Synthesis and characterization of novel biodegradable poly(carbonate‐co‐phosphate)s

Abstract

A series of aliphatic poly(carbonate-co-phosphate)s was synthesized in bulk using aluminium isopropoxide as initiator by ring-opening polymerization with various cyclic carbonates (trimethylene carbonate (TMC) and 5,5-dimethyltrimethylene carbonate (DTC)) and cyclic phosphates (ethylene ethyl phosphate (EEP), ethylene isobutyl phosphate (EIBP), ethylene lauryl phosphate (ELP) and ethylene stearyl phosphate (ESP)). The in¯uence of reaction conditions such as polymerization time, polymerization temperature and initiator concentration on the yield and molecular weight were investigated. The substituent effect of the cyclic monomers on the polymerization was also studied, and the results indicate that the substituents exert a marked in¯uence on the molecular weight of the copolymers obtained. The comonomer reactivity ratios were determined (TMC 0.88 and EEP 1.17). The copolymers with backbone chains rich in phosphate content exhibit better hydrophilicity than that of TMC homopolymer, and the degradation rate of the copolymers increases with the increase of phosphate content therein.

Fully degradable antibacterial poly(ester‐phosphoester)s by ring‐opening polymerization, “click” chemistry, and quaternization

“…Meanwhile, cyclic phosphate monomers exhibit good flexibility of their pendant groups based on the pentavalent phosphorus . In this work, we designed and synthesized a novel “clickable” cyclic phosphate monomer, 2‐(2‐propynyloxy)−2‐oxo‐1,3,2‐dioxaphospholane (propynyl ethylene phosphate, PEP) and used it as a comonomer for the ring‐opening copolymerization with CL, preparing poly(ester‐phosphoester)s with pendant alkyne groups.…”

Recent Progress in Polyphosphoesters: From Controlled Synthesis to Biomedical Applications

“…Random copolymers, including poly[( ε ‐caprolactone)‐ co ‐(methoxyethyl ethylene phosphate)],33 poly[(D,L‐lactide)‐ co ‐(methyl ethylene phosphate)],43 poly[(trimethylene carbonate)‐ co ‐(ethyl ethylene phosphate)], poly[(2,2‐dimethyl trimethylene carbonate)‐ co ‐(ethyl ethylene phosphate)],44 and poly[( p ‐dioxanone)‐ co ‐(ethyl ethylene phosphate)]45 have been synthesized by the ROP of cyclic phosphoate monomer with ε‐CL, D,L‐LA, trimethylene carbonate, 2,2‐dimethyl trimethylene carbonate, or p ‐dioxanone, respectively. The incorporation of phosphoester linkages into the polymer backbone increases the solubility of random copolymers in common organic solvents, and decreases the glass‐transition temperature.…”

Synthesis and properties of a novel hyperbranched polyphosphoramidate using an A2 + CB2 approach

“…Biodegradability and biocompatibility are two basic conditions of the application of synthesized polymers. So far, there have been numerous biodegradable synthesized polymers such as aliphatic polyesters, aliphatic polycarbonates and polyanhydrides . Polyphosphates and their copolymers have been of great interest and have been evaluated for drug delivery owing to their excellent biodegradability and biocompatibility .…”