Facile, One-Pot Synthesis of Aromatic Diamine-Based Benzoxazines and Their Advantages Over Diamines as Epoxy Hardeners
Facile, One-Pot Synthesis of Aromatic Diamine-Based Benzoxazines and Their Advantages Over Diamines as Epoxy Hardeners
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DOI：
10.1002/pola.24013
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发表时间：
2010-06-01
影响因子：
--
通讯作者：
Lin, Ching Hsuan
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文献类型：
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作者：
Chang, Sheng Lung;Lin, Ching Hsuan
分别以1,4 - 苯二胺（1）、4,4'-二氨基二苯醚（2）和4,4'-二氨基二苯甲烷（3）为原料，通过一种简便、清洁的一锅法成功制备了三种基于芳香二胺的苯并噁嗪。它们的结构通过核磁共振光谱和单晶衍射图得以确认。讨论了二胺的反应活性对所得苯并噁嗪纯度的影响。将所得苯并噁嗪用作甲酚酚醛环氧树脂（CNE）的固化剂。讨论了苯并噁嗪/CNE体系的加工窗口、潜伏固化特性和相容性。与二胺（1和3）相比，基于（1和3）的苯并噁嗪作为环氧固化剂表现出潜伏固化特性，并且可获得较宽的加工窗口。与在熔融状态下与CNE不相容的二胺（2）相比，基于（2）的苯并噁嗪与CNE表现出良好的相容性。动态力学分析表明，苯并噁嗪/CNE热固性材料的玻璃化转变温度（T(g)）高达242 - 243℃。热重分析表明所得热固性材料具有优异的热稳定性。（C）2010威利期刊公司，《聚合物科学A辑：聚合物化学》48：2430 - 2437，2010
Three aromatic diamine-based benzoxazines were successfully prepared by a facile, clean, one-pot procedure from 1,4-phenylenediamine (1), 4,4'-diaminodiphenyl ether (2), and 4,4'-diaminodiphenyl methane (3), respectively. Their structures were confirmed by NMR spectra and single crystal diffractogram. The effect of the reactivity of diamines on the purity of the resultant benzoxazines was discussed. The resultant benzoxazines were applied as hardeners for cresol novolac epoxy (CNE). The processing window, the latent curing characteristic, and the miscibility of benzoxazine/CNE systems were discussed. Compared with diamines (1 and 3), (1 and 3)-based benzoxazines show latent curing characteristic as epoxy hardeners, and wide processing windows can be obtained. Compared with diamine (2) which is immiscible with CNE in the molten state, (2)-based benzoxazine shows good miscibility with CNE. Dynamic mechanical analysis shows the T(g)s of the benzoxazine/CNE thermosets are as high as 242-243 degrees C. Thermogravimetric analysis shows the outstanding thermal stability of the resultant thermosets. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 2430-2437, 2010