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Linear polyurethanes made from naturally occurring tartaric acid

Authors

  • Romina Marín,

    1. Departament d'Enginyeria Química, Universitat Politècnica de Catalunya, ETSEIB, Diagonal 647, 08028 Barcelona, Spain
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  • Antxon Martínez de Ilarduya,

    1. Departament d'Enginyeria Química, Universitat Politècnica de Catalunya, ETSEIB, Diagonal 647, 08028 Barcelona, Spain
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  • Sebastián Muñoz-Guerra

    Corresponding author
    1. Departament d'Enginyeria Química, Universitat Politècnica de Catalunya, ETSEIB, Diagonal 647, 08028 Barcelona, Spain
    • Departament d'Enginyeria Química, Universitat Politècnica de Catalunya, ETSEIB, Barcelona 08028, Spain
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Abstract

Naturally occurring tartaric acid was used as raw material for the synthesis of novel linear polyurethanes (PURs) bearing two carboxylate side-groups in the repeating unit. Aliphatic and aromatic PURs were obtained by reaction in solution of alkyl and benzyl tartrates with hexamethylene diisocyanate and 4,4′-methylene-bis(phenyl isocyanate), respectively. All the novel PURs were thermally stable and optically active. The aliphatic carboxylate-containing PURs had Mw in the 40–70 kDa range, with PD between 2.1 and 2.5; all were semicrystalline polymers with melting temperatures between 100 and 150 °C and Tg in the 50–80 °C range. The aromatic PURs were amorphous materials with molecular weights between 18 kDa and 25 kDa and Tg above 130 °C. Hydrogenolysis of the PUR made from hexamethylene diisocyanate and benzyl tartrate yielded PURs containing up to 40% of free carboxylic side-groups. The tartrate-derived PURs displayed enhanced sensitivity to hydrolysis compared with their unsubstituted 2,6-PUR homologs. The PURs bearing free carboxylic groups were unique in being degraded by water upon incubation under physiological conditions. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2391–2407, 2009

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