Synthesis of azo carbonate monomers and biocompatibility study of poly(azo-carbonate-urethane)s

• Published in: RSC advances 2016-01, Vol.6 (83), p.79987-79997
• Main Authors: Capitão, R. M, Santo, R. D. E, Magalhães, A, Assis, D, da Silva, G. V. J, Scarim, C. B, Chelucci, R. C, Andrade, C. R, Chung, M. C, González, E. R. P
• Format: Article
• Language: English
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c6ra11075d

The present work describes the synthesis of azo carbonate monomers by a clean carbonylation synthetic route using di-methylcarbonate. The kinetics study showed a conversion of ∼98% to bis-carbonates after only six minutes of reaction using triazabicyclo[4.4.0]dec-5-ene (TBD) as the catalyst. The preparation of azo-carbonates by means of coupling aryldiazonium salts with bis-carbonate was performed. The reactivity of azo-carbonate monomers was tested in the polycondensation reaction with an aminoalcohol using TBD as a catalyst for the formation of non-isocyanate poly(azo-carbonate-urethane)s PCU 1 and PCU 2 . The copolymers' structures were confirmed by FT-IR, NMR and MALDI experiments, which allow us to determine the different terminal groups of the polymer chains formed. The molecular weights and the molecular weight distribution of PCU 1 and PCU 2 were determined by size-exclusion chromatography (SEC) experiments and thermal stabilities were also studied by TG analysis. The biocompatible properties of monomers 4 and 6 and polymers PCU 1 and PCU 2 were investigated by liver, kidney and colon histological analyses. The present study describes the synthesis of non-isocyanate poly(azo-carbonate-urethane)s and characterization by FT-IR, NMR, MALDI, GPC and TG. Biocompatible properties were investigated by the liver, kidney and colon histological analyses.