Synthesis of tri-aryl ketone amine isomers and their cure with epoxy resins

Larry Q. Reyes, Buu Dao, Wouter Vogel, Johan Bijleveld, Sam Tucker, Steve Christensen, Jeffrey Wiggins, Theo Dingemans, Russell J. Varley

Research output: Contribution to journalArticleScientificpeer-review

Abstract

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.

Original languageEnglish
Number of pages11
JournalPolymers for Advanced Technologies
DOIs
Publication statusPublished - 2019

Keywords

  • epoxy amine crosslinked networks
  • reaction kinetics
  • structure property relationships

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    Reyes, L. Q., Dao, B., Vogel, W., Bijleveld, J., Tucker, S., Christensen, S., Wiggins, J., Dingemans, T., & Varley, R. J. (2019). Synthesis of tri-aryl ketone amine isomers and their cure with epoxy resins. Polymers for Advanced Technologies. https://doi.org/10.1002/pat.4818