JP4993443B2 - Industrial disinfectant and disinfecting method using the same - Google Patents

Description

    TECHNICAL FIELD The present invention relates to an industrial disinfectant and a disinfecting method using the same, and more particularly to an industrial disinfectant used for an application object having a pH exceeding 8.0, and a disinfecting method using the industrial disinfectant.

Conventionally, harmful microorganisms such as bacteria, mold, and yeast are easily propagated in various industrial products, which causes a decrease in productivity and quality and generation of malodor. For this reason, it is widely known that industrial products are added with various industrial bactericides that exert a bactericidal effect on bacteria, molds and yeasts.
Examples of such industrial disinfectants include 5-chloro-2-methyl-4-isothiazolin-3-one (hereinafter abbreviated as Cl-MIT) and 2-methyl-4-isothiazolin-3-one (hereinafter referred to as “Cl-MIT”). It is widely known to add isothiazoline compounds such as MIT.

In addition, as such an industrial disinfectant, it has been proposed to use, for example, 1,3-di-n-dodecyl-2-methyl-imidazolium bromide (see, for example, Patent Document 1).
JP 51-115476 A

In addition, acrylic emulsions used for paints and the like may be adjusted to an alkalinity exceeding pH 8.0, for example, and industrial disinfectants that can be used for such alkaline acrylic emulsions are desired. ing.
However, in the case of Cl-MIT, when the application target is alkaline, there is a problem that Cl-MIT itself decomposes after a long period of time has elapsed after the addition.

  In addition, although MIT has bactericidal properties against bacteria but does not have fungicidal properties against mold and yeast, it is usually not 2-n-octyl-4-isothiazolin-3-one (hereinafter abbreviated as OIT). )), Since OIT is hydrophobic, there is a problem that the industrial disinfectant combined with MIT and OIT has poor solubility in water.

In addition, Patent Document 1 describes that 1,3-di-n-dodecyl-2-methyl-imidazolium bromide has bactericidal properties against bacteria. Although the application subject of sex (pH 4-8) is described, the use in the application subject exceeding pH 8.0 is not mentioned.
Therefore, the object of the present invention is to maintain excellent stability even when applied to an application object having good solubility in water and exceeding pH 8.0, and excellent for bacteria, molds and yeasts over a long period of time. An object of the present invention is to provide an industrial disinfectant that can exhibit bactericidal properties and a disinfecting method using the industrial disinfectant.

  In order to achieve the above object, the present inventors maintain excellent stability even when applied to an application target exceeding pH 8.0, and are superior to bacteria, molds, yeasts, etc. over a long period of time. As a result of diligent research on industrial disinfectants that can exhibit high bactericidal properties, and sterilization methods using the same, the application of imidazolium salts to applications exceeding pH 8.0 solves the above-mentioned problems. As a result of finding out that it can be done and further researching it, the present invention has been completed.

That is, the present invention
(1) An industrial disinfectant comprising an imidazolium salt and applied to an application subject exceeding pH 8.0,
(2) The industrial disinfectant according to (1), wherein the imidazolium salt is represented by the following general formula (1):

（一般式（１）中、Ｒ１およびＲ３は、同一または相異なって、水素または炭素数１〜１８の炭化水素基を、Ｒ２は、水素または炭素数１〜１２の炭化水素基を、Ｘ^-はアニオンを示す。）
（３） 上記一般式（１）中のＲ１およびＲ３のうち、いずれか一方は、炭素数８〜１８のアルキル基であり、他方は、炭素数７〜１０のアラルキル基であることを特徴とする、上記（２）に記載の工業用殺菌剤、
（４） 適用対象のｐＨが、８．０を超過し、１０．０以下であることを特徴とする、上記（１）〜（３）のいずれかに記載の工業用殺菌剤、
（５） 上記（１）〜（４）のいずれかに記載の工業用殺菌剤を用いて、ｐＨ８．０を超過する適用対象を殺菌することを特徴とする、殺菌方法、
を提供するものである。

(In the general formula (1), R1 and R3, same or different, hydrogen or a hydrocarbon group having 1 to 18 carbon atoms, R2 is hydrogen or a hydrocarbon group having 1 to 12 carbon atoms, X ^- Represents an anion.)
(3) One of R1 and R3 in the general formula (1) is an alkyl group having 8 to 18 carbon atoms, and the other is an aralkyl group having 7 to 10 carbon atoms. The industrial disinfectant according to (2) above,
(4) The industrial disinfectant according to any one of (1) to (3) above, wherein the pH to be applied exceeds 8.0 and is 10.0 or less,
(5) The sterilization method characterized by sterilizing the application object exceeding pH 8.0 using the industrial disinfectant according to any one of (1) to (4) above,
Is to provide.

