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Non‐isocyanate Polyurethanes from 1,1′‐Carbonyldiimidazole: A Polycondensation Approach
Author(s) -
Wolfgang Josh D.,
White B. Tyler,
Long Timothy E.
Publication year - 2021
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.202100163
Subject(s) - isocyanate , condensation polymer , monomer , polymer chemistry , polyurethane , materials science , surface modification , thermal stability , polymerization , catalysis , step growth polymerization , polyester , thermoplastic , organic chemistry , chemistry , polymer , composite material
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.