The newly designed methacrylic monomer series 4-phthalimidocyclohexyl methacrylate (PCMA), 4-hexahydrophthalimidocyclohexyl methacrylate (HPCMA) and 4-hexahydro-3,6-methanophthalimidocyclohexyl methacrylate (HMPCMA) were synthesized. Their homopolymers and methyl methacrylate (MMA) based copolymer series were polymerized by free-radical polymerization. The copolymer compositions were characterized using 1 H NMR spectra. The monomer reactivity ratios were calculated employing the Fineman−Ross (F-T) and Kelen−Tüdös (K-T) methods at low conversion. The values of r 1 and r 2 obtained by the F-T and K-T methods appear to be in close agreement (their average values are r 1 = 1.3061 and r 2 = 0.7336 for poly(PCMA-co-MMA), r 1 = 1.5169 and r 2 = 0.6840 for poly(HPCMA-co-MMA), r 1 = 1.7748 and r 2 = 0.5664 for poly(HMPCMA-co-MMA)) . The thermal stabilities and thermomechanical characteristics of the homopolymer and copolymer series were investigated by differential scanning calorimetry, thermogravimetric analysis and dynamic mechanical thermal analysis.