Bioderived Thiol–Ene Emulsion Polymerization for Hybrid Latex Particles

The thiol-ene emulsion polymerization of three dienes synthesized from bioderived compounds, and subsequent preparation of core-shell polymer latexes, is reported. Levoglucosan (LGA), levogucosenone (LGO) and isosorbide were first modified with 4-pentenoic acid to install polymerizable groups. These monomers were used along with a dithiol to prepare poly(thioether) particles via <i>ab initio</i> emulsion polymerization using potassium persulfate as initiator and sodium dodecyl sulfate as surfactant. The structure of the diene significantly influenced the size of the resulting polymer latex particles. Given their low glass transition temperature, the LGA-derived poly(thioether) particles were used as a seed for the seeded emulsion polymerization of either styrene or methyl methacrylate. Core-shell latex particles with a high <i>T</i>_g core and a low <i>T</i>_g bioderived shell were formed, as verified by electron microscopy and in agreement with theoretical predictions of the equilibrium particle morphology based on the interfacial tensions of each particle phase.