JP2007291049A - Antimicrobial agent and antimicrobial composition containing it - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a highly safe antimicrobial agent having a comparable or better antimicrobial activity to that of paraben and favorable sense of use as a cosmetic, and an antimicrobial composition with reinforced antimicrobial activity containing it. <P>SOLUTION: The antimicrobial agent comprises compounds shown by general formula(e) (1) and/or (2) wherein R and R' each independently represent a hydrogen atom or a 1-4C alkyl group, R" represents a 1-3C alkylene group and n represents a numeral of 0 or 1. The antimicrobial composition contains it/them with reinforced antimicrobial activity. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a novel antibacterial agent having antibacterial properties equivalent to or better than parabens, high safety, and excellent usability, and an antibacterial composition containing the same.

  Antibacterial agents are often used in cosmetics and cleaning agents for the purpose of preserving. Parabens are the most used as these antibacterial agents, but parabens have the disadvantage that the concentration range of use is limited due to high skin irritation and low safety, so in cosmetics The use concentration of parabens is limited to 1% or less. Recently, an increasing number of people have an allergic reaction to parabens, and the demand for cosmetics not containing parabens has increased.

Therefore, it is known to use alkanediols, alkyl glyceryl ethers and alkylene oxide adducts of alkanediol as antibacterial agents (see, for example, Patent Documents 1, 2, and 3). However, although these antibacterial agents are higher in safety to the human body than parabens, when actually used as cosmetics, some people may feel that the usability is poor.
Japanese Patent Laid-Open No. 11-322591 JP 51-76424 A JP 54-49322 A

  Therefore, the problem to be solved by the present invention is to improve the antibacterial agent and antibacterial agent having antibacterial properties equivalent to or better than parabens, high safety, and good usability when actually used as cosmetics. Another object is to provide an antibacterial composition.

  Accordingly, the present inventors diligently studied and found an antibacterial agent having antibacterial properties equivalent to or higher than parabens, high safety, and excellent usability, and led to the present invention. That is, the present invention provides the following general formula (1) and / or (2)

(In the formula, R and R ′ each represent an independent hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R ″ represents an alkylene group having 1 to 3 carbon atoms, and n represents a number of 0 or 1. It is an antibacterial agent consisting of a compound represented by

  The effect of the present invention is an antibacterial agent having antibacterial properties equivalent to or better than parabens, high safety, good usability when actually used as a cosmetic, and an antibacterial composition with improved antibacterial properties. It is in providing.

  The antibacterial agent of the present invention is a compound represented by the above general formula (1) and / or (2). In the general formulas (1) and (2), R and R ′ each represent an independent hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a tertiary butyl group. Among these substituents, a hydrogen atom or an alkyl group having 1 to 2 carbon atoms is preferable, a hydrogen atom or a methyl group is more preferable, and a hydrogen atom is still more preferable because of good antibacterial properties. R and R ′ may be the same or different, but one of them is preferably a hydrogen atom and more preferably a hydrogen atom because of good antibacterial properties.

  In general formulas (1) and (2), R ″ represents an alkylene group having 1 to 3 carbon atoms. Examples of the alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, a propylene group, and an isopropylene group. Among these, a methylene group and an ethylene group are preferable, and n represents a number of 0 or 1, and is preferably 0 from the viewpoint of feedability of raw materials.

  Examples of the cyclohexyl group having R, R ′ and R ″ include, for example, cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-ethylcyclohexyl group, 3-ethylcyclohexyl group. Group, 4-ethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 2-propylcyclohexyl group, 3-propylcyclohexyl group, 4-propylcyclohexyl group, 2-isopropylcyclohexyl group, 3-isopropylcyclohexyl group, 4-isopropylcyclohexyl group, 2-t-butylcyclo Hexyl group, 3-t-butylcyclohexyl group, 4-t-butylcyclohexyl group, 2-methyl-5-isopropylcyclohexyl group, 5-methyl-2-isopropylcyclohexyl group (the same is available), cyclohexylmethyl group, 1-cyclohexylethyl group, 2-cyclohexylethyl group, 4-methylcyclohexylmethyl group, 1-cyclohexylpropyl group, 2-cyclohexylpropyl group, 3-cyclohexylpropyl group, 2-cyclohexyl-1-methylethyl group, 2,4 -A dimethyl cyclohexyl methyl group, a 3, 5- dimethyl cyclohexyl methyl group, etc. are mentioned.

  Among these, because of its high antibacterial properties, cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-isopropylcyclohexyl group, 2-t-butylcyclohexyl group, cyclohexylmethyl group A cyclohexylethyl group is preferable, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, and a cyclohexylmethyl group are more preferable, and a cyclohexyl group is most preferable.

  As a method for producing the compounds represented by the general formulas (1) and (2), any known method can be used. For example, the following general formula (3)

(In the formula, R, R ′, R ″ and n are the same as defined in the general formulas (1) and (2).)
In the method of dehydration condensation reaction of alcohol and glycerin represented by formula, in the method of dehydrochlorination reaction of alcohol represented by general formula (3) and 1-chloro-2,3-propanediol, in general formula (3) A method of hydrolyzing the resulting glycidyl ether compound after reacting the alcohol represented by epichlorohydrin, a method of reacting the alcohol represented by general formula (3) and glycidol, represented by general formula (3) A method of hydrolyzing the glycidyl ether compound obtained by reacting the alcohol to be reacted with allyl chloride or allyl bromide and then oxidizing with hydrogen peroxide or the like, the following general formula (4)

(In the formula, R, R ′, R ″ and n are the same as defined in formulas (1) and (2), and X represents a halogen atom.)
And a method of dehydrohalogenating a compound represented by the formula and glycerin. The compound obtained by these methods is often a mixture of (1) and (2), but the rate of formation of (1) and (2) differs depending on the reaction catalyst. In addition, in the reaction using glycerin, the above reaction is performed using a partially esterified glycerin with a lower fatty acid, and a saponification reaction is performed after completion of the reaction, glycerin is ketalized with methyl ethyl ketone or the like. By performing the above-mentioned reaction after the reaction and removing the ketal after the reaction is completed, the ratio of the production of (1) and (2) can be greatly changed.

  The amount of the antibacterial agent of the present invention represented by the general formula (1) and / or (2) varies depending on the application to be used, and is not particularly limited. If the amount is too large, the effect of increase corresponding to the amount added may not be obtained, so 0.001 to 20% by mass is preferable, 0.01 to 5% by mass is more preferable, and 0.1 to 2% is preferable. More preferred is mass%.

  The antibacterial composition of the present invention contains a chelating agent, a low molecular polyol, and nitrogen as components (A) and (B) to (G) represented by the general formula (1) and / or (2). It contains one or more compounds selected from the group consisting of nonionic surfactants, nitrogen-containing amphoteric surfactants, plant-derived extracts and zinc compounds.

  Examples of the chelating agent for component (B) include aminopolycarboxylic acid chelating agents, aromatic or aliphatic carboxylic acid chelating agents, amino acid chelating agents, ether polycarboxylic acid chelating agents, phosphonic acid chelating agents, Examples thereof include phosphoric acid chelating agents, hydroxycarboxylic acid chelating agents, polymer electrolyte (including oligomer electrolyte) chelating agents, dimethylglyoxime, ascorbic acid, thioglycolic acid, phytic acid, glyoxylic acid, glyoxalic acid, and the like. These chelating agents may be in the free acid form or in the form of a salt such as sodium salt, potassium salt, or ammonium salt. Furthermore, they may be in the form of their ester derivatives which are hydrolysable.

  Examples of the aminopolycarboxylic acid chelating agent include ethylenediaminetetraacetic acid, ethylenediaminediacetic acid, cyclohexanediaminetetraacetic acid, nitrilotriacetic acid, iminodiacetic acid, N- (2-hydroxyethyl) iminodiacetic acid, diethylenetriaminepentaacetic acid, N- (2 -Hydroxyethyl) ethylenediaminetriacetic acid, glycol etherdiaminetetraacetic acid, glutamic acid diacetic acid, aspartic acid diacetic acid and their salts.

  Examples of aromatic or aliphatic carboxylic acid chelating agents include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, azelaic acid, itaconic acid, aconitic acid, pyruvic acid, salicylic acid, Examples include acetylsalicylic acid, hydroxybenzoic acid, aminobenzoic acid (including anthranilic acid), phthalic acid, fumaric acid, trimellitic acid, gallic acid, hexahydrophthalic acid and salts thereof, methyl esters, and ethyl esters.

  Examples of the amino acid chelating agent include glycine, serine, alanine, lysine, cystine, cysteine, ethionine, tyrosine, methionine, and salts and derivatives thereof.

  Examples of the ether polycarboxylic acid-based chelating agent include diglycolic acid, a compound represented by the following formula, and salts thereof.

