JP2009084159A - New disinfectant - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a disinfectant which is free from smell and the irritation by its vapor, having high safety, and having a high bactericidal property against bacterial spores, acid-resistant bacteria and the like. <P>SOLUTION: This disinfectant is characterized by containing permaleic acid at a concentration of 0.0001 to 50 mass% concentration as an active ingredient. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a disinfectant containing permaleic acid as an active ingredient.

Disinfectants are categorized in order of efficacy: high-level disinfectant, medium-level disinfectant, and low-level disinfectant (classification by Spalding). Among these, high-level disinfectants are important because of their broad antibacterial spectrum including bacteria, fungi, and viruses, including spores (which cannot be sterilized by medium-level disinfectants and low-level disinfectants).
A representative example of a peracid-based disinfectant / disinfectant is peracetic acid, but it has a strong irritating odor, and the steam irritates the mucous membranes of the eyes and respiratory organs. A mask and goggles to protect the mucous membrane are essential.
Aldehydic glutaral, phthalal, and chlorine dioxide are high-level disinfectants that have strong bactericidal properties like peracetic acid. However, each has a strong irritating odor like peracetic acid, and requires a mask and goggles to protect the mucous membrane. Further, it has been pointed out that aldehyde preparations such as glutaral have a weak bactericidal action against acid-fast bacteria.
Even peracids are not all highly effective as disinfectants, for example percarbonate has little ability to kill spores. This is confirmed by the applicant of the present invention that the number of viable bacteria is not reduced as a result of measuring the number of viable bacteria after exposing the spores to a 10% percarbonate aqueous solution for 10 minutes and growing on a normal agar medium. . Further, when the concentration of hydrogen peroxide is 7.5% and 20 ° C., it takes 6 hours to kill spores (Non-patent Document 1).
In this way, peracetic acid, glutarar and phthalal, which are high-level disinfectants, have a strong irritating odor, so steam strongly stimulates mucous membranes such as the eyes and respiratory organs, and requires a well-ventilated work place when handling. There was a drawback that a mask and goggles to protect the mucous membrane were indispensable. Therefore, the appearance of a disinfectant with little irritation has been desired.

Patent Document 1 describes the production of permaleic acid from maleic anhydride, but the production method uses sodium percarbonate, and the data that permaleic acid has antibacterial properties is as follows. Not shown.
Patent Documents 2 and 3 list Patent Document 1 as an example, but only describe that the bactericidal properties of permaleic acid are insufficient as compared with maleic anhydride. It does not suggest that the properties are excellent.
Patent Document 4 mentions permaleic acid as an example of a life-extending agent for cut flowers in organic oxides, but in the examples, only peracetic acid is used, and a specific description of permaleic acid is given. No.

German Patent No. 2815400 JP-A-1-221302 JP-A-10-72304 Japanese Patent No. 3011534 Published “Disinfectant Text New Edition”, Kyowa Planning Co., Ltd.

  An object of the present invention is to provide a highly safe disinfectant that has no odor and is free from irritation of steam, and has a high bactericidal property against bacterial spore bacteria and acid-fast bacteria.

  The present invention provides a disinfectant characterized by containing permaleic acid at a concentration of 0.0001 to 50% by mass as an active ingredient.

