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Zwitterion-containing water-soluble cross-linking agent as well as preparation method and application thereof

A solvent and reaction technology, applied in the preparation of peptides, organic compounds, sulfonates, etc., can solve the problems of limiting the application of zwitterionic monomers, and achieve excellent anti-biological pollution characteristics, high purity, and side effects little effect

Inactive Publication Date: 2014-06-25
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many studies on the preparation and application of zwitterionic monomers, but these studies are limited to the development of zwitterionic functional monomers containing one or no double bonds, and there are no zwitterionic monomers containing two double bonds. Therefore, the application of zwitterionic monomers is largely limited

Method used

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  • Zwitterion-containing water-soluble cross-linking agent as well as preparation method and application thereof
  • Zwitterion-containing water-soluble cross-linking agent as well as preparation method and application thereof
  • Zwitterion-containing water-soluble cross-linking agent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1, compound shown in synthetic formula IV

[0063] 1.17g (0.01mol) was attributed to the N-methyl-2,2'-diaminodiethylamine of the compound shown in formula II (at this time R 1 is methyl, R 2 is ethyl, R 3 is ethyl) in a 100mL single-necked flask, add 30mL of solvent dichloromethane, and add 5mL of 6mol / L sodium hydroxide aqueous solution into the reaction flask (sodium hydroxide is used here as an acid-binding agent to remove the hydrogen chloride generated during the reaction to ensure the reaction The smooth progress), magnetic stirring, 2.7g (0.03mol) acryloyl chloride belonging to the compound shown in formula III (at this time R 4 (for hydrogen) was slowly added to the above solution, and the amidation reaction was continued at 0°C for 5h. After the reaction, the solution is placed in a separatory funnel, and the lower layer solution is rotary evaporated to obtain the compound shown in the formula IV. The structure is as follows, and its hydrogen nuc...

Embodiment 2

[0066] Embodiment 2, compound shown in synthetic formula I

[0067] 2.25 g (0.01 mol) of the compound shown in Formula IV obtained in Example 1 was dissolved in 20 mL of solvent acetonitrile, and 1.83 g (0.015 mol) of 1-3' propane sultone belonging to the compound shown in Formula V was added (at this time R 5 methylene) and 4 mg of hydroquinone (inhibitor), reacted at 30°C for 8 hours to obtain a viscous solid precipitate, then repeatedly cleaned the solid precipitate with acetonitrile, and removed excess acetonitrile by rotary evaporation to obtain a white Powder precipitation.

[0068] Proton NMR spectrum analysis, the structure of the product is shown below, and its proton nuclear magnetic resonance spectrum is as attached figure 2 shown.

[0069]

[0070] Among them, attached figure 2 1 In the H NMR spectrum, the characteristic peaks with a chemical shift of 5.69-6.18ppm are the proton peaks at a and b; the characteristic peaks with a chemical shift of 3.47-3.51p...

Embodiment 3

[0074] Embodiment 3, compound shown in synthetic formula IV

[0075] According to the steps of Example 1, only 30mL of dichloromethane was replaced by 40mL of dichloromethane, and 2.7g (0.03mol) of acryloyl chloride was replaced by 0.9g (0.01mol) of acryloyl chloride belonging to the compound represented by formula III, and amidation reaction The temperature was replaced by 0°C to 25°C, and the time was replaced by 5 hours to 1 hour to obtain the compound shown in formula IV;

[0076] The structural verification data of this product is not substantially different from that of Example 1, and will not be repeated here.

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Abstract

The invention discloses a zwitterion-containing water-soluble cross-linking agent as well as a preparation method and application thereof. The structural formula of the compound is a formula I. The compound has good water solubility and anti-nonspecific adsorption feature, so that the compound can be used as a cross-linking agent to prepare the polymer with high cross-linking degree, the obtained polymer has excellent biological pollution resistant feature, and can be widely applied to the fields such as biomedicine and materials. The water-soluble cross-linking agent is capable of reducing the protein aggregation speed, so that the protein molecule can be more easily presented in crystal form, and therefore the water-soluble cross-linking agent can be used for synthesizing the biomaterial for promoting protein crystallization. Furthermore, the cross-linking agent molecule comprises two-NH-C=O groups capable of generating hydrogen bond interaction with the carbohydrate (-OH) abound on the surface of microorganism; therefore, the cross-linking agent molecule can be used as an additive to prepare a molecular imprinting film material so as to selectively separate the microorganism (structural formula).

Description

technical field [0001] The invention relates to a water-soluble crosslinking agent containing zwitterions, a preparation method and application thereof. Background technique [0002] Biomedical materials are new materials used to diagnose, treat, repair or replace the damaged tissues and organs of living organisms or enhance their functions. It shows that the industry of biomedical materials and related products will develop into a pillar industry of the world economy in this century. At present, polyester materials are widely used in the field of biomedical polymer materials. The synthesis of these materials requires a large number of cross-linking agents to bond and cross-link multiple linear molecules into a network structure. Due to the particularity of the biomedical field, there is a great demand for the water solubility of cross-linking agents. However, only a small amount of cross-linking agents that can undergo free radical polymerization have a certain degree of w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C303/32C08F220/56C08F222/38C07K1/30C12N1/20C07C233/38C07C231/02
Inventor 任雪芹胡玉峰申锋张庆喜
Owner CHINA AGRI UNIV
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