JP2000128716A - Antimicrobial composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of suppressing the decomposition of an isothiazolone compound and excellent in stability by including the specific isothiazolone compound and a specified aliphatic sulfonic acid. SOLUTION: This composition is obtained by including (A) preferably 0.1-10 wt.% of an isothiazolone compound represented by formula I or II [R1 is H, an alkyl, an alkenyl or the like; X and Y are each H or a halogen or both together with C atoms at the 4- and the 5-positions of the isothiazolone compound form a benzene ring; M is a cation of an alkali(ne earth) metal, a heavy metal or an amine; Z is an anion forming a compound of the cation M having a sufficient solubility to form a complex compound; (a) is 1 or 2; (n) is an integer such that the anion Z satisfies the valence of the cation M] and (B) an aliphatic sulfonic acid represented by the formula R2SO3H (R2 is a 1-4C alkyl) of the formula HO3SR3SO3H (R3 is a 1-4C alkylene) in a molar amount of preferably 0.1-10 times based on the ingredient A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an antibacterial composition. More specifically, the present invention relates to an antibacterial composition containing an isothiazolone compound and having excellent stability capable of suppressing decomposition of the isothiazolone compound.

[0002]

2. Description of the Related Art Isothiazolone compounds represented by 5-chloro-2-methyl-4-isothiazolin-3-one have excellent antibacterial activity, and are therefore used in cooling water systems, paper pulp, paints, adhesives, cutting oils, and the like. It is widely used as a slime control agent, an antibacterial agent, an antialgal agent and an antifungal agent for various systems such as human waste treatment. However, since isothiazolone compounds are extremely unstable compounds, studies to improve product stability are needed in order to effectively use chemicals containing these compounds. Has been done. For example, Japanese Patent Publication No. 54-2396
No. 8 discloses a biocidally active compound which is useful for controlling various biological organisms, especially microorganisms.
Resists decomposition by ordinary additives, contaminants and extreme conditions,
Particularly, as a complex having excellent thermal stability, a metal salt complex such as calcium chloride and zinc chloride of an isothiazolone compound has been proposed. US Patent No. 3870
No. 795 discloses that a solution of an isothiazolone compound is
It has been reported that by adding a metal nitrate such as calcium nitrate or magnesium nitrate or a metal nitrite such as sodium nitrite or calcium nitrite, decomposition of an isothiazolone compound can be suppressed and stabilized. Further, JP-A-61-56174 and JP-A-61-21 are disclosed.
No. 2576 discloses that an isothiazolone compound such as 5-chloro-2-methyl-4-isothiazolin-3-one is converted into a solution of propylene glycol, 1,5-pentanediol, benzyl alcohol or the like, and copper chloride, sodium chloride, Isothiazolone stabilizing solutions to which metal salts such as magnesium chloride and copper nitrate are added have been proposed.
Further, Japanese Patent Publication No. 4-20401 discloses an isothiazolone compound preparation which has excellent preparation stability and does not cause a shock even when added directly to a synthetic polymer emulsion. A non-medical sterilized aqueous preparation comprising the above anionic surfactant such as an aliphatic sulfonate or a nonionic surfactant having an HLB of 10 or more and water or an aqueous solvent has been proposed. However, when these preparations are used after further dilution with water or an organic solvent, the stability of the isothiazolone compound is significantly reduced, so that the decomposition of the isothiazolone compound can be effectively suppressed. There was a need for a composition.

[0003]

SUMMARY OF THE INVENTION The object of the present invention is to provide an antibacterial composition containing an isothiazolone compound and having excellent stability which can suppress the decomposition of the isothiazolone compound. is there.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that aliphatic sulfonic acid has an action of stabilizing an isothiazolone compound. Based on this, the present invention has been completed. That is, the present invention includes (1) an isothiazolone compound represented by the general formula [1] or [2] and an aliphatic sulfonic acid represented by the general formula [3] or [4]. An antibacterial composition,