  The industrial bactericidal agent of the present invention has good solubility in water and maintains excellent stability even when applied to an application subject having a pH exceeding 8.0. Can exhibit excellent bactericidal properties. Therefore, according to the sterilization method of the present invention, stable sterilization can be realized even in an application target exceeding pH 8.0. Therefore, in the application target exceeding pH 8.0, productivity and quality over a long period of time. It is possible to prevent the occurrence of odor and the generation of malodor.

The industrial disinfectant of the present invention contains an imidazolium salt.
Such an imidazolium salt is a salt formed from an imidazolium cation and an anion, and is represented, for example, by the following general formula (1).

（一般式（１）中、Ｒ１およびＲ３は、同一または相異なって、水素または炭素数１〜１８の炭化水素基を、Ｒ２は、水素または炭素数１〜１２の炭化水素基を、Ｘ^-はアニオンを示す。）
一般式（１）の式中、Ｒ１およびＲ３で示される炭素数１〜１８の炭化水素基としては、例えば、炭素数１〜１８のアルキル基、炭素数２〜１８のアルケニル基、炭素数２〜１８のアルキニル基、炭素数３〜１８のシクロアルキル基、炭素数６〜１８のアリール基、炭素数７〜１８のアラルキル基などが挙げられる。

(In the general formula (1), R1 and R3, same or different, hydrogen or a hydrocarbon group having 1 to 18 carbon atoms, R2 is hydrogen or a hydrocarbon group having 1 to 12 carbon atoms, X ^- Represents an anion.)
In the formula of the general formula (1), examples of the hydrocarbon group having 1 to 18 carbon atoms represented by R1 and R3 include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and 2 carbon atoms. -18 alkynyl group, C3-C18 cycloalkyl group, C6-C18 aryl group, C7-C18 aralkyl group, etc. are mentioned.

  Examples of the alkyl group having 1 to 18 carbon atoms include methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl, tert-butyl, pentyl, iso-pentyl, sec-pentyl, hexyl and heptyl. , N-octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and the like alkyl groups having 1 to 18 carbon atoms.

  Examples of the alkenyl group having 2 to 18 carbon atoms include vinyl, allyl, methallyl, isopropenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, butenyl, pentenyl, hexenyl, heptynyl, octenyl, nonenyl, Examples thereof include alkenyl groups having 2 to 18 carbon atoms such as decenyl, undecenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl and the like.

Examples of the alkynyl group having 2 to 18 carbon atoms include ethynyl, 1-propynyl, 2-propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tetradecynyl, hexadecynyl, octadecynyl and the like. The alkynyl group of number 2-18 is mentioned.
Examples of the cycloalkyl group having 3 to 18 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotetradecyl, cyclohexadecyl, and cyclooctadecyl. And a cycloalkyl group having 3 to 18 carbon atoms.

