Synthesis and structure-activity study of quaternary ammonium functionalized beta-cyclodextrin-carboxymethylcellulose polymers

Water Sci Technol. 2011;63(12):2827-32. doi: 10.2166/wst.2011.630.

Abstract

Carboxymethylcellulose (CMC) and beta-cyclodextrin (beta-CD)-based polymers functionalized with two types of quaternary ammonium compounds (QACs), the alkaquat DMB-451 (N-alkyl (50% C14, 40% C12, 10% C10) dimethylbenzylammonium chloride) (DMD-451) named polymer DMB-451, and FMB 1210-8 (a blend of 32 w% N-alkyl (50% C14, 40% C12, 10% C10) dimethylbenzylammonium chloride and 48 w% of didecyldimethylammonium chloride) named polymer FMB 1210-8, were synthethized and characterized by Fourier transform infrared spectroscopy. The antimicrobial activities of these polymers against Eschericia coli were also evaluated at 25 degrees C in wastewater. The results have indicated that the polymer FMB 1210-8 possesses a high-affinity binding with bacterial cells that induces a rapid disinfection process. Moreover, in the same experimental conditions of disinfection (mixture of 1.0 g of polymer and 100 mL of wastewater), the polymer FMB 1210-8 has a higher antimicrobial efficiency (99.90%) than polymer DMB-451 (92.8%). This phenomenon might be associated to a stronger interaction with bacterial cells due to stronger binding affinity for E. coli cells and greater killing efficiency of the C10 alkyl chains QAC of polymer FMB 1210-8 to disrupt the bacterial cell membrane as compared to N-alkyl (50% C14, 40% C12, 10% C10) dimethylbenzylammonium chloride. Together, these results suggest that the polymer FMB 1210-8 could constitute a good disinfectant against Escherichia coli, which could be advantageously used in wastewater treatments due to the low toxicity of beta-CD and CMC, and moderated toxicity of FMB 1210-8 to human and environment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxymethylcellulose Sodium / chemistry*
  • Disinfectants / chemical synthesis*
  • Disinfectants / chemistry
  • Disinfectants / pharmacology
  • Escherichia coli / drug effects
  • Escherichia coli / growth & development
  • Filtration
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Polymers / pharmacology
  • Quaternary Ammonium Compounds / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • Structure-Activity Relationship
  • Water Purification / methods*
  • beta-Cyclodextrins / chemistry*

Substances

  • Disinfectants
  • Polymers
  • Quaternary Ammonium Compounds
  • beta-Cyclodextrins
  • betadex
  • Carboxymethylcellulose Sodium