Synthesis and characterization of aromatic polyesteres and polyamide–esters from bisphenols and aromatic aminophenols, and 2,5‐bis(4‐chloroformyl)‐3,4‐diphenylthiophene

Abstract

SynopsisPolycondensation of 2,5bis(4chloroformyl)-3,4-diphenylthiophene (I) with various bisphen-01s afforded tetraphenylthiopheneontaining aromatic polyesters by the interfacial or solution polycondeneation method. Polyamide-esters were obtained from I and aminophenols by means of the interfacial technique. These polymers had inherent visctsities of 0.4-0.8 dL/g. All the polymers were readily soluble in various organic solvents, and could be cast into transparent and flexible films. Their glass transition temperatures were in the range of 235-335°C. These polymers did not lose weight below 4WC in either air or nitrogen. This paper constitutes the sixth in a series of articles dealing with tetraphenylthiophene-containing polymers, and reports the synthesis of new soluble aromatic polyesters and polyamide-esters that have high Td's by the interfacial or solution polycondensation of 2,!5-bis(4-chloroformyl)-3,4diphenylthiophene with various bisphenols and aminophenols. EXPERIMENTALMaterials 2,5Bis(4-~hloroformy1)-3,4,diphenylthiophene (I 1 was synthesized according to the method reported previously.8 2,2-Bis(4-hydroxyphenyl)propane (Ha) was purified by recrystallization from benzene. 344HydroxyphenyD

Synthesis and Characterization of Novel Polyarylates from 2,5-Bis(4-hydroxyphenyl)-3,4-diphenylthiophene and Various Aromatic Dicarboxylic Acids

“…26, No. 3,1994 the tetraphenylthiophene-containing polyarylates markedly differed from that of the structurally related tetraphenylfuran-and tetraphenylpyrrole-based polyarylates, 4 • 5 most of which were soluble easily in the above solvents. Figure l shows the wide angle X-ray diffraction diagrams of the polyarylates.…”

“…1 • 2 We already reported that the introduction of pendant phenyl groups through tetraphenylthiophene, 3 tetraphenylfuran, 4 and tetraphenylpyrrole units 5 into polyarylate backbones afforded organic-soluble polymers with high glass transition temperatures. The incorporation of these tetraphenylated heterocylic moieties were also found to be highly effective to produce aromatic polyamides and polyimides with the above desirable properties.…”

“…[6][7][8][9][10][11][12] 2, 5-bis( 4-hdroxyphenyl)-3 ,4-di pherw l thiophene, as an alternative monomer to the polyarylate-forming diacid, 2,5-bis( 4-carboxyphenyl)-3,4-diphenylthiophene. 3 This article deals with the synthesis of the tetraphenylthiophenediol as well as of new tetraphenylthiophene-containing polyarylates derived from various aromatic dicarboxylic acid chlorides. Their properties are also described, which are compared with those of the tetraphenylated heterocycle-containing polyarylates reported previously.…”

Synthesis and Characterization of New Unsaturated Polyesters Containing 4‐Phenylcyclohexanone Moiety in the Main Chain

“…Therefore, development of polyesters for use at high temperature with improved solubility is an important goal. One of the approaches to improve solubility of the polymers without extreme loss of their high thermal stability is the introduction of polar and flexible groups into the polymer backbone (9,10). The incorporation of bulky pendent groups can also provide beneficial effect for solubility because this approach produces a separation of chains and lowering the chain packing with a gain of free volumes.…”

Synthesis and properties of aliphatic spirodilactam diphenol containing polyesters

“…One of the approaches to improve solubility of the polymers without extreme loss of their high thermal stability is the introduction of polar and flexible groups into the polymer backbone [9][10][11][12][13]. The incorporation of bulky pendent groups can also provide beneficial effect for solubility because this approach produces a separation of chains and lowering the chain packing with a gain of free volumes.…”