Linear homo- and co-polycarbonates have been prepared from the sugar-based diols 2,3,4-tri-O-methyl-l-arabinitol and 2,3,4-tri-O-methylxylitol. Statistical co-polycarbonates were obtained from molar feed ratios of sugar:bisphenol A of 1:1 and 2:1. The polycarbonates were stable up to ∼280 °C with maximum decomposition rate above 345 °C. The arabinitol-based homopolymer was found to be semicrystalline whereas the xylitol-based one was amorphous. All the copolymers were amorphous with T g ranging between 60 and 80 °C. Both homo- and co-polycarbonates showed high resistance to chemical hydrolysis; however, they were enzymatically degraded in different degree. The xylitol-based polycarbonates were the more easily degraded by lipase B from Candida antarctica in acetonitrile at 70 °Cthis enzyme showing a high selectivity toward the configuration of the sugar-based moiety.
The synthesis and characterization of a new series of AABB-type polyamides based on l-arabinitol and xylitol are described. These linear polyamides were obtained by reaction of the aldaric acids or aliphatic dicarboxylic acids, with sugar-based diamine or aliphatic diamines. The pentaric diacids were activated as their pentachlorophenyl esters, and the diamino sugars were used as dihydrochlorides. Aliphatic diamines were used either as their activated trimethylsilyl derivatives or as the free bases. All the polyamides were soluble in the usual organic solvents, and those fully sugar-based were also soluble in water. All of them were very hygroscopic, especially those based on xylitol. DSC and X-ray powder diffraction studies showed that l-arabinitol-based polyamides were more crystalline than those derived from xylitol.
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