Quaternary ammonium disinfectant

Abstract: A disinfectant comprising at least one quaternary ammonium salt represented by the following general formula (1): wherein R 1 represents an alkyl group of 8-14 carbon atoms, R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms, and [B] represents two monovalent inorganic or organic anion groups or one divalent inorganic or organic anion group. The disinfectant has excellent bacteriocidal activity and is suitable as a disinfectant for medical care and working areas.

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to the use of quaternary ammonium salts as disinfectants. 2. Description of the Related Art Conventional disinfectants include gas type of ethylene oxide, etc., aldehyde type of glutaraldehyde, etc., alcohol type of ethanol, etc., peroxide type of hydrogen peroxide, etc., iodine type of iodine tincture, iodoform, etc., chlorine compound type of hypochlorous acid, chloramine, etc., and phenol type of phenol soap, etc. However, all such disinfectants have had drawbacks including odor, irritation and toxicity, as well as effects on containers and utensils, and therefore it has been necessary to determine their proper use depending on the purpose. Quaternary ammonium salts such as benzalkonium chloride, amphoteric surfactants such as alkyldiamino-ethylglycine hydrochloride and biguanide-based compounds such as chlorhexidine digluconate are used in a variety of different fields because they are odorless and have low toxicity and irritation, minimal effect on containers and utensils, and satisfactory bacterial action. In particular, the wide use of the biguanide-based disinfectant chlorhexidine gluconate for its excellent bacteriocidal effect has led to the discovery of many drug-resistant bacterial strains with resistance to the disinfectant. Future opportunistic infection by such drug-resistant microorganisms has become a risk, as seen in the problem of hospital infection by MRSA (methicillin-resistant Staphylococcus aureus ). Imam et al. disclose in Pharmazie 38 (1983), pages 308 to 310, α,α-p-xylenebis (decyldimethylammonium) dibromide and its antimicrobial activity. Yet, despite the more frequent appearance of strains resistant to chlorhexidine digluconate as compared to benzalkonium chloride or alkyldiaminoethylglycine hydrochloride, no superior disinfectant has yet been found. SUMMARY OF THE INVENTION It is an object of the present invention to provide a disinfectant comprising a quaternary ammonium salt compound which has a more excellent bacteriocidal action than benzalkonium chloride, alkyldiamino-ethylglycine hydrochloride or chlorhexidine digluconate and which is suitable as a disinfectant for medical care and working areas. As a result of diligent research aimed at overcoming the problems described above, the inventors have completed the present invention based on the finding that quaternary ammonium salts with two cationic groups in their compounds have strong bacteriocidal activity. That is, the present invention proposes to use a quaternary ammonium salt represented by the following general formula (1): wherein R 1 represents a dodecyl, tridecyl or tetradecyl group 12, R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms, and [B] represents two monovalent inorganic or organic anion groups or one divalent inorganic or organic anion group as disinfectant. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a 1 H-NMR spectrum of the compound obtained in Example 1. Fig. 2 is a 1 H-NMR spectrum of the compound obtained in Example 3. Fig. 3 is a 1 H-NMR spectrum of the compound obtained in Example 27. Fig. 4 is a 1 H-NMR spectrum of the compound obtained in Example 44. DESCRIPTION OF THE PREFERRED EMBODIMENTS According to the present invention, the inorganic or organic anion group [B] may preferably be a sulfate ion, phosphate ion, phosphite ion, hypophosphite ion, nitrate ion, nitrite ion, chlorate ion, chlorite ion, hypochlorite ion or any of the anion groups represented by the following general formulas (2)-(8). 2[X - ] wherein X represents a chlorine atom, bromine atom or iodine atom; 2[R 4 COO - ] wherein R 4 represents an alkyl group or alkenyl group of 1-7 carbon atoms which may have a hydroxyl group or carbonyl group; [ - OCO-R 5 -COO - ] wherein R 5 represents a direct bond or an alkylene group or alkenylene group of 1-8 carbon atoms which may have a hydroxyl group; wherein each R 6 represents an alkyl group of 1-8 carbon atoms, and the phosphate ester anion may be a single monoester or diester or a mixture thereof; wherein each R 7 represents an alkyl group of 1-8 carbon atoms, and the phosphonate ester anion may be a single monoester or diester or a mixture thereof; wherein R s represents an alkyl group of 1-2 carbon atoms; wherein R 9 and R 10 each represent a hydrogen atom, methyl group or carboxyl group. The quaternary ammonium salt represented by general formula (1) above used according to the invention may be produced by reaction of a quaternizing agent of the following general formula (9) and a tertiary