Composition and antibacterial method

Abstract

Provided are: a composition containing a compound (I) represented by general formula (1) and an antibacterial agent (II); and an antibacterial method.

Description

Composition and antibacterial method

[0001] The present invention relates to a composition and an antibacterial method.

[0002] Various antimicrobial treatments are carried out to prevent product spoilage and infectious diseases in humans and animals caused by bacteria, fungi, and other microorganisms. These treatments may involve the use of antimicrobial agents that kill or inhibit the growth of fungi.

[0003] Patent Document 1 discloses a method for suppressing the growth of bacteria contained in a water-based medium using an alcohol-containing composition, wherein the alcohol-containing composition comprises a specific alcohol and a preservative, and the bacteria include wastewater mixed bacteria.

[0004] Patent Document 2 discloses a disinfectant in which 0.001 to 1% by weight of a bactericide with a boiling point of 120°C or higher is dissolved in an aqueous solution in which 0.5 to 80% by weight of a water-soluble solvent that has a boiling point of 120°C or higher and is liquid at room temperature is dissolved.

[0005] Japanese Patent Publication No. 2022-21771 Japanese Patent Publication No. 2002-161001

[0006] In antimicrobial treatments using antimicrobial agents, it is desirable to improve the antimicrobial properties of the antimicrobial agent and obtain sufficient antimicrobial activity with a small amount of agent, in order to reduce the cost of the antimicrobial treatment or to reduce the impact of the antimicrobial agent on the quality and performance of the product being treated. However, the conventional methods described in Patent Documents 1 and 2 required further improvement in terms of antimicrobial activity.

[0007] This invention has been made in view of the above circumstances, and aims to provide a composition and an antibacterial method that exhibit excellent antibacterial properties.

[0008] The present inventors have conducted extensive research to achieve the above objectives and have found that the present invention can solve the problem as described below. That is, the present invention provides the following [1] to

[23] . [1] A composition containing a compound (I) represented by the following general formula (1), and an antibacterial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１and n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ where m is an integer from 1 to 4. When X is -C ｎ H ２ｎ＋１ and Y is -C ｍ H ２ｍ＋１ n + m is an integer from 2 to 7. R １ and R ２ are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and at least one of R １ and R ２ is an acyl group having 2 to 5 carbon atoms. R ３ and R ４ are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. When p is 2 or 3, the plurality of R ３ may be the same as or different from each other, and the plurality of R ４ may be the same as or different from each other. ) [2] The composition according to [1] above, wherein the compound (I) is represented by the following general formula (2). (In the formula, R １ and R ２ are the same as R １ and R ２ in the general formula (1). ) [3] The composition according to [2] above, which contains two or more selected from the group consisting of a compound represented by the following general formula (3), a compound represented by the following general formula (4), and a compound represented by the following general formula (5) as the compound (I) represented by the general formula (2). (In the formula, R ３(The acyl group having 2 to 5 carbon atoms is...) [4] The composition according to any one of [1] to [3] above, wherein the acyl group having 2 to 5 carbon atoms is an acetyl group. [5] The composition according to any one of [1] to [4] above, wherein the antibacterial agent (II) is at least one selected from the group consisting of isothiazolinoline antibacterial agents, phenolic antibacterial agents, quaternary ammonium antibacterial agents, biguanide antibacterial agents, pyridine antibacterial agents, oxazolidine antibacterial agents, alcohol antibacterial agents, carbamate antibacterial agents, sulfamide antibacterial agents, triazine antibacterial agents and imidazole antibacterial agents. [6] The composition according to any one of [1] to [5] above, wherein the antibacterial agent (II) is at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one. [7] The composition according to any one of [1] to [6], further comprising water or an organic solvent. [8] The composition according to any one of [1] to [7], further comprising water. [9] The composition according to any one of [1] to [8], wherein the content of compound (I) is 0.5 to 20% by mass with respect to the total amount of the composition.

[10] The composition according to any one of [1] to [9], wherein the content of antibacterial agent (II) is 0.01 to 5% by mass with respect to the total amount of the composition.

[11] The composition according to any one of [1] to

[10] , which is a coating composition, ink composition, adhesive composition, tack composition, glue composition, cleaning agent composition, deodorant composition, fragrance composition, repellent composition, wood preservative composition, pharmaceutical composition, pesticide composition, hair care composition, body care composition, skin care composition, fuel oil composition, machine lubricant composition, metalworking oil composition, refrigerant composition, or heat transfer medium composition.

[12] An antimicrobial method using a compound (I) represented by the following general formula (1) and an antimicrobial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (These may be identical or different from each other.)

[13] Use for antimicrobial purposes of a composition containing a compound (I) represented by the following general formula (1) and an antimicrobial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ They may be the same or different from each other.)

[14] The use described in

[13] above, wherein the compound (I) is represented by the following general formula (2). (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２(This is the same as above.)

[15] The use described in

[14] above, wherein the compound (I) represented by the general formula (2) includes two or more compounds selected from the group consisting of the compound represented by the following general formula (3), the compound represented by the following general formula (4), and the compound represented by the following general formula (5). (In the formula, R ３ (The acyl group having 2 to 5 carbon atoms is...)

[16] The use according to any one of

[13] to

[15] above, wherein the acyl group having 2 to 5 carbon atoms is an acetyl group.

[17] The use according to any one of

[13] to

[16] above, wherein the antibacterial agent (II) is at least one selected from the group consisting of isothiazolinoline antibacterial agents, phenolic antibacterial agents, quaternary ammonium antibacterial agents, biguanide antibacterial agents, pyridine antibacterial agents, oxazolidine antibacterial agents, alcohol antibacterial agents, carbamate antibacterial agents, sulfamide antibacterial agents, triazine antibacterial agents and imidazole antibacterial agents.

[18] The use according to any one of

[13] to

[17] above, wherein the antibacterial agent (II) is at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one.

[19] The use according to any one of

[13] to

[18] , wherein the composition further contains water or an organic solvent.

[20] The use according to any one of

[13] to

[19] , wherein the composition further contains water.

[21] The use according to any one of

[13] to

[20] , wherein the content of compound (I) is 0.5 to 20% by mass with respect to the total amount of the composition.

[22] The use according to any one of

[13] to

[21] , wherein the content of antimicrobial agent (II) is 0.01 to 5% by mass with respect to the total amount of the composition.

[23] The use according to any one of

[13] to

[22] above, wherein the composition is a coating composition, an ink composition, an adhesive composition, a tack composition, a glue composition, a cleaning agent composition, a deodorant composition, a fragrance composition, a repellent composition, a wood preservative composition, a pharmaceutical composition, a pesticide composition, a hair care composition, a body care composition, a skin care composition, a fuel oil composition, a machine lubricant composition, a metalworking oil composition, a refrigerant composition, or a heat transfer medium composition.

[0009] According to the present invention, it is possible to provide a composition and an antibacterial method that exhibit excellent antibacterial properties.

[0010] The following description will be based on an example of an embodiment of the present invention. However, the embodiments shown below are illustrative examples for embodying the technical concept of the present invention, and the present invention is not limited to the following description.

[0011] In this specification, preferred forms of embodiments are shown, but combinations of two or more individual preferred forms are also preferred forms. If there are several numerical ranges for a given item, a preferred form can be created by selectively combining the lower and upper limits of those ranges. In this specification, when a numerical range is described as "XX to YY," it means "XX or greater and YY or less."

[0012] [Composition] The composition of the present invention is a composition containing a compound (I) represented by the following general formula (1), and an antibacterial agent (II).

[0013] (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (The individuals may be identical or different from one another.)

[0014] The composition of the present invention exhibits excellent antibacterial properties by containing compound (I) and antibacterial agent (II). Although the detailed reasons for this are not entirely clear, it is presumed that one reason is that compound (I), having a hydrophobic acyl group, easily penetrates the phospholipids of the bacterial cell membrane, and effectively assists antibacterial agent (II) in entering the fungal cells.

