# US 2014/0193476 A1 · Chitosan hydrogel derivatives as a coating agent with broad spectrum of antimicrobial activities

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- Number: US 2014/0193476 A1
- Document ID: US20140193476A1
- Status: Published application
- Kind: A1
- Application number: 14/209,602
- Filed: 2014-03-13
- Published: 2014-07-10
- Earliest claimed: 2012-03-15
- Assignees: Nanyang Technological University; Menicon Co., Ltd.
- Inventors: Chan Bee Eng Mary; Poon Yin Fun; Mouad Lamrani; Shinichi Hamaguchi
- Web page: https://patentgrep.com/patent/US20140193476A1

## 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 quaternized chitosan derivative having polymerizable organic moieties.

### Claim 2 (depends on 1)

The quaternized chitosan derivative of claim 1, having an ammonium group represented by the following formula:
—N+(R1)3
where each R1 is independently selected from the group consisting of hydrogen and a substituted or unsubstituted alkyl group, two or three of R1s may combine to form a substituted or unsubstituted aliphatic cyclic group.

### Claim 3 (depends on 2)

The quaternized chitosan derivative of claim 2, wherein at least one of R1 is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms.

### Claim 4 (depends on 1)

The quaternized chitosan derivative of claim 1, wherein the polymerizable organic moiety is represented by the following formula:
—Y—P
where P is a polymerizable group; Y is a spacer group.

### Claim 5 (depends on 2)

The quaternized chitosan derivative of claim 2, wherein said —N+(R1)3 group is —N+R′R″2 where R′ and R″ are independently selected from the group consisting of hydrogen and a substituted or unsubstituted alkyl group, provided that R′ has more carbon atoms than R″.

### Claim 6

A method of producing a quaternized chitosan derivative having polymerizable organic moieties, comprising a step of reacting a quaternized chitosan derivative and a halide having a polymerizable organic moiety.

### Claim 7 (depends on 6)

The method of claim 6, wherein said halide is represented by the following formula:
X—P1
where P1 is a polymerizable organic moiety; X is a halogen atom.

### Claim 8 (depends on 1)

A method of producing a chitosan hydrogel, comprising a step of polymerizing a polymerizable composition comprising said quaternized chitosan derivative of claim 1, initiator, and water.

### Claim 9 (depends on 1, 8)

A method of producing a chitosan hydrogel of claim 8, wherein said polymerizing step comprises a step of irradiating ultraviolet (UV) to a photopolymerizable composition comprising said quaternized chitosan derivative of claim 1, photoinitiator, and water.

### Claim 10 (depends on 8)

A hydrogel produced by the method of claim 8.

### Claim 11 (depends on 10)

A medical device having a coating comprising the hydrogel of claim 10.

### Claim 12 (depends on 10)

A contact lens having a coating comprising the hydrogel of claim 10.

### Claim 13 (depends on 10)

A medical device containing the hydrogel of claim 10.

### Claim 14 (depends on 10)

A cosmetic containing the hydrogel of claim 10.