JP2007016018A - Antibacterial agent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an antibacterial agent having antibacterial property higher than that of parabens and excellent in safety. <P>SOLUTION: The antibacterial agent comprises a compound represented by formula (1) (wherein, R<SP>1</SP>is a 4-8C alkyl; and A is a residue removed of one hydroxy from an alcohol having ≥3 hydroxy groups) and/or a compound represented by formula (2) (wherein, R<SP>2</SP>is a 4-8C alkyl; and A is a residue removed of one hydroxy from an alcohol having ≥3 hydroxy groups). <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an antibacterial agent that is highly safe for the human body and has antibacterial properties equivalent to or higher than those of parabens.

  Parabens and the like are used as antibacterial agents in cosmetics (including quasi drugs) and detergents. However, parabens have the disadvantage that the use concentration range is limited due to high skin irritation and low safety, so the use limit concentration of parabens is 1%. In addition, there is a tendency to increase the number of people who cause allergic reactions to parabens, and there is a growing demand for cosmetics that are not formulated with parabens at all, or that the amount of parabens is reduced. It has increased.

（請求項１）；防腐殺菌剤として請求項１記載の防腐殺菌剤を配合したことを特徴とする化粧料組成物（請求項２）；メチルパラベンの配合量が組成物中０．２重量％未満であることを特徴とする請求項２記載の化粧料組成物（請求項３）が開示されている。 Therefore, it is known to reduce the blending amount of parabens by using parabens in combination with alkanediols and alkyl glyceryl ethers. For example, Patent Document 1 discloses at least one paraben represented by the following formula 1 (Chemical Formula 1), 1,2-pentanediol represented by the following Formula 2 (Chemical Formula 2), and Formula 3 (Chemical Formula 3). 1,2-hexanediol represented by the following formula (Chemical Formula 4) and one or more of 1,2-octanediol represented by the following formula (Formula 4): R in 1 represents an alkyl group having 1 to 4 carbon atoms).

(Claim 1); a cosmetic composition characterized in that the antiseptic disinfectant according to claim 1 is incorporated as an antiseptic disinfectant (Invention 2); the amount of methylparaben is less than 0.2% by weight in the composition A cosmetic composition according to claim 2 (claim 3) is disclosed.

  Patent Document 2 discloses the following components (A) and (B): (A) an antibacterial substance (B) an antibacterial composition containing a divalent or higher valent organic acid having a pKa1 value of 4 to 7 ( Claim 1); Component (A) is paraoxybenzoates, benzoic acid and salts thereof, phenoxyethanol, mono fatty acid (carbon number 8-12) glycerin ester, mono fatty acid (carbon number 8-12) polyglycerin ester, The antibacterial composition (Claim 2) according to claim 1, which is selected from the group consisting of monoalkyl (carbon number 8 to 12) glyceryl ether and alcohol; component (B) is succinic acid, adipic acid or cis The antibacterial composition according to claim 1 or 2, which is hexahydrophthalic acid; 0.005 to 10% by weight of component (A) and 0.001 to 10% by weight of component (B). One of 3 The antimicrobial composition of claim wherein (claim 4) is disclosed.

Japanese Patent Laid-Open No. 11-310506 JP, 2002-322090, A Claims

  However, even when parabens are used in combination with alkanediols or alkyl glyceryl ethers, the antibacterial properties are not sufficient, and parabens cannot be reduced so much in order to ensure the necessary antibacterial properties.

  Accordingly, an object of the present invention is to provide an antibacterial agent having antibacterial properties equal to or higher than parabens and having high safety.

（Ｒ^１は炭素数４〜８のアルキル基を表わし、Ａは３価以上のアルコールから１つの水酸基を取り除いた残基を表わす。）で表わされる化合物、及び／又は下記の一般式（２）

（Ｒ^２は炭素数４〜８のアルキル基を表わし、Ａは３価以上のアルコールから１つの水酸基を取り除いた残基を表わす。）で表わされる化合物からなることを特徴とする抗菌剤に係るものである。 In view of the above-described problems, the present inventors have intensively studied, and as a result, have found an antibacterial agent having an antibacterial property equivalent to or higher than that of parabens, and have reached the present invention.
That is, the present invention provides the following general formula (1)

(R ¹ represents an alkyl group having 4 to 8 carbon atoms, and A represents a residue obtained by removing one hydroxyl group from a trivalent or higher valent alcohol) and / or the following general formula (2)

(R ² represents an alkyl group of 4-8 carbon atoms, A represents. The residue obtained by removing one hydroxyl group from trihydric or higher alcohols) according to an antibacterial agent characterized by comprising a compound represented by Is.

  The effect of the present invention is to provide an antibacterial agent having antibacterial properties equivalent to or higher than those of parabens and having high safety.

In the general formulas (1) and (2), R ¹ and R ² represent an alkyl group having 4 to 8 carbon atoms. Examples of the alkyl group having 4 to 8 carbon atoms include butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, isopentyl group, secondary pentyl group, neopentyl group, tertiary pentyl group, hexyl group, Secondary hexyl group, heptyl group, secondary heptyl group, octyl group, 2-ethylhexyl group, secondary octyl group and the like can be mentioned.

Among these alkyl groups, an alkyl group having 5 to 7 carbon atoms is more preferable, and an alkyl group having 6 carbon atoms is most preferable because of good antibacterial properties. In addition, a linear alkyl group is more preferable than a branched alkyl group because of good antibacterial properties. When the carbon number of R ¹ and R ² is less than 4, the antibacterial property is weak and thus cannot be used practically. When the carbon number exceeds 8, the antibacterial property is weakened and the solubility in water is low. Since it becomes bad and it becomes difficult to mix | blend with the product of aqueous solution, it is not preferable.

