Amphiphilic building blocks as head groups in linear polymers

Starting with asymmetric A,A′-carbonate couplers A1–A4 via substitution reaction with primary amines at low temperatures (0–25 °C) followed by addition reaction with primary amines at higher temperatures (60–80 °C), bis(functional) compounds with a free hydroxyl group were prepared. These compounds were used: (i) as initiators for ring-opening polymerization of ε-caprolactone; (ii) as substrate for the preparation of an ATRP initiator for MMA polymerization; (iii) as substrate for the preparation of an activated carbonate for grafting of an amine end-functionalized linear polymer (Jeffamine® M1000). Via modifications (i)–(iii), amphiphilic end-functionalized poly(ε-caprolactone)s, poly(methyl methacrylate)s, and polyethers were prepared, respectively.

Graphical abstractStarting with asymmetric A,A′-carbonate couplers via substitution and addition reactions with primary amines, bis(functional) compounds with a free hydroxyl group were prepared. Using these compounds by grafting-from reaction, amphiphilic end-functionalized poly(ε-caprolactone) (PCL) and poly(methyl methacrylate) (PMMA) were prepared. Via polymer analogous reaction polyether with amphiphilic head groups was obtained.Figure optionsDownload full-size imageDownload as PowerPoint slide