That is, the gist of the present invention is as follows.
(1) A disinfectant comprising permaleic acid having a concentration of 0.0001 to 50% by mass as an active ingredient.
(2) The disinfectant according to (1), wherein the odor sensing concentration in terms of acetic acid when measured with a gas detector tube is 1 ppm or less.
(3) The disinfectant according to (1) or (2), further comprising maleic acid and / or hydrogen peroxide.
(4) A disinfection method using the disinfectant according to any one of (1) to (3), wherein the permaleic acid is applied to bacterial spores at a concentration of 10% by mass or more. Disinfecting method characterized.
(5) A disinfection method using the disinfectant according to any one of (1) to (3), wherein the permaleic acid is applied to acid-fast bacteria at a concentration of 2.5% by mass or more. A disinfection method characterized by:
(6) A disinfection method using the disinfectant according to any one of (1) to (3), wherein the permaleic acid is applied to bacteria at a concentration of 0.3% by mass or more. Disinfection method characterized by.
(7) A disinfection method using the disinfectant according to any one of (1) to (3), wherein the permaleic acid is applied to a fungus at a concentration of 1.25% by mass or more. Disinfection method characterized by.
(8) A disinfection method using the disinfectant according to any one of (1) to (3), wherein the permaleic acid is applied to a virus at a concentration of 0.1% by mass or more. Disinfection method characterized by.
(9) Human or animal health, packing, wrapping, medical equipment, industrial equipment, healthcare environment, industrial equipment, cooling tower, air conditioner conduit, food industry, (4) to (7) Disinfection method.
(10) A method for producing a disinfectant, comprising a step of generating permaleic acid by mixing hydrogen peroxide and maleic anhydride.
(11) A kit for producing a disinfectant comprising hydrogen peroxide and maleic anhydride as constituent components.

The disinfectant of the present invention has less odor and higher safety than a conventional peracid-based disinfectant (peracetic acid).
The disinfectant of the present invention also has a high bactericidal power and is effective against bacterial spores and acid-fast bacteria.

Hereinafter, the present invention will be described in detail.
The disinfectant of the present invention is a disinfectant containing permaleic acid as an active ingredient. The concentration of permaleic acid contained in the disinfectant of the present invention may be 0.0001 to 50% by mass, but when used for cell spores, the concentration of permaleic acid is 10 to 50% by mass. When used against acid-fast bacteria, the maleic acid concentration is preferably 2.5 to 50% by mass, and when used against bacteria, the maleic acid concentration Is preferably 0.3 to 50% by mass, and when used against fungi, the permaleic acid concentration is preferably 1.25 to 50% by mass and used against viruses The permaleic acid concentration is preferably 0.1 to 50% by mass.

The disinfectant containing permaleic acid of the present invention as an active ingredient may further contain maleic acid and / or hydrogen peroxide.
The disinfectant of the present invention may contain other components such as surfactants, metal chelating agents, buffer salts, anticorrosives, and colorants as additives.

As used herein, the term “disinfecting” means killing cell spores, mycobacteria, bacteria, fungi, viruses, etc., or stopping their proliferative function.
The term “disinfectant” as used herein has the ability to “disinfect” cell spores, acid-fast bacteria, bacteria, fungi, viruses, and the like, and includes antibacterial and bactericidal properties.
The term “bacterial spore” as used herein refers to a durable type formed by anaerobic bacilli Bacillus subtilis, anaerobic bacilli belonging to the genus Clostridium at the end of the growth phase. Means a cell.
As used herein, the term “acid-fast bacterium” refers to a positive acid-staining bacterium well known to those skilled in the art, and includes bacteria belonging to the genus Mycobacterium.

The disinfectant of the present invention includes cell spores (for example, Bacillus subtilis spores), acid-fast bacteria (for example, Mycobacterium sialium, Mycobacterium corsalis, Mycobacterium corsalis, Mycobacterium corsalis, Mycobacterium corsalis, Sactobacillus saccharus). Bacillus subtilis, Clostridium perfringens), fungi (eg, Aspergillus
niger, Penicillium citrinum), viruses (eg, Augeszky's disease virus, Infectious burst)
(dissease virus).

The permaleic acid contained in the disinfectant of the present invention can be obtained by dissolving commercially available maleic anhydride in a commercially available hydrogen peroxide solution as described in Example 1 of the present application. In this case, it is preferable to use a hydrogen peroxide solution having a hydrogen peroxide concentration of 10 to 60%, for example, 30%.
Thus, the disinfectant containing permaleic acid of the present invention can be used by generating permaleic acid from maleic anhydride and hydrogen peroxide at the site where disinfection is required.
Furthermore, the disinfection method of the present invention can be performed by immersing the object to be disinfected in a disinfectant liquid. Moreover, the aspect etc. which spray the liquid of a disinfectant to the disinfection object are also mentioned.
Such disinfection is done in human and animal health, packing, wrapping, medical equipment, industrial equipment, healthcare environment, industrial equipment, cooling towers, air conditioning conduits, food industry.

