JP2001302415A - Antimicrobial agent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain both an antimicrobial agent composition having a large effect and a slight influence on the human skin and an antimicrobial composition, in use in combination with an antimicrobial agent having strong irritation, capable of reducing the concentration of the antimicrobial agent having storing irritation and controlling irritation without decreasing its antimicrobial properties. SOLUTION: This antimicrobial agent comprises an amino acid derivative such as ethylenediamine-N,N-diacetic acid, N,N'-dilauroylethylenediamine-N,N'- diacetic acid, ehylenediamine-N,N'-disuccinic acid, etc., or its salt as a component (a); or comprises the component (a) and a cationic surfactant, an isothiocyanic acid ester, hinokitiol or the like as a component (b); or comprises the component (a), the component (b) and (S)-aspartic acid-N-acetate, (S)-aspartic acid-N,N-diacetate or the like as a component (c).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antibacterial agent composition, and more particularly to a compound having a high antibacterial activity and having an action of alleviating irritation when used in combination with an antibacterial agent having strong irritation.

[0002]

2. Description of the Related Art Conventionally, antibacterial agents for tableware and cooking utensils, disinfectants for cooks' hands, refrigerators and the like, alcohols, chlorine-based and oxygen-based agents, cationic antibacterial agents and isothiocyanate And hinokitiol were known. However, these antibacterial agents have been limited in use, amount and frequency of use due to their irritation. Cationic surfactants represented by benzalkonium salts are known to show excellent bactericidal activity, but benzalkonium salts and benzethonium chloride show irritation to eyes and skin at a certain concentration or more. Therefore, its use concentration and use frequency are limited.

[0003] Alcohols such as methanol, ethanol and propanol are said to have low antibacterial effects, and in order to obtain a sufficient effect, it is necessary to use a concentrated solution. I can't. Oxygen-based chemicals such as hydrogen peroxide and percarbonate are suitable for bleaching tableware and clothes, but have a low antibacterial effect, and thus need to be used in large amounts. Chlorine drugs such as sodium hypochlorite
Although it has a certain antibacterial effect, there is a problem that a pungent odor remains. These drugs have a large effect on human skin.
Isothiocyanate esters such as allyl isothiocyanate and hinokitiol are also commonly used germicides, but have a strong pungent odor and are difficult to handle.

[0004] In order to improve the above-mentioned disadvantage, Japanese Patent Application Laid-Open No.
JP-A-53504, JP-A-10-53507, JP-A-11-116406 and JP-A-11-302104 disclose adding an amino acid-N, N-diacetate derivative to a benzalkonium salt without reducing the antibacterial property. Methods for reducing the concentration of benzalkonium salts are described. JP-A-11-130608 and JP-A-11-130609 describe that an isothiocyanate and a ferrous salt are contained. Japanese Patent Application Laid-Open No. 9-136992 discloses a method in which chitosan is used as a base material and hinokitiol is added thereto. However, these methods have not been able to completely suppress strong irritating odors and irritation to the skin.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides an antibacterial agent composition having a large antibacterial effect and a small effect on human skin. An object of the present invention is to provide an antibacterial agent composition in which the concentration is reduced without lowering the antibacterial property and the irritation is suppressed.

[0006]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that an amino acid derivative represented by the following general formula (1) or a salt thereof has antibacterial properties, The present inventors have found that the antibacterial action can be increased without increasing the irritation of other antibacterial agents, and that the use concentration can be reduced, and the present invention has been completed.

[0007]

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[Wherein, R ^a and R ^b are the same or different and each is hydrogen or a straight-chain or branched-chain alkyl, alkenyl or acyl group having 1 to 24 carbon atoms which may be substituted by a hydroxyl group; A ^a and ^Ab are the same or different and each have a linear or branched carbon number of 1 to 6 which may be substituted by a hydroxyl group, a carboxyl group, a phenyl group or an amino group.
Wherein Y ^a and Y ^b are the same or different and each represent a carboxyl group or a sulfonic acid group, and W represents a linear or branched carbon number of 1 to 1 which may be substituted by a hydroxyl group or a carboxyl group. 6 represents an alkylene group. ]

That is, the present invention is characterized in that an antimicrobial composition comprising at least one compound selected from the amino acid derivatives represented by the general formula (1) or salts thereof as the component (a). An antimicrobial composition is provided.

