Study on synthesis and characterization of novel optically active poly(amide-imide)s based on bis(p-aminobezoic acid)-N-trimellitylimido-S-valine via direct polycondensation

Abstract

N-Trimellitylimido-S-valine (3) was prepared by reaction of trimellitic anhydride (1) with S-valine (2) in acetic acid solution at refluxing temperature. This diacid was reacted with thionyl chloride and N-trimellitylimido-S-valine diacid chloride (4) was obtained in quantitative yield. The reaction of this diacid chloride with p-aminobenzoic acid was carried out in dry tetrahydrofurane and bis(paminobenzoic acid)-N-trimellitylimido-S-valine (5) was obtained as a novel optically active amide-imide diacid monomer in high yield. The direct poly condensation of amide-imide diacid monomer with aromatic diamins such as 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ether, benzidine, 4,4'-diaminodiphenyl methane, 1,4- phenylene diamine and 2,5-diamino toluene was carried out in tosyl chloride/ pyridine/dimethylformamide system. The resulting novel optically active poly(amide-imide)s (PAIs) with inherent viscosities ranging from 0.24-0.76 dLg-1, were obtained in good yield. All of these polymers were fully characterized with FTIR spectroscopy and specific rotation. Some elemental analysis, thermal properties and 1H-NMR of these new optically active PAIs are also reported.

Advances in synthetic optically active condensation polymers - A review

“…A series of optically active poly(amide-esterimide)s (PAEI)s based on bis(p-aminobezoic acid)-N-trimellitylimido-S-valine or L-isoleucine were prepared via polyesterification reaction of synthetic chiral diacids and different aromatic diols using TsCl/Py/(DMF) as a condensing agent by Mallakpour and coworkers ( Figure 22) [225,226]. The effect of the amount of DMF, aging time, reaction temperature, and reaction time was studied on the reaction yields and polymer viscosities.…”

“…Figure 22. Preparation of optically active PAEIs [225,226] Li et al [227] prepared PAEIs from amino acid (4-aminobenzoic acid, 3-aminobenzoic acid, or 6-aminohexanoic acid) and N-(4-hydroxyphenyl) phthalimide-4-carboxylic acid, N-(3-hydroxyphenyl) phthalimide-4-carboxylic acid, or N-(2-methyl-4-hydroxyphenyl) phthalimide-4-carboxylic acid in the presence of diphenylchlorophosphate and Py as direct condensation agents. The inherent viscosities of PAEIs were in the range of 0.13-0.95 dl/g.…”

Effect of modified ZnO capped withN-trimellitylimido-L-alanine diacid as an optically active coupling agent on the morphology and thermal properties of poly (amide-imide)/ZnO nanocomposites

“…[6,7] On the other hand, chiral PAIs are of special attention from the point of view of material science, because a high degree of amino acid functionality and chirality can lead to polymers with enhanced solubility, biocompatibility, and biodegradability. [8,9] For these manifest properties, they are selected as a matrix in the NCs technology. [4] Ionic liquids (ILs) are materials that are composed of ions.…”

Preparation and characterization of new thermally stable and optically active polyesters by direct polycondensation reaction promoted by Vilsmeier adduct

“…A direct and efficient approach for synthesizing chiral polymers is to introduce chiral elements into the macromolecule backbone or the side chains [6]. We have synthesized a variety of novel chiral monomers and polymers [7][8][9][10].…”