The disinfectant of the present invention has little odor. For example, it is preferable that the odor sensing concentration in terms of acetic acid when measured with a gas detector tube (manufactured by GASTEC) is 1 ppm or less.
The place of disinfection of the present invention is not particularly limited, and can be carried out in a place where cell spores, acid-fast bacteria, bacteria, fungi, and viruses are present where disinfection is required.

The present invention also provides a method for producing a disinfectant comprising a step of generating permaleic acid by mixing hydrogen peroxide and maleic anhydride.
The present invention further provides a kit for producing a disinfectant comprising hydrogen peroxide and maleic anhydride as constituent components. The hydrogen peroxide contained in the kit is preferably a hydrogen peroxide solution having a hydrogen peroxide concentration of 10 to 60%, for example, 30%, and the kit contains instructions on how to mix and instructions for disinfection. Is preferred.

  Hereinafter, the present invention will be described in more detail with reference to examples. However, it goes without saying that the present invention is not limited to these examples.

Production Example 1 Production of permaleic acid and control drug peracetic acid
Permalic acid was produced by heating and dissolving 8.8 g of maleic anhydride (Wako Pure Chemicals: Special Grade) in 10 ml of 30% hydrogen peroxide (Wako Pure Chemicals: Special Grade). It was diluted with water to an appropriate concentration during the antibacterial test and used.
As a control agent, 6% aceside manufactured by Saraya Co., Ltd. was used as peracetic acid. The aceside is divided into 2 parts, 1st part (equal mixture containing 6% peracetic acid, hydrogen peroxide, acetic acid, other 1 component (stabilizer) and ion-exchanged water) and 2nd part (practical use) Used to adjust and stabilize the pH of the solution.10 ml of 9 components (containing buffering salt, stabilizer and sequestering agent) are mixed to make 3% peracetic acid, diluted with ion-exchanged water to an appropriate concentration during antibacterial testing Used.

Example 1. Antibacterial data of bacteria type A method according to the FDA carboxylic acid coefficient measurement method was used.
1) Test bacteria, test virus, test cell (1) Bacteria Staphylococcus aureus ATCC 6538
2. Streptococcus agalactiae Ulsan strain,
3. Escherichia coli ATCC 11775
4). Salmonella enteritidis L-58 strain,
5). Bacillus subtilis ATCC6633
6). Clostridium perfringens W1 was used.
(2) Filamentous fungi Aspergillus niger NBRC6341
8). Penicillium citrinum NBRC6352 was used.
(3) Bacterial spores Bacillus subtilis ATCC 6633 was cultured in liquid broth medium for 24 hours, and then Sterlinin, J. et al. M.M. And Mandelstem, J. et al. Biochem. J. et al. 1969; 113: 29, spores were prepared, suspended in sterilized distilled water, treated at 85 ° C. for 10 minutes to kill the vegetative form, stored at 5 ° C., and 10 ⁶ to 10 ^7. It was suspended in sterilized distilled water so as to be CFU / ml and used as a spore test solution. The number of spores was calculated from the number of colonies obtained by pour-culturing the test solution serially diluted 10 times on a bouillon agar medium.
(4) Mycobacterium Mycobacterium avium ATCC 15769
Mycobacterium intracellure ATCC 13950
Tested using Mycobacterium kansasii ATCC 25414.
Each of the above test strains was cultured in 1% Ogawa medium (Eiken Chemical Co., Ltd.) (hereinafter referred to as Ogawa medium), and the grown fungus 1 platinum ear was sterilized with 5 sterilized glass beads with a diameter of 5 mm. 10%
The sample was placed in a test tube with a screw cap containing 2 drops of Tween 80 solution, and shaken for 15 seconds with an automatic mixer. 4 ml of 7H9 broth (manufactured by Difco) was added thereto to obtain a homogeneous suspension of each test strain cell. The absorbance of this suspension was measured at a wavelength of 660 nm using a photometer (Mini photo 518, TAITEC), then diluted with sterilized distilled water and adjusted to 0.30 to obtain an inoculum solution. The number of viable bacteria in the inoculum was determined by diluting the inoculum to 10 ² , 10 ³ , 10 ⁴ , 10 ⁵ , 10 ⁶ times, and inoculating 100 μl of each diluted solution into the Ogawa medium at 37 ° C. It was determined by counting the number of colonies that had been cultured and developed.
20 μl of the inoculum solution is added to and mixed with 500 μl of the above-mentioned peracetic acid practical solution or permaleic acid solution, and kept at room temperature for a certain time (10 minutes) to bring the drug and bacteria into contact. (Bioloop, manufactured by ELKAY) was used to inoculate 7H9 broth and cultured at 37 ° C. After 4 weeks, the presence or absence of bacterial growth was observed. A sample in which bacterial growth was observed was defined as positive growth (+), and a sample in which growth was not observed was defined as negative growth (-).
(5) Test virus Augeszky's disease virus Yamagata S-81 strain Infectious burst disease virus J1 strain was used.
(6) Test cell CPK cell (pig kidney cell)
CEF cells (chicken embryo fibroblasts) were used.