Embedded image (Wherein, R ¹ is hydrogen, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group. X and Y
Is a compound which forms a benzene ring together with hydrogen or halogen, or carbon at the 4-position and 5-position of the isothiazolone compound. M is an alkali metal, an alkaline earth metal,
A cation of a heavy metal or amine, Z is an anion that forms a compound with a cation M that has sufficient solubility to form a complex compound. a is 1 or 2, n
Is an integer in which the anion Z satisfies the valence of the cation M. ) R ² SO ₃ H ... [3] (wherein, R ² is an alkyl group having 1 to 4 carbon atoms.) HO ₃ SR ³ SO ₃ H ... [4] ³ is an alkylene group having 1 to 4 carbon atoms.). Further, as a preferred embodiment of the present invention, (2) the content of the isothiazolone compound represented by the general formula [1] or [2] is as follows:
The antimicrobial composition according to item (1), which is 0.1 to 10% by weight, and (3) the content of the aliphatic sulfonic acid represented by the general formula [3] or [4] is: 0.1 to 0.1 of the isothiazolone compound represented by the general formula [1] or the general formula [2]
The antibacterial composition according to item (1) or (2), which is 10 mole times, can be mentioned.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The antibacterial composition of the present invention comprises an isothiazolone compound represented by the general formula [1] or [2] and a fat represented by the general formula [3] or [4]. Contains aromatic sulfonic acid.

Embedded image In the general formulas [1] and [2], R ¹ is hydrogen, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group. X and Y are hydrogen or halogen,
Alternatively, it forms a benzene ring together with the carbons at the 4 and 5 positions of the isothiazolone compound. M is a cation of an alkali metal, an alkaline earth metal, a heavy metal or an amine, and Z is an anion that forms a compound with a cation M having sufficient solubility to form a complex compound.
a is 1 or 2, and n is a cation M
Is an integer satisfying the valence of. R ² SO ₃ H [3] In the general formula [3], R ² is an alkyl group having 1 to 4 carbon atoms. HO ₃ SR ³ SO ₃ H [4] In the general formula [4], R ³ is an alkylene group having 1 to 4 carbon atoms.

The isothiazolone compound represented by the general formula [1] includes, for example, 5-chloro-2-methyl-4-
Isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 4,5-dichloro-2-methyl-4
-Isothiazolin-3-one, 2-ethyl-4-isothiazolin-3-one, 2-octyl-4-isothiazolin-3-one, 5-chloro-2-octyl-4-isothiazolin-3-one, 4.5 -Dichloro-2-octyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, and the like. Examples of the isothiazolone compound represented by the general formula [2] include, for example, magnesium chloride, magnesium nitrate, copper chloride, and the like of the isothiazolone compound represented by the general formula [1].
Complex compounds with copper nitrate, calcium chloride and the like can be mentioned. In the composition of the present invention, one kind of the isothiazolone compound represented by the general formula [1] or [2] may be used alone, or two or more kinds may be used in combination.

Examples of the aliphatic sulfonic acid represented by the general formula [3] include methanesulfonic acid, ethanesulfonic acid, 1-propanesulfonic acid, 2-propanesulfonic acid, 1-butanesulfonic acid, and 2-butane Sulfonic acid, 2
-Methyl-1-propanesulfonic acid, 2-methyl-2-
Propanesulfonic acid and the like can be mentioned. As the aliphatic sulfonic acid represented by the general formula [4], for example,
Methanedisulfonic acid, 1,2-ethanedisulfonic acid, 1,
Examples thereof include 3-propanedisulfonic acid and 1,4-butanedisulfonic acid. In the composition of the present invention,
One kind of the aliphatic sulfonic acid represented by the general formula [3] or [4] can be used alone, or 2
A combination of more than one species can also be used. Among the aliphatic sulfonic acids, an aliphatic disulfonic acid represented by the general formula [4] can be particularly preferably used because it has an excellent stabilizing effect on an isothiazolone compound. Instead of the aliphatic sulfonic acid represented by the general formula [3] or [4], a sodium salt, a potassium salt or the like of the aliphatic sulfonic acid represented by the general formula [3] or [4] is used. Although it can be used, the stabilizing effect of the aliphatic sulfonic acid salt on the isothiazolone compound is inferior to the stabilizing effect of the aliphatic sulfonic acid. It is preferable to use the aliphatic sulfonic acid obtained.

