7-Hydroxynadic Acid:  A New End Cap for Improved Oxidation Resistance in Addition Polyimides

We consider possible replacements for the norbornenyl end cap in addition polyimides that should favor bridge degradation and lead to lower weight loss in the resin system. Our preliminary evaluation demonstrates that molding powder made with 7-hydroxynorbornene-2,3-dicarboxylic acid, 17, as the end cap can be fully imidized at 200 °C. By differential scanning calorimetry (DSC), onset of cross-linking occurs approximately 50 °C lower than that for the unsubstituted end cap. The hydroxy-bearing carbon on 17 is more easily oxidized to carbonyl on aging in the polymer than the parent end cap. Therefore, the new end cap more highly favors bridge degradation. However, processing studies, long-term weight loss, and careful evaluation of degradation mechanisms must be carried out to fully assess 17 as a more thermo-oxidatively stable replacement for the parent norbornenyl end cap.