amine of the following general formula (10). wherein X represents a chlorine atom, bromine atom or iodine atom; wherein R 1 represents a dodecyl, tridecyl or tetradecyl group 12, and R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms. As compounds of general formula (9) above there may be mentioned, for example, halogenated compounds such as α,α'-dichloro-p-xylene, α,α'-dichloro-m-xylene, α,α'-dichloro-o-xylene, α,α'-dibromo-p-xylene, α,α'-dibromo-m-xylene, α,α'-dibromo-o-xylene, α,α'-diiodo-p-xylene, α,α'-diiodo-m-xylene and α,α'-diiodo-o-xylene. As compounds of general formula (10) above there may be mentioned, for example, tertiary amines such as N,N-dimethyl-dodecylamine, N,N-dimethyl-tridecylamine, N,N-dimethyl-tetradecylamine, N,N-diethyl-dodecylamine, N,N-diethyl-tridecylamine and N,N-diethyl-tetradecylamine. The quaternary ammonium salt represented by general formula (1) may be produced by reaction of a tertiary amine represented by the following general formula (11) and a quaternizing agent represented by the following general formula (12). wherein R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms; R 1 -X wherein R 1 represents a dodecyl, tridecyl or tetradecyl group 12 and X represents a chlorine atom, bromine atom or iodine atom. As compounds of general formula (11) above there may be mentioned, for example, tertiary amines such as 1,2-bis(N,N-dimethyl-aminomethyl)benzene, 1,3-bis(N,N-dimethyl-aminomethyl)benzene, 1,4-bis(N,N-dimethyl-aminomethyl)benzene, 1,2-bis(N,N-diethyl-aminomethyl)benzene, 1,3-bis(N,N-diethyl-aminomethyl)benzene, 1,4-bis(N,N-diethyl-aminomethyl)benzene. As compounds of general formula (12) above there may be mentioned, for example, alkyl halides such as dodecyl chloride, tridecyl chloride, tetradecyl chloride, dodecyl bromide, tridecyl bromide, tetradecyl bromide, dodecyl iodide, tridecyl iodide and tetradecyl iodide. The quaternary ammonium salt represented by general formula (1) may also be produced by reaction of a tertiary amine represented by the following general formula (13) and a quaternizing agent represented by the following general formula (14). wherein R 1 represents a dodecyl, tridecyl or tetradecyl group 12 and R 2 represents an alkyl group of 1-2 carbon atoms; R 3 -Y wherein R 3 represents an alkyl group of 1-2 carbon atoms and Y represents a chlorine atom, bromine atom, iodine atom or a group represented by one of the following general formulas (15), (16) or (17). wherein R 8 represents an alkyl group of 1-2 carbon atoms; wherein R 9 and R 10 each represent a hydrogen atom or methyl group; wherein R 11 represents an alkyl group of 1-2 carbon atoms. As compounds represented by general formula (13) above there may be mentioned, for example, tertiary amines such as 1,2-bis(N-dodecyl-N-methylaminomethyl)benzene, 1,2-bis(N-dodecyl-N-ethylaminomethyl)benzene, 1,2-bis(N-tridecyl-N-methylaminomethyl)benzene, 1,2-bis(N-tridecyl-N-ethylaminomethyl)benzene, 1,2-bis(N-tetradecyl-N-methylaminomethyl)benzene, 1,2-bis(N-tetradecyl-N-ethylaminomethyl)benzene, 1,3-bis(N-dodecyl-N-methylaminomethyl)benzene, 1,3-bis(N-dodecyl-N-ethylaminomethyl)benzene, 1,3-bis(N-tridecyl-N-methylaminomethyl)benzene, 1,3-bis(N-tridecyl-N-ethylaminomethyl)benzene, 1,3-bis(N-tetradecyl-N-methylaminomethyl)benzene, 1,3-bis(N-tetradecyl-N-ethylaminomethyl)benzene, 1,4-bis(N-dodecyl-N-methylaminomethyl)benzene, 1,4-bis(N-dodecyl-N-ethylaminomethyl)benzene, 1,4-bis(N-tridecyl-N-methylaminomethyl)benzene, 1,4-bis(N-tridecyl-N-ethylaminomethyl)benzene, 1,4-bis(N-tetradecyl-N-methylaminomethyl)benzene and 1,4-bis(N-tetradecyl-N-ethylaminomethyl)benzene. As compounds of general formula (14) there may be mentioned, for example, alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, methyl iodide and ethyl iodide; dialkylsulfuric acids such as dimethylsulfuric acid and diethylsulfuric acid; alkyl sulfonates such as methyl p-toluenesulfonate and ethyl p-toluenesulfonate; and trialkyl phosphates such as trimethyl phosphate and triethyl phosphate. As reaction solvents for quaternization of these tertiary amines with the quaternizing agent there may preferably be employed water, an alcohol, or a mixed solvent of water and alcohol, and as alcohols there may preferably employed methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol and t-butanol, although they are not limited to these solvents. The reaction temperature will depend on the alkyl chain lengths of the tertiary amine or quaternizing agent, but the reaction usually proceeds rapidly at 80°C or higher. The quaternary ammonium salt represented by general formula (1) may be produced by ion-exchange of a cationic group-containing quaternary ammonium salt compound of the following general formula (18) with sulfuric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, nitric acid, nitrous acid, chloric acid, chlorous acid, hypochlorous acid or a compound of any of general formulas (19), (20), (21), (22) or (23). wherein R 1 represents a dodecyl, tridecyl or tetradecyl group 12, and R 7 and R 3 each represent an alkyl group of 1-2 carbon atoms; R 4 -COOH wherein R 4 represents an alkyl group or alkenyl group of 1-7 carbon atoms which may have a hydroxyl group or carbonyl group; HOOC-R 5 -COOH wherein R 5 represents a direct bond or an alkylene group or alkenylene group of 1-8 carbon atoms which may have a hydroxyl group; wherein each R 6 represents an alkyl group of 1-8 carbon atoms, and the phosphate ester may be a single monoester or diester or a mixture thereof; wherein each R 7 represents an alkyl group of 1-8 carbon atoms, and the phosphonate ester may be a single monoester or diester or a mixture thereof; wherein R 9 and R 10 each represent a hydrogen atom, methyl group or carboxyl group. As compounds of general formula (19) above there may be mentioned, for example, carboxylic acids such as acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, caproic acid, caprylic acid, lactic acid, pyruvic acid, acetoacetic acid, acrylic acid and methacrylic acid, among which as preferred ones there may be mentioned acetic acid, propionic acid, butyric acid, isobutyric acid, lactic acid and acetoacetic acid. As compounds of general formula (20) there may be mentioned, for example, dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, tartaric acid, maleic acid and fumaric acid, among which as preferred ones there may be mentioned malonic acid, tartaric acid and maleic acid. As phosphate ester compounds of general formula (21) there may be mentioned, for example, monoesters and diesters with alkyl groups of 1-8 carbon atoms, and as preferred ones there may be mentioned monoesters and diesters in which the alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl. As phosphonate ester compounds of general formula (22) there may be mentioned, for example, monoesters and diesters with alkyl groups of 1-8 carbon atoms, and as preferred ones there may be mentioned monoesters and diesters in which the alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl. As compounds of general formula (23) there may be preferably employed, for example, sulfonic acids such as o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, o-xylene-4-sulfonic acid, m-xylene-4-sulfonic acid, p-xylenesulfonic acid and isophthalylsulfonic acid. The ion-exchange may be carried out easily by treatment in a column filled with an anion-exchange resin. The present invention will now be further explained by way of the following examples. Example 1 After charging 42.6g of dodecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-o-xylene and 100 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 200 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride to adjust the concentration to 10 wt%. The results of 1 H-nuclear magnetic resonance spectrum (hereinafter abbreviated to 1 H-NMR. Measuring apparatus: FT-NMR R-1900, product of Hitachi Laboratories) analysis using a 2% heavy methanol solution with a tetramethylsilane indicator (Fig. 1) identified it as the object compound. Example 2 After charging 42.6g of dodecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-m-xylene and 100 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 200 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride product to adjust the concentration to 10 wt%. Example 3 After charging 42.6g of dodecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-p-xylene and 200 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, the purified solution was cooled and the precipitated crystals were filtered off and washed with cold water. Water was added to the obtained 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride crystals to dissolve them, and the concentration was adjusted to 1 wt%. The results of 1 H-NMR analysis (Fig. 2) identified it as the object compound. Example 4 After charging 48.2g of tetradecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-o-xylene and 100 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 200 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,2-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride product to adjust the concentration to 10 wt%. Example 5 After charging 48.2g of tetradecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-m-xylene and 100 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 200 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,3-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride product to adjust the concentration to 5 wt%. Example 6 After charging 48.2g of tetradecyldimethylamine and 50 ml of water in a 500 ml reaction container the mixture was heated to 75°C. Next, a solution of 17.5g of α,α'-dichloro-p-xylene and 100 ml of isopropanol was slowly added dropwise. After the dropwise addition, a reaction was conducted for one hour while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 200 ml of water to distill off the alcohol portion. After the steam distillation, the purified solution was cooled and the precipitated crystals were filtered off and washed with cold water. Water was added to the obtained 1,4-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride crystals