Carbohydrate‐based polyurethanes: A comparative study of polymers made from isosorbide and 1,4‐butanediol

Abstract

A set of linear polyurethanes containing isosorbide units were synthesized by polymerization in solution from HDI and MDI diisocyanates and 1,4‐butanediol (BD), isosorbide (Is) or diisosorbide diurethanes (Is2HDI and Is2MDI) as diols. The thermal transitions, thermal stability, and crystal structure of the polyurethane homopolymers and copolymers containing isosorbide were evaluated and compared with those displayed by their polyurethane analogues entirely made of BD. It was found that incorporation of Is units in the polyurethane chain produced significant changes in Tg, Tm, and Td but no significant differences were noticed between copolymers made from Is or Is2 monomers. Degradation assays revealed that the presence of Is units increased slightly the hydrolysis rate of polyurethanes. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

Synthesis, structure and properties of fully biobased thermoplastic polyurethanes, obtained from a diisocyanate based on modified dimer fatty acids, and different renewable diols

“…This may be a consequence of the asymmetrical reactivity of both hydroxyl groups brought by ISO, inducing chain-terminating reaction (ending propagation). As recently reported by Munoz-Guerra et al in 2012 [24], ISO was found to mainly react on the endo hydroxyl group, which exhibits a higher reactivity than the exo one, whereas the exo hydroxyl group appears as the major chain end-group. Another explanation could be also linked to the effect of the byproducts during the synthesis of DDI with 2-heptyl-3,4-bis(9-isocyanatononyl)-1-pentylcyclohexane as the main chemical.…”

Thermoplastic polyurethanes with isosorbide chain extender

“…A non‐isocyanate route to polyurethanes using dicyclocarbonates from isosorbide and amines was also studied . A comparative study of polyurethanes from isosorbide and butane diol with two isocyanates showed that the presence of isosorbide increased glass transition temperature ( T g ) and melting point ( T m ), but was also responsible for an increased hydrolysis rate . In a related study, segmented polyurethanes were prepared from isosorbide or butane diol with MDI or hexamethylene diisocyanate (HDI) with polycaprolactone soft segments and their effect on polymerization rate and hydrolysis were analyzed …”

Renewable thermoplastic polyurethanes containing rigid spiroacetal moieties

“…The materials were also subjected to a visual test to check for transparency and crystallinity. The hydrolytic stability of the materials was evaluated over a wide pH range for a period of one month in order to assess potential degradation of the acetal units [33].…”