2) Bacteria and filamentous fungus preliminary tests For test bacteria 1 and 3-5, standard agar medium (Nissui Pharmaceutical), for test bacteria 2 using blood agar medium, and for test bacteria 6 using GAM agar medium The strain 1-5 was precultured at 37 ° C. for 16 hours using a sensitive bouillon (Nissui Pharmaceutical Co., Ltd.).
Test bacteria 6 were pre-cultured in GAM bouillon (Nissui Pharmaceutical) at 37 ° C. for 16 hours in an anaerobic state, and then centrifuged at 3000 rpm for 10 minutes.
Thereafter, the precipitate obtained by centrifugation was washed once with sterilized physiological saline, and resuspended in the same amount of sterilized physiological saline as that used during culture, which was used as an inoculum.
The test bacteria 7 and 8 were pre-cultured on a PDA agar medium (Eiken Chemical Co., Ltd.) at 25 ° C. for 10 days, then the spores were scraped and suspended in purified water supplemented with 0.1% Tween 80, and the number of spores was about 10 ⁶ / What was made into ml was used as the inoculum.
The following concentrations were prepared using sterile distilled water for both the test drug and the control drug.

  Each dilution series of the drug was dispensed 10 ml into a test tube, and the inoculum was left in a constant temperature water bath at 20 ° C., and the test was started 10 minutes after the temperature was constant. That is, after sufficiently inoculating the inoculum solution, add 1 ml to each diluted drug test tube, mix well, let it act for 10 minutes, and then use the white fungus ear (inner diameter 4 mm) for the post-culture medium (pre-culture) Same as: test bacteria 1-5 sensitive broth test bacteria; test bacteria 6 GAM broth; test bacteria 7,8 PDA agar medium). After the inoculation, the culture medium was cultured for sensitive broth and GAM broth at 37 ° C. for 24 hours, and the PDA agar medium was cultured at 25 ° C. for 5 days. The determination was based on the presence or absence of bacterial growth in the post-culture medium. The results of the preliminary test are shown in Table 1-2.

  The dilution factor was 3% “aceside” (6% undiluted solution + buffer) for peracetic acid, and 100% dilute for permaleic acid.