to dissolve them, and the concentration was adjusted to 1 wt%. Example 7 After charging 17.8g of 1,2-bis(N,N-dimethyl-aminomethyl)benzene, 40.9g of dodecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride product to adjust the concentration to 10 wt%. Example 8 After charging 17.8g of 1,3-bis(N,N-dimethyl-aminomethyl)benzene, 40.9g of dodecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride product to adjust the concentration to 5 wt%. Example 9 After charging 17.8g of 1,4-bis(N,N-dimethyl-aminomethyl)benzene, 40.9g of dodecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 2 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene dichloride product to adjust the concentration to 1 wt%. Example 10 After charging 17.8g of 1,2-bis(N,N-dimethyl-aminomethyl)benzene, 46.5g of tetradecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 3 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,2-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride product to adjust the concentration to 10 wt%. Example 11 After charging 17.8g of 1,3-bis(N,N-dimethyl-aminomethyl)benzene, 46.5g of tetradecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 3 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,3-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride product to adjust the concentration to 5 wt%. Example 12 After charging 17.8g of 1,4-bis(N,N-dimethyl-aminomethyl)benzene, 46.5g of tetradecyl chloride, 50 ml of water and 200 ml of isopropanol in a 500 ml reaction container, a reaction was conducted for 3 hours while heating to reflux to obtain a transparent homogeneous solution. After maturing for 3 hours, the solution was subjected to steam distillation while slowly adding 300 ml of water to distill off the alcohol portion. After the steam distillation, water was added to the 1,4-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene dichloride product to adjust the concentration to 1 wt%. Example 13 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 14 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 15 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 16 The compound obtained in Example 4 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 17 The compound obtained in Example 5 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 18 The compound obtained in Example 6 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a methyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene methyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 19 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with an ethyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene ethyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 20 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with an ethyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene ethyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 21 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with an ethyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene ethyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 22 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a propyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene propyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 23 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a propyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene propyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 24 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 6.8 ±0.2 with a propyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene propyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 25 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.3 with a butyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene butyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 26 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.3 with a butyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene butyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 27 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.3 with a butyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene butyl phosphate ester salt product to adjust the concentration to 1 wt%. The results of 1 H-NMR analysis (Fig. 3) identified it as the object compound. Example 28 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with a hexyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene hexyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 29 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with a hexyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene hexyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 30 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with a hexyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene hexyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 31 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with tartaric acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene tartrate salt product to adjust the concentration to 1 wt%. Example 32 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with