, but includes, for example, those described in the above [Substituent] column. 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 preferable, and a hydroxyl group is particularly preferable.

The hydrocarbon moiety may contain an oxygen atom. In this case, the hydrocarbon moiety includes the oxygen-containing group described above, and is not particularly limited. Examples include an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group and an ester bond. , amide bond, urea bond or urethane bond. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom" means that 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 the group is Including at the ends or when a hydrogen atom is substituted.

In terms of enhancing the effect of the present invention, the component (A) has a chemical structure that is a basic skeleton, such as a site where a functional group can be introduced in the component (A) (a nitrogen site, a carbon site that forms a ring with nitrogen, etc.) contained atoms) are replaced with organic groups, one or more of which have hydrogen-bonding functional groups. Alternatively, a hydrogen atom directly bonded to nitrogen constitutes a hydrogen-bonding functional group.

In the above organic group having a hydrogen-bonding functional group, the hydrogen-bonding functional group is not particularly limited. Examples include a hydrogen atom, and an oxygen-containing group is preferred.

Hydrogen-bonding functional groups in component (A) include, from the viewpoint of affinity for water and affinity for organic and inorganic materials capable of bonding and coordinating with hydrogen-bonding functional groups, hydroxyl group, carboxyl group, and the like. Groups, carboxylate groups, ester groups, ether groups, alkoxy groups, hydrogen atoms directly bonded to nitrogen are preferred. Among these, a hydroxyl group, a carboxy group, a carboxylate group, an ether group, an alkoxy group, and a hydrogen atom directly bonded to nitrogen are more preferable, and a hydroxyl group, a carboxy group, a carboxylate group, and a hydrogen atom directly bonded to nitrogen are more preferable. A hydrogen atom directly bonded to a hydroxyl group, a carboxy group, or nitrogen is particularly preferred, and a hydrogen atom directly bonded to a hydroxyl group or nitrogen is most preferred. A preferred example of the organic group having a hydrogen-bonding functional group is a hydrocarbon group having a hydrogen-bonding functional group. For example, the organic group having a hydrogen bonding functional group includes a hydrocarbon group containing a hydroxyl group (hydroxy hydrocarbon group), a hydrocarbon group containing a carboxy group (carboxy hydrocarbon group), and a hydrocarbon group containing a hydroxyl group and a carboxy group. (hydroxycarboxy hydrocarbon group), a hydrocarbon group containing a carboxylate group, a hydrocarbon group containing an ester group, a hydrocarbon group containing an ether group, a hydrocarbon group containing an alkoxy group, and the like.

From the viewpoint of safety, the component (A) is a hydroxyhydrocarbon having one or more hydroxyl groups, a straight-chain or branched hydrocarbon moiety, and the hydrocarbon moiety may contain an oxygen atom. It is preferred to have a group.

The hydrocarbon group includes a saturated or unsaturated aliphatic hydrocarbon group, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, etc., and a hydrocarbon group combining them. Common hydrocarbon groups can be used as these hydrocarbon groups. Among the above hydrocarbon groups, saturated aliphatic hydrocarbon groups are preferred. Examples of the hydrocarbon group include those described in the section [Hydrocarbon group] below.

For example, although not particularly limited, the hydroxy hydrocarbon group has one or more hydroxyl groups, and the hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, and still more preferably 1 to 1 carbon atoms. 12, particularly preferably straight or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.

Here, when the hydrocarbon portion 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 with the hydrocarbon portion. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom" means that 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 the group is Including at the ends or when a hydrogen atom is substituted.

As the hydroxy hydrocarbon group, a saturated or unsaturated aliphatic hydrocarbon group having one or more hydroxy groups, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a hydrocarbon combination thereof groups, preferably a saturated aliphatic hydrocarbon group having one hydroxy group (monohydroxyalkyl group, etc.), a saturated aliphatic hydrocarbon group having two or more hydroxy groups (polyhydroxyalkyl group, etc.), and the oxygen Containing groups may be included.

The saturated aliphatic hydrocarbon group having one hydroxy group (monohydroxyalkyl group) is not particularly limited, but examples thereof include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropane-1 -yl group, 2-hydroxypropan-1-yl group, 3-hydroxypropan-1-yl group, 1-hydroxypropan-2-yl group, 2-hydroxypropan-2-yl group, 2-hydroxymethylpropane- 2-yl group, 2-hydroxyethylpropan-2-yl group, 1-hydroxybutan-1-yl group, 2-hydroxybutan-1-yl group, 3-hydroxybutan-1-yl group, 4-hydroxybutane -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, 2-hydroxyethylpentan-2-yl group, 6-hydroxyhexan-1-yl group, 7-hydroxyheptane-1 -yl group, 8-hydroxyoctan-1-yl group, 9-hydroxynonan-1-yl group, 10-hydroxydecane-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-hydroxy Pentan-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-methyl Pentan-3-yl group, 2-ethyl-1-hydroxyhexan-2-y group, 1-hydroxy-2-propylhexan-2-yl group, 2-ethyl-1-hydroxyheptan-2-yl group, 2-ethyl-1-hydroxy-4-methylpentan-2-yl group, 1 -hydroxy-2-(1-methylethyl)pentan-2-yl group, 3-ethyl-4-hydroxyheptan-3-yl group and the like. 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.

