Thermally Induced Polymerization of Muconic Esters in the Solid State Studied by Infrared Microscope Spectroscopy under Temperature Control

The polymerization mechanism and kinetics for the thermally induced solid-state polymerization of muconic esters are revealed by infrared microscope spectroscopy using single crystals under temperature control combined with X-ray diffraction measurements. In the present study, a definite induction period during the initial stage of the solid-state polymerization of di(4-chlorobenzyl) and di(4-bromobenzyl) (Z,Z)-muconates upon heating in the dark is observed. Such a polymerization behavior is uniquely observed for the shrinking-type polymerization of these monomers, but not for the expanding polymerization of bis(3,4-methylenedioxybenzyl) (E,E)-muconate. The reaction mechanism is discussed on the basis of the experimental results for the kinetic analysis of the polymerization by infrared spectroscopy as well as structural determination by X-ray diffraction measurements.

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