In the composition of the present invention, the concentration of the isothiazolone compound represented by the general formula [1] or [2] is not particularly limited, but is preferably 0.1 to 10% by weight, preferably 0.1 to 10% by weight. More preferably, it is 3 to 5% by weight.
When the concentration of the isothiazolone compound represented by the general formula [1] or [2] is less than 0.1% by weight, the capacity of the antibacterial composition as a product becomes large, and the transportation and storage are economical. May be damaged. When the concentration of the isothiazolone compound represented by the general formula [1] or [2] exceeds 10% by weight, the stability of the antibacterial composition may be impaired. In the composition of the present invention,
There is no particular limitation on the concentration of the aliphatic sulfone represented by the general formula [3] or [4], but the concentration of the isothiazolone compound represented by the general formula [1] or the general formula [2] may be 0.1 to 10%.
The molar ratio is preferably 1 mol, more preferably 1 mol to 5 mol. When the concentration of the aliphatic sulfonic acid represented by the general formula [3] or [4] is less than 0.1 mol times the isothiazolone compound, the stability of the antibacterial composition is impaired, and the isothiazolone compound is decomposed. May be easier to do. The concentration of the aliphatic sulfonic acid represented by the general formula [3] or [4] is usually sufficient to be 10 mol times or less of the isothiazolone compound, and more than 10 mol times of the isothiazolone compound. Alternatively, even when the aliphatic sulfonic acid represented by the general formula [4] is contained, the stability of the antibacterial composition does not improve according to the content of the aliphatic sulfonic acid.

The solvent used in the composition of the present invention includes an isothiazolone compound represented by the general formula [1] or [2] and an aliphatic sulfonic acid represented by the general formula [3] or [4]. There is no particular limitation as long as it can dissolve the compound. However, since the target system is often an aqueous system, it is preferably water or a hydrophilic organic solvent. Examples of the hydrophilic organic solvent include amides such as dimethylformamide, glycols such as ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol; glycols such as methyl cellosolve, phenyl cellosolve, diethylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. Examples thereof include ethers, alcohols having 8 or less carbon atoms, esters such as methyl acetate, ethyl acetate, 3-methoxybutyl acetate, 2-ethoxyethyl acetate, 2-ethoxypropyl acetate, and propylene carbonate.

[0010] The antimicrobial composition of the present invention may further contain, if necessary, a corrosion inhibitor, a scale inhibitor, an antibacterial agent other than the isothiazolone compound, an antifoaming agent, a surfactant, an antialgal agent and the like. it can. As corrosion inhibitors, for example,
Tolyltriazole, benzotriazole, methylbenzotriazole, molybdic acid, tungstic acid, silicic acid, nitrous acid, 2-phosphonobutane-1,2,4-tricarboxylic acid, hydroxyethylidene diphosphonic acid, hexametaphosphoric acid, tripolyphosphoric acid, orthophosphoric acid And salts thereof, zinc chloride, zinc chloride acidic with hydrochloric acid, zinc sulfate, zinc ligninsulfonate, hydrazine and the like. Examples of the scale inhibitor include polyacrylic acid, a copolymer of acrylic acid / 2-hydroxyethyl methacrylate, a copolymer of acrylic acid / 2-hydroxyethyl methacrylate / methyl acrylate, and a copolymer of acrylic acid / allyl glycidyl ether. Polymer, acrylic acid /
2-hydroxy-3-allyloxy-1-propanesulfonic acid copolymer, acrylic acid / isoprenesulfonic acid copolymer, acrylic acid / vinylsulfonic acid copolymer,
Acrylic acid / allyl sulfonic acid copolymer, polymaleic acid, maleic acid or maleic anhydride / isobutylene copolymer, maleic acid or maleic anhydride / styrene sulfonic acid copolymer, maleic acid or maleic anhydride /
Acrylic acid copolymer, maleic acid or maleic anhydride / methyl acrylate copolymer, maleic acid or maleic anhydride / 2-acrylamido-2-methylpropanesulfonic acid copolymer, maleic acid or maleic anhydride / Examples thereof include a copolymer of amylene acid, a copolymer of maleic acid or maleic anhydride / allylated fluorescent substance (such as 5-allylbenzosuberenol), polyacrylamide, polyitaconic acid, and salts thereof.