3) Bacteria and filamentous fungi Main test (1) Preparation of inoculum solution Test bacteria 1 and 3-5 are standard agar medium (Nissui Pharmaceutical), test bacteria 2 are blood agar medium and test bacteria 6 Is fished from a single colony of a test strain purely cultured on a GAM agar medium. Test bacteria 1-5 are pre-cultured at 37 ° C. for 16 hours in a sensitive bouillon (Nissui Pharmaceutical), and test bacteria 6 is GAM. After precultured in an anaerobic state at 37 ° C. for 16 hours in bouillon (Nissui Pharmaceutical), the mixture was centrifuged at 3000 rpm for 10 minutes.
The precipitate obtained by centrifugation was washed once with sterilized physiological saline, and resuspended in the same amount of sterilized physiological saline as that used during culture to obtain an inoculum.
The number of bacteria in the inoculated bacterial solution was obtained by spreading a serial dilution with sterile physiological saline on a plate medium and counting the number of colonies formed after the culture.
The test bacteria 7 and 8 were pre-cultured on a PDA agar medium (Eiken Chemical Co., Ltd.) at 25 ° C. for 10 days, then the spores were scraped and suspended in purified water supplemented with 0.1% Tween 80, and the number of spores was about 10 ⁶ / What was made into ml was used as the inoculum.

(2) Preparation of test drug The following preparation concentrations were selected from the results of the preliminary test.
Sterile distilled water was used for the preparation (dilution) of both the control drug and the test drug.

(3) Measurement of the effective action time of the drug Each 10 ml of each dilution series of the drug is dispensed into two test tubes, and the inoculum is left in a constant temperature water bath at 20 ° C., and 10 minutes after the temperature is constant. The test was started.
After sufficiently stirring the inoculum, 1 ml was added to each diluted drug test tube and mixed thoroughly, and allowed to act for a predetermined time.
1 white fungus ear (inner diameter 4 mm) for each action time medium for post-culture (same as pre-culture: test bacteria 1-5 sensitive broth; test bacteria 6 GAM broth; test bacteria 7, 8 PDA agar medium) Inoculated.
The duration of action was 2.5, 5, 10, 15 minutes.
After inoculation, the culture medium for susceptibility and GAM broth were cultured at 37 ° C. for 24 hours and the PDA agar medium at 25 ° C. for 5 days.
The test was repeated twice, and the operation was simultaneously performed twice for each drug.

(4) Determination The presence or absence of bacterial growth in the post-culture medium was used as an index, and the maximum dilution rate of a drug in which bacterial growth was not observed after 10 minutes of action was compared between the test drug and the control drug.
The results of the bacterial test are shown in Tables 3-1 and 3-2. Table 3-3 shows the effective dilution factor based on the carboxylic acid coefficient measurement method. In the case of peracetic acid, the dilution rate was 3840 to 10240 times (2.9 to 9.0 ppm) for Gram-positive and negative bacteria other than Bacillus. In Bacillus, it was 60 times (563 ppm). In fungi, it was 10 to 20 times (1500 to 3000 ppm). In permaleic acid, it was 1920-3840 times (293-586 ppm) in Gram positive / negative bacteria other than Bacilllus, and 60 times (18750 ppm) in Bacillus. In fungi, it was 40 to 80 times (12500 to 25000 ppm).

The dilution factor is 3% “aceside” (6% stock solution + buffer solution) for peracetic acid,
About permaleic acid, it was set as the dilution factor of 100% of the errand preparation.

尚、試験に使用した接種菌液濃度を表３−４に示す。

The inoculum concentration used for the test is shown in Table 3-4.

試験の結果を表３−６に示した。 4) Test drug and control drug concentrations for bacterial spores Bacillus subtilis ATCC 6633 were prepared as follows. [Note: 2) and 3) tests are sterilization tests for live bacteria of Bacillus subtilis ATCC 6633]

The results of the test are shown in Table 3-6.