Examples of the aryl group having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms such as phenyl, tolyl, xylyl, biphenyl, naphthyl, anthryl, phenanthryl, and azulenyl.
Examples of the aralkyl group having 7 to 18 carbon atoms include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, diphenylmethyl, o, m or p-methyl. Benzyl, o, m or p-ethylbenzyl, o, m or p-isopropylbenzyl, o, m or p-tert-butylbenzyl, 2,3-, 2,4-, 2,5-, 2,6- 3,4- or 3,5-dimethylbenzyl, 2,3,4-, 3,4,5- or 2,4,6-trimethylbenzyl, 5-isopropyl-2-methylbenzyl, 2-isopropyl-5 -Methylbenzyl, 2-methyl-5-tert-butylbenzyl, 2,4-, 2,5- or 3,5-diisopropylbenzyl, 3,5-di-tert-butyl Rubenzyl, 2,6-diisopropyl-4-tert-butylbenzyl, 4-isopropyl-2,6-di-tert-butylbenzyl, 1- (2-methylphenyl) ethyl, 1- (3-methylphenyl) ethyl, 1- (4-methylphenyl) ethyl, 1- (2-isopropylphenyl) ethyl, 1- (3-isopropylphenyl) ethyl, 1- (4-isopropylphenyl) ethyl, 1- (2-tert-butylphenyl) Ethyl, 1- (4-tert-butylphenyl) ethyl, 1- (2-isopropyl-4-methylphenyl) ethyl, 1- (4-isopropyl-2-methylphenyl) ethyl, 1- (2,4-dimethyl) Phenyl) ethyl, 1- (2,5-dimethylphenyl) ethyl, 1- (3,5-dimethylphenyl) ethyl, 1- (3 Aralkyl group having 7 to 18 carbon atoms, such as 5-di -tert- butylphenyl) ethyl.

In general formula (1), in R1 and R3, preferably one of these is an alkyl group having 8 to 18 carbon atoms, and the other is an aralkyl group having 7 to 10 carbon atoms. .
Examples of the alkyl group having 8 to 18 carbon atoms of any one of R1 and R3 include, for example, an alkyl group having 8 to 18 carbon atoms among the above-described alkyl groups having 1 to 18 carbon atoms. Is dodecyl.

Examples of the other aralkyl group having 7 to 10 carbon atoms, which is the other of R1 and R3, include the aralkyl groups having 7 to 10 carbon atoms among the aralkyl groups having 7 to 18 carbon atoms described above, preferably , Benzyl.
In the formula of general formula (1), examples of the hydrocarbon group having 1 to 12 carbon atoms represented by R2 include an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and 2 to 12 carbon atoms. Alkynyl group, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, and the like.

As a C1-C12 alkyl group, the thing similar to a C1-C12 alkyl group is mentioned among the C1-C18 alkyl groups shown by R1 and R3 mentioned above, for example.
Examples of the alkenyl group having 2 to 12 carbon atoms include those similar to the alkenyl group having 2 to 12 carbon atoms among the alkenyl groups having 2 to 18 carbon atoms represented by R1 and R3 described above.

As a C2-C12 alkynyl group, the same thing as a C2-C12 alkynyl group among the C2-C18 alkynyl groups shown by R1 and R3 mentioned above is mentioned, for example.
Examples of the cycloalkyl group having 3 to 12 carbon atoms include those similar to the cycloalkyl group having 3 to 12 carbon atoms among the cycloalkyl groups having 3 to 18 carbon atoms represented by R1 and R3 described above. Can be mentioned.

Examples of the aryl group having 6 to 12 carbon atoms include those similar to the aryl group having 6 to 12 carbon atoms among the aryl groups having 6 to 18 carbon atoms represented by R1 and R3 described above.
Examples of the aralkyl group having 7 to 12 carbon atoms include those similar to the aralkyl group having 7 to 12 carbon atoms among the aralkyl groups having 7 to 18 carbon atoms represented by R1 and R3 described above.

Among these, as R2, Preferably, a C1-C12 alkyl group is mentioned, More preferably, methyl is mentioned.
In the general formula (1), the anion represented by X ⁻ is, for example, a monovalent anion, and examples of such a monovalent anion include an inorganic anion and an organic anion.

Examples of inorganic anions include halogen ions (eg, F ⁻ , Cl ⁻ , Br ⁻ , I ^−, etc.), iodate ions (IO ₃ ⁻ ), bromate ions (BrO ₃ ⁻ ), chlorate ions (ClO _3). ^- ), Periodate ion (IO ₄ ⁻ ), perchlorate ion (ClO ₄ ⁻ ), nitrate ion (NO ₃ ⁻ ), nitrite ion (NO ₂ ⁻ ), tetrafluoroborate ion (BF ₄ ⁻ ), Hexafluorophosphate ions (PF ₆ ⁻ ) and the like can be mentioned.

