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Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazolin-3-one-triazine-based monomer

A technology of antifouling resin and butyl acrylate, which can be used in biocide-containing paints, antifouling/underwater coatings, organic chemistry, etc., and can solve problems such as poor water solubility, severe dialysis, and short duration of efficacy.

Active Publication Date: 2021-09-17
HAINAN UNIV
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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]isothiazolin-3-one-triazine-based monomer
  • Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazolin-3-one-triazine-based monomer
  • Structure and preparation method of acrylate antifouling resin containing benzo[d]isothiazolin-3-one-triazine-based 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, 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-(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 anhydrou...

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Abstract

The present invention relates to the field of marine antifouling. Using 1,2-benzo[d]isothiazoline-3-one (BIT) and cyanuric chloride (CNC) as raw materials, a BIT-allyloxy triazine monomer, and its copolymerization reaction with acrylate monomer to prepare an acrylate antifouling resin grafted with BIT active structural unit. The method for preparing the BIT-triazine-based antifouling resin monomer comprises: at a temperature of 0-25°C, first reacting CNC with propenyl alcohol to obtain an alkenyloxytriazine, and then reacting with BIT to obtain a BIT-triazine base antifouling resin monomer. The invention also discloses the structure and method of the BIT-triazine-based marine antifouling resin prepared by the copolymerization reaction of the above-mentioned monomer and acrylate. The BIT-triazine-based antifouling resin monomer provided by the present invention has excellent polymerizability, self-polymerized or copolymerized with other monomers, and the obtained BIT-triazine-based antifouling resin has a higher molecular weight. The active substance is not easy to diffuse and lose, and at the same time, the release rate can be controlled by the hydrolysis of the ester bond, so that the antifouling active substance can be used efficiently, and it is expected to become a new type of green and efficient marine antifouling 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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Patent Type & Authority Patents(China)
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 UNIV
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