Synthesis of antibacterial amphiphilic elastomer based on polystyrene-block-polyisoprene-block-polystyrene via thiol-ene addition

Mater Sci Eng C Mater Biol Appl. 2013 Apr 1;33(3):1061-6. doi: 10.1016/j.msec.2012.11.029. Epub 2012 Nov 24.

Abstract

A new type of amphiphilic antibacterial elastomer has been described. Thermoplastic elastomer, polystyrene-block-polyisoprene-block-polystyrene (PS-b-PI-b-PS) triblock copolymer was functionalized in toluene solution by free radical mercaptan addition in order to obtain an amphiphilic antibacterial elastomer. Thiol terminated PEG was grafted through the double bonds of PS-b-PI-b-PS via free radical thiol-ene coupling reaction. The antibacterial properties of the amphiphilic graft copolymers were observed. The original and the modified polymers were used to create microfibers in an electro-spinning process. Topology of the electrospun micro/nanofibers were studied by using scanning electron microscopy (SEM). The chemical structures of the amphiphilic comb type graft copolymers were elucidated by the combination of elemental analysis, (1)H NMR, (13)C NMR, GPC and FTIR.

Keywords: Amphiphilic comb type elastomer; Electro-spinning; Polystyrene-isoprene synthetic elastomer; Thiol-ene coupling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Butadienes / chemical synthesis
  • Butadienes / chemistry*
  • Elastomers / chemical synthesis*
  • Elastomers / chemistry
  • Elastomers / pharmacology
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Pentanes / chemical synthesis
  • Pentanes / chemistry*
  • Polyethylene Glycols / chemical synthesis
  • Polyethylene Glycols / chemistry
  • Polystyrenes / chemical synthesis
  • Polystyrenes / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • Staphylococcus aureus / drug effects
  • Sulfhydryl Compounds / chemistry*
  • Surface-Active Agents / chemical synthesis*
  • Surface-Active Agents / chemistry

Substances

  • Anti-Bacterial Agents
  • Butadienes
  • Elastomers
  • Pentanes
  • Polystyrenes
  • Sulfhydryl Compounds
  • Surface-Active Agents
  • polystyrene-block-polyisoprene
  • Polyethylene Glycols