Synthesis and characterization of copolyamides derived from novel aliphatic bio‐based diamine

Abstract

Novel aliphatic nylon 6 (PA6) copolyamides were produced by melt polymerization reaction of our newly synthesized aliphatic bio‐based diamine monomer: N1, N6‐bis (4‐aminobutyl) adipamide (BABA). The pertinent long‐chain polyamide salt (BABA/SA) monomer was isolated as white solid, utterly characterized for the first time. The chemical structure of BABA, BABA/SA salt, and copolyamides (PA6‐BABA/SA) were investigated by 1H NMR and FTIR spectroscopy. Depending on the chemical compositions, the viscosity and molecular weight of the copolyamides were in the range of 20 275–12 652 and 2.81–2.12 dL/g. With increasing BABA/SA salt weight content in the synthesized copolyamides, their melting temperatures (Tm) and glass transition temperatures (Tg) decreased from 211.0 to 164.0 °C and 66.6 to 43.5 °C. In addition XRD results were investigated revealing all the copolyamides transferred from α‐form to γ‐form. Interestingly, the as‐synthesized all copolyamides possess nearly similar thermal stability (Td = 452.2–449.5 °C) as neat PA6. Mechanical testing data revealed that with increasing BABA/SA salt content, the elongation at break of copolyamides are increased (726.19–429.34%), while the tensile strength are decreased. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46878.

Isothermal Crystallization Kinetics Study of Fully Aliphatic PA6 Copolyamides: Effect of Novel Long-Chain Polyamide Salt as a Comonomer

“…BABA (N 1 , N 6 -bis (4-aminobutyl) adipamide) diamine, BABA/SA salt, and PA6-BABA/SA copolyamides (Scheme 1) were synthesized in our laboratory, as described in our earlier work [22]. Their chemical structure was confirmed by 1 H NMR and FTIR spectroscopy.…”

“…The RV of the polyamides was calculated using the solvent flow time and the polymer solution flow time in the viscometer. The molecular weight ( M w ) of the PA6-BABA/SA copolyamides were obtained from our previously published literature [22].…”

“…We found that the crystallization behavior of these two series of copolyamides may be regulated by the types of monomers and their amount. In a subsequent investigation [22], we synthesized a series of PA6 copolyamides (PA6-N 1 , N 6 -bis (4-aminobutyl) adipamide (BABA)/sebacic acid (SA)) using novel long-chain diamine (N 1 , N 6 -bis (4-aminobutyl) adipamide) diamine, BABA), and polyamide salt (BABA/SA) monomers. These polyamides have low-melting points that are comparable to that of neat PA6.…”

Modern biopolyamide-based materials: synthesis and modification

“…Examples of specific biopolyamides' properties in relation to the monomer type are collected in Table 1. The physical properties of polyamides, such as glass transition and melting temperature, mechanical strength and water absorption, can be adjusted by copolymerization of monomers with different chain length and structure [33,61].…”

Effect of Bis (2-Aminoethyl) Adipamide/Adipic Acid Segment on Polyamide 6: Crystallization Kinetics Study

“…BAEA has a significant effect on destroying the crystallinity of PA6, and its copolyamides have outstanding mechanical properties for hot melt adhesive applications [ 16 , 17 ]. Additionally, a series of low-melting PA6 copolyamide has already been successfully synthesized successfully using other novel diamines (i.e., bis(4-aminobutyl) terephthalamide (BABT), bis (4-aminobutyl) adipamide (BABA), bis-(2-aminoethyl)adipamide (BAEA)) and organic salts (i.e., bis(4-aminobutyl) terephthalamide/sebacic acid (BABT/SA), bis (4-aminobutyl) adipamide/sebacic acid (BABA/SA), bis (4-aminobutyl) adipamide/adipic acid (BABA/AA), bis (2-aminoethyl) adipamide/1,4-cyclohexanedicarboxylic acid (BAEA/CHDA)), and bis (2-aminoethyl) adipamide/adipic acid (BAEA/AA) prepared by our research group [ 17 , 18 , 19 , 20 , 21 ]. On the other hand, the effect of BABA/SA on the crystallization behavior in the main chain of PA6 was also described using the method of isothermal crystallization kinetics [ 22 ].…”