Synthesis of head-to-tail polyurethanes from nonsymmetric diisocyanate and ethylene glycol with organotin catalysts

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2001-02, Vol.39 (3), p.416-429
• Main Authors: Nishio, Akinori, Mochizuki, Amane, Sugiyama, Jun-Ichi, Takeuchi, Kazuhiko, Asai, Michihiko, Yonetake, Koichiro, Ueda, Mitsuru
• Format: Article
• Language: English
• Subjects: Applied sciences; constitutional isomerism; Exact sciences and technology; head-to-tail-ordered; nonsymmetric monomer; Organic polymers; p-isocyanatobenzyl isocyanate; Physicochemistry of polymers; Polycondensation; polyurethane; Preparation, kinetics, thermodynamics, mechanism and catalysts
• ISSN: 0887-624X; 1099-0518
• DOI: 10.1002/1099-0518(20010201)39:3<416::AID-POLA1009>3.0.CO;2-N

An ordered head‐to‐tail (HT) polyurethane was successfully prepared by the polyaddition reaction of p‐isocyanatobenzyl isocyanate with ethylene glycol with dibutyltin dilaurate as a catalyst. Furthermore, the HT regularity of polyurethane was improved to 83% with 1,1,3,3‐tetraphenyl‐1,3‐dichlorodistannoxane. The polymerization was conducted in N,N‐dimethylformamide at 30 °C with both monomers mixed at once. The microstructure of the polymer was investigated by 1H and 13C NMR spectroscopy, and the polymer obtained by the polyaddition reaction had the expected HT linkages. The constitutional regularity of the polymers influenced the thermal properties and crystallinity. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 416–429, 2001 A head‐to‐tail (HT) ordered polyurethane was prepared from p‐isocyanatobenzyl isocyanate as a nonsymmetric monomer with ethylene glycol as a symmetric monomer with organotin catalysts. The polymer obtained with a polyaddition reaction had the expected HT linkages. The constitutional regularity of the polymers influenced the thermal properties and crystallinity.