Synthesis and property evaluations of photocrosslinkable chitosan derivative and its photocopolymerization with poly(ethylene glycol)

Abstract

Photocrosslinkable polymers are clean and convenient materials for the biomedical uses. Chitosan, which owns excellent biocompatible and antimicrobial properties, is one of the choices while it is introduced with photosensitive functional groups. In this study, chitosan was N-phthaloylated to react with acryloyl chloride in the organic solvent homogeneously and the result has been verified by the solubility test. Fourier transformed infrared spectrometry and nuclear magnetic resonance spectrometer analysis indicated that the modification with the attachment of the photosensitive functional group, the acryloyl group, onto chitosan and poly(ethylene glycol) (PEG) was feasible. The differential scanning calorimetry analysis further indicated that the melting points of the N-phathaloylated chitosan were decreased as compared with the untreated chitosan control. Then photocrosslinkable chitosan derivative (CH-PAA) was photocopolymerized with PEG diacrylate (PEGA) under UV irradiation. The adhesion strength characterization and swelling capacity evaluation for this photocopolymer have shown obvious raises of the adhesiveness and water-adsorption abilities as compared with the photopolymer of CH-PAA.

Chemically modified light‐curable chitosans with enhanced potential for bone tissue repair

“…Because of its chemical structure, chitosan shows high biocompatibility leading to its being extensively applied in biomedical areas, for such uses as surgical sutures, dental implants, artificial skin, and so forth 9. In recent research, chitosan has been widely used as a scaffolding material for tissue engineering 15, 21–27. Many studies indicate that chitosan is suitable for orthopedic applications 1, 6, 11–14.…”

“…Many studies have indicated that chitosan is a good candidate for orthopedic applications 1, 6, 11–14. In cartilage tissue engineering, chitosan was shown to promote chondrocyte attachment and proliferation and maintain chondrogenic phenotype, which may be due to its structural similarity to various glycosaminoglycans (GAGs) found in articular cartilage 8, 11, 15, 16. Chitosan has also been extensively used in bone tissue engineering as it has been shown to facilitate growth and biomineralization by osteoblasts 14.…”

Photocrosslinkable chitosan hydrogels and their biomedical applications

“…Up to now, the most commonly used method to prepare photocrosslinkable CS is by grafting methacryloyl groups to CS molecular chain. For instance, Tsai et al prepared acryloyl CS (4 in Fig. ) by the reaction between N ‐phthaloylated CS and acryloyl chloride in the organic solvent homogeneously.…”

Preparation and properties of photo-crosslinkable hydrogel based on photopolymerizable chitosan derivative

“…Ma et al [8] prepared photopolymerizable chitosan derivative by chitosan and stearyl chloride in mixture of triethylamine and acetone. Moreover, Tsai et al [9] introduced acryloyl chloride into N-phthaloyl chitosan to obtain photosensitive chitosan derivative with unsaturated bond.…”