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

Abstract

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.

A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di‐O‐methyl‐L‐tartaryl chloride with diamines

“…There were two methods of polycondensation of dicarboxylic acid chloride with diamine: solution polycondensation and interfacial polycondersation. Owing to the rapid hydrolysis of the aliphatic dicarboxylic acid dichloride and premature precipitation of the polymers, high‐viscosity polyamides were rarely obtained using the interfacial polycondensation method,9 and therefore, the solution polycondensation method was used to prepare polyamides in this work (Scheme ). The structures of the obtained polyamides were verified by FTIR, 1 H‐NMR, and 13 C‐NMR spectroscopies.…”

“…When compared with Refs. 9 and 16, solution polycondensation of di‐ O ‐methyl‐ L ‐tartaryl chloride with diamines to prepare optically active polyamides does not need activation of the diamines and is characterized with shorter reaction time.…”

“…Some optically active polyamides can be used as chiral membrane separation materials or chiral stationary phases for high performance liquid chromatography because of the chiral recognition ability 2–6. In recent years, the use of carbohydrate derivatives to prepare polyamides has received much attention, and the interest arises not only from the naturally occurring character of the feedstock but also from the potential that such polymers are used for biodegradable and biocompatible materials in the biomedical field 7–12…”

Advances in synthetic optically active condensation polymers - A review

“…It was shown that these can be transformed into water-soluble polyacids upon saponification of ester side groups. PAs derived from carbohydrates are the object of current attention, because they are not only optically active, but also for its potential as biodegradable and biocompatible materials [72][73][74][75][76][77]. Mallakpour and coworkers [78][79][80] have investigated the synthesis of PAs from the polycondensation reaction of chiral 5-(4-methyl-2-phthalimidylpentanoylamino)isophthalic acid, (2S)-5-(3-phenyl-2-phthalimidylpro-panoylamino)iso-phthalic acid and 5-(3-methyl-2-phthalimidylpentanoylamino) isophthalic acid with several aromatic and aliphatic diisocyanates such as 4,4!-diphenylmethane diisocyanate (MDI), toluylene-2,4-diisocyanate (TDI), isophorone diisocyanate (IPDI) and hexamethylene diisocyanate (HDI) under microwave irradiation as well as conventional technique (Figure 2).…”

Synthesis and Characterization of Novel Biodegradable Polyamides Containingα-amino Acid

“…In recent years, sustained efforts have been devoted to rendering polyamides more degradable, to extend their applications to new fields demanding materials with lower environmental impact or displaying biodegradable and biocompatible properties (2).…”