The saturated aliphatic hydrocarbon group having two or more hydroxy groups (polyhydroxyalkyl group) is not particularly limited, and examples thereof include di-, tri-, tetra-, penta-, hexa-, hepta-, and octahydroxyalkyl groups. . Specifically, although not particularly limited, for example, dihydroxyethyl groups such as 1,2-dihydroxyethyl group; 1,2-dihydroxypropan-1-yl group, 2,3-dihydroxypropan-1-yl group dihydroxypropan-1-yl group; 1,2-dihydroxypropan-2-yl group, dihydroxypropan-2-yl group such as 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, etc. 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, trihydroxybutan-1-yl group such as 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, dihydroxy-2-methylpropan-1-yl group such as 2,3-dihydroxy-2-methylpropan-1-yl group; trihydroxy-2-methyl Propan-1-yl group; Tetrahydroxy-2-methylpropan-1-yl group; 1,2-dihydroxybutan-2-yl group, 1,3-dihydroxybutan-2-yl group, 1,4-dihydroxybutane -2-yl group, 2,3-dihydroxybutan-2-yl group, 2,4-dihydroxybutan-2-yl group, 3,4-dihydroxybutan-2-yl group and other dihydroxybutan-2-yl groups ; 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, 1,1-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; di, tri, tetra, penta, hexa, hepta , or an octahydroxyoctan-1-yl group. The polyhydroxyalkyl group preferably has 2 to 8 hydroxyl groups, more preferably 2 to 6 hydroxyl groups, and the alkyl group preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms. , those having 1 to 12 carbon atoms are more preferred, and those having 1 to 6 carbon atoms are particularly preferred. A branched polyhydroxyalkyl group represented by the following formula is also preferred.

(Wherein, R ⁷ is a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms), or a linear alkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms) indicates a hydroxyalkyl group.)

The group of the above formula is not particularly limited, but examples 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, 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-dihydroxybutane -2-yl group, 2,4-dihydroxybutan-2-yl group, 3,4-dihydroxybutan-2-yl group, tetrahydroxybutan-2-yl group, 1,3-dihydroxy-2-methylpropane- 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, 1,1-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, di-, tri-, tetra-, penta-, hexa-, hepta- or octahydroxyoctan-1-yl group.

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 preferable, and from the viewpoint of antibacterial properties, 1,3-dihydroxy-2-ethylpropan-2-yl group, 1, A 3-dihydroxy-2-hydroxymethylpropan-2-yl group is more preferred.

From the viewpoint of safety, when component (A) has a monohydroxyalkyl group, triethanolamine and diethanolamine are preferred, and triethanolamine is particularly preferred.

In addition, from the viewpoint of safety and use, component (A) is specified in the Standards for Quasi-drug Ingredients (Quasi-drugs Ingredients), Standards for Quasi-drug Additives, Japanese Pharmacopoeia (Japanese Pharmacopoeia), Japanese Pharmacopoeia Drugs It is preferable to use compounds listed in the Standards for Quasi-Drugs (Regulations), Pharmaceutical Additives Standards (Medicine Additives), and Food Additives Standards (Food Additives) as raw materials (e.g. acids, bases), especially 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. Among them, triethanolamine, 2- Amino-2-hydroxymethyl-1,3-propanediol is more preferred.

In component (A), one of the moieties in component (A) into which a functional group can be introduced (atoms contained in the chemical structure serving as a basic skeleton, such as a nitrogen moiety and a carbon moiety forming a ring together with nitrogen) is The above may be substituted with an organic group that does not have a hydrogen-bonding functional group. Such organic groups include, for example, hydrocarbon groups. Hydrocarbon groups include, for example, alkyl groups. The alkyl group is preferably linear or branched with 1 to 18 carbon atoms, more preferably linear or branched with 1 to 12 carbon atoms, and even more preferably linear or branched with 1 to 8 carbon atoms. , a linear or branched chain having 1 to 4 carbon atoms is more preferable.

When the component (A) is an ammonium compound, the anion is not particularly limited, but examples include hydroxide anions, halogen anions, sulfur anions, phosphorus anions, cyanide anions, and boron anions. , fluorine-based anions, nitrogen oxide-based anions, carboxylic acid-based anions, and the like, and among these, hydroxide anions are preferred.

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).

(In the formula, each R ¹ independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R ² is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and m is an integer of 0 to 3.)

In the above formula (I), m is preferably an integer of 1-3.

In formula (I) above, all R ² are preferably hydrogen atoms.

In the above formula (I), in the hydroxy hydrocarbon group, the hydrocarbon in the hydrocarbon moiety that may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.

In the formula (I), at least one of R ¹ has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. is preferred.

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

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

A combination of at least one of the above preferred examples shown in formula (I) can be a more preferred embodiment.

In the above formula (I), R ¹ has one hydroxyl group, the hydrocarbon moiety is a linear hydroxy hydrocarbon group having 1 to 6 carbon atoms, R ² is a hydrogen atom, and m is 1 to An integer of three is preferred.
In the above 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, R ² is a hydrogen atom, and m is An integer of 1 is preferred.
In the above formula (I), R ¹ has 2 to 6 hydroxyl groups, the hydrocarbon moiety is a linear hydroxy hydrocarbon group having 2 to 6 carbon atoms, R ² is a hydrogen atom, and m is An integer of 1 is preferred.

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

(In the formula, each R ³ independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R ⁴ is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, n represents an integer of 0 to 4, and X ⁻ represents an anion.)

In formula (II) above, the anion represented by X ⁻ is preferably a hydroxide ion.

In the above formula (II), n is preferably an integer of 1-4.

In formula (II), all R ⁴ are preferably hydrogen atoms.

In the above formula (II), in the hydroxy hydrocarbon group, the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.

In the above formula (II), at least one of R ³ has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is preferably a hydroxy hydrocarbon group in which the hydrocarbon is a saturated aliphatic hydrocarbon. .

In the formula (II), at least one of R ³ has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. Preferably.

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

A combination of at least one of the above preferred examples shown in formula (II) can be a more preferred embodiment.

In the above formula (II), R ³ has one hydroxyl group, the hydrocarbon moiety is a hydroxy hydrocarbon group having 1 to 3 carbon atoms, R ⁴ is a hydrocarbon group having 1 to 3 carbon atoms, and n preferably denotes an integer of 1.
In formula (II), R ⁴ is a hydrocarbon group having 1 to 4 carbon atoms, and n preferably represents an integer of 0.

Another preferred embodiment of the antibacterial agent of the present invention is an organic ammonium salt formed by component (A) and component (B).

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

In the present invention, the residue in the component (B) refers to an uncharged atom or atomic group (group), a cationic residue having a charge that becomes a cation, and an anionic residue that becomes an anion. and

In the present invention, the carboxylic acid or its salt of component (B) has a cationic residue and an anionic residue. The cationic residue is a hydrogen atom or a group (atomic group) that combines 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 protonated hydrogen and an anionic residue.

