WO2022225049A1 - Agent antibactérien, et composition antibactérienne ainsi que composition antivirale mettant en œuvre celui-ci - Google Patents

Agent antibactérien, et composition antibactérienne ainsi que composition antivirale mettant en œuvre celui-ci Download PDF

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Publication number
WO2022225049A1
WO2022225049A1 PCT/JP2022/018557 JP2022018557W WO2022225049A1 WO 2022225049 A1 WO2022225049 A1 WO 2022225049A1 JP 2022018557 W JP2022018557 W JP 2022018557W WO 2022225049 A1 WO2022225049 A1 WO 2022225049A1
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group
acid
hydrocarbon
formula
antibacterial agent
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PCT/JP2022/018557
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English (en)
Japanese (ja)
Inventor
亜紀良 矢下
大介 中村
和馬 竹腰
恒太郎 金子
功治 河合
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ミヨシ油脂株式会社
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Priority to JP2023515539A priority Critical patent/JPWO2022225049A1/ja
Publication of WO2022225049A1 publication Critical patent/WO2022225049A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to an antibacterial agent and an antibacterial composition and an antiviral composition using the same.
  • 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.
  • 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.
  • the antibacterial agent of the present invention is characterized by being a blend of the following components (A) and (B).
  • 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 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.
  • 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.
  • amine, imidazole, pyridine, pyrrolidine, piperidine, morpholine are preferred, and amines are more preferred.
  • these may contain substituents described in the section [Substituents] below.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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,
  • 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,
  • 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-y
  • the saturated or unsaturated alicyclic hydrocarbon group is preferably a saturated alicyclic hydrocarbon group and is not particularly limited.
  • 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-hepty
  • divalent hydrocarbon groups examples include groups obtained by removing one hydrogen atom from the above groups.
  • substituents examples 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.
  • hydrocarbon group examples include those listed in the above [hydrocarbon group].
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • a hydrogen atom directly bonded to nitrogen constitutes 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.
  • 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.
  • 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.
  • 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.
  • the hydroxy hydrocarbon group has one or more hydroxyl groups
  • 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.
  • 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.
  • 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.
  • 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 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-hydroxymethyl group, 2-hydroxybutan-2
  • the saturated aliphatic hydrocarbon group having two or more hydroxy groups is not particularly limited, and examples thereof include di-, tri-, tetra-, penta-, hexa-, hepta-, and octahydroxyalkyl groups. .
  • 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-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.
  • dihydroxyethyl groups such as 1,2-dihydroxyethyl group; 1,2-
  • 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-dihydroxy
  • 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.
  • 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
  • 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.
  • component (A) has a monohydroxyalkyl group
  • triethanolamine and diethanolamine are preferred, and triethanolamine is particularly preferred.
  • 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.
  • triethanolamine 2- Amino-2-hydroxymethyl-1,3-propanediol is more preferred.
  • one of the moieties in component (A) into which a functional group can be introduced is The above may be substituted with an organic group that does not have a hydrogen-bonding functional group.
  • 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.
  • 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.
  • component (A) is preferably an amine compound represented by the following formula (I).
  • 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.
  • m is preferably an integer of 1-3.
  • R 2 are preferably hydrogen atoms.
  • the hydrocarbon in the hydrocarbon moiety that may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.
  • 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.
  • 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.
  • the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
  • 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.
  • a combination of at least one of the above preferred examples shown in formula (I) can be a more preferred embodiment.
  • 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.
  • 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.
  • 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.
  • component (A) is an ammonium compound
  • said component (A) is preferably an ammonium compound represented by the following formula (II).
  • 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.
  • the anion represented by X ⁇ is preferably a hydroxide ion.
  • n is preferably an integer of 1-4.
  • R 4 are preferably hydrogen atoms.
  • the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.
  • 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.
  • 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 hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
  • the hydrocarbon in the hydrocarbon moiety which may contain an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
  • 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.
  • 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.
  • 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).
  • 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.
  • 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.
  • 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.
  • the acid of component (B) is a compound composed of protonated hydrogen and an anionic residue.
  • the organic ammonium salt includes an organic cation or NH 4 + having a nitrogen atom as the ion center, and an organic anion.
  • organic includes organic cations and organic anions.
  • organic is meant to include carbon and hydrogen as elements.
  • 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.
  • ammonium cation 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).
  • 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.
  • o is preferably an integer of 1-4.
  • R 6 are preferably hydrogen atoms.
  • the hydrocarbon in the hydrocarbon moiety that may contain an oxygen atom is preferably a saturated aliphatic hydrocarbon.
  • 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.
  • 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 hydrocarbon in the hydrocarbon moiety optionally containing an oxygen atom is a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • aromatic dicarboxylic acid include, but are not limited to, phthalic acid, isophthalic acid, terephthalic acid, and the like.
  • 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.
  • 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.
  • 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. .
  • 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.
  • 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.
  • 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.
  • carboxylic acid salt in component (B) examples include salts of the above carboxylic acid anions and cations (alkali metal cations, alkaline earth metal cations, ammonium cations, etc.).
  • carboxylic acids or salts thereof of component (B) 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.
  • 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).
  • 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.
  • 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).
  • 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.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.).
  • 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.).
  • 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.
  • component (B) is a saturated aliphatic hydroxy di- or tricarboxylic acid (malic acid, citric acid, tartaric acid, etc.).
  • 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.
  • 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).
  • 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 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.
  • 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.
  • 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.
  • existing antibacterial agents, antiviral agents, disinfectants, etc. can be blended at higher concentrations.
  • 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.
  • 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, hinokitio
  • 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.
  • 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.
  • 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
  • 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). .
  • 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.
  • 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
  • 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 ⁇ L. 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.
  • Adhesion evaluation and antibacterial evaluation 3 (halo test 2) of formulation (salt) 4-1.
  • Adhesion Evaluation 100 ⁇ L of the compound (salt) aqueous solution (Examples 9 to 11) having the concentration shown in Tables 2A and 2B was dropped onto a 21 ⁇ m/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).
  • 100 ⁇ L of water was dropped onto the filter paper and the filter paper was dried in a vacuum.
  • Weight of attached sample weight of filter paper after drying (mg) - weight of filter paper before test (mg) + correction value (1.15 mg)
  • Polyoxyethylene alkyl ether manufactured by Miyoshi Oil & Fat Co., Ltd.: Peletex 2465
  • alkyl glycoside manufactured by Tokyo Chemical Industry Co., Ltd.: n-octyl ⁇ -D-glucopyranoside
  • benzalco chloride which is an antiviral substance that is recognized to be effective against viruses
  • Nacalai Tesque benzalkonium chloride
  • benzethonium chloride manufactured by Tokyo Chemical Industry: benzethonium chloride
  • o-phthalaldehyde manufactured by Fuji Film Wako Pure Chemical: phthalaldehyde
  • the formulation (salt) of the present invention dissolves sparingly water-soluble antibacterial agents and other antiviral substances well, resulting in an antibacterial composition.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.

