JPS59483B2 - Antibacterial and antifungal composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel composition having an antibacterial and antifungal effect, and its purpose is to have a broad spectrum of antibacterial piles and prevent non-mercury, non-metallic environmental pollution. The objective is to provide a composition free of

The composition of the present invention has the following general formula [wherein R1 represents an alkyl group having 1 to 18 carbon atoms or a benzyl group].

R2 represents hydrogen, an alkyl group having 1 to 17 carbon atoms, a phenyl group, or a benzyl group.

R3 represents an alkyl group having 1 to 18 carbon atoms, a benzyl group, or a hydroxyethyl group.

Further, X represents a halogen atom, or when the above R3 is a lower alkyl group, represents SO, R'(R' is a lower alkyl group), or.

] A quaternary imidazolium compound represented by atom, potassium atom,
It is characterized by consisting of a phosphonobutane-tricarboxylic acid compound represented by [meaning at least one sodium atom].

It is already known that quaternary imidazolium compounds have antibacterial and antifungal effects (E, R, 5heparde
tal, J.A.C.S., 692269 (1947),
Japanese Patent Publication No. 45-3800) discovered that the antibacterial and antifungal effect of the compound could be improved by ten to several tens of times by combining the compound with an organic phosphoric acid compound, that is, a phosphonobutane-tricarboxylic acid compound, and completed the present invention. I ended up doing it.

The present inventors have conducted extensive research focusing on organic phosphoric acid compounds, particularly phosphonobutane-tricarboxylic acid compounds, as mutually effective agents for quaternary imidazolium compounds. The antibacterial and antifungal effect of the quaternary imidazolium compound can be improved by coexisting an organic phosphoric acid compound represented by the general formula (II), that is, a phosphonobutane-tricarboxylic acid compound, with the imidazolium compound.
They found that it can be improved by 0 to several tens of times.

It is unique to quaternary imidazolium compounds that the antibacterial and antifungal effects of quaternary imidazolium compounds are significantly activated by the presence of phosphonobutane-tricarboxylic acid.

Examples of the above quaternary imidazolium compounds are as follows.

1-Methyl-3-octylimidazolium chloride 1-octadecyl-2-methyl-3-benzylimidazolium bromide 1-benzyl-2-undecyl-3-methylimidazolium methyl sulfate ■-Dodecyl-2-methyl-3-benzylimidazolium Chloride 1-ethyl-2-haftatecyl-3-ethylimidazolium ethyl sulfate 1-benzyl-2-phenyl-3-dodecylimidazolium chloride 2-dibenzyl-3-octadecylimidazolium bromide 1-dodecyl-2-phenyl-3- Hydroxyethylimidazolium iodide 1-octyl-2-methyl-3-methylimidazolium toluenesulfonate ■-Tetradecyl-3-hydroxyethylimidazolium bromide The phosphonobutane-tricarboxylic acid compound used in the present invention is clear from BP1320449. For example, 2-phosphono-butane-1,2,4-tricarboxylic acid, 2-phosphono-butane-3-meth-1,2,4-
tricarboxylic acid, 2-phosphono-butane-3,4-dimethyl-1,2,4-tricarboxylic acid, 2-phosphono-butane-4-methyl-1,2,4-)! J carboxylic acid, 2-phosphono-butane-3-ethyl-1,2,4-tricarboxylic acid, 2-phosphono-butane-3-:r-f-4-methyl-1,2,4-tricarboxylic acid, 2 -phosphono-butane-3-propyl-1,2,4-tricarboxylic acid, 2-phosphono-butane-3-propyl-4-methyl-1,2,4-)! J carboxylic acid, 2-phosphono-butane-3-butyroto 2,4-tricarboxylic acid,
2-phosphono-butane-3-butyl-4-methyl-1.
Examples include 2,4-tricarboxylic acid and potassium and sodium salts thereof.

These phosphono-butane-tricarboxylic acid compounds may be used alone or in combination of two or more.

The amount of the phosphonobutane-tricarboxylic acid compound to be used in coexistence with the quaternary imidazolium compound can be used within a wide range, but the amount of phosphonobutane-tricarboxylic acid compound to be used in combination with the quaternary imidazolium compound is within a wide range. The acid compound is usually used in an amount of 0.01 to 100 parts, preferably 0.1 to 10 parts.

When the amount of the phosphonobutane-tricarboxylic acid compound is less than 0.01 part, it tends to be unable to exhibit the antibacterial and antifungal effect of the present invention, and when it is more than 1000 parts, the concentration of the quaternary imidazolium compound in the composition decreases. There is a tendency for the antibacterial and antifungal effect to decrease.

Next, regarding the effect of the present invention, the results of measuring the minimum growth inhibitory concentration (ppm) for filamentous fungi, bacteria, and yeast shown in Table 1 are shown in Table 2.

Typical examples of quaternary imidazolium compounds include 1-dodecyl-2-methyl-3-benzylimidazolium chloride (hereinafter abbreviated as IC), and phosphonobutane-tricarboxylic acid compounds include 2-phosphonobutane-1,2,4-tricarboxylic acid. 4Na (hereinafter abbreviated as PBT-4Na) was used.

