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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Industrial Chemistry Research Institute
2017
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| Online Access: | 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 |
| _version_ | 1825932590291353600 |
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| author | Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa |
| author_facet | Gabbas, Abdullahi Usman Garin Ahmad, Mansor B. Hj. Zainuddin, Norhazlin Ibrahim, Nor Azowa |
| author_sort | Gabbas, Abdullahi Usman Garin |
| collection | UPM |
| description | 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). |
| first_indexed | 2024-03-06T09:44:22Z |
| format | Article |
| id | upm.eprints-63371 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T09:44:22Z |
| publishDate | 2017 |
| publisher | Industrial Chemistry Research Institute |
| record_format | dspace |
| spelling | 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 |
| 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 |
| title | 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_short | 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 |
| 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 |
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