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. 2022 Dec 7;14(24):5334.
doi: 10.3390/polym14245334.

Curing of DER-331 Epoxy Resin with Arylaminocyclotriphosphazenes Based on o-, m-, and p-methylanilines

Artem A Rybyan  1 , Julia V Bilichenko  1 , Vyacheslav V Kireev  1 , Alexander A Kolenchenko  1 , Evgeniy M Chistyakov  1
Affiliations

Curing of DER-331 Epoxy Resin with Arylaminocyclotriphosphazenes Based on o-, m-, and p-methylanilines

Artem A Rybyan et al. Polymers (Basel). .

Abstract

As a result of this research, it was established that the chlorine atom replacement rates in hexa-chlorocyclotriphosphazene by o-, m-, and p-methylanilines' temperatures are crucial in determining which reaction is made. The speed of reaction practically does not affect the polarity of the synthesis solvent. For the formation of fully substituted o-, m-, and p-arilaminocyclotriphosphazenes, the reaction takes 5 h and is carried out in the diglyme at its boiling temperature. The structure of the synthesized AAP was confirmed by 31P and 1H NMR spectroscopy and MALDI-TOF mass spectrometry. By means of synchronous DSK and TGA, it is found that the synthesized AAP are crystalline and their thermal destruction has a stepped character. Thermal destruction is shown to be accompanied by the simultaneous removal of three aniline molecules from the AAP molecules. Conducted curing of epoxy resin DER-331 is carried out using the AAP as a curing agent. It has been established that due to steric difficulties, o- AAP does not interact with epoxy resin, unlike m- and p- AAP. The gel fraction in curing resin is measured, and the AAP relate to the stage processes of macromolecule formation. The result is that polymers based on DER-331 and m-, p-AAP have a gel fraction content up to 97 mass. %. These polymers have glass-transition temperatures 80 and 85 °C (m- and p-AAP-based, respectively) and demonstrate fire resistance to standard UL-94 of category V-0.

Keywords: aminocyclotriphosphazenes; cyclotriphosphazenes; deaminolysis; epoxy resin; modifiers.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Scheme of obtaining AAP.
Figure 2
Figure 2
31P (left), 1H (in the middle), and MALDI-TOF (right) spectra o-AAP, m-AAP, and p-AAP.
Figure 3
Figure 3
TGA and DSC curves AAP (arrows show which scale corresponds to which thermograms).
Figure 4
Figure 4
IR spectra preheating and post-heating (termal).
Figure 5
Figure 5
AAP pyrolysis flow circuit and the expected structure of the resulting product.
Figure 6
Figure 6
MALDI-TOF (A) and 31P NMR (B) spectra product pyrolysis m-AAP.
Figure 7
Figure 7
Diagram of the probable interaction of oxirane groups with AAP in the hardening of epoxy resin.
Figure 8
Figure 8
TGA and DSC thermogram of compositions based on DER-331 containing 15 mass. % m- or p-AAP (arrows show which scale corresponds to which thermograms).
See this image and copyright information in PMC

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