Examples of organic anions include free organic acids such as free organic carboxylic acids and free organic sulfonic acids.
Examples of the free organic carboxylic acid include saturated carboxylate ions such as formate ion (HCOO ⁻ ), acetate ion (CH ₃ COO ⁻ ), propionate ion (C ₂ H ₅ COO ⁻ ), for example, acrylate ion ( And unsaturated carboxylate ions such as CH ₂ ═CHCOO ⁻ ) and methacrylate ions (CH ₂ ═C (CH ₃ ) COO ⁻ ).

Examples of the free organic sulfonic acid include methyl sulfate ion ((CH ₃ ) SO ₄ ⁻ ), ethyl sulfate ion ((C ₂ H ₅ ) SO ₄ ⁻ ), and benzene sulfonate ion (C ₆ H ₄ SO ₃ ^−). ), Methylbenzenesulfonate ion (CH ₃ C ₆ H ₄ SO ₃ ⁻ ), and the like.
Among the anions represented by X ⁻ , a monovalent inorganic anion is preferable, a halogen ion is more preferable, and Cl ⁻ and Br ⁻ are particularly preferable.

The imidazolium salts are used alone or in combination.
In addition, since such an imidazolium salt is a salt formed from an imidazolium cation and an anion, it is usually water-soluble and has a solubility at 25 ° C. of, for example, 1 to 1000 g / 100 g of water, Preferably, it is 10-500 g / 100 g of water.
In the industrial disinfectant of the present invention, specific examples of imidazolium salts include 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 1-dodecyl-2-methyl-3-benzylimidazolium. Bromide, 1-tetradecyl-2-methyl-3-benzylimidazolium chloride, 1-hexadecyl-2-methyl-3-benzylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-octadecyl-2-methyl -3-Benzylimidazolium bromide, 1-benzyl-2-undecyl-3-methylimidazolium methyl sulfate, 1-dodecyl-2-phenyl-3-ethylimidazolium ethyl sulfate, 1-benzyl-2-phenyl-3- Dodecylimidazolium chlorai 1,2-dibenzyl-3-octadecylimidazolium bromide, 1-octyl-2-methyl-3-methylimidazolium toluenesulfonate, 1-dodecyl-2,3-dimethylimidazolium iodide, 1,3-didodecyl- 2-methylimidazolium bromide, 1,3-didodecyl-2-methylimidazolium chloride, 1,2-dimethyl-3-benzylimidazolium chloride, 1,3-dibenzyl-2-methylimidazolium chloride, 1-ethyl- 3-methylimidazolium bromide, 1-methyl-3-propylimidazolium iodide, 1,2-dimethyl-3-propylimidazolium iodide, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl- 3-methylimida Such as hexafluorophosphate and the like. Preferably, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 1-dodecyl-2-methyl-3-benzylimidazolium bromide, 1-tetradecyl-2-methyl-3-benzylimidazolium chloride, 1- Hexadecyl-2-methyl-3-benzylimidazolium chloride is mentioned, More preferably, 1-dodecyl-2-methyl-3-benzylimidazolium chloride is mentioned.

Such an imidazolium salt can be produced in accordance with, for example, the description of JP-A No. 51-115476.
In the industrial disinfectant of the present invention, the imidazolium salt described above can be used alone as it is. In addition, active ingredients other than imidazolium salts, additives, and the like can be further added and used at the time of manufacturing industrial disinfectants.

The active ingredient other than the imidazolium salt described above is not particularly limited, and has at least one of antibacterial, bactericidal, antiseptic, fungicidal, yeast-killing, and algicidal effects depending on its use and purpose. The active ingredient which has is mentioned.
Such an active ingredient is not particularly limited, and examples thereof include iodine compounds, triazole compounds, sulfamide compounds, bis quaternary ammonium salt compounds, quaternary ammonium salt compounds, phthalonitrile compounds, dithiol compounds. Thiophene compounds, thiocarbamate compounds, nitrile compounds, phthalimide compounds, haloalkylthio compounds, pyridine compounds, pyrithione compounds, benzothiazole compounds, triazine compounds, guanidine compounds, urea compounds, imidazole compounds Examples include compounds (excluding imidazolium salts), nitroalcohol compounds, phenylurea compounds, and the like.

