Ester derivative containing acrylamide indole, preparation method and application thereof

The technology of acrylamido indole and acrylamide group is applied in the field of ester derivatives containing acrylamido indole and the preparation thereof, and can solve the problems of reduced antifouling period effect, fast release rate, poor compounding performance and the like , to achieve the effect of uniform release, preventing adhesion and good antifouling performance

Inactive Publication Date: 2014-03-26
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of antifouling agent can only be applied to antifouling coatings in the form of addition, and the compounding performance with other components is poor, resulting in too fast release rate and greatly reducing the antifouling effect. This makes it stop at the application performance research in antifouling coatings

Method used

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  • Ester derivative containing acrylamide indole, preparation method and application thereof
  • Ester derivative containing acrylamide indole, preparation method and application thereof
  • Ester derivative containing acrylamide indole, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Preparation of 3-(3-((acrylamido) methyl)-1-indolyl) propionic acid methyl ester

[0048] 1. Preparation of 3-(1-indolyl) methyl propionate

[0049] Weigh 5.8g (0.05mol) of indole and 11.9g (0.05mol) of dimethyl β-dithiodipropionate and dissolve them in 50mL of anhydrous tetrahydrofuran (THF). Add 50mL of anhydrous THF and 3.6g (0.09mol) NaH (60% content) in sequence into a 250mL three-necked flask equipped with a stirring device and a thermometer, and add the THF solution of indole to the above system dropwise at 0°C. After dropping, the reaction was continued for 30 minutes, and the THF solution of dimethyl β-dithiodipropionate was added dropwise to the above system while maintaining 0°C. After dropping, the reaction was continued at room temperature for 3 hours. After the reaction, add 50mL of saturated NH 4 Cl solution, let it stand, take the oil layer, evaporate the solvent, wash with water, MgSO 4 A reddish-brown oil was obtained after drying for...

Embodiment 2

[0054] Example 2: Preparation of 3-(3-((acrylamido)methyl)-5-bromo-1-indolyl)propionic acid methyl ester

[0055] 1. Preparation of methyl 3-(5-bromo-1-indolyl)propionate

[0056] Weigh 9.8g (0.05mol) of 5-bromoindole and 11.9g (0.05mol) of dimethyl β-dithiodipropionate and dissolve them in 50mL of anhydrous tetrahydrofuran (THF). Add 50mL of anhydrous THF and 3.6g (0.09mol) NaH (60% content) in sequence into a 250mL three-necked flask equipped with a stirring device and a thermometer, and add the THF solution of indole to the above system dropwise at 0°C. After dropping, the reaction was continued for 30 minutes, and the THF solution of dimethyl β-dithiodipropionate was added dropwise to the above system while maintaining 0°C. After dropping, the reaction was continued at room temperature for 3 hours. After the reaction, add 50mL of saturated NH 4 Cl solution, let it stand, take the oil layer, evaporate the solvent, wash with water, MgSO 4 A reddish-brown oil was obtained...

Embodiment 3

[0061] Example 3: Preparation of ethyl 3-(3-((acrylamido)methyl)-5-bromo-1-indolyl)propionate

[0062] 1. Preparation of ethyl 3-(5-bromo-1-indolyl)propionate

[0063] Weigh 9.8g (0.05mol) of 5-bromoindole and 13.3g (0.05mol) of diethyl β-dithiodipropionate and dissolve them in 50mL of anhydrous tetrahydrofuran (THF). Add 50mL of anhydrous THF and 3.6g (0.09mol) NaH (60% content) in sequence into a 250mL three-necked flask equipped with a stirring device and a thermometer, and add the THF solution of indole to the above system dropwise at 0°C. After dropping, continue to react for 30 minutes, then add the THF solution of diethyl β-dithiodipropionate dropwise into the above system while keeping 0°C. After dropping, the reaction was continued at room temperature for 3 hours. After the reaction, add 50mL of saturated NH 4 Cl solution, let it stand, take the oil layer, evaporate the solvent, wash with water, MgSO 4 A reddish-brown oil was obtained after drying for 12 hours. U...

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Abstract

The invention relates to a formula (I) compound containing the structural formula (refer to the Specification), in the formula, X1 refers to H and Cl; X2 refers to H, Cl and Br; R refers to CH3, CH2CH3, CH2(CH3)2, CH2CH2CH2CH3 and CH2CH2CH2CH2CH2CH(CH3)2. The invention also relates to a preparation method for the formula (I) compound and an acyclic acid zinc/copper resin adopting the compound as a comonomer, and the invention further relates to application of the resin compound in marine antifouling paint. According to the formula (I) structure, the acyclic acid zinc/copper resin adopting an ester derivative containing acrylamide indole as the comonomer has a relatively good self-polishing property, can slowly release an antifouling gramine derived structure and can effectively prevent adhesion of marine fouling organisms.

Description

【Technical field】 [0001] The invention relates to an indole derivative, in particular to an ester derivative containing acrylamido indole, a preparation method and application thereof. 【Background technique】 [0002] In the process of marine antifouling coatings, antifouling agent plays a pivotal role as a key component. Antifouling agents from the earliest use of copper, lead and their compounds, to the later arsenic, mercury and their compounds, and the widely used tributyltin in the 1970s have been banned due to serious environmental pollution and ecological damage. In the existing commercialized antifouling coating products, most of the antifouling agents including chlorothalonil and cuprous oxide have also caused varying degrees of pollution to the marine environment, which makes the development of environmentally friendly antifouling agents imminent . In the development of environmentally friendly antifouling agents, finding substances with antifouling activity from ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14C08F220/60C08F220/18C08F220/14C08F220/06C08F4/04C08F8/44C09D133/24C09D133/12C09D133/08C09D7/12C09D5/16
CPCC07D209/14C08F8/44C08F220/14C08F220/18C08F220/1804C08F220/60C08F220/603C09D5/1662C09D133/08C09D133/12C09D133/24C08F220/06
Inventor 李霞闫雪峰倪春花赵海洲于良民姜晓辉董磊张志明李昌城夏树伟高学理
Owner OCEAN UNIV OF CHINA
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