In the present invention, the organic ammonium salt includes an organic cation or NH ₄ ⁺ having a nitrogen atom as the ion center, and an organic anion. In particular it includes organic cations and organic anions. As used herein, the term "organic" is meant to include carbon and hydrogen as elements.

Examples of cations derived from component (A) include ammonium cations (NH ₄ ⁺ , primary ammonium cations, secondary ammonium cations, tertiary ammonium cations), guanidinium cations, and imidazolium cations, although not particularly limited. pyridinium cation, pyrrolidinium cation, piperidinium cation, pyrrolinium catine, pyrazinium cation, triazolium cation, isoquinolinium cation, oxazolinium cation, thiazolinium cation, morpholinium cation, pyrimidinium cation cations derived from cyclic amines such as nium cations, piperazinium cations, triazinium cations, quinolinium cations, indolinium cations, quinoxalinium cations, isoxazolium cations, and cationic amino acids. be done. Among these, ammonium cation, imidazolium cation, pyridinium cation, pyrrolidinium cation, piperidinium cation, and morpholinium cation are preferred, and ammonium cation is more preferred.

The cation of the organic ammonium salt formed by the component (A) and the component (B) is preferably a cation represented by the following formula (III). Moreover, when the component (A) is an ammonium compound, its cation is also preferably a cation represented by the following formula (III).

(In the formula, each R ⁵ independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R ⁶ is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and o represents an integer of 0 to 4.)

In the above formula (III), o is preferably an integer of 1-4.

In formula (III), all R ⁶ are preferably hydrogen atoms.

In the above formula (III), in the hydroxy hydrocarbon group, the hydrocarbon in the hydrocarbon moiety that may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.

In formula (III), at least one of R ⁵ has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. is preferred.

In the above formula (III), at least one of R ⁵ has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. Preferably.

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

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

A combination of at least one of the above preferred examples shown in formula (III) can be a more preferred embodiment.

In the antibacterial agent of the present invention, component (B) is a carboxylic acid or its salt. The carboxylic acid is an organic acid having at least one carboxy group (--COOH) in the molecule, and has an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, a hydrocarbon group, and the like. may be Although not particularly limited, the carboxylic acid includes, for example, a saturated or unsaturated aliphatic hydrocarbon group, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, etc., and a hydrocarbon group combining them. those having a carboxy group, such as 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, carbonylcarboxylic acids, alkyl ether carboxylic acids, halogen carboxylic acids, etc. (the number of carbon atoms in the carboxylic acids listed below is carboxy group of carbon.).

The saturated aliphatic carboxylic acid is composed of 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 having one carboxy group and saturated aliphatic dicarboxylic acids having two carboxy groups.
The saturated aliphatic monocarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms. Specifically, but 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, pentadecyl acid, palmitic acid , margaric acid, stearic acid, arachidic acid, henicosyl acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid and the like.
The saturated aliphatic dicarboxylic acid is composed of 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.

The unsaturated aliphatic carboxylic acid is composed of 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 having one carboxy group and unsaturated aliphatic dicarboxylic acids having two carboxy groups.
The unsaturated aliphatic monocarboxylic acid is composed of a linear or branched unsaturated aliphatic hydrocarbon group and one carboxy group, and preferably has 1 to 22 carbon atoms.
Specifically, but not particularly limited, for example, acrylic acid, methacrylic acid, crotonic acid, octenoic acid, nonenoic acid, decenoic acid, undecenoic acid, undecylenic acid, dodecenoic acid, tridecenoic acid, tetradecenoic acid, myristoleic acid, pentadecene acid, hexadecenoic acid, palmitoleic acid, sapienic acid, heptadecenoic acid, octadecenoic acid, oleic acid, elaidic acid, vaccenic acid, nonadecenic acid, icosenoic acid, gadoleic acid, henicosenoic acid, docosenoic acid, erucic acid, octadienoic acid, nonadienoic acid, Decadienoic acid, undecadienoic acid, dodecadienoic acid, tridecadienoic 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 acid, eleostearic acid, nonadecatrienoic acid, icosatrienoic acid, mead acid, dihomo-γ-linolenic acid, henicosatrienoic acid, docosatrienoic acid, decatetraenoic acid, undecatetraenoic acid, dodecatetraenoic acid, tridecatetraene 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, tetradecapentaenoic acid, pentadecapentaenoic acid, hexadecapentaenoic acid Enoic acid, heptadecapentaenoic acid, octadecapentaenoic acid, boseopentaenoic acid, nonadecapentaenoic acid, icosapentaenoic acid, henicosapentaenoic acid, docosapentaenoic acid, sardine acid, tridecahexaenoic acid, tetradecahexaenoic acid , pentadecahexaenoic acid, hexadecahexaenoic acid, heptadecahexaenoic acid, octadecahexaenoic acid, boseohexaenoic acid, nonadecahexaenoic acid, icosahexaenoic acid, henicosahexaenoic acid, docosahexaenoic acid, and the like. .
The unsaturated aliphatic dicarboxylic acid is composed of a linear or branched unsaturated aliphatic hydrocarbon group and two carboxy groups, preferably having 1 to 22 carbon atoms.
Specific examples include, but are not particularly limited to, maleic acid and fumaric acid.

The saturated or unsaturated alicyclic carboxylic acid is composed of a saturated or unsaturated carbocyclic ring having no aromaticity and one or more carboxy groups, and preferably has 6 to 20 carbon atoms. Among them, a saturated alicyclic carboxylic acid having a cyclohexane ring skeleton is preferred.
Saturated or unsaturated alicyclic carboxylic acids include saturated or unsaturated alicyclic monocarboxylic acids having one carboxy group and saturated or unsaturated alicyclic dicarboxylic acids having two carboxy groups.
Examples of the saturated or unsaturated alicyclic monocarboxylic acid include, but are not particularly limited to, cyclohexanecarboxylic acid.
Examples of the saturated or unsaturated alicyclic dicarboxylic acid include, but are not particularly limited to, cyclohexanedicarboxylic acid, tetrahydrophthalic acid, and the like.

