Isomorphous replacement in nylon 6 by 4‐aminomethylcyclohexanecarboxylic acid

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Abstract
It was desired to determine the effect of geometric configuration on the ability of 4‐aminomethylcyclohexanecarboxylic acid (AMCC) to “isomorphously” replace ε‐aminocaproic acid residues in nylon 6. However, we found that cis‐AMCC isomerized to the more thermodynamically stable trans isomer during copolymerization with caprolactam (CL) and also during homopolymerization. A 20/80 cis/trans ratio of AMCC residues was found in the 50:50 copolyamides regardless of whether a high‐cis (72/28) or high‐trans (15/85) AMCC was used. Powder x‐ray diagrams showed similar interplanar spacings for the copolyamides made from both high‐cis and high‐trans AMCC. The x‐ray study also showed that the nylon 6 lattice can accommodate less than 30 mole‐% AMCC residues before a new structure appears. DTA and TGA data of the CL:AMCC copolyamide showed that AMCC raised the melting point, Tg, Tc, and stability of nylon 6.

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