  In the general formulas (1) and (2), A is a residue obtained by removing one hydroxyl group from a trivalent or higher alcohol. Examples of the trivalent or higher alcohol represented by A-OH include 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, trimethylol Ethane, 2,3,4-hexanetriol, 2-ethyl-1,2,3-butanetriol, trimethylolpropane, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3 , 4-pentanetriol and other trihydric alcohols; pentaerythritol, 1,2,3,4-pentatetrol, 2,3,4,5-hexatetrol 1,2,4,5-pentanetetrol, 1,3,4,5-hexanetetrol, diglycerin, sorbitan, N, N, N ′, N′-tetrakis (2-hydroxybutyl) ethylenediamine, N, Tetrahydric alcohols such as N, N ′, N′-tetrakis (hydroxyethyl) ethylenediamine; pentahydric alcohols such as adonitol, arabitol, xylitol, triglycerin; dipentaerythritol, sorbitol, mannitol, iditol, inositol, dulcitol, talose, Examples include hexahydric alcohols such as allose. Examples of the alcohol having a valence of 7 or more include polymers such as polyglycerin and oligosaccharide. Among these alcohols, since antibacterial properties are good, trivalent to hexavalent alcohols are preferable, trivalent alcohols are more preferable, and glycerin is most preferable.

Examples of the method for producing the compound represented by the general formula (1) and / or (2) include R ¹ CH (OH) CH ₂ (OH) and / or R ² CH (OH) CH ₂ (OH). A method in which a diol compound represented by the formula (I) and a polyol compound represented by A-OH are subjected to a dehydration condensation reaction, represented by R ¹ CH (OH) CH ₂ (OH) and / or R ² CH (OH) CH ₂ (OH) A method in which a diol compound and a halogenated polyol represented by AX (X is a halogen atom such as Cl and Br) are subjected to a condensation reaction with an alkali, R ¹ CH (OH) CH ₂ X and / or R ² CH ₂ CH ( OH) a method in which a compound represented by X and a polyol compound represented by A-OH are subjected to a condensation reaction with an alkali, 1,2-epoxy compounds such as α-olefin oxide and glycidol, The method or the like to an epoxy ring-opening reaction of the polyol compound represented by -OH and the like. In addition, a method of performing the above reaction using a partially esterified polyol compound represented by A-OH with a lower fatty acid and saponifying after completion of the reaction, or a polyol compound represented by A-OH If the above-mentioned reaction is carried out using a partially ketalized product and the ketal is removed after completion of the reaction, a product with high purity can be obtained. Among these, since reaction is easy, it is preferable to manufacture using a 1, 2- epoxy compound. When a 1,2-epoxy compound is used, for example, when an alkali catalyst is used, a compound represented by the general formula (1) can be formed as a main component, and when an acidic catalyst is used, a compound represented by the general formula (2) as a main component. Can do. The 1,2-epoxy compound can be obtained by oxidizing the terminal olefin compound with an oxidizing agent such as hydrogen peroxide. These may be purified and isolated by a method such as recrystallization or distillation, or may be used as a mixture as it is.

  As a method for causing the epoxy ring-opening reaction of the α-olefin oxide and the polyol compound represented by A-OH, the reaction may be carried out at a high temperature of 200 ° C. or more without a catalyst, but the condensation reaction of polyols occurs due to the high temperature. There is a case. Therefore, it is preferable to use a catalyst to lower the reaction temperature. Examples of catalysts include mineral acids such as sulfuric acid, hydrochloric acid, nitric acid and phosphoric acid; sulfonic acid compounds such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and m-xylenesulfonic acid; boron trifluoride and tin chloride Lewis acids such as iron chloride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide; trimethylamine, triethylamine, tributylamine, N, N, N ′, N ′ -Tetramethyl-1,2-ethylenediamine, N, N, N ′, N′-tetraethyl-1,2-ethylenediamine, N, N, N ′, N′-tetramethyl-1,6-hexanediamine, etc. 3 amine compounds; tetramethylammonium hydride, tetraethylammonium hydride, tetrabutylammonium Ammonium hydride such as Idoraido like. Moreover, you may use simultaneously the solvent which does not inhibit reactions, such as toluene and hexane.

  As a specific reaction method using a catalyst, for example, in the case of an acid catalyst, 0.001 to 5 mass% is added to the reaction system, and the reaction is performed at a reaction temperature of 10 to 90 ° C. for 1 to 5 hours. What is necessary is just to remove a catalyst, and in the case of an alkali catalyst, 0.001-5 mass% is added with respect to a reaction system, it reacts at reaction temperature 100-180 degreeC for 2 to 20 hours, and what is necessary is just to remove a catalyst at the end.

  The amount of the antibacterial agent comprising the compound represented by the general formula (1) and / or the compound represented by the general formula (2) of the present invention varies depending on the use used, and is not particularly limited. In some cases, the antibacterial effect may be low, and if the amount is too large, an increase effect corresponding to the addition amount may not be obtained, so 0.001 to 10% by mass is preferable with respect to the total amount of the system to be blended, and 0.01 to 3 mass% is more preferable and 0.1-2 mass% is still more preferable.