The aromatic carboxylic acid is composed of a single ring or a plurality of aromatic rings and one or more carboxylic acids, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acids having a benzene ring skeleton are preferred.
Examples of aromatic carboxylic acids include aromatic monocarboxylic acids having one carboxy group, aromatic dicarboxylic acids having two carboxy groups, and aromatic tricarboxylic acids having three carboxy groups.
Examples of aromatic monocarboxylic acids include, but are not limited to, benzoic acid, cinnamic acid, toluic acid, xyllic acid, hemellitic acid, mesitylene acid, prenityl acid, mesitic acid, cumic acid, anisic acid, and veratrum acid. mentioned.
Examples of the aromatic dicarboxylic acid include, but are not limited to, phthalic acid, isophthalic acid, terephthalic acid, and the like.
Examples of the aromatic tricarboxylic acid include, but are not limited to, trimesic acid, hemimellitic acid, and trimellitic acid.

The saturated aliphatic hydroxycarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 2 to 24 carbon atoms. Among them, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and having 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. The number of hydroxyl groups is preferably 1-5. Specifically, but not limited to, for example, glycolic acid, lactic acid, glyceric acid, hydroxyacetic acid, hydroxybutyric acid, 2-hydroxydecanoic acid, 3-hydroxydecanoic acid, 12-hydroxystearic acid, dihydroxystearic acid, cerebronic acid , leucic acid, mevalonic acid, pantoic acid, gluconic acid, galactonic acid, mannonic acid, arabinonic acid, fructuronic acid, tagaturonic acid, aldonic acid and the like.
The saturated aliphatic hydroxydicarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, two carboxy groups and one or more hydroxyl groups, and preferably has 4 to 24 carbon atoms. Among them, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and having 1 to 4 hydroxyl groups are preferred. Specific examples include, but are not particularly limited to, tartronic acid, malic acid, tartaric acid, citramalic acid, and the like.
The saturated aliphatic hydroxytricarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, three carboxy groups and one or more hydroxyl groups, and preferably has 4 to 24 carbon atoms. Among them, saturated aliphatic hydroxycarboxylic acids having 2 to 7 carbon atoms and having 1 to 4 hydroxyl groups are preferred. Specific examples include, but are not particularly limited to, citric acid, isocitric acid, and the like.

The unsaturated aliphatic hydroxycarboxylic acid is composed of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 3 to 22 carbon atoms. Specific examples include, but are not particularly limited to, ricinoleic acid, ricinoleic acid, ricineraidic acid, and the like.

The saturated or unsaturated alicyclic hydroxycarboxylic acid comprises a saturated or unsaturated carbocyclic ring having no aromaticity, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 4 to 20 carbon atoms. . Among them, saturated alicyclic hydroxycarboxylic acids having a 6-membered ring skeleton having 1 to 4 hydroxyl groups are preferable, and specifically, although not particularly limited, examples include hydroxycyclohexanecarboxylic acid, dihydroxycyclohexanecarboxylic acid, quinic acid ( 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid), shikimic acid, glucuronic acid, galacturonic acid, mannuronic acid, iduronic acid, guluronic acid and the like. A cyclic lactone having a hydroxyl group can also be preferably used, and specific examples thereof include, but are not limited to, ascorbic acid and erythorbic acid.

The aromatic hydroxycarboxylic acid is composed of an aromatic single ring or multiple rings, one or more carboxyl groups and one or more hydroxyl groups, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acids having a benzene ring skeleton having 1 to 5 hydroxyl groups are preferred, and specific examples include, but are not limited to, salicylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, and hydroxymethyl. Benzoic acid, vanillic acid, syringic acid, protocatechuic acid, gentisic acid, orceric acid, mandelic acid, benzilic acid, atrolactic acid, phloretic acid, coumaric acid, umberic acid, caffeic acid, ferulic acid, sinapic acid, cresotic acid, chlorogen acid, rosmarinic acid and the like.

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

The alkyl ether carboxylic acid is a carboxylic acid having 2 to 22 carbon atoms and having an ether group in the molecule, including a polyoxyalkylene alkyl ether carboxylic acid, and a carboxylic acid having 2 to 12 carbon atoms and having 1 to 2 ether groups. Alkyl carboxylic acids are preferred. Specific examples include, but are not particularly limited to, methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid, and the like.

As the halogen carboxylic acid, a halogen carboxylic acid having 2 to 22 carbon atoms is preferable. Specifically, but not particularly limited, for example, trifluoroacetic acid, trichloroacetic acid, tribromoacetic acid, pentafluoropropionic acid, pentachloropropionic acid, pentabromopropionic acid, perfluorononanoic acid, perchlorononanoic acid, perbromonanoic acid, etc. and halogen-substituted halogen carboxylic acids.

Examples of the carboxylic acid salt in component (B) include salts of the above carboxylic acid anions and cations (alkali metal cations, alkaline earth metal cations, ammonium cations, etc.).

Among the carboxylic acids or salts thereof of component (B), carboxylic acids are preferred, and carboxylic acids having a carboxy group and a hydroxyl group are more preferred from the viewpoint of antibacterial properties, and those having two or more carboxy groups and a hydroxyl group are preferred. More preferred. A carboxylic acid having a hydroxyl group is one of the preferred embodiments in terms of affinity with organic materials and inorganic materials.

In addition, from the viewpoint of safety and use, component (B) is specified in the Standards for Quasi-drug Ingredients (Quasi-drugs Ingredients), Standards for Quasi-drugs Additives, Japanese Pharmacopoeia (Japanese Pharmacopoeia), Japanese Pharmacopoeia It is preferable to use compounds listed in the Standards for Quasi-Drugs (Regulations), Standards for Pharmaceutical Additives (Medicine Additives), and Food Additives Standards (Food Additives) as raw materials. 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 etc. and salts thereof.

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

In the antibacterial agent of the present invention, the blending molar ratio of component (A) and 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, still more preferably 1:3 to 3:1, particularly preferably 1:2 to 2:1, most preferably 1:1.