Abstract

L'invention fournit un nouvel agent antibactérien hautement sûr et présentant des effets durables, une composition antibactérienne, et une composition antivirale.　L'agent antibactérien de l'invention consiste en un mélange des composants (A) et (B) suivants : (A) composé ammonium ou amine (à l'exclusion d'un acide aminé) possédant un groupe fonctionnel de liaison hydrogène ; et (B) acide carboxylique ou sel de celui-ci.
PCT/JP2022/018557 2021-04-23 2022-04-22 Agent antibactérien, et composition antibactérienne ainsi que composition antivirale mettant en œuvre celui-ci WO2022225049A1 (fr)

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JPS5198324A (en) * 1975-02-25 1976-08-30 Satsukin shodoku oyobi bofusoseibutsu
JPS5296734A (en) * 1976-02-05 1977-08-13 Tokyo Yuuki Kagaku Kougiyou Kk Nonnmedical expellent for noxious organism
JPH08511543A (ja) * 1993-06-09 1996-12-03 ロンザ インコーポレイテッド 第四級アンモニウム及び防水／防腐剤組成物
JPH1143405A (ja) * 1996-06-25 1999-02-16 Sanyo Chem Ind Ltd 低刺激性繊維用抗菌加工処理剤
JP2003081709A (ja) * 2001-09-13 2003-03-19 Asahi Denka Kogyo Kk 殺菌消毒液組成物及び殺菌消毒材
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JP2014019659A (ja) * 2012-07-13 2014-02-03 Niitaka:Kk 消毒液及び消毒方法
JP2015071589A (ja) * 2013-09-09 2015-04-16 吉田製薬株式会社 消毒剤
JP2017528463A (ja) * 2014-09-09 2017-09-28 ロンザ インコーポレーテッド 四級アンモニウム化合物を含有する消毒組成物
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JP2022058054A (ja) * 2020-09-30 2022-04-11 シーバイエス株式会社 皮膚消毒剤組成物

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