Novel linear homogeneous polyurethanes and polyureas with enhanced hydrophilic character have been successfully prepared from sugar‐based monomers having their hydroxyl groups free or partially protected. By the reaction of primary hydroxyl groups of xylitol with dimethyl hexamethylene dicarbamate (HMDC) or di‐tert‐butyl‐4,4′‐diphenyl methyl dicarbamate (MDC), two new linear semicrystalline polyurethanes [PU(X‐HMDC) and PU(X‐MDC)] have been prepared. Likewise, by the reaction of xylitol with the analogous diisocyanates hexamethylene diisocyanate (HMDI) or 4,4′‐methylenebis(phenyl isocyanate) (MDI), similar polyurethanes [PU(X‐HMDI) and PU(X‐MDI)] were obtained. However, these latter polyurethanes present some degree of crosslinking because of the higher reactivity of the diisocyanate comonomers. Linear hydrophilic polyureas having free hydroxyl groups joined to the main chain have also been prepared by the reaction of the same diisocyanates (HMDI and MDI) with 1,6‐diamino‐1,6‐dideoxy‐D‐mannitol and 1,6‐diamino‐1,6‐dideoxy‐3:4‐O‐isopropylidene‐D‐mannitol. As far as we are aware, this kind of polyhydroxylated polyurea has not been previously described in the literature. The new polymers were characterized by standard methods (elemental analyses, gel permeation chromatography, IR, and NMR). The polyurethanes were hydrolytically degradable under physiological conditions, in contrast with less‐hydrophilic linear polyurethanes previously described. The thermal properties of the novel polymers were investigated by thermogravimetric analysis and differential scanning calorimetry. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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The synthesis and characterization of a new series of aromatic polyesters based on D‐mannitol and galactitol are described. These polyesters were obtained by polycondensation reaction of the terephthaloyl chloride or isophthaloyl chloride and 2,3,4,5‐tetra‐O‐methyl‐D‐mannitol or 2,3,4,5‐tetra‐O‐methyl‐galactitol in o‐dichlorobenzene. All the new polyesters were characterized by elemental analyses, GPC, IR, and NMR. They were soluble in chloroform, but insoluble in water and other polar oxygenated solvents. They showed a notable hygroscopicity, lower for those containing isophthalic units. DSC and X‐ray diffraction studies showed that D‐mannitol‐based polyesters were stiffer and less crystalline than those derived from galactitol, which presented a noticeably lower thermal stability. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 4570–4577, 2005

Polycondensation of 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-D-mannitol or 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-L-iditol with aromatic and aliphatic dicarboxylic acids has been used to prepare a series of regio-and stereoregular AABB-type polyamides. We also describe the preparation of 1,6-diamino-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol and 1,6-diamino-1,6-dideoxy-2,5-di-O-methyl-3,4-O-isopropylidene-D-mannitol and their polycondensation reactions with the same dicarboxylic acids. The obtained polyamides were gummy solids that were optically active and had a pronounced affinity for water, although most of them were not soluble in this solvent. These polyamides were characterized by viscosimetry, gel-permeation chromatography, elemental analysis, and IR and NMR spectroscopies.

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