In particular, when the component (B) is a polybasic acid, the blending of the component (A) and the component (B) is such that the valence of the component (A) is equal to or less than the valence of the component (B). (When the component (B) is a polybasic acid, it may be a partially neutralized salt or a completely neutralized salt.), preferably less than equivalent in terms of antibacterial performance.

For example, when component (B) is a dibasic acid and component (A) has a valence of 1, the blending molar ratio of component (A) and component (B) can be 1:1 mol to 2:1 mol. can. Two or more kinds of components (A) may be used. From the point of view of antibacterial performance, it is preferable to use an unneutralized carboxyl group, and the molar ratio of component (A) to component (B) is preferably 1:1.

On the other hand, in terms of antibacterial performance, the ratio of the total number of amino groups to the total number of carboxy groups (total number of amino groups / total number of carboxy groups) of components (A) and (B) is less than 1. is preferably

When component (A) and component (B) form an organic ammonium salt, in addition to the carboxylate group generated by the dissociation of hydrogen ions from the carboxy group of component (A) or component (B), it participates in the formation of the salt. Component (A) or component (B) preferably has one or more carboxy groups that do not participate in salt formation, and more preferably component (B) has one or more carboxy groups that do not participate in salt formation.

In the antibacterial agent of the present invention, a mixture of component (A) and component (B) or a salt of component (A) and component (B) may be in an anhydrous state (anhydrous), and can absorb moisture in the air. It may be an absorbed hydrate. A hydrate refers to a compound that, when left in the air at 25°C, absorbs water and has a saturated moisture content. Compounds that do not absorb water when left in air at 25° C. are non-hydrated and anhydrous.

The antibacterial agent of the present invention is a mixture of components (A) and (B) or a salt of (A) and (B), anhydrides and hydrates at 25 ° C. Whether liquid or solid However, for example, if it is liquid at 25 ° C., it will remain as a liquid when the solvent evaporates after spraying or applying the liquid containing the antibacterial agent of the present invention to the part to be used, and the effect will be exhibited in a wide range, and crystals will precipitate. There are no problems in use such as coagulation or agglomeration and solidification. Moreover, when it is liquid at 25° C., it can be used as a solvent or base having antibacterial properties when used with other additives. From these points of view, the anhydride and/or hydrate are preferably liquid at 25°C.

The surface of the object on which the antibacterial agent of the present invention is used has functional groups that interact and bond with hydrogen-bonding functional groups such as oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and metals. In this case, it interacts and bonds with the hydrogen-bonding functional groups of component (A) and/or component (B), and the antibacterial agent of the present invention adheres well to the object for a long time and can exhibit its effect. be.

As a preferred embodiment of the combination of component (A) and component (B), from the viewpoint of antibacterial properties and safety, component (A) is preferably a saturated aliphatic compound having one or more linear or branched hydroxy groups. An amine compound having a hydrocarbon group, more preferably a monohydroxyalkyl group or a polyhydroxyalkyl group having 1 to 6 carbon atoms, more preferably triethanolamine, 2-amino-2-hydroxymethyl-1, 3-propanediol, 2-amino-2-ethyl-1,3-propanediol, and component (B) is preferably a saturated aliphatic hydroxycarboxylic acid (lactic acid, malic acid, citric acid, tartaric acid, etc.) and more preferably saturated aliphatic hydroxy di- or tricarboxylic acids (malic acid, citric acid, tartaric acid, etc.).
As a preferred embodiment of the combination of component (A) and component (B), component (A) is a saturated aliphatic hydrocarbon having one or more linear or branched hydroxy groups from the viewpoint of antibacterial properties and safety. It is an amine compound having a group, and component (B) is a saturated aliphatic hydroxycarboxylic acid (lactic acid, malic acid, citric acid, tartaric acid, etc.).
As a preferred embodiment of the combination of component (A) and component (B), component (A) is an amine having a monohydroxyalkyl group or a polyhydroxyalkyl group having 1 to 6 carbon atoms from the viewpoint of antibacterial properties and safety. compound, component (B) is a saturated aliphatic hydroxy di- or tricarboxylic acid (malic acid, citric acid, tartaric acid, etc.).
In a preferred embodiment of the combination of component (A) and component (B), component (A) is triethanolamine, 2-amino-2-hydroxymethyl-1,3-propane from the viewpoint of antibacterial properties and safety. diol or 2-amino-2-ethyl-1,3-propanediol and component (B) is malic acid, citric acid or tartaric acid.

When the antibacterial agent of the present invention is a salt of components (A) and (B), it is preferable from the viewpoint of maintaining the antibacterial effect over a long period of time without volatilizing even in a low-humidity environment.

The form of the antibacterial agent is not particularly limited, but can be, for example, liquid, solid, gel, or cream.

The antibacterial agent of the present invention may contain a solvent and other components in addition to components (A) and (B). Examples of solvents include, but are not limited to, 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, acetonitrile, etc. These may be used alone, You may use it in combination of 2 or more types.

(Antibacterial composition, antiviral composition)
The antibacterial composition or antiviral composition of the present invention is obtained by adding the antibacterial agent of the present invention explained above.

The antibacterial composition or antiviral composition of the present invention can be produced by mixing the antibacterial agent of the present invention, in which the components (A) and (B) have been blended in advance, with a solvent, other ingredients, etc. Others include blending components (A) and (B) prior to making the antimicrobial composition.

The properties of the antibacterial composition of the present invention are not particularly limited, but may be, for example, liquid, solid, gel, or the like. can do. The form of the antibacterial composition is not particularly limited, but examples thereof include a solution obtained by diluting the components (A) and (B) in a solvent, a mixture with other components, and the like. Additives and the like added at the time of production of these, and solvents such as existing antibacterial agents, antiviral agents, disinfectants, and the like can be mentioned.