[0010]

Embodiments of the present invention will be described below in detail. In the antimicrobial composition of the present invention, (a)
As the component, at least one selected from amino acid derivatives represented by the following general formula (1) or salts thereof is used.

[0011]

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Wherein R ^a and R ^b are the same or different and are hydrogen or a straight-chain or branched-chain alkyl, alkenyl or acyl group which may be substituted by a hydroxyl group; A ^a and ^Ab are the same or different and each have a linear or branched carbon number of 1 to 6 which may be substituted by a hydroxyl group, a carboxyl group, a phenyl group or an amino group.
Wherein Y ^a and Y ^b are the same or different and each represent a carboxyl group or a sulfonic acid group, and W represents a linear or branched carbon number of 1 to 1 which may be substituted by a hydroxyl group or a carboxyl group. 6 represents an alkylene group. ]

Specific examples of the linear or branched alkyl or alkenyl group having 1 to 24 carbon atoms which may be substituted on the hydroxyl group represented by R ^a or R ^b include the following. it can.

Examples of the linear alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, Henicosyl, docosyl, tricosyl and tetracosyl, and examples of the branched alkyl group include methylhexyl, ethylhexyl, methylheptyl, ethylheptyl, methylnonyl, methylundecyl, methylheptadecyl, hexyldecyl and octyldecyl. Can be mentioned.

Examples of the linear alkenyl group include ethenyl, propenyl, butenyl, pentenyl, hexenyl,
Heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl,
Examples include pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, icosenyl, henicocenyl, docosenyl, tricosenyl, tetracosenyl, and the like. Examples include groups such as enyl, methylheptadecenyl, hexyldecenyl, octyldecenyl and the like. Of these, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, decyl,
Undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, methylhexyl, ethylhexyl, methylheptyl, ethylheptyl, methylnonyl, methylundecyl, methylheptadecyl, hexyldecyl, octyldecyl, etc., and further methyl, ethyl, propyl , Butyl, hexyl, heptyl,
Groups such as octyl, nonyl, decyl, undecyl, dodecyl, methylhexyl, ethylhexyl and the like are preferred.

The above linear or branched alkyl group may be substituted with a hydroxyl group, a carboxyl group, a phenyl group or an amino group. The substitution position of the hydroxyl group, carboxyl group, phenyl group or amino group is not particularly limited.

From the viewpoint of the bacteriostatic effect when used as an antibacterial agent, R ^a and R ^b have a linear or branched carbon number of 1 to 4 which may be substituted by a hydroxyl group, a carboxyl group or a phenyl group. Preferred are 18 alkyl or alkenyl groups. More preferably, a 2-hydroxyethyl group,
n-nonanoyl, n-decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl.

[0018] In the general formula (1), A ^a, hydroxyl group represented by A ^b, a carboxyl group, a phenyl group or an alkylene group having 1 to 6 carbon atoms which may straight or branched chain optionally substituted amino group As methylene, ethylene, trimethylene, propylene, tetramethylene, pentamethylene,
Hexamethylene, 2-hydroxytrimethylene, 1-carboxyethylene, 2-carboxyethylene and the like can be mentioned. Among these, an alkylene group having 1 to 3 carbon atoms which may be substituted by a hydroxyl group or a carboxyl group,
Further, the hydroxyl group may have 1 to 3 carbon atoms.
And particularly preferably an unsubstituted alkylene group having 1 to 3 carbon atoms. A ^a and ^Ab may be the same or different. Y ^a, Y ^b are the same or different, are each a carboxyl group or a sulfonic acid group.

Examples of the linear or branched alkylene group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group or a carboxyl group represented by W include ethylene, trimethylene, propylene, tetramethylene, pentamethylene,
Hexamethylene, 2-hydroxytrimethylene and the like can be mentioned. Among these, an unsubstituted alkylene group having 2 to 6 carbon atoms, particularly ethylene, is preferred. Y ^a and Y ^b are the same or different and each represent a carboxyl group or a sulfonic acid group.

When the amino acid derivative represented by the general formula (1) has one or more asymmetric carbon atoms, some optical isomers may exist. Any of the isomers can be used alone or as a mixture. However, from the viewpoint of the effect on the environment, the structure of the amino acid moiety is excellent in biodegradability.
Body placement is preferred.

