Synthesis and characterization of a poly-O-methyl-[n]-polyurethane from a D-glucamine based monomer

ADRIANA A. KOLENDER; SILVINA M. ARCE; OSCAR VARELA

CARBOHYDRATE RESEARCH

ELSEVIER SCI LTD

Año: 2011 vol. 346 p. 1398 - 1405

0008-6215

The aminoalditol 1-amino-1-deoxy-D-sorbitol (1) was readily converted into the 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this -amino--phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and a higher purity than that obtained via the isocyanate. The [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermal and spectroscopically.