Synthesis and side‐chain crystallization of comb‐like polymers obtained from isopropenyl‐1,3,5‐triazines carrying two, three, and four long alkyl groups

Abstract

AbstractMonomers containing several octadecyl groups, e.g., 2‐isopropenyl‐4,6‐bis(octadecylamino)‐1,3,5‐triazine (2), 2‐dioctadecylamino‐4‐isopropenyl‐6‐octadecylamino‐1,3,5‐triazine (3) and 2,4‐bis(dioctadecylamino)‐6‐isopropenly‐1,3,5‐triazine (4) were prepared by the alkylation reaction of 2,4‐diamino‐6‐isopropenyl‐1,3,5‐triazine (1) with 1‐bromooctadecane in the presence of sodium hydride. In the free‐radical homopolymerization of these monomers, the polymer yield of 3 was lower than that of 2 due to a decrease in the ceiling temperature, and the polymerization of 4 did not proceed. Copolymerizations of these monomers with styrene or methyl methacrylate were carried out and the monomer reactivity ratios (r1 and r2) were determined. The monomer reactivity decreased with increasing the number of octadecyl groups in the monomers. Crystallinity of the octadecyl side chains in the resulting comb‐like polymers was evaluated by differential scanning calorimetry.