Poly(glycidyl amine) and copolymers with glycidol and glycidyl amine repeating units: Synthesis and characterization

摘要

The synthesis and characterization of poly(glycidol-co-glycidyl amine), poly(glycidol)-block-poly(glycidyl amine), and poly(glycidol) end-capped with a glycidyl amine unit is reported. Copolymerization of ethoxyethyl glycidyl ether with epichlorohydrin using tetraoctylammonium bromide/triisobutylaluminium as catalyst leads to statistical or block copolymers. Sequential addition of the monomers to the initiator leads to block copolymers while simultaneous copolymerization of the monomers results in statistical copolymers. The resulting polyethers with protected hydroxymethyl and chloromethyl side groups were converted in three steps to poly(epoxide)s with hydroxymethyl and aminomethyl side chains. These polymers have a high potential for the preparation of multifunctional polymers since amine and alcohol groups can be addressed selectively by electrophiles. An intermediate in the synthesis of these functional poly(epoxide)s are polyethers with hydroxymethyl and azidomethyl side chains. The azide group of these copolymers was further functionalized via a click reaction with propargyl alcohol proving the reactivity of the polymer bound azide group. Furthermore, preparation of poly(glycidol)s bearing a glycidyl amine end group is reported.