Synthesis of multitask star‐shaped oligoaniline: Introducing a novel, efficient epoxy hardener

Multitask star‐shaped oligoaniline (S‐TAH) was synthesized using microwave irradiation in three steps: preparation of phthalic acid‐ capped tetra‐aniline (as the arm), synthesis of a tetrafunctional biobased core, and subsequently, coupling arms to the core, using a divergent approach. A biobased co...

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Bibliographic Details
Published in:Polymers for advanced technologies 2023-08, Vol.34 (8), p.2437-2450
Main Authors: Shahkarami, F., Moini, N., Kabiri, K., Piri, F., Jahandideh, A.
Format: Article
Language:English
Subjects:
Aniline
Bisphenol A
Condensates
conductive
Corrosion prevention
electrical conductivity
epoxy resin
Epoxy resins
Fourier transforms
hardener
Heat stabilizers
Lactic acid
microwave
NMR spectroscopy
Protective coatings
Stabilizers (agents)
star‐shaped
tetra‐aniline
Thermal resistance
Thermal stability
Thermomechanical analysis
thermomechanical properties
Weight loss
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Summary:Multitask star‐shaped oligoaniline (S‐TAH) was synthesized using microwave irradiation in three steps: preparation of phthalic acid‐ capped tetra‐aniline (as the arm), synthesis of a tetrafunctional biobased core, and subsequently, coupling arms to the core, using a divergent approach. A biobased core was synthesized through a direct condensation reaction of pentaerythritol, with l‐lactic acid. The chemical structures were extensively characterized using Fourier‐transform infrared and proton nuclear magnetic resonance spectroscopy. The performance of S‐TAH, as a multitask hardener for bisphenol A‐based epoxy resin (EP), was evaluated using differential scanning calorimetry, thermal gravimetric analysis, dynamic thermomechanical analyses (DMTA), and four‐prob conductometry. Peaks of cure exotherms for S‐TAH/EP (1:1) systems appear at 135°C with a tail‐like peak around 175°C. Compared to conventional amine‐cured EP, the thermal stability of the S‐TAH/EP cured was significantly higher, that is, ~ 40°C enhancement in half weight loss temperature (T50). A three‐fold improvement in char yield was observed. From DMTA, the material cured with S‐TAH displays representative storage moduli in glassy (9.4 GPa) and rubbery (5.2 GPa) states reflecting a uniform network and viscoelastic behavior. The electrical conductivities (σ) of the pure S‐TAH and the epoxy systems cured with S‐TAH/EP are 4.3 × 10−4, and 2.65 × 10−4, respectively. T star‐shaped oligoaniline is a promising multitask hardener—functioning as hardener, thermal stabilizer, electrically conductive and toughening agents—which can be versatilely applied in thermal resistance anticorrosive coatings and conductive adhesives.
ISSN:1042-7147
1099-1581
DOI:10.1002/pat.6062