Bioderived Thiol–Ene\nEmulsion Polymerization\nfor Hybrid Latex Particles

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