Polymer Bulletin, Vol.77, No.3, 1433-1448, 2020
Synthesis and radical copolymerization of novel propyl cyanoacrylate monomers
Novel phenyl-trisubstituted propyl 3-(R-phenyl)-2-cyanoacrylates (where R is 2,4,5-trimethyl, 2,4,6-trimethyl, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 4-hydoxy-3,5-dimethyl, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3,4,5-trimethoxy) were prepared using piperidine-catalyzed condensation of substituted benzoic aldehydes and propyl ester of cyanoacetic acid with good yields (72-97 wt%). The ethenylbenzene copolymerization of cyanoacrylates (at 3/1 mol feed ratio) in solution with radical initiation at 70 degrees C resulted in formation of copolymers having M-W 3.9 to 27.8 kD and 8.4-25.8 mol% of cyanoacrylate. FTIR, H-1 and C-13 NMR were used to analyze the structure. Thermal behavior of the copolymers was analyzed by DSC, T-g (81-129 degrees C) and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500 degrees C range with residue (0.5-7.3 wt%)and then in the 500-800 degrees C range.