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Synthesis of tri‐aryl ketone amine isomers and their cure with epoxy resins
Author(s) -
Reyes Larry Q.,
Dao Buu,
Vogel Wouter,
Bijleveld Johan,
Tucker Sam,
Christensen Steve,
Wiggins Jeffrey,
Dingemans Theo,
Varley Russell J.
Publication year - 2020
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/pat.4818
Subject(s) - glass transition , diglycidyl ether , materials science , differential scanning calorimetry , aryl , benzene , ketone , ether , polymer chemistry , thermal stability , bisphenol a , bisphenol , epoxy , organic chemistry , polymer , chemistry , composite material , thermodynamics , alkyl , physics
Isomeric tri‐aryl ketone amines, 1,3‐bis(3‐aminobenzoyl)benzene (133 BABB), 1,3‐bis(4‐aminobenzoyl)benzene (134 BABB), and 1,4‐bis(4‐aminobenzoyl)benzene (144 BABB) are synthesized and cured with diglycidyl ether of bisphenol A and diglycidyl ether of bisphenol F in this work. Differential scanning calorimetry and near‐infrared spectroscopy reveal higher rate constants and enhanced secondary amine conversion with increasing para substitution attributed to resonance effects and the electron withdrawing nature of the carbonyl linkages. Glass transition temperatures increase from 133 BABB to 134 BABB, but decrease modestly for the 144 BABB hardener. With increasing para substitution, the flexural modulus and strength both decrease while the strain to failure increases but all BABB amines displaying higher mechanical properties than the corresponding 4,4‐diaminodiphenyl sulfone (44 DDS) networks. The thermal stability of the BABB networks is found to be modestly lower than 44 DDS, but char yields are significantly higher. Changes in thermal and mechanical properties are described in terms of molecular structure and equilibrium packing density.