Chitosan hydrogel derivatives as a coating agent with broad spectrum of antimicrobial activities

Patent metadata

Field	Value
Publication number	US-9750847-B2
Application number	US-201514922369-A
Country	US
Kind code	B2
Filing date	Oct 26, 2015
Priority date	Jul 13, 2009
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

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.

First claim

What is claimed is:

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 C 1 -C 18 alkyl, m is 2 or 3, n is 1 to 20.

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

3. 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—CH 2 COO(C m H 2m O) n COCH═CH 2

wherein X is a halogen atom.

Assignees

• Univ Nanyang Tech

Inventors

• Bee Eng Mary Chan
• Yin Fun Poon
• Lamrani Mouad
• Hamaguchi Shinichi

Classifications

• C08J2305/08

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

• C08J3/075

  Macromolecular gels · CPC title

• C08J3/28

  Treatment by wave energy or particle radiation · CPC title

• A61L31/042

  Polysaccharides · CPC title

• A61L31/16

  Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)} · CPC title