Colorless poly(ester imide)s derived from hydrogenated trimellitic anhydride

Abstract

Tetracarboxylic dianhydrides were synthesized from hydrogenated trimellitic anhydride (HTA) and some diols to obtain novel poly(ester imide)s (PEsIs). The HTA-derived tetracarboxylic dianhydrides showed much higher reactivity with various diamines than conventional cycloaliphatic tetracarboxylic dianhydrides and led to PEsI precursors with high molecular weights (Mw). The results can be explained in terms of a spacer effect. The PEsI films were essentially colorless regardless of diol and diamine components owing to inhibited charge-transfer interactions. The HTA-derived PEsIs also exhibited excellent combined properties: relatively high glass transition temperatures (Tg), relatively low water absorption (WA), and relatively low dielectric constants. The outstanding processability (thermoplasticity and solubility) observed for the HTA-derived PEsIs was discussed on the basis of a non-planar/bent structure at the HTA-based imide units. The use of a fluorene-containing diol component was effective for enhancing Tg’s by restricted internal rotation and for reducing WA by a decreased imide group content. On the other hand, the use of 4,4′-biphenol as another diol gave rise to a prominent toughening effect without sacrificing other target properties. One of the HTA-derived PEsI systems can be a promising candidate as plastic substrates because of its excellent combined properties: a high Tg close to 300°C, high optical transparency, significant toughness (elongation at break>100%), and good thermo- and solution-processability.