New Method of Synthesis of Poly(ester amide)s Derived from the Incorporation of Glycolic Acid Residues into Aliphatic Polyamides

Abstract

Summary: A new method for the preparation of poly(ester amide)s derived from glycolic acid units has been developed. Glycolic acid units can be incorporated with a high yield into a nylon‐n or a nylon‐n,m. The synthesis is based on a final thermal polycondensation with the formation of a metal halide salt as a driving force. New poly(ester amide)s have high molecular weights, good mechanical behaviour, and variable thermal properties, giving rise to a group of materials with potential interest as biodegradable materials in applications like surgical sutures.Results of the differential scanning calorimeter heating runs for the sodium (a) and potassium (b) salts of N‐chloroacetyl‐6‐aminohexanoic acid.magnified imageResults of the differential scanning calorimeter heating runs for the sodium (a) and potassium (b) salts of N‐chloroacetyl‐6‐aminohexanoic acid.

Degradable Poly(ester amide)s for Biomedical Applications

“…A thermal polycondensation reaction based on the elimination of a metal halide as a driving force was also applied to prepare PEAs based on chloroacetate derivatives of an -amino acid [35,36] or a diamine [35,37] (Figure 7). Polymerizations can take place in the solid phase, the liquefied phase, or both phases, depending on the length of the monomers (i.e., the number of methylene groups) and the metal cation involved (e.g., cesium, potassium or sodium).…”

Poly(ester amide) nanocomposites by in situ polymerization: Kinetic studies on polycondensation and crystallization

“…The monomer, sodium chloroacetylaminohexanoate, was synthesized following a previously reported method [20,21]. All reagents and solvents were purchased from Aldrich Chemical Company, (Milwaukee, WI, USA) and used as received.…”

“…All reagents and solvents were purchased from Aldrich Chemical Company, (Milwaukee, WI, USA) and used as received. Polymerization was based on a thermal polycondensation which rendered sodium chloride as a byproduct (Figure 1a) [20,21]. The nanocomposites were based on two organomodified layered phyllosilicates: methyl tallow bis(2-hydroxyethyl) ammonium montmorillonite (Closite 30B, Southern Clay Products, MT2EH, Gonzales, Texas, USA) and dimethyl dihydrogenated-tallow ammonium montmorillonite (Closite 20A, Southern Clay Products, 2MH2HT, Gonzales, Texas, USA).…”

“…The alternating poly(ester amide) derived from glycolic acid and 6-aminohexanoic acid (poly(glc-alt-amh)) has recently received attention for two main reasons: a) The simple synthesis procedure based on only two reaction steps ( Figure 1a), and b) A composition based on the main units of biodegradable polyesters (glycolic acid) and aliphatic polyamides (6-aminohexanoic acid). Poly(glc-alt-amh)) is obtained by a thermal polycondensation reaction based on the formation of a metal halide salt as the driving force of the condensation reaction [20,21], which seems an appropriate procedure to prepare nanocomposites by in situ polymerization. This is a highly attractive technique due to its versatility and compatibility with various reactive monomers, making it a valuable process for commercial applications [22,23].…”

Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

“…Recently, a new synthetic route to sequential PEAs has been investigated. In this method, thermal polycondensation of different metal salts of chloroacetyl-ω-amino acids leads to high-molecular-weight sequential PEAs [65][66][67][68][69].…”