  Examples of the iodine compound include 3-iodo-2-propynylbutylcarbamate (common name: IPBC), p-chlorophenyl-3-iodopropargyl formal (trade name: IF-1000, manufactured by Nagase Sangyo Co., Ltd.), 1 -[[(3-Iodo-2-propynyl) oxy] methoxy] -4-methoxybenzene, 3-bromo-2,3-diiodo-2-propenyl ethyl carbonate (trade name: Sampras, Sankyo Co., Ltd.) Etc.

  Examples of triazole compounds include 1-[[2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole. (Common name: propiconazole), α- [2- (4-chlorophenyl) ethyl] -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (common name: Tebuconazole), α- (4-chlorophenyl) -α- (1-cyclopropylethyl) -1H-1,2,4-triazole-1-ethanol (common name: cyproconazole), 1-[[2- ( 2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole (common name: azaconazole) and the like.

Examples of the sulfamide-based compound include N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenylsulfamide (trade name: Priventol A4 / S, manufactured by Bayer), N-dichlorofluoromethylthio-N ′. , N′-dimethyl-N-4-tolylsulfamide (trade name: Priventol A5, manufactured by Bayer) and the like.
Examples of bisquaternary ammonium salt compounds include N, N′-hexamethylenebis (4-carbamoyl-1-decylpyridinium bromide) (trade name: Dimer 38, manufactured by Inui Corporation), N, N′— Hexamethylene bis (4-carbamoyl-1-decylpyridinium acetate) (trade name: Dimer 38A, manufactured by Inui Corporation), 4,4 ′-(tetramethylenedicarbonyldiamino) bis (1-decylpyridinium bromide) (product) Name: Dimer 136, manufactured by Inui Corporation), 4,4 ′-(tetramethylenedicarbonyldiamino) bis (1-decylpyridinium acetate) (trade name: Dimer 136A, manufactured by Inui Corporation), and the like.

Examples of the quaternary ammonium salt compounds include di-n-decyl-dimethylammonium chloride, 1-hexadecylpyridinium chloride, hexadecyltrimethylammonium bromide, hexadecyltrimethylammonium chloride, benzalkonium chloride, and coatamine D10EPR (Kao ( Etc.).
Examples of the phthalonitrile-based compound include 2,4,5,6-tetrachloroisophthalonitrile (trade name: Nopcoside N-96, manufactured by San Nopco).

Examples of the dithiol-based compound include 4,5-dichloro-1,2-dithiol-3-one.
Examples of the thiophene compound include 3,3,4-trichlorotetrahydrothiophene-1,1-dioxide, 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide, and the like.

Examples of the thiocarbamate compound include tetramethylthiuram disulfide.
Examples of the nitrile compound include 2,4,5,6-tetrachloroisophthalonitrile.
Examples of the phthalimide compound include N-1,1,2,2-tetrachloroethylthio-tetrahydrophthalimide (Captafol), N-trichloromethylthio-tetrahydrophthalimide (Captan), N-dichlorofluoromethylthiophthalimide (Fluorolpet), N- And trichloromethylthiophthalimide (Folpet).

  Examples of the haloalkylthio compounds include N-dimethylaminosulfonyl-N-tolyl-dichlorofluoromethanesulfamide (Tolylfluoride), N-dimethylaminosulfonyl-N-phenyl-dichlorofluoromethanesulfamide (Dichlofluoride), N -(Fluorodichloromethylthio) -N, N′-dimethyl-N-phenyl-sulfamide and the like.

Examples of the pyridine-based compound include 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine.
Examples of the pyrithione compound include zinc pyrithione and sodium pyrithione.
Examples of the benzothiazole compound include 2- (4-thiocyanomethylthio) benzothiazole.

Examples of the triazine compound include 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine.
Examples of the guanidine compound include 1,6-di- (4′-chlorophenyldiguanide) -hexane, polyhexamethylene biguanidine hydrochloride, and the like.
Examples of urea compounds include 3- (3,4-dichlorophenyl) -1,1-dimethylurea.

Examples of the imidazole compound are those obtained by removing the imidazolium salt described above, and examples thereof include methyl-2-benzimidazole carbamate (common name: MBC), 2- (4-thiazolyl) -benzimidazole, and the like.
Examples of the nitroalcohol compound include 2-bromo-2-nitropropane-1,3-diol, 2,2-dibromo-2-nitro-1-ethanol, and the like.

