Synthesis and Characterization of new Monomers and Polymers Containing Hindered Piperidine Groups

Abstract

Two new methacryloyl ureas, 1-(2-methylacryloyl)-3-(2,2,6,6-tetra-methylpiperidin-4-yl)-urea and 1-butyl-3-(2-methylacryloyl)-1-(2,2,6,6-tetramethylpiperidin-4-yl)-urea (monomer I and monomer II), were prepared by the addition reaction of 2-methylacryloyl iso-cyanate with 2,2,6,6-tetramethylpiperidin-4-yl-amine or butyl-(2,2,6,6-tetramethylpiperidin-4-yl)-amine in a molar ratio of 1:1 at low or room temperature. In a similar way, the syntheses of two new methacryloyl carbamates, 1-(2,2,6,6-tetra-methylpiperidin-4-yl)-3-(2-methylacryloyl)-carbamate and l-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-3-(2-methylacryloyl)-carbamate (monomer III and monomer IV), were completed by the reaction of 2,2,6,6-tetra-methylpiperidin-4-ol or 1,2,2,6,6-pentamethylpiperidin-4-ol with 2-methylacryloyl isocyanate in the presence of dibutyltin dilaurate as catalyst at 60°C. The four new monomers were homopolymerized, and copolymerized with styrene by AIBN as initiator at 70°C. The structures of the new monomers and their polymers were characterized by FT-IR and NMR spectroscopy and by GPC.