One or more compounds selected from the group consisting of chelating agents, low molecular polyols, nitrogen-containing nonionic surfactants, nitrogen-containing amphoteric surfactants, plant-derived extracts, and zinc compounds in the antibacterial agent of the present invention If it contains, the antibacterial effect will increase.
Examples of chelating agents 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, phosphoric acid chelating agents, Examples include hydroxycarboxylic acid chelating agents, polymer electrolyte (including oligomer electrolyte) chelating agents, dimethylglyoxime, ascorbic acid, thioglycolic acid, phytic acid, glyoxylic acid, and glyoxalic acid. 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 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 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 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. Therefore, the blending amount of the chelating agent is the general formula (1) and / or the general formula (2). 0.5 parts by mass or more is preferable with respect to 100 parts by mass of the antibacterial agent comprising the compound represented by In addition, when the amount of chelating agent is increased, the antibacterial property is improved accordingly, but when the chelating agent exceeds a certain amount, the antibacterial property is not decreased, but the antibacterial property is not improved further. There is. Therefore, the blending amount of the chelating agent is more preferably 0.5 to 500 parts by mass, and 1 to 200 parts by mass with respect to 100 parts by mass of the antibacterial agent composed of the compound represented by the general formula (1) and / or the general formula (2). Part is more preferable, and 2 to 50 parts by mass is most 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.

  Examples of the low molecular polyol include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene 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-pentanediol, 2-methyl-1,2-butanediol, 2-methyl-2,3- Butanediol, 2-methyl-1,4-butanediol, 3-methyl Ru-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-hexanediol, 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-propanediol, 2,2-dimethyl-2,4-butanediol, 2,3-dimethyl-1,2-butane All, 1,2-heptanediol, 1,7-heptanediol, 3,4-heptanediol, 2-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-propane Diol, 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-propanedioe 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-octanediol, 1,2-undecanediol, 1,4-undecanediol, 1,11-undecane Diol, 6-ethyl-3-methyl-1,6-octanediol, 1,2-dodecanediol, 1,10-dodecanediol, 1,12-dodecanediol, 2,4 Diethyl-1,5-octanediol, 2,8,8-trimethyl-2,7-nonanediol, 1,2-tetradecanediol, 1,14-tetradecanediol, 7,8-tetradecanediol, 1,2-pentadecane Diol, 1,2-hexadecanediol, 1,16-hexadecanediol, 1,17-heptadecanediol, 1,2-octadecanediol, 1,12-octadecanediol, 1,2-eicosanediol, 1,2- Saturated diols or condensates thereof such as 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 Alicyclic diols such as 1,5-decalindiol, limonene glycol, 1,2-terpenediol, 4,4′-bicyclohexanediol, 1,2-cyclododecanediol;

  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. Alcohols;

  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, 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-cyclohexyl glyceryl ether, 2-cyclohexyl glyceryl ether, 1-phenyl glyceryl ether, 2-phenyl glyceryl ether;

  N-substituted diethanolamines such as N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-isopropyldiethanolamine, N-butyldiethanolamine, N-cyclohexyldiethanolamine, 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, tri Propylene 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-methyl -1,3-butanediol, glycerin, sorbitol, and 1-allyl glyceryl ether are more preferable.

  The compounding amount of the low molecular polyol is not particularly limited, but if the amount of the low molecular polyol is too small, the antibacterial improvement effect may not be obtained. Therefore, the compounding amount of the low molecular polyol is the general formula (1) and / or general 0.5 mass part or more is preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by Formula (2). In addition, as the amount of low molecular polyol is increased, the antibacterial property is improved accordingly, but when the amount of low molecular polyol exceeds a certain amount, the antibacterial property is not decreased, but the antibacterial property is further improved. May not. Therefore, 0.5-500 mass parts is more preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by General formula (1) and / or General formula (2), and low molecular polyol is 1-200 mass parts. More preferred is 2 to 50 parts by mass. 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.

（Ｒ^３はアルキル基又はアルケニル基を表わし、Ｒ^４はアルキル基、アルケニル基又は−(ＣＨ₂−ＣＨ₂Ｏ)_ＸＨで表わされる基を表わし、ａ及びＸはそれぞれ１〜２０の数を表す。） Examples of the nitrogen-containing nonionic surfactant include compounds represented by the following general formulas (3) to (9):

(R ³ represents an alkyl group or an alkenyl group, R ⁴ represents an alkyl group, an alkenyl group or a group represented by — (CH ₂ —CH ₂ O) _X H, and a and X each represent a number of 1 to 20). To express.)

In the compound represented by the general formula (3), R ³ preferably has 8 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms. R ⁴ is preferably a group represented by — (CH ₂ —CH ₂ O) _X H. Further, the total value of a and X is preferably a number of 2 to 10, more preferably a number of 2 to 4.

（Ｒ^５はアルキル基又はアルケニル基を表わし、Ｒ^６は炭素数２〜６のアルキレン基を表わし、ｂ、ｃ、及びｄはそれぞれ独立した１〜２０の数を表す。）

(R ⁵ represents an alkyl group or an alkenyl group, R ⁶ 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 (4), R ⁵ preferably has 8 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms. R ⁶ 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^７はアルキル基又はアルケニル基を表わす。）

(R ⁷ represents an alkyl group or an alkenyl group.)

In the compound represented by the general formula (5), R ⁷ preferably has 8 to 22 carbon atoms, more preferably 9 to 18 carbon atoms, and still more preferably 10 to 14 carbon atoms.

