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Acrylate amide anti-fouling agent and preparation method thereof

An ester-based amide and acrylate-based technology, which is applied in the field of acrylate amide antifouling agents and their preparation, can solve problems such as difficult degradation, marine environmental pollution, and high toxicity, and achieve anti-fouling organisms, simple preparation methods, The effect of controlling the release rate

Pending Publication Date: 2021-12-14
725TH RES INST OF CHINA SHIPBUILDING INDAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the 1980s, antifouling coatings for ships generally contained toxic antifouling agents such as mercury, arsenic, and organotin, which were highly toxic and difficult to degrade, causing serious pollution to the marine environment and endangering the growth and reproduction of marine organisms.
[0004] The above-mentioned antifouling agents are either expensive, or only through physical mixing with the resin, the release rate of the antifouling agent is affected by the matrix resin and the degree of physical mixing, the release of the antifouling agent in seawater is unstable, and the antifouling cycle short

Method used

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  • Acrylate amide anti-fouling agent and preparation method thereof
  • Acrylate amide anti-fouling agent and preparation method thereof
  • Acrylate amide anti-fouling agent and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] The technical process of the preparation method of the acrylate amide antifouling agent involved in the present invention comprises four steps of preparation, dripping, post-treatment and column chromatography:

[0027] (1) Preparation: Slowly add 50mmol of salamide antifouling agent, 60mmol of triethylamine and 25ml of dichloromethane into a three-necked flask to form a mixed system;

[0028] Slowly add 55mmol of acryloyl chloride and 25ml of dichloromethane into the constant pressure funnel to form a mixed solution;

[0029] (2) Dropping: feed nitrogen into the mixing system, and stir the mixing system at a speed of 500r / min under the condition that the temperature of the water bath is 20°C. After feeding nitrogen for 30 minutes, add the mixed solution dropwise to the mixing system to control The rate of addition is such that the dripping process of the mixed solution continues for 1.5 hours, and after the mixed solution and the mixed system react for 12 hours, the re...

Embodiment 2

[0033] This embodiment relates to the structural characterization of the acrylate amide antifouling agent prepared in Example 1:

[0034] Use NICOLETAVATAR-360 type infrared spectrophotometer to test the white needle-like crystals, get as follows image 3 In the infrared spectrogram shown, the ordinate is the transmittance (%), and the abscissa is the wave number (cm -1 ), of which, 3331.29cm -1 N-H stretching vibration absorption peak, 3000-2800cm -1 It is saturated C-H stretching vibration, 1735.34cm -1 It is the carbonyl absorption peak, 1639.50cm -1 It is the C=0 stretching vibration absorption peak in the amide group, 1606.25cm -1 、1573.00cm -1 and 1449.52cm -1 Both are benzene ring skeleton vibrations, 755.47cm -1 It is the C-H out-of-plane bending vibration, that is, the characteristic peak of the ortho-position substitution of the benzene ring, which is consistent with the molecular structure of Example 1.

[0035] Use the Bruker ultrafleXtreme MALDI TOF / TOF ma...

Embodiment 3

[0039] This example relates to the anti-fouling performance test of the acrylate amide antifouling agent prepared in Example 1 on diatoms: the acrylate amide antifouling agent was prepared with ethanol or DMSO to make 12.5 μg / ml and 50 μg / ml respectively and 200μg / ml 3 concentrations of A solution, add a pre-cut round glass slide to the microwell plate, add algae liquid, A solution and solvent (ethanol or DMSO) to the microwell plate, and place it in an artificial climate In the box, under the constant temperature condition of 23°C, standard culture light is adopted (6:00 am-6:00 pm, provide 5000lux light source irradiation; 6:00 pm-6:00 am the next morning, keep dark environment) After 72 hours, gently wash away the unattached algae on the round glass slide with sterilized seawater, observe the attachment of diatoms on the round glass slide with a fluorescence microscope, take random fluorescence photos of five fields of view, and use image pro to analyze the diatoms in the fl...

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Abstract

The invention belongs to the technical field of marine anti-fouling, and particularly relates to an acrylate amide anti-fouling agent and a preparation method thereof. The molecular structure of the acrylate amide anti-fouling agent is composed of a benzene ring, an acrylate group, an amido group and an alkyl chain R2, wherein the acrylate group and the amido group are connected to the benzene ring and are in an ortho-position relation, and the R2 group is located at the N position of an amino group and is connected with amide through a C-N bond. The preparation method of the acrylate amide anti-fouling agent comprises the following steps of: dropwise adding a dichloromethane solution in which acryloyl chloride is dissolved into a mixed system of dichloromethane in which an amide compound and triethylamine are dissolved under the condition of introducing nitrogen, reacting at normal temperature, washing, separating liquid, taking a lower-layer organic phase, adjusting the lower-layer organic phase to be neutral, drying, filtering, and carrying out rotary evaporation to obtain the acrylate amide anti-fouling agent. The acrylate amide anti-fouling agent with a modified structure is synthesized, is applied to a marine anti-fouling coating system, and can release anti-fouling components and prevent the growth of fouling organisms through ester group hydrolysis in a seawater environment.

Description

Technical field: [0001] The invention belongs to the technical field of marine antifouling, and specifically relates to an acrylic acid amide antifouling agent and a preparation method thereof. The molecular structure of the antifouling agent contains carbon-carbon double bonds, propylene groups, ester groups and amide groups, and is used in marine environments. Anti-biofouling on the surface of offshore facilities such as ships and offshore platforms. Background technique: [0002] Marine biofouling refers to the biofouling formed by the adsorption, growth and reproduction of marine microorganisms, plants and animals on the surface submerged in seawater, which causes great harm to marine engineering equipment such as ships, nuclear power plants and oil production platforms. For example: the hull becomes rough after being attached by marine organisms, and the sailing resistance and fuel consumption increase significantly. The most common solution to the problem of marine fo...

Claims

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Application Information

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IPC IPC(8): C07C235/60C07C231/12C07C231/24C09D5/16
CPCC07C235/60C09D5/1625C07C231/12C07C231/24
Inventor 郑纪勇荀靖懿蔺存国孙智勇邱峥辉张广龙
Owner 725TH RES INST OF CHINA SHIPBUILDING INDAL CORP
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