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New Selectively N-Substituted Quaternary Ammonium Chitosan Derivatives

2000; Springer Nature; Volume: 32; Issue: 4 Linguagem: Inglês

10.1295/polymj.32.334

1349-0540

Kenji Suzuki, Daisuke Oda, T Shinobu, Hiroyuki Saimoto, Yoshihiro Shigemasa,

Advanced Cellulose Research Studies

New chitosan derivatives were synthesized by N-selective introduction of quaternary ammonium-type side chains without protection of hydroxy groups, although direct quaternization of the amino group of chitosan using alkyl halides under alkaline conditions introduced alkyl groups not only to the amino group but also to the hydroxy groups. The reductive N-alkylation reaction of chitosan with quaternary ammonium-type aldehydes, such as 4-formyl-N-methylpyridinium iodide and [3-(4-formylphenoxy)propyl]trimethylammonium iodide, followed by anion-exchange reaction gave partially N-p-(N-methylpyridinio)methylated chitosan chloride (N-MP[Cl-]) and partially N-4-[3-(trimethyl-ammonio)propoxy] benzylated chitosan chloride (N-TMPB [Cl-]), respectively. From the viewpoint of utilization as antistatic material for functional textile, the electric resistance of newly prepared derivatives were investigated. In comparison with known quaternary ammonium chitosan derivatives (Q-CDs), such as 96% deacetylated chitin hydrochloride (DAC-96·HCl), partially O-methyl-N-trimethylated chitosan chloride (O-Me-N-TM[Cl-]), and partially N, O-(2-hydroxy-3-trimethylammonio) propylated chitosan chloride (N, O-HTMP [Cl-]), N-MP [Cl-]) showed the lowest specific resistance (ρ). N-TMPB [Cl-] whose ρ was comparable with that of N-TM [Cl-] showed lower water content compared with known Q-CDs noted above. Newly prepared Q-CDs thus appear as promising biocompatible antistatic materials.