Synthesis and in vitro degradation of novel copolymers of cyclic carbonate and D,L-lactide

• Published in: Journal of applied polymer science Vol. 101; no. 3; pp. 1988 - 1994
• Main Authors: Xu, Jian, Liu, Zhi-Lan, Zhuo, Ren-Xi
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 05.08.2006; Wiley
• Subjects: Applied sciences; biodegradable; enzymatic degradation; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; poly(carbonate-ester); Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; proteinase K; ring-opening polymerization; Biological properties; biodegradable; Biodegradability; Lactic acid copolymer; Deprotection; Mass copolymerization; enzymatic degradation; proteinase K; Hydrogenation; Spiran copolymer; Carbonate copolymer; Lactone copolymer; Cardic copolymer; Experimental study; Hydrolysis; Alcohol copolymer; Chemical modification; Preparation; Enzymatic digestion; Property structure relationship; Kinetics; Ring opening copolymerization; poly(carbonate-ester); Aliphatic copolymer; ring- opening polymerization
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.23719

Cyclic carbonate 9‐phenyl‐2,4,8,10‐tetraoxaspiro‐[5,5]undcane‐3‐one is a six‐membered carbonate monomer with a rigid side group. Novel biodegradable poly(carbonate‐ester), poly(9‐phenyl‐2,4,8,10‐tetraoxaspiro‐[5,5]undecan‐3‐one‐co‐D,L‐lactide) P(CC‐co‐DLLA), was synthesized by ring‐opening polymerization in bulk, using stannous octanoate catalyst. Effects of polymerization conditions such as catalyst concentration, reaction time, and reaction temperature on the polymerization were investigated. The structure of the copolymers was characterized by FTIR, 1H NMR, and 13C NMR. Their molecular weights and polydispersity index were determined by gel permeation chromatography. The protecting benzyl ketal group was removed subsequently by catalytic hydrogenation to give a poly(carbonate‐ester) containing pendant hydroxyl groups. The in vitro degradation of the copolymers was performed at (37 ± 0.5)°C in two media: phosphate buffer solution (pH 7.4) or Tris‐HCl buffer solution (pH 8.6) in the presence of proteinase K. The degradation rate can be regulated by adjusting the composition of two monomers. The pendant hydroxyl groups in the copolymers resulted in a prominent enhancement of the degradation rate in PBS. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 1988–1994, 2006