One-Step Approach to Amino-Functionalized Semiaromatic Polyamides: Modification and Cross-Linking

The new method for the one-step synthesis of semiaromatic polyamides bearing primary aromatic amine groups in the repeating units is presented. Various aliphatic and aromatic diamines were used: 2,2′-(ethylene­dioxy)­bis­(ethylamine) (3a), Jeffamine ED-600 (3b), 4,4′-oxidianiline (3c), and p-phenylene­diamine (3d). They react with bis­(N-carboxy­anhydrides) of aromatic β-amino acid (N-unsubstituted bis­(benzoxazine-2,4-diones)) yielding the corresponding semiaromatic polyamides (4a–4c). The obtained free amino groups were modified with 2-isocyanatoethyl methacrylate. These methacryl-functionalized polyamides can be cross-linked in the presence of N,N-dimethyl­arylamide via free radical polymerization.