[0015] In this invention, "antibacterial" is a term defined in "Antibacterial Technology and Market Trends 2016" (Publisher: CMC Publishing Co., Ltd., Publication Date: January 27, 2016, p. 166), and includes all terms such as sterilization, disinfection, sanitization, bacteriostatic, antimicrobial, preservative, antibacterial, and sanitization. In this invention, "antibacterial agent" means an agent having one or more functions selected from the group consisting of sterilization, disinfection, sanitization, bacteriostatic, antimicrobial, preservative, antibacterial, and sanitization. Here, sterilization means killing some or all of the fungi inside or outside the target object. Preservative means preventing the spoilage of food, pharmaceuticals, cosmetics, and other materials. Furthermore, fungi include all types of microorganisms such as bacteria and fungi. Bacteria include Staphylococcus aureus, etc. Fungi include mold, etc.

[0016] The components contained in the composition of the present invention will be described in order below.

[0017] <Compound (I)> In the above general formula (1), X is a hydrogen atom or -C ｎ H ２ｎ＋１ The expression is -C, where n is an integer from 1 to 4. ｎ H ２ｎ＋１ Examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, etc. X is selected from the viewpoint of the antibacterial properties of the composition, specifically from -C ｎ H ２ｎ＋１ A methyl group or an ethyl group is preferred, and a methyl group is even more preferred. In the above general formula (1), Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. -C is represented by Y. ｍ H ２ｍ＋１Examples of [the group represented by] R include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, and the like. From the viewpoint of the antibacterial property of the composition, Y is preferably -C ｍ H ２ｍ＋１ , more preferably a methyl group or an ethyl group, and even more preferably a methyl group. In the above general formula (1), when X is -C ｎ H ２ｎ＋１ and Y is -C ｍ H ２ｍ＋１ , n + m is an integer of 2 to 7, preferably an integer of 2 to 5, more preferably 2 or 3, and even more preferably 2, from the viewpoint of the antibacterial property of the composition.

[0018] In the above general formula (1), R １ and R ２ are each independently a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and at least one of R １ and R ２ is an acyl group having 2 to 5 carbon atoms. Examples of the acyl group having 2 to 5 carbon atoms represented by R １ and R ２ include an acetyl group, a propionyl group, a 2-methylpropionyl group, a 2,2-dimethylpropionyl group, a butyryl group, a 2-methylbutyryl group, a 3-methylbutyryl group, a pentanoyl group, and the like. Among these, from the viewpoint of easy availability, an acetyl group is preferred. In the above general formula (1), R ３ and R ４ are each independently a hydrogen atom or a methyl group, and preferably at least one of R ３ and R ４ is a hydrogen atom, and more preferably both R ３ and R ４ are hydrogen atoms. In the above general formula (1), p is an integer of 1 to 3, preferably 2 or 3, and more preferably 2, from the viewpoint of the antibacterial property of the composition. When p is 2 or 3, the plurality of R ３ may be the same as or different from each other, and the plurality of R ４ may be the same as or different from each other.

[0019] In the above general formula (1), from the viewpoint of the antibacterial property of the composition, X is -Cｎ H ２ｎ＋１ And Y is -C ｍ H ２ｍ＋１ And n+m is an integer from 2 to 5, R ３ and R ４ At least one of them is a hydrogen atom, p is preferably 2 or 3, and X is -C ｎ H ２ｎ＋１ And Y is -C ｍ H ２ｍ＋１ And n+m is an integer from 2 to 4, R ３ and R ４ At least one of them is a hydrogen atom, p is more preferably 2 or 3, X is a methyl group or an ethyl group, Y is a methyl group or an ethyl group, R ３ and R ４ At least one of them is a hydrogen atom, p is more preferably 2 or 3, X is a methyl group or an ethyl group, Y is a methyl group or an ethyl group, R ３ and R ４ R is a hydrogen atom, and it is more preferable that p is 2 or 3. Here, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0020] From the viewpoint of the antibacterial properties of the composition, compound (I) is preferably represented by the following general formula (2).

[0021] (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0022] Examples of compound (I) represented by the general formula (2) include the compound represented by the general formula (3) below (hereinafter also referred to as "compound (Ia)"), the compound represented by the general formula (4) below (hereinafter also referred to as "compound (Ib)"), the compound represented by the general formula (5) below (hereinafter also referred to as "compound (Ic)"), and so on.

[0023] (In the formula, R ５(This refers to an acyl group with 2 to 5 carbon atoms.)

[0024] The composition of the present invention may contain only one of compound (Ia), compound (Ib), and compound (Ic) as compound (I) represented by the general formula (2), or it may contain two or more compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic). Since compound (I) is usually obtained as a mixture containing two or more compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic), from the viewpoint of ease of manufacture, the composition of the present invention preferably contains two or more compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic), and more preferably contains compound (Ia) and compound (Ic).

[0025] If the composition of the present invention includes compound (Ia) and compound (I) other than compound (Ia) as compound (I) represented by the above general formula (2), the content of compound (Ia) in the total amount of compound (I) may be 50 to 99% by mass, 60 to 95% by mass, 70 to 93% by mass, or 75 to 90% by mass. If the composition of the present invention includes compound (Ic) and compound (I) other than compound (Ic) as compound (I) represented by the above general formula (2), the content of compound (Ic) in the total amount of compound (I) may be 0.5 to 40% by mass, 1 to 30% by mass, 2 to 20% by mass, or 3 to 10% by mass.

