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Structure and preparation method of acrylic antifouling resin grafted with benzisothiazolinone formate monomer

An acrylate-based, isothiazoline technology used in antifouling/underwater coatings, anti-corrosion coatings, biocide-containing paints, etc.

Active Publication Date: 2021-10-22
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 and preparation method of acrylic antifouling resin grafted with benzisothiazolinone formate monomer
  • Structure and preparation method of acrylic antifouling resin grafted with benzisothiazolinone formate monomer
  • Structure and preparation method of acrylic antifouling resin grafted with benzisothiazolinone formate monomer

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 (0.01mol) 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 ( Add 0.01 mol) benzo[d]isothiazolin-3-one, 1.35g (0.01 mol) 2-methylallyl chloroformate and catalytic amount of triethylamine into a 100 mL three-necked flask, add 25ml of toluene , 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, 1.48g (0.01 mol) 2-ethyl allyl chloroformate and a catalytic amount of triethylamine were added to a 100 mL three-necked flask, and 25ml 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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PUM

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Abstract

The invention relates to an antifouling resin containing a benzo[d]isothiazoline-3-ketone formate structure and a preparation method thereof, which is used in the field of marine antifouling materials. Using a mixed monomer composed of benzo[d]isothiazoline-3-ketone carboxylate alkenyl ester functional monomer and one or more than two alkenyl monomers, carry out copolymerization reaction in the presence of an initiator to obtain yellow and transparent An antifouling resin containing benzo[d]isothiazolin-3-one carboxylate alkenyl ester monomer structure. The antifouling resin containing benzo[d]isothiazoline-3-ketone carboxylate alkenyl ester monomer structure provided by the invention has simple preparation process and low raw material price, and is suitable for large-scale industrial production. At the same time, it exhibits excellent algae-inhibiting and bactericidal properties. The number average molecular weight of the synthesized resin polymer is between 10000-20000, and the release rate of the active substance can be controlled through the hydrolysis of the covalent bond, so that the coating can achieve long-term antifouling effect, which has good practical application value and broad development prospect.

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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Patent Type & Authority Patents(China)
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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