Monday, May 19, 2008 - 10:40 AM
Library Building, Rm LB-6 (Queensborough Community College)
167

Mother NATURE as a Source of NEW Materials: EVERYTHING Old IS NEW Again

James A. Moore, Rensselaer Polytechnic Institute, Troy, NY

In July, 1969 we began a preparing monomers from cellulose. Polymers were prepared by the standard methods of acid-catalyzed polyesterification and interfacial polycondensation of diacid chorides. The polymers were characterized using Infrared, and NMR Spectroscopy. Molecular weights were assessed by viscosity and gpc.

Cellulose can be hydrolysed to glucose which can be oxidized to glucaric acid. Elimination of water and cyclization yields 2,5-furan dicarboxylic acid (2,5-FDA). We have mostly used interfacial polycondensation of the acid chlorides of the various isomers of FDA (2,5; 2,4; 2,4; 3,4) as a route to polyesters and polyamides. Polymers with intrinsic viscosities in the range of 0.1 � 0.7 dl/g could be prepared. Nonactin, a macrocyclic tetraester acts by binding potassium ions and disrupting synaptic signal transmission.A casual examination of this molecule led us to try to generate a helical polymeric analog? We tested the general idea by making reduced derivatives of 2,5-FDA We also made polymers derived from the lactone and the analogous lactam from tetrahydro-2-hydroxymethyl-5 furoic acid and they exhibit varying degrees of ion binding ability.

The major hydrolytic degradation product of cellulose is levulinic acid which can be condensed with phenol to yield a bis-phenol called diphenolic acid which can be protected as a t-butyl ester The ester allowed us to prepare a variety of homo- and copolycarbonates in which, after selective removal of the t-butyl group, the carboxyl group can be used as a site for further modification.