Oligo(ether‐sulfones), 2. Synthesis of a novel macrocyclic aromatic ether sulfone bearing two carboxylic groups and the corresponding polyamide via direct condensation of the macrocycle with 4,4′‐diaminodiphenylmethane

Abstract

A new macrocyclic arylene ether sulfone bearing two carboxylic groups, 4, was prepared by use of pseudo high dilution techniques. In a first step, 4,4-bis[4-(4-(4-chlorophenylsulfonyl)phenoxy)phenyl]pentanoic acid (3) was prepared from bis(4-chlorophenyl) sulfone (1) and an excess of 4,4-bis(4-hydroxyphenyl)pentanoic acid (2). Then, the purified trimer 3 was cyclocondensed with 4,4-bis(4-hydroxyphenyl)pentanoic acid (2), yielding the bifunctionalized macrocycle 4. The existence of the ring-shaped molecule was proved by use of MALDI-TOF, NMR-and IR-spectroscopy. The free carboxylic groups of 4 were used to build up polyamides that contain the macrocycle in the main chain and 4.4'-diaminodiphenylmethane (5) as an aromatic diamine. a) part 1 : cf. ref. ')

Oligo(ether sulfones). 3. Block Copolymers via Condensation Reactions of Telechelic Oligo(ether sulfones) Bearing Phenolic Endgroups and Oligomeric α,ω-Diols

“…OES with Phenol Endgroups (3a, 3b). The synthesis was conducted similar to the preparation of oligo(ether sulfone)s bearing chlorophenyl endgroups described in earlier papers. , Bis(4-chlorophenyl)sulfone ( 2 ) was dissolved in a mixture of dry DMSO and toluene. K 2 CO 3 was added to the solution (Table ).…”

“…Recently some blockpolymers containing polysulfone segments were described in combination with LC polymers 12 or as a middle segment in triblock copolymers. 13,14 Up to now, these polysulfone segments were only synthesized from Bisphenol A and bis(4-chlorophenyl)sulfone (2). The synthesis of step-growth block copolymers with poly(aryl ether) segments, which have been combined with glassy polystyrene or polycarbonate blocks, has been reported by McGrath et al 15 However, no block copolymers bearing functionalized polysulfones as block components are known from the literature.…”

Trends in polymer chemistry 1997 Part 1: Pure research

“…265 8C and is thermally stable up to 380 8C. The synthesis of a new bifunctional macrocyclic ethersulfone through copolymerization using the high dilution technique and its polycondensation with aromatic diamines was described [55]. The resulting polyamide macromolecule, which contains macrocycles in its main chain, could be of interest in host -guest chemistry (Fig.…”

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

“…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).…”