The amino acid derivative represented by the general formula (1) can be produced according to a known method, for example, by reacting a diamine with a halide, an olefin compound or the like. Here, specific examples of the diamine include ethylenediamine, propylenediamine, trimethylenediamine, pentamethylenediamine, hexamethylenediamine, and 2-hydroxytrimethylenediamine. Specific examples of the halide include chloroacetic acid, bromoacetic acid, sodium chloroacetate, sodium bromoacetate, sodium chloropropionate, sodium bromopropionate, 2-chloroethanol, and 3-chloropropanol. Specific examples of the olefin compound include maleic acid, fumaric acid, methyl maleate, methyl fumarate, ethyl maleate, ethyl fumarate, methyl acrylate, ethyl acrylate, acrylonitrile, propyl fumarate, and the like.

The amino acid derivative represented by the general formula (1) can also be produced by a method such as reacting a dihalide or the like with an amino acid. Here, specific examples of the dihalide include dichloroethane, dibromoethane, dichloropropane, dibromopropane, dichlorobutane, dibromobutane, and the like. Specific examples of amino acids include alanine, valine, leucine, isoleucine, threonine, phenylalanine, glycine,
Serine, threonine, tyrosine, histidine, lysine,
Arginine, aspartic acid, glutamic acid and the like. Further, the amino acid derivative synthesized by the above method is
A substituent may be added by a known method. Known methods include alkylation using halides such as butyl bromide, acylation using fatty acid halides such as lauroyl chloride and acid anhydrides such as maleic anhydride,
Addition of a hydroxyethyl group using chlorohydrin such as chloroethanol.