Quaternary imidazolium compounds (IC) as shown in Table 2 above
The presence of PBT-4Na increases the growth inhibitory concentration by 10 to several tens of times.

It is thus clear that the antibacterial and antifungal composition of the present invention is effective at extremely low concentrations and has a broad antibacterial spectrum.

The composition of the present invention can be used as an aqueous solution, powder, emulsion, etc., with addition of colorants, fragrances, surfactants, and other additives as necessary.
It can be commercialized as a solution or other product depending on the purpose, and can be applied to all areas where microbial damage occurs in the various industrial fields described below.

(1) Slime control agent for paper manufacturing In the paper manufacturing industry, when pulp is made into paper using a large amount of water, various microorganisms enter the process from the water, wood, and air and multiply.

This becomes so-called slime and causes various problems in papermaking.

Examples include pulp contamination, paper breakage during the papermaking process, and product contamination, and preventing microorganisms that cause these problems is a major issue in the paper manufacturing industry.

For this reason, the necessary conditions for a slime control agent are:
It is necessary to have a broad inhibiting ability against various microorganisms, and the composition of the present invention is ideal for this purpose because it has a broad antibacterial and antimicrobial spectrum.

(2) Slime inhibitor for industrial cooling water Various microorganisms occur and multiply in industrial cooling water, causing so-called slime to adhere to heat exchangers, pulp, etc., and reducing the thermal conductivity of heat exchangers. drops, pipes become clogged,
Eventually it progresses to corrosion.

The composition of the present invention is suitable as a slime inhibitor for industrial cooling water because it suppresses the generation and propagation of slime due to its wide microbial activity when added to industrial cooling water.

(3) Emulsion paint, latex, paste, adhesive,
Addition to water-based cutting oil The common feature of the above applications is that the medium is water.
Furthermore, since various additives are added to these products, they also serve as nutrients and the generation and proliferation of microorganisms cannot be avoided.

It is well known that various microorganisms propagate regardless of the storage conditions before and after use, which significantly deteriorates the performance of the above-mentioned applications.

By adding the composition of the present invention to these, the generation and proliferation of microorganisms can be suppressed without impairing the original performance.

The composition of the present invention can be applied to fibers, genuine materials, resins, etc. in which various microorganisms significantly occur and multiply, causing the original functions to be lost.
Addition to cosmetics, ointments, etc. is also recommended.

The present invention will be described in detail with reference to Examples.

Example 1 Using wheat starch bulk powder as a test medium, JIS-Z-2
The minimum growth-inhibiting concentration of the quaternary imidazolium compound against filamentous fungi when a predetermined concentration of a phosphonobutane-tricarboxylic acid compound was present was determined in accordance with 911 (Mold Resistance Test Method).

These results are shown in Table 3.

(Filamentous fungi: Aspergillus niger,
Penicillium citrinum.

Rh1sopus nigricans, Clad
osporium herbarum and Chaetom
As is clear from Table 3, the composition of the present invention exhibits an extremely excellent antifungal effect (in the coexistence of five types of M. globosum).

Example 2 In a circulating cooling water system with a water capacity of 300 tons and a circulating water rate of 600 tons/hour, various antibacterial and antifungal compositions were added at once to a concentration of 10 ppm based on the amount of water held.

Returned water from the 1-hour sieve was collected, cultured on an agar plate, and the number of bacteria per 1 rrL was measured.

The results are shown in Table 4.

Table 4 shows that the antibacterial and antifungal composition of the present invention exhibits excellent antibacterial action.

Example 3 Various antibacterial and antifungal compositions (both PBT-4Na 10
ppm addition) were added, respectively.

After standing for 1 hour*, the slime was transferred onto Waxman's medium to determine whether the microorganisms in the slime were alive or dead, and the minimum lethal concentration thereof was determined.

The results are shown in Table 5.

Example 4 Hinyl acetate emulsion m material KPBT-4Na 0
．． 01% and 30ppm each of quaternary salts.
The resulting paint was applied to the bathroom and left for 6 months.

Later, contamination due to microbial growth on the painted surface was observed.

As shown in Table 6, only the combination of the quaternary imidazolium compound and PBT-4Na according to the present invention avoided microbial contamination of the painted surface.

However, in the table, - indicates no contamination at all, + indicates some contamination,
++ indicates total contamination.

Claims (1)

[Claims] [In the formula, R1 represents an alkyl group having 1 to 18 carbon atoms or a benzyl group. R2 represents hydrogen, an alkyl group having 1 to 17 carbon atoms, a phenyl group, or a benzyl group. R3 represents an alkyl group having 1 to 18 carbon atoms, a benzyl group, or a hydroxyethyl group. Further, X represents a halogen atom, or when the above R3 is a lower alkyl group, represents 5O4R'(R' is a lower alkyl group) or. [However, in the above formula, R4 means a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a carboxyl group, R6 means a hydrogen atom or a methyl group, and M atom, potassium atom,
1. An antibacterial and antifungal composition comprising a phosphonobutane-tricarboxylic acid compound represented by the following formula, meaning at least one sodium atom.