（Ｒ^８はアルキル基又はアルケニル基を表わし、Ｒ^９は水素原子、炭素数１〜４のアルキル基又は−(ＡＯ)_ｙＨで表わされる基を表わし、Ａは炭素数２〜３のアルキレン基を表わし、ｅ及びｙはそれぞれ独立に１〜２０の数を表す。）

(R ⁸ represents an alkyl group or an alkenyl group, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a group represented by — (AO) _y H, and A represents an alkylene group having 2 to 3 carbon atoms. E and y each independently represents a number of 1 to 20.)

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

（Ｂ及びＦは、エチレン基又はプロピレン基を表わし、ｆ〜ｌ及びｏはそれぞれ独立した１〜２００の数を表す。ただし、ＢとＦが同じ基になることはない。）

(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 (7), 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^１０は炭素数８〜１８のアルキル基を表わす。）

(R ¹⁰ represents an alkyl group having 8 to 18 carbon atoms.)

In the compound represented by the general formula (8), 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.

（Ｒ^１１は炭素数７〜２１のアルキル基を表わす。）

(R ¹¹ represents an alkyl group having 7 to 21 carbon atoms.)

In the compound represented by the general formula (9), 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.

  Among these nitrogen-containing nonionic surfactants, compounds represented by general formulas (3), (5), (6), (8), and (9) are preferable, and general formulas (5) and (6) , (9) is more preferable, and general formula (6) is most preferable.

  The blending amount of the nitrogen-containing nonionic surfactant is not particularly limited, but if the nitrogen-containing nonionic surfactant is too small, the antibacterial improvement effect may not be obtained, so the blending amount of the nitrogen-containing nonionic surfactant is 0.5 mass part or more is preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by General formula (1) and / or General formula (2). In addition, as the amount of the nitrogen-containing nonionic surfactant is increased, the antibacterial property is improved accordingly, but when the nitrogen-containing nonionic surfactant exceeds a certain amount, the antibacterial property is not decreased, Further antibacterial properties may not improve. Therefore, the nitrogen-containing nonionic surfactant is more preferably 0.5 to 500 parts by mass with respect to 100 parts by mass of the antibacterial agent composed of the compound represented by the general formula (1) and / or the general formula (2), Part by mass is more preferable, and 2 to 50 parts by mass is most 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.

（Ｒ^１２は炭素数８〜２２のアルキル基を表わし、ｐは１〜３の数を表す。） Examples of the nitrogen-containing amphoteric surfactant include compounds represented by the following general formulas (10) to (15):

(R ¹² 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 (10), R ¹² 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^１３は炭素数７〜２１のアルキル基又はアルケニル基を表わし、ｑは２〜３の数を表す。）

(R ¹³ 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 (11), 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. The value of q is preferably 3.

（Ｒ^１４は炭素数７〜２１のアルキル基又はアルケニル基を表わし、ｒは２〜３の数を表す。）

(R ¹⁴ represents an alkyl 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 (12), R ¹⁴ 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^１５は炭素数７〜２１のアルキル基又はアルケニル基を表わす。）

(R ¹⁵ represents an alkyl or alkenyl group having 7 to 21 carbon atoms.)

In the compound represented by the general formula (13), 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.

（Ｒ^１６は炭素数８〜２２のアルキル基又はアルケニル基を表わし、ｓは２〜３の数を表す。）

(R ¹⁶ represents an alkyl 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 (14), R ¹⁶ 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^１７は炭素数７〜２１のアルキル基又はアルケニル基を表わし、ｔは２〜３の数を表す。）

(R ¹⁷ 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 (15), R ¹⁷ 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, compounds represented by general formulas (10), (11), and (12) are preferable, general formulas (11) and (12) are more preferable, and general formula (11 ) Is most preferred.

