Photopolymerizable chitosan derivative as well as preparation method and application thereof

A chitosan derivative, photopolymerization technology, applied in the field of biopolymer materials, can solve the problems of difficult control of reaction conditions, complicated post-processing, long gel time, etc., and achieves environmental protection, good biocompatibility, simple steps

Active Publication Date: 2013-04-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is following shortcoming in the method for above-mentioned preparation hydrogel: 1, reaction condition is difficult to control
2. Toxic substances ar

Method used

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  • Photopolymerizable chitosan derivative as well as preparation method and application thereof
  • Photopolymerizable chitosan derivative as well as preparation method and application thereof
  • Photopolymerizable chitosan derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add chitosan (deacetylation degree DD=70%, weight average molecular weight Mw=50,000) into 2wt% acetic acid solution, stir at room temperature for 0.5h, and prepare 1% by weight chitosan solution. Adding methacryloylglycine, EDC and NHS added to 15mL deionized water with an amount of 2 times the amino molar number on the chitosan, the mol ratio of methacryloylglycine, EDC, NHS is 1: 2: 2, The carboxyl group was activated by magnetic stirring for 2 h. It was slowly added dropwise to the acetic acid solution of chitosan, and reacted at room temperature for 6h. Adjust the pH value to 8 with 1mol / L NaOH solution, dialyze with deionized water, and freeze-dry to obtain photopolymerizable chitosan derivatives. The product structure is as follows:

[0039]

[0040] Wherein, n=0.7, m=0.3, 0

[0041] Figure 1A with 1B The IR spectrum and H NMR spectrum of the product methacryloylglycyl chitosan are given respectively.

[0042] The prepared photopolymerizable chito...

Embodiment 2

[0044] Add chitosan (deacetylation degree DD=90%, weight average molecular weight Mw=100,000) into 2wt% acetic acid solution, stir at room temperature for 1 hour, and prepare chitosan solution with a weight percentage of 1%. Adding methacryloylglycine, EDC and NHS added to 15mL deionized water with an amount of 2 times the molar amino group on the chitosan, the mol ratio of methacryloylglycine, EDC, NHS is 1: 4: 4, The carboxyl group was activated by magnetic stirring for 2 h. It was slowly added dropwise to the acetic acid solution of chitosan, and reacted at room temperature for 8h. Adjust the pH value to 8 with 1mol / L NaOH solution, dialyze with deionized water, and freeze-dry to obtain photopolymerizable chitosan derivatives. The product structure is as follows:

[0045]

[0046] Wherein, n=0.9, m=0.1, 0

[0047] The prepared photopolymerizable chitosan derivative is dissolved in 2wt% acetic acid solution to form a solution of 85% by weight, adding 1% of photopo...

Embodiment 3

[0049] Add chitosan (deacetylation degree DD=80%, weight average molecular weight Mw=50,000) into 2wt% acetic acid solution, stir at room temperature for 2h, and prepare 2wt% chitosan solution. Adding methacryloylglycine, EDC and NHS added to 15 mL of deionized water with an amount of 1 times the molar amino group on chitosan, the mol ratio of methacryloylglycine, EDC, NHS is 3: 2: 2, The carboxyl group was activated by magnetic stirring for 3 h. It was slowly added dropwise to the acetic acid solution of chitosan, and reacted at room temperature for 8h. Adjust the pH value to 8 with 1mol / L NaOH solution, dialyze with deionized water, and freeze-dry to obtain photopolymerizable chitosan derivatives. The product structure is as follows:

[0050]

[0051] Wherein, n=0.8, m=0.2, 0

[0052] The prepared photopolymerizable chitosan derivative is dissolved in 2wt% acetic acid solution to form a solution of 80% by weight, and 2% of the photopolymerizable chitosan derivat...

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PUM

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Abstract

The invention discloses a photopolymerizable chitosan derivative. The derivative is prepared by adding an activated mixed solution of methacrylamide carboxylic acid or acrylamide carboxylic acid, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) into an acetic acid solution of chitosan dropwise, reacting at room temperature, regulating the pH value to 8, dialyzing with deionized water and lyophilizing. The derivative remains the original bioactivity and biocompatibility of chitosan, and introduces a new photopolymerizable group, can be polymerized through initiation of an initiator 2959 under ultraviolet radiation, and has the advantages of mild reaction condition, simple steps, easiness for control and environmentally-friendly post-treatment; and the prepared hydrogel has the advantages of low toxicity and excellent biocompatibility.

Description

technical field [0001] The invention relates to a biopolymer material, in particular to a photopolymerizable chitosan derivative; the invention also relates to a preparation method of the derivative and its application in hydrogel preparation. Background technique [0002] Chitin widely exists in the shells of insects, marine invertebrates, and fungal cells. It is the second largest natural biopolymer in nature after cellulose. Chitosan is a deacetylated derivative of chitin. The only natural active polysaccharide with cations in nature, has good biocompatibility, biodegradability, non-toxic antibacterial and non-immunogenicity, etc. It is widely used in cosmetics, tissue printing and dyeing, agriculture, food industry, tissue engineering, burns, etc. It is widely used in dressings and drug carriers. [0003] There are hydroxyl groups and amino groups in the molecular structure of chitosan, which can form intramolecular and intermolecular hydrogen bonds, making chitosan ins...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08J3/24C08J3/075C08F122/38C08F2/48
Inventor 马贵平聂俊徐娟朱晓群
Owner BEIJING UNIV OF CHEM TECH
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