[0026] Specific examples of compound (I) represented by the above general formula (1) include compounds represented by the following general formula (6), such as 4-hydroxy-4-methyl-1-pentyl acetate, 4-acetoxy-4-methyl-1-pentanol, 4-acetoxy-4-methyl-1-pentyl acetate, 4-hydroxy-4-methyl-1-pentylpropionate, 4-propionyloxy-4-methyl-1-pentanol, 4-propionyloxy-4-methyl-1-pentylpropionate, 4-hydroxy-4-methyl-1-pentyl butyrate, 4-butyryloxy-4-methyl-1-pentanol, 4-butyryloxy-4-methyl-1-pentyl butyrate, 4-hydroxy-4-methyl-1-pentylpentanoate, 4-pentanoyloxy-4-methyl-1-pentylpentanoate, etc. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0027] Compounds represented by the following general formula (7), such as 3-hydroxy-3-methyl-1-butyl acetate, 3-acetoxy-3-methyl-1-butanol, 3-acetoxy-3-methyl-1-butyl acetate, 3-hydroxy-3-methyl-1-butyl propionate, 3-propionyloxy-3-methyl-1-butanol, 3-propionyloxy-3-methyl-1-butyl propionate, 3-hydroxy-3-methyl-1-butyl butyrate, 3-butyryloxy-3-methyl-1-butanol, 3-butyryloxy-3-methyl-1-butyl butyrate, 3-hydroxy-3-methyl-1-butylpentanoate, 3-pentanoyloxy-3-methyl-1-butanol, and 3-pentanoyloxy-3-methyl-1-butylpentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0028] Compounds represented by the following general formula (8), such as 2-hydroxy-2-methyl-1-propyl acetate, 2-acetoxy-2-methyl-1-propanol, 2-acetoxy-2-methyl-1-propyl acetate, 2-hydroxy-2-methyl-1-propyl propionate, 2-propionyloxy-2-methyl-1-propanol, 2-propionyloxy-2-methyl-1-propyl propionate, 2-hydroxy-2-methyl-1-propyl butyrate, 2-butyryloxy-2-methyl-1-propanol, 2-butyryloxy-2-methyl-1-propyl butyrate, 2-hydroxy-2-methyl-1-propylpentanoate, 2-pentanoyloxy-2-methyl-1-propanol, and 2-pentanoyloxy-2-methyl-1-propylpentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0029] Compounds represented by the following general formula (9), such as 4-hydroxy-4-ethyl-1-hexylacetate, 4-acetoxy-4-ethyl-1-hexanol, 4-acetoxy-4-ethyl-1-hexylacetate, 4-hydroxy-4-ethyl-1-hexylpropionate, 4-propionyloxy-4-ethyl-1-hexanol, 4-propionyloxy-4-ethyl-1-hexylpropionate, 4-hydroxy-4-ethyl-1-hexylbutyrate, 4-butyryloxy-4-ethyl-1-hexanol, 4-butyryloxy-4-ethyl-1-hexylbutyrate, 4-hydroxy-4-ethyl-1-hexylpentanoate, 4-pentanoyloxy-4-ethyl-1-hexylpentanoate, etc. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0030] Compounds represented by the following general formula (10), such as 3-hydroxy-3-ethyl-1-pentyl acetate, 3-acetoxy-3-ethyl-1-pentanol, 3-acetoxy-3-ethyl-1-pentyl acetate, 3-hydroxy-3-ethyl-1-pentylpropionate, 3-propionyloxy-3-ethyl-1-pentanol, 3-propionyloxy-3-ethyl-1-pentylpropionate, 3-hydroxy-3-ethyl-1-pentyl butyrate, 3-butyryloxy-3-ethyl-1-pentanol, 3-butyryloxy-3-ethyl-1-pentyl butyrate, 3-hydroxy-3-ethyl-1-pentylpentanoate, 3-pentanoyloxy-3-ethyl-1-pentylpentanoate, etc. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0031] Compounds represented by the following general formula (11), such as 2-hydroxy-2-ethyl-1-butyl acetate, 2-acetoxy-2-ethyl-1-butanol, 2-acetoxy-2-ethyl-1-butyl acetate, 2-hydroxy-2-ethyl-1-butyl propionate, 2-propionyloxy-2-ethyl-1-butanol, 2-propionyloxy-2-ethyl-1-butyl propionate, 2-hydroxy-2-ethyl-1-butyl butyrate, 2-butyryloxy-2-ethyl-1-butanol, 2-butyryloxy-2-ethyl-1-butyl butyrate, 2-hydroxy-2-ethyl-1-butylpentanoate, 2-pentanoyloxy-2-ethyl-1-butanol, and 2-pentanoyloxy-2-ethyl-1-butylpentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0032] Compounds represented by the following general formula (12), such as 4-hydroxy-4-propyl-1-heptyl acetate, 4-acetoxy-4-propyl-1-heptanol, 4-acetoxy-4-propyl-1-heptyl acetate, 4-hydroxy-4-propyl-1-heptylpropionate, 4-propionyloxy-4-propyl-1-heptanol, 4-propionyloxy-4-propyl-1-heptylpropionate, 4-hydroxy-4-propyl-1-heptyl butyrate, 4-butyryloxy-4-propyl-1-heptanol, 4-butyryloxy-4-propyl-1-heptyl butyrate, 4-hydroxy-4-propyl-1-heptylpentanoate, 4-pentanoyloxy-4-propyl-1-heptanoate, and 4-pentanoyloxy-4-propyl-1-heptylpentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0033] Compounds represented by the following general formula (13), such as 3-hydroxy-3-propyl-1-hexylacetate, 3-acetoxy-3-propyl-1-hexanol, 3-acetoxy-3-propyl-1-hexylacetate, 3-hydroxy-3-propyl-1-hexylpropionate, 3-propionyloxy-3-propyl-1-hexanol, 3-propionyloxy-3-propyl-1-hexylpropionate, 3-hydroxy-3-propyl-1-hexylbutyrate, 3-butyryloxy-3-propyl-1-hexanol, 3-butyryloxy-3-propyl-1-hexylbutyrate, 3-hydroxy-3-propyl-1-hexylpentanoate, 3-pentanoyloxy-3-propyl-1-hexylpentanoate, etc. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0034] Compounds represented by the following general formula (14), such as 2-hydroxy-2-propyl-1-pentyl acetate, 2-acetoxy-2-propyl-1-pentanol, 2-acetoxy-2-propyl-1-pentyl acetate, 2-hydroxy-2-propyl-1-pentylpropionate, 2-propionyloxy-2-propyl-1-pentanol, 2-propionyloxy-2-propyl-1-pentylpropionate, 2-hydroxy-2-propyl-1-pentyl butyrate, 2-butyryloxy-2-propyl-1-pentanol, 2-butyryloxy-2-propyl-1-pentyl butyrate, 2-hydroxy-2-propyl-1-pentylpentanoate, 2-pentanoyloxy-2-propyl-1-pentylpentanoate, etc. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0035] Compounds represented by the following general formula (15), such as 1,4-butanediol monoacetate, 1,4-butanediol diacetate, 1,4-butanediol monopropionate, 1,4-butanediol dipropionate, 1,4-butanediol monobutyrate, 1,4-butanediol dibutyrate, 1,4-butanediol monopentanoate, and 1,4-butanediol dipentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0036] Compounds represented by the following general formula (16), such as 1,3-propanediol monoacetate, 1,3-propanediol diacetate, 1,3-propanediol monopropionate, 1,3-propanediol dipropionate, 1,3-propanediol monobutyrate, 1,3-propanediol dibutyrate, 1,3-propanediol monopentanoate, and 1,3-propanediol dipentanoate; (In the formula, R １and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0037] Compounds represented by the following general formula (17), such as ethylene glycol monoacetate, ethylene glycol diacetate, ethylene glycol monopropionate, ethylene glycol dipropionate, ethylene glycol monobutyrate, ethylene glycol dibutyrate, ethylene glycol monopentanoate, and ethylene glycol dipentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0038] Compounds represented by the following general formula (18), such as 1,2-propanediol-1-monoacetate, 2-acetoxy-1-propanol, 1,2-propanediol diacetate, 1,2-propanediol-1-monopropionate, 2-propionyloxy-1-propanol, 1,2-propanediol dipropionate, 1,2-propanediol-1-monobutyrate, 2-butyryloxy-1-propanol, 1,2-propanediol dibutyrate, 1,2-propanediol-1-monopentanoate, 2-pentanoyloxy-1-propanol, and 1,2-propanediol dipentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0039] Compounds represented by the following general formula (19), such as 1,3-butanediol-1-monoacetate, 3-acetoxy-1-butanol, 1,3-butanediol diacetate, 1,3-butanediol-1-monopropionate, 3-propionyloxy-1-butanol, 1,3-butanediol dipropionate, 1,3-butanediol-1-monobutyrate, 3-butyryloxy-1-butanol, 1,3-butanediol dibutyrate, 1,3-butanediol-1-monopentanoate, 3-pentanoyloxy-1-butanol, and 1,3-butanediol dipentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0040] Compounds represented by the following general formula (20), such as 3-hydroxy-1,3-dimethyl-1-butyl acetate, 3-acetoxy-1,3-dimethyl-1-butanol, 3-acetoxy-1,3-dimethyl-1-butyl acetate, 3-hydroxy-1,3-dimethyl-1-butyl propionate, 3-propionyloxy-1,3-dimethyl-1-butanol, 3-propionyloxy-1,3-dimethyl-1-butyl propionate, 3-hydroxy-1,3-dimethyl-1-butyl butyrate, 3-butyryloxy-1,3-dimethyl-1-butanol, 3-butyryloxy-1,3-dimethyl-1-butyl butyrate, 3-hydroxy-1,3-dimethyl-1-butylpentanoate, 3-pentanoyloxy-1,3-dimethyl-1-butanol, and 3-pentanoyloxy-1,3-dimethyl-1-butylpentanoate; (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0041] Examples include compounds represented by the following general formula (21), such as 2-methyl-1,3-propanediol monoacetate, 2-methyl-1,3-propanediol diacetate, 2-methyl-1,3-propanediol monopropionate, 2-methyl-1,3-propanediol dipropionate, 2-methyl-1,3-propanediol monobutyrate, 2-methyl-1,3-propanediol dibutyrate, 2-methyl-1,3-propanediol monopentanoate, and 2-methyl-1,3-propanediol dipentanoate. (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

