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Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization
Author(s) -
TundidorCamba Alain,
Araya Nélida,
GonzálezHenríquez Carmen M.,
Tagle Luis H.,
Hauyon René A.,
Sobarzo Patricio A.,
RodríguezGonzález Fidel E.,
Jessop Ignacio A.,
RecabarrenGajardo Gonzalo,
Terraza Claudio A.
Publication year - 2019
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.48055
Subject(s) - polymer chemistry , thermal stability , gel permeation chromatography , differential scanning calorimetry , condensation polymer , monomer , thermogravimetry , ether , epoxide , diamine , chemistry , alkyl , materials science , polymer , organic chemistry , catalysis , inorganic chemistry , physics , thermodynamics
Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether‐azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4‐formylbiphenyl‐4‐yl)dialkylsilane (alkyl: methyl, phenyl) with 84–93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy ( 1 H, 13 C, and 29 Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2–11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV–vis region. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 48055.