Examples of the amino acid derivative represented by the general formula (1) include ethylenediamine-N, N'-diacetic acid,
N, N'-bis (2-hydroxyethyl) ethylenediamine-N, N'-diacetic acid, N, N'-di (n-nonanoyl) ethylenediamine-N, N'-diacetic acid, N, N'-
Di (n-decanoyl) ethylenediamine-N, N′-diacetate, N, N′-dilauroylethylenediamine-N,
N'-diacetic acid, N, N'-dimyristoylethylenediamine-N, N'-diacetic acid, N, N'-dipalmitoylethylenediamine-N, N'-diacetic acid, N, N'-distearoylethylenediamine-N , N'-diacetic acid, N,
N′-dioleoylethylenediamine-N, N′-diacetic acid, ethylenediamine-N, N′-disuccinic acid, N,
N′-bis (2-hydroxyethyl) ethylenediamine-N, N′-disuccinic acid, N, N′-di (n-nonanoyl) ethylenediamine-N, N′-disuccinic acid, N,
N'-di (n-decanoyl) ethylenediamine-N,
N′-disuccinic acid, N, N′-dilauroylethylenediamine-N, N′-disuccinic acid, N, N′-dimyristoylethylenediamine-N, N′-disuccinic acid, N,
N'-dipalmitoylethylenediamine-N, N'-disuccinic acid, N, N'-distearoylethylenediamine-N, N'-disuccinic acid, N, N'-dioleoylethylenediamine-N, N'-disuccinic acid, Ethylenediamine-N, N'-dipropionic acid, N, N'-bis (2-
(Hydroxyethyl) ethylenediamine-N, N′-dipropionic acid, N, N′-di (n-nonanoyl) ethylenediamine-N, N′-dipropionic acid, N, N′-di (n-decanoyl) ethylenediamine-N , N'-dipropionic acid, N, N'-dilauroylethylenediamine-N, N'-dipropionic acid, N, N'-dimyristoylethylenediamine-N, N'-dipropionic acid, N,
N'-dipalmitoylethylenediamine-N, N'-dipropionic acid, N, N'-distearoylethylenediamine-N, N'-dipropionic acid, N, N'-dioleoylethylenediamine-N, N'-di Propionic acid, ethylenediamine-N, N'-diglutaric acid, N, N'-
Bis (2-hydroxyethyl) ethylenediamine-N,
N'-diglutaric acid, N, N'-di (n-nonanoyl)
Ethylenediamine-N, N'-diglutaric acid, N, N '
-Di (n-decanoyl) ethylenediamine-N, N'-
Diglutaric acid, N, N′-dilauroylethylenediamine-N, N′-diglutaric acid, N, N′-dimyristoylethylenediamine-N, N′-diglutaric acid, N,
N'-dipalmitoylethylenediamine-N, N'-diglutaric acid, N, N'-distearoylethylenediamine-N, N'-diglutaric acid, N, N'-dioleoylethylenediamine-N, N'-diglutaric acid; Ethylenediamine-N, N'-bis-2-ethanesulfonic acid,
N, N′-bis (2-hydroxyethyl) ethylenediamine-N, N′-bis-2-ethanesulfonic acid,
N'-di (n-nonanoyl) ethylenediamine-N,
N'-bis-2-ethanesulfonic acid, N, N'-di (n
-Decanoyl) ethylenediamine-N, N'-bis-2
-Ethanesulfonic acid, N, N'-dilauroylethylenediamine-N, N'-bis-2-ethanesulfonic acid,
N, N'-dimyristoylethylenediamine-N, N '
-Bisethanesulfonic acid, N, N'-palmitoylethylenediamine-N, N'-bis-2-ethanesulfonic acid, N, N'-distearoylethylenediamine-N,
N'-bis-2-ethanesulfonic acid, N, N'-dioleoyl-ethylenediamine-N, N'-bisethanesulfonic acid, trimethylenediamine-N, N'-diacetic acid,
N, N'-di-2-hydroxyethyl-trimethylenediamine-N, N'-diacetate, N, N'-di-n-nonanoyl-trimethylenediamine-N, N'-diacetic acid,
N'-di (n-decanoyl) trimethylenediamine-
N, N'-diacetate, N, N'-dilauroyltrimethylenediamine-N, N'-diacetate, N, N'-dimyristoyltrimethylenediamine-N, N'-diacetic acid, N,
N'-dipalmitoyl trimethylenediamine-N, N '
-Diacetate, N, N'-distearoyl trimethylenediamine-N, N'-diacetate, N, N'-dioleoyltrimethylenediamine-N, N'-diacetate, trimethylenediamine-N, N '-Disuccinic acid, N, N'-bis (2-
(Hydroxyethyl) trimethylenediamine-N, N'-
Disuccinic acid, N, N′-di (n-nonanoyl) trimethylenediamine-N, N′-disuccinic acid, N, N′-di (n-decanoyl) trimethylenediamine-N, N′-
Disuccinic acid, N, N'-dilauroyltrimethylenediamine-N, N'-disuccinic acid, N, N'-dimyristoyltrimethylenediamine-N, N'-disuccinic acid, N,
N'-dipalmitoyl trimethylenediamine-N, N '
-Disuccinic acid, N, N'-di-stearoyl trimethylene diamine-N, N'-disuccinic acid, N, N'-dioleoyl trimethylene diamine-N, N'-disuccinic acid,
Trimethylenediamine-N, N'-dipropionic acid,
N, N'-bis (2-hydroxyethyl) trimethylenediamine-N, N'-dipropionic acid, N, N'-di (n-nonanoyl) trimethylenediamine-N, N'-
Dipropionic acid, N, N′-di (n-decanoyl) trimethylenediamine-N, N′-dipropionic acid, N,
N'-dilauroyltrimethylenediamine-N, N'-
Dipropionic acid, N, N'-dimyristoyl trimethylene diamine-N, N'-dipropionic acid, N, N'-dipalmitoyl trimethylene diamine-N, N'-dipropionic acid, N, N'-di Stearoyl trimethylenediamine-N, N'-dipropionic acid, N, N'-dioleoyltrimethylenediamine-N, N'-dipropionic acid, trimethylenediamine-N, N'-diglutaric acid,
N, N'-bis (2-hydroxyethyl) trimethylenediamine-N, N'-diglutaric acid, N, N'-di (n
-Nonanoyl) trimethylenediamine-N, N'-diglutaric acid, N, N'-di (n-decanoyl) trimethylenediamine-N, N'-diglutaric acid, N, N'-dilauroyltrimethylenediamine-N , N'-Diglutaric acid, N, N'-Dimiristoyltrimethylenediamine-
N, N'-diglutaric acid, N, N'-dipalmitoyl trimethylenediamine-N, N'-diglutaric acid,
N'-distearoyl trimethylenediamine-N, N '
-Diglutaric acid, N, N'-dioleoyl trimethylenediamine-N, N'-diglutaric acid, trimethylenediamine-N, N'-bis-2-ethanesulfonic acid, N,
N'-bis (2-hydroxyethyl) trimethylenediamine-N, N'-bis-2-ethanesulfonic acid, N,
N'-di (n-nonanoyl) trimethylenediamine-
N, N'-bisethanesulfonic acid, N, N'-di (n-
Decanoyl) trimethylenediamine-N, N'-bis-
2-ethanesulfonic acid, N, N'-dilauroyltrimethylenediamine-N, N'-bis-2-ethanesulfonic acid, N, N'-dimyristoyltrimethylenediamine-
N, N'-bis-2-ethanesulfonic acid, N, N'-dipalmitoyl trimethylenediamine-N, N'-bis-
2-ethanesulfonic acid, N, N'-distearoyl trimethylenediamine-N, N'-bis-2-ethanesulfonic acid, N, N'-dioleoyltrimethylenediamine-
N, N'-bis-2-ethanesulfonic acid and the like can be mentioned.