The dilution factor is 3% “aceside” (6% stock solution + buffer solution) for peracetic acid,
About permaleic acid, it was set as the dilution factor of 100% of the errand preparation.
It was found that the effective concentration required for sterilization against bacterial spores (Bacillus subtilis ATCC 6633) was 10 to 20 times (1500 to 3000 ppm) with peracetic acid, and 5 to 10 times (100,000 to 200,000 ppm) permaleic acid.

5) The results of examining the bactericidal effects of peracetic acid and permaleic acid of the present invention against mycobacteria (Mycobacterium avium ATCC 15769, Mycobacterium intracellulare ATCC 13950, Mycobacterium kansasii ATCC 25414) are shown in Table 3 below.

As shown in Table 3-7, there was a slight difference in sensitivity depending on the type and strain of acid-fast bacteria.
With a 10 minute disinfection time, peracetic acid was completely sterilized 20 to 40 times (750 to 1500 ppm), and permaleic acid was completely sterilized 20 to 40 times (50,000 to 100,000 ppm).

6) Virus test method (1) Preliminary test Confirmation test of the effect of the reagent on the cultured cells It is necessary to confirm the toxicity of the reagent on the cultured cells used when conducting the virucidal test. Therefore, only the reagent reagent was serially diluted, and the cultured cells were inoculated simultaneously in a 96-well microplate and inoculated by two methods after cell sheet formation, and cultured for 5 days at 37 ° C. under 5% carbon dioxide conditions.
As a result, in CEF cells, after sheet formation, CPK cells had no effect on cells to a higher concentration in co-inoculation. In addition, IBD virus (Infectious burst disease virus J1 strain) after CEF cell sheet formation, and AD virus (Aujeszy's disease virus Yamagata S-81 strain) was considered to have no problem in proliferation ability in CPK cell co-culture. This test was conducted by this method.
Table 4-1 shows the results of a test for confirming the effect of the reagent on the cultured cells.

The dilution factor is 3% “aceside” (6% stock solution + buffer solution) for peracetic acid,
About permaleic acid, it was set as the dilution factor of 100% of the errand preparation.
**: Experiment performed 4 times for CEF cells, 3 times for CPK cells
***: CEF cells are inoculated after the formation of geets. ****: CPK cells are inoculated simultaneously.

  From the results shown in Table 4-1, peracetic acid must be diluted 100000 times, overmalein should be diluted 300,000 times at the time of CEF cell inoculation, peracetic acid must be diluted 30000 times, and overmalein should be diluted 300,000 times at the time of CPK cell inoculation. I understood it.

(2) Main test Based on the results of the preliminary test, after adjusting each concentration of the reagent, sensitize the pathogenic virus at 20 ° C for 10 minutes, and dilute to a concentration that does not affect the reagent on each cultured cell. And then inoculated into cultured cells.
The virus is IBDV (Infectious burst disease virus)
The C1 cells were cultured with CEF cells, and the ADV (Aujeszky's disease virus Yamagata S-81 strain) was cultured with CPK cells at 37 ° C. for 3 to 5 days using GM. When 80% CPE appeared, the culture solution was extracted and centrifuged at 3000 rpm for 5 minutes, and the supernatant was stored frozen. After thawing the stock virus solution, the virus titer (TCID50) was measured.
The virus solution stored at the same time was used for this test.
The dilution stage of the reagent was as follows.

Sensitization was carried out as follows so that the virus concentration was 10 ^2.3 (200) TCID 50 at the time of cell inoculation.
An antiseptic solution (diluted with sterilized PBS) having a concentration twice that of the above was prepared. 10 ^6. Created ¹ TCID50 virus concentration solution (MM). 1 ml of disinfectant solution and 1 ml of virus solution were sensitized (20 ° C. for 10 minutes). After sensitization, the cells were inoculated with MM diluted 3000 times.
After sensitization, in the case of simultaneous inoculation, 50 μl of the diluted solution after the sensitization and 50 μl of the cell suspension were dispensed into 4 wells of a 96-well microplate and cultured at 37 ° C. under 5% carbon dioxide conditions for 5 days.
In the case of the sheet formation, the GM of the microplate in which sheet formation has been recognized in advance is extracted, 50 μl of MM is added, and then 50 μl of the diluted solution after the sensitization is added in 4 wells at 37 ° C. under 5% carbon dioxide conditions. And cultured for 5 days.
In the cell culture, the presence or absence of cell degeneration was observed in cell culture, and those that were denatured (CPE) were regarded as virus positive and those that did not denature (CPE) were regarded as virus negative.

