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Chitosan quaternary ammonium salt containing triazole, and preparation method and application thereof

A technology of chitosan quaternary ammonium salt and triazole, which is applied in the field of marine chemical engineering, can solve the problems of expanding the use range of chitosan, poor water solubility, and affecting the use range of chitosan, and achieves antifungal activity and water solubility Improvement, biological activity improvement effect

Active Publication Date: 2014-10-08
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor water solubility of chitosan itself, the scope of use of chitosan has been seriously affected. Through chemical modification of chitosan, derivatives with better water solubility and good biological activity can be obtained, which can expand the use of chitosan. scope of use

Method used

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  • Chitosan quaternary ammonium salt containing triazole, and preparation method and application thereof
  • Chitosan quaternary ammonium salt containing triazole, and preparation method and application thereof
  • Chitosan quaternary ammonium salt containing triazole, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The triazole-containing chitosan quaternary ammonium salt is a compound represented by formula (1). At the same time, its preparation process is recorded as follows:

[0025]

[0026] The average value of n ranges from 20 to 3000; R is bromomethyl, phenyl or 1-hydroxyethyl.

[0027] In this example, the target compound a was synthesized according to the above synthetic route.

[0028] (1) Compounds 1-4 were synthesized by referring to the method in the literature (Ifuku, S., Wada, M., Morimoto, M., Saimoto, H. Preparation of highly regioselective chitosan derivatives via "click chemistry". Carbohydrate Polymers, 2011, 85, 653 –657).

[0029] (2) 0.72 g of the product (compound 4) obtained in step (1), 2.16 g of sodium iodide, 4 mL of sodium hydroxide solution (15%) and 4 mL of methyl iodide were added to 40 mL of N-methylpyrrolidone, and the temperature was raised to 60° C. Reaction for 1h. After the reaction, the reaction solution was poured into 100 mL of ethan...

Embodiment 2

[0035] In this example, the target compound b was synthesized according to the above synthetic route. The difference from Example 1 is that:

[0036] (1) 0.72 g of compound 4, 5.58 g of sodium iodide, 10 mL of sodium hydroxide solution (15%) and 10 mL of methyl iodide were added to 40 mL of N-methylpyrrolidone, and the temperature was raised to 40° C. to react for 3 h. After the reaction, the reaction solution was poured into 100 mL of ethanol, and a precipitate was deposited. The precipitate was filtered with suction, washed with ethanol, and 1.1 g of the product (compound 5) dried at 60° C. was used for later use.

[0037] (2) 0.54 g of compound 5, 14 mg of cuprous iodide, 4.1 mL of triethylamine and 0.49 mL of phenylacetylene were added to 45 mL of dimethyl sulfoxide, and the temperature was raised to 90° C. to react for 48 h. After the reaction, the reaction solution was suction filtered, and the filtrate was poured into 50 mL of ethanol to precipitate a precipitate. Th...

Embodiment 3

[0041] In this example, the target compound c was synthesized according to the above synthetic route. The difference from Example 1 is that:

[0042] (1) 0.72 g of compound 4, 0.74 g of sodium iodide, 1.4 mL of sodium hydroxide solution (15%) and 1.4 mL of methyl iodide were added to 40 mL of N-methylpyrrolidone, and the temperature was raised to 50° C. to react for 2 h. After the reaction, the reaction solution was poured into 100 mL of ethanol, and a precipitate was deposited. The precipitate was filtered with suction, washed with ethanol, and 1.1 g of the product (compound 5) dried at 60° C. was used for later use.

[0043] (2) 0.54 g of compound 5, 7 mg of cuprous iodide, 3.1 mL of triethylamine and 0.23 mL of 3-butyn-1-ol were added to 50 mL of dimethyl sulfoxide, and the temperature was raised to 80° C. to react for 60 h. After the reaction, the reaction solution was suction filtered, and the filtrate was poured into 50 mL of ethanol to precipitate a precipitate. The ...

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Abstract

The invention relates to the technical field of the marine chemical industry engineering, and concretely relates to a chitosan quaternary ammonium salt containing triazole, and a preparation method and an application thereof. The chitosan quaternary ammonium salt containing triazole is represented by formula (1); and in the general formula, the average value of n is 20-3000, and R is aliphatic hydrocarbon or aromatic hydrocarbon. The above substance obtained in the invention has good fungus inhibition activity, and can be widely used in the biological field, the medicinal field, the food field, the chemical industry field and the like.

Description

technical field [0001] The invention relates to the technical field of marine chemical engineering, in particular to a triazole-containing chitosan quaternary ammonium salt and a preparation method and application thereof. Background technique [0002] Chitosan is a kind of natural aminopolysaccharide with abundant sources, second only to cellulose yield in nature, with no toxic side effects, good biocompatibility and degradability, and its own and its derivatives have many With unique physiological and pharmacological properties, it is widely used in medicine, food, agriculture, daily chemicals, environmental protection and other industries. Chitosan itself has special structure and properties, has bactericidal and bacteriostatic activities, as well as non-toxic and non-polluting properties, and can be used as the object of modification in order to develop secondary lead compounds. Chitosan contains active -OH, -NH 2 , other active groups can be introduced on N or O, whic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A01P3/00
Inventor 郭占勇李青董方王刚
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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