From the viewpoint of the bacteriostatic effect when used as an antibacterial agent, ethylenediamine-N, N'-diacetic acid,
N, N'-dilauroylethylenediamine-N, N'-
Diacetic acid, N, N'-distearoylethylenediamine-
N, N'-diacetic acid, ethylenediamine-N, N'-disuccinic acid, N, N'-bis (2-hydroxyethyl) ethylenediamine-N, N'-disuccinic acid, N, N'-dilauroylethylenediamine-N , N'-disuccinic acid,
N, N'-distearoylethylenediamine-N, N '
-Disuccinic acid, ethylenediamine-N, N'-diglutaric acid, ethylenediamine-N, N'-bis-2-ethanesulfonic acid, trimethylenediamine-N, N'-disuccinic acid. More preferably, ethylenediamine-N, N'-diacetic acid, N, N'-dilauroylethylenediamine-N, N'-diacetic acid, N, N'-, which are excellent in biodegradability.
Distearoylethylenediamine-N, N'-diacetic acid,
(S, S) -ethylenediamine-N, N'-disuccinic acid, (S, S) -N, N'-bis (2-hydroxyethyl) ethylenediamine-N, N'-disuccinic acid, (S,
S) -N, N'-dilauroylethylenediamine-N,
N′-disuccinic acid, (S, S) -N, N′-distearoylethylenediamine-N, N′-disuccinic acid, (S,
S) -ethylenediamine-N, N'-diglutaric acid and ethylenediamine-N, N'-bis-2-ethanesulfonic acid.

The amino acid derivative represented by the general formula (1) includes a carboxyl group (-COOH) and a sulfonic acid group (-
(SO ₃ H), it can form salts with various cations. Such salts include, for example, alkali metal salts, alkaline earth metal salts, heavy metal salts, amine salts, basic amino acid salts, ammonium salts and the like. Specifically, sodium, potassium, lithium, magnesium,
Examples include salts with calcium, silver, copper, zinc, tin, chromium, titanium, nickel, cobalt, trimethylamine, triethylamine, tributylamine, monoethanolamine, diethanolamine, triethanolamine, lysine, arginine, choline, ammonia, and the like. The above salts may be used as a mixture, or may contain a plurality of cations in one molecule. These salts may be partially neutralized salts. Among these salts, there are salts with metals having high antibacterial action such as silver, but they can be used without any problem as long as the irritation of the antibacterial agent composition is not increased. Among these, lithium, sodium, potassium, ammonia, silver, copper, zinc, tin, or chromium salts are preferred. Further, these salts may be partially neutralized salts.

In the antimicrobial composition of the present invention, an antimicrobial agent other than the component (a) can be used in combination as the component (b).
Examples of the antibacterial agent of the component (b) include alcohols such as methanol, ethanol, and propanol; cationic surfactants such as benzalkonium salts and benzethonium chloride; isothiocyanates such as allyl isothiocyanate;
Examples include natural extract antibacterial agents such as hinokitiol and chitosan. Among them, cationic surfactants are preferable, and at least one compound selected from antibacterial agents represented by the following general formula (2) is more preferable. Examples of the antibacterial agent represented by the general formula (2) include a benzalkonium salt and benzethonium chloride.

