Zwitterionic monomer containing bisamide structure and preparation method of zwitterionic monomer

A technology of zwitterion and bisamide, which is applied in the field of zwitterion compound synthesis, can solve the problems of increased sailing resistance of the hull, blocked and destroyed pipelines, and reduced sailing speed, and achieves the effects of less by-products, low cost and mild reaction conditions.

Inactive Publication Date: 2021-03-19
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Marine biofouling leads to increased sailing resistance of the hull, reduced sailing speed, blockage and destruction of pipelines; biofouling of implanted equipment can cause adverse reactions such as thrombosis, coagulation, immunity, and infection in the human body

Method used

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  • Zwitterionic monomer containing bisamide structure and preparation method of zwitterionic monomer
  • Zwitterionic monomer containing bisamide structure and preparation method of zwitterionic monomer
  • Zwitterionic monomer containing bisamide structure and preparation method of zwitterionic monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 3.08g of N,N'-methylenebisacrylamide (MBAA), dissolve 5.00mL of dimethylamine in 80mL of methanol, stir the reaction at 20°C for 48h, and then rotate the mixture after the reaction. Add 20mL acetone and 3mL acrylic acid to the rotary steamed product, stir and react at 20°C for 48h, add 20mL triethylamine and stir for 24h, after centrifugation, wash with acetone, dimethyl sulfoxide (DMSO), diethyl ether for several times, centrifuge, vacuum After drying, a white zwitterionic monomer powder containing a bisamide structure is obtained.

[0022] Such as figure 2 As shown, the structure of the zwitterionic monomer containing the bisamide structure obtained in Example 1 is characterized by proton nuclear magnetic resonance: 1H-NMR (400MHz, D 2 O): δ6.26(2H), 5.83(1H), 4.69(2H), 3.67(2H), 3.60(2H), 3.11(6H), 2.86(2H), 2.76(3H). Among them, 6.26 and 5.83 are the characteristic peaks of the double bond of the monomer; 4.69 is the characteristic peak of the methylene betw...

Embodiment 2

[0024] Take 13g of N,N'-methylenebisacrylamide (MBAA), dissolve 35mL of dimethylamine in 250mL of methanol and stir the reaction at 10°C for 12h, then rotate the mixture after the reaction. Add 200mL of acetone and 19mL of acrylic acid to the rotary evaporated product, stir and react at 25°C for 48h, add 60mL of triethylamine and stir for 12h, wash with acetone, dimethyl sulfoxide (DMSO) and ether several times after centrifugation, centrifuge, vacuum After drying, a white zwitterionic monomer powder containing a bisamide structure is obtained.

Embodiment 3

[0026] Take 8g of N,N'-methylenebisacrylamide (MBAA), dissolve 50mL of dimethylamine in 150mL of methanol and stir the reaction at 40°C for 12h, then rotate the mixture after the reaction. Add 200mL of acetone and 15mL of acrylic acid to the rotary evaporated product, stir and react at 30°C for 72h, add 55mL of triethylamine and stir for 24h, wash with acetone, dimethyl sulfoxide (DMSO) and ether for several times after centrifugation, centrifuge, vacuum After drying, a white zwitterionic monomer powder containing a bisamide structure is obtained.

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PUM

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Abstract

The invention provides a zwitterionic monomer containing a bisamide structure and a preparation method thereof. The preparation method comprises the steps that firstly, N,N'-methylenebisacrylamide (MBAA) and dimethylamine serve as raw materials and undergo a Michael addition reaction to obtain an MBAA product with one end having undergone tertiary amination, namely a first-step product; and with the first-step product and acrylic acid as raw materials, the zwitterionic monomer containing the bisamide structure is finally prepared under the action of triethylamine. According to the invention, the preparation method for the monomer is simple in process and mild in reaction condition, and large-batch preparation can be achieved; a zwitterionic material is easy to prepare through a polymerization reaction; and the zwitterionic material has good biological pollution resistance and is widely applied to ship body pollution resistance and biomedical instruments.

Description

technical field [0001] The invention relates to the technical field of synthesizing zwitterionic compounds, in particular to a zwitterionic monomer containing a bisamide structure and a preparation method thereof. Background technique [0002] Zwitterionic materials such as carboxybetaine (CB) and sulfobetaine (SB) materials have high dipole moments and high charge groups, but are still electrically neutral overall. This unique molecular structure makes them have different applications . Currently, as a biocompatible material, zwitterionic materials can resist non-specific protein adsorption in serum, increase the stability of enzymes in urea without inactivation, and do not induce immune responses during blood circulation. Studies have shown ultra-low contamination in single protein solutions and undiluted serum plasma due to the ultra-strong hydration of the zwitterionic material. Compared with sulfobetaine (SB), carboxybetaine (CB) material has stronger antifouling abil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/10C07C231/12
CPCC07C237/10
Inventor 刘文广陈薪羽杨建海
Owner TIANJIN UNIV
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