[0042] Among these, at least one selected from the group consisting of the compound represented by general formula (7), the compound represented by general formula (16), the compound represented by general formula (18), the compound represented by general formula (19), the compound represented by general formula (20), and the compound represented by general formula (21) is preferred, and the compound represented by general formula (7) is more preferred. More specifically, 3-hydroxy-3-methyl-1-butyl acetate, 3-acetoxy-3-methyl-1-butanol, 3-acetoxy-3-methyl-1-butyl acetate, 3-hydroxy-3-methyl-1-butyl propionate, 3-propionyloxy-3-methyl-1-butanol, 3-propionyloxy-3-methyl-1-butyl propionate, 3-hydroxy-3-methyl-1-butyl butyrate, 3-butyryloxy-3 -Methyl-1-butanol, 3-butyryloxy-3-methyl-1-butylbutyrate, 3-hydroxy-3-methyl-1-butylpentanoate, 3-pentanoyloxy-3-methyl-1-butanol, 3-pentanoyloxy-3-methyl-1-butylpentanoate, 1,3-propanediol monoacetate, 1,3-propanediol diacetate, 1,3-propanediol monopropionate, 1,3-propanediol dipro Pionate, 1,3-propanediol monobutyrate, 1,3-propanediol dibutyrate, 1,3-propanediol monopentanoate, 1,3-propanediol dipentanoate, 1,2-propanediol-1-monoacetate, 2-acetoxy-1-propanol, 1,2-propanediol diacetate, 1,2-propanediol-1-monopropionate, 2-propionyloxy-1-propanol, 1,2-prop Butanediol dipropionate, 1,2-propanediol-1-monobutyrate, 2-butyryloxy-1-propanol, 1,2-propanediol dibutyrate, 1,2-propanediol-1-monopentanoate, 2-pentanoyloxy-1-propanol, 1,2-propanediol dipentanoate, 1,3-butanediol-1-monoacetate, 3-acetoxy-1-butanol, 1,3-butanediol diacetate, 1,3-Butanediol-1-monopropionate, 3-propionyloxy-1-butanol, 1,3-butanediol dipropionate, 1,3-butanediol-1-monobutyrate, 3-butyryloxy-1-butanol, 1,3-butanediol dibutyrate, 1,3-butanediol-1-monopentanoate, 3-pentanoyloxy-1-butanol, 1,3-butanediol dipentanoate 3-hydroxy-1,3-dimethyl-1-butylacetate, 3-acetoxy-1,3-dimethyl-1-butanol, 3-acetoxy-1,3-dimethyl-1-butylacetate, 3-hydroxy-1,3-dimethyl-1-butylpropionate, 3-propionyloxy-1,3-dimethyl-1-butanol, 3-propionyloxy-1,3-dimethyl-1-butylpropionate, 3-hydroxy-1,3-dimethyl-1-butylbutyrate, 3-butyryloxy-1,3-dimethyl-1-butanol, 3-butyryloxy-1,3-dimethyl-1-butylbutyrate, 3-hydroxy-1,3-dimethyl-1-butylpentanoate, 3-pentanoyloxy-1,3-dimethyl-1-butylpentanoate, 2-methyl-1,3- Propanediol monoacetate, 2-methyl-1,3-propanediol diacetate, 2-methyl-1,3-propanediol monopropionate, 2-methyl-1,3-propanediol dipropionate, 2-methyl-1,3-propanediol monobutyrate, 2-methyl-1,3-propanediol dibutyrate, 2-methyl-1,3-propanediol monopentanoate, 2-methyl-1,3-propanediol dipentanoate is preferred, and 3-hydroxy-3-methyl-1-butyl acetate, 3-acetoxy-3-methyl-1-butanol, 3-acetoxy-3-methyl-1-butyl acetate, 3-hydroxy-3-methyl-1-butyl propionate, 3-propionyloxy-3-methyl-1-butanol, 3-propionyloxy-3-methyl-1-butyl propionate, 3-hydroxy-3-methyl-1-butyl butyrate, 3-butyryloxy-3-methyl-1-butanol, 3-butyryloxy-3-methyl-1-butyl butyrate, 3-hydroxy-3-methyl-1-butylpentanoate, 3-pentanoyloxy-3-methyl-1-butanol, and 3-pentanoyloxy-3-methyl-1-butylpentanoate are more preferred.

[0043] (Method for producing compound (I)) The method for producing compound (I) is not particularly limited, but for example, it can be produced by acylating at least one of the two hydroxyl groups of the diol compound represented by the following general formula (1').

[0044] (In the formula, X, Y, R ３ , R ４ and p are X, Y, R in the general formula (1) above. ３ , R ４ (and is the same as p.)

[0045] In the above general formula (1'), X, Y, R ３ , R ４The explanations for and p are the same as those for general formula (1) above, and the preferred embodiments are also the same. Acylation of a diol compound can be carried out by reacting the diol compound with an acyling agent (hereinafter also referred to as the "acylation reaction"). Examples of acyling agents include organic acids such as acetic acid, propionic acid, butyric acid, and isobutyric acid; and acid anhydrides, halides, esters, etc., of these organic acids. One acyling agent may be used alone, or two or more may be used in combination. In the acylation reaction, the amount of acyling agent used relative to the diol compound [acyling agent / diol compound] is not particularly limited, but from the viewpoint of the yield of compound (I), etc., it may be, for example, 1.0 to 10.0, 1.1 to 5.0, 1.3 to 3.0, 1.5 to 2.5, or 1.8 to 2.2 in molar terms.

[0046] From the viewpoint of reactivity, the acylation reaction is preferably carried out under heating. From the viewpoint of reaction rate and yield of compound (I), the reaction temperature for the acylation reaction is preferably 80 to 170°C, more preferably 100 to 160°C, and even more preferably 120 to 150°C. The reaction time for the acylation reaction can be appropriately determined according to the desired progress of the reaction, but for example, it may be 1 to 70 hours, 10 to 60 hours, or 20 to 50 hours. A solvent may or may not be used in the acylation reaction. Examples of solvents include ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as tetrahydrofuran, diethyl ether, and diisopropyl ether; non-aromatic hydrocarbon solvents such as hexane and cyclohexane; aromatic hydrocarbon solvents such as toluene; and chlorine-based solvents such as chloroform. One solvent may be used alone, or two or more may be used in combination. When a solvent is used in the acylation reaction, the solvent content is preferably 1 to 60% by mass, more preferably 3 to 30% by mass, and even more preferably 5 to 10% by mass, relative to the total volume of the reaction solution containing the solvent. After the reaction is complete, if necessary, purification such as distillation or washing may be performed to remove unreacted materials, by-products, etc.

[0047] (Content of Compound (I)) The content of Compound (I) in the composition of the present invention is preferably 0.5 to 20% by mass, more preferably 0.6 to 15% by mass, even more preferably 0.6 to 12% by mass, even more preferably 0.7 to 10% by mass, and even more preferably 0.8 to 5.0% by mass, based on the total amount of the composition of the present invention. Alternatively, the content of Compound (I) in the composition of the present invention is preferably 0.5 to 18% by mass, more preferably 0.8 to 15% by mass, even more preferably 2.0 to 13% by mass, even more preferably 3.0 to 12% by mass, and even more preferably 3.5 to 10% by mass, based on the total amount of the composition of the present invention. When the content of Compound (I) is above the lower limit above, it is easier to exhibit superior antibacterial activity. Also, when the content of Compound (I) is below the upper limit above, it is easier to obtain the effects of other components.

[0048] <Antibacterial agent (II)> The composition of the present invention contains antibacterial agent (II). Antibacterial agent (II) may be used alone or in combination of two or more types.

[0049] Examples of antimicrobial agents (II) include isothiazolinoline antimicrobial agents, phenolic antimicrobial agents, quaternary ammonium antimicrobial agents, biguanide antimicrobial agents, pyridine antimicrobial agents, oxazolidine antimicrobial agents, alcohol antimicrobial agents, carbamate antimicrobial agents, sulfamide antimicrobial agents, triazine antimicrobial agents, imidazole antimicrobial agents, thiazole antimicrobial agents, and iodine antimicrobial agents.

[0050] Examples of isothiazolin-based antibacterial agents include 2-methyl-4-isothiazolin-3-one, 2-ethyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2-ethyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-butyl-benzoisothiazolin-3-one, and 4-chloro-2-n-octyl-4-isothiazolin-3-one. Examples include 5-chloro-2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-t-octyl-4-isothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 4,5-dichloro-2-methyl-4-isothiazolin-3-one, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, and 4,5-dichloro-2-cyclohexyl-4-isothiazolin-3-one.

[0051] Examples of phenolic antimicrobial agents include phenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, 4,4'-dichloro-2-hydroxydiphenyl ether, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 2-benzyl-4-chlorophenol, 2-methyl-3-chlorophenol, 4-chloro-3,5-dimethylphenol, 2-isopropyl-5-methylphenol, 4-isopropyl-3-methylphenol, o-phenylphenol, metacresol, orthocresol, paracresol, methyl-p-hydroxybenzoate, ethyl-p-hydroxybenzoate, propyl-p-hydroxybenzoate, butyl-p-hydroxybenzoate, and benzoic acid.