[0027]

Embedded image

(Wherein R ¹ , R ² , R ³ and R ⁴ are the same or different and each have 1 to 24 carbon atoms which may have an ether bond, an aromatic ring, a heterocyclic ring, a carboxyl group or an amino group) Represents a linear or branched alkyl group, and X ⁻ represents an anion.)

The antimicrobial composition of the present invention may contain, in addition to the above components, an anionic, amphoteric or nonionic surfactant for the purpose of imparting cleaning performance. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkenyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbite fatty acid ester, alkyl polyglycoside, sucrose fatty acid ester, and alkyl polyglycerin ether. No.

The amount of the amino acid derivative represented by the general formula (1) or a salt thereof in the composition of the present invention is 0.005.
The effect is exhibited at 40% by weight, but is preferably 0.05 to 10% by weight, more preferably 0.1 to 2% by weight when used. The ratio of the antibacterial agent to the amino acid derivative represented by the general formula (1) or a salt thereof is preferably 2 times or less, more preferably 0.2 to 2 times, particularly preferably 0.5 to 1 time. The above composition may be diluted with a solvent such as water and used after adjusting to a working concentration.

In the antibacterial agent composition of the present invention, (S) -aspartic acid-N-acetic acid, (S) -aspartic acid-N, N-diacetic acid, (S) -aspartic acid- N-propionic acid, (S, S) -iminodisuccinic acid,
(S, R) -iminodisuccinic acid, (S) -aspartic acid-N-methanesulfonic acid, (S) -aspartic acid-
N-2-ethanesulfonic acid, (S) -glutamic acid-
N, N-diacetate, (S) -glutamic acid-N-methanesulfonic acid, (S) -glutamic acid-N-2-ethanesulfonic acid, (S) -α-alanine-N, N-diacetic acid,
The antibacterial property is increased by adding at least one selected from the group consisting of (S) -serine-N, N-diacetate, (S) -phenylalanine-N, N-diacetate and salts thereof. Is possible. The amount of addition is preferably 0.05 to 50 times, more preferably 0.1 to 10 times, the mole of the component (a).

The chelating agent of the component (c) has the general formula (1)
In the same manner as the amino acid derivative represented by
COOH), since having a sulfonic acid group (-SO ₃ H), can form salts between the various cations. Such salts include, for example, alkali metal salts, alkaline earth metal salts, heavy metal salts, amine salts, basic amino acid salts, ammonium salts and the like. Specifically, sodium, potassium, lithium, magnesium, calcium, silver, copper,
Examples include salts with zinc, tin, chromium, titanium, nickel, cobalt, trimethylamine, triethylamine, tributylamine, monoethanolamine, diethanolamine, triethanolamine, lysine, arginine, choline, ammonia and the like. The above salts may be used as a mixture, or may contain a plurality of cations in one molecule. These salts may be partially neutralized salts. Among these salts, there are salts with metals having high antibacterial action such as silver, but they can be used without any problem as long as the irritation of the antibacterial agent composition is not increased. Among these, lithium,
Sodium, potassium, ammonia, silver, copper, zinc, tin, chromium or chromium salts are preferred. Further, these salts may be partially neutralized salts.

The antimicrobial composition of the present invention may contain, in addition to the above components, an anionic, amphoteric or nonionic surfactant for the purpose of imparting cleaning performance. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkenyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbite fatty acid ester, alkyl polyglycoside, sucrose fatty acid ester, and alkyl polyglycerin ether. No.

The antimicrobial composition of the present invention may further contain other additives, if necessary, such as a pH adjuster, a thickener, a thickener, an emulsifier, a chelating agent, a builder, a solvent, a fragrance, a humectant, and the like. Colorants, inorganic salts, dispersants, enzymes, reducing agents, bleaching agents, fluorescent dyes, solubilizers, anti-caking agents, enzyme activators, antioxidants, preservatives, pigments, enzyme stabilizers, penetrants An organic solvent deodorant, a flameproofing agent, an anticorrosion, a fertilizer, a building material, and the like can be appropriately compounded within a range that does not impair the effects of the present invention.

