JPS6038361B2 - industrial antifungal agent - Google Patents

Description

[Detailed description of the invention] The present invention relates to industrial antifungal agents.

More specifically, methylene bisthiocyanate and bromoacetic acid alkyl ester (alkyl group has 6 to 18 carbon atoms) are used to prevent staining of various industrial materials or their additives by fungi. processing agents whose main ingredients are ethylene bisthiocyanate
The present invention relates to a processing agent in which an alkylamine (alkyl group means an alkyl group having 8 to 18 carbon atoms) is added to an alkyl bromoacetate ester (an alkyl group means an alkyl group having 6 to 1 carbon atoms).

The many damages caused by the action of microorganisms are not limited to human and animal diseases, damage to food and agricultural products, but also aircraft, aluminum materials, and electricity.

The products are used in a wide range of applications, including electronics, plastics materials, building materials, paints, adhesives, cutting agents, food packaging materials, cosmetics, daily necessities, textile products, wood processing, civil engineering work, etc. Particularly problematic is the expansion of the scope of use of the polymer industry.
Microorganisms propagate using these polymeric materials themselves, additives such as plasticizers and fillers added during processing, or organic matter that adheres during use as a nutrient source, and as a result, the products are significantly contaminated and undesirable from a hygienic point of view. In many cases, this not only reduces the aesthetic value of the molded product, but also causes a host of problems such as deterioration of the properties of the molded product and loss of mechanical, chemical, or electrical properties. In order to solve the above problems, it is said that treatment with chemicals is necessary, and as a countermeasure, treatments such as adding or mixing compounds or compositions with microbial activity into polymer materials have been proposed. It is being carried out.

In addition, antibacterial agents and preservatives are added to the paint to form a protective film to prevent attacks from microorganisms, but current control methods involve decomposition by ultraviolet rays, release of chemicals by wind and rain, and kneading. In such cases, there are problems such as compatibility between the drug and the polymeric material, and as no perfect drug has been found, there is a strong desire for a long-term effective drug. As an attempt to do this, research is currently being carried out on drugs with long-lasting activity by polymerizing tin compounds, but this is not perfect as it involves problems such as metal compounds, odor, and safety (toxicity, etc.) from the perspective of pollution. I think that the.

The present inventors previously discovered and published in JP-A No. 50-31031 that promacetate is effective as a slime control agent for use in industrial water systems.
Furthermore, we continued to investigate the effects and usability of the compound.

As a result, it was found that bromoacetic acid ester is effective as an industrial antibacterial agent, and also has a synergistic effect when combined with other drugs, which led to the present invention. The purpose of the present invention is to provide a non-irritating and safe antifungal agent, and to have a growth inhibiting effect on fungi even in a small amount compared to conventional antifungal agents, and to prevent the growth of these fungi on various industrial materials. An object of the present invention is to provide an antifungal agent having a remarkable effect of preventing contamination.

As mentioned above, the alkyl bromoacetate, which is one of the components of the antibacterial agent of the present invention, is a known compound, but methylene bisthiothianate and alkylamines are also described in, for example, Chemical Abstracts Vol. 51, Chapters b-c of 13302 (
195 King) and Applied Miku. Biology, 1
4, 308 (King, 1966), both are known to have antimicrobial activity. However, as a result of studies conducted by the present inventors, when the two components, bromoacetic acid alkyl ester and methylene bisthiocyanate, are used together, they have a synergistic action and effect on inhibiting fungal growth compared to when each is used alone. It was also found that when using the three components of bromoacetic acid alkyl ester, methylene bisthiocyanate, and an alkyl amine in combination, it has a synergistic effect compared to when each is used alone. . In the present invention, the alkyl group of the bromoacetate alkyl ester shown above includes straight chain alkyl groups such as n-hexyl, n-octyl, n-decyl, n-lauryl, n-myristyl and n-cetyl, and well-known straight chain alkyl groups thereof. It includes branched alkyl groups, among which the most preferred compound is lauryl bromoacetate.

Although bromoacetate can generally be used as a single compound, two alcohols are used as raw materials for production.
Two or more types of bromoacetic esters may be used if they are available at low cost as a mixture of two or more types. Further, in the present invention, the alkyl group of the alkylamine includes straight mirror alkyl groups such as n-octyl, n-decyl, n-lauryl, n-myristyl, and n-cetyl, and the most preferred compound among these is laurylamine. The drug component of the present invention can be used in various dosage forms, but from the standpoint of practicality, it is most preferable to use it as a liquid dosage form.

The three compounds that are the active ingredients of the present invention include dimethylformamide, diethylene glycol, dipropylene glycol, dioctyl phthalate, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, toluene, acetone, xylene, and ethylene alcohol. Since the active ingredient is soluble in organic solvents, when it is used as a liquid, it can be appropriately diluted with these organic solvents. Agents, especially nonionic surfactants, are added. In the present invention, the compounding ratio in which methylene bisthiocyanate and bromoacetic acid ester exhibit a synergistic effect compared to when each component compound is used alone is about 2:8 to 8:2 by weight. , preferably about 3:7 to 7:3, particularly preferably about 5
:5.