The antibacterial composition or antiviral composition of the present invention contains the antibacterial agent of the present invention as an essential ingredient, and other ingredients may be added to the extent that the effects of the present invention are not impaired.
Other ingredients are not particularly limited, but for example, the above solvents, existing antibacterial agents other than the antibacterial agent of the present invention, antiviral agents, bacteria such as disinfectants, agents having an effect on viruses, surfactants ( anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc.), resins, UV absorbers (including organic and inorganic), fragrances, moisturizers, metal oxides , neutralizers, pH adjusters, coloring agents, antioxidants, corrosion inhibitors, rust inhibitors, metal deactivators, antifoaming agents and the like. These may be used individually by 1 type, and may be used in combination of 2 or more type.

The content of components (A) and (B) in the antibacterial composition or antiviral composition of the present invention is not particularly limited, but is, for example, 1 to 100% by mass relative to the total amount of the composition, or 10 to 90% by mass.

These organic ammonium salts are non-volatile, and liquid compounds in particular can be uniformly coated in a high-concentration state after the volatile components evaporate, providing effective and long-lasting antibacterial properties. In addition, it also exerts an effect as a solvent for drugs that are effective against bacteria and viruses, such as existing antibacterial agents, antiviral agents, and disinfectants. As a result, existing antibacterial agents, antiviral agents, disinfectants, etc. can be blended at higher concentrations. In addition, even a solid drug can be maintained in a dissolved state and uniformly coat the surface of the object. Therefore, in addition to the antibacterial properties of the antibacterial agent of the present invention, it is possible to sufficiently exhibit the effects of existing antibacterial agents, antiviral agents, disinfectants, and the like. Furthermore, a synergistic effect can be expected between the formulation of the present invention and existing antibacterial agents, antiviral agents, and disinfectants, and antibacterial and antiviral properties can be obtained at lower concentrations.

Examples of the existing antibacterial agents include, but are not limited to, paraoxybenzoic acid esters such as methylparaben and sodium salts thereof, benzoic acid and salts thereof, salicylic acid and salts thereof, sorbic acid and salts thereof, dehydroacetic acid and salts thereof, Chlorcresol, resorcinol, pantothenyl ethyl benzoate, isopropylmethylphenol (cymen-5-ol), cetylpyridinium chloride, photosensitizer, phenol, sodium lauryldiaminoethylglycinate, benzalkonium chloride, benzethonium chloride, chlorhexidine and its salts , orthophenylphenol and its salts, chloroxylenol, chlorphenesin, alkylisoquinolinium bromide, thianthol, thymol, trichlorocarbanilide, parachlorophenol, halocarbane, hinokitiol, zinc pyrithione, piroctone olamine, butyl Carbamate propynyl iodide polyaminopropyl biguanide, methylisothiazolinone, paradimethylaminostyrylheptylmethylthiazolium iodide, β-lactam antibiotics (penicillins, cephems, carbapenems, monobactams, penems), aminoglycosides antibiotics, lincomycin antibiotics, fosfomycin antibiotics, tetracycline antibiotics, chloramphenicol antibiotics, macrolide antibiotics, ketolide antibiotics, polypeptide constituents, glycopeptide antibiotics, Examples include streptogramin antibiotics, quinolone antibiotics, sulfa drugs, oxazolidinone antibiotics, and the like. The drug effective against viruses is not particularly limited, but examples include sodium linear alkylbenzene sulfonate, alkyl glycoside, alkylamine oxide, benzalkonium chloride, benzethonium chloride, dialkyldimethylammonium chloride, polyoxyethylene alkyl ether, Fatty acid potassium, fatty acid sodium, chlorhexidine gluconic acid, polyhexamethylene biguanide, o-phthalaldehyde (phthalal), glutaraldehyde (glutaral), povidone iodine, sodium hypochlorite, peracetic acid and the like.

The amount of the above-mentioned existing antibacterial agents, antiviral agents, antiseptics, 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. However, it can be 0.01% to 10% by weight of the antibacterial composition, and the weight ratio with the antibacterial agent of the present invention can be 1:99 to 99:1.

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

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 without departing from the scope of the invention. In addition, each of the above preferred examples shown in formula (I), each of the above preferred examples shown in formula (II), and each of the above preferred examples shown in formula (III) are at least any of them. Any combination can be a more preferable embodiment based on the results of the examples. At least one combination of all of the above preferred examples shown in formulas (I) to (III) can be a more preferred embodiment based on the results of the examples. Also, combinations of them with the respective preferred examples shown above for anions, and further combinations thereof with the properties of mixtures of components (A) and (B) or salts of (A) and (B) Or, furthermore, a combination of each of them and preferable examples of the polymer compound can be a more preferable embodiment based on the results of the examples.

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

The following reagents and the like were used for minimum inhibitory concentration (MIC) measurement and halo test.
Staphylococcus aureus strain NBRC15035: NITE
Potassium lactate: Medium manufactured by Fujifilm Wako Pure Chemicals Muller-Hinton broth: Medium manufactured by Becton, Dickinson and Company L-Dried product restoration medium "Daigo": Calcium chloride manufactured by Fujifilm Wako Purechemicals: Magnesium chloride manufactured by Fujifilm Wako Pure Chemicals : Fuji Film Wako Pure Chemical Sodium Chloride : Fuji Film Wako Pure Chemical Skim Milk : Snow Brand Megmilk Meat Extract : Solabia Biokar Diagnostics Peptone : Solabia Biokar Diagnostics Sodium Chloride : Fuji Film Wako Pure Chemical Agar : Fuji Film Wako Pure Chemical Made

1. Preparation of formulations (salts) The formulations (salts) of Examples 1 to 8 and 21 to 43 were prepared by the method described in JP 2019-023185, and the state at 25 ° C. was confirmed (Tables 1A to 1D). .

2. Antibacterial evaluation 1 (minimum inhibitory concentration) of formulation (salt)
Examples 1 to 8, 21 to 43, Comparative Examples 1, 8, and 9 shown in Tables 1A to 1D, 2A, and 2B for Staphylococcus aureus minimal inhibitory concentrations (MIC) were measured by the microdilution method (Japanese Society of Chemotherapy standard (described in the law) to confirm the antibacterial activity of various compounds (salts). Formulation (salt) concentrations of 250, 200, 150, 100, 50, 25, 12.5, 8, 4, 2, 0.8, 0.4, 0.2, 0.1, 0.05 mg/mL were evaluated and the MICs are shown in Tables 1A-1D. A lower MIC value indicates better antibacterial activity.