[0052] Examples of quaternary ammonium-based antimicrobial agents include benzalkonium chloride, benzethonium chloride, tododecylmethylammonium chloride, lauryltrimethylammonium chloride, hexadecyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, N-polyoxyethylene-N,N,N-trimethylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, distearyldimethylammonium chloride, dioctadecyldimethylammonium chloride, 3-(trimethoxysilyl)propyldimethyloctadecylammonium chloride, tetradecyldimethylbenzylammonium chloride, tetraethylammonium chloride, tetrabutylammonium chloride, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide.

[0053] Examples of biguanide antibacterial agents include polyhexamethylene biguanide hydrochloride, polyhexamethylene biguanide stearate, chlorohexidine gluconate, chlorohexidine digluconate, chlorohexidine diacetate, chlorohexidine dihydrochloride, and chlorohexidine diphosphanylate.

[0054] Examples of pyridine-based antibacterial agents include 2-chloro-6-trichloromethylpyridine, 2-chloro-4-trichloromethyl-6-methoxypyridine, 2-chloro-4-trichloromethyl-6-(2-furylmethoxy)pyridine, di(4-chlorophenyl)pyridylmethanol, 2,3,5-trichloro-4-(n-propylsulfonyl)pyridine, 2,3,5,6-tetrachloro-4-methylsulfonylpyridine, 2,2'-dithiobispyridine-1-oxide, 2-pyridinethiol-1-oxide sodium, 2-pyridylthiol-1-oxide zinc, and 2-pyridylthiol-1-oxide copper.

[0055] Examples of oxazolidine antimicrobial agents include N-[[3-(3-fluoro-4-morpholinophenyl)-2-oxoxazolidine-5α-yl]methyl]acetamide and 4,4-dimethyl-1,3-oxazolidine.

[0056] Examples of alcohol-based antibacterial agents include ethanol, isopropyl alcohol, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, chlorobutanol, phenylethyl alcohol, 2-(hydroxymethylamino)ethanol, and 2-(hydroxymethylamino)-2-methylpropanol.

[0057] Examples of carbamate-based antibacterial agents include sodium N-methyldithiocarbamate, N,N'-ethylenebis(dithiocarbamate)manganese, N,N'-ethylenebis(dithiocarbamate)zinc, bis(N,N-dimethyldithiocarbamate)zinc, and bis(N,N-dimethyldithiocarbamate)N,N'-ethylenebis(thiocarbamoylthiozinc).

[0058] Examples of sulfamide-based antibacterial agents include N-(dichlorofluoromethylthio)-N',N'-dimethyl-N-phenylsulfamide and N-(dichlorofluoromethylthio)-N',N'-dimethyl-N-p-tolylsulfamide.

[0059] Examples of triazine-based antibacterial agents include hexahydro-1,3,5-trimethyl-1,3,5-triazine and 2,4-dichloro-6-methoxy-1,3,5-triazine.

[0060] Examples of imidazole-based antibacterial agents include methyl 1H-2-bentzimidazole carbamate, methyl 1-butylcarbamoyl-2-bentzimidazole carbamate, methyl 6-benzoyl-1H-2-bentzimidazole carbamate, methyl 6-(2-thiophenecarbonyl)-1H-2-bentzimidazole carbamate, methyl 1H-2-thiocyanomethylthiobentzimidazole, 1-dimethylaminosulfonyl-2-cyano-4-bromo-6-trifluoromethylbentzimidazole, 2-(4-thiazolyl)-1H-bentzimidazole, 2-(2-chlorophenyl)-1H-bentzimidazole, 2-(1-(3,5-dimethylpyrazolyl))-1H-bentzimidazole, and 2-(2-furyl)-1H-bentzimidazole.

[0061] Examples of thiazole antibacterial agents include 2-(4-thiocyanomethylthio)benzothiazole, 2-(isothiocyanatomethylthio)benzothiazole, 2-mercaptobenzothiazole zinc, 2-mercaptobenzothiazole sodium, 2-mercaptobenzothiazole potassium, 2-mercaptobenzothiazole calcium, 2-(chloromethylthio)benzothiazole, 2-(fluoromethylthio)benzothiazole, 2-(difluoromethylthio)benzothiazole, 2-(dibutylaminomethylthio)benzothiazole, 2-(diisobutylaminomethylthio)benzothiazole, 2-(dioctylaminomethylthio)benzothiazole, 2-(2-naphthylmethylthio)benzothiazole, and 2-(2-thienylmethylthio)benzothiazole.

[0062] Examples of iodine-based antibacterial agents include diiodomethyl-p-tolylsulfone, 1-diiodomethylsulfonyl-4-methylbenzene, 1-diiodomethylsulfonyl-4-chlorobenzene, 3-iodo-2-propargylbutylcarbamic acid, 4-chlorophenyl-3-iodopropargylformal, 3-ethoxycarbonyloxy-1-brom-1,2-diiodo-1-propene, and 2,3,3-triiodaryl alcohol.

[0063] Among the above antibacterial agents (II), at least one selected from the group consisting of isothiazolinine antibacterial agents, phenolic antibacterial agents, quaternary ammonium antibacterial agents, biguanide antibacterial agents, pyridine antibacterial agents, oxazolidine antibacterial agents, alcohol antibacterial agents, carbamate antibacterial agents, sulfamide antibacterial agents, triazine antibacterial agents and imidazole antibacterial agents is preferred, at least one selected from the group consisting of isothiazolinine antibacterial agents, phenolic antibacterial agents and quaternary ammonium antibacterial agents is more preferred, at least one selected from the group consisting of isothiazolinine antibacterial agents and phenolic antibacterial agents is even more preferred, and isothiazolinine antibacterial agents are even more preferred. When using isothiazolinoline antibacterial agents, at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, and 1,2-benzisothiazolin-3-one is preferred, at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one is more preferred, and a combination of 2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one is even more preferred. When using phenolic antibacterial agents, at least one selected from the group consisting of 2-isopropyl-5-methylphenol, 4-isopropyl-3-methylphenol, and o-phenylphenol is preferred, at least one selected from the group consisting of 2-isopropyl-5-methylphenol and 4-isopropyl-3-methylphenol is more preferred. When using a quaternary ammonium-based antibacterial agent, at least one selected from the group consisting of didecyldimethylammonium chloride and benzalkonium chloride is preferred, with didecyldimethylammonium chloride being more preferred.

[0064] The antimicrobial agent (II) in the composition of the present invention is preferably at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-isopropyl-5-methylphenol, 4-isopropyl-3-methylphenol, and o-phenylphenol; more preferably at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-isopropyl-5-methylphenol, and 4-isopropyl-3-methylphenol; and even more preferably at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, and 4-isopropyl-3-methylphenol.

[0065] The aforementioned antibacterial agent (II) can also be used as a preservative.

[0066] (Content of antibacterial agent (II)) The content of antibacterial agent (II) in the composition of the present invention is preferably 0.005 to 5% by mass, more preferably 0.01 to 5% by mass, even more preferably 0.01 to 2% by mass, even more preferably 0.02 to 1% by mass, even more preferably 0.03 to 0.5% by mass, even more preferably 0.04 to 0.3% by mass, and even more preferably 0.04 to 0.1% by mass, based on the total amount of the composition of the present invention. When the content of antibacterial agent (II) is above the lower limit above, better antibacterial properties tend to be exhibited. Also, when the content of antibacterial agent (II) is below the upper limit above, skin irritation tends to be lower.

[0067] <Content ratio of compound (I) and antibacterial agent (II) in the composition> In the composition of the present invention, the ratio of the mass-based content of compound (I) to the mass-based content of antibacterial agent (II) [(I) / (II)] is preferably 1 to 1000, more preferably 5 to 500, even more preferably 10 to 300, and even more preferably 15 to 100. When the content ratio [(I) / (II)] is within the above range, superior antibacterial activity is more likely to be exhibited.

