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Polyamides obtained by direct polycondesation of 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl] fluoren‐9‐YL]‐2‐methyl‐phenoxy]aniline with dicarboxylic acids based on a diphenyl‐silane moiety
Author(s) -
TundidorCamba Alain,
Terraza Claudio A.,
Tagle Luis H.,
Coll Deysma
Publication year - 2010
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.33443
Subject(s) - moiety , fluorene , polymer chemistry , diamine , aniline , silane , monomer , condensation polymer , glass transition , chemistry , inherent viscosity , thermal decomposition , materials science , polymer , intrinsic viscosity , organic chemistry
Polyamides (PAs) containing fluorene, oxyether, and diphenyl‐silane moieties in the repeating unit were synthesized in > 85% yield by direct polycondesation between a diamine and four dicarboxylic acids. Alternatively, one PA was synthesized from an acid dichloride. The diamine 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl]fluoren‐9‐yl]‐2‐methyl‐phenoxy]aniline ( 3 ) was obtained from the corresponding dinitro compound, which was synthesized by nucleophilic aromatic halogen displacement from p ‐chloronitrobenzene and 9,9‐bis (4‐hydroxy‐3‐methyl‐phenyl)fluorene ( 1 ). Monomers and polymers were characterized by FTIR and 1 H, 13 C, and 29 Si‐NMR spectroscopy and the results were in agreement with the proposed structures. PAs showed inherent viscosity values between 0.14 and 0.43 dL/g, indicative of low molecular weight species, probably of oligomeric nature. The glass transition temperature ( T g ) values were observed in the 188–211°C range by DSC analysis. Thermal decomposition temperature (TDT 10% ) values were above 400°C due to the presence of the aromatic rings in the diamine. All PAs showed good transparency in the visible region (>88% at 400 nm) due to the incorporation of the fluorene moiety. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011