Synthesis and Characterization of New Stereoregular AABB-Type Polyamides from Carbohydrate-based Monomers Having d-manno and l-ido Configurations

Polycondensation of 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra- O -methyl- d -mannitol or 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra- O -methyl- l -iditol with aromatic and aliphatic dicarboxylic acids has been used to prepare a series of regio- and stereoregular AABB-type polyamides. We also describe the preparation of 1,6-diamino-1,6-dideoxy-3,4- O -isopropylidene- d -mannitol and 1,6-diamino-1,6-dideoxy-2,5-di- O -methyl-3,4- O -isopropylidene- d -mannitol and their polycondensation reactions with the same dicarboxylic acids. The obtained polyamides were gummy solids that were optically active and had a pronounced affinity for water, although most of them were not soluble in this solvent. These polyamides were characterized by viscosimetry, gel-permeation chromatography, elemental analysis, and IR and NMR spectroscopies.