Preparation method of O-carboxymethyl chitosan

A technology of carboxymethyl chitosan and chitosan, which is applied in the field of preparation of O-carboxymethyl chitosan, can solve the problems of being susceptible to temperature fluctuations, and achieves accelerated wound healing, good adsorption effect, and strong load capacity. Effect

Inactive Publication Date: 2015-11-25
JIANGSU SHUANGLIN MARINE BIOLOGICAL PHARM CO LTD
View PDF0 Cites 15 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is the preparation of O-carboxymethyl chitosan, and domestic reports are more to adopt at lower temperature to react with chloroacetic acid in alkaline medium to introduce carboxymethyl into the O-position of chitosan, but There will still be a small amount of N-position carboxymethyl chitosan product under the above reaction conditions, especially in order to obtain a product with a higher degree of substitution or when the reaction time is longer, the appearance of the N-position product will be more obvious, and the reaction process will be susceptible to temperature fluctuations

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of O-carboxymethyl chitosan
  • Preparation method of O-carboxymethyl chitosan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] (1) Chitosan C 2 Protection of amino groups: Accurately weigh 3.0g of CTS and dissolve in 240ml of 1% acetic acid solution, dissolve completely at 25°C and slowly add 180ml of methanol. Accurately weigh 3.0g benzaldehyde and dissolve it in 45ml methanol, mix evenly and add dropwise, heat up to 60°C and stir for 4h. Slowly add 240ml of 5% NaOH solution and 60ml of methanol, and continue stirring for 8h. After the reaction, the precipitate was filtered by suction, washed with 95% ethanol and dehydrated with absolute ethanol to remove unreacted benzaldehyde, and dried at 55°C. Respond many times to accumulate the product for later use.

[0013] (2) Carboxymethyl reaction: Take 5.0 g of chitosan after the above reaction (passed through a 60-mesh sieve) and suspend it in 50 ml of isopropanol, and swell at 55° C. for 5 hours. Cool to 25°C, and slowly add 25ml of 20% NaOH solution dropwise with stirring at a rate of 3 s / d. After the dropwise addition, continue stirring for...

Embodiment 2

[0016] (1) Chitosan C 2 Protection of amino groups: Accurately weigh 3.0g of CTS and dissolve in 240ml of 1% acetic acid solution, dissolve completely at 25°C and slowly add 180ml of methanol. Accurately weigh 3.0g benzaldehyde and dissolve it in 45ml methanol, mix evenly and add dropwise, heat up to 60°C and stir for 4h. Slowly add 240ml of 5% NaOH solution and 60ml of methanol, and continue stirring for 8h. After the reaction, the precipitate was filtered by suction, washed with 95% ethanol and dehydrated with absolute ethanol to remove unreacted benzaldehyde, and dried at 55°C. Respond many times to accumulate the product for later use.

[0017] (2) Carboxymethyl reaction: Take 5.0 g of chitosan after the above reaction (passed through a 60-mesh sieve) and suspend it in 50 ml of isopropanol, and swell at 55° C. for 5 hours. Cool to 25°C, slowly add 25ml of 25% NaOH solution dropwise with stirring at a rate of 3 s / d. After the dropwise addition, continue stirring for 1 h...

Embodiment 3

[0020] (1) Chitosan C 2 Protection of amino groups: Accurately weigh 3.0g of CTS and dissolve in 240ml of 1% acetic acid solution, dissolve completely at 25°C and slowly add 180ml of methanol. Accurately weigh 3.0g benzaldehyde and dissolve it in 45ml methanol, mix evenly and add dropwise, heat up to 60°C and stir for 4h. Slowly add 240ml of 5% NaOH solution and 60ml of methanol, and continue stirring for 8h. After the reaction, the precipitate was filtered by suction, washed with 95% ethanol and dehydrated with absolute ethanol to remove unreacted benzaldehyde, and dried at 55°C. Respond many times to accumulate the product for later use.

[0021] (2) Carboxymethyl reaction: Take 5.0 g of chitosan after the above reaction (passed through a 60-mesh sieve) and suspend it in 50 ml of isopropanol, and swell at 55° C. for 5 hours. Cool to 25°C, slowly add 25ml of 25% NaOH solution dropwise with stirring at a rate of 3 s / d. After the dropwise addition, continue stirring for 1 h...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a preparation method of single-C6-site selectively-substituted O-carboxymethyl chitosan. The preparation method comprises the following steps: 1) reacting a raw material chitosan to generate benzaldehyde-modified carboxymethyl chitosan, wherein an imine structure generated by the reaction between benzaldehyde and amino Schiff base is utilized to protect the amino group on the chain; 2) carrying out carboxymethyl reaction on the reaction product and chloroacetic acid under alkaline conditions by using isopropanol as a medium to generate benzaldehyde-modified O-carboxymethyl chitosan; and 3) immersing the benzaldehyde-modified O-carboxymethyl chitosan under acidic conditions for 48 hours to remove benzaldehyde, thereby generating the single-C6-site selectively-substituted O-carboxymethyl chitosan. Compared with the N,O-carboxymethyl chitosan and N-carboxymethyl chitosan, the prepared O-carboxymethyl chitosan contains both amino and carboxy groups, and thus, has better procoagulant activity, biodegradability and bacteriostatic action. The O-carboxymethyl chitosan can accelerate injury healing and effectively prevent tissue adhesion and scar formation. The O-carboxymethyl chitosan has favorable adsorbing effects on acid ions and proteins, can be connected with multiple biological active substances, has high loading capacity for heavy metal ions, and is widely used in the fields of food, medicine, chemical industry and the like.

Description

technical field [0001] The present invention relates to a kind of preparation method of O-carboxymethyl chitosan, relate in particular to a kind of single C 6 Preparation method of position-selectively substituted O-carboxymethyl chitosan. Background technique [0002] Carboxymethyl chitosan is a water-soluble chitosan derivative, which has gradually gained popularity in the medical field because of its good water solubility, film-forming properties, moisturizing properties, biocompatibility, non-toxicity and biodegradability. Pay attention to. Since there are 2 hydroxyl groups in the molecular structure of chitosan (C 3 bit and C 6 position) and 1 amino group (C 2 position) carboxymethylation can occur at all three positions. Therefore, the products are N, O-CMC, N-CMC and O-CMC. O-CMC is a biodegradable positive polysaccharide containing both active amino groups and carboxyl groups. It can be connected with a variety of biologically active substances in medicine, gre...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
Inventor 张军孙进姜红玲侯惠民贺芬马列李博
Owner JIANGSU SHUANGLIN MARINE BIOLOGICAL PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap