Synthesis and characterization of poly(ɛ-caprolactone-co-ethylene glycol) star-type amphiphilic copolymers by “click” chemistry and ring-opening polymerization

Abstract

The synthesis of poly(ɛ-caprolactone-co-ethylene glycol) AAB star-type amphiphilic copolymers were carried out by use of a “click” chemistry reaction to block propargyl polyethylene glycol (propargyl-PEG) to terminally azide poly(ɛ-caprolactone) (PCL-N₃). For this purpose, propargyl-PEG was synthesized by the reaction of PEGs (3000 Da, 2000 Da, 1500 Da, and 1000 Da) and propargyl chloride. Terminally chloride poly(ɛ-caprolactone) (PCL-Cl) was carried out by means of ring-opening polymerization (ROP) of ɛ-caprolactone (CL) and 3-chloro-1,2-propanediol. Synthesis of PCL-N₃ was obtained by the chemical interaction of PCL-Cl and sodium azide. By reacting propargyl-PEG and PCL-N₃, the star-type amphiphilic copolymers were obtained. The characterization of products was accomplished by using multiple instruments including ¹H-NMR, FT-IR, GPC, TGA, contact angles, and elemental analysis techniques.

Keywords:

• “Click” chemistry
• ring-opening polymerization
• star-type amphiphilic copolymer
• terminally azide poly(ɛ-caprolactone)
• propargyl polyethylene glycol