(3) Results In the virus test, as shown in Table 4-3, with peracetic acid, the IBDV (Infectious burst disease virus J1 strain) had a virucidal value of 3.357 (× 2280) and ADV (Aujessky's disease virus Yamagata S-81). In the case of permaleic acid, the virucidal value against IBDV was 3.238 (x1732), and ADV was 3.607 (x4054).

The dilution factor is 3% “aceside” (6% stock solution + buffer solution) for peracetic acid,
About permaleic acid, it was set as the dilution factor of 100% of the errand preparation.
* Experiment repeated 4 times * IBDV (CEF cells) inoculated after formation of the diet * ADV (CPK cells) co-inoculated

7) Comparison of bactericidal and virucidal effects of permaleic acid and peracetic acid Using two drugs of permaleic acid and peracetic acid aceside, a comparative test of the disinfection effect against 8 types of bacteria and 2 types of viruses was conducted. It implemented according to the measuring method.
As a result, in order to show the same disinfection effect as peracetic acid, permaleic acid is about 30 to 100 times for gram-positive / negative bacteria, about 4 to 20 times for fungi, and about 40 times for viruses with no envelope. It was found that an ADV virus carrying an envelope requires a concentration of about 150 times. In addition, about 7 times the concentration was required for bacterial spores. (Table 5)

Both drugs showed the same tendency with respect to the effectiveness of the disinfection effect against Gram-positive bacteria, Gram-negative bacteria, and spore bacteria, the strongest against Gram-negative bacteria, and maleic acid is more potent than Bacillus and Peracetic acid compared to peracetic acid. For acid-fast bacteria, a concentration of about 30 times was required. For Clostridium, both drugs showed the same bactericidal effect as other Gram-positive bacteria. For fungi, both drugs required high concentrations.
From this, it was judged that the bactericidal effect of permaleic acid can obtain the bactericidal effect similar to that of peracetic acid by adjusting the concentration.
Although the concentration of virus in permaleic acid was also high, it was judged that the virus-killing effect similar to that of peracetic acid can be expected. In addition, there was a small difference in permaleic acid regarding the virucidal effect when the envelope was possessed and when it was not, so there was a possibility that it was difficult to be influenced by whether or not the envelope was retained.

Example 2 Analysis by titration The cerium sulfate-sodium thiosulfate method was used to determine the concentration of peracid (peracetic acid, permaleic acid) and hydrogen peroxide, which is an equilibrium mixture with these compounds. The following is an overview.
(i) Hydrogen peroxide concentration determination method
In a 100 ml conical beaker, 1 ml of a peracid preparation aqueous solution (peracid concentration 50 to 5,000 ppm) is taken with a micropipette, and 10 ml of 10% sulfuric acid solution is added. Titrate with 0.1N cerium sulfate standard solution, and the point where the yellow color of cerium sulfate disappears is taken as the end point (Aml). The hydrogen peroxide concentration was quantified by the following formula.
Hydrogen peroxide concentration (% (w / w)) = A × 0.17 × f1
f1: Factor of 0.1N cerium sulfate standard solution
(ii) Peracid concentration determination method 1 ml of 10% potassium iodide solution is added to the solution after measuring the hydrogen peroxide concentration. Titrate to light yellow with 0.01N sodium thiosulfate standard solution, add about 1 ml of 1% soluble starch solution,
The end point (Bml) is where the dark blue color disappears.
Measurement of blank: After collecting 1 ml of purified water, the procedures of the hydrogen peroxide concentration analysis method and the peracetic acid concentration analysis method described above are repeated to obtain a blank value (B ₀ ml).
The peracid concentration was determined by the following formula.
(Peracid concentration)
Peracetic acid concentration (% (w / w)) = (B−B ₀ ) × 0.038 × f 2
Permaleic acid concentration (% (w / w)) = (B−B ₀ ) × 0.066 × f 2
f2: 0.01N sodium thiosulfate standard solution factor

