9(10)‐Carboxyoctadecylamine and 9(10)‐aminomethyloctadecanoic acid: Synthesis and polymerization to polyamides with lateral substitution

Abstract 9(10)‐Carboxyoctadecylamine (I) and 9(10)‐aminomethyloctadecanoic acid (II) have been prepared from selectively hydroformylated oleonitrile and oleic acid, respectively. Polymerization of I gave a transparent hard, somewhat brittle, polyamide, whereas polymerization of II gave a soft, rubbery polymer that flowed slowly at room temperature. Copolymers of I with II had properties reflecting those of the component homopolymers, although II exercised a disproportionate softening effect. The same was generally true of copolymers of I or II with nylon‐66 salt, caprolactam, and 9‐aminononanoic acid. The copolymer of I with 25 mole % nylon‐66 salt was transparent, was also elastic, and could be either drawn into fibers or made into a coherent film. The properties of the two amino acids and of their polymers agreed with those expected from simpler alkyl‐substituted amino acids.