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Structure of acrylate antifouling resin grafted with benzisothiazolinone formate monomers and preparation method of acrylate antifouling resin

An acrylate, isothiazoline technology, applied in antifouling/underwater coatings, anticorrosion coatings, biocide-containing paints, etc., to achieve the effects of simple structure, convenient preparation, and good inhibition ability

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, benzo [d] isothiazolin-3-ketone is reacted with propylene chloroformate, and then copolymerized with acrylate to obtain the marine antifouling coating of acrylic resin side chain grafted BIT active structural unit. to report

Method used

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  • Structure of acrylate antifouling resin grafted with benzisothiazolinone formate monomers and preparation method of acrylate antifouling resin
  • Structure of acrylate antifouling resin grafted with benzisothiazolinone formate monomers and preparation method of acrylate antifouling resin
  • Structure of acrylate antifouling resin grafted with benzisothiazolinone formate monomers and preparation method of acrylate antifouling resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of benzo[d]isothiazolin-3-one-2-carboxylate allyl alcohol ester monomer: in a 100 ml three-necked flask equipped with a stirring device, a condenser tube and a thermometer, add 1.51g (0.01 mol ) benzo [d] Isothiazolin-3-one, 1.21 g (0.01 mol ) allyl alcohol chloroformate and a catalytic amount of triethylamine were added to a 100 mL three-necked flask, and 25 ml of toluene was added. After the dissolution was complete, the reaction was stirred at room temperature for 2.0 Hours, TLC tracking reaction to complete. The reactant was cooled to room temperature, filtered with suction, and the filtrate was collected, washed with water, neutralized, dried, concentrated and evaporated to dryness, and the residue was separated and purified to obtain a light yellow solid with a yield of 84.5%.

Embodiment 2

[0029] The preparation of benzo [d] isothiazolin-3-one-2-formic acid-2-methallyl alcohol ester monomer: in the 100 ml there-necked flask equipped with stirring device, condenser and thermometer, add 1.51g ( 0.01 mol) benzo[d]isothiazolin-3-one, 1.35 g (0.01 mol) 2-methylallyl chloroformate and a catalytic amount of triethylamine were added to a 100 mL three-necked flask, and 25 ml of toluene was added , after the dissolution was complete, the reaction was stirred at 50° C. for 2.0 hours, followed by TLC until the reaction was complete. The reactant was cooled to room temperature, filtered with suction, and the filtrate was collected, washed with water, neutralized, dried, concentrated and evaporated to dryness, and the residue was separated and purified to obtain a white solid with a yield of 83%.

Embodiment 3

[0031] Preparation of benzo[d]isothiazolin-3-one-2-formic acid-2-ethyl allyl alcohol ester monomer: in a 100 ml three-necked flask equipped with stirring device, condenser and thermometer, add 1.51g ( 0.01 mol) benzo[d]isothiazolin-3-one, 1.48 g (0.01 mol) 2-ethyl allyl chloroformate and catalytic amount of triethylamine were added to a 100 mL three-necked flask, and 25 ml of toluene was added , after the dissolution was complete, the reaction was stirred at 50° C. for 2.0 hours, followed by TLC until the reaction was complete. The reactant was cooled to room temperature, filtered with suction, and the filtrate was collected, washed with water, neutralized, dried, concentrated and evaporated to dryness, and the residue was separated and purified to obtain a white solid with a yield of 79.5%.

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Abstract

The invention relates to antifouling resin containing a benzo[d]isothiazoline-3-one alkenyl formate structure and a preparation method of the antifouling resin, belonging to the field of marine antifouling materials. The yellow transparent antifouling resin containing the benzo[d]isothiazoline-3-one alkenyl formate monomer structure is obtained by carrying out a copolymerization reaction on mixedmonomers consisting of a benzo[d]isothiazoline-3-one alkenyl formate functional monomer and one or more than one other alkenyl monomers in the presence of an initiator. The antifouling resin containing the benzo[d]isothiazoline-3-one alkenyl formate monomer structure in the invention is simple in preparation process, low in raw material price and suitable for industrial large-scale production. Atthe same time, the antifouling resin shows excellent alga inhibition and sterilization performance. The number-average molecular weight of a synthesized resin polymer is 10000-20000, and the release rate of active substances can be controlled through hydrolysis of covalent bonds, so a coating achieves a long-term antifouling effect, and very good practical application value and broad development prospects are achieved.

Description

technical field [0001] The invention relates to the field of marine antifouling coatings, in particular to a structure of a side chain branched benzo[d]isothiazolin-3-one-2-carboxylate functional monomer and a preparation method thereof. The structure of this type of copolymer contains benzo[d]isothiazolin-3-one active units, which can be used in marine antifouling and anticorrosion coatings, industrial bactericidal coatings and the like. Background technique [0002] The International Maritime Organization stipulates that since the use of organotin antifouling coatings has been banned worldwide since January 2008, the resins used in existing antifouling coatings are mostly acrylic acid resins, chlorinated rubber and epoxy resins. It has no antifouling effect by itself, and needs to rely on physical addition of antifouling agents such as cuprous oxide, zinc oxide, DDT, chlorothalonil, zinc pyrithione, 4,5-dichloro-2-n-octyl-4-isothiazole Phenin-3-one and other insecticidal ...

Claims

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Application Information

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IPC IPC(8): C08F220/14C08F220/18C08F218/12C09D133/12C09D5/16C09D5/08C09D5/14C07D275/04
CPCC07D275/04C08F220/14C08F220/18C09D5/08C09D5/14C09D5/1662C09D133/12
Inventor 杨建新董苗王雪梅王向辉林强
Owner HAINAN UNIVERSITY
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