Synthesis of poly (hydroxyurethane) by ring-opening polyaddition offive-membered cyclic carbonate and α-methyl amines at room temperature using bicyclic guanidine catalyst

Abstract

The ring-opening polyaddition between 5-membered cyclic carbonate and polyetheramine with α-methyl group at room temperature using 1,5,7-triazabicyclo [4.4.0] deca-5-ene (TBD) as catalyst was investigated. The reaction of monofunctional 5-membered cyclic carbonate with bifunctional polyetheramine having α-methyl groups proceeded via ring-opening addition to form polyether bearing hydroxyurethane moiety at room temperature by the addition of 30 mol% of TBD. Based on the model reaction, polyaddition with a bifunctional five-membered cyclic carbonate was performed to oligomers with a M_n of about 6900 g/mol. Furthermore, networked polymers bearing hydroxyurethane linkage were synthesized by the polyaddition of bifunctional five-membered cyclic carbonate with trifunctional polyetheramine with α-methyl groups.