  The compounding amount of the nitrogen-containing amphoteric surfactant is not particularly limited, but if the amount of the nitrogen-containing amphoteric surfactant is too small, the antibacterial improvement effect may not be obtained. 0.5 mass part or more is preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by General formula (1) and / or General formula (2). In addition, as 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 is not decreased, Further antibacterial properties may not improve. Therefore, the nitrogen-containing amphoteric surfactant is more preferably 0.5 to 500 parts by mass with respect to 100 parts by mass of the antibacterial agent composed of the compound represented by the general formula (1) and / or the general formula (2), and 1 to 200. Part by mass is more preferable, and 2 to 50 parts by mass is most 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 is the whole plant or algae or fungi, or specific parts such as flowers, leaves, stems, fruits, bark, roots, seeds, resins, etc. From what is obtained by extracting with a solvent at normal temperature or under heating, it means what is dissolved 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 Mythonis, Alpinia Officinalum, Alfalfa (Acacia palma), 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, Opuntia Tuna, Dutch Mustard, Dutch Peonies, Olives, Origanum Heracreoticum, Orthosiphon Stamineus, Ormenis murkis , Orange, Orobankerapum, Gardenia Tahitensis, Carnation, Khaya Sene Galensis, Cacao, Oyster, Cassia, Cashew Nut, Cascara Sagrada, Cassia Italiana, Kappa Ficus Albarezi, Cattleya, Canadian Hydratis, Canary Tree, Canina Rose , Birch bamboo, turnip, cattail (cocoon), chamomile (chamomile), komi bouuki, cayupte, chrysanthemum man, oats, oats, moss Toki, guarana, garikkabara, cauliflower, karin, caruna (carrot), garcinia cambodia, carrot, crayfish, ginseng, licorice, kantachibi, kistrawberry, kiwi, kikarasuuri, chrysanthemum, kigeria africana, yellowfin aloe Quinoa, yellowfin, yellow-bellied white bean, yellow-spotted peas, millet, gymnema, yellow magnolia, cassava, cabbage, caraway, cucumber (cucumber), yellowfish, gyory, gyoryubai, kiraya, kiri, gimba, watermelon, watermelon Guava, quince seed, queercas alba, kuinoki, wolfberry, celandine, kudu, camphor, damselfly, gardenia, bearberry, kumazasa, ku Tsutsura, Anemonefish, Cumin, Clamelli Atriandra, Clara, Granbury, Chris Mummaritimum, Grindelarobusta, Clintonia Borealis, Burma Sow, Walnut, Grapefruit, Clematis, Black pepper, Blackcurrant, Black-bellied Blackberry, Globe, Blackcurrant , Caquette, Kay (Cinnamon), Geum Urbanum, Geum Rivere, Cape Aloe, Poppy, Geckavidin, Geckoge, Ghetto, Kemiyama Zorina, Gentiana, Gentiana Prostrata, Gennoshoko, Kemponashi, Koki, Kokuchitan, Koukeiten, Kou Iga , Koganebana, Coccinia Indica, Cocktan, Cochlearia officinalis, Cowberry, Coco , Gosho Strawberry, Pepper, Koshiro no Sendangsa, Cochineal Cactus, Kocho Sekkoku, Kochoran, Konara, Kochakobe, Burdock, Sesame, Wheat, Rice, Koranoki, Coriander, Coleus, Coleus Barbatus, Gorenshi, Koroha, Conzurango, Comfrey Tammicransum, Sisal Asa, Saisin, Cyperus Esculentus, Cypress, Cypress, South Rare Involcata, Saximas Button Kale, Sakura, Sakurabukanboku, Pomegranate, Sugar Maple, Sugarcane, Sugar Pine, Sasanca, Sassafrasoki, Saffron, Sabon Soup Salix nigra, crape myrtle, sanguinaria canadensis, hawthorn, sansikisumire, sanchinin carrot, sanshuyu, sansho , Sunpens, Citea medullaris, Cyanotis Arachnoidea, Shea butter, Shiozaki, Shisimbrium Irio, Sistrose (Rabdanum), Sistus smuperiensis, Sisturanifels, Perilla, Sichenge, Linden, Shimbugi, Gypterix Odrata, Siberian fir, Shimalba, Shimifugadafurika, Shimotsukeso, potato, peonies, jasmine, janohige, janomerica, shukusha, juzudama, shukkonikamisou, juniper mexicana, junesai, ginger, shozuk Dioscorea, Birch, Silane, Logaris, White-faced Silica, White-faced Lupine, White-faced Cotton, Shinkonakarisaya, Synthpalm dulcificum, Symbidium , Symprocosacemosa, Sweet Acacia, Watermelon, Honeysuckle, Scabiosa Albensis, Sugina, Scutellaria Galericulata, Stevia, Strobe Pine, Spiny Bamboo, Spirulina Platensis, Spirulina Maxima, Suveruhiyu, Sperm Wheat, Sumilux Alice, Sumilux Alice Trothiaehoria, Acacia, Acacia, Acacia, Nettle, Psyllium psyllium, Hypericum perforatum, Acacia serrata, Acacia serrata, Acacia caladium, Acacia carrot, Acacia vulgara, Acacias edulis, Acacias azalea , Linden tree, white willow, dandelion, boxwood, horse chestnut, seiyo Sea urchins, pears, eustoma, rowan, ceylon nikki, elderflowers, carrots, gerbils, yarrow, hazel, antelope, holly, holly, cherry blossoms, primroses, primroses Strawberry, Ceylon Nikkei, Sage, Cecropia obtusifolia, Sequoia cedar, Cecil Oak, Sedum