Isosorbide and succinic acid are promising biobased feedstocks for the preparation of biorenewable materials. Some studies on isosorbide-succinate polyesters had previously been reported, but the properties of monomeric materials derived from these two building blocks were unknown. We designed a diisocyanate that is prepared from isosorbide and succinic acid in a short reaction sequence featuring a Curtius rearrangement. The diisocyanate synthesis does not require any stoichiometric petroleum-based reagents and has been scaled past 100 grams. This diisocyanate allows polyurethanes with up to 100% bio-content to be prepared, and the thermo-mechanical characterization of representative polyurethanes is ongoing. We also discovered that a synthetic precursor to the diisocyanate is a promising tackifier. Characterization of a family of related tackifiers revealed that simple structural changes allow the temperature at which the material is most tacky to be adjusted without reducing the level of maximum tack.

Diisocyanates and tackifiers from isosorbide

249th National Meeting (2015)

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