succinic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene succinate salt product to adjust the concentration to 1 wt%. Example 33 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with malonic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene malonate salt product to adjust the concentration to 1 wt%. Example 34 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with adipic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene adipate salt product to adjust the concentration to 1 wt%. Example 35 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with acetic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene acetate salt product to adjust the concentration to 1 wt%. Example 36 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with lactic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene lactate salt product to adjust the concentration to 1 wt%, Example 37 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with gluconic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene gluconate salt product to adjust the concentration to 1 wt%. Example 38 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with tartaric acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene tartrate salt product to adjust the concentration to 1 wt%. Example 39 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with succinic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene succinate salt product to adjust the concentration to 1 wt%. Example 40 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with malonic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene malonate salt product to adjust the concentration to 1 wt%. Example 41 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with adipic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene adipate salt product to adjust the concentration to 1 wt%. Example 42 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with acetic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene acetate salt product to adjust the concentration to 1 wt%. Example 43 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with lactic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene lactate salt product to adjust the concentration to 1 wt%. Example 44 The compound obtained in Example 3 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with gluconic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene gluconate salt product to adjust the concentration to 1 wt%. The results of 1 H-NMR analysis (Fig. 4) identified it as the object compound. Example 45 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with tartaric acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene tartrate salt product to adjust the concentration to 1 wt%. Example 46 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with succinic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene succinate salt product to adjust the concentration to 1 wt%. Example 47 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with malonic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene malonate salt product to adjust the concentration to 1 wt%. Example 48 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with adipic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene adipate salt product to adjust the concentration to 1 wt%. Example 49 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with acetic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene acetate salt product to adjust the concentration to 1 wt%. Example 50 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with lactic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene lactate salt product to adjust the concentration to 1 wt%. Example 51 The compound obtained in Example 2 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with gluconic acid, and water was added to the 1,3-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene gluconate salt product to adjust the concentration to 1 wt%. Example 52 The compound obtained in Example 4 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with butyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,2-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene butyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 53 The compound obtained in Example 6 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with butyl phosphate ester (monoester/diester = 50/50), and water was added to the 1,4-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene butyl phosphate ester salt product to adjust the concentration to 1 wt%. Example 54 The compound obtained in Example 4 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with gluconic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene gluconate ester salt product to adjust the concentration to 1 wt%. Example 55 The compound obtained in Example 6 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.5 with gluconic acid, and water was added to the 1,4-bis(N,N-dimethyl-N-tetradecylammoniomethyl)benzene gluconate ester salt product to adjust the concentration to 1 wt%. Example 56 