Synthesis and characterization of organosoluble poly(arylate‐imide)s prepared from direct polycondensation of bis(trimellitimide)‐diacids and various bisphenols

Abstract

Three diimide-diacids, 2,2-bis[4-(4-trimellitimidophenoxy)phenyl]hexafluoropropane (I-A), 2,2-bis[4-(4-trimellitimidophenoxy)phenyl]propane (I-B), and 5,5Ј-bis[4-(4-trimellitimidophenoxy)phenyl]hexahydro-4,7-methanoindan (I-C), were prepared by the azeotropic condensation of trimellitic anhydride with three analogous diamines. Three series of alternating aromatic poly(arylate-imide)s, having inherent viscosities of 0.41-0.82 dL/g, were synthesized from these diimide-diacids (I-A, I-B, and I-C) with various bisphenols by direct polycondensation using diphenyl chlorophosphate and pyridine as condensing agents. All of the polymers were readily soluble in a variety of organic solvents such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, and even in the less polar tetrahydrofuran. These polymers could be cast into transparent and tough films, which had strength at break values ranging from 73 to 98 MPa, elongation at break from 6 to 11%, and initial modulus from 1.6 to 2.2 GPa. The softening temperatures of the polymers were recorded at 145-248°C. They had 10% weight loss at a temperature above 450°C and left 35-51% residue even at 800°C in nitrogen.

Synthesis and characterization of poly(ester‐ether‐imide)s derived from 5‐(4‐trimellitimidophenoxy)‐1‐trimellitimido naphthalene

“…The reaction between aromatic diamines and trimellitic anhydride is a usual manner to prepare imide ring‐containing aromatic dicarboxylic acids 1–7. This route is widely used in the field of polymeric materials for the synthesis of some copolyimides such as poly(amide‐imide)s8–12 and poly(ester‐imide)s 13–17. According to this strategy, 5‐(4‐aminophenoxy)‐1‐naphthylamine reacted with two mole equivalents of trimellitic anhydride in refluxing glacial acetic acid to obtain 5‐(4‐trimellitimidophenoxy)‐1‐trimellitimido naphthalene ( 1 ).…”

Synthesis and characterization of new optically active and organosoluble poly(ester-imide)s based on bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide by direct polycondensation

“…However, these polymers are generally intractable and lack the properties essential for successful fabrication into useful forms because of their high melting or glass-transition temperatures and limited solubility in organic solvents [3]. One of the successful approaches to improving solubility is the incorporation of other functional groups, such as amide, ether, ester and siloxane linkages, along the polymer skeleton and, consequently, the preparation of the appropriate copolyimides [4][5][6][7][8][9][10][11][12].…”

<b>Synthesis and characterization of new optically active poly(amide-imide)s based on <i>N</i>-trimellitimido-<i>L</i>-amino acid and trimethylene units</b>

“…However, these polymers are generally intractable and lack the properties essential for successful fabrication into useful forms because of their high melting or glass-transition temperatures and limited solubility in organic solvents. Therefore, copolyimides, such as poly(amide-imide)s and poly(acrylat-imide)s, have been developed [3][4][5][6][7]. Poly(amideimide)s (PAIs) are well known as a class of polymers with good compromise between thermal stability and processability.…”