Synthesis of functional polycarbonates by copolymerization of carbon dioxide with allyl glycidyl ether

Abstract

Functional aliphatic polycarbonate was synthesized by copolymerization of carbon dioxide and allyl glycidyl ether in the presence of a catalyst system based on ZnEt2 and pyrogallol at a molar ratio of 2 : 1. The polycarbonate obtained was oxidized with m‐chloroperbenzoic acid to give poly(epoxycarbonate). These polymers were degraded in an aqueous buffer of pH 7.4 at 37°C. Hydrolytic degradation was monitored by determination of the weight loss.

Synthesis and Modification of Functional Polycarbonates with Pendant Allyl Groups

“…[25,26] A solution of pyrogallol (7.5 mmol in 25 cm 3 of dioxane) was slowly added to a stirred solution of ZnEt 2 (15 mmol in 35 cm 3 of dioxane) at room temperature. After the addition was completed, stirring was continued until the evolution of ethane stopped.…”

“…[26,27] This is described in detail elsewhere. [25] Briefly, a solution of the catalyst (ca. 4 mmol) and 100 mmol of GE were placed into a stainless steel autoclave filled with argon.…”

“…[25] The concentration of the polymers in the reaction solution (0.5-5.0% w/w) and the duration of the reaction (48-168 h) were varied in order to achieve total oxidation.…”

“…[25] They were synthesized by the copolymerization of AGE and CO 2 in the presence of the catalyst system: diethyl zinc-pyrogallol (ZnEt 2 /PG). The copolymerization of oxiranes with carbon dioxide in the presence of the ZnEt 2 /PG system is considered to be an anionic coordination one.…”

“…[25] In this work functional oxirane (AGE) and one of two saturated oxiranes, namely butyl glycidyl ether (BGE) or isopropyl glycidyl ether (IGE), were copolymerized with CO 2 to yield high-molecular-weight polycarbonates, which were than epoxidized to poly(epoxycarbonate)s.…”