Example 3 FIG. Odor Measurement Diluted solutions of peracetic acid and permaleic acid were prepared as described below, and odors at the same concentration were compared. For the measurement, a gas detector tube (manufactured by GASTEC, N0.81) and a gas detector (manufactured by GASTEC) were used.
A diluted solution of aceside (peracetic acid concentration 6 mass%, 0.8 mol%) was prepared, 1 ml of each was collected and placed in a 1000 ml Erlenmeyer flask. After 1 hour, the organic acid concentration in the Erlenmeyer flask was measured with a gas detector tube.
Maleic anhydride is added to a 30% hydrogen peroxide solution at a mass ratio of 1: 1 and dissolved to produce permaleic acid. When the concentration is measured by titration, the permaleic acid concentration is 4 mol%, so this solution is diluted 1/5 with distilled water to make a solution with a permaleic acid concentration of 0.8 mol%. 1 ml each was placed in a 1000 ml Erlenmeyer flask. Similarly, after 1 hour, the organic acid concentration in the Erlenmeyer flask was measured with a gas detector tube. The results are shown below.
As can be seen from the table, permaleic acid has no odor and is known to be a disinfectant that is gentle to the operator.

以上のように、本発明の過マレイン酸を有効成分とする消毒剤は、過酢酸を有効成分とする消毒剤と比較して、臭気がなく、同様に高い殺菌性を有することが分かった。

As mentioned above, it turned out that the disinfectant which uses permaleic acid of this invention as an active ingredient does not have an odor compared with the disinfectant which uses peracetic acid as an active ingredient, and has high bactericidal property similarly.

  According to the present invention, a disinfectant having no odor and high bactericidal properties can be provided. The disinfectant of the present invention can be used in the fields of medicine, industry, agriculture and food industry.

Claims (11)

A disinfectant comprising permaleic acid having a concentration of 0.0001 to 50% by mass as an active ingredient. The disinfectant according to claim 1, wherein an odor sensing concentration in terms of acetic acid when measured with a gas detector tube is 1 ppm or less. The disinfectant according to claim 1 or 2, further comprising maleic acid and / or hydrogen peroxide. A disinfection method using the disinfectant according to any one of claims 1 to 3, wherein the permaleic acid is applied to bacterial spores at a concentration of 10% by mass or more. Method. It is a disinfection method using the disinfectant according to any one of claims 1 to 3, wherein the permaleic acid is applied to acid-fast bacteria at a concentration of 2.5% by mass or more. How to disinfect. A disinfection method using the disinfectant according to any one of claims 1 to 3, wherein the permaleic acid is applied to bacteria at a concentration of 0.3% by mass or more. Disinfection method. A disinfection method using the disinfectant according to any one of claims 1 to 3, wherein the permaleic acid is applied to a fungus at a concentration of 1.25% by mass or more. Disinfection method. A disinfecting method using the disinfectant according to any one of claims 1 to 3, wherein the permaleic acid is applied to a virus at a concentration of 0.1% by mass or more. Disinfection method. The disinfection method according to any one of claims 4 to 7, which is for human and animal health, packing, wrapping, medical equipment, industrial equipment, healthcare environment, industrial equipment, cooling tower, air conditioner conduit, and food industry. A method for producing a disinfectant, comprising a step of mixing hydrogen peroxide and maleic anhydride to generate permaleic acid. A kit for producing a disinfectant comprising hydrogen peroxide and maleic anhydride as constituents.