Preparation of new poly(amide–imide)s with chiral architectures via direct polyamidation reaction

Abstract

N-trimellitylimido-L-methionine (3) was prepared by reaction of trimellitic anhydride (1) with -L-methionine (2) in acetic acid solution at refluxing temperature. This diacid was reacted with thionyl chloride, and N-trimellitylimido-L-methionine diacid chloride (4) was obtained in quantitative yield. The resulting diacid chloride was reacted with p-aminobenzoic acid in dry acetone and bis(p-aminobenzoic acid)-N-trimellitylimido-L-methionine (5) was obtained as a novel optically active amide-imide diacid monomer in high yield. The direct polycondensation of amide-imide diacid monomer 5 with several aromatic diamines was carried out with tosyl chloride (TsCl)/pyridine (Py)/dimetheylformamide (DMF) system. The resulting thermally stable poly(amideimide)s (PAIs) were obtained in good yields and inherent viscosities ranging between 0.24 and 0.46 dL g À1 and were characterized with FTIR, 1 H NMR, CHN, and TGA techniques.

Advances in synthetic optically active condensation polymers - A review

“…The optically active PAIs were obtained after a short time of 3 min in good yields (53-95%) and inherent viscosities in the range of 0.17 to 0.61 dL/g. Moreover, this group [174,175] studied the direct polyamidation of above monomer with different aromatic diamines in order to prepare another series of optically active PAIs with inherent viscosities of 0.22-0.52 dL/g, based on L-leucine and L-methionine amino acids. Because of combination of aromatic backbone and aliphatic side chain in the presence of several functional groups, the solubility of these polymers was improved without significant loss in their thermal properties.…”

Construction and Characterization of Bionanocomposites Based on Optically Active Poly(Ester-Imide) Containing L-Amino Acids Using Nano-ZnO Surface-Coupled by γ-Methacryloxypropyl-Trimethoxysilane

“…Ultrasonic irradiation was carried out with the probe of the ultrasonic horn immersed directly in the mixture solution system with a frequency of 2.25 × 10 4 Hz and 100 W power. (2) as a diacid and PEI (3) were prepared according to previous works [24][25][26].…”

Synthesis and Properties of Novel Co-poly(Amide-Ester-Imide)s Containing a PEG-600 Linkage in the Main Chain

“…Therefore, the preparation of soluble PIs without a perceptible loss of favorable properties has been a major research interest and a great deal of effort has been expended to improve the processing characteristics of these relatively intractable polymers [3][4][5]. One of the successful approaches to improving solubility and processability is the incorporation of other functional groups, such as amide [6], ether [7], ester [8] and siloxane linkages [6,9,10], along the polymer skeleton and, consequently, the preparation of the appropriate co-PIs. Most conventional processing techniques for preparation of PIs involve the fabrication of poly(amic acid) precursors followed by thermal or chemical imidization.…”