Synthesis of Novel Biodegradable Poly(ester-anhydride)s
Polymers and High Performance Materials
Poly(epsilon-caprolactone)s containing one and variable numbers of anhydride functions along the polymer backbone were synthesized and characterized. The inclusion of a single anhydride unit involved the coupling of monofunctional carboxylic acid-terminated prepolymers using diphenyl chlorophosphate. The prepolymers were produced using standnous octoate as catalyst and ethanol as the initiator, yielding monofunctional hydroxyl-terminated intermediates which were reacted with succinic anhydride in the presence of 1-methylimidazole. Diphenyl chlorophosphate was then added to a solution of the carboxylic acid-terminated prepolymer and triethylamine in 1,2-dichloroethane, and the reaction was carried out for 5 hours at room temperature to yield a polyester containing a single anhydride unit. The synthesis of polymers containing a variable number of anhydride linkages per chain was carried out in a similar manner using difunctional carboxylic acid-terminated prepolymers as chain-extending segments, and monofunctional carboxylic acid-terminated prepolymers as end-capping units. The difunctional hydroxyl-terminated poly(epsilon-caprolactone) prepolymers were produced using diethylene glycol as the initiator, and then reacted with succinic anhydride to form difunctional carboxylic acid-terminated prepolymers.
Journal of Macromolecular Science: Pure and Applied Chemistry
Storey, R. F.,
Taylor, A. E.
(1997). Synthesis of Novel Biodegradable Poly(ester-anhydride)s. Journal of Macromolecular Science: Pure and Applied Chemistry, A34(2), 265-280.
Available at: https://aquila.usm.edu/fac_pubs/5236