Synthesis, Characterization, and Thermal Properties of Alkyl-Functional Naphthoxazines

UYAR, Tamer
Hacaloğlu, Jale
Ishida, Hatsuo
A series of alkyl-functional naphthoxazine resins having various alkyl chain lengths from C1 to C18 are synthesized with a high yield and high purity by the reactions of 1,5-dihydroxynaphthalene, formaldehyde, and aliphatic amines. The proposed chemical structures of the naphthoxazines are confirmed by high-resolution mass spectrometry, H-1 nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and pyrolysis mass spectrometry studies. The alkyl-functional naphthoxazines have shown low polymerization temperature characteristics where polymerization of these monomers is achieved in the range of 150-170 degrees C yielding cross-linked polynaphthoxazines. The low-temperature polymerization characteristics and the associated thermal degradation behaviors are studied. (C) 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 127: 3114-3123, 2013


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Uyar, Tamer; Koyuncu, Zeynep; Ishida, Hatsuo; Hacaloğlu, Jale (2008-12-01)
Pyrolysis mass spectrometry (MS) analysis of aromatic amine-based naphthoxazine monomer (15-Na) and Poly15-Na has been carried out. Evaporation and degradation of the monomer are detected during the curing process while the polymerisation proceeded. The polymerisation and degradation mechanisms are proposed for 15-Na and Poly15-Na, respectively. The proposed polymerisation mechanism for naphthoxazine monomer was through the aniline units either by coupling of the radicals generated by cleavage of the side r...
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2-[(3-Thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate (TOET) was synthesized via the reaction of 3-thionylcarboxylic acid with ethylene glycol, and electrochemically polymerized with thiophene (Th) and pyrrole (Py) by using tetrabutylannnonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (ACN). Characterization of the resulting copolymers were performed via cyclic voltammetry, FTIR, and scanning electron microscopy (SEM). Electrical conductivities are measured by the four-probe ...
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Segmented polyurethanes were synthesized by the reactions of poly(epsilon-caprolactone) (PCL)-diol and 1,6-hexamethylene diisocyanate through bulk polymerization without using solvent, initiator, or catalyst. Phase separation and hydrogen bond formation between hard segments or between hard and soft segments were examined by Fourier transform infrared spectroscopy (FTIR)-ATR and X-ray diffraction (XRD), while physical and mechanical properties were studied by atomic force microscope, differential scanning c...
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The host-guest complex of a proline-thiourea bipyridine trifluoromethanesulfonic acid salt can catalyze organocatalytic asymmetric reactions such as aldol, Michael, and Mannich in polar protic medium with high stereoselectivities. The privileged bipyridine backbone and the thiourea motif are essential to the activity and enantioselectivity through hydrogen bonding interactions.
Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives
Khan, Rehan; Ulusan, Sinem; Banerjee, Sreeparna; Doğan, Özdemir (Wiley, 2019-11-01)
New aziridine 2-phosphonic acids were prepared by monohydrolysis of the aziridine 2-phosphonates that were obtained by the modified Gabriel-Cromwell reaction of vinyl phosphonate or alpha-tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT-116 colorectal cancer cell lines and the CCD-18Co normal colon fibroblast lines using the MTT assay. Three of the synthesized phosphonic acid derivatives 2e (ethyl hydrogen {(2S)-1-[(1S)-1-...
Citation Formats
T. UYAR, J. Hacaloğlu, and H. Ishida, “Synthesis, Characterization, and Thermal Properties of Alkyl-Functional Naphthoxazines,” JOURNAL OF APPLIED POLYMER SCIENCE, pp. 3114–3123, 2013, Accessed: 00, 2020. [Online]. Available: