Electrochemical synthesis of chloro-chitosan

Patent metadata

Field	Value
Publication number	US-9518077-B2
Application number	US-201314374948-A
Country	US
Kind code	B2
Filing date	Feb 1, 2013
Priority date	Feb 3, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The present disclosure provides methods for producing chitosan derivatives and the derivatives formed by these methods. The processes of the present disclosure utilize electrochemical methods to functionalize and/or modify amine and/or hydroxyl groups present on chitosan, to form new derivatives. In embodiments, a chloro-chitosan derivative may be prepared. The altered cationic affinity of these derivatives make them excellent candidates for biomedical applications, including pharmaceuticals, as well as food applications.

First claim

What is claimed is:

1. A process comprising:
contacting chitosan with a solvent selected from the group consisting of water, alcohols and combinations thereof, with heating to a temperature from about 25° C. to about 70° C. to form a chitosan solution having chitosan present in an amount from about 1% to about 10% by weight of the solution;
adding to the chitosan solution an acid selected from the group consisting of hydrochloric acid, hypochlorous acid, and combinations thereof, to reduce the pH of the chitosan solution to a pH from about 1 to about 6;
applying a positive potential of from about 1.5 volts to about 50 volts to the chitosan solution by the introduction of a cathode and anode into the chitosan solution;
forming a chloro-chitosan as a froth in the chitosan solution; and
recovering the chloro-chitosan from the froth of the chitosan solution, wherein the chloro-chitosan includes a monomer of the following formula:

2. The process of claim 1 , wherein the chitosan solution is formed with mixing at a rate of from about 1 revolution per minute to about 1000 revolutions per minute.

3. The process of claim 1 , wherein the chitosan solution is formed over a period of time from about 1 minute to about 48 hours.

4. The process of claim 1 , further comprising contacting a drug with the chloro-chitosan to form a drug delivery device.

5. The process of claim 1 , further comprising contacting a polyethoxylated fatty acid ester of sorbitan with the chloro-chitosan to form a hydrogel.

Assignees

• Univ New York State Res Found

Inventors

• Halada Gary P
• Jha Prashant Kumar

Classifications

• A61L27/54

  Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)} · CPC title

• A61L2300/404

  Biocides, antimicrobial agents, antiseptic agents · CPC title

• C08L5/08 Primary

  Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof · CPC title

• A61K47/36

  Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin · CPC title

• C08J3/075

  Macromolecular gels · CPC title