Examples of the phenylurea compound include 3- (3,4-dichlorophenyl) -1,1-dimethylurea.
These active ingredients are used alone or in combination.
The additive is not particularly limited, and examples thereof include a surfactant, an antioxidant, and a light stabilizer.

The surfactant is not particularly limited, and may be a known interface such as soaps, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, and polymer surfactants. An activator is mentioned, Preferably, a nonionic surfactant and an anionic surfactant are mentioned.
Examples of the nonionic surfactant include polyoxyalkylene aryl phenyl ether, polyoxyethylene nonyl phenyl ether, block copolymer of ethylene oxide and propylene oxide, sorbitan fatty acid ester, sucrose fatty acid ester, and the like.

As an anionic surfactant, for example, alkylbenzenesulfonic acid metal salt, alkylnaphthalenesulfonic acid metal salt, polycarboxylic acid type surfactant, dialkylsulfosuccinic acid ester metal salt, polyoxyethylene distyrenated phenyl ether sulfate ammonium salt, Examples thereof include lignin sulfonic acid metal salts. Moreover, as these metal salts, a sodium salt, potassium salt, magnesium salt etc. are mentioned, for example.

These surfactants are used alone or in combination.
The antioxidant is not particularly limited. For example, phenol-based oxidation such as 2,6-di-t-butyl-4-methylphenol and 2,2′-methylenebis [4-methyl-6-t-butylphenol]. Examples of the antioxidant include amine-based antioxidants such as alkyldiphenylamine and N, N′-di-s-butyl-p-phenylenediamine. These antioxidants are used alone or in combination.

The light stabilizer is not particularly limited, and examples thereof include hindered amine light stabilizers such as bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate and the like, and are used alone or in combination. .
These additives are used alone or in combination.
In the industrial disinfectant of the present invention, when an active ingredient other than the imidazolium salt is added, the blending ratio of such an active ingredient is, for example, 5 to 1000 weights with respect to 100 parts by weight of the imidazolium salt. Parts, preferably 10 to 500 parts by weight.

  Moreover, in the industrial disinfectant of the present invention, when additives are added, the blending ratio of each additive is, for example, 0.1 to 100 parts by weight of the imidazolium salt. 30 parts by weight, preferably 0.2 to 20 parts by weight, for antioxidants, for example, 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, for light stabilizers, for example, 0. 1 to 10 parts by weight, preferably 0.2 to 5 parts by weight.

Subsequently, the sterilization method of this invention which sterilizes the application object using the industrial disinfectant of this invention is demonstrated.
In the sterilization method of the present invention, in order to sterilize the application object using the above-described industrial disinfectant of the present invention, the industrial disinfectant of the present invention may be added to the application object as it is. Also, depending on the purpose and application, for example, it is formulated into a known dosage form such as a liquid (including water suspension and oil), paste, powder, granule, microcapsule, etc. and added to the application target You can also In addition, it may be prepared as an inclusion compound in formulation, and further supported on montmorillonite such as layered silicate (such as smectites) or adsorbed on clay, silica, white carbon, talc, etc. It is also possible to add those prepared by (1).

In the sterilization method of the present invention, the application target to which the above-described industrial disinfectant is applied is an aqueous system, and its pH exceeds 8.0. Specifically, for example, the pH exceeds 8.0 and is 10.0 or less, preferably the pH is 8.5 to 9.5, and more preferably the pH is 9.0. ~ 9.5.
In addition, the application target is not particularly limited as long as the above-described aqueous system has a pH exceeding 8.0. For example, various industrial water such as a paper pulp factory and a cooling water circulation process, cutting oil, etc. Metal processing oil, casein, starch powder, glue, coated paper, paper coating liquid, sizing agent, paper strength enhancer, paint, adhesive, synthetic rubber latex, ink, polyvinyl alcohol film, vinyl chloride film, resin Examples include various industrial products such as products, cement admixtures, sealing agents, and joint preparations.

More specifically, application targets include acrylic emulsions used for paints and adhesives.
Moreover, in the sterilization method of the present invention, the industrial bactericidal agent of the present invention may be appropriately determined depending on the application target, for example, 5 to 1000 mg (imidazolium salt) / kg (application target), preferably Is added as a concentration of 10 to 500 mg (imidazolium salt) / kg (application object).

  And the industrial disinfectant of the present invention has good solubility in water and maintains excellent stability even when applied to an application subject exceeding pH 8.0, and it can be used over a long period of time. It can exhibit excellent bactericidal properties against yeast and the like. Therefore, according to the sterilization method of the present invention, stable sterilization can be realized even in an application target exceeding pH 8.0, that is, industrial water and industrial products (acrylic emulsion, etc.) exceeding pH 8.0. Therefore, in industrial water and industrial products exceeding pH 8.0, it is possible to prevent productivity, quality deterioration, and generation of malodors over a long period of time.

Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples.
Example 1
1-dodecyl-2-methyl-3-benzylimidazolium chloride was subjected to evaluation described later as an industrial disinfectant.
Comparative Example 1
1,3-dodecyl-2-methylimidazolium bromide was subjected to the evaluation described later as an industrial disinfectant.

Comparative Example 2
5-Chloro-2-methyl-4-isothiazolin-3-one (Cl-MIT) was subjected to evaluation described later as an industrial disinfectant.
Comparative Example 3
2-Methyl-4-isothiazolin-3-one (MIT) was subjected to evaluation described later as an industrial disinfectant.

Comparative Example 4
1-dodecyl-2-methylimidazole was subjected to evaluation described later as an industrial disinfectant.
Evaluate (1) sterilizing test glucose agar medium (Glucose-bouillon agar), first, each adjusted to pH shown in Table 1 and Table 2, then Example 1, contact and that these above, Comparative Example 1, Predetermined amounts of 3 and 4 industrial fungicides were added, respectively, and then the following test bacteria (bacteria, mold, yeast) were inoculated.

  Thereafter, the bacteria were cultured at 33 ° C. for 18 hours, and the mold and yeast were cultured at 33 ° C. for 18 hours, and further cultured at 28 ° C. for 2 days. After the culture, the minimum inhibitory concentration (MIC, μg / ml) was determined by the Agar dilution method (1000 to 2.0 μg / ml, 10-step dilution). The results are shown in Tables 1 and 2.

なお、表１および表２中、「Ｎｏ．」に対応する試験菌（細菌、カビ、酵母）は以下の通りである。
＜細菌＞
Ｎｏ．１：バチルス・ズブチリス（Ｂａｃｉｌｌｕｓ ｓｕｂｔｉｌｌｉｓ、枯草菌、グラム陽性菌）
Ｎｏ．２：スタフィロコッカス・アウレウス（Ｓｔａｐｈｙｌｏｃｏｃｃｕｓ ａｕｒｅｕｓ、黄色ぶどう球菌、グラム陽性菌）
Ｎｏ．３：エシュリアヒア・コリー（Ｅｓｃｈｅｒｉａｃｈｉａ ｃｏｌｉ、大腸菌、グラム陰性菌）
Ｎｏ．４：シュードモナス・エルギノーサ（Ｐｓｅｕｄｏｍｏｎａｓ ａｅｒｕｇｉｎｏｓａ、緑膿菌、グラム陰性菌）
Ｎｏ．５：セラチア・マルセッセンス（Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ、霊菌、グラム陰性菌）
＜カビ＞
Ｎｏ．６：アスペルギルス・ニガー（Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ、黒カビ）
Ｎｏ．７：ペニシリウム・シトリナム（Ｐｅｎｉｃｉｌｌｉｕｍ ｃｉｔｒｉｎｕｍ、青カビ）
Ｎｏ．８：クラドスポリウム・クラドスポリオイデス（Ｃｌａｄｏｓｐｏｒｉｕｍ ｃｌａｄｏｓｐｏｒｉｏｉｄｅｓ、クロカワカビ）
Ｎｏ．９：アウレオバシヂウム・プルランス（Ａｕｒｅｏｂａｓｉｄｉｕｍ、ｐｕｌｌｕｌａｎｓ、黒色酵母様菌）
Ｎｏ．１０：アルタナリア・スピーシーズ（Ａｌｔｅｒｎａｒｉａ ｓｐ．、ススカビ）
Ｎｏ．１１：グリオクラヂウム・ヴィレンス（Ｇｌｉｏｃｌａｄｉｕｍ ｖｉｒｅｎｓ）
Ｎｏ．１２：ムコール・スピネッセンス（Ｍｕｃｏｒ ｓｐｉｎｅｓｃｅｎｓ、毛カビ）
＜酵母＞
Ｎｏ．１３：ロドトルラ・ルブラ（Ｒｈｏｄｏｔｏｒｕｌａ ｒｕｂｒａ、赤色酵母）
Ｎｏ．１４：サッカロマイセス・セレビシアエ（Ｓａｃｃｈａｒｏｍｙｃｅｓ ｃｅｒｅｖｉｓｉａｅ、白色酵母）
（２） 安定性試験
実施例１の工業用殺菌剤の１０重量％水溶液を用意し、これを１Ｎ水酸化ナトリウム水溶液により、ｐＨ７．０、ｐＨ８．０およびｐＨ９．５に、それぞれ調整した。

