Evaluation of degradation of furanic polyamides synthesized with different solvents

Abstract

Aromatic polyamides have properties of industrial relevance. However, the industrial and technological advancement has followed the trend of sustainability by seeking renewable source materials. In this work, polyamides were synthetized using 2,5-furandicarboxylic acid with p-phenylene diamine, triphenyl phosphite and two solvents (NMP and DMAc). To evaluate the influence of solvents on the reaction, a kinetic study of degradation was carried out by thermogravimetric analysis (TGA), X-ray diffraction (XRD) and viscometric analysis. The viscosity value was in the range 70-80 mL/g. The TGA showed a higher thermal stability and activation energy for sample prepared with DMAc than the NMP. The XRD analysis showed that the PAF DMAc presents more defined crystalline forms due to its higher solvation capability. The crystalline form can be correlated with the differences of Ea, because the crystalline orientation and the number of hydrogens bonds in sample PAF NMP may be lower than the structure attributed to PAF DMAc .

Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

“…159 Polyamides from p -phenylene diamine were synthesized in different solvents to evaluate their degradation stability depending on the material microstructure. 160 It was shown that the usage of N , N -dimethylacetamide leads to more thermally stable materials compared to N -methyl-2-pyrrolidone-derived materials. Copolycondensation of FDCA and TPA chloroanhydrides with prepolymerized fluorinated diamino-polyamide, followed by the treatment of materials with acetic anhydride, results in partially biobased block copoly(amide-imide)s suitable for colorless transparent film casting.…”

Structure, thermal and mechanical properties of copoly(ester amide)s based on 2,5‐furandicarboxylic acid

“…The work, therefore, focused mainly on the development of the synthesis method itself. Thus, one can find publications describing, among others, solution polymerization of the diamines with various FDCA derivatives [22][23][24][25][26], direct polycondensation method [25,27,28], interfacial polymerization [25,26,29,30] as well as solid-state polymerization [31,32]. The byproducts produced during the syntheses make that a method that would allow obtaining a large amount of pure material with high molecular weight is still sought after.…”

100% Bio-Based Polyamide with Temperature/Ultrasound Dually Triggered Reversible Cross-Linking

“…Furan-2,5-dicarboxylic acid (FDCA) and its derivatives (e.g., dimethyl furan-2,5-dicarboxylate (DMFDCA)) are the typical useful bio-derived platform compounds (industrial production in BASF), which were widely utilized to replace the conventional aromatic monomers for the synthesis of polyesters or polyamides. − Semi-bio-based polyamides with varied properties were synthesized by employing FDCA/DMFDCA and fossil-derived diamines. − The reversible Diels–Alder (DA) reaction enables more functionality for postmodification. − Compared to the commercial hexamethylene diamine, which is the monomer for fossil-based PA66, 1,5-pentanediamine (PDA) is a renewable but expensive monomer (industrial production in Cathay Biotech) that is produced from biomass lysine. − Recently, Ouyang, Chen, and co-workers developed a highly efficient biocatalytic approach to prepare PDA. , By using PDA to replace petroleum-based diamines, semi-bio-based aliphatic polyamides, such as PA56, were developed with better dimensional stability, lower density, and other superior properties. , …”