Purpleum, Zeniaoi, Senega, Geranium, Sercidium Florida, Cereus grandiflorus, Celery, Senkyu, Centifolia rose, Centipeda Cunninghammy, Senninkoku, Sempukuka, Semburi, Sojutsu, Sawakuhi, Saw Palmetto, Sokei, 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, Tea (tea), Chaboteisou, Tuberose, Clove, Datura, Chung bean, Chileatmentosa, Tsukushimanabeetsubi, Tsukubakusa, Tsurugumi, Tsurugukudami, Tsurureishi, Tea Tree, Dioscorea Composita, Dioscoreavirosa, Dioscorea mexicana, Teuchigurumi, Tecoma clear squirrel, Tetsuzainoki, Duke, DuBoisley Cardiac, Terminaria, Tencha, Germany Spruce, German spruce, Capsicum, Capsicum, Toki, Toki-Senka, Tonin, Capsicum spruce, Spruce, Corn, Corn silk, Capsicum, Tosa, Dokudami, Dokuninjin, Toshi (Plum), Tomato, Tomato, Trigonellafoenum Tormentilla, Toro-Aoimodoki, Nagabagi-shigishi, Nagii-kada, eggplant, natsuna, jujube, feverfew, jujube, jujube, jujube, nanyo-sou, nanbanai, nanbansafuji, nioisumire, niyu-teigai Leek, carrot, garlic, nymphea alba, white deer, white rose, white rose, white violet, wild rose, wild rose, pineapple, high Viscous, Pinus, Baobab, Bacchusia triodora, Bacmondo, Bacopamonniera, Hagoromogusa, Lotus, Parsley, Patchouli, Pepper crab, Baccarius genisteroides, Passiflora arata, pearl barley, banana, Hanahaku, honeysuckle, vanilla, vanilla Cis, Hanesenna, Papaya, Paphiopedilum Maudiae, Haberlea Rhodopensis, Hermanus, Hamamelis, Hayatouri, Rose, Parietalia, Harienju, Harpagophyta, Palmarosa, Baros Mabetzulina, Van Turmeric, Pansy, Bambara Egret, Beet, Holly , Bitter almond, bitter orange, hydrastis canadensis, daisies, daisies, binankazura, pinusheda, hinoki Ki, Hibamata, daisies, Hipofaerarum noides, sunflowers, Himekouji, Himekora, Himetsunichinichiso, Himena Air Kulbaril, Himefuuro, Sandalwood, Chickpea, Hiramame, Himehariso, Bellows, Pirocarpus pirophyrus Paniculata, Fusenkazura, Pueraria Mirifica, Ferula Garvaniflua, Bukit Dandelion, Bukkuri, Fusazaki Sesen, Fusagisuri, Fusagifugi, Fusanus Spicatus, Petit Glen, Petit Petalum Orakoides, Bussouge, Butcher Bloom, Pterocarp Grapes, beetle, beech, scallops, scallops, scallops, fragalia chiroensis, brazil nuts, french caigan Leopard, French lavender, Plantago goat, Plantago gossip, Plantago gossilium, Primula shikimensis, Prunes, Prunus africana, Prunus serotica, Plumeria, Plectrants barbatas, Bretcia hyacinthina, Propolis, Bay, Hayflower, Hazelnut , Pecan, vetiver, loofah, penny royal mint, garlic, safflower, safflower assembly, pepo pumpkin, hera plantain, pelargonium capitatum, helicrism arenarium, helicopter angstiphorium, helichmus italicum, bergamotchi peltholda , Peruvian balsam, Bergamot, Berberis aquiholium, Veronica kaficinaris, henna, henrouda, broomfish, boushuboku, boushunka,
Spinach, spinach, spinach, hawkweed, honoki, Hokubayofuroso, bocoa prouasensis, boswellia serrata, hosobasena, josobabarengiku, bodaiju, button, hop, poterium officinale, jojoba, polygonum mulchiflorum, boulder, pom , Magnolia Officinalis, Magnolia Biondi, Magwa, Magella, Masaki, Madake, Pine, Matsurika, Matecha, Madonna Lily, Majorana, Maria Thistle, Malpigia grabra, Quince, Marronie, Mango, Mangosteen, Manscapella , Manjugiku, Mandarin Orange, Mandrake, Mishima Psycho, Mizuhakka, Mizu Lemon, Michiyanagi, Mitsugashi, Mitra Carpath Skaba , Mimosa Tenui Flora, Myrcia duvia, Myrrh (Mulaceae), Mirotamnus flaverifolia, Mirobaran, Mukuroji, Murasaki, Murasakikib, Murasakikiburi, Murasakibareniku, Murayako Enji, Meboki, Memyo rush, Melia azajirakuta , Merirot, Melosria, Melon, Mentaalbensis, Moukomomogi, Mourera fulviachiris, magnolia, moscata rose, moss bean, motsuyakuju, peach, momotana, yak moso, cornflower, yashabushi, yachiyanagi, mugwort, mugwort Yugao, Eucalyptus, Eupatium Ayapana, Eupatium Rebaudian Mumbertoni, Yukinoshita, Yuzu, Yuso I, Yucha, Yucca Grauca, Yukka Shijigera, Lily, Yotsutsurumkinbai, Yuzusukikiki, Yorus pokeweed, European red-billed ginseng, European raspberry, European red chestnut, European black porcupine, European white birch, European beech, European mantis, European fir, Artemisia , Artemisia, Lychee, Lima Bean, Lime, Rye, Lilac, Radiata Pine, Latania, Peanut, Ranunculus Ficaria, Labandula Hybrida, Raffma, Lavender, Larix Europaea, La Rare di Balikata, Rare Mexicana, Rambutan, Riso, lysosamnium calcolumn, lithoea glutinosa, longan, lirios omabataki, apple, rooibos, lupine bucarnos , Lubusviros, Lumpuyan, Borage, Rurihienso, Respeda, Lesedar Teora, Lettuce, Redama, Redam Pulse Tre, Lebanese Cedar, Levischium Officinale, Lemon, Lemongrass, Forsythia, Rosewood, Rosemary, Low Bush Blueberry, Rome Plants such as chamomile, laurel, logwood, robusta coffee, wild thyme, wasabi, horseradish, wasabi, cottonweed, cotton bud, walteria indica, walmocow;