Y represents a hydrogen atom, —CH ₂ COOH or —COOH, and Z represents a hydrogen atom, —CH ₂ COOH or

を表す。

Represents.

  Examples of the phosphonic acid-based chelating agent include iminodimethylphosphonic acid, alkyldiphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid, and salts thereof.

  Examples of the phosphoric acid chelating agent include orthophosphoric acid, pyrophosphoric acid, triphosphoric acid, and polyphosphoric acid.

  Examples of the hydroxycarboxylic acid chelating agent include malic acid, citric acid, glycolic acid, gluconic acid, heptonic acid, tartaric acid, lactic acid, and salts thereof.

  Examples of the polymer electrolyte (including oligomer electrolyte) chelating agent include acrylic acid polymer, maleic anhydride polymer, α-hydroxyacrylic acid polymer, itaconic acid polymer, and two constituent monomers of these polymers. The copolymer which consists of the above and an epoxy succinic acid polymer are mentioned.

  Among these chelating agents, ethylenediaminetetraacetic acid, ethylenediaminediacetic acid, nitrilotriacetic acid, iminodiacetic acid, N- (2-hydroxyethyl) iminodiacetic acid, glutamic acid diacetic acid, aspartic acid diacetic acid, succinic acid, salicylic acid, oxalic acid, lactic acid , Fumaric acid, citric acid, tartaric acid, 1-hydroxyethane-1,1-diphosphonic acid and salts thereof are preferred, ethylenediaminetetraacetic acid, nitrilotriacetic acid, iminodiacetic acid, N- (2-hydroxyethyl) iminodiacetic acid, glutamic acid di Acetic acid, aspartic acid diacetic acid, succinic acid, lactic acid, tartaric acid and salts thereof are more preferred, and ethylenediaminetetraacetic acid, glutamic acid diacetic acid, aspartic acid diacetic acid and salts thereof are most preferred.

  The blending amount of the chelating agent is not particularly limited, but if the chelating agent is too small, the antibacterial improvement effect may not be obtained. Further, when the amount of the chelating agent is increased, the antibacterial property is improved accordingly, but when the chelating agent exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.5-500 mass parts is preferable with respect to 100 mass parts of (A) component, as for a chelating agent, 1-200 mass parts is more preferable, and 2-50 mass parts is still more preferable. If the content of the chelating agent is less than 0.5 parts by mass, the antibacterial improvement effect due to the addition of the chelating agent may not be sufficiently obtained, and if it exceeds 500 parts by mass, the antibacterial properties can be further improved. It may disappear. Moreover, when using 2 or more types of chelating agents, it is preferable that the total compounding quantity becomes said range.

  The component (C) low molecular polyol is a polyol having a molecular weight of 50 to 1000, preferably 50 to 500, such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, Propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2-methyl-1,2-propanediol, 2 -Methyl-1,3-propanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,3-pentanediol, 2,4-pentane Diol, 2-methyl-1,2-butanediol, -Methyl-2,3-butanediol, 2-methyl-1,4-butanediol, 3-methyl-1,2-butanediol, 3-methyl-1,3-butanediol, 2-ethyl-1,3 -Propanediol, 2,2-dimethyl-1,3-propanediol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 3,3-hexane Diol, 2-methyl-1,3-pentanediol, 2-methyl-1,5-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 3-methyl- 2,3-pentanediol, 3-methyl-2,4-pentanediol, 4-methyl-1,2-pentanediol, 2-ethyl-2-methyl-1,3-propanedio 2,2-dimethyl-2,4-butanediol, 2,3-dimethyl-1,2-butanediol, 1,2-heptanediol, 1,7-heptanediol, 3,4-heptanediol, -Propyl-2-methyl-1,3-propanediol, 2-isopropyl-2-methyl-1,3-propanediol, 1,2-octanediol, 1,8-octanediol, 3,6-octanediol, 2-ethyl-1,3-hexanediol, 2-sec-butyl-2-butyl-1,3-propanediol, 2,2-dimethyl-1,3-hexanediol, 2,5-dimethyl-2,5 -Hexanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,2-nonanediol, 1,3-nonanediol, 1,9-nonanediol, 3,6- Octanediol, 2-ethyl-2- (2-methyl) propyl-1,3-propanediol, 2,2,4-trimethyl-1,6-hexanediol, 2,4,4-trimethyl-1,6- Hexanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 2-methyl-1,8-octanediol, 1,2-decanediol, 1 , 10-decanediol, 5,6-decanediol, 3,6-dimethyl-3,6-octanediol, 3,7-dimethyl-1,6-octanediol, 3,7-dimethyl-1,7-octane Diol, 1,2-undecanediol, 1,4-undecanediol, 1,11-undecanediol, 6-ethyl-3-methyl-1,6-octanediol, 1,2- Decanediol, 1,10-dodecanediol, 1,12-dodecanediol, 2,4-diethyl-1,5-octanediol, 2,8,8-trimethyl-2,7-nonanediol, 1,2-tetradecane Diol, 1,14-tetradecanediol, 7,8-tetradecanediol, 1,2-pentadecanediol, 1,2-hexadecanediol, 1,16-hexadecanediol, 1,17-heptadecanediol, 1,2-octadecane Saturated diols or condensates thereof such as diol, 1,12-octadecanediol, 1,2-eicosanediol, 1,2-docosanediol, 1,2-tetracosanediol.

  2-butene-1,4-diol, 3-butene-1,2-diol, 2-methylene-1,3-propanediol, 2-butyne-1,4-diol, 5-hexene-1,2-diol 3-methyl-2-pentene-1,5-diol, 3-methylenepentane-1,5-diol, 1,5-hexadiene-3,4-diol, 7-octene-1,2-diol, 2, 5-dimethyl-3-hexene-2,5-diol, 9-decene-1,2-diol, 2,6-dimethyl-7-octene-2,6-diol, 3,7-dimethyl-7-octene- 1,6-diol, 13-tetradecene-1,2-diol, 12-hydroxy-9-octadecenol, 2-pentyne-1,4-diol, 3-hexyne-2,5-diol, 4-methyl-2- Pentin , 4-diol, 3-heptin-2,5-diol, 4-methyl-2-pentyne-1,4-diol, 3,4-dimethyl-1-pentyne-3,4-diol, 2,5-dimethyl -3-hexyne-2,5-diol, 5-decyne-4,7-diol, 2,6-dimethyl-7-octyne-2,6-diol, 3,6-dimethyl-4-octyne-3,6 -Diol, 2,3,6,7-tetramethyl-4-octyne-3,6-diol, 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 2,5,8 , 11-tetramethyl-6-dodecin-5,8-diol, 1,1,4,4-tetraisopropyl-4-octyne-3,6-diol, 5,10-diethyl-7-tetradecine-6,9 -Unsaturated diols such as diols.

  1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cycloheptanediol, 2,3-norbornane Diol, 2,5-norbornanediol, 2,7-norbornanediol, 1,2-cyclooctanediol, 1,4-cyclooctanediol, 1,2-cyclodecanediol, 5-cyclooctene-1,2-diol 1,5-decalindiol, limonene glycol, 1,2-terpenediol, 4,4′-bicyclohexanediol, 1,2-cyclododecanediol, and the like.

  Glycerin, 1,2,3-butanetriol, 1,2,4-butanetriol, 2-methyl-1,2,3-propanetriol, 1,2,3-pentanetriol, 1,2,4-pentanetriol 1,3,5-pentanetriol, 2,3,4-pentanetriol, 2-methyl-2,3,4-butanetriol, trimethylolethane, 2,3,4-hexanetriol, 2-ethyl-1 , 2,3-butanetriol, trimethylolpropane, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, triethanolamine, triisopropanolamine, etc. Alcoholic alcohol.

  Erythritol, pentaerythritol, 1,2,3,4-pentatetrol, 2,3,4,5-hexatetrol, 1,2,4,5-pentanetetrol, 1,3,4,5-hexane Tetrahydric alcohols such as tetrol, diglycerin, sorbitan, N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine, N, N, N ′, N′-tetrakis (hydroxyethyl) ethylenediamine;

  Pentavalent alcohols such as adonitol, arabitol, xylitol, triglycerin;

  Hexavalent alcohols such as dipentaerythritol, sorbitol, mannitol, iditol, inositol, dulcitol, talose and allose.

