Chitosan modification via nitroxide-mediated polymerization and grafting to approach in homogeneous media. (12th June 2015)

• Record Type: Journal Article
• Authors: García-Valdez, Omar; George, Sean; Champagne-Hartley, Rachel; Saldívar-Guerra, Enrique; Champagne, Pascale; Cunningham, Michael F.
• Is Part Of: Polymer. Volume 67(2015)
• Page Start: 139
• Page End: 147
• Publication Date: 2015-06-12
• Subjects: Chitosan -- Chemical modification -- Nitroxide mediated polymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2015.04.043
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: A novel and facile strategy to modify chitosan (CTS) with a wide catalog of well-defined molecular weight graft hydrophilic and hydrophobic polymers and copolymers via nitroxide-mediated polymerization (NMP) in homogeneous media is reported. This strategy involves three steps: functionalization of CTS with glycidyl methacrylate (GMA) and sodium dodecylbenzenesulfonate (SDBS) to yield CTS-SDBS- g -GMA, which is soluble in organic media; synthesis of SG1-terminated polymers including poly(styrene) (PS), poly(butyl acrylate) (PBA), poly(acrylic acid) (PAA), poly(styrene-b-acrylic acid) (PS- b -PAA), and poly(styrene-r-acrylic acid) (PS-r-PAA) via SG1-based nitroxide-mediated polymerization; and grafting of the SG1-functionalized polymers or copolymers to CTS-SDBS- g -GMA. Following polymerization, the SDBS was removed from the new CTS-based materials. NMR, TGA, and FT-IR were used to confirm the synthesis of CTS-SDBS-g-GMA, CTS-SDBS- g -GMA-PS, CTS-SDBS -g -GMA-PBA, CTS-SDBS- g -GMA-PAA, CTS-SDBS- g -GMA-PS- b -PAA, and CTS-SDBS- g -GMA-PS- r -PAA. The SDBS was then fully removed from the new CTS-based graft copolymers. New CTS-based materials could find potential applications in fields such as biomedical, water and wastewater treatment, biopharmaceutics and agriculture. Graphical abstract: Highlights: A 3-step strategy was developed to graft chitosan with well controlled polymers. Chitosan was first functionalized with GMA as a source of double bonds. Chitosan-GMA was further functionalized with SDBS to solubilize it in DMSO. Well controlled SG1-end capped polymers were grafted to chitosan-GMA-SDBS. The strategy is robust and versatile and is performed in homogeneous media in DMSO.