Synthesis and thermal behavior of novel poly(thiourea-amide)s derived from 1-(4-aminobenzoyl)-3-(3-aminophenyl) thiourea

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The novel difunctional monomer, 1-(4-aminobenzoyl)-3-(3-aminophenyl) thiourea (ABAPT), was synthesized by the reduction of NBNPT (1-(4-nitrobenzoyl)-3-(3-nitrophenyl) thiourea). The characterization of the monomers was carried out using spectroscopic and elemental analyses. A series of novel aromatic and aromatic-aliphatic poly (thiourea-amide)s (PAMDs) were obtained through the condensation of ABAPT with various diacid chlorides (terephthaloyl, isophthaloyl, sebacoyl and adipoyl chloride). Structural elucidation of the resulting polyamides was carried out by FTIR, (1)H- and (13)C-NMR techniques along with solvent miscibility, viscosity, molecular weight, crystallinity, non-flammable and thermal studies. The polymers bearing phenylthiourea moieties in the backbone were obtained in quantitative yield. PAMDs having inherent viscosities of 1.02-1.32 dL g(-1) exhibited good organosolubility in amide solvents (N,N-dimethylacetamide, dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone). X-ray diffraction studies specified crystalline behavior of new polyamides. Gel permeation chromatography measurements disclosed M(w) around 34 000-65 000. The thermogravimetric analyses and limiting oxygen index measurements indicated that aromatic polyamides were stable up to 500 degrees C and were adequately flame retardant. Moreover, their glass transition temperatures were found to be 265-273 degrees C.
Publisher
SAGE PUBLICATIONS LTD
Issue Date
2011
Language
English
Article Type
Article
Keywords

ONE-POT SYNTHESIS; AROMATIC POLYAMIDES; EFFICIENT SYNTHESIS; POLYMERS; ISOTHIOCYANATES; ETHER; PHENYLTHIOUREA; CONDENSATION; TEMPERATURE; POLYIMIDES

Citation

HIGH PERFORMANCE POLYMERS, v.23, no.6, pp.424 - 433

ISSN
0954-0083
URI
http://hdl.handle.net/10203/99945
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