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Isosorbide vs Isomannide

 

Isosorbide (IS) and isomannide (IM) are rigid chiral isomers derived from the natural sugars, glucose and fructose. These compounds are identical with the exception of one stereogenic center bearing an exo or endo alcohol functionality. Therefore, these platform chemicals are uniquely suited to study stereochemistry effects in polymer properties. 

Success in our group has harnessed new strategies for utilizing these precursors to develop new plastics. The image to the right is a new type of polyurethane comprised of 90% (w/w/) biobased feedstocks. 

Isohexide polyurethane
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Comonomers for PVEs

 

Polyvinylethers (PVE)s are typically viscous fluids used in release coating and adhesives. Here we show that IS can be selectively modified into a cyclic vinyl ether (glycal) monomer (3) that may be used as a rigid comonomer in PVE synthesis. Incorporating up to 42 mol% of (3) raised the glass transition temperature of poly(isobutyl vinyl ether) by 25 C.

Towards New Polymers from Renewable Biomass

Pine Sap Plastics

α-Pinene, the primary volatile components of pine sap, is a sustainably sourced hydrocarbon precursor to new polymeric materials. While α-pinene itself is difficult to polymerize, we have modified its structure through a few synthetic steps to produce the isomer δ-pinene. It was discovered that δ-pinene is capable of undergoing ring opening metathesis polymerization (ROMP) to produce a very promising plastic with a very specific and chiral macromolecular structure. Salient features, such as high molar mass, low dispersity, and a high glass transition temperature (~100 °C) positions this material as a promising precursor to new biomass-derived plastics.