title: Hydrophobically modified chitosan: a bio-based material for antimicrobial active film.
abstract: The objective of the present research was to improve the hydrophobicity of chitosan, while retaining its antibacterial activity, through the grafting of dodecenyl succinyl chains onto phthaloyl chitosan, mainly at the C-6 position. Dodecenyl succinylated phthaloyl chitosan (DS-g-PHCTS) was synthesized via phthaloylation-dodecenyl succinylation-hydrazinolysis. The obtained derivatives were characterized by FTIR, (1)H NMR and XRD. Hydrazinolysis time was found to be a key factor in controlling the substitution of dodecenyl succinyl chains and phthalimido groups of the final product. DS-g-PHCTS - with a grafting degree of dodecenyl succinyl chains and a substitution degree of phthalimido groups of 0.73 and 0.39, respectively - exhibited an anhydrous crystal structure and the same solubility behavior as native chitosan. The introduction of hydrophobic alkyl chains provided DS-g-PHCTS with enhanced antibacterial activity against Gram-positive bacteria. In addition, DS-g-PHCTS film showed more effective bacterial growth inhibition and better water vapor barrier property under neutral pH condition than chitosan film. The results suggested that DS-g-PHCTS film could be potentially used as antibacterial active film.
authors: Department of Packaging and Materials Technology, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand.
authors: Orathai
authors: O
authors: Inta
authors: Department of Packaging and Materials Technology, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand; Center for Advanced Studies in Nanotechnology and its Applications in Chemical, Food and Agricultural Industries, Kasetsart University, Bangkok 10900, Thailand. Electronic address: rangrong.y@ku.ac.th.
authors: Rangrong
authors: R
authors: Yoksan
authors: Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand; NANOTEC Center of Excellence, National Nanotechnology Center, Kasetsart University, and Center of Nanotechnology, Kasetsart University Research and Development Institute, Bangkok 10900, Thailand.
authors: Jumras
authors: J
authors: Limtrakul
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001672:Biocompatible Materials / Q000737:chemistry* / Q000494:pharmacology; D048271:Chitosan / Q000737:chemistry* / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D010795:Phthalic Acids; D012995:Solubility; D055672:Static Electricity; D013227:Steam
chemical_list: D000900:Anti-Bacterial Agents; D001672:Biocompatible Materials; D010795:Phthalic Acids; D013227:Steam; C032279:phthalic acid; D048271:Chitosan
keywords: Antibacterial film; Bio-based material; Chitosan; Hydrophobically modified chitosan; Phthaloylation; Succinylation