期刊
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
卷 54, 期 15, 页码 2394-2402出版社
WILEY
DOI: 10.1002/pola.28114
关键词
copolymerization; biodegradable polymers; organo catalysis; polyamides; polyesters; poly(ester amide)s; ring-opening polymerization; sulfonic acids
资金
- Euskampus Fundazioa
- Spanish Ministery of Economy and Competition [CTQ2014-53458-1]
- European Commission [SUSPOL-EJD 642671, FP7-PEOPLE-212-ITN 316832-OLIMPIA]
- MINECO [FDI 16507]
- Convocatoria de Contratacion para la especializacion de personal investigador doctor en la UPV/EHU
Polyamides (PA) constitute one of the most important classes of polymeric materials and have gained strong position in different areas, such as textiles, fibers, and construction materials. Whereas most PA are synthesized by stepgrowth polycondensation, PA 6 is synthesized by ring opening polymerization (ROP) of epsilon-caprolactam (epsilon-CLa). The most popular ROP methods involve the use of alkaline metal catalyst difficult to handle at large scale. In this article, we propose the use of organic acids for the ROP of epsilon-CLa in bulk at 180 degrees C (below the polymer's melting point). Among evaluated organic acids, sulfonic acids were found to be the most effective for the polymerization of epsilon-CLa, being the Bronsted acid ionic liquid: 1-(4-sulfobutyl)-3-methylimidazolium hydrogen sulfate the most suitable due to its higher thermal stability. End-group analysis by H-1 nuclear magnetic resonance and model reactions provided mechanistic insights and suggested that the catalytic activity of sulfonic acids was a function of not only the acid strength, but of the nucleophilic character of conjugate base as well. Finally, the ability of sulfonic acid to promote the copolymerization of epsilon-CLa and epsilon-caprolactone is demonstrated. As a result, poly(e-caprolactam-co-epsilon-caprolactone) copolymers with considerably randomness are obtained. This benign route allows the synthesis of poly(ester amide)s with different thermal and mechanical properties. (C) 2016 Wiley Periodicals, Inc.
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