TY - JOUR
T1 - Non-isocyanate Polyurethanes from 1,1′-Carbonyldiimidazole
T2 - A Polycondensation Approach
AU - Wolfgang, Josh D.
AU - White, B. Tyler
AU - Long, Timothy E.
N1 - Funding Information:
This work was supported by Honeywell Federal Manufacturing Technologies, LLC, which operates the Kansas City National Security Campus for the United States Department of Energy/National Nuclear Security Administration under Contract Number DE‐NA0002839 (Grant 418967).
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2021/7
Y1 - 2021/7
N2 - 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.
AB - 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.
KW - engineering polymers
KW - non-isocyanate
KW - sustainability
KW - thermoplastic polyurethane
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U2 - 10.1002/marc.202100163
DO - 10.1002/marc.202100163
M3 - Article
C2 - 34031942
AN - SCOPUS:85106217916
SN - 1022-1336
VL - 42
JO - Macromolecular Rapid Communications
JF - Macromolecular Rapid Communications
IS - 13
M1 - 2100163
ER -