Degradable Thermoset Fibers from Carbohydrate-Derived Diols via Thiol–Ene Photopolymerization

Abstract

Carbohydrate-derived monomers were synthesized, and thiol–ene photopolymerization was employed to produce thermoset films and fibers from the biobased dienes isosorbide 10-undecenoate (IU) and glucarodilactone 10-undecenoate (GDLU) and multifunctional thiols. The resulting materials, comprising up to 94% biorenewable content, were flexible and cross-linked and had mechanical and thermal properties that varied with IU and GDLU content (e.g., rubbery plateau storage moduli = 6.1 to 10.5 MPa at 40 °C above the glass transition temperature; glass transition temperatures = −9.9 to 27 °C by differential scanning calorimetry; degradation temperatures = 238 to 347 °C by thermogravimetric analysis). By combining electrospinning with in-situ UV irradiation and carefully controlling the monomer mixture viscoelasticity and orifice-to-collector flight time, we produced uniformly cured fibers directly from the monomer feed when the ene monomers contained either 100% GDLU or 50% GDLU/50% IU. The resulting GDLU-containin...