From the results in Tables 1A to 1D, Examples 1 to 8 and 21 to 43 exhibited higher antibacterial properties 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 could not inhibit bacterial growth even in the test at a concentration of 250 mg/mL. When comparing the formulations of the same component (B) of Examples 1, 2, 6 and Comparative Examples 1, 8, Examples 1, 2, 6 having a hydrogen-bonding functional group (hydroxyl group) in Component (A) It was confirmed to have high antibacterial properties. Further, when comparing Example 1 with Examples 21 and 22, Example 2 with Examples 3 and 5, and Example 6 with Examples 7 and 8 of the same component (A), the carboxylate group in component (B) When comparing Examples 3 and 7 of the same component (B), the compound (salt) of component (A) in which R ⁷ in the above formula is an alkyl group is It tended to be highly antibacterial.

3. Antibacterial evaluation 2 of compound (salt) (halo test 1)
A halo test was performed using Staphylococcus aureus with reference to JISL1902. Filter paper for Kiriyama funnel (manufactured by Kiriyama Seisakusho) of 21 φm / m was used as a test piece, and the filter paper was placed on the medium containing the bacterial cells, and the formulation (salt) aqueous solution (execution Examples 9 to 11 and Comparative Examples 2 to 4) were added dropwise at 100 μL. After that, culture was performed, and the presence or absence of halos was visually confirmed, and the presence or absence of halos is shown in Tables 2A and 2B.

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

4-2. Hello test 2
Using Staphylococcus aureus with reference to JISL1902, sterilize in advance and 4-1. A halo test was performed using a filter paper as a test piece, which was vacuum-dried at 60.degree. After the test, the presence or absence of halos was visually confirmed, and the presence or absence of halos is shown in Tables 2A and 2B.

　From the results of the halo test 1, ethanol, which is widely known for its bactericidal and antibacterial effects, volatilized during culture and could not demonstrate any antibacterial effects, and no halo was observed. On the other hand, halos were observed in the formulations of the examples. It was suggested that the compound of the present invention is non-volatile, so that it does not volatilize while adhering to the filter paper and can exhibit antibacterial effects for a long period of time.

In the halo test 2, ethanol volatilized and did not adhere to the filter paper. Even after drying, it was confirmed that antibacterial properties persist for a long period of time due to non-volatility.

5. 50% by mass aqueous solution of the formulation (salt) shown in Tables 3A and B (Examples 12 to 18, Comparative Example 5 is a 50% by mass aqueous solution of potassium lactate, Comparative Example 6 is water only), 4-methylparaben (manufactured by Tokyo Kasei, hereinafter referred to as paraben), which is a poorly water-soluble antibacterial agent, is dissolved at 1.0, 0.5, 0.25% by mass at 80 ° C., and an antibacterial composition was prepared. After that, it was allowed to stand at 25° C. for 24 hours under closed conditions, and the appearance of each antibacterial composition was visually confirmed, and the solubility was evaluated according to the following criteria (Table 3A, B).
◎: 1.0% by mass or more, no crystal precipitation, transparent dissolution ○: 0.5% by mass or more and less than 1.0% by mass, no crystal precipitation, transparent dissolution △: 0.25% by mass or more, less than 0.5% by mass, crystal precipitation None, transparent dissolution ×: Less than 0.25% by mass Crystal precipitation or cloudiness

Polyoxyethylene alkyl ether (manufactured by Miyoshi Oil & Fat Co., Ltd.: Peletex 2465), alkyl glycoside (manufactured by Tokyo Chemical Industry Co., Ltd.: n-octyl β-D-glucopyranoside), benzalco chloride, which is an antiviral substance that is recognized to be effective against viruses (manufactured by Nacalai Tesque: benzalkonium chloride), benzethonium chloride (manufactured by Tokyo Chemical Industry: benzethonium chloride), and o-phthalaldehyde (manufactured by Fuji Film Wako Pure Chemical: phthalaldehyde). was evaluated for solubility (Table 3A, B).

The formulation (salt) of the present invention dissolves sparingly water-soluble antibacterial agents and other antiviral substances well, resulting in an antibacterial composition. When comparing Examples 13 to 14 and Examples 16 to 18 of the same component (B), it was confirmed that the compound (salt) of component (A) in which R ⁷ in the above formula is an alkyl group tends to have a higher solubility in parabens. did.

6. Antibacterial evaluation of antibacterial composition (minimum inhibitory concentration)
Examples 19 and 20 prepared so as to contain the same amounts of the formulations of components (A) and (B) shown in Tables 4A and B and paraben, respectively, and Comparative Example 8 containing only paraben were prepared in 2. above. In the same test method as above, the paraben concentration of 1.0 mg / mL (the antibacterial composition of Examples 19 and 20 is a total of 2.0 mg / mL of antibacterial agents) was evaluated, and the presence or absence of bacterial growth The presence or absence was evaluated.

1 mg/mL of the parabens or the formulations (salts) of Comparative Example 1 and Reference Examples 1 and 2 alone do not exhibit antibacterial properties, but the parabens and the formulations (salts) are mixed at 1 mg/mL each to give a total of 2 mg/mL. Examples 19 and 20, which were antibacterial compositions, showed antibacterial properties as a composition because the antibacterial effect of paraben was added to the antibacterial effect of the formulation (salt).

In other words, by adding another additive to the formulation (salt) of the present invention, the effect of the additive can be imparted to the composition containing the formulation (salt) of the present invention. The composition obtained by adding (dissolving) the antiviral substance in (1) is endowed with antiviral properties in addition to antibacterial properties.

7. Stability Evaluation of Antibacterial Composition Dissolve paraben (additive) in 50% by weight aqueous solution of Formulation 4 or 8 and water to give a 0.25% by weight solution and place in a sample bottle with an open top. and allowed to stand at 50° C. for 48 hours. After the test, the appearance of each antibacterial composition was visually confirmed.

