Perfluoroalkyl sulfamide active amine acrylate compound and preparation method

A technology of active amine acrylate and perfluoroalkyl sulfonamide, which is applied in the preparation of sulfonate amide, organic chemistry, polyurea/polyurethane coating, etc., can solve the problem of difficult to wipe, can not be effectively inhibited or overcome, light-cured coating surface Not resistant to stains and other problems, to achieve the effect of high surface firmness, perfect surface curing, anti-fouling and wipe resistance

Active Publication Date: 2018-08-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to overcome the problem that the light-cured coating additives in the prior art cannot effectively inhibit or overcome the oxygen inhibition on the coating surface, which leads to the problem that the surface of the light-cured coating is not stain-resistant and difficult to wipe. The perfluoroalkylsulfonamide

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  • Perfluoroalkyl sulfamide active amine acrylate compound and preparation method

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Embodiment 1

[0044] A perfluoroalkylsulfonamide active amine acrylate compound, its structure is as follows: 1 :

[0045] , Formula M 1 ;

[0046] The above-mentioned perfluoroalkylsulfonamide active amine acrylate compound (M1) is prepared by the following method:

[0047] S1. Take N-aminoethylpiperazine and perfluorooctyl sulfonyl fluoride as raw materials to prepare a fluorocarbon chain compound A1 containing primary or secondary amine sulfonamide groups. The structure of compound A1 is as follows:

[0048] , A 1 ;

[0049] Using tetrahydrofur as the solvent, add 1 mol of perfluorooctyl sulfonyl fluoride dropwise to 3 mol of N-aminoethyl piperazine at 0°C. After the addition is complete, stir for 30 minutes and react at room temperature for 3 hours. A white precipitate is produced. ; Filter, wash with acetone 3 times, and dry to obtain white powdery solid compound A 1 , The yield is 76.13%. After NMR testing, the testing data is: 1 H NMR (400 MHz, DMSO) δ3.08 – 3.02 (1H), 2.82 (2H), 2.77 – 2....

Embodiment 2

[0053] A preparation of perfluoroalkyl sulfonamide active amine acrylate compound (M 1 The method of ), except that the raw material feeding ratio, reaction temperature, and reaction time are different, other conditions are the same as in Example 1;

[0054] Wherein, the method is carried out according to the following steps:

[0055] S1. Using tetrahydrofur as the solvent, add 1 mol of perfluorooctyl sulfonyl fluoride to 1 mol of N-aminoethyl piperazine dropwise at -30°C, and after the addition is complete, stir for 30 minutes and react at room temperature for 5 hours. White precipitate is produced; filtered, washed with acetone 3 times, and dried to obtain white powdery solid compound A 1 .

[0056] S2. Put 1mol of compound A 1 , 1mol 1,6-hexanediol diacrylate was added to the acetonitrile solution, stirred at 50°C for 12 hours, and the solvent was spin-dried to obtain a light brown liquid; after nuclear magnetic testing, the obtained light brown liquid contained the product perflu...

Embodiment 3

[0058] A preparation of perfluoroalkyl sulfonamide active amine acrylate compound (M 1 The method of ), except that the raw material feeding ratio, reaction temperature, and reaction time are different, other conditions are the same as in Example 1;

[0059] Wherein, the method is carried out according to the following steps:

[0060] S1. Using tetrahydrofur as the solvent, add 1 mol of perfluorooctyl sulfonyl fluoride to 10 mol of N-aminoethyl piperazine dropwise at 30°C. After the addition is complete, stir for 30 minutes and react at room temperature for 4 hours, white. Precipitation occurs; filtered, washed with acetone 3 times, and dried to obtain white powdery solid compound A 1 .

[0061] S2. Put 1mol of compound A 1 , 5mol 1,6-hexanediol diacrylate was added to the acetonitrile solution, stirred at 100°C for 24 hours, and the solvent was spin-dried to obtain a light brown liquid; after nuclear magnetic testing, the obtained light brown liquid contained the product perfluoroal...

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Abstract

The invention discloses a perfluoroalkyl sulfamide active amine acrylate compound and a preparation method. The structure of the compound is as shown in a formula (M) in the specification, wherein n=1-10, an R1 group comprises at least one (methyl) acrylate double-bonded structure, an R2 group comprises H atoms, the R1 group, alkyl with 1-8 carbon atoms or trimethylene alkylamine formed by combining R2 with R3, an R3 group comprises alkylene with 2-12 carbon atoms, an R4 group comprises H atoms or the R1 group, n=1-18 in a fluorocarbon chain, and preferably, n=8-12. The monomer is connected into the fluorocarbon chain through sulfamide bonds and accordingly achieves low surface tension, so that the monomer can float to the surface of a coating/ink layer in a photocurable coating formula system, and surface oxygen inhibition of a photocurable coating can be effectively inhibited. Besides, the photocurable coating is used with a hydrogen abstraction photoinitiator, photoinitiator conversion can be effectively accelerated, surface curing is perfected, the photocurable coating is high in surface firmness, and fouling and wiping resistance is remarkably improved.

Description

Technical field [0001] The invention relates to the field of photocuring of polymer materials, in particular to a perfluoroalkylsulfonamide active amine acrylate compound and a preparation method. Background technique [0002] Light curing refers to the instantaneous polymerization, cross-linking and curing technology of organic formula material system under ultraviolet light irradiation. Its composition mainly includes light curing resin, light curing reactive diluent monomer, photoinitiator, and auxiliary agent. It is mainly used in coatings and inks. , Adhesive field. Traditional free radical photoinitiators initiate the polymerization reaction. Although the curing speed is fast, due to the common oxygen inhibition effect of free radical polymerization, there is always an indispensable oxygen inhibition on the surface of the photocurable coating, which leads to polymerization and crosstalk on the surface of the coating. Insufficient connection, insufficient surface abrasion r...

Claims

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Application Information

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IPC IPC(8): C07D295/15C07C311/05C07C311/04C07C303/38C09D175/14C09D5/16C09D7/63
CPCC09D175/14C07C303/38C07C311/04C07C311/05C07D295/15C09D5/1687C08K5/435
Inventor 黄李江廖焕妍杨建文曾兆华
Owner SUN YAT SEN UNIV
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