Non-isocyanate Polyurethanes from 1,1′-Carbonyldiimidazole: A Polycondensation Approach

Josh D. Wolfgang, B. Tyler White, Timothy E. Long

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Article number2100163
JournalMacromolecular Rapid Communications
Volume42
Issue number13
DOIs
StatePublished - Jul 2021
Externally publishedYes

Keywords

  • engineering polymers
  • non-isocyanate
  • sustainability
  • thermoplastic polyurethane

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Fingerprint

Dive into the research topics of 'Non-isocyanate Polyurethanes from 1,1′-Carbonyldiimidazole: A Polycondensation Approach'. Together they form a unique fingerprint.

Cite this