As the antibacterial agent, for example, 2-bromo-2
-Nitro-1,3-propanediol, halogenated aliphatic nitro compounds such as 2,2-dibromo-2-nitroethanol and their esters, alkylenebisthiocyanates such as dibromonitrillopropionamide, methylenebisthiocyanate, 4-bisbromoacetoxy-2-butene, hexabromodimethylsulfone, 5
Isophthalonitrile compounds such as -chloro-2,4,6-trifluoroisophthalonitrile and tetrachloroisophthalonitrile, dimethyldithiocarbamate,
5-dichloro-1,2-dithiol-3-one, 3,3,
4,4, -tetrachlorotetrahydrothiophene-1,1
Aldehyde compounds such as dioxide, triiodoallyl alcohol, bromonitrostyrene, glutaraldehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, dichloroglyoxime, α-chlorobenzaldoxime acetate, α-chlorobenzaldoxime, Benzaldoxime compounds such as 5-methylhydantoin and the like can be mentioned. As antifoaming agents, for example, silicone-based and non-silicone-based antifoaming agents, as surfactants, for example, anionic, cationic, nonionic, amphoteric surfactants, as anti-algal agents, for example, Amethrin and the like can be mentioned.

As one embodiment of the composition of the present invention, 0.1 to 10% by weight of the isothiazolone compound represented by the general formula [1] or [2], the general formula [3] or the general formula [4]
0.1 to 20% by weight of an aliphatic sulfonic acid represented by the formula: 0 to 50% by weight of a corrosion inhibitor, 0 to 50% by weight of a scale inhibitor, 0 to 30% by weight of an antibacterial agent, and 0 to 10% by weight of an antifoaming agent And an antibacterial composition containing 0 to 10% by weight of a surfactant, 0 to 10% by weight of an antialgal agent, and 30 to 99% by weight of water or a hydrophilic organic solvent. The concentration of the antibacterial composition of the present invention can be appropriately selected and used according to the object and purpose. For example, for the purpose of preventing slime in paper and paper making systems and cooling water systems, the concentration of the isothiazolone-based compound is preferably 0.1 to 25 g / m ³ , and synthetic resin emulsion, starch paste, starch slurry, For the purpose of preserving paints and metal working oils, the concentration of the isothiazolone compound is 1 to 5,000 g /
m ³ is preferred. The antibacterial composition of the present invention,
It contains an isothiazolone compound and an aliphatic sulfonic acid, has excellent stability over time and heat stability, does not cause decomposition of the isothiazolone compound even when stored for a long time, and exhibits an excellent antibacterial effect based on the isothiazolone compound.

[0013]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. Example 1 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3
-One in an ethylene glycol solution containing 1% by weight [Z
ONEN-F, manufactured by Ichikawa Gosei Chemical Co., Ltd.] 5.0 parts by weight, 0.79 parts by weight of methanesulfonic acid and 94.21 parts by weight of water were mixed and uniformly dissolved to prepare an antibacterial composition. This antibacterial composition contains methanesulfonic acid in an amount of 2 mole times the total number of moles of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one. I do. Instead of methanesulfonic acid, 5-chloro-2-methyl-4-methyl-4-sulfonic acid was used as aliphatic sulfonic acid using ethanesulfonic acid, 1-propanesulfonic acid, ethanedisulfonic acid and 1,3-propanedisulfonic acid.
11% by weight of isothiazolin-3-one, 2-methyl-
Ethylene glycol solution containing 1% by weight of 4-isothiazolin-3-one [ZONEN-F, Ichikawa Gosei Chemical
5.0 parts by weight, 5-chloro-2-methyl-4-
Aliphatic sulfonic acid and water having a total amount of 100 parts by weight relative to the total number of moles of isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one are mixed and uniformly dissolved, Four more antimicrobial compositions were prepared. The above five antimicrobial compositions were left at room temperature for one month, but all of the antimicrobial compositions remained in a transparent liquid state,
No precipitate was observed. Comparative Example 1 5-chloro-2-methyl-4-isothiazolin-3-one (11% by weight), 2-methyl-4-isothiazolin-3
-One in an ethylene glycol solution containing 1% by weight [Z
ONEN-F, manufactured by Ichikawa Gosei Kagaku Co., Ltd.] and 95.0 parts by weight of water were mixed and uniformly dissolved to prepare an antibacterial composition. When this antibacterial composition was allowed to stand at room temperature for one month, generation of a yellow-orange precipitate was observed. Table 1 shows the results of Example 1 and Comparative Example 1.

