Synthesis and characterization of poly(vinyl chloride-g-ε-caprolactone) brush type graft copolymers by ring-opening polymerization and “click” chemistry

Abstract

Synthesis of poly(vinyl chloride-g-ε-caprolactone) [poly(VC-g-CL)] brush type graft copolymers were archived by “click” chemistry of polyvinyl chloride propargyl (PVC-propargyl) and terminally azido poly(ε-caprolactone) ester (PCL-N₃). For this purpose, 2-(2-azidoethoxy)ethan-1-ol (N₃-ol) was obtained by reaction of 2-(2-chloroethoxy)ethan-1-ol and sodium azide. Synthesis of PCL-N₃ was carried out by means of ring-opening polymerization (ROP) of ε-caprolactone and N₃-ol. Furthermore, PCL-N₃ was synthesized by using polycaprolactone and N₃-ol. PVC-propargyl was obtained by the reaction of purified polyvinyl chloride with propargyl alcohol. By using PCL-N₃ and PVC-propargyl, poly(VC-g-CL) brush type graft copolymers were obtained via “click” chemistry. The products were characterized by ¹H-nuclear magnetic resonance spectroscopy (¹H-NMR), Fourier-transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). The multi instruments studies of the brush type graft copolymers show that the graft copolymers easily built as a result of combination of “click” chemistry and ROP. This work is an example of a type of combination reaction, from ROP to “click” chemistry. The synthesis pathways of this study can pioneer to newer and well-designed materials for wide range applications. This method for synthesis of graft copolymer is simple and efficient.

Graphical Abstract

Keywords:

• “Click” chemistry
• ring-opening polymerization
• brush type graft copolymer
• polyvinyl chloride
• ε-caprolactone
• 2-(2-azidoethoxy)ethan-1-ol