Functionalized polysulfones from 4,4‐bis(4‐hydroxyphenyl)pentanoic acid, 2,2‐isopropylidenediphenol and bis(4‐chlorophenyl) sulfone: synthesis, behaviour and polymer analogous amidation of the carboxylic groups

Abstract

Two reactive polysulfones with carboxylic side groups were synthesized by polycondensation of different amounts of 4,4-bis(4-hydroxyphenyl)pentanoic acid (1) and 2,2'-isopropylidenediphenol (bisphenol-A, 2) with bis(4-chlorophenyl) sulfone (3). The amorphous polycondensate 4a was cast from solution in N,N-dimethylformamide (DMF) to produce a homogeneous membrane which is clear and colourless. With ethanol/water as permeate, preferred permeability of water occurs. Additionally, the carboxylic groups of 4 a were condensed with several alkylamines via the acyl chlorides. The obtained polysulfones with pendant alkylamido groups show a strong dependence of the glass transition temperature on the side chain length.

Synthesis and Characterization of Copoly(Ether Sulfone)s with Different Percentages of Diphenolic Acid Units

“…Figure S1 show FT-IR spectra of all copolymers. The adsorption bands at about 1347 cm −1 and 1140 cm −1 due to the asymmetric and symmetric stretching SO 2 moiety, respectively, were assigned in accord to the literature [17,20,[27][28][29].…”

Recent advances in the preparation of functionalized polysulfones

“…Polycondensation of 4,4‐bis(4‐hydroxyphenyl) pentanoic acid with bis(4‐chlorophenyl)sulfone yielded polysulfones with pendant carboxylic acid groups. This functionality readily condensed with alkylamines or alkoxy‐phenols to modify the solubility and glass transition of the polysulfones in a wide range …”

Thermal Degradation Processes of Aromatic Poly(Ether Sulfone) Random Copolymers Bearing Pendant Carboxyl Groups

“…These polymers have aroused a remarkable scientific and industrial interest, founding applications as adhesives for metal-to-metal bonds [ 2 ], membranes for separating gases and solids from solution or isolation of proteins [ 3 ], matrices for fiber-reinforced composites, as toughening agents for thermosetting resins [ 5 , 6 , 7 , 8 , 9 , 10 ] and for the manufacture of optical waveguiding materials [ 11 , 12 ]. It has been reported [ 16 , 17 , 18 , 19 , 20 , 21 ] that a wide spectrum of thermal, chemical and mechanical properties, as well as morphological behavior, can be obtained by varying the type of monomer units in the corresponding copolymers or by derivatization of preformed commercial PESs. In this work, we report the studies of thermal degradation processes on a series of functionalized random copoly(ether sulfones) having pendant carboxylic acid groups.…”

“…The thermal degradation behaviors of the copolymers were compared with those of the corresponding homopolymers: P(ESES) (commonly noted as PES) and P(ESDPA), synthesized in the same experimental conditions. As the knowledge of the degradation pattern of a polymer is an important step in choosing a material for product manufacture, the thermal degradation of either the homopolymers (PESs) [ 14 , 15 , 16 , 17 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ] or copoly(arylene ether sulfone) (referred as PES-PPO) was extensively studied [ 13 ]. Considerable efforts have been made to reveal the thermal degradation mechanisms and the thermal degradation products by mass spectrometry [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 32 , 33 ], thermogravimetry [ 30 ] and gas chromatography [ 31 ].…”

“…Pyrolysis products containing biphenyl and dibenzofuran units were also observed in the thermal degradation of PES-PPO copolymers at temperature higher than 500 °C [ 13 , 24 ]. Despite some previous studies on poly(ether sulfones) containing DPA units [ 16 , 17 , 18 , 19 , 34 , 35 , 36 ], until now, no detailed information on the thermal degradation mechanisms occurring during the thermal degradation of the P(ESDPA)-based polymers have been available in the literature. In this work, we aimed to obtain this information by direct-pyrolysis mass spectrometry (DPMS), stepwise pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) and thermogravimetric analysis (TGA).…”