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

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Capitao, R. M. [UNESP]
Santo, R. D. E. [UNESP]
Magalhaes, A.
Assis, D.
Silva, G. V. J. da
Scarim, C. B. [UNESP]
Chelucci, R. C. [UNESP]
Andrade, C. R. [UNESP]
Chung, M. C. [UNESP]
Gonzalez, E. R. P. [UNESP]

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Royal Soc Chemistry


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 similar to 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.



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Rsc Advances. Cambridge: Royal Soc Chemistry, v. 6, n. 83, p. 79987-79997, 2016.