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Water-soluble chitosan antibacterial derivative and preparation method thereof

A water-soluble chitosan, chitosan technology, applied in the directions of botanical equipment and methods, chemicals for biological control, biocides, etc. Functionalization and other issues to achieve the effect of ensuring antibacterial and antibacterial properties, ensuring biosafety, and enhancing water solubility

Active Publication Date: 2019-03-19
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, whether it is the hydrophilic modification of chitosan or the positive charge modification, these works only perform a single function on chitosan, which improves the antibacterial properties of chitosan and reduces its biological safety; or improves the antibacterial properties of chitosan. Biosafety without significant improvement in antibacterial properties, which seriously affects its further application

Method used

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  • Water-soluble chitosan antibacterial derivative and preparation method thereof
  • Water-soluble chitosan antibacterial derivative and preparation method thereof
  • Water-soluble chitosan antibacterial derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Preparation of polyethylene glycol modified chitosan

[0041] Weigh 0.16 grams of molecular weight 2×10 5 Chitosan with a Da deacetylation degree of 99% was added to 10mL MES buffer (25mM, pH=4.90), and 0.1mL HCl was dropped into 0.1mL HCl and stirred at room temperature for half an hour to completely dissolve the chitosan, thereby obtaining a mass volume percentage concentration of 1.6% homogeneous solution; then 20 mL of a mixed solution of carboxypolyethylene glycol monomethyl ether, NHS and EDC HCl activated at room temperature for 1 hour (the solvent is MES buffer solution of 25 mM pH=4.90) was added to the above reaction solution , keep stirring and reacting at room temperature for 24 hours, wherein the ratio of the amount of chitosan, carboxypolyethylene glycol monomethyl ether, NHS, EDC·HCl is 1:1:2:2; Polyethylene glycol monomethyl ether and other substances such as hydroxylamine hydrochloride terminate the reaction, and then the reaction solution is trans...

Embodiment 2

[0045] (1) Preparation of polyethylene glycol modified chitosan

[0046] Weigh 0.10 grams of molecular weight 10 6 Chitosan with a Da deacetylation degree of 80% was added to 100mL MES buffer (10mM pH=7.50), and 0.4mL CH 3 COOH was stirred at room temperature for half an hour to completely dissolve chitosan, thereby obtaining a homogeneous solution with a mass volume percentage concentration of 0.1%; then carboxypolyethylene glycol monomethyl ether, NHS and Add 20mL of EDC·HCl mixed solution (10mM solvent, MES buffer solution with pH=7.50) into the above reaction solution, and continue to stir and react at 0°C for 72 hours, wherein chitosan, carboxypolyethylene glycol monomethyl ether, The ratio of the amount of substances of NHS and EDC·HCl is 20:2:1:1; after the reaction is completed, add hydroxylamine hydrochloride with the amount of carboxypolyethylene glycol monomethyl ether and other substances to terminate the reaction, and then transfer the reaction solution to the in...

Embodiment 3

[0050] (1) Preparation of polyethylene glycol modified chitosan

[0051] Weigh 5.00 grams of chitosan with a molecular weight of 1000Da and a degree of deacetylation of 50% and add it to 10mL of MES buffer (100mMpH=4.50), and stir at room temperature for half an hour to completely dissolve the chitosan, thereby obtaining a concentration of 50% by mass volume. Homogeneous solution; then 50mL of a mixed solution of carboxypolyethylene glycol monomethyl ether, NHS and EDC HCl activated at 35°C for 0.5 hours (the solvent is MES buffer solution of 100mM pH=4.50) was added to the above reaction solution, and Continue to stir and react at 35°C for 12 hours, wherein the ratio of the amount of chitosan, carboxypolyethylene glycol monomethyl ether, NHS, EDC·HCl is 1:10:5:5; Hydroxylamine hydrochloride in the amount of ethylene glycol monomethyl ether and other substances terminates the reaction, and then the reaction solution is transferred to a dialysis bag with a molecular weight cut-...

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Abstract

The invention discloses a water-soluble chitosan antibacterial derivative and a preparation method thereof. The water-soluble chitosan antibacterial derivative comprises a chitosan framework and a bifunctional group for modifying amino on the chitosan framework, wherein the bifunctional group comprises guanidino and carbonyl methoxy polyethylene glycol. The side chain of chitosan is modified withguanidino and short-chain polyethylene glycol, and the chitosan achieves good antibacterial property and higher biological safety. According to the preparation method, firstly, the chitosan reacts with the carbonyl methoxy polyethylene glycol, water solubility of the chitosan is sufficiently improved, and biological safety is greatly improved; secondly, the chitosan reacts with thiourea trioxide,participation of the amino in subsequent reaction is effectively avoided if the guanidino is grafted in the first step, rich positive charge of the guanidino is effectively retained, and the positivecharge density of the water-soluble chitosan antibacterial derivative is ensured, so that the antibacterial effect of the water-soluble chitosan antibacterial derivative is better.

Description

technical field [0001] The invention relates to the field of antibacterial materials, in particular to a water-soluble chitosan antibacterial derivative and a preparation method thereof. Background technique [0002] Chitin is the second most abundant natural renewable resource in nature and can be isolated from the exoskeletons of arthropods, fungi, insects and annelids. Chitin is deacetylated until it can be dissolved in dilute acid solution to become a transparent aqueous solution, and the polymer at this time is chitosan. Compared with chitin, a large number of free amino groups endow chitosan with relatively high solubility and low crystallinity, thereby improving its application space to a certain extent. In addition, in addition to good biodegradability and biocompatibility, chitosan also has certain anti-inflammatory and promotes the penetration and absorption of drugs on the surface of biofilms, so it can be widely used in medicine, food, chemical industry, etc. a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A01N47/44A01P1/00A01P3/00
CPCA01N47/44C08B37/003
Inventor 牛忠伟朱萌蒋士冬
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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