The antimicrobial composition of the present invention may optionally contain
Porous microparticles can be added. As the porous fine particles in this case, crystalline silicate such as zeolite, diatomaceous earth, clay such as bentonite, silica, alumina,
Examples include metal oxides such as magnesium oxide, titania, alumina, and zirconia.

The antimicrobial composition of the present invention can be used in the form of a solution, a slurry, an emulsified state, a solid, or the like, depending on its use.

The antimicrobial composition of the present invention can be used for various objects such as fibers, metals, glass, resins, ceramics, skin, and hair. Further, it may be kneaded into a polyolefin resin such as polyethylene or polypropylene, or a synthetic fiber such as polyester to form an antibacterial resin or an antibacterial / deodorant fiber.

[0038]

EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples.

Examples 1 to 15 and Comparative Examples 1 to 4 The antibacterial compositions shown in Table 2 were prepared using the compounds shown in Table 1 in the following manner, and were subjected to a halo test and a patch test to show antibacterial properties and skin irritation. Were compared. Table 3 shows the results.

[Hello Test] Preparation of Sample for Halo Test 150 pieces of 2 cm × 2 cm cotton broad (raw cloth, undyed cloth) were immersed in 25 g of an antibacterial composition having the composition shown in Table 1 at room temperature for 10 minutes. Then, after centrifugal dehydration for 1 minute, the treated cloth pressed and dried at 140 ° C. for 30 seconds was used as a test sample for the halo test.

2. Preparation of bacterial solution 10 g of peptone, 5 g of beef extract, 5 g of sodium chloride
Was dissolved in 1 liter of distilled water and adjusted to pH 6.8 with 2N-NaOH to prepare a culture solution. This culture solution 1
0 ml was dispensed into a test tube and sterilized at 120 ° C. and 1 atm for 20 minutes. The strain was transplanted to this, and cultured at 37 ° C. for 24 hours to prepare a bacterial solution.

3. 1. Preparation of bacterial inoculated agar medium To 980 ml of the culture solution not used in the section, 1.5% by mass of the agar based on the culture solution was added and sufficiently dissolved. Next, it sterilized at 120 degreeC and 1 atm for 20 minutes.
After cooling to 45 ° C., 1 ml of the bacterial solution was inoculated into the cooled solution to prepare a bacterial inoculated agar culture solution. The bacterial inoculated agar culture was dispensed into a petri dish to prepare a bacterial inoculated agar medium.

4. Halo test The sample for the halo test was gently pressed onto the agar medium inoculated with the bacteria, and attached. After affixing, agar-inoculated agar medium was added to 37
C. for 24 hours. After the culture, the width of the inhibition zone around the test piece was measured from the back through the bottom of the petri dish. Depending on the presence or absence of Staphylococcus aureus growth around the sample for halo test,
That is, the antibacterial activity was evaluated by the halo width (mm number) formed around the sample. The larger the value of the halo width means the greater the antibacterial activity, and 0 for a blank.

5. Bacterial species used Two types of Staphylococcus aureus and Bacillus subtilis were used in this test.

[Patch Test] An upper arm closed patch test was conducted for 20 subjects using a 5% by weight aqueous solution of a surfactant for 5 days. Judgment was made based on the number of people with abnormalities such as redness and rash after the test.

<Judgment Criteria> ：: Abnormal redness, rash, etc. 0: ○: Abnormality of redness, rash, etc. 1: △: Abnormality of redness, rash, etc. 2: ×: Redness, rash, etc. 3 More than

[0047]

[Table 1]

* In the general formula (2), R ¹ = C ₁₂ H
^{_{25 ~C 14 H 29, R 2}} , R 3 = CH 3, R 4 = CH 2 -C 6 H 5,
X ^- = Cl ^- compound (average molecular weight 354) ** benzyl dimethyl {2- [2- (p-1,1,3 ,
3-tetramethylbutylphenoxy) ethoxy] ethyl} ammonium chloride

[0049]

[Table 2]

[0050]

[Table 3]

[0051]

