Heterobifunctional Poly(Ethylene Oxide): Synthesis of α-Methoxy-ω-Amino and α-Hydroxy-ω-Amino PEOs with the Same Molecular Weights

Well-defined a-methoxy-ω-amino and α-hydroxy-ω-amino poly(ethylene oxide)s (PEOs) were obtained after chemical modifications of α-hydroxy-ω-allyl PEO which was synthesized by anionic polymerization of ethylene oxide (EO) with allyl alcoholate as initiator; molecular weights of the prepolymer were controlled by the monomer/initiator ratio. Addition of methyl iodide on the hydroxy function of this prepolymer led to an α-methoxy-ω-allyl PEO; completion of the reaction and purity of the resulting polymer were demonstrated by, ¹H ¹³C NMR and GPC studies. Addition reactions of 2-aminoethanethiol hydrochloride on α-hydroxy-ω-allyl PEO and α-methoxy-ω-allyl PEO in the presence of azobisisobutyronitrile (AIBN) led to the expected homopolymers without any side reactions as shown by and ¹H ¹³C NMR spectra.