# US 9,750,847 B2 · Chitosan hydrogel derivatives as a coating agent with broad spectrum of antimicrobial activities

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- Number: US 9,750,847 B2
- Document ID: US9750847B2
- Status: Granted
- Kind: B2
- Application number: 14/922,369
- Filed: 2015-10-26
- Published: 2016-02-11
- Granted: 2017-09-05
- Earliest claimed: 2014-03-13
- Assignees: Nanyang Technological University
- Applicants: Nanyang Technological University
- Inventors: Chan Bee Eng Mary; Poon Yin Fun; Mouad Lamrani; Shinichi Hamaguchi
- Web page: https://patentgrep.com/patent/US9750847B2

## CPC

- A61L 27/34: Macromolecular materials
- A61K 8/042: {Gels}
- A61K 8/736: {Chitin; Chitosan; Derivatives thereof}
- A61L 27/20: Polysaccharides
- A61L 27/52: Hydrogels or hydrocolloids
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 29/043: {Polysaccharides}
- A61L 29/085: {Macromolecular materials}
- A61L 29/145: {Hydrogels or hydrocolloids}
- A61L 31/042: {Polysaccharides}
- A61L 31/10: Macromolecular materials
- A61L 31/145: {Hydrogels or hydrocolloids}
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61Q 19/00: Preparations for care of the skin
- 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}
- C08F 290/10: Polymers provided for in subclass C08B
- C08G 81/00: Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42})
- C08J 3/075: Macromolecular gels
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 3/28: Treatment by wave energy or particle radiation
- G02B 1/043: {Contact lenses}
- A61L 2300/232: Monosaccharides, disaccharides, polysaccharides, lipopolysaccharides
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- C08J 2305/08: Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
- 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)
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

The present invention relates to water soluble quaternized chitosan derivatives which form hydrogel matrix with broad antimicrobial properties for the protection and coating of medical device. Hydrogel is attractive as an antimicrobial coating since its hydrophilicity intrinsically prevents the reversible nonspecific attachment of microbes. In order to achieve hydrogel formation, quaternized chitosan can be grafted with polymerizable groups, especially photocrosslinkable groups, such as methacrylates, PEG derivatives and be converted into hydrogels through a thermal or UV polymerization process. Hydrogels are hydrated cross-linked polymeric systems that contain water in an equilibrium state forming cushion water shield. The present invention is widely used in many medical devices. This invention describes the formation of novel hydrogels based on quaternized ammonium chitosan derivatives which has been grafted with photocrosslinkable groups, hence providing hydrogels as antimicrobial water shield coating agent.

## Claims

### Claim 1

A method of producing a chitosan hydrogel, comprising a step of polymerizing a polymerizable composition comprising a quaternized chitosan derivative having polymerizable organic moieties, initiator, and water,
wherein said polymerizing comprises a step of irradiating ultraviolet (UV) to a photopolymerizable composition comprising a quaternized chitosan derivative having polymerizable organic moieties, photoinitiator, and water,
wherein said quaternized chitosan derivative has the following formula,
wherein R′ and R″ are independently selected from the group consisting of optionally substituted C1-C18 alkyl, m is 2 or 3, n is 1 to 20.

### Claim 2 (depends on 1)

The method of claim 1, wherein R′ has more carbon atoms than R″.

### Claim 3 (depends on 1)

The method of claim 1, wherein said quaternized chitosan derivative is produced by a method comprising a step of reacting a quaternized chitosan derivative and a halide represented by the following formula:
X—CH2COO(CmH2mO)nCOCH═CH2
wherein X is a halogen atom.