  1-methyl glyceryl ether, 2-methyl glyceryl ether, 1-ethyl glyceryl ether, 2-ethyl glyceryl ether, 1-propyl glyceryl ether, 2-propyl glyceryl ether, 1-isopropyl glyceryl ether, 2-isopropyl glyceryl ether, 1- Butyl glyceryl ether, 2-butyl glyceryl ether, 1-isobutyl glyceryl ether, 2-isobutyl glyceryl ether, 1-pentyl glyceryl ether, 2-pentyl glyceryl ether, 1-hexyl glyceryl ether, 2-hexyl glyceryl ether, 1-heptyl glyceryl Ether, 2-heptyl glyceryl ether, 1-octyl glyceryl ether, 2-octyl glyceryl ether, 1- (2-ethylhexyl) Lyceryl ether, 2- (2-ethylhexyl) glyceryl ether, 1-nonyl glyceryl ether, 2-nonyl glyceryl ether, 1-decyl glyceryl ether, 2-decyl glyceryl ether, 1-undecyl glyceryl ether, 2-undecyl glyceryl Ether, 1-dodecyl glyceryl ether, 2-dodecyl glyceryl ether, 1-tridecyl glyceryl ether, 2-tridecyl glyceryl ether, 1-tetradecyl glyceryl ether, 2-tetradecyl glyceryl ether, 1-hexadecyl glyceryl ether, 2 -Hexadecyl glyceryl ether, 1-octadecyl glyceryl ether, 2-octadecyl glyceryl ether, 1-branched octadecyl glyceryl ether, 2-branched octadecyl glycerin Ryl ether, 1-eicosyl glyceryl ether, 2-eicosyl glyceryl ether, 1-allyl glyceryl ether, 2-allyl glyceryl ether, 1-undecenyl glyceryl ether, 2-undecenyl glyceryl ether, 1-oleyl glyceryl ether, Glycerin monoethers such as 2-oleyl glyceryl ether, 1-phenyl glyceryl ether, and 2-phenyl glyceryl ether.

  N-substituted diethanolamines such as N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-isopropyldiethanolamine, N-butyldiethanolamine, N-cyclohexyldiethanolamine and N- (2-ethylhexyl) diethanolamine.

  N-methyldiisopropanolamine, N-ethyldiisopropanolamine, N-propyldiisopropanolamine, N-isopropyldiisopropanolamine, N-butyldiisopropanolamine, N-cyclohexyldiisopropanolamine, N- (2-ethylhexyl) di N-substituted diisopropanolamines such as isopropanolamine.

  3-dimethylamino-1,2-propanediol, 3-diethylamino-1,2-propanediol, 3-dipropylamino-1,2-propanediol, 3-diisopropylamino-1,2-propanediol, 3- Examples include N, N-disubstituted-3-amino-1,2-propanediols such as dibutylamino-1,2-propanediol.

  Among these low molecular polyols, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1 , 2-pentanediol, 3-methyl-1,3-butanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 2-ethyl-1,3-hexanediol, 1, 2-nonanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,2-decanediol, 1,10-decanediol, glycerin, triethanolamine, triisopropanolamine, erythritol, diglycerin, sorbitan , N, N, N ′, N′-Te Lakis (2-hydroxypropyl) ethylenediamine, N, N, N ′, N′-tetrakis (hydroxyethyl) ethylenediamine, sorbitol, 1-methylglyceryl ether, 1-ethylglyceryl ether, 1-propylglyceryl ether, 1-butylglyceryl Ether, 1-octyl glyceryl ether, 1- (2-ethylhexyl) glyceryl ether, 1-decyl glyceryl ether, 1-allyl glyceryl ether are preferred, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene Glycol, 1,3-butanediol, 3-methyl-1,3-butanediol, 1,2-octanediol, glycerin, triethanolamine, diglyceride , Sorbitan, N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine, sorbitol, 1-allylglyceryl ether are more preferable, propylene glycol, dipropylene glycol, 1,3-butanediol, 3- More preferred are methyl-1,3-butanediol, glycerin, sorbitol, and 1-allyl glyceryl ether.

  The blending amount of the low molecular polyol is not particularly limited, but if the low molecular polyol is too small, the antibacterial improvement effect may not be obtained. Further, when the amount of the low molecular polyol is increased, the antibacterial property is improved accordingly, but when the amount of the low molecular polyol exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.5-500 mass parts is preferable with respect to 100 mass parts of (A) component, as for a low molecular polyol, 1-200 mass parts is more preferable, and 2-50 mass parts is still more preferable. If the content of the low molecular polyol is less than 0.5 parts by mass, the antibacterial effect may not be sufficiently obtained by the addition of the low molecular polyol. If the content exceeds 500 parts by mass, the antibacterial property is further improved. May not be possible. Moreover, when using 2 or more types of low molecular polyols, it is preferable that the total compounding quantity becomes said range.

  As a nitrogen-containing nonionic surfactant of (D) component, the structure represented by the following general formula (7)-(13) is mentioned, for example.

(R ¹ represents an alkyl group or an alkenyl group, R ² represents an alkyl group, an alkenyl group, or a group represented by — (CH ₂ —CH ₂ O) _y H, and a and y each represent a number of 1 to 20. To express.)

In the compound represented by the general formula (7), R ¹ preferably has 8 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms. R ² is preferably a group represented by — (CH ₂ —CH ₂ O) _y H. Furthermore, the total value of a and y is preferably a number of 2 to 10, more preferably a number of 2 to 4.

(R ³ represents an alkyl group or an alkenyl group, R ⁴ represents an alkylene group having 2 to 6 carbon atoms, and b, c, and d each represent an independent number of 1 to 20)

In the compound represented by the general formula (8), R ³ preferably has 8 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms. R ⁴ preferably has 2 to 3 carbon atoms, and more preferably 3 carbon atoms. Furthermore, the total value of b, c and d is preferably a number of 3 to 10, and more preferably 3 to 5.

(R ⁵ represents an alkyl group or an alkenyl group.)

In the compound represented by the general formula (9), R ⁵ preferably has 8 to 22 carbon atoms, more preferably 9 to 18 carbon atoms, and still more preferably 10 to 14 carbon atoms.

(R ⁶ represents an alkyl group or an alkenyl group, R ⁷ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a group represented by — (AO) _z H, and A represents an alkylene group having 2 to 3 carbon atoms. E and z each independently represents a number from 1 to 20.)

In the compound represented by the general formula (10), R ⁶ preferably has 8 to 22 carbon atoms, more preferably 9 to 18 carbon atoms, and still more preferably 10 to 14 carbon atoms. R ⁷ is preferably a hydrogen atom, a methyl group, or —CH ₂ —CH ₂ OH, more preferably a hydrogen atom or a methyl group. Further, when R ⁷ is a hydrogen atom, e is preferably a number from 1 to 3, more preferably A is an ethylene group and e is 1. When R ⁷ is a methyl group, A is preferably an ethylene group, more preferably A is an ethylene group and e is 1. When R ⁷ is —CH ₂ —CH ₂ OH, it is preferable that A is an ethylene group and e is 1.

  (B and F represent an ethylene group or a propylene group, and f to l and o each represent an independent number of 1 to 200, provided that B and F are not the same group.)

  In the compound represented by the general formula (11), it is preferable that B is a propylene group and F is an ethylene group. The total value of f, h, j, and l is preferably 30 to 70, more preferably 40 to 55, and still more preferably 45 to 50. Furthermore, the total value of g, i, k, o is preferably 10 to 200%, more preferably 20 to 150%, and even more preferably 50 to 100% with respect to the total value of f, h, j, and l. preferable.

(R ⁸ represents an alkyl group having 8 to 18 carbon atoms.)

In the compound represented by the general formula (12), R ⁸ preferably has 9 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and still more preferably 10 to 14 carbon atoms.

(R ⁹ represents an alkyl group having 7 to 21 carbon atoms.)

In the compound represented by the general formula (13), R ⁹ preferably has 8 to 17 carbon atoms, more preferably 9 to 15 carbon atoms, and still more preferably 9 to 13 carbon atoms.

  Among these nitrogen-containing nonionic surfactants, compounds represented by the general formulas (7), (9), (10), (12), and (13) are preferable, and the general formulas (9) and (10) , (13) is more preferable, and general formula (10) is most preferable.

  Although the compounding quantity of nitrogen-containing nonionic surfactant is not specifically limited, If there are too few nitrogen-containing nonionic surfactants, an antibacterial improvement effect may not be acquired. Further, when the amount of the nitrogen-containing nonionic surfactant is increased, the antibacterial property is improved accordingly, but when the amount of the nitrogen-containing nonionic surfactant exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.5-500 mass parts is preferable with respect to 100 mass parts of (A) component, as for a nitrogen-containing nonionic surfactant, 1-200 mass parts is more preferable, and 2-50 mass parts is still more preferable. If the content of the nitrogen-containing nonionic surfactant is less than 0.5 parts by mass, the antibacterial improvement effect due to the addition of the nitrogen-containing nonionic surfactant may not be sufficiently obtained. May not be able to improve further. Moreover, when using 2 or more types of nitrogen-containing nonionic surfactant, it is preferable that the total compounding quantity becomes said range.

