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Preparation and properties of poly(amide‐thioether)s from bis( p ‐aminophenyl)sulfide and various aliphatic diacids
Author(s) -
Zhang J. K.,
Zhu C. S.,
Wang Y. W.,
Cao S. K.
Publication year - 1999
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/(sici)1099-1581(199901/02)10:1/2<48::aid-pat765>3.0.co;2-b
Subject(s) - condensation polymer , thioether , monomer , polyamide , polymer chemistry , amide , pyridine , sulfide , dimethylformamide , diamine , organic chemistry , salt (chemistry) , materials science , polymer , chemistry , solvent
Aromatic‐aliphatic poly(amide‐thioether)s were prepared by conventional polycondensation of bis(p‐aminophenyl)sulfide (BAPS) with aliphatic diacyl chlorides or one‐pot polycondensation of BAPS with aliphatic diacids. The dinitro compound for the preparation of diamine monomer was prepared through the nucleophilic displacement of sodium sulfide (Na 2 S) with p‐chloronitrobenzene in N, N‐dimethylformamide (DMF). BAPS was then obtained through the reduction of the dinitro compound with iron in EtOH/H 2 O. After acidifying. BAPS was finally obtained as a hydrochloride salt. The conventional polycondensation of BAPS with different aliphatic diacyl chlorides was carried out in N‐methyl‐2‐pyrrolidone (NMP) containing 3–4 wt% of CaCl 2 with pyridine as acid acceptor, and the poly(amide‐thioether)s obtained had inherent viscosities of 0.25–0.5 dl/g in DMF/NMP (1:4, with 3 wt% of CaCl 2 ) at 30 ± 0.2°C. One‐pot polycondensations of BAPS dihydrochloride salt (BAPS‐DS) with aliphatic diacids were carried out using SOCl 2 as the condensing agent at 70°C for 3 hr in DMF, yielding polymers having relative viscosities of 1.5–1.65 in H 2 SO 4 (98.5%) at 30 ± 0.2°C. Thermal analysis illustrated that the melting points and decomposition temperatures of the obtained polymers are in accordance with the length of the methylene segments derived from the aliphatic diacid monomers. Copyright © 1999 John Wiley & Sons, Ltd.