JPH0231043B2 - SUICHUSEIBUTSUKIHIZAI - Google Patents

Description

[Detailed description of the invention]

The present invention relates to an aquatic organism repellent containing a maleimide compound and a benzanilide compound as active ingredients. At all times, such as the bottom of ships, fishing nets, buoys, and other underwater structures, underwater structures such as dam equipment, condenser cooling water in thermal power plants, heat exchanger cooling water intake channels in various industries, etc. Shellfish such as barnacles, oysters, mussels, hydrobugs, serpura, bryozoans, sea squirts, sea lettuce, blue seaweed, and seaweed, as well as algae, adhere to and propagate on parts that come into contact with water. This not only causes deceleration and increased fuel consumption, but also
This will result in economic losses due to cleaning costs for cleaning the bottom of the ship or suspension of ship operations during this cleaning period, and will cause inconvenience in handling underwater structures.
The amount of water intake decreases in intake channels for heat exchangers, etc.
Not only does this reduce cooling efficiency, but the biomass that falls off the channel walls and is washed away causes major losses, such as deteriorating the performance of equipment. Therefore, conventionally, such seawater and
In order to prevent damage caused by the attachment and propagation of freshwater pests, various aquatic organism repellents are applied and impregnated on ship bottoms, fishing nets, underwater equipment, etc.; To achieve a long-lasting aquatic biofouling effect, it is necessary to employ aquatic biorepellents containing heavy metal compounds such as cuprous oxide and organotin compounds. However, as is well known, the use of these heavy metal compounds may cause environmental pollution such as rivers or seawater, and may also have a negative impact on the human body through fish, causing social problems. It cannot be said that it is desirable. Therefore, it is desired to develop an aquatic organism repellent that does not contain such harmful elements and has an excellent aquatic organism repellent effect, and various aquatic organism repellents have been proposed. However, it cannot be said that there has been sufficient development yet of a material that exhibits an excellent repellent effect on aquatic organisms comparable to those containing harmful elements such as heavy metal compounds. For example, JP-A-54-59325 discloses a water-based antifouling agent containing a benzanilide compound as an active ingredient, but according to tests conducted by the present inventors, this agent is not effective against barnacles. However, it has the serious drawback that it is not effective against other animals, such as the common caterpillar, the common caterpillar, and the mussel, and is not effective at all against algae. The present inventors have conducted various studies to overcome the drawbacks of conventional aquatic life repellents and to develop an aquatic life repellent that does not contain harmful elements. The antifouling effect was significantly improved by combining the maleimide compound (Japanese Patent Application Laid-open No. 53-9320), which was proposed for use as an anti-fouling compound, with the above-mentioned benzanilide compound, making it more effective than conventional cuprous oxide, organotin compounds, etc. It has been found that an excellent antifouling effect equivalent to that of the aquatic organism repellent contained as a component can be obtained. The present invention has been made based on this knowledge. That is, the present invention has the general formula (In the formula, R represents a halogen atom, a lower alkyl group, or a lower alkoxy group, and n represents an integer of 1 to 3.) A maleimide compound represented by the general formula (In the formula, X represents a halogen atom, a methyl group or a trifluoromethyl group, and R' represents a lower alkyl group.) An aquatic organism repellent characterized by containing a benzanilide compound represented by the following as an active ingredient This is what we provide. In the present invention, the maleimide compound represented by the general formula () and the benzanilide represented by the general formula () are mixed in a weight ratio of 10 to 90:90 to 10.
It is preferable to use the ratio of 50-70:50-30.
It is particularly preferable to mix at a ratio of . Specific examples of the maleimide compound represented by the general formula () include those in which R _o is as shown below.

[Table] Examples of the benzanilide compound of the general formula () include compounds in which X and R' are as shown in the table below.

