Preparation of a 6-OH quaternized chitosan derivative through click reaction and its application to novel thermally induced/polyelectrolyte complex hydrogels

Colloids Surf B Biointerfaces. 2017 Oct 1;158:431-440. doi: 10.1016/j.colsurfb.2017.07.028. Epub 2017 Jul 11.


In the present study, a chitosan derivative with long chain quaternary ammonium locating grafted at 6-OH (CTS-6-QAS) was designed and prepared via a novel click reaction. The structure and thermal stability of the products of each step were determined with Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD) and thermogravimetric analysis (TGA). Rheological tests indicate that CTS-6-QAS possesses excellent thermally induced hydrogel formation property in the presence of β-glycerophosphate (β-GP). Based on these results, a novel thermally induced/polyelectrolyte complex CTS-6-QAS/alginate (SA)/β-GP dual-network hydrogel was designed. This controllable preparation method can avoid the disadvantages of the preparation methods for single thermo-induced hydrogels and polyelectrolyte complex hydrogels, and promote the homogeneity of the hydrogel. Porous sponges were prepared by freeze-drying the CTS-6-QASSA/β-GP hydrogels. The effects of hydrogel preparation conditions on the porous structure and swelling property of the sponges were quantitatively investigated. Tea tree oil (TTO), a natural antibacterial agent, was successfully embedded in the hydrogel due to the lipophilicity of the long chain quaternary ammonium grafted at 6-OH of chitosan. The sustained release of TTO from the hydrogel was studied.

Keywords: Click reaction; Dual-network hydrogel; Locating graft; Polyelectrolyte complex; Tea tree oil; Thermally induced.

MeSH terms

  • Chitosan / chemistry
  • Glycerophosphates / chemistry*
  • Hydrogels / chemistry*
  • Polyelectrolytes / chemistry
  • Spectroscopy, Fourier Transform Infrared / methods*
  • Tea Tree Oil / chemistry


  • Glycerophosphates
  • Hydrogels
  • Polyelectrolytes
  • Tea Tree Oil
  • Chitosan
  • beta-glycerophosphoric acid