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O-thiazolidine methyl ester-n-trimethyl chitosan quaternary ammonium salt and its preparation method and application

A technology of trimethyl chitosan and thiazolidine methyl ester is applied in the field of polymer compound materials, which can solve problems such as limited application, and achieve the effects of enhancing antibacterial activity and hydrophilicity, good antibacterial property, and expanding the scope of application.

Inactive Publication Date: 2016-03-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chitosan is insoluble in water, which limits its application in antibacterial

Method used

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  • O-thiazolidine methyl ester-n-trimethyl chitosan quaternary ammonium salt and its preparation method and application
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  • O-thiazolidine methyl ester-n-trimethyl chitosan quaternary ammonium salt and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0030] A kind of O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0031] (1) Dissolve 4g of chitosan in 200mL of deionized water and 15mL of formic acid, stir and heat up to 70°C, add 10mL of formaldehyde solution, mix well and transfer to a microwave normal pressure reactor, adjust the microwave power to 400W React at 30°C for 240 minutes; adjust the pH to alkaline with 15% NaOH solution, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone (NMP) after drying, add 20mL methyl iodide , react at 40° C. for 120 h; add twice the volume of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N-trimethyl chitosan.

[0032] The substitution degree of N-trimethyl chitosan quaternary ammonium salt is 63% through photoelectron spectroscopy quantitative analysis (XPS) for C and N element analysis.

[0033] (2) Pipette 10 g o...

Embodiment 2

[0036] A kind of O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0037] (1) Dissolve 4g of chitosan in 200mL of deionized water and 15mL of formic acid, stir and heat up to 70°C, add 10mL of formaldehyde solution, mix well and transfer to a microwave normal pressure reactor, adjust the microwave power to 500W React at 40°C for 180min; adjust the pH to alkaline with 15% NaOH solution, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone after drying, add 40mL methyl iodide, 40°C React for 120 h; add two volumes of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N-trimethyl chitosan.

[0038] The substitution degree of N-trimethyl chitosan quaternary ammonium salt is 69% through photoelectron spectroscopy quantitative analysis (XPS) for C and N element analysis.

[0039] (2) Pipette 10 g of L-cysteine ​​hydroch...

Embodiment 3

[0042] A kind of O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0043] (1) Dissolve 4g of chitosan in 200mL of deionized water and 15mL of formic acid, stir and heat up to 70°C, add 10mL of formaldehyde solution, mix well and transfer to a microwave normal pressure reactor, adjust the microwave power to 600W React at a temperature of 50°C for 120 minutes; use 15% NaOH solution to adjust the pH to alkaline, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone after drying, add 60mL methyl iodide, 40°C React for 120 h; add two volumes of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N-trimethyl chitosan.

[0044] The substitution degree of N-trimethyl chitosan quaternary ammonium salt is 73% through photoelectron spectroscopy quantitative analysis (XPS) for C and N element analysis.

[0045] (2) Pipette 10 g...

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Abstract

The invention belongs to the field of the high polymer compound materials and discloses an O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt as well as a preparation method and application thereof. The preparation method of the O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt comprises the following steps: carrying out a microwave reaction on starting raw materials (including chitosan, formaldehyde and formic acid) to obtain a chitosan Schiff base and then reacting the chitosan Schiff base with methyl iodide to obtain N-trimethyl chitosan; preparing thiazolidine formyl chloride by using L-thiazolidine-4-formic acid and thionyl chloride, adding the thiazolidine formyl chloride to N-trimethyl chitosan to obtain the O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt. The O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt is greatly improved in term of antibacterial property in contrast with the chitosan, and thus can be applied to various fields such as antibacterial materials, chemical products of daily use and industrial wastewater treatment.

Description

technical field [0001] The invention belongs to the field of polymer compound materials, and in particular relates to a chitosan chemically modified functional derivative O-thiazolidine methyl ester-N-trimethyl chitosan quaternary ammonium salt and a preparation method and application thereof. Background technique [0002] With the development of society and the advancement of science and technology, people pay more and more attention to antibacterial materials. There are three main types of antibacterial agents commonly used in daily life: inorganic metal mineral materials, organic heterocyclic antibacterial materials and natural antibacterial materials. Because natural antibacterial preservatives come from nature, are highly safe to the human body, and meet the requirements of green environmental protection, they have been welcomed by people in recent years. The research, development and utilization of natural antibacterial agents have become a hot spot in applied chemistr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A01P1/00
Inventor 杨仁党李知函杨文光
Owner SOUTH CHINA UNIV OF TECH
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