Preparation and properties of aromatic polyamide‐esters from aminophenols and aromatic diacid chlorides

Abstract

Aromatic polyamide‐esters of moderately high molecular weight were prepared from various combinations of three aminophenols (m‐ and p‐aminophenol, and 4‐(4′‐aminophenoxy) phenol) and two aromatic diacid chlorides (isophthaloyl and terephthaloyl) by interfacial polycondensation in a cyclohexanone/water system and two‐phase polycondensation in a dichloromethane/water system with phase‐transfer catalysts. The solution polycondensation in dichloromethane/N,N‐dimethylacetamide was also successful for the production of high‐molecular‐weight polymers. The solubility of the aromatic polyamide‐esters varied markedly with polymer structure. Except for two polyamide‐esters derived from terephthaloyl chloride, all the other polymers were almost amorphous. These polymers had glass transition temperatures at around 200°C and showed 10% weight losses at about 400°C in both air and nitrogen atmospheres.

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

“…These results are quite similar to those reported previously. 1 Thus aromatic polyesters and polyamide-esters having inherent viscosities of 0.35-0.78 dL/g were readily obtained in almost quantitative yields that imply the formation of high-molecular-weight polymers.…”

“…The polycondensations of tetraphenylthiophene diacid chloride I with bisphenols I1 and those with aminophenols I11 affording polyesters IV and polyamide-esters V , respectively, proceed according to eqs. (1) and (2):…”

Interfacial Polymerization of Linear Aromatic Poly(ester amide)s

“…The choice of the organic solvent is more important since it will affect several other polymerization factors such as the potential partition of reactants between the two phases, the diffusion of the reactants, reaction rate and the solubility, swelling or permeability of the growing polymer [21]. It has been reported [24] that attempts to prepare polyester amides with high molecular weights by interfacial polymerization in a nonpolar solvent-water system failed because of early polymer precipitation. Therefore, inert polar solvents that are water-immiscible or at least partially water-soluble were chosen for interfacial polycondensation, as shown in Table 1, for the synthesis of representative polyester-amide (2CCBC-BPA) using identical reaction conditions.…”

“…In an attempt to prepare polymers of high glass transition temperature Tg, Imai et al [2,3] synthesized poly(ester amide)s (PEAs) of high molecular weight and Terephthaloyl chloride (TPCl) was prepared by the reaction of TPA with excess thionyl chloride, in the presence of a few drops of pyridine as catalyst. It was purified by crystallization from n-hexane.…”

Synthesis of aromatic polyesters having pendant carboxyl groups in the side chains and conversion of the carboxyl groups to other reactive groups

“…Since interfacial polycondensation of polyesters has been reported by Schnell and Conix,'" a variety of aromatic polymers are prepared by organic phase/ water phase polycondensation using phase transfer catalyst (PTC). [3][4][5][6] Recently, attention has been paid to reactive aromatic polyesters and p~lyamides.~ Aromatic polyesters having pendant carboxyl groups is an important class of functional polymers. Although the polymers having pendant carboxyl groups are synthesized and the pendant carboxyl groups are used for polymer reaction^,^^^ most of them are vinyl-type addition polymers.…”