Synthesis, Properties, and Biodegradation of Sequential Poly(Ester Amide)s Containing γ-Aminobutyric Acid

Abstract

Poly(ester amide)s are attracting attention because they potentially have excellent thermal and mechanical properties as well as biodegradability. In this study, we synthesized a series of novel poly(ester amide)s by introducing γ-aminobutyric acid (GABA) regularly into polyesters, and investigated their properties and biodegradabilities. GABA is the monomer unit of biodegradable polyamide 4 (PA4). The new poly(ester amide)s were synthesized from the reaction of ammonium tosylate derivatives of alkylene bis(γ-aminobutylate) and p-nitrophenyl esters of dicarboxylic acids. All the obtained polymers showed relatively high melting temperatures (Tm). Their thermal decomposition temperatures were improved in comparison with that of PA4 and higher enough than their Tm. The poly(ester amide)s exhibited higher biodegradability in seawater than the corresponding homopolyesters. Their biodegradabilities in activated sludge were also studied.

A Novel Approach of Bioesters Synthesis through Different Technologies by Highlighting the Lowest Energetic Consumption One

“…In contrast the polyester amides series [ 52 ] and the esters obtained by transesterification of palm oil-based methyl ester to trimethylolpropane esters [ 53 ] show better thermal stability compared to our samples.…”

CuSO4/H2O2 induced polydopamine/polysulfobetaine methacrylate co-deposition on poly(amino acid) membranes for improved anti-protein adsorption and antibacterial activity

“…This phenomenon arises from the increase in GABA content, which enhances the formation of polyamide 4 polypeptide chains within the polymer. These chains have been demonstrated to be biodegradable, thereby further improving the degradation characteristics of the PAA film [50,51]. When the reaction temperature remains unchanged and the reaction time is shortened, the degradation rate of PAA-5 membrane is the highest, with a weight loss of 15.13% on the fourth day.…”

One-Pot Synthesis of Marine-Biodegradable Poly(Ethylene Succinate)-Based Ester Amide Copolymers Containing Amino Acid

“…14 Furthermore, Nakayama et al introduced γ-aminobutyric acid (GABA) into the PES backbone, resulting in good thermal properties and marine biodegradability. 33 In their study, using GABA, which is the monomer unit of marine-biodegradable polyamide 4, as the amino acid was crucial. Thus, introducing amino acid units can add various functions, and several syntheses of poly(ester amide)s containing SA units have been reported.…”

“…The syntheses of SA-containing poly­(ester amide)­s with functional groups such as carboxyl, amine, and guanidine groups on their side chains using a similar method with acid chlorides were also reported. , An improved hydrophilicity and biocompatibility compared to those of polyesters are expected due to the introduction of the amide moieties and functional groups, and several applications of poly­(ester amide)­s in the field of biomaterials have been examined . Furthermore, Nakayama et al introduced γ-aminobutyric acid (GABA) into the PES backbone, resulting in good thermal properties and marine biodegradability . In their study, using GABA, which is the monomer unit of marine-biodegradable polyamide 4, as the amino acid was crucial.…”