[0068] <Total Content of Compound (I) and Antimicrobial Agent (II) in the Composition> In the composition of the present invention, the total content of Compound (I) and Antimicrobial Agent (II) is preferably 0.5 to 20% by mass, more preferably 0.6 to 15% by mass, even more preferably 0.7 to 10% by mass, and even more preferably 0.8 to 5.0% by mass, based on the total amount of the composition of the present invention. When the total content of Compound (I) and Antimicrobial Agent (II) is above the lower limit, superior antimicrobial activity is more likely to be exhibited. Also, when the total content of Compound (I) and Antimicrobial Agent (II) is below the upper limit, the effects of other components are more likely to be obtained.

[0069] <Water or Organic Solvent> Depending on the intended use of the composition, the composition may further contain water or an organic solvent. Examples of water include tap water, pure water, ultrapure water, ion-exchanged water, and distilled water. One of the above types of water may be used alone, or two or more may be used in combination. Examples of organic solvents include alcoholic solvents such as methanol, ethanol, butanol, octanol, ethylene glycol, and triethylene glycol; ketone solvents such as acetone and methyl ethyl ketone; carbonyl group-containing solvents such as methyl acetate, ethyl acetate, propyl acetate, dimethyl carbonate, diethyl carbonate, and diisopropyl carbonate; hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and cumene; halogenated solvents such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene, and dichlorobenzene; ether solvents such as diisopropyl ether, cyclopentyl methyl ether, diglyme, triglyme, tetrahydrofuran, and 1,4-dioxane; aliphatic hydrocarbon solvents such as hexane, heptane, and octane; and polar solvents such as N-methylpyrrolidone, dimethylformamide, and dimethyl sulfoxide. One of the above organic solvents may be used alone, or two or more may be used in combination.

[0070] (Content of water or organic solvent) In the composition of the present invention, the content of water or organic solvent is preferably 50.0 to 99.6% by mass, more preferably 60.0 to 99.4% by mass, even more preferably 70.0 to 99.2% by mass, and even more preferably 80.0 to 99.0% by mass, based on the total amount of the composition of the present invention.

[0071] The composition of the present invention may further contain water and organic solvents, depending on the intended use of the composition. In the composition of the present invention, the total content of water and organic solvents is preferably 50.0 to 99.6% by mass, more preferably 60.0 to 99.4% by mass, even more preferably 70.0 to 99.2% by mass, and even more preferably 80.0 to 99.0% by mass, based on the total amount of the composition of the present invention.

[0072] The composition of the present invention may further contain water, depending on the intended use of the composition. In the composition of the present invention, the water content is preferably 50.0 to 99.6% by mass, more preferably 60.0 to 99.4% by mass, even more preferably 70.0 to 99.2% by mass, and even more preferably 80.0 to 99.0% by mass, based on the total amount of the composition of the present invention.

[0073] The composition of the present invention may contain a diol compound represented by the above general formula (1'). The diol compound represented by the above general formula (1') may be included in the composition of the present invention as an unreacted raw material when the diol compound represented by the above general formula (1') is used as a raw material for compound (I) contained in the composition of the present invention. The content of the diol compound represented by the above general formula (1') in the composition of the present invention may be 0.01 to 50% by mass, 0.1 to 40% by mass, 1 to 30% by mass, 5 to 25% by mass, or 10 to 20% by mass, based on the total amount of compound (I) and the diol compound represented by the above general formula (1').

[0074] <Other Components> The compositions of the present invention may contain other components in addition to the components listed above. The other components may be appropriately selected according to the intended use of the compositions of the present invention, as described later. Examples of other components include pigments, dyes, resins, monomers, catalysts, curing agents, inorganic particles, organic particles, fibers, coupling agents, radical scavengers, chelating agents, oils, emulsifiers, surfactants, antioxidants, mineral components, plant extracts, pH adjusters, viscosity reducers, viscosity enhancers, enzyme stabilizers, defoamers, bleaching agents, fragrances, humectants, pharmacoactive substances, ultraviolet absorbers, ultraviolet scattering agents, antistatic agents, cleaning dispersants, friction modifiers, extreme pressure agents, rust inhibitors, viscosity index improvers, metal deactivators, etc. Each of the other components may be used individually or in combination of two or more. The content of the other components is not particularly limited and should be adjusted according to the intended use of the composition.

[0075] Examples of surfactants include nonionic surfactants, anionic surfactants, and cationic surfactants. Examples of nonionic surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, and polyoxyethylene stearyl ether; polyoxypropylene alkyl ethers such as polyoxypropylene butyl ether; polyoxyethylene polyoxypropylene alkyl ethers such as polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene cetyl ether, and polyoxyethylene polyoxypropylene stearyl ether; polyoxyethylene fatty acid esters, polyoxyethylene castor oil, polyoxyethylene castor oil fatty acid esters, polyoxyethylene hydrogenated castor oil, polyoxyethylene hydrogenated castor oil fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyglycerin fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene polyoxypropylene glycol, alkyl glucosides, alkyl polyglucosides, (poly)alkylglyceryl ethers, fatty acid alkanolamides, and sucrose fatty acid esters. Among these, polyoxyethylene lauryl ether is preferred from the viewpoint of suppressing the hydrolysis of the ester component.

[0076] Examples of chelating agents include sodium citrate and EDTA-2Na. Examples of pH adjusting agents include sodium acetate, sodium benzoate, sodium phosphate, tricalcium phosphate, calcium chloride, and sodium chloride. Among these, sodium acetate and sodium benzoate are preferred as pH adjusting agents from the viewpoint of maintaining the pH of the washing solution at a weakly basic level and suppressing the hydrolysis of ester components.

[0077] The composition of the present invention is preferably a composition that has been treated with an antimicrobial agent by containing compound (I) and antimicrobial agent (II). In other words, the composition of the present invention is preferably in a state in which the composition itself is antimicrobial, that is, in a state in which the growth of fungi is suppressed, by containing compound (I) and antimicrobial agent (II). The antimicrobial treatment containing compound (I) and antimicrobial agent (II) suppresses the amount of fungi in the composition, and the composition becomes less susceptible to deterioration such as spoilage.

[0078] The composition of the present invention may also be used for antimicrobial treatment of an antimicrobial target, such as a composition other than the composition of the present invention. For example, the composition of the present invention can be incorporated into a composition other than the composition of the present invention to treat the other composition with antimicrobial properties.

[0079] <Method for Producing the Composition> The method for producing the composition of the present invention is not particularly limited and can be obtained by mixing compound (I), antibacterial agent (II), water, organic solvent, and other components as needed. The method of mixing each component is not particularly limited and, for example, known mixing methods using a stirrer can be applied. Alternatively, the composition of the present invention can be produced by preparing another composition as the antibacterial target and mixing compound (I) and antibacterial agent (II) with it. Here, "another composition" may be a commercially available composition or a composition produced by mixing desired materials.

[0080] <Uses of the Composition> The uses of the composition of the present invention are not particularly limited, and can be used, for example, as a coating composition, ink composition, adhesive composition, sizing agent composition, glue composition, cleaning agent composition, deodorant composition, fragrance composition, repellent composition, wood preservative composition, pharmaceutical composition, pesticide composition, hair care composition, body care composition, skin care composition, fuel oil composition, machine lubricating oil composition, metalworking oil composition, refrigerant composition, or heat transfer medium composition.

[0081] The coating composition is not particularly limited as long as it is a composition applied to an object, but examples include coloring paint compositions, primer layer forming compositions, gas barrier layer forming compositions, hard coat layer forming compositions, waterproof layer forming compositions, antifouling layer forming compositions, rust prevention layer forming compositions, chemical resistance layer forming compositions, antibacterial layer forming compositions, heat shielding layer forming compositions, antistatic layer forming compositions, photocatalytic layer forming compositions, anti-reflective layer forming compositions, and the like.

[0082] Examples of ink compositions include inkjet ink compositions, printing ink compositions, writing instrument ink compositions, thermal transfer recording ink compositions, and stamp ink compositions.

[0083] Examples of adhesive compositions include heat-curing adhesive compositions, ultraviolet-curing adhesive compositions, moisture-curing adhesive compositions, solvent-evaporation adhesive compositions, and thermal-melt adhesive compositions.

[0084] Examples of adhesive compositions include (meth)acrylic adhesive compositions, urethane adhesive compositions, silicone adhesive compositions, polyester adhesive compositions, polyamide adhesive compositions, polyether adhesive compositions, fluorine adhesive compositions, and rubber adhesive compositions.

[0085] Examples of adhesive compositions include starch paste, solid paste, liquid paste, and spray paste.

[0086] Examples of cleaning agent compositions include: laundry detergent compositions; body detergent compositions; dishwashing detergent compositions; hard surface detergent compositions for floors, walls, windows, furniture, bathtubs, toilets, etc.; industrial detergent compositions such as detergent compositions for electronic equipment, optical equipment, transportation equipment, manufacturing equipment, and building materials.

[0087] Examples of deodorizing compositions include those for use on the body, clothing, bedding, shoes, rooms, cars, or toilets.

[0088] Examples of fragrance compositions include those for use on the body, clothing, bedding, shoes, rooms, cars, or toilets.

[0089] Examples of repellent compositions include insect repellent compositions for mites, mosquitoes, flies, horseflies, fleas, lice, etc.; termite repellent compositions; rodent repellent compositions; and the like.

[0090] Examples of wood preservative compositions include antifungal compositions, antifungal compositions, antistain compositions, and crack-preventing compositions.

[0091] Examples of pharmaceutical compositions include bactericidal compositions, disinfectant compositions, ointments, and the like.

[0092] Examples of pesticide compositions include fertilizer compositions, herbicide compositions, insecticide compositions, fungicide compositions, plant growth regulator compositions, plant activator compositions, and spreading agent compositions.

[0093] Examples of hair care compositions include shampoos, conditioners, rinses, treatments, hair oils, hair tonics, hair liquids, hair sprays, hair packs, and hair growth products.

[0094] Examples of body care compositions include facial cleansers, body soaps, body creams, hand soaps, hand creams, bar soaps, bath additives, and antiperspirants.

[0095] Examples of skincare compositions include lotions, serums, emulsions, creams, foundations, mascaras, lipsticks, lip balms, face masks, and sunscreens.

[0096] Examples of fuel oil compositions include gasoline, kerosene, diesel fuel, and heavy oil.

[0097] Examples of mechanical lubricating oil compositions include refrigeration oil, turbine oil, lubricating oil for internal combustion engines, gear oil, bearing oil, and electrical insulating oil.

[0098] Examples of metalworking oil compositions include cutting oils, rolling oils, pressing oils, drawing oils, heat treatment oils, and rust-preventive oils.

[0099] Examples of refrigerant compositions or heat transfer fluid compositions include water; organic solvents such as ethylene glycol, propylene glycol, ethanol, methanol, and isopropyl alcohol; and so on.

[0100] [Antibacterial Method] The antibacterial method of the present invention is an antibacterial method that uses a compound (I) represented by the following general formula (1) and an antibacterial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (The individuals may be identical or different from one another.)

[0101] The compounds (I) and antibacterial agents (II) used in the antibacterial method of the present invention are described above.

[0102] The antibacterial method of the present invention is not particularly limited as long as it uses compound (I) and antibacterial agent (II). Examples of the antibacterial method of the present invention include a method in which compound (I) and antibacterial agent (II) are contained in an object to be antibacterialized, and a method in which compound (I) and antibacterial agent (II) are brought into contact with a solid object to be antibacterialized.

[0103] According to the method of incorporating compound (I) and antibacterial agent (II) into an antimicrobial target, the antimicrobial target becomes a composition containing compound (I) and antibacterial agent (II), and in this composition, compound (I) and antibacterial agent (II) exhibit antibacterial function. As a result, the composition itself becomes antibacterial, that is, the growth of fungi is suppressed, and the composition becomes less susceptible to deterioration such as spoilage. The antimicrobial target containing compound (I) and antibacterial agent (II) may be a commercially available product or a manufactured product. The composition produced by incorporating compound (I) and antibacterial agent (II) into an antimicrobial target corresponds to the composition of the present invention described above. Therefore, examples of such compositions include the various compositions exemplified as compositions of the present invention described above, and the preferred embodiments, such as the content of compound (I) and antibacterial agent (II), are all as described above. When incorporating compound (I) and antibacterial agent (II) into an antimicrobial target, compound (I) and antibacterial agent (II) may be added simultaneously or at different timings. Furthermore, when compound (I) and antibacterial agent (II) are added simultaneously, compound (I) and antibacterial agent (II) may be added separately, or compound (I) and antibacterial agent (II) may be mixed beforehand before addition.

[0104] Examples of methods for bringing compound (I) and antibacterial agent (II) into contact with a solid object to be sterilized include spraying or coating compound (I) and antibacterial agent (II) onto the solid object to be sterilized, and immersing the solid object to be sterilized in a composition containing compound (I) and antibacterial agent (II). These methods are performed, for example, for the purpose of sterilizing or disinfecting the surface of the solid object to be sterilized. After the antibacterial treatment, compound (I) and antibacterial agent (II) may be removed from the surface of the object to be sterilized, and the object to be sterilized may no longer contain compound (I) and antibacterial agent (II). However, the method of use may leave compound (I) and antibacterial agent (II) on the surface, inside, etc., of the object to be sterilized.

[0105] [Use] The present invention provides a composition containing a compound (I) represented by the following general formula (1) and an antimicrobial agent (II) for use in antimicrobial purposes. (In the formula, X is a hydrogen atom or -C) ｎH ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (The individuals may be identical or different from one another.)

[0106] The composition used in the present invention is preferably the composition of the present invention as described above. Therefore, the preferred embodiments, such as the components contained in the composition and their content, the object to be antibacterialized by the composition, and the antibacterial method, are all as described above and will be omitted here.

[0107] The present invention will be described in more detail below using examples and comparative examples, but the present invention is not limited to the following examples.

[0108] [Gas Chromatography Analysis Conditions] The gas chromatography analysis of compound (I) produced in Production Example 1 was performed under the following conditions: • Analytical instrument: GC-2014S (Shimadzu Corporation) • Column: DB-1 (Agilent Technologies, Inc.) • Carrier gas: Helium • Injection temperature: 270°C • Detector temperature: 270°C • Column oven temperature: Increased from 80°C to 280°C at a rate of 5°C / min.

[0109] [Preparation of Compound (I)] Preparation Example 1 320.8 g (3.08 mol) of 3-methyl-1,3-butanediol (manufactured by Kuraray Co., Ltd., "isoprene glycol"), 370.4 g (6.17 mol) of acetic acid, and 48 g of cyclohexane were added to a three-necked flask. The mixture was then heated to 140°C and the reaction was carried out under a nitrogen atmosphere and stirring with a magnetic stirrer, maintaining the reaction mixture temperature at 140°C. 38 hours after the start of the reaction, gas chromatography analysis under the above conditions confirmed that the decrease in the amount of 3-methyl-1,3-butanediol had stopped. After this, heating was stopped and the mixture was cooled to room temperature. From the obtained crude product, cyclohexane and unreacted acetic acid were recovered at a pressure of 6.4 kPa and a distillation temperature of 108°C. Subsequently, at a pressure of 6.4 kPa and a distillation temperature of 127.8°C, 193.7 g of a 3-methyl-1,3-butanediol-acetate mixture (hereinafter also referred to as "compound (I) mixture") was obtained as the main fraction. Gas chromatography analysis of the obtained compound (I) mixture under the above conditions revealed that it contained 12.6% by mass of the starting material 3-methyl-1,3-butanediol, 83.4% by mass of 3-hydroxy-3-methyl-1-butyl acetate (corresponding to compound (I)), and 4.0% by mass of 3-acetoxy-3-methyl-1-butyl acetate.

[0110] [Preparation of Compositions] The materials used in the preparation of the compositions in the examples and comparative examples are as follows:

[0111] (Solvents) • Compound (I) mixture: Compound (I) mixture obtained in Production Example 1 • Propylene glycol: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. • 3-Methyl-1,3-Butanediol: Manufactured by Kuraray Co., Ltd. • 3-Methoxy-3-methyl-1-butanol: Manufactured by Kuraray Co., Ltd. • 3-Methyl-1,5-Pentanediol: Manufactured by Kuraray Co., Ltd. • Ethanol: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.