  Examples of the nitrogen-containing amphoteric surfactant as the component (E) include structures represented by the following general formulas (14) to (19).

(R ¹⁰ represents an alkyl group having 8 to 22 carbon atoms, and p represents a number of 1 to 3)

In the compound represented by the general formula (14), R ¹⁰ preferably has 9 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and still more preferably 10 to 14 carbon atoms. The value of p is preferably 1.

(R ¹¹ represents an alkyl group or alkenyl group having 7 to 21 carbon atoms, and q represents a number of 2 to 3)

In the compound represented by the general formula (15), R ¹¹ preferably has 8 to 17 carbon atoms, more preferably 9 to 15 carbon atoms, and still more preferably 9 to 13 carbon atoms. The value of q is preferably 3.

(R ¹² represents an alkyl group or alkenyl group having 7 to 21 carbon atoms, and r represents a number of 2 to 3)

In the compound represented by the general formula (16), R ¹² preferably has 8 to 17 carbon atoms, more preferably 9 to 15 carbon atoms, and still more preferably 9 to 13 carbon atoms. The value of r is preferably 3.

(R ¹³ represents an alkyl or alkenyl group having 7 to ²¹ carbon atoms.)

In the compound represented by the general formula (17), R ¹³ preferably has 8 to 17 carbon atoms, more preferably 9 to 15 carbon atoms, and still more preferably 9 to 13 carbon atoms.

(R ¹⁴ represents an alkyl group or alkenyl group having 8 to 22 carbon atoms, and s represents a number of 2 to 3)

In the compound represented by the general formula (18), R ¹⁴ preferably has 9 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and still more preferably 10 to 14 carbon atoms. The value of s is preferably 3.

(R ¹⁵ represents an alkyl group or alkenyl group having 7 to 21 carbon atoms, and t represents a number of 2 to 3)

In the compound represented by the general formula (19), R ¹⁵ preferably has 8 to 17 carbon atoms, more preferably 9 to 15 carbon atoms, and still more preferably 9 to 13 carbon atoms. The value of t is preferably 3.

  Among these nitrogen-containing amphoteric surfactants, the compounds represented by the general formulas (14), (15) and (16) are preferable, the general formulas (15) and (16) are more preferable, and the general formula (15 ) Is most preferred.

  Although the compounding quantity of nitrogen-containing amphoteric surfactant is not specifically limited, If there are too few nitrogen-containing amphoteric surfactants, an antibacterial improvement effect may not be acquired. Further, when the amount of the nitrogen-containing amphoteric surfactant is increased, the antibacterial property is improved accordingly, but when the nitrogen-containing amphoteric surfactant exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.5-500 mass parts is preferable with respect to 100 mass parts of (A) component, and nitrogen-containing amphoteric surfactant has more preferable 1-200 mass parts, and 2-50 mass parts is still more preferable. If the content of the nitrogen-containing amphoteric surfactant is less than 0.5 parts by mass, the antibacterial improvement effect due to the addition of the nitrogen-containing amphoteric surfactant may not be sufficiently obtained. May not be able to improve further. Moreover, when using 2 or more types of nitrogen-containing amphoteric surfactant, it is preferable that the total compounding quantity becomes said range.

  The plant-derived extract, which is the component (F) of the antibacterial composition of the present invention, refers to all plants, algae or fungi, or specific parts such as flowers, leaves, stems, fruits, bark, roots, seeds, and resins. It is obtained as it is or after being subjected to pressing, drying and pulverization or fermentation, and then extracted with a solvent at room temperature or under heating, and is soluble in water, ethanol, propylene glycol or oil. Alternatively, the extract may be diluted, concentrated or dried. Further, it may be an essential oil obtained by using a steam distillation method, an extraction method, a chromatography method or the like.

  As an extraction solvent, those usually used for extraction of natural product components, such as water; alcohols such as methanol, ethanol, propanol and butanol; polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol and glycerin; acetone and methyl ethyl ketone Ketones such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, diethyl ether and polyethylene glycol; halogenated hydrocarbons such as dichloroethane and chloroform; aliphatics such as petroleum ether, n-hexane and cyclohexane Hydrocarbons; aromatic hydrocarbons such as toluene; pyridines; sodium chloride solution, and the like. Water, ethanol, propylene glycol, and butylene glycol are particularly preferable.

  Plants that can be used as plant-derived extracts include, for example, arch chalk, almond, eye, Aisenhard thia polystacia, eyebright, blue-green agave, aomoji, acacia concina, acacia senegal, acacia senegal gum, acacia decreens, red clover, Akaharunire, Akayamajiou, Agi, Agrimonia eupatoria, Akebobi, Asagaokakaraksa, thistle, reed, ashitaba, ajugatsu kestanika, azuki, asunaro, asparagus, asparagus sine alice, acerola, asenayaku, asenayakashi, atlas Gaith Suleio Calps, Avenas Trigosa, Avocado, Ama, Amacha, Amacharu, Amadokoro, Amamo, Amiris Balsamifera, American Pikachi, America Shaw, American Shaw, American Carrot, Amomu Aromachiku, Aracasi, Arcana, Arctium Majus, Arctium Minus, Arnica, Arnica Mysonis, Alpinia Officinalum, Alfalfa (Acacia vera), Aloe Vera, Ansange, Apricot, Angelica, Antilis Brunellaria, Amperopsis Grocedentata, Anmarok, Ikarisou, Izayoi Rose, Itadori, Italian Cypress, Strawberry, Fig, Ichiyakuso, Ginkgo, Itlan, Carob, Ibukitorano, Imosemiru, Nettle, Iran Iran, Iris Iris Parida, Iwabenkei, Iwamituba, common bean, fennel, witania somunifera, turmeric, usubasaicin, moray moth, udo, sea urchin Ume, Uyaku, Urarkanthus, Uri, Wurbaraktsuka, Ulmus Davidiana, Uncarriagementa, Unshimichikan, Ages, Eilan Thai, Edelweiss, Ezoukogi, Ezo Snake Strawberry, Ezomisohagi, Echinashi, Echinaceaparida, Enishida, Ebine, Ebine , Enju, Pea, Emperor juniper, Enmeiso, Soryo mugwort, Oren, Milk thistle, Giant scorpion, Ozodenda, Giant peony, Okis macata, Okis muscara, Orchid, Orc (European oak), Ogulma, Oval Japanese cypress, Greater Crape myrtle, Greater Orange, Greater Palm, Ominocephalus, Barley, Allspice, Okazeri, Okra, Osiroy Bana, Ginseng, Hypericum, Onigashi, Onisarubia, Onihamadakon, Onis, Opuntia Tuna, Opuntia Streptacantha, Dutch Mustard, Dutch Peonies, Olives, Origanum Heracreoticum, Ortosihon Stamineus, Ormenis Murchicaulis, Orange, Oromu ,

  Gardenia Tahitensis, Carnation, Cara Senegalensis, Cacao, Oyster, Cassia, Cashew Nut, Cascara Sagrada, Cassiaa Tarica, Kappa Ficus Albarezi, Cattleya, Canada Hydrastis, Canary Tree, Canina Rose, Ganoderma, Hippopotamus, Cub, Catfish (clam), chamomile (camomile), ginkgo biloba, cayupute, carax salmon man, oats, oats, cara touki, guarana, garikkabara, cauliflower, karin, caruna (Goryu modoki), garcinia cambodia, carrot, ivy-belli , Kistrawberry, kiwi, kikarasuuri, kikunigana, kigeria africana, yellow aloe vera, yellowfin mint, linden, quinoa, yellowfin, yellowtail Suzushiro, Kiwananohachiwame, Millet, Gymnema, Kimokuren, Cassava, Cabbage, Caraway, Cucumber (Cucumber), Kyo-o, Gyoryu, Gyorybai, Kiraya, Kiri, Gimbaika (Watermelon), Guar, Guava, Quince Seed, Cuerce , Kuchinoki, wolfberry, celandine, sardine, camphor, damselfly, gardenia, bearberry, kumazasa, geese, anemonefish, cumin, clamelatriandra, clara, granberry, chrysanthemum maritimum, grindelia borealis, clintonia borealis , Walnut, grapefruit, clematis, black pepper, black walnut, black-faced toad, glove, black currant, black whale, mulberry, keiketto, kei ( Namon), Geum Urbanum, Geum Rivere, Cape Aloe, Poppy, Gekkavidin, Bay geuge, Ghetto, Keyama Zorina, Gentian, Gentian Prostrata, Gennoshoco, Kemponashi, Kouki, Kokuchitan, Kokeiten, Kousigai, Kobo Ichigo, Kobo Indica, Cocktan, Cochlearia officinalis, Cowberry, Coco, Gosho strawberry, Pepper, Coccillosa cactus, Cochineal cactus, Gypsophila, Coleoptera, Quercus, Kochakobe, Burdock, Sesame, Wheat, Rice, Koranoki, Coriander, Coleus, Coleus , Koroha, Conzu Lango, Comfrey

  Sisal Asa, Saisin, Cyperus Esculentus, Cypress, Cyprianthus, South Rare Involcata, Saxima Button Crab, Sakura, Sakuraba Kanboku, Pomegranate, Sugar Maple, Sugarcane, Sugar Pine, Sasanca, Sassafrasnoki, Saffron, Savonsau, Salas , Sanguinaria canadensis, hawthorn, sansikimire, sanshininjin, sanshuyu, salamander, sunpens, ciatea medullaris, cyanotis araknoidea, shea butter, shiozakiso, shinshinburi irio, cyst rose (labdanum), cistus mons Periensis, Cystula danifells, perilla, turkey, linden, shibamugi, dipterix odorata, siberian fir, simalba, simushi Gadafrika, Shimotsuke, Potato, Peonies, Jasmine, Janohige, Janome Erica, Shukusha, Juzudama, Gypsophila, Juniperus mexicana, Junsai, Ginger, Shozukaku (Cardamom), Shobu, Dioscorea, Silva, Indiana Sokei, Shirobanupin, Shirobanawata, Shinkonakarisaya, Synthpalm Dulcificum, Cymbidium, Simprocosacemosa, Sweet Acacia, Watermelon, Honeysuckle, Scabiosa Albensis, Sugina, Scutariaria relicata, Stevia, Strobe pine, Spiny bamboo Spirulina platensis, Spirulina maxima, Purslane, spelled wheat, Sumio cherry, Sumirax aristolothiae Rear, Acacia, Scots pine, Acacia serrata, Atlantic nettle, Psyllium psyllium, Hypericum perforatum, Psyllium serrata, Pepper pumpkin, Pseudocarina, Prunus serrata, Prunus vulgaris, Prunus serrata, Prunus vulgaris, Pepper White willow, dandelion, dandelion, european tree, horse chestnut, ash, pear, sunflower, rowan ash, seiron nikki, elderberry, carrot, swan, sunflower, antelope, sunflower Cherry blossoms, cornflowers, barberry, mistletoe Yeobu Strawberry, Ceylon Nikkei, Sage, Cecropia of Tsusihoria, Sequoia Osugi, Cecil Oak, Sedum Purpleum, Xenia Mallow, Senega, Geranium, Sercidium Florida, Cereus Grandiflorus, Celery, Senkyu, Centifolia Rose, Centipedakunningamimi, Senninkoku, Sempukuka, Semburi, Sojutsu, Sakuhakuhi, Saw Palmetto, Sokakei, Buckwheat, Soranum Ricokarpum,

  Daiukyo, Daikon, Daisanchiku, Soybean, Taisou, Daidai, Taitsuogi, Thyme, Hinoki, Takasaburo, Tachibakuso, Tachibana, Tabinoki, Tabebia Abernedae, Tamasaki Tsumufuji, Damask Rose, Onion, Damiana, Tara Gong Fira, Chigaya, Cha (tea), Chaboteisou, Tuberose, Clove, Datura, Chickpea, Chileatmentosa, Tsukushimanabeetsumi, Tsuboksa, Tsurugumi, Tsurugukudami, Tsurureishi, Tea Tree, Dioscorea Composita, Dioscoreavirosa, Dioscorea mexicana, Teuchigurumi, Tecoma clear squirrel, Tetsuzainoki, Duke, DuBoisley Cardiochi, Terminaria, Tencha, Germany , German spruce, red pepper, red pepper, red snapper, red pepper, corn, corn silk, pearl millet, licorice, dolphin, red carrot, red pepper, red pepper, tomato, trigonellafoenum, Tormentilla, Trolloaoimodoki,

  Nagabagishigishi, Nagii Kada, Eggplant, Nazuna, Natsume, Natsushigiku, Natsubo Daiju, Dateme, Date Palm, Nansou, Nanbanai, Nanbanksafuji, Nioisumire, Niotenjikuaoi, Niohihiba, Nigayuguni, Nikusuguni, Nikuzuni , Nymphair Alba, Prunus, Neubara, Nousen Hallen, Nozomire, Novara, Novorogiku,

  Pineapple, hibiscus, high pine, baobab, bakuchia citriodora, bakumondo, bacopamonniera, hagoromogusa, lotus, parsley, patchouli, mint crab, baccaris genisteroides, passiflora arata, pearl barley, banana, hanahakka, honeysuckle Tahitensis, Honeysenna, Papaya, Paphiopedilum maudae, Haberlear rhodopensis, Hermanus, Hamamelis, Hayatouri, Rose, Parietalia, Harienju, Harpagophyta, Palmarosa, Barrosma beetulina, Van turmeric, Pansy, Bambaragi, Beet, Holly , Bisnagabella, Bitter Almond, Bitter Orange, Hydratiskanadensis, Daisies, Daisies, Vinankazura Pinus Hedda, Cypress, Hibamata, Hiiragiku, Hipofaerarumnoides, Sunflower, Himekouji, Himekora, Himetsunichinichi, Himena Air-Kurbaril, Himefuuro, Sandalwood, Chickpea, Robin, Robbin Phaffia Paniculata, Fusenkazura, Pueraria Mirifica, Ferula Garvaniflua, Fuquidan Popo, Bukkuri, Fusazakisen, Fusagisuri, Fusafujitsugi, Fusanus Spicatus, Petit Glen, Petit Petalum Orakoides, Bussouge, Buchal Plum Umum, Grapes, Futsomomo, Beech, Fuyuzansho, Fuyubodaiju, Fuyumushinatsutake, Fragalia chiroensis, Brazil nut French Caenshaw, French Lavender, Plantago Goura, Plantago Gobata, Plantagogosylium, Primula Siemens, Prunes, Prunus Africana, Prunus Serochina, Plumeria, Plectrantus Barbatas, Bretcia Hiacinchina, Propolis, Bay, Hayflower , Hazelnuts, pecans, vetiver, loofah, penny royal mint, beech, safflower, safflower assembly, pepo pumpkin, hera plantain, pelargonium capitum, helichry arena, helichrymus angsitorium, helichry italium, bergamot Dasilachis, peruvian balsam, bergamot, berberis aquiholium, veronica kaficinaris, henna, henruuda, scallop, boushuboku , Bow shunka, spinach, spinach fern, spinach, hawkweed, honoki, hokbei fusoso, bocoa plow sensis, boswellia serata, hosobasena, josobabareniku, bodaiju, button, hop, poterium officinale, jojoba, polygonatum murch Ponkan,

  Macadamia, Magnolia Officinalis, Magnolia Biondi, Magwa, Magella, Magi, Madake, Pine, Matsuri, Matecha, Madonna Lily, Majorana, Maria Thistle, Malpigia Grabra, Quince, Marronie, Mango, Mangosteen, Manshuuokajika Red pine, Manjugiku, Mandarin orange, Mandrake, Mishima psycho, Mizuhakka, Mizuemon, Mitsyanagi, Mitsugasashi, Mitra carpath skater, Mimosa nuflora, Mircaria dubia, Myrrh (Motsukyaku), Milottam flavifolia, Milobara sword , Murasakikibib, murasaki assembly, murasakibarengiku, murayakoenji, mebouki, matsutake rush, melia azalacta, melissa (cous Peppermint), sweet clover, Merosuria, melon, mental Al Ben cis, Moukoyomogi, Mower these Fulvia subtilis, magnolia, Mosukatabara, Vigna Aconitifolia, Motsuyakuju, peach, Terminalia catappa,

  Yaksou, cornflower, yashabushi, yachiyanagi, willow mint, willow orchid, yamagwa, yamazakura, yamanoimo, yamagi, yuugao, eucalyptus, eupatium ayapana, eupatium rebaudium mubertuni, yukinoshita, yuzucha , Lily, scotskin beetle, physalis vulgaris, pokeweed, european blackberry, european yellowtail, european chestnut, european white willow, european birch, european beech, european mangusa, european fir, wormwood, wormwood,

  Lychee, Lima, Lime, Lime, Lilac, Radiata, Pine, Latania, Peanut, Ranunculus ficaria, Labandula hybrida, Luffa, Lavender, Larix Europaea, La Rare di Balikata, Rare Mexicana, Rambutan, Riso, Riso Samnium Calcolumn, Lithosea Glutinosa, Longan, Liriosma Obataki, Apple, Rooibos, Lupine Subucarnosus, Lubusvilos, Lumpuyan, Lurisisa, Lurichiensou, Respeda, Lesedarteola, Lettuce, Redamasto, Ledam Pulse Tre, Lebanese Giant Levis Chicum Officinale, Lemon, Lemongrass, Astragalus, Rosewood, Rosemary, Low Bush Blueberry, Roman Chamomile, Laurel (Laurel), Logwood, Busuta Coffea,

  Wild thyme, horseradish, horseradish, horseradish, cottontail, cotton bud, walteria indica, walnut.