【table】

[Table] The aquatic organism repellent of the present invention is used without any limitation in the form of use, and may be used as a paint, solution, emulsion, or hydrating agent as appropriate. For example, by blending the aquatic organism repellent of the present invention with a film forming agent to prepare an antifouling paint, and applying this to the bottom of a ship, underwater structures, or walls of cooling water intake passages, aquatic organisms can be prevented. can prevent the adhesion and propagation of At this time, as the coating film forming agent, for example, oil varnish, synthetic resin, artificial rubber, etc. are used. Pigments and the like can be further added to the antifouling paint as desired. When preparing an antifouling paint, there is no upper limit to the concentration of the aquatic organism repellent of the present invention as long as a coating film can be formed, but it is preferably blended in a proportion of up to 15% by weight based on the antifouling paint. For the purpose of preventing the adhesion and propagation of aquatic organisms in cooling water intake channels, the aquatic organism repellent of the present invention may be added into the intake channels in the form of a solution or emulsion, but it will not have a long-term antifouling effect. For long-lasting effects, it is preferable to apply it in the form of a paint. Furthermore, the aquatic organism repellent of the present invention can be applied to fishing nets made of any material; in this case, the present repellent is dissolved together with a resin in an organic solvent (hereinafter referred to as resin liquid), and this resin liquid is dissolved. This is done by impregnating fishing nets and drying them. When preparing this resin liquid, the aquatic organism repellent of the present invention should be added to the resin liquid.
The resin is dissolved in the organic solvent to a concentration of less than 50% by weight, preferably from 5 to 25% by weight. Examples of the resin used for preparing the resin liquid include vinyl chloride resin, phenol resin, alkyd resin, and chlorinated rubber. In addition, examples of organic solvents include benzene, toluene, xylene,
Chloroform etc. are used. Furthermore, if the resin is difficult to dissolve, dimethylformamide,
Dimethylacetamide or dimethylsulfoxide can be used and mixed as appropriate. Moreover, it can be used by dispersing it in a suspended state in a solution. Each active ingredient in the aquatic organism repellent of the present invention has an antifouling effect on aquatic organisms, but each active ingredient in the aquatic organism repellent of the present invention has an antifouling effect against barnacles, other animals, and algae. It has the characteristic of exhibiting an excellent antifouling effect beyond what would be expected if it were used alone. Furthermore, the aquatic organism repellent of the present invention does not contain harmful substances such as cuprous oxide and organic tin compounds, and is highly safe, with almost no fear of environmental pollution or adverse effects on the human body mediated by fish and shellfish. It also has the advantage that it has little effect on the human body during painting and there are no problems with fish toxicity, so it can be used in aquaculture tanks and the like. Next, the present invention will be explained in more detail based on examples. In addition, % in an example shows weight %. The compounds used in the examples are as follows. 1 Maleimide compound Compound 1 N-(2,4,6-trichlorophenyl)maleimide compound 2 N-(2,6-diethylphenyl)maleimide compound 3 N-(2,6-dichlorophenyl)maleimide compound 4 N -(3-isopropoxyphenyl)maleimide compound 5 N-(3-bromophenyl)maleimide 2 Benzanilide compound compound 6 2-Methyl-3'-methoxybenzanilide compound 7 2-Methyl-3'-isopropoxybenz Anilide compound 8 2-trifluoromethyl-3'-ethoxybenzanilide compound 9 2-trifluoromethyl-3'-isopropoxybenzanilide compound 10 2-iodo-3'-isopropoxybenzanilide compound 11 2 -Chloro-3'-isopropoxybenzanilide Example 1 (Seawater immersion test) N-(2,4,6-trichlorophenyl)maleimide (compound 1) and 2-methyl-3'-isopropoxybenzanilide (Compound 7) 2:1
(weight ratio), and further blended in the following ratio, thoroughly ground and mixed in a ball mill to prepare an antifouling paint. (Ingredients) (Amount) Compound (1) 10% Compound (2) 5% Petal 13% Talc 15% Zinc white 10% CR-20 (Chlorinated rubber resin: manufactured by Asahi Denka) 15% DOP 1% Xylene 31% Total 100% Apply this antifouling paint once with a wash primer.
A test plate was prepared by brush painting twice on a steel plate (300 x 100 x 1 mm) that had been primed twice with an anti-corrosive paint (no chemicals added). This test plate was fitted into a wooden frame and suspended from an immersion raft in seawater and maintained at a depth of 1.5 m.
The test board that had been immersed in seawater was pulled up after 6 and 12 months, and the degree of adhesion of living things such as shellfish and algae on the test board was expressed as a percentage of the total area of adhesion, and the results are shown in Table 3. show. Examples 2 to 10 Paints were prepared in the same manner as in Example 1 using Compounds 1 to 11, changing the maleimide compound or benzanilide compound, or changing the ratio of both, and conducted a seawater immersion test. Ivy. The result is the third
Shown in the table. Comparative Example 1 A test plate treated once with a wash primer and twice with an anticorrosive paint (no chemicals added) was prepared, and a seawater immersion test was conducted in the same manner as in Example 1. The results are shown in Table 3. Comparative Example 2 A paint was prepared in the same manner as in Example 1 except that Compound 1 was not used and only Compound 7 was blended at 15%, and a seawater immersion test was conducted. The results are shown in Table 3. Comparative Example 3 A paint was prepared in the same manner as in Example 1 except that Compound 7 was not used and only Compound 1 was blended at 15%, and a seawater immersion test was conducted. The results are shown in Table 3. Comparative example 4 Compound 7 only at 5.0%, compound 1 equivalent 10
A paint was prepared in the same manner as in Example 1, except that % was uniformly blended with other pigments, and a seawater immersion test was conducted.
The results are shown in Table 3. Comparative Example 5 Compound 1 only at 10.0%, equivalent to Compound 7
Example 1 except that 5.0% was uniformly distributed to other pigments
A paint was prepared in the same manner as above, and a seawater immersion test was conducted. The results are shown in Table 3. Comparative Examples 6 and 7 A paint was prepared in the same manner as in Example 9, except that the same amount of triphenyltin hydroxide was blended in place of Compound 1 or 2, and a seawater immersion test was conducted. The results are shown in Table 3.

【table】

Claims (1)

[Claims] 1. General formula (In the formula, R represents a halogen atom, a lower alkyl group, or a lower alkoxy group, and n represents an integer of 1 to 3.) A maleimide compound represented by the general formula (In the formula, X represents a halogen atom, a methyl group, or a trifluoromethyl group, and R' represents a lower alkyl group.) An aquatic organism repellent characterized by containing a benzanilide compound represented by the following as an active ingredient.