Simple Preparation of Thiol-Ene Particles in Glycerol and Surface Functionalization by Thiol-Ene Chemistry (TEC) and Surface Chain Transfer Free Radical Polymerization (SCT-FRP)

Macromol Rapid Commun. 2018 Jan;39(2). doi: 10.1002/marc.201700394. Epub 2017 Oct 24.

Abstract

Thiol-ene (TE)-based polymer particles are traditionally prepared via emulsion polymerization in water (using surfactants, stabilizers, and cosolvents). Here, a green and simple alternative is presented with excellent control over particle size, while avoiding the addition of stabilizers. Glycerol is applied as a dispersing medium for the preparation of off-stoichiometric TE microparticles, where sizes in the range of 40-400 µm are obtained solely by changing the mixing speed of the emulsions prior to crosslinking. Control over surface chemistry is achieved by surface functionalization of excess thiol groups via photochemical thiol-ene chemistry resulting in a functional monolayer. In addition, surface chain transfer free radical polymerization is used for the first time to introduce a thicker polymer layer on the particle surface. The application potential of the system is demonstrated by using functional particles as adsorbent for metal ions and as a support for immobilized enzymes.

Keywords: enzyme immobilization; polymer particles; surface functionalization; suspension polymerization; thiol-ene chemistry.

MeSH terms

  • Free Radicals / chemical synthesis
  • Free Radicals / chemistry
  • Glycerol / chemistry*
  • Molecular Structure
  • Particle Size
  • Photochemical Processes
  • Polymerization
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Surface Properties

Substances

  • Free Radicals
  • Polymers
  • Sulfhydryl Compounds
  • Glycerol