Simultaneous Anionic Ring-Opening and Condensation Reactions for the Synthesis of Aliphatic–N-Alkyl Aromatic Copolyamides

Abstract

The copolymerization of ε-caprolactam with ethyl 4-(butylamino)benzoate was shown to occur in the presence of sodium salts and an acyllactam as activator in a one-step bulk reaction. The mechanism is based on the deprotonation of the two monomers yielding activated species able to attack an acyllactam or an ester group at the polymer chain ends. Novel copolyamides with different percentages of aromatic/aliphatic units were synthesized in a one-step bulk copolymerization within a few minutes at 140 °C and characterized by NMR spectroscopy, size exclusion chromatography, and thermal analysis (DSC). This methodology, combining simultaneous anionic ring-opening and condensation reactions, affords a new synthetic pathway to introduce an aromatic unit in an aliphatic polyamide backbone, and more specifically a polyamide 6 containing about 20 mol % of N-alkyl aromatic amides was prepared.

Effect of Oleic Acid Coating of Iron Oxide Nanoparticles on Properties of Magnetic Polyamide-6 Nanocomposite

“…22 The favoured NP morphology and crystalline phases obtained after functionalization can significantly affect the magnetic properties and crystallinity of the synthesized nanocomposites. 23 The use of oleic acid as a capping agent results in hydrophobic coating, as polar end groups attach to the NP surface and form a strongly bonded protective monolayer, which enhances the uniform dispersion of the NPs. 24 In order to study the effect of oleic acid (OA) loading in the coating of iron oxide NPs on nanocomposite properties, a magnetic nanocomposite was prepared by keeping the 1 wt.% iron oxide NP concentration constant but varying the OA loading on the surface of the NPs.…”

Poly(ε-lysine) and its derivatives via ring-opening polymerization of biorenewable cyclic lysine

“…Functional polyamides that feature tunable mechanical properties, low toxicity, therapeutic potential, and structural similarity to peptides (amide bonds) exhibit enormous potential in the application of biomedical materials and other fields. [22][23][24]47,[63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79] We have developed a cyclization reaction of biorenewable lysine to yield ε-lactam monomer with a protected α-amino group. ROP of the obtained monomer, followed by deprotection, afforded polyamides bearing pendant amines [ poly(ε-lysine)].…”

Polymers and Related Composites via Anionic Ring-Opening Polymerization of Lactams: Recent Developments and Future Trends

“…Bakkali-Hassani et al [ 86 ] developed a novel route for copolymerization thereby combining the AROP of CL with condensation reaction using esters (ethyl-4-butylaminobenzoate). The authors varied the content of the aromatic units in this aliphatic- N -alkyl aromatic copolymer between 3 and 27 mol %.…”