  Ascofilm Nodosum, Aname, Oukimo, Okinawa Mozuku, Gigalchinasterata, Kujermaniela Girata, Sargassum Filipendula, Sargassum Fusifom, Sargassum Muticam, Sphaceraria scoparia, Durvillea Antarcica, Padina Pavonica, Himantalia Elongata, Fucus Serats, Pervetian Canarikurata, Macrocystis pirifera, Mitsushi Kombu, Laminaria kurosutika, Laminaria Kroosutoni, Laminaria diguitta, Laminaria Hiperborea, Wakame, Asparagopsis armata, Igis, Kaguibaranori , Catamen giraffe rhinoceros, geridium curchira guineum, saimi, striped primrose, duls, chinolimo, tochaka, porphyridium cruentum, marbatis macronori Lysosamnium cororioides, anaoaosa, chlorella emersoni, chlorella pyrenoidosa, duna riela salina, duna riela daudawil, hiraaonori, spirulina platensis, spirulina maxima, hasrea austria, dereceria sanguinea, picarolobista Algae such as les, haematococcus prubiaris, cyanobacteria, condor crisps, corals, sea whip, red algae.

  Examples include lichens and fungi such as Ebernia furfracea, horned moss, Usnia barbata, Oshagujitake, birch bamboo, shiitake mushroom, nymph mushroom, Japanese pine mushroom, Fuyushinatsutake, birch bamboo, Cordillera edulis.

  Among these, akebi stalk extract, asunalo extract, amamo extract, altea extract, arnica extract, aloe vera extract, izayoi rose extract, imosemiru extract, irisu root extract, fennel extract, ages extract, ougon extract (koganebana root extract), lauren extract , Ginseng extract, hypericum extract, Dutch mustard extract, orange oil, cattail extract, chamomile extract, oat extract, carrot extract, raspberry extract, kiwi extract, kidachi aloe extract, yellowfin bark extract (Obaku extract), quince seed extract, gardenia extract , Clara extract, grapefruit extract, clematis extract, chlorella extract, cape aloe extract, ginger pepper extract, kohone extract, savonsowe , Hawthorn extract, sage extract, perilla extract, linden extract, cypress extract, peony extract, ginger root extract, birch extract, cedar extract, pheasant extract, yarrow extract, sage extract, sage oil, mallow extract, assembly extract, soybean extract, Soybean extract, Taiso extract, tea extract, tuberose extract, Tounin extract, dokudami extract, wild rose extract, buckthorn root extract, peppermint oil, pearl barley extract, hamamelis extract, buffalo extract, hibamata extract, loquat leaf extract, fukidan popo extract, butcher bloom extract, beech extract , Peppermint extract, Majorana extract, Marronnier extract, Mishima psycho root extract, Mukuroji extract, Melissa extract, Merirot extract , Peach leaf extract, cabbage berry extract, eucalyptus extract, eucalyptus oil, saxifrage extract, citrus extract, lily extract, Yokuinin extract (seed extract of pearl barley), mugwort extract, lavender extract, lavender oil, litchi extract, lemon extract, rosemary extract , Rosemary oil, wild thyme extract, bituminous extract, hydrolyzed rice extract, hydrolyzed yeast extract, brown algae extract, red algae extract, brown sugar extract, rice extract hydrolyzate, green algae extract, green tea extract, asunalo extract, altea Extract, Izayoi Rose Extract, Iris Root Extract, Ogon Extract, Panax Ginseng Extract, Orange Oil, Chamomile Extract, Carrot Extract, Kidachia Aloe Extract, Yellowfin Bark Extract, Clara Extract, Chlorella Extract, Peonies Extract, Birch extract, Achillea millefolium extract, Sage oil, Tea extract, Tuberose, Dokudami extract, Novara extract, Hamamelis extract, Loquat leaf extract, Beech extract, Maronnier extract, Melissa extract, Merilot extract, Eucalyptus extract, Eucalyptus oil, Yukinoshita extract, Yuzu extract, Lily extract, Mugwort extract, lavender extract, lavender oil, rosemary extract, brown algae extract, red algae extract, rice extract hydrolyzate, green algae extract, green tea extract are more preferred, asunaro extract, izayoi rose extract, eel extract, ginseng extract, chamomile extract, Yellowfin bark extract, Clara extract, Chlorella extract, Birch extract, Achillea millefolium extract, Tuberose, Hamamelis extract, Loquat leaf extract, Beech extract, Lissa extract, Eucalyptus extract, Eucalyptus oil, Yukinoshita extract, Lily extract, Artemisia extract, Brown algae extract, Green tea extract are more preferable, Asunaro extract, Panax ginseng extract, Chamomile extract, Yellowfin bark extract, Chlorella extract, Birch extract, Tuberose, Hamamelis extract, Eucalyptus Most preferred are extracts, yukinoshita extract, and brown algae extract.

  The blending amount of the plant-derived extract is not particularly limited, but if the plant-derived extract is too small, the antibacterial improvement effect may not be obtained. Further, when the amount of plant-derived extract is increased, the antibacterial property is improved accordingly, but when the plant-derived extract exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.1-1000 mass parts is preferable with respect to 100 mass parts of (A) component, as for a plant origin extract, 0.5-200 mass parts is more preferable, and 1-100 mass parts is still more preferable. If the content of the plant-derived extract is less than 0.1 part by mass, the antibacterial improvement effect due to the addition of the plant-derived extract may not be sufficiently obtained, and if it exceeds 1000 parts by mass, the antibacterial property is further improved. May not be possible. Moreover, when using 2 or more types of plant origin extracts, it is preferable that the total compounding quantity becomes said range.

  Examples of the zinc compound of component (G) include zinc acetate, zinc laurate, zinc myristate, zinc palmitate, zinc ricinoleate, zinc undecylenate, zinc aspartate, zinc acetylmethionine, zinc gluconate, zinc citrate Organic acid zinc salts such as zinc polypyrrolidone carboxylate and zinc picolinate; zinc sulfonate salts such as zinc p-phenolsulfonate; zinc ester phosphates such as zinc ascorbyl phosphate, sodium cetyl phosphate and DNA zinc; Zinc complexes such as zinc pyrithione; Zinc-supported zeolite such as (silver / zinc / ammonium) zeolite, silicic acid (ammonium / silver / zinc / aluminum); aluminum oxide / zinc, aluminum oxide / zinc / cerium, aluminum oxide / zinc / iron Baked aluminum hydroxide, etc. Materials: Inorganic zinc salts such as zinc sulfate, zinc sulfide, zinc chloride, zinc bromide, zinc nitrate, zinc chloride ammonium, zinc aluminum sulfate, potassium zinc sulfate, zinc iodide, basic zinc carbonate; (hydroxide / carbonic acid) (Mg / Al / zinc), zinc oxide and the like. Among these, a compound that easily dissolves in water to become zinc ions is preferable, the solubility in 100 g of water at 20 ° C. is preferably 5 g or more, and the solubility is more preferably 10 g or more. Examples of such zinc compounds include zinc sulfate, zinc chloride, zinc gluconate, zinc bromide, zinc nitrate, zinc ammonium chloride, zinc aluminum sulfate, potassium zinc sulfate, and zinc iodide.

  Although the compounding quantity of a zinc compound is not specifically limited, If there are too few zinc compounds, an antimicrobial improvement effect may not be acquired. Further, when the amount of the zinc compound is increased, the antibacterial property is improved accordingly, but when the zinc compound exceeds a certain amount, the antibacterial property may not be further improved. Therefore, 0.02-10 mass parts is preferable with respect to 100 mass parts of (A) component, as for a zinc compound, 0.05-5 mass parts is more preferable, and 0.1-2 mass parts is still more preferable. If the content of the zinc compound is less than 0.1 parts by mass, the antibacterial effect of adding the zinc compound may not be sufficiently obtained. If the content exceeds 1000 parts by mass, the antibacterial properties can be further improved. It may disappear. Moreover, when using 2 or more types of zinc compounds, it is preferable that the total compounding quantity becomes said range.

  The method of using the antibacterial agent and antibacterial composition of the present invention is not particularly limited, and is used in the same manner as known antibacterial agents, disinfectants, disinfectants, and antifungal agents for the purpose of antibacterial, sterilizing, disinfecting, and antifungal. can do. For example, commonly employed methods such as a method of spraying on an object to be subjected to antibacterial treatment, a method of applying, a method of impregnating the object, and a method of immersing the object can be used as they are. Applications include medical cleaning agents for the purpose of disinfecting and cleaning medical instruments and affected areas, household cleaning agents for sterilizing and cleaning dishes, body cleaning agents, food industry cleaning agents, and lubricants for container transfer conveyors. Antibacterial agent for antibacterial processing of food packaging film, fiber, synthetic resin, wood, daily necessities, cosmetics, softener for clothing, wet or non-aqueous paint, non-woven fabric, wet tissue or toilet seat cleaner, fiber When used as an antibacterial agent, all fibers such as cotton, polyester, acrylic and nylon may be treated by a general method such as stirring, dipping or spraying. Moreover, it can also apply | coat or spray on the surface for wood, daily necessities, etc. Furthermore, when using about synthetic resin etc., you may make it adhere to the surface by apply | coating or spraying after shaping | molding, and can also knead | mix at the time of a shaping | molding process etc. in order to maintain an antimicrobial effect. Among these, since the antibacterial composition of the present invention has high safety to the human body, it is preferable to use it for those directly touching the human body such as cosmetics and cleaning agents.

  The cosmetic of the present invention is a cosmetic containing the antibacterial agent or antibacterial composition of the present invention. Such cosmetics include, for example, face-wash cream, face-wash foam, cleansing cream, cleansing milk, cleansing lotion, massage cream, cold cream, moisture cream, shaving cream, sunscreen cream, hair nourishing agent, hair cream, hair liquid, set lotion, Hair bleach, color rinse, permanent wave liquid, hand cream, lipstick, various packs, foundation, lotion, cosmetic liquid, milky lotion, eau de cologne, nail cosmetics, shampoo, rinse, etc. Is 0.001 to 10% by mass, preferably 0.001 to 3% by mass, more preferably about 0.01 to 2% by mass.

  Furthermore, the cleaning agent of the present invention is a cleaning agent containing the antibacterial agent or antibacterial composition of the present invention and a surfactant. Examples of such cleaners include household cleaners such as kitchen cleaners, toilet cleaners, and bath cleaners; body cleaners such as shampoos, hand soaps, and body soaps, and the antibacterial agent of the present invention. Is about 0.001 to 10% by mass, preferably about 0.001 to 3% by mass, and more preferably about 0.01 to 2% by mass.

  Examples of the surfactant that can be used in the cleaning agent of the present invention include an anionic surfactant, a cationic surfactant, and a nonionic surfactant. Among these, it is particularly preferable to use an anionic surfactant or a nonionic surfactant for the cleaning agent of the present invention.

  Examples of the anionic surfactant include higher fatty acid salts, higher alcohol sulfate esters, sulfurized olefin salts, higher alkyl sulfonates, α-olefin sulfonates, sulfated fatty acid salts, sulfonated fatty acid salts, and phosphate esters. Salt, sulfate ester of fatty acid ester, glyceride sulfate ester salt, sulfonate salt of fatty acid ester, α-sulfo fatty acid methyl ester salt, polyoxyalkylene alkyl ether sulfate ester salt, polyoxyalkylene alkyl phenyl ether sulfate ester salt, polyoxy Alkylene alkyl ether carboxylates, acylated peptides, sulfate esters of fatty acid alkanolamides or their alkylene oxide adducts, salts of sulfosuccinates, alkyl benzene sulfonates, alkyl naphthalene sulphate Honates, alkylbenzimidazolesulfonates, polyoxyalkylenesulfosuccinates, N-acyl-N-methyltaurine salts, N-acylglutamic acids or salts thereof, acyloxyethanesulfonates, alkoxyethanesulfonates, N -Acyl-β-alanine or its salt, N-acyl-N-carboxyethyltaurine or its salt, N-acyl-N-carboxymethylglycine or its salt, acyl lactate, N-acyl sarcosine salt, and alkyl or alkenyl Examples thereof include aminocarboxymethyl sulfate. Counter ions of such anionic surfactant salts include alkali metal ions such as lithium, sodium and potassium; alkaline earth metal ions such as calcium and magnesium; ammonium; monoethanolammonium, diethanolammonium and triethanolammonium And organic ammonium such as monoisopropanolammonium, diisopropanolammonium and triisopropanolammonium.

  As the higher fatty acid salt, a salt of a fatty acid having 12 to 18 carbon atoms is preferable, and coconut oil fatty acid salt, dodecanoate, tetradecanoate, hexadecanoate, and oleate are more preferable. Similarly, as the higher alkyl sulfate salt, alkyl having 10 to 18 carbon atoms is preferable, and one having 12 to 16 carbon atoms is more preferable. The polyoxyethylene alkyl ether sulfate ester salt preferably has 10 to 18 carbon atoms, and more preferably 12 to 16 carbon atoms. Moreover, 1-12 are preferable, as for the average degree of polymerization of a polyoxyethylene group, 2-10 are more preferable, and 3-8 are still more preferable.

  Among these anionic surfactants, since they are less irritating to the skin etc., higher fatty acid salts, higher alkyl sulfate esters, α-sulfo fatty acid methyl ester salts, higher alcohol sulfate esters, polyoxyethylene alkyl ethers Sulfuric acid ester salts, polyoxyethylene sulfosuccinic acid alkyl ester salts, and monoalkyl phosphoric acid ester salts are preferable, and higher fatty acid salts, higher alkyl sulfuric acid ester salts, and polyoxyethylene alkyl ether sulfuric acid ester salts are more preferable. For the same reason, sodium ions, potassium ions, ammonium and triisopropanolammonium are preferred as the counter ion of the salt of the anionic surfactant.

  Nonionic surfactants include, for example, polyoxyalkylene alkyl ethers, polyoxyalkylene alkenyl ethers, polyoxyethylene polyoxypropylene alkyl ethers (the addition form of ethylene oxide and propylene oxide is either random or block). Polyethylene glycol propylene oxide adduct, polypropylene glycol ethylene oxide adduct, glycerin fatty acid ester or its ethylene oxide adduct, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, alkyl polyglucoside, sucrose fatty acid ester, alkyl ( Poly) glycerin ether, polyglycerin fatty acid ester, polyethylene glycol fatty acid ester, fatty acid methyl ester Ethoxylates and the like.

  Among such nonionic surfactants, polyoxyethylene alkyl ether is preferable, and polyoxyethylene (average addition mole number of ethylene oxide is preferably 4 to 18) alkyl (preferably 12 to 16 carbon atoms) ether is more preferable. preferable. In addition, said surfactant can be used also for the cosmetics of this invention.

  In addition to the surfactant component described above, the cosmetic and cleaning agent of the present invention are other components, for example, silicone oils, thickeners, oils, powders (pigments, pigments) as long as the object of the present invention is not impaired. Resin), other antibacterial agents, fragrances, moisturizers, physiologically active ingredients, salts, solvents, antioxidants, chelating agents, pearling agents, neutralizing agents, pH adjusters, enzymes, etc. Can do.

  Examples of the thickener include dimethyldiallylammonium chloride / acrylamide copolymer, acrylamide / acrylic acid / dimethyldiallylammonium chloride copolymer, cellulose or derivatives thereof, keratin and collagen or derivatives thereof, calcium alginate, pullulan, agar , Gelatin, tamarind seed polysaccharide, xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, caraya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, β-glucan, gellan gum And dextran.

  Examples of the oil agent include volatile and non-volatile oil agents, solvents, and resins that are usually used in cosmetics. The oil agent may be a liquid, a paste, or a solid at room temperature, but a liquid that is excellent in handling is preferable. Examples of the oil agent include higher alcohols such as cetyl alcohol, stearyl alcohol, isostearyl alcohol, lauryl alcohol, behenyl alcohol, octyldodecanol, and lanolin alcohol, fatty acids such as isostearic acid, undecylenic acid, and oleic acid, myristyl myristate, and lauric acid. Esters such as hexyl, decyl oleate, isopropyl myristate, hexyl decyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, ethylene glycol monostearate, octyl oxystearate, hydrocarbons such as liquid paraffin, petrolatum, squalane , Wax such as beeswax, lanolin, reduced lanolin, carnauba wax, mink oil, cocoa butter, coconut oil, palm kernel oil, camellia oil, egoma oil, castor oil, Leave oil, corn oil, jojoba oil, oils and fats of rapeseed oil, and the like.

  Examples of the powder include pigments such as red No. 201, yellow No. 4, blue No. 1, black No. 401, lake pigments such as yellow No. 4 Al lake, yellow No. 203 Ba lake, nylon powder, silk powder, and silicone powder. , Polymers such as cellulose powder, silicone elastomer spherical powder, polyethylene powder, yellow iron oxide, red iron oxide, chromium oxide, carbon black, colored pigments such as ultramarine and bitumen, white pigments such as zinc oxide and titanium oxide, talc Body pigments such as mica, sericite and kaolin, pearl pigments such as mica and titanium, metal salts such as barium sulfate, calcium carbonate, magnesium carbonate and magnesium silicate, inorganic powders such as silica and alumina, bentonite, smectite and nitriding Boron etc. are mentioned. There are no particular restrictions on the shape of these powders (spherical, rod-like, needle-like, plate-like, indeterminate, flake-like, spindle-like, etc.).

