Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers
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 co...
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Industrial Chemistry Research Institute
2017
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my.upm.eprints.633712018-10-16T09:26:50Z http://psasir.upm.edu.my/id/eprint/63371/ Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa 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, H-1 NMR and C-13 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). Industrial Chemistry Research Institute 2017 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/63371/1/Synthesis%2C%20characterization%20and%20thermal%20polymerization%20of%20new%203%2C4-dihydro-2H-1%2C3-naphthoxazine%20monomers.pdf Gabbas, Abdullahi Usman Garin and Ahmad, Mansor B. Hj. and Zainuddin, Norhazlin and Ibrahim, Nor Azowa (2017) Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers. Polimery, 62 (2). pp. 86-92. ISSN 0032-2725 10.14314/polimery.2017.086 |
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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, H-1 NMR and C-13 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). |
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Article |
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Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa |
spellingShingle |
Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
author_facet |
Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa |
author_sort |
Gabbas, Abdullahi Usman Garin |
title |
Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
title_short |
Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
title_full |
Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
title_fullStr |
Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
title_full_unstemmed |
Synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2H-1, 3-naphthoxazine monomers |
title_sort |
synthesis, characterization and thermal polymerization of new 3, 4-dihydro-2h-1, 3-naphthoxazine monomers |
publisher |
Industrial Chemistry Research Institute |
publishDate |
2017 |
url |
http://psasir.upm.edu.my/id/eprint/63371/1/Synthesis%2C%20characterization%20and%20thermal%20polymerization%20of%20new%203%2C4-dihydro-2H-1%2C3-naphthoxazine%20monomers.pdf http://psasir.upm.edu.my/id/eprint/63371/ |
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1643837784261132288 |
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13.18916 |