[0014]

[Table 1]

As seen in Table 1, 5-chloro-2
The antibacterial composition of Comparative Example 1 containing -methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and not containing aliphatic sulfonic acid was left at room temperature for one month. Although a precipitate is generated, the antibacterial composition of Example 1 containing the aliphatic sulfonic acid shows no change in appearance even when left at room temperature for one month, indicating that it has excellent stability over time. . Example 2 After leaving the five kinds of antibacterial compositions prepared in Example 1 in a thermostat kept at 60 ° C. for 48 hours, 5-chloro-2 was used.
The content of -methyl-4-isothiazolin-3-one was measured by high performance liquid chromatography, and the residual ratio was calculated. The residual ratio of 5-chloro-2-methyl-4-isothiazolin-3-one in the antibacterial composition containing methanesulfonic acid was 93%. Other antimicrobial compositions of 5-chloro-2-methyl-4-isothiazoline-3-
Table 2 shows the ON ratio. Comparative Example 2 The antibacterial composition containing no aliphatic sulfonic acid prepared in Comparative Example 1 was allowed to stand in a thermostat maintained at 60 ° C. for 48 hours, and then was treated with 5-chloro-2-methyl-4-isothiazoline-3. An attempt was made to measure the content of -one by high performance liquid chromatography. The peak of 5-chloro-2-methyl-4-isothiazolin-3-one does not appear in the chromatogram, and 5-chloro-2-methyl-4-isothiazolin-3
-On had completely decomposed. Comparative Example 3 5-chloro-2-methyl-4-isothiazolin-3-one (11% by weight), 2-methyl-4-isothiazolin-3
-One in an ethylene glycol solution containing 1% by weight [Z
ONEN-F, manufactured by Ichikawa Gosei Chemical Co., Ltd.] 5.0 parts by weight, 1.1 parts by weight of potassium methanesulfonate and 93.9 parts by weight of water were mixed and uniformly dissolved to prepare an antibacterial composition. .
Also, 1.1 parts by weight of potassium methanesulfonate and 9 parts of water
An antibacterial composition was similarly prepared using 1.9 parts by weight of disodium ethanedisulfonate and 93.1 parts by weight of water instead of 3.9 parts by weight. These antimicrobial compositions comprise 5-chloro-2-methyl-4-isothiazoline-3
It contains potassium methanesulfonate or disodium ethanedisulfonate in an amount of 2 moles per mole of the total number of -one and 2-methyl-4-isothiazolin-3-one. These antimicrobial compositions were placed in a thermostat maintained at 60 ° C. for 48 hours.
After standing for a time, the content of 5-chloro-2-methyl-4-isothiazolin-3-one was measured by high performance liquid chromatography, and the residual ratio was calculated. The residual ratio of 5-chloro-2-methyl-4-isothiazolin-3-one is 48% for the antibacterial composition containing potassium methanesulfonate, and the antibacterial composition containing disodium ethanedisulfonate is 48%. 56%. Table 2 shows the results of Example 2 and Comparative Examples 2 and 3.

[0016]

[Table 2]