In the case of methylene bisthiocyanate, fromoacetate and alkylamines, the weight ratio of each compound is preferably about 3:3:4. The amount of the antifungal agent of this invention to be added varies slightly depending on the properties of the target industrial material, the usage environment, etc., but it is sufficient to add at least 0.01% by weight to the normal material; Addition of more than % by weight is economically wasteful.

The antifungal agent of the present invention can be mixed into materials when preparing post-adhesives for interior and exterior wall materials of buildings, handicrafts, and industrial applications, or can be applied in an appropriate dosage form to the surface of wood, textile products, and leather products. The remarkable effects of the present invention can be improved by applying a treatment method, such as forming a film on a storage area for kitchen materials such as an electric refrigerator, or even dispersing materials during the paper manufacturing process. It exhibits excellent antibacterial power and can completely prevent mold growth, which should be avoided.

Next, the present invention will be explained with experimental examples, formulation examples, and examples.

Experimental Example Antifungal Efficacy Test A 0.005% aqueous solution of sodium dioctyl sulfosuccinate was sterilized using an autoclave.

Next, two platinum loops of mold spores separated from paints and adhesives that are causing mold problems are suspended in this solution. Dispense 10 portions of Abec medium having the following composition into L-shaped test tubes, add the drug to each concentration, and add a fixed amount of the above spore suspension. 270 for 4 days.

The efficacy of the drug is determined by visually observing the growth state of the bacterial cells.
(Completely inhibiting concentration is shown in the table)
PH…7.3 Sweet pork loin
30 Sodium Nitrate
Potassium hydrogen phosphate
1T magnesium sulfate heptahydrate 0.5T potassium chloride 0.5T iron sulfate
Heptahydrate 0.01ta pure water
1000 [Methylene pisthiocyanate...A test drug lauryl bromoacetate
・・・・・・B laurylamine ……C ratio is % by weight Formulation Example Example 1 0.1% of the element composition of the present invention shown in Formulation Example 1 was added to vinyl acetate-CMC latex adhesive, and The mixture was applied to a glass cloth (5 kites x 5) at a rate of 100 coats per coat.

Next, place the cloth on top of 10 drops of malt agar in a Petri dish.
Add 1 platinum loop of Asbergillus niger to 1 part of sterilized water, then spray 0.3 of the spore suspension onto a cloth with a pipette, cover with a lid, and leave in the temperature tank of 270. We observed the status of bacterial growth over the course of the day. Similarly, formulation examples 2, 3, 4, 5
Experiments were also conducted for the case where 0.1% of the composition was added. As a control example, an experiment was also conducted in which no antifungal agent was added. The results are shown in Table 1. Table 1 Judgment method -: No mold was observed on the base material or test cloth. O+
: Mold is observed only on the top of the tower.O: Mold is observed on the culture medium and test cloth.

Example 2 0.05% of the composition of the present invention shown in Formulation Example 1 was added to a commercially available vinyl acetate emulsion vent,
The surface of a plywood board (0.3 x 5 x 5 cm) was brushed to a coating of 150 yen. Next, put potatoes in a petri dish.
Place on top of 10' of dextrose agar medium, sprinkle 0.3 of the spore suspension obtained by adding 1 loop of Benicillium citrinum into 1' of sterile water with a pipette, and close the lid. It was then left in a 270 temperature bath. The status of bacterial growth was observed over time. Similarly, formulation examples 2, 3, 4, 5
An experiment was conducted by adding 0.05% of the composition. As a control example, an experiment was also conducted in which no antifungal agent was added. The determination method is the same as in Example 1. The results are shown in Table 2.

Table 2

Claims (1)

[Claims] 1 Contains methylene bisthiocyanate and bromoacetic acid alkyl ester (alkyl group means one having 6 to 18 carbon atoms) as main components, and the blending ratio of the two components is based on weight. An industrial antifungal agent characterized in that the ratio is about 2:8 to 8:2. 2. The industrial antifungal agent according to claim 1, wherein the alkyl bromoacetate is lauryl bromoacetate. 3 Contains methylene bisthiocyanate and bromoacetic acid alkyl ester (alkyl group means one having 6 to 18 carbon atoms) in a weight ratio of about 2:8 to 8:2, and further contains alkylamine (alkyl An industrial antifungal agent characterized by adding a group having 8 to 18 carbon atoms. 4. The industrial antifungal agent according to claim 3, wherein the alkyl bromoacetate is lauryl bromoacetate. 5. The industrial antifungal agent according to claim 3 or 4, wherein the alkylamine is laurylamine.