Synthesis of an acid-labile diacrylate crosslinker for cleavable michael addition networks

A novel acid-cleavable diacrylate crosslinker, DCDA, was used as a difunctional Michael acceptor in the synthesis of acid-cleavable crosslinked networks via base-catalyzed Michael addition of telechelic poly(ethylene glycol) bis(acetoacetate). Michael addition networks containing DCDA were degraded in the presence of catalytic quantities of acids to form soluble polymeric products. Michael addition networks of non-degradable diacrylate crosslinkers were chemically unchanged under identical reaction conditions and remained insoluble. Thermal degradation of DCDA-containing networks was also investigated using TGA, which confirmed the thermal reactivity and concentration of the acid-labile crosslink points.