Nylon 6,6 is a versatile engineering thermoplastic with high strength, stiffness and thermal stability. These properties make it widely applicable in the automotive, electronics, and food packaging industries, amongst others. However, despite its widespread use, Nylon 6,6 is moisture-sensitive which results in undesirable softening, dimensional instability and susceptibility to corrosive environments. Therefore, there are unmet needs for hydrophobic variants of Nylon 6,6. Due to the great interest in green alternatives to petroleum-based polymers, here, we present a value opportunity for “bioenabled” polymers that can be derived from biologically-produced intermediates such as muconic acid. In this study, we demonstrate the introduction of mono-unsaturated trans-3 hexenedioic acid (t3-HDA) as a platform that provides unique advantages in differentiating Nylon 6,6 through copolymerization. Specifically, a new family of hydrophobic “BioAdvantaged” Nylon 6,6 (BAN-H) have been prepared from mixtures of alkyl-chain-derivatized trans-3 hexenedioic acid, adipic acid (AA) and hexamethylendiamine (HMDA). The resultant BAN-H polyamides were fully tested for moisture absorption and characterized using a broad set of techniques including TGA, DSC, WAXS, DMA, and SEM. Our results illustrate the utility of unsaturation sites in polymer property customization by demonstrating a reduction in hygroscopicity by up to 93% without deleterious effects on the thermal and mechanical properties. Moreover, the chemical stability of BAN-H against aggressive corrosive agents such as zinc chloride is dramatically improved (Figure 1).

Bioadvantaged hydrophobic nylon-6,6 copolymers

2019 Spring National Meeting

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