New thermosetting materials were developed for reworkable adhesive applications by introducing acetal ester groups as thermally degradable linkages into maleimide compounds. The synthesis of compounds containing maleimide functionality and acetal ester linkages was conducted by a one-step neat reaction from commercially available materials. The polymerization process and thermal degradation of the synthesized materials were studied. It was found that the acetal ester linkage degraded rapidly above 225 degrees C, and introduction of this linkage into the adhesive formulation led to improved reworkability of adhesively bonded substrates. A mechanism for reworkability was proposed based on the insight provided by experimental and modeling work. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1073-1084,2009