To make polymethacrylates such as PMMA inherently recyclable degradable monomer units need to be incorporated in a precise manner. Under industrially relevant conditions this implies a radical polymerization route such as rROP. In the present work, we have demonstrated that these degradable units can be DOT-based, provided that an auxiliary monomer is used such as MA or PhMal. Supported by CMMC modeling, the most promising results are obtained using PhMal-based terpolymerization, with also is characterized by the most reliable reactivity ratios.