When only water was used, the water evaporated and paraben crystals precipitated. On the other hand, in the 50% by mass aqueous solution of Formulation 4 or 8, the liquid did not completely evaporate, and no crystal precipitation was observed. It maintains the solubility of the agent and has good stability, and the effects of the compound (salt) and additives can be efficiently exhibited for a long period of time.

8. Sustainability evaluation of antibacterial composition 300 μL of each compound (salt) was applied to an unsterilized 21 φm / m filter paper for Kiriyama funnel, placed in a petri dish with the upper part open, and placed in a room with active people coming and going for 1 week. left undisturbed. 3. Place the coated surface in contact with the agar medium. was placed on an agar medium having the same composition as that used in 1. and cultured at 37° C. for one day. The backing paper was removed, culture was carried out at 37° C. for one day, and growth of the bacteria was confirmed visually.
Example 44: 50 wt% tromethamine/citric acid (Formulation No. 4) aqueous solution Comparative Example 10: Water Comparative Example 11: 70 wt% ethanol (Formulation No. 10) aqueous solution

Comparing Example 44 with Comparative Examples 10 and 11, growth of bacteria was not observed in Example 44, but growth of bacteria was confirmed in Comparative Examples 10 and 11. Further, when comparing Comparative Examples 10 and 11, it was confirmed that Comparative Example 10 proliferated a larger amount of cells.
In Comparative Example 10, it was confirmed that the bacteria that had originally adhered to the filter paper and the bacteria that had adhered to the filter paper during the standing period proliferated, and in Comparative Example 11, the bacteria that had adhered to the filter paper were inactivated by the bactericidal action of ethanol. , it is considered that the adhered bacterial cells were confirmed after ethanol volatilization. On the other hand, in Example 44, since the composition of the present invention was non-volatile, the composition adhered to the paper after water evaporation in a high-concentration state, and the antibacterial effect was maintained. Conceivable.
Therefore, it was suggested that the composition of the present invention is non-volatile, so that it does not volatilize while adhering to the filter paper and can exhibit antibacterial effects for a long period of time.

Claims

An antimicrobial agent which is a blend of components (A) and (B) below.
(A) an amine or ammonium compound having a hydrogen-bonding functional group (excluding amino acids);
(B) carboxylic acid or salt thereof
2. The component (A) has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched, and the hydrocarbon moiety has a hydroxyhydrocarbon group which may contain an oxygen atom. Antibacterial agent according to.
The component (A) has the following formula (I) or (II):

(In the formula, each R 1 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R 2 independently represents a hydrogen atom or an organic group having 1 to 22 carbon atoms, and m represents an integer of 0 to 3.)

(In the formula, each R 3 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R 4 independently represents a hydrogen atom or an organic group having 1 to 22 carbon atoms, n represents an integer of 0 to 4, and X − represents an anion.)
The antibacterial agent according to claim 1 or 2, represented by.
The antibacterial agent according to claim 3, wherein m is an integer of 1 to 3 in the formula (I), and n is an integer of 1 to 4 in the formula (II).
5. The antibacterial agent according to claim 3 or 4, wherein in formula (I), all R2 are hydrogen atoms, and in formula (II), all R4 are hydrogen atoms.
In the formula (I), at least one of R 1 has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. ,
In the formula (II), at least one of R 3 has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. The antibacterial agent according to any one of claims 3-5.
In the above formula (I), at least one of R 1 has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. can be,
In the formula (II), at least one of R 3 has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. The antibacterial agent according to any one of claims 3-5.
In the formula (I), at least one of R 1 has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom. is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group,
In the formula (II), at least one of R 3 has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom. is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.
The antibacterial agent according to any one of claims 3 to 8, wherein in formula (II), X - is a hydroxide ion.
The antibacterial agent according to any one of claims 3 to 8, wherein the component (A) is represented by the formula (I).
With a cation derived from the component (A) according to any one of claims 1 to 10, which may have a cationic residue of the component (B) according to any one of claims 1 to 10 and an antibacterial agent containing an organic ammonium salt formed by an anion derived from the anionic residue of component (B).
The antibacterial agent according to claim 11, wherein the cation is an ammonium cation.
The cation of the organic ammonium salt formed by the component (A) and the component (B) has the following formula (III):

(In the formula, each R 5 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom. represents a good hydroxy hydrocarbon group, each R 6 independently represents a hydrogen atom or an organic group having 1 to 22 carbon atoms, and o represents an integer of 0 to 4. Antibacterial agent as described.
The antibacterial agent according to claim 13, wherein o is an integer of 1 to 4 in the formula (III).
15. The antibacterial agent according to claim 13 or 14, wherein in formula (III), all R6 are hydrogen atoms.
In formula (III), at least one of R 5 has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. The antibacterial agent according to any one of claims 13-15.
In the above formula (III), at least one of R 5 has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group. The antibacterial agent according to any one of claims 13-15.
In the formula (III), at least one of R 5 has one or more hydroxyl groups, the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom. is a hydroxy hydrocarbon group of a saturated aliphatic hydrocarbon.
When at least one of R 6 of the cation represented by the formula (III) is a hydrogen atom, the proton corresponding to the hydrogen atom is derived from the component (B). Antibacterial agent as described.
The antibacterial agent according to any one of claims 1 to 19, wherein the component (B) is a carboxylic acid.
The antibacterial agent according to any one of claims 1 to 20, wherein component (B) is a carboxylic acid having a hydroxyl group and a carboxy group in the hydrocarbon moiety.
The ratio of the total number of amino groups to the total number of carboxy groups (total number of amino groups/total number of carboxy groups) of said component (A) and said component (B) is less than 1. The antibacterial agent according to any one of the clauses.
23. Any one of claims 1 to 22, wherein the mixture of components (A) and (B) or the salt of (A) and (B) is an anhydride and/or hydrate liquid at 25°C. Antibacterial agent according to.
An antibacterial composition to which the antibacterial agent according to any one of claims 1 to 23 is added.
An antiviral composition to which the antibacterial agent according to any one of claims 1 to 23 is added.