As can be seen in Table 2, 5-chloro-2
The antibacterial composition of Comparative Example 2 containing -methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and not containing aliphatic sulfonic acid was heated at 60 ° C.
For 48 hours.
Isothiazolin-3-one is completely decomposed. In contrast, the antimicrobial composition of Example 2 containing an aliphatic sulfonic acid had a residual ratio of 5-chloro-2-methyl-4-isothiazolin-3-one even after being left at 60 ° C. for 48 hours. And high thermal stability. In particular, two kinds of antibacterial compositions containing disulfonic acid as an aliphatic sulfonic acid include 5-chloro-2-methyl-4-isothiazoline-
3-one remains without any decomposition and is particularly excellent in thermal stability. On the other hand, in the antibacterial composition of Comparative Example 3 containing an aliphatic sulfonic acid salt, although 5-chloro-2-methyl-4-isothiazolin-3-one remains, the residual ratio is aliphatic sulfonic acid. Is lower than the antimicrobial composition containing the compound. From the results, it can be understood that the aliphatic sulfonic acid has a greater effect on improving the thermal stability than the aliphatic sulfonic acid salt. Example 3 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3
-One in an ethylene glycol solution containing 1% by weight [Z
ONEN-F, manufactured by Ichikawa Gosei Chemical Co., Ltd.] 5.0 parts by weight, 0.79 parts by weight of methanesulfonic acid and 94.21 parts by weight of water were mixed and uniformly dissolved to prepare an antibacterial composition. This antibacterial composition contains methanesulfonic acid in an amount of 2 mole times the total number of moles of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one. I do. Bacillus Subtillu
The growth inhibitory effect of this antibacterial composition was examined using s. Bacillus Sub was added to a pH 7 liquid medium containing 1 g / l of peptone and 1 g / l of yeast extract.
tilus was inoculated at 10 ⁶ cells / ml, and the above-mentioned antibacterial composition was added at concentrations of 20 mg / l, 60 mg / l and 100 mg / l, and 3
Shaking culture was performed at 0 ° C. for 24 hours. The concentration of the antimicrobial composition is 2
In the case of 0 mg / liter, no growth inhibitory effect was observed, but when the concentration was 60 mg / liter or 100 mg / liter, the growth inhibitory effect was observed. After the above antibacterial composition was allowed to stand at room temperature for one month, the growth inhibitory effect was examined again in the same manner. When the concentration of the antibacterial composition was 20 mg / l, no growth inhibitory effect was observed, but when the concentrations were 60 mg / l and 100 mg / l, the growth inhibitory effect was observed. Comparative Example 4 5-chloro-2-methyl-4-isothiazolin-3-one (11% by weight), 2-methyl-4-isothiazolin-3
-One in an ethylene glycol solution containing 1% by weight [Z
ONEN-F, manufactured by Ichikawa Gosei Chemical Co., Ltd.] and 95.0 parts by weight of water were mixed and uniformly dissolved to prepare an antibacterial composition. Bacillus S of this antibacterial composition
The growth inhibitory effect on Utilus was examined in the same manner as in Example 3. When the concentration of the antibacterial composition was 20 mg / l, no growth inhibitory effect was observed, but when the concentrations were 60 mg / l and 100 mg / l, the growth inhibitory effect was observed. After the above antibacterial composition was allowed to stand at room temperature for one month, the growth inhibitory effect was examined again in the same manner. The concentration of the antibacterial composition is 20 mg / liter, 6
No growth inhibitory effect was observed in any of the cases of 0 mg / liter and 100 mg / liter. Table 3 shows the results of Example 3 and Comparative Example 4.

[0018]

[Table 3]

As shown in Table 3, when the antibacterial composition containing no aliphatic sulfonic acid prepared in Comparative Example 4 was left at room temperature for one month, Bacillus Subtill was obtained.
while the growth inhibitory effect on us is completely lost
The antibacterial composition containing methanesulfonic acid prepared in Example 3 has a growth inhibitory effect even after being left at room temperature for one month, indicating that the antibacterial composition of the present invention has excellent temporal stability.

[0020]

The antibacterial composition of the present invention contains an isothiazolone compound and an aliphatic sulfonic acid, has excellent stability over time and heat stability, and can cause decomposition of the isothiazolone compound even when stored for a long period of time. And exhibits an excellent antibacterial effect based on the isothiazolone compound.

Claims (1)

[Claims] (1) An isothiazolone compound represented by the general formula [1] or [2] and an aliphatic sulfonic acid represented by the general formula [3] or [4]. Antimicrobial composition. Embedded image (Wherein, R ¹ is hydrogen, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group. X and Y
Is a compound which forms a benzene ring together with hydrogen or halogen, or carbon at the 4-position and 5-position of the isothiazolone compound. M is an alkali metal, an alkaline earth metal,
A cation of a heavy metal or amine, Z is an anion that forms a compound with a cation M that has sufficient solubility to form a complex compound. a is 1 or 2, n
Is an integer in which the anion Z satisfies the valence of the cation M. ) R ² SO ₃ H ... [3] (wherein, R ² is an alkyl group having 1 to 4 carbon atoms.) HO ₃ SR ³ SO ₃ H ... [4] ³ is an alkylene group having 1 to 4 carbon atoms.)