Toward Intrinsically Flame-Retardant, Bioenabled Nitrogen Aromatic Nylon 6,6 Comonomers

Abstract

Muconic acid and its hydrogenation product trans-3-hexenedioic acid (t3HDA) are promising diacid monomers for inserting property enhancements as functionalities into nylon 6,6. A present challenge is related to low reaction yields and the high sophistication of syntheses. A green, atom-economical functionalization reaction that minimizes processing steps is desired. In this work base catalyzed isomerization was used to produce trans-2-hexenedioic acid (t2HDA) under mild conditions, and graft nitrogen based aromatic thiols to t2HDA via Michael addition in gamma-Valerolactone (GVL). The grafted monomers were co-polymerized with adipic acid and hexamethylenediamine (HMDA), and the flame-retardant properties of the synthesized polyamides screened to identify promising nitrogen-containing aromatics to afford improvements in end use performance without compromising on the polyamide’s properties.This is a manuscript of an article published as Hadel, Joseph, Sohaima Noreen, Marco Nazareno Dell’anna, Dhananjay Dileep, Brent H. Shanks, Jean-Philippe Tessonnier, and Eric W. Cochran. "Toward Intrinsically Flame-Retardant, Bioenabled Nitrogen Aromatic Nylon 6, 6 Comonomers." In Sustainable Green Chemistry in Polymer Research. Volume 2. Sustainable Polymers and Applications, pp. 163-176. American Chemical Society, 2023. doi:10.1021/bk-2023-1451.ch008. Posted with Permission. Copyright © 2023American Chemical Societ