Polyhydroxypolyamides

We have recently developed a synthetic procedure for the preparation of polyhydroxypolyamides (hydroxylated nylons) of general structure I (1-2). While our synthetic method has some unique... 

Polyhydroxypolyamides have attracted significant attention since they are more hydrophilic and biodegradable than nylons. Sugar amino acids [65] or aldaric acid... 

Scheme 21 Synthesis of polyhydroxypolyamides from gfucaric acid...

Given that D-glucose, produced on a massive scale worldwide by starch hydrolysis, is by far the most available and inexpensive aldose, the corresponding aldaric acid, D-glucaric acid, would appear to be the most attractive aldaric acid for commercial development. This report will focus on several potentially important aldaric acids, consider some of their applications as standalone chemicals, and describe how diey can be used as diacid monomers for the preparation of assorted polyamides, labeled polyhydroxypolyamides (PHPAs) or Hy oxylated Nylons. 

Our current major interest in aldaric acids is as monomers for polycondensation reactions with diamines to yield a broad class of polymers called polyhydroxypolyamides (PHPAs) or Hydroxylated Nylons (10). The original reports of examples of this class of polyamides were from the laboratory of N. Ogata and coworkers in Japan, beginning in the 1970s (11). More recent reports on these polymers have come from the laboratories of Hashimoto and coworkers (12) and those of author (13). Our general preparation of these polyamides, exemplified with a generic hexaric acid, is outlined in Figure 2. 

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