Non‐isocyanate Polyurethanes from 1, 1′‐Carbonyldiimidazole: A Polycondensation Approach. Issue 13 (24th May 2021)

• Record Type: Journal Article
• Authors: Wolfgang, Josh D.; White, B. Tyler; Long, Timothy E.
• Is Part Of: Macromolecular rapid communications. Volume 42:Issue 13(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-05-24
• Subjects: engineering polymers -- non‐isocyanate -- sustainability -- thermoplastic polyurethane; Macromolecules -- Periodicals; Polymers -- Periodicals; Chemistry -- Periodicals; 547.705
• DOI: 10.1002/marc.202100163
• Languages: English
• ISSNs: 1022-1336

Abstract

Abstract: 1, 1′‐Carbonyldiimidazole (CDI) provides a platform to generate high molecular weight polyurethanes from industrially relevant diols and diamines. CDI, which is described in the literature for its use in amidation and functionalization reactions, enables the production of well‐defined and stable polyurethane precursors, thus eliminating the need for isocyanates. Herein, the functionalization of 1, 4‐butanediol with CDI yields an electrophilic biscarbamate, bis‐carbonylimidazolide (BCI), which is suitable for further step‐growth polymerization in the presence of amines. Elevated reaction temperatures enable the solvent‐, catalyst‐, and isocyanate‐free polycondensation reaction between the BCI monomer and various diamines. The thermoplastic polyurethanes produced from this reaction demonstrate high thermal stability, tunable glass transition temperatures based on incorporation of flexible polyether segments, and mechanically ductile thin films. CDI functionalized diols will allow the preparation of diverse polyurethanes without the use of isocyanate‐containing monomers. Abstract : 1, 1′‐Carbonyldiimidazole (CDI) provides a route toward thermoplastic polyurethanes, without the use of isocyanates. The reaction proceeds in a two‐step, polycondensation reaction. The initial step includes the functionalization of diols with CDI and the second step follows with the displacement of the imidazole end groups with nucleophilic diamines. This alternative approach to polyurethanes allows for significant tunability for the diol/diamine compositions.