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Z-protected glutamic acid-based biodegradable thermoplastic and thermosetting polyesters: Synthesis and characterization

✍ Scribed by R. M. Tadros; H. Noureddini; D. C. Timm

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
195 KB
Volume
73
Category
Article
ISSN
0021-8995

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✦ Synopsis

Biodegradable polymers were formed from N-benzyloxycarbonyl-L-glutamic acid with the comonomers ethylene glycol, diglycidyl ether of 1,4-butanediol, and diglycidyl ether of bisphenol A. The three polymers were a linear and a crosslinked heterochain polyester and a crosslinked polyester that contained aromatic units within its network chains. The thermoplastic resin and the soluble fractions for the thermosetting resins were characterized by gel permeation chromatography. Conversions for carboxylic acid were determined by titrations. A quality, 22,000 molecular weight thermoplastic resin was formed. The two thermosets were cured past their gel points. Gelation analysis revealed that the relative rate constants for the sequential oxirane/ acid and alcohol/acid reactions were distinct. With diglycidyl ether of 1,4-butanediol, the ratio of the respective rate constants was 3; with diglycidyl ether of bisphenol A, the ratio approached 200. The resins hydrolyzed to monomers in the presence of lipase, but in the presence of a mixed microbial culture, only the first two resins decayed to biomass, respiratory gases, and water. The third resin was inert during the period of observation.

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