  These powders are treated with conventionally known surface treatments such as fluorine compound treatment, silicone treatment, silicone resin treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil agent treatment, N-acylated lysine treatment, Surface treatment may be performed in advance by acrylic acid treatment, metal soap treatment, amino acid treatment, inorganic compound treatment, plasma treatment, mechanochemical treatment, or the like.

  Other antibacterial agents include, for example, paraben antibacterial agents such as methylparaben and ethylparaben; imidazole antibacterial agents such as thiabendazole and 2-benzimidazolylcarbamate methylpreventol; and carbanilides such as trichlorocarbanilide and cloflucarban Antibacterial agents; thiazole antibacterial agents such as benzothiazole; triazine antibacterial agents such as debuconazole and cabinone; biguanide antibacterial agents such as chlorhexidine hydrochloride and polyhexamethylene biguanide, etc. Should be used with caution in consideration of irritation to the human body.

  Examples of humectants include biopolymers such as diethylene glycol monoethyl ether, deoxyribonucleic acid, mucopolysaccharide, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, amino acids, sodium lactate, Examples include urea, sodium pyrrolidonecarboxylate, betaine, and whey.

  Examples of the solvent include purified water, ethanol, light liquid isoparaffin, lower alcohol, ethers, LPG, fluorocarbon, N-methylpyrrolidone, fluoroalcohol, and next-generation chlorofluorocarbon.

  Hereinafter, the present invention will be specifically described by way of examples. In the following examples and the like,% and ppm are based on mass unless otherwise specified.

<Compounds used in the experiment>
A component (product of the present invention)
(A-1) 3-cyclohexyloxy-1,2-propanediol (A-2) 3- (4-methylcyclohexyloxy) -1,2-propanediol (A-3) 3- (4-t-butyl Cyclohexyloxy) -1,2-propanediol (A-4) 3-cyclohexylmethoxy-1,2-propanediol (A-5) 3-cyclohexyloxy-1,2-propanediol and 2-cyclohexyloxy-1 , 3-propanediol 1: 1 (molar ratio) mixture chelating agent (component B):
(B-1) disodium ethylenediaminetetraacetate (B-2) tetrasodium glutamate diacetate low molecular weight polyol (component C):
(C-1) 1,3-butanediol (C-2) glycerol nitrogen-containing nonionic surfactant (component D):
(D-1) Palm fatty acid monoethanolamide (D-2) Lauramidopropylamine oxide (3-dodecylamidopropyl-N, N-dimethylamine oxide)
(D-3) POE (3) laurylamine nitrogen-containing amphoteric surfactant (E component):
(E-1) Palm oil fatty acid amide ethyl hydroxyethyl glycine sodium (sodium cocoamphoacetate)
Plant-derived extract (F component):
(F-1) Chamomile extract (F-2) Camelis extract (F-3) Brown algae extract zinc compound (G component):
(G-1) Zinc sulfate (G-2) Zinc p-phenolsulfonate The plant-derived extracts (F-1) to (F-3) are liquids containing water or organic solvents. Was formulated based on the solid content from which these water and organic solvents were removed.

H component (comparative component)
(H-1) 3-n-octoxy-1,2-propanediol (H-2) 1,2-decandiol (H-3) 1- (2-hydroxyethoxy) -2-decanol (H-4) Methyl paraben

<Example 1>
Antibacterial test (minimum growth concentration) -1 (Evaluation with a single product)
Using the bacterial solution which had been pre-cultured in broth medium, the bacterial solution which had been adjusted to 10 ⁷ levels, placed in 0.27ml microplate, the A~C component was adjusted to various concentrations between 10240~0.625μg / ml Was added and stirred well. This mixed solution was cultured at 37 ° C. for 24 hours. After completion of the culture, the turbidity of the microplate was measured, and the minimum concentration of the preservative that inhibited the growth of the test bacteria was defined as the minimum growth concentration (MIC). The fungi used are as follows. The results are shown in Table 1.
Bacteria 1: Bacillus subtilis IFO3134 (B. subtilis)
Fungus 2: Escherichia coli ATCC 14948 (Escherichia coli)
Fungus 3: Staphylococcus aureus IFO13276 (S. aureus)

  From the above results, it can be seen that the antibacterial agent of the present invention has an antibacterial property equivalent to or higher than that of methylparaben (H-4). Moreover, it was confirmed that the antibacterial property is high even when compared with (H-1) to (H-3) which are approximate compounds.

<Example 2>
Antibacterial test (minimum growth concentration) -2 (evaluation in combination system)
MIC was measured by blending B to F components diluted to the same concentration at a ratio shown in the table below with respect to 100 parts by mass of the A component diluted to various concentrations in the above test. However, the number of MIC is expressed by the concentration of the A component, and the antibacterial synergistic effect by blending the B to F components is confirmed. The results are shown in Table 2.

  From the above results, it was confirmed that the antibacterial property of the present invention is improved by using the B component to the F component in combination rather than using the antibacterial agent alone.

<Example 3>
Skin irritation test The above compounds were evaluated for skin irritation by a patch test. That is, 100 mg of the above compound was applied to the gauze part of the adhesive bandage for patch test and pasted on the back side of the upper arm part. After 48 hours, the adhesive bandage was peeled off and left for 3 hours, and then the presence or absence of erythema was visually observed. The test was conducted on 40 people and evaluated according to the following criteria. The results are shown in Table 3.
(Evaluation criteria)
A: No one had erythema.
○: There were 1 to 3 people with erythema.
Δ: There were 4 to 7 people with erythema.
X: There were 8 or more people with erythema.

  From the above results, it was confirmed that the safety of the present invention was higher than that of parabens.

<Example 4>
Usability test A lotion was prepared with the following composition. To 20 female monitors, after washing the face, lotion was applied to the face, and the feeling of use was evaluated according to the following criteria. The results are shown in Table 3.
○: Everyone feels uncomfortable on the coated part and excellent in usability.
Δ: 1 to 3 people feel uncomfortable at the coated part, and the feeling of use is slightly inferior.
X: Four or more people feel a sense of incongruity in the application part, and the usability is inferior.

＊比較品：１，２−オクタンジオール、ｎ−グリセリルエーテル <Composition and amount other than component A>

* Comparative products: 1,2-octanediol, n-glyceryl ether

以上の結果により、本発明は従来のアルカンジオール類・エーテル類に比べ、化粧品等に配合した際の使用感等も優れていることが確認された。

From the above results, it was confirmed that the present invention is superior in the feeling of use when blended in cosmetics and the like as compared with conventional alkanediols and ethers.

Claims (10)

The following general formula (1) and / or (2)

(In the formula, R and R ′ each represent an independent hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R ″ represents an alkylene group having 1 to 3 carbon atoms, and n represents a number of 0 or 1. An antibacterial agent characterized by comprising a compound represented by (A) The antibacterial agent of Claim 1 as a component, and the following (B)-(G) component,
(B) a chelating agent,
(C) a low molecular polyol other than the general formulas (1) and (2),
(D) Nitrogen-containing nonionic surfactant (E) Nitrogen-containing amphoteric surfactant (F) Plant-derived extract (G) The component contains one or more components selected from the group consisting of zinc compounds. An antibacterial composition characterized by the above.   The antibacterial composition according to claim 2, wherein the chelating agent of the component (B) is 0.5 to 500 parts by mass with respect to 100 parts by mass of the component (A).   The antibacterial composition according to claim 2, wherein the low molecular polyol of the component (C) is 0.5 to 500 parts by mass with respect to 100 parts by mass of the component (A).   The antibacterial composition according to claim 2, wherein the nitrogen-containing nonionic surfactant of the component (D) is 0.5 to 500 parts by mass with respect to 100 parts by mass of the component (A).   The antibacterial composition according to claim 2, wherein the nitrogen-containing amphoteric surfactant of the component (E) is 0.5 to 500 parts by mass with respect to 100 parts by mass of the component (A).   The antibacterial composition according to claim 2, wherein the plant-derived extract of the component (F) is 0.1 to 1000 parts by mass with respect to 100 parts by mass of the component (A).   The antibacterial composition according to claim 2, wherein the zinc compound of component (G) is 0.02 to 10 parts by mass with respect to 100 parts by mass of component (A).   A cosmetic comprising the antibacterial agent according to claim 1 or the antibacterial composition according to any one of claims 2 to 8.   A cleaning agent comprising the antibacterial agent according to claim 1 or the antibacterial composition according to any one of claims 2 to 8.