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Polymerizable chitosan derivative and preparation method thereof

A chitosan derivative, chitosan technology, applied in the field of chitosan modification, can solve problems such as limiting the application range of chitosan, and achieve the effects of broadening the modification range, easy control, and mild reaction conditions

Inactive Publication Date: 2014-10-08
ZHANGJIAGANG SHANMU NEW MATERIAL TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are hydroxyl groups and amino groups in the molecular structure of chitosan, which can form intramolecular and intermolecular hydrogen bonds, making chitosan insoluble in neutral, alkaline and general organic solvents, and only soluble in some dilute acid solutions such as acetic acid and hydrochloric acid. , which greatly limits the scope of application of chitosan

Method used

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  • Polymerizable chitosan derivative and preparation method thereof
  • Polymerizable chitosan derivative and preparation method thereof
  • Polymerizable chitosan derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Mix benzaldehyde and methanol at a volume ratio of 4% to obtain solution A; dissolve 2-amino-4-pentenoic acid in water to obtain a 4wt% aqueous solution, then add 80 mL of methanol and stir to obtain solution B; The molar ratio of benzaldehyde in solution B to 2-amino-4-pentenoic acid in solution B is 2: 1. Add solution A dropwise to solution B, stir while adding, and react at a constant temperature of 60°C after the addition is completed. 24h, rotary evaporated to precipitate, washed repeatedly with deionized water and methanol for 3 times, and dried at 60°C to obtain intermediate product a; chitosan with a weight average molecular weight of 3000 and a deacetylation degree of 90% was added to 1 wt% aqueous acetic acid , stirred at room temperature for 2h until chitosan was completely dissolved to obtain solution C; intermediate product a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) was Added to solution C at a ratio of 1:3 and stirred at room temp...

Embodiment 2

[0025] Mix benzaldehyde and methanol at a volume ratio of 3% to obtain solution A; dissolve 2-amino-4-pentenoic acid in water to obtain a 5wt% aqueous solution, then add 60 mL of methanol and stir to obtain solution B; The molar ratio of benzaldehyde and 2-amino-4-pentenoic acid in solution B is 3:2, add solution A dropwise to solution B, stir while adding, and react at a constant temperature of 60°C after dropping 24h, rotary evaporated to precipitate, washed repeatedly with deionized water and methanol for 3 times, and dried at 60°C to obtain intermediate product a; chitosan with a weight average molecular weight of 12000 and a deacetylation degree of 80% was added with 1 wt% aqueous acetic acid , stirred at room temperature for 3h until chitosan was completely dissolved to obtain solution C; intermediate product a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) was Ratio 2: 3 was added to solution C and stirred at room temperature for 4 h, wherein the amo...

Embodiment 3

[0027] Mix benzaldehyde and methanol at a volume ratio of 5% to obtain solution A; dissolve 2-amino-4-pentenoic acid in water to obtain a 5wt% aqueous solution, then add 70mL of methanol and stir to obtain solution B; The molar ratio of benzaldehyde and 2-amino-4-pentenoic acid in solution B is 3:1, add solution A dropwise to solution B, stir while adding, and react at a constant temperature of 60°C after the addition is completed 24h, rotary evaporated to precipitate, washed repeatedly with deionized water and methanol for 3 times, and dried at 60°C to obtain intermediate product a; chitosan with a weight average molecular weight of 50,000 and a deacetylation degree of 85% was added to 2wt% acetic acid aqueous solution , stirred at room temperature for 3h until chitosan was completely dissolved to obtain solution C; intermediate product a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) was Added to solution C at a ratio of 2:1 and stirred at room temperatur...

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Abstract

The invention discloses a polymerizable chitosan derivative and a preparation method thereof. According to the invention, benzaldehyde is used for protecting the amino group of 2-amino-4-pentenoic acid, and the material is subjected to a reaction with the amino group on chitosan; when the reaction is finished, hydrochloric acid is used for deprotection, such that the polymerizable chitosan derivative is prepared. According to the invention, a double bond group which can be subjected to further polymerization reaction is introduced into chitosan molecular chain, such that the original biological activity and biocompatibility of chitosan are maintained in the obtained polymerizable chitosan derivative. During the preparation process, reaction conditions are mild, and the process is easy to control. According to the invention, a new chitosan derivative is provided, and chitosan modification range is expanded.

Description

technical field [0001] The invention relates to the field of chitosan modification, in particular to a polymerizable chitosan derivative, and also relates to a preparation method of the derivative. Background technique [0002] Chitosan is a deacetylated derivative of chitin. It is the only natural active polysaccharide with cations in nature. It has good biocompatibility, biodegradability, non-toxic antibacterial and non-immunogenicity. It is widely used in cosmetics, tissue printing and dyeing, agriculture, food industry, tissue engineering, burn dressing, drug carrier, etc. There are hydroxyl groups and amino groups in the molecular structure of chitosan, which can form intramolecular and intermolecular hydrogen bonds, making chitosan insoluble in neutral, alkaline and general organic solvents, and only soluble in some dilute acid solutions such as acetic acid and hydrochloric acid. , which greatly limits the scope of application of chitosan. However, because chitosan h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
Inventor 顾钰霞
Owner ZHANGJIAGANG SHANMU NEW MATERIAL TECH DEV
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