Synthesis of phenol formaldehyde-containing pendant itaconamic, itaconimide and poly[N-(substituted) itaconimides]

Ortho- and meta-aminophenols were allowed to react with itaconic anhydride, forming N-ortho- and N-meta-hydroxyphenyl itaconamic acids in good yields. The above substituted itaconamic acids were allowed to react with formaldehyde in conditions similar to those of Novolac preparation and novel phenol formaldehyde resins were obtained having pendant itaconamic acids. Similarly, formaldehyde was allowed to react with N-ortho- and N-meta-hydroxyphenyl itaconimides, producing novel resins. Furthermore, the itacon vinyls of the pendant groups of itaconamic acids as well as their corresponding imides were polymerized free radically using AIBN as an initiator and tough cross-linked resins were obtained.