Polyurethanes 1,4:3,6-dianhydrohexitols

Keywords a,co-Alkanediamines, l,4 3,6-Dianhydrohexitols, Aldaric acids, Aldo-nolactones, Aminoalditols, o-Glucitol, Diaminoalditols, D-Mannitol, D-Xyhtol application, Erythritols, Isoidide, Isomannide, Isosorbide, L-Arabinitol, Lipase-catalysis, Polyamides, Polycarbonates, Polyesteramides, Polyesters, Polyethers, Polyureas, Polyurethanes, Super-acid, Tartaric acids... 

A similar approach was used by Thiem and Lueders23,25,195 for generating polyurethanes 132 and 133 from 129 or aliphatic diamines and 1,4 3,6-dianhydrohexitol-derived bis(chloroformates) 131. A preparation for 129, starting from mesylates and proceeding by way of azides, was provided in this connection (see Scheme 31). 

F. Bachmann, J. Reimer, M. Ruppenstein, and J. Thiem, Synthesis of novel polyurethanes and polyureas by polyaddition reactions of dianhydrohexitol configurated diisocyanates, Macromol. Chem. Phys., 202 (2001) 3410-3419. 

In addition, isosorbide and other l,4 3,6-dianhydrohexitols (isomannide derived from D-mannose, isoidide derived from L-fructose) are also attractive to serve as monomers for polymer production due to their rigidity, chirality, and non-toxicity (Fig. 6). Such features may introduce special properties into the polymers formed, such as enhanced Jg and/or special optical properties. Their innocuous nature also opens the possibility of applications in packaging or medical devices. As a bifunctional monomer, isosorbide can be polymerized with other bifunctional monomers via condensation polymerization. A recent review described various isosorbide-based polymers synthesized, including polyesters, polyamides, poly(ester amide)s, poly(ester imide)s, polycarbonates, polyurethanes, and so on [308], and the present... 

Carbohydrates such as saccharose, D-glucitol, and diaminosaccharides such as trehalose, have been widely used for the syntheses of highly functionalized polyol-based polyurethanes. The preparation of pol5Uirethanes by the reaction of dianhydrohexitols with aliphatic diisocyanates was explored in 1983, and technical applications of dianhydrohexitols were found as chain extenders in polyurethane syntheses, as patented. 

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