# US 9,518,077 B2 · Electrochemical synthesis of chloro-chitosan

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- Number: US 9,518,077 B2
- Document ID: US9518077B2
- Status: Granted
- Kind: B2
- Application number: 14/374,948
- Filed: 2013-02-01
- Published: 2015-01-08
- Granted: 2016-12-13
- Earliest claimed: 2012-02-03
- Assignees: The Research Foundation for The State University of New York
- Applicants: The Research Foundation for the State University of New York
- Inventors: Gary P. Halada; Prashant Kumar Jha
- Web page: https://patentgrep.com/patent/US9518077B2

## CPC

- C07H 5/00: Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- A61L 27/20: Polysaccharides
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61P 31/04: Antibacterial agents
- C05C 11/00: Other nitrogenous fertilisers
- C08B 37/003: {Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof}
- C08J 3/075: Macromolecular gels
- C08L 5/08: Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
- C25B 3/07: Oxygen containing compounds
- C25B 3/09: Nitrogen containing compounds
- C25B 3/23: Oxidation (halogenation C25B3/27)
- A61K 47/36: Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- C08J 2305/08: Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C05C: NITROGENOUS FERTILISERS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## 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.

## Claims

### Claim 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:

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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