[0112] (Antibacterial agents) ・Isothiazoline-based antibacterial agent: "AN1000" (manufactured by Arxada, a mixture of 2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one) ・Phenol-based antibacterial agent: 4-isopropyl-3-methylphenol, manufactured by Fujifilm Wako Pure Chemical Industries Ltd.

[0113] (Water) ・Purified water

[0114] <Examples 1-7, Comparative Examples 1-9> Compositions (hereinafter also referred to as "antibacterial agent-containing compositions") were obtained by mixing the solvent, antibacterial agent, and water in the amounts shown in Tables 1-3 and stirring by hand at 23°C for 1 minute. When the appearance of the antibacterial agent-containing compositions obtained in each example was visually inspected, no separation of components was observed.

[0115] [Antibacterial Test] The antibacterial test was conducted using a method based on the preservative efficacy test of the Japanese Pharmacopoeia (18th edition of the Japanese Pharmacopoeia). The following bacterial species were used in the antibacterial test: ・Bacteria-1: Staphylococcus aureus ・Bacteria-2: Aspergillus brasiliensis ・Bacteria-3: Penicillium citrinum (1) Preparation of test bacterial suspensions Test bacterial suspensions 1 to 3 were prepared using bacteria-1 to 3 according to the following procedure. Bacteria-1 was pre-cultured on SCD (Soybean-Casein Digest) agar at 32.5°C for 20 hours, then scraped off with a platinum loop and suspended in sterile physiological saline for about 10 minutes. ８ The culture was prepared at a concentration of 1 / g to obtain test bacterial suspension 1. Bacteria 2 and 3 were pre-cultured on Sabouraud glucose agar at 22.5°C for 6-10 days, scraped with a platinum loop, suspended in sterile physiological saline with 80.005% polysorbate, filtered through a quarter-folded sterile gauze, and then approximately 10 ７ The bacterial count was adjusted to 1 / g to obtain test bacterial solution 2 and test bacterial solution 3. (2) Preparation and storage of samples 20 g of the antimicrobial agent-containing composition prepared in each example and comparative example was placed in a sterile vial, and 0.15 mL of the test bacterial solution was added thereto (when the bacterial count was 10 ５ ~10 ６ The sample was inoculated (in an amount that results in 10 cells / g). The sample consisted of 20 g of one type of antibacterial agent-containing composition and 0.15 mL of one type of test bacterial solution (with a bacterial count of 10) in one sterile vial. ５ ~10 ６The sample was prepared by adding an amount that would result in cells / g. One sample was prepared for each antimicrobial agent-containing composition in combination with each of the three test bacterial solutions. The samples were stored at 25°C, and in antimicrobial test 1 (preservative test), the number of viable cells was measured after 7, 14, and 21 days. In antimicrobial test 2 (bactericidal test), the number of viable cells was measured after 5, 15, and 30 minutes. (3) Method of measuring the number of viable cells In the case of test bacterial solution 1, SCDLP (Soybean-Casein Digest Agar with Lecithin and Polysorbate 80) agar medium was used as the culture medium, and the agar plate pour plate method was used. In the agar plate pour plate method, the test sample was serially diluted, 1 mL was taken in a petri dish, mixed with 15-20 mL of SCDLP agar medium, solidified into a plate, and incubated at 30°C for 3 days. The number of colonies produced was then measured and converted to the number of viable cells per gram of test sample. As the diluent, LP diluent (1 g polypeptone, 0.7 g egg lecithin, 20 g polysorbate 80, 980 mL purified water) was used. For test bacterial suspension 2 and test bacterial suspension 3, Sabouraud glucose LP agar medium was used as the culture medium, and the number of viable cells was measured by the agar plate pour plate method described above.

[0116]

[0117]

[0118]

[0119] Tables 1 and 2 show that the compositions of Examples 1 to 7, which are the compositions of the present invention, have excellent antibacterial properties (more specifically, antiseptic properties). Furthermore, Table 3 shows that the composition of Example 5, which is the composition of the present invention, has excellent antibacterial properties (more specifically, bactericidal properties) even in a short period of time.

Claims

1. A composition containing a compound (I) represented by the following general formula (1) and an antibacterial agent (II). (In the formula, X is a hydrogen atom or -C ｎ H ２ｎ＋１ ; n is an integer from 1 to 4; Y is a hydrogen atom or -C ｍ H ２ｍ＋１ ; m is an integer from 1 to 4. When X is -C ｎ H ２ｎ＋１ and Y is -C ｍ H ２ｍ＋１ , n + m is an integer from 2 to 7. R １ and R ２ are each independently a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and at least one of R １ and R ２ is an acyl group having 2 to 5 carbon atoms. R ３ and R ４ are each independently a hydrogen atom or a methyl group. p is an integer from 1 to 3. When p is 2 or 3, the plurality of R ３ may be the same as or different from each other, and the plurality of R ４ may be the same as or different from each other.) 2. The composition according to claim 1, wherein the compound (I) is represented by the following general formula (2). (In the formula, R １ and R ２ R in the general formula (1) is １ and R ２ It is the same as this.

3. The composition according to claim 2, wherein the compound (I) represented by the general formula (2) comprises two or more compounds selected from the group consisting of the compound represented by the following general formula (3), the compound represented by the following general formula (4), and the compound represented by the following general formula (5). (In the formula, R ３ (This refers to an acyl group with 2 to 5 carbon atoms.) 4. The composition according to any one of claims 1 to 3, wherein the acyl group having 2 to 5 carbon atoms is an acetyl group.

5. The composition according to any one of claims 1 to 4, wherein the antibacterial agent (II) is at least one selected from the group consisting of isothiazolinoline antibacterial agents, phenolic antibacterial agents, quaternary ammonium antibacterial agents, biguanide antibacterial agents, pyridine antibacterial agents, oxazolidine antibacterial agents, alcohol antibacterial agents, carbamate antibacterial agents, sulfamide antibacterial agents, triazine antibacterial agents, and imidazole antibacterial agents.

6. The composition according to any one of claims 1 to 5, wherein the antimicrobial agent (II) is at least one selected from the group consisting of 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, and 1,2-benzisothiazolin-3-one.

7. The composition according to any one of claims 1 to 6, further comprising water or an organic solvent.

8. The composition according to any one of claims 1 to 7, further comprising water.

9. The composition according to any one of claims 1 to 8, wherein the content of compound (I) is 0.5 to 20% by mass relative to the total amount of the composition.

10. The composition according to any one of claims 1 to 9, wherein the content of the antimicrobial agent (II) is 0.01 to 5% by mass relative to the total amount of the composition.

11. A composition according to any one of claims 1 to 10, which is a coating composition, ink composition, adhesive composition, tack composition, glue composition, cleaning agent composition, deodorant composition, fragrance composition, repellent composition, wood preservative composition, pharmaceutical composition, pesticide composition, hair care composition, body care composition, skin care composition, fuel oil composition, machine lubricant composition, metalworking oil composition, refrigerant composition, or heat transfer medium composition.

12. An antimicrobial method using a compound (I) represented by the following general formula (1), and an antimicrobial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (The individuals may be identical or different from one another.) 13. Use for antimicrobial purposes of a composition containing compound (I) represented by the following general formula (1) and an antimicrobial agent (II). (In the formula, X is a hydrogen atom or -C) ｎ H ２ｎ＋１ Here, n is an integer from 1 to 4, and Y is a hydrogen atom or -C ｍ H ２ｍ＋１ And m is an integer from 1 to 4. X is -C ｎ H ２ｎ＋１ , and Y is -C ｍ H ２ｍ＋１ In this case, n+m is an integer between 2 and 7. １ and R ２ These are, independently of each other, a hydrogen atom or an acyl group having 2 to 5 carbon atoms, and R １ and R ２ At least one of them is an acyl group having 2 to 5 carbon atoms. ３ and R ４ R are, independently of each other, a hydrogen atom or a methyl group. p is an integer from 1 to 3. If p is 2 or 3, multiple R ３ The Rs may be identical or different from each other, and there may be multiple Rs. ４ (The individuals may be identical or different from one another.)

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