Synthesis and free-radical polymerization of triazinylstyrene derivatives

Reaction of 2,4-dichloro-6-p-vinylphenyl-1,3,5-triazine with nucleophilic reagents such as diethylamine, ethanol, diethyleneglycol monomethylether, and ethanthiol in the presence of a base in THF gave the corresponding substituted compounds in moderate to high yields. The resulting monomers, which have two functional groups, polymerized readily in the presence of AIBN at 60 degrees C to afford the corresponding homopolymers. The copolymerization parameters of each monomer were calculated from their copolymerization with styrene. Q values of these monomers were larger than that of styrene, indicating participation of the triazine ring to resonance of the monomers. On the other hand, e values of these monomers were approximately zero because of the electron-withdrawing character of the triazinyl group.