Synthesis of poly(glycolic acid‐alt‐12‐aminododecanoic acid): The thermal polymerization kinetics of sodium N‐chloroacetyl‐12‐aminododecanoate

Abstract

A new regular poly(ester amide) consisting of glycolic acid and 12‐aminododecanoic acid was synthesized by a thermal polycondensation method involving the formation of a metal halide salt. Polymerization could start in liquefied or solid phases, depending on the reaction temperature. The polymerization kinetics were investigated by isothermal and nonisothermal isoconversional methods. The reaction model was selected with both Coats–Redfern and isokinetic relationships. The activation energy was higher when the reaction took place mainly in the solid state. A compensation effect was found between the frequency factor and the activation energy. The thermal properties of the new polymer were studied as well as the isothermal crystallization from the melt state. Melt‐grown spherulites were studied by means of polarizing optical microscopy. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 1199–1213, 2006

Copolymerization of potassium chloroacetate and potassium N‐chloroacetyl‐6‐aminohexanoate

“…Several studies were performed to determine the polymerization kinetics, thermal stability, and properties of these new PEAs. [12][13][14] Copolymerization of chloroacetate with N-chloroacetyl-x-aminoalkanoates is also an interesting topic since it may render random copoly(ester amide)s with tunable properties as a result of the control over the ester/amide ratio. 15 This work specifically focuses on the copolymerization between a chloroacetate salt and the AH derivative.…”

“…New monomers were easily synthesized, in this case, by the reaction of chloroacetyl chloride with the appropriated ω‐amino acid and by subsequent neutralization with the selected metal hydroxide. This synthesis rendered high molecular weight samples when ω‐amino acids had a high methylene content [i.e., 6‐aminohexanoic (AH),10 11‐aminoundecanoic,11 and 12‐aminododecanoic acid12 derivatives]. Polymerizations could occur in the solid, liquid, or both phases, depending on the number of methylene groups and the kind of salt.…”

Alternating poly(ester amide)s of glycolic acid and ω‐amino acids: Crystalline morphology and main crystallographic data

“…A new method of synthesis (Scheme ) based on a thermal polycondensation reaction with formation of metal halide salts as a driving force has proved to be highly effective and raised again interest in this series of polymers 23, 24. As a result, the polymerization kinetics,25 thermal stability and degradability,26 and crystallization kinetics27 of some samples have been studied. The main goal of this work is to report the main structural data of aminohexanoic and aminoundecanoic derivatives, which were chosen for being representative of polymers with an even and an odd number of methylene groups in the repeat unit, and also for having very different methylene/amide ratios.…”