Synthesis, characterization and thermal polymerization
of new 3,4-dihydro-2H-1,3-naphthoxazine monomers

A. U. G. Gabbas; M. B. H. Ahmad; N. Zainuddin; N. A. Ibrahim

doi:10.14314/polimery.2017.086

Published : 2021-01-15

Vol. 62 No. 2 (2017)

Synthesis, characterization and thermal polymerization of new 3,4-dihydro-2H-1,3-naphthoxazine monomers

A. U. G. Gabbas M. B. H. Ahmad N. Zainuddin N. A. Ibrahim

DOI: https://doi.org/10.14314/polimery.2017.086

Abstract

Two new 1,3-naphthoxazine monomers (M-A and M-B) were synthesized via a modified stepwise procedure in which methylene bromide was used for the ring-closure reaction. Condensation of 2-hydroxy-1-naphthaldehyde with 1,6-hexamethylenediamine or 1,4-phenylenediamine gives imine compounds, which were converted to 2-hydroxynaphthylamines by reduction with NaBH₄ in methanol. Ring-closure reaction between the 2-hydroxynaphthylamines and methylene bromide results in the formation of 1,3-naphthoxazine monomers M-A or M-B with good yields. The structures of the synthesized monomers were confirmed using different spectroscopic techniques (including FT-IR, ¹H NMR and ¹³C NMR), mass spectrometry, and elemental analysis. Thermal polymerization of the monomers was investigated by FT-IR and differential scanning calorimetry (DSC). Both the 1,3-naphthoxazine monomers undergo ring-opening polymerization, leading to the formation of the corresponding polynaphthoxazines [P(M-A) and P(M-B)]. The thermal stability of the polynaphthoxazines was thereafter studied by thermogravimetric analysis (TGA).

Keywords

1,3-naphthoxazine ; polynaphthoxazine ; thermal polymerization ; thermal properties 1,3-naftoksazyna ; polinaftoksazyna ; polimeryzacja termiczna ; właściwości termiczne

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Gabbas, A. U. G., Ahmad, M. B. H., Zainuddin, N., & Ibrahim, N. A. (2021). Synthesis, characterization and thermal polymerization of new 3,4-dihydro-2H-1,3-naphthoxazine monomers. Polimery, 62(2), 86–92. https://doi.org/10.14314/polimery.2017.086

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A. U. G. Gabbas abduusmangbs@gmail.com

Affiliation
University Putra Malaysia, Faculty of Sciences, Department of Chemistry, 43400 Serdang, Selangor, Malaysia

M. B. H. Ahmad

Affiliation
University Putra Malaysia, Faculty of Sciences, Department of Chemistry, 43400 Serdang, Selangor, Malaysia

N. Zainuddin

Affiliation
University Putra Malaysia, Faculty of Sciences, Department of Chemistry, 43400 Serdang, Selangor, Malaysia

N. A. Ibrahim

Affiliation
University Putra Malaysia, Faculty of Sciences, Department of Chemistry, 43400 Serdang, Selangor, Malaysia