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Water-soluble chitosan derivatives as well as preparation method and uses thereof

A technology of water-soluble chitosan and derivatives, applied in medical science, prosthesis, etc., can solve the problems of intense reaction conditions, many reaction steps, and low yield, and achieve the effect of simple operation process and mild reaction conditions

Inactive Publication Date: 2008-07-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of these two methods are: although the unsaturated carbon-carbon double bond is introduced, the product cannot be water-soluble, and the reaction conditions are intense and harsh; although the polymerizable group and the water-soluble group are introduced through a two-step reaction, the reaction There are many steps, the product purification steps are cumbersome, and the yield is not high

Method used

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  • Water-soluble chitosan derivatives as well as preparation method and uses thereof
  • Water-soluble chitosan derivatives as well as preparation method and uses thereof
  • Water-soluble chitosan derivatives as well as preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Add 68.75g of acryloyl chloride dropwise to 500ml of toluene solution containing 76.88g of triethylamine and 89.88g of hydroxyethyl methacrylate, and react at 0-5°C. After 4 hours of reaction, the reaction is terminated , washed with 105 ml of water, 100 ml of 1M hydrochloric acid, and 100 ml of 1M NaOH aqueous solution to remove unreacted substances and by-products to obtain 90.01 g of acryloyloxyethyl methacrylate.

[0023] (2) At normal temperature, 6.0 g of chitosan raw material (viscosity-average molecular weight is 150,000, deacetylation degree is 85%) is dissolved in 200 ml of aqueous solution of 2.4 ml glacial acetic acid, then 200 ml of ethanol is added, stirred evenly, and then Add 5.64g of acryloyloxyethyl methacrylate and react at 50°C. After 48 hours of reaction, dialyze to remove unreacted substances and by-products, and freeze-dry to obtain methacryloyloxyethyl carboxyethyl shell Polysaccharide 5.2g, its structural formula is as follows:

[0024] ...

Embodiment 2

[0032] (1) Add 68.75g of acryloyl chloride dropwise to 500ml of toluene solution containing 76.88g of triethylamine and 89.88g of hydroxyethyl methacrylate, and react at 0-5°C. After 4 hours of reaction, the reaction is terminated , washed with 105 ml of water, 100 ml of 1M hydrochloric acid, and 100 ml of 1M NaOH aqueous solution to remove unreacted substances and by-products to obtain 90.01 g of acryloyloxyethyl methacrylate.

[0033] (2) At normal temperature, 6.0 g of chitosan raw material (viscosity-average molecular weight is 150,000, deacetylation degree is 85%) is dissolved in 200 ml of aqueous solution of 2.4 ml glacial acetic acid, then 200 ml of ethanol is added, stirred evenly, and then Add 11.28g of acryloyloxyethyl methacrylate and react at 50°C. After 48 hours of reaction, dialyze to remove unreacted substances and by-products, freeze-dry to obtain methacryloyloxyethyl carboxyethyl shell Polysaccharide 5.1g, its structural formula is as follows:

[0034]

[...

Embodiment 3

[0042](1) Add 68.75g of acryloyl chloride dropwise to 500ml of toluene solution containing 76.88g of triethylamine and 89.88g of hydroxyethyl methacrylate, and react at 0-5°C. After 4 hours of reaction, the reaction is terminated , washed with 105 ml of water, 100 ml of 1M hydrochloric acid, and 100 ml of 1M NaOH aqueous solution to remove unreacted substances and by-products to obtain 90.01 g of acryloyloxyethyl methacrylate.

[0043] (2) At normal temperature, 6.0 g of chitosan raw material (viscosity-average molecular weight is 150,000, deacetylation degree is 85%) is dissolved in 200 ml of aqueous solution of 2.4 ml glacial acetic acid, then 200 ml of ethanol is added, stirred evenly, and then Add 16.92g of acryloyloxyethyl methacrylate and react at 50°C. After 48 hours of reaction, dialyze to remove unreacted substances and by-products, freeze-dry to obtain methacryloyloxyethyl carboxyethyl shell Polysaccharide 5.1g, its structural formula is as follows:

[0044]

[0...

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Abstract

The invention relates to a water soluble chitosan derivative and the preparation method and application of the water soluble chitosan derivative. The water soluble chitosan derivative adopts the chitosan as raw material to synthesize substitutional derivatives on the chitosan -NH2 with the following structural formula (I). The preparation method is making the chitosan react with an ester with a methacrylic oxyl on one end and a propylene oxyl on the other end in the medium of water, acetic acid and ethanol, obtaining the chitosan derivative with both polymerized unsaturated carbon-carbon double bond and water solubility at the same time. The the preparation method for the water soluble chitosan derivative has the advantages of mild conditions, simple operation, natural and non toxic prepared chitosan derivatives, biodegradation and biocompatibility, and ability to be used as injectable hydrogel support and cartilage repair materials for tissue engineering scaffold material after further polymerization.

Description

technical field [0001] The invention relates to a water-soluble chitosan derivative and its preparation method and application. Background technique [0002] Chitosan is the only natural alkaline polysaccharide that exists in nature. It widely exists in the shells of crustaceans such as shrimps and crabs and the cell walls of various fungi. In nature, its annual biosynthesis capacity reaches more than 1 billion tons. It is an inexhaustible renewable resource. [0003] Chitosan has biodegradability and excellent biocompatibility, and is widely used in drug carriers and tissue engineering. Due to the strong hydrogen bond force between molecules and molecules, chitosan cannot be dissolved in water and common organic solvents, but can only be dissolved in acidic aqueous solution, and the molecular weight of chitosan can be reduced after being dissolved in acidic solution. And then greatly limit its wide application. This is one of its disadvantages. [0004] The hydrogel tis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61L27/20
Inventor 聂俊周应山杨冬芝高暄钥王沺
Owner BEIJING UNIV OF CHEM TECH
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