((DIETHYLAMINO)ETHYL)CHITINS - PREPARATION AND PROPERTIES OF NOVEL AMINATED CHITIN DERIVATIVES

Procedures for (diethylamino)ethylation of chitin with (diethylamino)ethyl chloride have been established. ((Diethylamino)ethyl)chitins (DEAE-chitins) were prepared in dispersion in organic solvents with a small amount of aqueous sodium hydroxide. Among the solvents examined, dimethyl sulfoxide was confirmed to be most suitable, and degrees of substitution above 1.2 were achieved. The substitution reactions in solution in aqueous sodium hydroxide also proceeded smoothly, and DEAE-chitins with substitution degrees above 1.4 were obtained. Addition of a phase-transfer catalyst to the aqueous solution enhanced the reaction efficiency considerably. The resulting DEAE-chitins exhibited highly improved affinity to water and organic solvents, and these properties were dependent on both the mode of preparation and substitution extent. The derivatives prepared in aqueous solution showed much better solubility and swelling; they were readily water soluble and swelled remarkably in common solvents such as benzene and alcohols. The separation behavior of these DEAE-chitins for organic dyes was studied, and those with high substitution degrees proved useful as adsorbents and separating materials. © 1990, American Chemical Society. All rights reserved.