Introduction of amino, aliphatic, and aliphatic carboxylic acid side groups onto poly(arylene ether sulfone)s via transimidization reactions

Abstract

A versatile approach for the functionalization of a bisphenolic monomer, 3,8‐bis(4‐hydroxyphenyl)‐N‐phenyl‐1,2‐naphthalimide (1) as well as its corresponding poly(N‐phenyl imido aryl ether sulphone) via transimidization reactions with hydrazine monohydrate, aliphatic amines, and an amino acid (11‐amino undecanoic acid) is reported. The reactions proceeded in high conversion and high isolated yield to the desired novel functionalized monomers or polymers with N‐amino, N‐aliphatic, and N‐aliphatic acid pendant groups. The N‐amino functionalized monomer, 2, was reacted cleanly with naphthalic anhydride to form a bisimide. Polymers with phthalimide (7), 3‐carboxy phthalimide (9), and bisphenol‐A‐(monoimide monoanhydride) (8) pendant groups were also formed by imidization of 6. A polymer with a cyclopropyl amide functional group, 10, was formed by reacting 6 with cyclopropyl carbonyl chloride. A brief description of the transimidization reactions and the properties of the functionalized polymers is included. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 1095–1108, 1997

Synthesis and functionalization of poly(ether sulfone)s based on 1,1,1‐tris(4‐hydroxyphenyl)ethane

“…These properties include high stability against hydrolysis, high thermal stability, high stability against oxidation and UV light, low inflammability, high glass‐transition temperatures, and good transparency when the PESs are amorphous. To vary their properties and broaden their applications, numerous research groups have synthesized functionalized PESs either by direct synthesis from functionalized monomers1–7 or by derivatization of preformed (commercial) PESs 8–17. A third approach consists of the preparation of star‐shaped or hyperbranched PESs 18, 19.…”

Dielectric properties of sol–gel synthesized polysulfone–ZnO nanocomposites

“…These thermoplastic, amorphous, and rigid polymers offer useful physical, mechanical, and electrical properties which are maintained over a broad temperature range, due to their morphological structure. It has a good thermo-oxidative stability and flame retardancy, so it is a superior replacement of polycarbonate [18,19]; polysulfone provides a resistance to high temperature, acts as a flame retardant without compromising its strength that usually results from addition of flame retardants, and is used as a dielectric in capacitors [20]. ZnO one of the multifunctional inorganic nanoparticles has drawn increasing attention of many researchers in recent years due to its significant physical and chemical stabilities, high catalysis activity, and intensive ultraviolet and infrared adsorption [21].…”

Crosslinked polysulfone obtained by Wittig‐Horner reaction in biphase system

“…[9] also by this process, it is possible to increase the reactivity of the main chain by introducing new reactive functional groups that permit further chemical reactions. The chemical modification of polysulfones has been reported using sulfonation [10, 11], nitration [12], lithiation [13], and by the introduction of various functional groups, such as carboxylic (COOH) [14, 15], fluorine (F) [16], amine (NH 2 ) [17], azide (N 3 ) [18], and aliphatic unsaturated end groups [19]. Chloromethylation of polysulfone, as an example of chemical modification, has been performed by many research groups by different synthetic routes [20, 21].…”