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Difunctional-group-modified chitosan derivative and preparation method thereof

A technology of chitosan derivatives and bifunctional groups, which is applied in the field of chitosan preparation, can solve the problems of reducing biological safety, affecting applications, and no obvious improvement in antibacterial properties, so as to avoid antibacterial function or biological safety Decrease, increase rapid penetration, improve the effect of water solubility

Active Publication Date: 2017-08-01
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these works all modify chitosan with a single functional group, which either improves the antibacterial properties of chitosan and reduces its biosafety, or improves the biosafety without significantly improving the antibacterial properties. It greatly affects its further application

Method used

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  • Difunctional-group-modified chitosan derivative and preparation method thereof
  • Difunctional-group-modified chitosan derivative and preparation method thereof
  • Difunctional-group-modified chitosan derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] A bifunctional group modified chitosan derivative, its molecular structure is shown below

[0049]

[0050] Among them, x, y, n are natural numbers, 07 , 07 , 10 2 ≦n≦10 7 .

[0051] The specific preparation method of the above chitosan derivative is as follows:

[0052] Weigh 0.1 g of chitosan and add it to 100 ml of deionized water, and stir it mechanically for half an hour at room temperature to dissolve the chitosan completely, thereby obtaining a uniform solution with a concentration of 0.1% by mass and volume; Slowly add thiourea trioxide to the system, the molar ratio of thiourea trioxide to chitosan is 10:1, the feeding time is 30 minutes, and the reaction is maintained at room temperature for 60 minutes; then the refined is activated in an ice-water mixed bath for 3 hours A mixed solution of acid, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) (solvent 30mmol / 20ml of 2-(N-morpholino)ethanesulfonic acid (MES) buf...

Embodiment 2

[0061] A bifunctional group modified chitosan derivative, its molecular structure is shown below

[0062]

[0063] Among them, x, y, n are natural numbers, 07 , 07 , 10 2 ≦n≦10 7 .

[0064] The specific preparation method of the above chitosan derivative is as follows:

[0065] Weigh 0.5 g of chitosan and add it to 100 ml of dilute hydrochloric acid with a concentration of 0.1 mol / L, and mechanically stir for half an hour at room temperature to dissolve the chitosan completely, thereby obtaining a uniform solution with a concentration of 0.5% by mass and volume; Next, slowly add thiourea trioxide to the dilute acid solution system of chitosan, the molar ratio of thiourea trioxide to chitosan is 5:1, the feeding time is 30 minutes, and the reaction is maintained at room temperature for 60 minutes; Arginine, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) activated for 3 hours in a mixed bath 20ml of mixed solution (the solvent is ...

Embodiment 3

[0067] A bifunctional group modified chitosan derivative, its molecular structure is shown below

[0068]

[0069] Among them, x, y, n are natural numbers, 07 , 07 , 10 2 ≦n≦10 7 .

[0070] The specific preparation method of the above chitosan derivative is as follows:

[0071] Weigh 1.0 g of chitosan and add it to 100 ml of dilute hydrochloric acid with a concentration of 0.1 mol / L, and stir it mechanically for one hour at 35°C in a water bath to dissolve the chitosan completely, thereby obtaining a concentration of 1% by mass and volume. Homogeneous solution; slowly add thiourea trioxide to the dilute acid solution system of chitosan in a 35℃ water bath. The molar ratio of thiourea trioxide to chitosan is 4:1. The feeding time is 40 minutes, and the reaction is maintained at room temperature for 50 minutes. ; Then arginine, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) activated at room temperature for 2 hours ·HCl) mixed solutio...

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Abstract

The invention discloses a difunctional-group-modified chitosan derivative and a preparation method thereof. The chitosan derivative has a molecular structural formula (I) shown as in the description. According to the preparation method, chitosan is reacted with thiourea trioxide and arginine, respectively, under a certain condition to obtain the difunctional-group-modified chitosan derivative. The difunctional-group-modified chitosan derivative is treated through a deionized water dialytic method to remove micromolecular by-products or impurities for sample purification. The dialyzed aqueous solution is dried through freeze drying to obtain the final product. Chitosan is subjected to difunctional modification, and guanidine radicals and arginine modify the molecular chain of chitosan at the same time, so that chitosan is endowed with excellent antibacterial property and better biological safety. The preparation method is mild in reaction condition and suitable for industrial production. The modified derivative is good in water solubility and greatly improved in antibacterial effect, is excellent in biological safety, is a high-quality natural polysaccharide-modified green antibacterial material, and has great development prospects in the market.

Description

Technical field [0001] The invention relates to the field of chitosan preparation. More specifically, it relates to a bifunctional group-modified chitosan derivative and a preparation method thereof. Background technique [0002] Chitin is a natural renewable resource with reserves second only to cellulose on the earth, and chitosan obtained by deacetylation of chitin is a polycationic alkaline polysaccharide. In addition to being non-toxic, non-immunogenic, and good In addition to biodegradability and biocompatibility, it also has anti-inflammatory effects that many polymer materials do not have and promotes the penetration and absorption of drugs on the surface of biofilms. Therefore, chitosan is used in medicine, food, and chemical industries. And environmental protection industries. However, due to the relatively stable chemical properties of chitosan, it is difficult to dissolve in water, which greatly limits its wide application in many of the above fields. [0003] The ch...

Claims

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Application Information

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IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 牛忠伟蒋士冬
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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