In Tables 1 and 2, the test bacteria (bacteria, mold, yeast) corresponding to “No.” are as follows.
<Bacteria>
No. 1: Bacillus subtilis (Bacillus subtilis, Bacillus subtilis, Gram-positive bacteria)
No. 2: Staphylococcus aureus (Staphylococcus aureus, Staphylococcus aureus, Gram-positive bacteria)
No. 3: Escherichia coli, Escherichia coli, gram-negative bacteria
No. 4: Pseudomonas aeruginosa (Pseudomonas aeruginosa, Pseudomonas aeruginosa, Gram-negative bacteria)
No. 5: Serratia marcescens (Serratia marcescens)
<Mold>
No. 6: Aspergillus niger (black mold)
No. 7: Penicillium citrinum (blue mold)
No. 8: Cladosporium cladosporioides (Kurokawa mold)
No. 9: Aureobasidium pullulans (Aureobasidium, pullulans, black yeast-like fungus)
No. 10: Alternaria sp. (Alternaria sp.)
No. 11: Gliocladium virens
No. 12: Mucor spinesence (Mucor spinescens)
<Yeast>
No. 13: Rhodotorula rubra (red yeast)
No. 14: Saccharomyces cerevisiae (white yeast)
(2) Stability test A 10% by weight aqueous solution of the industrial bactericide of Example 1 was prepared and adjusted to pH 7.0, pH 8.0, and pH 9.5 with a 1N aqueous sodium hydroxide solution, respectively.

Further, the industrial bactericides of Comparative Example 2 and Comparative Example 3 were mixed at a weight ratio of 1: 3 to prepare a 10% by weight mixed aqueous solution of these total amounts, which was adjusted to pH 7. with a 1N sodium hydroxide aqueous solution. The pH was adjusted to 0, pH 8.0, and pH 9.5, respectively.
After pH adjustment, the aqueous solution of Example 1 and the mixed aqueous solution of Comparative Examples 2 and 3 were allowed to stand at 60 ° C. for 14 days, and then the remaining industrial disinfectant was obtained by high performance liquid chromatography (HPLC). Each was analyzed quantitatively to determine the residual rate of each industrial disinfectant. The results are shown in Table 3.

  The industrial disinfectant of the present invention is applied as an agent that imparts bactericidal properties by adding it to an object of application exceeding pH 8.0, specifically, industrial water or industrial product exceeding pH 8.0. be able to.

Claims (3)

Including an imidazolium salt represented by the following general formula (1) ,
An industrial disinfectant characterized by being applied to an application subject exceeding pH 8.0.

(In General Formula (1), one of R1 and R3 is an alkyl group having 8 to 18 carbon atoms, the other is an aralkyl group having 7 to 10 carbon atoms, and R2 is hydrogen or carbon. (The hydrocarbon group having a number of 1 to 12 and X ⁻ represents an anion.) The industrial disinfectant according to claim 1 , wherein the pH to be applied is more than 8.0 and not more than 10.0. The sterilization method characterized by disinfecting the application object which exceeds pH 8.0 using the industrial disinfectant of Claim 1 or 2 .