Reactive poly(2-vinyl-4,4-dimethyl-5-oxazolone) and poly[(2-vinyl-4,4-dimethyl-5-oxazolone)-co-(methyl methacrylate)]s. Synthesis, characterization and chemical modification with 4-methoxy-4'-(β-aminoethoxy)biphenyl

Abstract

Poly(2-vinyl-4,4-dimethyl-5-oxazolone) (P0) and poly[(2-vinyl-4,4-dimethyl-5-oxazolone)-co-(methyl methacrylate)]s with increasing content of methyl methacrylate units (P1–P4) were synthesized and characterized. NMR spectra were discussed in terms of monomer sequence distribution and tacticity effects. The reaction of 4-methoxy-4′-hydroxybiphenyl (1) with 2-ethyl-2-oxazoline was utilized to prepare 4-methoxy-4′-(β-aminoethoxy)biphenyl (3) through the intermediate 4-methoxy-4′-[(N-propanoyl)-β-aminoethoxy]biphenyl (2). The homopolymer P0 and two copolymers P2 and P3 were functionalized with 4-methoxybiphenyl side groups by reaction with 3 via a ring-opening process in N,N-dimethylformamide (DMF) or 1,2-dichloroethane. The resulting copolymers P5–P8 were characterized by 1H and 13C NMR. The highest degree of functionalized units was obtained in DMF at 80°C.