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.2 with sulfuric acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene sulfate salt product to adjust the concentration to 1 wt%. Example 57 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.2 with nitric acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene nitrate salt product to adjust the concentration to 1 wt%. Example 58 The compound obtained in Example 1 was treated in a column filled with an anion-exchange resin. The treatment solution was adjusted to pH 7.0 ±0.2 with p-toluenesulfonic acid, and water was added to the 1,2-bis(N,N-dimethyl-N-dodecylammoniomethyl)benzene p-toluenesulfonate salt product to adjust the concentration to 1 wt%. Comparative Example 1 Benzalkonium chloride. Comparative Example 2 Chlorhexidine digluconate Evaluation method The minimum bacteriocidal concentration (MBC) of the non-volatile portions of the compounds of Examples 1 to 71 and Comparative Examples 1 and 2 were measured according to the Standards of the Japan Chemotherapy Institute, using 2 strains of methicillin-resistant Staphylococcus aureus ( S . aureus (MRSA)), 2 strains of Staphylococcus aureus ( S . aureus), 3 strains of Escherichia coli ( E . coli ), 3 strains of Pseudomonas aeruginosa ( P . aeruginosa), 2 strains of Klebsiella pneumoniae ( K . pneumoniae), 2 strains of Serratia marcescens ( S . marcescens ) and 2 strains of Salmonella enteritidis ( S . enteritidis ), and the bacteriocidal effects were compared. The results are shown in Tables 1 to 18. Bacteria strain MBC (µg/ml) Comp.Ex.1 Comp.Ex.2 Example 1 Example 2 S. aureus (MRSA) A 50 25 2.5 2.5 S. aureus (MRSA) B 50 25 2.5 2.5 S. aureus A 25 25 2.5 2.5 S . aureus B 25 50 2.5 2.5 E. coli A 25 5 2.5 2.5 E. coli B 25 10 2.5 2.5 E. coli C 25 10 2.5 2.5 P. aeruginosa A 25 25 2.5 2.5 P. aeruginosa B 50 25 2.5 2.5 P. aeruginosa C 50 100 2.5 2.5 K. pneumoniae A 50 5 5 5 K . pneumoniae B 50 5 5 5 S. marcescens A 25 25 5 5 S. marcescens B 25 10 5 5 S. enteritidis A 25 5 5 5 S. enteritidis B 25 5 5 5 Bacteria strain MBC (µg/ml) Example 3 Example 4 Example 5 Example 6 S . aureus (MRSA) A 2.5 10 5 10 S. aureus (MRSA) B 2.5 5 10 5 S. aureus A 2.5 5 5 5 S. aureus B 2.5 5 5 5 E . coli A 2.5 5 5 5 E . coli B 2.5 5 10 5 E. coli C 2.5 10 5 10 P. aeruginosa A 2.5 25 25 25 P. aeruginosa B 2.5 5 5 5 P. aeruginosa C 2.5 5 5 5 K. pneumoniae A 5 25 10 25 K . pneumoniae B 5 10 25 10 S. marcescens A 5 10 10 10 S. marcescens B 5 10 10 10 S. enteritidis A 5 5 10 10 S. enteritidis B 5 5 10 10 Bacteria strain MBC (µg/ml) Example 7 Example 8 S . aureus (MRSA) A 2.5 2.5 S . aureus (MRSA) B 2.5 2.5 S . aureus A 2.5 2.5 S . aureus B 2.5 2.5 E. coli A 2.5 2.5 E. coli B 2.5 2.5 E. coli C 2.5 2.5 P. aeruginosa A 2.5 2.5 P. aeruginosa B 2.5 2.5 P. aeruginosa C 2.5 2.5 K. pneumoniae A 5 5 K. pneumoniae B 5 5 S. marcescens A 5 5 S. marcescens B 5 5 S. enteritidis A 5 5 S. enteritidis B 5 5 Bacteria strain MBC (µg/ml) Example 9 Example 10 Example 11 Example 12 S. aureus (MRSA) A 2.5 10 10 10 S. aureus (MRSA) B 2.5 10 10 10 S. aureus A 2.5 5 5 5 S . aureus B 2.5 5 5 5 E. coli A 2.5 5 5 5 E. coli B 2.5 10 10 10 E. coli C 2.5 5 5 5 P. aeruginosa A 2.5 5 5 5 P. aeruginosa B 2.5 25 25 25 P. aeruginosa C 2.5 5 5 5 K. pneumoniae A 5 25 25 25 K. pneumoniae B 5 10 10 10 S. marcescens A 5 10 10 10 S. marcescens B 5 10 10 10 S. enteritidis A 5 10 10 10 S. enteritidis B 5 10 10 10 Bacteria strain MBC (µg/ml) Example 13 S. aureus (MRSA) A 2.5 S. aureus (MRSA) B 2.5 S . aureus A 2.5 S. aureus B 2.5 E. coli A 2.5 E. coli B 2.5 E. coli C 2.5 P. aeruginosa A 2.5 P. aeruginosa B 2.5 P. aeruginosa C 2.5 K. pneumoniae A 5 K . pneumoniae B 5 S. marcescens A 5 S. marcescens B 5 S. enteritidis A 5 S. enteritidis B 5 Bacteria strain MBC (µg/ml) Example 14 Example 15 Example 16 Example 17 S . aureus (MRSA) A 2.5 2.5 10 10 S . aureus (MRSA) B 2.5 2.5 10 10 S . aureus A 2.5 2.5 5 5 S . aureus B 2.5 2.5 5 5 E . coli A 2.5 2.5 5 5 E. coli B 2.5 2.5 10 10 E . coli C 2.5 2.5 5 5 P . aeruginosa A 2.5 2.5 5 5 P . aeruginosa B 2.5 2.5 25 25 P . aeruginosa C 2.5 2.5 5 5 K . pneumoniae A 5 5 25 25 K. pneumoniae B 5 5 10 10 S . marcescens A 5 5 10 10 S. marcescens B 5 5 10 10 S. enteritidis A 5 5 10 10 S. enteritidis B 5 5 10 10 Bacteria strain MBC (µg/ml) Example 18 Example 19 Example 29 Example 21 S . aureus (MRSA) A 10 2.5 2.5 2.5 S . aureus (MRSA) B 10 2.5 2.5 2.5 S . aureus A 5 2.5 2.5 2.5 S. aureus B 5 5 2.5 5 E . coli A 5 2.5 2.5 2.5 E . coli B 10 2.5 2.5 2.5 E. coli C 5 2.5 2.5 2.5 P . aeruginosa A 5 5 5 5 P . aeruginosa B 25 5 5 5 P . aeruginosa C 5 5 5 5 K . pneumoniae A 25 5 5 5 K . pneumoniae B 10 5 5 5 S . marcescens A 10 5 5 5 S . marcescens B 10 5 5 5 S . enteritidis A 10 5 5 5 S . enteritidis B 10 5 5 5 Bacteria strain MBC (µg/ml) Example 22 Example 23 Example 24 Example 25 S . aureus (MRSA) A 2.5 2.5 2.5 2.5 S . aureus (MRSA) B 2.5 2.5 2.5 2.5 S . aureus A 5 2.5 5 5 S . aureus B 5 2.5 5 5 E . coli A 2.5 2.5 5 2.5 E. coli B 2.5 2.5 5 2.5 E . coli C 2.5 2.5 5 2.5 P . aeruginosa A 5 5 5 5 P. aeruginosa B 5 5 5 5 P. aeruginosa C 5 5 5 5 K . pneumoniae A 5 5 5 5 K. pneumoniae B 5 5 5 5 S . marcescens A 5 5 5 5 S. marcescens B 5 5 5 5 S. enteritidis A 5 5 5 5 S. enteritidis B 5 5 5 5 Bacteria strain MBC (µg/ml) Example 26 Example 27 Example 28 Example 29 S . aureus (MRSA) A 2.5 2.5 2.5 2.5 S . aureus (MRSA) B 2.5 2.5 2.5 2.5 S . aureus A 2.5 2.5 5 2.5 S . aureus B 2.5 2.5 5 2.5 E . coli A 2.5 5 2.5 2.5 E . coli B 2.5 5 2.5 2.5 E . coli C 2.5 5 2.5 2.5 P . aeruginosa A 5 5 5 5 P . aeruginosa B 5 5 5 5 P . aeruginosa C 5 5 5 5 K . pneumoniae A 2.5 5 5 5 K . pneumoniae B 2.5 5 5 5 S. marcescens A 2.5 5 5 5 S . marcescens B 2.5 5 5 5 S . enteritidis A 5 5 5 5 S . enteritidis B 5 5 5 5 Bacteria strain MBC (µg/ml) Example 30 Example 31 Example 32 Example 33 S . aureus (MRSA) A 2.5 2.5 5 2.5 S . aureus (MRSA) B 2.5 2.5 5 2.5 S . aureus A 2.5 5 5 2.5 S . aureus B 2.5 5 5 2.5 E. coli A 5 5 5 2.5 E. coli B 5 5 5 2.5 E. coli C 5 5 5 2.5 P. aeruginosa A 5 10 10 2.5 P. aeruginosa B 5 10 10 5 P. aeruginosa C 5 10 10 5 K. pneumoniae A 5 5 5 5 K. pneumoniae B 5 5 5 2.5 S. marcescens A 5 10 10 5 S . marcescens B 5 10 10 5 S . enteritidis A 5 10 10 5 S . enteritidis B 5 10 10 5 Bacteria strain MBC (µg/ml) Example 34 Example 35 Example 36 Example 37 S . aureus (MRSA) A 2.5 2.5 2.5 2.5 S . aureus (MRSA) B 2.5 2.5 2.5 2.5 S . aureus A 2.5 2.5 2.5 2.5 S . aureus B 2.5 2.5 2.5 2.5 E. coli A 2.5 2.5 2.5 5 E. coli B 2.5 2.5 2.5 5 E. coli C 2.5 2.5 2.5 5 P. aeruginosa A 2.5 5 5 5 P. aeruginosa B 5 5 5 5 P. aeruginosa C 5 5 5 5 K. pneumoniae A 2.5 2.5 2.5 2.5 K. pneumoniae B 2.5 2.5 2.5 2.5 S. marcescens A 5 5 5 5 S. marcescens B 5 5 5 5 S. enteritidis A 5 5 5 2.5 S. enteritidis B 5 5 5 2.5 Bacteria strain MBC (µg/ml) Example 38 Example 39 Example 40 Example 41 S . aureus (MRSA) A 2.5 5 2.5 2.5 S . aureus (MRSA) B 2.5 5 2.5 2.5 S . aureus A 5 5 2.5 2.5 S. aureus B 5 5 2.5 2.5 E. coli A 5 5 2.5 2.5 E. coli B 5 5 2.5 2.5 E. coli C 5 5 2.5 2.5 P. aeruginosa A 10 10 2.5 2.5 P. aeruginosa B 10 10 5 5 P. aeruginosa C 10 10 5 5 K . pneumoniae A 5 5 5 2.5 K. pneumoniae B 5 5 2.5 2.5 S . marcescens A 10 10 5 5 S . marcescens B 10 10 5 5 S. enteritidis A 10 10 5 5 S . enteritidis B 10 10 5 5 Bacteria strain MBC (µg/ml) Example 42 Example 43 Example 44 Example 45 S. aureus (MRSA) A 2.5 2.5 2.5 2.5 S. aureus (MRSA) B 2.5 2.5 2.5 2.5 S. aureus A 2.5 2.5 5 5 S. aureus B 2.5 2.5 5 5 E . coli A 2.5 2.5 5 5 E . coli B 2.5 2.5 5 5 E . coli C 2.5 2.5 5 5 P . aeruginosa A 5 5 5 10 P . aeruginosa B 5 5 5 10 P . aeruginosa C 5 5 5 10 K . pneumoniae A 2.5 2.5 10 5 K . pneumoniae B 2.5 2.5 5 5 S. marcescens A 5 5 5 10 S. marcescens B 5 5 5 10 S. enteritidis A 5 5 2.5 10 S. enteritidis B 5 5 2.5 10 Bacteria strain MBC (µg/ml) Example 46 Example 47 Example 48 Example 49 S . aureus (MRSA) A 5 2.5 2.5 2.5 S . aureus (MRSA) B 5 2.5 2.5 2.5 S . aureus A 5 2.5 2.5 2.5 S . aureus B 5 2.5 2.5 2.5 E. coli A 5 2.5 2.5 2.5 E. coli B 5 2.5 2.5 2.5 E. coli C 5 2.5 2.5 2.5 P . aeruginosa A 10 2.5 2.5 5 P . aeruginosa B 10 5 5 5 P . aeruginosa C 10 5 5 5 K . pneumoniae A 5 5 2.5 2.5 K . pneumoniae B 5 2.5 2.5 2.5 S . marcescens A 10 5 5 5 S . marcescens B 10 5 5 5 S . enteritidis A 10 5 5 5 S . enteritidis B 10 5 5 5 Bacteria strain MBC (µg/ml) Example 50 Example 51 S . aureus (MRSA) A 2.5 2.5 S . aureus (MRSA) B 2.5 5 S . aureus A 2.5 5 S . aureus B 2.5 2.5 E. coli A 2.5 2.5 E. coli B 2.5 2.5 E. coli C 2.5 2.5 P. aeruginosa A 2.5 2.5 P. aeruginosa B 5 2.5 P. aeruginosa C 5 5 K. pneumoniae A 2.5 5 K. pneumoniae B 2.5 5 S. marcescens A 5 2.5 S. marcescens B 5 2.5 S . enteritidis A 5 2.5 S . enteritidis B 5 2.5 Bacteria strain MBC (µg/ml) Example 52 Example 53 S . aureus (MRSA) A 5 5 S . aureus (MRSA) B 5 5 S . aureus A 5 5 S . aureus B 10 10 E. coli A 5 5 E. coli B 5 5 E. coli C 5 5 P. aeruginosa A 10 25 P. aeruginosa B 10 5 P. aeruginosa C 5 10 K. pneumoniae A 10 10 K. pneumoniae B 10 10 S . marcescens A 25 25 S . marcescens B 25 25 S. enteritidis A 10 25 S . enteritidis B 10 25 Bacteria strain MBC (µg/ml) Example 54 Example 55 Example 56 Example 57 S. aureus (MRSA) A 5 5 2.5 2.5 S. aureus (MRSA) B 5 5 2.5 2.5 S. aureus A 5 5 2.5 2.5 S. aureus B 5 5 5 5 E. coli A 5 5 2.5 2.5 E. coli B 5 5 2.5 2.5 E. coli C 5 5 2.5 2.5 P. aeruginosa A 10 25 5 5 P . aeruginosa B 10 10 5 5 P. aeruginosa C 10 10 5 5 K. pneumoniae A 10 10 5 5 K. pneumoniae B 10 10 5 5 S. marcescens A 25 25 5 5 S. marcescens B 25 25 5 5 S. enteritidis A 25 25 5 5 S. enteritidis B 25 25 5 5 Bacteria strain MBC (µg/ml) Example 58 S. aureus (MRSA) A 5 S. aureus (MRSA) B 5 S . aureus A 5 S . aureus B 5 E . coli A 5 E . coli B 5 E . coli C 5 P . aeruginosa A 10 P . aeruginosa B 10 P . aeruginosa C 10 K . pneumoniae A 5 K . pneumoniae B 5 S . marcescens A 10 S . marcescens B 10 S . enteritidis A 10 S . enteritidis B 10 The quaternary ammonium salt used according to the present invention exhibits a stronger bacteriocidal effect than the conventional disinfectant benzalkonium chloride, while also having equivalent or greater bacteriocidal performance than chlorhexidine digluconate, and it is therefore useful as a disinfectant or the like.

