A kind of chitosan bispyridine quaternary ammonium salt and its preparation method and application

A technology of double quaternary ammonium salt and chitosan, applied in the field of daily chemicals, can solve the problems of affecting the use range of chitosan, poor water solubility, etc., and achieve the effects of good antioxidant activity, low cost, and weakening of hydrogen bonds.

Active Publication Date: 2018-01-23
烟台美嘉全生物科技有限公司
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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 can be obtained to expand the scope of use of chitosan

Method used

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  • A kind of chitosan bispyridine quaternary ammonium salt and its preparation method and application
  • A kind of chitosan bispyridine quaternary ammonium salt and its preparation method and application
  • A kind of chitosan bispyridine quaternary ammonium salt and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Chitosan diquaternary ammonium salt is a compound shown in formula 1, formula 2 and formula 3.

[0021] Preparation of chitosan diquaternary ammonium salt: 1.61g chitosan was dissolved in 50mL volume ratio of 2% acetic acid solution, after dissolving chitosan was added to 30mmol2-pyridineformaldehyde and 3-pyridine dissolved in 10mL absolute ethanol respectively Formaldehyde or 4-pyridine formaldehyde, continue to stir at room temperature for 2h, after stirring, add 45mmol sodium borohydride dropwise at a rate of 2mL per minute, stir for 2h, pour into excess acetone after stirring, precipitate, suction filter, dry at 60°C, grind , to obtain solid powders of N-substituted chitosan derivatives, respectively. Take 0.5g of the solid powder obtained in the previous step and disperse them in 30mL of N-methyl-2-pyrrolidone, stir at room temperature for 12h, add 0.1mL of 1M sodium hydroxide solution, 0.75g of sodium iodide and 4mL of methyl iodide, stir at 50°C for 20h, and rea...

Embodiment 2

[0024] The difference from Example 1 is:

[0025] Preparation of chitosan diquaternary ammonium derivatives: 1.61g chitosan was dissolved in 50mL volume ratio of 2% acetic acid solution. Or in 4-pyridine formaldehyde, continue to stir at room temperature for 1.5h, after stirring, add 45mmol sodium borohydride dropwise at a rate of 2mL per minute, stir for 2h, pour into excess acetone after stirring, precipitate, filter with suction, and dry at 60°C. Grinding to obtain solid powders of N-substituted chitosan derivatives respectively. Take 0.5 g of the solid powder obtained in the previous step and disperse them in 30 mL of N-methyl-2-pyrrolidone, stir at room temperature for 12 h, add 0.1 mL of 1M sodium hydroxide solution, 0.75 g of sodium iodide, and 4 mL of methyl iodide, stir at 50 ° C for 20 h, and react Pour into excess acetone, precipitate, filter with suction, wash with acetone for 3 times, and dry at 60°C to obtain the chitosan diquaternary ammonium salt derivative sh...

Embodiment 3

[0027] 1.61g chitosan was dissolved in 50mL volume ratio of 2% acetic acid solution, after dissolving chitosan was added to 30mmol 2-pyridine formaldehyde, 3-pyridine formaldehyde or 4-pyridine formaldehyde dissolved in absolute ethanol respectively, and stirring was continued at room temperature 2h, after stirring, add 45mmol sodium borohydride dropwise at a rate of 2mL per minute, stir for 2h, pour into excess acetone after stirring, precipitate, filter with suction, dry at 60°C, and grind to obtain N-substituted chitosan derivatives respectively of solid powder. Disperse 0.5 g of the solid powder obtained in the previous step into 30 mL of N-methyl-2-pyrrolidone, stir at room temperature for 6 h, add 0.1 mL of 1M sodium hydroxide solution, 0.75 g of sodium iodide, and 4 mL of methyl iodide, stir at 50 °C for 20 h, and react Pour into excess acetone, precipitate, filter with suction, wash with acetone for 3 times, and dry at 60°C to obtain the chitosan diquaternary ammonium ...

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Abstract

The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a preparation method and application of a chitosan diquaternary ammonium salt derivative. Chitosan diquaternary ammonium derivatives are qcts2Py, qcts3Py or qcts4Py shown in formula (1), (2) or (3); with chitosan as raw material, the corresponding pyridine aldehydes are synthesized to generate corresponding Schiff base, and then reduced by sodium borohydride to obtain N-substituted chitosan, and then reacted with methyl iodide to obtain biquaternary ammonium chitosan derivatives. Compared with the chitosan raw material, the shown biquaternary ammonium salt derivative has good antioxidant activity. The present invention has synthesized chitosan diquaternary ammonium salt derivatives through effective synthetic means, and water solubility is better, and antioxidant activity is significantly improved, has strengthened the biological activity of chitosan, expanded the application scope of chitosan, can Used in daily chemical and pharmaceutical industries and other fields.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a preparation method and application of a chitosan diquaternary ammonium salt derivative. Background technique [0002] Chitosan (Chitosan) is a kind of natural amino polysaccharide with rich sources, second only to cellulose in nature, renewable, non-toxic and side effects, good biocompatibility and degradability. It itself and its derivatives have many With unique physiological and pharmacological functional properties, it is widely used in various industries such as medicine, food, agriculture, daily chemicals, and environmental protection. Chitosan itself has a special structure and properties, has bactericidal, antibacterial activity, and non-toxic, non-polluting characteristics, it can be used as the object of modification in order to develop secondary lead compounds. Active groups on chitosan molecules include hydroxyl and amino groups, which...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
Inventor 董方郭占勇李青王刚李琬聪胡云霞周婷婷
Owner 烟台美嘉全生物科技有限公司
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