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Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazoline-3-one-triazinyl monomer

An antifouling resin and triazine-based technology, applied in biocide-containing paints, antifouling/underwater coatings, organic chemistry, etc., can solve the problem of short duration of drug effect, limited application range, poor water solubility, etc. Problems, to achieve the effect of not easy to spread and lose, low cost, and good development prospects

Active Publication Date: 2020-08-25
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, from a structural point of view, BIT is a small molecular compound, so its use is mainly based on physical addition and mixing. In the actual application process, there are disadvantages such as poor water solubility, severe dialysis, and short duration of drug effect, which limits its use to a certain extent. limits

Method used

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  • Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazoline-3-one-triazinyl monomer
  • Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazoline-3-one-triazinyl monomer
  • Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazoline-3-one-triazinyl monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] BIT-triazine-based antifouling resin monomer 1 ( figure 1 -Synthesis of a): In a two-necked flask with a stirring device, add 10 mL of allyl alcohol, control the temperature below 5°C in an ice-water bath, add 1.85 g of cyanuric chloride and 1.05 g of sodium bicarbonate in sequence, and react for 0.5 After 2 h, the temperature was naturally raised to room temperature, and the stirring reaction was continued for 2 h, and the reaction was stopped. Mix the reaction solution with ethyl acetate, extract and wash with water, repeat the operation three times, dry with anhydrous magnesium sulfate for 12 h, and filter the filtrate, which is 2-propenyloxy-4,6-dichloro-1,3,5-tri Zinc. Continue to add 3.02 g of BIT, adjust the pH with triethylamine during the reaction, stir at room temperature for 8 h, and stop the reaction. The filtrate was separated by suction filtration, extracted with ethyl acetate, washed three times with deionized water, and dried with anhydrous magnesium s...

Embodiment 2

[0018] BIT-triazine-based antifouling resin monomer 2 ( figure 1 -b) Synthesis: In a two-necked flask with a stirring device, add 10 mL of methallyl alcohol, control the temperature below 5°C in an ice-water bath, add 1.85 g of cyanuric chloride and 1.05 g of sodium bicarbonate in sequence , after 0.5 h of reaction, the temperature was naturally raised to room temperature, and the stirring reaction was continued for 3 h, and the reaction was stopped. Mix the reaction solution with ethyl acetate, extract and wash with water, repeat the operation three times, dry with anhydrous magnesium sulfate for 12 h, and filter the filtrate, which is 2-(2-methacryloxy)-4,6-dichloro-1 ,3,5-Triazine. Continue to add 3.02 g of BIT, adjust the pH with triethylamine during the reaction, stir at room temperature for 8 h, and stop the reaction. The filtrate was separated by suction filtration, extracted with ethyl acetate, washed three times with deionized water, and dried with anhydrous magnesi...

Embodiment 3

[0020] BIT-triazine-based antifouling resin monomer 3 ( figure 1 -c) Synthesis: In a two-necked flask with a stirring device, add 10 mL of 3-butenol, control the temperature below 5°C in an ice-water bath, add 1.85 g of cyanuric chloride and 1.05 g of sodium bicarbonate in sequence, After reacting for 0.5 h, the temperature was naturally raised to room temperature, and the stirring reaction was continued for 5 h to stop the reaction. Mix the reaction solution with ethyl acetate, extract and wash with water, repeat the operation three times, dry with anhydrous magnesium sulfate for 12 h, and filter the filtrate, which is 2-(3-butenyloxy)-4,6-dichloro-1, 3,5-Triazine. Then 3.32 g of BIT was added, the pH was adjusted with triethylamine during the reaction, and the reaction was stopped by stirring at room temperature for 6 h. The filtrate was separated by suction filtration, extracted with ethyl acetate, washed with deionized water three times, and dried with anhydrous magnesiu...

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Abstract

The invention relates to the field of marine antifouling. According to the invention, 1,2-benzo[d]isothiazoline-3-one (BIT) and cyanuric chloride (CNC) are used as raw materials to prepare a BIT-allyloxy triazine monomer, and a copolymerization reaction is conducted on the BIT-allyloxy triazine monomer and an acrylate monomer to prepare the acrylate antifouling resin grafted with a BIT active structural unit. A method for preparing a BIT-triazinyl antifouling resin monomer comprises the steps that under the condition of a temperature in a range of 0 DEG C to 25 DEG C, CNC reacts with allyl alcohol to obtain alkenyloxytriazine, and then the alkenyloxytriazine reacts with BIT to obtain the BIT-triazinyl antifouling resin monomer. The invention also discloses a structure and a method of BIT-triazinyl marine antifouling resin prepared through a copolymerization reaction of the monomer and acrylate. The BIT-triazinyl antifouling resin monomer provided by the invention has excellent polymerizability; and the BIT-triazinyl anti-fouling resin obtained through self-polymerization of the BIT-triazinyl antifouling resin or copolymerization of the BIT-triazinyl antifouling resin monomer with other monomers has high molecular weight, active substances are not prone to diffusion and loss in the using process of the resin, and meanwhile, a release rate can be controlled through hydrolysis ofester bonds, so the anti-fouling active substances are efficiently utilized, and the BIT-triazinyl anti-fouling resin is expected to become a green efficient novel marine anti-fouling coating.

Description

technical field [0001] The present invention relates to the field of marine antifouling coatings, in particular to the structure of a benzo[d]isothiazolin-3-one-triazine-based antifouling resin monomer and its copolymerized acrylate antifouling resin, and their Preparation. The antifouling resin copolymer contains benzo[d]isothiazolin-3-one structural unit, and can be used in marine antifouling paints, industrial bactericidal paints and the like. Background technique [0002] As a treasure house of resources and energy for human survival, the ocean has created rich material wealth and convenient transportation for the development of human society. The rational development and utilization of marine resources has become a development strategy for all countries. my country has a vast sea area, with an area of ​​more than 3 million square kilometers. The development and utilization of marine resources has become the only way for economic and social development. Marine biofouli...

Claims

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Application Information

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IPC IPC(8): C08F216/14C08F220/14C08F220/18C07D417/14C09D133/08C09D133/14C09D129/10C09D5/16
CPCC07D417/14C08F216/1466C08F220/14C08F220/18C09D5/14C09D5/1668C09D129/10C09D133/08C09D133/14
Inventor 杨建新董苗王雪梅林强王向辉
Owner HAINAN UNIVERSITY
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