From the above test results, the antibacterial agent composition of the present invention has a high antibacterial activity even when the amino acid derivative represented by the above general formula (1) is used alone, and can be used in combination with a highly irritating antibacterial agent. It has an effect of improving antibacterial activity and relaxing irritation. Further, (S) -aspartic acid-N-acetic acid, (S) -aspartic acid-N, N-diacetic acid, (S) -aspartic acid-N-propionic acid,
(S, S) -iminodisuccinic acid, (S, R) -iminodisuccinic acid, (S) -aspartic acid-N-methanesulfonic acid, (S) -aspartic acid-N-2-ethanesulfonic acid, (S)- Glutamic acid-N, N-diacetic acid, (S)
-Glutamic acid-N-methanesulfonic acid, (S) -glutamic acid-N-2-ethanesulfonic acid, (S) -α-alanine-N, N-diacetic acid, (S) -serine-N, N-diacetic acid By adding at least one selected from the group consisting of (S) -phenylalanine-N, N-diacetic acid and salts thereof, it is possible to obtain a higher antibacterial property without increasing irritation. .

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 35/06 A01N 35/06 43/16 43/16 A 47/46 47/46 59/00 59/00 A 59/08 59/08 A 63/00 63/00 A

Claims (7)

[Claims] 1. An antimicrobial composition comprising as component (a) at least one compound selected from the group consisting of an amino acid derivative represented by the following general formula (1) and a salt thereof. Embedded image [Wherein, R ^a and R ^b are the same or different and each may be a straight-chain or branched-chain alkyl, alkenyl, or acyl group having 1 to 24 carbon atoms which may be substituted with hydrogen or a hydroxyl group;
A ^a and ^Ab are the same or different and each have a hydroxyl group,
A carboxyl group, a phenyl group or an amino group represents a linear or branched alkylene group having 1 to 6 carbon atoms which may be substituted, and Y ^a and Y ^b are the same or different, and represent a carboxyl group or a sulfonic acid group, respectively. W represents a linear or branched alkylene group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group or a carboxyl group. ] 2. The component (a) according to claim 1, further comprising (b) an alcohol, a chlorine-based or oxygen-based drug, a cationic surfactant, an isothiocyanate, hinokitiol and chitosan. An antibacterial agent composition comprising at least one antibacterial agent selected from the group. 3. The antimicrobial composition according to claim 2, wherein the antimicrobial agent of the component (b) is a cationic surfactant. 4. The antibacterial agent of the component (b) is represented by the following general formula (2)
The antibacterial agent composition according to claim 2, which is an antibacterial agent represented by the formula: Embedded image (Wherein, R ¹ , R ² , R ³ , and R ⁴ are the same or different and each have a linear chain having 1 to 24 carbon atoms which may have an ether bond, an aromatic ring, a heterocyclic ring, a carboxyl group, or an amino group. or branched chain alkyl group, X ^- represents an anion). 5. Further, as the component (c), (S) -aspartic acid-N-acetic acid and (S) -aspartic acid-
N, N-diacetic acid, (S) -aspartic acid-N-propionic acid, (S, S) -iminodisuccinic acid, (S, R)-
Iminodisuccinic acid, (S) -aspartic acid-N-methanesulfonic acid, (S) -aspartic acid-N-2-ethanesulfonic acid, (S) -glutamic acid-N, N-diacetate, (S) -glutamic acid- N-methanesulfonic acid,
(S) -glutamic acid-N-2-ethanesulfonic acid,
(S) -α-alanine-N, N-diacetate, (S) -serine-N, N-diacetate, (S) -phenylalanine-N,
At least one chelating agent selected from the group consisting of N-diacetate and salts thereof is added to component (a) in an amount of 0.05
The antibacterial agent composition according to any one of claims 1 to 4, wherein the amount of the antibacterial agent is from 50 to 50 times the molar amount. 6. The salt of the amino acid derivative represented by the general formula (1) according to claim 1, wherein the salt is a lithium, sodium, potassium, ammonia, silver, copper, zinc, tin, or chromium salt. The antibacterial composition according to any one of claims 1 to 5. 7. The amino acid derivative represented by the general formula (1) according to claim 1 and a salt thereof are ethylenediamine-
N, N'-diacetate, S, S-ethylenediamine-N,
N'-disuccinic acid, S, S-ethylenediamine-N,
The compound is at least one compound selected from N'-diglutaric acid, derivatives thereof, and salts thereof.
The antibacterial agent composition according to any one of claims 6 to 6.