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Synthesis and Characterization of Salicylic Acid-Based Poly(Anhydride-Ester) Copolymers

Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854-8087, USA

Kathryn E. Uhrich

Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854-8087, USA, uhrich{at}rutchem.rutgers.edu

A series of poly(anhydride-esters) based on poly(1,10-bis(o-carboxyphenoxy)decanoate) (CPD) and poly(1,6-bis(p-carboxyphenoxy)hexane) (p-CPH) were synthesized by melt-condensation polymerization. Poly-(anhydride-esters) that contain CPD hydrolytically degraded into salicylic acid, however, these homopolymers have mechanical and thermal characteristics that limit their use in clinical applications. The synthesis and characterization of copolymers of CPD with p-CPH, a monomer known to generate mechanically stable homopolymers, was investigated. By changing the CPD to p-CPH monomer ratios, the salicylic acid loading and thermal/mechanical properties of the copolymers was a controlling factor; increasing the CPD concentration increased the salicylate loading but decreased the polymer stability; whereas increasing the p-CPH concentration increased the thermal and mechanical stability of the copolymers. Specifically, decreasing the CPD:p-CPH ratio resulted in lower salicylate loading and increased thermal decomposition temperatures. The glass transition temperatures (°C) varied from 27 to 38°C, a desirable range for elastomeric biomedical implants.

Key Words: poly(anhydride-ester) • salicylic acid • drug loading • thermal properties • degradation • polyanhydride stability

Journal of Bioactive and Compatible Polymers, Vol. 21, No. 2, 123-133 (2006)
DOI: 10.1177/0883911506062976


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