Claims: The use of a quaternary ammonium salt represented by the following general formula (1): wherein R 1 represents a dodecyl, tridecyl or tetradecyl group, R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms, and [B] represents two monovalent inorganic or organic anion groups or one divalent inorganic or organic anion group as disinfectant. The use according to claim 1, wherein said inorganic or organic anion group [B] is a sulfate ion, phosphate ion, phosphite ion, hypophosphite ion, nitrate ion, nitrite ion, chlorate ion, chlorite ion, hypochlorite ion or any one of the anion groups represented by the following general formulas (2)-(8). 2[X - ] wherein X represents a chlorine atom, bromine atom or iodine atom; 2[R 4 COO - ] wherein R 4 represents an alkyl group or alkenyl group of 1-7 carbon atoms which may have a hydroxyl group or carbonyl group; [ - OCO-R 5 -COO - ] wherein R 5 represents a direct bond or an alkylene group or alkenylene group of 1-8 carbon atoms which may have a hydroxyl group; wherein each R 6 represents an alkyl group of 1-8 carbon atoms, and the phosphate ester anion may be a single monoester or diester or a mixture thereof; wherein each R 7 represents an alkyl group of 1-8 carbon atoms, and the phosphonate ester anion may be a single monoester or diester or a mixture thereof; wherein R 8 represents an alkyl group of 1-2 carbon atoms; wherein R 9 and R 10 each represent a hydrogen atom, methyl group or carboxyl group. The use according to claim 1, wherein said quaternary ammonium salt is synthesized by reaction between a compound of the following general formula (9) and a compound of the following general formula (10). wherein X represents a chlorine atom, bromine atom or iodine atom; wherein R 1 represents a dodecyl, tridecyl or tetradecyl group, and R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms. The use according to claim 1, wherein said quaternary ammonium salt is synthesized by reaction between a compound of the following general formula (11) and a compound of the following general formula (12). wherein R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms; R 1 -X wherein R 1 represents a dodecyl, tridecyl or tetradecyl group and X represents a chlorine atom, bromine atom or iodine atom. The use according to claim 1, wherein said quaternary ammonium salt is synthesized by reaction between a compound of the following general formula (13) and a compound of the following general formula (14). wherein R 1 represents a dodecyl, tridecyl or tetradecyl group and R 2 represents an alkyl group of 1-2 carbon atoms; R 3 -Y wherein R 3 represents an alkyl group of 1-2 carbon atoms and Y represents a chlorine atom, bromine atom, iodine atom or a group represented by one of the following general formulas (15), (16) or (17): wherein R 8 represents an alkyl group of 1-2 carbon atoms; wherein R 9 and R 10 each represent a hydrogen atom or methyl group; wherein R 11 represents an alkyl group of 1-2 carbon atoms. The use according to claim 1, wherein said quaternary ammonium salt is produced by ion-exchange of a cationic group-containing quaternary ammonium salt compound of the following general formula (18) using sulfuric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, nitric acid, nitrous acid, chloric acid, chlorous acid, hypochlorous acid or a compound of any one of the following general formulas (19), (20), (21), (22) or (23). wherein R 1 represents a dodecyl, tridecyl or tetradecyl group, and R 2 and R 3 each represent an alkyl group of 1-2 carbon atoms; R 4 -COOH wherein R 4 represents an alkyl group or alkenyl group of 1-7 carbon atoms which may have a hydroxyl group or carbonyl group; HOOC-R 5 -COOH wherein R 5 represents a direct bond or an alkylene group or alkenylene group of 1-8 carbon atoms which may have a hydroxyl group; wherein each R 6 represents an alkyl group of 1-8 carbon atoms, and the phosphate ester may be a single monoester or diester or a mixture thereof; wherein each R 7 represents an alkyl group of 1-8 carbon atoms, and the phosphonate ester may be a single monoester or diester or a mixture thereof; wherein R 9 and R 10 each represent a hydrogen atom, methyl group or carboxyl group.

Inventors: KAMEOKA IKUO, KUROSE MIKIHIKO, MAKINO MASAHIRO, KAMEOKA, IKUO, KUROSE, MIKIHIKO, MAKINO, MASAHIRO
Applicants: NICCA CHEMICAL CO, NICCA CHEMICAL CO., LTD.
Application year: 1997
Main classification: C07C211
IPC codes: A01N33, C07C211