  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 amount of the plant-derived extract is too small, the antibacterial improvement effect may not be obtained. Therefore, the blending amount of the plant-derived extract is the general formula (1) and / or general 0.1 mass part or more is preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by Formula (2). In addition, 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 is not decreased, but the antibacterial property is further improved. May not. Therefore, as for a plant origin extract, 0.1-1000 mass parts is more preferable with respect to 100 mass parts of antibacterial agents consisting of a compound denoted by general formula (1) and / or general formula (2), and 0.5-200 masses. Part is more preferable, and 1 to 100 parts by mass is most 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.

  Zinc compounds include, for example, zinc acetate, zinc laurate, zinc myristate, zinc palmitate, zinc ricinoleate, zinc undecylenate, zinc aspartate, zinc acetylmethionine, zinc gluconate, zinc citrate, polypyrrolidone carboxylic acid Organic acid zinc salts such as zinc and zinc picolinate; Zinc sulfonic acid zinc salts such as zinc p-phenolsulfonate, Ascorbyl zinc phosphate, Sodium cetyl phosphate, zinc zinc phosphate such as DNA zinc; Zinc pyrithione and other zinc complexes Zinc supported zeolite such as (silver / zinc / ammonium) zeolite and silicic acid (ammonium / silver / zinc / aluminum); aluminum hydroxide such as aluminum oxide / zinc, aluminum oxide / zinc / cerium, aluminum oxide / zinc / iron Baked products such as sulfuric acid , Zinc sulfide, Zinc chloride, Zinc bromide, Zinc nitrate, Zinc ammonium chloride, Zinc aluminum sulfate, Zinc zinc sulfate, Zinc iodide, Basic zinc carbonate and other inorganic zinc salts; (Hydroxylation / 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.

  The compounding amount of the zinc compound is not particularly limited, but if the amount of the zinc compound is too small, the antibacterial improvement effect may not be obtained. Therefore, the compounding amount of the zinc compound is the general formula (1) and / or the general formula (2). 0.02 parts by mass or more is preferable with respect to 100 parts by mass of the antibacterial agent composed of the compound represented by In addition, when the amount of zinc compound is increased, the antibacterial property is improved accordingly, but when the zinc compound exceeds a certain amount, the antibacterial property is not decreased, but the antibacterial property is not further improved. There is. Therefore, as for a zinc compound, 0.02-10 mass parts is more preferable with respect to 100 mass parts of antibacterial agents which consist of a compound represented by General formula (1) and / or General formula (2), 0.05-5 mass parts Is more preferable, and 0.1 to 2 parts by mass is most 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 of the present invention is not particularly limited, and can be used in the same manner as known antibacterial agents, disinfectants, disinfectants, and antifungal agents for the purpose of antibacterial, sterilization, disinfection, antifungal and the like. 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. In addition, medical equipment and medical cleaning agents for disinfecting and cleaning affected areas, household cleaning agents for sterilizing dishes, food industry cleaning agents, lubricants for container transfer conveyors, food packaging films Impregnating antibacterial agent, shampoo, rinse, hand soap, body soap, cleansing cream, cosmetics, clothing softener, aqueous or non-aqueous paint, non-woven fabric, etc. for antibacterial processing of fibers, synthetic resins, wood, daily necessities, etc. When used as a wet tissue, toilet seat cleaner, or antibacterial agent for fibers, 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 agent 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 washing cream, face washing foam, cleansing cream, cleansing milk, cleansing lotion, massage cream, cold cream, moisture 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, emulsion, eau de cologne, nail cosmetics, shampoo, rinse, etc. The amount of the antibacterial agent of the present invention is 0 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. In addition, what contains surfactant in the antibacterial composition of this invention may become the cleaning agent of this invention even if it is as it is. 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 nitrogen-free nonionic surfactant. Among these, it is particularly preferable to use an anionic surfactant or a nitrogen-free nonionic surfactant as 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.

  Examples of the nitrogen-free nonionic surfactant that can be preferably used in combination with the antibacterial composition of the present invention include polyoxyalkylene alkyl ether, polyoxyalkylene alkenyl ether, polyoxyethylene polyoxypropylene alkyl ether ( The addition form of ethylene oxide and propylene oxide may be 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, poly Oxyethylene sorbitan fatty acid ester, alkyl polyglucoside, sucrose fatty acid ester, alkyl (poly) glycerin ether, polyglycerin fatty acid ester Polyethylene glycol fatty acid esters, fatty acid methyl ester ethoxylate.

  Among such nitrogen-free nonionic surfactants, polyoxyethylene alkyl ether is preferable, and polyoxyethylene (average added mole number of ethylene oxide is preferably 4 to 18) alkyl (preferably having 12 to 16 carbon atoms) Ether is more preferred. 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, isostearyl alcohol, lauryl alcohol, hexadecyl alcohol and octyldodecanol, fatty acids such as isostearic acid, undecylenic acid and oleic acid, myristyl myristate, hexyl laurate, and oleic acid. Decyl, isopropyl myristate, hexyldecyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, ethylene glycol monostearate, octyl oxystearate, hydrocarbons such as liquid paraffin, petrolatum, squalane, lanolin, reduction Examples include waxes such as lanolin and carnauba wax, oils and fats such as mink oil, cacao butter, coconut oil, palm kernel oil, camellia oil, sesame oil, castor oil and olive oil.

  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. , Cellulose powder, silicone elastomer spherical powder, polymers such as 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, kaolin, pearl pigments such as titanium mica, metal salts such as barium sulfate, calcium carbonate, magnesium carbonate, magnesium silicate, inorganic powders such as silica and alumina, bentonite, smectite, boron nitride Etc. 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 the humectant include biopolymers such as diethylene glycol monoethyl ether, sorbitol, deoxyribonucleic acid, mucopolysaccharide, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, amino acids, lactic acid Sodium, urea, sodium pyrrolidonecarboxylate, betaine, whey and the like can be mentioned.

