Aliphatic polycarbonates and poly(ester carbonate)s from fatty acid derived monomers
Résumé
Fatty acid derivatives were efficiently used as starting materials for the synthesis of polycarbonates and poly(ester carbonate)s. A novel AB-type self-condensable monomer, ethyl(9-hydroxy-10-methoxyoctadecyl)carbonate (EHMOC) and a dicarbonate monomer, 4-[(ethoxycarbonyl)oxy]butyl-12-[(ethoxycarbonyl)oxy]octadec-9-enoate (EOBEOE) were prepared from oleyl alcohol and ricinoleic acid, respectively. Of these, EHMOC was polymerized by the alcohol-carbonate exchange self-polycondensation approach, while EOBEOE was polycondensed with various biobased diols to give polycarbonates and poly(ester carbonate) s, respectively. The monomers and polymers were well characterized by FTIR and H-1-NMR spectroscopy. The C-13-NMR spectroscopy revealed the formation of randomly distributed sequences in the poly(ester carbonate) s due to the carbonate interchange reaction. An unexpected formation of polyricinoleate was observed and confirmed by NMR and MALDI-TOF spectroscopy. Most of the polymers displayed good thermal stability with the temperature at 10% weight loss in the range 273-325 degrees C. Due to the presence of aliphatic segments, these materials exhibit very low glass transition temperature.