Microwave‐promoted rapid synthesis of new optically active poly(amide imide)s derived from N,N′‐(pyromellitoyl)‐bis‐L‐isoleucine diacid chloride and aromatic diamines

Abstract

ABSTRACT:A pyromellitic dianhydride (benzene-1,2,4,5-tetracarboxylic dianhydride) was reacted with l-isoleucine in acetic acid, and the resulting imide acid [N,NЈ-(pyromellitoyl)-bis-l-isoleucine] (4) was obtained in a high yield. 4 was converted into N,NЈ-(pyromellitoyl)-bis-l-isoleucine diacid chloride by a reaction with thionyl chloride. The polycondensation reaction of this diacid chloride with several aromatic diamines, including 1,4-phenylenediamine, 4,4Ј-diaminodiphenyl methane, 4,4Ј-diaminodiphenylsulfone (4,4Ј-sulfonyldianiline), 4,4Ј-diaminodiphenylether, 2,4-diaminotoluene, and 1,3-phenylenediamine, was developed with two methods. The first method was polymerization under microwave irradiation, and the second method was low-temperature solution polymerization, with trimethylsilyl chloride used as an activating agent for the diamines. The polymerization reactions proceeded quickly and produced a series of optically active poly(amide imide)s with good yields and moderate inherent viscosities of 0.17-0.25 dL/g. All of the aforementioned polymers were fully characterized by IR, elemental analyses, and specific rotation. Some structural characterization and physical properties of these optically active poly(amide imide)s are reported.

Microwave‐Assisted Polymer Synthesis: State‐of‐the‐Art and Future Perspectives

“…beginning of this Section). [41] Findings from the above-described series were successfully transferred to the synthesis of polymers from N,N 0 -(4,4 0 -carbonyldiphthaloyl)-bis-L-alanine diacid chloride with bulky derivatives of tetrahydropyrimidone and Scheme 3. Poly(amide imide)s prepared in microwave reactors, Part I: (a) optically active poly(amide imide)s from pyromellitic diacid anhydride, L-amino acids, and 5,5-disubstituted hydantoin derivatives; (b) polymers containing a carbonyldiphthaloyl unit; (c) poly(amide imide)s with tetrahydro-2-thioxopyrimidines in the main chain.…”

Optically active and organosoluble poly(amide-imide)s derived fromN,N′-(Pyromellitoyl)bis-l-histidine and various diamines: Synthesis and characterization

“…So these polymers are readily soluble in polar amidic solvents rather than another N,N'-(pyromellitoyl)bis-L-amino acid. [32][33][34] Optically active, thermal stability and organosoluble properties can make these polymers attractive for practical applications such as processable high-performance engineering plastics, constructing chiral media for asymmetric synthesis, chiral stationary phases for resolution of racemic mixtures by chromatographic techniques, chiral liquid crystals in ferroelectrics and nonlinear optical devices. [35][36][37] …”

The effect of carboxylated multi-walled carbon nanotubes on reinforcement efficiency of thiazole-bearing poly(amide-imide) composites

“…Synthesis and structural characterization of monomers Diacid monomer was synthesized by the condensation reaction of an equimolar amount of pyromellic anhydride and S-valine amino acid in reflux acetic acid solution. [26] Iron oxide hydroxide catalyst was prepared according to the literature. [23] 3,5-Dinitro-N-(thiazol-2-yl)benzamide (3) was also prepared according to the reported procedure.…”