  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>
Invention product (A-1) 3- (2-hydroxyhexyloxy) -1,2-propanediol
<R ¹ in General Formula (1): C4, A: Glycerin Residue>
(A-2) 3- (2-hydroxyoctoxy) -1,2-propanediol
<R ¹ in General Formula (1): C6, A: Glycerin Residue>
(A-3) 3- (2-hydroxydecyloxy) -1,2-propanediol
<R ¹ in General Formula (1): C8, A: Glycerin Residue>
(A-4) 4- (2-hydroxyoctoxy) -1,2,3-butanetriol
<R ¹ in General Formula (1): C6, A: Erythritol Residue>
(A-5) 2-Ethyl-2- (1-hydroxyoctoxymethyl) -1,3-propanediol
<R ² in General Formula (2): C6, A: Trimethylolpropane Residue>
(A-6) Reaction product of 1,2-epoxydecane and diglycerin (the following mixture)
<R ¹ : 8 carbon atoms, A: 80% by mass of the component of general formula (1) of diglycerin residue>
^{<R 2:} carbon atoms 8, A: general formula diglycerin residue component 20 wt% of (2)>

Comparative product (B-1) 3- (2-hydroxybutyro) -1,2-propanediol
<R ¹ in the general formula (1): 2 carbon atoms, A: glycerin residue>
(B-2) 3- (2-Hydroxydodecyloxy) -1,2-propanediol
<R ¹ in General Formula (1): C10, A: Glycerin Residue>
(B-3) 3- (2-Hydroxyoctoxy) -1-octanol
<R ¹ in General Formula (1): C6, A: 1,8-octanediol residue>
(B-4) Monodecyl ether of glycerin (B-5) methyl paraben

Other ingredients chelating agent:
(C-1) ethylenediaminetetraacetic acid disodium (C-2) glutamic acid diacetate 4 sodium low molecular weight polyol:
(C-3) 1,3-butanediol (C-4) glycerol nitrogen-containing nonionic surfactant:
(C-5) Palm fatty acid monoethanolamide (C-6) Lauryldimethylamine oxide (C-7) POE (5) Laurylamine nitrogen-containing amphoteric surfactant (C-8) Palm oil fatty acid amide ethyl hydroxyethylglycine sodium (Sodium cocoamphoacetate)
Plant-derived extract:
(C-9) Chamomile extract (C-10) Hammeris extract (C-11) Brown algae extract zinc compound:
(C-12) Zinc sulfate (C-13) Zinc paraphenol sulfonate

<Example 1: Antibacterial test (minimum growth concentration)>
Using the bacterial solution pre-cultured in bouillon medium, the bacterial solution adjusted to the 10 ⁷ level was placed in a 0.27 ml microplate, and the above-mentioned compound adjusted to various concentrations between 10240 and 0.625 μg / ml was added to 0. 03 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 lowest concentration of the antibacterial agent 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.
Furthermore, the MIC was measured by blending the C component diluted to the same concentration at a ratio described in Table 2 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 represented by the concentration of the component A, and the antibacterial synergistic effect by adding the component C is confirmed. For comparison, combinations of B-5 components were added, and the results are shown in Table 2.
Bacteria 1: Bacillus subtilis IFO3134 (B. subtilis)
Fungus 2: Escherichia coli ATCC 14948 (Escherichia coli)
Fungus 3: Staphylococcus aureus IFO13276 (Staphylococcus aureus)

<Example 2: Skin irritation test>
About the said compound, skin irritation was evaluated by the 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 Tables 1 and 2.
(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.

<Example 3: Shampoo and lotion>
Shampoos and lotions were prepared with the following formulation.
(Shampoo composition)
Polyoxyethylene (3) sodium lauryl ether sulfate 25.0% by mass
Laurylamine oxide 3.0% by mass
Laurylamine propyl betaine 18.0 mass%
Propylene glycol 3.2% by mass
Hydroxyethyl cellulose 0.5% by mass
A-1 0.1% by mass
Purified water residue

(Composition of lotion)
Glycerin 3.0% by mass
Trimethylglycine 1.0% by mass
Dipropylene glycol 3.0% by mass
Sake lees extract 5.0% by mass
A-2 0.05 mass%
pH adjuster Suitable amount Water Residue

  When 10 subjects used the shampoo and lotion of the above composition, they could be used as a shampoo and lotion without any problems. Furthermore, when a sensory test for irritation was performed, There was no one and all 10 people could use it without any problems.

  The use of the antibacterial agent of the present invention is not particularly limited, and can be used in the same manner as known antibacterial agents, disinfectants, disinfectants, and antifungal agents for the purpose of antibacterial, sterilization, disinfection, antifungal and the like.

Claims (8)

The following general formula (1)

(R ¹ represents an alkyl group having 4 to 8 carbon atoms, and A represents a residue obtained by removing one hydroxyl group from a trivalent or higher valent alcohol) and / or the following general formula (2)

(R ² represents an alkyl group of 4-8 carbon atoms, A represents. The residue obtained by removing one hydroxyl group from trihydric or higher alcohols) antimicrobial agent characterized by comprising a compound represented by. In the general formula (1) and (2), ^{R 1} and ^{R 2} is an alkyl group of 5-7 carbon atoms, the antimicrobial agent according to claim 1. The antibacterial agent of Claim ² whose R < ¹ > and R < ² > is a C6 alkyl group in General formula (1) and (2).   The antibacterial agent according to any one of claims 1 to 3, wherein in the general formulas (1) and (2), A is a glycerin residue.   The antibacterial agent according to any one of claims 1 to 4, and a chelating agent, a low molecular polyol, a nitrogen-containing nonionic surfactant, a nitrogen-containing amphoteric surfactant, a plant-derived extract, and a zinc compound. 1. An antibacterial composition comprising one or more compounds.   A cosmetic comprising the antibacterial agent or antibacterial composition according to any one of claims 1 to 5.   A cleaning agent comprising the antibacterial agent or antibacterial composition according to any one of claims 1 to 5, and a surfactant.   The detergent according to claim 7, wherein the surfactant is one or more selected from the group consisting of an anionic surfactant, a cationic surfactant, and a nitrogen-free nonionic surfactant.