Synthesis of chitosan-based polymeric surfactants and their adsorption properties for heavy metals and fatty acids

Chitosan-based polymeric surfactants (CBPSs) were prepared by N-acylation of chitosans (chitosan 10 and 500) with several acid anhydrides such as hexanoic (C-6), lauric (C-12), and palmitic (C-16) anhydrides. Among the CBPS samples, CBPSs having a good solubility at pH 4.0 were selected and observed for viscosity, surface tension, and adsorption of heavy metals (Cd2+, Co2+, Cr2O72-, and Pb2+) as well as the fatty acid (n-octanoic acid). The H-1 NMR spectrum of chitosan 10 modified with C-16 at the substitution ratio of 0.4 (CBPS (10) - C-16,C-0.4) showed 85% of acylation in 1% DCl/D2O solutions. CBPS10 with the substitution ratio less than 0.4 showed a good solubility because of shorter repeating units and lesser amounts of hydrophobic substituents. The intrinsic viscosity of CBPS10 was slightly increased, while that of CBPS500 was decreased. As the substitution ratio and length of the carbon chain increased, the surface tension of CBPS10 tended to decrease. CBPS10 - C-16,C-0.2 had high adsorption ability for cationic metal ions such as Cd2+, Co2+, and Pb2+ comparable to chitosan. Interestingly, CBPS10 - C-16,C-0.2 showed a unique pH optimum for the anionic metal ion such as Cr2O72-. In addition, CBPS10 - C-16,C-0.2 exhibited the highest adsorption ability for n-octanoic acid among the tested CBPS 10 with different carbon chains. (c) 2005 Elsevier B.V. All rights reserved.